JP4716249B2 - Polymerizable composition - Google Patents

Description

  The present invention relates to an optical material composition having excellent optical properties and high mechanical strength and heat resistance, and an optical material resin obtained by polymerizing this optical material composition.

  Plastic optical materials generally have advantages such as being lighter, easier to mold and dyeable than inorganic materials such as glass. Therefore, it has been widely used in recent years for various optical materials, particularly spectacle lenses.

  In addition to low specific gravity, the main performance required for eyeglass lenses is excellent optical performance (high refractive index, high Abbe number), chromaticity (high transparency, low yellowness), high strength (high impact resistance), etc. Is mentioned.

  Diethylene glycol diallyl carbonate resin called CR39, which has been widely used as a spectacle lens material until now, has a high Abbe number of 58 but a low refractive index of 1.50. For this reason, when used as a lens, there is a problem that a particularly strong lens has an increased outer thickness and a center thickness, resulting in poor appearance and heavy weight. Furthermore, it has a drawback that the falling ball impact strength is 100 g or less and is easily broken.

  For the purpose of improving the refractive index, synthetic resin optical materials containing sulfur atoms having a high atomic refractive index have been developed. For example, a thermosetting optical material having a thiourethane structure obtained by a reaction between a polythiol compound and a polyisocyanate compound has been proposed (see Patent Document 1 and Patent Document 2). Various novel polythiol compounds as raw materials for these thiourethanes have also been proposed. For example, a branched polythiol compound having four sulfur atoms in one molecule (see Patent Document 3), a branched polythiol compound having five sulfur atoms in one molecule (see Patent Document 4), and dithiane in the molecule. Examples include polythiol compounds having a ring structure (see Patent Document 5). These materials have excellent optical characteristics with a refractive index of about 1.66 at maximum and an Abbe number of 33-40. Furthermore, an episulfide resin having extremely excellent optical properties such as a refractive index of 1.70 and an Abbe number of 36 has been proposed (see Patent Document 6 and Patent Document 7).

  However, the impact resistance of these materials is not satisfactory, especially when a practical hard coat is applied, the impact resistance is greatly reduced, and as it is, the eyeglass lens safety standards set by the FDA (Food and Drug Administration) It is known that it cannot pass (16g or more). Therefore, in general, impact resistance is improved by applying a special hard coat such as addition of a cushion coat, but there is a big problem that productivity is remarkably lowered.

  As impact-resistant lenses, lenses using polycarbonate, which is a thermoplastic resin, are increasingly used mainly in the United States. Polycarbonate lenses have a very high drop ball impact strength of 1 kg or more, but due to the structure containing a large number of benzene rings, optical distortion occurs, and the Abbe number is as low as 30, resulting in a great disadvantage that optical unevenness occurs. There is also a problem that secondary workability such as cutting workability, hard coat workability and dyeability is poor.

  In addition, a polyurethane material containing an aliphatic linear oligomer has been proposed as a material having high impact resistance (see Patent Document 8 and Patent Document 9). The Abbe number is as high as 46, and the impact strength is 1 kg or more, and the impact resistance is as high as that of a polycarbonate lens. However, it has a very low refractive index of about 1.53.

Japanese Patent Publication No. 4-58489 JP-A-5-148340 JP-A-5-148340 Japanese Patent Laid-Open No. 2-270859 JP-A-6-192250 Japanese Patent Laid-Open No. 9-110979 Japanese Patent Laid-Open No. 9-255781 US Pat. No. 5,962,617 US Pat. No. 6,127,505

  The problem to be solved by the present invention is to provide an optical material composition having excellent optical properties and high mechanical strength and heat resistance, and a resin for optical materials obtained by polymerizing the composition for optical materials. It is.

  As a result of intensive studies to achieve the above object, the present inventors have found that the following (A), (B1), and a polymerizable composition containing the three components (C), and the following (A), ( It succeeded in solving the said subject with resin obtained by polymerizing and hardening the polymeric composition containing 4 components of B1), (C), and (D).

The present invention provides the following (A), (B1), it viewed including the four components (C) and (D),
(A) The component is in the range of 5 to 30% by weight,
(B1) component is in the range of 10 to 50% by weight,
Component (C) is in the range of 15 to 45% by weight,
(D) It is related with the lens which consists of a thermosetting polymeric composition which is 20-50 weight% of components, the manufacturing method of the optical material which polymerizes and cures the composition, an optical material, and an optical material.
(A) A compound having two or more mercapto groups, a compound having two or more mercapto groups in one molecule and a compound having three or more mercapto groups (B1) All or part of the terminals A polyurethane prepolymer and / or a polythiourethane prepolymer (C) comprising a mercapto group (C) a polyisocyanate compound and / or a polyisothiocyanate compound (D) two structures represented by the following formula (1) in one molecule Compounds

（式中、Ｒ^１は炭素数１〜１０の炭化水素又は単結合、Ｒ^２、Ｒ^３及びＲ^４はそれぞれ炭素数１〜１０の炭化水素基又は水素を示す。ＹはＯ、Ｓ、Ｓｅ又はＴｅを表す。ｍ＝１〜５、ｎ＝０〜５である。）

(In the formula, R ¹ represents a hydrocarbon or single bond having 1 to 10 carbon atoms, R ² , R ³ and R ⁴ each represent a hydrocarbon group or hydrogen having 1 to 10 carbon atoms. Y represents O, S or Se. Or Te, where m = 1 to 5 and n = 0 to 5.

An optical material obtained by polymerizing and curing the composition of the present invention has been found to have a well-balanced optical material having a high refractive index and a good Abbe number and having both high strength and heat resistance. As a result, the lens can be made thinner.

  Hereinafter, the present invention will be described in detail. The present invention relates to an optical material composition having a high refractive index and a high Abbe number, and having both high impact resistance and heat resistance, and a polymer thereof.

In the present invention, the proportions of the components (A), (B1), (C), and (D) are not generally determined by the refractive index and viscosity of each component, various physical properties of the optical material obtained, etc. A) 1 to 40% by weight, (B1) 1 to 70% by weight, (C) 1 to 50% by weight, (D) 0 to 70% by weight. When these ranges are exceeded, the high impact resistance that is the object of the present invention cannot be obtained. In addition, problems such as insufficient heat resistance, a deteriorated color tone of the cured product, and a high refractive index and a high Abbe number cannot be obtained. More preferably, it is in the range of 5 to 40% by weight of component (A), 10 to 60% by weight of component (B1), 10 to 50% by weight of component (C), and 10 to 60% by weight of component (D), more preferably Component (A) is in the range of 5 to 30% by weight, component (B1) is in the range of 10 to 50% by weight, component (C) is in the range of 15 to 45% by weight, and component (D) is in the range of 20 to 50% by weight. In order to obtain preferable optical characteristics and mechanical characteristics, the component (A) preferably has two or more mercapto groups per molecule. (C) Component It is preferable to have two or more isocyanate groups and / or isothiocyanate groups per molecule, and (D) component to have two or more structures represented by the formula (1) in one molecule. preferable. In order to develop a high refractive index, R ¹ in the formula (1) of the component (D) is preferably a hydrocarbon having 0 to 2 carbon atoms, and R ² , R ³ in the formula (1) and R ⁴ is preferably hydrogen or a methyl group. More preferably, R ¹ is a hydrocarbon having 0 or 1 carbon atoms, and R ² , R ³ and R ⁴ are hydrogen.

  The component (A) of the present invention includes mercaptans having one or more mercapto groups per molecule, thiophenols, and mercaptans having unsaturated groups such as vinyl, aromatic vinyl, methacryl, acryl, allyl, thio Examples include phenols.

Specific examples include methyl mercaptan, ethyl mercaptan, n-propyl mercaptan, n-butyl mercaptan, allyl mercaptan, n-hexyl mercaptan, n-octyl mercaptan, n-decyl mercaptan, n-dodecyl mercaptan, n-tetradecyl mercaptan, n-hexadecyl mercaptan, n-octadecyl mercaptan, cyclohexyl mercaptan, i-propyl mercaptan, t-butyl mercaptan, t-nonyl mercaptan, t-dodecyl mercaptan, phenyl mercaptan, benzyl mercaptan, 3-methylphenyl mercaptan, 4-methylphenyl Mercaptan, 4-chlorobenzyl mercaptan, 4-vinylbenzyl mercaptan, 3-vinylbenzyl mercaptan, methyl mercapto Lopionate, ethyl thioglycolate, n-butyl butyl glycolate, n-octyl thioglycolate, methyl (3-mercaptopropionate), ethyl (3-mercaptopropionate), 3-methoxybutyl (3- Mercaptopropionate), n-butyl (3-mercaptopropionate), 2-ethylhexyl (3-ercaptopropionate), n-octyl (3-mercaptopropionate), 2-mercaptoethanol, 3- Mercapto-1,2-propanediol, 2-mercapto-1,3-propanediol, mercaptoacetic acid, mercaptoglycolic acid, mercaptopropionic acid, methanedithiol, methanetrithiol, 3-mercaptopropanol, 2-mercaptopropanol, 2- Phenyl-2-me Captoethanol, 1,2-dimercaptoethane, 1,2-dimercaptopropane, 1,3-dimercaptopropane, 2,2-dimercaptopropane, 1,4-dimercaptobutane, 1,6-dimercaptohexane Bis (2-mercaptoethyl) ether, bis (2-mercaptoethyl) sulfide, 1,2-bis (2-mercaptoethyloxy) ethane, 1,2-bis (2-mercaptoethylthio) ethane, 2,3 Dimercapto-1-propanol, 1,3-dimercapto-2-propanol, 1,2,3-trimercaptopropane, 2-mercaptomethyl-1,3-dimercaptopropane, 2-mercaptomethyl-1,4-di Mercaptobutane, 2- (2-mercaptoethylthio) -1,3-dimercaptopropane, 1,2-bis [ (2-mercaptoethyl) thio] -3-mercaptopropane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 2,4-dimercaptomethyl-1,5-dimercapto-3-thiapentane, 4 , 8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 5,7 -Dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 1,1,1-tris (mercaptomethyl) propane, 1,1,2,2-tetrakis (mercaptomethylthio) ethane, , 1,3,3-tetrakis (mercaptomethylthio) propane, 1,5-dimercapto-3-mercaptothio-2,4-dithia Tantalum, tetrakis (mercaptomethyl) methane, ethylene glycol bis (2-mercaptoacetate), ethylene glycol bis (3-mercaptopropionate), diethylene glycol bis (2-mercaptoacetate), diethylene glycol bis (3-mercaptopropionate) 1,4-butanediol bis (2-mercaptoacetate), 1,4-butanediol bis (3-mercaptopropionate), trimethylolpropane tris (2-mercaptoacetate), trimethylolpropane tris (3-mercapto Propionate), pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetrakis (3-mercaptopropionate), 1,2-dimercaptocyclohexane, 1 3-dimercaptocyclohexane, 1,4-dimercaptocyclohexane, 1,3-bis (mercaptomethyl) cyclohexane, 1,4-bis (mercaptomethyl) cyclohexane, 2,5-bis (mercaptomethyl) -1,4- Dithiane, 2,5-bis (2-mercaptoethyl) -1,4-dithiane, 2,5-bis (2-mercaptoethylthiomethyl) -1,4-dithiane, 2,5-bis (mercaptomethyl)- 1-thian, 2,5-bis (2-mercaptoethyl) -1-thian, 2,5-bis (mercaptomethyl) thiophene, thiophenol, 4-tert-butylthiophenol, 2-methylthioph-methylthiophenol, 3 -Methylthiophenol, 4-methylthiophenol, 2-vinylthiophenol, 3-vinylthiophene Nord, 4-vinylthiophenol, 2-hydroxythiophenol, 3-hydroxythiophenol, 4-hydroxythiophenol, 1,2-dimercaptobenzene, 1,3-dimercaptobenzene, 1,4-dimercaptobenzene, 1,3-bis (mercaptomethyl) benzene, 1,4-bis (mercaptomethyl) benzene, 2,2′-dimercaptobiphenyl, 4,4′-dimercaptobiphenyl, bis (4-mercaptophenyl) methane, 2 , 2-bis (4-mercaptophenyl) propane, bis (4-mercaptophenyl) ether, bis (4-mercaptophenyl) sulfide, bis (4-mercaptophenyl) sulfone, bis (4-mercaptomethylphenyl) methane, , 2-Bis (4-mercaptomethylphenyl) propa Bis (4-mercaptomethylphenyl) ether, bis (4-mercaptomethylphenyl) sulfide, mercaptobenzoic acid, 2-mercaptoimidazole, 2-mercapto-1-methylimidazole, 2,5-dimercapto-1,3,4 -Thiadiazole, 3,4-thiophenedithiol, glyceryl dithioglycolate, 2-selenoethanol, bis (2-mercaptoethyl) selenide, bis (1,3-dimercapto-2-propyl) selenide, 2,3-bis (mercapto) Ethylseleno) -1-propanethiol, 2-mercaptomethyl-1,5-dimercapto-3-selenapentane, 4,8-bis (mercaptomethyl) -1,11-dimercapto-3,9-dithia-6-selena Undecane, 4,8-bis (mercaptomethyl) -1 , 11-dimercapto-6-thia-3,9-diselenaundecane, 4,8-bis (mercaptomethyl) -1,11-dimercapto-3,6,9-triselenaundecane, bis (hydroxymercaptoethylselenomethyl) ) Benzene, 1,4-dimercapto-2,3-bis (mercaptoethylseleno) butane, 1,2,3,4-tetrakis (mercaptoethylseleno) butane, 1,9-dimercapto-5,5-bis (mercapto) Methyl) -3,7-diselenanane, tris (mercaptomethyl) -1,8-dimercapto-6-thia-3-selenaoctane, bis (mercaptoethylselenomethyl) benzene, 2,5-diseleno-1,4-dithiane 2,5-bis (selenomethyl) -1,4-dithiane, 2,5-bis (mercaptoethylselenomethy) ) -1,4-dithiane, 2,6-dimercapto-1-selena-4-thiane, 3,5-dimercapto-1-selena-4-thiane, 2,6-bis (mercaptomethyl) -1-selena- 4-thiane, 3,5-bis (mercaptomethyl) -1-selena-4-thiane, 2,5-dimercapto-1,4-diselenane, 2,6-dimercapto-1,4-diselenane, 2,5- Bis (mercaptomethyl) -1,4-diselenane, 2,6-bis (mercaptomethyl) -1,4-diselenane, 2,5-dimercaptoselenane, 3,4-dimercaptoselenane, 2,5- Bis (mercaptomethyl) selenane, 3,4-bis (mercaptomethyl) selenane, 2,5-bis (selenomethyl) selenane, 3,4-bis (selenomethyl) selenane, 4,5-dimercapto- , 3-diselenolane, 4,5-bis (mercaptomethyl) -1,3-diselenolane, 3,6-dimercaptotriselenocyclooctane-dimercaptotriselenocyclooctane, 3,6-bis (mercaptomethyl) triseleno Mercaptans such as cyclooctane, 3,6-diselenotriselenocyclooctane, and 3,6-bis (selenomethyl) triselenocyclooctane, and among these polymercaptans, oligomers of the dimer to 20-mer form. However, it is not limited to these.

These may be used alone or in combination of two or more. Among the components (A) described above, a compound having two or more mercapto groups in one molecule is preferable. More preferably, a compound having two or more mercapto groups is used in combination with a compound having two mercapto groups in one molecule.

  Component (B1) of the present composition is a polyurethane prepolymer and / or polythiourethane having a mercapto group at all or part of the ends. Specific examples thereof include component (B) and component (C) shown below. It is synthesized from a polyurethane prepolymer and / or a polythiourethane prepolymer in which the components have been reacted in advance, and a compound having at least one hydroxyl group among the compounds having at least one mercapto group as component (A). A compound having a mercapto group instead of a hydroxyl group, that is, a compound having two or more mercapto groups in one molecule may be used. However, a compound having a hydroxyl group is preferable because it is less reactive than a hydroxyl group.

  As the component (B) in the polyurethane prepolymer (B1) and / or the polythiourethane prepolymer, an aliphatic linear oligomer having a number average molecular weight of 100 to 3000 that serves as a soft segment is used. Typical aliphatic linear oligomers include polyol compounds or polythiol compounds having one or more OH groups or SH groups, preferably two or more per molecule. When the number average molecular weight is less than 100, the ability as a soft segment is not sufficient, and the impact resistance of the obtained molded article is lowered. On the other hand, when the number average molecular weight exceeds 3000, the viscosity becomes high and handling becomes difficult.

  Specific examples include polyether polyols, polyoxyethylene glycol, polyoxypropylene glycol, polyoxytetramethylene glycol, polyether polyols such as polyoxypentamethylene glycol and polyether polyols having side chains, adipic acid, sebacic acid, One or more of dibasic acids such as maleic acid, glycols such as ethylene glycol, propylene glycol, butanediol, hexamethylene glycol, cyclohexane methanol, or glycerin, phloroglucinol, hexanetriol, trimethylolethane, trimethylolpropane Polyester polyols, polycaprolactones, polyvalerolactones, etc. obtained from one or more polyols such as Polycarbonate polyols such as lactone polyol, polyhexamethylene carbonate polyol, neopentylene carbonate polyol, polyester thiol, polythioester thiol, polyethylene sulfide thiol, polyethylene disulfide thiol, polyethylene polysulfide thiol and other polysulfide thiols, polyethylene sulfide diol, polyethylene disulfide diol, polyethylene Polysulfide diols such as polysulfide diol, oligo (2,5-dithiane) disulfide obtained by oxidizing 2,5-dimercaptodithiane, polythiocarbonate thiol and the like are preferably used. Furthermore, polyol compounds such as polydimethylsiloxane diol are also included. Moreover, a block copolymer of a plurality of polyol compounds, a random copolymer, a mixture of a plurality of polyol compounds, and the like can be given, but the invention is not limited thereto.

One or more of these polyols may be used in combination with polyols such as glycerin, phloroglicinol, hexanetriol, trimethylolethane, trimethylolpropane, pentaerythritol, 3-methylpentane-1,3,5-triol. it can.

  The component (C) of the present invention includes all compounds having two or more isocyanate groups and / or isothiocyanate groups per molecule. Although the specific example is given to the following, it is not limited to them.

  Specific examples thereof include diethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, 1,2-bis (isocyanato) ethoxyethane, trimethylhexamethylene diisocyanate, cyclohexane diisocyanate, 1,3-bis (isocyanatomethyl) cyclohexane, 1, 4-bis (isocyanatomethyl) cyclohexane, isophorone diisocyanate, 2,6-bis (isocyanatomethyl) decahydronaphthalene, lysine triisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, o-tolidine Diisocyanate, 4,4'-diphenylmethane diisocyanate, diphenyl ether diisocyanate, 3- (2'-isocyanatocyclohexyl) propiyl Isocyanate, tris (phenylisocyanate) thiophosphate, isopropylidenebis (cyclohexyl isocyanate), 2,2'-bis (4-isocyanatophenyl) propane, triphenylmethane triisocyanate, bis (diisocyanatotolyl) phenylmethane, 4,4 ' , 4 ″ -triisocyanate-2,5-dimethoxyphenylamine, 3,3′-dimethoxybenzidine-4,4′-diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 4,4′- Diisocyanatobiphenyl, 4,4′-diisocyanato-3,3′-dimethylbiphenyl, dicyclohexylmethane-4,4′-diisocyanate, 1,1′-methylenebis (4-isocyanatobenzene), 1,1 -Methylenebis (3-methyl-4-isocyanatobenzene), m-xylylene diisocyanate, p-xylylene diisocyanate, 1,3-bis (1-isocyanate-1-methylethyl) benzene, 1,4-bis (1 -Isocyanate-1-methylethyl) benzene, 1,3-bis (2-isocyanato-2-propyl) benzene, α, α, α ′, α′-tetramethyl-1,3-xylene, 2,6-bis (Isocyanatomethyl) naphthalene, 1,5-naphthalene diisocyanate, bis (isocyanatomethyl) tetrahydrodicyclopentadiene, bis (isocyanatomethyl) dicyclopentadiene, bis (isocyanatomethyl) tetrahydrothiophene, 2,5-diisocyanatomethylnorbornene, bis (Isocyanate methyl Adamantane, dimer acid diisocyanate, 1,3,5-tri (1-isocyanatohexyl) isocyanuric acid, thiodiethyl diisocyanate, thiodipropyl diisocyanate, thiodihexyl diisocyanate, bis [(4-isocyanatomethyl) phenyl] sulfide, 2 , 5-diisocyanato-1,4-dithiane, 2,5-diisocyanatomethyl-1,4-dithiane, 2,5-diisocyanatomethylthiophene, dithiodiethyl diisocyanate, dithiodipropyl diisocyanate and the like, and Can include compounds in which all or part of the isocyanate groups of the above isocyanates are replaced with isothiocyanate groups. Among the above, polyisocyanates include isocyanates such as dimers, cyclized trimers and adducts of alcohols or thiols by a burette type reaction. These may be used alone or in combination of two or more. Among the components (C) described above, a compound having two iso (thio) cyanate groups in one molecule is particularly preferable.

  The polyurethane prepolymer and / or the polythiourethane prepolymer (B1) in which all or part of the terminals are composed of mercapto groups can be prepared by a commonly used method. For example, an aliphatic linear oligomer having a number average molecular weight of 100 to 3000 having (C) component polyiso (thio) cyanate and (B) component SH group or OH group is 0.9 to 4.0 (NCO / OH). Or SH), and a polyurethane prepolymer and / or polythiourethane prepolymer obtained by reacting at 90 to 140 ° C. for 3 to 5 hours, and at least one mercapto group of component (A) It is obtained by mixing a compound having one or more hydroxyl groups among the compounds having a ratio of 0.9 to 4.0 (NCO / OH or SH) and reacting at 90 to 140 ° C. for 3 to 5 hours.

  The end of the polyurethane prepolymer and / or polythiourethane prepolymer (B1) is more mercapto group than isocyanate group which is easily affected by moisture, etc., so that the prepolymer has better storage and stability. It is also preferable in terms of solubility.

  As the component (D) used in the present invention, an episulfide compound having one or more structures represented by the following formula (1) in one molecule is used.

（式中、Ｒ^１は炭素数１〜１０の炭化水素又は単結合、Ｒ^２、Ｒ^３、及びＲ^４はそれぞれ炭素数１〜１０の炭化水素基又は水素を示す。ＹはＯ、Ｓ、Ｓｅ又はＴｅを表す。ｍ＝１〜５、ｎ＝０〜５である。）

(In the formula, R ¹ represents a hydrocarbon or a single bond having 1 to 10 carbon atoms, R ² , R ³ and R ⁴ each represent a hydrocarbon group or hydrogen having 1 to 10 carbon atoms. Y represents O, S, Represents Se or Te, where m = 1-5 and n = 0-5.)

Specific examples include bis (β-epithiopropyl) sulfide, bis (β-epithiopropyl) disulfide, bis (β-epithiopropyl) selenide, bis (β-epithiopropyl) diselenide, 1,1-bis (Epithioethyl) methane, 1- (epithioethyl) -1- (β-epithiopropyl) methane, 1,1-bis (β-epithiopropyl) methane 1- (epithioethyl) -1- (β-epithiopropyl) Ethane, 1,2-bis (β-epithiopropyl) ethane, 1- (epithioethyl) -3- (β-epithiopropyl) butane, 1,3-bis (β-epithiopropyl) propane, 1- ( Epithioethyl) -4- (β-epithiopropyl) pentane, 1,4-bis (β-epithiopropyl) butane, 1- (epithioethyl) -5- (β-epithio (Lopyl) hexane, 1- (epithioethyl) -2- (γ-epithiobutylthio) ethane, 1- (epithioethyl) -2- [2- (γ-epithiobutylthio) ethylthio] ethane, tetrakis (β-epi Thiopropyl) methane, 1,1,1-tris (β-epithiopropyl) propane, 1,3-bis (β-epithiopropyl) -1- (β-epithiopropyl) -2-thiapropane, 1, 5-bis (β-epithiopropyl) -2,4-bis (β-epithiopropyl) -3-thiapentane, (1,3 or 1,4) -bis (epithioethyl) cyclohexane, (1,3 or 1 , 4) -bis (β-epithiopropyl) cyclohexane, bis [4- (epithioethyl) cyclohexyl] methane, bis [4- (β-epithiopropyl) cyclohexyl] methane 2,2-bis [4- (epithioethyl) cyclohexyl] propane, 2,2-bis [4- (β-epithiopropyl) cyclohexyl] propane, bis [4- (β-epithiopropyl) cyclohexyl] sulfide, Bis [4- (epithioethyl) cyclohexyl] sulfide, 2,5-bis (epithioethyl) -1,4-dithiane, 2,5-bis (β-epithiopropyl) -1,4-dithiane, 4-epithioethyl-1 , 2-cyclohexene sulfide, 4-epoxy-1,2-cyclohexene sulfide, (2,3 or 2,5 or 2,6) -bis (1,2-epithioethyl) -1,4-diselenane, (2,3 Or 2,5 or 2,6) -bis (2,3-epithiopropyl) -1,4-diselenane, (2,4 or 2,5 or 2,6 ) -Bis (1,2-epithioethyl) -1,3-diselenan, (2,4 or 2,5 or 2,6) -bis (2,4-epithiopropyl) -1,3-diselenan, (2 , 3 or 2,5 or 2,6 or 3,5) -bis (1,2-epithioethyl) -1-thia-4-selenane, (2,3 or 2,5 or 2,6 or 3,5) -Bis (2,3-epithiopropyl) -1-thia-4-selenane, (2,4 or 4,5) -bis (1,2-epithioethyl) -1,3-diselenolane, (2,4 or 4,5) -bis (2,4-epithiopropyl) -1,3-diselenolane, (2,4 or 2,5 or 4,5) -bis (1,2-epithioethyl) -1-thia-3 -Selenolane, (2,4 or 2,5 or 4,5) -bis (2,4-epithio) (Lopyl) -1-thia-3-selenolane, (2,3 or 2,4 or 2,5 or 3,4) -bis (1,2-epithioethyl) selenophane, (2,3 or 2,4 or 2) , 5 or 3,4) -bis (2,3-epithiopropyl) selenophan, (2,3 or 2,5 or 2,6) -bis (1,2-epithioethyl) -1,4-diterlan, (2,3 or 2,5 or 2,6) -bis (2,3-epithiopropyl) -1,4-diterlan, (2,4 or 2,5 or 2,6) -bis (1,2 -Epithioethyl) -1,3-diterlan, (2,4 or 2,5 or 2,6) -bis (2,4-epithiopropyl) -1,3-diterlan, (2,3 or 2,5 or 2,6 or 3,5) -bis (1,2-epithioethyl) -1-thio -4-tellulane, (2,3 or 2,5 or 2,6 or 3,5) -bis (2,3-epithiopropyl) -1-thia-4-terlan, (2,4 or 4,5 ) -Bis (1,2-epithioethyl) -1,3-ditellolane, (2,4 or 4,5) -bis (2,4-epithiopropyl) -1,3-ditellolane, (2,4 or 2) , 5 or 4,5) -bis (1,2-epithioethyl) -1-thia-3-tellurolane, (2,4 or 2,5 or 4,5) -bis (2,4-epithiopropyl)- 1-thia-3-tellurolane, (2,3 or 2,4 or 2,5 or 3,4) -bis (1,2-epithioethyl) tellurophane, (2,3 or 2,4 or 2,5 or 3 , 4) -bis (2,3-epithiopropyl) terenophane, (1,3 1,4) -bis (epithioethyl) benzene, (1,3 or 1,4) -bis (β-epithiopropyl) benzene, bis [4- (epithioethyl) phenyl] methane, bis [4- (β -Epithiopropyl) phenyl] methane, 2,2-bis [4- (epithioethyl) phenyl] propane, 2,2-bis [4- (β-epithiopropyl) phenyl] propane, bis [4- (epithioethyl) Phenyl] sulfide, bis [4- (β-epithiopropyl) phenyl] sulfide, bis [4- (epithioethyl) phenyl] sulfone, bis [4- (β-epithiopropyl) phenyl] sulfone, 4,4′- Episulfides having a chain aliphatic skeleton such as bis (epithioethyl) biphenyl and 4,4′-bis (β-epithiopropyl) biphenyl, , 5-bis (2,3-epithiopropyl) -1,2,4,5-tetrathiapentane, 1,6-bis (2,3-epithiopropyl) -1,2,5,6-tetra Episulfides having a disulfide bond such as thiahexane, 1,2,3-tris (4,5-epithio-1,2-dithiapentyl) propane, bis (β-epithiopropyl) disulfide, methylthioglycidyl ether, ethylthioglycidyl Thioglycidyl ethers such as ether, propylthioglycidyl ether, butylthioglycidyl ether, bis (β-epithiopropyl) ether, bis (β-epithiopropyloxy) methane, 1,2-bis (β-epithiopropyl) Oxy) ethane, 1,3-bis (β-epithiopropyloxy) propane, 1,2-bis (β-epithiop) (Lopyroxy) propane, 1- (β-epithiopropyloxy) -2- (β-epithiopropyloxymethyl) propane, 1,4-bis (β-epithiopropyloxy) butane, 1,3-bis (β -Epithiopropyloxy) butane, 1- (β-epithiopropyloxy) -3- (β-epithiopropyloxymethyl) butane, 1,5-bis (β-epithiopropyloxy) pentane, 1- ( β-epithiopropyloxy) -4- (β-epithiopropyloxymethyl) pentane, 1,6-bis (β-epithiopropyloxy) hexane, 1- (β-epithiopropyloxy) -5- ( β-epithiopropyloxymethyl) hexane, 1- (β-epithiopropyloxy) -2-[(2-β-epithiopropyloxyethyl) oxy] ethane, 1- (β Epithiopropyloxy) -2-[[2- (2-β-epithiopropyloxyethyl) oxyethyl] oxy] ethane, bis (5,6-epithio-3-oxahexyl) selenide, bis (5,6- Epithio-3-oxahexyl) telluride, tetrakis (β-epithiopropyloxymethyl) methane, 1,1,1-tris (β-epithiopropyloxymethyl) propane, 1,5-bis (β-epithiopropyl) Oxy) -2- (β-epithiopropyloxymethyl) -3-thiapentane, 1,5-bis (β-epithiopropyloxy) -2,4-bis (β-epithiopropyloxymethyl) -3- Thiapentane, 1- (β-epithiopropyloxy) -2,2-bis (β-epithiopropyloxymethyl) -4-thiahexane, 1,5,6-tri (Β-epithiopropyloxy) -4- (β-epithiopropyloxymethyl) -3-thiahexane, 1,8-bis (β-epithiopropyloxy) -4- (β-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropyloxy) -4,5 bis (β-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,8-bis (β-epi Thiopropyloxy) -4,4-bis (β-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropyloxy) -2,4,5-tris (β- Epithiopropyloxymethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropyloxy) -2,5-bis (β-epithiopropyloxymethyl) -3,6-dithiaocta 1,9-bis (β-epithiopropyloxy) -5- (β-epithiopropyloxymethyl) -5-[(2-β-epithiopropyloxyethyl) oxymethyl] -3,7- Dithianonane, 1,10-bis (β-epithiopropyloxy) -5,6-bis [(2-β-epithiopropyloxyethyl) oxy] -3,6,9-trithiadecane, 1,11-bis ( β-epithiopropyloxy) -4,8-bis (β-epithiopropyloxymethyl) -3,6,9-trithiaundecane, 1,11-bis (β-epithiopropyloxy) -5,7 -Bis (β-epithiopropyloxymethyl) -3,6,9-trithiaundecane, 1,11-bis (β-epithiopropyloxy) -5,7-[(2-β-epithiopropyloxy Ethyl) oxymethyl -3,6,9-trithiaundecane, 1,11-bis (β-epithiopropyloxy) -4,7-bis (β-epithiopropyloxymethyl) -3,6,9-trithia Undecane, (1,3 or 1,4) -bis (β-epithiopropyloxy) cyclohexane, (1,3 or 1,4) -bis (β-epithiopropyloxymethyl) cyclohexane, bis [4- ( β-epithiopropyloxy) cyclohexyl] methane, 2,2-bis [4- (β-epithiopropyloxy) cyclohexyl] propane, bis [4- (β-epithiopropyloxy) cyclohexyl] sulfide, 2,5 -Bis (β-epithiopropyloxymethyl) -1,4-dithiane, 2,5-bis (β-epithiopropyloxyethyloxymethyl) -1,4-dithiane , (2,4 or 4,5) -bis (3,4-epithio-1-oxabutyl) -1,3-diselenolane, (2,4 or 4,5) -bis (4,5-epithio-2- Oxapentyl) -1,3-diselenolane, (2,4 or 2,5 or 4,5) -bis (3,4-epithio-1-oxabutyl) -1-thia-3-selenolane, (2,4 or 2,5 or 4,5) -bis (4,5-epithio-2-oxapentyl) -1-thia-3-selenolane, bis (3,4-epithio-1-oxabutyl) tricycloselenaoctane, bis ( 3,4-epithio-1-oxabutyl) dicycloselenanane, (2,3 or 2,4 or 2,5 or 3,4) -bis (3,4-epithio-1-oxabutyl) selenophane, (2 , 3 or 2,4 or 2,5 Or 3,4) -bis (4,5-epithio-2-oxapentyl) selenophane, (2,3 or 2,5 or 2,6) -bis (3,4-epithio-1-oxabutyl)- 1,4-diselenane, (2,3 or 2,5 or 2,6) -bis (4,5-epithio-2-oxapentyl) -1,4-diselenane, (2,4 or 2,5 or 2 , 6) -bis (3,4-epithio-1-oxabutyl) -1,3-diselenane, (2,4 or 2,5 or 2,6) -bis (4,5-epithio-2-oxapentyl) -1,3-diselenane, (2,3 or 2,5 or 2,6 or 3,5) -bis (3,4-epithio-1-oxabutyl) -1-thia-4-selenane, (2,3 Or 2,5 or 2,6 or 3,5) -bis (4,5-epithio- -Oxapentyl) -1-thia-4-selenane, (2,4 or 4,5) -bis (3,4-epithio-1-oxabutyl) -1,3-ditellolane, (2,4 or 4,5 ) -Bis (4,5-
Epithio-2-oxapentyl) -1,3-ditellolane, (2,4 or 2,5 or 4,5) -bis (3,4-epithio-1-oxabutyl) -1-thia-3-tellurolane, 2,4 or 2,5 or 4,5) -bis (4,5-epithio-2-oxapentyl) -1-thia-3-tellurolane, bis (3,4-epithio-1-oxabutyl) tricyclotella Octane, bis (3,4-epithio-1-oxabutyl) dicyclotellanonane, (2,3 or 2,4 or 2,5 or 3,4) -bis (3,4-epithio-1-oxabutyl) tellurophane , (2,3 or 2,4 or 2,5 or 3,4) -bis (4,5-epithio-2-oxapentyl) tellurophane, (2,3 or 2,5 or 2,6) -bis ( 3,4-epichi -1-oxabutyl) -1,4-ditellulane, (2,3 or 2,5 or 2,6) -bis (4,5-epithio-2-oxapentyl) -1,4-ditellan, (2,4 Or 2,5 or 2,6) -bis (3,4-epithio-1-oxabutyl) -1,3-diterlan, (2,4 or 2,5 or 2,6) -bis (4,5-epithio -2-oxapentyl) -1,3-diterlan, (2,3 or 2,5 or 2,6 or 3,5) -bis (3,4-epithio-1-oxabutyl) -1-thia-4- Tellurane, (2,3 or 2,5 or 2,6 or 3,5) -bis (4,5-epithio-2-oxapentyl) -1-thia-4-terlan, (1,3 or 1,4 ) -Bis (β-epithiopropyloxy) benzene, (1,3 or 1, 4) -bis (β-epithiopropyloxymethyl) benzene, bis [4- (β-epithiopropyl) phenyl] methane, 2,2-bis [4- (β-epithiopropylthio) phenyl] propane, Epi such as bis [4- (β-epithiopropylthio) phenyl] sulfide, bis [4- (β-epithiopropylthio) phenyl] sulfone, 4,4′-bis (β-epithiopropylthio) biphenyl Episulfides having one or more thioalkyloxy groups, bis (epithioethyl) sulfide, bis (epithioethyl) disulfide, bis (β-epithiopropyl) sulfide, bis (β-epithiopropyl) disulfide, bis (β-epithio) Propyl) trisulfide, bis (β-epithiopropylthio) methane, 1,2-bis (β-epithiopro) Ruthio) ethane, 1,3-bis (β-epithiopropylthio) propane, 1,2-bis (β-epithiopropylthio) propane, 1- (β-epithiopropylthio) -2- (β- Epithiopropylthiomethyl) propane, 1,4-bis (β-epithiopropylthio) butane, 1,3-bis (β-epithiopropylthio) butane, 1- (β-epithiopropylthio) -3 -(Β-epithiopropylthiomethyl) butane, 1,5-bis (β-epithiopropylthio) pentane, 1- (β-epithiopropylthio) -4- (β-epithiopropylthiomethyl) pentane 1,6-bis (β-epithiopropylthio) hexane, 1- (β-epithiopropylthio) -5- (β-epithiopropylthiomethyl) hexane, 1- (β-epithiopropylthio) -2- [(2-β-epithiopropylthioethyl) thio] ethane, 1- (β-epithiopropylthio) -2-[[2- (2-β-epithiopropylthioethyl) thioethyl] thio] ethane, Tetrakis (β-epithiopropylthiomethyl) methane, 1,1,1-tris (β-epithiopropylthiomethyl) propane, 1,5-bis (β-epithiopropylthio) -2- (β-epi Thiopropylthiomethyl) -3-thiapentane, 1,5-bis (β-epithiopropylthio) -2,4-bis (β-epithiopropylthiomethyl) -3-thiapentane, 1- (β-epithio Propylthio) -2,2-bis (β-epithiopropylthiomethyl) -4-thiahexane, 1,5,6-tris (β-epithiopropylthio) -4- (β-epithiopropylthiomethyl) − -Thiahexane, 1,8-bis (β-epithiopropylthio) -4- (β-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropylthio) -4 , 5bis (β-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropylthio) -4,4-bis (β-epithiopropylthiomethyl) -3, 6-dithiaoctane, 1,8-bis (β-epithiopropylthio) -2,4,5-tris (β-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (β-epi Thiopropylthio) -2,5-bis (β-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,9-bis (β-epithiopropylthio) -5- (β-epithiopropylthiomethyl) ) -5-[(2 -Β-epithiopropylthioethyl) thiomethyl] -3,7-dithianonane, 1,10-bis (β-epithiopropylthio) -5,6-bis [(2-β-epithiopropylthioethyl) thio ] -3,6,9-trithiadecane, 1,11-bis (β-epithiopropylthio) -4,8-bis (β-epithiopropylthiomethyl) -3,6,9-trithiaundecane, , 11-bis (β-epithiopropylthio) -5,7-bis (β-epithiopropylthiomethyl) -3,6,9-trithiaundecane, 1,11-bis (β-epithiopropylthio) ) -5,7-[(2-β-epithiopropylthioethyl) thiomethyl] -3,6,9-trithiaundecane, 1,11-bis (β-epithiopropylthio) -4,7-bis (Β-epithiopropylthiomethy ) -3,6,9-trithiaundecane, tetra [2- (β-epithiopropylthio) acetylmethyl] methane, 1,1,1-tri [2- (β-epithiopropylthio) acetylmethyl ] Propane, tetra [2- (β-epithiopropylthiomethyl) acetylmethyl] methane, 1,1,1-tri [2- (β-epithiopropylthiomethyl) acetylmethyl] propane, bis (5,6 -Epithio-3-thiahexyl) selenide, 2,3-bis (6,7-thioepoxy-1-selena-4-thiaheptyl) -1- (3,4-thioepoxy-1-thiabutyl) propane, 1,1,3 , 3, -Tetrakis (4,5-thioepoxy-2-thiapentyl) -2-selenapropane, bis (4,5-thioepixy-2-thiapentyl) -3,6,9-triselenau Decane-1,11-bis (3,4-thioepoxy-1-thiabutyl), 1,4-bis (3,4-thioepoxy-1-thiabutyl) -2,3-bis (6,7-thioepoxy-1- Selena-4-thiaheptyl) butane, tris (4,5-thioepoxy-2-thiapentyl) -3-selena-6-thiaoctane-1,8-bis (3,4-thioepoxy-1-thiabutyl), bis (5 6-epithio-3-thiahexyl) telled, 2,3-bis (6,7-thioepoxy-1-tella-4-thiaheptyl) -1- (3,4-thioepoxy-1-thiabutyl) propane, 1,1, 3,3, -Tetrakis (4,5-thioepoxy-2-thiapentyl) -2-tellapropane, bis (4,5-thioepoxy-2-thiapentyl) -3,6,9-triteraun Decane-1,11-bis (3,4-thioepoxy-1-thiabutyl), 1,4-bis (3,4-thioepoxy-1-thiabutyl) -2,3-bis (6,7-thioepoxy-1- Tellura-4-thiaheptyl) butane, tris (4,5-thioepoxy-2-thiapentyl) -3-tella-6-thiaoctane-1,8-bis (3,4-thioepoxy-1-thiabutyl), (1,3 Or 1,4) -bis (β-epithiopropylthio) cyclohexane, (1,3 or 1,4) -bis (β-epithiopropylthiomethyl) cyclohexane, bis [4- (β-epithiopropylthio) ) Cyclohexyl] methane, 2,2-bis [4- (β-epithiopropylthio) cyclohexyl] propane, bis [4- (β-epithiopropylthio) cyclohexyl] sulfur 2,5-bis (β-epithiopropylthiomethyl) -1,4-dithiane, 2,5-bis (β-epithiopropylthioethylthiomethyl) -1,4-dithiane, (2, 3 or 2,5 or 2,6) -bis (3,4-epithio-1-thiabutyl) -1,4-diselenane, (2,3 or 2,5 or 2,6) -bis (4,5- Epithio-2-thiapentyl) -1,4-diselenane, (2,4 or 2,5 or 5,6) -bis (3,4-epithio-1-thiabutyl) -1,3-diselenane, (2,4 Or 2,5 or 5,6) -bis (4,5-epithio-2-thiapentyl) -1,3-diselenane, (2,3 or 2,5 or 2,6 or 3,5) -bis (3 , 4-epithio-1-thiabutyl) -1-thia-4-selenane, (2,3 Or 2,5 or 2,6 or 3,5) -bis (4,5-epithio-2-thiapentyl) -1-thia-4-selenane, (2,4 or 4,5) -bis (3 4-epithio-1-thiabutyl) -1,3-diselenolane, (2,4 or 4,5) -bis (4,5-epithio-2-thiapentyl) -1,3-diselenolane, (2,4 or 2) , 5 or 4,5) -bis (3,4-epithio-1-thiabutyl) -1-thia-3-selenolane, (2,4 or 2,5 or 4,5) -bis (4,5-epithio -2-thiapentyl) -1-thia-3-selenolane, 2,6-bis (4,5-epithio-2-thiapentyl-1,3,5-triselenane, bis (3,4-epithio-1-thiabutyl) Tricycloselenaoctane, bis (3,4-epithio-1-thio Abutyldicycloselenanane, (2,3 or 2,4 or 2,5 or 3,4) -bis (3,4-epithio-1-thiabutyl) selenophane, (2,3 or 2,4 or 2 , 5 or 3,4) -bis (4,5-epithio-2-thiapentyl) selenophane, 2- (4,5-thioepoxy-2-thiapentyl) -5- (3,4-thioepoxy-1-thiabutyl) -1-selenacyclohexane, (2,3 or 2,4 or 2,5 or 2,6 or 3,4 or 3,5 or 4,5) -bis (3,4-thioepoxy-1-thiabutyl) -1 -Selenacyclohexane, (2,3 or 2,4 or 2,5 or 2,6 or 3,4 or 3,5 or 4,5) -bis (4,5-thioepoxy-2-thiapentyl) -1-selena Cyclohexa , (2,3 or 2,5 or 2,6) -bis (3,4-epithio-1-thiabutyl) -1,4-diterlan, (2,3 or 2,5 or 2,6) -bis ( 4,5-epithio-2-thiapentyl) -1,4-diterlan, (2,4 or 2,5 or 5,6) -bis (3,4-epithio-1-thiabutyl) -1,3-diterlan, (2,4 or 2,5 or 5,6) -bis (4,5-epithio-2-thiapentyl) -1,3-diterlan, (2,3 or 2,5 or 2,6 or 3,5) -Bis (3,4-epithio-1-thiabutyl) -1-thia-4-tellulane, (2,3 or 2,5 or 2,6 or 3,5) -bis (4,5-epithio-2- Thiapentyl) -1-thia-4-terlan, (2,4 or 4,5) -bis (3,4 Epithio-1-thiabutyl) -1,3-ditellolane, (2,4 or 4,5) -bis (4,5-epithio-2-thiapentyl) -1,3-ditellolane, (2,4 or 2,5 Or 4,5) -bis (3,4-epithio-1-thiabutyl) -1-thia-3-tellurolane, (2,4 or 2,5 or 4,5) -bis (4,5-epithio-2) -Thiapentyl) -1-thia-3-tellurolane, 2,6-bis (4,5-epithio-2-thiapentyl-1,3,5-triterulan, bis (3,4-epithio-1-thiabutyltricyclo) Tellaoctane, bis (3,4-epithio-1-thiabutyl) dicyclotellanonane, (2,3 or 2,4 or 2,5 or 3,4) -bis (3,4-epithio-1-thiabutyl) Tellurophan, (a few more Is 2,4 or 2,5 or 3,4) -bis (4,5-epithio-2-thiapentyl) tellurophan, 2- (4,5-thioepoxy-2-thiapentyl) -5- (3,4-thioepoxy -1-thiabutyl) -1-
Telluracyclohexane, (2,3 or 2,4 or 2,5 or 2,6 or 3,4 or 3,5 or 4,5) -bis (3,4-thioepoxy-1-thiabutyl) -1-tellacyclohexane (2,3 or 2,4 or 2,5 or 2,6 or 3,4 or 3,5 or 4,5) -bis (4,5-thioepoxy-2-thiapentyl) -1-tellacyclohexane, etc. (1,3 or 1,4) -bis (β-epithiopropylthio) benzene, (1,3 or 1,4) -bis (β-epithiopropylthiomethyl) benzene, bis [4- (β- Epithiopropylthio) phenyl] methane, 2,2-bis [4- (β-epithiopropylthio) phenyl] propane, bis [4- (β-epithiopropylthio) phenyl] sulfide, bis [4- ( β-epithiopropylthio) phenyl] sulfone, episulfides having one or more epithioalkylthio groups such as 4,4′-bis (β-epithiopropylthio) biphenyl, bis (β-epithiopropyl) selenide, Bis (β-epithiopropyl) diselenide, bis (β-epithiopropyl) triselenide, bis (β-epithiopropylseleno) methane, 1,2-bis (β-epithiopropylseleno) ethane, 1,3- Bis (β-epithiopropylseleno) propane, 1,2-bis (β-epithiopropylseleno) propane, 1- (β-epithiopropylseleno) -2- (β-epithiopropylselenomethyl) propane, 1,4-bis (β-epithiopropylseleno) butane, 1,3-bis (β-epithiopropylseleno) butane, 1- (β-epi Opropylseleno) -3- (β-epithiopropylselenomethyl) butane, 1,5-bis (β-epithiopropylseleno) pentane, 1- (β-epithiopropylseleno) -4- (β-epi Thiopropylselenomethyl) pentane, 1,6-bis (β-epithiopropylseleno) hexane, 1- (β-epithiopropylseleno) -5- (β-epithiopropylselenomethyl) hexane, 1- (β -Epithiopropylseleno) -2-[(2-β-epithiopropylselenoethyl) thio] ethane, 1- (β-epithiopropylseleno) -2-[[2- (2-β-epithiopropyl) Selenoethyl) selenoethyl] thio] ethane, tetrakis (β-epithiopropylselenomethyl) methane, 1,1,1-tris (β-epithiopropylselenomethyl) propane, , 5-Bis (β-epithiopropylseleno) -2- (β-epithiopropylselenomethyl) -3-thiapentane, 1,5-bis (β-epithiopropylseleno) -2,4-bis (β -Epithiopropylselenomethyl) -3-thiapentane, 1- (β-epithiopropylseleno) -2,2-bis (β-epithiopropylselenomethyl) -4-thiahexane, 1,5,6-tris ( β-epithiopropylseleno) -4- (β-epithiopropylselenomethyl) -3-thiahexane, 1,8-bis (β-epithiopropylseleno) -4- (β-epithiopropylselenomethyl)- 3,6-dithiaoctane, 1,8-bis (β-epithiopropylseleno) -4,5bis (β-epithiopropylselenomethyl) -3,6-dithiaoctane, 1,8-bis (β-et Pithiopropylseleno) -4,4-bis (β-epithiopropylselenomethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropylseleno) -2,4,5-tris (β -Epithiopropylselenomethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropylseleno) -2,5-bis (β-epithiopropylselenomethyl) -3,6-dithiaoctane, , 9-bis (β-epithiopropylseleno) -5- (β-epithiopropylselenomethyl) -5-[(2-β-epithiopropylselenoethyl) selenomethyl] -3,7-dithianonane, 1, 10-bis (β-epithiopropylseleno) -5,6-bis [(2-β-epithiopropylselenoethyl) thio] -3,6,9-trithiadecane, 1,11-bis (β-epithio) Propylseleno) -4,8-bis (β-epithiopropylselenomethyl) -3,6,9-trithiaundecane, 1,11-bis (β-epithiopropylseleno) -5,7-bis (β -Epithiopropylselenomethyl) -3,6,9-trithiaundecane, 1,11-bis (β-epithiopropylseleno) -5,7-[(2-β-epithiopropylselenoethyl) selenomethyl] 3,6,9-trithiaundecane, 1,11-bis (β-epithiopropylseleno) -4,7-bis (β-epithiopropylselenomethyl) -3,6,9-trithiaundecane, Tetra [2- (β-epithiopropylseleno) acetylmethyl] methane, 1,1,1-tri [2- (β-epithiopropylseleno) acetylmethyl] propane, tetra [2- (β-epithiop) Pyrselenomethyl) acetylmethyl] methane, 1,1,1-tri [2- (β-epithiopropylselenomethyl) acetylmethyl] propane, bis (5,6-epithio-3-selenohexyl) selenide, 2, 3-bis (6,7-thioepoxy-1-selena-4-selenoheptyl) -1- (3,4-thioepoxy-1-selenobutyl) propane, 1,1,3,3-tetrakis (4,5- Thioepoxy-2-selenopentyl) -2-selenapropane, bis (4,5-thioepoxy-2-selenopentyl) -3,6,9-triselenaundecane-1,11-bis (3,4-thioepoxy-1) -Selenobutyl), 1,4-bis (3,4-thioepoxy-1-selenobutyl) -2,3-bis (6,7-thioepoxy-1-selena-4-selenoheptyl) Tan, Tris (4,5-thioepoxy-2-selenopentyl) -3-selena-6-thiaoctane-1,8-bis (3,4-thioepoxy-1-selenobutyl), bis (5,6-epithio-3) -Selenohexyl) tellured, 2,3-bis (6,7-thioepoxy-1-tellura-4-selenoheptyl) -1- (3,4-thioepoxy-1-selenobutyl) propane, 1,1,3,3 , -Tetrakis (4,5-thioepoxy-2-selenopentyl) -2-tellapropane, bis (4,5-thioepoxy-2-selenopentyl) -3,6,9-triteraundecane-1,11-bis (3,4-thioepoxy-1-selenobutyl), 1,4-bis (3,4-thioepoxy-1-selenobutyl) -2,3-bis (6,7-thioepoxy-1-teller) -Selenoheptyl) butane, tris (4,5-thioepoxy-2-selenopentyl) -3-tella-6-thiaoctane-1,8-bis (3,4-thioepoxy-1-selenobutyl), (1,3 or 1,4) -bis (β-epithiopropylseleno) cyclohexane, (1,3 or 1,4) -bis (β-epithiopropylselenomethyl) cyclohexane, bis [4- (β-epithiopropylseleno) Cyclohexyl] methane, 2,2-bis [4- (β-epithiopropylseleno) cyclohexyl] propane, bis [4- (β-epithiopropylseleno) cyclohexyl] sulfide, 2,5-bis (β-epithio) Propylselenomethyl) -1,4-dithiane, 2,5-bis (β-epithiopropylselenoethylthiomethyl) -1,4-dithiane, (2,3 or 2,5 or 2,6) -bis (3,4-epithio-1-selenobutyl) -1,4-diselenane, (2,3 or 2,5 or 2,6) -bis (4 , 5-epithio-2-selenopentyl) -1,4-diselenane, (2,4 or 2,5 or 5,6) -bis (3,4-epithio-1-selenobutyl) -1,3-diselenane, (2,4 or 2,5 or 5,6) -bis (4,5-epithio-2-selenopentyl) -1,3-diselenane, (2,3 or 2,5 or 2,6 or 3,5 ) -Bis (3,4-epithio-1-selenobutyl) -1-thia-4-selenane, (2,3 or 2,5 or 2,6 or 3,5) -bis (4,5-epithio-2) -Selenopentyl) -1-thia-4-selenane, (2,4 or 4,5) -bis 3,4-epithio-1-selenobutyl) -1,3-diselenolane, (2,4 or 4,5) -bis (4,5-epithio-2-selenopentyl) -1,3-diselenolane, (2, 4 or 2,5 or 4,5) -bis (3,4-epithio-1-selenobutyl) -1-thia-3-selenolane, (2,4 or 2,5 or 4,5) -bis (4 5-epithio-2-selenopentyl) -1-thia-3-selenolane, 2,6-bis (4,5-epithio-2-selenopentyl-1,3,5-triselenane, bis (3,4-epithio) -1-selenobutyl) tricycloselenaoctane, bis (3,4-epithio-1-selenobutyl) dicycloselenanane, (2,3 or 2,4 or 2,5 or 3,4) -bis (3,4 -Epithio-1-selenobutyl Selenophan, (2,3 or 2,4 or 2,5 or 3,4) -bis (4,5-epithio-2-selenopentyl) selenophan, 2- (4,5-thioepoxy-2-selenopentyl) ) -5- (3,4-thioepoxy-1-selenobutyl) -1-selenacyclohexane, (2,3 or 2,4 or 2,5 or 2,6 or 3,4 or 3,5 or 4,5) -Bis (3,4-thioepoxy-1-selenobutyl) -1-selenacyclohexane, (2,3 or 2,4 or 2,5 or 2,6 or 3,4 or 3,5 or 4,5) -bis (4,5-thioepoxy-2-selenopentyl) -1-selenacyclohexane, (2,3 or 2,5 or 2,6) -bis (3,4-epithio-1-selenobutyl) -1,4-diterlan , (2 , 3 or 2,5 or 2,6) -bis (4,5-epithio-2-selenopentyl) -1,4-diterlan, (2,4 or 2,5 or 5,6) -bis (3 4-epithio-1-selenobutyl) -1,3-diterlan, (2,4 or 2,5 or 5,6) -bis (4,5-epithio-2-selenopentyl) -1,3-diterlan, 2,3 or 2,5 or 2,6 or 3,5) -bis (3,4-epithio-1-selenobutyl) -1-thia-4-terlan, (2,3 or 2,5 or 2,6 Or 3,5) -bis (4,5-epithio-2-selenopentyl) -1-thia-4-terlan, (2,4 or 4,5) -bis (3,4-epithio-1-selenobutyl) -1,3-ditellolane, (2,4 or 4,5) -bis (4,5-epi O-2-selenopentyl) -1,3-ditellolane, (2,4 or 2,5 or 4,5) -bis (3,4-epithio-1-selenobutyl) -1-thia-3-tellurolane, 2,4 or 2,5 or 4,5) -bis (4,5-epithio-2-selenopentyl) -1-thia-3-tellurolane, 2,6-bis (4,5-epithio-2-seleno) Pentyl-1,3,5-triterlane, bis (3,4-epithio-1-selenobutyl) tricyclotellaoctane, bis (3,4-epithio-1-selenobutyl) dicyclotellanonane, (2,3 or 2 , 4 or 2,5 or 3,4) -bis (3,4-epithio-1-selenobutyl) tellurophane, (2,3 or 2,4 or 2,5 or 3,4) -bis (4,5- Epithio-2-seleno pliers ) Tellurophan, 2- (4,5-thioepoxy-2-selenopentyl) -5- (3,4-thioepoxy-1-selenobutyl) -1-tellulacyclohexane, (2,3 or 2,4 or 2,5 or 2,6 or 3,4 or 3,5 or 4,5) -bis (3,4-thioepoxy-1-selenobutyl) -1-tellulacyclohexane, (2,3 or 2,4 or 2,5 or 2, 6 or 3,4 or 3,5 or 4,5) -bis (4,5-thioepoxy-2-selenopentyl) -1-tellacyclohexane, (1,3 or 1,4) -bis (β-epithio) Propylseleno) benzene, (1,3 or 1,4) -bis (β-epithiopropylselenomethyl) benzene, bis [4- (β-epithiopropylseleno) phenyl] methane, 2,2-bi [4- (β-epithiopropylseleno) phenyl] propane, bis [4- (β-epithiopropylseleno) phenyl] sulfide, bis [4- (β-epithiopropylseleno) phenyl] sulfone, 4, 4
Episulfides having one or more epithioalkylseleno groups such as' -bis (β-epithiopropylseleno) biphenyl, bis (β-epithiopropyl) telledo, bis (β-epithiopropyl) ditelled, bis (β -Epithiopropyl) tritelredo, bis (β-epithiopropyltelluro) methane, 1,2-bis (β-epithiopropyltelluro) ethane, 1,3-bis (β-epithiopropyltelluro) propane, 1, 2-bis (β-epithiopropyltelluro) propane, 1- (β-epithiopropyltelluro) -2- (β-epithiopropyltelluromethyl) propane, 1,4-bis (β-epithiopropyltelluro) Butane, 1,3-bis (β-epithiopropyltelluro) butane, 1- (β-epithiopropyltelluro) -3- (β-epithiopropylte) (Romethyl) butane, 1,5-bis (β-epithiopropyltelluro) pentane, 1- (β-epithiopropyltelluro) -4- (β-epithiopropyltelluromethyl) pentane, 1,6-bis (β -Epithiopropyltelluro) hexane, 1- (β-epithiopropyltelluro) -5- (β-epithiopropyltelluromethyl) hexane, 1- (β-epithiopropyltelluro) -2-[(2-β -Epithiopropyltelluroethyl) thio] ethane, 1- (β-epithiopropyltelluro) -2-[[2- (2-β-epithiopropyltelluroethyl) telluroethyl] thio] ethane, tetrakis (β-epi Thiopropyltelluromethyl) methane, 1,1,1-tris (β-epithiopropyltelluromethyl) propane, 1,5-bis (β-epithiopropyltelluro) -2- ( -Epithiopropyltelluromethyl) -3-thiapentane, 1,5-bis (β-epithiopropyltelluro) -2,4-bis (β-epithiopropyltelluromethyl) -3-thiapentane, 1- (β- Epithiopropyltelluro) -2,2-bis (β-epithiopropyltelluromethyl) -4-thiahexane, 1,5,6-tris (β-epithiopropyltelluro) -4- (β-epithiopropyltelluro) Methyl) -3-thiahexane, 1,8-bis (β-epithiopropyltelluro) -4- (β-epithiopropyltelluromethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropyl) Tellurium) -4,5bis (β-epithiopropyltelluromethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropyltelluro) -4,4-bis (β-epithio) Propyltelluromethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropyltelluro) -2,4,5-tris (β-epithiopropyltelluromethyl) -3,6-dithiaoctane, 1, 8-bis (β-epithiopropyltelluro) -2,5-bis (β-epithiopropyltelluromethyl) -3,6-dithiaoctane, 1,9-bis (β-epithiopropyltelluro) -5- ( β-epithiopropyltelluromethyl) -5-[(2-β-epithiopropyltelluroethyl) selenomethyl] -3,7-dithianonane, 1,10-bis (β-epithiopropyltelluro) -5,6- Bis [(2-β-epithiopropyltelluroethyl) thio] -3,6,9-trithiadecane, 1,11-bis (β-epithiopropyltelluro) -4,8-bis (β-epithiopropy Luterlomethyl) -3,6,9-trithiaundecane, 1,11-bis (β-epithiopropyltelluro) -5,7-bis (β-epithiopropyltelluromethyl) -3,6,9-trithia Undecane, 1,11-bis (β-epithiopropyltelluro) -5,7-[(2-β-epithiopropyltelluroethyl) selenomethyl] -3,6,9-trithiaundecane, 1,11-bis (Β-epithiopropyltelluro) -4,7-bis (β-epithiopropyltelluromethyl) -3,6,9-trithiaundecane, tetra [2- (β-epithiopropyltelluro) acetylmethyl] methane 1,1,1-tri [2- (β-epithiopropyltelluro) acetylmethyl] propane, tetra [2- (β-epithiopropyltelluromethyl) acetylmethyl] methane, 1,1 1-tri [2- (β-epithiopropyltelluromethyl) acetylmethyl] propane, bis (5,6-epithio-3-tellohexyl) selenide, 2,3-bis (6,7-thioepoxy-1-selena- 4-telluroheptyl) -1- (3,4-thioepoxy-1-tellulobutyl) propane, 1,1,3,3-tetrakis (4,5-thioepoxy-2-tellopentyl) -2-selenapropane, bis (4 , 5-thioepoxy-2-tellopentyl) -3,6,9-triselenaundecane-1,11-bis (3,4-thioepoxy-1-tellulobutyl), 1,4-bis (3,4-thioepoxy-1) -Tellurobutyl) -2,3-bis (6,7-thioepoxy-1-selena-4-telloheptyl) butane, tris (4,5-thioepoxy-2-tellope) Nthyl) -3-selena-6-thiaoctane-1,8-bis (3,4-thioepoxy-1-tellulobutyl), bis (5,6-epithio-3-tellohexyl) telledo, 2,3-bis (6 7-thioepoxy-1-tellla-4-telluroheptyl) -1- (3,4-thioepoxy-1-tellulobutyl) propane, 1,1,3,3-tetrakis (4,5-thioepoxy-2-tellopentyl)- 2-tellurapropane, bis (4,5-thioepoxy-2-tellopentyl) -3,6,9-triteraundecane-1,11-bis (3,4-thioepoxy-1-tellulobutyl), 1,4-bis (3,4-thioepoxy-1-tellulobutyl) -2,3-bis (6,7-thioepoxy-1-tellla-4-telluroheptyl) butane, tris (4,5-thioe Xyl-2-tellulopentyl) -3-tellla-6-thiaoctane-1,8-bis (3,4-thioepoxy-1-tellulobutyl), (1,3 or 1,4) -bis (β-epithiopropyltelluro) ) Cyclohexane, (1,3 or 1,4) -bis (β-epithiopropyltelluromethyl) cyclohexane, bis [4- (β-epithiopropyltelluro) cyclohexyl] methane, 2,2-bis [4- ( β-epithiopropyltelluro) cyclohexyl] propane, bis [4- (β-epithiopropyltelluro) cyclohexyl] sulfide, 2,5-bis (β-epithiopropyltelluromethyl) -1,4-dithiane, 2, 5-bis (β-epithiopropyltelluroethylthiomethyl) -1,4-dithiane, (2,3 or 2,5 or 2,6) -bis (3,4 Epithio-1-tellulobutyl) -1,4-diselenane, (2,3 or 2,5 or 2,6) -bis (4,5-epithio-2-tellopentyl) -1,4-diselenane, (2,4 Or 2,5 or 5,6) -bis (3,4-epithio-1-tellulobutyl) -1,3-diselenane, (2,4 or 2,5 or 5,6) -bis (4,5-epithio 2-telluropentyl) -1,3-diselenane, (2,3 or 2,5 or 2,6 or 3,5) -bis (3,4-epithio-1-tellulobutyl) -1-thia-4-selenane , (2,3 or 2,5 or 2,6 or 3,5) -bis (4,5-epithio-2-terlopentyl) -1-thia-4-selenane, (2,4 or 4,5)- Bis (3,4-epithio-1-tellurobutyl) -1,3-di Selenolane, (2,4 or 4,5) -bis (4,5-epithio-2-tellopentyl) -1,3-diselenolane, (2,4 or 2,5 or 4,5) -bis (3,4 -Epithio-1-tellulobutyl) -1-thia-3-selenolane, (2,4 or 2,5 or 4,5) -bis (4,5-epithio-2-tellopentyl) -1-thia-3-selenolane 2,6-bis (4,5-epithio-2-telluropentyl-1,3,5-triselenane, bis (3,4-epithio-1-tellulobutyl) tricycloselenaoctane, bis (3,4-epithio- 1-tellulobutyl) dicycloselenanane, (2,3 or 2,4 or 2,5 or 3,4) -bis (3,4-epithio-1-tellulobutyl) selenophane, (2,3 or 2,4 Or 2,5 Is 3,4) -bis (4,5-epithio-2-tellopentyl) selenophan, 2- (4,5-thioepoxy-2-tellopentyl) -5- (3,4-thioepoxy-1-tellulobutyl) -1 -Selenacyclohexane, (2,3 or 2,4 or 2,5 or 2,6 or 3,4 or 3,5 or 4,5) -bis (3,4-thioepoxy-1-tellulobutyl) -1-selena Cyclohexane, (2,3 or 2,4 or 2,5 or 2,6 or 3,4 or 3,5 or 4,5) -bis (4,5-thioepoxy-2-tellopentyl) -1-selenacyclohexane, (2,3 or 2,5 or 2,6) -bis (3,4-epithio-1-tellulobutyl) -1,4-diterlan, (2,3 or 2,5 or 2,6) -bis (4 , 5-D Thio-2-tellulopentyl) -1,4-diterlan, (2,4 or 2,5 or 5,6) -bis (3,4-epithio-1-tellulobutyl) -1,3-diterlan, (2,4 Or 2,5 or 5,6) -bis (4,5-epithio-2-terlopentyl) -1,3-diterlan, (2,3 or 2,5 or 2,6 or 3,5) -bis (3 , 4-epithio-1-tellulobutyl) -1-thia-4-tellane, (2,3 or 2,5 or 2,6 or 3,5) -bis (4,5-epithio-2-telluropentyl) -1 -Thia-4-tellrane, (2,4 or 4,5) -bis (3,4-epithio-1-tellulobutyl) -1,3-ditellurolane, (2,4 or 4,5) -bis (4 5-epithio-2-telluropentyl) -1,3-ditellurolane, (2,4 or 2,5 or 4,5) -bis (3,4-epithio-1-tellulobutyl) -1-thia-3-tellurolane, (2,4 or 2,5 or 4,5) -bis (4,5-epithio-2-telluropentyl) -1-thia-3-tellurolane, 2,6-bis (4,5-epithio-2-tellopentyl-1,3,5-tritellane, bis (3,4- Epithio-1-tellulobutyl) tricyclotellalaoctane, bis (3,4-epithio-1-tellulobutyl) dicyclotelllanonane, (2,3 or 2,4 or 2,5 or 3,4) -bis (3 4-epithio-1-tellulobutyl) tellophane, (2,3 or 2,4 or 2,5 or 3,4) -bis (4,5-epithio-2-tellopentyl) tellurophan, 2- (4,5-thioepoxy -2- Luropentyl) -5- (3,4-thioepoxy-1-tellulobutyl) -1-tellulacyclohexane, (2,3 or 2,4 or 2,5 or 2,6 or 3,4 or 3,5 or 4,5 ) -Bis (3,4-thioepoxy-1-tellulobutyl) -1-tellulacyclohexane, (2,3 or 2,4 or 2,5 or 2,6 or 3,4 or 3,5 or 4,5)- Bis (4,5-thioepoxy-2-telluropentyl) -1-tellulacyclohexane, (1,3 or 1,4) -bis (β-epithiopropyltelluro) benzene, (1,3 or 1,4) -bis (Β-epithiopropyltelluromethyl) benzene, bis [4- (β-epithiopropyltelluro) phenyl] methane, 2,2-bis [4- (β-epithiopropyltelluro) phenyl] propyl Lopan, bis [4- (β-epithiopropyltelluro) phenyl] sulfide, bis [4- (β-epithiopropyltelluro) phenyl] sulfone, 4,4′-bis (β-epithiopropyltelluro) biphenyl, etc. Episulfides having at least one epithioalkyltelluro group, episulfides having an unsaturated group such as vinylphenylthioglycidyl ether, vinylbenzylthioglycidyl ether, thioglycidyl methacrylate, thioglycidyl acrylate, allylthioglycidyl ether, ethylene sulfide , Propylene sulfide, thioglycidol, thioglycidyl acetate, thioglycidyl propionate, thioglycidyl benzoate and other episulfides, and the episulfide compounds listed above And episulfides in which one or more hydrogens of the epithio group of the product are substituted with methyl groups. These may be used alone or in combination of two or more.

  Furthermore, you may have an unsaturated group. Specific examples of these include vinyl phenyl thioglycidyl ether, vinyl benzyl thioglycidyl ether, thioglycidyl methacrylate, thioglycidyl acrylate, allyl thioglycidyl ether and the like.

  Specific examples of the most preferable component (D) include bis (β-epithiopropyl) sulfide, bis (β-epithiopropyl) disulfide, bis (β-epithiopropyl) selenide, and bis (β-epi). Thiopropyl) diselenide, and a chain, branched compound, aliphatic ring, aromatic compound, and heterocyclic compound having two or more β-epithiopropylthio groups and β-epithiopropylseleno groups. Of these, bis (β-epithiopropyl) sulfide, bis (β-epithiopropyl) disulfide, bis (β-epithiopropyl) selenide, and bis (β-epithiopropyl) diselenide are particularly preferred.

  The composition of the present invention can be heat-polymerized to produce a resin in the presence or absence of a curing catalyst. A preferable method is a method using a curing catalyst, and examples of the curing catalyst include amines, phosphine, quaternary ammonium salts, quaternary phosphonium salts, tertiary sulfonium salts, secondary iodonium salts, mineral acids, Lewis acids, organic acids, silicic acids, tetrafluoroboric acids, peroxides, azotized compounds, condensates of aldehydes and ammonia compounds, guanidines, thioureas, thiazoles, sulfenamides, thiuram , Dithiocarbamates, xanthates, acidic phosphates and the like. The typical examples of these are shown below.

(A) Ethylamine, n-propylamine, sec-propylamine, n-butylamine, sec-butylamine, i-butylamine, tert-butylamine, pentylamine, hexylamine, heptylamine, octylamine, decylamine, laurylamine, mistyri Ruamine, 1,2-dimethylhexylamine, 3-pentylamine, 2-ethylhexylamine, allylamine, aminoethanol, 1-aminopropanol, 2-aminopropanol, aminobutanol, aminopentanol, aminohexanol, 3-ethoxypropylamine 3-propoxypropylamine, 3-isopropoxypropylamine, 3-butoxypropylamine, 3-isobutoxypropylamine, 3- (2-ethylhexyloxy) propylamine Primary amines such as ethylene, aminocyclopentane, aminocyclohexane, aminonorbornene, aminomethylcyclohexane, aminobenzene, benzylamine, phenethylamine, α-phenylethylamine, naphthylamine, furfurylamine; ethylenediamine, 1,2-diaminopropane, 1, 3-diaminopropane, 1,2-diaminobutane, 1,3-diaminobutane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 1,7-diaminoheptane, 1,8 -Diaminooctane, dimethylaminopropylamine, diethylaminopropylamine, bis- (3-aminopropyl) ether, 1,2-bis- (3-aminopropoxy) ethane, 1,3-bis- (3-aminopropoxy)- 2,2'-dimethyl Propane, aminoethylethanolamine, 1,2-, 1,3- or 1,4-bisaminocyclohexane, 1,3- or 1,4-bisaminomethylcyclohexane, 1,3- or 1,4-bisamino Ethylcyclohexane, 1,3- or 1,4-bisaminopropylcyclohexane, hydrogenated 4,4′-diaminodiphenylmethane, 2- or 4-aminopiperidine, 2- or 4-aminomethylpiperidine, 2- or 4-amino Ethylpiperidine, N-aminoethylpiperidine, N-aminopropylpiperidine, N-aminoethylmorpholine, N-aminopropylmorpholine, isophoronediamine, menthanediamine, 1,4-bisaminopropylpiperazine, o-, m-, or p -Phenylenediamine, 2,4 Or 2,6-tolylenediamine, 2,4-toluenediamine, m-aminobenzylamine, 4-chloro-o-phenylenediamine, tetrachloro-p-xylylenediamine, 4-methoxy-6-methyl-m- Phenylenediamine, m-, or p-xylylenediamine, 1,5- or 2,6-naphthalenediamine, benzidine, 4,4′-bis (o-toluidine), dianisidine, 4,4′-diaminodiphenylmethane, 2,2- (4,4′-diaminodiphenyl) propane, 4,4′-diaminodiphenyl ether, 4,4′-thiodianiline, 4,4′-diaminodiphenylsulfone, 4,4′-diaminoditolylsulfone, methylenebis (O-chloroaniline), 3,9-bis (3-aminopropyl) 2,4,8,10-tetrao Saspiro [5,5] undecane, diethylenetriamine, iminobispropylamine, methyliminobispropylamine, bis (hexamethylene) triamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, N-aminoethylpiperazine, N-amino Primary polyamines such as propylpiperazine, 1,4-bis (aminoethylpiperazine), 1,4-bis (aminopropylpiperazine), 2,6-diaminopyridine, bis (3,4-diaminophenyl) sulfone; Dipropylamine, di-n-butylamine, di-sec-butylamine, diisobutylamine, di-n-pentylamine, di-3-pentylamine, dihexylamine, octylamine, di (2-ethylhexyl) amine, methyl Ruhexylamine, diallylamine, pyrrolidine, piperidine, 2-, 3-, 4-picoline, 2,4-, 2,6-, 3,5-lupetidine, diphenylamine, N-methylaniline, N-ethylaniline, dibenzylamine , Methylbenzylamine, dinaphthylamine, pyrrole, indoline, indole, morpholine and other secondary amines; N, N′-dimethylethylenediamine, N, N′-dimethyl-1,2-diaminopropane, N, N′-dimethyl- 1,3-diaminopropane, N, N′-dimethyl-1,2-diaminobutane, N, N′-dimethyl-1,3-diaminobutane, N, N′-dimethyl-1,4-diaminobutane, N , N′-dimethyl-1,5-diaminopentane, N, N′-dimethyl-1,6-diaminohexane, N, N′-dimethyl-1,7 Diaminoheptane, N, N′-diethylethylenediamine, N, N′-diethyl-1,2-diaminopropane, N, N′-diethyl-1,3-diaminopropane, N, N′-diethyl-1,2- Diaminobutane, N, N′-diethyl-1,3-diaminobutane, N, N′-diethyl-1,4-diaminobutane, N, N′-diethyl-1,6-diaminohexane, piperazine, 2-methyl Piperazine, 2,5- or 2,6-dimethylpiperazine, homopiperazine, 1,1-di- (4-piperidyl) methane, 1,2-di- (4-piperidyl) ethane, 1,3-di- ( Secondary polyamines such as 4-piperidyl) propane, 1,4-di- (4-piperidyl) butane; trimethylamine, triethylamine, tri-n-propylamine, tri-iso-propyl Min, tri-1,2-dimethylpropylamine, tri-3-methoxypropylamine, tri-n-butylamine, tri-iso-butylamine, tri-sec-butylamine, tri-pentylamine, tri-3-pentylamine, Tri-n-hexylamine, tri-n-octylamine, tri-2-ethylhexylamine, tri-dodecylamine, tri-laurylamine, dicyclohexylethylamine, cyclohexyldiethylamine, tri-cyclohexylamine, N, N-dimethylhexylamine, N-methyldihexylamine, N, N-dimethylcyclohexylamine, N-methyldicyclohexylamine, N, N-diethylethanolamine, N, N-dimethylethanolamine, N-ethyldiethanolamine, triethanol Amine, tribenzylamine, N, N-dimethylbenzylamine, diethylbenzylamine, triphenylamine, N, N-dimethylamino-p-cresol, N, N-dimethylaminomethylphenol, 2- (N, N-dimethyl) Aminomethyl) phenol, N, N-dimethylaniline, N, N-diethylaniline, pyridine, quinoline, N-methylmorpholine, N-methylpiperidine, 2- (2-dimethylaminoethoxy) -4-methyl-1,3 , 2-dioxabornane and the like; tetramethylethylenediamine, pyrazine, N, N′-dimethylpiperazine, N, N′-bis ((2-hydroxy) propyl) piperazine, hexamethylenetetramine, N, N, N ′ , N′-tetramethyl-1,3-butanamine, 2-dimethylamino-2 Tertiary polyamines such as hydroxypropane, diethylaminoethanol, N, N, N-tris (3-dimethylaminopropyl) amine, 2,4,6-tris (N, N-dimethylaminomethyl) phenol, heptamethylisobiguanide; Imidazole, N-methylimidazole, 2-methylimidazole, 4-methylimidazole, N-ethylimidazole, 2-ethylimidazole, 4-ethylimidazole, N-butylimidazole, 2-butylimidazole, N-undecylimidazole, 2- Undecylimidazole, N-phenylimidazole, 2-phenylimidazole, N-benzylimidazole, 2-benzylimidazole, 2-mercaptoimidazole, 2-mercapto-N-methylimidazole, 2-mercaptobenzoy Midazole, 3-mercapto-4-methyl-4H-1,2,4-triazole, 5-mercapto-1-methyl-tetrazole, 2,5-dimercapto-1,3,4-thiadiazole 1-benzyl-2-methyl Imidazole, N- (2′-cyanoethyl) -2-methylimidazole, N- (2′-cyanoethyl) -2-undecylimidazole, N- (2′-cyanoethyl) -2-phenylimidazole, 3,3-bis Various imidazoles such as-(2-ethyl-4-methylimidazolyl) methane, an adduct of alkyl imidazole and isocyanuric acid; 1,8-diazabicyclo (5,4,0) undecene-7, 1,5-diazabicyclo ( 4,3,0) nonene-5,6-dibutylamino-1,8-diazabicyclo (5,4,0) undecene-7 Amine compounds represented by above; emissions such.
(B) A complex of the amines of (a) with borane and boron trifluoride.
(C) Trimethylphosphine, triethylphosphine, tri-iso-propylphosphine, tri-n-butylphosphine, tri-n-hexylphosphine, tri-n-octylphosphine, tricyclohexylphosphine, triphenylphosphine Fins, tribenzylphosphine, tris (2-methylphenyl) phosphine, tris (3-methylphenyl) phosphine, tris (4-methylphenyl) phosphine, tris (diethylamino) phosphine, tris (4-methylphenyl) phosphine, dimethylphenyl Phosphine such as phosphine, diethylphenylphosphine, dicyclohexylphenylphosphine, ethyldiphenylphosphine, diphenylcyclohexylphosphine, chlorodiphenylphosphine .
(D) Tetramethylammonium chloride, tetramethylammonium bromide, tetramethylammonium acetate, tetraethylammonium chloride, tetraethylammonium bromide, tetraethylammonium acetate, tetra-n-butylammonium fluoride, tetra-n-butylammonium chloride, tetra-n -Butylammonium bromide, tetra-n-butylammonium iodide, tetra-n-butylammonium acetate, tetra-n-butylammonium borohydride, tetra-n-butylammonium hexafluorophosphite, tetra-n-butylammonium hydrogensal Fight, tetra-n-butylammonium tetrafluoroborate, tetra-n-butyl Ruammonium tetraphenylborate, tetra-n-butylammonium paratoluenesulfonate, tetra-n-hexylammonium chloride, tetra-n-hexylammonium bromide, tetra-n-hexylammonium acetate, tetra-n-octylammonium chloride, Tetra-n-octylammonium bromide, tetra-n-octylammonium acetate, trimethyl-n-octylammonium chloride, trimethyldecylammonium chloride, trimethyldodecylammonium chloride, trimethylcetylammonium chloride, trimethyllaurylammonium chloride, trimethylbenzylammonium chloride, trimethyl Benzyl ammonium bromide, trie Ru-n-octylammonium chloride, triethylbenzylammonium chloride, triethylbenzylammonium bromide, tri-n-butyl-n-octylammonium chloride, tri-n-butylbenzylammonium fluoride, tri-n-butylbenzylammonium chloride, tri -N-butylbenzylammonium bromide, tri-n-butylbenzylammonium iodide, n-butyldimethylbenzylammonium chloride, n-octyldimethylbenzylammonium chloride, decyldimethylbenzylammonium chloride, dodecyldimethylbenzylammonium chloride, cetyldimethylbenzylammonium Chloride, lauryldimethylbenzylammonium chloride, methyl Rutriphenylammonium chloride, methyltribenzylammonium chloride, methyltriphenylammonium bromide, methyltribenzylammonium bromide, ethyltriphenylammonium chloride, ethyltribenzylammonium chloride, ethyltriphenylammonium bromide, ethyltribenzylammonium bromide, n-butyl Triphenylammonium chloride, n-butyltribenzylammonium chloride, n-butyltriphenylammonium bromide, n-butyltribenzylammonium bromide, 1-methylpyridinium chloride, 1-methylpyridinium bromide, 1-ethylpyridinium chloride, 1-ethyl Pyridinium bromide, 1-n-butyl Lidinium chloride, 1-n-butylpyridinium bromide, 1-n-hexylpyridinium chloride, 1-n-hexylpyridinium bromide, 1-n-octylpyridinium bromide, 1-n-dodecylpyridinium chloride, 1-n-dodecylpyridinium Bromide, 1-n-cetylpyridinium chloride, 1-n-cetylpyridinium bromide, 1-phenylpyridinium chloride, 1-phenylpyridinium bromide, 1-benzylpyridinium chloride, 1-benzylpyridinium bromide, 1-methylpicolinium chloride, 1 -Methylpicolinium bromide, 1-ethylpicolinium chloride, 1-ethylpicolinium bromide, 1-n-butylpicolinium chloride, 1-n-butyl Rupicolinium bromide, 1-n-hexylpicolinium chloride, 1-n-hexylpicolinium bromide, 1-n-octylpicolinium chloride, 1-n-octylpicolinium bromide, 1-n-dodecylpicolinium chloride, 1-n-dodecylpicolinium bromide, 1-n-cetylpicolinium chloride, 1-n-cetylpicolinium bromide, 1-phenylpicolinium chloride, 1-phenylpicolinium bromide 1-benzylpicolinium chloride, 1-benzyl Quaternary ammonium salts such as picolinium bromide.
(E) Tetramethylphosphonium chloride, tetramethylphosphonium bromide, tetraethylphosphonium chloride, tetraethylphosphonium bromide, tetra-n-butylphosphonium chloride, tetra-n-butylphosphonium bromide, tetra-n-butylphosphonium iodide, tetra-n- Hexylphosphonium bromide, tetra-n-octylphosphonium bromide, methyltriphenylphosphonium bromide, methyltriphenylphosphonium iodide, ethyltriphenylphosphonium bromide, ethyltriphenylphosphonium iodide, n-butyltriphenylphosphonium bromide, n-butyltri Phenylphosphonium iodide, n-hexyltriphenylphosphonium bromide De, n- octyl triphenylphosphonium bromide, tetraphenylphosphonium bromide, tetrakis hydroxymethyl phosphonium chloride, tetrakis hydroxymethyl phosphonium bromide, tetrakis hydroxyethyl phosphonium chloride, phosphonium salts such as tetrakis hydroxybutyl phosphonium chloride.
(F) Trimethylsulfonium bromide, triethylsulfonium bromide, tri-n-butylsulfonium chloride, tri-n-butylsulfonium bromide, tri-n-butylsulfonium iodide, tri-n-butylsulfonium tetrafluoroborate, tri-n- Sulfonium salts such as hexylsulfonium bromide, tri-n-octylsulfonium bromide, triphenylsulfonium chloride, triphenylsulfonium bromide, triphenylsulfonium iodide.

(G) Iodonium salts such as diphenyliodonium chloride, diphenyliodonium bromide, and diphenyliodonium iodide.
(H) Mineral acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid and carbonic acid, and half esters thereof.
(I) Boron trifluoride, boron trifluoride etherate, aluminum fluoride, aluminum chloride, triphenylaluminum, potassium octoate, calcium acetate, tetraisopropoxy titanium, tetrabutoxy titanium, tetrachloro titanium, 2-titanate 2- Ethylhexyl, dimethyltin oxide, dimethyltin dichloride, dibutyltin diacetate, dibutyltin acetate, dibutyltin dilaurate, dibutyltin laurate, dibutyltin octanoate, dibutyltin bis (dodecyl mercaptide), dibutyltin bis (isooctylthioglycolate), dibutyltin oxide, Butyltin trichloride, dibutyltin dichloride, tributyltin chloride, tetrabutyltin, dioctyltin diacetate, dioctyl Acetate, dioctyltin dilaurate, dioctyltin laurate, dioctyltin diricinolate, dioctyltin dioleate, dioctyltin di (6-hydroxy) caproate, dioctyltin bis (isooctylthioglycolate), dioctyltin oxide, dioctyl Tin dichloride, dioctyl tin maleate, dioctyl tin bis (butyl maleate), didodecyl tin diricinolate, tin stearate, zinc chloride, acetylacetone zinc, copper oleate, acetylacetone copper, acetylacetone iron, naphthenate iron, iron lactate Lewis acids represented by iron citrate, iron gluconate and the like.
(J) Organic acids and their half esters.
(K) Silicic acid, tetrafluoroboric acid.
(L) Cumyl peroxyneodecanoate, diisopropyl peroxydicarbonate, diallyl peroxydicarbonate, di-n-propyl peroxydicarbonate, dimyristyl peroxydicarbonate, cumyl peroxyneohexanoate, tert- Hexyl peroxyneodecanoate, tert-butylperoxyneodecanoate, tert-hexylperoxyneohexanoate, tert-butylperoxyneohexanoate, 2,4-dichlorobenzoyl peroxide, benzoyl peroxide Peroxides such as dicumyl peroxide and di-ter-butyl peroxide; peroxides such as cumene hydroperoxide and tert-butyl hydroperoxide.
(M) 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile), 2,2′-azobis (2-cyclopropylpropionitrile), 2,2′-azobis (2,4- Dimethylvaleronitrile), 2,2′-azobisisobutyronitrile, 2,2′-azobis (2-methylbutyronitrile), 1,1′-azobis (cyclohexane-1-carbonitrile), 1- [ (1-Cyano-1-methylethyl) azo] formamide, 2-phenylazo-4-methoxy-2,4-dimethyl-valeronitrile 2, 2′-azobis (2-methylpropane), 2,2′-azobis ( 2, 4, 4-trimethylpentane) and the like.
(N) Acetaldehyde and ammonia reaction product, formaldehyde and paraylidine condensate, acetaldehyde and paraylidine condensate, formaldehyde and aniline reaction product, acetaldehyde and aniline reaction product, butyraldehyde and aniline reaction product, formaldehyde and acetaldehyde reaction product Reaction product of aniline, reaction product of acetaldehyde, butyraldehyde and aniline, condensation product of butyraldehyde and monobutylamine, reaction product of butyraldehyde and butylideneaniline, reaction product of heptaldehyde and aniline, reaction of tricrotonylidene-tetramine , Condensates of aldehydes and amine compounds, such as condensates of α-ethyl-β-propylacrolein and aniline, condensates of formaldehyde and alkylimidazoles.
(O) diphenylguanidine, phenyltolylguanidine, phenylxylylguanidine, tolyloxysilylguanidine, diortolylguanidine, orthotolylguanide, diphenylguanidine phthalate, tetramethylguanidine, diorthotolylguanidine salt of dicatecholboric acid, etc. Guanidines.
(P) Thioureas such as thiocarbonanilide, diortolylthiourea, ethylenethiourea, diethylthiourea, dibutylthiourea, dilaurylthiourea, trimethylthiourea, dimethylethylthiourea, tetramethylthiourea, and the like.

(Q) 2-mercaptobenzothiazole, dibenzothiazyl disulfide, cyclohexylamine salt of 2-mercaptobenzothiazole, 2- (2,4-dinitrophenylthio) benzothiazole, 2- (morpholinodithio) benzothiazole, 2- ( 2,6-dimethyl-4-morpholinothio) benzothiazole, N, N-diethylthiocarbamoyl-2-benzothiazolyl sulfide, 1,3-bis (2-benzothiazolylmercaptomethyl) urea, benzothiadiadi Thiazoles such as ruthiobenzoate, 2-mercaptothiazoline, sodium salt of 2-mercaptobenzothiazole, zinc salt of 2-mercaptobenzothiazole, complex salt of dibenzothiazyl disulfide and zinc chloride.
(R) N-cyclohexyl-2-benzothiazylsulfenamide, N-tert-butyl-2-benzothiazylsulfenamide, N-tert-octyl-2-benzothiazylsulfenamide, N-oxydiethylene 2-benzothiazylsulfenamide, N, N-diethyl-2-benzothiazylsulfenamide, N, N-diisopropyl-2-benzothiazylsulfenamide, N, N-dicyclohexyl-2-benzothia Sulfenamides such as dirusulfenamide.
(S) Tetramethylthiuram monosulfide, tetraethylthiuram monosulfide, tetrabutylthiuram monosulfide, dipentamethylenethiuram monosulfide, tetramethylthiuram disulfide, tetraethylthiuram disulfide, tetrabutylthiuram disulfide, N, N′-dimethyl-N, Thiurams such as N′-diphenylthiuram disulfide, N, N′-diethyl-N, N′-diphenylthiuram disulfide, dipentamethylenethiuram disulfide, dipentamethylenethiuram tetrasulfide, and cyclic thiuram.
(T) sodium dimethyldithiocarbamate, sodium diethyldithiocarbamate, sodium dibutyldithiocarbamate, sodium pentamethylenedithiocarbamate, sodium cyclohexylethyldithiocarbamate, potassium dimethyldithiocarbamate, lead dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc diethyldithiocarbamate, Zinc dibutyldithiocarbamate, zinc dibenzyldithiocarbamate, zinc pentamethylenedithiocarbamate, zinc dimethylpentamethylenedithiocarbamate, zinc ethylphenyldithiocarbamate, bismuth dimethyldithiocarbamate, cadmium diethyldithiocarbamate, cadmium pentamethylenedithiocarbamate, dimethyldithioca Selenium bamates, selenium diethyldithiocarbamate, tellurium dimethyldithiocarbamate, tellurium diethyldithiocarbamate, iron dimethyldithiocarbamate, copper dimethyldithiocarbamate, diethylammonium diethyldithiocarbamate, dibutyldithiocarbamate N, N-cyclohexylammonium, pentamethylenedithiocarbamate piperidine Dithiocarbamates such as sodium cyclohexylethylammonium cyclohexylethyldithiocarbamate, pipecoline methylpentamethylenedithiocarbamate, and a complex compound of zinc pentamethylenedithiocarbamate and piperidine.
(U) Xanthates such as sodium isopropylxanthate, zinc isopropylxanthate, zinc butylxanthate, and dibutylxanthate disulfide. (V) mono- and / or dimethyl phosphate, mono- and / or diethyl phosphate, mono- and / or dipropyl phosphate, mono- and / or dibutyl phosphate, mono- and / or dihexyl phosphate, mono- and / Or acid such as dioctyl phosphate, mono- and / or didecyl phosphate, mono- and / or didodecyl phosphate, mono- and / or diphenyl phosphate, mono- and / or dibenzyl phosphate, mono- and / or didecanol phosphate Phosphate esters.

  As mentioned above, although the polymerization catalyst at the time of carrying out the polymerization hardening of the composition of this invention was illustrated, if the effect of polymerization hardening is expressed, it will not be limited to these listed compounds. These may be used alone or in combination of two or more. The addition amount of the catalyst used in the present invention is 0.0001 to 10.0 parts by weight, preferably 0 with respect to 100 parts by weight of any of the compositions represented by (1) or (2). .0005 to 5.0 parts by weight. When the amount of the curing catalyst is more than 10.0 parts by weight, the refractive index and heat resistance of the cured product are lowered, and coloring occurs. On the other hand, if it is less than 0.0001 part by weight, it will not be cured sufficiently and the heat resistance will be insufficient.

  In the composition for optical materials of the present invention, for the purpose of improving various performances such as oxidation resistance, weather resistance, dyeability, strength, and optical properties, a compound capable of reacting with some or all of the composition components is used as a performance improver. It is also possible to add and cure polymerization. In this case, a polymerization curing catalyst can be added separately as necessary for this reaction.

  Compounds that can react with some or all of the composition components include epoxy compounds, carboxylic acids, carboxylic anhydrides, phenols, amines, vinyl compounds, allyl compounds, acrylic compounds, methacrylic compounds, etc. Can be mentioned. The typical examples of these are shown below.

  (A) Manufactured by condensation of monohalo compounds such as ethylene oxide and propylene oxide, hydroquinone, catechol, resorcin, bisphenol A, bisphenol F, bisphenol ether, halogenated bisphenol A, novolac resin and the like and epihalohydrin Phenolic epoxy compounds, methanol, ethanol, propanol, butanol, ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, 1,3-propanediol, 1,4-butanediol 1,6-hexanediol, neopentyl glycol, glycerin, trimethylolpropane, pentaerythrito 1,3- and 1,4-cyclohexanediol, 1,3- and 1,4-cyclohexanedimethanol, hydrogenated bisphenol A, bisphenol A / ethylene oxide adduct, bisphenol A / propylene oxide adduct, etc. Alcohol epoxy compounds produced by condensation of compounds and epihalohydrins, urethane epoxy compounds produced from the above-mentioned alcohols and phenol compounds and diisocyanates, acetic acid, propionic acid, benzoic acid, adipic acid, sebacic acid, dodecanedicarboxylic acid, Dimer acid, phthalic acid, iso, terephthalic acid, tetrahydrophthalic acid, methyltetrahydrophthalic acid, hexahydrophthalic acid, het acid, nadic acid, maleic acid, succinic acid, fumaric acid, trimellitic acid, benze Glycidyl ester epoxy compounds produced by condensation of carboxylic acid compounds such as tetracarboxylic acid, benzophenone tetracarboxylic acid, naphthalene dicarboxylic acid, diphenyl dicarboxylic acid, acrylic acid, methacrylic acid, maleic acid, fumaric acid and epihalohydrin, ethylenediamine, 1 , 2-diaminopropane, 1,3-diaminopropane, 1,2-diaminobutane, 1,3-diaminobutane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 1, 7-diaminoheptane, 1,8-diaminooctane, bis- (3-aminopropyl) ether, 1,2-bis- (3-aminopropoxy) ethane, 1,3-bis- (3-aminopropoxy) -2 , 2'-dimethylpropane, 1,2-, 1,3- or 1 , 4-bisaminocyclohexane, 1,3- or 1,4-bisaminomethylcyclohexane, 1,3- or 1,4-bisaminoethylcyclohexane, 1,3- or 1,4-bisaminopropylcyclohexane, water 4,4'-diaminodiphenylmethane, isophoronediamine, 1,4-bisaminopropylpiperazine, m- or p-phenylenediamine, 2,4- or 2,6-tolylenediamine, m- or p-xylyl Range amine, 1,5- or 2,6-naphthalenediamine, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl ether, 2,2- (4,4'-diaminodiphenyl) propane, 2-amino Benzenethiol, 3-aminobenzenethiol, 4-aminobenzenethiol N, N′-dimethylethylenediamine, N, N′-dimethyl-1,2-diaminopropane, N, N′-dimethyl-1,3-diaminopropane, N, N′-dimethyl-1,2-diamino Butane, N, N′-dimethyl-1,3-diaminobutane, N, N′-dimethyl-1,4-diaminobutane, N, N′-dimethyl-1,5-diaminopentane, N, N′-dimethyl -1,6-diaminohexane, N, N′-dimethyl-1,7-diaminoheptane, N, N′-diethylethylenediamine, N, N′-diethyl-1,2-diaminopropane, N, N′-diethyl -1,3-diaminopropane, N, N′-diethyl-1,2-diaminobutane, N, N′-diethyl-1,3-diaminobutane, N, N′-diethyl-1,4-diaminobutane, N, '-Diethyl-1,6-diaminohexane, piperazine, 2-methylpiperazine, 2,5- or 2,6-dimethylpiperazine, homopiperazine, 1,1-di- (4-piperidyl) -methane, 1,2 -Amine-based epoxy compounds produced by condensation of 1,3-di- (4-piperidyl) -propane, 1,4-di- (4-piperidyl) -butane and epihalohydrin Bis (β-epoxypropyl) sulfide, bis (β-epoxypropylthio) methane, 1,2-bis (β-epoxypropylthio) ethane, 1,3-bis (β-epoxypropylthio) propane, 1, 2-bis (β-epoxypropylthio) propane, 1- (β-epoxypropylthio) -2- (β-epoxypropylthiomethyl) propane, 1 , 4-bis (β-epoxypropylthio) butane, 1,3-bis (β-epoxypropylthio) butane, 1- (β-epoxypropylthio) -3- (β-epoxypropylthiomethyl) butane, , 5-bis (β-epoxypropylthio) pentane, 1- (β-epoxypropylthio) -4- (β-epoxypropylthiomethyl) pentane, 1,6-bis (β-epoxypropylthio) hexane, -(Β-epoxypropylthio) -5- (β-epoxypropylthiomethyl) hexane, 1- (β-epoxypropylthio) -2-[(2-β-epoxypropylthioethyl) thio] ethane, 1- (Β-epoxypropylthio) -2-[[2- (2-β-epoxypropylthioethyl) thioethyl] thio] ethane, tetrakis (β-epoxypropylthio Til) methane, 1,1,1-tris (β-epoxypropylthiomethyl) propane, 1,5-bis (β-epoxypropylthio) -2- (β-epoxypropylthiomethyl) -3-thiapentane, , 5-Bis (β-epoxypropylthio) -2,4-bis (β-epoxypropylthiomethyl) -3-thiapentane, 1- (β-epoxypropylthio) -2,2-bis (β-epoxypropyl) Thiomethyl) -4-thiahexane, 1,5,6-tris (β-epoxypropylthio) -4- (β-epoxypropylthiomethyl) -3-thiahexane, 1,8-bis (β-epoxypropylthio) -4- (β-epoxypropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (β-epoxypropylthio) -4,5bis (β-epoxypropylthio) Methyl) -3,6-dithiaoctane, 1,8-bis (β-epoxypropylthio) -4,4-bis (β-epoxypropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (β- Epoxypropylthio) -2,4,5-tris (β-epoxypropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (β-epoxypropylthio) -2,5-bis (β-epoxypropyl) Thiomethyl) -3,6-dithiaoctane, 1,9-bis (β-epoxypropylthio) -5- (β-epoxypropylthiomethyl) -5-[(2-β-epoxypropylthioethyl) thiomethyl]- 3,7-dithianonane, 1,10-bis (β-epoxypropylthio) -5,6-bis [(2-β-epoxypropylthioethyl) thio] -3,6,9-trithiadecane 1,11-bis (β-epoxypropylthio) -4,8-bis (β-epoxypropylthiomethyl) -3,6,9-trithiaundecane, 1,11-bis (β-epoxypropylthio) -5,7-bis (β-epoxypropylthiomethyl) -3,6,9-trithiaundecane, 1,11-bis (β-epoxypropylthio) -5,7-[(2-β-epoxypropyl Thioethyl) thiomethyl] -3,6,9-trithiaundecane, 1,11-bis (β-epoxypropylthio) -4,7-bis (β-epoxypropylthiomethyl) -3,6,9-tri Thiaundecane, 1,3 and 1,4-bis (β-epoxypropylthio) cyclohexane, 1,3 and 1,4-bis (β-epoxypropylthiomethyl) cyclohexane, bis [4- (β-epoxy Xylpropylthio) cyclohexyl] methane, 2,2-bis [4- (β-epoxypropylthio) cyclohexyl] propane, bis [4- (β-epoxypropylthio) cyclohexyl] sulfide, 2,5-bis (β- Epoxypropylthiomethyl) -1,4-dithiane, 2,5-bis (β-epoxypropylthioethylthiomethyl) -1,4-dithiane, 1,3 and 1,4-bis (β-epoxypropylthio) Benzene, 1,3 and 1,4-bis (β-epoxypropylthiomethyl) benzene, bis [4- (β-epoxypropylthio) phenyl] methane, 2,2-bis [4- (β-epoxypropylthio) ) Phenyl] propane, bis [4- (β-epoxypropylthio) phenyl] sulfide, bis [4- (β-epoxypropylthio) Nyl] sulfone, sulfur-containing epoxy compounds such as 4,4′-bis (β-epoxypropylthio) biphenyl, 3,4-epoxycyclohexyl-3,4-epoxycyclohexanecarboxylate, vinylcyclohexanedioxide, 2- ( 3,4-epoxycyclohexyl) -5,5-spiro-3,4-epoxycyclohexane-meta-dioxane, alicyclic epoxy compounds such as bis (3,4-epoxycyclohexyl) adipate, cyclopentadiene epoxide, large epoxidation Epoxy compounds produced by epoxidation of unsaturated compounds such as soybean oil, epoxidized polybutadiene, vinylcyclohexene epoxide, vinyl phenyl glycidyl ether, vinyl benzyl glycidyl ether, glycidyl methacrylate, glycidyl acrylate DOO, epoxy compounds epoxy compounds, etc. having an unsaturated group such as allyl glycidyl ether.

(B) Carboxylic acids exemplified as the starting material of the partner to be reacted with the epihalohydrin described in the epoxy compound of (a).
(C) Carboxylic anhydrides exemplified as the raw material of the partner to be reacted with the epihalohydrin described in the epoxy compound of (a).
(D) Phenols exemplified as the starting material of the partner to be reacted with the epihalohydrin described in the epoxy compound of (a).
(E) Amines exemplified as the starting material of the partner to be reacted with the epihalohydrin described in the epoxy compound of (a).
(F) Vinyl ether, ethyl vinyl ether, isobutyl vinyl ether, 2-ethylhexyl vinyl ether, phenyl vinyl ether, benzyl vinyl ether, 2-chloroethyl vinyl ether, cyclohexyl vinyl ether, vinyl glycidyl ether, vinyl alcohol, methyl vinyl carbinol, ethylene glycol monovinyl ether, ethylene glycol Divinyl ether, diethylene glycol monovinyl ether, diethylene glycol divinyl ether, tetramethylene glycol monovinyl ether, divinyl sulfide, vinyl ethyl sulfide, vinyl phenyl sulfide, methyl vinyl ketone, divinyl dicarbonate, vinyl diglycol carbonate, vinylene carbonate, vinyl acetate, chloro Vinyl acetate, vinyl propionate, vinyl butyrate, vinyl hexanoate, vinyl 2-ethylhexanoate, divinyl adipate, vinyl benzoate, vinyl salicylate, vinyl acrylate, vinyl methacrylate, vinyl bromide, vinyl iodide, vinyl phosphate, Vinylurea, styrene, 2-methylstyrene, 3-methylstyrene, 4-methylstyrene, α-methylstyrene, 2,4,6-trimethylstyrene, 4-t-butylstyrene, stilbene, vinylphenol, 3-vinylbenzyl Alcohol, 4-vinylbenzyl alcohol, 2- (4-vinylphenylthio) ethanol, 2- (3-vinylphenylthio) ethanol, 2- (4-vinylbenzylthio) ethanol, 2- (3-vinylbenzylthio) Ethanol, 1,3-bis (4- Vinylbenzylthio) -2-propanol, 1,3-bis (3-vinylbenzylthio) -2-propanol, 2,3-bis (4-vinylbenzylthio) -1-propanol, 2,3-bis (3 -Vinylbenzylthio) -1-propanol, cinnamyl alcohol, cinnamaldehyde, 1,3-divinylbenzene, 1,4-divinylbenzene, trivinylbenzene, divinylphthalate, 2-chlorostyrene, 3-chlorostyrene, 4- Chlorostyrene, 3-chloromethylstyrene, 4-chloromethylstyrene, 4-aminostyrene, 3-cyanomethylstyrene, 4-cyanomethylstyrene, 4-vinylbiphenyl, 2,2'-divinylbiphenyl, 4,4'- Divinylbiphenyl, 2,2'-distyryl ether, 4,4'-distyryl ether 2,2′-distyryl sulfide, 4,4′-distyryl sulfide, 2,2-bis (4-vinylphenyl) propane, bis (4-vinylphenyl) ether, 2,2-bis (4-vinyl) Vinyl compounds such as (roxyphenyl) propane;
(G) Allyl compounds in which some or all of the vinyl groups of the compounds exemplified as the vinyl compounds in (f) are replaced with allyl groups.
(H) Methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, cyclohexyl acrylate, 2-hydroxyethyl acrylate, 3-hydroxypropyl acrylate, 2-hydroxypropyl acrylate, 3-phenoxy-2-hydroxypropyl acrylate, trimethylolpropane mono Acrylate, 2-hydroxyethyl isocyanurate monoacrylate, 2-hydroxyethyl isocyanurate diacrylate, 2-hydroxyethyl cyanurate monoacrylate, 2-hydroxyethyl cyanurate diacrylate, ethylene glycol diacrylate, diethylene glycol diacrylate, 1,3 -Butylene glycol diacrylate, triethylene glycol diacrylate Polyethylene glycol diacrylate, propylene glycol diacrylate, 1,3-propanediol diacrylate, 1,3-butanediol diacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, neopentyl glycol diacrylate Acrylate, polypropylene glycol diacrylate, 2-hydroxy-1,3-diacryloxypropane, 2,2-bis [4- (acryloxyethoxy) phenyl] propane, 2,2-bis [4- (acryloxyethoxy) Cyclohexyl] propane, 2,2-bis [4- (2-hydroxy-3-acryloxypropoxy) phenyl] propane, 2,2-bis [4- (acryloxy-diethoxy) phenyl] propane, 2,2-bis [ 4- (Acryl Polyethoxy) phenyl] propane, trimethylolpropane triacrylate, pentaerythritol monoacrylate, pentaerythritol diacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, pentaacrylate of bis (2,2,2-trimethylolethyl) ether , Acrylic compounds such as hexaacrylate of bis (2,2,2-trimethylolethyl) ether, bis (4-acryloylthiophenyl) sulfide.
(I) Methacrylic compounds in which part or all of the acrylic groups of the compounds exemplified as the acrylic compounds of (h) are replaced with methacrylic groups.

  It is also possible to use an inorganic compound containing a sulfur atom and / or selenium atom for the purpose of improving the refractive index. Specific examples of the refractive index improving component include sulfur, hydrogen sulfide, carbon disulfide, carbon selenosulfide, ammonium sulfide, sulfur dioxide, sulfur trioxide, and other sulfur oxides, thiocarbonate, sulfuric acid and its salts, hydrogen sulfate. Salts, sulfites, hyposulfites, persulfates, thiocyanates, thiosulfates, sulfur dichloride, thionyl chloride, thiophosgene and other halides, boron sulfide, nitrogen sulfide, silicon sulfide, phosphorus sulfide, arsenic sulfide, metal Excluding inorganic compounds having sulfur atoms such as sulfides and metal hydrosulfides, and selenium sulfide, all inorganic compounds satisfying this condition are included. Specific examples include selenium oxides such as selenium, hydrogen selenide, selenium dioxide, carbon diselenide, ammonium selenide, selenium dioxide, selenic acid and salts thereof, selenite and salts thereof, hydrogen selenate salts, seleno Sulfuric acid and salts thereof, selenopyrosulfuric acid and salts thereof, halides such as selenium tetrabromide and selenium oxychloride, selenium atoms such as selenocyanate, boron selenide, phosphorus selenide, arsenic selenide and metal selenides Examples include inorganic compounds. These inorganic compounds having a sulfur atom and a selenium atom may be used alone or in combination of two or more.

  When an optical material is obtained by polymerizing and curing the composition of the present invention, known additives such as antioxidants, ultraviolet absorbers, yellowing inhibitors, bluing agents, pigments, etc. are added, and the practicality of the resulting material Of course, it is possible to improve further. Further, when the composition of the present invention is easily peeled off from the mold during polymerization, a known external and / or internal adhesion improver is used or added to control and improve the adhesion between the obtained cured material and the mold. Is also necessary. Examples of the internal adhesion improving agent mentioned here include 3-methacryloxypropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, 3 Examples include silane compounds such as mercaptopropyltrimethoxysilane, and 0.00001 to 5 parts by weight can be used with respect to 100 parts by weight of the composition of the present invention. Conversely, when the composition of the present invention is difficult to peel off from the mold after polymerization, a known external and / or internal mold release agent is used or added to improve the mold releasability from the mold of the resulting cured material. Is also possible. The internal mold release agent mentioned here is a fluorine-based nonionic surfactant, a silicon-based nonionic surfactant, an alkyl quaternary ammonium salt, a phosphate ester, an acidic phosphate ester, an oxyalkylene-type acidic phosphate ester, an alkali of an acidic phosphate ester. Metal salts, alkali metal salts of oxyalkylene acid phosphates, metal salts of higher fatty acids, higher fatty acid esters, paraffins, waxes, higher aliphatic amides, higher aliphatic alcohols, polysiloxanes, aliphatic amine ethylene oxide adducts, etc. For example, and can be used in an amount of 0.00001 to 5 parts by weight based on 100 parts by weight of the composition of the present invention.

  In the present invention, the method for producing an optical material includes a composition comprising any of the polymerizable composition represented by the above (1) or (2) and a performance improver, a catalyst, an adhesion improver or a mold release improver. After mixing, homogenizing additives such as antioxidants, UV absorbers, yellowing inhibitors, bluing agents, pigments, etc., and then injecting them into glass or metal molds, and proceeding with the polymerization and curing reaction by heating , Manufactured out of mold.

  In the method for producing a cured resin optical material of the present invention, a part or all of the composition comprising any of the polymerizable composition represented by (1) or (2) and the performance improver is cast before casting. After preliminarily polymerizing at −100 to 160 ° C. for 0.1 to 480 hours with or without stirring in the presence or absence of a catalyst, a composition for optical material is prepared and cast. It is also possible to perform. In particular, when the compound in the composition for optical materials contains a solid component and handling is not easy, this preliminary polymerization is effective. The preliminary polymerization conditions are preferably −10 to 120 ° C. for 0.1 to 240 hours, more preferably 0 to 100 ° C. for 0.1 to 120 hours. Additives such as property improvers, antioxidants, ultraviolet absorbers, yellowing inhibitors, bluing agents and pigments may be added simultaneously.

  The manufacturing method of the cured resin optical material of the present invention is as follows in more detail. As mentioned above, the main raw material and auxiliary raw material are mixed and then injected and cured into a mold, but they react with a polymerizable composition containing a polyurethane prepolymer and a part or all of the composition components used as a performance improver. Possible compounds, catalysts, adhesion improvers or mold release improvers, antioxidants, UV absorbers, anti-yellowing agents, bluing agents, pigments, etc. are all stirred together in the same container. Even if it mixes, each raw material may be added and mixed in steps, or several components may be mixed separately and then remixed in the same container. Each raw material, additive and the like may be mixed in any order. In mixing, the set temperature, the time required for this, etc., basically need only be the conditions that each component is sufficiently mixed, but the excessive temperature, time is an undesirable reaction between each raw material and additive, Furthermore, the viscosity is increased, making the casting operation difficult, and so on. The mixing temperature should be about −50 ° C. to 100 ° C., preferably −30 ° C. to 70 ° C., more preferably −5 ° C. to 50 ° C. The mixing time is 1 minute to 12 hours, preferably 5 minutes to 10 hours, and most preferably about 5 minutes to 6 hours. Performing the degassing operation under reduced pressure before, during or after mixing the raw materials and additives is a preferable method from the viewpoint of preventing the generation of bubbles during the subsequent cast polymerization curing. The degree of decompression at this time is about 0.1 mmHg to 700 mmHg, and preferably 0.5 mmHg to 300 mmHg. Furthermore, it is preferable to further refine the quality of the optical material of the present invention by purifying the mixture or the main and sub raw materials before mixing with a filter having a pore size of about 0.05 to 3 μm to purify impurities and the like. . After pouring into a glass or metal mold, polymerization and curing is performed with an electric furnace, water or an oil bath, etc., but the curing time is 0.1 to 100 hours, usually 1 to 72 hours, and the curing temperature is −10 to 160. ° C, usually 0 to 140 ° C. The polymerization can be carried out by holding at a predetermined polymerization temperature for a predetermined time, raising the temperature from 0.1 ° C. to 100 ° C./h, lowering the temperature from 0.1 ° C. to 100 ° C./h, and a combination thereof. In addition, after the curing is completed, annealing the material at a temperature of 50 to 150 ° C. for about 10 minutes to 5 hours is a preferable treatment for removing the distortion of the optical material of the present invention. Furthermore, surface treatment such as dyeing, hard coating, antireflection, antifogging and impact resistance can be performed as necessary.

  Hereinafter, the present invention will be specifically described with reference to Examples and Comparative Examples. The present invention is not limited in any way by these examples. Among the performance tests of the obtained lenses, the refractive index, Abbe number, heat resistance, appearance, and falling ball impact strength were measured and evaluated by the following methods.

(A) Refractive index (n _D ), Abbe number (ν _D ): Measured at 25 ° C. using a precision refractometer KPR-200 manufactured by Kalnew.
(B) Heat resistance: TMA measurement was performed with a load of 98 mN (10 gf) using a pin with a diameter of 0.5 mm by a TMA apparatus manufactured by Rigaku Corporation, and the peak temperature of the chart obtained by heating at 10 ° C./min evaluated.
(C) Impact resistance: A ball drop test was performed in which a lens with a center thickness of 2.5 mm was dropped in order from a light steel ball to a heavy steel ball from a height of 127 cm, and the weight of the steel ball when broken was measured as a ball drop impact value. It was.

Synthesis example 1
Preparation of Prepolymer (1) A mixture of 9.69 g of Plaxel 205 (number average molecular weight 522) and 38.77 g of Plaxel 212 (number average molecular weight 1229) manufactured by Daicel Chemical Industries, which is a polycaprolactone diol, was heated to 90 ° C. and stirred. Then, deaeration was performed under reduced pressure for 1 hour. After restoring the pressure, 26.23 g (0.1 mol) of dicyclohexylmethane-4,4′-diisocyanate (HMDI) was mixed and reacted at 135 ° C. for 1 hour to obtain a polyurethane polymer. The NCO value of the polyurethane polymer after the reaction was measured and found to be 1.34 mmol / g.
The polyurethane polymer was mixed with 7.81 g (0.1 mol) of 2-mercaptoethanol and reacted at 130 ° C. for 1 hour to obtain a polyurethane prepolymer having a number average molecular weight of 3100 and having a mercapto group at the end.

Synthesis example 2
Preparation of prepolymer (2)
A mixture of 11.41 g of Plaxel 205 (number average molecular weight 522) and 45.64 g of Plaxel 212 (number average molecular weight 1229), which are polycaprolactone diols, manufactured by Daicel Chemical Industries, Ltd. is heated to 90 ° C. and stirred for 1 hour under reduced pressure. Deaeration was performed. After restoring the pressure, 20.60 g (0.12 mol) of tolylene diisocyanate (TDI) was mixed and reacted at 90 ° C. for 1 hour to obtain a polyurethane polymer. The NCO value of the polyurethane polymer after the reaction was measured and found to be 1.52 mmol / g.
This polyurethane polymer was mixed with 9.30 g (0.12 mol) of 2-mercaptoethanol, reacted at 105 ° C. for 1 hour, and further reacted at 115 ° C. for 1 hour, whereby a polyurethane prepolymer having a terminal end composed of a mercapto group ( A number average molecular weight of 2000) was obtained.

Synthesis example 3
Preparation of prepolymer (3)
86.21 g of Plaxel 210 (number average molecular weight 983) manufactured by Daicel Chemical Industries, which is a polycaprolactone diol, was heated to 90 ° C. and deaerated under reduced pressure for 1 hour while stirring. After restoring the pressure, 30.54 g (0.18 mol) of tolylene diisocyanate was mixed and reacted at 110 ° C. for 1 hour to obtain a polyurethane polymer having an NCO value of 1.50 mmol / g.
This polyurethane polymer was mixed with 13.71 g (0.18 mol) of 2-mercaptoethanol, reacted at 105 ° C. for 1 hour, and further reacted at 125 ° C. for 1 hour, whereby a polyurethane prepolymer (terminal end of a mercapto group) Number average molecular weight 2000) was obtained.

Synthesis example 4
Preparation of Prepolymer (4) Instead of Placel 210 manufactured by Daicel Chemical Industries, which is a polycaprolactone diol in Synthesis Example 3, 61.45 g of Plaxel 212 and 17.42 g (0.10 mol) of tolylene diisocyanate were used. Preparation was carried out in the same manner as in Synthesis Example 3 to obtain a polyurethane polymer having an NCO value of 1.27 mmol / g.
Furthermore, 2-mercaptoethanol 7.81 (0.10 mol) was mixed with this polyurethane polymer, and a polyurethane prepolymer (number average molecular weight 2200) having a terminal mercapto group was prepared by adjusting under the same conditions as in Synthesis Example 3. Got.

Example 1
26.5 parts by weight of prepolymer (1) and 7.4 parts by weight of bis (2-mercaptomethylsulfide) prepared according to Synthesis Example 1, 8.5 parts by weight of trimethylolpropane tris (3-mercaptopropionate) , 23.6 parts by weight of dicyclohexylmethane-4,4′-diisocyanate, 34.0 parts by weight of bis (β-epithiopropyl) sulfide, 0.05 parts by weight of dibutyltin dichloride, 0.05 parts of tetrabutylphosphonium bromide The parts by weight were mixed to make a uniform solution. Further, this was filtered through a 0.5 μm PTFE filter, poured into a 2.5 mm thick flat lens mold, heated in an oven from 10 ° C. to 130 ° C. over 30 hours, polymerized and cured. A lens was manufactured. The obtained lens had good transparency and surface condition. Table 1 shows the measurement results of the refractive index, Abbe number, impact resistance and heat resistance of the lens.

Examples 2-5
Example 1 was repeated except that the composition shown in Table 1 was used. Table 1 shows the physical properties of the obtained molded product.

Comparative Example 1
A mixture of bis (β-epithiopropyl) sulfide and 0.01 parts by weight of tetrabutylammonium chloride as a catalyst is uniformly stirred and poured into two lens-molding glass molds at 50 ° C. for 10 hours, then 60 A polymer was obtained by heat polymerization at 120 ° C. for 5 hours and further at 120 ° C. for 3 hours. Table 1 shows various physical properties of the obtained polymer. As can be seen from Table 1, the polymer of Comparative Example 1 had a very high refractive index of 1.71 and a relatively high ν _D of 36, but the impact resistance was low.

Comparative Example 2
Uniform mixing of 55.7 parts by weight of pentaerythritol tetrakismercaptopropionate (4TP) and 44.3 parts by weight of 1,3-bisisocyanatomethylcyclohexane (BIC) with 0.10 parts by weight of dibutyltin dichloride as a catalyst Liquid. Further, this was filtered through a 0.5 μm PTFE filter, poured into a 2.5 mm thick flat lens mold, heated in an oven from 10 ° C. to 130 ° C. over 30 hours, polymerized and cured. A lens was manufactured. The obtained lens had good transparency and surface condition. Table 1 shows the measurement results of the refractive index, Abbe number, impact resistance and heat resistance of the lens.
As can be seen from Table 1, the polymer of Comparative Example 2 had a relatively high heat resistance of 91 ° C. but a low impact resistance.

ＤＭＤＳ：ビス（２−メルカプトエチル）スルフィド
３ＴＰ：トリメチロールプロパントリス（３−メルカプトプロピオナート）
４ＴＰ：ペンタエリスリトールテトラキスメルカプトプロピオネート
ＨＭＤＩ：ジシクロヘキシルメタン-４，４’-ジイソシアネート
ＴＤＩ：トリレンジイソシアネート
ＢＩＣ：１，３−ビスイソシアナトメチルシクロヘキサン
Ｄ１：ビス（β-エピチオプロピル）スルフィド
プレポリマー（１）：プラクセル２０５とプラクセル２１２の混合物（重量比１：４）とジシクロヘキシルメタン−４，４’−ジイソシアネートと２−メルカプトエタノールのプレポリマー（モル比１：２：２）
プレポリマー（２）：プラクセル２０５とプラクセル２１２の混合物（重量比１：４）とトリレンジイソシアネートと２−メルカプトエタノールのプレポリマー（モル比１：２：２）
プレポリマー（３）：プラクセル２１０とトリレンジイソシアネートと２−メルカプトエタノールのプレポリマー（モル比１：２：２）
プレポリマー（４）：プラクセル２１２とトリレンジイソシアネートと２−メルカプトエタノールのプレポリマー（モル比１：２：２）
Ｄ１：ビス（β−エピチオプロピル）スルフィド

DMDS: bis (2-mercaptoethyl) sulfide 3TP: trimethylolpropane tris (3-mercaptopropionate)
4TP: pentaerythritol tetrakismercaptopropionate HMDI: dicyclohexylmethane-4,4′-diisocyanate TDI: tolylene diisocyanate BIC: 1,3-bisisocyanatomethylcyclohexane D1: bis (β-epithiopropyl) sulfide prepolymer ( 1): A mixture of Plaxel 205 and Plaxel 212 (weight ratio 1: 4) and a prepolymer of dicyclohexylmethane-4,4′-diisocyanate and 2-mercaptoethanol (molar ratio 1: 2: 2)
Prepolymer (2): A mixture of Plaxel 205 and Plaxel 212 (weight ratio 1: 4), prepolymer of tolylene diisocyanate and 2-mercaptoethanol (molar ratio 1: 2: 2)
Prepolymer (3): Prepolymer of Plaxel 210, tolylene diisocyanate and 2-mercaptoethanol (molar ratio 1: 2: 2)
Prepolymer (4): Prepolymer of Plaxel 212, tolylene diisocyanate and 2-mercaptoethanol (molar ratio 1: 2: 2)
D1: Bis (β-epithiopropyl) sulfide

Claims (4)

Following (A), (B1), viewed including the four components (C) and (D),
(A) The component is in the range of 5 to 30% by weight,
(B1) component is in the range of 10 to 50% by weight,
Component (C) is in the range of 15 to 45% by weight,
(D) The thermosetting polymeric composition whose component is the range of 20-50 weight% .
(A) A compound having two or more mercapto groups, which is a compound having two mercapto groups in one molecule and a compound having three or more mercapto groups in combination (B1) All or part of the terminals A polyurethane prepolymer and / or a polythiourethane prepolymer (C) comprising a mercapto group (C) a polyisocyanate compound and / or a polyisothiocyanate compound (D) two structures represented by the following formula (1) in one molecule Compounds

(In the formula, R ¹ represents a hydrocarbon or a single bond having 1 to 10 carbon atoms, R ² , R ³ and R ⁴ each represent a hydrocarbon group or hydrogen having 1 to 10 carbon atoms. Y represents O, S, Represents Se or Te, where m = 1-5 and n = 0-5.) A method of polymerizing and curing the composition according to claim 1 to obtain an optical material. An optical material obtained by the method according to claim 2 . An optical lens made of the optical material according to claim 3 .