[0001]The present invention relates to an optical material for the polymerizable composition containing a photochromic compound, an optical material and a plastic lens obtained from the composition.
BACKGROUND
[0002]Plastic lenses are hardly cracked lightweight, dyeing spectacle lenses for possible has been rapidly spread as an optical material such as a camera lens, moldings for lenses with various plastic materials can be used is developed so far ing.
　Representative examples, and allyl resins obtained from diethylene glycol bis allyl carbonate and diallyl isophthalate, and (meth) obtained from acrylate (meth) acrylic resins, polythiourethane resin obtained from isocyanates and thiols.
[0003]
　Recently has been developed a high-performance plastic lenses that various functions are applied, for example, a lens that blocks light harmful wavelengths, the lens damaged was suppressed on the surface or the lens surface caused by temperature difference, cloudiness is known lens that has been suppressed. Plastic lens having a photochromic performance is one such high-performance plastic lenses, has been developed. By using the plastic lens having such photochromic performance, and functions as an ordinary transparent color glasses indoors, the lens in response to sunlight (UV) outdoors gray, is colored brown, from glare it can be obtained glasses of expressing functional to protect the eyes. The spectacles need not redial glasses indoors and outdoors as sunglasses, a highly functional glasses that can be supported for use with one of the glasses in both indoor and outdoor, in recent years, its demand it has expanded worldwide.
[0004]
　Such a plastic lens having photochromic properties, it is required that the response of the coloring and decoloring exerts fast that and good coloring performance.
[0005]
　For example, certain aliphatic, by using alicyclic isocyanate, a urethane resin-based optical material or thiourethane resin optical material and plastic lenses comprising a photochromic compound can be obtained without causing performance degradation of the photochromic compound (Patent Document 1).
　Further, according to the optical material for the polymerizable composition containing a specific polyol compound, without causing performance degradation of the photochromic compound, as well as excellent photochromic properties, excellent in physical properties such as mechanical strength, photochromic polyurethane optical materials or polythiourethane optical material containing the compound can be obtained (Patent Document 2).
[0006]
　Also, by improving the dispersibility by suppressing aggregation of the photochromic compounds of an optical material for the polymerizable composition or an optical material for resin, a technique for improving the photochromic properties of the resin it has been proposed. Such techniques, for example, polymer fine particles comprising a photochromic compound in a polymer has been proposed (Patent Documents 3-7). The optical material for a resin having a refractive index of 1.695 from 1.595 comprising including nanoparticles of the photochromic compound has been proposed (Patent Document 8).
CITATION
Patent Document
[0007]
Patent Document 1: WO 2014/002844 Patent
Patent Document 2: WO 2015/115648
Patent Document 3: WO 2014/007154 Patent
Patent Document 4: JP-T 2008-506031 Patent Publication
Patent Document 5: JP Publication Sho 64-29489
Patent Document 6: JP-a 1-152182 Patent Publication
JP 7: DE102009052986
Patent Document 8: WO 2004/011506
Non-patent literature
[0008]
Non-Patent Document 1: P. Alexandridis, TA Hatton / Colloids Surfaces A: Physicochem Eng Aspects 96 (1995) 1-46..
Non-Patent Document 2: Phys Chem Chem Phys, 1999 , 1, 3331-3334....
Summary of the Invention
Problems that the Invention is to Solve
[0009]
　And naphthopyran photochromic dye and a polyolefin terminally branched copolymer in Patent Document 3, as a polymerizable monomer 1,2-bis (2-mercaptoethyl) thio-3-mercapto propane, pentaerythritol tetra (3- Merukaputopuro Pioneto) and and norbornene diisocyanate, a method for producing a photochromic dye-containing polythiourethane resin from a polymerizable composition comprising is disclosed. However, since it is necessary to produce a resin is mixed with a polymerizable monomer after preliminarily prepared polymer particles containing a photochromic dye from polyolefin based terminally branched copolymer and naphthopyran photochromic dye, the manufacturing process is long becomes resin the production efficiency is disadvantageously significantly reduced.
[0010]
　Further, the case where the polymer particles were mixed polymerizable monomer, the pot life of the polymer particles and easily viscosity of the polymerizable composition because of its high reactivity with the polymerizable monomer is increased polymerizable composition is shortened , there is room for improvement, such may not be producing the resin molded body efficiently.
Means for Solving the Problems
[0011]
　The present inventors have conducted extensive studies results, by using a specific polymer, it is possible to obtain a polymerizable composition excellent in handling properties increase in the viscosity is suppressed, better photochromic properties, heat resistance and mechanical properties found to be able to provide an optical material comprising, the present invention has been completed.
　That is, the present invention can be illustrated below.
[0012]
[1] the following general formula (1) to (4) consists of one or more compounds selected from compounds represented by the polymer and (a),
　the compound absorption characteristics by sensing changes in the environment changes ( and b)
　polymerizing the reactive compound (c) (polymer (a) except for.),
including, for optical materials polymerizable composition.
[Formula 1]

In (formula (1), .R A represents a polyolefin chain 1 and R 2 represent a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, is at least one hydrogen atom. X 1 and X 2 are the same or different, formula (1a) or formula represented by any one of (1c).
[formula 2]

in (formula (1a), E is an oxygen atom or a sulfur atom represents, X 3 is. a group represented by polyalkylene glycol group or a group represented by formula (1b))
[formula 3]

in (formula (1b), R 3 .G is representative of the m + 1-valent hydrocarbon group the same or different, -OX 4 , -N + R 4X 5 X 6 Q 1- (X 4 - X 6 represents a polyalkylene glycol group, R 4 represents a hydrogen atom, a polyalkylene glycol group substituted by 1 carbon atoms which may be ~ 18 alkyl group, an aromatic alkyl It represents a group, Q 1- is a group represented by a halogen ion, carboxylate anion or inorganic acid anion.). m is, R 3 represents an integer of is 1 to 10 and the number of bonds and the G. )
[Formula 4]

　in (formula (1c), X 7 , X 8 are the same or different, a group represented by polyalkylene glycol group or the general formula (1b), R 5 is a hydrogen atom, an alkylene an aromatic alkyl group of the alkyl group or having 6 to 18 glycol-carbon atoms 1 be substituted with a group 18, Q 2 - represents an anion of a halogen ion, carboxylate anion or an inorganic acid. )
[Chemical formula 5]

in (formula (2), a represents an n-valent organic radical, R 2 represents alkyl group having 1 carbon atoms which may have 20 substituted, substituted carbon atoms 7 also be ~ 20 aralkyl group, an aryl group substituted carbon atoms 6 even to 20, R 3 represents a hydrocarbon group or alkyleneoxy group having 1 to 20 carbon atoms having 1 to 20 carbon atoms having a hydroxyl group, R 4 represents an organic group which may having 1 to 20 carbon atoms which may have a hydroxyl group, R 5 represents an organic group having a hydrogen atom or a carbon atoms 1 ~ 20, R 6 , R 7 , R 8 each independently represent a hydrogen atom or a methyl group, n represents an integer of 1 ~ 20, a, b is each represent an integer of 1 to 200 independently. R presence of a plurality of 2 ~ R 8 may be the same or different. )
[Formula 6]

in (formula (3), A is derived from a polyol compound having two or more hydroxyl groups, C in the repeating unit (= O) - combine with a group which forms an ester bond, R 1 represents alkyl group having 1 carbon atoms which may have 20 substituted, substituted carbon atoms 7 also be ~ 20 aralkyl group, an aryl group substituted carbon atoms 6 even to 20, R 2Represents a hydrocarbon group or alkyleneoxy group having 1 to 20 carbon atoms having 1 to 20 carbon atoms having a hydroxyl group, R 3 represents a hydrogen atom or a methyl group, m represents an integer of 1 ~ 1000, o is A indicating the number following values of the hydroxyl groups of the polyol compound constituting the. R presence of a plurality of 1 ~ R 3 may be the same or different. )
[Chemical Formula 7]

In (formula (4), A 1 , A 2 .R represents a respectively different polymer chains 1 is an n-valent organic group, R 2 linking group which connects the two polymer chains and a, R 3 is an integer of which .n 1-6 organic group.)
[2] the compound (b) is a chromic compound, an optical material for the polymerizable composition according to [1].
[3] the chromic compound is a photochromic compound, an optical material for the polymerizable composition according to [2].
[4] the photochromic compound is a naphthopyran derivative, the optical material for the polymerizable composition according to [3].
[5] polymerizable compound (c), polyiso (thio) cyanate compound, (thio) epoxy compounds, oxetanyl compound, thietanyl compound, (meth) acryloyl compounds, (meth) allyl compounds, alkene compounds, alkyne compounds, di- functional or more active hydrogen compound, and is selected from an acid anhydride containing one or more compounds, [1] ~ for optical materials polymerizable composition according to any one of [4].
[6] polymerizable compound (c) comprises the polyiso (thio) cyanate compound and bifunctional or more of the active hydrogen compound,
　the polyiso (thio) cyanate compound, an aliphatic polyiso (thio) cyanate compound, fat alicyclic polyiso (thio) cyanate compound, an aromatic polyiso (thio) cyanate compound, an optical material for the polymerizable composition according to [5].
[7] including the micro phase separation structure of the polymer (a), [1] ~ for optical materials polymerizable composition according to any one of [6].
[8] and micro-phase separation structure having the following general formula (1) to (4) consists of one or more compounds selected from compounds represented by the polymer (a),
　by sensing a change in environment absorbance compounds characteristic changes (b),
　a resin is polymerized (. excluding polymer (a)) polymerizable compound (c),
including, cured product.
[Formula 8]

(In the general formula (1), A represents a polyolefin chain .R 1 and R 2Represents a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, and at least one of a hydrogen atom. X 1 and X 2 are the same or different, represented by any of formulas (1a) or formula (1c).
[Chemical Formula 9]

(In the general formula (1a), E represents an oxygen atom or a sulfur atom, X 3 represents a group represented by the polyalkylene glycol group or a group represented by formula (1b).)
[Formula 10]

(General wherein (1b), R 3 is .G representing the (m + 1) -valent hydrocarbon group are the same or different, -OX 4 , -N + R 4 X 5 X 6 Q 1- (X 4 ~ X 6 are polyalkylene It represents a glycol group, R 4 represents a hydrogen atom, a polyalkylene glycol group substituted by 1 carbon atoms which may be ~ 18 alkyl group, an aromatic group, Q 1-Represents a halogen ion, carboxylate anion or inorganic acid anion. ) Is a group represented by. m is, R 3 represents an integer of is 1 to 10 and the number of bonds and the G. )
[Formula 11]

　in (formula (1c), X 7 , X 8 are the same or different, a group represented by polyalkylene glycol group or the general formula (1b), R 5 is a hydrogen atom, an alkylene an aromatic alkyl group of the alkyl group or having 6 to 18 glycol-carbon atoms 1 be substituted with a group 18, Q 2 - represents an anion of a halogen ion, carboxylate anion or an inorganic acid. )
[formula 12]

in (general formula (2), a represents an n-valent organic group, R 2 is alkyl group having 1 carbon atoms which may have 20 substituted, carbon atoms, which may optionally be substituted 7 aralkyl group to 20, an aryl group which may be substituted carbon atoms 6 to 20, R 3 represents a hydrocarbon group or alkyleneoxy group having 1 to 20 carbon atoms having 1 to 20 carbon atoms having a hydroxyl group , R 4 is not a hydroxyl group Represents also a good organic group having a carbon number of 1 ~ 20, R 5 represents an organic group having a hydrogen atom or a carbon atoms 1 ~ 20, R 6 , R 7 , R 8 each independently represent a hydrogen atom or a methyl group, n is an integer from 1 to 20, a, b is an integer of 1 to 200 independently. R presence of a plurality of 2 ~ R 8 may be the same or different. ) [Formula
13]

in (formula (3), A is derived from a polyol compound having two or more hydroxyl groups, C in the repeating unit (= O) - combine with a group which forms an ester bond, R 1 represents alkyl group having 1 carbon atoms which may have 20 substituted, substituted carbon atoms 7 also be ~ 20 aralkyl group, an aryl group substituted carbon atoms 6 even to 20, R 2 represents a hydrocarbon group or alkyleneoxy group having 1 to 20 carbon atoms having 1 to 20 carbon atoms having a hydroxyl group, R 3 represents a hydrogen atom or a methyl group, m represents an integer of 1 ~ 1000, o the R to. plurality of indicating the number following values of the hydroxyl groups of the polyol compound constituting the a 1 ~ R 3 may be the the same or different.)
[formula 14]

in (formula (4), a 1 , A 2Each represent different polymer chains. R 1 is an n-valent organic group, R 2 is a linking group linking two polymer chains, R 3 is an organic group. n is an integer of 1 to 6. )
[9] [1] ~ molded body was cured optical material for the polymerizable composition according to any one of [7].
[10] includes a microphase-separated structure of the polymer (a), the molded body according to [9].
Optical material comprising a molded product according to [11] [9] or [10].
[12] a plastic lens composed of a molded product according to [9] or [10].
[13] the following general formula (1) to (4) consists of one or more compounds selected from compounds represented by the polymer and (a), the compound absorption characteristics is changed by changes in the environment and (b) , polymerizable reactive compound and (. excluding polymer (a)) (c), comprising the mixing process, a manufacturing method of an optical material for the polymerizable composition.
[Formula 15]

in (formula (1), .R A represents a polyolefin chain 1 and R 2 represent a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, is at least one hydrogen atom. X 1 and X 2It is the same or different and is represented by any one of formulas (1a) or formula (1c).
[Formula 16]

(In the general formula (1a), E represents an oxygen atom or a sulfur atom, X 3 represents a group represented by the polyalkylene glycol group or a group represented by formula (1b).)
[Formula 17]

(General wherein (1b), R 3 is .G representing the (m + 1) -valent hydrocarbon group are the same or different, -OX 4 , -N + R 4 X 5 X 6 Q 1- (X 4 ~ X 6 are polyalkylene It represents a glycol group, R 4 is a hydrogen atom, a polyalkylene glycol group substituted by 1 carbon atoms which may be ~ 18 alkyl group, an aromatic group, Q 1- halogen ions, carboxylate anions, or represents an inorganic anion.) is a group represented by .m is, R 3 represents an integer of a bond number 1-10 and the G.)
[Formula 18]

　in (formula (1c), X 7 , X 8 are the same or different, a group represented by polyalkylene glycol group or the general formula (1b), R 5 is a hydrogen atom, an alkylene glycol an aromatic alkyl group of the alkyl group or having 6 to 18 is to 1 carbon atoms which may 18 optionally substituted with a group, Q 2 - represents an anion of a halogen ion, a carboxylate anion or inorganic acid).
[formula 19]

in (general formula (2), a represents an n-valent organic group, R 2 is an optionally substituted alkyl group having 1 to 20 carbon atoms, substituted carbon atoms and optionally 7 to 20 aralkyl group, an aryl group which may be substituted carbons 6 ~ 20, R 3 represents a hydrocarbon group or alkyleneoxy group having 1 to 20 carbon atoms having 1 to 20 carbon atoms having a hydroxyl group, R 4 is have a hydroxyl group It represents an organic group which may carbons 1 ~ 20, R 5 represents an organic group having a hydrogen atom or a carbon atoms ~ 20 1, R 6 , R 7 , R 8Each independently represent a hydrogen atom or a methyl group, n is an integer from 1 to 20, a, b is an integer of 1 to 200 independently. R presence of a plurality of 2 ~ R 8 may be the same or different. )
[Formula 20]

in (formula (3), A is derived from a polyol compound having two or more hydroxyl groups, C in the repeating unit (= O) - combine with a group which forms an ester bond, R 1 represents alkyl group having 1 carbon atoms which may have 20 substituted, substituted carbon atoms 7 also be ~ 20 aralkyl group, an aryl group substituted carbon atoms 6 even to 20, R 2 represents a hydrocarbon group or alkyleneoxy group having 1 to 20 carbon atoms having 1 to 20 carbon atoms having a hydroxyl group, R 3 represents a hydrogen atom or a methyl group, m represents an integer of 1 ~ 1000, o the R to. plurality of indicating the number following values of the hydroxyl groups of the polyol compound constituting the a 1 ~ R 3 may be the same or different.)
[formula 21]

in (formula (4), a 1 , a 2 .R representing a respective different polymer chains Is an n-valent organic radical, R 2 is a linking group linking two polymer chains, R 3 is an organic group. n is an integer of 1 to 6. )
[14] The polymer (a), the step of mixing the compound (b) and polymerization reactivity compound (c) is
　a step of forming a polymer particles containing a polymer (a) and compound (b),
　the polymer comprising the steps of mixing particles in the polymerization reaction of the compound (c),
the manufacturing method, including, for optical materials polymerizable composition according to [13].
[15] polymerizable compound (c) consists of two or more compounds,
　polymer (a), the step of mixing the compound (b) and polymerization reactivity compound (c) is
　the polymer (a), a step of mixing a portion of the compound (b) and polymerization reactive compound (c),
　a step of mixing the remainder of the polymerizable reactive compound (c) to the mixture obtained in the above step,
including, [13] method for producing an optical material for the polymerizable composition according to.
[16] Compound (b) is a chromic compound, [13] The method for producing an optical material for the polymerizable composition according to any one of - [15].
[17] the chromic compound is a photochromic compound, method for producing an optical material for the polymerizable composition according to [16].
[18] The photochromic compound is naphthopyran derivatives, method for producing an optical material for the polymerizable composition according to [17].
Comprising the step of polymerizing and curing the optical material for the polymerizable composition according to any one of [19] [1] to [7],
　wherein the process is
　a polymerization reactive compound (c) is formed by polymerizing a resin with polymer (a) forms a microphase-separated structure, comprising the step of forming a cured body made from said resin said a microphase separation structure compound (b), the production method of the cured product.
[20] [1] - comprising the step of forming a lens substrate by cast polymerization of the optical material for the polymerizable composition according to any one of [7] The method of manufacturing a plastic lens.
[21] the step of forming a lens base material,
　a polymerization reactive compound (c) is polymerized polymer to form the resin (a) forms a micro phase separation structure, wherein said resin microphase comprising the step of forming a lens base material made from an isolation structure compound (b), method of manufacturing a plastic lens according to [20].
Effect of the invention
[0013]
　The optical material for the polymerizable composition of the present invention is excellent in handling properties increase in the viscosity is suppressed, it is possible to provide an optical material having excellent photochromic properties, heat resistance and mechanical properties.
BRIEF DESCRIPTION OF THE DRAWINGS
[0014]
　Above objects, and other objects, features and advantages, preferred embodiments described below, and become more apparent from the following drawings associated therewith.
Is a TEM photograph of the molded article prepared by [1] Example a11.
[2] is a TEM photograph of the molded article prepared by Example b21.
3 is a TEM photograph of the molded article prepared by Example b22.
4 is a TEM photograph of the molded article prepared by Example d8.
5 is a TEM photograph of the molded article prepared by Example d92.
[6] Based on Example e1, e2, e3, e16, and e17 result, a graph plotting the relationship between the mixing ratio and the decoloring rate F1 / 2 of the block copolymer.
[7] Example e4, e5, e16, and based on the results of e18, a graph plotting the relationship between the mixing ratio and the decoloring rate F1 / 2 of the block copolymer.
[8] Example e6, e7, e17, and based on the results of e19, a graph plotting the relationship between the mixing ratio and the decoloring rate F1 / 2 of the block copolymer.
[9] based on Examples e8, e9, e10, e17, and e20 result, a graph plotting the relationship between the mixing ratio and the decoloring rate F1 / 2 of the block copolymer.
[10] Example e11, e17, and based on the results of e21, a graph plotting the relationship between the mixing ratio and the decoloring rate F1 / 2 of the block copolymer.
[11] Based on the embodiment e12, e13, e17, and e22 result, a graph plotting the relationship between the mixing ratio and the decoloring rate F1 / 2 of the block copolymer.
[12] Example e14, e15, e18, and based on the results of e22, a graph plotting the relationship between the mixing ratio and the decoloring rate F1 / 2 of the block copolymer.
DESCRIPTION OF THE INVENTION
[0015]
　The optical material for the polymerizable composition of the present invention includes a polymer (a), the compound absorption characteristics vary by sensing changes in the environment (b), the polymerization reactive compound and (c).
　Hereinafter, it will be explained using embodiments of the present invention.
[0016]
[Polymer (a)]
　In the present embodiment, the polymer (a) comprises one or more selected from compounds represented by the following general formula (1) to (4).
[0017]
(Formula (a compound represented by 1))
　In the present embodiment, it is possible to use a compound represented by the following general formula as the polymer (a) (1).
[Of 22]

[0018]
　In the formula (1), A represents a polyolefin chain.
　The polyolefin chain is obtained by polymerizing an olefin having 2 to 20 carbon atoms. Examples of the olefin having 2 to 20 carbon atoms, ethylene, propylene, 1-butene, include α- olefins such as 1-hexene. In the present embodiment, it may be a homopolymer or a copolymer of these olefins, or may be copolymerized with other polymerizable unsaturated compounds within a range not to impair the properties. Especially ethylene Among these olefins, propylene, 1-butene is preferred.
[0019]
　R 1 and R 2 represent a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, and at least one of a hydrogen atom. Examples of the alkyl group having 1 to 18 carbon atoms, a methyl group, an ethyl group, a propyl group.
　X 1 and X 2 are the same or different, represented by any of formulas (1a) or formula (1c).
[0020]
[Of 23]

[0021]
　In the general formula (1a), E represents an oxygen atom or a sulfur atom, X 3 represents a group represented by the polyalkylene glycol group or a group represented by formula (1b).
[0022]
[Of 24]

[0023]
　In the general formula (1b), R 3 represents a (m + 1) -valent hydrocarbon radical. G is the same or different, -OX 4 , -N + R 4 X 5 X 6 Q 1- (X 4 ~ X 6 represents a polyalkylene glycol group, R 4 is substituted with a hydrogen atom, a polyalkylene glycol group which may be an alkyl group having 1 to 18 carbon atoms, an aromatic group, Q 1- represents a group represented by a halogen ion, carboxylate anion or inorganic acid anion.). m is, R 3 represents an integer of is 1 to 10 and the number of bonds and the G.
　In formula (1a), from the viewpoint of the effect of the present invention, E is an oxygen atom, X 3 is preferably a polyethylene glycol group.
[0024]
[Of 25]

[0025]
　In the general formula (1c), X 7 , X 8 are the same or different, represents a group represented by polyalkylene glycol group or the general formula (1b), R 5 is substituted with a hydrogen atom or an alkylene glycol group and an aromatic alkyl group of the alkyl group or having 6 to 18 carbon atoms which may 1 ~ 18, Q 2 - represents an anion of a halogen ion, carboxylate anion or an inorganic acid.
　In the general formula (1c), from the viewpoint of the effect of the present invention, R 5 is an aromatic group, X 7 and X 8 are preferably both is a polyalkylene glycol group.
[0026]
　In the present embodiment, as the compound represented by the general formula (1), R 1 and R 2 are hydrogen atoms, X 1 and X 2 in the general formula a group represented by (1a) and the general formula (1c) it is preferably a combination of the group represented.
[0027]
　Examples of the compound represented by the general formula (1) can be used a compound represented by specifically the following general formula (1-1).
[0028]
[Of 26]

[0029]
　In the general formula (1-1), R 6 and R 7 represent a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, is at least one hydrogen atom. R 8 and R 9 represent a hydrogen atom or a methyl group, is at least one hydrogen atom, R 10 and R 11 represent a hydrogen atom or a methyl group, and at least one of a hydrogen atom, R 12 and R 13 represent a hydrogen atom or a methyl group, at least either a hydrogen atom, R 14 is or an alkyl group having a hydrogen atom or an alkylene glycol to 1 carbon atoms which may be substituted with a group 18 an aromatic alkyl group, Q 3 - represents an anion of a halogen ion, carboxylate anion or an inorganic acid. l + m + o is an integer of 3 or more 450 or less. n represents an integer of 20 to 300.
　In the present embodiment, it is possible to use at least one selected from compounds represented by the general formula as the polymer (a) (1).
[0030]
(General formula (compound represented by the 2))
　In the present embodiment, it is possible to use a compound represented by the following general formula as the polymer (a) (2).
[0031]
[Of 27]

[0032]
　In the formula (2), A represents an n-valent organic group, R 2 is alkyl group having 1 carbon atoms which may have 20 substituted, substituted carbon atoms and optionally 7-20 aralkyl group, optionally substituted aryl group having a carbon number of 6 ~ 20, R 3 represents a hydrocarbon group or alkyleneoxy group having 1 to 20 carbon atoms having 1 to 20 carbon atoms having a hydroxyl group, R 4 is a hydroxyl group has also represent an organic group which may carbons 1 ~ 20, R 5 represents an organic group having a hydrogen atom or a carbon atoms 1 ~ 20, R 6 , R 7 , R 8 are each independently hydrogen or methyl It represents a radical, n represents an integer of 1 to 20, a, b is an integer of 1 to 200 independently. R presence of a plurality of 2 ~ R 8 may be the same or different.
　R 2 , examples of the substituent of the "substituted alkyl group having 1 to 20 carbon atoms, substituted aralkyl group having 7 to 20 carbon atoms, substituted aryl group having 6 to 20 carbon atoms" include halogen atom, hydroxyl group, a cyano group, a nitro group, a sulfonyl group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, etc. haloalkoxy group having 1 to 6 carbon atoms be able to.
[0033]
　Examples of the compound represented by the general formula (2), specifically, n is 1, structure A in the block copolymer is represented by the following general formula (2a), using a compound represented by any one of (2b) be able to.
[0034]
[Formula 28]

[0035]
　In the general formula (2a), B represents a structure having a monoalkoxy group.
[0036]
　As B of the general formula (2a), is specifically induced monoalkoxy structure or derived from terminally branched copolymer, pentaerythritol, dipentaerythritol, glycerol, from diglycerol, polyglycerol and saccharides and the like can be given monoalkoxy structure.
[0037]
　The terminally branched copolymer can be used a compound of WO 2014/007154 Patent forth, it is preferable to use a polymer represented by the following general formula (2c) or (2d).
[0038]
[Of 29]

[0039]
　In the general formula (2c), R 4 and R 5 represent a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, and at least one of a hydrogen atom. The alkyl group is preferably an alkyl group having 1-9 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms.
　R 6 and R 7 represent a hydrogen atom or a methyl group, and at least one of a hydrogen atom. R 8 and R 9 represent a hydrogen atom or a methyl group, and at least one of a hydrogen atom. R presence of a plurality of 4 ~ R 9 may be the same or different.
　l + m is 2 or more 450 or less, preferably an integer of 5 to 200.
　n is 20 to 300, preferably an integer of 25 to 200.
[0040]
[Formula 30]

[0041]
　In the general formula (2d), R 4 and R 5 represent a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, and at least one of a hydrogen atom. The alkyl group is preferably an alkyl group having 1-9 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms.
　R 6 and R 7 represent a hydrogen atom or a methyl group, and at least one of a hydrogen atom. R 8 and R 9 represent a hydrogen atom or a methyl group, and at least one of a hydrogen atom. R 10 and R 11 represent a hydrogen atom or a methyl group, and at least one of a hydrogen atom. R presence of a plurality of 4 ~ R 11 may be the same or different.
　l + m + o is 3 or more 450 or less, preferably an integer of 5 to 200.
　n is 20 to 300, preferably an integer of 25 to 200.
[0042]
　The polymer represented by the general formula (2d), more preferable to use a polymer represented by the following general formula (2e).
[0043]
[Of 31]

[0044]
　In the general formula (2e), l + m + o, n is the same as in the general formula (2d).
[0045]
[Formula 32]

[0046]
　In the general formula (2b), R 6 represents an organic group which ~ 1 carbon atoms which may have 20 substituted. As the organic group include a benzyl group and the like.
[0047]
　In the present embodiment, from the viewpoint of the effect of the present invention, compounds represented by the general formula (2) is, n is 1, A is the general formula (2a) or (2b), R 2 may be substituted an aryl group having a carbon number of 6 ~ 20, R 3 hydrocarbon radical, R having 1 to 20 carbon atoms having a hydroxyl group 4 are organic groups may 1 to 20 carbon atoms which may have a hydroxyl group, R 5 is a hydrogen atom it is preferable that.
　In the present embodiment, it is possible to use at least one selected from compounds represented by the general formula as the polymer (a) (2).
[0048]
(General formula (compound represented by 3))
　In the present embodiment, it is possible to use a compound represented by the following general formula as the polymer (a) (3).
[0049]
[Formula 33]

[0050]
　In formula (3), A is derived from a polyol compound having two or more hydroxyl groups, C in the repeating unit (= O) - combine with a group which forms an ester bond, R 1 is optionally substituted alkyl group having 1 to 20 carbon atoms be, substituted carbon atoms 7 even though 1-20 aralkyl group, an aryl group which may be substituted carbon atoms 6 to 20, R 2 has a hydroxyl group represents a hydrocarbon group or alkyleneoxy group having 1 to 20 carbon atoms having 1 to 20 carbon atoms, R 3 represents a hydrogen atom or a methyl group, m represents an integer of 1 ~ 1000, o is a polyol that constitutes the a indicating the number following values of the hydroxyl groups of compounds. R presence of a plurality of 1 ~ R 3 may be the same or different.
　R 1 , examples of the substituent of the "substituted alkyl group having 1 to 20 carbon atoms, substituted aralkyl group having 7 to 20 carbon atoms, substituted aryl group having 6 to 20 carbon atoms" include halogen atom, hydroxyl group, a cyano group, a nitro group, a sulfonyl group, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, etc. haloalkoxy group having 1 to 6 carbon atoms be able to.
[0051]
　In the present embodiment, from the viewpoint of the effect of the present invention, A is a pentaerythritol, dipentaerythritol, glycerol, a group derived from diglycerol, polyglycerol and saccharides, o is 1, m is 1 ~ 1000 integers, R 1 is an aryl group-C6 optionally substituted 20, R 2 is preferably a hydrocarbon group having 1 to 20 carbon atoms having a hydroxyl group.
　In the present embodiment, it is possible to use at least one selected from compounds represented by the general formula as the polymer (a) (3).
[0052]
(General formula (compound represented by the 4))
　In the present embodiment, it is possible to use a compound represented by the following general formula as the polymer (a) (4).
[0053]
[Formula 34]

[0054]
　In the general formula (4), A 1 , A 2 represent different polymer chains, respectively. R 1 is an n-valent organic group, R 2 is a linking group linking two polymer chains, R 3 is an organic group. n is an integer of 1 to 6.
　The polymer chains, polyalkylene chain, a polyester chain, polysiloxane chain, polyethyleneimine chain include polyalkylene oxide chain or the like. Examples of the polymer chains, polyalkylene oxide chain.
[0055]
　The polyalkylene chain is a polymer chain, polyethylene chain, a polypropylene chain, polystyrene chain, poly (meth) acrylic acid ester chain, poly (meth) acrylic acid chain, a polymethylene indane chain like.
　The polyester chain is a polymer chain, poly α- acetolactone chain, poly β- propiolactone chain, poly γ- butyrolactone chain, poly δ- valerolactone chain, poly ε- caprolactone chains, polylactic acid chains, polyglycolic acid chain, polylactic glycolic acid copolymer chains, and polyethylene terephthalate chain or the like.
　The polysiloxane chain is a polymer chain include polydimethylsiloxane chains, polymethyl phenyl siloxane chain or the like.
　The polyethyleneimine chain is a polymer chain include polyethyleneimine chain, polypropylene propionyl aziridine chain, poly acetyl aziridine chain, a poly-formyl aziridine chain like.
[0056]
　The polyalkylene oxide chain is a polymer chain include polyethylene glycol chain, a polypropylene glycol chain, polybutylene glycol chain, poly pentene glycol chain, poly-hexene glycol chain, a poly-heptene glycol chain or the like. Further, when n is 2 or more, plural A 1 , A 2 may have a different polyalkylene oxide chain, respectively.
[0057]
　R 1 is 1-6 monovalent organic group.
　The monovalent organic group, a methoxy group, an ethoxy group, 1-propanoxy group, 2-propanoxy group, an alkoxy group such as methoxyethoxy group, a methyl mercapto group, an ethyl alkylthio group such as a mercapto group, and an acetyl group .
　Examples of the divalent organic group, an ethylene glycolate, propylene glycolate group, bifunctional alkoxy groups such as a butylene glycolate group, ethane dithiolate groups, such as bifunctional thiolate groups such as propane dithiolate groups.
　The trifunctional organic group, glycerolate group, trioxyethyl amine group, such as a trifunctional alkoxy groups such as tri-oxy (alkyl) ammonium salts.
　The tetrafunctional organic group, tetravalent amino groups such as ethylene diamino group or its alkyl ammonium salts, tetra oxyethylenediamine group include tetravalent alkoxy groups such as oxy of pentaerythritol.
　The 6-functional organic group, oxy and the like of the dipentaerythritol.
[0058]
　R 2 is a two divalent linking group having 1 to 10 carbon atoms linking the polymer chains.
　Examples of the divalent linking group, ethylene glycol group, ether-type linking groups such as propylene glycol group, beta-mercaptopropionic acid and (meth) bis carboxylate form linking group such as Michael adducts of acrylic acid, glycol and ether carboxylate-type linking groups such as an acid group, and may be any linking group according to the synthesis method of block copolymer.
[0059]
　R 3 is a terminal functional group, affecting the dispersibility of the compound (a). From the viewpoint of maintaining the dispersion state of the nano-domains after polymerization of the composition R 3 is preferably a polymerizable organic group having reactivity with the polymerizable functional group (c) is.
　Such polymerizable organic example as the hydroxyethyl group of group, hydroxypropyl group, hydroxybutyl group, an organic group having a hydroxyl group such as dihydroxypropyl group; aminoethyl group, an organic having amino groups such as amino propyl the organic group having an epoxy group such as glycidyl ether groups; Chiogurishijiru mercaptoethyl group, mercaptopropionic acid, mercaptoethyl group, mercaptopropyl group, an organic group having a mercapto group such as thioglycolic acid groups: group the organic group having a carboxylic acid such as glycolic acid ether; organic group having a thioepoxy group such as ether group vinyl group, an allyl group, an acrylate group, an organic group having an unsaturated double bond at a terminal, such as a methacrylate group ; end such as propargyl Organic group having an unsaturated triple bond.
[0060]
　Incidentally, R 3 , depending on the type of block copolymer in some cases may not reactive with the polymerizable functional group (c).
　The organic group not reactive, methoxymethyl group, methoxyethyl group, methoxypropyl group, methoxybutyl group, ethoxymethyl group, ethoxyethyl group, ethoxypropyl group, an ethoxy butyl group, propylidene oxymethyl group, propylidene oxyethyl group , propyl propyl group, propyl oxy butyl group, Buchirokishimechiru group, Buchirokishiechiru group, butyronitrile hydroxypropyl group, etc. Buchirokishibuchiru group.
[0061]
　Specific examples of the compound represented by formula (4), compounds represented by the following general formula (4a), compound (a) can be exemplified ~ (v) the like.
[0062]

　In the present embodiment, as the compound represented by the general formula (4) represented by the following general formula (4a) may be a compound.
[0063]
[Formula 35]

[0064]
　In the general formula (4a), R 1 and R 2 represent a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, is at least one hydrogen atom. R presence of a plurality of 1 to each other may be the same or different, R presence of a plurality of 2 to each other may be the same or different. m is 15 or more and 500 or less, preferably an integer of 30 or more and 500 or less.
　Examples of the compound represented by general formula (4a), the number-average molecular weight of 150 or more, preferably can be used in more than 200.
[0065]
　Examples of the compound represented by general formula (4a), can be used a compound represented by specifically the following general formula (4a-1). Specifically, in the general formula (4), R 1 is an alkylene (C2 ~ C20) glycolate group, A 1 is polyalkylene (C2 ~ C20) glycol chain, R 2 is an oxypropylene group, A 2 is polyethylene glycol chain, R 3 is hydroxy ethylene group, when n is 2 valency propylene glycolate group, the compound represented by the following general formula (4a-1).
[0066]
[Formula 36]

[0067]
　In the formula (4a-1), R 3 and R 4 represent a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, is at least one hydrogen atom. a + c is 2 or more and 600 or less, preferably 2 to 400 of integers, b is 1 to 300, preferably an integer of 1 to 100 inclusive. R presence of a plurality of 3 and R 4 may be the same or different.
　And the like manufactured by BASF Pluronic (Pluronic) Series Examples of such compounds. The structures of the compounds contained in the Pluronics shown in Non-Patent Document 1.
　Incidentally, the terminal hydroxyl group of the compound represented by the general formula (4a) may also react with the polymerizable compound such as isocyanate (c).
[0068]
　Of the proportion of mixed compound is not particularly limited but the compound represented by the general formula (4a), compound (Pluronic L64) and the compound (Pluronic P65) when the using, these total 100 wt% relative to the compound (Pluronic L64) 0.1 to 99.9% by weight, preferably 5 to 95 wt%, more preferably 10 to 90% by weight, particularly preferably it can include 20 to 80 wt%.
　When used by mixing a plurality of compounds as the polymer (a), observed improvement of growth and decoloring rate of discoloration concentration, it is possible to provide a plastic lens having more excellent photochromic properties, further transparent sex can be further improved resin properties, such as improved.
[0069]

　In the present embodiment, there can be used compounds as represented by Formula (4) (a) ~ (v).
[0070]
(A) difunctional block polyols
　in the general formula (4), R 1 is propylene glycolate group, A 1 is a polypropylene glycol chain, R 2 is an oxypropylene group, A 2 is a polyethylene glycol chain, R 3 is hydroxyethylene group, when n is 2 valency propylene glycolate group, the compound represented by the following general formula (a-1).
[0071]
[Formula 37]

[0072]
　In formula (a-1), a, b, c each represent a number of units, are each independently a 3 to 300. integers.
　Like Pluronic series (BASF) Examples of such compounds.
[0073]
　As similar compounds, in the general formula (4), R 1 is ethylene glycolate group, A 1 is a polyethylene glycol chain, R 2 is an oxyethylene group, A 2 is a polypropylene glycol chain, R 3 is hydroxy propylene group, when n is 2 valency propylene glycolate group, the compound represented by the following general formula (a-2).
[0074]
[Formula 38]

[0075]
　In formula (a-2), a, b, c each represent a number of units, are each independently a 3 to 300. integers.
　Like Pluronic R series (BASF) Examples of such compounds.
[0076]
(B) 3 functional block polyols
　general formula (4), R 1 is a glycerolate group, A 1 is a polypropylene glycol chain, R 2 is an oxypropylene group, A 2 is a polyethylene glycol chain, R 3 is hydroxy ethylene group, when n is 3 valence glycerol group, the compound represented by the following general formula (b-1).

claims

Following general formula (1) to (4) consists of one or more compounds selected from compounds represented by the polymer and (a),
　the compound absorption characteristics vary by sensing changes in the environment and (b) ,
　polymerizable reactive compound and (c) (excluding the polymer (a).),
including, for optical materials polymerizable composition.
[Formula 1]

In (formula (1), .R A represents a polyolefin chain 1 and R 2 represent a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, is at least one hydrogen atom. X 1 and X 2 are the same or different, formula (1a) or formula represented by any one of (1c).
[formula 2]

in (formula (1a), E is an oxygen atom or a sulfur atom represents, X 3 is. a group represented by polyalkylene glycol group or a group represented by formula (1b))
[formula 3]

in (formula (1b), R 3 .G is representative of the m + 1-valent hydrocarbon group the same or different, -OX 4 , -N + R 4X 5 X 6 Q 1- (X 4 - X 6 represents a polyalkylene glycol group, R 4 represents a hydrogen atom, a polyalkylene glycol group substituted by 1 carbon atoms which may be ~ 18 alkyl group, an aromatic alkyl It represents a group, Q 1- is a group represented by a halogen ion, carboxylate anion or inorganic acid anion.). m is, R 3 represents an integer of is 1 to 10 and the number of bonds and the G. )
[Formula 4]

　in (formula (1c), X 7 , X 8 are the same or different, a group represented by polyalkylene glycol group or the general formula (1b), R 5 is a hydrogen atom, an alkylene an aromatic alkyl group of the alkyl group or having 6 to 18 glycol-carbon atoms 1 be substituted with a group 18, Q 2 - represents an anion of a halogen ion, carboxylate anion or an inorganic acid. )
[Chemical formula 5]

in (formula (2), a represents an n-valent organic radical, R 2 represents alkyl group having 1 carbon atoms which may have 20 substituted, substituted carbon atoms 7 also be ~ 20 aralkyl group, an aryl group substituted carbon atoms 6 even to 20, R 3 represents a hydrocarbon group or alkyleneoxy group having 1 to 20 carbon atoms having 1 to 20 carbon atoms having a hydroxyl group, R 4 represents an organic group which may having 1 to 20 carbon atoms which may have a hydroxyl group, R 5 represents an organic group having a hydrogen atom or a carbon atoms 1 ~ 20, R 6 , R 7 , R 8 each independently represent a hydrogen atom or a methyl group, n represents an integer of 1 ~ 20, a, b is each represent an integer of 1 to 200 independently. R presence of a plurality of 2 ~ R 8 may be the same or different. )
[Formula 6]

in (formula (3), A is derived from a polyol compound having two or more hydroxyl groups, C in the repeating unit (= O) - combine with a group which forms an ester bond, R 1 represents alkyl group having 1 carbon atoms which may have 20 substituted, substituted carbon atoms 7 also be ~ 20 aralkyl group, an aryl group substituted carbon atoms 6 even to 20, R 2Represents a hydrocarbon group or alkyleneoxy group having 1 to 20 carbon atoms having 1 to 20 carbon atoms having a hydroxyl group, R 3 represents a hydrogen atom or a methyl group, m represents an integer of 1 ~ 1000, o is A indicating the number following values of the hydroxyl groups of the polyol compound constituting the. R presence of a plurality of 1 ~ R 3 may be the same or different. )
[Chemical Formula 7]

In (formula (4), A 1 , A 2 .R represents a respectively different polymer chains 1 is an n-valent organic group, R 2 linking group which connects the two polymer chains in and, R 3 is an organic radical .n is an integer of 1-6.)
[Requested item 2]
　The compound (b) is a chromic compound, an optical material for the polymerizable composition according to claim 1.
[Requested item 3]
　The chromic compound is a photochromic compound, an optical material for the polymerizable composition according to claim 2.
[Requested item 4]
　The photochromic compound is a naphthopyran derivative, the optical material for the polymerizable composition of claim 3.
[Requested item 5]
　Polymerizable compound (c) is, polyiso (thio) cyanate compound, (thio) epoxy compounds, oxetanyl compound, thietanyl compound, (meth) acryloyl compounds, (meth) allyl compounds, alkene compounds, alkyne compounds, having two or more functional active hydrogen compound, and one kind selected from an acid anhydride or a two or more compounds, for optical materials polymerizable composition according to any one of claims 1 to 4.
[Requested item 6]
　Polymerizable compound (c) comprises the polyiso (thio) cyanate compound and bifunctional or more of the active hydrogen compound,
　the polyiso (thio) cyanate compound, an aliphatic polyiso (thio) cyanate compound, alicyclic polyiso (thio) cyanate compound, or an aromatic polyiso (thio) cyanate compound, an optical material for the polymerizable composition according to claim 5.
[Requested item 7]
　Comprising a microphase-separated structure of the polymer (a), an optical material for the polymerizable composition according to any one of claims 1 to 6.
[Requested item 8]
　Following general formula (1) to (4) and microphase separation structure of a polymer comprising one or more compounds selected (a) from the compound represented by the
　sensitive and absorption characteristics change a change in environment to compound (b),
　a resin (excluding. polymer (a)) is polymerized polymerizable compound (c),
including, cured product.
[Formula 8]

in (formula (1), .R A represents a polyolefin chain 1 and R 2 represent a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, is at least one hydrogen atom. X 1 and X 2 are the same or different, formula (1a) or formula represented by any one of (1c).
[Chemical formula 9]

in (formula (1a), E is an oxygen atom or a sulfur atom represents, X 3 is. a group represented by polyalkylene glycol group or a group represented by formula (1b))
[formula 10]

in (formula (1b), R 3 .G is representative of the m + 1-valent hydrocarbon group the same or different, -OX 4 , -N + R 4X 5 X 6 Q 1- (X 4 - X 6 represents a polyalkylene glycol group, R 4 represents a hydrogen atom, a polyalkylene glycol group substituted by 1 carbon atoms which may be ~ 18 alkyl group, an aromatic alkyl It represents a group, Q 1- is a group represented by a halogen ion, carboxylate anion or inorganic acid anion.). m is, R 3 represents an integer of is 1 to 10 and the number of bonds and the G. )
[Formula 11]

　in (formula (1c), X 7 , X 8 are the same or different, a group represented by polyalkylene glycol group or the general formula (1b), R 5 is a hydrogen atom, an alkylene an aromatic alkyl group of the alkyl group or having 6 to 18 glycol-carbon atoms 1 be substituted with a group 18, Q 2 - represents an anion of a halogen ion, carboxylate anion or an inorganic acid. )
[formula 12]

in (general formula (2), a represents an n-valent organic radical, R 2 represents alkyl group having 1 carbon atoms which may have 20 substituted, substituted carbon atoms 7 also be ~ 20 aralkyl group, an aryl group substituted carbon atoms 6 even to 20, R 3 represents a hydrocarbon group or alkyleneoxy group having 1 to 20 carbon atoms having 1 to 20 carbon atoms having a hydroxyl group, R 4 represents an organic group which may having 1 to 20 carbon atoms which may have a hydroxyl group, R 5 represents an organic group having a hydrogen atom or a carbon atoms 1 ~ 20, R 6 , R 7 , R 8 each independently represent a hydrogen atom or a methyl group, n represents an integer of 1 ~ 20, a, b is each represent an integer of 1 to 200 independently. R presence of a plurality of 2 ~ R 8 may be the same or different. )
[Formula 13]

in (formula (3), A is derived from a polyol compound having two or more hydroxyl groups, C in the repeating unit (= O) - combine with a group which forms an ester bond, R 1 represents alkyl group having 1 carbon atoms which may have 20 substituted, substituted carbon atoms 7 also be ~ 20 aralkyl group, an aryl group substituted carbon atoms 6 even to 20, R 2Represents a hydrocarbon group or alkyleneoxy group having 1 to 20 carbon atoms having 1 to 20 carbon atoms having a hydroxyl group, R 3 represents a hydrogen atom or a methyl group, m represents an integer of 1 ~ 1000, o is A indicating the number following values of the hydroxyl groups of the polyol compound constituting the. R presence of a plurality of 1 ~ R 3 may be the same or different. )
[Formula 14]

in (formula (4), A 1 , A 2 .R represents a respectively different polymer chains 1 is an n-valent organic group, R 2 linking group which connects the two polymer chains in and, R 3 is an organic radical .n is an integer of 1-6.)
[Requested item 9]
　Molded cured optical material for polymerizable composition according to any one of claims 1 to 7.
[Requested item 10]
　Comprising a microphase-separated structure of the polymer (a), the molded body according to claim 9.
[Requested item 11]
　Optical material comprising a molded body according to claim 9 or 10.
[Requested item 12]
　Plastic lenses made of molded product according to claim 9 or 10.
[Requested item 13]
　Following general formula (1) to (4) consists of one or more compounds selected from compounds represented by the polymer and (a), the compound absorption characteristics is changed by a change in environment (b), the polymerization reaction (excluding polymer (a).) sexually compound (c) and a, including mixing method of manufacturing an optical material for the polymerizable composition.
[Formula 15]

in (formula (1), .R A represents a polyolefin chain 1 and R 2 represent a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, is at least one hydrogen atom. X 1 and X 2 are the same or different, formula (1a) or formula. represented by any one of (1c)
[Chemical formula 16]

in (formula (1a), E is an oxygen atom or a sulfur atom represents, X 3 is. a group represented by polyalkylene glycol group or a group represented by formula (1b))
[formula 17]

in (formula (1b), R 3 .G is representative of the m + 1-valent hydrocarbon group the same or different, -OX 4 , -N + R 4 X 5 X 6 Q 1- (X 4 - X 6 represents a polyalkylene glycol group, R 4 represents a hydrogen atom, a polyalkylene glycol group substituted by 1 carbon atoms which may be ~ 18 alkyl group, an aromatic group , Q 1- is a group represented by a halogen ion, carboxylate anion or inorganic acid anion.). m is, R 3 represents an integer of is 1 to 10 and the number of bonds and the G. )
[Formula 18]

　in (formula (1c), X 7 , X 8 are the same or different, a group represented by polyalkylene glycol group or the general formula (1b), R 5 is a hydrogen atom, an alkylene an aromatic alkyl group of the alkyl group or having 6 to 18 glycol-carbon atoms 1 be substituted with a group 18, Q 2 - represents an anion of a halogen ion, carboxylate anion or an inorganic acid. )
[formula 19]

in (general formula (2), a represents an n-valent organic group, R 2Represents the alkyl group having 1 carbon atoms which may have 20 substituted, substituted carbon atoms 7 also be ~ 20 aralkyl group, an aryl group substituted carbon atoms 6 even to 20, R 3 represents a hydrocarbon group or alkyleneoxy group having 1 to 20 carbon atoms having 1 to 20 carbon atoms having a hydroxyl group, R 4 represents an organic group which may having 1 to 20 carbon atoms which may have a hydroxyl group, R 5 represents an organic group having a hydrogen atom or a carbon atoms 1 ~ 20, R 6 , R 7 , R 8 each independently represent a hydrogen atom or a methyl group, n represents an integer of 1 ~ 20, a, b are respectively independently an integer of from 1 to 200. R presence of a plurality of 2 ~ R 8 may be the same or different. )
[Formula 20]

in (formula (3), A is derived from a polyol compound having two or more hydroxyl groups, C in the repeating unit (= O) - combine with a group which forms an ester bond, R 1 represents alkyl group having 1 carbon atoms which may have 20 substituted, substituted carbon atoms 7 also be ~ 20 aralkyl group, an aryl group substituted carbon atoms 6 even to 20, R 2Represents a hydrocarbon group or alkyleneoxy group having 1 to 20 carbon atoms having 1 to 20 carbon atoms having a hydroxyl group, R 3 represents a hydrogen atom or a methyl group, m represents an integer of 1 ~ 1000, o is A indicating the number following values of the hydroxyl groups of the polyol compound constituting the. R presence of a plurality of 1 ~ R 3 may be the same or different. )
[Formula 21]

in (formula (4), A 1 , A 2 .R represents a respectively different polymer chains 1 is an n-valent organic group, R 2 linking group which connects the two polymer chains in and, R 3 is an organic radical .n is an integer of 1-6.)
[Requested item 14]
　Wherein the step of mixing the polymer (a), compound (b) and polymerization reactive compound (c) includes
　the steps of forming a polymer particles containing a polymer (a) and compound (b),
　the polymer particles to a mixing polymerization reactivity compound (c),
including, method for producing an optical material for the polymerizable composition of claim 13.
[Requested item 15]
　Polymerizable compound (c) consists of two or more compounds,
　wherein the step of mixing the polymer (a), compound (b) and polymerization reactive compound (c) is
　the polymer (a), compound (b ) a step of mixing and polymerization compound a part of (c),
　, the mixing rest of the polymerizable reactive compound (c) to the mixture obtained in the step
including, according to claim 13 method for producing an optical material for the polymerizable composition.
[Requested item 16]
　Compound (b) it is a chromic compound, method for producing an optical material for the polymerizable composition according to any one of claims 13-15.
[Requested item 17]
　The chromic compound is a photochromic compound, method for producing an optical material for the polymerizable composition of claim 16.
[Requested item 18]
　The photochromic compound is a naphthopyran derivative, method for producing an optical material for the polymerizable composition of claim 17.
[Requested item 19]
　Comprising the step of polymerizing and curing the optical material for the polymerizable composition according to any one of claims 1-7,
　wherein the process is
　a polymer with a polymerization-reactive compound (c) is formed by polymerizing a resin (a ) forms a microphase-separated structure, comprising the step of forming a cured body made from said resin said a microphase separation structure compound (b), the production method of the cured product.
[Requested item 20]
　Comprising the step of forming a lens substrate by cast polymerization of the optical material for the polymerizable composition according to any one of claims 1 to 7, a manufacturing method of a plastic lens.
[Requested item 21]
　It said step of forming a lens base material,
　a polymerization reactive compound (c) is polymerized polymer to form the resin (a) forms a micro phase separation structure, the microphase-separated structure and the resin comprising the step of forming a lens base material made from and compound (b), method of manufacturing a plastic lens according to claim 20.