Polymerizable Composition For Optical Materials And Use Thereof Patent Application (2024)

U.S. patent application number 17/611368 was filed with the patent office on 2022-07-07 for polymerizable composition for optical materials and use thereof.This patent application is currently assigned to MITSUI CHEMICALS, INC.. The applicant listed for this patent is MITSUI CHEMICALS, INC.. Invention is credited to Shinsuke ITO, Yuuki KASORI.

POLYMERIZABLE COMPOSITION FOR OPTICAL MATERIALS AND USE THEREOF

Abstract

A polymerizable composition for optical materials of the presentinvention contains (A) a polyisocyanate compound, (B) a polythiolcompound, (C) a photochromic compound, (D) a polyether compoundhaving a number-average molecular weight of 50 to 10,000, and (E) apolyether-modified siloxane compound having a viscosity of 1 mPasor more and less than 1,600 mPas.

Foreign Application Data

Claims

1. A polymerizable composition for optical materials, comprising:(A) a polyisocyanate compound; (B) a polythiol compound; (C) aphotochromic compound; (D) a polyether compound having anumber-average molecular weight of 50 to 10,000; and (E) apolyether-modified siloxane compound having a viscosity of 1 mPasor more and less than 1,600 mPas.

2. The polymerizable composition for optical materials according toclaim 1, wherein the polyether compound (D) is at least onecompound selected from a compound represented by the followingGeneral Formula (d1) and a compound represented by the followingGeneral Formula (d2), and the polyether-modified siloxane compound(E) is a compound represented by the following General Formula (e),##STR00028## wherein, in General Formula (d1), R.sub.1 and R.sub.2each represent a hydrogen atom or an alkyl group having 1 to 18carbon atoms, at least one of R.sub.1 and R.sub.2 is a hydrogenatom, a plurality of R.sub.1's may be the same or different fromeach other, a plurality of R.sub.2's may be the same or differentfrom each other, and m represents an integer of 15 to 500,##STR00029## wherein, in General Formula (d2), Q represents an(n+f)-valent hydrocarbon group, n represents an integer of 0 ormore, f represents an integer of 1 or more, n+f is 3 or more, and mrepresents an integer of 2 to 58, ##STR00030## wherein, in GeneralFormula (e), R.sub.1 to R.sub.8 may be the same or different fromeach other, at least one of R.sub.1 to R.sub.8 represents apolyether group represented by the following General Formula (i)and the rest of R.sub.1 to R.sub.8 may be the same or differentfrom each other and each represent a linear or branched alkyl grouphaving 1 to 20 carbon atoms, a linear or branched alkoxy grouphaving 1 to 20 carbon atoms, a hydroxyl group, or a polysiloxygroup, a plurality of R.sub.2's to R.sub.5's may be the same ordifferent from each other, and m and n may be the same or differentfrom each other and each represent an integer of 0 or more,##STR00031## wherein, in General Formula (i), R.sub.25 represents alinear or branched alkylene group having 1 to 20 carbon atoms,R.sub.26 represents a hydrogen atom, a linear or branched alkylgroup having 1 to 20 carbon atoms, a linear or branched alkenylgroup having 2 to 20 carbon atoms, or a linear or branched alkynylgroup having 2 to 20 carbon atoms, a plurality of R.sub.25's may bethe same or different from each other, and k represents an integerof 1 or more.

3. The polymerizable composition for optical materials according toclaim 1, wherein the polyether-modified siloxane compound (E) is acompound represented by the following General Formula (e-1), acompound represented by the following General Formula (e-2), or amixture of these, ##STR00032## wherein, in General Formula (e-1),a+c is an integer of 1 to 100, b is an integer of 1 to 100, d is aninteger of 10 to 1,000, and e is an integer of 1 to 100,##STR00033## wherein, in General Formula (e-2), f+h is preferablyan integer of 1 to 100, and g is an integer of 1 to 100.

4. The polymerizable composition for optical materials according toclaim 1, wherein the photochromic compound (C) is a compoundrepresented by General Formula (c1) or General Formula (c2),PC-L-Chain (c1) PC-L-Chain-L'-PC' (c2) wherein PC and PC' eachrepresent any of General Formulas (1) to (4), and PC and PC' may bethe same or different from each other, ##STR00034## wherein, inGeneral Formulas (1) to (4), R.sup.1 to R.sup.18 each representhydrogen, a halogen atom, a carboxyl group, an acetyl group, aformyl group, a C1-C20 aliphatic group which is optionallysubstituted, a C3-C20 alicyclic group which is optionallysubstituted, or a C6-C20 aromatic organic group which is optionallysubstituted, R.sup.1 to R.sup.18 may be the same or different fromeach other, these aliphatic group, alicyclic group, and aromaticorganic group may have an oxygen atom or a nitrogen atom, any onegroup contained in the compounds represented by General Formulas(1) to (4) is bonded to L or L' which is a divalent organic group,L and L' each represent a divalent organic group including one ormore groups selected from an oxyethylene chain, an oxypropylenechain, a (thio)ester group, and a (thio)amide group, and Chainrepresents a monovalent or divalent organic group including one ormore chains selected from a polysiloxane chain and apolyoxyalkylene chain.

5. The polymerizable composition for optical materials according toclaim 1, wherein the polyisocyanate compound (A) is at least onecompound selected from2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane,2,6-bis(isocyanatomethyl)bicyclo-[2.2.1] heptane, m-xylylenediisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate,dicyclohexylmethane diisocyanate,1,3-bis(isocyanatomethyl)cyclohexane,1,4-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate,1,6-hexamethylene diisocyanate, and 1,5-pentamethylenediisocyanate.

6. The polymerizable composition for optical materials according toclaim 1, wherein the polythiol compound (B) is at least onecompound selected from4-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,pentaerythritol tetrakis(3-mercaptopropionate),bis(mercaptoethyl)sulfide, pentaerythritoltetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethyl)-1,4-dithiane,1,1,3,3-tetrakis(mercaptomethylthio)propane,4,6-bis(mercaptomethylthio)-1,3-dithiane, and2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane.

7. The polymerizable composition for optical materials according toclaim 1, wherein a content of the polyether-modified siloxanecompound (E) is 0.001% to 2% by weight.

8. The polymerizable composition for optical materials according toclaim 1, wherein a ratio of a content of the polyether-modifiedsiloxane compound (E) with respect to a content of the polyethercompound (D) (E (parts by weight)/D (parts by weight)) is 0.01 to1.0.

9. The polymerizable composition for optical materials according toclaim 1, further comprising: a microphase-separated structure ofthe polyether compound (D).

10. A molded product obtained by curing the polymerizablecomposition for optical materials according to claim 1.

11. The molded product according to claim 10, comprising: amicrophase-separated structure of the polyether compound (D).

12. An optical material comprising: the molded product according toclaim 10.

13. A plastic lens composed of the molded product according toclaim 10.

14. A method for manufacturing a polymerizable composition foroptical materials, comprising: a step of mixing together apolyisocyanate compound (A), a photochromic compound (C), apolyether compound (D) having a number-average molecular weight of50 to 10,000, and a polyether-modified siloxane compound (E) havinga viscosity of 1 mPas or more and less than 1,600 mPas; and a stepof mixing a mixed solution obtained by the above step with apolythiol compound (B).

15. The method for manufacturing a polymerizable composition foroptical materials according to claim 14, wherein the polyethercompound (D) is at least one compound selected from a compoundrepresented by the following General Formula (d1) and a compoundrepresented by the following General Formula (d2), and thepolyether-modified siloxane compound (E) is a compound representedby the following General Formula (e), ##STR00035## wherein, inGeneral Formula (d1), R.sub.1 and R.sub.2 each represent a hydrogenatom or an alkyl group having 1 to 18 carbon atoms, at least one ofR.sub.1 and R.sub.2 is a hydrogen atom, a plurality of R.sub.1'smay be the same or different from each other, a plurality ofR.sub.2's may be the same or different from each other, and mrepresents an integer of 15 to 500, ##STR00036## wherein, inGeneral Formula (d2), Q represents an (n+f)-valent hydrocarbongroup, n represents an integer of 0 or more, f represents aninteger of 1 or more, n+f is 3 or more, and m represents an integerof 2 to 58, ##STR00037## wherein, in General Formula (e), R.sub.1to R.sub.8 may be the same or different from each other, at leastone of R.sub.1 to R.sub.8 represents a polyether group representedby the following General Formula (i) and the rest of R.sub.1 toR.sub.8 may be the same or different from each other and eachrepresent a linear or branched alkyl group having 1 to 20 carbonatoms, a linear or branched alkoxy group having 1 to 20 carbonatoms, a hydroxyl group, or a polysiloxy group, a plurality ofR.sub.2's to R.sub.8's may be the same or different from eachother, and m and n may be the same or different from each other andeach represent an integer of 0 or more, ##STR00038## wherein, inGeneral Formula (i), R.sub.25 represents a linear or branchedalkylene group having 1 to 20 carbon atoms, R.sub.26 represents ahydrogen atom, a linear or branched alkyl group having 1 to 20carbon atoms, a linear or branched alkenyl group having 2 to 20carbon atoms, or a linear or branched alkynyl group having 2 to 20carbon atoms, a plurality of R.sub.25's may be the same ordifferent from each other, and k represents an integer of 1 ormore.

16. The method for manufacturing a polymerizable composition foroptical materials according to claim 14, wherein thepolyether-modified siloxane compound (E) is a compound representedby the following General Formula (e-1), a compound represented bythe following General Formula (e-2), or a mixture of these,##STR00039## wherein, in General Formula (e-1), a+c is an integerof 1 to 100, b is an integer of 1 to 100, d is an integer of 10 to1,000, and e is an integer of 1 to 100, ##STR00040## wherein, inGeneral Formula (e-2), f+h is preferably an integer of 1 to 100,and g is an integer of 1 to 100.

Description

TECHNICAL FIELD

[0001] The present invention relates to a polymerizable compositionfor optical materials that contains a photochromic compound, and anoptical material and a plastic lens that are obtained from thecomposition.

BACKGROUND ART

[0002] Hitherto, the development of plastic lenses havingphotochromic performance has been in progress.

[0003] Patent Document 1 discloses a polymerizable composition foroptical materials that contains a polythiol compound, apolyisocyanate compound, a photochromic compound, and a blockcopolymer component. Patent Document 1 describes that thepolymerizable composition for optical materials can provide opticalmaterials excellent in photochromic properties, heat resistance,and mechanical properties.

[0004] Patent Document 2 discloses a polymerizable composition foroptical materials that contains a predetermined polyether-modifiedsiloxane compound and a polymerizable compound. Patent Document 2describes that the addition of a predetermined polyether-modifiedsiloxane compound suppresses the formation of striae on a lens.

[0005] Patent Document 3 discloses a polymerizable composition foroptical materials that contains an allyloxycarbonylgroup-containing compound, a radical polymerization initiator, anda polyether-modified siloxane compound. Patent Document 3 describesthat the polymerizable composition for optical materials suppressesthe occurrence of cracks during polymerization or the breakageduring mold release while maintaining excellent transparency.

RELATED DOCUMENT

Patent Document

[0006] [Patent Document 1] International Publication No.WO2018/070383 [0007] [Patent Document 2] International PublicationNo. WO2016/125786 [0008] [Patent Document 3] InternationalPublication No. WO2018/155475

Non-Patent Document

[0008] [0009] [Non-Patent Document 1] P. Alexandridis, T. A.Hatton/Colloids Surfaces A: Physicochem. Eng. Aspects 96 (1995)1-46

SUMMARY OF THE INVENTION

Technical Problem

[0010] However, in a case where a polyether-modified siloxanecompound is added to a polymerizable composition for opticalmaterials that contains a polymerizable compound, a photochromiccompound, and a block copolymer component, sometimes thephotochromic performance deteriorates and white turbidity occurs,which leads to the reduction of transparency or the occurrence ofstriae.

Solution to Problem

[0011] As a result of intensive studies, the inventors of thepresent invention have found that optical materials which haveexcellent photochromic performance, are inhibited from causingwhite turbidity, have excellent transparency, and are inhibitedfrom forming striae can be obtained from a composition having apredetermine makeup.

[0012] That is, the present invention can be described asbelow.

[0013] [1] A polymerizable composition for optical materialscontaining (A) a polyisocyanate compound,

[0014] (B) a polythiol compound,

[0015] (C) a photochromic compound,

[0016] (D) a polyether compound having a number-average molecularweight of 50 to 10,000, and

[0017] (E) a polyether-modified siloxane compound having aviscosity of 1 mPas or more and less than 1,600 mPas.

[0018] [2] The polymerizable composition for optical materialsdescribed in [1], in which the polyether compound (D) is at leastone compound selected from a compound represented by the followingGeneral Formula (d1) and a compound represented by the followingGeneral Formula (d2), and

[0019] the polyether-modified siloxane compound (E) is a compoundrepresented by the following General Formula (e),

##STR00001##

[0020] wherein, in General Formula (d1), R.sub.1 and R.sub.2 eachrepresent a hydrogen atom or an alkyl group having 1 to 18 carbonatoms, and at least one of R.sub.1 and R.sub.2 is a hydrogen atom.A plurality of R.sub.1's may be the same or different from eachother, and a plurality of R.sub.2's may be the same or differentfrom each other. m represents an integer of 15 to 500,

##STR00002##

[0021] wherein, in General Formula (d2), Q represents an(n+f)-valent hydrocarbon group. n represents an integer of 0 ormore, f represents an integer of 1 or more, and n+f is 3 or more. mrepresents an integer of 2 to 58,

##STR00003##

[0022] wherein, in General Formula (e), R.sub.1 to R.sub.8 may bethe same or different from each other, at least one of R.sub.1 toR.sub.8 represents a polyether group represented by the followingGeneral Formula (i), and the rest of R.sub.1 to R.sub.8 may be thesame or different from each other and each represent a linear orbranched alkyl group having 1 to 20 carbon atoms, a linear orbranched alkoxy group having 1 to 20 carbon atoms, a hydroxylgroup, or a polysiloxy group. A plurality of R.sub.2's to R.sub.5'smay be the same or different from each other. m and n may be thesame or different from each other and each represent an integer of0 or more,

##STR00004##

[0023] wherein, in General Formula (i), R.sub.25 represents alinear or branched alkylene group having 1 to 20 carbon atoms, andR.sub.26 represents a hydrogen atom, a linear or branched alkylgroup having 1 to 20 carbon atoms, a linear or branched alkenylgroup having 2 to 20 carbon atoms, or a linear or branched alkynylgroup having 2 to 20 carbon atoms. A plurality of R.sub.25's may bethe same or different from each other. k represents an integer of 1or more.

[0024] [3] The polymerizable composition for optical materialsdescribed in [1] or [2], in which the polyether-modified siloxanecompound (E) is a compound represented by the following GeneralFormula (e-1), a compound represented by the following GeneralFormula (e-2), or a mixture of these.

##STR00005##

[0025] wherein, in General Formula (e-1), a+c is an integer of 1 to100, b is an integer of 1 to 100, d is an integer of 10 to 1,000,and e is an integer of 1 to 100,

##STR00006##

[0026] wherein, in General Formula (e-2), f+h is preferably aninteger of 1 to 100, and g is an integer of 1 to 100.

[0027] [4] The polymerizable composition for optical materialsdescribed in any one of [1] to [3], in which the photochromiccompound (C) is a compound represented by General Formula (c1) orGeneral Formula (c2).

PC-L-Chain (c1)

PC-L-Chain-L'-PC' (c2)

[0028] wherein PC and PC' each represent any of General Formulas(1) to (4). PC and PC' may be the same or different from eachother,

##STR00007##

[0029] wherein, in General Formulas (1) to (4), R.sup.1 to R.sup.18each represent hydrogen, a halogen atom, a carboxyl group, anacetyl group, a formyl group, a C1-C20 aliphatic group which isoptionally substituted, a C3-C20 alicyclic group which isoptionally substituted, or a C6-C20 aromatic organic group which isoptionally substituted. R.sub.1 to R.sub.18 may be the same ordifferent from each other. These aliphatic group, alicyclic group,and aromatic organic group may have an oxygen atom or a nitrogenatom. Any one group contained in the compounds represented byGeneral Formulas (1) to (4) is bonded to L or L' which is adivalent organic group. L and L' each represent a divalent organicgroup including one or more groups selected from an oxyethylenechain, an oxypropylene chain, a (thio)ester group, and a(thio)amide group. Chain represents a monovalent or divalentorganic group including one or more chains selected from apolysiloxane chain and a polyoxyalkylene chain.

[0030] [5] The polymerizable composition for optical materialsdescribed in any one of [1] to [4], in which the polyisocyanatecompound (A) is at least one compound selected from2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane,2,6-bis(isocyanatomethyl)bicyclo-[2.2.1] heptane, m-xylylenediisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylenediisocyanate,dicyclohexylmethane diisocyanate,1,3-bis(isocyanatomethyl)cyclohexane,1,4-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate,1,6-hexamethylene diisocyanate, and 1,5-pentamethylenediisocyanate.

[0031] [6] The polymerizable composition for optical materialsdescribed in any one of [1] to [5], in which the polythiol compound(B) is at least one compound selected from4-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,pentaerythritol tetrakis(3-mercaptopropionate),bis(mercaptoethyl)sulfide, pentaerythritoltetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethyl)-1,4-dithiane,1,1,3,3-tetrakis(mercaptomethylthio)propane,4,6-bis(mercaptomethylthio)-1,3-dithiane, and2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane. [7] Thepolymerizable composition for optical materials described in anyone of [1] to [6], in which a content of the polyether-modifiedsiloxane compound (E) is 0.001% to 2% by weight.

[0032] [8] The polymerizable composition for optical materialsdescribed in any one of [1] to [7], in which a ratio of a contentof the polyether-modified siloxane compound (E) with respect to acontent of the polyether compound (D) (E (parts by weight)/D (partsby weight)) is 0.01 to 1.0.

[0033] [9] The polymerizable composition for optical materialsdescribed in any one of [1] to [8], further including amicrophase-separated structure of the polyether compound (D).

[0034] [10] A molded product obtained by curing the polymerizablecomposition for optical materials described in anyone of [1] to[9].

[0035] [11] The molded product described in [10], including amicrophase-separated structure of the polyether compound (D).

[0036] [12] An optical material formed of the molded productdescribed in [10] or [11].

[0037] [13] A plastic lens composed of the molded product describedin [10] or [11].

[0038] [14] A method for manufacturing a polymerizable compositionfor optical materials, including a step of mixing together apolyisocyanate compound (A), a photochromic compound (C), apolyether compound (D) which has a number-average molecular weightof 50 to 10,000, and a polyether-modified siloxane compound (E)which has a viscosity of 1 mPas or more and less than 1,600 mPas,and

[0039] a step of mixing a mixed solution obtained by the above stepwith a polythiol compound (B).

[0040] [15] The method for manufacturing a polymerizablecomposition for optical materials described in [14], in which thepolyether compound (D) is at least one compound selected from acompound represented by the following General Formula (d1) and acompound represented by the following General Formula (d2), and thepolyether-modified siloxane compound (E) is a compound representedby the following General Formula (e);

##STR00008##

[0041] wherein, in General Formula (d1), R.sub.1 and R.sub.2 eachrepresent a hydrogen atom or an alkyl group having 1 to 18 carbonatoms, and at least one of R.sub.1 and R.sub.2 is a hydrogen atom.A plurality of R.sub.1's may be the same or different from eachother, and a plurality of R.sub.2's may be the same or differentfrom each other. m represents an integer of 15 to 500,

##STR00009##

[0042] wherein, in General Formula (d2), Q represents an(n+f)-valent hydrocarbon group. n represents an integer of 0 ormore, f represents an integer of 1 or more, and n+f is 3 or more. mrepresents an integer of 2 to 58,

##STR00010##

[0043] wherein, in General Formula (e), R.sub.1 to R.sub.8 may bethe same or different from each other, at least one of R.sub.1 toR.sub.8 represents a polyether group represented by the followingGeneral Formula (i), and the rest of R.sub.1 to R.sub.8 may be thesame or different from each other and each represent a linear orbranched alkyl group having 1 to 20 carbon atoms, a linear orbranched alkoxy group having 1 to 20 carbon atoms, a hydroxylgroup, or a polysiloxy group. A plurality of R.sub.2's to R.sub.5'smay be the same or different from each other. m and n may be thesame or different from each other and each represent an integer of0 or more,

##STR00011##

[0044] wherein, in General Formula (i), R.sub.25 represents alinear or branched alkylene group having 1 to 20 carbon atoms, andR.sub.26 represents a hydrogen atom, a linear or branched alkylgroup having 1 to 20 carbon atoms, a linear or branched alkenylgroup having 2 to 20 carbon atoms, or a linear or branched alkynylgroup having 2 to 20 carbon atoms. A plurality of R.sub.25's may bethe same or different from each other. k represents an integer of 1or more.

[0045] [16] The method for manufacturing a polymerizablecomposition for optical materials described in [14] or [15], inwhich the polyether-modified siloxane compound (E) is a compoundrepresented by the following General Formula (e-1), a compoundrepresented by the following General Formula (e-2), or a mixture ofthese,

##STR00012##

[0046] wherein, in General Formula (e-1), a+c is an integer of 1 to100, b is an integer of 1 to 100, d is an integer of 10 to 1,000,and e is an integer of 1 to 100,

##STR00013##

[0047] wherein, in General Formula (e-2), f+h is preferably aninteger of 1 to 100, and g is an integer of 1 to 100.

Advantageous Effects of Invention

[0048] The polymerizable composition for optical materials of thepresent invention can provide optical materials which haveexcellent photochromic performance, are inhibited from causingwhite turbidity, have excellent transparency, are inhibited fromforming striae, and look beautiful. In other words, thepolymerizable composition for optical materials of the presentinvention can provide optical materials having these propertiesthat are well balanced.

DESCRIPTION OF EMBODIMENTS

[0049] The polymerizable composition for optical materialsaccording to the present invention will be described based on thefollowing embodiments. In the present embodiment, unless otherwisespecified, "A to B" represents "A or more" and "B or less".

[0050] The polymerizable composition for optical materials of thepresent embodiment contains a polyisocyanate compound (A), apolythiol compound (B), a photochromic compound (C), a polyethercompound (D), and a polyether-modified siloxane compound (E).Hereinafter, each component will be described.

[0051] [Polyisocyanate Compound (A)]

[0052] As the polyisocyanate compound (A), conventionally knowncompounds can be used as long as the compounds bring about theeffects of the present invention. Examples of the compounds includean aliphatic isocyanate compound, an alicyclic isocyanate compound,an aromatic isocyanate compound, a heterocyclic isocyanatecompound, an aromatic aliphatic isocyanate compound, and the like.One of these may be used alone, or two or more of these may be usedby being mixed together. These isocyanate compounds may include adimer, a trimer, and a prepolymer. Examples of these isocyanatecompounds include the compounds exemplified in WO2011/055540.

[0053] The polyisocyanate compound (A) is preferably at least onecompound selected from2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane,2,6-bis(isocyanatomethyl)bicyclo-[2.2.1] heptane, m-xylylenediisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate,dicyclohexylmethane diisocyanate,1,3-bis(isocyanatomethyl)cyclohexane,1,4-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate,1,6-hexamethylene diisocyanate, and 1,5-pentamethylenediisocyanate, and more preferably at least one compound selectedfrom 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane,2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, andbis(isocyanatomethyl)cyclohexane.

[0054] [Polythiol Compound (B)]

[0055] The polythiol compound (B) is a compound having two or moremercapto groups. Conventionally known polythiol compounds can beused as long as the compounds bring about the effects of thepresent invention. Examples thereof include the compoundsexemplified in WO2016/125736.

[0056] In the present embodiment, from the viewpoint of effects ofthe present invention, the polythiol compound (B) is preferably atleast one compound selected from4-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,pentaerythritol tetrakis(3-mercaptopropionate),bis(mercaptoethyl)sulfide, pentaerythritoltetrakis(2-mercaptoacetate), 2,5-bis(mercaptomethyl)-1,4-dithiane,1,1,3,3-tetrakis(mercaptomethylthio)propane,4,6-bis(mercaptomethylthio)-1,3-dithiane, and2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithietane, and morepreferably at least one compound selected from4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, pentaerythritoltetrakis(3-mercaptopropionate), pentaerythritoltetrakis(2-mercaptoacetate), and2,5-bis(mercaptomethyl)-1,4-dithiane.

[0057] [Photochromic Compound (C)]

[0058] The photochromic compound is a compound which has amolecular structure reversibly changing by the irradiation withlight of a specific wavelength and undergoes change of absorptioncharacteristics (absorption spectrum) by the structural change.

[0059] Examples of the photochromic compound (C) used in thepresent embodiment include compounds whose absorptioncharacteristics (absorption spectrum) change by light of a specificwavelength.

[0060] In the present embodiment, the photochromic compound (C) isnot particularly limited. From the conventionally knownphotochromic compounds that can be used in photochromic lenses, anycompound can be appropriately selected and used. For example, it ispossible to use one compound or two or more compounds among aspiropyran-based compound, a spirooxazine-based compound, afulgide-based compound, a naphthopyran-based compound, abisimidazole compound, and the like, depending on the desired colorto be added. In the present embodiment, it is preferable to use anaphthopyran-based compound as the photochromic compound (C).

[0061] In the present embodiment, it is preferable to use at leastone photochromic compound selected from General Formula (c1) andGeneral Formula (c2).

PC-L-Chain (c1)

PC-L-Chain-L'-PC' (c2)

PC and PC' each represent a monovalent group derived from thecompounds represented by General Formulas (1) to (4). PC and PC'may be the same or different from each other.

##STR00014##

[0062] In Formulas (1) to (4), R.sub.1 to R.sub.18 each representhydrogen, a halogen atom, a carboxyl group, an acetyl group, aformyl group, a C1-C20 aliphatic group which is optionallysubstituted, a C3-C20 alicyclic group which is optionallysubstituted, or a C6-C20 aromatic organic group which is optionallysubstituted. R.sub.1 to R.sub.18 may be the same or different fromeach other. These aliphatic group, alicyclic group, and aromaticorganic group may have an oxygen atom or a nitrogen atom. Any onegroup contained in the compounds represented by General Formulas(1) to (4) is bonded to L or L' which is a divalent organicgroup.

[0063] Examples of the C1-C20 aliphatic group which is optionallysubstituted include a linear or branched C1-C10 alkyl group, alinear or branched C1-C10 alkoxy group, a linear or branched C2-C10alkenyl group, a C1-C10 hydroxyalkyl group, a C1-C10 hydroxyalkoxygroup, a C1-C10 alkyl group substituted with a C1-C10 alkoxy group,a C1-C10 alkoxy group substituted with a C1-C10 alkoxy group, aC1-C5 haloalkyl group, a C1-C5 dihaloalkyl group, a C1-C5trihaloalkyl group, a C1-C10 alkylamino group, a C1-C10 aminoalkylgroup, a linear or branched C1-C20 alkoxycarbonyl group, and thelike.

[0064] Examples of the C3-C20 alicyclic group which is optionallysubstituted include a C3-C20 cycloalkyl group, a C6-C20bicycloalkyl group, and the like.

[0065] Examples of the C6-C20 aromatic organic group which isoptionally substituted include a phenyl group, a C7-C16alkoxyphenyl group, an arylamino group, a diarylamino group, anaryl C1-C5 alkylamino group, a cyclic amino group, an arylcarbonylgroup, and aroyl group, and the like.

[0066] As R.sub.1 and R.sub.2, for example, a hydrogen atom; ahalogen atom;

[0067] a C1-C20 aliphatic group which is optionally substituted,such as a linear or branched C1-C10 alkyl group, a linear orbranched C1-C10 alkoxy group, a C1-C10 hydroxyalkoxy group, aC1-C10 alkoxy group substituted with a C1-C10 alkoxy group, a C1-C5haloalkyl group, a C1-C5 dihaloalkyl group, a C1-C5 trihaloalkylgroup, or a C1-C5 alkylamino group;

[0068] a C6-C20 aromatic organic group which is optionallysubstituted, such as a phenyl group, a C7-C16 alkoxyphenyl group, aC1-C5 dialkylamino group, an arylamino group, a diarylamino group,an aryl C1-C5 alkylamino group, or a cyclic amino group; and thelike are preferable. R.sub.1 and R.sub.2 may be the same ordifferent from each other.

[0069] As R.sub.3, for example, a hydrogen atom; a halogen atom; acarboxyl group; an acetyl group;

[0070] a C1-C20 aliphatic group which is optionally substituted,such as a linear or branched C1-C10 alkyl group, a linear orbranched C2-C10 alkenyl group, a linear or branched C1-C10 alkoxygroup, a C1-C10 hydroxyalkyl group, a C1-C10 alkyl groupsubstituted with a C1-C10 alkoxy group, a C1-C10 aminoalkyl group,or a linear or branched C1-C20 alkoxycarbonyl group;

[0071] a C3-C20 alicyclic group which is optionally substituted,such as a C3-C20 cycloalkyl group or a C6-C20 bicycloalkylgroup;

[0072] a C6-C20 aromatic organic group which is optionallysubstituted, such as an arylcarbonyl group, a formyl group, or anaroyl group; and the like are preferable.

[0073] As R.sub.4, for example, a hydrogen atom; a halogen atom; acarboxyl group; an acetyl group; a formyl group;

[0074] a C1-C20 aliphatic group which is optionally substituted,such as a linear or branched C1-C10 alkyl group, a linear orbranched C2-C10 alkenyl group, a linear or branched C1-C10 alkoxygroup, a C1-C10 hydroxyalkyl group, a C1-C10 alkyl groupsubstituted with a C1-C10 alkoxy group, a C1-C10 aminoalkyl group,or a linear or branched C1-C20 alkoxycarbonyl group;

[0075] a C3-C20 alicyclic group which is optionally substituted,such as a C3-C20 cycloalkyl group or a C6-C20 bicycloalkylgroup;

[0076] a C6-C20 aromatic organic group which is optionallysubstituted, such as an arylcarbonyl group, an aroyl group, aphenyl group, a C7-C16 alkoxyphenyl group, a C1-C10 dialkoxyphenylgroup, a C1-C10 alkylphenyl group, or a C1-C10 dialkylphenyl group;and the like are preferable.

[0077] R.sub.3 and R.sub.4 may be bonded to each other. In a casewhere R.sub.3 and R.sub.4 are bonded to each other to form a ringstructure, for example, a structure represented by General Formula(5) or (6) is formed. The portion of the dotted line represents abond between a carbon atom to which R.sub.3 is bonded and a carbonatom to which R.sub.4 is bonded.

##STR00015##

[0078] R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10,R.sub.14, R.sub.15, and R.sub.16 represent the same functionalgroup as R.sub.1 and R.sub.2. A plurality of R.sub.5's to R.sub.7'smay be the same or different from each other.

[0079] As R.sub.11, for example, a hydrogen atom; a halogenatom;

[0080] a C1-C20 aliphatic group which is optionally substituted,such as a linear or branched C1-C20 alkyl group, a C1-C5 haloalkylgroup, a C1-C5 dihaloalkyl group, or a C1-C5 trihaloalkylgroup;

[0081] a C3-C20 alicyclic group which is optionally substituted,such as a C3-C20 cycloalkyl group, a C6-C20 bicycloalkyl group, aC3-C20 cycloalkyl group substituted with a C1-C5 alkyl group, or aC6-C20 bicycloalkyl group substituted with a C1-C5 alkyl group; aC6-C20 aromatic organic group which is optionally substituted, suchas an aryl group substituted with a C1-C5 alkyl group; and the likeare preferable.

[0082] As R.sub.12 and R.sub.13, for example, a hydrogen atom; ahalogen atom;

[0083] a C1-C20 aliphatic group which is optionally substituted,such as a C1-C10 alkyl group or a C1-C5 alkylalkoxycarbonyl group;a C3-C20 alicyclic group which is optionally substituted, such as aC5-C7 cycloalkyl group; and the like are preferable.

[0084] As R.sub.17 and R.sub.18, for example, a hydrogen atom; ahalogen atom;

[0085] a C1-C20 aliphatic group which is optionally substituted,such as a linear or branched C1-C10 alkyl group or a C1-C10hydroxyalkyl group; a C3-C20 alicyclic group which is optionallysubstituted, such as a C5-C7 cycloalkyl group; and the like arepreferable.

[0086] L and L' in General Formula (c1) or (c2) each represent adivalent organic group including at least one group selected froman oxyethylene chain, an oxypropylene chain, a (thio) ester group,and a (thio) amide group.

[0087] Specifically, L and L' are represented by General Formulas(7) to (13). L and L' may be the same or different from eachother.

##STR00016##

[0088] In Formulas (7) to (13),

[0089] Y represents oxygen or sulfur.

[0090] R.sub.19 represents hydrogen or a linear or branched C1-C10alkyl group.

[0091] R.sub.20 represents a linear or branched C1-C10 alkylgroup.

[0092] p represents an integer of 0 to 15, and r represents aninteger of 0 to 10.

[0093] Q represents a linear or branched C1-C10 alkylene group, aC1-C10 alkenylene group, a divalent group derived from asubstituent aryl group at the 1,2-, 1,3-, or 1,4-position, adivalent group derived from a substituent heteroaryl group, and thelike.

[0094] *1 and *2 each represent a bond. *1 is bonded to amonovalent or divalent organic group represented by "Chain", and *2is bonded to a monovalent organic group represented by PC orPC'.

[0095] "Chain" in General Formula (c1) or (c2) represents amonovalent or divalent organic group having at least one chainselected from a polysiloxane chain and a polyoxyalkylene chain.

[0096] Examples of the polysiloxane chain include apolydimethylsiloxane chain, a polymethylphenylsiloxane chain, apolymethylhydrosiloxane chain, and the like.

[0097] Examples of the polyoxyalkylene chain include apolyoxyethylene chain, a polyoxypropylene chain, apolyoxyhexamethylene chain, and the like.

[0098] Specifically, in a case where the photochromic compound isrepresented by General Formula (c1), "Chain" represents amonovalent organic group represented by General Formula (14) or(15).

##STR00017##

[0099] In a case where the photochromic compound is represented byGeneral Formula (c2), "Chain" represents a divalent organic grouprepresented by General Formula (16) or (17).

##STR00018##

[0100] In Formulas (14) to (17),

[0101] R.sub.21 represents a linear or branched C1-C10 alkylgroup.

[0102] R.sub.22 represents a linear or branched C1-C10 alkylgroup.

[0103] R.sub.23 represents hydrogen, a methyl group, or an ethylgroup.

[0104] n represents an integer of 4 to 75, and m represents aninteger of 1 to 50.

[0105] q represents an integer of 1 to 3.

[0106] *3 and *4 each represent a bond. *3 is bonded to a divalentorganic group represented by L, and *4 is bonded to a divalentorganic group represented by L'.

[0107] The photochromic compound (C) of the present embodiment isobtained by the methods described in WO2009/146509, WO2010/20770,WO2012/149599, and WO2012/162725.

[0108] Examples of the photochromic compound (C) of the presentembodiment include Reversacol Humber Blue (polydimethylsiloxanechain, naphthopyran-based chromophore (General Formula (1)),Reversacol Calder Blue (polydimethylsiloxane chain,naphthopyran-based chromophore (General Formula (1)), ReversacolTrent Blue (polydimethylsiloxane chain, naphthopyran-basedchromophore (General Formula (1)), Reversacol Pennine Green(polydimethylsiloxane chain, naphthopyran-based chromophore(General Formula (1)), Reversacol Heath Green (polyoxyalkylenechain, naphthopyran-based chromophore (General Formula (1)),Reversacol Chilli Red (polydimethylsiloxane chain,naphthopyran-based chromophore (General Formula (1)), ReversacolWembley Grey (polyoxyalkylene chain, naphthopyran-based chromophore(General Formula (1)), and Reversacol Cayenne Red (polyoxyalkylenechain, naphthopyran-based chromophore (General Formula (1)),Peaco*ck Blue (polyoxyalkylene chain, naphthopyran-based chromophore(General Formula (1)), Jalapeno Red (polyoxyalkylene chain,naphthopyran-based chromophore (General Formula (1)) manufacturedby Vivimed Labs Limited, and the like. One photochromic compoundcan be used alone, or two or more photochromic compounds can beused in combination.

[0109] In the present embodiment, it is preferable to use at leastone compound selected from Reversacol Trent Blue, Reversacol HeathGreen, Reversacol Chilli Red, Reversacol Wembley Grey, ReversacolCayenne Red, Peaco*ck Blue, Jalapeno Red.

[0110] The photochromic compound (C) can also be added using apremix of the photochromic compound (C) and the polyisocyanatecompound (A). The total amount of the polyisocyanate compound (A)used in the present embodiment includes the amount of thepolyisocyanate compound (A) used in the premix.

[0111] [Polyether Compound (D)]

[0112] The polyether compound (D) is at least one compound selectedfrom compounds having a number-average molecular weight of 50 to10,000. The number-average molecular weight of the polyethercompound (D) is preferably 100 to 8,000, more preferably 500 to5,000, even more preferably 1,000 to 4,000, and particularlypreferably 1,500 to 3,500.

[0113] The polyether compound (D) to be used can be selected fromknown compounds having a number-average molecular weight in theabove range, as long as the compounds can bring about the effectsof the present invention.

[0114] The polyether compound (D) is preferably at least onecompound selected from a compound (d1) represented by the followingGeneral Formula (d1) and a compound (d2) represented by thefollowing General Formula (d2).

##STR00019##

[0115] In General Formula (d1), R.sub.1 and R.sub.2 each representa hydrogen atom or an alkyl group having 1 to 18 carbon atoms, andat least one of R.sub.1 and R.sub.2 is a hydrogen atom. A pluralityof R.sub.1's may be the same or different from each other, and aplurality of R.sub.2's may be the same or different from eachother. m represents an integer of 15 to 500, and preferablyrepresents an integer of 30 to 500.

[0116] As the compound represented by General Formula (d1), it ispossible to use a compound which has a number-average molecularweight of 150 or more and preferably has a number-average molecularweight of 200 or more.

[0117] As the compound (d1), specifically, a compound representedby the following General Formula (d1-1) and a compound representedby General Formula (d1-2) can be used.

##STR00020##

[0118] In General Formula (d1-1), R.sub.3 and R.sub.4 eachrepresent a hydrogen atom or an alkyl group having 1 to 18 carbonatoms, and at least one of R.sub.3 and R.sub.4 is a hydrogen atom.a+c is an integer which is 2 to 600, and preferably 2 to 400. brepresents an integer which is 1 to 300, and preferably 1 to 100. Aplurality of R.sub.3's and R.sub.4's may be the same or differentfrom each other.

[0119] Examples of such a compound include the Pluronic seriesmanufactured by BASF SE. The structures of the compounds includedin Pluronic are shown in Non-Patent Document 1.

[0120] Sometimes the terminal hydroxyl group of the compoundrepresented by General Formula (d1) may react with a polymerizablecompound such as isocyanate.

[0121] Specifically, examples of the compound represented byGeneral Formula (d1-1) include a compound represented by thefollowing General Formula (d1-1').

##STR00021##

[0122] In General Formula (d1-1'), a, b, and c each represent thenumber of units. a, b, and c each independently represent aninteger of 3 to 300.

[0123] Examples of such a compound include the Pluronic series(manufactured by BASF SE), and the like.

##STR00022##

[0124] In General Formula (d1-2), a, b, and c each represent thenumber of units. a, b, and c each independently represent aninteger of 3 to 300.

[0125] Examples of such a compound include the Pluronic R series(manufactured by BASF SE) and the like.

##STR00023##

[0126] In General Formula (d2), Q represents an (n+f)-valenthydrocarbon group. n represents an integer of 0 or more, frepresents an integer of 1 or more, and n+f is 3 or more. mrepresents an integer of 2 to 58.

[0127] In General Formula (d2), the (HO).sub.n--R--(O).sub.f--group is a group having a valence of 3 or more which is derivedfrom a polyol having three or more primary hydroxyl groups.

[0128] Examples of the compound (d2) include CAPA (R)polycaprolactone polyol (manufactured by PERSTORP), PLACCEL (R)(manufactured by Daicel Corporation), and the like.

[0129] [Polyether-Modified Siloxane Compound (E)]

[0130] The polyether-modified siloxane compound (E) is at least onecompound selected from compounds having a viscosity of 1 mPas ormore and less than 1,600 mPas. The viscosity of thepolyether-modified siloxane compound (E) is preferably 5 to 1,000mPas, more preferably 10 to 500 mPas, even more preferably 15 to400 mPas, and particularly preferably 20 to 200 mPas.

[0131] The polyether-modified siloxane compound (E) to be used canbe selected from known compounds having a viscosity in the aboverange, as long as the compounds can bring about the effects of thepresent invention.

[0132] As the polyether-modified siloxane compound (E), forexample, it is preferable to use a compound represented by thefollowing General Formula (e).

##STR00024##

[0133] R.sub.1 to R.sub.8 may be the same or different from eachother, at least one of R.sub.1 to R.sub.8 represents a polyethergroup represented by the following General Formula (i), and therest of R.sub.1 to R.sub.8 may be the same or different from eachother and each represent a linear or branched alkyl group having 1to 20 carbon atoms, a linear or branched alkoxy group having 1 to20 carbon atoms, a hydroxyl group, or a polysiloxy group. Aplurality of R.sub.2's to R.sub.5's may be the same or differentfrom each other. m and n may be the same or different from eachother and each represent an integer of 0 or more, preferablyrepresent an integer of 1 to 20, and more preferably represent aninteger of 1 to 10.

##STR00025##

[0134] In General Formula (i), R.sub.25 represents a linear orbranched alkylene group having 1 to 20 carbon atoms, R.sub.26represents a hydrogen atom, a linear or branched alkyl group having1 to 20 carbon atoms, a linear or branched alkenyl group having 2to 20 carbon atoms, or a linear or branched alkynyl group having 2to 20 carbon atoms. A plurality of R.sub.25's may be the same ordifferent from each other. k represents an integer of 1 ormore.

[0135] k which represents the number of polymerized polyethermoieties can be appropriately selected from integers of 1 or more.k preferably represents an integer of 1 to 20, and more preferablyrepresents an integer of 1 to 10.

[0136] In one embodiment, from the viewpoint of effects of thepresent invention, k preferably represents an integer of 1 to1,000, more preferably represents an integer of 40 to 600, and evenmore preferably represents an integer of 55 to 550.

[0137] In one embodiment, R.sub.26 of the polyether grouprepresented by General Formula (i) preferably represents a hydrogenatom or a linear or branched alkyl group having 1 to 20 carbonatoms.

[0138] In one embodiment, R.sub.26 of the polyether grouprepresented by General Formula (i) represents a linear or branchedalkenyl group having 2 to 20 carbon atoms or a linear or branchedalkynyl group having 2 to 20 carbon atoms.

[0139] In one embodiment, from the viewpoint of effects of thepresent invention, R.sub.26 of the polyether group represented byGeneral Formula (i) is preferably a hydrogen atom or a linear orbranched alkenyl group having 2 to 20 carbon atoms, and morepreferably a hydrogen atom or a linear or branched alkenyl grouphaving 2 to 8 carbon atoms.

[0140] Specific examples of the substituents in the above GeneralFormula (e) include the following groups.

[0141] Examples of the linear or branched alkylene group having 1to 20 carbon atoms include a methylene group, an ethylene group, an-propylene group, an isopropylene group, a n-butylene group, anisobutylene group, a t-butylene group, a n-pentylene group, anisopentylene group, a t-pentylene group, a n-hexylene group, an-heptylene group, an isoheptylene group, a n-octylene group, anisooctylene group, a n-nonylene group, an isononylene group, an-decylene group, an isodecylene group, a n-undecylene group, anisoundecylene group, a n-dodecylene group, an isododecylene group,a cyclopentylene group, a cyclohexylene group, a cycloheptylenegroup, a cyclooctylene group, a cyclononylene group, amethylcyclopentylene group, a methylcyclohexylene group, and thelike. Among these, a linear or branched alkylene group having 1 to8 carbon atoms is preferable.

[0142] Examples of the linear or branched alkyl group having 1 to20 carbon atoms include a methyl group, an ethyl group, a n-propylgroup, an isopropyl group, a n-butyl group, an isobutyl group, at-butyl group, a n-pentyl group, an isopentyl group, a t-pentylgroup, a n-hexyl group, a n-heptyl group, an isoheptyl group, an-octyl group, an isooctyl group, a n-nonyl group, an isononylgroup, a n-decyl group, an isodecyl group, a n-undecyl group, anisoundecyl group, a n-dodecyl group, an isododecyl group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, a cyclononyl group, a methylcyclopentyl group, amethylcyclohexyl group, and the like.

[0143] Among these, a linear or branched alkyl group having 1 to 8carbon atoms is preferable.

[0144] Examples of the linear or branched alkoxy group having 1 to20 carbon atoms include a methoxy group, an ethoxy group, an-propyloxy group, an isopropyloxy group, a n-butyloxy group, anisobutyloxy group, a t-butyloxy group, a n-pentyloxy group, anisopentyloxy group, a t-pentyloxy group, a n-hexyloxy group, an-heptyloxy group, an isoheptyloxy group, a n-octyloxy group, anisooctyloxy group, a n-nonyloxy group, an isononyloxy group, an-decyloxy group, an isodecyloxy group, a n-undecyloxy group, anisoundecyloxy group, a n-dodecyloxy group, an isododecyloxy group,a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxygroup, a cyclooctyloxy group, a cyclononyloxy group, amethylcyclopentyloxy group, a methylcyclohexyloxy group, and thelike.

[0145] Among these, a linear or branched alkoxy group having 1 to 8carbon atoms is preferable.

[0146] Examples of the linear or branched alkenyl group having 2 to20 carbon atoms include a vinyl group, a 1-propenyl group, a2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenylgroup, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group,a 4-pentenyl group, a 1-hexenyl group, a 2-hexenyl group, a3-hexenyl group, a 4-hexenyl group, a 5-hexenyl group, a 6-heptenylgroup, a 7-octenyl group, a 8-nonenyl group, a 9-decenyl group, a2-methyl-1-propenyl group, a 2-methyl-2-propenyl group, a3-methyl-3-butenyl group, a 4-methyl-4-pentenyl group, a2-cyclohexyl-2-propenyl group, and the like.

[0147] Among these, a linear or branched alkenyl group having 2 to8 carbon atoms is preferable.

[0148] Examples of the linear or branched alkynyl group having 2 to20 carbon atoms include an ethynyl group, a 1-propynyl group, a2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynylgroup, a 2-methyl-2-propynyl group, a 3-methyl-1-butynyl group, a4-pentynyl group, a 5-hexynyl group, a 6-heptynyl group, a7-octynyl group, a 8-nonynyl group, a 9-decynyl group, and thelike.

[0149] Among these, a linear or branched alkynyl group having 2 to8 carbon atoms is preferable.

[0150] Examples of the compound represented by General Formula (e)include POLYFLOW KL-100, POLYFLOW KL-600, and GLANOL 410 (tradename, manufactured by KYOEISHA CHEMICAL Co., LTD.);

[0151] BYK-302, BYK-307, BYK-322, BYK-323, BYK-331, BYK-333,BYK-347, BYK-348, and BYK-349 (trade name, manufactured byBYK-Chemie GmbH);

[0152] KF-351, KF-353, KF-354L, KF-355, KF-355A, KF-615A, andKF-618 (trade name, manufactured by Shin-Etsu Chemical Co.,Ltd.);

[0153] SH3746, SH3771, SH8400, and SF8410 (trade name, manufacturedby Dow Corning Toray Co., Ltd.);

[0154] TSF4440, TSF4445, TSF4446, and TSF4452 (trade name,manufactured by Toshiba Silicones Co., Ltd.); and the like.However, the present invention is not limited to these examplecompounds. One of these may be used alone, or two or more of thesemay be used as a mixture.

[0155] Among the above examples, POLYFLOW KL-100 and POLYFLOWKL-600 (trade name manufactured by KYOEISHA CHEMICAL Co., LTD.) areparticularly preferable.

[0156] From the viewpoint of effects of the present invention, thecompound represented by General Formula (e) is preferably one ormore compounds selected from POLYFLOW KL-100 and POLYFLOW KL-600(trade name manufactured by KYOEISHA CHEMICAL Co., LTD.), and morepreferably POLYFLOW KL-100.

[0157] From the viewpoint of effects of the present invention, thepolyether-modified siloxane compound (E) preferably includes atleast one compound selected from a compound represented by GeneralFormula (e) in which R.sub.26 of the polyether group represented byGeneral Formula (i) is a hydrogen atom and a compound representedby General Formula (e) in which R.sub.26 of the polyether grouprepresented by General Formula (i) is a linear or branched alkenylgroup having 2 to 20 carbon atoms;

[0158] more preferably includes at least one compound selected froma compound represented by General Formula (e) in which R.sub.26 ofthe polyether group represented by General Formula (i) is ahydrogen atom and a compound represented by General Formula (e) inwhich R.sub.26 of the polyether group represented by GeneralFormula (i) is a linear or branched alkenyl group having 2 to 8carbon atoms;

[0159] even more preferably includes at least one compound selectedfrom a compound represented by General Formula (e) in whichR.sub.26 of the polyether group represented by General Formula (i)is a hydrogen atom and a compound represented by General Formula(e) in which R.sub.26 of the polyether group represented by GeneralFormula (i) is a linear or branched alkenyl group having 2 to 8carbon atoms; and still more preferably includes a compoundrepresented by the following General Formula (e-1) and a compoundrepresented by the following General Formula (e-2).

##STR00026##

[0160] From the viewpoint of effects of the present invention, a+cin the above General Formula (e-1) is preferably an integer of 1 to100, and more preferably an integer of 5 to 50.

[0161] From the same viewpoint as above, b in the above GeneralFormula (e-1) is preferably an integer of 1 to 100, and morepreferably an integer of 5 to 50.

[0162] From the same viewpoint as above, d in the above GeneralFormula (e-1) is preferably an integer of 10 to 1,000, and morepreferably an integer of 50 to 500.

[0163] From the same viewpoint as above, e in the above GeneralFormula (e-1) is preferably an integer of 1 to 100, and morepreferably an integer of 5 to 50.

[0164] From the same viewpoint as above, the molecular weight ofthe compound represented by the above General Formula (e-1) ispreferably 100 to 10,000, and more preferably 1,000 to 5,000.

##STR00027##

[0165] From the viewpoint of effects of the present invention, f+hin the above General Formula (e-2) is preferably an integer of 1 to100, and more preferably an integer of 1 to 20.

[0166] From the same viewpoint as above, g in the above GeneralFormula (e-2) is preferably an integer of 1 to 100, and morepreferably an integer of 1 to 10.

[0167] From the same viewpoint as above, the molecular weight ofthe compound represented by the above General Formula (e-2) ispreferably 100 to 10,000, and more preferably 500 to 5,000.

[0168] In a case where the polyether-modified siloxane compound (E)includes the compounds represented by General Formula (e-1) andGeneral Formula (e-2), from the viewpoint of effects of the presentinvention, the mass ratio of the compound represented by GeneralFormula (e-1) and the compound represented by General Formula (e-2)in the polyether-modified siloxane compound (E) is set, so that theratio of the mass of the compound represented by General Formula(e-1) to the total mass of the compound represented by GeneralFormula (e-1) and the compound represented by General Formula (e-2)is preferably 50% to 90%, and more preferably 60% to 80%.

[0169] [Other Components]

[0170] In the present embodiment, the polymerizable composition mayfurther contain an internal release agent, an ultraviolet absorber,a hindered amine-based light stabilizer, a dye, a resin modifier, apolymerization catalyst, and the like, in addition to theaforementioned components (A) to (E).

[0171] As the internal release agent, an acidic phosphoric acidester or unreactive silicone oil can be used. Examples of theacidic phosphoric acid ester include a phosphoric acid monoesterand a phosphoric acid diester. One of these can be used alone, ortwo or more of these esters can be used in combination.

[0172] Examples of the ultraviolet absorber include variousultraviolet absorbers such as a benzotriazole-based ultravioletabsorber, a triazine-based ultraviolet absorber, abenzophenone-based ultraviolet absorber, a benzoate-basedultraviolet absorber, a propanedioic acid ester-based ultravioletabsorber, and an oxanilide-based ultraviolet absorber. One of thesecan be used alone, or two or more of these can be used incombination.

[0173] Examples of the dye include an anthraquinone-based dye, aperinone-based dye, a monoazo-based dye, a diazo-based dyes, aphthalocyanine-based dye, and the like. One of these can be usedalone, or two or more of these can be used in combination.

[0174] Examples of the resin modifier include olefin compoundsincluding a polyoxyalkylene alkyl ether compound, a polyoxyalkylenefatty acid ester, an episulfide compound, an alcohol compound, anamine compound, an epoxy compound, an organic acid and anhydridesthereof, a (meth)acrylate compound, and the like. One of these canbe used alone, or two or more of these can be used incombination.

[0175] <Polymerizable Composition for Optical Materials>

[0176] The polymerizable composition for optical materials of thepresent embodiment contains the aforementioned components (A) to(E) and contains, if necessary, other components.

[0177] The ratio of the polyisocyanate compound (A) and thepolythiol compound (B) used is not particularly limited. Generally,a molar ratio of SH group/NCO group is in a range of 0.5 to 3.0,preferably in a range of 0.6 to 2.0, and more preferably in a rangeof 0.8 to 1.3.

[0178] From the viewpoint of photochromic performance, the ratio ofthe photochromic compound (C) with respect to 100 parts by weightof the polyether compound (D) is 0.01 to 100 parts by weight, andmore preferably 1 to 10 parts by weight.

[0179] From the viewpoint of effects of the present invention, theamount of the polyether compound (D) used can be set such that thecontent of the compound (D) with respect to 100% by weight of thepolymerizable composition for optical materials is 0.5% to 10% byweight, preferably 1.0% to 9.0% by weight, and more preferably 2.0%to 8.0% by weight.

[0180] From the viewpoint of effects of the present invention, theamount of the polyether-modified siloxane compound (E) used can beset such that the content of the compound (E) with respect to 100%by weight of the polymerizable composition for optical materials is0.001% to 2% by weight, and preferably 0.01% to 1% by weight.

[0181] From the viewpoint of effects of the present invention, theratio of the content of the polyether-modified siloxane compound(E) to the content of the polyether compound (D) (E (partsbyweight)/D (parts by weight)) can be set such that the ratio is0.01 to 1.0, preferably 0.05 to 0.5, more preferably 0.10 to 0.40,and even more preferably 0.15 to 0.20. In a case where thepolyether compound (D) is used, the larger the amount of thecompound (D) added, the further the photochromic performance isimproved, but the further the striae tend to occur, which meansthat there is a trade-off relationship between the improvement ofphotochromic performance and the suppression of striae. In thepresent invention, the ratio (E/D) is in the above range. As aresult, both the improvement of photochromic performance and thesuppression of striae can be accomplished, and optical materialscan be obtained which have higher photochromic performance, furtherinhibited from forming striae, and look beautiful (have excellenttransparency). In other words, the polymerizable composition foroptical materials of the present invention can provide opticalmaterials having these properties that are well balanced.

[0182] The polymerizable composition for optical materials of thepresent embodiment can be prepared by mixing together theaforementioned components (A) to (E) and, if necessary, othercomponents described above.

[0183] In the present embodiment, it is preferable that thepolymerizable composition for optical materials be prepared by amanufacturing method including Step a of mixing together thepolyisocyanate compound (A), the photochromic compound (C), thepolyether compound (D), and the polyether-modified siloxanecompound (E), and a step b of mixing the mixed solution obtained byStep a with the polythiol compound (B).

[0184] Step a can also be a step of preparing a premix of thephotochromic compound (C) and the polyisocyanate compound (A) andmixing the premix with the polyisocyanate compound (A), thepolyether compound (D), and the polyether-modified siloxanecompound (E).

[0185] Depending on the preparation conditions, sometimes thepolyether compound (D) forms a microphase-separated structure insome parts of the polymerizable composition for optical materialsin the present embodiment.

[0186] <Cured Product>

[0187] It is possible to obtain a cured product by polymerizing andcuring the polymerizable composition for optical materials in thepresent embodiment. The molded product of the present embodimentcontains a microphase-separated structure of the polyether compound(D), the photochromic compound (C), and a thiourethane resinobtained by polymerizing the polyisocyanate compound (A) and thepolythiol compound (B). Examples of the microphase-separatedstructure include polymer particles (micellar particles) having amicrophase-separated structure composed of the polyether compound(D). The cured product including the microphase-separated structurecan provide an optical material excellent in photochromicproperties, heat resistance, and mechanical properties.

[0188] At least a part of the photochromic compound (C) may beencapsulated in the microphase-separated structure composed of thepolyether compound (D). In this case, the effects described aboveare particularly excellent.

[0189] The 50% volume-based average particle size of the polymerparticles, which are a microphase-separated structure, is 1 nm to1,000 nm. This structure can be confirmed using a transmissionelectron microscope.

[0190] (Microphase-Separated Structure)

[0191] The microphase-separated structure will be described below.A block copolymer is a polymer consisting of a plurality ofdifferent copolymer moieties connected to each other throughcovalent bonds.

[0192] These copolymer moieties have different physical propertiesand affinities. For example, in an amphipathic block copolymer, thecopolymer moieties tend to separate from each other due to strongrepulsive force and are not intermixed just as water and oil, whichleads to phase separation. However, because the copolymer moietiesare chemically bonded to each other, complete macroscopic phaseseparation found in a simple mixture of two hom*opolymers does notoccur. On the other hand, in the microphase separation of a blockcopolymer consisting of different copolymer moieties A and B, amicroaggregate of a moiety rich in the copolymer A and a moietyrich in the copolymer B is formed. As a result, depending on thestructure of block copolymer, several morphologies such asnano-sized spherical polymer micelles can be observed. Details ofthe microphase separation of such a block copolymer are described,for example, in a reference (Chem. Soc. Rev., 2012, 41, 5969-5985).By having a microphase-separated structure such as polymerparticles including a microphase-separated structure, the obtainedcured product can have transparency with less turbidity.

[0193] The method for manufacturing the cured product of thepresent embodiment includes a step of polymerizing and curing thepolymerizable composition for optical materials. Specifically, inthis step, the polyisocyanate compound (A) and the polythiolcompound (B) are polymerized to form a resin, the polyethercompound (D) forms a microphase-separated structure, and a moldedproduct consisting of the resin, the microphase-separatedstructure, and the photochromic compound (C) is formed.

[0194] In this step, by heating or irradiating the polymerizablecomposition for optical materials with radiation other thaninfrared rays, such as ultraviolet rays, it is possible topolymerize and cure the composition and to obtain a cured product.The polymerization conditions are appropriately selected.

[0195] <Molded Product>

[0196] In order to manufacture the resin that is obtained byheating and polymerizing the composition of the present embodimentand to manufacture a molded product formed of the resin, ifnecessary, various additives described above and the like areadded. Furthermore, as long as the effects of the presentembodiment are not impaired, polymerizable compounds, additives,and the like that are not described in the present application maybe added to the composition in the present embodiment. Just as thecured product, the molded product of the present embodimentincludes a microphase-separated structure of the polyether compound(D).

[0197] <Use>

[0198] In the present embodiment, by varying the shape of moldsused in polymerizing the aforementioned polymerizable compositionfor optical materials, it is possible to obtain molded products invarious shapes and optical materials formed of the molded products.The molded product of the present embodiment that is shaped asdesired and provided with a coat layer, other members, and the likeformed as needed can be used as various optical materials.

[0199] Examples of the optical materials include a plastic lens,alight emitting diode (LED), a prism, optical fiber, an informationrecording substrate, a filter, and the like. Particularly, theoptical materials are suitable as a plastic lens.

[0200] <Plastic Lens>

[0201] The plastic lens of the present embodiment is usuallymanufactured by a cast polymerization method using theaforementioned polymerizable composition for optical materials.Specifically, the method for manufacturing the plastic lens of thepresent embodiment includes a step of performing castpolymerization on the polymerizable composition for opticalmaterials so as to form a lens substrate.

[0202] In this step, the obtained composition of the presentembodiment is injected into a cavity consisting of a cavity moldand a gasket or tape and heated so that the composition ispolymerized and cured. In this way, a resin of the presentembodiment and a plastic lens substrate formed of the resin ismanufactured. By this step, the polyisocyanate compound (A) and thepolythiol compound (B) are polymerized to form a resin, and thepolyether compound (D) forms a microphase-separated structure,which makes it possible to obtain a plastic lens substrate formedof the resin, the microphase-separated structure, and thephotochromic compound (C).

[0203] The polymerization conditions are not limited because theygreatly vary with the type and used amount of the polymerizablecomposition for optical materials and the catalyst, the mold shape,and the like. Generally, the polymerization is performed for 1 to50 hours at -50.degree. C. to 150.degree. C. In some cases, it ispreferable to cure the composition for 1 to 25 hours at atemperature that is fixed or slowly raised within a range of10.degree. C. to 150.degree. C.

[0204] If necessary, after being released from the mold, theobtained plastic lens may be subjected to a re-heating treatment(annealing).

[0205] The surface of the cured resin of the present embodiment andthe surface of the plastic lens composed of the resin may beprovided with functional coat layers such a hardcoat, anantireflection coat, a light controlling coat, a lubricating coator a lubricating treatment, and an antistatic coat. Furthermore,for the surface of the cured resin and the plastic lens, a coloringtreatment for fashion, a surface or edge polishing treatment, andthe like may be performed. In addition, a polarizing film may beput into the resin or the plastic lens or attached to the surfaceof the resin or the plastic lens so that the polarizing propertiesare added, and various types of processing for adding functions mayalso be performed.

[0206] The plastic lens of the present embodiment can be used asvarious lenses such as a spectacle lens, a camera lens, a pickuplens, a Fresnel lens, a prism lens, and a lenticular lens. Theplastic lens is particularly preferably used as a spectacle lens, acamera lens, and a pickup lens having a smooth surface, among theabove.

[0207] Hitherto, the embodiments of the present invention have beendescribed. However, the embodiments are merely examples of thepresent invention, and various configurations other than the abovecan be adopted as long as the effects of the present invention arenot impaired.

EXAMPLE

[0208] Hereinafter, the present invention will be more specificallydescribed with reference to examples, but the present invention isnot limited thereto. The transparency and striae of the moldedproduct manufactured in examples and comparative examples wereevaluated by the following methods.

[0209] Transparency

[0210] Transparency was evaluated based on a devitrification level.First, a circular plate-like lens having a thickness of 9 mm and adiameter of 75 mm was prepared. Then, the lens plate was irradiatedwith a light source (Luminar Ace LA-150A manufactured byHAYASHI-REPIC CO., Ltd.), and the image was measured using agreyscale imaging device. The captured image was processed into agreyscale image to digitize the devitrification level. Based on theobtained values of devitrification level, transparency wasevaluated according to the following criteria. The lens wasvisually observed as well for evaluation.

[0211] 3: The devitrification level is less than 150(transparent).

[0212] 2: The devitrification level is less than 200 (slight whiteturbidity occurs, but the lens is transparent).

[0213] 1: The devitrification level is 200 or more (white turbidityoccurs).

[0214] Striae

[0215] The molded product was illuminated with an ultra-highpressure mercury lamp (light source model OPM-252HEG: manufacturedby Ushio Inc.), and the projected image was visually observed toevaluate whether or not striae exist. Striae was evaluatedaccording to the following criteria.

[0216] A: No striae

[0217] B: There are faint striae in the peripheral portion.

[0218] C: Faint striae are observed all over the moldedproduct.

[0219] D: Moderate striae are observed all over the moldedproduct.

[0220] E: Marked striae are observed all over the moldedproduct.

Example 1

[0221] Reversacol Wembley Grey (0.036 parts by weight), 0.060 partsby weight of Reversacol Heath Green, 0.030 parts by weight ofPeaco*ck Blue, and 0.024 parts by weight of Jalapeno Red asphotochromic compounds manufactured by Vivimed Labs Limited and0.075 parts by weight of HOSTAVIN PR-25 as an ultraviolet absorberwere dissolved in 9.8 parts by weight of a composition containing2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, thereby preparinga master solution. The obtained master solution (10 parts byweight) was added to 30.05 parts by weight of a compositioncontaining 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, followed bystirring. ADEKA PLURONIC L-64 (2.52 parts by weight) manufacturedby ADEKA Corporation, 0.05 parts by weight of JP-506H as an acidicphosphoric acid ester manufactured by JOHOKU CHEMICAL CO., LTD, and0.4 parts by weight of a polyether-modified siloxane compound(POLYFLOW KL-100: manufactured by KYOEISHA CHEMICAL Co., LTD.) wereadded to the obtained mixed solution, and the obtained mixedsolution was stirred for 30 minutes at a temperature of 15.degree.C. to 20.degree. C.

[0222] Pentaerythritoltetrakis(3-mercaptopropionate) (19.98 partsby weight) and 27.25 parts by weight of4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane were added to themixed solution obtained as above, and the mixed solution wasstirred for 15 minutes at a temperature of 15.degree. C. to20.degree. C.

[0223] Dimethyltindichloride (0.015 parts by weight) was added to10 part by weight of a composition containing2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and uniformlydissolved, thereby preparing a solution. This solution was added tothe mixed solution obtained as above and stirred for 15 minutes ata temperature of 15.degree. C. to 20.degree. C., thereby obtaininga polymerizable composition.

[0224] Thereafter, the polymerizable composition was stirred anddegassed for 1 hour at a temperature of 15.degree. C. to 20.degree.C. in an environment with a reduced pressure of 400 Pa or less,then filtered through a 1.0 .mu.m PTFE filter, and cast into aglass mold. The polymerizable composition was polymerized for 48hours in a range of 10.degree. C. to 130.degree. C., then the moldwas taken out of the furnace and removed, and a molded productobtained by the polymerization was taken out.

[0225] The molded product was colorless and transparent and hadexcellent light control performance in which the molded productdevelops color as soon as being exposed to solar rays and isdecolored when the light rays are blocked. The molded product wasfound to have transparency suitable for optical materials and haveno striae. Table 1 shows the evaluation results of the obtainedmolded products.

Example 2

[0226] A polymerizable composition and a molded product wereprepared in the same manner as in Example 1, except that the amountof the polyether-modified siloxane compound (POLYFLOW KL-100:manufactured by KYOEISHA CHEMICAL Co., LTD.) added in Example 1 waschanged to 0.5 parts by weight.

[0227] The molded product was colorless and transparent and hadexcellent light control performance in which the molded productdevelops color as soon as being exposed to solar rays and isdecolored when the light rays are blocked. The molded product wasfound to have transparency suitable for optical materials and haveno striae. Table 1 shows the evaluation results of the obtainedmolded products.

Example 3

[0228] A polymerizable composition and a molded product wereprepared in the same manner as in Example 1, except that the amountof the polyether-modified siloxane compound (POLYFLOW KL-100:manufactured by KYOEISHA CHEMICAL Co., LTD.) added in Example 1 waschanged to 0.05 parts by weight.

[0229] The molded product was colorless and transparent and hadexcellent light control performance in which the molded productdevelops color as soon as being exposed to solar rays and isdecolored when the light rays are blocked. Furthermore, the moldedproduct was found to have transparency suitable for opticalmaterials and have moderate striae all over the molded product.Table 1 shows the evaluation results of the obtained moldedproducts.

Example 4

[0230] A polymerizable composition and a molded product wereprepared in the same manner as in Example 1, except that the amountof the polyether-modified siloxane compound (POLYFLOW KL-100:manufactured by KYOEISHA CHEMICAL Co., LTD.) added in Example 1 waschanged to 0.1 parts by weight.

[0231] The molded product was colorless and transparent and hadexcellent light control performance in which the molded productdevelops color as soon as being exposed to solar rays and isdecolored when the light rays are blocked. Furthermore, the moldedproduct was found to have transparency suitable for opticalmaterials and have moderate striae all over the molded product.Table 1 shows the evaluation results of the obtained moldedproducts.

Example 5

[0232] A polymerizable composition and a molded product wereprepared in the same manner as in Example 1, except that the amountof the polyether-modified siloxane compound (POLYFLOW KL-100:manufactured by KYOEISHA CHEMICAL Co., LTD.) added in Example 1 waschanged to 0.2 parts by weight.

[0233] The molded product was colorless and transparent and hadexcellent light control performance in which the molded productdevelops color as soon as being exposed to solar rays and isdecolored when the light rays are blocked. Furthermore, the moldedproduct was found to have transparency suitable for opticalmaterials and have moderate striae all over the molded product.Table 1 shows the evaluation results of the obtained moldedproducts.

Example 6

[0234] A polymerizable composition and a molded product wereprepared in the same manner as in Example 1, except that the amountof the polyether-modified siloxane compound (POLYFLOW KL-100:manufactured by KYOEISHA CHEMICAL Co., LTD.) added in Example 1 waschanged to 0.3 parts by weight.

[0235] The molded product was colorless and transparent and hadexcellent light control performance in which the molded productdevelops color as soon as being exposed to solar rays and isdecolored when the light rays are blocked. The molded product wasfound to have transparency suitable for optical materials and havefaint striae all over the molded product. Table 1 shows theevaluation results of the obtained molded products.

Example 7

[0236] A polymerizable composition and a molded product wereprepared in the same manner as in Example 1, except that the amountof the polyether-modified siloxane compound (POLYFLOW KL-100:manufactured by KYOEISHA CHEMICAL Co., LTD.) added in Example 1 waschanged to 1.0 part by weight.

[0237] The molded product was colorless and transparent and hadexcellent light control performance in which the molded productdevelops color as soon as being exposed to solar rays and isdecolored when the light rays are blocked. Furthermore, the moldedproduct was found to have transparency suitable for opticalmaterials and have faint striae in the peripheral portion. Table 1shows the evaluation results of the obtained molded products.

Example 8

[0238] Reversacol Wembley Grey (0.0745 parts by weight) and 0.061parts by weight of Reversacol Heath Green as photochromic compoundsmanufactured by Vivimed Labs Limited and 0.075 parts by weight ofHOSTAVIN PR-25 as an ultraviolet absorber were dissolved in 9.8parts by weight of a composition containing2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, thereby preparinga master solution. The obtained master solution (10 parts byweight) was added to 29.99 parts by weight of a compositioncontaining 2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane, followed bystirring. ADEKA PLURONIC L-64 (1.94 parts by weight) manufacturedby ADEKA Corporation, 0.05 parts by weight of JP-506H as an acidicphosphoric acid ester manufactured by JOHOKU CHEMICAL CO., LTD, and0.1 parts by weight of a polyether-modified siloxane compound(POLYFLOW KL-100: manufactured by KYOEISHA CHEMICAL Co., LTD.) wereadded to the obtained mixed solution, and the mixed solution wasstirred for 30 minutes at a temperature of 15.degree. C. to20.degree. C.

[0239] Pentaerythritoltetrakis(3-mercaptopropionate) (23.35 partsby weight) and 24.92 parts by weight of4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane were added to themixed solution obtained as above, and the mixed solution wasstirred for 15 minutes at a temperature of 15.degree. C. to20.degree. C.

[0240] Dimethyltindichloride (0.025 parts by weight) was added to10 part by weight of a composition containing2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and uniformlydissolved, thereby preparing a solution. This solution was added tothe mixed solution obtained as above and stirred for 15 minutes ata temperature of 15.degree. C. to 20.degree. C., thereby obtaininga polymerizable composition.

[0241] Thereafter, the polymerizable composition was stirred anddegassed for 1 hour at a temperature of 15.degree. C. to 20.degree.C. in an environment with a reduced pressure of 400 Pa or less,then filtered through a 1.0 .mu.m PTFE filter, and cast into aglass mold. The polymerizable composition was polymerized for 48hours in a range of 10.degree. C. to 130.degree. C., then the moldwas taken out of the furnace and removed, and a molded productobtained by the polymerization was taken out.

[0242] The molded product was colorless and transparent and hadexcellent light control performance in which the molded productdevelops color as soon as being exposed to solar rays and isdecolored when the light rays are blocked. The molded product wasfound to have transparency suitable for optical materials and havefaint striae in the peripheral portion. Table 1 shows theevaluation results of the obtained molded products.

Example 9

[0243] A polymerizable composition and a molded product wereprepared in the same manner as in Example 1, except that the amountof the polyether-modified siloxane compound (POLYFLOW KL-100:manufactured by KYOEISHA CHEMICAL Co., LTD.) added in Example 1 waschanged to 0.2 parts by weight.

[0244] The molded product was colorless and transparent and hadexcellent light control performance in which the molded productdevelops color as soon as being exposed to solar rays and isdecolored when the light rays are blocked. The molded product wasfound to have transparency suitable for optical materials and havefaint striae in the peripheral portion. Table 1 shows theevaluation results of the obtained molded products.

Example 10

[0245] A polymerizable composition and a molded product wereprepared in the same manner as in Example 1, except that the amountof the polyether-modified siloxane compound (POLYFLOW KL-100:manufactured by KYOEISHA CHEMICAL Co., LTD.) added in Example 1 waschanged to 0.3 parts by weight.

[0246] The molded product was colorless and transparent and hadexcellent light control performance in which the molded productdevelops color as soon as being exposed to solar rays and isdecolored when the light rays are blocked. The molded product wasfound to have transparency suitable for optical materials and havefaint striae all over the molded product. Table 1 shows theevaluation results of the obtained molded products.

Comparative Example 1

[0247] A polymerizable composition and a molded product wereprepared in the same manner as in Example 1, except that thepolyether-modified siloxane compound (POLYFLOW KL-100: manufacturedby KYOEISHA CHEMICAL Co., LTD.) was not added.

[0248] The molded product had excellent light control performancein which the molded product develops color as soon as being exposedto solar rays and is decolored when the light rays are blocked.Table 1 shows the results of evaluation on transparency and striaeof the molded product.

Comparative Example 2

[0249] A polymerizable composition and a molded product wereprepared in the same manner as in Example 1, except that the amountof the polyether-modified siloxane compound (KF-352A: manufacturedby Shin-Etsu Chemical Co., Ltd.) was changed to 0.5 parts byweight.

[0250] The molded product had excellent light control performancein which the molded product develops color as soon as being exposedto solar rays and is decolored when the light rays are blocked.Table 1 shows the results of evaluation on transparency and striaeof the molded product.

Comparative Example 3

[0251] A polymerizable composition and a molded product wereprepared in the same manner as in Example 1, except that the amountof the polyether-modified siloxane compound (X-22-4515:manufactured by Shin-Etsu Chemical Co., Ltd.) was changed to 0.5parts by weight.

[0252] The molded product had excellent light control performancein which the molded product develops color as soon as being exposedto solar rays and is decolored when the light rays are blocked.Table 1 shows the results of evaluation on transparency and striaeof the molded product.

TABLE-US-00001 TABLE 1 E (parts A D by component component Eweight)/D (Parts by B component C component (Parts by component(parts by weight) (Parts by weight) (Parts by weight) weight) (ppm)weight) Transparency Striae Example 1 A1 B1 B2 C1 C2 C3 C4 D1 E10.159 3 A (49.85) (27.25) (19.98) (0.036) (0.060) (0.030) (0.024)(2.52) (4,000) Example 2 A1 B1 B2 C1 C2 C3 C4 D1 E1 0.198 3 A(49.85) (27.25) (19.98) (0.036) (0.060) (0.030) (0.024) (2.52)(5,000) Example 3 A1 B1 B2 C1 C2 C3 C4 D1 E1 0.020 3 D (49.85)(27.25) (19.98) (0.036) (0.060) (0.030) (0.024) (2.52) (500)Example 4 A1 B1 B2 C1 C2 C3 C4 D1 E1 0.040 3 D (49.85) (27.25)(19.98) (0.036) (0.060) (0.030) (0.024) (2.52) (1,000) Example 5 A1B1 B2 C1 C2 C3 C4 D1 E1 0.079 3 D (49.85) (27.25) (19.98) (0.036)(0.060) (0.030) (0.024) (2.52) (2,000) Example 6 A1 B1 B2 C1 C2 C3C4 D1 E1 0.119 3 C (49.85) (27.25) (19.98) (0.036) (0.060) (0.030)(0.024) (2.52) (3,000) Example 7 A1 B1 B2 C1 C2 C3 C4 D1 E1 0.397 2B (49.85) (27.25) (19.98) (0.036) (0.060) (0.030) (0.024) (2.52)(10,000) Example 8 A1 B1 B2 C1 C2 -- -- D1 E1 0.052 3 B (49.79)(24.92) (23.35) (0.0745) (0.061) (1.94) (1,000) Example 9 A1 B1 B2C1 C2 -- -- D1 E1 0.103 3 B (49.79) (24.92) (23.35) (0.0745)(0.061) (1.94) (2,000) Example 10 A1 B1 B2 C1 C2 -- -- D1 E1 0.1552 C (49.79) (24.92) (23.35) (0.0745) (0.061) (1.94) (3,000)Comparative A1 B1 B2 C1 C2 C3 C4 D1 -- 0.000 3 E Example 1 (49.85)(27.25) (19.98) (0.036) (0.060) (0.030) (0.024) (2.52) ComparativeA1 B1 B2 C1 C2 C3 C4 D1 E2 0.198 1 E Example 2 (49.85) (27.25)(19.98) (0.036) (0.060) (0.030) (0.024) (2.52) (5,000) ComparativeA1 B1 B2 C1 C2 C3 C4 D1 E3 0.198 1 E Example 3 (49.85) (27.25)(19.98) (0.036) (0.060) (0.030) (0.024) (2.52) (5,000)

[0253] The components listed in Table 1 are as follows.

[0254] A1: Composition containing2,5-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane and2,6-bis(isocyanatomethyl)bicyclo-[2.2.1]-heptane

[0255] B1: 4-Mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane

[0256] B2: Pentaerythritol tetrakis(3-mercaptopropionate)

[0257] C1: Reversacol Wembley Grey (polyoxyalkylene chain,naphthopyran-based chromophore (General Formula (1)), manufacturedby Vivimed Labs Limited)

[0258] C2: Reversacol Heath Green (polyoxyalkylene chain,naphthopyran-based chromophore (General Formula (1)), manufacturedby Vivimed Labs Limited)

[0259] C3: Peaco*ck Blue (polyoxyalkylene chain, naphthopyran-basedchromophore (General Formula (1)), manufactured by Vivimed LabsLimited)

[0260] C4: Jalapeno Red (polyoxyalkylene chain, naphthopyran-basedchromophore (General Formula (1)), manufactured by Vivimed LabsLimited)

[0261] D1: ADEKA PLURONIC L-64 (block copolymer of polyethyleneglycol and polypropylene glycol having a number-average molecularweight of 2,900 (General Formula (d1-1'))

[0262] E1: POLYFLOW KL-100 (polyether-modified siloxane compound(General Formula (e)), manufactured by KYOEISHA CHEMICAL Co.,LTD.)

[0263] E2: KF-352A (polyether-modified siloxane compound,manufactured by Shin-Etsu Silicone)

[0264] E3: X-22-4515 (polyether-modified siloxane compound,manufactured by Shin-Etsu Silicone)

[0265] This application claims a priority based on Japanese PatentApplication No. 2019-092679 filed on May 16, 2019, the entirecontent of which is incorporated into the presentspecification.

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