JP2002302549A - Polymerization regulator for episulfide compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a polymerization regulator for episulfide compounds that can facilitate control of the polymerization rate of episulfide compounds and can increase the homogeneity of the resultant polymer. SOLUTION: The compound represented by the following formula (1) (wherein R<1> , R<2> and R<3> are each a 1-10C hydrocarbon group or H; R<4> is a 1-10C hydrocarbon group or a single bond; X is F, Cl, Br, I, As, SH, OH, a 1-10C alkoxy, a 1-10C alkylthio or a 1-10C mercaptoalkylthio; m is 1-5) is used as a polymerization regulator to properly control the polymerization rate.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a plastic lens,
The present invention relates to a method for manufacturing optical materials such as a prism, an optical fiber, an information recording substrate, and a filter, and particularly to a method for manufacturing a plastic lens for spectacles.

[0002]

2. Description of the Related Art Plastic materials are widely used in various optical materials, especially for spectacle lenses in recent years, because they are lightweight, rich in toughness and easy to dye. Optical materials, especially the performance required especially for spectacle lenses, have low specific gravity, high transparency and low yellowness, high refractive index and high Abbe number as optical performance, and high refractive index reduces the thickness of lenses. Enable, and a high Abbe number reduces the chromatic aberration of the lens. The present inventors have a refractive index having a small thickness and a low chromatic aberration.
A novel episulfide compound capable of producing an optical material having a molecular weight of 7 or more and an Abbe number of 35 or more was found, and a patent application was previously filed (Japanese Patent Application Laid-Open Nos. 9-71580 and 9-11).
0979, JP-A-9-255781). In these inventions, an optical material is produced by polymerizing and curing an episulfide compound. In general, ionic polymerization is applied to polymerization. In this ionic polymerization, it is difficult to control the polymerization rate, and particularly when producing a resin for an optical material, optical distortion, striae, coloring, peeling from the mold during the polymerization are liable to occur, and the product yield is reduced. Cause.

[0003]

DISCLOSURE OF THE INVENTION The present invention has been made in view of such circumstances, and it is intended to make it easier to control the polymerization rate of an episulfide compound and to improve the uniformity of the obtained polymer. It is to provide a regulator.

[0004]

Means for Solving the Problems The present inventors have made intensive studies to solve these problems, and as a result, by using a compound represented by the following formula (1) as a polymerization regulator, I found that I could control the speed properly.

[0005]

Embedded image (Wherein, R ¹ , R ² , and R ³ each represent a hydrocarbon group having 1 to 10 carbon atoms or hydrogen, and R ⁴ represents a hydrocarbon group having 1 to 10 carbon atoms. X represents F, Cl, Br, I, As, SH,
OH, alkoxy having 1 to 10 carbons, alkylthio having 1 to 10 carbons or mercaptoalkylthio having 1 to 10 carbons is shown. m shows 1-5. That is, the first aspect of the present invention is that a compound represented by the formula (1) is preferable as a polymerization regulator of an episulfide compound. Second, in the method for producing a resin for an optical material by polymerizing an episulfide compound, the polymerization is carried out using 0.0001 to 1 part by weight of a compound represented by the formula (1) with respect to 100 parts by weight of the episulfide compound. Thereby, the polymerization rate is appropriately controlled. Here, to use 0.0001 to 1 part by weight of the compound represented by the formula (1) with respect to 100 parts by weight of the episulfide compound,
The amount of the compound represented by the formula (1) during or after the polymerization is not necessarily required to be in this range, as long as the compound is present in the reaction system in this range at the start of the polymerization reaction.

[0006]

BEST MODE FOR CARRYING OUT THE INVENTION The polymerization modifier for an episulfide compound of the present invention is a compound represented by the formula (1), and specific examples thereof are mercaptomethylthiirane, methylthiomethylthiirane, ethylthiomethylthiirane, 2-mercapto Ethylthiomethylthiirane, methoxymethylthiirane, ethoxymethylthiirane, chloromethylthiirane,
Bromomethylthiirane, iodomethylthiirane and the like can be mentioned. Preferred are mercaptomethylthiirane, methoxymethylthiirane, chloromethylthiirane, bromomethylthiirane and the like, but are not limited only to these exemplified compounds. These compounds may be used as a mixture of two or more kinds. These compounds are appropriately selected according to the type of the episulfide compound. Furthermore, the amount of these compounds used depends on the type of episulfide compound,
Although it is appropriately selected depending on the polymerization conditions, it is usually used in an amount of 0.0001 to 1 part by weight, preferably 0.001 to 0.5 part by weight, per 100 parts by weight of the episulfide compound.

The episulfide compound used in the present invention exhibits a high refractive index, a high Abbe number and a good balance between the two when used as an optical material, and the structure represented by the above formula (2) has one molecule. It has two or more inside.

The episulfide compound of the present invention having two or more structures represented by the formula (2) in one molecule includes all the organic compounds satisfying this condition, and more preferably the episulfide compound represented by the following formula (3). Compound.

Embedded image (Wherein, R ¹¹ and R ^{12 each} represent a hydrocarbon having 1 to 10 carbon atoms or a single bond, and R ^{8 to} R ¹⁰ and R ^{13 to} R ¹⁵ each represent a hydrocarbon group having 1 to 10 carbon atoms or hydrogen. .Y represents O, S, Se or Te, and p represents 1 to 5.)

Specific examples of the episulfide compound having two or more structures represented by the formula (2) in one molecule include the following. (A) Organic compound having epithio group (B) Organic compound having epithioalkyloxy group (C) Organic compound having epithioalkylthio group (D) Organic compound having epithioalkyl seleno group (E) Epithioalkyl Organic compound having telluro group The above organic compounds (A), (B), (C), (D) and (E) are chain compounds, branched compounds, aliphatic cyclic compounds, aromatic compounds, or nitrogen. , Oxygen, sulfur, selenium,
Having a main skeleton of a heterocyclic compound containing a tellurium atom, and having an epithio group, an epithioalkyloxy group, an epithioalkylthio group, an epithioalkylseleno group, and an epithioalkyltelluro group simultaneously in one molecule. It doesn't matter. Further, these compounds may contain a bond such as sulfide, selenide, telluride, ether, sulfone, ketone, ester, amide, or urethane in the molecule.

Preferred specific examples of the organic compound having an epithio group (A) include the following. Organic compound having a linear aliphatic skeleton: bis (β-epithioethyl) sulfide bis (β-epithioethyl) disulfide 1,1-bis (epithioethyl) methane 1- (epithioethyl) -1- (β-epithiopropyl) methane 1,1 -Bis (β-epithiopropyl) methane 1- (epithioethyl) -1- (β-epithiopropyl) ethane 1,1,2-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-epithiopropyl) hexane, 1- (epithioethyl) -2- (γ-epithiobutylthio) ethane, 1- (epithioethyl) -2-
[2- (γ-epithiobutylthio) ethylthio] ethane, tetrakis (β-epithiopropyl) methane,
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-epithio Propyl) -3-thiapentane, a compound having an aliphatic cyclic skeleton: 1,3 or 1,4-
Bis (epithioethyl) cyclohexane, 1,3 or 1,4-bis (β-epithiopropyl) cyclohexane, 2,5-bis (epithioethyl) -1,4-dithiane, 2,5-bis (β-epithiopropyl ) -1,4-
Compounds having one aliphatic cyclic structure such as dithiane, 4-epithioethyl-1,2-cyclohexene sulfide, 4-epoxy-1,2-cyclohexene sulfide, and 2,2-bis [4- (epithioethyl) cyclohexyl] Propane, 2,2-bis [4- (β-epithiopropyl) cyclohexyl] propane, bis [4- (epithioethyl) cyclohexyl] methane, bis [4- (β
Compounds having two aliphatic cyclic structures, such as -epithiopropyl) cyclohexyl] methane, bis [4- (β-epithiopropyl) cyclohexyl] sulfide, and bis [4- (epithioethyl) cyclohexyl] sulfide. Compounds having an aromatic skeleton: compounds having one aromatic skeleton such as 1,3 or 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′-bis (epithioethyl) biphenyl,
4,4′-bis (β-epithiopropyl) biphenyl,
Having two aromatic skeletons. Further, compounds in which at least one hydrogen of the epithio group of these compounds is substituted with a methyl group are also exemplified.

Preferred specific examples of the organic compound having an epithioalkyloxy group (B) include the following. Organic compound having a linear aliphatic skeleton: bis (β-epithiopropyloxy) ether bis (β-epithiopropyloxy) methane, 1,2-
Bis (β-epithiopropyloxy) ethane, 1,3-
Bis (β-epithiopropyloxy) propane, 1,2
-Bis (β-epithiopropyloxy) 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-
chain organic compounds such as β-epithiopropyloxyethyl) oxyethyl] oxy] ethane and the like; tetrakis (β-epithiopropyloxymethyl) methane;
1,1-tris (β-epithiopropyloxymethyl)
Propane, 1,5-bis (β-epithiopropyloxy) -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-tris (β-epithiopropyloxy) -4- (β-epithiopropyloxymethyl) -3-thiahexane, 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-epithiopropyloxy) -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-dithiaoctane, 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-epithiopropyloxyethyl) oxymethyl] -3,6,9-trithiaundecane, 1,1
1-bis (β-epithiopropyloxy) -4,7-bis (β-epithiopropyloxymethyl) -3,6,9
Compounds having an aliphatic cyclic skeleton, such as -trithiaundecane: 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-epithiopropyl) Oxy) cyclohexyl] propane, bis [4- (β-epithiopropyloxy) cyclohexyl] sulfide, 2,5-bis (β-
Epithiopropyloxymethyl) -1,4-dithiane,
Compounds having an aromatic skeleton such as 2,5-bis (β-epithiopropyloxyethyloxymethyl) -1,4-dithiane: 1, 3 or 1,4-bis (β-epithiopropyloxy) benzene, 1,3 or 1,4-bis (β-epithiopropyloxymethyl)
A compound having one aromatic skeleton such as benzene, bis [4- (β-epithiopropyloxy) phenyl] methane, 2,2-bis [4- (β-epithiopropyloxy) phenyl] propane, Bis [4- (β-epithiopropyloxy) phenyl] sulfide, bis [4- (β
-Epithiopropyloxy) phenyl] sulfone,
Compounds having two aromatic skeletons, such as 4,4'-bis (β-epithiopropyloxy) biphenyl. Moreover,
Compounds in which at least one hydrogen of the epithio group of these compounds is substituted with a methyl group are also examples.

Preferred examples of the organic compound having an epithioalkylthio group (C) include an epoxyalkylthio group (specifically, a β-epoxypropylthio group) of an epoxy compound derived from a compound having a mercapto group and epihalohydrin. ) Is substituted by an epithioalkylthio group. If a more specific example method is used, the following can be given as typical examples. Organic compounds having a linear aliphatic skeleton: bis (β-epithiopropyl) sulfide, bis (β-epithiopropyl) disulfide bis (β-epithiopropylthio) methane, 1,2-bis (β-epithio) Propylthio) ethane, 1,3-bis (β-epithiopropylthio) propane, 1,2-bis (β-epithiopropylthio) propane, 1- (β-epithiopropylthio) -2- (β -Epithiopropylthiomethyl) propane, 1,2,3-tris (β-epithiopropylthio) propane, 1,4-bis (β-epithiopropylthio) butane, 1,3-bis (β-epi Thiopropylthio) butane, 1- (β-epithiopropylthio) -3- (β-epithiopropylthiomethyl) butane, 1,5-bis (β-epithiopropylthio) pentane, 1- (β- Epithiopropylthio) -4- (β-epithiopropylthiomethyl) pentane, 1,5-bis (β-epithiopropylthio) -2- (β-epithiopropylthiomethyl) -3-thiapentane, , 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-epithiopropylthiomethyl) -3-thiapentane, 1,5-bis (β-epithiopropylthio ) -2,4-Bis (β-epithiopropylthiomethyl) -3-thiapentane, 1-
(Β-epithiopropylthio) -2,2-bis (β-epithiopropylthiomethyl) -4-thiahexane, 1,
5,6-tris (β-epithiopropylthio) -4-
(Β-epithiopropylthiomethyl) -3-thiahexane, 1,8-bis (β-epithiopropylthio) -4-
(Β-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropylthio)
-4,5 bis (β-epithiopropylthiomethyl)-
3,6-dithiaoctane, 1,8-bis (β-epithiopropylthio) -4,4-bis (β-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (β-epi Thiopropylthio) -2,4,5-tris (β-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropylthio)
-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, 1,11
-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-epithiopropylthiomethyl)-
A chain compound having an ester group and an epithioalkylthio group such as 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, etc. Compounds having an aliphatic cyclic skeleton: 1,3 or 1,4-
Bis (β-epithiopropylthio) cyclohexane,
1,3 or 1,4-bis (β-epithiopropylthiomethyl) cyclohexane 2,5-bis (β-epithiopropylthiomethyl) -1,4-dithiane, 2,5-bis (β-epithio Propylthioethylthiomethyl) -1,
Aliphatics such as 4-dithia 2,5-bis (β-epithiopropylthiomethyl) -1,4-dithiane and 2,5-bis (β-epithiopropylthioethylthiomethyl) -1,4-dithia Compounds having one cyclic skeleton, bis [4-
(Β-epithiopropylthio) cyclohexyl] methane, 2,2-bis [4- (β-epithiopropylthio)
Compounds having two aliphatic cyclic skeletons such as cyclohexyl] propane and bis [4- (β-epithiopropylthio) cyclohexyl] sulfide. Compounds having an aromatic skeleton: aromatics such as 1,3 or 1,4-bis (β-epithiopropylthio) benzene and 1,3 or 1,4-bis (β-epithiopropylthiomethyl) benzene Compounds having one skeleton or 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] Compounds having two aromatic skeletons, such as sulfone and 4,4′-bis (β-epithiopropylthio) biphenyl. Furthermore, compounds in which at least one hydrogen of the β-epithiopropyl group of these compounds is substituted with a methyl group are also specific examples.

(D) Preferred specific examples of the organic compound having an epithioalkylseleno group include selenium compounds such as metal selenium, alkali metal selenide, alkali metal selenol, alkyl (aryl) selenol, hydrogen selenide and epihalohydrin. A typical example is a compound in which one or more epoxyalkylseleno groups (specifically, β-epoxypropylseleno groups) of an epoxy compound are substituted with epithioalkylseleno groups.
If a more specific example method is used, the following can be given as typical examples. Organic compounds having a linear aliphatic skeleton: 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, 1,2,3
-Tris (β-epithiopropylseleno) propane,
1,4-bis (β-epithiopropylseleno) butane,
1,3-bis (β-epithiopropylseleno) butane,
1- (β-epithiopropylseleno) -3- (β-epithiopropylselenomethyl) butane, 1,5-bis (β
-Epithiopropylseleno) pentane, 1- (β-epithiopropylseleno) -4- (β-epithiopropylselenomethyl) pentane, 1,5-bis (β-epithiopropylseleno) -2- (β -Epithiopropylselenomethyl) -3-thiapentane, 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-epithiopropylselenoethyl)
Selenoethyl] thio] ethane, tetrakis (β-epithiopropylselenomethyl) methane, 1,1,1-tris (β-epithiopropylselenomethyl) propane, 1,
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-epithiopropylseleno)-
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, 1,9-bis (β-epithiopropylselenomethyl) -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-epithiopropylseleno) -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-epithiopropylselenomethyl) 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) butane, tris (4,5-thioepoxy-2-selenopentyl) -3-selena- 6-thiaoctane-1,
8-bis (3,4-thioepoxy-1-selenobutyl), bis (5,6-epithio-3-selenohexyl)
Telluride, 2,3-bis (6,7-thioepoxy-1-
Tellurium-4-selenoheptyl) -1- (3,4-thioepoxy-1-selenobutyl) propane, 1,1,3,3
3, -tetrakis (4,5-thioepoxy-2-selenopentyl) -2-tellurapropane, bis (4,5-thioepoxy-2-selenopentyl) -3,6,9-tritereoundoundane-1,11- Bis (3,4-thioepoxy-1-selenobutyl), 1,4-bis (3,4-thioepoxy-1-selenobutyl) -2,3-bis (6,7
-Thioepoxy-1-tellura-4-selenoheptyl) butane, tris (4,5-thioepoxy-2-selenopentyl) -3-tellura-6-thiaoctane-1,8-bis (3,4-thioepoxy-1-) Compounds having an aliphatic cyclic skeleton such as (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-epithiopropylselenomethyl) -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,
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-diselenolan, (2,4 or 4,5) -bis (4,5-epithio-2-selenopentyl) -1,3-
Diselenolan, (2,4 or 2,5 or 4,5)-
Bis (3,4-epithio-1-selenobutyl) -1-thia-3-selenolan, (2,4 or 2,5 or 4,
5) -Bis (4,5-epithio-2-selenopentyl)
-1-thia-3-selenolan, 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) selenophane, (2,3
Or 2,4 or 2,5 or 3,4) -bis (4,
5-epithio-2-selenopentyl) selenophane, 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-ditelluran,
(2,3 or 2,5 or 2,6) -bis (4,5-
Epithio-2-selenopentyl) -1,4-ditelluran, (2,4 or 2,5 or 5,6) -bis (3,
4-epithio-1-selenobutyl) -1,3-ditelluran, (2,4 or 2,5 or 5,6) -bis (4
5-epithio-2-selenopentyl) -1,3-ditelluran, (2,3 or 2,5 or 2,6 or 3,
5) -Bis (3,4-epithio-1-selenobutyl)-
1-thia-4-telluran, (2,3 or 2,5 or 2,6 or 3,5) -bis (4,5-epithio-2-
Selenopentyl) -1-thia-4-telluran, (2,4
Or 4,5) -bis (3,4-epithio-1-selenobutyl) -1,3-ditellolane, (2,4 or 4,
5) -Bis (4,5-epithio-2-selenopentyl)
-1,3-ditellolane, (2,4 or 2,5 or 4,5) -bis (3,4-epithio-1-selenobutyl) -1-thia-3-tellurolan, (2,4 or 2,
5 or 4,5) -bis (4,5-epithio-2-selenopentyl) -1-thia-3-tellurolan, 2,6-bis (4,5-epithio-2-selenopentyl-1,3,3)
5-tritellurane, bis (3,4-epithio-1-selenobutyl) tricyclotelluraoctane, bis (3,4-
Epithio-1-selenobutyl) dicyclotelluranonane,
(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-selenopentyl) tellurophan, 2- (4,5-thioepoxy-2-selenopentyl) -5- (3,4-thioepoxy-1-selenobutyl) -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-selenobutyl) -1-telluracyclohexane,
(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-telluracyclohexane and the like Compound having group skeleton: (1,3 or 1,4)-
Bis (β-epithiopropylseleno) benzene, (1,
3 or 1,4) -bis (β-epithiopropylselenomethyl) benzene, bis [4- (β-epithiopropylseleno) phenyl] methane, 2,2-bis [4- (β-
Epithiopropylseleno) phenyl] propane, bis [4- (β-epithiopropylseleno) phenyl] sulfide, bis [4- (β-epithiopropylseleno) phenyl] sulfone, 4,4′-bis (β- Further, specific examples thereof include compounds in which at least one hydrogen of the β-epithiopropyl group of these compounds is substituted with a methyl group.

Preferred examples of the (E) organic compound having an epithioalkyltelluro group include a tellurium compound such as metal tellurium, alkali metal telluride, alkali metal tellurol, alkyl (aryl) tellurol, hydrogen telluride and epihalohydrin. A typical example is a compound in which one or more epoxyalkyltelluro groups (specifically, β-epoxypropyltelluro group) of an epoxy compound are substituted with epithioalkyltelluro groups.
If a more specific example method is used, the following can be given as typical examples. Organic compounds having a linear aliphatic skeleton: bis (β-epithiopropyl) telluride, bis (β-epithiopropyl)
Ditelluride, bis (β-epithiopropyl) tritelluride, 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-
Epithiopropyl telluromethyl) propane, 1, 2, 3
-Tris (β-epithiopropyltelluro) propane,
1,4-bis (β-epithiopropyltelluro) butane,
1,3-bis (β-epithiopropyltelluro) butane,
1- (β-epithiopropyltelluro) -3- (β-epithiopropyltelluromethyl) butane, 1,5-bis (β
-Epithiopropyltelluro) pentane, 1- (β-epithiopropyltelluro) -4- (β-epithiopropyltelluromethyl) pentane, 1,5-bis (β-epithiopropyltelluro) -2- (β -Epithiopropyltelluromethyl) -3-thiapentane, 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-epithiopropyltelluromethyl) methane, 1,1,1-tris (β-epithiopropyltelluromethyl) propane,
5-bis (β-epithiopropyltelluro) -2- (β-
Epithiopropyl telluromethyl) -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-epithiopropyltelluromethyl) -3-thiahexane, 1,8-bis (β-epithiopropyltelluro)- 4- (β-epithiopropyltelluromethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropyltelluromethyl) -4,5bis (β-epithiopropyltelluromethyl) -3,6- Dithiaoctane, 1,8-bis (β-epithiopropyltelluro)-
4,4-bis (β-epithiopropyltelluromethyl)-
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-epithiopropyltelluromethyl) -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-epithiopropyltelluromethyl) -3,6,9-trithiaundecane, 1,11 -Bis (β-epithiopropyltelluro)
-5,7-bis (β-epithiopropyltelluromethyl)
-3,6,9-trithiaundecane, 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-tellurohexyl) selenide, 2,3-bis (6,7-thioepoxy-1-selena-4-telluroheptyl) -1 − (3,4
-Thioepoxy-1-tellurobutyl) propane, 1,
1,3,3-tetrakis (4,5-thioepoxy-2
-Telluropentyl) -2-selenapropane, bis (4,
5-thioepoxy-2-tellulopentyl) -3,6,9
-Triselenaundecane-1,11-bis (3,4-thioepoxy-1-tellurobutyl), 1,4-bis (3,
4-thioepoxy-1-tellurobutyl) -2,3-bis (6,7-thioepoxy-1-selena-4-telluroheptyl) butane, tris (4,5-thioepoxy-2-telluropentyl) -3-selena-6 Thiaoctane-1,
8-bis (3,4-thioepoxy-1-tellurobutyl), bis (5,6-epithio-3-tellurohexyl)
Telluride, 2,3-bis (6,7-thioepoxy-1-
Tellurium-4-telluroheptyl) -1- (3,4-thioepoxy-1-tellurobutyl) propane, 1,1,3,
3, -tetrakis (4,5-thioepoxy-2-tellulopentyl) -2-tellurapropane, bis (4,5-thioepoxy-2-telluropentyl) -3,6,9-tritereoundecan-1,1,11-bis ( 3,4-thioepoxy-1-tellurobutyl), 1,4-bis (3,4-thioepoxy-1-tellurobutyl) -2,3-bis (6,7
-Thioepoxy-1-tellura-4-telluroheptyl) butane, tris (4,5-thioepoxy-2-tellulopentyl) -3-tellura-6-thiaoctane-1,8-bis (3,4-thioepoxy-1-tellurobutyl) Compounds having an aliphatic cyclic skeleton: (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-tellurobutyl) -1,4-diselenane, (2,3 or 2,5 or 2,6) -bis (4,5-epithio-
(2-telluropentyl) -1,4-diselenane, (2,4
Or 2,5 or 5,6) -bis (3,4-epithio-1-tellurobutyl) -1,3-diselenane, (2,4
Or 2,5 or 5,6) -bis (4,5-epithio-2-telluropentyl) -1,3-diselenane,
3 or 2,5 or 2,6 or 3,5) -bis (3,4-epithio-1-tellurobutyl) -1-thia-
4-selenane, (2,3 or 2,5 or 2,6 or 3,5) -bis (4,5-epithio-2-tellulopentyl) -1-thia-4-selenane, (2,4 or 4,
5) -Bis (3,4-epithio-1-tellurobutyl)-
1,3-diselenolane, (2,4 or 4,5) -bis (4,5-epithio-2-telluropentyl) -1,3-
Diselenolan, (2,4 or 2,5 or 4,5)-
Bis (3,4-epithio-1-tellurobutyl) -1-thia-3-selenolan, (2,4 or 2,5 or 4,
5) -Bis (4,5-epithio-2-telluropentyl)
-1-thia-3-selenolan, 2,6-bis (4,5-
Epithio-2-telluropentyl-1,3,5-triselenane, bis (3,4-epithio-1-tellurobutyl) tricycloselenaoctane, bis (3,4-epithio-1
-Tellurobutyl) dicycloselennananan, (2,3 or 2,4 or 2,5 or 3,4) -bis (3,4-
Epithio-1-tellurobutyl) selenophane, (2,3
Or 2,4 or 2,5 or 3,4) -bis (4,
5-epithio-2-telluropentyl) selenophane, 2
-(4,5-thioepoxy-2-telluropentyl) -5
-(3,4-thioepoxy-1-tellurobutyl) -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-tellurobutyl) -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-telluropentyl) -1-selenacyclohexane,
(2,3 or 2,5 or 2,6) -bis (3,4-
Epithio-1-tellurobutyl) -1,4-ditellurane,
(2,3 or 2,5 or 2,6) -bis (4,5-
Epithio-2-telluropentyl) -1,4-ditelluran, (2,4 or 2,5 or 5,6) -bis (3,
4-epithio-1-tellurobutyl) -1,3-ditelluran, (2,4 or 2,5 or 5,6) -bis (4
5-epithio-2-telluropentyl) -1,3-ditellurane, (2,3 or 2,5 or 2,6 or 3,
5) -Bis (3,4-epithio-1-tellurobutyl)-
1-thia-4-telluran, (2,3 or 2,5 or 2,6 or 3,5) -bis (4,5-epithio-2-
Telluropentyl) -1-thia-4-telluran, (2,4
Or 4,5) -bis (3,4-epithio-1-tellurobutyl) -1,3-ditellolane, (2,4 or 4,
5) -Bis (4,5-epithio-2-telluropentyl)
-1,3-ditellolane, (2,4 or 2,5 or 4,5) -bis (3,4-epithio-1-tellurobutyl) -1-thia-3-tellurolan, (2,4 or 2,
5 or 4,5) -bis (4,5-epithio-2-telluropentyl) -1-thia-3-tellurolan, 2,6-bis (4,5-epithio-2-tellulopentyl-1,3,3)
5-tritellurane, bis (3,4-epithio-1-tellurobutyl) tricyclotelluraoctane, bis (3,4-
Epithio-1-tellurobutyl) dicyclotelluranonane,
(2,3 or 2,4 or 2,5 or 3,4) -bis (3,4-epithio-1-tellurobutyl) tellurophan, (2,3 or 2,4 or 2,5 or 3,4)
-Bis (4,5-epithio-2-tellulopentyl) tellurophan, 2- (4,5-thioepoxy-2-tellulopentyl) -5- (3,4-thioepoxy-1-tellurobutyl) -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-tellurobutyl) -1-telluracyclohexane,
(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-telluracyclohexane Compound having a skeleton: (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] propane, bis [4- (β-epithiopropyltelluro) phenyl] sulfide, bis [4- (β-epithiopropyltelluro) phenyl] sulfone, 4,4′-bis (β- Further, specific examples thereof include compounds in which at least one hydrogen of the β-epithiopropyl group of these compounds is substituted with a methyl group.

Further, organic compounds having an unsaturated group are also included in the above (A) to (E). Preferred specific examples thereof include vinylphenylthioglycidyl ether, vinylbenzylthioglycidyl ether, thioglycidyl methacrylate, thioglycidyl acrylate, allylthioglycidyl ether and the like.

The polymerization catalyst used for producing an optical material in the present invention includes amines, phosphines, and quaternary amines.
Quaternary ammonium salts, quaternary phosphonium salts, tertiary sulfonium salts, secondary iodonium salts, mineral acids,
Lewis acids, organic acids, silicic acids, tetrafluoroboric acids and the like can be mentioned. Specific examples include (1) ethylamine, n-propylamine, sec-propylamine, n-butylamine, sec-butylamine, i-butylamine, tert-butylamine, pentylamine, hexylamine, heptylamine, octylamine, decylamine, Laurylamine, mystyrylamine, 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, aminocyclopentane, aminocyclohexane, aminonorbornene, aminomethylcyclohexane, aminobenzene, benzylamine, phenethylamine, α-phenylethylamine, naphthylamine, furfurylamine, etc. Primary amines: 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'-dimethylpropane,
Aminoethylethanolamine, 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, hydrogenated 4,4'-diaminodiphenylmethane, 2- or 4-aminopiperidine, 2- or 4-aminomethylpiperidine, 2- or 4-aminoethylpiperidine, 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′-diaminodiphenyl sulfone, 4,4′-diaminoditolyl sulfone, methylenebis (o-chloroaniline), 3,9-bis (3-aminopropyl) 2
4,8,10-tetraoxaspiro [5,5] undecane, diethylenetriamine, iminobispropylamine, methyliminobispropylamine, bis (hexamethylene) triamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, N −
Aminoethylpiperazine, N-aminopropylpiperazine, 1,4-bis (aminoethylpiperazine), 1,4
Primary polyamines such as -bis (aminopropylpiperazine), 2,6-diaminopyridine, bis (3,4-diaminophenyl) sulfone; diethylamine, dipropylamine, di-n-butylamine, di-sec-butylamine, diisobutyl Amines, di-n-pentylamine, di-3-pentylamine, dihexylamine, octylamine, di (2-ethylhexyl) amine, methylhexylamine, diallylamine, pyrrolidine, piperidine,
2-, 3-, 4-picoline, 2,4-, 2,6-, 3,
Secondary amines such as 5-lupetidine, diphenylamine, N-methylaniline, N-ethylaniline, dibenzylamine, methylbenzylamine, dinaphthylamine, pyrrole, indoline, indole, and morpholine; 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-methylpiperazine, 2,5- or 2,6-dimethylpiperazine, homopiperazine, 1,1
-Di- (4-piperidyl) methane, 1,2-di- (4-
Piperidyl) ethane, 1,3-di- (4-piperidyl)
Secondary polyamines such as propane, 1,4-di- (4-piperidyl) butane, tetramethylguanidine; trimethylamine, triethylamine, tri-n-propylamine, tri-iso-propylamine, tri-1,2-dimethylpropyl Amine, 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, N-diethylcyclohexylamine, N-methyldicyclohexylamine, N, N-diethylethanolamine, N, N-dimethylethanolamine, N-ethyldiethanolamine, triethanolamine, tribenzylamine, N, N-dimethylbenzylamine , Diethylbenzylamine, triphenylamine, N, N-dimethylamino-p-cresol, N, N-dimethylaminomethylphenol, 2- (N, N-dimethylaminomethyl) phenol, N, N-dimethylaniline, N , N-
Tertiary amines such as diethylaniline, pyridine, quinoline, N-methylmorpholine, N-methylpiperidine, 2- (2-dimethylaminoethoxy) -4-methyl-1,3,2-dioxabornane; tetramethylethylenediamine, pyrazine, N, N'-dimethylpiperazine, N,
N'-bis ((2-hydroxy) propyl) piperazine, hexamethylenetetramine, N, N, N ', N'-
Tetramethyl-1,3-butanamine, 2-dimethylamino-2-hydroxypropane, diethylaminoethanol, N, N, N-tris (3-dimethylaminopropyl) amine, 2,4,6-tris (N, N- Tertiary polyamines such as dimethylaminomethyl) phenol and 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- methyl imidazole, 2-mercaptobenzimidazole, 3-mercapto-4-methyl-4H-1,2,4-triazole,
5-mercapto-1-methyl-tetrazole, 2,5-
Dimercapto-1,3,4-thiadiazole, 1-benzyl-2-methylimidazole, N- (2'-cyanoethyl) -2-methylimidazole, N- (2'-cyanoethyl) -2-undecylimidazole, N- (2'-
Cyanoethyl) -2-phenylimidazole, 3,3-
Various imidazoles such as bis- (2-ethyl-4-methylimidazolyl) methane, an adduct of alkylimidazole and isocyanuric acid, and a condensate of alkylimidazole and formaldehyde; 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
And the like; amine compounds represented by the above. (2) A complex of the amines of (1) with borane and boron trifluoride. (3) trimethylphosphine, triethylphosphine, tri-iso-propylphosphine, tri-n-
Butylphosphine, tri-n-hexylphosphine, tri-n-octylphosphine, tricyclohexylphosphine, triphenylphosphine, tribenzylphosphine, tris (2-methylphenyl) phosphine, tris (3-methylphenyl) phosphine , Tris (4-methylphenyl) phosphine, tris (diethylamino) phosphine, tris (4-methylphenyl)
Phosphines such as phosphine, dimethylphenylphosphine, diethylphenylphosphine, dicyclohexylphenylphosphine, ethyldiphenylphosphine, diphenylcyclohexylphosphine, and chlorodiphenylphosphine; (4) 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 hydrogensulfite, tetra-n-butylammonium tetrafluoroborate, tetra-n-butylammonium tetraphenylborate, tetra-n-butylammonium paratoluenesulfonate, tetra-n-hexylammonium chloride, tetra-n -Hexyl ammonium bromide, tetra-n-hexylammonium acetate,
Tetra-n-octylammonium chloride, tetra-n-octylammonium bromide, tetra-n-
Octyl ammonium acetate, trimethyl-n-octyl ammonium chloride, trimethyl benzyl ammonium chloride, trimethyl benzyl ammonium bromide, triethyl-n-octyl ammonium chloride, triethyl benzyl ammonium chloride, triethyl benzyl ammonium bromide, tri-n-butyl-n-octyl ammonium Chloride,
Tri-n-butylbenzylammonium fluoride,
Tri-n-butylbenzylammonium chloride, tri-n-butylbenzylammonium bromide, tri-n-butylbenzylammonium iodide, methyltriphenylammonium chloride, methyltriphenylammonium bromide, ethyltriphenylammonium chloride, ethyltriphenylammonium Bromide, n-butyltriphenylammonium chloride, n-butyltriphenylammonium bromide, 1-methylpyridinium bromide, 1-ethylpyridinium bromide, 1-n-butylpyridinium bromide, 1-n-hexylpyridinium bromide,
1-n-octylpyridinium bromide, 1-n-dodecylpyridinium bromide, 1-n-phenylpyridinium bromide, 1-methylpicolinium bromide, 1-ethylpicolinium bromide, 1-n-butylpicolinium bromide, 1-n -Hexylpicolinium bromide, 1-n-octylpicolinium bromide, 1-n-dodecylpicolinium bromide, 1-
quaternary ammonium salts such as n-phenylpicolinium bromide; (5) 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-butyltriphenylphosphonium iodide, n-hexyltriphenylphosphonium bromide, n-octyltriphenylphosphonium bromide, tetraphenylphosphonium bromide, tetrakishydroxymethylphosphonium chloride , Tetrakishydroxymethylphosphonium bromide, tetrakis Hydroxyethyl phosphonium chloride, phosphonium salts such as tetrakis hydroxybutyl phosphonium chloride. (6) trimethylsulfonium bromide, triethylsulfonium bromide, tri-n-butylsulfonium chloride, tri-n-butylsulfonium bromide, tri-n-butylsulfonium iodide, tri-
n-butylsulfonium tetrafluoroborate, tri-n-hexylsulfonium bromide, tri-n-
Sulfonium salts such as octylsulfonium bromide, triphenylsulfonium chloride, triphenylsulfonium bromide, and triphenylsulfonium iodide. (7) Iodonium salts such as diphenyliodonium chloride, diphenyliodonium bromide, and diphenyliodonium iodide. (8) Mineral acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, and carbonic acid and half esters thereof. (9) Lewis acids represented by boron trifluoride etherate of boron trifluoride. (10) Organic acids and their half esters. (11) Silicic acid, tetrafluoroboric acid. And so on. Of these, quaternary ammonium salts, quaternary phosphonium salts, tertiary sulfonium salts and secondary iodonium salts are preferred. More preferred are quaternary ammonium salts and quaternary phosphonium salts. These may be used alone or as a mixture of two or more.

The amount of the polymerization catalyst used is 0.001 to 3.0 with respect to 100 parts by weight of the episulfide compound.
Parts by weight, preferably 0.005 to 2.0 parts by weight.

In order to impart good oxidation resistance to the cured material, phenols and compounds having at least one SH group may be used alone or in combination with known antioxidants as antioxidants. It is possible. The phenols referred to here include phenol, cresol, catechol, resorcin, and the like, and the compound having one or more SH groups include:
Mercaptans and thiophenols, as well as mercaptans and thiophenols having unsaturated groups such as vinyl, aromatic vinyl, methacrylic, acryl, and allyl are exemplified. Specific examples thereof include those described in JP-A-9-255781.

It is also possible to use a compound having at least one active hydrogen other than the SH group for the purpose of improving the performance such as dyeability and strength. The term "active hydrogen" used herein means, for example, hydrogen of a hydroxyl group, a carboxyl group, an amide group, and 1,2-diketone, 1,3-dicarboxylic acid and its ester, and 3-ketocarboxylic acid and its ester.
Compounds having at least one active hydrogen per molecule include alcohols, phenols, mercapto alcohols, hydroxythiophenols, carboxylic acids, mercaptocarboxylic acids, hydroxycarboxylic acids, amides, and the like. , 3-diketones, 1,3-dicarboxylic acids and esters thereof, 3-ketocarboxylic acids and esters thereof, and alcohols having unsaturated groups such as vinyl, aromatic vinyl, methacryl, acryl, and allyl, and phenol , Mercapto alcohols, hydroxythiophenols, carboxylic acids, mercaptocarboxylic acids, hydroxycarboxylic acids, amides,
Examples thereof include 1,3-diketones, 1,3-dicarboxylic acid and esters thereof, and 3-ketocarboxylic acid and esters thereof. As a specific example, see Japanese Patent Application Laid-Open No. 9-2557.
No. 81 publication.

Further, it is also possible to use a compound having one or more isocyanate groups for the purpose of improving the strength. Specific examples of the compound having one or more isocyanate groups include those described in Japanese Patent Application No. 10-028481.

In the method for producing a high refractive index resin of the present invention, it is of course possible to further improve the practicality of the obtained resin by adding known additives such as an antioxidant and an ultraviolet absorber. Further, when producing an optical material comprising the high refractive index resin of the present invention, there is a tendency that the optical material is easily peeled off from a mold during polymerization, and a known external and / or internal adhesion improving agent is used or added as necessary. It is also effective to improve the adhesion between the obtained optical material and the mold.

The method for producing a high refractive index resin according to the present invention comprises an episulfide compound as a raw material, the above-mentioned catalyst, and, if necessary, an adhesion improver, an ultraviolet absorber, a radical polymerization initiator, and various performance improvers. After the additives are mixed and made uniform, the mixture is poured into a glass or metal mold, the polymerization and curing reaction is advanced by heating, and then the mold is removed from the mold.

Prior to casting, a part or all of the episulfide compound is preliminarily polymerized in the presence or absence of a catalyst, with stirring or without stirring at -100 to 160 ° C. for 0.1 to 72 hours. After that, the composition can be prepared and cast. The preliminary polymerization conditions are preferably at -10 to 100C for 1 to 48 hours, more preferably 0 to 100 hours.
Performed at ６０60 ° C. for 1-48 hours.

The method for producing the resin for an optical material of the present invention will be described in more detail below. As described above, the main raw material and the auxiliary raw material are mixed and then injected and cured into a mold. The episulfide compound, the catalyst and the polymerization modifier of the present invention are optionally combined with an adhesion improver, a stabilizer, and a radical polymerization initiator. The agents and the like may all be mixed in the same container under stirring at the same time, each raw material may be added and mixed stepwise, or several components may be separately mixed and then mixed again in the same container.
The respective raw materials and the auxiliary raw materials may be mixed in any order. Upon mixing, the set temperature, the time required for the mixing, and the like may be basically set as long as the components are sufficiently mixed, but an excessive temperature and time may cause an undesired reaction between the raw materials and additives, Further, it is not appropriate, for example, because the viscosity increases and the casting operation becomes difficult. The mixing temperature should be in the range of about -50 ° C to 100 ° C, the preferred temperature range is -30 ° C to 50 ° C, more preferably,
-5 ° C to 30 ° C. The mixing time is 1 minute to 5 hours, preferably 5 minutes to 2 hours, more preferably 5 minutes to 30 minutes, and most preferably about 5 minutes to 15 minutes. Performing a degassing operation under reduced pressure before, during or after mixing of the raw materials and additives is a preferable method from the viewpoint of preventing the formation of bubbles during the subsequent medium-sized polymerization curing.
At this time, the degree of pressure reduction is from about 0.1 mmHg to 700 mmHg, preferably from 10 mmHg to 300 mmHg.
Hg. Further, it is preferable to purify the mixture or the main and auxiliary raw materials before mixing with a filter having a pore size of about 0.05 to 3 μm by filtering impurities and the like from the viewpoint of further improving the quality of the optical material of the present invention. . After pouring into a glass or metal mold, polymerization curing is performed using an electric furnace or the like. The curing time is 0.1 to 100 hours, usually 1 to 48 hours, and the curing temperature is -10 to 160 ° C, usually -10. ~ 1
40 ° C. The polymerization is held at a predetermined polymerization temperature for a predetermined time, the temperature is raised from 0.1 ° C to 100 ° C / h, and 0.1 ° C to 10 ° C.
It can be carried out at a temperature of 0 ° C./h or a combination thereof. Also, after the curing is completed, annealing the material at a temperature of 50 to 150 ° C. for about 10 minutes to 5 hours,
This is a preferable treatment for removing the distortion of the optical material of the present invention. Further, if necessary, a surface treatment such as dyeing, hard coating, anti-reflection and anti-fogging property can be performed.

[0025]

According to the present invention, the polymerization of an episulfide compound can be appropriately controlled by using the compound represented by the formula (1) as a polymerization regulator for an episulfide compound.

[0026]

EXAMPLES The present invention will now be described specifically with reference to examples, but the present invention is not limited to these examples. The evaluation criteria for optical distortion, striae, and peeling from the mold during polymerization are as follows. ：: yield of 95% or more (good) ：: yield of 90% or more and less than 95% (good) ×: yield of less than 90% (bad) The evaluation criteria for visual coloring are as follows. ：: colorless and transparent (good) ：: slightly yellow (good) ×: clearly yellow (poor)

Example 1 4000 g of bis (β-epithiopropyl) sulfide,
20 g of N, N-diethylethanolamine as a catalyst,
32 g of mercaptomethylthiirane was mixed as a polymerization regulator, and the mixture was separately poured into 100 sets of molds for -6D lenses composed of two glass plates. Subsequently, the temperature was raised from 20 ° C. to 120 ° C. in an oven over 20 hours to polymerize and cure. Table 1 shows the optical distortion, striae, coloring and peeling of the obtained lens. Optical distortion, striae, coloring and peeling were all good.

Example 2 4000 g of bis (β-epithiopropyl) sulfide,
20 g of N, N-diethylethanol as a catalyst and 0.02 g of mercaptomethylthiirane as a polymerization regulator were mixed, and thereafter the same operation as in Example 1 was performed. Optical distortion,
Striae, coloring and peeling were all good.

EXAMPLE 3 4000 g of bis (β-epithiopropyl) sulfide,
20 g of N, N-diethylethanolamine as a catalyst,
8 g of mercaptomethylthiirane was mixed as a polymerization regulator, and thereafter the same operation as in Example 1 was performed. Optical distortion,
Striae, coloring and peeling were all good.

Example 4 4000 g of bis (β-epithiopropyl) sulfide,
20 g of N, N-diethylethanolamine as a catalyst,
16 g of methoxymethylthiirane was mixed as a polymerization regulator, and thereafter the same operation as in Example 1 was performed. Optical distortion,
Striae, coloring and peeling were all good.

Example 5 4000 g of bis (β-epithiopropyl) sulfide,
20 g of N, N-diethylethanolamine as a catalyst,
0.4 g of chloromethylthiirane was mixed as a polymerization regulator, and thereafter the same operation as in Example 1 was performed. Optical distortion,
Striae, coloring and peeling were all good.

Comparative Example 1 The same operation as in Example 1 was performed except that no polymerization regulator was used. Optical distortion, striae, coloring and peeling were all poor.

Example 6 4000 g of bis (β-epithiopropyl) sulfide
4 g of tetra-n-butylphosphonium bromide as a catalyst, 0.4 g of chloromethylthiirane as a polymerization regulator
Were mixed, and thereafter the same operation as in Example 1 was performed. Optical distortion, striae, coloring and peeling were all good.

Comparative Example 2 The same operation as in Example 5 was performed except that no polymerization regulator was used. Optical distortion, striae, coloring and peeling were all poor.

Example 7 1,2-Bis (β-epithiopropylthio) ethane 40
00g, N, N-diethylethanolamine 20g as a catalyst, mercaptomethylthiirane 6 as a polymerization regulator
g, and then the same operation as in Example 1 was performed. Optical distortion, striae, coloring and peeling were all good.

Comparative Example 3 The same operation as in Example 6 was performed except that no polymerization regulator was used. Optical distortion, striae, coloring and peeling were all poor.

Example 8 1- (β-epithiopropylthio) -2- [2-β-epithiopropylthioethylthio] ethane 4000 g, N, N-diethylethanolamine 20 g as a catalyst, methoxy as a polymerization regulator Mix 4g of methylthiirane,
Thereafter, the same operation as in Example 1 was performed. Optical distortion, striae, coloring and peeling were all good.

Comparative Example 4 The same operation as in Example 7 was performed except that no polymerization regulator was used. Optical distortion, striae, coloring and peeling were all poor.

Example 9 2,5-bis (β-epithiopropylthiomethyl)-
4000 g of 1,4-dithiane, 30 g of N, N-diethylethanolamine as a catalyst, and 0.8 g of chloromethylthiirane as a polymerization regulator were mixed, and thereafter the same operation as in Example 1 was performed. Optical distortion, striae, coloring and peeling were all good.

Comparative Example 5 The same operation as in Example 8 was performed except that no polymerization regulator was used. Optical distortion, striae, coloring and peeling were all poor.

Example 10 4000 g of 1,2,3-tris (β-epithiopropylthio) propane, 15 g of N, N-dimethylcyclohexylamine as a catalyst, and 6 g of mercaptomethylthiirane as a polymerization regulator were mixed. The same operation as in Example 1 was performed. Optical distortion, striae, coloring and peeling were all good.

Comparative Example 6 The same operation as in Example 9 was performed except that no polymerization regulator was used. Optical distortion, striae, coloring and peeling were all poor.

Example 11 1,5-bis (β-epithiopropylthio) -2- (β
-Epithiopropylthiomethyl) -3-thiapentane 4
000 g, N, N-dimethylcyclohexylamine (15 g) as a catalyst, and methoxymethylthiirane (4 g) as a polymerization regulator were mixed. Thereafter, the same operation as in Example 1 was performed. Optical distortion, striae, coloring and peeling were all good.

Comparative Example 7 The same operation as in Example 10 was performed except that no polymerization regulator was used. Optical distortion, striae, coloring and peeling were all poor.

Example 12 Bis (β-epithiopropyl) disulfide 4000
g, 13 g of N, N-dimethylcyclohexylamine as a catalyst and 2 g of chloromethylthiirane as a polymerization regulator were mixed, and thereafter the same operation as in Example 1 was performed. Optical distortion, striae, coloring and peeling were all good.

Comparative Example 8 The same operation as in Example 11 was performed except that no polymerization regulator was used. Optical distortion, striae, coloring and peeling were all poor.

[0047]

[Table 1] 1) In the table, the symbols in the monomer column indicate the following. A: bis (β-epithiopropyl) sulfide B: 1,2-bis (β-epithiopropylthio) ethane C: 1- (β-epithiopropylthio) -2- [2-β
-Epithiopropylthioethylthio] ethane D: 2,5-bis (β-epithiopropylthiomethyl)
-1,4-dithiane E: 1,2,3-tris (β-epithiopropylthio)
Propane F: 1,5-bis (β-epithiopropylthio) -2-
(Β-epithiopropylthiomethyl) -3-thiapentane G: bis (β-epithiopropyl) disulfide 2) In the table, the symbols in the polymerization catalyst column indicate the following. a: N, N-dimethylethanolamine b: Tetra-n-butylphosphonium bromide c: N, N-dimethylcyclohexylamine

 ──────────────────────────────────────────────────続 き Continued on the front page F term (reference) 4C063 AA03 BB08 CC97 DD91 EE10 4J030 BA04 BB03 BG25

Claims (2)

[Claims] 1. A polymerization regulator for an episulfide compound having two or more structures represented by the following formula (2) per molecule, comprising a compound represented by the following formula (1). Embedded image (Wherein, R ¹ , R ² , and R ³ each represent a hydrocarbon group having 1 to 10 carbon atoms or hydrogen, and R ⁴ represents a hydrocarbon group having 1 to 10 carbon atoms or a single bond. X represents F or Cl. , Br,
I, As, SH, OH, alkoxy having 1 to 10 carbon atoms,
C1-C10 alkylthio or C1-C10 mercaptoalkylthio is shown. m shows 1-5. ) (In the formula, R ⁵ , R ⁶ , and R ⁷ each represent a hydrocarbon group having 1 to 10 carbon atoms or hydrogen. N represents 1 to 5.) 2. A method for producing a resin for an optical material by polymerizing an episulfide compound according to claim 1, wherein 0.0001 to 1 part by weight of the polymerization modifier according to claim 1 is added to 100 parts by weight of the episulfide compound. A method for producing a resin for an optical material, comprising using: