Molded parts and components with polymerization properties for optical materials.
Patent Information
- Application Number
- TH1801001538
- Authority / Receiving Office
- TH · TH
- Patent Type
- Patents
- Current Assignee / Owner
- Filing Date
- 2016-09-16
- Publication Date
- 2026-10-02
- Estimated Expiration
- 2036-09-15
AI Technical Summary
Photochromic performance in poly(thio)urethane resin compositions deteriorates over time due to the reaction of isocyanate with photochromic compounds at the monomer stage, leading to loss of photochromic properties, and existing solutions do not effectively stabilize this performance.
A polymerizable composition for optical materials is developed, comprising a polyisocyanate compound, a polyol compound, a bifunctional or more active hydrogen compound, and a photochromic compound, with a specific molar ratio of NCO groups to OH and SH groups, which is optimized to suppress the concentration of residual SH groups and maintain photochromic performance.
The composition effectively stabilizes photochromic performance by reducing residual SH groups, preventing deterioration and ensuring long-term photochromic functionality in molded optical materials.
Abstract
Description
Molded article and polymerizable composition for optical materials The present invention relates to a molded article containing a photochromic compound and a polymerizable composition for optical materials. Plastic lenses have rapidly spread to optical elements such as spectacle lenses and camera lenses because they are lighter and less likely to break than inorganic lenses. In recent years, the development of plastic lenses having photochromic performance has been underway. Among them, lenses obtained from poly(thio)urethane are attracting attention because they have a high refractive index and excellent physical properties such as strength. Patent Document 1 describes a lens comprising a composition containing a predetermined photochromic compound and a di(meth)acrylate compound. Paragraph 0009 states that when a urethane resin or a thiourethane resin having a high refractive index is used, isocyanate, which is a resin raw material at the monomer stage, reacts with the photochromic compound and the photochromic performance is completely lost. Patent Document 2 discloses a lens provided with a coating layer comprising a composition containing a photochromic compound having a chromene skeleton and a phenol compound on the surface of a thiourethane-based plastic lens. Patent Document 3 discloses a photochromic lens having a lens substrate made of a thiourethane resin and a photochromic film formed by applying a solution containing a photochromic compound and a radically polymerizable monomer on the substrate. Patent Document 4 discloses a compound having photochromic properties. Patent Document 5 discloses a polymerizable composition for optical materials containing one or more isocyanate compounds selected from aliphatic isocyanate compounds and alicyclic isocyanate compounds, a polyfunctional active hydrogen compound, and a photochromic compound. Patent Document 6 discloses a polymerizable composition for an optical material containing a polyisocyanate compound, a predetermined polyol compound, a bifunctional or higher-functional active hydrogen compound, and a photochromic compound. In this document, it is described that the molar ratio of the NCO groups contained in the polyisocyanate compound to the total of the OH groups and SH groups contained in the active hydrogen compound and the polyol compound (NCO groups / (OH groups + SH groups)) is in the range of 0.8 to 1.2, and the most preferable range is in the range of 0.9 to 1.1. Japanese Patent Application Laid-Open No. 8-272036, Japanese Patent Application Laid-Open No. 2005-23238, Japanese Patent Application Laid-Open No. 2008-30439, Japanese Patent Application Laid-Open No. 2011-144181, International Publication No. 2014 / 002844 Pamphlet, International Publication No. 2015 / 115648 Pamphlet, U.S. Patent No. 6506538, Japanese Patent Application Laid-Open No. 2005-305306, International Publication No. 2005 / 087829 Pamphlet, International Publication No. 2006 / 109765 Pamphlet, International Publication No. 2007 / 020817 Pamphlet, International Publication No. 2007 / 020818 Pamphlet, International Publication No. 2014 / 002844 Pamphlet, International Publication No. 2015 / 115648 Pamphlet The present inventors investigated the photochromic performance of the resin molded body obtained in the examples of Patent Document 6. As a result, it was found that when the "molar ratio of the NCO groups contained in the polyisocyanate compound to the total of the OH groups and SH groups contained in the active hydrogen compound and the polyol compound (NCO groups / (OH groups + SH groups))" in the resin composition is more than 1.0, the deterioration of the photochromic performance is suppressed as compared with the case where the ratio is 1.0. Therefore, the present inventors confirmed the residue concentrations of NCO groups and SH groups in the resin molded body by IR analysis, and found that there is a correlation between the stability of the photochromic performance of the resin molded body and the remaining SH group concentration in the resin molded body. Note that no correlation was confirmed between the stability of the photochromic performance and the remaining NCO group concentration. Furthermore, it was found that if the molar ratio in the resin composition is in a specific range exceeding 1.0, the remaining SH group concentration in the resin molded body can be suppressed. That is, it was found that by setting the molar ratio in the resin composition within a predetermined range containing a large amount of NCO groups and reducing the remaining SH group concentration in the resin molded body to less than a predetermined value, the deterioration of the photochromic performance over time can be suppressed. The present invention can be shown as follows. [1] (A) A polyisocyanate compound, (B) The following general formula (1) (In formula (1), m represents a numerical value from 1 to 20, k represents 0 to 2m, n represents a numerical value from 1 to 20, l represents 0 to 2n, a represents a numerical value of 0 or more, b represents a numerical value of 0 or more, d represents a numerical value of 0 or more, and e represents a numerical value of 1 or more. Q 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and a plurality of Qs 1 may be the same or different. Q 2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and a plurality of Qs 2 may be the same or different. Z represents a divalent organic group having 1 to 30 carbon atoms which may contain an aromatic group, and a plurality of Zs may be the same or different.) represented by, and a polyol compound having a number average molecular weight of 100 or more, (C) A polyfunctional active hydrogen compound (excluding the compound (B)), (D) A photochromic compound, A molded body obtained by polymerizing and curing a polymerizable composition containing A molded body having an SH group concentration of less than 1.0 wt% by IR analysis. The molded article according to [1], wherein the polyisocyanate compound (A) is at least one selected from the group consisting of hexamethylene diisocyanate, pentamethylene diisocyanate, xylylene diisocyanate, isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane, dicyclohexylmethane diisocyanate, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, tolylene diisocyanate, phenylene diisocyanate, and diphenylmethane diisocyanate. The molded article according to [1] or [2], wherein the polyol compound (B) is at least one compound selected from the compounds represented by the following general formula (I) to the following general formula (IV); (In formula (I), p represents a numerical value of 4 to 100, X represents a hydrogen atom or a methyl group, and a plurality of Xs may be the same or different.) (In formula (II), q and r may be the same or different and each represents a numerical value of 1 or more, and the sum of q and r represents a numerical value of 2 to 100. R 1 and R 2 may be the same or different and each represents a hydrogen atom or a methyl group, and a plurality of Rs 1 or Rs 2 may be the same or different. Z represents a divalent aromatic group which may be substituted or unsubstituted, or a divalent aliphatic group which may contain a substituted or unsubstituted aromatic group having 1 to 20 carbon atoms.) (In formula (III), q and r may be the same or different and each represents a numerical value of 1 or more, and the sum of q and r represents a numerical value of 2 to 100. R 1 and R 2 may be the same or different and each represents a hydrogen atom or a methyl group, and a plurality of Rs 1 or Rs 2 may be the same or different.) (In formula (IV), m represents a numerical value from 1 to 20, k represents 0 to 2m, n represents a numerical value from 1 to 20, l represents 0 to 2n, f represents a numerical value of 0 or more, g represents a numerical value of 1 or more, h represents a numerical value of 1 or more, and j represents a numerical value of 1 or more. Q 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and a plurality of Q 1 may be the same or different. Q 2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and a plurality of Q 2 may be the same or different. R 3 represents a linear or branched alkylene group having 1 to 20 carbon atoms, or a phenylene group which may have a linear or branched alkyl group having 1 to 10 carbon atoms as a substituent, and a plurality of R 3 may be the same or different.) [4] The molded article according to [3], wherein the polyol compound (B) is a compound represented by general formula (I), general formula (III) or general formula (IV). [5] The molded article according to [3] or [4], wherein the compound represented by general formula (I) is polyethylene glycol or polypropylene glycol. [6] The molded article according to any one of [3] to [5], wherein the number average molecular weight of the compound represented by general formula (I) is 200 to 4000. [7] The molded article according to any one of [3] to [5], wherein the number average molecular weight of the compound represented by general formula (I) is 300 to 3000. [8] The molded article according to [3], wherein the number average molecular weight of the compound represented by general formula (II) is 400 to 2000. [9] The molded article according to [3] or [4], wherein the number average molecular weight of the compound represented by general formula (III) is 400 to 2000.
[10] The molded article according to [3] or [4], wherein the number average molecular weight of the compound represented by general formula (IV) is 600 to 3000.
[11] The molded article according to any one of [1] to
[10] , wherein the active hydrogen compound (C) is at least one selected from the group consisting of a polyol compound, a polythiol compound, and a thiol compound having a hydroxy group.
[12] The molded article according to any one of [1] to
[11] , wherein the active hydrogen compound (C) is a trifunctional or higher functional active hydrogen compound.
[13] The molded article according to any one of [1] to
[12] , wherein the active hydrogen compound (C) is at least one selected from the group consisting of glycerin, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, and trimethylolpropane tris(3-mercaptopropionate).
[14] The molded article according to any one of [1] to
[13] , wherein the photochromic compound (D) is represented by the following general formula (5); (In the formula, R 1 and R 2 may be the same or different and are independently hydrogen; a linear or branched alkyl group having 1 to 12 carbon atoms; a cycloalkyl group having 3 to 12 carbon atoms; an aryl group having 6 to 24 carbon atoms or a heteroaryl group having 4 to 24 carbon atoms, which may be substituted or unsubstituted (as substituents, a halogen atom, a hydroxy group, a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkoxy group having 1 to 12 carbon atoms, a linear or branched haloalkyl group having 1 to 12 carbon atoms substituted with at least one halogen atom, a linear or branched haloalkoxy group having 1 to 12 carbon atoms substituted with at least one halogen atom, a phenoxy group or a naphthoxy group substituted with at least one linear or branched alkyl group or alkoxy group having 1 to 12 carbon atoms, a linear or branched alkenyl group having 2 to 12 carbon atoms, -NH 2 group, -NHR group, -N(R) 2a group (wherein R is a linear or branched alkyl group having 1 to 6 carbon atoms. When two Rs are present, the two Rs may be the same or different), and having at least one substituent selected from a methacryloyl group or an acryloyl group.); an aralkyl or heteroaralkyl group (wherein a linear or branched alkyl group having 1 to 4 carbon atoms is substituted with the above aryl group or heteroaryl group) represents R3s may be the same or different and are independently a halogen atom; a linear or branched alkyl group having 1 to 12 carbon atoms; a cycloalkyl group having 3 to 12 carbon atoms; a linear or branched alkoxy group having 1 to 12 carbon atoms; a linear or branched haloalkyl group having 1 to 12 carbon atoms substituted with at least one halogen atom, a halocycloalkyl group having 3 to 12 carbon atoms substituted with at least one halogen atom, a linear or branched haloalkoxy group having 1 to 12 carbon atoms substituted with at least one halogen atom; an aryl group having 6 to 24 carbon atoms or a heteroaryl group having 4 to 24 carbon atoms, which is substituted or unsubstituted (as substituents, a halogen atom, a hydroxy group, a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkoxy group having 1 to 12 carbon atoms, a linear or branched haloalkyl group having 1 to 12 carbon atoms substituted with at least one halogen atom, a linear or branched haloalkoxy group having 1 to 12 carbon atoms substituted with at least one halogen atom, a phenoxy group or a naphthoxy group substituted with at least one linear or branched alkyl group or alkoxy group having 1 to 12 carbon atoms, a linear or branched alkenyl group having 2 to 12 carbon atoms, and an amino group, and having at least one substituent selected therefrom.); an aralkyl or heteroaralkyl group (wherein a linear or branched alkyl group having 1 to 4 carbon atoms is substituted with the above aryl group or heteroaryl group); a substituted or unsubstituted phenoxy or naphthoxy group (having at least one substituent selected from a linear or branched alkyl group or alkoxy group having 1 to 6 carbon atoms as a substituent); -NH2, -NHR, -CONH2, or -CONHR (R is a linear or branched alkyl group having 1 to 6 carbon atoms.); -OCOR8 or -COOR8 (wherein R8 is a linear or branched alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms, or in R1, R2, a phenyl group or an unsubstituted phenyl group substituted by at least one of the substituents of a substituted aryl or substituted heteroaryl group.); represents m is an integer from 0 to 4; A is an annelated ring of the following formula (A2) or formula (A4) represents, and in these annelated rings, the dotted line represents the carbon C5 - carbon C6 bond of the naphthopyran ring of the general formula (5); the α - bond of the annelated ring (A4) can be bonded to carbon C5 or carbon C6 of the naphthopyran ring of the general formula (5); R4 is the same or different and independently represents OH, a linear or branched alkyl group or alkoxy group having 1 to 6 carbon atoms, or two R4s form a carbonyl (CO); R5 is a halogen; a linear or branched alkyl group having 1 to 12 carbon atoms; a linear or branched haloalkyl group having 1 to 6 carbon atoms substituted by at least one halogen atom; a cycloalkyl group having 3 to 12 carbon atoms; a linear or branched alkoxy group having 1 to 6 carbon atoms; a substituted or unsubstituted phenyl or benzyl group (as a substituent, when the R 1 and R 2 groups independently correspond to an aryl or heteroaryl group, it has at least one of the substituents described above in the definition of the R1, R2 groups.). -NH2, -NHR (wherein R is a linear or branched alkyl group having 1 to 6 carbon atoms.); A phenoxy or naphthoxy group which is substituted or unsubstituted (having, as a substituent, at least a linear or branched alkyl group or alkoxy group having 1 to 6 carbon atoms). -COR9, -COOR9 or -CONHR9 group (wherein R9 is a linear or branched alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted phenyl or benzyl group (as a substituent, R in general formula (5) 1 , R 2 When the group corresponds to an aryl or heteroaryl group independently, it has at least one of the substituents described above in the definition of R1 and R2 groups). When A represents (A 4 ), n is an integer from 0 to 2, p is an integer from 0 to 4, and when A represents (A 2 ), n is an integer from 0 to 2.).
[15] A molded article according to any one of [1] to
[14] , wherein the functional group equivalent ratio (B / A) of the polyol compound (B) to the polyisocyanate compound (A) is 0.02 to 0.6, and the functional group equivalent ratio (C / A) of the active hydrogen compound (C) to the polyisocyanate compound (A) is 0.4 to 0.98.
[16] An optical material comprising a molded article according to any one of [1] to
[15] .
[17] A plastic lens comprising a molded article according to any one of [1] to
[15] .
[18] A plastic polarizing lens comprising a polarizing film and a base material layer formed on at least one surface of the polarizing film, the base material layer comprising a molded article according to any one of [1] to
[15] .
[19] (A) A polyisocyanate compound, and (B) The following general formula (1) (In formula (1), m represents a numerical value from 1 to 20, k represents 0 to 2m, n represents a numerical value from 1 to 20, l represents 0 to 2n, a represents a numerical value of 0 or more, b represents a numerical value of 0 or more, d represents a numerical value of 0 or more, and e represents a numerical value of 1 or more. Q 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and a plurality of Qs 1 may be the same or different. Q2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and a plurality of Qs 2 may be the same or different. Z represents a divalent organic group having 1 to 30 carbon atoms which may contain an aromatic group, and a plurality of Zs may be the same or different. ) represented by a polyol compound having a number average molecular weight of 100 or more, and (C) a polyfunctional active hydrogen compound (excluding the compound (B)), and (D) a photochromic compound, and is a polymerizable composition containing The molar ratio of the NCO groups contained in the polyisocyanate compound (A) to the total of the OH groups and SH groups contained in the active hydrogen compound (C) and the polyol compound (B) (NCO groups / (OH groups + SH groups)) is in the range of 1.1 to 1.6, a polymerizable composition for optical materials.
[20] (A) a polyisocyanate compound, and (B) the following general formula (1) (In the formula (1), m represents a numerical value of 1 to 20, k represents 0 to 2m, n represents a numerical value of 1 to 20, l represents 0 to 2n, a represents a numerical value of 0 or more, b represents a numerical value of 0 or more, d represents a numerical value of 0 or more, and e represents a numerical value of 1 or more. Q 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and a plurality of Qs 1 may be the same or different. Q 2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and a plurality of Qs 2 may be the same or different. Z represents a divalent organic group having 1 to 30 carbon atoms which may contain an aromatic group, and a plurality of Zs may be the same or different. ) represented by a polyol compound having a number average molecular weight of 100 or more, and (C) a polyfunctional active hydrogen compound (excluding the compound (B)), and Step of preparing a polymerizable composition for an optical material by mixing (D) a photochromic compound with a polyisocyanate compound (A) such that the molar ratio of the NCO groups contained in the polyisocyanate compound (A) to the total of the OH groups and SH groups contained in the active hydrogen compound (C) and the polyol compound (B) (NCO groups / (OH groups + SH groups)) is in the range of 1.1 to 1.6. Step of forming a lens substrate by casting and polymerizing the polymerizable composition for an optical material in a mold. A method for manufacturing a plastic lens, comprising the above steps.
[21] (A) A polyisocyanate compound, (B) A polyol compound represented by the following general formula (1) (In formula (1), m represents a numerical value from 1 to 20, k represents 0 to 2m, n represents a numerical value from 1 to 20, l represents 0 to 2n, a represents a numerical value of 0 or more, b represents a numerical value of 0 or more, d represents a numerical value of 0 or more, and e represents a numerical value of 1 or more. Q 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and a plurality of Qs 1 may be the same or different. Q 2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and a plurality of Qs 2 may be the same or different. Z represents a divalent organic group having 1 to 30 carbon atoms which may contain an aromatic group, and a plurality of Zs may be the same or different.) having a number average molecular weight of 100 or more, (C) A polyfunctional active hydrogen compound (excluding the compound (B)), (D) A photochromic compound, are mixed such that the molar ratio of the NCO groups contained in the polyisocyanate compound (A) to the total of the OH groups and SH groups contained in the active hydrogen compound (C) and the polyol compound (B) (NCO groups / (OH groups + SH groups)) is in the range of 1.1 to 1.6 to prepare a polymerizable composition for an optical material. Step of fixing a polarizing film in a lens casting mold in a state separated from the mold. A step of injecting the polymerizable composition for an optical material into at least one of the voids formed between the polarizing film and the mold; A step of polymerizing and curing the polymerizable composition for an optical material to laminate a base material layer on at least one surface of the polarizing film; A method for manufacturing a plastic polarizing lens, comprising: According to the molded body of the present invention, the deterioration of the photochromic performance over time is suppressed, and the photochromic performance can be stably exhibited, and a polyurethane-based optical material or a polythiourethane-based optical material containing a photochromic compound can be provided from the molded body. According to the polymerizable composition for an optical material of the present invention, the molded body can be preferably obtained. The molded body of the present invention is obtained by polymerizing and curing a polymerizable composition containing the following compounds (A) to (D), and the SH group concentration by IR analysis is less than 1.0 wt%. (A) Polyisocyanate compound (B) A polyol compound represented by the following general formula (1) and having a number average molecular weight of 100 or more (C) A polyfunctional active hydrogen compound (excluding the compound (B)) (D) Photochromic compound In formula (1), m represents a numerical value from 1 to 20, k represents a numerical value from 0 to 2m, n represents a numerical value from 1 to 20, l represents a numerical value from 0 to 2n, a represents a numerical value of 0 or more, b represents a numerical value of 0 or more, d represents a numerical value of 0 or more, and e represents a numerical value of 1 or more. Q 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and a plurality of Qs 1 may be the same or different. Q 2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and a plurality of Qs 2 may be the same or different. Z represents a divalent organic group having 1 to 30 carbon atoms which may contain an aromatic group, and a plurality of Zs may be the same or different. According to the molded body of the present invention, the deterioration of the photochromic performance over time is suppressed, and the photochromic performance can be stably exhibited. The molded article of the present invention can be obtained by using the polymerizable composition for an optical material of the present embodiment. First, the polymerizable composition for an optical material will be described based on the following embodiments. The polymerizable composition for an optical material of the present embodiment is (A) a polyisocyanate compound, (B) a polyol compound represented by the following general formula (1) and having a number average molecular weight of 100 or more, (C) a polyfunctional active hydrogen compound (excluding the compound (B)), and (D) a photochromic compound. The molar ratio of the NCO groups contained in the polyisocyanate compound (A) to the total of the OH groups and SH groups contained in the active hydrogen compound (C) and the polyol compound (B) (NCO groups / (OH groups + SH groups)) is in the range of 1.1 to 1.6. In formula (1), m represents a numerical value from 1 to 20, k represents 0 to 2m, n represents a numerical value from 1 to 20, l represents 0 to 2n, a represents a numerical value of 0 or more, b represents 0 or more, d represents a numerical value of 0 or more, and e represents a numerical value of 1 or more. Q 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and a plurality of Qs 1 may be the same or different. Q 2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and a plurality of Qs 2 may be the same or different. Z represents a divalent organic group having 1 to 30 carbon atoms which may contain an aromatic group, and a plurality of Zs may be the same or different. The polymerizable composition for an optical material according to this embodiment is presumed to effectively suppress the hindrance of the isomerization reaction of the photochromic compound (D) in the polymer matrix of the composition by including the compounds (A) to (C) in its constitution. That is, by adding the compound (B), which is an essential component of the present invention, to a conventional resin used for spectacle lenses and the like composed of the compounds (A) and (C), an appropriate space is formed in the matrix molecular chain such that the isomerization reaction of the photochromic compound easily occurs. As a result, it is considered that good photochromic performance is realized. Further, with this configuration, it is possible to provide an optical material with excellent balance that exhibits high photochromic performance and has excellent mechanical physical properties, which are characteristics of poly(thio)urethane-based resins. Furthermore, according to the polymerizable composition for an optical material of the present invention, it is possible to provide a molded article in which the deterioration of the photochromic compound over time is suppressed and the photochromic performance can be stably exhibited. Hereinafter, each component will be described. [(A) Polyisocyanate compound] Examples of the polyisocyanate compound (A) include aliphatic polyisocyanate compounds such as hexamethylene diisocyanate, pentamethylene diisocyanate, 2,2,4-trimethylhexane diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, lysine diisocyanatomethyl ester, lysine triisocyanate, m-xylylene diisocyanate, o-xylylene diisocyanate, p-xylylene diisocyanate, xylylene diisocyanate, α,α,α′,α′-tetramethylxylylene diisocyanate, bis(isocyanatomethyl)naphthalene, 1,3,5-tris(isocyanatomethyl)benzene, bis(isocyanatomethyl)sulfide, bis(isocyanatoethyl)sulfide, bis(isocyanatomethyl)disulfide, bis(isocyanatoethyl)disulfide, bis(isocyanatomethylthio)methane, bis(isocyanatoethylthio)methane, bis(isocyanatoethylthio)ethane, bis(isocyanatomethylthio)ethane; Aliphatic polyisocyanate compounds such as isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane, 1,2-bis(isocyanatomethyl)cyclohexane, 1,3-bis(isocyanatomethyl)cyclohexane, 1,4-bis(isocyanatomethyl)cyclohexane, dicyclohexylmethane diisocyanate, dicyclohexylmethane-4,4'-diisocyanate, dicyclohexylmethane-2,4'-diisocyanate, cyclohexane diisocyanate, methylcyclohexane diisocyanate, dicyclohexyldimethylmethane isocyanate, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 3,8-bis(isocyanatomethyl)tricyclodecane, 3,9-bis(isocyanatomethyl)tricyclodecane, 4,8-bis(isocyanatomethyl)tricyclodecane, 4,9-bis(isocyanatomethyl)tricyclodecane; Aromatic polyisocyanate compounds such as diphenyl sulfide-4,4-diisocyanate, tolylene diisocyanate, phenylene diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, diphenylmethane diisocyanate; Heterocyclic polyisocyanate compounds such as 2,5-diisocyanatothiophene, 2,5-bis(isocyanatomethyl)thiophene, 2,5-diisocyanatotetrahydrothiophene, 2,5-bis(isocyanatomethyl)tetrahydrothiophene, 3,4-bis(isocyanatomethyl)tetrahydrothiophene, 2,5-diisocyanato-1,4-dithiane, 2,5-bis(isocyanatomethyl)-1,4-dithiane, 4,5-diisocyanato-1,3-dithiolane, 4,5-bis(isocyanatomethyl)-1,3-dithiolane and the like can be mentioned. As the polyisocyanate compound (A), at least one selected from these can be used. As the polyisocyanate compound (A), in addition to monomers, cases of modified products and / or mixtures with modified products are also included. Examples of modified products of isocyanate include multimers, biuret-modified products, allophanate-modified products, oxadiazinetrione-modified products, polyol-modified products, and the like. Examples of multimers include dimers such as uretdione, uretoimine, and carbodiimide, and multimers of trimer or higher such as isocyanurate and iminooxadiazinedione. As the polyisocyanate compound (A), hexamethylene diisocyanate, pentamethylene diisocyanate, m-xylylene diisocyanate, isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane, dicyclohexylmethane diisocyanate, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, tolylene diisocyanate, phenylene diisocyanate, diphenylmethane diisocyanate are preferred. m-Xylylene diisocyanate, isophorone diisocyanate, bis(isocyanatomethyl)cyclohexane, dicyclohexylmethane diisocyanate, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane are more preferred. These polyisocyanate compounds may be used alone or as a mixture of two or more. [(B) Polyol compound] In this embodiment, as the polyol compound (B), one or more compounds selected from compounds represented by the following general formula (1) and having a number average molecular weight of 100 or more can be used. The number average molecular weight of the polyol compound (B) has a lower limit of 100 or more, preferably 200 or more, more preferably 300 or more, still more preferably 400 or more, and an upper limit of 4000 or less, more preferably 3000 or less, still more preferably 2000 or less. The upper limit and the lower limit can be appropriately combined. In formula (1), m represents a numerical value from 1 to 20, preferably from 1 to 10, and more preferably from 2 to 5. n represents a numerical value from 1 to 20, preferably from 1 to 10, and more preferably from 2 to 5. a represents a numerical value of 0 or more, preferably from 0 to 100, and more preferably from 0 to 25. b represents a numerical value of 0 or more, preferably from 0 to 200, and more preferably from 0 to 100. d represents a numerical value of 0 or more, preferably from 1 to 200, and more preferably from 1 to 100. e represents a numerical value of 1 or more, preferably from 1 to 200, and more preferably from 1 to 100. k represents 0 to 2m, and l represents 0 to 2n. Q 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. A plurality of Qs 1 may be the same or different. Q 2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. A plurality of Qs 2 may be the same or different. Z is a divalent organic group having 1 to 30 carbon atoms which may contain an aromatic group, preferably a divalent organic group having 1 to 20 carbon atoms which may contain an aromatic group. A plurality of Zs may be the same or different. Examples of the "divalent organic group having 1 to 30 carbon atoms which may contain an aromatic group" include substituted or unsubstituted chain or cyclic aliphatic groups having 1 to 30 carbon atoms such as methylene group, ethylene group, trimethylene group, tetramethylene group, pentamethylene group, cyclopentylene group, hexamethylene group, cyclohexylene group, heptamethylene group, octamethylene group, nonamethylene group, decamethylene group, undecamethylene group, dodecamethylene group, tridecamethylene group, tetradecamethylene group, pentadecamethylene group, etc.; Substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, such as a phenylene group, a naphthylene group, an anthracene group, a diphenylmethane group, a 1,1-diphenylethane group, a 1,1,1-methyldiphenylethane group, a diphenylpropane group, a diphenyl ether group, a diphenyl sulfide group, a diphenyl sulfoxide group, a diphenyl sulfone group, a diphenyl ketone group, a phenyl benzoate group, a biphenyl group, a stilbene group, a diazobenzene group, an aniline benzylidene group; -C6H4-CH2- group, -CH2-C6H4-CH2- group, -CH2-C6H3(Cl)-CH2- group, -C 10 H6-CH2- group, -CH2-C 10 H6-CH2- group, -CH2CH2-C6H4-CH2CH2- group and other substituted or unsubstituted aromatic-aliphatic groups having 6 to 30 carbon atoms; or -C(O)-R 7 -C(O)-(R 7 represents a substituted or unsubstituted linear or branched alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms. ), -C(O)-R 8 -(R 8 represents a substituted or unsubstituted linear or branched alkylene group having 1 to 20 carbon atoms. ) and other carbonyl group-containing compounds having 1 to 30 carbon atoms; and the like. These organic groups may be substituted with a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or the like. In order to impart good coloring performance to the polymer (molded body) obtained from the polymerizable composition of the present embodiment, it is necessary to set the molecular weight of the polyol compound (B) to be added within an appropriate range. In the present embodiment, as the polyol compound (B), one or more compounds selected from the compounds represented by the general formulas (I) to (IV) can be used. (Compound represented by general formula (I)) In formula (I), p represents a numerical value from 4 to 100, preferably a numerical value from 15 to 50. X represents a hydrogen atom or a methyl group, and a plurality of Xs may be the same or different. X is preferably a methyl group. Examples of the compound represented by the general formula (I) include polyethylene glycol and polypropylene glycol. These may contain low molecular weight oligomers such as ethylene glycol, diethylene glycol, and triethylene glycol, and may be used alone or as a mixture of two or more. The number average molecular weight of the compound represented by the general formula (I) has a lower limit of 100 or more, preferably 200 or more, more preferably 300 or more, and even more preferably 400 or more, and an upper limit of 4000 or less, more preferably 3000 or less, and even more preferably 2000 or less. The upper and lower limits can be appropriately combined. When the number average molecular weight of the compound represented by the general formula (I) is within the above range, the photochromic performance can be effectively exhibited without impairing excellent properties such as the mechanical strength of the poly(thio)urethane resin. For example, when the compound represented by the general formula (I) is polyethylene glycol, the coloring performance is further improved and the turbidity of the polymer is further suppressed when the number average molecular weight is from 400 to 2000. Also, when the compound represented by the general formula (I) is polypropylene glycol, the coloring performance is further improved and the turbidity of the polymer is further suppressed when the number average molecular weight is from 400 to 1000. In addition, in the case of polypropylene glycol, the resulting polymer gives higher heat resistance and rigidity than polyethylene glycol. Therefore, polypropylene glycol may be more preferable than polyethylene glycol for applications used in various environments and conditions such as ophthalmic lenses. (Compound represented by general formula (II)) In formula (II), q and r may be the same or different and each represents a numerical value of 1 or more, preferably a numerical value of 6 to 25. q and r can take numerical values such that the sum of q and r satisfies a numerical value of 2 to 100, preferably a numerical value of 12 to 50. R 1 and R 2 may be the same or different and each represents a hydrogen atom or a methyl group, and a plurality of R 1 or R 2 may each be the same or different. Z represents a substituted or unsubstituted divalent aromatic group, or a divalent aliphatic group which may contain a substituted or unsubstituted aromatic group having 1 to 20 carbon atoms. Note that Z does not contain -Ph-C(CH 3 )( 2 -Ph-(Ph: phenylene group). Examples of the substituted or unsubstituted divalent aromatic group include a phenylene group, a naphthylene group, an anthracene group, a diphenylmethane group, a 1,1-diphenylethane group, a 1,1,1-methyldiphenylethane group, a 1,3-diphenylpropane group, a 1,2-diphenylpropane group, a diphenyl ether group, a diphenyl sulfide group, a diphenyl sulfoxide group, a diphenyl sulfone group, a diphenyl ketone group, a phenyl benzoate group, a biphenyl group, a stilbene group, a diazobenzene group, an aniline benzylidene group, and derivatives thereof. Examples of the divalent aliphatic group which may contain a substituted or unsubstituted aromatic group having 1 to 20 carbon atoms include a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a divalent group derived from a bisalkoxy aromatic compound having 1 to 20 carbon atoms, and the like. Examples of the substituted or unsubstituted alkylene group having 1 to 20 carbon atoms include a butylene group, a pentylene group, a nonylene group, and the like. Examples of the bisalkoxy aromatic compound having 1 to 20 carbon atoms include 1,4-bis(hydroxyethoxy)benzene, (1,3-bis(m-hydroxyethoxy)benzene, 2,2-[(1,1-biphenyl)-4,4-diylbis(oxy)]bisethanol, and the like. Examples of the substituents of the divalent aromatic group and the divalent aliphatic group include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and the like. In this embodiment, Z is preferably a phenylene group, a naphthylene group, or a biphenylene group. Examples of the compound represented by the general formula (II) include polyethylene glycol adducts such as 1,4-butanediol, 3-methyl-1,5-pentanediol, 1,9-nonanediol, 1,4-bis(hydroxyethoxy)benzene, 1,3-bis(m-hydroxyethoxy)benzene, 2,2-[(1,1-biphenyl)-4,4-diylbis(oxy)]bisethanol, and polypropylene glycol adducts. These may be used alone or as a mixture of two or more. Note that the compound represented by the general formula (II) does not include the compound represented by the general formula (III). The number average molecular weight of the compound represented by the general formula (II) has a lower limit of 200 or more, preferably 300 or more, more preferably 400 or more, and even more preferably 500 or more, and an upper limit of 4000 or less, preferably 3000 or less, more preferably 2000 or less, and even more preferably 1000 or less. The upper and lower limits can be appropriately combined. When the number average molecular weight of the compound represented by the general formula (II) is within the above range, the photochromic performance can be effectively exhibited without impairing excellent properties such as the mechanical strength of the poly(thio)urethane resin. (Compound represented by the general formula (III)) In the formula (III), q and r may be the same or different and each represents a numerical value of 1 or more, preferably a numerical value of 6 to 25. q and r can take numerical values such that the sum of q and r satisfies a numerical value of 2 to 100, preferably 12 to 50. R 1 and R 2 may be the same or different and each represents a hydrogen atom or a methyl group, and a plurality of R 1 or R 2 may be the same or different from each other. Examples of the compound represented by the general formula (III) include polyethylene glycol adducts of bisphenol A and polypropylene glycol adducts of bisphenol A. These may be used alone or as a mixture of two or more. The number average molecular weight of the compound represented by the general formula (III) has a lower limit of 316 or more, preferably 400 or more, more preferably 500 or more, and an upper limit of 4000 or less, preferably 3000 or less, more preferably 2000 or less, still more preferably 1500 or less. The upper and lower limits can be combined as appropriate. When the number average molecular weight of the compound represented by the general formula (III) is within the above range, the photochromic performance can be effectively exhibited without impairing excellent properties such as the mechanical strength of the poly(thio)urethane resin. For example, when the compound represented by the general formula (III) is a polyethylene glycol adduct of bisphenol A or a polypropylene glycol adduct of bisphenol A, the coloring performance is further improved and the turbidity of the polymer is further suppressed when the number average molecular weight is 400 to 1000. (Compound represented by the general formula (IV)) In the formula (IV), m represents a numerical value of 1 to 20, preferably 1 to 10, more preferably 2 to 5. n represents a numerical value of 1 to 20, preferably 1 to 10, more preferably 2 to 5. f represents a numerical value of 0 or more, preferably 0 to 100, more preferably 0 to 25. g represents a numerical value of 1 or more, preferably 1 to 200, more preferably 1 to 100. h represents a numerical value of 1 or more, preferably 1 to 200, more preferably 1 to 100. j represents a numerical value of 1 or more, preferably 1 to 200, more preferably 1 to 100. k represents 0 to 2m, and l represents 0 to 2n. Q 1 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. A plurality of Qs 1They may be the same or different. Q 2 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. When there are a plurality of Qs 2 they may be the same or different. R 3 represents a linear or branched alkylene group having 1 to 20 carbon atoms, or a phenylene group which may have a linear or branched alkyl group having 1 to 10 carbon atoms as a substituent. When there are a plurality of Rs 3 they may be the same or different. Examples of the compound represented by the general formula (IV) include polyester compounds composed of a diol compound and a dicarboxylic acid. The diol compound constituting the polyester compound is not particularly limited, but aliphatic diols having 2 to 12 carbon atoms in the main chain are preferably used. Examples thereof include ethylene glycol, propylene glycol, 1,4 - butanediol, 3 - methyl - 1,5 - pentanediol, 1,9 - nonanediol and the like. Also, the dicarboxylic acid constituting the polyester compound is not particularly limited, but aliphatic dicarboxylic acids and aromatic dicarboxylic acids having 2 to 12 carbon atoms in the main chain are preferably used. Examples thereof include succinic acid, adipic acid, sebacic acid, isophthalic acid, terephthalic acid and the like. The polyester compound can be used by appropriately combining one or more of these diol compounds and one or more of the dicarboxylic acids. In addition, polyester compounds obtained by ring - opening polymerization of lactones can also be used in the present invention. Examples of the lactone compound include α - acetolactone, β - propiolactone, γ - butyrolactone, δ - valerolactone and the like. The number - average molecular weight of the compound represented by the general formula (IV) has a lower limit of 600 or more, preferably 800 or more, more preferably 1000 or more, and an upper limit of 4000 or less, more preferably 3000 or less, still more preferably 2000 or less. The upper limit and the lower limit can be appropriately combined. When the number average molecular weight of the compound represented by the general formula (IV) is within the above range, the photochromic performance can be effectively exhibited without impairing excellent properties such as the mechanical strength of the poly(thio)urethane resin. For example, when the compound represented by the general formula (IV) is a polyester compound obtained by reacting 3-methyl-1,5-pentanediol with an equimolar mixture of adipic acid and isophthalic acid in an equimolar amount, the color development performance is more improved and the polymer turbidity is more suppressed when the number average molecular weight is 1000 to 2000. By using the polyol compound (B) composed of the above compounds, the photochromic performance can be effectively exhibited. In the present embodiment, as the polyol compound (B), one or more compounds selected from the compounds represented by the general formula (I) to the compounds represented by the general formula (IV) can be used, and from the viewpoint of the above effects, the compounds represented by the general formula (I), the general formula (III) or the general formula (IV) can be preferably used. In the present embodiment, the polyol compound (B) can be used in the range of 0.3 to 6 times by weight based on the weight of the bifunctional or higher active hydrogen compound (C). In the present embodiment, it is used within the above range so that the resin performance required depending on the application can be obtained while maintaining high photochromic performance. Preferably, it is in the range of 0.7 to 5 times by weight. When the weight multiple of the polyol compound (B) with respect to the active hydrogen compound (C) is within the above range, high dimming performance, that is, a high color development density and a fast density change can be preferably exhibited. Furthermore, since the crosslinking density is in an optimal range, an optical material having more excellent properties such as rigidity, surface hardness, and heat resistance can be obtained. [(C) Bifunctional or higher active hydrogen compound] The bifunctional or higher active hydrogen compound (C) (hereinafter simply referred to as "active hydrogen compound (C)") is not particularly limited, and examples thereof include polyol compounds, polythiol compounds, thiol compounds having a hydroxy group, and the like. These can be used in appropriate combinations. It is not possible to select only polyol compounds. For the active hydrogen compound (C), the molar ratio of the SH group to the total of the SH group and the OH group (SH / (SH + OH)) is 0.01 to 1.0, preferably 0.1 to 1.0, more preferably 0.3 to 1.0. Note that the active hydrogen compound (C) does not contain the polyol compound (B). Examples of the polyol compound include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, butylene glycol, neopentyl glycol, glycerin, trimethylolethane, trimethylolpropane, ditrimethylolpropane, butanetriol, 1,2-methyl glucoside, pentaerythritol, dipentaerythritol, tripentaerythritol, sorbitol, erythritol, threitol, ribitol, arabinitol, xylitol, allitol, mannitol, dulcitol, iditol, glycol, inositol, hexanetriol, triglycerose, digliperol, triethylene glycol, polyethylene glycol, tris(2-hydroxyethyl) isocyanurate, cyclobutanediol, cyclopentanediol, cyclohexanediol, cycloheptanediol, cyclooctanediol, cyclohexanedimethanol, hydroxypropylcyclohexanol, tricyclo 2,6 [5.2.1.0]decane-dimethanol, bicyclo[4.3.0]-nonanediol, dicyclohexanediol, tricyclo[5.3.1.1]dodecanediol, bicyclo[4.3.0]nonanedimethanol, tricyclo[5.3.1.1]dodecane-diethanol, hydroxypropyltricyclo[5.3.1.1]dodecanol, spiro[3.4]octanediol, butylcyclohexanediol, 1,1'-bicyclohexylidenediol, cyclohexanetriol, maltitol, lactose and other aliphatic polyols; Aromatic polyols such as dihydroxynaphthalene, trihydroxynaphthalene, tetrahydroxynaphthalene, dihydroxybenzene, benzenetriol, biphenyltetraol, pyrogallol, (hydroxynaphthyl)pyrogallol, trihydroxyphenanthrene, bisphenol A, bisphenol F, xylylene glycol, di(2-hydroxyethoxy)benzene, bisphenol A-bis-(2-hydroxyethyl ether), tetrabromobisphenol A, tetrabromobisphenol A-bis-(2-hydroxyethyl ether); Halogenated polyols such as dibromoneopentyl glycol; And polymer polyols such as epoxy resins. In this embodiment, at least one selected from these can be used in combination. In addition, as the polyol compound, a condensation reaction product of an organic acid such as oxalic acid, glutamic acid, adipic acid, acetic acid, propionic acid, cyclohexanecarboxylic acid, β-oxocyclohexanepropionic acid, dimer acid, phthalic acid, isophthalic acid, salicylic acid, 3-bromopropionic acid, 2-bromoglycol, dicarboxycyclohexane, pyromellitic acid, butanetetracarboxylic acid, bromophthalic acid and the above polyol; An addition reaction product of the above polyol and an alkylene oxide such as ethylene oxide or propylene oxide; An addition reaction product of an alkylene polyamine and an alkylene oxide such as ethylene oxide or propylene oxide; furthermore, Bis-[4-(hydroxyethoxy)phenyl]sulfide, bis-[4-(2-hydroxypropoxy)phenyl]sulfide, bis-[4-(2,3-dihydroxypropoxy)phenyl]sulfide, bis-[4-(4-hydroxycyclohexyloxy)phenyl]sulfide, bis-[2-methyl-4-(hydroxyethoxy)-6-butylphenyl]sulfide and compounds obtained by adding an average of 3 molecules or less of ethylene oxide and / or propylene oxide per hydroxyl group to these compounds; Examples of the polyol containing a sulfur atom include di-(2-hydroxyethyl) sulfide, 1,2-bis-(2-hydroxyethyl mercapto) ethane, bis(2-hydroxyethyl) disulfide, 1,4-dithiane-2,5-diol, bis(2,3-dihydroxypropyl) sulfide, tetrakis(4-hydroxy-2-thiabutyl) methane, bis(4-hydroxyphenyl) sulfone (trade name: bisphenol S), tetrabromobisphenol S, tetramethylbisphenol S, 4,4'-thiobis(6-tert-butyl-3-methylphenol), 1,3-bis(2-hydroxyethylthioethyl)-cyclohexane, and the like. In the present embodiment, at least one selected from these can be used in combination. Examples of the polythiol compound include methanedithiol, 1,2-ethanedithiol, 1,2,3-propanetrithiol, 1,2-cyclohexanedithiol, bis(2-mercaptoethyl) ether, tetrakis(mercaptomethyl)methane, diethylene glycol bis(2-mercaptoacetate), diethylene glycol bis(3-mercaptopropionate), ethylene glycol bis(2-mercaptoacetate), ethylene glycol bis(3-mercaptopropionate), trimethylolpropane tris(2-mercaptoacetate), trimethylolpropane tris(3-mercaptopropionate), trimethylolethane tris(2-mercaptoacetate), trimethylolethane tris(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), bis(mercaptomethyl) sulfide, bis(mercaptomethyl) disulfide, bis(mercaptoethyl) sulfide, bis(mercaptoethyl) disulfide, bis(mercaptopropyl) sulfide, bis(mercaptomethylthio)methane, bis(2-mercaptoethylthio)methane, bis(3-mercaptopropylthio)methane, 1,2-bis(mercaptomethylthio)ethane, 1,2-bis(2-mercaptoethylthio)ethane, 1,2-bis(3-mercaptopropylthio)ethane, 1,2,3-tris(mercaptomethylthio)propane, 1,2,3-tris(2-mercaptoethylthio)propane, 1,2,3-tris(3-mercaptopropylthio)propane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, tetrakis(mercaptomethylthiomethyl)methane, tetrakis(2-mercaptoethylthiomethyl)methane, tetrakis(3-mercaptopropylthiomethyl)methane, bis(2,3-dimercaptopropyl) sulfide, 2,5-dimercaptomethyl-1,4-dithiane, 2,5-dimercapto-1,4-dithiane, 2,5-dimercaptomethyl-2,5-dimethyl-1,4-dithiane, and esters of these with thioglycolic acid and mercaptopropionic acid, hydroxymethylsulfide bis(2-mercaptoacetate), hydroxymethylsulfide bis(3-mercaptopropionate), hydroxyethylsulfide bis(2-mercaptoacetate), hydroxyethylsulfide bis(3-mercaptopropionate), hydroxymethyldisulfide bis(2-mercaptoacetate), hydroxymethyldisulfide bis(3-mercaptopropionate), hydroxyethyldisulfide bis(2-mercaptoacetate), hydroxyethyldisulfide bis(3-mercaptopropionate), 2-mercaptoethyl ether bis(2-mercaptoacetate), 2-mercaptoethyl ether bis(3-mercaptopropionate), thiodiglycolic acid bis(2-mercaptoethyl ester), thiodipropionic acid bis(2-mercaptoethyl ester), dithiodiglycolic acid bis(2-mercaptoethyl ester), dithiodipropionic acid bis(2-mercaptoethyl ester), 1,1,3,3-tetrakis(mercaptomethylthio)propane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, tris(mercaptomethylthio)methane, tris(mercaptoethylthio)methane and other aliphatic polythiol compounds; 1,2-dimercaptobenzene, 1,3-dimercaptobenzene, 1,4-dimercaptobenzene, 1,2-bis(mercaptomethyl)benzene, 1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl)benzene, 1,2-bis(mercaptoethyl)benzene, 1,3-bis(mercaptoethyl)benzene, 1,4-bis(mercaptoethyl)benzene, 1,3,5-trimercaptobenzene, 1,3,5-tris(mercaptomethyl)benzene, 1,3,5-tris(mercaptomethyleneoxy)benzene, 1,3,5-tris(mercaptoethyleneoxy)benzene, 2,5-toluenedithiol, 3,4-toluenedithiol, 1,5-naphthalenedithiol, 2,6-naphthalenedithiol and other aromatic polythiol compounds; 2-methylamino-4,6-dithiol-sym-triazine, 3,4-thiophenedithiol, bismuthiol, 4,6-bis(mercaptomethylthio)-1,3-dithiane, 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane and other heterocyclic polythiol compounds; Compounds represented by the following general formula (2); etc. can be mentioned, but it is not limited only to these exemplified compounds. In this embodiment, at least one selected from these can be used in combination. In formula (2), a and b independently represent an integer of 1 to 4, and c represents an integer of 1 to 3. Z is a hydrogen or methyl group, and when there are a plurality of Zs, they may be the same or different from each other. Examples of the thiol compound having a hydroxy group include 2-mercaptoethanol, 3-mercapto-1,2-propanediol, glycerin bis(mercaptoacetate), 4-mercaptophenol, 2,3-dimercapto-1-propanol, pentaerythritol tris(3-mercaptopropionate), pentaerythritol tris(thioglycolate), etc. can be mentioned, but it is not limited only to these exemplified compounds. Furthermore, oligomers of these active hydrogen compounds, halogenated substituents such as chlorine-substituted products and bromine-substituted products may be used. These active hydrogen compounds can be used alone or in combination of two or more. In this embodiment, from the viewpoint of physical properties such as the mechanical strength of the obtained molded article, it is preferable to use a trifunctional or higher functional active hydrogen compound as the active hydrogen compound (C). Specifically, at least one selected from glycerin, pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, trimethylolpropane tris(3-mercaptopropionate) is preferably used. The active hydrogen compound (C) is preferably a bifunctional or higher functional active hydrogen compound having at least one SH group. Also, as a preferable combination of the polyol compound (B) and the active hydrogen compound (C), a combination of polyethylene glycol and at least one selected from glycerin, pentaerythritol tetrakis(2-mercaptoacetate), and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, a combination of polypropylene glycol and at least one selected from pentaerythritol tetrakis(2-mercaptoacetate) and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, a combination of a polypropylene glycol adduct of bisphenol A and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, Combinations include, but are not limited to, at least one selected from polyester compounds composed of 3-methyl-1,5-pentanediol, adipic acid, and isophthalic acid, and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, etc. [(D) Photochromic compound] In this embodiment, the photochromic compound (D) is not particularly limited, and any one can be appropriately selected from conventionally known compounds that can be used in photochromic lenses. For example, one or more kinds can be used according to the desired coloring from spiro pyran compounds, spiro oxazine compounds, fulgide compounds, naphtho pyran compounds, bisimidazole compounds, and at least one selected from general formula (a) and general formula (b) described below can also be used. Examples of the spiro pyran compounds include various substituents in which the indole ring and benzene ring of indolinospirobenzopyran are substituted with halogen, methyl, ethyl, methylene, ethylene, hydroxyl group, etc., various substituents in which the indole ring and naphthalene ring of indolinospironaphthopyran are substituted with halogen, methyl, ethyl, methylene, ethylene, hydroxyl group, etc., various substituents in which the indole ring of indolinospiroquinolinopyran is substituted with halogen, methyl, ethyl, methylene, ethylene, hydroxyl group, etc., various substituents in which the indole ring of indolinospiropyridopyran is substituted with halogen, methyl, ethyl, methylene, ethylene, hydroxyl group, etc., and the like. Examples of the spirooxazine compounds include various substituted products of indolinospirophenoxazine substituted with halogen, methyl, ethyl, methylene, ethylene, hydroxyl group, etc. on the indole ring and benzene ring; various substituted products of indolinospironaphthoxazine substituted with halogen, methyl, ethyl, methylene, ethylene, hydroxyl group, etc. on the indole ring and naphthalene ring; various substituted products of indolinospiro phenanthroxazine substituted with halogen, methyl, ethyl, methylene, ethylene, hydroxyl group, etc. on the indole ring; various substituted products of indolinospiroquinolinooxazine substituted with halogen, methyl, ethyl, methylene, ethylene, hydroxyl group, etc. on the indole ring; various substituted products of piperidinospironaphthoxazine substituted with halogen, methyl, ethyl, methylene, ethylene, hydroxyl group, etc. on the piperidine ring and naphthalene ring, and the like. Examples of the fulgide compounds include N-cyanomethyl-6,7-dihydro-4-methyl-2-phenylspiro(5,6-benzo[b]thiophene dicarboximide-7,2'-tricyclo[3.3.1.1 3,7 decane], N-cyanomethyl-6,7-dihydro-2-(p-methoxyphenyl)-4-methylspiro(5,6-benzo[b]thiophene dicarboximide-7,2'-tricyclo[3.3.1.1 3,7 decane), 6,7-dihydro-N-methoxycarbonylmethyl-4-methyl-2-phenylspiro(5,6-benzo[b]thiophene dicarboximide-7,2'-tricyclo[3.3.1.1 3,7 decane), 6,7-dihydro-4-methyl-2-(p-methylphenyl)-N-nitromethylspiro(5,6-benzo[b]thiophene dicarboximide-7,2'-tricyclo[3.3.1.1 3,7 decane), N-cyanomethyl-6,7-dihydro-4-cyclopropyl-3-methylspiro(5,6-benzo[b]thiophene dicarboximide-7,2'-tricyclo[3.3.1.1 3,7 decane), N-cyanomethyl-6,7-dihydro-4-cyclopropylspiro(5,6-benzo[b]thiophene dicarboximide-7,2'-tricyclo[3.3.1.1 3,7〕decane), N-cyanomethyl-6,7-dihydro-2-(p-methoxyphenyl)-4-cyclopropylspiro(5,6-benzo[b]thiophenedicarboximide-7,2'-tricyclo[3.3.1.1 3,7 〕decane), etc. Examples of the naphthopyran-based compound include spiro[norbornane-2,2'-[2H]benz[h]chromene], spiro[bicyclo[3.3.1]nonane-9,2'-[2H]benz[h]chromene], 7'-methoxyspiro[bicyclo[3.3.1]nonane-9,2'-[2H]benz[h]chromene], 7'-methoxyspi[norbornane-2,2'-[2H]benz[f]chromene], 2,2-dimethyl-7-octyloxy[2H]benz[h]chromene, spiro[2-bicyclo[3.3.1]nonene-9,2'-[2H]benz[h]chromene], spiro[2-bicyclo[3.3.1]nonene-9,2'-[2H]benz[f]chromene], 6-morpholino-3,3-bis(3-fluoro-4-methoxyphenyl)-3H-benzo(f)chromene, 5-isopropyl-2,2-diphenyl-2H-benzo(h)chromene, etc., and compounds represented by the following general formula (3) and compounds represented by the following general formula (4). In general formula (3) and general formula (4), R 1 and R 2 may be the same or different and are independently hydrogen; a linear or branched alkyl group having 1 to 12 carbon atoms; a cycloalkyl group having 3 to 12 carbon atoms; a substituted or unsubstituted aryl group having 6 to 24 carbon atoms or a heteroaryl group having 4 to 24 carbon atoms; an aralkyl or heteroaralkyl group (a linear or branched alkyl group having 1 to 4 carbon atoms is substituted with the above aryl group or heteroaryl group). The substituents of the substituted aryl group having 6 to 24 carbon atoms or the substituted heteroaryl group having 4 to 24 carbon atoms are a halogen atom, a hydroxy group, a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkoxy group having 1 to 12 carbon atoms, a linear or branched haloalkyl group having 1 to 12 carbon atoms substituted with at least one halogen atom, a linear or branched haloalkoxy group having 1 to 12 carbon atoms substituted with at least one halogen atom, a phenoxy group or a naphthoxy group substituted with at least one linear or branched alkyl group or alkoxy group having 1 to 12 carbon atoms, a linear or branched alkenyl group having 2 to 12 carbon atoms, -NH 2 group, -NHR group, -N(R) 2 group (R is a linear or branched alkyl group having 1 to 6 carbon atoms. When two Rs are present, the two Rs may be the same or different.), and at least one selected from a methacryloyl group or an acryloyl group. R 3 may be the same or different and are independently a halogen atom; a linear or branched alkyl group having 1 to 12 carbon atoms; a cycloalkyl group having 3 to 12 carbon atoms; a linear or branched alkoxy group having 1 to 12 carbon atoms; a linear or branched haloalkyl group having 1 to 12 carbon atoms substituted with at least one halogen atom, a halocycloalkyl group having 3 to 12 carbon atoms substituted with at least one halogen atom, a linear or branched haloalkoxy group having 1 to 12 carbon atoms substituted with at least one halogen atom; An aryl group having 6 to 24 carbon atoms or a heteroaryl group having 4 to 24 carbon atoms, which may be substituted or unsubstituted (as substituents, a halogen atom, a hydroxy group, a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkoxy group having 1 to 12 carbon atoms, a linear or branched haloalkyl group having 1 to 12 carbon atoms substituted with at least one halogen atom, a linear or branched haloalkoxy group having 1 to 12 carbon atoms substituted with at least one halogen atom, a phenoxy group or a naphthoxy group substituted with at least one linear or branched alkyl group or alkoxy group having 1 to 12 carbon atoms, a linear or branched alkenyl group having 2 to 12 carbon atoms, and an amino group, and having at least one substituent selected therefrom); An aralkyl or heteroaralkyl group (a linear or branched alkyl group having 1 to 4 carbon atoms is substituted with the above aryl group or heteroaryl group); A substituted or unsubstituted phenoxy or naphthoxy group (having at least one substituent selected from a linear or branched alkyl group or alkoxy group having 1 to 6 carbon atoms as a substituent); -NH2, -NHR, -CONH2, or -CONHR (R is a linear or branched alkyl group having 1 to 6 carbon atoms); -OCOR8 or -COOR8 (wherein R8 is a linear or branched alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms, or a phenyl group substituted with at least one of the substituents of a substituted aryl or substituted heteroaryl group or an unsubstituted phenyl group in R1, R2); represents. At least two adjacent Rs 3 are bonded to each other, and one or more aromatic ring groups or non-aromatic ring groups can be formed including the carbon atom to which R 3 is bonded. The aromatic ring group or non-aromatic ring group includes one ring or two fused rings which may contain a hetero atom selected from the group consisting of oxygen, sulfur, and nitrogen. l is an integer from 0 to 2. m is an integer from 0 to 4. In addition, other naphthopyran compounds include compounds in which a light control dye molecule is added to at least one end of a polysiloxane oligomer, a polyalkylene oxide, or a polyalkyl ester described in WO2013 / 78086, WO2012 / 149599, WO2010 / 020770, and WO2009 / 146509, and compounds in which the structures represented by the general formula (3) or (4) described above are bonded by a linking group and contain two or more naphthopyran rings in one molecule. In the naphthopyran compound represented by the general formula (3), the compound represented by the following general formula (5) (hereinafter also referred to as compound (5)) is cited as a preferred example. R 1 、R 2 、R 3 、m are the same as described above, and A represents a fused ring of the following formulas (A 1 )~(A 5 ). In these fused rings (A1) to (A5), the dotted line represents the carbon C5-carbon C6 bond of the naphthopyran ring of the general formula (5). The α bond of the fused ring (A4) or (A5) is bonded to carbon C5 or carbon C6 of the naphthopyran ring of the general formula (5). R4s are the same or different and independently represent OH, a linear or branched alkyl group or alkoxy group having 1 to 6 carbon atoms, or two R4s form a carbonyl (CO). R5, R6, and R7 are independently a halogen atom (preferably fluorine, chlorine, or bromine); a linear or branched alkyl group having 1 to 12 carbon atoms (preferably a linear or branched alkyl group having 1 to 6 carbon atoms); a linear or branched haloalkyl group having 1 to 6 carbon atoms substituted by at least one halogen atom (preferably a fluoroalkyl group); a cycloalkyl group having 3 to 12 carbon atoms; a linear or branched alkoxy group having 1 to 6 carbon atoms; A substituted or unsubstituted phenyl or benzyl group (as substituents, R in general formula (5)) 1 and R 2 , when the group corresponds to an aryl or heteroaryl group independently, R 1 and R 2 has at least one of the substituents described above in the definition of the group.). -NH2, -NHR (wherein R is a linear or branched alkyl group having 1 to 6 carbon atoms.); A substituted or unsubstituted phenoxy or naphthoxy group (having, as substituents, at least a linear or branched alkyl group or alkoxy group having 1 to 6 carbon atoms.); -COR9, -COOR9 or -CONHR9 group (wherein R9 is a linear or branched alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms, or a substituted or unsubstituted phenyl or benzyl group (as substituents, R in general formula (5)) 1 and R 2 , when the group corresponds to an aryl or heteroaryl group independently, has at least one of the substituents described above in the definition of R1 and R2 groups).). n is an integer from 0 to 6, o is an integer from 0 to 2, p is an integer from 0 to 4, and q is an integer from 0 to 3. In addition, when A represents (A 4 ), n is an integer from 0 to 2, p is an integer from 0 to 4, and when A represents (A 2 ), n is an integer from 0 to 2. The photochromic compound (D) of general formula (5) is combined with the discoloration reaction rate applicable to the required use and has high coloring suitability even at 40°C. The colors that can be easily achieved range from orange to blue. In addition, in the present embodiment, a mixture of compounds (5) belonging to at least one different type selected from the group consisting of compound (5) where A = (A1), compound (5) where A = (A2), compound (5) where A = (A3), compound (5) where A = (A4), and compound (5) where A = (A5) is also included. In this embodiment, as the compound (5), a compound represented by the following general formula (6) can be preferably used. Ar 1 and Ar 2 are aromatic groups, which may be the same or different and represent a benzene ring or a thiophene ring which may be substituted. Examples of the substituent of the benzene ring or the thiophene ring include a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, and a linear or branched alkyl mono (or di) substituted amino group having 1 to 6 carbon atoms. R 3 and R 4 and R 5 and m, n, p have the same meanings as described above. As the compound (5), a compound represented by the following general formula (7) can be more preferably used. In formula (7), R 10 and R 11 may be the same as or different from each other and represent a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 10 carbon atoms, or a linear or branched alkyl mono (or di) substituted amino group having 1 to 6 carbon atoms. When m is 2, adjacent R 3 can be bonded to each other to form a ring structure including the carbon atom to which R 3 is bonded. r and s are integers from 0 to 4. The above ring structure is an aryl group having 6 to 24 carbon atoms or a heteroaryl group having 3 to 24 carbon atoms which may be substituted or unsubstituted. R 3 and R 4 and R 5 and m, n, p have the same meanings as described above. Specific examples of the compound represented by the general formula (7) include compounds represented by the following formula (8) or the following formula (9). In this embodiment, the compounds represented by formula (8) and formula (9) are preferred. The compound represented by the general formula (5), which is the photochromic compound (D), can be synthesized by a known method. For example, it can also be synthesized by the method described in JP-T-2004-500319. Further, as specific examples of the naphthopyran compound represented by the general formula (3), the compound represented by the following formula (10) can be mentioned as a preferable example. As the naphthopyran compound, one or more compounds selected from the compounds described above may be used. As the photochromic compound (D) in the present embodiment, at least one selected from the general formula (a) and the general formula (b) can also be used. PC-L-Chain (a) PC-L-Chain-L'-PC' (b) PC and PC' represent monovalent groups derived from the compounds of the general formulas (c) to (f). PC and PC' may be the same or different. In the formulas (c) to (f), R 1 to R 18 represent hydrogen, a halogen atom, a carboxyl group, an acetyl group, a formyl group, an optionally substituted C1-C20 aliphatic group, an optionally substituted C3-C20 alicyclic group, or an optionally substituted C6-C20 aromatic organic group, and may be the same or different from each other. These aliphatic groups, alicyclic groups or aromatic organic groups may contain an oxygen atom or a nitrogen atom. Any one of the groups contained in the compounds represented by the general formulas (c) to (f) is bonded to the divalent organic group L or L'. Examples of the C1-C20 aliphatic group that may be substituted include linear or branched C1-C10 alkyl groups, linear or branched C1-C10 alkoxy groups, linear or branched C2-C10 alkenyl groups, C1-C10 hydroxyalkyl groups, C1-C10 hydroxyalkoxy groups, C1-C10 alkyl groups substituted with C1-C10 alkoxy groups, C1-C10 alkoxy groups substituted with C1-C10 alkoxy groups, C1-C5 haloalkyl groups, C1-C5 dihaloalkyl groups, C1-C5 trihaloalkyl groups, C1-C10 alkylamino groups, C1-C10 aminoalkyl groups, linear or branched C1-C20 alkoxycarbonyl groups, and the like. Examples of the C3-C20 alicyclic group that may be substituted include C3-C20 cycloalkyl groups, C6-C20 bicycloalkyl groups, and the like. Examples of the C6-C20 aromatic organic group that may be substituted include phenyl groups, C7-C16 alkoxyphenyl groups, arylamino groups, diarylamino groups, aryl C1-C5 alkylamino groups, cyclic amino groups, arylcarbonyl groups, aroyl groups, and the like. R 1 and R 2 are preferably a hydrogen atom; a halogen atom; linear or branched C1-C20 aliphatic groups that may be substituted, such as linear or branched C1-C10 alkyl groups, linear or branched C1-C10 alkoxy groups, C1-C10 hydroxyalkoxy groups, C1-C10 alkoxy groups substituted with C1-C10 alkoxy groups, C1-C5 haloalkyl groups, C1-C5 dihaloalkyl groups, C1-C5 trihaloalkyl groups, C1-C5 alkylamino groups; phenyl groups, C7-C16 alkoxyphenyl groups, C1-C5 dialkylamino groups, arylamino groups, diarylamino groups, aryl C1-C5 alkylamino groups, cyclic amino groups, and other C6-C20 aromatic organic groups that may be substituted; and the like. R 1 and R 2 may be the same or different from each other. R 3As such, preferably, a hydrogen atom; a halogen atom; a carboxyl group; an acetyl group; a linear or branched C1-C10 alkyl group, a linear or branched C2-C10 alkenyl group, a linear or branched C1-C10 alkoxy group, a C1-C10 hydroxyalkyl group, a C1-C10 alkyl group substituted with a C1-C10 alkoxy group, a C1-C10 aminoalkyl group, a linear or branched C1-C20 alkoxycarbonyl group, etc., a C1-C20 aliphatic group which may be substituted; a C3-C20 cycloalkyl group, a C6-C20 bicycloalkyl group, etc., a C3-C20 alicyclic group which may be substituted; an arylcarbonyl group, a formyl group, an aroyl group, etc., a C6-C20 aromatic organic group which may be substituted; and the like can be mentioned. R 4 As such, preferably, a hydrogen atom; a halogen atom; a carboxyl group; an acetyl group; a formyl group; a linear or branched C1-C10 alkyl group, a linear or branched C2-C10 alkenyl group, a linear or branched C1-C10 alkoxy group, a C1-C10 hydroxyalkyl group, a C1-C10 alkyl group substituted with a C1-C10 alkoxy, a C1-C10 aminoalkyl group, a linear or branched C1-C20 alkoxycarbonyl group, etc., a C1-C20 aliphatic group which may be substituted; a C3-C20 cycloalkyl group, a C6-C20 bicycloalkyl group, etc., a C3-C20 alicyclic group which may be substituted; an arylcarbonyl group, an aroyl group, a phenyl group, a C7-C16 alkoxyphenyl group, a C1-C10 dialkoxyphenyl group, a C1-C10 alkylphenyl group, a C1-C10 dialkylphenyl group, etc., a C6-C20 aromatic organic group which may be substituted; and the like can be mentioned. R 3 and R 4 may be bonded to each other. R 3 and R 4 When R and R are bonded to each other to form a ring structure, the general formula (g) or (h) can be mentioned. The dotted line part is R 3represents the bond between the carbon atom to which it is attached and R 4 represents the bond between the carbon atom to which it is attached and R R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 14 、R 15 、R 16 is, R 1 、R 2 represents the same functional group as R, R. R5 to R7 may be the same or different when multiple. R 11 is preferably a hydrogen atom; a halogen atom; a C1-C20 aliphatic group which may be substituted, such as a linear or branched C1-C20 alkyl group, a C1-C5 haloalkyl group, a C1-C5 dihaloalkyl group, a C1-C5 trihaloalkyl group, etc.; a C3-C20 alicyclic group which may be substituted, such as a C3-C20 cycloalkyl group, a C6-C20 bicycloalkyl group, a C3-C20 cycloalkyl group substituted with a C1-C5 alkyl group, a C6-C20 bicycloalkyl group substituted with a C1-C5 alkyl group, etc.; a C6-C20 aromatic organic group which may be substituted, such as an aryl group substituted with a C1-C5 alkyl group, etc. can be mentioned. R 12 and R 13 is preferably a hydrogen atom; a halogen atom; a C1-C20 aliphatic group which may be substituted, such as a C1-C10 alkyl group, a C1-C5 alkylalkoxycarbonyl group, etc.; a C3-C20 alicyclic group which may be substituted, such as a C5-C7 cycloalkyl group, etc. can be shown. R 17 and R 18 is preferably a hydrogen atom; a halogen atom; a C1-C20 aliphatic group which may be substituted, such as a linear or branched C1-C10 alkyl group, a C1-C10 hydroxyalkyl group, etc.; a C3-C20 alicyclic group which may be substituted, such as a C5-C7 cycloalkyl group, etc. can be shown. In the general formula (a) or (b), L and L' represent a divalent organic group containing one or more selected from an oxyethylene chain, an oxypropylene chain, a (thio)ester group, and a (thio)amide group. Specifically, L and L' are represented by general formulas (i) to (o). L and L' may be the same or different. In formulas (i) to (o), Y represents oxygen or sulfur. R 19 represents hydrogen or a linear or branched C1-C10 alkyl group. R 20 represents a linear or branched C1-C10 alkyl group. p represents an integer from 0 to 15, and r represents an integer from 0 to 10. Q represents a linear or branched C1-C10 alkylene group, a C1-C10 alkenylene group, a divalent group derived from a 1,2-, 1,3-, or 1,4-substituted aryl group, a divalent group derived from a substituted heteroaryl group, etc. *1 and *2 represent bonds. *1 is bonded to a monovalent or divalent organic group represented by "Chain", and *2 is bonded to a monovalent organic group represented by PC or PC'. "Chain" in the general formula (a) or (b) represents a monovalent or divalent organic group containing one or more selected from a polysiloxane chain and a polyoxyalkylene chain. Examples of the polysiloxane chain include a polydimethylsiloxane chain, a polymethylphenylsiloxane chain, and a polymethylhydrosiloxane chain. Examples of the polyoxyalkylene chain include a polyoxyethylene chain, a polyoxypropylene chain, and a polyoxyhexamethylene chain. Specifically, when the photochromic compound is of the general formula (a), "Chain" represents a monovalent organic group of the general formula (p) or (q). "Chain" represents a divalent organic group of general formula (r) or (s) when the photochromic compound has the general formula (b). In formulas (p) to (s), R 21 represents a linear or branched C1-C10 alkyl group. R 22 represents a linear or branched C1-C10 alkyl group. R 23 represents hydrogen, a methyl group, or an ethyl group. n represents an integer from 4 to 75, and m represents an integer from 1 to 50. q represents an integer from 1 to 3. *3 and *4 represent bonds. *3 is bonded to the divalent organic group represented by L, and *4 is bonded to the divalent organic group represented by L'. The photochromic compound of the present invention can be obtained by the methods described in WO2009 / 146509, WO2010 / 20770, WO2012 / 149599, and WO2012 / 162725. Examples of the photochromic compound (D) in the present embodiment include Reversacol Humber Blue (polydimethylsiloxane chain, naphthopyran chromophore (general formula (c))), Reversacol Calder Blue (polydimethylsiloxane chain, naphthopyran chromophore (general formula (c))), Reversacol Trent Blue (polydimethylsiloxane chain, naphthopyran chromophore (general formula (c))), Reversacol Pennine Green (polydimethylsiloxane chain, naphthopyran chromophore (general formula (c))), Reversacol Heath Green (polyoxyalkylene chain, naphthopyran chromophore (general formula (c))), Reversacol Chilli Red (polydimethylsiloxane chain, naphthopyran chromophore (general formula (c))), Reversacol Wembley Grey (polyoxyalkylene chain, naphthopyran chromophore (general formula (c))), Reversacol Cayenne Red (polyoxyalkylene chain, naphthopyran chromophore (general formula (c))) manufactured by Vivimed. [Other components] In this embodiment, in addition to the above components (A) to (D), a polymerization catalyst, an internal release agent, a resin modifier, etc. may further be included. Examples of the polymerization catalyst include a tertiary amine compound and its inorganic acid salt or organic acid salt, a metal compound, a quaternary ammonium salt, or an organic sulfonic acid. As the internal release agent, an acidic phosphate ester can be used. Examples of the acidic phosphate ester include a phosphoric acid monoester and a phosphoric acid diester, and they can be used alone or in a mixture of two or more. Examples of the resin modifier include an olefin compound containing an episulfide compound, an alcohol compound, an amine compound, an epoxy compound, an organic acid and its anhydride, a (meth)acrylate compound, etc. <Manufacturing method of the polymerizable composition for optical materials> The polymerizable composition for optical materials of this embodiment can be prepared by mixing an isocyanate compound (A), a polyol compound (B), an active hydrogen compound (C), and a photochromic compound (D). In this embodiment, the functional group equivalent ratio (B / A) of the polyol compound (B) to the polyisocyanate compound (A) has a lower limit of 0.02 or more, preferably 0.10 or more, more preferably 0.15 or more, still more preferably 0.20 or more, particularly preferably 0.25 or more, and an upper limit of 0.60 or less, preferably 0.50 or less, more preferably 0.40 or less, still more preferably 0.30 or less. The upper limit and the lower limit can be combined as appropriate. The functional group equivalent ratio (C / A) of the active hydrogen compound (C) to the polyisocyanate compound (A) has a lower limit of 0.30 or more, preferably 0.40 or more, more preferably 0.50 or more, still more preferably 0.60 or more, and an upper limit of 0.99 or less, preferably 0.98 or less, more preferably 0.90 or less, still more preferably 0.80 or less. The upper limit and the lower limit can be combined as appropriate. By being in the range of the equivalent ratio, it is possible to provide an optical material with excellent balance, which exhibits high photochromic performance and has excellent mechanical physical properties that are characteristic of poly(thio)urethane resins. For example, when the compound represented by the general formula (I) is polyethylene glycol, the color development performance is further improved and the cloudiness of the polymer is further suppressed when the functional group equivalent ratio (B / A) is 0.1 to 0.6. Also, when the compound represented by the general formula (I) is polypropylene glycol, the color development performance is further improved and the cloudiness of the polymer is further suppressed when the functional group equivalent ratio (B / A) is 0.06 to 0.6. Regarding the compound represented by the general formula (II), the color development performance is further improved and the cloudiness of the polymer is further suppressed when the functional group equivalent ratio (B / A) is 0.06 to 0.6. Also, when the compound represented by the general formula (III) is a polyethylene glycol adduct of bisphenol A or a polypropylene glycol adduct of bisphenol A, the color development performance is further improved and the cloudiness of the polymer is further suppressed when the functional group equivalent ratio (B / A) is 0.06 to 0.6. Also, when the compound represented by the general formula (IV) is a polyester compound obtained by reacting 3-methyl-1,5-pentanediol with an equimolar mixture of adipic acid and isophthalic acid in an equimolar amount, the color development performance is further improved and the cloudiness of the polymer is further suppressed when the functional group equivalent ratio (B / A) is 0.02 to 0.2. In the composition, the molar ratio of the NCO groups contained in the polyisocyanate compound (A) to the total of the OH groups and SH groups contained in the active hydrogen compound (C) and the polyol compound (B) (NCO groups / (OH groups + SH groups)) is in the range of 1.1 to 1.6, preferably in the range of 1.25 to 1.6, more preferably in the range of 1.25 to 1.5, and particularly preferably in the range of 1.25 to 1.4. When the molar ratio of NCO groups / (OH groups + SH groups) is within the above range, the molded body obtained from the polymerizable composition of the present invention can suppress the temporal decrease in photochromic performance, and thus can stably exhibit photochromic performance. The photochromic compound (D) can be used in an amount of 10 ppm to 5000 ppm based on the total amount of the isocyanate compound (A), polyol compound (B), and active hydrogen compound (C). When preparing a polymerizable composition by mixing a polyisocyanate compound (A), a polyol compound (B), an active hydrogen compound (C), a photochromic compound (D), and other additives, the temperature is usually 25°C or lower. From the perspective of the pot life of the polymerizable composition, it may be preferable to lower the temperature further. However, when the solubility of the catalyst, internal release agent, and additives in the monomer is not good, it is also possible to warm them in advance and dissolve them in the monomer and resin modifier. The mixing order and method of each component in the composition are not particularly limited as long as each component can be uniformly mixed, and can be carried out by known methods. Examples of known methods include a method of preparing a masterbatch containing a predetermined amount of additives and dispersing / dissolving this masterbatch in a solvent. In this embodiment, a molded article can be obtained by polymerizing and curing the polymerizable composition. The SH group concentration of the molded article can be determined by IR analysis. For example, using an IR analyzer Spectrum One manufactured by PERKIN-ELMER, measure the IR spectrum of a resin sample cut and polished to a thickness of 0.35 mm, and use the absorption of NCO at 2257 cm -1 , and SH at 2550 cm -1 to obtain the absorbance by the baseline method, and it can be determined by calculation using the following formula from a calibration curve prepared in advance. The SH group concentration of the molded article measured in this way is less than 1.0 wt%, preferably 0.5 wt% or less, more preferably 0.3 wt% or less, and particularly preferably 0.1 wt% or less. It is most preferable that the SH group of the molded article is not substantially detected. The molded article within this range can suppress the decrease in photochromic performance over time, and thus can stably exhibit photochromic performance. The molded article of this embodiment can be used as an optical material. In this embodiment, the manufacturing method of the optical material is not particularly limited, but casting polymerization can be mentioned as a preferable manufacturing method. First, a polymerizable composition is injected between molding molds held by a gasket, a tape, or the like. At this time, depending on the physical properties required for the obtained plastic lens, it is often preferable to perform a defoaming treatment under reduced pressure, a filtration treatment such as pressurization or reduced pressure, etc. as necessary. Regarding the polymerization conditions, since the conditions vary greatly depending on the composition of the polymerizable composition, the type and amount of the catalyst used, the shape of the mold, etc., they are not limited, but are generally carried out at a temperature of -50 to 150°C for 1 to 50 hours. In some cases, it is preferable to hold or gradually raise the temperature in the temperature range of 10 to 150°C and cure it in 1 to 25 hours. The optical material may be subjected to a treatment such as annealing as necessary. The treatment temperature is usually carried out between 50 and 150°C, preferably at 90 to 140°C, and more preferably at 100 to 130°C. In this embodiment, when molding the resin, in addition to the above-mentioned "other components", various additives such as a chain extender, a crosslinking agent, a light stabilizer, an ultraviolet absorber, an antioxidant, a bluing agent, an oil-soluble dye, a filler, and an adhesion improver may be added in the same manner as known molding methods according to the purpose. <Usage> The polymerizable composition of this embodiment can be obtained as molded bodies of various shapes by changing the type of mold during casting polymerization. The molded body has photochromic performance, a high refractive index, and high transparency, and can be used for various optical materials such as plastic lenses. In particular, it can be suitably used as a plastic spectacle lens or a plastic polarizing lens. [Plastic spectacle lens] The plastic spectacle lens using the lens substrate made of the molded body of this embodiment may be used with a coating layer provided on one side or both sides as necessary. The plastic spectacle lens of this embodiment is composed of a lens substrate made of the above-mentioned polymerizable composition and a coating layer. As the coating layer, specifically, a primer layer, a hard coat layer, an antireflection layer, an antifogging coat layer, an antifouling layer, a water repellent layer, etc. can be mentioned. These coating layers can be used individually or in a multilayered structure with multiple coating layers. When applying the coating layer on both sides, the same coating layer or different coating layers can be applied to each side. These coating layers may each be used in combination with an ultraviolet absorber for the purpose of protecting the lens and eyes from ultraviolet rays, an infrared absorber for the purpose of protecting the eyes from infrared rays, a light stabilizer or antioxidant for the purpose of improving the weather resistance of the lens, a dye or pigment for the purpose of enhancing the fashionability of the lens, an antistatic agent, and other known additives for enhancing the performance of the lens. For the layer to be coated by application, various leveling agents for the purpose of improving the coatability may be used. The primer layer is usually formed between the hard coat layer described later and the lens. The primer layer is a coating layer intended to improve the adhesion between the hard coat layer formed thereon and the lens, and in some cases, it is also possible to improve the impact resistance. Any material can be used for the primer layer as long as it has high adhesion to the obtained lens, but usually, a primer composition mainly composed of a urethane resin, an epoxy resin, a polyester resin, a melanin resin, polyvinyl acetal, etc. is used. The primer composition may use a suitable 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. The primer layer can be formed by either a coating method or a dry method. When using the coating method, after applying the primer composition to the lens by a known coating method such as spin coating or dip coating, the primer layer is formed by solidifying it. When performing by the dry method, it is formed by a known dry method such as CVD method or vacuum deposition method. When forming the primer layer, for the purpose of improving the adhesion, the surface of the lens may be pretreated, such as alkali treatment, plasma treatment, ultraviolet treatment, etc., if necessary. The hard coat layer is a coating layer intended to impart functions such as scratch resistance, abrasion resistance, moisture resistance, hot water resistance, heat resistance, and weather resistance to the lens surface. Generally, the hard coat layer is composed of a curable organosilicon compound and one or more oxide fine particles of elements selected from the element group of Si, Al, Sn, Sb, Ta, Ce, La, Fe, Zn, W, Zr, In, and Ti and / or one or more fine particles composed of a composite oxide of two or more elements selected from these element groups. A hard coat composition containing them is used. In addition to the above components, the hard coat composition preferably contains at least one of amines, amino acids, metal acetylacetonate complexes, metal organic salts, perchloric acids, salts of perchloric acids, acids, metal chlorides, and polyfunctional epoxy compounds. An appropriate solvent that does not affect the lens may be used for the hard coat composition, or it may be used without a solvent. 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 it. Examples of the curing method include heat curing and curing by irradiation with energy rays such as ultraviolet rays and visible light. In order to suppress the generation of interference fringes, the refractive index of the hard coat layer preferably has a difference in refractive index from the lens in the range of ±0.1. The antireflection layer is usually formed on the hard coat layer as necessary. There are inorganic and organic types of antireflection layers. In the case of an inorganic type, inorganic oxides such as SiO 2 , TiO 2 are used and formed by a dry method such as vacuum evaporation, sputtering, ion plating, ion beam assist method, or CVD method. In the case of an organic type, a composition containing an organosilicon compound and silica-based fine particles having internal cavities is used and formed by a wet method. The antireflection layer can be single-layer or multilayer. When used as a single layer, it is preferably at least 0.1 or more lower in refractive index than that of the hard coat layer. To effectively exhibit the antireflection function, it is preferably a multilayer antireflection film. In that case, a low refractive index film and a high refractive index film are alternately laminated. Also in this case, the refractive index difference 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 such as ZnO, TiO 2 , CeO 2 , Sb 2 O 5 , SnO 2 , ZrO 2 , Ta 2 O 5 etc. Examples of the low refractive index film include SiO 2 films etc. On the antireflection layer, an antifogging layer, an anti-contamination layer, and a water-repellent layer may be formed as necessary. As methods for forming the antifogging layer, the anti-contamination layer, and the water-repellent layer, as long as they do not have an adverse effect on the antireflection function, there are no particular limitations on the treatment method, treatment material, etc., and known antifogging treatment methods, anti-contamination treatment methods, water-repellent treatment methods, and materials can be used. For example, in the antifogging treatment method and the anti-contamination treatment method, there are methods such as covering the surface with a surfactant, adding a hydrophilic film to the surface to make it water-absorbent, covering the surface with fine irregularities to increase water absorption, using photocatalytic activity to make it water-absorbent, and performing super water-repellent treatment to prevent water droplets from adhering. Also, in the water-repellent treatment method, there are methods such as forming a water-repellent treatment layer by vapor deposition or sputtering of a fluorine-containing silane compound, or dissolving a fluorine-containing silane compound in a solvent and then coating to form a water-repellent treatment layer. [Plastic Polarizing Lens] The plastic polarizing lens of the present embodiment includes a polarizing film and a base material layer formed by curing the polymerizable composition for optical materials of the present embodiment on at least one surface of the polarizing film. The polarizing film in this embodiment can be composed of a thermoplastic resin. Examples of the thermoplastic resin include thermoplastic polyester, thermoplastic polycarbonate, thermoplastic polyolefin, and thermoplastic polyimide. From the viewpoints of water resistance, heat resistance, and moldability, thermoplastic polyester and thermoplastic polycarbonate are preferred, and thermoplastic polyester is more preferred. Examples of the thermoplastic polyester include polyethylene terephthalate, polyethylene naphthalate, and polybutylene terephthalate. From the viewpoints of water resistance, heat resistance, and moldability, polyethylene terephthalate is preferred. Specific examples of the polarizing film include a dichroic dye-containing thermoplastic 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. Furthermore, in order to improve the adhesion with an acrylic resin, the polarizing film may be used after performing one or more pretreatment selected from primer coating treatment, chemical treatment (chemical liquid treatment such as gas or alkali), corona discharge treatment, plasma treatment, ultraviolet irradiation treatment, electron beam irradiation treatment, roughening treatment, and flame treatment. Among such pretreatment, one or more selected from primer coating treatment, chemical treatment, corona discharge treatment, and plasma treatment are particularly preferred. The plastic polarizing lens of this embodiment can be obtained by providing a base material layer obtained by curing the polymerizable composition for optical materials of this embodiment on at least one surface of such a polarizing film. The manufacturing method of the plastic polarizing lens is not particularly limited, but preferably, the casting polymerization method can be mentioned. The manufacturing method of the plastic polarizing lens of this embodiment is, for example, a step of fixing the polarizing film in a lens casting mold in a state separated from the mold, and A step of injecting the polymerizable composition for an optical material into at least one of the gaps formed between the polarizing film and the mold; A step of polymerizing and curing the polymerizable composition for an optical material to laminate a base material layer on at least one surface of the polarizing film, can be included. The mold for lens casting is generally composed of two substantially disk-shaped glass molds held by a gasket. A polarizing film is placed in the space of this mold for lens casting so that the film surface is parallel to the inner surface of the front mold where the film surfaces face each other. A gap is formed between the polarizing film and the mold. Note that the polarizing film may be pre-shaped. The polymerization conditions of the polymerizable composition for an optical material vary depending on the composition of the polymerizable composition, the type and amount of the catalyst, the shape of the mold, etc., but are carried out at a temperature of 5 to 140°C for 1 to 50 hours. In some cases, it is preferably cured in 1 to 25 hours by holding or gradually raising the temperature in the temperature range of 5 to 130°C. The laminate cured by polymerization can be released from the mold to obtain the plastic polarizing lens of the present embodiment. In the present embodiment, the laminate after polymerization and release may be subjected to heat treatment such as annealing as necessary. The treatment temperature is carried out between 90 and 150°C from the viewpoint of the effects of the present invention, preferably at 110 to 130°C, and more preferably at 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 effects of the present invention. Note that a coating layer similar to that of a plastic spectacle lens may be formed on the surface of the obtained base material layer. Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited by these examples. In the examples and comparative examples, the methods and apparatuses used for evaluation are as follows. (Evaluation of the stability of photochromic performance (Accelerated test)) Using a QUV / SE accelerated weathering tester QUV manufactured by Q-Lab Corporation equipped with a UVA-340 type lamp, the irradiation intensity is 0.50 W / m 2、The acceleration test was carried out under the conditions of an irradiation time of 150 hours and a temperature of 50°C, and the dimming performance evaluation (light transmittance at the time of color development) before and after the acceleration was measured by the following method. The smaller the difference in transmittance before and after the acceleration test, the less the deterioration of the photochromic performance, and it can be judged that it is stable. (Dimming performance evaluation) Using a metal halide lamp (180W) light source device, at a temperature of 19°C and an ultraviolet intensity of 1.2 mW / cm measured by an integrating photometer 2 Under the conditions, the spectrum when a molded body sample processed to a thickness of 2.0 mm is colored for 5 minutes is measured by a transmission measurement system. ・Light transmittance at the time of color development: The light transmittance at 550 nm when colored under the above conditions When this value is small, the light-shielding property at the time of color development is high, and the photochromic performance is high. ・Light source: Metal halide light source device "LA-180ME" manufactured by Hayashi Watch Industry Co., Ltd. ・Integrating photometer: Integrating photometer "UIT-102 (light receiver UVD365PD)" manufactured by Ushio Inc. ・Transmission measurement system: "MV-3150" manufactured by JASCO Corporation (Analysis of residual functional groups by IR measurement) The IR spectrum of a resin sample cut and polished to a thickness of 0.35 mm was measured using an IR analyzer Spectrum One manufactured by PERKIN-ELMER. NCO is 2257 cm -1 , SH is 2550 cm -1 The absorbance was determined by the baseline method using the absorption at, and was determined by the calculation of the following formula from a calibration curve prepared in advance. [Comparative Example 1] To 41.0 parts by mass of 2,5(2,6)-bis(isocyanatomethyl)bicyclo[2.2.1]heptane, 0.05 part by mass of the compound of the formula (9) as a photochromic compound and 0.10 part by mass of dimethyltin dichloride were added, and the mixture was stirred and dissolved. To this mixed solution, 22.5 parts by mass of polypropylene glycol having a number average molecular weight of 700 and 36.5 parts by mass of pentaerythritol tetrakis(2-mercaptoacetate) were added and mixed and stirred. When each solution became uniform, it was degassed under 5 mmHg for 20 minutes, and these solutions were each injected into a polyethylene sheet mold. These were put into a furnace at 20 °C and kept for 8 hours, and then the temperature was raised to 120 °C over 12 hours. After heating at 120 °C as it was for 3 hours, the mold was taken out of the furnace, the mold was removed, and a molded body (a disk shape with a diameter of 45 mm and a thickness of 2.0 mm) obtained by polymerization was taken out. The molded body was colorless and transparent, had good light control performance of immediately coloring purple under sunlight and fading when the light was shielded. Next, the quantification of the residual -NCO groups and -SH groups of the molded body was carried out by IR analysis. Also, the light control performance of these molded bodies before and after the acceleration test was evaluated. These results are shown in Table 1. [Comparative Example 2, Examples 1 to 3] A molded body was prepared in the same manner as in Comparative Example 1 except that the addition amounts of 2,5(2,6)-bis(isocyanatomethyl)bicyclo[2.2.1]heptane, polypropylene glycol having a number average molecular weight of 700, and pentaerythritol tetrakis(2-mercaptoacetate) were changed as shown in Table 1. Each molded body was colorless and transparent, had good light control performance of immediately coloring purple under sunlight and fading when the light was shielded. Next, the quantification of the residual -NCO groups and -SH groups of these molded bodies was carried out by IR analysis. Also, the light control performance of these molded bodies before and after the acceleration test was evaluated. These results are shown in Table 1. From the results of Comparative Examples 1 and 2 described in Table 1, when the remaining amount of SH groups in the molded body increased to 1.0 wt% or more, the transmittance after the acceleration test increased significantly and the light control function was almost lost, and deterioration of the photochromic performance was observed. On the other hand, as in Examples 1 to 3, when the remaining amount of SH groups in the molded body was less than 1.0 wt%, the change amount of the transmittance was small, and it was confirmed that the photochromic performance was stable. In addition, it was presumed that similar results could be obtained for plastic polarizing lenses. This application claims the priority based on Japanese Patent Application No. 2015-183494 filed on September 16, 2015, and the priority based on Japanese Patent Application No. 2015-240357 filed on December 9, 2015, and incorporates the entire disclosure thereof herein.
Claims
Revised 3 May 2019, Page 1 of 1 page. Claims 1. Molded workpieces obtained by the solidification polymerization of polymerization compounds consisting of (A) polyisocyanate compounds and (B) polyol compounds, which are represented by the following general formula (1) [Chemistry 1] (Chemical Formula) (In Formula (1), m is a number of 1-20, k is 0-2m, n is a number of 1-20, I is 0-2n, a is a number of 0 or higher, b is a number of 0 or higher, d is a number of 0 or higher, e is a number of 1 or higher, Q1 is a hydrogen atom or group. (C) alkyl compounds with 1-6 carbon atoms, Q1 which may be multiples of the same or different, Q2 which are hydrogen atoms or alkyl groups with 1-6 carbon atoms, Q2 which may be multiples of the same or different, Z which are divalent organic groups with 1-30 carbon atoms which may include aromatic groups, Z which may be multiples of the same or different) with an average molecular weight of 100 or more and (C) active hydrogen compounds which have two or more functions (except for the compounds (B) mentioned above) and (D) photochromic compounds.Molded specimens with SH concentrations determined by IR analysis to be less than 1.0% by weight. -------------------------------------------------------------------------- Page 1 of 10 pages. Claims 1. Molded specimens obtained by the solidification polymerization of polymerization compounds consisting of (A) polyisocyanate compounds and (B) polyol compounds, which are represented by the following general formula (1): [Chemistry 1] Chemical formula structure (in formula (1), a is a number of 1-20, k is 0-2m, n is a number of 1-20, I is 0-2n, a is a number of 0 or higher, b is a number of 0 or higher, d is a number of 0 or higher, e is a number of 1 or higher, Q1 is a hydrogen atom or alkyl group with 1-6 carbon atoms, Q1, which may be the same or different, Q2 is a hydrogen atom or alkyl group with 1-6 carbon atoms, Q2, which may be the same or different, Z is a divalent organic group with 1-30 carbon atoms, which may include aromatic groups.(A) multiple Z compounds which may be the same or different) with an average molecular weight of 100 or more and (C) active hydrogen compounds which have two or more functions (except for the compounds (B) mentioned above) and (D) photochromic compounds, molded samples with a concentration of SH groups by IR analysis of less than 1.0% by weight.
2. Molded samples specified in claim 1 in which one or more polyisocyanate compounds (A) are selected from groups obtained from hexamethylene diisocyanate, pentamethylen diisocyanate, xylylene diisocyanate, isofarone diisocyanate, bis(isocyanate 2,5-bis(isocyanatomethyl)cyclohexane, dicyclohexylmethane diisocyanate, 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, toliline diisocyanate, phenylene diisocyanate and diphenylmethane diisocyanate. Page 2 of 10. Page 3. The formulations specified in claim 1 or 2, in which polyol compounds (B) are one or more compounds selected from the compounds represented by the following general formulas (I) - the following general formulas (IV); [Chemistry 2] chemical formula structure (I) (in formula (I), P is the number of 4-100, X is the atom of 1 hydrogen or methyl group,X, which can be the same or different, [Chemistry 3] Chemical formula structure (II) (in formula (II), q, can be the same or different, each is a number from 1 onwards, the sum of q and r is a number from 2-100, R1 and R2 can be the same or different, are hydrogen atoms or methyl groups, R1 or R2, which can be the same or different, each is the same or different, Z is a divalent aliphatic group which will consist of a divalent aromatic group that is replaced or not replaced, an aromatic group with 1-20 carbons that is replaced or not replaced. [Chemistry 4] Chemical formula structure (iii) (In formula (III), q, r may be the same or different, each is a number of 1 or higher, including the sum of q and r are numbers of 2-100, R1 and R2 may be the same or different, each is a hydrogen atom or methyl group, R1 or R2 which have multiples, each may be the same or different) Page 3 of 10 pages [Chemistry 5] Chemical formula structure (iv) (In formula (IV), t is a number of 1-20, k is 0-2t, a is a number of 1-20, I is 0-2t, f is a number of 0 or higher, g is a number of 1 or higher, h is a number of 1 or higher,J is a number starting with 1 or higher. Q1 is a hydrogen atom or alkyl group with 1-6 carbon atoms. Multiple Q1s may be the same or different. Q2 is a hydrogen atom or alkyl group with 1-6 carbon atoms. Multiple Q2s may be the same or different. R3 is a tenylene I group, which may have a straight-chain or branched alkyl group with 1-20 carbon atoms or a straight-chain or branched alkyl group with 1-10 carbon atoms as a substitute. Multiple R3s may be the same or different.
4. The manufactured product specified in claim 3, where polyol compound (B) is the compound represented by the general formula (I).General Formula (III) or General Formula (IV) 5. A molded workpiece specified in Reputation 3 or 4 in which the compounds represented by such General Formula (I) are polyethylene glycol or polypropylene glycol.
6. A molded workpiece specified in any of Reputation 3-5 in which the number average molecular weight of the compounds represented by such General Formula (I) is 200-4000.
7. A molded workpiece specified in any of Reputation 3-5 in which the number average molecular weight of the compounds represented by such General Formula (I) is 300-3000.
8. A molded workpiece specified in Reputation 3 in which 9. A molded product specified in Reputation 3 or 4 in which the average molecular weight by the number of compounds represented by the general formula (II) is 400-2000.
10. A molded product specified in Reputation 3 or 4 in which the average molecular weight by the number of compounds represented by the general formula (IV) is 600-3000.
11. A molded product specified in Reputation 1-10 in which one active hydrogen compound (C) is of a type selected from the polyol compounds.Polythiol compounds and thiol compounds containing hydroxyl groups, page 4 of 10, page 12.13.51014.152025, workpieces formed as specified in one of the claims 1-11 in which the active hydrogen compound (C) is a trifunctional active hydrogen compound, or workpieces formed as specified in one of the claims 1-12 in which the active hydrogen compound (C) is one type, selected from the group of glycerin, penta-erythritol tetrakis(2-mercapto acetate), penta-erythritol tetrakis(r-mercaptopropionate), 4-mercapto thylt-bur-i. Dimercapto-r,th-dithioctane,5,7-dimercaptomethyl-bu-dimercapto-r,6,9-trithiandecaine,4,7-dimercaptomethyl-bu11-dimercapto-r,6,9-trithiandecaine,4,r-dimercaptomethyl-bu11-dimercapto-r,6,9-trithiandecaine,111,r,r-tetrakis(mercaptomethylthio)propane,and trimethylolpropanes(r-mercaptopropionate)works formed in any one of the claims1-13 in which the photochromic compound(a) is represented by the following general formula(5);[Chemistry6](in the formula, R, and R2 may be the same or different,Unrelated groups include hydrogen; straight or branched alkyl groups with 1-12 carbon atoms; 'cycloalkyl groups with 1 carbon atom and 3-12 carbon atoms; ARE groups with 1 carbon atom and 6-24 carbon atoms; or heteroalkyl groups with 4-24 carbon atoms, either substituted or unsubstituted (substitute groups with at least one substituted group chosen from a halogen atom, hydroxyl group, straight or branched alkyl group with 1-12 carbon atoms, straight or branched alkoxy group with 1-12 carbon atoms, straight or branched haloalkyl group with 1-12 carbon atoms that have been substituted). A halogen atom, a straight-chain or branched haloalkoxy group with carbon atoms 1-12 replaced by at least one halogen atom, a phantom or naphthoxy group replaced by at least one alkyl or straight-chain or branched alkoxy group on the face of 5 of 10 carbon atoms 1-12, a straight-chain or branched alkyl group with carbon atoms 2-12, a -NH2 group, a -NHR group, or a -N(R)2 group (R is a straight-chain or branched alkyl group with carbon atoms 1-6 in the case of 2 Rs; the 2 Rs may be the same or different).and methacryl or acryl groups); 5. Aralkyl or heteroaralkyl groups (straight or branched alkyl groups with 1-4 carbon atoms replaced by an erl group or such heteroerl group), R3 may be the same or different, unrelated, including halogen atoms; alkyl groups, straight or branched with 1-12 carbon atoms; 'cycloalkyl groups with 3-12 carbon atoms; 10. Straight-chain or branched alkyl groups with 1-12 carbon atoms; straight-chain or branched haloalkyl groups with 1-12 carbon atoms replaced by at least one halogen atom; halocycloalkyl groups with 3-12 carbon atoms replaced by at least one halogen atom; straight-chain or branched haloalkoxy groups with 1-12 carbon atoms replaced by at least one halogen atom; 15 Earl groups with 6-24 carbon atoms or heteroall groups with 4-24 carbon atoms, replaced or unreplaced (substantiated groups with at least one substantiated group selected from a halogen atom); hydroxyl groups; straight-chain or branched alkyl groups with 1-12 carbon atoms; straight-chain or branched alkoxy groups with 1-12 carbon atoms.
20. Straight-chain or branched haloalkyl groups with 1-12 carbon atoms replaced by at least one halogen atom; 20. Straight-chain or branched haloalkoxy groups with 1-12 carbon atoms replaced by at least one halogen atom; 30. Tenoxy or naphthoxy groups replaced by at least one alkyl or straight-chain or branched alkoxy group with 1-12 carbon atoms; 30. Straight-chain or branched alkynyl groups with 2-12 carbon atoms and an amino group; 25. Aralkyl or heteroaralkyl groups (straight-chain or branched alkyl groups with 1-4 carbon atoms replaced by such aryl or heteroaryl groups); 30. Tenoxy or naphthoxy groups replaced or not replaced (substances with at least one substituted group chosen from straight-chain or branched alkyl or alkoxy groups with 1-6 carbon atoms); 30. -NH2,-NHR,-CONH2, or -CONHR(R refers to straight-chain or branched alkyl groups with 1-6 carbon atoms); page 6 of 10 pages -OCORgVf or -COORg(in this case, Rg refers to straight-chain or branched alkyl groups with 1-6 carbon atoms, or cycloalkyl groups with 3-6 carbon atoms, or where R,,R2 is the substituted thylenyl group with a substituted etheryl group or a substituted heteroetheryl group which is at least one substitute or an unsubstituted thylenyl group); 1 is an integer from 0 to 4; A is the annealed ring of the following formulas (A2) or (A4) [Chemistry 7]. In these annealed rings, play the carbon C5-carbon C6 bonds of the naphtopyran ring of general formula 2. The a bonds of the annealed ring (A4) can form bonds with the carbon C5-carbon C6 of the naphtopyran ring of general formula (5); R4 is the same or different, unrelated, OH, Alkyl or alkoxy groups, straight or branched, with 1-6 carbon atoms, or two R4 atoms, are classified as carbonyls (CO); R5 is a halogen; straight or branched alkyl groups with 1-12 carbon atoms; straight or branched alkyl groups with 1-6 carbon atoms replaced by at least one halogen atom; 'cycloalkyl' groups with 1 carbon atom and 3-12 carbon atoms; straight or branched alkoxy groups with 1-6 carbon atoms; tenel or benchle groups, replaced or unreplaced (for substituents, if it is an R, R2 group in the general formula,(5) which is not directly related to the eryl or heteroeryl groups, will have at least one of the above-mentioned substituent groups in the definition of RvR2);-NH2,-NHR(in this case R is a straight-chain or branched alkyl group with 1-6 carbons);? I *..ะ??*?*I* #I ** ?? ? ? # * ? *Page 7 of 10 pages 51015.15 16.17.18.20 19.25 Substituted or unsubstituted rl noxy or naphthoxy groups (at least one substituent will have alkyl or alkoxy groups of straight or branched chains with 1-6 carbon atoms); -CORg, -COORg or -CONHRg groups (where Rg is alkyl groups of straight or branched chains with 1-6 carbon atoms, or 1 cycloalkyl groups with 1-3-6 carbon atoms, or phenyl or benzyl groups that are substituted or unsubstituted (for the substituents ', if it is the case that the R,,R2 groups of the general formula (5) which are not related to the eryl or heteroeryl groups, will have at least one substituent group as mentioned above in the definition of R,,R2 groups); in the case where A means (AJ, which is an integer (from 0 to 2), P is an integer from 0 to 4, in the case where A means (A2),(Integers from 0 to 2) A workpiece in the form specified in any of the claims 1-14, in which the equivalent ratio of the functional group (B / A) of the posiol compound (B) to the posi isocyanate compound (A) is 0.02-0.6, and the equivalent ratio of the functional group (C / A) of the active hydrogen compound (C) to the posi isocyanate compound (A) is 0.4-0.
98. Optical materials derived from the workpiece. A molded plastic lens obtained from a ... (B) Posiol compounds represented by the following general formula(1)[Chemistry8]HH2m-k0-CnH2n.|(in formula(1), a is a number of 1-20, k is 0-2n, t is a number of 1-20, I is 0-2n, a is a number of 0 or higher, b is a number of 0 or higher, d is a number of 0 or higher, e is a number of 1 or higher, Q1 is a hydrogen atom or alkyl group with 1-6 carbon atoms,Q1, which has many of the same or different ones, Q2, which is an atom (1)..ะ.ะ..?? ?* tf#? I page 8 of 10 pages, hydrogen or alkyl groups with 1-6 carbon atoms, Q2, which has many of the same or different ones, Z, which is a 1-divalent organic group with 1-30 carbon atoms which may contain aromatic groups, Z, which has many of the same or different ones) with an average molecular weight of 100 or more, and (C) active hydrogen compounds which have two or more functions (except for the compounds (B) mentioned above), and (a) photochromic compounds. The process of forming plastic lenses involves the preparation of polymerization compounds for the blended materials (A), polyisocyanate compounds (A), to the sum of OH and SH groups in the active hydrogen compound (C) and polyol compound (B) in the range of 1.1-1.
6. The process of forming plastic lenses involves the preparation of polymerization compounds for the blended materials (A), polyisocyanate compounds and (B) polyol compounds, represented by the following general formula (1) [Chemistry9] (in formula (1), t is a number of 1-20, k is 0-2t, t is a number of 1-20,I represents 0-2, L represents numbers from 0 onwards, C represents numbers from 0 onwards, d represents numbers from 0 onwards, and e represents numbers from 1 onwards. Q1 represents a hydrogen atom or alkyl group with 1-6 carbon atoms; multiple Q1s may be the same or different. Q2 represents a hydrogen atom or alkyl group with 1-6 carbon atoms; multiple Q2s may be the same or different. Z represents a divalent organic group with 1-30 carbon atoms, which may include aromatic groups.Z (which may be the same or different) with an average molecular weight of 100 or more and (C) active hydrogen compounds which have two functions (except for the aforementioned compound (B)) and (D) photochromic compounds with a mole ratio (NCO groups / (OH groups + SH groups)) of 9 of 10 pages 521.10 of the NCO groups present in the polyisocyanate compound (A) to the sum of the OH and SH groups present in the active hydrogen compound (C) and polyol compound (B) in the range of 1.1-1.6 and the lens base material shaping process by casting polymerization of the polymerizing compounds with the properties of such optical materials within a mold. The method of producing plastic polarized lenses consists of a process of preparing the polymerizing compounds with the properties of such optical materials by combining (A) polyisocyanate compounds and (B) Polyol compounds represented by the following general formula(1)[Chemistry10] (1)(in formula(1), a is a number of 1-20, k is 0-2n, t is a number of 1-20, I15 is 0-2n, a is a number of 0 or more, c is a number of 0 or more, c is a number of 0 or more, e is a number of 1 or more, Q1 is a hydrogen atom or alkyl group with 1-6 carbon atoms,Q1, which can be multiple and may be the same or different; Q2, which can be hydrogen atoms or alkyl groups with 1-6 carbon atoms; Z, which can be divalent organic groups with 1-30 carbon atoms, and may include aromatic groups.(Z) which may be the same or different (with an average molecular weight of 100 or more and (C) active hydrogen compounds which have a long function (except for the compound (B) mentioned above) and (a) photochromic compounds with a mole ratio of (NCO group / (OH group + SH group))25 The ratio of NCO groups present in the polyisocyanate compound (A) to the sum of OH and SH groups present in the active hydrogen compound (C) and polyol compound (B) is in the range of 1.1-1.6, and the process of attaching the polarizing film within the lens casting mold in a condition separated from the mold and page 10 of 10 pages, the process of injecting the polymerizing compound for the optical material into at least one gap created between the polarizing film and the mold, and the process of polymerizing and solidifying the polymerizing compound for the optical material and then laminating the base material on at least one side of the polarizing film;