Technical field
[0001]
　The present invention relates to an optical material for the polymerizable composition containing the ultraviolet absorber, an optical material and a plastic lens obtained from the composition.
BACKGROUND
[0002]
　Plastic lenses, a high refractive index compared with inorganic lenses, a high Abbe number, difficult to crack lightweight, dyeing spectacle lenses because it can, it has rapidly spread as an optical material such as a camera lens. This variety of lens molded articles have so far been developed and used.
　Representative examples among them, and allyl resins obtained from diethylene glycol bis allyl carbonate and diallyl isophthalate, and (meth) obtained from acrylate (meth) acrylic resins, polythiourethane resin obtained from isocyanates and thiols.
[0003]
　Lens comprising allyl resin, the polymerization catalyst used, cracking during generation and release of cracks that are observed are known at the time of polymerization.
　Patent Document 1, a diethylene glycol bis allyl carbonate, a composition comprising a diisopropyl peroxydicarbonate, a predetermined block copolymers are disclosed in the Examples. In Patent Document 1, although organic peroxide compounds other than diisopropyl peroxydicarbonate is illustrated, specific examples were prepared lenses by using the compound is not disclosed.
[0004]
　In recent years, development of a plastic lens having a function of UV rays (UV) have been developed.
　Conventionally, the negative effects of the eye exposed to ultraviolet light, has been problematic. Furthermore, in recent years, natural light, and a liquid crystal display of office equipment, by the blue light included in the light emitting from the display, such as a smart phone or a portable device such as a mobile phone, such as the feel eye fatigue and pain, and the impact to the eye problem it has been, eye, reduce the amount of exposure to blue light of relatively short wavelength of about 420nm from an ultraviolet it has been desired.
[0005]
　The effect to the eye of 420nm approximately short wavelength blue light, is described in Non-Patent Document 1.
　In this document, it is to verify the damage to the retinal nerve cells by irradiation of different blue LED light having a peak wavelength of 411nm and 470 nm (cultured retinal neurons R28 rat cells). As a result, irradiation of the blue light (4.5 W / m with a peak wavelength of 411 nm 2 to cause cell death of retinal nerve cells within) is 24 hours, the blue light having a peak wavelength at 470 nm, the same amount of has been shown to change the cell does not occur in the irradiation, have been shown to suppress the 400 ~ 420 nm wavelength of light exposure is important failure prevention eye.
　Also, long exposure to the irradiation of blue light in the eye, be subject to eye strain and stress are concerned, it is considered a cause of age-related macular degeneration.
[0006]
　Patent Document 2, or the wavelength 300 nm, the average light transmittance at 400nm following range is 0.5% or less, the plastic lens containing an ultraviolet absorbing agent is disclosed.
　Patent Document 3, diethylene glycol bis-allyl carbonate polymer in a benzophenone ultraviolet absorber, an amount more and wavelength 440nm light transmittance of the light transmittance of the wavelength 380nm is 0% is added than the amount that the 90% manufacturing method of diethylene glycol bis-allyl carbonate polymer according to the radical polymerization is disclosed.
[0007]
　Patent Document 4, the polymerizable composition comprising a polymerizable allyl carbonate and a photochromic compound, the polymerizable composition in an amount not to exceed 1 part by weight per 100 parts by weight of an ultraviolet absorber polymerizable allyl carbonate is disclosed It is. Furthermore, the polymerizable allyl carbonate is bis (allyl carbonate) of a mixture of diethylene glycol monomer or monomers and oligomers, of bis (allyl carbonate) of a mixture of monomer or monomers and oligomers of neopentyl glycol, pentaerythritol tetrakis (allyl it is disclosed that may include carbonate) and the like.
[0008]
　Patent Document 5, a mixture of diallyl carbonate and phthalic acid esters, one or more 2-8 straight or side chain type are polymerizable obtained by reacting trans-esterified with a polyol containing a carbon atom composition, it is disclosed that may include an ultraviolet absorber.
　Patent Document 6, the allyl ester compound, a bis (allyl carbonate) compound, an organic peroxide, a polymerizable composition containing an organic dye in a predetermined amount is disclosed, further contain an ultraviolet absorber it has been described better. In an embodiment, the Macrolex Blue RR, Solvaperm Red BB is used as the organic dye.
[0009]
　Patent Document 7, a compound containing two or more allyloxycarbonyl group, and a predetermined ultraviolet absorber, comprising a radical polymerization initiator, and a dye, and optical materials polymerizable compositions are disclosed.
[0010]
　Patent Document 8, a specific polymerizable compound, a polymerizable composition comprising a polyether-modified silicone compound is disclosed, molded product obtained from the composition is described as dyeing defects is improved. Patent Document 9, a specific polymerizable compound, a polymerizable composition comprising a polyether-modified silicone compound is disclosed, molded product obtained from the composition are described as striae can be improved.
CITATION
Patent Document
[0011]
Patent Document 1: JP-T 2003-517064 Patent Publication
Patent Document 2: JP-A-10-186291
Patent Document 3: JP 60-245607 Patent Publication
Patent Document 4: JP-A 7-2938 discloses
Patent Document 5: International Publication No. 2001/16194
Patent Document 6: WO 2000/31584 Patent
Patent Document 7: WO 2017/090725
Patent Document 8: JP-a 11-77841 discloses
Patent Document 9: WO 2016/125786
Non-patent literature
[0012]
Non-Patent Document 1: The European journal of neuroscience, vol.34, Iss.4, 548-58, (2011)
Summary of the Invention
Problems that the Invention is to Solve
[0013]
　However, the the Patent Documents described technology there is room for improvement in the following points.
　It used in the examples of Patent Document 1, diisopropyl peroxydicarbonate as a catalyst, since there is a safety problem during lens manufacturing using stability and it during storage, avoiding the use of the compound it has been desired. On the other hand, when using a catalyst other than the compounds, there are cases where cracking during generation and release of cracks during polymerization of those above point is improved is observed.
　The polymerizable composition as described in Patent Documents 1 to 9, or cracks occur, cracks during release there occur during polymerization.
Means for Solving the Problems
[0014]
　The present inventors have found that such prior art problems result of studies to solve the, by using a combination of specific components, while maintaining good clarity, crack generation or release during polymerization crack when is inhibited, it was found to be excellent in productivity.
[0015]
　That is, the present invention can be illustrated below.
[1] (A) the following formula represented by (a), a compound containing two or more allyloxycarbonyl group,
　(B) peroxy ketal radical polymerization initiator, peroxy monocarbonate based radical polymerization initiator and at least one radical polymerization initiator is selected from the group consisting of peroxyester polymerization initiator,
　(C) a polyether modified siloxane compound represented by the following general formula (c1) or the following general formula (c2 ), a modifier selected from a polyol compound represented by
including, for optical materials polymerizable composition;
formula 1]

in (formula (a), n is an integer of 2 ~ 6 .R 1 is a hydrogen atom or a methyl group, more present R 1 may optionally be the same or different .X is a straight-chain or branched aliphatic oxygen atoms have good carbon atoms 3 be ~ 12 have Po Divalent to hexavalent organic group a derived from polyol, divalent to hexavalent organic group b or a carbon atom, contain an oxygen atom derived from alicyclic polyols good carbon atoms 5-16 6 to a 12 aromatic compounds 2 to hexavalent organic group derived from c, an organic group a or an organic group b is combined with an allyloxycarbonyl group through an oxygen atom derived from a hydroxyl group they comprise Te to form an allyl carbonate group.)
[formula 2]

in (formula (c1), R 1 ~ R 8May be the same or different, R 1 ~ R 8 at least one represents a polyether group represented by the following general formula (c1a), other R 1 ~ R 8 are be the same or different well, a linear or branched alkyl group, a linear or branched alkoxy group having 1 to 20 carbon atoms, a hydroxyl group or a polysiloxy group, having 1 to 20 carbon atoms. R presence of a plurality of 2 ~ R 5 may be the same or different. m, n may be the same or different, represent an integer of 0 or greater. ),
[Chemical Formula 3]

In (formula (c1a), R 25 is a linear or branched alkylene group, R having 1 to 20 carbon atoms 26 is hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms , C 2-20 straight or branched alkenyl group or C 2-20 straight-chain or indicating a branch alkynyl groups. multiple present R 25 is good .k be the same or different 1 or more represents an integer.)
[formula 4]

in (formula (c2), R 2 represents a hydroxyl group, a -OX group or a linear or branched alkyl group having a carbon number of 1 ~ 4, .R 3 represents a hydrogen atom, X group, or a linear or branched alkyl group having 1 to 4 carbon atoms. R 4 represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms. Q 1 ~ Q 7 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, -CH 2 represents an -OX group or -OX group. p represents an integer of 1 ~ 4, s represents an integer of 0 ~ 4, t is an integer of 0 ~ 4, r is an integer of 1 to 1,000. Q presence of a plurality of 1 ～ Q 7 , X, S, T may be the same or different. * Represents a bond. ).
[2] In addition, (D) containing the ultraviolet absorbent represented by the following general formula (d), the optical material for the polymerizable composition according to [1];
[Chemical Formula 5]

In (formula (d), R 1 is a hydrogen atom, a linear or branched alkyl group having a carbon number of 1 to 20. R presence of a plurality of 1 each other may be the same or different .m is an integer of 1 to 3, n represents 1 to 3 of an integer, the sum of m and n is an integer of 3-6.).
[3] In addition, according to the (E) anthraquinone dyes, perinone dyes, monoazo dyes, at least one dye selected from diazo dyes, and phthalocyanine dyes, [1] or [2] The optical material for the polymerizable composition.
[4] 2 or more compounds containing allyloxycarbonyl group (A) is
allyl carbonate polymerizable compound represented by the following general formula (a1) (A1) and its oligomers,
the following general formula (a2-1) or the following formula (a2-2) allyl ester polymerizable compound represented by (A2) and oligomers thereof or
a polymerizable compound containing at least one of the allyl ester group and an allyl carbonate group represented by the following general formula (a3) ( A3) and oligomers thereof, [1] to an optical material for the polymerizable composition according to any one of [3];
[Chemical formula 6]

in the (formula (a1), X is 3 carbon atoms It represents a linear or branched divalent to hexavalent group or divalent to hexavalent group derived from alicyclic polyols carbon atoms 5-16 derived from aliphatic polyols ~ 12, n is 2 Represents an integer of 6.)
[Chemical Formula 7]

[Chemical Formula 8]

In (formula (a2-2), 2 X is derived from a straight-chain or branched aliphatic diols having 2 to 8 carbon atoms -valent radical or a linear or branched 3-6 monovalent group derived from an aliphatic polyol having 3 to 10 carbon atoms having 3-6 hydroxyl groups,, n represents an integer of 2-6. ),
[Formula 9]

(In the general formula (a3), X is a divalent group derived from a straight-chain or branched aliphatic diols having 2 to 8 carbon atoms or 3-10 carbon atoms having 3-6 hydroxyl groups, It represents a linear or branched 3-6 monovalent group derived from an aliphatic polyol, m and n represents an integer of 0-6, and the sum of m and n is an integer of 2-6.) .
[5] The allyl carbonate polymerizable compound (A1), diethylene glycol, dipropylene glycol, triethylene glycol, tetraethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1 , 6-hexanediol, neopentyl glycol, 3-methyl-1,5-pentanediol, 2-methyl-2-ethyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, 2 , 2,4-trimethyl-1,3-pentanediol, 1,4-dimethylolcyclohexane and 4,8-bis (hydroxymethyl) - [5.2.1.0 2, 6 ] is selected from tricyclodecane at least one diol bis (allyl carbonate) compounds that,
glycerol, trimethylene Tris of at least one triol selected from trimethylol propane and tris (hydroxyethyl) isocyanurate (allyl carbonate) compounds,
pentaerythritol, at least one tetraol tetra (allyl selected from diglycerol and ditrimethylolpropane carbonate) compounds,
hexa (allyl carbonate dipentaerythritol) compounds, and
The diols, the triol, the mixed poly (allyl carbonate) compound of at least two compounds selected from tetraols and the dipentaerythritol, comprises at least one selected from, the optical material according to [4] use polymerizable composition.
[6] The allyl carbonate polymerizable compound (A1),
(i) diethylene glycol bis (allyl carbonate) compounds and mixtures and oligomers thereof,
(ii) bis diethylene glycol and mixtures of neopentyl glycol (allyl carbonate) compounds, and a mixture of oligomers thereof,
(iii) poly diethylene glycol and tris (hydroxyethyl) mixture of isocyanurate (allyl carbonate) compounds and mixtures and oligomers thereof,
(iv) poly diethylene glycol and a mixture of trimethylol propane (allyl carbonate) compounds and mixtures and oligomers thereof,
(v) poly (allyl carbonate) of a mixture of diethylene glycol and pentaerythritol compounds and mixtures and oligomers thereof,
(vi) diethylene Gris Lumpur and poly neopentyl glycol and mixtures of pentaerythritol (allyl carbonate) compounds and mixtures thereof with oligomers, and
a (vii) poly (allyl carbonate) of diethylene glycol and neopentyl glycol and mixtures of pentaerythritol compound and its oligomer and a mixture of,
Diethylene glycol bis (allyl carbonate) compounds, and poly (allyl carbonate) mixture comprising a mixture of oligomers thereof, and
comprises at least one member selected from, for optical materials polymerizable composition according to [4].
[7] The allyl ester polymerizable compound (A2) or the polymerizable compound (A3),
diallyl isophthalate, diallyl phthalate compound selected from diallyl terephthalate and diallylorthophthalate,
said diallyl phthalate compound, ethylene glycol, diethylene glycol , dipropylene glycol, triethylene glycol, tetraethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, neopentyl glycol, 3-methyl-1,5-pentanediol, 2-methyl-2-ethyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, 2,2,4-trimethyl -1 , 3-pentane Diol, 1,4 least one diol diallyl ester compounds and oligomers obtained by transesterification of a mixture of selected from dimethylol cyclohexane,
and the diallyl phthalate compound, glycerol, trimethylol propane, tris (hydroxy ethyl) isocyanurate, pentaerythritol, diglycerol, ditrimethylolpropane, at least one polyol transesterification polyallyl ester compound and its oligomer obtained by the mixture of selected from dipentaerythritol, and
Dialkyl isophthalate having an alkyl group having 1 to 3 carbon atoms, a dialkyl terephthalate, a mixture of at least one dialkyl phthalate selected from dialkyl ortho phthalate, allyl alcohol, diallyl carbonate, and the diol or the polyol obtained by transesterification, allyl ester compound, allyl carbonate compound, and a compound having an allyl carbonate group and an allyl ester group and containing at least one oligomer thereof, is selected from polymerizable optical material according to [4] gender composition.
[8] The allyl ester polymerizable compound (A2) or the polymerizable compound (A3) is,
(i) diallyl terephthalate and, said diallyl terephthalate against 30% by weight of diethylene glycol bis (allyl carbonate) compounds and oligomers thereof a mixture of,
(ii) diallyl terephthalate and allyl ester compound obtained by transesterification of a mixture of propylene glycol,
allyl ester compound, a 20% by weight relative to the allyl ester compound of (iii) (ii) diethylene glycol bis (allyl carbonate) compounds and mixtures and oligomers thereof,
(iv) dimethyl terephthalate, allyl alcohol, obtained by the transesterification of diallyl carbonate, and mixtures of diethylene glycol, allyl ester Compound, allyl carbonate compound, and mixtures of compounds having the allyl ester group and an allyl carbonate group, and
including (v) and the mixture obtained in (iv), and 10 wt% of diethylene glycol bis (allyl carbonate) compounds and oligomers thereof to the mixture, the mixture, at least one member selected from the [4 the optical material for the polymerizable composition according to.
[9] The compound containing two or more allyloxycarbonyl group (A),
　and the allyl ester polymerizable compound (A2) and / or the polymerizable compound (A3) and their oligomers according to [7], the allyl carbonate polymer compound (A1) and an optical material for the polymerizable composition according to the oligomer, a mixture of [4] according to [5].
[10] ultraviolet absorber (D) is 2,2'-dihydroxy-4-methoxybenzophenone, 2,2 ', 4,4'-tetra-hydroxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxy benzophenone, an optical material for the polymerizable composition according to [2].
[11] the radical polymerization initiator (B) is 10-hour half-life temperature of 80 ° C. or more peroxy ketal polymerization initiator represented by the following general formula (b1), is represented by the following general formula (b2) 10-hour half-life temperature of from 80 ° C. or more peroxy monocarbonate based polymerization initiator, and 10-hour half-life temperature of 65 ° C. or more peroxyester polymerization initiator represented by the following general formula (b3) that is at least one selected from the group, [1] to an optical material for the polymerizable composition according to any one of [10];
[formula 10]

in the (general formula (b1), R 3 is a tertiary alkyl group, R 1 and R 2 -methyl each independently, ethyl, alkyl group selected from propyl and butyl, said alkyl group can have an alkyl ester group at the chain end, or R 1 and R 2 is and they are attached together with the carbon atom to which there can be formed a cycloalkylene group, the cycloalkylene group may have 1 to 3 alkyl substituents. ),
[Formula 11]

in the (general formula (b2), R 1 is a tertiary alkyl group having a carbon number of 3 to 6, R 2 is a linear or branched alkyl group having 3 to 8 carbon atoms some.),
[formula 12]

in the (general formula (b3), R 1 is a tertiary alkyl group having a carbon number of 3 to 6, R 2 is a straight-chain or branched alkyl having carbon atoms 3 to 9 is a group or a phenyl group.).
[12] The R of the polyether group represented by the general formula (c1a) 26 is a linear or branched alkyl group having a hydrogen atom or a C 1 to 20 in any one of [1] to [11] the optical material for polymerizable composition.
[13] R polyether group represented by the above general formula (c1a) 26Represents a linear or branched alkynyl group having a linear or branched alkenyl group or C 2-20 2 to 20 carbon atoms, [1] to the polymerizable composition for an optical material according to any one of [11] object.
[14] [1 ~ [13] molded body obtained by curing the optical material for the polymerizable composition according to any one of.
Optical material comprising a molded product according to [15] [14].
[16] a plastic lens composed of a molded product according to [14].
[17] (A) the following formula represented by (a), a compound containing two or more allyloxycarbonyl group,
　(B) peroxy ketal radical polymerization initiator, peroxy monocarbonate based radical polymerization initiator and at least one radical polymerization initiator is selected from the group consisting of peroxyester polymerization initiator,
　(C) a polyether modified siloxane compound represented by the following general formula (c1) or the following general formula (c2 a modifier selected from represented by the polyol compound) were mixed, and the step of preparing an optical material for the polymerizable composition,
　a lens by cast polymerization of the optical material for the polymerizable composition and forming a substrate, a method of manufacturing a plastic lens;
formula 13]

in (formula (a), n is an integer of 2 ~ 6 .R 1 is hydrogen atom or A methyl radical, R presence of a plurality of 1It may be the same or different. X is which may have a linear or branched aliphatic polyol divalent to hexavalent organic group a derived from the oxygen atom has optionally 1-3 carbon atoms which may atom 12, an oxygen atom carbon an alicyclic divalent to hexavalent organic group b derived from a polyol or divalent to hexavalent organic group c derived from an aromatic compound having 6 to 12 carbon atoms, the atoms 5-16, organic group a or an organic group b is combined with an allyloxycarbonyl group through an oxygen atom derived from a hydroxyl group to which they are provided to form the allyl carbonate groups. )
[Formula 14]

in (formula (c1), R 1 ~ R 8 may be the same or different, R 1 ~ R 8 polyether group wherein at least one of which is represented by the following general formula (c1a) are shown, other R 1 ~ R 8 , which may be identical or different, linear or branched alkyl group having 1 to 20 carbon atoms, straight-chain or branched alkoxy group having 1 to 20 carbon atoms, a hydroxyl group or R is. plurality of showing a polysiloxy group 2 ~ R 5 are optionally the same or different from each .m, n may be the same or different, represent an integer of 0 or greater.)
[Formula 15 ]

(in the general formula (c1a), R 25A linear or branched alkylene group having 1 to 20 carbon atoms, R 26 is a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, C 2-20 linear or branched alkenyl group or a carbon a linear or branched alkynyl group having 2 to 20. R presence of a plurality of 25 may be the same or different. k is an integer of 1 or more. )
[Formula 16]

in (formula (c2), R 2 represents a hydroxyl group, .R represents an -OX group or a linear or branched alkyl group having 1 to 4 carbon atoms, 3 is a hydrogen atom, X group, or .R represents a linear or branched alkyl group having 1 to 4 carbon atoms 4 is .Q represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, 1 ~ Q 7 are each independently represent hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, -CH 2 .p representing the -OX group or -OX group, represents an integer of 1-4, s is 0-4 an integer, t is an integer of 0 ~ 4, r is Q is. plurality of indicating an integer of 1 to 1,000 1 ~ Q 7 , X, s, t may be the same or different. * is a bond.)
[18] The step of preparing the optical material for the polymerizable composition further (D) a mixture of UV absorber represented by the following general formula (d), to prepare an optical material for the polymerizable composition is a process, method of manufacturing a plastic lens according to [17];
[formula 17]

(in the general formula (d), R 1 represents a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms . plurality of R to 1 each other may be the same or different .m is an integer of 1 to 3, n is an integer of 1 to 3, the sum of m and n is an integer of 3-6.).
[19] The step of preparing the optical material for the polymerizable composition further (E) anthraquinone dyes, perinone dyes, monoazo dyes, at least one selected from diazo dyes, and phthalocyanine dyes a mixture of dyes, is a step of preparing an optical material for the polymerizable composition, method of manufacturing a plastic lens according to [17] or [18].
[0016]
　In the present invention, the polymerization time of cracks, when forming the molded body by heating and curing the optical material for the polymerizable composition in the mold, cracks occur in any part of the molded body in the mold It represents the in which state. Further, the cracking during the release, after forming a molded body by heat curing the optical material for the polymerizable composition in a mold, in the step of releasing the molded body from the mold, any part of the molded body representing a state in which the cracking has occurred in.
The invention's effect
[0017]
　According to the optical material for the polymerizable composition of the present invention, it is possible to suppress the cracking during formation of cracks and release during polymerization, it is possible to provide an excellent optical material transparent appearance. Such an optical material of the present invention has excellent transparent appearance, since the excellent productivity can be particularly suitably used as a plastic spectacle lens.
DESCRIPTION OF THE INVENTION
[0018]
　The optical material for the polymerizable composition of the present invention will be described with reference to the following embodiments.
　The optical material for the polymerizable composition of the present embodiment,
　(A) the following general formula (a) represented by a compound containing two or more allyloxycarbonyl group,
　(B) peroxy ketal radical polymerization initiator , and at least one radical polymerization initiator is selected from the group consisting of peroxy monocarbonate based radical polymerization initiator and peroxyester polymerization initiator,
　poly (C) represented by the following general formula (c1) ether-modified siloxane compound or a modifier selected from a polyol compound represented by the following general formula (c2),
including, for optical materials polymerizable composition;
[0019]
[Chem. 18]

[0020]
　式（ａ）中、ｎは２～６の整数である。Ｒ １は水素原子またはメチル基を示し、複数存在するＲ １は同一でも異なっていてもよい。Ｘは、酸素原子を有していてもよい炭素原子数３～１２の直鎖または分岐の脂肪族ポリオールから誘導される２～６価の有機基ａ、酸素原子を有していてもよい炭素原子数５～１６の脂環族ポリオールから誘導される２～６価の有機基ｂ、または炭素原子数６～１２の芳香族化合物から誘導される２～６価の有機基ｃであり、有機基ａまたは有機基ｂは、これらが備える水酸基由来の酸素原子を介してアリルオキシカルボニル基と結合してアリルカーボネート基を形成する。
[0021]
[化19]

[0022]
　一般式（ｃ１）中、Ｒ １～Ｒ ８は同一または異なっていてもよく、Ｒ １～Ｒ ８の少なくとも一つは下記一般式（ｃ１ａ）で表されるポリエーテル基を示し、その他のＲ １～Ｒ ８は、同一または異なっていてもよく、炭素数１～２０の直鎖もしくは分岐のアルキル基、炭素数１～２０の直鎖もしくは分岐のアルコキシ基、ヒドロキシル基、またはポリシロキシ基を示す。複数存在するＲ ２～Ｒ ５は、それぞれ同一または異なっていてもよい。ｍ、ｎは同一または異なっていてもよく、０以上の整数を示す。
[0023]
[化20]

[0024]
　一般式（ｃ１ａ）中、Ｒ ２５は炭素数１～２０の直鎖もしくは分岐のアルキレン基、Ｒ ２６は水素原子、炭素数１～２０の直鎖もしくは分岐のアルキル基、炭素数２～２０の直鎖もしくは分岐のアルケニル基または炭素数２～２０の直鎖もしくは分岐のアルキニル基を示す。複数存在するＲ ２５は同一でも異なっていてもよい。ｋは１以上の整数を示す。
[0025]
[化21]

[0026]
　Wherein (c2), R 2 represents a hydroxyl group, a -OX group or a linear or branched alkyl group having 1 to 4 carbon atoms. R 3 represents a hydrogen atom, X group, or a linear or branched alkyl group having 1 to 4 carbon atoms. R 4 represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms. Q 1 ~ Q 7 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, -CH 2 represents an -OX group or -OX group. p represents an integer of 1 ~ 4, s represents an integer of 0 ~ 4, t is an integer of 0 ~ 4, r is an integer of 1 to 1,000. Q presence of a plurality of 1 ～ Q 7 , X, S, T may be the same or different. * Represents a bond.
[0027]
　The optical material for the polymerizable composition of the present embodiment, by using a combination of component (A) ~ Component (C), while maintaining a good hue and transparency, further crack generation and release during polymerization cracking of the time is suppressed, and excellent in productivity.
　Each component is explained below.
[0028]
[Compound (A) containing two or more allyloxycarbonyl group]
　in the present embodiment, a compound containing two or more allyloxycarbonyl group (A) can be represented by the following general formula (a).
[0029]
[Formula 22]

[0030]
　In the general formula (a), n is an integer of 2-6. R 1 represents a hydrogen atom or a methyl radical, R presence of a plurality of 1 may be the same or different.
[0031]
　X represents a linear or branched bivalent to hexavalent derived from an aliphatic polyol a1 of the organic groups a oxygen atom has optionally 1-3 carbon atoms which may atom 12 may have an oxygen atom 2-6 divalent organic group b or 2 to be derived from an aromatic compound c1 having 6 to 12 carbon atoms hexavalent organic group c, derived from alicyclic polyols b1 carbon atoms 5-16 There, an organic group a or an organic group b is combined with an allyloxycarbonyl group through an oxygen atom derived from a hydroxyl group to which they are provided to form the allyl carbonate groups.
　These polyols, 2-6 in the normal molecule, preferably containing 2 to 4 hydroxyl groups.
[0032]
　The aliphatic polyol a1, diethylene glycol, dipropylene glycol, triethylene glycol, tetraethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, neo neopentyl glycol, 3-methyl-1,5-pentanediol, 2-methyl-2-ethyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, 2,2,4-trimethyl - 1,3-pentanediol, glycerol, trimethylolpropane, tris (hydroxyethyl) isocyanurate, pentaerythritol, and di pentaerythritol.
　Examples of the alicyclic polyols b1, 1,4-dimethylolcyclohexane, 4,8-bis (hydroxymethyl) - [5.2.1.0 2, 6 ] can be given tricyclodecane and the like.
　The aromatic compounds c1, benzene, toluene, xylene, naphthalene and the like.
　As the compound containing two or more allyloxycarbonyl group (A), specifically, the allyl carbonate polymer compound (A1), allyl ester polymerizable compound (A2), at least one allyl carbonate group and allyl ester group polymerizable compounds containing (A3) can be exemplified.
[0033]
　Compounds containing 2 or more allyloxycarbonyl group (A) may contain the oligomer. Compounds containing 2 or more allyloxycarbonyl group, at room temperature a liquid product, the viscosity measured at 25 ° C. is 10 ~ 1000 cSt, the oligomer content can vary within wide limits, for example, 0 to about 80 in weight percent.
[0034]
(Allyl carbonate polymer compound (A1))
　allyl carbonate polymer compound (A1) can be represented by the following general formula (a1), and may include oligomers thereof. Oligomer is a poly via carbonate groups produced by transesterification of allyl carbonate and a polyol produced by the production process 2 molecules or more polyols linked (allyl carbonate).
[0035]
　The allyl carbonate polymer compound is a straight-chain or poly (allyl carbonate) of branched aliphatic polyol compounds having 3 to 12 carbon atoms. Poly (allyl carbonate) compounds of alicyclic polyols having from 5 to 16 carbon atoms in the molecule are also suitable for this purpose. These polyols, 2-6 in the normal molecule, preferably having 2 to 4 hydroxyl groups. Mixed poly (allyl carbonate) compounds, i.e. derived from two or more polyols, one can be obtained by mechanical mixing of poly (allyl carbonate) compounds each polyol, or starting from a mixture with diallyl carbonate polyol it is also possible to use those which can be obtained directly by a chemical reaction.
[0036]
　Finally, all of the poly (allyl carbonate) compounds these may be in the form of a mixture of monomer or monomers and oligomers. In general, allyl carbonate polymer compound is a liquid product at room temperature, the viscosity measured at 25 ° C. is 10 ~ 1000 cSt, the oligomer content can vary within wide limits, for example, 0 to about 80 in weight percent.
[0037]
[Of 23]

[0038]
　In the general formula (a1), X is derived from alicyclic polyols having 2 to 6 valent group or a carbon atom number of 5 to 16 which is derived from a straight-chain or branched aliphatic polyol having 3 to 12 carbon atoms It represents a divalent to hexavalent groups, n represents an integer of 2-6.
[0039]
　Polyols constituting the X in the general formula (a1), as a specific example, diethylene glycol, dipropylene glycol, triethylene glycol, tetraethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5 pentanediol, 1,6-hexanediol, neopentyl glycol, 3-methyl-1,5-pentanediol, 2-methyl-2-ethyl-1,3-propanediol, 2,2-diethyl-1,3 propanediol, 2,2,4-trimethyl-1,3-pentanediol, 1,4-dimethylolcyclohexane, 4,8-bis (hydroxymethyl) - [5.2.1.0 2, 6 ] tricyclo decane, glycerol, trimethylolpropane, tris (hydroxyethyl) isocyanurate, Pentae Suritoru, diglycerol, ditrimethylolpropane, and di pentaerythritol.
[0040]
　Accordingly, examples of the allyl carbonate compound, for example, diethylene glycol, dipropylene glycol, triethylene glycol, tetraethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6 - hexanediol, neopentyl glycol, 3-methyl-1,5-pentanediol, 2-methyl-2-ethyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, 2,2 , 4-trimethyl-1,3-pentanediol, 1,4-dimethylolcyclohexane and 4,8-bis (hydroxymethyl) - [5.2.1.0 2, 6 ] at least selected from tricyclodecane one diol bis (allyl carbonate) compounds, glycerol, DOO Trimethylolpropane and tris (hydroxyethyl) at least one triol tris (allyl carbonate) is selected from the isocyanurate compound, pentaerythritol, at least one tetraol tetra (allyl selected from diglycerol and ditrimethylolpropane carbonate) compounds, selected hexa dipentaerythritol (allyl carbonate) compounds, and the diols, the triol, mixed poly (allyl carbonate) compounds of at least two compounds selected from tetraols and the dipentaerythritol, from It is the at least one.
[0041]
　Note that "at least two bis mixture of diol (allyl carbonate)", for example, if the diol is diethylene glycol and neopentyl glycol is obtained as a mixture of monomer component and oligomer component follows.
Monomer component
(1) diethylene glycol bis (allyl carbonate)
(2) neopentyl glycol bis (allyl carbonate)
oligomer component
(3) linear through the oligomer (diethylene glycol carbonate bond containing only diethylene glycol-derived hydrocarbons (and ether) Jo compound having the structure of which is replaced by two hydroxyl allyl carbonate groups of the compounds oligomerize)
(4) neopentyl glycol oligomers containing only hydrocarbons from (neopentyl glycol through a carbonate linkage linear the compounds in which two hydroxyl groups have a structure which is replaced by allyl carbonate groups of the compounds oligomerize)
(5) of diethylene glycol derived from hydrocarbons (and ether) and neopentyl glycol-derived charcoal Two hydroxyl allyl carbonate groups composite oligomer (diethylene glycol compound neopentyl glycol oligomerized linearized with any sequence in the same molecule via a carbonate bond to include both in the same molecule of hydrogen compounds having replaced structure)
[0042]
　Of those following, the preferred examples of suitable allyl carbonate polymer compound to the purpose (A1) of the present invention, includes at least one selected from these.
(i) diethylene glycol bis (allyl carbonate) and mixtures thereof with oligomers
　of diethylene glycol bis (allyl carbonate) can be defined by the formula (I).
[0043]
[Of 24]

[0044]
　Also, oligomers of diethylene glycol bis (allyl carbonate) can be defined by the formula (II).
[0045]
[Of 25]

[0046]
　In formula (II), n is 2 to 10.
　Compound (I), for example, "Encyclopedia of Chemical Technology", Kirk-Othmer, III Edition, Volume 2, as described in 111-112 pages, reacting diethylene glycol bis (chloroformate) with allyl alcohol it can be produced by. Mixtures of diethylene glycol bis (allyl carbonate) (Formula (I)) and oligomers thereof (formula (II)), for example, European as described in patent 35.304, the presence of a basic catalyst by operating at, it can be conveniently prepared by transesterification of diallyl carbonate and diethylene glycol. These mixtures usually contain up to about 80 wt% oligomers.
[0047]
(ii) diethylene glycol bis (allyl carbonate) of a mixture of neopentyl glycol compounds and mixtures and oligomers thereof
　The bis (allyl carbonate) compounds, except for replacing diethylene glycol with a mixture of diethylene glycol and neopentyl glycol, wherein diethylene glycol bis (i) is the same as (allyl carbonate) compounds.
[0048]
(iii) diethylene glycol and tris poly (allyl carbonate) of a mixture of (hydroxyethyl) isocyanurate compounds and mixtures and oligomers thereof
　The poly (allyl carbonate) compounds, for example, is described in U.S. Patent No. 4,812,545 and as can be obtained by transesterification of diethylene glycol and tris diallyl carbonate of a mixture of (hydroxyethyl) isocyanurate.
[0049]
(iv) diethylene glycol and poly (allyl carbonate) of a mixture of trimethylol propane compounds and mixtures and oligomers thereof
　The poly (allyl carbonate) compounds, except for replacing tris (hydroxyethyl) isocyanurate with trimethylolpropane, it is similar to the poly (allyl carbonate) compound of (iii).
[0050]
(v) diethylene glycol and poly (allyl carbonate) of a mixture of pentaerythritol compound and a mixture of oligomers thereof
　The poly (allyl carbonate) compounds, except for replacing tris (hydroxyethyl) isocyanurate with pentaerythritol, the ( iii) poly (allyl carbonate) is similar to the compound.
[0051]
(vi) diethylene glycol and poly (allyl carbonate) of neopentyl glycol and mixtures of pentaerythritol compound and a mixture of oligomers thereof
　The poly (allyl carbonate) compounds, the diethylene glycol being substituted by two diols diethylene glycol neopentyl glycol it addition, the poly (allyl carbonate) of the (v) is the same as compound.
[0052]
(vii) diethylene glycol and neopentyl glycol and poly (allyl carbonate) of a mixture of pentaerythritol compound and a mixture of oligomers thereof,
poly comprising a mixture of diethylene glycol bis (allyl carbonate) compound and its oligomer, a (allyl carbonate) blend
[0053]
(Allyl ester polymerizable compound (A2), the polymerizable compound (A3))
　allyl ester polymerizable compound (A2) is diallyl phthalate and its oligomer represented by the following general formula (a2-1), the following general formula ( represented by a2-2), allyl ester compound obtained by the transesterification of a mixture of diallyl phthalate with a polyol and can be given its oligomers. As the polymerizable compound (A3), it can be mentioned a polymerizable compound and its oligomer comprising at least one of the allyl ester group and an allyl carbonate group represented by the following general formula (a3).
[0054]
　Polymerizable compound represented by the general formula (a3) is a dialkyl obtained by transesterification of a mixture of phthalate and allyl alcohol and diallyl carbonate with a polyol, an allyl ester compound, allyl carbonate compound, and an allyl ester group and an allyl comprising a mixture of a compound having a carbonate group.
　In the present embodiment, the following general formula (a2-1), the formula (a2-2), the compound of the general formula (a3) are those containing positional isomers.
[0055]
[Of 26]

[0056]
　Diallyl phthalate represented by the general formula (a2-1) is at least one selected diallyl isophthalate, diallyl terephthalate, and diallyl ortho phthalate.
[0057]
[Of 27]

[0058]
　In the general formula (a2-2), X is a divalent group or a hydroxyl group of 3 to 6 3 carbon atoms having ~, derived from a straight-chain or branched aliphatic diols having 2 to 8 carbon atoms It represents a linear or branched 3-6 monovalent group derived from an aliphatic polyol 10, n is an integer of 2-6.
[0059]
[Formula 28]

[0060]
　In the general formula (a3), X is 3 to 10 carbon atoms having 3-6 divalent group or a hydroxyl group, which are derived from linear or branched aliphatic diols having 2 to 8 carbon atoms It represents 3-6 monovalent group derived from a straight or branched aliphatic polyols, m and n represents an integer of 0-6, and the sum of m and n is an integer of 2-6.
[0061]
　Diallyl phthalate used, as a specific example is diallyl isophthalate, diallyl terephthalate, diallyl ortho phthalate,
dialkyl phthalate is phthalic diester having an alkyl group having 1 to 3 carbon atoms, Jimechiruiso specific examples phthalates, dimethyl terephthalate, dimethyl ortho phthalate, diethyl isophthalate, diethyl terephthalate, diethyl ortho phthalate, dipropyl isophthalate, dipropyl terephthalate, include dipropyl ortho phthalate.
[0062]
　The polyol constituting the X in the general formula (a2-2) and the formula (a3) ​​(aliphatic diols, aliphatic polyols), as a specific example, ethylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tetra ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, neopentyl glycol, 3-methyl-1,5 pentanediol, 2-methyl-2-ethyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, 2,2,4-trimethyl-1,3-pentanediol, 1,4 diol and glycerol dimethylol cyclohexane, trimethylol propane der Triols and tris (hydroxyethyl) isocyanurate, pentaerythritol, diglycerol, ditrimethylolpropane, a polyol is dipentaerythritol.
[0063]
　Formula (a2-2) and compound of general formula (a3) ​​may comprise the oligomer. Oligomers are those produced by transesterification of the allyl ester compound and a polyol produced by the production process in the general formula (a2-2). Oligomers in the general formula (a3) ​​are those allyl ester compound was produced in the manufacturing process or allyl carbonate compound is produced by a transesterification reaction of a polyol.
[0064]
　Thus, the allyl ester polymerizable compound (A2) or the polymerizable compound (A3) is, for example, diallyl isophthalate, diallyl terephthalate, and diallyl phthalate compound selected from diallylorthophthalate,
said diallyl phthalate compound, ethylene glycol , diethylene glycol, dipropylene glycol, triethylene glycol, tetraethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, neopentyl glycol, 3-methyl-1,5-pentanediol, 2-methyl-2-ethyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, 2,2,4-trimethyl - , 3-pentanediol, 1,4 least one diallyl ester compounds and oligomers obtained by transesterification of mixtures of diols dimethylolcyclohexane the like is selected,
and the diallyl phthalate compound, glycerol, trimethylol triol propane, tris (hydroxyethyl) isocyanurate, pentaerythritol, diglycerol, ditrimethylolpropane, transesterification polyallyl ester compound obtained by reaction of a mixture of at least one polyol selected from dipentaerythritol and oligomers thereof,
Dimethyl isophthalate, dimethyl terephthalate, dimethyl ortho phthalate, diethyl isophthalate, diethyl terephthalate, diethyl ortho phthalate, dipropyl isophthalate, dipropyl terephthalate, number of at least one carbon atom is selected from dipropyl ortho phthalate 1 to 3 dialkyl phthalate, and allyl alcohol, diallyl carbonate, obtained by transesterification of a mixture of the above-mentioned diol or polyol, an allyl ester compound, allyl carbonate compound, and a compound having an allyl carbonate group and allyl ester group and their oligomers, containing at least one selected from.
[0065]
　The allyl ester polymerizable compound (A2) or the polymerizable compound (A3) is, more specifically,
(i) diallyl terephthalate and 30 wt% of diethylene glycol bis (allyl carbonate) with respect to the diallyl terephthalate compound and its oligomer, a mixture of,
(ii) diallyl tele allyl ester compound obtained by transesterification of a mixture of phthalate and propylene glycol,
allyl ester compound (iii) (ii), relative to the allyl ester compound 20 wt% of diethylene glycol bis (allyl carbonate) compounds and oligomer, mixtures,
(iv) dimethyl terephthalate, allyl alcohol, obtained by the transesterification of diallyl carbonate, and mixtures of diethylene glycol, Riruesuteru compound, allyl carbonate compound, and mixtures of compounds having the allyl ester group and an allyl carbonate group, and
(v) (iv) and the mixture obtained in, diethylene glycol bis (allyl 10% by weight based on the mixture carbonate) compounds and oligomer, mixtures preferably comprises at least one member selected from.
[0066]
　The following are preferred examples of suitable allyl ester polymerizable compound for the purposes of the present invention (A2) or the polymerizable compound (A3).
(i) dimethyl terephthalate, allyl alcohol, diallyl carbonate, and obtained by transesterification of a mixture of diethylene glycol, allyl ester compound, a mixture of allyl carbonate compound, and a compound having an allyl ester group and an allyl carbonate group
　the allyl ester polymer sexual compound (A2) or the polymerizable compound (A3) may be defined by the formula (III) ~ (V), a main component diallyl terephthalate of the formula (III), each of which exchange reaction polyol with ester containing oligomer obtained by.
[0067]
[Of 29]

[0068]
　In this embodiment, said compound containing two or more allyloxycarbonyl group (A), from the viewpoint of the effect of the present invention, the allyl ester polymerizable compound (A2) and / or the polymerizable compound (A3) and their it can be an oligomer of the above allyl carbonate polymer compound (A1) and oligomers thereof, and mixtures for.
[0069]
[Radical polymerization initiator (B)]
　The radical polymerization initiator in the present embodiment (B) is peroxy ketal radical polymerization initiator, from peroxy monocarbonate based radical polymerization initiator and peroxyester polymerization initiator at least one radical polymerization initiator selected from the group consisting of.
　More specifically, examples of the radical polymerization initiator of the present embodiment (B), represented by (a) 10-hour half-life temperature of 80 ° C. or more peroxy ketal radical polymerization initiator and the following general formula (b1) / or represented by the following general formula (b2) (b) 10-hour half-life temperature is represented by more than 80 ° C. the peroxy monocarbonate based radical polymerization initiator and / or the following general formula (b3) (c) 10-hour half-life temperature using 65 ° C. or more peroxyester polymerization initiator.
[0070]
[Formula 30]

[0071]
　In formula (b1), R 3 is a tertiary alkyl group, R 1 and R 2 are alkyl groups selected independently from methyl, ethyl, propyl and butyl, said alkyl group is for example a chain of ends can have a functional group such as an alkyl ester group, or R 1 and R 2 are bonded to each other, together with the carbon atoms to which they are attached can form a cycloalkylene group, the cycloalkylene group may have 1 to 3 alkyl substituents.
[0072]
[Of 31]

[0073]
　In formula (b2), R 1 is a tertiary alkyl group having a carbon number of 3 to 6, R 2 is a straight-chain or branched alkyl group having 3 to 8 carbon atoms.
[0074]
[Formula 32]

[0075]
　In formula (b3), R 1 is a tertiary alkyl group having a carbon number of 3 to 6, R 2 is a straight-chain or branched alkyl group or a phenyl group having a carbon number of 3 to 9.
[0076]
　Peroxy ketal radical polymerization initiator (a) in {() shows the 10 hour half-life temperature. The},
1,1-bis (t-butylperoxy) -3,3,5-trimethylcyclohexane (83 °
C.), 1,1-bis (t-hexyl peroxy) -3,3,5-trimethyl cyclohexane (90 °
C.), 2,2-bis (t-butylperoxy) butane (107 °
C.), n-butyl-4,4-bis (t-butylperoxy) Vallee rate (109 ° C.),
ethyl-3 , 1,3-bis (t-butylperoxy) Vallee rate (114 °
C.), 1,1-bis (t-butylperoxy) cyclohexane (91 °
C.), 1,1-bis (t-butylperoxy) -2 - methylcyclohexane (83 °
C.), 1,1-bis (t-amyl peroxy) cyclohexane (93 °
C.), 1,1-bis (t-hexyl peroxy) cyclohexane (87 ° C.),
1,1-bis t- hexyl peroxy) -3,3,5-trimethylcyclohexane (87 °
C.), 2,2-bis [4,4- (di -t- butyl peroxy) cyclohexyl] propane (95 ° C.)
and the like it can.
[0077]
　Peroxy monocarbonate based radical polymerization initiator (b) in {() shows the 10 hour half-life temperature. The},
OO- (t-butyl) -O- isopropyl monoperoxycarbonate (99 °
C.), OO- (t-amyl) -O- isopropyl monoperoxycarbonate (96 °
C.), OO- (t-butyl ) -O- (2-ethylhexyl) monoperoxycarbonate (99 °
C.), OO- (t-amyl) -O- (2-ethylhexyl) monoperoxycarbonate (99 ° C.)
can be mentioned.
[0078]
　Peroxyester radical polymerization initiator (c) in {() shows the 10 hour half-life temperature. The},
t-butyl peroxy-2-ethylhexanoate (72 °
C.), t-butyl peroxy isobutyrate (82 °
C.), t-butyl peroxy-3,3,5-trimethyl hexanoate (97 °
C.), t-butyl peroxy acetate (102 °
C.), t-butylperoxy isononanoate Na benzoate (102 °
C.), t-butyl peroxybenzoate (104 °
C.), t-amyl peroxy-2-ethylhex Noeto (75 °
C.), t-amyl peroxy-n-octoate (96 °
C.), t-amyl peroxy acetate (100 ° C.),
t-amyl peroxy isononanoate Na benzoate (96 °
C.), t-amyl peroxybenzoate (100 °
C.), t-hexyl peroxy-2-ethylhexanoate (70 °
C.), t-hexyl peroxybenzoate Benzoate (99 °
C.), 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanoate (65 ° C.)
can be mentioned.
　Diisopropyl peroxydicarbonate (IPP) catalyst is excellent in catalytic activity, there is a problem in terms of handling and storage stability are excellent in moldability. On the other hand, the above-mentioned radical polymerization initiator, as compared to the IPP catalyst, although superior in handling and storage stability, poor catalysis. In the present embodiment, by combination with the components (A) and (C), even in the case of using these radical polymerization initiators, excellent moldability, crack generation or release during polymerization it is possible to suppress the cracking of the time.
[0079]
　In the present embodiment, as a radical polymerization initiator (B), it is preferable to use a peroxy ketal radical polymerization initiator or (b) of the peroxy monocarbonate based radical polymerization initiator (a), specifically It is, OO- (t-butyl) -O- (2-ethylhexyl) monoperoxycarbonate, OO- (t-amyl) -O- (2-ethylhexyl) monoperoxycarbonate, 1,1-bis (t- butylperoxy) cyclohexane, 1,1-bis (t-amyl peroxy) cyclohexane, 1,1-bis (t-hexyl peroxy) cyclohexane, 1,1-bis (t-hexyl peroxy) -3,3 , it is preferable to use 5-trimethyl cyclohexane and the like.
[0080]
　In the present embodiment, the amount of the radical polymerization initiator (B), the type of polymerization conditions and initiator, purity and diluent used in the initiator varies depending on the composition of the compound (A), it can not be limited unconditionally the compounds containing allyloxycarbonyl group (a) 0.3 ~ 5.0 parts by weight per 100 parts by weight, preferably 0.5 to 3.0 parts by weight, of two or more radical polymerization initiators it is also possible to use a combination of agents.
[0081]
　Further, when the polymerization of the optical material for the polymerizable composition of the present embodiment, among the polymerization conditions, the effect on the properties of the cured product particularly temperature is obtained gives. The temperature condition is, can not unconditionally limit is affected by the type and amount and type of monomers of a radical polymerization initiator (B), generally starts at a relatively low temperature polymerization, slowly the temperature gradually raised, it is preferable to cure at a high temperature at the end of polymerization. Time also differs depending on factors temperature as well as various polymerization, the advance but it is preferable to determine the optimum time according to these conditions, typically choose conditions such that polymerization at 12-24 hours to complete It is preferred. Further, the optical material for the polymerizable composition of the present embodiment, 35 ° C. without strict control of the following, even in a pattern starting from 60 ° C. or higher are possible curing, because molding is easy, and high yield.
[0082]
[Modifier C)]
　In the present embodiment, the modifier (C) of the general formula (c1) polyether-modified siloxane compound represented by (C1) or represented by a polyol compound of general formula (c2) ( it can be selected from C2).
[0083]
(Polyether-modified siloxane compound (C1))
[0084]
　The polyether-modified siloxane compound (C1) in the present embodiment, it is possible to use a compound represented by the following general formula (c1).
[0085]
[Formula 33]

[0086]
　R 1 ~ R 8 may be the same or different, R 1 ~ R 8 at least one represents a polyether group represented by the following general formula (c1a), other R 1 ~ R 8 are the same or it may be different, a linear or branched alkyl group, a linear or branched alkoxy group having 1 to 20 carbon atoms, a hydroxyl group or a polysiloxy group, having 1 to 20 carbon atoms. R presence of a plurality of 2 ~ R 5 may be the same or different. m, n may be the same or different, an integer of 0 or more, preferably an integer of 1 to 20, more preferably an integer of 1-10.
[0087]
[Formula 34]

[0088]
　In the general formula (c1a), R 25 is a linear or branched alkylene group having 1 to 20 carbon atoms, R 26 is a linear or branched alkyl group having a hydrogen atom, 1 to 20 carbon atoms, having 2 to 20 carbon atoms a linear or branched, linear or branched alkynyl group an alkenyl group or a C 2-20. R presence of a plurality of 25 may be the same or different. k is an integer of 1 or more.
[0089]
　Incidentally, k indicating the number of polymerization units of the polyether moiety may be appropriately selected from an integer of 1 or more, but preferably an integer of 1 to 20, more preferably an integer of 1-10.
　Also, in one embodiment, the cracking at the time of generation and release of cracks from the viewpoint of suppressing during polymerization, k is preferably an integer of 1 to 1,000, more preferably an integer from 40 to 600, even more preferably an integer of 55 to 550.
[0090]
　Further, in one embodiment, R polyether group represented by the general formula (c1a) 26 is preferably a linear or branched alkyl group having a hydrogen atom or a C 1-20.
[0091]
　Also, In one embodiment, R polyether group represented by the general formula (c1a) 26 is a linear or branched alkynyl group having a linear or branched alkenyl group or C 2-20 2 to 20 carbon atoms It is shown.
[0092]
　Also, in one embodiment, the cracking at the time of generation and release of cracks from the viewpoint of suppressing during polymerization, R polyether group represented by the general formula (c1a) 26 , the number is preferably a hydrogen atom or a carbon 2 a straight or branched alkenyl group having 1-20, more preferably a straight-chain or branched alkenyl group having a hydrogen atom or a C 2-8.
[0093]
　Incidentally, as each substituent in the general formula (c1), in particular can be mentioned those shown below.
[0094]
　Examples of the straight-chain or branched alkylene group having 1 to 20 carbon atoms, e.g., methylene, ethylene, n- propylene, isopropylene, n- butylene group, isobutylene group, t-butylene group, n- pentylene , isopentylene, t-pentylene, n- hexylene, n- heptylene group, Isohepuchiren group, n- octylene, Isookuchiren group, n- nonylene, Isononiren group, n- decylene group, Isodeshiren group, n- undecylene , it can be exemplified Isoundeshiren group, n- dodecylene group, Isododeshiren group, cyclopentylene group, cyclohexylene group, cycloheptylene group, cyclooctylene group, cyclononylene group, methyl cyclopentylene group, a methyl cyclohexylene group. Preferably, a linear or branched alkylene group having 1 to 8 carbon atoms.
[0095]
　Examples of the straight-chain or branched alkyl group having 1 to 20 carbon atoms, such as methyl group, ethyl group, n- propyl group, an isopropyl group, n- butyl group, an isobutyl group, t- butyl group, n- pentyl group, isopentyl, t-pentyl group, n- hexyl, n- heptyl, isoheptyl, n- octyl group, isooctyl group, n- nonyl group, isononyl group, n- decyl group, isodecyl group, n- undecyl group, isoundecyl group, n- dodecyl group, and isododecyl group, a cyclopentyl group, a cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, methylcyclopentyl group, etc. methylcyclohexyl group.
　Preferably, a linear or branched alkyl group having 1 to 8 carbon atoms.
[0096]
　Examples of the straight-chain or branched alkoxy group having 1 to 20 carbon atoms, e.g., methoxy, ethoxy, n- propyloxy group, isopropyloxy group, n- butyloxy group, isobutyl group, t-butyloxy group, n- pentyloxy group, isopentyloxy group, t-pentyloxy group, n- hexyloxy group, n- heptyloxy group, iso-heptyl group, n- octyl group, isooctyl group, n- nonyloxy group, isononyl oxy group, n- decyloxy group, isodecyl group, n- undecyl group, iso-undecyl group, n- dodecyloxy group, iso-dodecyloxy group, cyclopentyloxy group, cyclohexyloxy group, cycloheptyl group, cyclooctyloxy group, a cycloalkyl nonyl group, Mechirushi Ropenchiruokishi group, and the like can be given methylcyclohexyl group.
　Preferably, a straight-chain or branched alkoxy group having 1 to 8 carbon atoms.
[0097]
　The linear or branched alkenyl group having 2 to 20 carbon atoms, e.g., vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl group , 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-hexenyl group, 2-hexenyl, 3-hexenyl group, 4-hexenyl, 5-hexenyl, 6-heptenyl, 7-octenyl , 8-nonenyl, 9-Dekeniru group, 2-methyl-1-propenyl group, 2-methyl-2-propenyl group, 3-methyl-3-butenyl group, 4-methyl-4-pentenyl group, 2-cyclohexyl 2-propenyl group and the like.
　Preferably, a straight-chain or branched alkenyl group having 2 to 8 carbon atoms.
[0098]
　The linear or branched alkynyl group having 2 to 20 carbon atoms, e.g., ethynyl, 1-propynyl, 2-propynyl, 1-butynyl group, 2-butynyl, 3-butynyl, 2-methyl - 2-propynyl group, 3-methyl-1-butynyl group, 4-pentynyl group, 5-hexynyl group, 6-heptynyl, 7-octynyl, 8-nonynyl group, and a 9-decynyl group.
　Preferably, a linear or branched alkynyl group having 2 to 8 carbon atoms.
[0099]
　As the compound represented by formula (c1), for example, POLYFLOW KL-100, POLYFLOW KL-600, Granol 410 (manufactured by Kyoeisha trade
name Chemical (Co.)); BYK-302, BYK-307, BYK-322, BYK -323, BYK-331, BYK- 333, BYK-347, BYK-348, BYK-349 (BYK-Chemie ( trade name)
manufactured); KF-351, KF-352, KF-353, KF-354L, KF-355, KF-355A, KF-615A, KF-618 ( Shin-Etsu Chemical Co., trade
name); SH3746, SH3771, SH8400, SF8410 (manufactured by Dow Corning Toray Co., Ltd. trade
name); TSF4440, TSF4445 , TSF4446, TSF4452 (Toshiba silicone Co., Ltd. trade name); It can be exemplified, but the invention is not limited only to these exemplified compounds. These may be used alone or may be used as a mixture of two or more thereof.
　Particularly preferred examples are POLYFLOW KL-100, a POLYFLOW KL-600 (manufactured by Kyoeisha Chemical Co., Ltd. trade name).
　Further, from the viewpoint of suppressing cracking during formation of cracks and release during the polymerization, the compound represented by the general formula (c1) is preferably POLYFLOW KL-100 and POLYFLOW KL-600 (manufactured by Kyoeisha Chemical Co., is at least one selected from trade names), more preferably POLYFLOW KL-100.
[0100]
　Further, from the viewpoint of suppressing cracking during formation of cracks and release during polymerization, polyether-modified siloxane compound (E) is a preferably a compound represented by the general formula (c1) in the general formula (c1a) R polyether group represented 26 are hydrogen atoms compounds and the general formula (c1) R polyether group represented by a compound represented by the general formula (c1a) 26 is 2 to 20 carbon atoms ; a linear or comprises at least one member selected from the group consisting of compounds which are branched alkenyl group
poly more preferably represented by a compound represented by the general formula (c1) the general formula (c1a) R ether group 26 is a hydrogen atom compounds and the general formula (c1) polyether group R represented by compounds wherein a and formula (c1a), represented by 26 is if linear from 2 to 8 carbon atoms ; Ku comprises at least one member selected from the group consisting of compounds which are branched alkenyl group
polyether represented by even more preferably a compound represented by the general formula (c1) the general formula (c1a) R group 26 and compound are hydrogen atoms, the general formula (c1) a compound represented by the general formula R a polyether group represented by (c1a) 26 of 2 to 8 carbon atoms straight-chain or at least one member selected from the group consisting of compounds which are branched alkenyl group, an include;
More preferably includes a compound represented by the compound represented by the following general formula (c1-1) and the following general formula (c1-2).
[0101]
[Formula 35]

[0102]
　The cracking during generation and release of cracks from the viewpoint of suppressing during polymerization, in the general formula (c1-1), a + c is preferably 1 to 100, more preferably from 5 to 50.
　From the same viewpoint, in the general formula (c1-1), b is preferably 1 to 100, more preferably from 5 to 50.
　From the same viewpoint, in the general formula (c1-1), d is preferably from 10 to 1000, more preferably from 50 to 500.
　From the same viewpoint, in the general formula (c1-1), e is preferably 1 to 100, more preferably from 5 to 50.
　From the same viewpoint, the molecular weight of the compound represented by the general formula (c1-1) is preferably from 100 to 10,000, more preferably 1,000 to 5,000.
[0103]
[Formula 36]

[0104]
　The cracking during generation and release of cracks from the viewpoint of suppressing during polymerization, in the general formula (c1-2), f + h is preferably 1 to 100, more preferably from 1 to 20.
　From the same viewpoint, in the general formula (c1-2), g is preferably 1 to 100, more preferably 1 to 10.
　From the same viewpoint, the molecular weight of the compound represented by the general formula (c1-2) is preferably from 100 to 10,000, more preferably from 500 to 5,000.
[0105]
　Further, when the polyether-modified compound comprising the general formula (c1-1) and the formula (c1-2) compounds represented by a compound represented by the general formula (c1-1) in the polyether-modified compound and weight ratio of the compound represented by the formula (c1-2), the cracking of the event and the release of cracks from the viewpoint of suppressing during polymerization, compounds generally represented by the formula (c1-1) weight ratio of the compound represented by formula (c1-1) with respect to total mass of the compound represented by the formula (c1-2) is preferably 50% to 90%, more preferably 60% to 80% it is.
[0106]
　In the present embodiment, the amount of the polyether-modified siloxane compound, wherein the compound (A) 0.001 ~ 2 parts by weight per 100 parts by weight, preferably from 0.01 to 1 part by mass.
[0107]
(Polyol compound (C2))
　As the polyol compound in the present embodiment (C2), it is possible to use a compound represented by the following general formula (c2).
[0108]
[Formula 37]

[0109]
　In the general formula (c2), R 2 represents a hydroxyl group, a -OX group or a linear or branched alkyl group having 1 to 4 carbon atoms. R 3 represents a hydrogen atom, X group, or a linear or branched alkyl group having 1 to 4 carbon atoms. R 4 represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms. Q 1 ~ Q 7 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, -CH 2 represents an -OX group or -OX group. p represents an integer of 1 ~ 4, s represents an integer of 0 ~ 4, t is an integer of 0 ~ 4, r is an integer of 1 to 1,000. Q presence of a plurality of 1 ～ Q 7 , X, S, T may be the same or different. * Represents a bond.
　Examples of the compound represented by formula (c2), the number-average molecular weight of 150 or more, preferably can be used in more than 200.
[0110]
　The represented polyol compound of general formula (c2) (C), there can be mentioned the compounds represented by the following general formula (c2-1) ~ (c2-8).
[0111]
[Formula 38]

[0112]
　In formula (c2-1), Q 1 , Q 2 , Q 4 , s, p is the general formula (c2) synonymous. Q there are a plurality of 1 , Q 2 , Q 4 , s may be the same or different.
[0113]
[Of 39]

[0114]
　In formula (c2-2) ~ formula (C2-8), the substituent X is as in formula (c2) synonymous, X existing in plural numbers may be the same or different.
[0115]
　In this embodiment, the polyol compound (C), from the viewpoint of the effect of the present invention, the compound (A) 0.0005 ~ 1 weight parts relative to 100 parts by weight, preferably 0.0005 to 0.5 part by weight , more preferably to 0.001 to 0.1 part by weight.
[0116]
[Ultraviolet absorber (D)]
　for an optical material polymerizable composition of the present embodiment may further include an ultraviolet absorber (D). As the ultraviolet absorber (D), there can be mentioned the compounds represented by the following formula (d). By using ultraviolet absorber (D), while maintaining the above effects, the order of 420nm from harmful UV high shielding effect of the blue light, is reduced impact on the eye of the harmful light eyestrain and stress such as it is possible to suppress the fault.
[0117]
[Of 40]

[0118]
　In the general formula (d), R 1 represents a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms. R presence of a plurality of 1 to each other may be the same or different.
　R 1 as a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, butyl group, isobutyl group, sec- butyl group, tert- butyl group, a pentyl group, a hexyl group, heptyl group, octyl group, 2- ethylhexyl group, a nonyl group, a linear or branched alkyl group having 1 to 20 carbon atoms such as a decyl group are preferable, particularly preferably a hydrogen atom, a methyl group, an ethyl group, a propyl group.
　m is an integer of 1 to 5, preferably an integer of 1 to 3,
　n is an integer of 1 to 5, preferably an integer of 1 to 3,
　and the sum of m and n is an integer of 2 to 10 , and the preferably an integer of 3-6.
[0119]
　Such ultraviolet absorber (D), 2,2 ', 4-trihydroxy benzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4-ethoxy-benzophenone, 2,2 '- dihydroxy -4-n-propoxy, 2,2'-dihydroxy-4-isopropoxy, 2,2'-dihydroxy -4-n-butoxy, 2,2'-dihydroxy -4-t-butoxy benzophenone, 2-hydroxy-4,4'-dimethoxy benzophenone, 2-hydroxy-4,4'-diethoxy benzophenone, 2-hydroxy-4,4'--n- propoxy benzophenone, 2-hydroxy-4,4 '- diisopropoxy benzophenone, 2-hydroxy-4,4'-di -n- Butokishiben Phenone, 2-hydroxy-4,4'-t- butoxy benzophenone, 2-hydroxy-4-methoxy-4'-ethoxy benzophenone, 2-hydroxy-4-methoxy-4'-n-propoxy benzophenone, 2-hydroxy 4-methoxy-4'-isopropoxy benzophenone, 2-hydroxy-4-methoxy-4'-n-butoxy benzophenone, 2-hydroxy-4-methoxy-4'-t-butoxy benzophenone, 2-hydroxy-4- ethoxy-4'-methoxybenzophenone, 2-hydroxy-4-ethoxy-4'-n-propoxy benzophenone, 2-hydroxy-4-ethoxy-4'-isopropoxy benzophenone, 2-hydroxy-4-ethoxy-4'- n- butoxy benzophenone, 2-hydroxy-4-ethoxy-4'-t - butoxy benzophenone, 2-hydroxy -4-n-propoxy-4'-methoxybenzophenone, 2-hydroxy -4-n-propoxy-4 ' - ethoxy benzophenone, 2-hydroxy -4-n-propoxy-4'-isopropoxy benzophenone, 2-hydroxy -4-n-propoxy-4'-n-butoxy benzophenone, 2-hydroxy -n--propoxy-4'- t- butoxy benzophenone, 2-hydroxy-4-isopropoxy-4'-methoxybenzophenone, 2-hydroxy-4-isopropoxy-4'-ethoxy benzophenone, 2-hydroxy-4-isopropoxy-4'-n-propoxy benzophenone, 2-hydroxy-4-isopropoxy-4'-n-butoxy benzophenone, 2-hydroxy - isopropoxy-4'-t-butoxy benzophenone, 2-hydroxy -4-n-butoxy-4'-methoxybenzophenone, 2-hydroxy -4-n-butoxy-4'-et Butoxy benzophenone, 2-hydroxy -4-n-butoxy-4'-n-propoxy benzophenone, 2-hydroxy -4-n-butoxy-4'-isopropoxy benzophenone, 2-hydroxy -4-n-butoxy-4 ' -t- butoxy benzophenone, 2-hydroxy -4-t-butoxy-4'-methoxybenzophenone, 2-hydroxy -4-t-butoxy-4'-ethoxy benzophenone, 2-hydroxy -4-t-butoxy-4 ' -n- propoxy benzophenone, 2-hydroxy -4-t-butoxy-4'-isopropoxy benzophenone, 2-hydroxy -4-t-butoxy-4'-n-butoxy benzophenone, 2,2 ', 4,4' - tetrahydroxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxy benzophenone, 2, '- dihydroxy-4,4'-diethoxy benzophenone, 2,2'-dihydroxy-4,4'-di -n- propoxy benzophenone, 2,2' - dihydroxy-4,4'-di - iso propoxy, 2,2'-dihydroxy-4,4'--n- butoxy, 2,2'-dihydroxy-4,4'-di -t- butoxy benzophenone, 2,2'-dihydroxy-4-methoxy-4'-diethoxy benzophenone, 2,2'-dihydroxy-4-methoxy-4'-n-propoxy, 2,2'-dihydroxy-4-methoxy - 4'-isopropoxyphenyl, 2,2'-dihydroxy-4-methoxy-4'-n-butoxy, 2,2'-dihydroxy-4-methoxy-4'-t-butoxy, 2,2' dihydroxy-4-ethoxy-4'-n-propoxy, 2,2'-dihydroxy-4-ethoxy-4'-isopropoxy-benzo Phenone, 2,2'-dihydroxy-4-ethoxy-4'-n-butoxy, 2,2'-dihydroxy-4-ethoxy-4'-t-butoxy, 2,2'-dihydroxy -4-n - propoxy-4'-isopropoxy benzophenone, 2,2'-dihydroxy -4-n-propoxy-4'-n-butoxy, 2,2'-dihydroxy -4-n-propoxy-4'-t-butoxy benzophenone, 2,2'-dihydroxy-4-isopropoxy-4'-n-butoxy, 2,2'-dihydroxy-4-isopropoxy-4'-t-butoxy, 2,2'-dihydroxy -4 -n- butoxy-4'-t-butoxy benzophenone, 2,2 ', 4-trimethoxy-benzophenone, 2,2', 4-triethoxy Benzophenone, 2,2 ' , 4-tri -n- propoxy benzophenone, 2,2 ', 4-tri-isopropoxy benzophenone, 2,2', 5-trimethoxy benzophenone, 2,2 ', 5-triethoxy benzophenone, 2,2', 5 - tri -n- propoxy benzophenone, 2,2 ', 5-tri-isopropoxy benzophenone, 2,4,4'-methoxybenzophenone, 2,4,4-triethoxy benzophenone, 2,4,4' -n- propoxy benzophenone, 2,4,4'-isopropoxy benzophenone, 3,4 ', 5-trimethoxy benzophenone, 3,4', 5-triethoxy benzophenone, 3,4 ', 5-tri -n - propoxy benzophenone, 3,4 ', 5-tri-isopropoxy, 2,4-dimethoxy-4'-hydroxy-benzo phenol , 2,4-diethoxy-4'-hydroxybenzophenone, 2,4-di -n- propoxy-4'-hydroxybenzophenone, 2,4-diisopropoxy-4'-hydroxybenzophenone, 2,2 ', 4, 4'-tetramethoxy-benzophenone, 2,2 ', 4,4'-tetra-ethoxy benzophenone, 3,3', 4,4'-tetramethoxy-benzophenone, 3,3 ', 4,4'-tetra-ethoxy-benzophenone, 2 , 3,3 ', 4'-tetramethoxy-benzophenone, 2,3,3', 4'-tetra-ethoxy-benzophenone, and the like. Among these, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxy benzophenone, 2,2 ', 4,4'-tetra hydroxybenzophenone is particularly preferable. , 4-tri-isopropoxy benzophenone, 2,2 ', 5-trimethoxy benzophenone, 2,2', 5-triethoxy benzophenone, 2,2 ', 5-tri -n- propoxy benzophenone, 2,2', 5 - triisopropoxy benzophenone, 2,4,4'-methoxybenzophenone, 2,4,4-triethoxy benzophenone, 2,4,4'--n- propoxy benzophenone, 2,4,4' isopropoxycarbonyl benzophenone, 3,4 ', 5-trimethoxy benzophenone, 3,4', 5-triethoxy benzophenone, 3,4 ', 5-tri -n- propoxy benzophenone, 3,4', 5-tri-isopropoxy benzophenone, 2,4-dimethoxy-4'-hydroxybenzophenone, 2,4-diethoxy-4'-hydroxyphenyl benzophenanthridine Emissions, 2,4-di -n- propoxy-4'-hydroxybenzophenone, 2,4-diisopropoxy-4'-hydroxybenzophenone, 2,2 ', 4,4'-tetramethoxy-benzophenone, 2,2' , 4,4'-tetra-ethoxy benzophenone, 3,3 ', 4,4'-tetramethoxy-benzophenone, 3,3', 4,4'-tetra-ethoxy benzophenone, 2,3,3 ', 4'-tetramethoxy benzophenone, 2,3,3 ', 4'-tetra-ethoxy-benzophenone, and the like. Among these, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxy benzophenone, 2,2 ', 4,4'-tetra hydroxybenzophenone is particularly preferable. , 4-tri-isopropoxy benzophenone, 2,2 ', 5-trimethoxy benzophenone, 2,2', 5-triethoxy benzophenone, 2,2 ', 5-tri -n- propoxy benzophenone, 2,2', 5 - triisopropoxy benzophenone, 2,4,4'-methoxybenzophenone, 2,4,4-triethoxy benzophenone, 2,4,4'--n- propoxy benzophenone, 2,4,4' isopropoxycarbonyl benzophenone, 3,4 ', 5-trimethoxy benzophenone, 3,4', 5-triethoxy benzophenone, 3,4 ', 5-tri -n- propoxy benzophenone, 3,4', 5-tri-isopropoxy benzophenone, 2,4-dimethoxy-4'-hydroxybenzophenone, 2,4-diethoxy-4'-hydroxyphenyl benzophenanthridine Emissions, 2,4-di -n- propoxy-4'-hydroxybenzophenone, 2,4-diisopropoxy-4'-hydroxybenzophenone, 2,2 ', 4,4'-tetramethoxy-benzophenone, 2,2' , 4,4'-tetra-ethoxy benzophenone, 3,3 ', 4,4'-tetramethoxy-benzophenone, 3,3', 4,4'-tetra-ethoxy benzophenone, 2,3,3 ', 4'-tetramethoxy benzophenone, 2,3,3 ', 4'-tetra-ethoxy-benzophenone, and the like. Among these, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxy benzophenone, 2,2 ', 4,4'-tetra hydroxybenzophenone is particularly preferable. , 5-triethoxy benzophenone, 2,2 ', 5-tri -n- propoxy benzophenone, 2,2', 5-tri-isopropoxy benzophenone, 2,4,4'-methoxybenzophenone, 2,4,4 ' - triethoxysilane benzophenone, 2,4,4'--n- propoxy benzophenone, 2,4,4'-isopropoxy benzophenone, 3,4 ', 5-trimethoxy benzophenone, 3,4', 5-tri ethoxy benzophenone, 3,4 ', 5-tri -n- propoxy benzophenone, 3,4', 5-tri-isopropoxy, 2,4-dimethoxy-4'-hydroxybenzophenone, 2,4-diethoxy-4'- hydroxybenzophenone, 2,4-di -n- propoxy-4'-hydroxybenzophenone, 2,4-diisopropoxy 4'-hydroxybenzophenone, 2,2 ', 4,4'-tetramethoxy-benzophenone, 2,2', 4,4'-tetra-ethoxy benzophenone, 3,3 ', 4,4'-tetramethoxy-benzophenone, 3 , 3 ', 4,4'-tetra-ethoxy benzophenone, 2,3,3', 4'-tetramethoxy-benzophenone, 2,3,3 ', 4'-tetra-ethoxy-benzophenone, and the like. Among these, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxy benzophenone, 2,2 ', 4,4'-tetra hydroxybenzophenone is particularly preferable. , 5-triethoxy benzophenone, 2,2 ', 5-tri -n- propoxy benzophenone, 2,2', 5-tri-isopropoxy benzophenone, 2,4,4'-methoxybenzophenone, 2,4,4 ' - triethoxysilane benzophenone, 2,4,4'--n- propoxy benzophenone, 2,4,4'-isopropoxy benzophenone, 3,4 ', 5-trimethoxy benzophenone, 3,4', 5-tri ethoxy benzophenone, 3,4 ', 5-tri -n- propoxy benzophenone, 3,4', 5-tri-isopropoxy, 2,4-dimethoxy-4'-hydroxybenzophenone, 2,4-diethoxy-4'- hydroxybenzophenone, 2,4-di -n- propoxy-4'-hydroxybenzophenone, 2,4-diisopropoxy 4'-hydroxybenzophenone, 2,2 ', 4,4'-tetramethoxy-benzophenone, 2,2', 4,4'-tetra-ethoxy benzophenone, 3,3 ', 4,4'-tetramethoxy-benzophenone, 3 , 3 ', 4,4'-tetra-ethoxy benzophenone, 2,3,3', 4'-tetramethoxy-benzophenone, 2,3,3 ', 4'-tetra-ethoxy-benzophenone, and the like. Among these, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxy benzophenone, 2,2 ', 4,4'-tetra hydroxybenzophenone is particularly preferable. - triethoxysilane benzophenone, 2,4,4'--n- propoxy benzophenone, 2,4,4'-isopropoxy benzophenone, 3,4 ', 5-trimethoxy benzophenone, 3,4', 5-tri ethoxy benzophenone, 3,4 ', 5-tri -n- propoxy benzophenone, 3,4', 5-tri-isopropoxy, 2,4-dimethoxy-4'-hydroxybenzophenone, 2,4-diethoxy-4'- hydroxybenzophenone, 2,4-di -n- propoxy-4'-hydroxybenzophenone, 2,4-diisopropoxy-4'-hydroxybenzophenone, 2,2 ', 4,4'-tetramethoxy-benzophenone, 2,2 ', 4,4'-tetra-ethoxy benzophenone, 3,3', 4,4'-tetramethoxy-benzophenone, 3,3 ', 4,4'-tetra-ethoxy benzophenone, 2,3,3', 4'-tetramethoxy-benzophenone, 2,3,3 ', 4'-tetra-ethoxy-benzophenone, and the like. Among these, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxy benzophenone, 2,2 ', 4,4'-tetra hydroxybenzophenone is particularly preferable. - triethoxysilane benzophenone, 2,4,4'--n- propoxy benzophenone, 2,4,4'-isopropoxy benzophenone, 3,4 ', 5-trimethoxy benzophenone, 3,4', 5-tri ethoxy benzophenone, 3,4 ', 5-tri -n- propoxy benzophenone, 3,4', 5-tri-isopropoxy, 2,4-dimethoxy-4'-hydroxybenzophenone, 2,4-diethoxy-4'- hydroxybenzophenone, 2,4-di -n- propoxy-4'-hydroxybenzophenone, 2,4-diisopropoxy-4'-hydroxybenzophenone, 2,2 ', 4,4'-tetramethoxy-benzophenone, 2,2 ', 4,4'-tetra-ethoxy benzophenone, 3,3', 4,4'-tetramethoxy-benzophenone, 3,3 ', 4,4'-tetra-ethoxy benzophenone, 2,3,3', 4'-tetramethoxy-benzophenone, 2,3,3 ', 4'-tetra-ethoxy-benzophenone, and the like. Among these, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxy benzophenone, 2,2 ', 4,4'-tetra hydroxybenzophenone is particularly preferable. - hydroxybenzophenone, 2,4-di -n- propoxy-4'-hydroxybenzophenone, 2,4-diisopropoxy-4'-hydroxybenzophenone, 2,2 ', 4,4'-tetramethoxy-benzophenone, 2, 2 ', 4,4'-tetra-ethoxy benzophenone, 3,3', 4,4'-tetramethoxy-benzophenone, 3,3 ', 4,4'-tetra-ethoxy benzophenone, 2,3,3', 4'- tetra-methoxybenzophenone, 2,3,3 ', 4'-tetra-ethoxy-benzophenone, and the like. Among these, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxy benzophenone, 2,2 ', 4,4'-tetra hydroxybenzophenone is particularly preferable. - hydroxybenzophenone, 2,4-di -n- propoxy-4'-hydroxybenzophenone, 2,4-diisopropoxy-4'-hydroxybenzophenone, 2,2 ', 4,4'-tetramethoxy-benzophenone, 2, 2 ', 4,4'-tetra-ethoxy benzophenone, 3,3', 4,4'-tetramethoxy-benzophenone, 3,3 ', 4,4'-tetra-ethoxy benzophenone, 2,3,3', 4'- tetra-methoxybenzophenone, 2,3,3 ', 4'-tetra-ethoxy-benzophenone, and the like. Among these, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxy benzophenone, 2,2 ', 4,4'-tetra hydroxybenzophenone is particularly preferable.
[0120]
[Dye (E)]
　The optical material for the polymerizable composition of the present embodiment may further comprise a dye (E). The dye (E), anthraquinone dyes, perinone dyes, monoazo dyes, diazo dyes, mention may be made of phthalocyanine dyes may be used alone or in combination. It is possible to obtain transparency, excellent optical material appearance.
[0121]
　The anthraquinone dye, Solvent Blue 36 (1,4-bis (isopropylamino) anthracene-9,10-dione), Solvent Blue 63 (1-(methylamino)-4-(m-tolylamino) anthracene-9, 10- dione), Solvent Blue 94 (1-amino-2-bromo-4- (phenylamino) anthracene-9,10-dione), Solvent Blue 97 (1,4-bis ((2,6-diethyl -4 - methylphenyl) amino) anthracene-9,10-dione), Solvent Blue 104 (1,4-bis (Meshichiruamino) anthracene-9,10-dione), Solvent Violet 13 (1-hydroxy-4-(p-tolylamino ) anthracene-9,10-dione), Solvent Violet 13 (1,5- bis (p- tolylamino) anthracene-9,10-dione), Solvent Red 52 (3- methyl - 6- (p-tolylamino) -3H- naphtho [1,2,3-de] quinoline-2,7-dione), Solvent Red 168 (1- (cyclohexylamino) anthracene-9,10-dione), Solvent Red 207 (1,5-bis (cyclohexylamino) anthracene-9,10-dione), Disperse Red 22 (1- (phenylamino) anthracene-9,10-dione), Disperse Red 60 (1-amino-4-hydroxy 2-phenoxy-9,10-dione), Solvent Violet 59 (1,4- diamino-2,3-diphenyl-9,10-dione), Solvent Green 28 (1,4- bis ((4- butylphenyl) amino) -5,8-dihydroxy-9,10-dione), and the like.
[0122]
　The perinone dyes, Solvent Orange 60 (12H- Isoindoro [2,1-a] perimidin-12-one), Solvent Orange 78, Solvent Orange 90, Solvent Red 135 (8,9,10,11- tetrachloro - 12H- Isoindoro [2,1-a] perimidin-12-one), cited Solvent Red 162, Solvent Red 179 (14H- benzo [4,5] Isokinorino [2,1-a] perimidin-14-one), etc. be able to.
[0123]
　The monoazo dyes, mention may be made of Solvent Red 195, Fast orange R, Oil Red, the oil yellow, or the like.
　The diazo dye, Chicago Sky Blue 6B (Sodiumu 6,6 '- ((1E, 1'E ) - (3,3'- dimethoxy - [1,1'-biphenyl] -4,4'-diyl) bis (diazene-2,1-diyl)) bis (4-amino-5-hydroxynaphthalene-1,3-disulfonate)), Evans blue (Sodiumu 6,6 '- ((1E, 1'E ) - ( 3,3'-dimethyl - [1,1'-biphenyl] -4,4'-diyl) bis (diazene-2,1-diyl)) bis (1,3-4-amino-5-hydroxynaphthalene-di sulfonate)), direct Blue 15 (Sodiumu 3,3 '- ((1E, 1'E ) - (3,3'- dimethoxy - [1,1'-biphenyl] -4,4'-diyl) bis (diazene 2,1-diyl)) bis (5-amino-4-hydroxynaphthalene-2,7-disulfonate)), trypan blue (Sodiumu 3,3 '- ((1E, 1'E ) - (3,3 '- dimethyl - [1,1'-biphenyl] -4,4'-diyl) bis (diazene-2,1-diyl)) bis (5-amino-4-hydroxynaphthalene-2,7-disulfonate)) , Benzopuru Phosphorus 4B (Sodiumu 3,3 '- ((1E, 1'E ) - (3,3'- dimethyl - [1,1'-biphenyl] -4,4'-diyl) bis (diazene-2,1 diyl)) bis (4-amino-naphthalene-1-sulfonate)), Congo Red (Sodiumu 3,3 '- ((1E, 1'E ) - [1,1'- biphenyl] -4,4'-diyl bis ( diazene -2,
　The phthalocyanine dye, C. I. Direct Blue 86, C. I. Mention may be made of the Direct Blue 199 and the like.
[0124]
　In the present embodiment, blue light blocking effects of the order of 420 nm, from the viewpoint of obtaining a yellowness (YI), excellent transparency optical material, preferably, Solvent Blue 94, Solvent Blue 97, Solvent Blue 104, Solvent Violet 59, Solvent Red 195, Disperse Red 60, a Solvent Green 28, Solvent Orange 60, may be used alone also combinations of two or more use.
[0125]
　The optical material for the polymerizable composition of the present embodiment, a compound containing two or more allyloxycarbonyl group (A), by comprising a radical polymerization initiator (B), and modifier (C), during the polymerization is cracking during generation and release of cracks suppression, it is possible to provide an excellent optical material in the production of the resin molded body for a polymerizable composition. Further, the refractive index, is excellent in optical properties such as the Abbe number.
[0126]
　It should be noted that, as described above, in recent years, natural light, and a liquid crystal display of office equipment, by the blue light included in the light emitting from the display, such as a smart phone or a portable device such as a mobile phone, such as the feel eye fatigue and pain, eye and effect becomes a problem to, eye, reduce the amount of exposure to a relatively short wavelength of the blue light of about 420nm from an ultraviolet have been desired.
[0127]
　Incidentally, the benzophenone ultraviolet absorber are diethylene glycol bis-allyl carbonate polymer described in Patent Document 3, an amount more and wavelength 440nm light transmittance of the light transmittance of the wavelength 380nm is 0 percent more than the amount that the 90% It was added in diethylene glycol bis-allyl carbonate polymer obtained by radical polymerization, although the following UV wavelength 380nm can be completely shut off, there is no disclosure of being able to block the blue light of relatively short wavelength of about 420 nm.
[0128]
　To block the blue light of about 420 nm, if you increase the amount of the ultraviolet absorber to the compound containing two or more allyloxycarbonyl group, there are problems such that the hue of the resulting resin may deteriorate It was. Moreover, if the hue is deteriorated, it is using a dye or a method for improving the hue of the resin or the like, for example, a dye is decomposed by peroxide compounds used as a polymerization catalyst of the polymerizable allyl carbonate, a resin color there was a problem such as that can not be well adjusted to. Further, an ultraviolet absorber is decomposed by peroxide compounds used as a polymerization catalyst of the polymerizable allyl carbonate, there may not be obtained the effect of blocking the blue light of about 420 nm.
　The polymerizable composition as described above, or cracks occur, cracks during release there occur during polymerization.
[0129]
　The optical material for the polymerizable composition of the present embodiment, by containing (A) ~ was added to the component (C), more specific ultraviolet absorber (D) and / or dyes (E), maintains the effect while, an ultraviolet absorber (D) and the dye (E) without being decomposed, high blocking effect of 420nm approximately blue light from harmful ultraviolet radiation, is reduced impact on the eye of the harmful light eyestrain and stress it can suppress the disorder, such as, it is possible to obtain a resin having a good hue and transparency. From the viewpoint of the effect, preferably also contain any component (D) and (E) component.
[0130]
　Ultraviolet absorber (D) is the compound (A) 100 parts by weight of the above, 0.2 to 10 parts by weight, preferably by using 0.5 to 3 parts by weight, the blue of about 420nm from harmful ultraviolet radiation it can be more efficiently exhibited the effect of blocking light.
　Dye (E), the compound (A) 0.1 ~ 100 ppm by weight with respect to 100 parts by weight, preferably by using 1 to 20 wt ppm, the effect of blocking 420nm approximately blue light from harmful ultraviolet radiation it can be more efficiently exhibited.
[0131]
[Other Components]
　In the present embodiment, in addition to the (A) ~ (E) component, the internal mold release agent may further contain additives such as a resin modifier.
[0132]
　As the internal mold release agent, it can be used acidic phosphoric acid ester, a non-reactive silicone oil. The acidic phosphoric acid esters, phosphoric acid monoesters, there may be mentioned phosphoric acid diester, can be used as a mixture either alone or two or more kinds.
[0133]
　The resin modifier, for example, polyoxyalkylene alkyl ether compounds, polyoxyalkylene fatty acid esters, episulfide compound, a polyol compound other than an alcohol compound represented by the general formula (c2), an amine compound, an epoxy compound, and organic acids their anhydrides, include olefin compounds containing (meth) acrylate compounds.
[0134]

　for an optical material polymerizable composition of the present embodiment includes
a compound containing represented by two or more allyloxycarbonyl group (A) the general formula (a),
(B) peroxy ketal radical polymerization initiator, and at least one radical polymerization initiator is selected from the group consisting of peroxy monocarbonate based radical polymerization initiator and peroxyester polymerization initiator,
(C) can be prepared by mixing the modifier, the.
[0135]
　Furthermore, at least one selected from (D) Formula (d) an ultraviolet absorbent represented by, and / or (E) anthraquinone dyes, perinone dyes, monoazo dyes, diazo dyes, and phthalocyanine dyes in the case of using the seeds of the dye can be prepared for optical material polymerizable composition by mixing them together with components (a) ~ (C) component.
[0136]
　Components (A) ~ (C) component, the temperature in the preparation of further component (D) and / or component (E) were mixed with the polymerizable composition it is usually carried out in a 25 ° C. or less. From the viewpoint of pot life of the polymerizable composition, it may be preferable further to a low temperature. However, catalysts, internal release agents, if solubility in monomer additive is not satisfactory, it is also possible to dissolve beforehand warmed, monomers, a resin modifier.
[0137]
　In the present embodiment, a manufacturing method of the resin molded body is not particularly limited, and a casting polymerization as a preferred production method. First, injecting the polymerizable composition between molding mold held by a gasket or tape. At this time, depending on the properties required for the plastic lens obtained, if necessary, a defoaming treatment under reduced pressure or pressurization, it is often preferable to perform the filtration treatment and the like of reduced pressure or the like.
[0138]
　The polymerization conditions, the composition of the polymerizable composition, type and amount of catalyst used, but is not limited for different conditions largely by the shape or the like of the mold, about 1 to 50 hours at a temperature of 0 ~ 0.99 ° C. It is done over. In some cases, hold or gradually heated in a temperature range of 20 ~ 130 ° C., is thereby is preferably cured for 1 to 48 hours.
[0139]
　Resin molding, if necessary, may be subjected to a treatment such as annealing. Although the process is carried out at a temperature usually between 50 ~ 0.99 ° C., preferably performed at 90 ~ 140 ° C., and more preferably at 100 ~ 130 ° C..
[0140]
　In the present embodiment, in molding the resin, in addition to the above "other components" in the same manner as in a known molding method depending on the purpose, chain extenders, crosslinking agents, light stabilizers, antioxidants, solvent dye, filler, various additives may be added, such as an adhesion improver.
[0141]

　poly obtained from an optical material for the polymerizable composition of the present embodiment (allyl carbonate) and poly (allyl ester) resins, as shaped bodies having various shapes by changing the type of mold during casting polymerization Obtainable.
　The resin compact of this exemplary embodiment is excellent in crack generation and the release time of cracking productivity are suppressed in during the polymerization. (A) was added to ~ (C) component, by further containing a specific ultraviolet absorber (D) and / or dyes (E), while maintaining the above effect, disconnected from the harmful ultraviolet rays of about 420nm blue light effective and is excellent in transparency and appearance, it can be used in various optical materials such as plastic lenses. In particular, it can be suitably used as a plastic spectacle lens.
[0142]
[Plastic spectacle lenses]
　plastic spectacle lens using a lens substrate made of molded body of the present embodiment may optionally be used after the coating layer on one or both sides.
　Plastic spectacle lens of the present embodiment is composed of a lens substrate and the coating layer comprising a polymerizable composition described above.
[0143]
　As a coating layer, specifically, a primer layer, a hard coat layer, an antireflection layer, anti-fogging coat layer, anti-fouling layer, a water repellent layer, and the like. It may also be used in multi-layered multiple coating layers using each of these coating layers alone. When applying a coating layer on both sides, even if subjected to the same coating layer on each side may be subjected to a different coating layers.
[0144]
　Each of these coating layers, the infrared absorbing agent for the purpose of protecting the eyes from infrared rays, a light stabilizer or antioxidant for the purpose of improving the weather resistance of the lens, the photochromic compound, purpose dyes or pigments to enhance the fashion of the lens , antistatic agents, other may be used in combination known additive for increasing the performance of the lens.
　It may be used various leveling agents for the purpose of improving the coating properties with respect to the layer to perform coating by the coating.
[0145]
　The primer layer is usually formed between the hard coat layer and the lens to be described later. The primer layer is a coating layer for the purpose of improving the adhesion between the hard coat layer and the lens formed thereon, it is possible to improve impact resistance in some cases. Primers can also be used in any material as long as high adhesion to the lens obtained in the primer layer, which usually, urethane resins, epoxy resins, polyester resins, melanin resins, a main component a polyvinyl acetal such compositions are used. The primer composition may be used a suitable solvent which does not affect the lens in order to adjust the viscosity of the composition. Of course, it may be used in solvent-free.
[0146]
　The primer layer can be formed by a coating method, any method of a dry method. When using the coating method, the primer composition was applied to the lens by a known coating method such as spin coating, dip coating, a primer layer is formed by solidifying. When performing a dry method, it is formed by a known dry method such as CVD method or a vacuum evaporation method. When forming the primer layer, for the purpose of enhancing adhesion, the surface of the lens if necessary, alkali treatment, plasma treatment, may be previously subjected to pre-treatment such as UV treatment.
　The hard coat layer, the scratch resistance on the lens surface, wear resistance, moisture resistance, hot water resistance, heat resistance, a coating layer for the purpose of giving weather resistance function.
[0147]
　The hard coat layer, an organosilicon compound typically having curability and Si, Al, Sn, Sb, Ta, Ce, La, Fe, Zn, W, Zr, the element selected from the group consisting of In and Ti hardcoat composition comprising one or more particulate composed of a composite oxide of two or more elements selected from one or more and / or these elements groups oxide microparticles are used.
[0148]
　Amines other than the above components in the hard coat composition, amino acids, at least the metal acetylacetonate complexes, organic acid metal salts, perchloric acids, salts of perchloric acids, acids, metal chlorides and polyfunctional epoxy compounds it is preferable to include either. It may be used a suitable solvent which does not affect the lens in the hard coat composition may be used without a solvent.
[0149]
　The hard coat layer is usually spin coating a hard coat composition was applied by a known coating method such as dip coating, it is formed by curing. As the curing method, thermosetting, a curing method such as by energy ray irradiation such as ultraviolet or visible light and the like. To suppress the occurrence of interference fringe, the refractive index of the hard coat layer, the difference in refractive index of the lens is preferably in the range of ± 0.1.
[0150]
　Antireflection layer is usually formed on the hard coat layer as needed. The anti-reflection layer has inorganic and organic, if inorganic, SiO 2 , TiO 2 using an inorganic oxide such as a vacuum deposition method, a sputtering method, an ion plating method, an ion beam assisted method, CVD method It is formed by a dry method such as. If organic, using an organosilicon compound, a composition comprising a silica-based fine particles having internal cavities are formed by a wet.
[0151]
　Antireflective layer has a single-layer and multilayer, it is preferable that a refractive index higher than the refractive index of the hard coat layer is lower at least 0.1 or more when used as a single layer. It is preferable that the express effectively anti-reflection function is a multi-layer film anti-reflection film, in which case, alternately laminating a low refractive index film and the high refractive index film. It is preferred in this case the refractive index difference between the low refractive index film and the high refractive index film is 0.1 or more. The high refractive index film, ZnO, TiO 2 , CeO 2 , Sb 2 O 5 , SnO 2 , ZrO 2 , Ta 2 O 5 has such a film, the low refractive index film, SiO 2 include films and the like .
[0152]
　On the antireflection layer, anti-fogging layer optionally antifouling layer, may be formed a water-repellent layer. Antifogging, antifouling layer, a method of forming a water-repellent layer, as long as they do not result in a negative effect on the anti-reflection function, a processing method thereof, and the like without particular limitation on the processing material, known anti-fogging method, antifouling treatment method, water repellent treatment method, the material can be used. For example, a method antifogging method, the anti-fouling treatment method, a method of covering the surface with a surfactant, a method of water absorption by adding a hydrophilic film on the surface, to increase the water-absorbing covering the surface with fine unevenness , a method of using a photocatalytic activity to water absorption, a method of preventing the adhesion of water droplets by subjecting the superhydrophobic treatment. Further, the method in the water-repellent treatment method, for forming a fluorine-containing silane compound or the like and a method of forming a water-repellent treatment layer by vapor deposition or sputtering, after the fluorine-containing silane compound is dissolved in a solvent, the water-repellent treatment layer by coating etc. the.
Example
[0153]
　Hereinafter, the present invention Example A, is specifically described on the basis of B, the present invention is not limited to these examples.
[0154]

　Evaluation of molded article and a plastic lens comprising a cured resin was performed by the following method.
　Winding the following glass molding two of the outer circumference of the curved surface in this embodiment by adhesive tape cured using a mold assembled in parallel with a gap (mold 1-4) the polymerizable composition, and molded.
[0155]
(Mold 1)
　Base Curve: convex: 6.00, concave: 6.00
　- center thickness: 10 mm
　- Mold diameter: 81 mm
(mold 2)
　Base Curve: convex: 6.25, concave: 6.25
　- center thickness: 10 mm
　- mold diameter: 75 mm
(mold 3)
　base curve: convex: 4.25, concave: 6.25
　- central thickness: 8 mm
　- mold diameter: 75 mm
(mold 4)
　base curve: convex: 0.00 , concave: 0.00
　- center thickness: 2 mm
　- mold diameter: 75 mm
[0156]
[Evaluation of Physical Properties]
(1) occurrence of cracks during the polymerization
　in the present embodiment was prepared a plurality of lenses, a lens crack is generated in the edge portion during the polymerization was rejected, was evaluated by the following criteria pass rate .
　- pass rate of 90% or more: ◎
　-pass rate of 50% or more, less than 90%: ￮
　-pass rate of less than 50%: ×
[0157]
(2) generation of cracks at the time of releasing
　the plurality of lenses prepared in this example, a lens that crack is generated in addition to the outer peripheral portion of the lens at the time of release was rejected, was evaluated by the following criteria pass rate .
　- pass rate of 90% or more: ◎
　-pass rate of 50% or more, less than 90%: ￮
　-pass rate of less than 50%: ×
[0158]
(3) light-cutting rate of 420nm wavelength
　obtained formed body transmittance at a wavelength of 420nm (the flat plate of thickness 2 mm) at Shimadzu Corp. UV-visible spectrophotometer UV-1600 was measured, the following equation in calculating the light-cutting rate of 420nm defined.
Rays cut rate of 420nm wavelength (%) = 100 (%) - (transmittance at a wavelength of 420nm) (%)
[0159]
　Using the following components in the embodiment.
(Compound
(A)) · RAV 7MC (diethylene glycol, poly (allyl carbonates of neopentyl glycol and pentaerythritol) manufactured compounds and oligomers thereof, ACOMON Co.)
[0160]
(Radical polymerization initiator
(B)) · LUPEROX 531M80 (1,1-bis (t-amyl peroxy) 80% solution of cyclohexane, manufactured by Arkema Yoshitomi, Ltd.)
[0161]
(Siloxane compound (C1))
· the compounds of the formula 68 wt% represented by (c1-1), polyether-modified siloxane compound containing 29 wt% of a compound represented by the general formula (c1-2)
Incidentally, the molecular weight of the compound represented by formula (c1-1) is about 2000, the molecular weight of the compound represented by formula (c1-2) is about 1000.
　Further, in the general formula (c1-1), a a + c = 5 ~ 50, b = 5 ~ 50, d = 50 ~ 500, e = 5 ~ 50, in the general formula (c1-2), f + h = 1 ~ 20, it is g = 1 ~ 10.
[0162]
(Ultraviolet absorber
(D)) · SEESORB 107 (2,2'-dihydroxy-4,4'-dimethoxy benzophenone, manufactured by Shipro Kasei Co., Ltd.)
[0163]
(Dye
(E)) · Plast Blue 8520 (Solvent Blue 94, Arimoto Chemical Industry Co.,
Ltd.) · Solvaperm Red BB (Solvent Red 195, manufactured by Clariant Co., Ltd.)
[0164]
(Example
　A1) RAV 7MC against (ACOMON Ltd.) 99.1 parts by weight, SEESORB 107 (Shipro Kasei Co., Ltd.) 0.75 parts by weight, Plast Blue 8520 (Arimoto Chemical Co., Ltd.) 5ppm, Solvaperm Red BB (Clariant) 2.75 ppm dissolved at 80 ° C. the, LUPEROX 531M80 (Arkema Yoshitomi, Ltd.) 0.8 parts by weight as a radical polymerization initiator after cooling to room temperature, 0.1 weight polyether-modified siloxane compound parts were added, after degassing by decompression, and poured into a mold 1 and mold 4 above, were polymerized while gradually raising the temperature to 105 ° C. from 25 ° C.. And releasing a molded body from the mold after subsequent cooling to 60 ° C.. Curing in the mold 4, the molding was 2mm thick flat plate light rays 420nm cut about 55%, the hue was more good transparency. Mold 1 was produced 10 pieces of lenses were used to evaluate the cracking of at development and release of cracks during polymerization. The results are shown in Table 1.
[0165]
(Example
　A2) RAV 7MC against (ACOMON Ltd.) 99.1 parts by weight, SEESORB 107 (Shipro Kasei Co., Ltd.) 0.75 parts by weight, Plast Blue 8520 (Arimoto Chemical Co., Ltd.) 5ppm, Solvaperm Red BB (Clariant) 2.75 ppm dissolved at 80 ° C. the, LUPEROX 531M80 (Arkema Yoshitomi, Ltd.) 0.8 parts by weight as a radical polymerization initiator after cooling to room temperature, 0.1 weight polyether-modified siloxane compound parts were added, after degassing by decompression, and poured into a mold 2 and the mold 4 above, were polymerized while gradually raising the temperature to 105 ° C. from 25 ° C.. And releasing a molded body from the mold after subsequent cooling to 60 ° C.. Curing in the mold 4, the molding was 2mm thick flat plate light rays 420nm cut about 55%, the hue was more good transparency. Mold 2 to produce 10 pieces of lenses were used to evaluate the cracking of at development and release of cracks during polymerization. The results are shown in Table 1.
[0166]
(Example
　A3) RAV 7MC against (ACOMON Ltd.) 99.1 parts by weight, SEESORB 107 (Shipro Kasei Co., Ltd.) 0.75 parts by weight, Plast Blue 8520 (Arimoto Chemical Co., Ltd.) 5ppm, Solvaperm Red BB (Clariant) 2.75 ppm dissolved at 80 ° C. the, LUPEROX 531M80 (Arkema Yoshitomi, Ltd.) 0.8 parts by weight as a radical polymerization initiator after cooling to room temperature, 0.1 weight polyether-modified siloxane compound parts were added, after degassing by decompression, and poured into a mold 3 and mold 4 above, were polymerized while gradually raising the temperature to 105 ° C. from 25 ° C.. And releasing a molded body from the mold after subsequent cooling to 60 ° C.. Curing in the mold 4, the molding was 2mm thick flat plate light rays 420nm cut about 55%, the hue was more good transparency. By using a mold 3 lens to produce ten to evaluate the occurrence of cracks at the time of development and release of cracks during polymerization. The results are shown in Table 1.
[0167]
(Comparative Example
　A1) with respect to RAV 7MC (ACOMON Ltd.) 99.1 parts by weight, SEESORB 107 (Shipro Kasei Co., Ltd.) 0.75 parts by weight, Plast Blue 8520 (Arimoto Chemical Co., Ltd.) 5ppm, Solvaperm Red BB (Clariant) 2.75 ppm dissolved at 80 ° C. was then added LUPEROX 531M80 (Arkema Yoshitomi, Ltd.) 0.8 parts by weight as a radical polymerization initiator after cooling to room temperature, after degassing by decompression, the aforementioned mold It was poured into 1 and the mold 4, and polymerized while gradually raising the temperature to 105 ° C. from 25 ° C.. And releasing a molded body from the mold after subsequent cooling to 60 ° C.. Curing in the mold 4, the molding was 2mm thick flat plate light rays 420nm cut about 55%, the hue was more good transparency. Mold 1 was produced 10 pieces of lenses were used to evaluate the cracking of at development and release of cracks during polymerization. The results are shown in Table 1.
[0168]
(Comparative Example
　A2) relative RAV 7MC (ACOMON Ltd.) 99.1 parts by weight, SEESORB 107 (Shipro Kasei Co., Ltd.) 0.75 parts by weight, Plast Blue 8520 (Arimoto Chemical Co., Ltd.) 5ppm, Solvaperm Red BB (Clariant) 2.75 ppm dissolved at 80 ° C. was then added LUPEROX 531M80 (Arkema Yoshitomi, Ltd.) 0.8 parts by weight as a radical polymerization initiator after cooling to room temperature, after degassing by decompression, the aforementioned mold It was poured into 2 and the mold 4, and polymerized while gradually raising the temperature to 105 ° C. from 25 ° C.. And releasing a molded body from the mold after subsequent cooling to 60 ° C.. Curing in the mold 4, the molding was 2mm thick flat plate light rays 420nm cut about 55%, the hue was more good transparency. Mold 2 to produce 10 pieces of lenses were used to evaluate the cracking of at development and release of cracks during polymerization. The results are shown in Table 1.
[0169]
(Comparative Example
　A3) relative RAV 7MC (ACOMON Ltd.) 99.1 parts by weight, SEESORB 107 (Shipro Kasei Co., Ltd.) 0.75 parts by weight, Plast Blue 8520 (Arimoto Chemical Co., Ltd.) 5ppm, Solvaperm Red BB (Clariant) 2.75 ppm dissolved at 80 ° C. was then added LUPEROX 531M80 (Arkema Yoshitomi, Ltd.) 0.8 parts by weight as a radical polymerization initiator after cooling to room temperature, after degassing by decompression, the aforementioned mold 3 and then poured into a mold 4, and polymerized while gradually raising the temperature to 105 ° C. from 25 ° C.. And releasing a molded body from the mold after subsequent cooling to 60 ° C.. Curing in the mold 4, the molding was 2mm thick flat plate light rays 420nm cut about 55%, the hue was more good transparency. By using a mold 3 lens to produce ten to evaluate the occurrence of cracks at the time of development and release of cracks during polymerization. The results are shown in Table 1.
[0170]
[Table 1]

[0171]

　Evaluation of molded article and a plastic lens comprising a cured resin was performed by the following method.
　The following outer periphery of the two glass mold curved surface in this embodiment wound with adhesive tape, cured using a mold assembled in parallel with a gap polymerizable composition and molded.
(Mold 1)
Base Curve: convex: 2.00, concave: 6.00
- center thickness: 10 mm
- Mold diameter: 81 mm
(mold 2)
Base Curve: convex: 4.00, concave: 4.00
- center thickness: 2 mm
· mold diameter: 81mm
[0172]
[Evaluation of Physical Properties]
(1) occurrence of cracks during the polymerization
　in the present embodiment was prepared a plurality of lenses, a lens crack is generated in the edge portion during the polymerization was rejected, was evaluated by the following criteria pass rate .
　- pass rate of 80% or more: ◎
　-pass rate of 50% or more, less than 80%: ￮
　-pass rate of less than 50%: ×
[0173]
(2) generation of cracks at the time of demolding
　a plurality of lenses prepared in this example, a lens that cracks occurs in addition to the outer peripheral portion of the lens at the time of release was rejected, was evaluated by the following criteria pass rate .
　- pass rate of 90% or more: ◎
　-pass rate of 50% or more, less than 90%: ￮
　-pass rate of less than 50%: ×
[0174]
　Using the following components in the embodiment.
(Polymerizable compound
(A)) · RAV 7MC (diethylene glycol, neopentyl glycol and pentaerythritol poly (allyl carbonate) compounds and oligomers thereof, manufactured ACOMON Inc.)
(a radical polymerization initiator
(B)) · LUPEROX 531M80 (1, 1,1-bis (t-amyl peroxy) 80% solution of cyclohexane, Arkema Yoshitomi, Ltd.)
[0175]
(Polyol compound (C2))
, polyethylene glycol, diol type, 600 (average molecular weight 600, manufactured by Wako Pure Chemical Industries, Ltd.)
, polypropylene glycol, diol type, 700 (average molecular weight 700, manufactured by Wako Pure Chemical Industries, Ltd.)
, polypropylene glycol , triol type, 700 (average molecular weight 700, manufactured by Wako Pure Chemical Industries, Ltd.)
, polypropylene glycol, diol type, 1000 (average molecular weight 1000, manufactured by Wako Pure Chemical Industries, Ltd.)
, polypropylene glycol, diol type, 2000 (average molecular weight 2000, manufactured by Wako Pure Chemical Industries, Ltd.)
, Adeka pluronic L-64 (polyoxyethylene - polyoxypropylene - polyoxyethylene block copolymer, manufactured by ADEKA Corporation)
[0176]
(Ultraviolet absorber
(D)) · SEESORB 107 (2,2'-dihydroxy-4,4'-dimethoxy benzophenone, manufactured by Shipro Kasei Co., Ltd.)
(dye
(E)) · Plast Blue 8520 (Solvent Blue 94, Arimoto Chemical Kogyo Co.,
Ltd.) · Solvaperm Red BB (Solvent Red 195, manufactured by Clariant Co., Ltd.)
[0177]
(Example
　B1) RAV 7MC (ACOMON Co.) with respect to 100.0 parts by weight, SEESORB 107 (Shipro Kasei Co., Ltd.) 0.76 parts by weight, Plast Blue 8520 (Arimoto Chemical Co., Ltd.) 5ppm, Solvaperm Red BB (Clariant) 2.77Ppm dissolved at 80 ° C. the, LUPEROX 531M80 (Arkema Yoshitomi, Ltd.) as a radical polymerization initiator after cooling to room temperature 0.8 parts by weight of polypropylene glycol, diol type, 2000 (Wako pure Chemical It was added 0.05 parts by weight Kogyo Co., Ltd.), after degassing by decompression, and poured into a mold of the above was polymerized while gradually raising the temperature to 105 ° C. from 25 ° C.. And releasing the molded body from the mold after subsequent cooling to 60 ° C.. The evaluation results of crack occurrence at the time of development and release of cracks at the time of polymerization of the molded lens in molded lenses and the mold 2 in the mold 1 shown in Table 2. It should be noted, was excellent in appearance is a clear any of the lens.
[0178]
(Example
　B2) RAV 7MC against (ACOMON Ltd.) 100.0 parts by weight, SEESORB 107 (Shipro Kasei Co., Ltd.) 0.76 parts by weight, Plast Blue 8520 (Arimoto Chemical Co., Ltd.) 5ppm, Solvaperm Red BB (Clariant) 2.77Ppm dissolved at 80 ° C. the, LUPEROX 531M80 (Arkema Yoshitomi, Ltd.) as a radical polymerization initiator after cooling to room temperature 0.8 parts by weight of polypropylene glycol, diol type, 1000 (Wako pure Chemical It was added 0.05 parts by weight Kogyo Co., Ltd.), after degassing by decompression, and poured into a mold of the above was polymerized while gradually raising the temperature to 105 ° C. from 25 ° C.. And releasing the molded body from the mold after subsequent cooling to 60 ° C.. The evaluation results of crack occurrence at the time of development and release of cracks at the time of polymerization of the molded lens in molded lenses and the mold 2 in the mold 1 shown in Table 2. It should be noted, was excellent in appearance is a clear any of the lens.
[0179]
(Example
　B3) RAV 7MC against (ACOMON Ltd.) 100.0 parts by weight, SEESORB 107 (Shipro Kasei Co., Ltd.) 0.76 parts by weight, Plast Blue 8520 (Arimoto Chemical Co., Ltd.) 5ppm, Solvaperm Red BB (Clariant) 2.77Ppm dissolved at 80 ° C. the, LUPEROX 531M80 (Arkema Yoshitomi, Ltd.) as a radical polymerization initiator after cooling to room temperature 0.8 parts by weight of polypropylene glycol, diol type, 700 (Wako pure Chemical It was added 0.05 parts by weight Kogyo Co., Ltd.), after degassing by decompression, and poured into a mold of the above was polymerized while gradually raising the temperature to 105 ° C. from 25 ° C.. And releasing the molded body from the mold after subsequent cooling to 60 ° C.. The evaluation results of crack occurrence at the time of development and release of cracks at the time of polymerization of the molded lens in molded lenses and the mold 2 in the mold 1 shown in Table 2. It should be noted, was excellent in appearance is a clear any of the lens.
[0180]
(Example
　B4) RAV 7MC against (ACOMON Ltd.) 100.0 parts by weight, SEESORB 107 (Shipro Kasei Co., Ltd.) 0.76 parts by weight, Plast Blue 8520 (Arimoto Chemical Co., Ltd.) 5ppm, Solvaperm Red BB (Clariant) 2.77Ppm dissolved at 80 ° C. the, LUPEROX 531M80 (Arkema Yoshitomi, Ltd.) as a radical polymerization initiator after cooling to room temperature 0.8 parts by weight of polypropylene glycol, triol type, 700 (Wako pure Chemical It was added 0.05 parts by weight Kogyo Co., Ltd.), after degassing by decompression, and poured into a mold of the above was polymerized while gradually raising the temperature to 105 ° C. from 25 ° C.. And releasing the molded body from the mold after subsequent cooling to 60 ° C.. The evaluation results of crack occurrence at the time of development and release of cracks at the time of polymerization of the molded lens in molded lenses and the mold 2 in the mold 1 shown in Table 2. It should be noted, was excellent in appearance is a clear any of the lens.
[0181]
(Example
　B5) RAV 7MC against (ACOMON Ltd.) 100.0 parts by weight, SEESORB 107 (Shipro Kasei Co., Ltd.) 0.76 parts by weight, Plast Blue 8520 (Arimoto Chemical Co., Ltd.) 5ppm, Solvaperm Red BB (Clariant) 2.77Ppm dissolved at 80 ° C. the, LUPEROX 531M80 (Arkema Yoshitomi, Ltd.) as a radical polymerization initiator after cooling to room temperature 0.8 parts by weight of polyethylene glycol, diol type, 600 (Wako pure Chemical It was added 0.05 parts by weight Kogyo Co., Ltd.), after degassing by decompression, and poured into a mold of the above was polymerized while gradually raising the temperature to 105 ° C. from 25 ° C.. And releasing the molded body from the mold after subsequent cooling to 60 ° C.. The evaluation results of crack occurrence at the time of development and release of cracks at the time of polymerization of the molded lens in molded lenses and the mold 2 in the mold 1 shown in Table 2. It should be noted, was excellent in appearance is a clear any of the lens.
[0182]
(Example
　B6) RAV 7MC against (ACOMON Ltd.) 100.0 parts by weight, SEESORB 107 (Shipro Kasei Co., Ltd.) 0.76 parts by weight, Plast Blue 8520 (Arimoto Chemical Co., Ltd.) 5ppm, Solvaperm Red BB (Clariant) 2.77Ppm dissolved at 80 ° C. the, LUPEROX 531M80 (Arkema Yoshitomi, Ltd.) 0.8 parts by weight as a radical polymerization initiator after cooling to room temperature, Adeka pluronic L-64 a (ADEKA Corporation) It was added 0.05 part by weight, after degassing by decompression, and poured into a mold of the above was polymerized while gradually raising the temperature to 105 ° C. from 25 ° C.. And releasing the molded body from the mold after subsequent cooling to 60 ° C.. The evaluation results of crack occurrence at the time of development and release of cracks at the time of polymerization of the molded lens in molded lenses and the mold 2 in the mold 1 shown in Table 2. It should be noted, was excellent in appearance is a clear any of the lens.
[0183]
(Comparative Example
　B1) with respect to RAV 7MC (ACOMON Ltd.) 100.0 parts by weight, SEESORB 107 (Shipro Kasei Co., Ltd.) 0.76 parts by weight, Plast Blue 8520 (Arimoto Chemical Co., Ltd.) 5ppm, Solvaperm Red BB (Clariant) 2.77Ppm dissolved at 80 ° C. was then added LUPEROX 531M80 (Arkema Yoshitomi, Ltd.) 0.8 parts by weight as a radical polymerization initiator after cooling to room temperature, after degassing by decompression, the aforementioned mold It was injected into, and 43 hours polymerized with increasing gradually the temperature to 105 ° C. from room temperature. And releasing the molded body from the mold after subsequent cooling to 60 ° C.. The evaluation results of crack occurrence at the time of development and release of cracks at the time of polymerization of the molded lens in molded lenses and the mold 2 in the mold 1 shown in Table 2.
[0184]
[Table 2]

[0185]
　This application, and based on Japanese Patent Application No. 2017-118598, filed on priority and June 16, 2017 based on Japanese Patent Application No. 2017-030270, filed on February 21, 2017 the priority to be claimed, the entire disclosure of which is incorporated herein.

The scope of the claims
[Requested item 1](A) represented by the following general formula (a), a compound containing two or more allyloxycarbonyl group,
　(B) peroxy ketal radical polymerization initiator, peroxy monocarbonate based radical polymerization initiator and peroxy and at least one radical polymerization initiator is selected from the group consisting of ester-based radical polymerization initiator,
　tables in (C) polyether-modified siloxane compound represented by the following general formula (c1) or the following general formula (c2) a modifier selected from polyol compounds
containing, for optical materials polymerizable composition;
formula 1]

(in the general formula (a), n is an integer of 2 ~ 6 .R 1 is hydrogen indicates an atom or a methyl group, more present R 1 may optionally be the same or different .X is a straight-chain or branched aliphatic oxygen atom has optionally 1-3 carbon atoms which may atom 12 a polyol Divalent to hexavalent organic group a, divalent to hexavalent organic group b derived from alicyclic polyol oxygen atoms to 5 carbon atoms which may atoms have 16 or the number of carbon atoms, derived from 6 to a divalent to hexavalent organic group c derived from an aromatic compound of 12, an organic group a or an organic group b is combined with an allyloxycarbonyl group through an oxygen atom derived from a hydroxyl group they comprise forming an allyl carbonate group.)
[formula 2]

in (formula (c1), R 1 ~ R 8 may be the same or different, R 1~ R 8 at least one represents a polyether group represented by the following general formula (c1a), other R 1 ~ R 8 , which may be identical or different, straight-chain having 1 to 20 carbon atoms or branched alkyl groups, linear or branched alkoxy group having 1 to 20 carbon atoms, hydroxyl groups, and polysiloxy groups. R presence of a plurality of 2 ~ R 5 may be the same or different. m, n may be the same or different, represent an integer of 0 or greater. ),
[Chemical Formula 3]

In (formula (c1a), R 25 is a linear or branched alkylene group, R having 1 to 20 carbon atoms 26 is hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms , C 2-20 straight or branched alkenyl group or C 2-20 straight-chain or indicating a branch alkynyl groups. multiple present R 25 is good .k be the same or different 1 or more represents an integer.)
[formula 4]

in (formula (c2), R 2 represents a hydroxyl group, .R represents an -OX group or a linear or branched alkyl group having 1 to 4 carbon atoms, 3Represents a hydrogen atom, X group, or a linear or branched alkyl group having 1 to 4 carbon atoms. R 4 represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms. Q 1 ~ Q 7 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, -CH 2 represents an -OX group or -OX group. p represents an integer of 1 ~ 4, s represents an integer of 0 ~ 4, t is an integer of 0 ~ 4, r is an integer of 1 to 1,000. Q presence of a plurality of 1 ～ Q 7 , X, S, T may be the same or different. * Represents a bond. ).
[Requested item 2]
　Further, (D) containing the ultraviolet absorbent represented by the following general formula (d), the optical material for the polymerizable composition according to claim 1;
Formula 5]

In (formula (d), R 1 is a hydrogen atom, a linear or branched alkyl group having a carbon number of 1 ~ 20. R presence of a plurality of 1 each other good .m be the same or different an integer of 1 to 3, n represents an integer of 1 to 3 are shown, the sum of m and n is an integer of 3-6.).
[Requested item 3]
　Additionally, (E) anthraquinone dyes, perinone dyes, monoazo dyes, at least one dye selected from diazo dyes, and phthalocyanine dyes, optical material for the polymerization of claim 1 or 2 Composition.
[Requested item 4]
　Compounds containing 2 or more allyloxycarbonyl group (A) is
allyl carbonate polymerizable compound represented by the following general formula (a1) (A1) and its oligomers,
the following general formula (a2-1) or the following general formula ( allyl ester polymerizable compound represented by a2-2) (A2) and oligomers thereof or
a polymerizable compound containing at least one of the allyl ester group and an allyl carbonate group represented by the following general formula (a3) (A3) and including oligomers thereof, the optical material for the polymerizable composition according to any one of claims 1 to 3;
[formula 6]

in (formula (a1), X is a straight chain of 3 to 12 carbon atoms or an divalent to hexavalent group derived from alicyclic polyols having 2 to 6 valent group or a carbon atom number of 5 to 16 are derived from branched aliphatic polyol, n represents an integer of 2-6 The represented.),
[Chemical Formula 7]

[Chemical Formula 8]

In (formula (a2-2), X is a divalent group derived from a straight-chain or branched aliphatic diols having 2 to 8 carbon atoms , or represents a linear or branched 3-6 monovalent group derived from an aliphatic polyol having 3 to 10 carbon atoms having 3-6 hydroxyl groups, n is an integer of 2-6.)
[ of 9]

(in the general formula (a3), X is the number of carbon atoms having 3 to 6 a divalent group or a hydroxyl group, which are derived from linear or branched aliphatic diols having 2 to 8 carbon atoms 3 represents a linear or branched 3-6 monovalent group derived from an aliphatic polyol ~ 10, m and n are 0 to an integer of 6, and the sum of m and n is an integer of from 2 to 6 is there.).
[Requested item 5]
　The allyl carbonate polymer compound (A1) is diethylene glycol, dipropylene glycol, triethylene glycol, tetraethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6 hexanediol, neopentyl glycol, 3-methyl-1,5-pentanediol, 2-methyl-2-ethyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, 2,2, 4-trimethyl-1,3-pentanediol, 1,4-dimethylolcyclohexane and 4,8-bis (hydroxymethyl) - [5.2.1.0 2, 6 ] at least one selected from tricyclodecane bis (allyl carbonate) compound species of diol,
glycerol, Torimechiro Propane and tris least one triol tris (allyl carbonate) is selected from (hydroxyethyl) isocyanurate compounds,
pentaerythritol, at least one tetraol tetra (allyl carbonate selected from diglycerol and ditrimethylolpropane ) compounds,
hexa dipentaerythritol (allyl carbonate) compounds, and
the diols, the triol, mixed poly (allyl carbonate) compounds of at least two compounds selected from tetraols and said dipentaerythritol is selected from including at least one kind of an optical material for the polymerizable composition according to claim 4 that.
[Requested item 6]
　The allyl carbonate polymerizable compound (A1),
(i) diethylene glycol bis (allyl carbonate) compounds and mixtures and oligomers thereof,
and (ii) bis (allyl carbonate) of a mixture of diethylene glycol and neopentyl glycol compounds and oligomers thereof mixture,
(iii) diethylene glycol and tris poly (allyl carbonate) of a mixture of (hydroxyethyl) isocyanurate compounds and mixtures and oligomers thereof,
(iv) diethylene glycol and poly (allyl carbonate) of a mixture of trimethylol propane compounds and a mixture of oligomers,
(v) diethylene glycol and poly (allyl carbonate) of a mixture of pentaerythritol compound and its mixture with oligomers,
and (vi) diethylene glycol Poly neopentyl glycol and mixtures of pentaerythritol (allyl carbonate) compounds and mixtures and oligomers thereof, and
(vii) poly (allyl carbonate) of diethylene glycol and neopentyl glycol and mixtures of pentaerythritol compound and a mixture of oligomers thereof and ,
diethylene glycol bis (allyl carbonate) compounds and mixtures and poly (allyl carbonate) mixture comprising, and its oligomers
containing at least one selected from, for optical materials polymerizable composition according to claim 4.
[Requested item 7]
　The allyl ester polymerizable compound (A2) or the polymerizable compound (A3),
diallyl isophthalate, diallyl phthalate compound selected from diallyl terephthalate and diallylorthophthalate,
said diallyl phthalate compound, ethylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tetraethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, neopentyl glycol, 3 - methyl-1,5-pentanediol, 2-methyl-2-ethyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, 2,2,4-trimethyl-1,3 Pentanjio 1,4 least one diol diallyl ester compounds and oligomers obtained by transesterification of a mixture of selected from dimethylol cyclohexane,
and the diallyl phthalate compound, glycerol, trimethylolpropane, tris (hydroxyethyl ) isocyanurate, pentaerythritol, diglycerol, ditrimethylolpropane, at least one polyol transesterification polyallyl ester compound and its oligomer obtained by the mixture of selected from dipentaerythritol, and
Dialkyl isophthalate having an alkyl group having 1 to 3 carbon atoms, a dialkyl terephthalate, a mixture of at least one dialkyl phthalate selected from dialkyl ortho phthalate, allyl alcohol, diallyl carbonate, and the diol or the polyol obtained by transesterification, allyl ester compound, allyl carbonate compound, and a compound having an allyl carbonate group and an allyl ester group and containing at least one oligomer thereof, is selected from polymerizable optical material according to claim 4 gender composition.
[Requested item 8]
　The allyl ester polymerizable compound (A2) or the polymerizable compound (A3),
(i) diallyl terephthalate and, said diallyl terephthalate against 30% by weight of diethylene glycol bis (allyl carbonate) compounds and mixtures and oligomers thereof ,
(ii) allyl ester compound obtained by transesterification of a mixture of diallyl terephthalate and propylene glycol,
(iii) allyl ester compound of (ii) and, 20 wt% of diethylene glycol bis relative to the allyl ester compound (allyl carbonate) compounds and mixtures and oligomers thereof,
(iv) dimethyl terephthalate, allyl alcohol, obtained by the transesterification of diallyl carbonate, and mixtures of diethylene glycol, allyl ester compound Allyl carbonate compounds, and mixtures of compounds having the allyl ester group and an allyl carbonate group, and
(v) the mixture obtained in (iv) and, 10 wt% of diethylene glycol bis to the mixture (allyl carbonate) compound and its oligomer, mixtures, comprising at least one member selected from, for optical materials polymerizable composition according to claim 4.
[Requested item 9]
　The compound containing two or more allyloxycarbonyl group (A) is,
　with the allyl ester polymerizable compound (A2) and / or the polymerizable compound (A3) and their oligomers according to claim 7, claim 5 the allyl carbonate polymer compound (A1) and its oligomer, mixtures for optical material polymerizable composition according to claim 4 is as set forth in.
[Requested item 10]
　Ultraviolet absorber (D) is 2,2'-dihydroxy-4-methoxybenzophenone, 2,2 ', 4,4'-tetra hydroxybenzophenone, is 2,2'-dihydroxy-4,4'-dimethoxy benzophenone the optical material for the polymerizable composition according to claim 2.
[Requested item 11]
　10 hours the radical polymerization initiator (B) is 10-hour half-life temperature of 80 ° C. or more peroxy ketal polymerization initiator represented by the following general formula (b1), represented by the following general formula (b2) select half-life temperature of 80 ° C. or more peroxy monocarbonate based polymerization initiator, and the group 10-hour half-life temperature represented by the following general formula (b3) is from 65 ° C. or more peroxyester polymerization initiator at least one element, the optical material for the polymerizable composition according to any one of claims 1 to 10;
[formula 10]

in (formula (b1), R 3 is a tertiary alkyl group, R 1 and R 2 are alkyl groups selected independently from methyl, ethyl, propyl and butyl, said alkyl group can have an alkyl ester group at the chain end, or R 1 and R 2 is Together with the carbon atom to which these are attached can form a cycloalkylene group, the cycloalkylene group may have 1 to 3 alkyl substituents.),
[Formula 11 ]

(in the general formula (b2), R 1 is a tertiary alkyl group having a carbon number of 3 to 6, R 2 is a straight-chain or branched alkyl group having 3 to 8 carbon atoms.),
[ of 12]

(In the general formula (b3), R 1 is a tertiary alkyl group having a carbon number of 3 to 6, R 2 is a straight-chain or branched alkyl group or a phenyl group having a carbon number of 3-9.) .
[Requested item 12]
　R polyether group represented by the general formula (c1a) 26 is a linear or branched alkyl group having a hydrogen atom or a C 1-20, for optical material according to any one of claims 1 to 11 polymerizable composition.
[Requested item 13]
　Formula R polyether group represented by (c1a) 26 is a linear or branched alkynyl group having a linear or branched alkenyl group or C 2-20 2 to 20 carbon atoms, claim 1 the optical material for the polymerizable composition according to any one of 1 to 11.
[Requested item 14]
　Molded body obtained by curing the optical material for the polymerizable composition according to any one of claims 1 to 13.
[Requested item 15]
　Optical material comprising a molded body according to claim 14.
[Requested item 16]
　Plastic lenses made of molded product according to claim 14.
[Requested item 17]
　(A) represented by the following general formula (a), a compound containing two or more allyloxycarbonyl group,
　(B) peroxy ketal radical polymerization initiator, peroxy monocarbonate based radical polymerization initiator and peroxy and at least one radical polymerization initiator is selected from the group consisting of ester-based radical polymerization initiator,
　tables in (C) polyether-modified siloxane compound represented by the following general formula (c1) or the following general formula (c2) a modifier selected from a polyol compound, by mixing, a process of preparing an optical material for the polymerizable composition,
　a lens substrate by cast polymerization of the optical material for the polymerizable composition and forming, a method of manufacturing a plastic lens;
formula 13]

in (formula (a), n is an integer of 2 ~ 6 .R 1 is a hydrogen atom or a methyl group Shown, R presence of a plurality of 1 good be the same or different .X is 2 ~ derived from a straight-chain or branched aliphatic polyol oxygen atom has optionally 1-3 carbon atoms which may atoms 12 6 valent organic group a, 2 ~ 6-valent organic group b derived from alicyclic polyol oxygen atoms to 5 carbon atoms which may atoms have 16 or aromatics having 6 to 12 carbon atoms, a divalent to hexavalent organic group c derived from an organic group a or an organic group b is combined with an allyloxycarbonyl group through an oxygen atom derived from a hydroxyl group to which they are provided to form the allyl carbonate groups. )
[formula 14]

in (formula (c1), R 1~ R 8 may be the same or different, R 1 ~ R 8 at least one represents a polyether group represented by the following general formula (c1a), other R 1 ~ R 8 are the same or different even well, a linear or branched alkyl group, a linear or branched alkoxy group having 1 to 20 carbon atoms, a hydroxyl group or a polysiloxy group, having 1 to 20 carbon atoms. R presence of a plurality of 2 ~ R 5 may be the same or different. m, n may be the same or different, represent an integer of 0 or greater. ),
[Formula 15]

in (formula (c1a), R 25 is a linear or branched alkylene group, R having 1 to 20 carbon atoms 26 is hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms , C 2-20 straight or branched alkenyl group or C 2-20 straight-chain or indicating a branch alkynyl groups. multiple present R 25 is good .k be the same or different 1 or more represents an integer.)
[formula 16]

in (formula (c2), R 2Represents a hydroxyl group, a -OX group or a linear or branched alkyl group having 1 to 4 carbon atoms. R 3 represents a hydrogen atom, X group, or a linear or branched alkyl group having 1 to 4 carbon atoms. R 4 represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms. Q 1 ~ Q 7 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, -CH 2 represents an -OX group or -OX group. p represents an integer of 1 ~ 4, s represents an integer of 0 ~ 4, t is an integer of 0 ~ 4, r is an integer of 1 to 1,000. Q presence of a plurality of 1 ～ Q 7 , X, S, T may be the same or different. * Represents a bond. )
[Requested item 18]
　Wherein the step of preparing the optical material for the polymerizable composition further (D) a mixture of UV absorber represented by the following general formula (d), is a step of preparing an optical material for the polymerizable composition the method of manufacturing a plastic lens according to claim 17;
formula 17]

in (formula (d), R 1 . is a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms plurality of R is 1 each other may be the same or different .m is an integer of 1 to 3, n is an integer of 1 to 3, the sum of m and n is an integer of 3-6.).
[Requested item 19]
　Wherein step further (E) mixing the anthraquinone dyes, perinone dyes, monoazo dyes, diazo dyes, and at least one dye selected from the phthalocyanine dye for preparing the optical material for the polymerizable composition to a process for preparing an optical material for the polymerizable composition, method of manufacturing a plastic lens according to claim 17 or 18.