Composition for optical material Number:7,091,307 from the United States Patent and Trademark Office (PTO) owispatent The present invention relates to a composition for optical materials, comprising (a) a compound having in one molecule at least one structure represented by the following Formula 1: ##STR00001## wherein R.sup.1 is a single bond or a C.sub.1-10 hydrocarbon group, each of R.sup.2, R.sup.3 and R.sup.4 is a C.sub.1-10 hydrocarbon group or hydrogen, Y is O, 5, Se or Te, m is 1 to 5, and n is 0 to 5; (b) a compound having in one molecule at least one isocyanate group and/or at least one isothiocyanate group; (c) a compound having in one molecule at least one mercapto group; and (d) an inorganic compound having sulfur atom and/or selenium atom, and also relates to an optical material produced by polymerization curing the composition, a production method thereof, and an optical lens comprising the optical material. The present invention provides a high refractive, high Abbe's number optical material having an improved impact resistance.<H Composition, material, Composition, for, 7091307.html, Patent, pto, 7091307

Title: Composition for optical material

Abstract: The present invention relates to a composition for optical materials, comprising (a) a compound having in one molecule at least one structure represented by the following Formula 1: ##STR00001## wherein R.sup.1 is a single bond or a C.sub.1-10 hydrocarbon group, each of R.sup.2, R.sup.3 and R.sup.4 is a C.sub.1-10 hydrocarbon group or hydrogen, Y is O, 5, Se or Te, m is 1 to 5, and n is 0 to 5; (b) a compound having in one molecule at least one isocyanate group and/or at least one isothiocyanate group; (c) a compound having in one molecule at least one mercapto group; and (d) an inorganic compound having sulfur atom and/or selenium atom, and also relates to an optical material produced by polymerization curing the composition, a production method thereof, and an optical lens comprising the optical material. The present invention provides a high refractive, high Abbe's number optical material having an improved impact resistance.

Patent Number: 7,091,307 Issued on 08/15/2006 to Yoshimura, et al.

Inventors: Yoshimura; Yuichi (Mie, JP), Takeuchi; Motoharu (Tokyo, JP), Horikoshi; Hiroshi (Tokyo, JP)
Assignee: Mitsubishi Gas Chemical Company, Inc. (Tokyo, JP)

Appl. No.: 10/398,188

Filed: October 11, 2001

PCT Filed: October 11, 2001

PCT No.: PCT/JP01/08926

371(c)(1),(2),(4) Date: April 02, 2003

PCT Pub. No.: WO02/33448

PCT Pub. Date: April 25, 2002

Foreign Application Priority Data


Oct 13, 2000 [JP]			2000-314385

Current U.S. Class: 528/377 ; 528/378; 528/380; 528/381; 528/387; 528/388; 528/389

Current International Class: C08G 75/06 (20060101); C08G 75/30 (20060101)

Field of Search: 528/377,378,380,381,387,388,389

References Cited [Referenced By]

U.S. Patent Documents


6124424	September 2000	Okazaki et al.
6130307	October 2000	Amagai et al.
6444146	September 2002	Yoshimura et al.
6472495	October 2002	Yoshimura et al.
6531532	March 2003	Yoshimura et al.
6534589	March 2003	Yoshimura et al.
2004/0026658	February 2004	Yoshimura et al.

Foreign Patent Documents


785194	Jul., 1997	EP
1 046 931	Oct., 2000	EP
1 319 966	Jun., 2003	EP

Other References

Supplementary European Search Report mailed Apr. 5, 2004, for EP No. 01 97 4784. cited by other.

Primary Examiner: Robertson; Jeffrey B.
Attorney, Agent or Firm: Antonelli, Terry, Stout and Kraus, LLP.

Claims

What is claimed is:

1. A composition for optical materials, comprising: (a) a compound having in one molecule at least one structure represented by the following Formula 1: ##STR00004## wherein R.sup.1 is a single bond or a C.sub.1-10 hydrocarbon group, each of R.sup.2, R.sup.3 and R.sup.4 is a C.sub.1-10 hydrocarbon group or hydrogen, Y is O, S, Se or Te, m is 1 to 5, and n is 0 to 5; (b) a compound having in one molecule at least one isocyanate group and/or isothiocyanate group; (c) a compound having in one molecule at least one mercapto group; and (d) an inorganic compound having sulfur atom and/or selenium atom, wherein the compound (d) is sulfur, carbon disulfide, selenium, lead selenide or selenium sulfide.

2. The composition for optical materials according to claim 1, wherein the compound (a) is represented by the following Formula 2: ##STR00005## wherein R.sup.1 is a single bond or a C.sub.1-10 hydrocarbon group, each of R.sup.2, R.sup.3 and R.sup.4 is a C.sub.1-10 hydrocarbon group or hydrogen, Y is O, S, Se or Te, m is 1 to 5, and n is 0 to 5.

3. The composition for optical materials according to claim 1, wherein the compound (a) is represented by Formula 1 wherein Y is S or Se, m is 1, and n is 0 to 2.

4. The composition for optical materials according to claim 2, wherein the compound (a) is represented by Formula 2 wherein Y is S or Se, m is 1, and n is 0 to 2.

5. The composition for optical materials according to claim 1, wherein the compound (c) has a sulfide linkage.

6. The composition for optical materials according to claim 2, wherein the compound (c) has a sulfide linkage.

7. An optical material produced by polymerization curing the composition as defined in claim 1.

8. An optical material produced by polymerization curing the composition as defined in claim 2.

9. An optical lens comprising the optical material as defined in claim 7.

10. An optical lens comprising the optical material as defined in claim 8.

11. A method of producing an optical material, comprising a step of polymerization curing the composition as defined in claim 1.

12. A method of producing an optical material, comprising a step of polymerization curing the composition as defined in claim 2.

13. The composition for optical materials according to claim 1, wherein a total amount of the compound (a) and the inorganic compound (d) included in the composition is 5 to 95 parts by weight.

14. The composition for optical materials according to claim 13, wherein a total amount of the compound (b) and the compound (c) is 5 to 95 parts by weight.

15. The composition for optical materials according to claim 1, wherein a total amount of the compound (b) and the compound (c) is 5 to 95 parts by weight.

16. The composition for optical materials according to claim 1, wherein the total amount of the compound (a) and the inorganic compound (d) is 20 to 90 parts by weight, and the total amount of the compound (b) and the compound (c) is 10 to 90 parts by weight.

Description

TECHNICAL FIELD

The present invention relates to a composition suitable for producing an optical material such as plastic lens, prism, optical fiber, information recording medium, and filter, particularly, for producing a plastic spectacle lens. The present invention further relates to an optical material produced by polymerization curing the composition, a production method thereof, and an optical lens comprising the optical material.

BACKGROUND ART

Plastic materials are recently widely used in manufacturing optical materials, particularly, spectacle lenses because of their light weight, toughness and easiness of dyeing. Optical materials, particularly, spectacle lenses are required to have, in addition to a low specific gravity, a high refractive index and a large Abbe's number for optical properties, and a high heat resistance and a high impact resistance for physical properties. A large refractive index makes it possible to reduce the thickness of lens. A high Abbe's number reduces the chromatic aberration of lens. A high heat resistance and a high impact strength facilitate the fabrication process and are important in view of safety in use.

The inventors found a novel sulfur compound capable of providing a thin optical material having a low chromatic aberration, and filed applications for patent (Japanese Patent Application Laid-Open Nos. 9-71580, 9-110979 and 9-255781, and Japanese Patent Application No.2000-20627). The inventors further found a resin composition capable of enhancing the impact resistance, and filed applications for patent (Japanese Patent Application Laid-Open Nos. 11-292950 and 11-318960). However, the refractive index decreased with increasing impact resistance, because the component for improving the impact resistance, in turn, reduces the refractive index. Therefore, the novel sulfur compound, found by the inventors, capable of providing a thin optical material having a low chromatic aberration fails to exert its effect sufficiently in the resin composition having an improved impact resistance.

DISCLOSURE OF INVENTION

An object of the present invention is to provide a high refractive, high Abbe's number optical material having a higher impact resistance.

The present invention provides a composition for optical materials, comprising:

(a) a compound having in one molecule at least one structure represented by the following Formula 1:

##STR00002## wherein R.sup.1 is a single bond or a C.sub.1-10 hydrocarbon group, each of R.sup.2, R.sup.3 and R.sup.4 is a C.sub.1-10 hydrocarbon group or hydrogen, Y is O, S, Se or Te, m is 1 to 5, and n is 0 5;

(b) a compound having in one molecule at least one isocyanate group and/or isothiocyanate group;

(c) a compound having in one molecule at least one mercapto group; and

(d) an inorganic compound having sulfur atom and/or selenium atom.

The present invention further provides an optical material produced by polymerization curing the composition, a production method thereof, and an optical lens comprising the optical material.

BEST MODE FOR CARRYING OUT THE INVENTION

Each proportion of the compound (a), compound (b), compound (c) and compound (d) in the composition for optical materials is not determined unequivocally because it depends on the refractive index or viscosity of each compound and the properties of the resulting resin. To maintain a high refractive index, the total amount of the compound (a) and the compound (d) is preferably 5 to 95 parts by weight. To enhance the impact resistance, the total amount of the compound (b) and the compound (c) is preferably 5 to 95 parts by weight. If exceeding the above ranges, a high impact resistance intended by the present invention is not achieved. In addition, there occur several disadvantages such as insufficient heat resistance, discoloration of the cured product and failure in achieving one of the objects of the present invention, i.e., a high refractive index and a high Abbe's number. Preferably, the total amount of the compound (a) and the compound (d) is 5 to 95 parts by weight and the total amount of the compound (b) and the compound (c) is 5 to 95 parts by weight. More preferably, the total amount of the compound (a) and the compound (d) is 10 to 90 parts by weight and the total amount of the compound (b) and the compound (c) is 10 to 90 parts by weight. Most preferably, the total amount of the compound (a) and the compound (d) is 20 to 90 parts by weight and the total amount of the compound (b) and the compound (c) is 10 to 90 parts by weight.

To further enhance the impact resistance of the optical material obtained by polymerization curing, the compound (a) preferably has in one molecule two or more structure represented by Formula 1, and more preferably the compound (a) is represented by the following Formula 2:

##STR00003## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, Y, m and n are as defined in Formula 1; the compound (b) preferably has in one molecule two or more isocyanate groups and/or isothiocyanate groups; and the compound (c) preferably has in one molecule two or more mercapto groups.

To achieve a high refractive index, one of the objects of the present invention, R.sup.1 of Formula 1 representing the compound (a) is preferably a C.sub.0-2 hydrocarbon group, and each of R.sup.2, R.sup.3 and R.sup.4 of Formula 1 is preferably hydrogen or methyl group. More preferably, R.sup.1 is a C.sub.0-1 hydrocarbon group, and each of R.sup.2, R.sup.3 and R.sup.4 is hydrogen. A preferred compound (b) is one having a sulfur atom, and more preferred is one having a sulfide linkage. A preferred compound (c) is one having a sulfur atom in addition to a mercapto group, and more preferred is one having a sulfide linkage. The compound (d) is an inorganic compound. The inorganic compound referred to herein has the meaning described in "Standard Dictionary of Chemical Terms", compiled by The Chemical Society of Japan, 1991, Maruzen. Namely, as described in the above document, the inorganic compound referred to herein means compounds having no carbon atom and relatively simple compounds even when having carbon atom. Therefore, carbon disulfide, potassium thiocyanate, etc. which are generally not classified into organic compounds are regarded herein as inorganic compounds. The compound (d) is preferably at least one compound selected from the group consisting of sulfur, carbon disulfide, selenium, selenium sulfide and lead selenide.

The compound (a) includes any compounds having in one molecule at least one structure of Formula 1. Examples of preferred compounds are: (A) Compounds having in one molecule at least one structure of Formula 1 wherein n is zero; (B) Compounds having in one molecule at least one structure of Formula 1 wherein Y is O; (C) Compounds having in one molecule at least one structure of Formula 1 wherein Y is S; (D) Compounds having in one molecule at least one structure of Formula 1 wherein Y is Se; and (E) Compounds having in one molecule at least one structure of Formula 1 wherein Y is Te.

The compounds (A), (B), (C), (D) and (E) are mainly constituted by a chain backbone, a branched backbone, an alicyclic backbone, an aromatic backbone or a heterocyclic backbone having nitrogen, oxygen, sulfur, selenium or tellurium. The compounds may have in one molecule two or more of these backbone structures simultaneously. The compounds may also have a sulfide linkage, a selenide linkage, a telluride linkage, an ether linkage, a sulfone linkage, a ketone linkage, an ester linkage, an amide linkage or a urethane linkage.

(A) Preferred examples of the compounds having in one molecule at least one structure of Formula 1 wherein n is zero include:

Organic compounds having aliphatic chain backbone:

1,1-bis(epithioethyl)methane, 1,1-bis(epithioethyl)methane, 1-(epithioethyl)-1-(.beta.-epithiopropyl)methane, 1,1-bis(.beta.-epithiopropyl)methane, 1-(.beta.epithioethyl)-1-(.beta.-epithiopropyl)ethane, 1,2-bis(.beta.-epithiopropyl)ethane, 1,2-bis(.beta.-epithiopropyl)ethane, 1-(epithioethyl)-3-(.beta.-epithiopropyl)butane, 1,3-bis(,-epithiopropyl)propane, 1-(epithioethyl)-4-(.beta.-epithiopropyl)pentane, 1,4-bis(.beta.-epithiopropyl)butane, 1-(epithioethyl)-5-(.beta.-epithiopropyl)hexane, 1-(epithioethyl)-2-(.gamma.-epithiobutylthio)ethane, 1-(epithioethyl)-2-[2-(.gamma.-epithiobutylthio)ethylthio]ethane, tetrakis(.beta.-epithiopropyl)methane, 1,1,1-tris(.beta.-epithiopropyl)propane, 1,3-bis(p-epithiopropyl)-1-(.beta.-epithiopropyl)-2-thiapropane and 1,5-bis(.beta.-epithiopropyl)-2,4-bis(.beta.-epithiopropyl)-3-thiapentane- ;

Compounds having alicyclic backbone:

1,3- or 1,4-bis(epithioethyl)cyclohexane, 1,3- or 1,4-bis(.beta.-epithiopropyl)cyclohexane, bis [4-(epithioethyl)cyclohexyl]methane, bis[4-(.beta.-epithiopropyl)cyclohexyl]methane, 2,2-bis[4-(.beta.-epithioethyl)cyclohexyl]propane, 2,2-bis[4-(.beta.-epithiopropyl)cyclohexyl]propane, bis[4-(.beta.-epithiopropyl)cyclohexyl] sulfide, bis[4-(epithioethyl)cyclohexyl] sulfide, 2,5-bis(epithioethyl)1,4-dithiane, 2,5-bis(.beta.-epithiopropyl)-1,4-dithiane, 4-epithioethyl-1,2-cyclohexene sulfide, 4-epoxy-1,2-cyclohexene sulfide, 2,3-, 2,5-or 2,6-bis(1,2-epithioethyl)-1,4-diselenane, 2,3-, 2,5- or 2,6-bis(2,3-epithiopropyl)-1,4-diselenane, 2,4-, 2,5- or 2,6-bis(1,2-epithioethyl)-1,3-diselenane, 2,4-, 2,5- or 2,6-bis(2,4-epithiopropyl)-1,3-diselenane, 2,3-, 2,5-, 2,6-or 3,5-bis(1,2-epithioethyl)-1-thia-4-selenane, 2,3-, 2,5-, 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-, 2,5- or 4,5-bis(1,2-epithioethyl)-1-thia-3-selenolane, 2,4-, 2,5- or 4,5-bis(2,4-epithiopropyl)-1-thia-3-selenolane, 2,3-, 2,4-, 2,5- or 3,4-bis(1,2-epithioethyl)selenophane, 2,3-,2,4-, 2,5- or 3,4-bis(2,3-epithiopropyl)selenophane, 2,3-, 2,5- or 2,6-bis(1,2-epithioethyl)-1,4-ditellurane, 2,3-, 2,5- or 2,6-bis(2,3-epithiopropyl)-1,4-ditellurane, 2,4-, 2,5- or 2,6-bis(1,2-epithioethyl)-1,3-ditellurane, 2,4-, 2,5- or 2,6-bis(2,4-epithiopropyl)-1,3-ditellurane, 2,3-, 2,5-, 2,6- or 3,5-bis(1,2-epithioethyl)-1-thia-4-tellurane, 2,3-, 2,5-, 2,6- or 3,5-bis(2,3-epithiopropyl)-1-thia-4-tellurane, 2,4- or 4,5-bis(1,2-epithioethyl)-1,3-ditellurolane, 2,4- or 4,5-bis(2,4-epithiopropyl)-1,3-ditellurolane, 2,4-, 2,5- or 4,5-bis(1,2-epithioethyl)-1-thia-3-tellurolane 2,4-, 2,5- or 4,5-bis(2,4-epithiopropyl)-1-thia-3-selenolane, 2,3-, 2,4-, 2,5- or 3,4-bis(1,2-epithioethyl)tellurophane, and 2,3-, 2,4-, 2,5- or 3,4-bis(2,3-epithiopropyl)tellurophane;

Compounds having aromatic backbone:

1,3- or 1,4-bis(epithioethyl)benzene, 1,3- or 1,4-bis(.beta.-epithiopropyl)benzene, bis [4-(epithioethyl)phenyl]methane, bis[4-(.beta.-epithiopropyl)phenyl]methane, 2,2-bis[4-(epithioethyl)phenyl]propane, 2,2-bis[4-(.beta.-epithiopropyl)phenyl]propane, bis[4-(epithioethyl)phenyl] sulfide, bis[4-(.beta.-epithiopropyl)phenyl] sulfide, bis[4-(epithioethyl)phenyl] sulfone, bis[4-(.beta.-epithiopropyl)phenyl] sulfone, 4,4'-bis(epithioethyl)biphenyl, and 4,4'-bis (.beta.-epithiopropyl)biphenyl; and

Compounds obtained by replacing at least one hydrogen of the epithio group in the above compounds with methyl.

(B) Preferred examples of the compounds having in one molecule at least one structure of Formula 1 wherein Y is O include:

Organic compounds having aliphatic chain backbone:

bis(.beta.-epithiopropyl) ether, bis(.beta.-epithiopropyl) ether, bis(.beta.-epithiopropyloxy)methane, 1,2-bis(.beta.-epithiopropyloxy)ethane, 1,3-bis(.beta.-epithiopropyloxy)propane, 1,2-bis(.beta.-epithiopropyloxy)propane, 1-(.beta.-epithiopropyloxy)-2-(.beta.-epithiopropyloxymethyl)propane, 1,4-bis(.beta.-epithiopropyloxy)butane, 1,3-bis(.beta.-epithiopropyloxy)butane, 1-(.beta.-epithiopropyloxy)-3-(.beta.-epithiopropyloxymethyl)butane, 1,5-bis(.beta.-epithiopropyloxy)pentane, 1-(.beta.-epithiopropyloxy)-4-(.beta.-epithiopropyloxymethyl)pentane, 1,6-bis(.beta.-epithiopropyloxy)hexane, bis(epithioethyl) ether, 1-(.beta.-epithiopropyloxy)-5-(.beta.-epithiopropyloxymethyl)hexane, 1-(.beta.-epithiopropyloxy)-2-[(2-.beta.-epithiopropyloxyethyl)oxy]ethane- , 1-(.beta.-epithiopropyloxy)-2-[[2-(2-.beta.-epithiopropyloxyethyl)oxyeth- yl]oxy]ethane, bis(5,6-epithio-3-oxahexyl) selenide, bis(5,6-epithio-3-oxahexyl) telluride, tetrakis(.beta.-epithiopropyloxymethyl)methane, 1,1,1-tris(.beta.-epithiopropyloxymethyl)propane, 1,5-bis(.beta.-epithiopropyloxy)-2-(.beta.-epithiopropyloxymethyl)-3-thia- pentane, 1,5-bis(.beta.-epithiopropyloxy)-2,4-bis(.beta.-epithiopropyloxym- ethyl)-3-thiapentane, 1-(.beta.-epithiopropyloxy)-2,2-bis(.beta.-epithiopropyloxymethyl)-4-thia- hexane, 1,5,6-tris(.beta.-epithiopropyloxy)-4-(.beta.-epithiopropyloxymeth- yl)-3-thiahexane, 1,8-bis(.beta.-epithiopropyloxy)-4-(.beta.-epithiopropyloxymethyl)-3,6-di- thiaoctane, 1,8-bis(.beta.-epithiopropyloxy)-4,5-bis(.beta.-epithiopropyloxymethyl)-3- ,6-dithiaoctane, 1,8-bis(.beta.-epithiopropyloxy)-4,4-bis(.beta.-epithiopropyloxymethyl)-3- ,6-dithiaoctane, 1,8-bis(.beta.-epithiopropyloxy)-2,4,5-tris(.beta.-epithiopropyloxymethyl- )-3,6-dithiaoctane, 1,8-bis(.beta.-epithiopropyloxy)-2,5-bis(.beta.-epithiopropyloxymethyl)-3- ,6-dithiaoctane, 1,9-bis(.beta.-epithiopropyloxy)-5-(.beta.-epithiopropyloxymethyl)-5-[(2-- .beta.-epithiopropyloxyethyl)oxymethyl]-3,7-dithianonane, 1,10-bis(.beta.-epithiopropyloxy)-5,6-bis [(2-.beta.-epithiopropyloxyethyl)oxy]-3,6,9-trithiadecane, 1,11-bis(.beta.-epithiopropyloxy)-4,8-bis(.beta.-epithiopropyloxymethyl)-- 3,6,9-trithiaundecane, 1,11-bis(.beta.-epithiopropyloxy)-5,7-bis(.beta.-epithiopropyloxymethyl)-- 3,6,9-trithiaundecane, 1,11-bis(.beta.-epithiopropyloxy)-5,7-[(2-.beta.-epithiopropyloxyethyl)ox- ymethyl]-3,6,9-trithiaundecane, and 1,11-bis(.beta.-epithiopropyloxy)-4,7-bis(.beta.-epithiopropyloxymethyl)-- 3,6,9-trithiaundecane;

Compounds having alicyclic backbone:

1,3- or 1,4-bis(.beta.-epithiopropyloxy)cyclohexane, 1,3- or 1,4-bis(.beta.-epithiopropyloxymethyl)cyclohexane, bis [4-(.beta.-epithiopropyloxy)cyclohexyl]methane, 2,2-bis[4-(.beta.-epithiopropyloxy)cyclohexyl]propane, bis[4-(.beta.-epithiopropyloxy)cyclohexyl] sulfide, 2,5-bis(.beta.-epithiopropyloxymethyl)-1,4-dithiane, 2,5-bis(.beta.-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-, 2,5- or 4,5-bis(3,4-epithio-1-oxabutyl)-1-thia-3-selenolane, 2,4-, 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)dicycloselenanonane, 2,3-, 2,4-, 2,5- or 3,4-bis(3,4-epithio-1-oxabutyl)selenophane, 2,3-, 2,4-, 2,5- or 3,4-bis(4,5-epithio-2-oxapentyl)selenophane, 2,3-, 2,5- or 2,6-bis(3,4-epithio-1-oxabutyl)-1,4-diselenane, 2,3-, 2,5- or 2,6-bis(4,5-epithio-2-oxapenyyl)-1,4-diselenane, 2,4-,2,5- or 2,6-bis(3,4-epithio-1-oxabutyl)-1,3-diselenane, 2,4-, 2,5- or 2,6-bis(4,5-epithio-2-oxapentyl)-1,3-diselenane, 2,3-, 2,5-, 2,6- or 3,5-bis(3,4-epithio-1-oxabutyl)-1-thia-4-selenane, 2,3-, 2,5-, 2,6- or 3,5-bis(4,5-epithio-2-oxapentyl)-1-thia-4-selenane, 2,4- or 4,5-bis(3,4-epithio-1-oxabutyl)-1,3-ditellurolane, 2,4-or 4,5-bis(4,5-epithio-2-oxapentyl)-1,3-ditellurolane, 2,4-, 2,5- or 4,5-bis(3,4-epithio-1-oxabutyl)-1-thia-3-tellurolane, 2,4-, 2,5- or 4,5-bis(4,5-epithio-2-oxapentyl)-1-thia-3-tellurolane, bis(3,4-epithio-1-oxabutyl)tricyclotelluraoctane, bis(3,4-epithio-1-oxabutyl)dicyclotelluranonane, 2,3-, 2,4-, 2,5- or 3,4-bis(3,4-epithio-1-oxabutyl)tellurophane, 2,3-, 2,4-, 2,5- or 3,4-bis(4,5-epitho-2-oxapentyl)tellurophane, 2,3-, 2,5- or 2,6-bis(3,4-epithio-1-oxabutyl)-1,4-ditellurane, 2,3-, 2,5- or 2,6-bis(4,5-epithio-2-oxapentyl)-1,4-ditellurane, 2,4-,2,5- or 2,6-bis(3,4-epithio-1-oxabutyl)-1,3-ditellurane, 2,4-, 2,5- or 2,6-bis(4,5-epithio-2-oxapentyl)-1,3-ditellurane, 2,3-, 2,5-, 2,6- or 3,5-bis(3,4-epithio-1-oxabutyl)-1-thia-4-tellurane, and 2,3-, 2,5-, 2,6- or 3,5-bis(4,5-epithio-2-oxapentyl)-1-thia-4-tellurane;

Compounds having aromatic backbone:

1,3- or 1,4-bis(.beta.-epithiopropyloxy)benzene, 1,3- or 1,4-bis(.beta.-epithiopropyloxymethyl)benzene, bis[4-(.beta.-epithiopropyl)phenyl]methane, 2,2-bis [4-(.beta.-epithiopropylthio)phenyl]propane, bis[4-(.beta.-epithiopropylthio)phenyl] sulfide, bis[4-(.beta.-epithiopropylthio)phenyl] sulfone, and 4,4'-bis(.beta.-epithiopropylthio)biphenyl; and

Compounds obtained by replacing at least one hydrogen of the epithio group in the above compounds with methyl.

(C) Preferred examples of the compounds having in one molecule at least one structure of Formula 1 wherein Y is S include:

Organic compounds having aliphatic chain backbone:

bis(.beta.-epithiopropyl) sulfide, bis(.beta.-epithiopropyl) sulfide, bis(.beta.-epithiopropyl) disulfide, bis(.beta.-epithiopropyl) disulfide, bis(.beta.-epithiopropyl) trisulfide, bis(.beta.-epithiopropylthio)methane, 1,2-bis(.beta.-epithiopropylthio)ethane, 1,3-bis(.beta.-epithiopropylthio)propane, 1,2-bis(.beta.-epithiopropylthio)propane, bis(epithioethyl) sulfide, bis(epithioethyl) disulfide, 1-(.beta.-epithiopropylthio)-2-(.beta.-epithiopropylthiomethyl)propane, 1,4-bis(.beta.-epithiopropylthio)butane, 1,3-bis(.beta.-epithiopropylthio)butane, 1-(.beta.-epithiopropylthio)-3-(.beta.-epithiopropylthiomethyl)butane, 1,5-bis(.beta.-epithiopropylthio)pentane, 1-(.beta.-epithiopropylthio)-4-(.beta.-epithiopropylthiomethyl)pentane, 1,6-bis(.beta.-epithiopropylthio)hexane, 1-(.beta.-epithiopropylthio)-5-(.beta.-epithiopropylthiomethyl)hexane, 1-(.beta.-epithiopropylthio)-2-[(2-.beta.-epithiopropylthioethyl)thio]eth- ane, 1-(.beta.-epithiopropylthio)-2-[[2-(2-.beta.-epithiopropylthioethyl)t- hioethyl]thio]ethane, tetrakis(.beta.-epithiopropylthiomethyl)methane, 1,1,1-tris(.beta.-epithiopropylthiomethyl)propane, 1,5-bis(.beta.-epithiopropylthio)-2-(.beta.-epithiopropylthiomethyl)-3-th- iapentane, 1,5-bis(.beta.-epithiopropylthio)-2,4-bis(.beta.-epithiopropylt- hiomethyl)-3-thiapentane, 1-(.beta.-epithiopropylthio)-2,2-bis(.beta.-epithiopropylthiomethyl)-4-th- iahexane, 1,5,6-tris(.beta.-epithiopropylthio)-4-(.beta.-epithiopropylthio- methyl)-3-thiahexane, 1,8-bis(.beta.-epithiopropylthio)-4-(.beta.-epithiopropylthiomethyl)-3,6-- dithiaoctane, 1,8-bis(.beta.-epithiopropylthio)-4,5-bis(.beta.-epithiopropylthiomethyl)- -3,6-dithiaoctane, 1,8-bis(.beta.-epithiopropylthio)-4,4-bis(.beta.-epithiopropylthiomethyl)- -3,6-dithiaoctane, 1,8-bis(.beta.-epithiopropylthio)-2,4,5-tris(.beta.-epithiopropylthiometh- yl)-3,6-dithiaoctane, 1,8-bis(.beta.-epithiopropylthio)-2,5-bis(.beta.-epithiopropylthiomethyl)- -3,6-dithiaoctane, 1,9-bis(.beta.-epithiopropylthio)-5-(.beta.-epithiopropylthiomethyl)-5-[(- 2-.beta.-epithiopropylthioethyl) thiomethyl]-3,7-dithianonane, 1,10-bis(.beta.-epithiopropylthio)-5,6-bis [(2-.beta.-epithiopropylthioethyl)thio]-3,6,9-trithiadecane, 1,11-bis(.beta.-epithiopropylthio)-4,8-bis(.beta.-epithiopropylthiomethyl- )-3,6,9-trithiaundecane, 1,11-bis(.beta.-epithiopropylthio)-5,7-bis(.beta.-epithiopropylthiomethyl- )-3,6,9-trithiaundecane, 1,11-bis(.beta.-epithiopropylthio)-5,7-[(2-.beta.-epithiopropylthioethyl)- thiomethyl]-3,6,9-trithiaundecane, 1,11-bis(.beta.-epithiopropylthio)-4,7-bis(.beta.-epithiopropylthiomethyl- )-3,6,9-trithiaundecane, tetra[2-(.beta.-epithiopropylthio)acetylmethyl]methane, 1,1,1-tri[2-(.beta.-epithiopropylthio)acetylmethyl]propane, tetra[2-(.beta.-epithiopropylthiomethyl)acetylmethyl]methane, 1,1,1-tri[2-(.beta.-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-thioepoxy-2-thiapentyl)-3,6,9-triselenaundecane-1,11-bis(3,4-thio- epoxy-1-thiabutyl), 1,4-bis(3,4-thioepoxy-1-thiabutyl)-2,3-bis(6,7-thioepoxy-1-selena-4-thiah- eptyl)butane, tris(4,5-thioepoxy-2-thiapentyl)-3-selena-6-thiaoctane-1,8-bis(3,4-thioep- oxy-1-thiabutyl), bis(5,6-epithio-3-thiahexyl) telluride, 2,3-bis(6,7-thioepoxy-1-tellura-4-thiaheptyl)-1-(3,4-thioepoxy-1-thiabuty- l)propane, 1,1,3,3-tetrakis(4,5-thioepoxy-2-thiapentyl)-2-tellurapropane, bis(4,5-thioepoxy-2-thiapentyl)-3,6,9-tritelleraundecane-1,11-bis(3,4-thi- oepoxy-1-thiabutyl), 1,4-bis(3,4-thioepoxy-1-thiabutyl)-2,3-bis(6,7-thioepoxy-1-tellura-4-thia- heptyl)butane and tris(4,5-thioepoxy-2-thiapentyl)-3-tellura-6-thiaoctane-1,8-bis(3,4-thioe- poxy-1-thiabutyl);

Compounds having alicyclic backbone:

1,3- or 1,4-bis(.beta.-epithiopropylthio)cyclohexane, 1,3- or 1,4-bis(.beta.-epithiopropylthiomethyl)cyclohexane, bis[4-(.beta.-epithiopropylthio)cyclohexyl]methane, 2,2-bis [4-(.beta.-epithiopropylthio)cyclohexyl]propane, bis[4-(.beta.-epithiopropylthio)cyclohexyl] sulfide, 2,5-bis(.beta.-epithiopropylthiomethyl)-1,4-dithiane, 2,5-bis(.beta.-epithiopropylthioethylthiomethyl)-1,4-dithiane, 2,3-, 2,5- or 2,6-bis(3,4-epithio-1-thiabutyl)-1,4-diselenane, 2,3-, 2,5- or 2,6-bis(4,5-epithio-2-thiapentyl)-1,4-diselenane, 2,4-, 2,5- or 5,6-bis(3,4-epithio-1-thiabutyl)-1,3-diselenane, 2,4-, 2,5-or 5,6-bis(4,5-epithio-2-thiapentyl)-1,3-diselenane, 2,3-, 2,5-, 2,6- or 3,5-bis(3,4-epithio-1-thiabutyl)-1-thia-4-selenane, 2,3-, 2,5-, 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-, 2,5-or 4,5-bis(3,4-epithio-1-thiabutyl)-1-thia-3-selenolane, 2,4-, 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-thiabutyl)dicycloselenanonane, 2,3-, 2,4-, 2,5- or 3,4-bis(3,4-epithio-1-thiabutyl)selenophane, 2,3-, 2,4-, 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-selenacycl- ohexane, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or 4,5-bis(3,4-thioepoxy-1-thiabutyl)-1-selenacyclohexane, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or 4,5-bis(4,5-thioepoxy-2-thiapentyl)-1-selenacyclohexane, 2,3-, 2,5- or 2,6-bis(3,4-epithio-1-thiabutyl)-1,4-ditellurane, 2,3-, 2,5- or 2,6-bis(4,5-epithio-2-thiapentyl)-1,4-ditellurane, 2,4-, 2,5- or 5,6-bis(3,4-epithio-1-thiabutyl)-1,3-ditellurane, 2,4-, 2,5- or 5,6-bis(4,5-epithio-2-thiapentyl)-1,3-ditellurane, 2,3-,2,5-, 2,6- or 3,5-bis(3,4-epithio-1-thiabutyl)-1-thia-4-tellurane, 2,3-, 2,5-, 2,6-3,5-bis(4,5-epithio-2-thiapentyl)-1-thia-4-tellurane, 2,4- or 4,5-bis(3,4-epithio-1-thiabutyl)-1,3-ditellurolane, 2,4- or 4,5-bis(4,5-epithio-2-thiapentyl)-1,3-ditellurolane, 2,4-, 2,5- or 4,5-bis(3,4-epithio-1-thiabutyl)-1-thia-3-tellurolane, 2,4-, 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-tritellurane, bis(3,4-epithio-1-thiabutyl)tricyclotelluraoctane, bis(3,4-epithio-1-thiabutyl)dicyclotelluranonane, 2,3-, 2,4-, 2,5- or 3,4-bis(3,4-epithio-1-thiabutyl)tellurophane, 2,3-, 2,4-, 2,5- or 3,4-bis(4,5-epithio-2-thiapentyl)tellurophane, 2-(4,5-thioepoxy-2-thiapentyl)-5-(3,4-thioepoxy-1-thiabutyl)-1-telluracyc- lohexane, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or 4,5-bis(3,4-thioepoxy-1-thiabutyl)-1-telluracyclohexane, and 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-or 4,5-bis(4,5-thioepoxy-2-thiapentyl)-1-telluracyclohexane;

Compounds having aromatic backbone:

1,3- or 1,4-bis(.beta.-epithiopropylthio)benzene, 1,3- or 1,4-bis(.beta.-epithiopropylthiomethyl)benzene, bis[4-(.beta.-epithiopropylthio)phenyl]methane, 2,2-bis[4-(.beta.-epithiopropylthio)phenyl]propane, bis[4-(.beta.-epithiopropylthio)phenyl] sulfide, bis[4-(.beta.-epithiopropylthio)phenyl] sulfone, and 4,4'-bis(.beta.-epithiopropylthio)biphenyl; and

Compounds obtained by replacing at least one hydrogen of the .beta.-epithiopropyl group in the above compounds with methyl.

(D) Preferred examples of the compounds having in one molecule at least one structure of Formula 1 wherein Y is Se include:

Organic compounds having aliphatic chain backbone:

bis(.beta.-epithiopropyl) selenide, bis(.beta.-epithiopropyl) selenide, bis(.beta.-epithiopropyl) diselenide, bis(.beta.-epithiopropyl) diselenide, bis(.beta.-epithiopropyl) triselenide, bis(.beta.-epithiopropylseleno)methane, 1,2-bis(.beta.-epithiopropylseleno)ethane, 1,3-bis(.beta.-epithiopropylseleno)propane, 1,2-bis(.beta.-epithiopropylseleno)propane, bis(epithioethyl) selenide, bis(epithioethyl) diselenide, 1-(.beta.-epithiopropylseleno)-2-(.beta.-epithiopropylselenomethyl)propan- e, 1,4-bis(.beta.-epithiopropylseleno)butane, 1,3-bis(.beta.-epithiopropylseleno)butane, 1-(.beta.-epithiopropylseleno)-3-(.beta.-epithiopropylselenomethyl)butane- , 1,5-bis(.beta.-epithiopropylseleno) pentane, 1-(.beta.-epithiopropylseleno)-4-(.beta.-epithiopropylselenomethyl)pentan- e, 1,6-bis(.beta.-epithiopropylseleno)hexane, 1-(.beta.-epithiopropylseleno)-5-(.beta.-epithiopropylselenomethyl)hexane- , 1-(.beta.-epithiopropylseleno)-2-[(2-.beta.-epithiopropylselenoethyl)thi- o]ethane, 1-(.beta.-epithiopropylseleno)-2-[[2-(2-.beta.-epithiopropylsele- noethyl)selenoethyl]thio]ethane, tetrakis(.beta.-epithiopropylselenomethyl)methane, 1,1,1-tris(.beta.-epithiopropylselenomethyl)propane, 1,5-bis(.beta.-epithiopropylseleno)-2-(.beta.-epithiopropylselenomethyl)-- 3-thiapentane, 1,5-bis(.beta.-epithiopropylseleno)-2,4-bis(.beta.-epithiopropylselenomet- hyl)-3-thiapentane, 1-(.beta.-epithiopropylseleno)-2,2-bis(.beta.-epithiopropylselenomethyl)-- 4-thiahexane, 1,5,6-tris(.beta.-epithiopropylseleno)-4-(, -epithiopropylselenomethyl)-3-thiahexane, 1,8-bis(.beta.-epithiopropylseleno)-4-(.beta.-epithiopropylselenomethyl)-- 3,6-dithiaoctane, 1,8-bis(.beta.-epithiopropylseleno)-4,5-bis(.beta.-epithiopropylselenomet- hyl)-3,6-dithiaoctane, 1,8-bis(.beta.-epithiopropylseleno)-4,4-bis(.beta.-epithiopropylselenomet- hyl)-3,6-dithiaoctane, 1,8-bis(.beta.-epithiopropylseleno)-2,4,5-tris(.beta.-epithiopropylseleno- methyl)-3,6-dithiaoctane, 1,8-bis(.beta.-epithiopropylseleno)-2,5-bis(.beta.-epithiopropylselenomet- hyl)-3,6-dithiaoctane, 1,9-bis(.beta.-epithiopropylseleno)-5-(.beta.-epithiopropylselenomethyl)-- 5-[(2-.beta.-epithiopropylselenoethyl)selenomethyl]-3,7-dithianonane, 1,10-bis(.beta.-epithiopropylseleno)-5,6-bis[(2-.beta.-epithiopropylselen- oethyl)thio]-3,6,9-trithiadecane 1,11-bis(.beta.-epithiopropylseleno)-4,8-bis(.beta.-epithiopropylselenome- thyl)-3,6,9-trithiaundecane, 1,11-bis(.beta.-epithiopropylseleno)-5,7-bis(.beta.-epithiopropylselenome- thyl)-3,6,9-trithiaundecane, 1,11-bis(.beta.-epithiopropylseleno)-5,7-[(2-.beta.-epithiopropylselenoet- hyl)selenomethyl]-3,6,9-trithiaundecane, 1,11-bis(.beta.-epithiopropylseleno)-4,7-bis(.beta.-epithiopropylselenome- thyl)-3,6,9-trithiaundecane, tetra[2-(.beta.-epithiopropylseleno)acetylmethyl]methane, 1,1,1-tri[2-(.beta.-epithiopropylseleno)acetylmethyl]propane, tetra[2-(.beta.-epithiopropylselenomethyl)acetylmethyl]methane, 1,1,1-tri[2-(.beta.-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-selenob- utyl)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-th- ioepoxy-1-selenobutyl), 1,4-bis(3,4-thioepoxy-1-selenobutyl)-2,3-bis(6,7-thioepoxy-1-selena-4-sel- enoheptyl)butane, tris(4,5-thioepoxy-2-selenopentyl)-3-selena-6-thiaoctane-1,8-bis(3,4-thio- epoxy-1-selenobutyl), bis(5,6-epithio-3-selenohexyl) telluride, 2,3-bis(6,7-thioepoxy-1-tellura-4-selenoheptyl)-1-(3,4-thioepoxy-1-seleno- butyl)propane, 1,1,3,3-tetrakis(4,5-thioepoxy-2-selenopentyl)-2-tellurapropane, bis(4,5-thioepoxy-2-selenopentyl)-3,6,9-tritelluraundecane-1,11-bis(3,4-t- hioepoxy-1-selenobutyl), 1,4-bis(3,4-thioepoxy-1-selenobutyl)-2,3-bis(6,7-thioepoxy-1-tellura-4-se- lenoheptyl)butane and tris(4,5-thiepoxy-2-selenopentyl)-3-tellura-6-thiaoctane-1,8-bis(3,4-thio- epoxy-1-selenobutyl);

Compounds having alicyclic backbone:

1,3- or 1,4-bis(.beta.-epithiopropylseleno)cyclohexane, 1,3- or 1,4-bis(.beta.-epithiopropylselenomethyl)cyclohexane, bis[4-(.beta.-epithiopropylseleno)cyclohexyl]methane, 2,2-bis [4-(.beta.-epithiopropylseleno)cyclohexyl]propane, bis[4-(.beta.-epithiopropylseleno)cyclohexyl] sulfide, 2,5-bis(.beta.-epithiopropylselenomethyl)-1,4-dithiane, 2,5-bis(.beta.-epithiopropylselenoethylthiomethyl)-1,4-dithiane, 2,3-2,5- or 2,6-bis(3,4-epithio-1-selenobutyl)-1,4-diselenane, 2,3-, 2,5- or 2,6-bis(4,5-epithio-2-selenopentyl)-1,4-diselenane, 2,4-, 2,5- or 5,6-bis(3,4-epithio-1-selenobutyl)-1,3-diselenane, 2,4-, 2,5- or 5,6-bis(4,5-epithio-2-selenopentyl)-1,3-diselenane, 2,3-, 2,5-, 2,6- or 3,5-bis(3,4-epithio-1-selenobutyl)-1-thia-4-selenane, 2,3-, 2,5-, 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-, 2,5- or 4,5-bis(3,4-epithio-1-selenobutyl)-1-thia-3-selenolane, 2,4-, 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-epitbio-1-selenobutyl)tricycloselenaoctane, bis(3,4-epithio-1-selenobutyl)dicycloselenanonane, 2,3-, 2,4-, 2,5- or 3,4-bis(3,4-epithio-1-selenobutyl)selenophane, 2,3-, 2,4-, 2,5-, 3,4-bis(4,5-epithio-2-selenopentyl)selenophane, 2-(4,5-thioepoxy-2-selenopentyl)-5-(3,4-thioepoxy-1-selenobutyl)-1-selena- cyclohexane, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or 4,5-bis(3,4-thioepoxy-1-selenobutyl)-1-selenacyclohexane, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or 4,5-bis(4,5-thioepoxy-2-selenopentyl)-1-selenacyclohexane, 2,3-, 2,5- or 2,6-bis(3,4-epithio-1-selenobutyl)-I,4-ditellurane, 2,3-, 2,5- or 2,6-bis(4,5-epithio-2-selenopentyl)-1,4-ditellurane, 2,4-, 2,5- or 5,6-bis(3,4-epithio-1-selenobutyl)-1,3-ditellurane, 2,4-, 2,5- or 5,6-bis(4,5-epithio-2-selenopentyl)-1,3-ditellurane, 2,3-, 2,5-, 2,6- or 3,5-bis(3,4-epithio-1-selenobutyl)-1-thia-4-tellurane, 2,3-, 2,5-, 2,6- or 3,5-bis(4,5-epithio-2-selenopentyl)-1-thia-4-tellurane, 2,4- or 4,5-bis(3,4-epithio1-selenobutyl)-1,3-ditellurolane, 2,4- or 4,5-bis(4,5-epithio-2-selenopentyl)-1,3-ditellurolane, 2,4-, 2,5- or 4,5-bis(3,4-epithio-1-selenobutyl)-1-thia-3-telluroane, 2,4-, 2,5- or 4,5-bis(4,5-epithio-2-selenopentyl)-1-thia-3-tellurolane, 2,6-bis(4,5-epithio-2-selenopentyl)-1,3,5-tritellurane, bis(3,4-epithio-1-selenobutyl)tricyclotelluraoctane, bis(3,4-epithio-1-selenobutyl)dicyclotelluranonane, 2,3-, 2,4-, 2,5- or 3,4-bis(3,4-epithio-1-selenobutyl)tellurophane, 2,3-, 2,4-, 2,5- or 3,4-bis(4,5-epithio-2-selenopentyl)tellurophane, 2-(4,5-thioepoxy-2-selenopentyl)-5-(3,4-thioepoxy-1-selenobutyl)-1-tellur- acyclohexane, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or 4,5-bis(3,4-thioepoxy-1-selenobutyl)-1-telluracyclohexane, and 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or 4,5-bis(4,5-thioepoxy-2-selenopentyl)-1-telluracyclohexane;

Compounds having aromatic backbone:

1,3- or 1,4-bis(.beta.-epithiopropylseleno)benzene, 1,3- or 1,4-bis(.beta.-epithiopropylselenomethyl)benzene, bis[4-(.beta.-epithiopropylseleno)phenyl]methane, 2,2-bis [4-(.beta.-epithiopropylseleno)phenyl]propane, bis[4-(.beta.-epithiopropylseleno)phenyl] sulfide, bis[4-(.beta.-epithiopropylseleno)phenyl] sulfone and 4,4'-bis(.beta.-epithiopropylseleno)biphenyl; and

Compounds obtained by replacing at least one hydrogen of the .beta.-epithiopropyl group in the above compounds with methyl.

(E) Preferred examples of the compounds having in one molecule at least one structure of Formula 1 wherein Y is Te include:

Organic compounds having aliphatic chain backbone:

bis(.beta.-epithiopropyl) telluride, bis(.beta.-epithiopropyl) telluride, bis(.beta.-epithiopropyl) ditelluride, bis(.beta.-epithiopropyl) ditelluride, bis(.beta.-epithiopropyl) tritelluride, bis(.beta.-epithiopropyltelluro)methane, 1,2-bis(.beta.-epithiopropyltelluro)ethane, 1,3-bis(.beta.-epithiopropyltelluro)propane, 1,2-bis(.beta.-epithiopropyltelluro)propane, bis(epithioethyl) telluride, bis(epithioethyl) ditelluride, 1-(.beta.-epithiopropyltelluro)-2-(.beta.-epithiopropyltelluromethyl)prop- ane, 1,4-bis(.beta.-epithiopropyltelluro)butane, 1,3-bis(.beta.-epithiopropyltelluro)butane, 1-(.beta.-epithiopropyltelluro)-3-(.beta.-epithiopropyltelluromethyl)buta- ne, 1,5-bis(.beta.-epithiopropyltelluro)pentane, 1-(.beta.-epithiopropyltelluro)-4-(.beta.-epithiopropyltelluromethyl)pent- ane, 1,6-bis(.beta.-epithiopropyltelluro)hexane, 1-(.beta.-epithiopropyltelluro)-5-(.beta.-epithiopropyltelluromethyl)hexa- ne, 1-(.beta.-epithiopropyltelluro)-2-[(2-.beta.-epithiopropyltelluroethyl- )thio]ethane, 1-(.beta.-epithiopropyltelluro)-2-[[2-(2-.beta.-epithiopropyltelluroethyl- )telluroethyl]thio]ethane, tetrakis(.beta.-epithiopropyltelluromethyl)methane, 1,1,1-tris(.beta.-epithiopropyltelluromethyl)propane, 1,5-bis(.beta.-epithiopropyltelluro)-2-(.beta.-epithiopropyltelluromethyl- )-3-thiapentane, 1,5-bis(P -epithiopropyltelluro)-2,4-bis(.beta.-epithiopropyltelluromethyl)-3-thiap- entane, 1-(.beta.-epithiopropyltelluro)-2,2-bis(.beta.-epithiopropyltellur- omethyl)-4-thiahexane, 1,5,6-tris(.beta.-epithiopropyltelluro)-4-(.beta.-epithiopropyltelluromet- hyl)-3-thiahexane, 1,8-bis(.beta.-epithiopropyltelluro)-4-(.beta.-epithiopropyltelluromethyl- )-3,6-dithiaoctane, 1,8-bis(.beta.-epithiopropyltelluro)-4,5-bis(.beta.-epithiopropyltellurom- ethyl)-3,6-dithiaoctane, 1,8-bis(.beta.-epithiopropyltelluro)-4,4-bis(.beta.-epithiopropyltellurom- ethyl)-3,6-dithiaoctane, 1,8-bis(.beta.-epithiopropyltelluro)-2,4,5-tris(.beta.-epithiopropyltellu- romethyl)-3,6-dithiaoctane, 1,8-bis(.beta.-epithiopropyltelluro)-2,5-bis(.beta.-epithiopropyltellurom- ethyl)-3,6-dithiaoctane, 1,9-bis(.beta.-epithiopropyltelluro)-5-(.beta.-epithiopropyltelluromethyl- )-5-[(2-.beta.-epithiopropyltelluroethyl)selenomethyl]-3,7-dithianonane, 1,10-bis(.beta.-epithiopropyltelluro)-5,6-bis[(2-.beta.-epithiopropyltell- uroethyl)thio]-3,6,9-trithiadecane, 1,11-bis(.beta.-epithiopropyltelluro)-4,8-bis(.beta.-epithiopropyltelluro- methyl)-3,6,9-trithiaundecane, 1,11-bis(.beta.-epithiopropyltelluro)-5,7-bis(.beta.-epithiopropyltelluro- methyl)-3,6,9-trithiaundecane, 1,11-bis(.beta.-epithiopropyltelluro)-5,7-[(2-.beta.-epithiopropyltelluro- ethyl)selenomethyl]-3,6,9-trithiaundecane, 1,11-bis(.beta.-epithiopropyltelluro)-4,7-bis(.beta.-epithiopropyltelluro- methyl)-3,6,9-trithiaundecane, tetra[2-(.beta.-epithiopropyltelluro)acetylmethyl] methane, 1,1,1-tri[2-(.beta.-epithiopropyltelluro)acetylmethyl]propane, tetra[2-(.beta.-epithiopropyltelluromethyl)acetylmethyl]methane, 1,1,1-tri[2-(.beta.-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-tellur- obutyl)propane, 1,1,3,3-tetrakis(4,5-thioepoxy-2-telluropentyl)-2-selenapropane, bis(4,5-thioepoxy-2-telluropentyl)-3,6,9-triselenaundecane-1,11-bis(3,4-t- hioepoxy-1-tellurobutyl), 1,4-bis(3,4-thioepoxy-1-tellurobutyl)-2,3-bis(6,7-thioepoxy-1-selena-4-te- lluroheptyl)butane, tris(4,5-thioepoxy-2-telluropentyl)-3-selena-6-thiaoctane-1,8-bis(3,4-thi- oepoxy-1-tellurobutyl), bis(5,6-epithio-3-tellurohexyl) telluride, 2,3-bis(6,7-thioepoxy-1-tellura-4-telluroheptyl)-1-(3,4-thioepoxy-1-tellu- robutyl)propane, 1,1,3,3-tetrakis(4,5-thioepoxy-2-telluropentyl)-2-tellurapropane, bis(4,5-thioepoxy-2-telluropentyl)-3,6,9-tritelleraundecane-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-t- elluroheptyl)butane and tris(4,5-thiepoxy-2-telluropentyl)-3-tellura-6-thiaoctane-1,8-bis(3,4-thi- oepoxy-1-tellurobutyl);

Compounds having alicyclic backbone:

1,3- or 1,4-bis(.beta.-epithiopropyltelluro)cyclohexane, 1,3- or 1,4-bis(.beta.-epithiopropyltelluromethyl)cyclohexane, bis[4-(.beta.-epithiopropyltelluro)cyclohexyl]methane, 2,2-bis[4-(.beta.-epithiopropyltelluro)cyclohexyl]propane, bis [4-(.beta.-epithiopropyltelluro)cyclohexyl] sulfide, 2,5-bis(.beta.-epithiopropyltelluromethyl)-1,4-dithiane, 2,5-bis(.beta.-epithiopropyltelluroethylthiomethyl)-1,4-dithiane, 2,3-, 2,5- or 2,6-bis(3,4-epithio-1-tellurobutyl)-1,4-diselenane, 2,3-, 2,5- or 2,6-bis(4,5-epithio-2-telluropentyl)-1,4-diselenane, 2,4-, 2,5- or 5,6-bis(3,4-epithio-1-tellurobutyl)-1,3-diselenane, 2,4-, 2,5- or 5,6-bis(4,5-epithio-2-telluropentyl)-1,3-diselenane, 2,3-, 2,5-, 2,6- or 3,5-bis(3,4-epithio-1-tellurobutyl)-1-thia-4-selenane, 2,3-, 2,5-, 2,6- or 3,5-bis(4,5-epithio-2-telluropentyl)-1-thia-4-selenolane, 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-diselenolane, 2,4-, 2,5- or 4,5-bis(3,4-epithio-1-tellurobutyl)-1-thia-3-selenoolane, 2,4-, 2,5- or 4,5-bis(4,5-epithio-2-telluropentyl)-1-thia-3-selenolane, 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)dicycloselenanonane, 2,3-, 2,4-, 2,5- or 3,4-bis(3,4-epithio-1-tellurobutyl)selenophane, 2,3-, 2,4-, 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-sele- nacyclohexane, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or 4,5-bis(3,4-thioepoxy-1-tellurobutyl)-1-selenacyclohexane, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or 4,5-bis(4,5-thioepoxy-2-telluropentyl)-1-selenacyclohexane, 2,3-, 2,5- or 2,6-bis(3,4-epithio-1-tellurobutyl)-1,4-ditellurane, 2,3-, 2,5- or 2,6-bis(4,5-epithio-2-telluropentyl)-1,4-ditellurane, 2,4-, 2,5- or 5,6-bis(3,4-epithio-1-tellurobutyl)-1,3-ditellurane, 2,4-, 2,5- or 5,6-bis(4,5-epithio-2-telluropentyl)-1,3-ditellurane, 2,3-, 2,5-, 2,6- or 3,5-bis(3,4-epithio-1-tellurobutyl)-1-thia-4-tellurane, 2,3-, 2,5-, 2,6- or 3,5-bis(4,5-epithio-2-telluropentyl)-1-thia-4-tellurane, 2,4- or 4,5-bis(3,4-epithio-1-tellurobutyl)-1,3-ditellurolane, 2,4- or 4,5-bis(4,5-epithio-2-telluropentyl)-1,3-ditellurolane, 2,4-, 2,5- or 4,5-bis(3,4-epithio-1-tellurobutyl)-1-thia-3-tellurolane, 2,4-, 2,5- or 4,5-bis(4,5-epithio-2-telluropentyl)-1-thia-3-tellurolane, 2,6-bis(4,5-epithio-2-telluropentyl)-1,3,5-tritellurane, bis(3,4-epithio-1-tellurobutyl)tricyclotelluraoctane, bis(3,4-epithio-1-tellurobutyl)dicyclotelluranonane, 2,3-, 2,4-, 2,5- or 3,4-bis(3,4-epithio-1-tellurobutyl)tellurophane, 2,3-, 2,4-, 2,5- or 3,4-bis(4,5-epithio-2-telluropentyl)tellurophane, 2-(4,5-thioepoxy-2-telluropentyl)-5-(3,4-thioepoxy-1-tellurobutyl)-1-tell- uracyclohexane, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or 4,5-bis(3,4-thioepoxy-1-tellurobutyl)-1-telluracyclohexane, and 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or 4,5-bis(4,5-thioepoxy-2-telluropentyl)-1-telluracyclohexane;

Compounds having aromatic backbone:

1,3- or 1,4-bis(.beta.-epithiopropyltelluro)benzene, 1,3- or 1,4-bis(.beta.-epithiopropyltelluromethyl)benzene, bis[4-(.beta.-epithiopropyltelluro)phenyl] methane, 2,2-bis [4-(.beta.-epithiopropyltelluro)phenyl]propane, bis [4-(.beta.-epithiopropyltelluro)phenyl] sulfide, bis[4-(.beta.-epithiopropyltelluro)phenyl] sulfone, and 4,4'-bis(.beta.-epithiopropyltelluro)biphenyl; and

Compounds obtained by replacing at least one hydrogen of the .beta.-epithiopropyl group in the above compounds with methyl.

The compounds (A) to (E) may include those having an unsaturated group. Examples thereof include vinylphenyl thioglycidyl ether, vinylbenzyl thioglycidyl ether, thioglycidyl methacrylate, thioglycidyl acrylate and allyl thioglycidyl ether.

The compound (a) is not limited to those mentioned above and may be used alone or in combination of two or more.

Of the above compounds, preferred are the compounds (B) having in one molecule at least one structure of Formula 1 wherein Y is 0, the compounds (C) having in one molecule at least one structure of Formula 1 wherein Y is S, the compounds (D) having in one molecule at least one structure of Formula 1 wherein Y is Se. More preferred are the compounds (C) and (D). Still more preferred are the compounds (C) and (D) wherein m is 1 or 2, and n is 1 or 2, and the most preferred are the compounds (C) and (D) wherein m is 1 and n is 1 or 2.

Examples of the most preferred compounds include bis(.beta.-epithiopropyl) sulfide, bis(.beta.-epithiopropyl) disulfide, bis(.beta.-epithiopropyl) selenide, bis(.beta.-epithiopropyl) diselenide, and compounds having two or more .beta.-epithiopropylthio groups or .beta.-epithiopropylseleno groups together with the chain backbone, the branched backbone, the alicyclic backbone, the aromatic backbone or the heterocyclic backbone mentioned above. Especially preferred of the above are chain or branched compounds having two or more .beta.-epithiopropylthio groups or .beta.-epithiopropylseleno groups, bis(.beta.-epithiopropyl) sulfide, bis(.beta.-epithiopropyl) disulfide, bis(.beta.-epithiopropyl) selenide, and bis(.beta.-epithiopropyl) diselenide.

The compound (b) includes any compounds having in one molecule at least one isocyanate group and/or isothiocyanate group. Examples thereof include isocyanate compounds such as methyl isocyanate, ethyl isocyanate, propyl isocyanate, isopropyl isocyanate, n-butyl isocyanate, sec-butyl isocyanate, tert-butyl isocyanate, pentyl isocyanate, hexyl isocyanate, octyl isocyanate, dodecyl isocyanate, cyclohexyl isocyanate, phenyl isocyanate, tolyl isocyanate, diethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, 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-tolydyne diisocyanate, 4,4'-diphneylmethane diisocyanate, diphenyl ether diisocyanate, 3-(2'-isocyanatocyclohexyl)propyl isocyanate, tris(phenylisocyanate) thiophosphate, isopropylidene bis(cyclohexylisocyanate), 2,2'-bis(4-isoisocyanatophenyl)propane, triphenylmethane triisocyanate, bis(diisocyanatotolyl)phenylmethane, 4,4',4''-triisocyanato-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, dicyclohexylmethan-4,4'-diisocyanate, 1,1'-methylenebis(4-isocyanatobenzene), 1,1'-methylenebis(3-methyl-4-isocyanatobenzene), m-xylylene diisocyanate, .beta.-xylylene diisocyanate, 1,3-bis(1-isocyanato-1-methylethyl)benzene, 1,4-bis(1-isocyanato-1-methylethyl)benzene, 1,3-bis(2-isocyanato-2-propyl)benzene, 2,6-bis(isocyanatomethyl)naphthalene, 1,5-naphthalene diisocyanate, bis(isocyanatomethyl)tetrahydrodicyclopentadiene, bis(isocyanatomethyl)dicyclopentadiene, bis(isocyanatomethyl)tetrahydrothiophene, 2,5-diisocyanatomethylnorbornene, bis(isocyanatomethyl)adamantane, dimeric acid diisocyanate, 1,3,5-tri(1-isoisocyanatohexyl)isocyanuric acid, thiodiethyl diusocyanate, thiodipropyl diisocyanate, thiodihexyl diisocyanate, bis[(4-isocyanatomethyl)phenyl] sulfide, 2,5-diisocyanato-1,4-dithiane, 2,5-diisocyanatomethyl-1,4-dithiane, 2,5-diisocyanatomethyl thiophene, dithiodiethyl diisocyanate, and dithiodipropyl diisocyanate; and compounds derived from the above isocyanate compounds by replacing all or a part of the isocyanate group thereof with isothiocyanate group. The polyisocyanate compounds mentioned above includes dimers produced by biuret reaction, cyclic trimers, alcohol adducts and thiol adducts.

The compound (b) is not limited to those mentioned above and may be used alone or in combination of two or more. Preferred compounds (b) are those having in one molecule two or more isocyanate groups and/or isothiocyanate groups.

The compound (c) includes any compounds having in one molecule at least one mercapto group. Examples thereof include mercaptans such as 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, isopropyl mercaptan, tert-butyl mercaptan, tert-nonyl mercaptan, tert-dodecyl mercaptan, phenyl mercaptan, benzyl mercaptan, 3-methylphenyl mercaptan, 4-methylphenyl mercaptan, 4-chlorobenzyl mercaptan, 4-vinylbenzyl mercaptan, 3-binylbenzyl mercaptan, methyl mercaptopropionate, ethyl thioglycolate, n-butyl thioglycolate, n-octyl thioglycolate, methyl 3-mercaptopropionate, ethyl 3-mercaptopropionate, 3-methoxybutyl 3-mercaptopropionate, n-butyl 3-mercaptopropionate, 2-ethylhexyl 3-mercaptopropionate, 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-mercaptoethanol, 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-dimecrapto-1-propanol, 1,3-dimercapto-2-propanol, 1,2,3-trimercaptopropane, 2-mercaptomethyl-1,3-dimercaptopropane, 2-mercaptomethyl-1,4-dimercaptobutane, 2-(2-mercaptoethylthio)-1,3-dimercaptopropane, 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, 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-mercaptopropionate), 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-thiane, 2,5-bis(2-mercaptoethyl)-1-thiane, 2,5-bis(mercaptomethyl)thiophene, thiophenol, 4-tert-butylthiophenol, 2-methylthiophenol, 3-methylthiophenol, 4-methylthiophenol, 2-vinylthiophenol, 3-vinylthiophenol, 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, 2,2-bis(4-mercaptomethylphenyl)propane, 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(mercaptoethylseleno)-1-propanethiol, 2-mercaptomethyl-1,5-dimercapto-3-selenapentane, 4,8-bis(mercaptomethyl)-1,11-dimercapto-3,9-dithia-6-selenaundecane, 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(mercaptomethyl)-3,7-diselenanonane, 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(mercaptoethylselenomethyl)-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-1,3-diselenorane, 4,5-bis(dimercapto)-1,3-diselenorane, 3,6-dimercaptotriselenocyclooctane, 3,6-bis(mercaptomethyl)triselenocyclooctane, 3,6-diselenotriselenocyclooctane, and 3,6-bis(selenomethyl)triselenocycloocatane. The polymercaptans mentioned above include oligomers of about 2 to 20 polymerization degree.

The compound (c) is not limited to those mentioned above and may be used alone or in combination of two or more. Preferred compounds (c) are those having in one molecule two or more mercapto groups. More preferred are those having a sulfur atom in addition to the mercapto groups, and still more preferred are those having a sulfide linkage.

The compound (d) includes any inorganic compounds having at least one sulfur atom and/or selenium atom. The total amount of sulfur atom and/or selenium atom in the inorganic compound is preferably 30% by weight or more. When the amount is less than 30%, the effect of increasing the refractive index of resin is lowered because the amount of sulfur atom and/or selenium atom in the composition for optical materials increases not so much.

Examples of the inorganic compounds having sulfur atom include sulfur, hydrogen sulfide, carbon disulfide, carbon selenosulfide, ammonium sulfide, sulfur oxides such as sulfur dioxide and sulfur trioxide, salts of thiocarbonic acid, sulfuric acid, salts of sulfuric acid, salts of hydrogensulfuric acid, salts of sulfurous acid, salts of hyposulfurous acid, salts of persulfuric acid, salts of thiocyanic acid, salts of thiosulfuric acid, halides such as sulfur dichloride, thionyl chloride and thiophosgen, boron sulfide, nitrogen sulfide, silicon sulfide, phosphorus sulfide, arsenic sulfide, selenium sulfide, metal sulfides and metal hydrogensulfides. Among these compounds, sulfur, carbon disulfide, phosphorus sulfide, selenium sulfide, metal sulfides and metal hydrogensulfides are preferable, and sulfur, carbon disulfide and selenium sulfide are more preferable.

Examples of the inorganic compounds having selenium atom include, in addition to carbon selenosulfide and selenium sulfide mentioned above as the examples for the inorganic compound having sulfur atom, selenium, hydrogen selenide, selenium dioxide, carbon diselenide, ammonium selenide, oxides of selenium such as selenium dioxide, selenic acid, salts of selenic acid, selenous acid, salts of selenous acid, salts of hydrogenselenic acid, selenosulfuric acid, salts of selenosulfuric acid, selenopyrosulfuric acid, salts of selenopyrosulfuric acid, halides such as selenium tetrabromide and selenium oxychloride, salts of selenocyanic acid, boron selenide, phosphorus selenide, arsenic selenide and metal selenides. Among these compounds, selenium, carbon diselenide, phosphorus selenide and metal selenides are preferable, and selenium and carbon diselenide are more preferable. These inorganic compounds having at least one sulfur atom and/or selenium atom may be used alone or in combination of two or more.

The compound (d) is not limited to those mentioned above and may be used alone or in combination of two or more.

The composition of the present invention comprising the compound (a), compound (b), compound (c) and compound (d) is polymerized to a resin under heating in the presence or absence of a curing catalyst, preferably in the presence of a curing catalyst. As the curing catalyst, usable are amines, quaternary ammonium salts, phosphines, quaternary phosphonium salts, tertiary sulfonium salts, secondary iodonium salts, mineral acids, Lewis acids, organic acids, silicic acids, tetrafluoroboric acids, peroxides, azo compounds, condensates of aldehyde and amine compound, guanidine compounds, thiourea compounds, thiazole compounds, sulfenamide compounds, thiuram compounds, salts of dithiocarbamic acid, salts of xanthogenic acid, and acid phosphates.

Examples of the curing catalysts are mentioned below.

(1) Amines

Primary amines such as ethylamine, n-propylamine, sec-propylamine, n-butylamine, sec-butylamine, isobutylamine, tert-butylamine, pentylamine, hexylamine, heptylamine, octylamine, decylamine, laurylamine, myristylamine, 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, phenetylamine, a-phenylethylamine, naphthylamine and furfurylamine; primary polyamines such as 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-bisaminopropylpiperadine, o-, m- or p-phenylenediamine, 2,4- or 2,6-tolylenediamine, 2,4-toluenediamine, m-aminobenzylamine, 4-chloro-o-phenylenediamine, tetrachloro-p-xylylenedia