Specification
Title of Invention: Polymerizable Compositions and Molds for Optical Materials
Technical field
[0001]
　The present invention relates to polymerizable compositions and molded articles for optical materials.
Background technology
[0002]
　Compared to inorganic lenses, plastic lenses are lighter and harder to break, so they are rapidly becoming widespread in optical elements such as spectacle lenses and camera lenses. Since it is easy to add various additives to plastic lenses, studies have been conducted to impart desired functions by using various additives. Further, when a polymerizable composition containing a predetermined compound is polymerized to form a plastic lens, a radical polymerization initiator is widely used as a polymerization initiator.
[0003]
　Patent Document 1 is selected from the group consisting of about 55 to about 90% by weight of polyol (allyl carbonate), about 10 to about 40% by weight of aliphatic polyurethane having ethylenically unsaturated terminal, and allyl methacrylate and allyl acrylate. It is disclosed that a material having an excellent photo-alteration response can be provided by containing a polyol (allyl carbonate) component consisting of about 0 to about 5% by weight of the bifunctional monomer and an organic photo-alteration substance. The document states that the material may contain a radical polymerization initiator.
[0004]
　Patent Document 2 describes a low-temperature polymerization step in which a raw material solution containing two types of radical polymerization initiators having different half-life temperatures is heated in a low temperature range of less than 90 ° C, and a subsequent low-temperature polymerization step in the range of 90 ° C to 100 ° C. A method for producing a plastic lens for spectacles, which is polymerized by a high temperature polymerization step of heating in a high temperature region, is disclosed. The document states that plastic lenses for spectacles can contain an ultraviolet absorber.
[0005]
　Patent Document 3 discloses a method for producing a plastic lens, which comprises a step of radically polymerizing a composition containing a (meth) acrylate-based monomer and two or more kinds of organic peroxides having different half-lives. The document states that a plastic lens can contain an ultraviolet absorber.
　Patent Document 4 discloses a composition for a plastic lens containing a polymerizable monomer containing an allyl group and two types of aliphatic organic peroxides having different half-life temperatures.
[0006]
　In Patent Document 5, a monomer containing dimetalylphthalate as a main component and two types of aliphatic organic peroxides having different half-life temperatures as a polymerization initiator are blended in a desired lens mold. A method for producing a plastic lens in which a compound is polymerized is disclosed.
Prior art literature
Patent documents
[0007]
Patent Document 1:
Japanese Patent Application Laid-Open No. 04-502931 Patent Document 2: Japanese Patent Application Laid-Open No. 2013-213937
Patent Document 3: Japanese Patent Application Laid-Open No. 10-14769
Patent Document 4: Japanese Patent Application Laid-Open No. 08-127608
Patent Document 5: Special Publication No. Kaisho 61-144601
Patent Document 6: Japanese Patent Application Laid-Open No. 2009-19157
Outline of the invention
Problems to be solved by the invention
[0008]
　The techniques described in the above literature had the following points to be improved.
　The phototautomerizing material composed of allyl carbonate and acrylic, which has a large amount ratio of allyl carbonate as in Patent Document 1, has low transparency and has room for improvement.
[0009]
　Further, when a predetermined polymerizable monomer and two types of radical polymerization initiators having different half-life temperatures are used as in Patent Documents 2 to 6, there is room for improvement in the moldability of the lens.
　Furthermore, when two types of radical polymerization initiators having different half-life temperatures are used as in Patent Documents 2 to 6, even if an ultraviolet absorber, a dye, or the like is added, the effect of adding these agents cannot be sufficiently exhibited. In some cases, it may not be possible to use an additive that exerts a desired effect.
[0010]
　Therefore, as a result of diligent studies, the present inventors have obtained a plastic lens having excellent surface hardness without impairing transparency by copolymerizing a specific diallyl carbonate and (meth) acrylate at a specific ratio. It was found that the moldability was excellent and the yield of the product was improved. Furthermore, it has been found that by using two different types of radical polymerization initiators having a specific radical residual ratio, additives such as an ultraviolet absorber and a dye can stably exert a desired effect.
Means to solve problems
[0011]
　The present invention can be shown below.
[1] (A) An allyl carbonate compound containing two or more allyloxycarbonyl groups represented by the general formula (1), and
(B) two (meth) acrylic groups represented by the general formula (2). A (meth) acrylate compound containing at least one,
(C) a compound represented by the general formulas (3) to (6), at least one compound selected from the following dyes, and
(D) at least a radical polymerization initiator ( A polymerization initiator containing D1) and a radical polymerization initiator (D2), and the
　compound (A) is contained in an amount of more than 0% by weight and 30% by weight in a total of 100% by weight of the compound (A) and the compound (B). % Or less, compound (B) is contained in an amount of 70% by weight or more and less than 100% by weight, and the
　radical polymerization initiator (D1) has a radical residual rate of 20% or more and less than 100% after 5 hours at 50 ° C. and 70 ° C. The radical residual rate after 5 hours is 0% or more and less than 30%, and the
　radical polymerization initiator (D2) has a radical residual rate of 30% or more and less than 98% after 5 hours at 70 ° C., and is polymerizable for optical materials. Composition;
[Chemical

formula 1] (In general formula (1), R 1 is a 2- to 20-valent radical or hetero atom derived from a chain or branched C3-C35 aliphatic radical which may contain a hetero atom. Indicates a 2-6-valent radical derived from a cyclic aliphatic polyol of C5-C40 which may contain. M represents an integer of 2-20. R 1Does not contain an allyloxycarbonyl group. ),
[Chemical

formula 2] (In the general formula (2), R 2 represents a 2- to tetravalent organic group having 1 to 30 carbon atoms which may contain a hetero atom or an aromatic group. R 3 is Indicates a hydrogen atom or a methyl group. N indicates an integer of 2 to 4.),
[Chemical

formula 3] (In the general formula (3), R 1 and R 2 are alkyl groups or halogen atoms of C1 to C8. indicated, identical or different. more existing R 1 s or more existing R, 2 are each other may be the same or different .m is an integer of 0 to 3, n represents an integer of 0 to 3 , P represents an integer of 0 to 1, R 3 represents a functional group of C2 to C15 containing an ester bond.),
[Chemical

formula 4] (In general formula (4), Z 3 is substituted. aromatic organic group optionally C6 ~ C20, showed an alicyclic group which may be substituted C5 ~ have C20, Z 4 and Z 5 may be the same or different, C1 ~ C6 alkyl group, C1 ~ C6 Shows an alkoxy group.),
[Chemical Formula 5]

In (formula (5), A 1 ~ A 8 , X 1 ~ X 4 each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, hydroxy group, an amino group, a carboxyl group, a sulfonic Acid group, linear, branched or cyclic alkyl group with 1 to 20 carbon atoms, alkoxy group with 1 to 20 carbon atoms, aryloxy group with 6 to 20 carbon atoms, monoalkylamino group with 1 to 20 carbon atoms, carbon A dialkylamino group having 2 to 20 carbon atoms, a dialkylamino group having 7 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group, an alkylthio group having 6 to 20 carbon atoms, .A an arylthio group having a carbon number of ~ 20 6 1 ~ a 8 mAY form a ring except an aromatic ring via a linking group .n represents 0 or 1 .Q 1 ~ Q 4 is Each independently represents a carbon atom and a nitrogen atom. M represents two hydrogen atoms, a divalent metal atom, a divalent monosubstituted metal atom, a tetravalent disubstituted metal atom, or an oxymetal atom.) ,
[Chemical formula 6]

(in the general formula (6), R 1 represents a hydrogen atom, a linear or branched alkyl group having a carbon number of 1 ~ 20. R presence of a plurality of 1They may be the same or different. m is an integer of 1 to 3, n is an integer of 1 to 3, and the sum of m and n is an integer of 3 to 6. ),
　Dyes: At least one selected from anthraquinone dyes, perinone dyes, monoazo dyes, diazo dyes, and phthalocyanine dyes.
[2] The compound (A) 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- At least one selected from trimethyl-1,3-pentanediol, 1,4-dimethylolcyclohexane and 4,8-bis (hydroxymethyl)-[5.2.1.0 2,6 ] tricyclodecane.
Select from at least one triol tris (allyl carbonate) compound,
pentaerythritol, diglycerol and ditrimethylol propane selected from diol bis (allyl carbonate) compounds, glycerol, trimethylol propane and tris (hydroxyethyl) isocyanurate. Includes at least one selected from the group consisting of at least one tetraol tetra (allyl carbonate) compound,
dipentaerythritol hexa (allyl carbonate) compound, and
bispentaerythritol hexa (allyl carbonate) compound. ,
　The polymerizable composition for an optical material according to [1], which comprises the allyl carbonate compound (A) or a mixture of the allyl carbonate compound (A) and an oligomer thereof.
[3] Compound (A) is
(i) bis (allyl carbonate) compound of
diethylene glycol , (ii) bis (allyl carbonate) compound of a mixture of diethylene glycol and neopentyl glycol,
(iii) diethylene glycol and tris (hydroxyethyl) isocia. Poly (allyl carbonate) compound of a mixture of nurate,
(iv) Poly (allyl carbonate) compound of a mixture of diethylene glycol and trimethylolpropane,
(v) Poly (allyl carbonate) compound of a mixture of diethylene glycol and pentaerythritol,
(vi) Diethylene glycol And a poly (allyl carbonate) compound of a mixture of neopentyl glycol and pentaerythritol, and
(vii) a poly (allyl carbonate) compound of a mixture of diethylene glycol, neopentyl glycol and pentaerythritol, and
a bis (allyl carbonate) compound of diethylene glycol. The
　polymerizable composition for an optical material according to [1] or [2], which is at least one selected from a poly (allyl carbonate) mixture containing, and comprises a mixture of the allyl carbonate compound (A) and an oligomer thereof. Stuff.
[4] The optical material according to any one of [1] to [3], wherein the compound (B) is selected from the compounds represented by the general formula (2-1) and the general formula (2-2). Polymerizable composition.
[Chemical formula 7]

(p indicates a numerical value from 1 to 100, R 3 indicates a hydrogen atom or a methyl group, and they do not have to be the same.)
[Chemical formula 8]

(q indicates a numerical value of 1 or more, respectively. The sum of the two qs represents a number from 2 to 100. R 3 represents a hydrogen atom or a methyl group, which may not be the same. X is a substituted or unsubstituted divalent aromatic group. Indicates a divalent aliphatic group which may contain a substituted or unsubstituted aromatic group having 1 to 20 carbon atoms.)
[5] The compound (B) has a p in the general formula (2-1). The polymerizable composition for an optical material according to [4], which is selected from the compounds represented by 2 to 4.
[6] A molded product obtained by curing the polymerizable composition for an optical material according to any one of [1] to [5].
[7] An optical material made of the molded product according to [6].
[8] A plastic lens made of the molded product according to [6].
[9] A
　plastic polarizing lens comprising a polarizing film and a base material layer made of the molded product according to [6] formed on at least one surface of the polarizing film.
[0012]
　In the present invention, for example, the "bis (allyl carbonate) compound of a diol" means a compound having a structure in which two hydroxyl groups of a diol are replaced with an allyl carbonate group. The diol may be used alone or in combination of two or more.
　Further, in the present invention, for example, the "bis (allyl carbonate) compound of a mixture of diethylene glycol and neopentyl glycol" is
(1) a compound having a structure in which two hydroxyl groups of diethylene glycol are replaced with an allyl carbonate group,
(2). ) It means a compound having a structure in which two hydroxyl groups of neopentyl glycol are replaced with an allyl carbonate group.
　Further, in the present invention, for example, the "oligomer of a bis (allyl carbonate) compound of a mixture of diethylene glycol and neopentyl glycol" is
selected from any of the following (3), (4), or (5), or any of these. It means a mixture of two or more kinds to be produced.
(3) Oligomer of bis (allyl carbonate) compound
　of diethylene glycol A compound having a structure in which two or more molecules of diethylene glycol are oligomerized via a carbonate bond and the terminal hydroxyl group is replaced with an allyl carbonate group.
(4) Oligomer of bis (allyl carbonate) compound of
　neopentyl glycol A compound having a structure in which two or more neopentyl glycols are oligomerized via a carbonate bond and the terminal hydroxyl group is replaced with an allyl carbonate group.
(5) Oligomer of bis (allyl carbonate) compound
　of diethylene glycol and neopentyl glycol One or more molecules of diethylene glycol and one or more molecules of neopentyl glycol are oligomerized in the same molecule in a random combination via a carbonate bond. A compound having a structure in which the terminal hydroxyl group is replaced with an allyl carbonate group.
　The same applies to the case of "bis (allyl carbonate) compound of trifunctional or higher functional polyol" and "bis (allyl carbonate) compound using two or more kinds of diol and trifunctional or higher functional polyol".
　In the case of "an oligomer of a bis (allyl carbonate) compound of a trifunctional or higher-functional polyol" and "an oligomer of a bis (allyl carbonate) compound using two or more types of a diol and a trifunctional or higher-functional polyol", all the hydroxyl groups at the ends are It includes a structure in which an allyloxycarbonate group is replaced, and a structure in which some hydroxyl groups at the terminal are replaced with an allyloxycarbonate group.
　Further, in the present invention, for example, "1 to 10" means "1 or more and 10 or less".
　Further, in the present invention, the hetero atom means an atom other than C and H.
Effect of the invention
[0013]
　According to the polymerizable composition for an optical material of the present invention, it is possible to provide a plastic lens having excellent surface hardness without impairing transparency, and at the same time, it is excellent in moldability and the yield of the plastic lens is improved. To. Further, by combining a specific radical polymerization initiator, the obtained plastic lens can stably exert a desired effect with additives such as an ultraviolet absorber and a dye.
Mode for carrying out the invention
[0014]
　The polymerizable composition for an optical material of the present invention will be described based on the following embodiments.
　The polymerizable composition for an optical material of the present embodiment is
represented by (A) an allyl carbonate compound represented by the general formula (1) and containing two or more allyloxycarbonyl groups, and
(B) the general formula (2). A (meth) acrylate compound containing two or more (meth) acrylic groups, and
(C) at least one compound selected from the compounds represented by the general formulas (3) to (6) and dyes.
(D) Includes at least a polymerization initiator containing a radical polymerization initiator (D1) and a radical polymerization initiator (D2).
　In the total 100% by weight of the compound (A) and the compound (B), the compound (A) is contained in an amount of more than 0% by weight and 30% by weight or less, and the compound (B) is contained in an amount of 70% by weight or more and less than 100% by weight.
　The radical polymerization initiator (D1) has a radical residual rate of 20% or more and less than 100% after the lapse of 5 hours at 50 ° C. and a radical residual rate of 0% or more and less than 30% after the lapse of 5 hours at 70 ° C. In (D2), the radical residual rate after the lapse of 5 hours at 70 ° C. is 30% or more and less than 100%.
　The polymerizable composition for optical materials of the present embodiment does not contain a photochromic compound.
[0015]
　According to the polymerizable composition for an optical material of the present embodiment, it is possible to provide a plastic lens having excellent surface hardness without impairing transparency, and it is also excellent in moldability and the yield of the plastic lens is improved. Will be done. Further, by combining a specific radical polymerization initiator, the obtained plastic lens can stably exert the desired effect of the compound (C) as an additive.
　Hereinafter, each component will be described.
[0016]
[(A) Allyl carbonate compound]
　The allyl carbonate compound (A) in the present embodiment can be represented by the following formula.
[0017]
[Chemical 9]

[0018]
　R 1 is derived from a 2- to 20-valent group derived from a chain or branched C3-C35 aliphatic polyol which may contain a heteroatom or a C5-C40 cyclic aliphatic polyol which may contain a heteroatom. Indicates a group having a valence of 2 to 20 or less. m represents an integer of 2 to 20. R 1 does not contain an allyloxycarbonyl group.
[0019]
　The polymerizable composition for an optical material of the present embodiment can contain an oligomer thereof together with the allyl carbonate compound (A).
　The oligomer is, for example, a poly (allyl carbonate) in which two or more molecules of a polyol are linked via a carbonate bond, which is produced by a transesterification reaction between diallyl carbonate and a polyol.
[0020]
　This polyol can usually have 2 or more and 8 or less, preferably 2 or more and 6 or less hydroxyl groups in the molecule. This allyl carbonate compound is a chain-like or branched-chain aliphatic polyol poly (allyl carbonate) having 3 or more and 35 or less carbon atoms. Poly (allyl carbonate), a cyclic aliphatic polyol having 5 or more and 40 or less carbon atoms in the molecule, is also suitable for this purpose. A mixed poly (allyl carbonate), that is, one derived from two or more types of polyols and can be obtained by mixing a single polyol poly (allyl carbonate), or by a chemical reaction starting from a mixture of polyols and diallyl carbonate. It is also possible to use what can be obtained directly. Finally, all these polys (allyl carbonates) can be in the form of monomers or mixtures of monomers with oligomers.
[0021]
Specific examples of the polyol constituting 　R 1 of the general formula (1) include diethylene glycol, dipropylene glycol, triethylene glycol, tetraethylene glycol, 1,3-propanediol, 1,4-butanediol, and 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 ] tri Cyclodecane, glycerol, trimethylolpropane, tris (hydroxyethyl) isocyanurate, pentaerythritol, diglycerol, ditrimethylolpropane, dipentaerythritol, bispentaerythritol and the like can be mentioned.
[0022]
　Therefore, the allyl carbonate compound (A) is diethylene glycol, dipropylene glycol, triethylene glycol, tetraethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexane. Diol, neopentyl glycol, 3-methyl-1,5-pentanediol, 2-methyl-2-ethyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, 2,2,4 At least one selected from -trimethyl-1,3-pentanediol, 1,4-dimethylolcyclohexane and 4,8-bis (hydroxymethyl)-[5.2.1.0 2,6 ] tricyclodecane. From bis (allyl carbonate) compounds of diols, glycerol, trimethylolpropane and trisol (allyl carbonate) compounds of at least one triol selected from tris (hydroxyethyl) isocyanurate, pentaerythritol, diglycerol and ditrimethylol propane. At least one selected from the group consisting of at least one tetraol tetra (allyl carbonate) compound, dipentaerythritol hexa (allyl carbonate) compound, and bispentaerythritol hexa (allyl carbonate) compound. Including.
　The allyl carbonate compound (A) and its oligomer consist of a mixed poly (allyl carbonate) compound of at least two compounds selected from the diol, the triol, the tetraol, the dipentaerythritol, and the bispentaerythritol. Includes at least one selected.
[0023]
　The "bis (allyl carbonate) of a mixture of at least two types of diols" is, for example, a mixture of the following monomer components (allyl carbonate compound (A)) and an oligomer component when the diols are diethylene glycol and neopentyl glycol. can get.
Monomer component
(1) Diethylene glycol bis (allyl carbonate)
(2) Neopentyl glycol bis (allyl carbonate)
oligomer component
(3) Polycarbonate containing only diethylene glycol-derived hydrocarbon (and ether)
(4) Neopentyl glycol-derived hydrocarbon
Monomers containing only (5) Composite oligomers containing both diethylene glycol-derived hydrocarbons (and ethers) and neopentyl glycol-derived hydrocarbons
[0024]
　The following are preferred examples of the allyl carbonate polymerizable compound (A) and its oligomers suitable for the purposes of the present invention.
(i) Diethylene glycol bis (allyl carbonate) compound and a mixture thereof with an oligomer
　Diethylene glycol bis (allyl carbonate) can be defined by the formula (1-1).
[0025]
[Chemical 10]

[0026]
　Further, the oligomer of diethylene glycol bis (allyl carbonate) can be defined by the formula (1-2).
[0027]
[Chemical 11]

[0028]
　In the formula, r is 2 or more.
　Compound (1-1) reacts diethylene glycol bis (chloroformate) with allyl alcohol, for example, as described in "Encyclopedia of Chemical Technology", Kirk-Othmer, Edition III, Volume 2, pp. 111-112. It can be manufactured by letting it. Mixtures of diethylene glycol bis (allyl carbonate) (formula (1-1)) and its oligomers (formula (1-2)) are based, for example, as described in European Patent No. 35,304. It can be easily produced by transesterification of diallyl carbonate and diethylene glycol by operating in the presence of a sex catalyst. These mixtures usually contain up to about 80% by weight of oligomers.
[0029]
(ii) Mixture of bis (allyl carbonate) compound of mixture of diethylene glycol and neopentyl glycol and its oligomer
　This bis (allyl carbonate) compound is described above except that diethylene glycol is replaced with a mixture of diethylene glycol and neopentyl glycol. It is the same as the bis (allyl carbonate) of (i).
[0030]
(iii) Poly (allyl carbonate) compound of a mixture of diethylene glycol and tris (hydroxyethyl) isocyanurate and a mixture of an oligomer thereof
　The poly (allyl carbonate) compound is described in, for example, US Pat. No. 4,812,545. As such, it can be obtained by ester exchange of diallyl carbonate in a mixture of diethylene glycol and tris (hydroxyethyl) isocyanurate.
[0031]
(iv) Poly (allyl carbonate) compound of a mixture of diethylene glycol and trimethylolpropane and a mixture thereof with an oligomer
　This poly (allyl carbonate) compound has a tris (hydroxyethyl) isocyanurate replaced with trimethylolpropane. It is the same as the poly (allyl carbonate) of (iii) above.
[0032]
(v) A mixture of a poly (allyl carbonate) compound of diethylene glycol and pentaerythritol and a mixture thereof, the poly (allyl carbonate) compound
　described above, except that tris (hydroxyethyl) isocyanurate was replaced with pentaerythritol. It is the same as the poly (allyl carbonate) compound of (iii).
[0033]
(vi) Poly (allyl carbonate) compound of a mixture of diethylene glycol, neopentyl glycol and pentaerythritol and a mixture of an oligomer thereof In
　this poly (allyl carbonate) compound, diethylene glycol was replaced with two diols, diethylene glycol and neopentyl glycol. Except for this, it is the same as the poly (allyl carbonate) compound of (v) above.
[0034]
(vii) A poly (allyl carbonate) containing a mixture of a poly (allyl carbonate) compound of a mixture of diethylene glycol, neopentyl glycol and pentaerythritol and an oligomer thereof, and a mixture of
a bis (allyl carbonate) compound of diethylene glycol and an oligomer thereof. mixture
[0035]
　Hereinafter, "allyl carbonate compound (A) or a mixture of allyl carbonate compound (A) and its oligomer" is collectively referred to as "allyl carbonate compound (A)".
[0036]
[(B) (Meta) Acrylate Compound]
　The (meth) acrylate compound (B) in the present embodiment can be represented by the following formula.
[0037]
[Chemical 12]

[0038]
　R 2 represents a di to tetravalent organic group having 1 to 30 carbon atoms which may contain a hetero atom or an aromatic group. R 3 represents a hydrogen atom or a methyl group. n represents an integer of 2 to 4.
　Moreover, as the (meth) acrylate compound (B), the compound represented by the general formula (2-1) and the general formula (2-2) can be mentioned.
[0039]
[Chemical 13]

[0040]
　p represents a numerical value from 1 to 100, and R 3 represents a hydrogen atom or a methyl group, which do not have to be the same. For p, a numerical value of 1 to 50 is preferable, a numerical value of 1 to 20 is more preferable, a numerical value of 2 to 10 is further preferable, and a numerical value of 2 to 4 is particularly preferable.
[0041]
　The (meth) acrylate compound represented by the general formula (2-1) is ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, ethylene glycol diacrylate, diethylene glycol diacrylate, or triethylene. Glycol diacrylate, tetraethylene glycol diacrylate, propylene glycol dimethacrylate, dipropylene glycol dimethacrylate, tripropylene glycol dimethacrylate, tetrapropylene glycol dimethacrylate, propylene glycol diacrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, At least one selected from tetrapropylene glycol diacrylate can be mentioned.
[0042]
[Chemical 14]

[0043]
　Each of q indicates a numerical value of 1 or more, and the sum of the two qs indicates a numerical value of 2 to 100. R 3 represents a hydrogen atom or a methyl group and does not have to be the same. X represents a substituted or unsubstituted divalent aromatic group and a divalent aliphatic group which may contain a substituted or unsubstituted aromatic group having 1 to 20 carbon atoms.
[0044]
　Examples of the (meth) acrylate compound represented by the general formula (2-2) include bisphenol A dimethacrylate, methylene-bis- (4,1-phenylene) -bis- (2-methacrylate), bisphenol A diacrylate, and methylene. -Bis- (4,1-phenylene) -bis- (2-acrylate), 2,2-bis- (4-methacryloyloxyphenyl) propane, 2,2-bis- (4-acryloyloxyphenyl) propane, 2 -(4-methacryloyloxyphenyl) -2- (4-methacryloyloxyethoxyphenyl) propane, 2- (4-acryloyloxyphenyl) -2- (4-acryloyloxyethoxyphenyl) propane, 2,2-bis- ( 4-methacryloyloxyethoxyphenyl) propane, 2,2-bis- (4-acryloyloxyethoxyphenyl) propane, 2- (4-methacryloyloxyethoxyphenyl) -2- (4- (methacryloyloxyethoxy) ethoxyphenyl) propane , 2- (4-Acryloyloxyethoxyphenyl) -2- (4- (Acryloyloxyethoxy) ethoxyphenyl) propane, 2,2-bis- (4- (methacryloyloxyethoxy) ethoxyphenyl) propane, 2,2- At least one selected from bis- (4- (acryloyloxyethoxy) ethoxyphenyl) propane can be mentioned.
[0045]
　Examples of the (meth) acrylate compound other than the above include butanediol dimethacrylate, hexamethylene dimethacrylate, 2,2-bis (4-methacryloyloxyethoxy-3,5-dibromophenyl) propane, and 2,2-bis- (4). -Methacryloxypentaethoxyphenyl) propane, pentaerythritol triacrylate, pentaerythritol tetraacrylate, trimethylolpropane triacrylate, dipentaerythritol hexaacrylate, bispentaerythritol hexaacrylate, bisphenol A-diglycidyl ether diacrylate, bisphenol A- At least one selected from the group consisting of diglycidyl ether dimethacrylate-based, tetrabromobisphenol A-diglycidyl ether diacrylicate-based, and tetrabromobisphenol A-diglycidyl ether dimethacrylate-based can be mentioned.
[0046]
　Among these exemplified compounds, the (meth) acrylate compound (B) is diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, dipropylene glycol dimethacrylate, tripropylene glycol dimethacrylate, and dimethacrylate. At least one selected from propylene glycol diacrylate and tripropylene glycol diacrylate is preferable, and at least one selected from
　diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, diethylene glycol diacrylate, and triethylene glycol diacrylate is more preferable. Preferably,
at least one selected from diethylene glycol dimethacrylate and triethylene glycol dimethacrylate is particularly preferred.
[0047]
　In the total 100% by weight of the compound (A) and the compound (B), the allyl carbonate compound (A) is more than 0% by weight and 30% by weight or less, preferably 5% by weight or more and 30% by weight or less, and more preferably 5% by weight. % Or more and 28% by weight or less, particularly preferably 5% by weight or more and 25% by weight or less, and the (meth) acrylate compound (B) is 70% by weight or more and less than 100% by weight, preferably 70% by weight or more and 95% by weight or less. More preferably, it can contain 72% by weight or more and 95% by weight or less, and particularly preferably 75% by weight or more and 95% by weight or less.
　When the allyl carbonate compound (A) is contained, the mechanical strength of the lens is improved. Further, when it is 30% by weight or less, the transparency is excellent. When the (meth) acrylate compound (B) is contained in an amount of 70% by weight or more, the weight of the lens can be reduced, and the transparency and weather resistance are excellent. That is, by including the compound (A) and the compound (B) in the above range, the obtained resin molded product can exhibit sufficient mechanical strength, white turbidity is suppressed, and the transparency is excellent. Further, it is excellent in moldability and the yield of the plastic lens is improved.
[0048]
[(C) Compound]
　The compound (C) in the present embodiment contains at least one selected from the compounds represented by the general formulas (3) to (6) and dyes. Hereinafter, the compounds represented by the general formulas (3) to (6) will be described as compounds (3) to (6), respectively.
[0049]
(Compound (3))
　Compound (3) is represented by the general formula (3).
[0050]
[Chemical 15]

[0051]
　In the general formula (3), R 1 and R 2 represent alkyl groups or halogen atoms of C1 to C8, and may be the same or different. More existing R 1 s or more existing R, 2 to each other may be the same or different. m represents an integer of 0 to 3, n represents an integer of 0 to 3, p represents an integer of 0 to 1, and R 3 represents a functional group of C2 to C15 containing an ester bond.
[0052]
　Examples of the compound (3) include 2- (2-hydroxy-5-t-octylphenyl) benzotriazole, 2- (2-hydroxy-5-t-butylphenyl) benzotriazole, and 2- (2-hydroxy-5-). Methylphenyl) benzotriazole, 2- (5-t-octyl-3- (phenylpropan-2-yl) -2-hydroxyphenyl) benzotriazole, 2- (5-t-butyl-3- (phenylpropane-2) -Il) -2-hydroxyphenyl) benzotriazole, 2- (5-methyl-3- (phenylpropan-2-yl) -2-hydroxyphenyl) benzotriazole, 2- (5-octylpropionate-2-) Hydroxyphenyl) benzotriazole, 2- (5-t-octyl-2-hydroxyphenyl) benzotriazole, 2- (3,5-di-t-butyl-2-hydroxyphenyl) benzotriazole, 2- (3,5) -Di-t-pentyl-2-hydroxyphenyl) benzotriazole, 2- (3,5-bis- (phenylpropan-2-yl) -2-hydroxyphenyl) benzotriazole, 2- (3,5-di- t-Butyl-2-hydroxyphenyl) -5-chlorobenzotriazole, 2- (3-t-butyl-2-hydroxy-5-methylphenyl) -5-chlorobenzotriazole, 2- (4-octyloxy-2) -Hydroxyphenyl) benzotriazole, 2- (5-methyl-3-n-dodecyl-2-hydroxyphenyl) benzotriazole, 2- (5-methyl-2-hydroxyphenyl) benzotriazole, 2- (5-t- It is preferably at least one selected from the group consisting of butyl-2-hydroxyphenyl) benzotriazole.
[0053]
　さらに好ましくは、２－（２－ヒドロキシ－５－ｔ－オクチルフェニル)ベンゾトリアゾール、２－（２－ヒドロキシ－５－ｔ－ブチルフェニル)ベンゾトリアゾール、２－（２－ヒドロキシ－５－メチルフェニル)ベンゾトリアゾール、２－（５－t－オクチル－３－（フェニルプロパン－２－イル）－２－ヒドロキシフェニル）ベンゾトリアゾール、２－（５－t－ブチル－３－（フェニルプロパン－２－イル）－２－ヒドロキシフェニル）ベンゾトリアゾール、２－（５－メチル－３－（フェニルプロパン－２－イル）－２－ヒドロキシフェニル）ベンゾトリアゾール、２－（５－オクチルプロピオネート－２－ヒドロキシフェニル）ベンゾトリアゾール、２－（３，５－ジ－t－ペンチル－２－ヒドロキシフェニル）ベンゾトリアゾール、２－（３，５－ビス－（フェニルプロパン－２－イル）－２－ヒドロキシフェニル）ベンゾトリアゾール、２－（３，５－ジ－t－ブチル－２－ヒドロキシフェニル）－５－クロロベンゾトリアゾール、２－（３－ｔ－ブチル－２－ヒドロキシ－５－メチルフェニル）－５－クロロベンゾトリアゾール、２－（４－オクチルオキシ－２－ヒドロキシフェニル）ベンゾトリアゾール、より好ましくは２－（２－ヒドロキシ－５－ｔ－オクチルフェニル)ベンゾトリアゾール、２－（２－ヒドロキシ－５－ｔ－ブチルフェニル)ベンゾトリアゾール、２－（２－ヒドロキシ－５－メチルフェニル)ベンゾトリアゾール、２－（５－t－オクチル－３－（フェニルプロパン－２－イル）－２－ヒドロキシフェニル）ベンゾトリアゾール、２－（５－t－ブチル－３－（フェニルプロパン－２－イル）－２－ヒドロキシフェニル）ベンゾトリアゾール、２－（５－メチル－３－（フェニルプロパン－２－イル）－２－ヒドロキシフェニル）ベンゾトリアゾール、特に好ましくは２－（２－ヒドロキシ－５－ｔ－オクチルフェニル)ベンゾトリアゾール、２－（２－ヒドロキシ－５－ｔ－ブチルフェニル)ベンゾトリアゾール、２－（２－ヒドロキシ－５－メチルフェニル)ベンゾトリアゾールからなる群から少なくとも１種を選択することである。
[0054]
　In the present embodiment, the amount of the compound (3) used is 0.0005 parts by weight or more and 5 parts by weight or less, preferably 0.005 parts by weight or more, based on 100 parts by weight of the total of the compounds (A) and (B). It can be 3 parts by weight or less, more preferably 0.01 parts by weight or more and 2 parts by weight or less.
[0055]
(Compound (4))
　Compound (4) is represented by the general formula (4).
[0056]
[Chemical 16]

[0057]
　In the general formula (4), Z 3 represents an aromatic organic group of C6 to C20 which may be substituted, and an alicyclic group group of C5 to C20 which may be substituted. Z 4 and Z 5 may be the same or different and represent C1-C6 alkyl groups and C1-C6 alkoxy groups.
[0058]
　Examples of the aromatic organic group of C6 to C20 include a phenyl group, a benzyl group, a benzoyl group, a p-methoxybenzyl group and the like. Examples of the alicyclic group of C5 to C20 include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentanyl group, a cyclodecanyl group and the like.
　Examples of the substituent of the substituted aromatic organic group of C6 to C20 or the substituent of the substituted alicyclic group of C5 to C20 include C1 to C6 alkyl group and C1 to C6 alkoxy group.
[0059]
　Examples of the compound (4) include dimethyl (p-methoxybenzylidene) malonate and diethyl (p-methoxybenzylidene) malonate. Two or more kinds of these ultraviolet absorbers can be used in combination.
[0060]
　In the present embodiment, the amount of the compound (4) used is 0.0005 parts by weight or more and 5 parts by weight or less, preferably 0.005 parts by weight or more, based on 100 parts by weight of the total of the compounds (A) and (B). It can be 3 parts by weight or less, more preferably 0.01 parts by weight or more and 2 parts by weight or less.
[0061]
(Compound (5))
　Compound (5) is represented by the general formula (5).
[0062]
[Chemical 17]

[0063]
　In the general formula (5), A 1 to A 8 and X 1 to X 4 are independently hydrogen atom, halogen atom, nitro group, cyano group, hydroxy group, amino group, carboxyl group, sulfonic acid group and carbon number. 1 to 20 linear, branched or cyclic alkyl groups, 1 to 20 carbons alkoxy groups, 6 to 20 carbon aryloxy groups, 1 to 20 carbon monoalkylamino groups, 2 to 20 carbons Dialkylamino group, dialkylamino group with 7 to 20 carbon atoms, aralkyl group with 7 to 20 carbon atoms, aryl group with 6 to 20 carbon atoms, heteroaryl group, alkylthio group with 6 to 20 carbon atoms, 6 to 20 carbon atoms Represents the arylthio group of. A 1 to A 8 may form a ring excluding the aromatic ring via a linking group. n represents 0 or 1. Q 1 ~ Q 4 each independently represent a carbon atom, a nitrogen atom. M represents two hydrogen atoms, a divalent metal atom, a divalent monosubstituted metal atom, a tetravalent disubstituted metal atom, or an oxymetal atom.
[0064]
　As the compound represented by the general formula (5), the compound represented by the following general formula (5-1) is preferable.
[0065]
[Chemical 18]

[0066]
　In the general formula (5-1), A 1 to A 8 and M are synonymous with the general formula (5).
[0067]
　Regarding the tetraazaporphyrin compound represented by the general formula (5) or the general formula (5-1), in the general formula (5) or the general formula (5-1), M is more preferably divalent copper. .. Specific examples include a tetra-t-butyl-tetraazaporphyrin-copper complex represented by the following formula (5a), which corresponds to the product number name of PD-311S (manufactured by Mitsui Chemicals, Inc.). ..
[0068]
[Chemical 19]

[0069]
　In the present embodiment, the amount of the compound (5) used is 0.01 ppm or more and 50 ppm or less, preferably 0.1 ppm or more and 30 ppm or less, more preferably 0, based on the weight of the compounds (A) and (B). It can be 5.5 ppm or more and 20 ppm or less.
[0070]
(Compound (6))
　Compound (6) is represented by the general formula (6).
[0071]
[Chemical 20]

[0072]
　In the general formula (6), 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. m is an integer of 1 to 3, n is an integer of 1 to 3, and the sum of m and n is an integer of 3 to 6.
[0073]
　Examples of the linear or branched alkyl group having 1 to 20 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group and hexyl group. A heptyl group, an octyl group, a 2-ethylhexyl group, a nonyl group, a decyl group and the like are preferable, and a hydrogen atom, a methyl group, an ethyl group and a propyl group are particularly preferable.
　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 an integer of 3 to 6 is preferable.
[0074]
　, 4-tri-n-propoxybenzophenone, 2,2', 4-triisopropoxybenzophenone, 2,2', 5-trimethoxybenzophenone, 2,2', 5-triethoxybenzophenone, 2,2', 5 -Tri-n-propoxybenzophenone, 2,2', 5-triisopropoxybenzophenone, 2,4,4'-trimethoxybenzophenone, 2,4,4'-triethoxybenzophenone, 2,4,4'-tri -N-propoxybenzophenone, 2,4,4'-triisopropoxybenzophenone, 3,4', 5-trimethoxybenzophenone, 3,4', 5-triethoxybenzophenone, 3,4', 5-tri-n -Propoxybenzophenone, 3,4', 5-triisopropoxybenzophenone, 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'-tetramethoxybenzophenone, 2,2', 4,4'-tetraethoxybenzophenone, 3, 3', 4,4'-Tetramethoxybenzophenone, 3,3', 4,4'-Tetraethoxybenzophenone, 2,3,3', 4'-Tetramethoxybenzophenone, 2,3,3', 4'- Tetraethoxybenzophenone, etc. can be mentioned. Of these, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, and 2,2', 4,4'-tetrahydroxybenzophenone are particularly preferable. , 4-triisopropoxybenzophenone, 2,2', 5-trimethoxybenzophenone, 2,2', 5-triethoxybenzophenone, 2,2', 5-tri-n-propoxybenzophenone, 2,2', 5 -Triisopropoxybenzophenone, 2,4,4'-trimethoxybenzophenone, 2,4,4'-triethoxybenzophenone, 2,4,4'-tri-n-propoxybenzophenone, 2,4,4'-tri Isopropoxybenzophenone, 3,4', 5-trimethoxybenzophenone, 3,4', 5-triethoxybenzophenone, 3,4', 5-tri-n-propoxybenzophenone, 3,4', 5-triisopropoxy Benzophenone, 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'-tetramethoxybenzophenone, 2,2', 4,4'-tetraethoxybenzophenone, 3,3', 4,4'-tetramethoxybenzophenone, 3, Examples thereof include 3', 4,4'-tetraethoxybenzophenone, 2,3,3', 4'-tetramethoxybenzophenone, 2,3,3', 4'-tetraethoxybenzophenone, and the like. Of these, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, and 2,2', 4,4'-tetrahydroxybenzophenone are particularly preferable. , 4-triisopropoxybenzophenone, 2,2', 5-trimethoxybenzophenone, 2,2', 5-triethoxybenzophenone, 2,2', 5-tri-n-propoxybenzophenone, 2,2', 5 -Triisopropoxybenzophenone, 2,4,4'-trimethoxybenzophenone, 2,4,4'-triethoxybenzophenone, 2,4,4'-tri-n-propoxybenzophenone, 2,4,4'-tri Isopropoxybenzophenone, 3,4', 5-trimethoxybenzophenone, 3,4', 5-triethoxybenzophenone, 3,4', 5-tri-n-propoxybenzophenone, 3,4', 5-triisopropoxy Benzophenone, 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'-tetramethoxybenzophenone, 2,2', 4,4'-tetraethoxybenzophenone, 3,3', 4,4'-tetramethoxybenzophenone, 3, Examples thereof include 3', 4,4'-tetraethoxybenzophenone, 2,3,3', 4'-tetramethoxybenzophenone, 2,3,3', 4'-tetraethoxybenzophenone, and the like. Of these, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, and 2,2', 4,4'-tetrahydroxybenzophenone are particularly preferable. , 5-triethoxybenzophenone, 2,2', 5-tri-n-propoxybenzophenone, 2,2', 5-triisopropoxybenzophenone, 2,4,4'-trimethoxybenzophenone, 2,4,4' -Triethoxybenzophenone, 2,4,4'-tri-n-propoxybenzophenone, 2,4,4'-triisopropoxybenzophenone, 3,4', 5-trimethoxybenzophenone, 3,4', 5-tri Ethoxybenzophenone, 3,4', 5-tri-n-propoxybenzophenone, 3,4', 5-triisopropoxybenzophenone, 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'-tetramethoxybenzophenone, 2,2 ', 4,4'-Tetraethoxybenzophenone, 3,3', 4,4'-Tetramethoxybenzophenone, 3,3', 4,4'-Tetraethoxybenzophenone, 2,3,3', 4'-Tetra Examples thereof include methoxybenzophenone, 2,3,3', 4'-tetraethoxybenzophenone, and the like. Of these, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, and 2,2', 4,4'-tetrahydroxybenzophenone are particularly preferable. , 5-triethoxybenzophenone, 2,2', 5-tri-n-propoxybenzophenone, 2,2', 5-triisopropoxybenzophenone, 2,4,4'-trimethoxybenzophenone, 2,4,4' -Triethoxybenzophenone, 2,4,4'-tri-n-propoxybenzophenone, 2,4,4'-triisopropoxybenzophenone, 3,4', 5-trimethoxybenzophenone, 3,4', 5-tri Ethoxybenzophenone, 3,4', 5-tri-n-propoxybenzophenone, 3,4', 5-triisopropoxybenzophenone, 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'-tetramethoxybenzophenone, 2,2 ', 4,4'-Tetraethoxybenzophenone, 3,3', 4,4'-Tetramethoxybenzophenone, 3,3', 4,4'-Tetraethoxybenzophenone, 2,3,3', 4'-Tetra Examples thereof include methoxybenzophenone, 2,3,3', 4'-tetraethoxybenzophenone, and the like. Of these, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, and 2,2', 4,4'-tetrahydroxybenzophenone are particularly preferable. -Triethoxybenzophenone, 2,4,4'-tri-n-propoxybenzophenone, 2,4,4'-triisopropoxybenzophenone, 3,4', 5-trimethoxybenzophenone, 3,4', 5-tri Ethoxybenzophenone, 3,4', 5-tri-n-propoxybenzophenone, 3,4', 5-triisopropoxybenzophenone, 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'-tetramethoxybenzophenone, 2,2 ', 4,4'-Tetraethoxybenzophenone, 3,3', 4,4'-Tetramethoxybenzophenone, 3,3', 4,4'-Tetraethoxybenzophenone, 2,3,3', 4'-Tetra Examples thereof include methoxybenzophenone, 2,3,3', 4'-tetraethoxybenzophenone, and the like. Of these, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, and 2,2', 4,4'-tetrahydroxybenzophenone are particularly preferable. -Triethoxybenzophenone, 2,4,4'-tri-n-propoxybenzophenone, 2,4,4'-triisopropoxybenzophenone, 3,4', 5-trimethoxybenzophenone, 3,4', 5-tri Ethoxybenzophenone, 3,4', 5-tri-n-propoxybenzophenone, 3,4', 5-triisopropoxybenzophenone, 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'-tetramethoxybenzophenone, 2,2 ', 4,4'-Tetraethoxybenzophenone, 3,3', 4,4'-Tetramethoxybenzophenone, 3,3', 4,4'-Tetraethoxybenzophenone, 2,3,3', 4'-Tetra Examples thereof include methoxybenzophenone, 2,3,3', 4'-tetraethoxybenzophenone, and the like. Of these, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, and 2,2', 4,4'-tetrahydroxybenzophenone are particularly preferable. -Hydroxybenzophenone, 2,4-di-n-propoxy-4'-hydroxybenzophenone, 2,4-diisopropoxy-4'-hydroxybenzophenone, 2,2', 4,4'-tetramethoxybenzophenone, 2, 2', 4,4'-Tetraethoxybenzophenone, 3,3', 4,4'-Tetramethoxybenzophenone, 3,3', 4,4'-Tetraethoxybenzophenone, 2,3,3', 4'- Examples thereof include tetramethoxybenzophenone, 2,3,3', 4'-tetraethoxybenzophenone, and the like. Of these, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, and 2,2', 4,4'-tetrahydroxybenzophenone are particularly preferable. -Hydroxybenzophenone, 2,4-di-n-propoxy-4'-hydroxybenzophenone, 2,4-diisopropoxy-4'-hydroxybenzophenone, 2,2', 4,4'-tetramethoxybenzophenone, 2, 2', 4,4'-Tetraethoxybenzophenone, 3,3', 4,4'-Tetramethoxybenzophenone, 3,3', 4,4'-Tetraethoxybenzophenone, 2,3,3', 4'- Examples thereof include tetramethoxybenzophenone, 2,3,3', 4'-tetraethoxybenzophenone, and the like. Of these, 2,2'-dihydroxy-4-methoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, and 2,2', 4,4'-tetrahydroxybenzophenone are particularly preferable.
[0075]
　In the present embodiment, the amount of compound (6) used is 0.0005 parts by weight or more and 5 parts by weight or less, preferably 0.005 parts by weight or more, based on 100 parts by weight of the compounds (A) and (B) in total. It can be 3 parts by weight or less, more preferably 0.01 parts by weight or more and 2 parts by weight or less.
[0076]

　Examples of the (dye) dye include anthraquinone dyes, perinone dyes, monoazo dyes, diazo dyes, phthalocyanine dyes and the like, and one type or a combination of two or more types can be used.
[0077]
　Examples of anthracene dyes include Solvent Blue 36 (1,4-bis (isopropylamino) anthracene-9,10-dione) and 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 (mesitylamino) 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 -Naft [1,2,3-de] quinoline-2,7-dione), Solvent Red 168 (1- (cyclohexylamino) anthracene-9,10-dione), Solvent Red 207 (1,5-bis (cyclohexyl)) Amino) anthracene-9,10-dione), Disperse Red 22 (1- (phenylamino) anthracene-9,10-dione), Disperse Red 60 (1-amino-4-hydroxy-2-phenoxyanthracene-9,10) -Dione), Solvent Violet 59 (1,4-diamino-2,3-diphenylanthracene-9,10-dione), Solvent Green 28 (1,4-bis ((4-butylphenyl) amino) -5,8 -Dihydroxyanthracene-9,10-dione), Last Blue 8514 (1-hydroxy-4-[(4-methylphenyl) amino] -9,10-Anthracene Zion) and the like.
[0078]
　Examples of perinone dyes include Solvent Orange 60 (12H-isoindro [2,1-a] perimidin-12-on), Solvent Orange 78, Solvent Orange 90, and Solvent Red 135 (8,9,10,11-tetrachloro-). 12H-isoindro [2,1-a] perimidine-12-on), Solvent Red 162, Solvent Red 179 (14H-benzo [4,5] isoquinolino [2,1-a] perimidine-14-on), etc. be able to.
[0079]
　Examples of the monoazo dye include Solvent Red 195, Fast Orange R, Oil Red, Oil Yellow and the like.
　As a diazo dye, Chicago Sky Blue 6B (Sodium 6,6'-((1E, 1'E)-(3,3'-dimethoxy- [1,1'-biphenyl] -4,4'-diyl)) Bis (diazen-2,1-diyl)) Bis (4-amino-5-hydroxynaphthalene-1,3-disulfonate)), Evans blue (Sodium 6,6'-((1E, 1'E)-( 3,3'-dimethyl- [1,1'-biphenyl] -4,4'-diyl) bis (diazen-2,1-diyl)) bis (4-amino-5-hydroxynaphthalene-1,3-diyl) Sulfonate)), Direct Blue 15 (Sodium 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 (Sodium 3,3'-((1E, 1'E)-(3,3) '-Dimethyl- [1,1'-biphenyl] -4,4'-diyl) bis (diazen-2,1-diyl)) bis (5-amino-4-hydroxynaphthalene-2,7-disulfonate)) , Benzopurpurin 4B (Sodium 3,3'-((1E, 1'E)-(3,3'-dimethyl- [1,1'-biphenyl] -4,4'-diyl) bis (diazen-2) , 1-diyl)) Bis (4-aminonaphthalene-1-sulfonate)), Congo Red (Sodium 3,3'-((1E, 1'E)-[1,1'-biphenyl] -4,4' -Jiylvis (Ziazen-2,
　Examples of the phthalocyanine dye include C.I. I. Direct Blue 86, C.I. I. Direct blue 199 and the like can be mentioned.
[0080]
　In the present embodiment, from the viewpoint of obtaining an optical material having an excellent effect of blocking blue light of about 420 nm, yellowness (YI), and transparency, it is preferable that Solvent Blue 94, Solvent Blue 97, Solvent Blue 104, Solvent. Violet 59, Solvent Red 195, Disperse Red 60, Solvent Green 28, Solvent Orange 60, and Last Blue 8514, which may be used alone or in combination of two or more.
[0081]
　In the present embodiment, the amount of the dye used is 0.01 ppm or more and 50 ppm or less, preferably 0.1 ppm or more and 30 ppm or less, more preferably 0.5 ppm or more, based on the weight of the compounds (A) and (B). It can be 20 ppm or less.
[0082]
　In the present embodiment, the compound (C), which is at least one selected from the compounds represented by the general formulas (3) to (6) and the dye, is a case where a composition containing a conventional radical polymerization initiator is polymerized. In some cases, the structure and chemical properties of the product may change and the desired effect may not be exhibited. When these compounds cannot exert the desired effect, the compounds represented by the general formulas (3) to (4) and (6) and the dyes have a broken skeleton, and the compounds represented by the general formula (5) are broken. It is assumed that the central metal comes off or the skeleton breaks.
[0083]
　However, by using the radical polymerization initiators (D1) and (D2), the effect of the compound (C) can be stably exhibited, and a desired effect can be imparted to the plastic lens. For example, when the specific wavelength absorbing dye which is the compound (C) exerts a desired effect, the transmittance of the lens at the specific wavelength is 60% or less. When the ultraviolet absorber which is the compound (C) exerts a desired effect, b * is 20 or less. When the blue dye which is the compound (C) exerts a desired effect, b * is less than 0.
[0084]
[(D) Radical Polymerization Initiator] In the
　present embodiment, the radical polymerization initiator (D) includes at least the following radical polymerization initiator (D1) and the following radical polymerization initiator (D2).
　The radical polymerization initiator (D1) has a radical residual rate of 20% or more and less than 100% after the lapse of 5 hours at 50 ° C., and a radical residual rate of 0% or more and less than 30% after the lapse of 5 hours at 70 ° C. The radical polymerization initiator (D2) has a radical residual rate of 30% or more and less than 98% after the lapse of 5 hours at 70 ° C.
[0085]
　The radical residual rate of the radical polymerization initiator can be calculated as follows.
　By the following equation, thermal decomposition rate k of the radical polymerization initiator at a given temperature T d is calculated.
　k d = Aexp (−ΔE / RT)
　　　A: Pre-exponential factor
　　　ΔE: Activation energy
　　　R: Gas constant (8.314 J / mol · K)
　　　T: Absolute temperature (T) A predetermined temperature is determined by the
　above thermal decomposition rate k d. The radical residual rate of the radical polymerization initiator after the t-time reaction at T can be calculated.
Radical remaining ratio (%) = exp (-k d t) × 100
　　t: time (hr)
[0086]
　The radical polymerization initiator (D1) has a radical residual rate of 20% or more and less than 100%, preferably 20% or more and 90% or less, more preferably 40% or more and 85% or less, and 70 after the lapse of 5 hours at 50 ° C. The radical residual rate after the lapse of 5 hours at ° C. is 0% or more and less than 30%, preferably 0% or more and 20% or less, and more preferably 0% or more and 10% or less.
　The radical polymerization initiator (D2) has a radical residual rate of 30% or more and less than 98%, preferably 40% or more and less than 98%, and more preferably 50% or more and less than 98% after the lapse of 5 hours at 70 ° C.
　The above ranges can be combined as appropriate.
[0087]
　Examples of the radical polymerization initiator (D1) include a peroxyester-based radical polymerization initiator, a peroxydicarbonate-based radical polymerization initiator, an azo-based radical polymerization initiator, and the like, and at least one of them can be used. In the following, the numerical values ​​in parentheses indicate "radical residual rate after lapse of 50 ° C. for 5 hours" and "radical residual rate after lapse of 70 ° C. for 5 hours", respectively.
[0088]
　Examples of the peroxyester radical polymerization initiator include t-amyl-peroxyneodecanoate (54.5%, 0.0%) and t-butyl-peroxyneodecanoate (57.6%). , 0.2%), t-hexyl peroxypivalate (80.2%, 5.5%), t-hexyl peroxyneodecanoate, 1,1,3,3-tetramethylbutylperoxy Neodecanoate (27.9%, 0.0%), t-butylperoxypivalate (82.6%, 7.9%), and the like can be mentioned.
[0089]
　Examples of the peroxydicarbonate-based radical polymerization initiator include diisopropyl peroxydicarbonate (24.8%, 0%), di-n-propyl peroxydicarbonate (28.7%, 0%), and bis (28.7%, 0%). 4-t-Butylcyclohexyl) peroxydicarbonate (28.2%, 0%), di-2-ethylhexyl peroxydicarbonate (40.4%, 0%), di-sec-butylperoxydicarbonate (40.4%, 0%) 29.4%, 0%) and the like.
　Examples of the (azo) -based radical polymerization initiator include 2-2'-azobis (2,4-dimethylvaleronitrile) (73.8%, 2.0%).
[0090]
　Examples of the radical polymerization initiator (D2) include a peroxyester-based radical polymerization initiator, a peroxyketal-based radical polymerization initiator, a peroxydicarbonate-based radical polymerization initiator, an azo-based radical polymerization initiator, and the like. , At least one type can be used. In the following, the numerical values ​​in parentheses indicate "radical residual rate after the lapse of 5 hours at 70 ° C."
[0091]
　Examples of the peroxyester radical polymerization initiator include 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate (53.8%) and t-butylperoxy2-ethylhexanoate. Ate (76.8%), t-amylperoxy-2-ethylhexanoate: TRIGONOX121 (78.5%) manufactured by Kayaku Akzo Corporation, t-amylperoxy-2-ethylhexanoate: Alchema Yoshitomi LUPEROX 575 (84.4%), t-hexylperoxy2-ethylhexanoate (70.9%) and the like.
[0092]
　Examples of the peroxyketal radical polymerization initiator include 1,1-di (t-hexyl peroxy) cyclohexane (96.2%) and 1,1-di (t-butylperoxy) cyclohexane (97.5%). %), Etc. can be mentioned.
　Examples of the azo radical polymerization initiator include 2-2'-azobis (isobutyronitrile) (50.2%) and 2-2'-azobis (2-methylbutyronitrile) (60.0%). , 1,1'-azobis (cyclohexane-1-carbonitrile) (97.7%) and the like.
[0093]
　The amount of the radical polymerization initiator (D) added varies depending on the polymerization conditions, the type of the initiator, and the composition of the above-mentioned monomer, and is not unconditionally limited, but is 0.1 with respect to 100 parts by weight of the polymerizable composition. The range is 6 parts by weight or more, preferably 0.2 parts by weight or more and 4 parts by weight or less. When it is in the above range, the curability is excellent, and the occurrence of distortion and the like is suppressed in the molded product.
　In the combination of the radical polymerization initiator (D1) and (D2), from the viewpoint of the effect of the present invention, 0.1 part by weight or more of the polymerization initiator (D1) is added to 100 parts by weight of the polymerizable composition. It contains 0.0 parts by weight or less, preferably 0.2 parts by weight or more and 3.0 parts by weight or less, and contains the polymerization initiator (D2) in excess of 0 parts by weight and 1.0 parts by weight or less, preferably 0.001 parts by weight or more. It can contain 0.5 parts by weight or less. The above ranges can be combined as appropriate.
[0094]
　When the monomer composition is cured using these radical polymerization initiators (D1) and (D2), decomposition of the compound (C) can be suppressed during curing, and the compound (C) as an additive can be used. It is possible to stably exert the desired effect.
[0095]
　In the present embodiment, from the viewpoint of the effect of the present invention, the radical polymerization initiator (D) preferably contains a combination of (D1) and (D2).
　In the present embodiment, by including the radical polymerization initiator (D1) and the radical polymerization initiator (D2), (D1) generates radicals on the lower temperature side, and (D2) generates radicals on the higher temperature side. Since it is easy to carry out, radicals remain in the system within a certain concentration range during polymerization, so that the polymerization proceeds under mild conditions, the lens cracks and the polymerization peels off, the decomposition of the additive compound (C), etc. Is particularly suppressed and the moldability is improved, so that the yield of the product is greatly improved. Further, the decomposition of the compound (C) as an additive is suppressed, and the desired additive effect can be stably exhibited.
[0096]
　In this embodiment, by using an allyl carbonate compound (A), a (meth) acrylate compound (B), a compound (C), and a combination of a radical polymerization initiator (D1) and (D2), It is possible to provide a plastic spectacle lens having excellent surface hardness without impairing the transparency, and cracking and peeling of the lens during polymerization are particularly suppressed, and the moldability is excellent, so that the yield of the product is high. It will be greatly improved. Further, by combining a specific radical polymerization initiator, the obtained plastic lens can stably exert the desired effect of the compound (C) as an additive.
[0097]
　The polymerization initiator (D) is preferably a combination of the following compound which is the radical polymerization initiator (D1) and the following compound which is the radical polymerization initiator (D2).
(1) Combination of
t- butylperoxyneodecanoate and 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate (2) t-butylperoxyneodecanoate and t -Combination with Amylperoxy-2-ethylhexanoate In
　order to cure the polymerizable composition for optical materials of the present embodiment, a radical polymerization initiator (D) is added to the monomer composition, and then It can be obtained by curing by a heat curing method or an active energy ray curing method.
[0098]
[Other components] In the
　present embodiment, in addition to the above components (A) to (D), a resin modifier, an internal mold release agent, and the like may be further contained.
　As the resin modifier, a radically polymerizable monomer other than the (meth) acrylate compound (B) may be added as long as the effects of the present invention are not impaired.
[0099]
　Examples of the radically polymerizable monomer other than the (meth) acrylate compound (B) include styrene, alphamethylstyrene, alphamethylstyrenedimer, benzylmethacrylate, chlorostyrene, bromostyrene, methoxystyrene, monobenzylfumarate, and dibenzylfuma. One or more compounds selected from the group composed of rate, dibutyl fumarate, monopentyl fumarate, dipentyl fumarate can be used.
[0100]

　The polymerizable composition for optical materials of the present embodiment includes an allyl carbonate compound (A), a (meth) acrylate compound (B), a compound (C), and if necessary. The radical polymerization initiator (D) is mixed and obtained.
　The mixing method is batch mixing, or compound (A) and compound (B) (masterbatch) containing compound (C) and, if necessary, a radical polymerization initiator (D) at a high concentration are once prepared and then mixed. A masterbatch can also be prepared by diluting and mixing compound (A) and compound (B). When a masterbatch is used, the dilution ratio of the masterbatch varies depending on the compound (C), but is usually 2 times or more and 50 times or less, preferably 4 times or more and 20 times or less, and more preferably 5 times or more and 15 times or less. Since the compound (C) is uniformly dispersed in this range, it can be suitably adopted.
[0101]
　The temperature at which the compound (A), the compound (B) and the compound (C), and the radical polymerization initiator (D) are mixed to prepare a polymerizable composition is usually 40 ° C. or lower, preferably 30 ° C. or lower. .. From the viewpoint of pot life of the polymerizable composition, it may be preferable to lower the temperature further. However, if the solubility of the catalyst or additive in the monomer is not good, it is possible to preheat the catalyst or additive to dissolve it in the monomer or resin modifier.
[0102]
　In the present embodiment, the method for producing the resin molded product is not particularly limited, but a preferred production method includes cast polymerization. First, the polymerizable composition is injected between the molding molds held by a gasket, tape or the like. At this time, depending on the physical properties required for the obtained plastic lens, it is often preferable to perform defoaming treatment under reduced pressure, filtration treatment such as pressurization and depressurization, and the like, if necessary.
[0103]
　The polymerization conditions are not limited because they differ greatly depending on the composition of the polymerizable composition, the type and amount of the catalyst used, the shape of the mold, etc., but are not limited, but are approximately 1 to 50 at a temperature of -50 to 150 ° C. It takes time. In some cases, it is preferable to keep the temperature in the temperature range of 10 to 150 ° C. or gradually raise the temperature to cure in 1 to 48 hours.
[0104]
　The resin molded product may be subjected to a treatment such as annealing, if necessary. The treatment temperature is usually between 50 and 150 ° C., but is preferably 90 to 140 ° C., more preferably 100 to 130 ° C.
[0105]
　In the present embodiment, when molding the resin, in addition to the above-mentioned "other components", a chain extender, a cross-linking agent, a radical scavenger, a light stabilizer, as in a known molding method depending on the purpose. Various additives such as UV stabilizers, antioxidants, brewing agents, oil-soluble dyes, fillers, adhesion improvers, antibacterial agents, and antistatic agents may be added.
[0106]

　The resin of the present embodiment can be obtained as a molded product having various shapes by changing the type of mold at the time of casting polymerization.
[0107]
　The molded product obtained from the polymerizable composition for optical materials of the present embodiment can be used for various optical materials such as plastic lenses because a material having excellent surface hardness can be obtained without impairing transparency. It is possible. In particular, it can be suitably used as a plastic spectacle lens or a plastic polarized lens.
[0108]
[Plastic spectacle lens]
　A plastic spectacle lens using a lens base material made of a molded product of the present embodiment may be used by applying a coating layer on one side or both sides, if necessary.
　The plastic spectacle lens of the present embodiment comprises a lens base material made of the above-mentioned polymerizable composition and a coating layer.
[0109]
　Specific examples of the coating layer include a primer layer, a hard coat layer, an antireflection layer, an antifogging coat layer, an antifouling layer, and a water repellent layer. Each of these coating layers can be used alone, or a plurality of coating layers can be used in multiple layers. When the coating layers are applied to both surfaces, the same coating layer may be applied to each surface, or different coating layers may be applied.
[0110]
　Each of these coating layers is an infrared absorber to protect the eyes from infrared rays, a light stabilizer or antioxidant to improve the weather resistance of the lens, a photochrome compound, and a dye or pigment to improve the fashionability of the lens. , Antistatic agents, and other known additives for enhancing the performance of the lens may be used in combination.
　Various leveling agents for the purpose of improving coatability may be used for the layer to be coated by coating.
[0111]
　The primer layer is usually formed between the hard coat layer described later and the lens. The primer layer is a coating layer for the purpose of improving the adhesion between the hard coat layer formed on the primer and the lens, and it is also possible to improve the impact resistance in some cases. Any material can be used for the primer layer as long as it has high adhesion to the obtained lens, but usually, a primer containing urethane resin, epoxy resin, polyester resin, melanin resin, and polyvinyl acetal as main components. Compositions and the like are used. The primer composition may use an appropriate solvent that does not affect the lens for the purpose of adjusting the viscosity of the composition. Of course, it may be used without a solvent.
[0112]
　The primer layer can be formed by either a coating method or a dry method. When the coating method is used, the primer layer is formed by applying the primer composition to the lens by a known coating method such as spin coating or dip coating and then solidifying the lens. When the dry method is used, it is formed by a known dry method such as a CVD method or a vacuum vapor deposition method. When forming the primer layer, the surface of the lens may be subjected to pretreatment such as alkali treatment, plasma treatment, and ultraviolet treatment, if necessary, for the purpose of improving adhesion.
　The hard coat layer is a coating layer for the purpose of imparting functions such as scratch resistance, abrasion resistance, moisture resistance, temperature water resistance, heat resistance, and weather resistance to the lens surface.
[0113]
　The hard coat layer is generally composed of a curable organic silicon compound and an element selected from the element group of Si, Al, Sn, Sb, Ta, Ce, La, Fe, Zn, W, Zr, In and Ti. A hard coat composition containing one or more fine oxide particles and / or one or more fine particles composed of a composite oxide of two or more elements selected from these element groups is used.
[0114]
　In addition to the above components, the hard coat composition includes at least amines, amino acids, metal acetylacetonate complexes, organic acid metal salts, perchloric acids, perchloric acid salts, acids, metal chlorides and polyfunctional epoxy compounds. It is preferable to include any of them. A suitable solvent that does not affect the lens may be used for the hard coat composition, or a solvent-free solvent may be used.
[0115]
　The hard coat layer is usually formed by applying a hard coat composition by a known coating method such as spin coating or dip coating and then curing the hard coating composition. Examples of the curing method include heat curing and a curing method by irradiation with energy rays such as ultraviolet rays and visible light. In order to suppress the occurrence of interference fringes, the refractive index of the hard coat layer is preferably in the range of ± 0.1 in the difference in refractive index from the lens.
[0116]
　The antireflection layer is usually formed on the hard coat layer as needed. The antireflection layer includes an inorganic type and an organic type. In the case of the inorganic type, an inorganic oxide such as SiO 2 or TiO 2 is used, and a vacuum deposition method, a sputtering method, an ion plating method, an ion beam assist method, or a CVD method is used. It is formed by a dry method such as. In the case of an organic system, it is formed by a wet process using a composition containing an organosilicon compound and silica-based fine particles having internal cavities.
[0117]
　The antireflection layer has a single layer and a plurality of layers, and when used as a single layer, it is preferable that the refractive index is at least 0.1 or more lower than the refractive index of the hard coat layer. In order to effectively exhibit the antireflection function, a multilayer antireflection film is preferable, and in that case, a low refractive index film and a high refractive index film are alternately laminated. In this case as well, the difference in refractive index between the low refractive index film and the high refractive index film is preferably 0.1 or more. Examples of the high-refractive index film include films of ZnO, TiO 2 , CeO 2 , Sb 2 O 5 , SnO 2 , ZrO 2 , Ta 2 O 5, and the like, and examples of the low-refractive index film include SiO 2 film. ..
[0118]
　An antifogging layer, an antifouling layer, and a water repellent layer may be formed on the antireflection layer, if necessary. The method for forming the antifogging layer, the antifouling layer, and the water repellent layer is not particularly limited as long as it does not adversely affect the antireflection function, and the treatment method, treatment material, and the like are not particularly limited. Methods, antifouling treatment methods, water repellent treatment methods, materials can be used. For example, in the anti-fog treatment method and the anti-fouling treatment method, a method of covering the surface with a surfactant, a method of adding a hydrophilic film to the surface to make it water-absorbent, and a method of covering the surface with fine irregularities to improve water absorption. , A method of making water absorbable by utilizing photocatalytic activity, a method of applying a super-water repellent treatment to prevent the adhesion of water droplets, and the like. Further, in the water repellent treatment method, a method of forming a water repellent treatment layer by vapor deposition or sputtering of a fluorine-containing silane compound or the like, or a method of dissolving a fluorine-containing silane compound in a solvent and then coating it to form a water repellent treatment layer. And so on.
[0119]
[Plastic Polarizing Lens]
　The plastic polarizing lens of the present embodiment comprises a polarizing film and a molded product obtained by curing a polymerizable composition for an optical material of the present embodiment, which is formed on at least one surface of the polarizing film. It includes a base material layer.
[0120]
　The polarizing film in this embodiment can be made of a thermoplastic resin. Examples of the thermoplastic resin include polyester resin, polycarbonate resin, polyolefin resin, polyimide resin, polyvinyl alcohol resin, polyvinyl chloride resin and the like. From the viewpoint of water resistance, heat resistance and molding processability, polyester resin and polycarbonate resin are preferable, and polyester resin is more preferable.
[0121]
　Examples of the polyester resin include polyethylene terephthalate, polyethylene naphthalate, and polybutylene terephthalate, and polyethylene terephthalate is preferable from the viewpoint of water resistance, heat resistance, and molding processability.
[0122]
　Specific examples of the polarizing film include a dichroic dye-containing polyester polarizing film, an iodine-containing polyvinyl alcohol polarizing film, and a dichroic dye-containing polyvinyl alcohol polarizing film.
　The polarizing film may be used after being heat-treated for drying and stabilization.
　Further, in order to improve the adhesion of the polarizing film to the acrylic resin, primer coating treatment, chemical treatment (chemical treatment such as gas or alkali), corona discharge treatment, plasma treatment, ultraviolet irradiation treatment, electron beam irradiation treatment , One kind or two or more kinds of pretreatments selected from roughening treatment, flame treatment and the like may be performed before use. Among such pretreatments, one or more selected from primer coating treatment, chemical treatment, corona discharge treatment, and plasma treatment is particularly preferable.
[0123]
　The plastic polarizing lens of the present embodiment is on one surface of such a polarizing film on the objective surface side surface or the eyepiece surface side surface, or on both the objective surface side surface and the eyepiece surface side surface. , The base material layer obtained by curing the polymerizable composition for an optical material of the present embodiment is laminated.
[0124]
　When the base material layer in the present embodiment is formed on one surface of the polarizing film, the base material layer formed on the other surface of the polarizing film is derived from the polymerizable composition for an optical material of the present embodiment. It can be formed from plastic materials such as acrylic resin, allyl carbonate resin, polycarbonate resin, polyurethane resin, polythiourethane resin, and polysulfide resin.
[0125]
　The plastic polarizing lens of the present embodiment is not particularly limited, and examples thereof include a method of sticking a lens base material on both sides of a polarizing film, a method of casting and polymerizing a polymerizable composition on both sides of a polarizing film, and the like. In this embodiment, an example formed by the casting polymerization method will be described.
[0126]
　In the method for producing a plastic polarizing lens of the present embodiment, for example, in a
　mold, a first polymerizable composition layer is formed on a surface of the polarizing film on the objective surface side, and a second polymerization is performed on the other surface of the polarizing film. It can include a step of forming the sex composition layer and a step
　of polymerizing and curing the polymerizable composition layer and laminating a base material layer on both surfaces of the polarizing film.
　The first polymerizable composition layer is formed from the polymerizable composition for optical materials of the present embodiment.
[0127]
　The lens casting mold is generally composed of two substantially disk-shaped glass molds held by gaskets. In the space of the lens casting mold, the polarizing film is installed so that the film surface is parallel to the inner surface of the mold on the front side facing each other. A gap is formed between the polarizing film and the mold. The polarizing film may be attached in advance.
　Then, the first polymerizable composition is injected between the mold and the surface of the polarizing film on the objective surface side to form a layer of the first polymerizable composition, and then the surface of the polarizing film on the eyepiece side and the mold are formed. The second polymerizable composition can be injected into the gap between the two and the second polymerizable composition to form a layer of the second polymerizable composition.
[0128]
　Further, in this step, the first polymerizable composition is placed on a forming surface for forming the objective surface of the lens of the mold, and the first polymerizable composition is spread over the entire surface of the forming surface with a polarizing film. In order to separate the mold and the surface of the polarizing film on the objective surface side by a predetermined distance through the layer of the first polymerizable composition formed by spreading, and then to form the polarizing film and the eyepiece surface of the lens of the mold. It can also be carried out by injecting the second polymerizable composition into the gap with the forming surface of the second polymerizable composition to form a layer of the second polymerizable composition.
[0129]
　The polymerization conditions of the polymerizable composition vary depending on the composition of the polymerizable composition, the type and amount of the catalyst used, the shape of the mold, and the like, but are carried out at a temperature of 5 to 140 ° C. over 1 to 50 hours. In some cases, it is preferable to keep the temperature in the temperature range of 5 to 130 ° C. or gradually raise the temperature to cure in 1 to 25 hours.
　The plastic polarized lens of the present embodiment can be obtained by releasing the laminate cured by polymerization from a mold.
[0130]
　In the present embodiment, the laminate after polymerization / release may be subjected to heat treatment such as annealing, if necessary. From the viewpoint of the effect of the present invention, the treatment temperature is between 90 and 150 ° C., preferably 110 to 130 ° C., and more preferably 115 to 125 ° C. The treatment time is in the range of 1 to 10 hours, preferably 2 to 5 hours from the viewpoint of the effect of the present invention.
　The coating layer similar to that of a plastic spectacle lens may be formed on the surface of the obtained base material layer.
Example
[0131]
　Next, the present invention will be described in more detail by way of examples, but the present invention is not limited to these examples. In the examples and comparative examples, the method used for evaluation and the apparatus used are as follows.
[0132]
Confirmation of effect expression of compound (C)
・ Transmittance: Ultraviolet-visible light spectrum (380-800 nm) using Shimadzu spectrophotometer UV-1600 manufactured by Shimadzu Corporation as a measuring instrument and a 2 mm thick planau lens. ) Was measured, and the transmittance at 585 nm was measured. When the transmittance of the lens is 60% or less, it is determined that the specific wavelength absorbing dye which is the compound (C) exerts the effect (judgment: ○), and when the transmittance of the lens exceeds 60%, It was determined that the specific wavelength absorbing dye did not exhibit the effect (determination: ×).
B *: A 2 mm thick flat plate was measured using a color difference meter CR-5 manufactured by Konica Minolta. The observation light source was D65 / 10, and the color measurement results were expressed in the CIE 1976 (L *, a *, b *) color space. L * represents brightness, a * represents red, and b * represents yellow.
　When b * is 20 or less, it is determined that the ultraviolet absorber which is compound (C) exerts the effect (judgment: ◯), and when b * exceeds 20, the ultraviolet absorber has the effect. Was not expressed (judgment: ×).
　When b * is less than 0, it is determined that the dye which is compound (C) exerts the effect (determination: ◯), and when b * is 0 or more, the dye exerts the effect. It was judged that it was not (judgment: ×).
[0133]
-Transparency: The transparency of the molded product processed to a thickness of 9 mm was visually judged.
-Rockwell hardness: Measured on the M scale in accordance with ISO2039-2.
[0134]
Moldability
/ Lens cracking: "Lens cracking" is a phenomenon in which a lens cracks during polymerization. Five Plano 4C (2 mm thick) lenses were created, and one or more lenses that were broken after the polymerization was completed were "lens cracked" (productivity failure, judgment x), and those that were not broken at all were "no lens cracked". (Good productivity, judgment ○).
-Polymerization peeling: "Polymerization peeling" is a phenomenon in which a molded product is peeled off from a glass mold during polymerization in a glass mold. Those that did not peel off during the polymerization were marked with ⊚, those that peeled off during the polymerization but no circular pattern was confirmed, and those that peeled off during the polymerization and confirmed a circular pattern were marked with x. The circular pattern means, for example, a phenomenon in which an unpolymerized portion is formed because the molded body is peeled off from the glass mold during polymerization and appears mainly as a circular pattern on the lens surface.
-Pulse: "Pulse" is a phenomenon that is locally different from the normal refractive index of the surroundings due to differences in composition, etc., and is observed as stripes. The prepared sample was projected with a high-pressure mercury lamp (light source model OPM-252HEG: manufactured by Ushio, Inc.), and the transmitted image was visually observed for the presence or absence of pulse. Those in which no stripes were observed were marked with ◯, and those in which stripes were observed were marked with x.
-Release crack: Five lenses of Plano 4C (2 mm thick) were prepared, and when the mold and the lens were separated after the polymerization was completed, those that did not crack at all were marked with "○" and one or more lenses were cracked. Those with "Δ" and those with four or more broken pieces were evaluated as "x".
[0135]
(Ingredients used)
Allyl carbonate compound (A)
/ RAV7AT (poly (allyl carbonate) compound of diethylene glycol and pentaerythritol and its oligomer, manufactured by ACOMON)
[0136]
(Meta) Acrylate Compound (B)
/ Triethylene Glycol Dimethacrylate (NK Ester 3G, manufactured by Shin Nakamura Chemical Industry Co., Ltd.)
[0137]
Compound (C)
, PD-311S (product name, manufactured by Mitsui Chemicals, Inc.): Tetra-t-butyl-tetraazaporphyrin, copper complex represented by formula (5a),
Viosorb 583 (product name, Kyodo Yakuhin Co., Ltd.) (
Manufactured by): 2- (2-Hydroxy-5-t-octylphenyl) benzotriazole / TINUVIN 326 (Product name, manufactured by BASF): 2- (3-t-Butyl-2-hydroxy-5-methylphenyl)- 5-Chlorobenzotriazole
, Hostavin PR-25 (product name, manufactured by CLARIANT): (p-methoxybenzylidene) Dimethyl malate
, Plast Blue 8514 (product name, manufactured by Arimoto Chemical Industry Co., Ltd.): Anthraquinone dye
[0138]
Radical polymerization initiator (D)
t-butyl-peroxyneodecanoate (Perbutyl ND, manufactured by Nichiyu Co., Ltd.)
　　　Radical residual rate after 50 ° C. for 5 hours: 57.6% Radical residual rate after
　　　70 ° C. for 5 hours Rate: 0.2%
Bis (4-t-butylcyclohexyl) Peroxydicarbonate (Peroyl TCP, manufactured by Nichiyu Co., Ltd.)
　　　Radical residual rate after 50 ° C for 5 hours: 28.2%
　　　70 ° C after 5 hours Radical residual rate: 0.0%
t-Amil-peroxyneodecanoate (LUPEROX546, manufactured by Alchema)
　　　Radical residual rate after 5 hours at 50 ° C: 54.5%
　　　Radical residual rate after 5 hours at 70 ° C : 0.0%
2-2'-azobis (2,4-dimethylvaleronitrile) (V65, manufactured by Fujifilm Wako)
　　　Radical residual rate after 5 hours at 50 ° C: 73.8%
　　　70 ° C after 5 hours Radical residual rate in: 2.0%
1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate (PerOcta O, manufactured by Nichiyu Co., Ltd.)
　　　Radical residual rate at 70 ° C. after 5 hours: 53 .8%
t-Amilperoxy-2-ethylhexanoate (TRIGONOX121, manufactured by Chemical Axo)
　　　Radical residual rate after 5 hours at 70 ° C: 78.5%
1,1-di (t-amylperoxy) cyclohexane (LUPEROX 531, manufactured by Arkema)
　　　Radical residual rate after 5 hours at 70 ° C: 98.6 %
[0139]
[Example 1]
　Additives to 12.0 parts by weight of polyallyl carbonate RAV 7AT (manufactured by Acomon), 88.0 parts by weight of triethylene glycol dimethacrylate NK ester 3G (manufactured by Shin-Nakamura Chemical Co., Ltd.), and 2.0 parts by weight of α-methylstyrene dimer. PD-311S (manufactured by Yamamoto Kasei Co., Ltd.) 0.001 parts by weight, as an initiator, t-butyl-peroxyneodecanoate 0.55 parts by weight, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexa 0.15 parts by weight of Noate was added, and the mixture was mixed and stirred to dissolve. Degassed for 60 minutes under 5 mmHg. Filtration was performed with a 1 μm PTFE filter, and the mixture was injected into a mold made of a glass mold and tape. After putting this mold into an oven, the temperature was gradually raised from 35 ° C. to 95 ° C. over 24 hours for polymerization. After completion of the polymerization, the mold was taken out from the oven and released to obtain a 2.0 mm thick resin flat plate. The obtained resin flat plate was further annealed at 110 ° C. for 1 hour. The obtained molded product was colorless and transparent. It was confirmed that the Rockwell hardness was 82, showing a good hardness. The 585 nm transmittance was 45%. The results obtained are shown in Table-1.
[0140]
[Example 2]
　Additives to 12.0 parts by weight of polyallyl carbonate RAV 7AT (manufactured by Acomon), 88.0 parts by weight of triethylene glycol dimethacrylate NK ester 3G (manufactured by Shin-Nakamura Chemical Co., Ltd.), and 2.0 parts by weight of α-methylstyrene dimer. VIOSOR B583 (manufactured by Kyodo Yakuhin Co., Ltd.) 0.20 parts by weight, as an initiator, t-butyl-peroxyneodecanoate 0.55 parts by weight, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate 0.15 parts by weight was added, and the mixture was mixed and stirred to dissolve. Degassed for 60 minutes under 5 mmHg. Filtration was performed with a 1 μm PTFE filter, and the mixture was injected into a mold made of a glass mold and tape. After putting this mold into an oven, the temperature was gradually raised from 35 ° C. to 95 ° C. over 24 hours for polymerization. After completion of the polymerization, the mold was taken out from the oven and released to obtain a 2.0 mm thick resin flat plate. The obtained resin flat plate was further annealed at 110 ° C. for 1 hour. The obtained molded product was colorless and transparent. It was confirmed that the Rockwell hardness was 81, showing a good hardness. In addition, b * was 1.2. The results obtained are shown in Table-1.
[0141]
[Example 3]
　Additives to 12.0 parts by weight of polyallyl carbonate RAV 7AT (manufactured by Acomon), 88.0 parts by weight of triethylene glycol dimethacrylate NK ester 3G (manufactured by Shin-Nakamura Chemical Co., Ltd.), and 2.0 parts by weight of α-methylstyrene dimer. As TINUVIN 326 (manufactured by BASF) 1.5 parts by weight, as an initiator, t-butyl-peroxyneodecanoate 0.55 parts by weight, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate 0.15 parts by weight was added, and the mixture was mixed and stirred to dissolve. Degassed for 60 minutes under 5 mmHg. Filtration was performed with a 1 μm PTFE filter, and the mixture was injected into a mold made of a glass mold and tape. After putting this mold into an oven, the temperature was gradually raised from 35 ° C. to 95 ° C. over 24 hours for polymerization. After completion of the polymerization, the mold was taken out from the oven and released to obtain a 2.0 mm thick resin flat plate. The obtained resin flat plate was further annealed at 110 ° C. for 1 hour. The obtained molded product was colorless and transparent. It was confirmed that the Rockwell hardness was 78, showing a good hardness. In addition, b * was 5.8. The results obtained are shown in Table-1.
[0142]
[Example 4]
　Additives to 12.0 parts by weight of polyallyl carbonate RAV 7AT (manufactured by Acomon), 88.0 parts by weight of triethylene glycol dimethacrylate NK ester 3G (manufactured by Shin-Nakamura Chemical Co., Ltd.), and 2.0 parts by weight of α-methylstyrene dimer. Hostavin PR-25 (manufactured by Clariant) 0.10 parts by weight, as initiator, t-butyl-peroxyneodecanoate 0.55 parts by weight, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexa 0.15 parts by weight of Noate was added, and the mixture was mixed and stirred to dissolve. Degassed for 60 minutes under 5 mmHg. Filtration was performed with a 1 μm PTFE filter, and the mixture was injected into a mold made of a glass mold and tape. After putting this mold into an oven, the temperature was gradually raised from 35 ° C. to 95 ° C. over 24 hours for polymerization. After completion of the polymerization, the mold was taken out from the oven and released to obtain a 2.0 mm thick resin flat plate. The obtained resin flat plate was further annealed at 110 ° C. for 1 hour. The obtained molded product was colorless and transparent. It was confirmed that the Rockwell hardness was 82, showing a good hardness. In addition, b * was 1.1. The results obtained are shown in Table-1.
[0143]
[Example 5]
　Additives added to 12.0 parts by weight of polyallyl carbonate RAV 7AT (manufactured by Acomon), 88.0 parts by weight of triethylene glycol dimethacrylate NK ester 3G (manufactured by Shin-Nakamura Chemical Co., Ltd.), and 2.0 parts by weight of α-methylstyrene dimer. As Plast Blue 8514 (manufactured by Arimoto Chemical Co., Ltd.) 0.001 part by weight, as an initiator, t-butyl-peroxyneodecanoate 0.55 part by weight, 1,1,3,3-tetramethylbutylperoxy-2-ethyl 0.15 parts by weight of hexanoate was added, and the mixture was mixed and stirred to dissolve. Degassed for 60 minutes under 5 mmHg. Filtration was performed with a 1 μm PTFE filter, and the mixture was injected into a mold made of a glass mold and tape. After putting this mold into an oven, the temperature was gradually raised from 35 ° C. to 95 ° C. over 24 hours for polymerization. After completion of the polymerization, the mold was taken out from the oven and released to obtain a 2.0 mm thick resin flat plate. The obtained resin flat plate was further annealed at 110 ° C. for 1 hour. The obtained molded product was colorless and transparent. It was confirmed that the Rockwell hardness was 82, showing a good hardness. In addition, b * was -5.5. The results obtained are shown in Table-1.
[0144]
[Examples 6 to 8] As
　shown in Table 1, polymerization was carried out in the same manner as in Example 5 except that the type of initiator was changed to obtain a molded product. The amount of the initiator added is the same as in Example 5. The results obtained are shown in Table-1.
[0145]
[Example 9] As
　shown in Table 1, 0.55 parts by weight of t-butyl-peroxyneodecanoate was added to 0.20 parts by weight of 2-2'-azobis (2,4-dimethylvaleronitrile) (V65). Polymerization was carried out in the same manner as in Example 5 except that the results were changed to obtain a molded product. The results obtained are shown in Table-1.
[0146]
[Comparative Examples 1 to 3] As
　shown in Table 1, polymerization was carried out in the same manner as in Example 1 except that the type of initiator was changed to obtain a molded product. The amount of the initiator added is the same as in Example 1. The results obtained are shown in Table-1.
[0147]
[Comparative Examples 4 to 6] As
　shown in Table 1, polymerization was carried out in the same manner as in Example 2 except that the type and amount of the compound (C) and the type of the initiator were changed to obtain a molded product. The amount of the initiator added is the same as in Example 2. The results obtained are shown in Table-1.
[0148]
[Comparative Examples 7 to 9] As
　shown in Table 1, polymerization was carried out in the same manner as in Example 5 except that the type of initiator was changed to obtain a molded product. The amount of the initiator added is the same as in Example 5. The results obtained are shown in Table-1.
[0149]
[table 1]

[0150]
[Table 2]

[0151]
　This application claims priority on the basis of Japanese application Japanese Patent Application No. 2017-234197 filed on December 6, 2017 and Japanese application Japanese Patent Application No. 2018-104866 filed on May 31, 2018. , All of its disclosures are taken here.
The scope of the claims
[Claim 1]
It contains (A) an allyl carbonate compound represented by the general formula (1) and containing two or more allyloxycarbonyl groups, and
(B) two or more (meth) acrylic groups represented by the general formula (2). The (meth) acrylate compound,
(C) at least one compound selected from the compounds represented by the general formulas (3) to (6) and the following dyes, and
(D) at least the radical polymerization initiator (D1). A polymerization initiator containing a radical polymerization initiator (D2), and the
　compound (A) is contained in an amount of more than 0% by weight and 30% by weight or less in a total of 100% by weight of the compound (A) and the compound (B). The compound (B) is contained in an amount of 70% by weight or more and less than 100% by weight, and the
　radical polymerization initiator (D1) has a radical residual rate of 20% or more and less than 100% after the lapse of 5 hours at 50 ° C. The subsequent radical residual rate is 0% or more and less than 30%, and the
　radical polymerization initiator (D2) is a polymerizable composition for an optical material having a radical residual rate of 30% or more and less than 98% after 5 hours at 70 ° C.;
[Chemical

formula 1] (In the general formula (1), R 1 contains a 2- to 20-valent radical or hetero atom derived from a chain or branched C3- to C35 aliphatic polyol which may contain a hetero atom. .m showing a divalent to hexavalent group derived from a cyclic aliphatic polyols ~ C40 C5 which can have is an integer of 2-20. Note that, R 1 does not include the allyloxycarbonyl group.)
[Formula 2]

(In the general formula (2), R 2 represents a bi to tetravalent organic group having 1 to 30 carbon atoms which may contain a hetero atom or an aromatic group. R 3 represents a hydrogen atom or a methyl group. N indicates an integer of 2 to 4),
[Chemical

formula 3] (In the general formula (3), R 1 and R 2 indicate an alkyl group or a halogen atom of C1 to C8, which are the same but different. and may. more existing R 1 s or more existing R, 2 are each other may be the same or different .m is an integer of 0 to 3, n is an integer of 0-3, p is 0-1 R 3 represents a functional group of C2 to C15 containing an ester bond.),
[Chemical

formula 4] (In general formula (4), Z 3 is an aromatic of C6 to C20 which may be substituted. family organic group, an alicyclic group optionally substituted C5 ~ also be C20, Z 4 and Z 5 may be the same or different, C1 ~ C6 alkyl group, a C1 ~ C6 alkoxy group.) ,
[Chemical 5]

(In general formula (5), A 1~ A 8 and X 1 to X 4 are independently hydrogen atom, halogen atom, nitro group, cyano group, hydroxy group, amino group, carboxyl group, sulfonic acid group, linear, branched or branched with 1 to 20 carbon atoms. Cyclic alkyl group, alkoxy group with 1 to 20 carbon atoms, aryloxy group with 6 to 20 carbon atoms, monoalkylamino group with 1 to 20 carbon atoms, dialkylamino group with 2 to 20 carbon atoms, 7 to 20 carbon atoms Dialkylamino group, aralkyl group having 7 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, heteroaryl group, alkylthio group having 6 to 20 carbon atoms, and arylthio group having 6 to 20 carbon atoms. A 1 to A 8 may form a ring excluding the aromatic ring via a linking group. n represents 0 or 1. Q 1 ~ Q 4 each independently represent a carbon atom, a nitrogen atom. M represents two hydrogen atoms, a divalent metal atom, a divalent monosubstituted metal atom, a tetravalent disubstituted metal atom, or an oxymetal atom. ),
[Chemical Formula 6]

In (formula (6), R 1 represents a hydrogen atom, R is. Plurality of a linear or branched alkyl group having 1 to 20 carbon atoms 1 even each other be the same or different Good. M is an integer of 1 to 3, n is an integer of 1 to 3, and the sum of m and n is an integer of 3 to 6).
　Dyes: At least one selected from anthraquinone dyes, perinone dyes, monoazo dyes, diazo dyes, and phthalocyanine dyes.
[Claim 2]
　The compound (A) 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 ] bis of at least one diol selected from tricyclodecane. At
least one selected from at least one triol triol (allyl carbonate) compound,
pentaerythritol, diglycerol and ditrimethylolpropane selected from (allyl carbonate) compounds, glycerol, trimethylolpropane and tris (hydroxyethyl) isocyanurate. The 　allyl comprises at least one selected from the group consisting of a tetra (allyl carbonate) compound of tetraol,
a hexa (allyl carbonate) compound of
dipentaerythritol , and a hexa (allyl carbonate) compound of
bispentaerythritol. The polymerizable composition for an optical material according to claim 1, which is a carbonate compound (A) or a mixture of the allyl carbonate compound (A) and an oligomer thereof.
[Claim 3]
　Compound (A) is
(i) a bis (allyl carbonate) compound of
diethylene glycol , (ii) a bis (allyl carbonate) compound of a mixture of diethylene glycol and neopentyl glycol, and
(iii) a mixture of diethylene glycol and tris (hydroxyethyl) isocyanurate. Poly (allyl carbonate) compound,
(iv) Poly (allyl carbonate) compound of a mixture of diethylene glycol and trimethylolpropane,
(v) Poly (allyl carbonate) compound of a mixture of diethylene glycol and pentaerythritol,
(vi) Diethylene glycol and neopentyl A poly containing a poly (allyl carbonate) compound of a mixture of glycol and pentaerythritol, and a poly (allyl carbonate) compound of a mixture of
(vii) diethylene glycol, neopentyl glycol and pentaerythritol, and
a bis (allyl carbonate) compound of diethylene glycol. The
　polymerizable composition for an optical material according to claim 1 or 2, which is at least one selected from the (allyl carbonate) mixture, and comprises a mixture of the allyl carbonate compound (A) and an oligomer thereof.
[Claim 4]
　The polymerizable composition for an optical material according to any one of claims 1 to 3, wherein the compound (B) is selected from the compounds represented by the general formula (2-1) and the general formula (2-2).
[Chemical formula 6]

(p indicates a numerical value of 1 to 100, R 3 indicates a hydrogen atom or a methyl group, and they do not have to be the same.)
[Chemical formula 7]

(q indicates a numerical value of 1 or more, respectively. The sum of the two qs represents a number from 2 to 100. R 3 represents a hydrogen atom or a methyl group, which may not be the same. X is a substituted or unsubstituted divalent aromatic group. Indicates a divalent aliphatic group which may contain a substituted or unsubstituted aromatic group having 1 to 20 carbon atoms.)
[Claim 5]
　The polymerizable composition for an optical material according to claim 4, wherein the compound (B) is selected from the compounds in which p is represented by 2 to 4 in the general formula (2-1).
[Claim 6]
　A molded product obtained by curing the polymerizable composition for an optical material according to any one of claims 1 to 5.
[Claim 7]
　An optical material comprising the molded product according to claim 6.
[Claim 8]
　A plastic lens made of the molded product according to claim 6.
[Claim 9]
　A
　plastic polarizing lens comprising a polarizing film and a base material layer made of the molded product according to claim 6, which is formed on at least one surface of the polarizing film.