U.S. patent application number 09/757629 was filed with the patent office on 2001-07-19 for process for production of optical material.
Invention is credited to Takeuchi, Motoharu, Yoshimura, Yuichi.
Application Number | 20010008278 09/757629 |
Document ID | / |
Family ID | 18538971 |
Filed Date | 2001-07-19 |
United States Patent
Application |
20010008278 |
Kind Code |
A1 |
Yoshimura, Yuichi ; et
al. |
July 19, 2001 |
Process for production of optical material
Abstract
An improved process for producing optical materials with
minimized yellowing is described. The process is characterized by
polymerizing/curing a composition for optical materials after
adding a bluing agent. With the use of the bluing agent, the
yellowing is minimized even when a large amount of an ultraviolet
light absorber is used to improve a light resistance of the
resultant optical material, thereby enabling the production of
optical materials having a colorless and transparent appearance and
excellent optical properties.
Inventors: |
Yoshimura, Yuichi;
(Chiba-ken, JP) ; Takeuchi, Motoharu; (Tokyo,
JP) |
Correspondence
Address: |
ANTONELLI TERRY STOUT AND KRAUS
SUITE 1800
1300 NORTH SEVENTEENTH STREET
ARLINGTON
VA
22209
|
Family ID: |
18538971 |
Appl. No.: |
09/757629 |
Filed: |
January 11, 2001 |
Current U.S.
Class: |
252/582 |
Current CPC
Class: |
G02B 1/04 20130101; C08G
75/08 20130101; G02B 1/04 20130101; C08L 81/04 20130101; C08L 81/00
20130101 |
Class at
Publication: |
252/582 |
International
Class: |
G03C 001/00 |
Foreign Application Data
Date |
Code |
Application Number |
Jan 19, 2000 |
JP |
11044/2000 |
Claims
What is claimed is:
1. A process for producing an optical material, comprising: adding
a bluing agent to a composition for optical materials comprising a
compound having a radical represented by the formula (I): 2wherein
R.sup.1 is C.sub.1-C.sub.10 hydrocarbon group; R.sup.2, R.sup.3 and
R.sup.4 are each independently C.sub.1-C.sub.10 hydrocarbon group
or hydrogen; Y is O, S, Se or Te; p is 0 or 1; m is an integer of 1
to 5; and n is an integer of 0 to 5, thereby preparing a molding
composition; and subjecting the molding composition to
polymerization and curing in a mold.
2. The process according to claim 1, wherein the amount of the
compound having the radical represented by the formula (I) is 10%
by weight or more based on the total weight of the composition for
optical materials.
3. The process according to claim 1, wherein the bluing agent is
added to the composition for optical materials in an amount of
0.000001 to 0.5 part by weight based on 100 parts by weight of the
composition.
4. The process according to claim 1, wherein the bluing agent is an
anthraquinone compound.
5. The process according to claim 1, wherein the molding
composition is prepared by mixing at -50 to 100.degree. C. for one
minute to 5 hours.
6. The process according to claim 1, wherein the molding
composition is subjected to pre-polymerization at -100 to
160.degree. C. for 0.1 to 288 hours prior to injecting the molding
composition into the mold.
7. The process according to claim 1, wherein the molding
composition is subjected to polymerization/curing at -10 to
160.degree. C. for 0.1 to 100 hours.
8. The process according to claim 1, wherein the composition for
optical materials is further added with a red anthraquinone
compound, an orange anthraquinone compound or a brown anthraquinone
compound.
9. The process according to claim 8, wherein the red anthraquinone
compound, an orange anthraquinone compound or a brown anthraquinone
compound is added in an amount of 0.000001 to 0.0005 part by weight
based on 100 parts by weight of the composition for optical
materials.
10. An optical material produced by the process according to claim
1.
Description
BACKGROUND OF THE INVENTION
[0001] 1. Field of the Invention
[0002] The present invention relates to a process for producing an
optical material such as plastic lens, prisms, optical fibers,
information recording substrates and filters, especially plastic
spectacle lens.
[0003] 2. Description of the Prior Art
[0004] Recently, plastic materials have been more widely used for
the production of various optical materials, especially spectacle
lens, due to their light weight, excellent toughness and high
affinity to dye. These optical materials, especially spectacle
lens, have been required to have in addition to low specific
gravity, high transparency, low yellowness and good optical
properties such as high refractive index and high Abbe's number.
The high refractive index reduces the thickness of the lens, and
the high and high Abbe's number reduces the chromatic aberration of
the lens. The present inventors have found the novel episulfide
compound capable of producing an optical material having a small
thickness and a low chromatic aberration, i.e., a refractive index
of 1.7 or more and an Abbe's number of 35 or more, and have filed
patent applications relating thereto (U.S. Pat. Nos. 5,807,975 and
5,945,504, European Patent Publications 0978513 and 1024223, and
Japanese Patent Application Laid-Open No. 11-180977, which are
incorporated herein by reference).
[0005] However, these high-refractive index optical materials tend
to be colored yellow upon polymerization. In particular, the
yellowing of the materials is remarkable when a large amount of an
ultraviolet light absorber is added to the optical materials to
improve a light resistance.
SUMMARY OF THE INVENTION
[0006] Therefore, an object of the present invention is to improve
the color tone of these high-refractive index optical
materials.
[0007] As a result of extensive researches in view of the above
object, the present inventors have found that a polymerizable
composition for optical materials added with a bluing agent
produces, through polymerization and curing, a colorless and
transparent optical material having excellent optical properties.
The present invention has been accomplished based on this
finding.
[0008] Thus, the present invention provides a process for producing
an optical material, comprising (1) adding a bluing agent to a
composition for optical materials comprising a compound having at
least one radical represented by the formula (I): 1
[0009] wherein R.sup.1 is C.sub.1-C.sub.10 hydrocarbon group;
R.sup.2, R.sup.3 and R.sup.4 are each independently
C.sub.1-C.sub.10 hydrocarbon group or hydrogen; Y is O, S, Se or
Te; p is 0 or 1; m is an integer of 1 to 5; and n is an integer of
0 to 5; and
[0010] subjecting the resultant composition to polymerization and
curing.
DETAILED DESCRIPTION OF THE INVENTION
[0011] The optical materials produced from the compound having a
radical represented by the formula (I) exhibit a high refractive
index and a high Abbe's number and are well-balanced between both
the properties. In the formula (I), R.sup.1 is preferably methylene
or ethylene, more preferably methylene; R.sup.2, R.sup.3 and
R.sup.4 are preferably hydrogen or methyl, more preferably
hydrogen; p is 0 or 1, preferably 1; m is an integer of 1 to 5,
preferably 1 or 2, more preferably 1; n is an integer of 0 to 5,
preferably 0 to 4, more preferably 0 to 2; and Y is O, S, Se or Te,
preferably O, S or Se, more preferably S or Se. The compound having
the radical represented by the formula (I) may be use alone or in
combination of two or more.
[0012] Examples of the compound having the radical represented by
the formula (I) are listed below while classified into the groups
(A) to (E):
[0013] (A) Compounds having in one molecule at least one radical
represented by the formula (I) wherein n is 0;
[0014] (B) Compounds (a) having in one molecule at least one
radical represented by the formula (I) wherein Y is O;
[0015] (C) Compounds (a) having in one molecule at least one
radical represented by the formula (I) wherein Y is S;
[0016] (D) Compounds (a) having in one molecule at least one
radical represented by the formula (I) wherein Y is Se; and
[0017] (E) Compounds (a) having in one molecule at least one
radical represented by the formula (I) wherein Y is Te.
[0018] The group (A) to (E) compounds has a backbone structure
derived from a chain compound, a branched compound, an alicyclic
compound, an aromatic compound or a heterocyclic compound having
nitrogen, oxygen, sulfur, selenium or tellurium as the heteroatom.
The compounds may have a plurality of the above structures in one
molecule. 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 in the molecule.
[0019] Examples of the group (A) compound include:
[0020] Organic compounds having a chain aliphatic backbone
structure such as 1,1-bis(epithioethyl)methane,
1,1-bis(epidithioethyl)methane, 1-(epithioethyl)-1-(.beta.
-epithiopropyl)-methane, 1,1-bis(.beta.-epithiopropyl)-methane,
1-(epithioethyl)-1-(.beta.-epithio- propyl)ethane,
1,2-bis(.beta.-epithiopropyl)ethane, 1,2-bis(.beta.
-epidithiopropyl)ethane,
1-(epithioethyl)-3-(.beta.-epithiopropyl)butane, 1,3-bis(.beta.
-epithiopropyl)propane, 1-(epithioethyl)-4-(.beta.-epithio-
propyl)pentane, 1,4-bis(.beta. -epithiopropyl)butane,
1-(epithioethyl)-5-(.beta.-epithiopropyl)hexane,
1-(epithioethyl)-2-(.gam- ma.-epithiobutylthio)ethane,
1-(epithioethyl)-2-[2-(.gamma. -epithiobutylthio)ethylthio]ethane,
tetrakis(.beta.-epithiopropyl)methane- ,
1,1,1-tris(.beta.-epithiopropyl)propane,
1,3-bis(.beta.-epithiopropyl)-1-
-(.beta.-epithiopropyl)-2-thiapropane and
1,5-bis(.beta.-epithiopropyl)-2,-
4-bis(.beta.-epithiopropyl)-3-thiapentane;
[0021] Compounds having an alicyclic backbone structure such as
1,3-bis(epithioethyl)cyclohexane, 1,4-bis(epithioethyl)cyclohexane,
1,3-bis(.beta.-epithiopropyl)cyclohexane,
1,4-bis(.beta.-epithiopropyl)cy- clohexane,
bis[4-(epithioethyl)cyclohexyl]methane, bis[4-(.beta.-epithiopr-
opyl)cyclohexyl]methane,
2,2-bis[4-(epithioethyl)cyclohexyl]propane, 2,2-bis[4-(.beta.
-epithiopropyl)cyclohexyl]propane,
bis[4-(.beta.-epithiopropyl)cyclohexyl] sulfide,
bis[4-(epithioethyl)cycl- ohexyl] sulfide,
2,5-bis(epithioethyl)-1,4-dithiane,
2,5-bis(.beta.-epithiopropyl)-1,4-dithiane,
4-epithioethyl-1,2-cyclohexen- e sulfide, 4-epoxy-1,2-cyclohexene
sulfide, 2,3-bis(1,2-epithioethyl)-1,4-- diselenane,
2,5-bis(1,2-epithioethyl)-1,4-diselenane,
2,6-bis(1,2-epithioethyl)-1,4-diselenane,
2,3-bis(2,3-epithiopropyl)-1,4-- diselenane,
2,5-bis(2,3-epithiopropyl)-1,4-diselenane,
2,6-bis(2,3-epithiopropyl)-1,4-diselenane,
2,4-bis(1,2-epithioethyl)-1,3-- diselenane,
2,5-bis(1,2-epithioethyl)-1,3-diselenane,
2,6-bis(1,2-epithioethyl)-1,3-diselenane,
2,4-bis(2,4-epithiopropyl)-1,3-- diselenane,
2,5-bis(2,4-epithiopropyl)-1,3-diselenane,
2,6-bis(2,4-epithiopropyl)-1,3-diselenane,
2,3-bis(1,2-epithioethyl)-1-th- ia-4-selenane,
2,5-bis(1,2-epithioethyl)-1-thia-4-selenane,
2,6-bis(1,2-epithioethyl)-1-thia-4-selenane,
3,5-bis(1,2-epithioethyl)-1-- thia-4-selenane,
2,3-bis(2,3-epithiopropyl)-1-thia-4-selenane,
2,5-bis(2,3-epithiopropyl)-1-thia-4-selenane,
2,6-bis(2,3-epithiopropyl)-- 1-thia-4-selenane,
3,5-bis(2,3-epithiopropyl)-1-thia-4-selenane,
2,4-bis(1,2-epithioethyl)-1,3-diselenolane,
4,5-bis(1,2-epithioethyl)-1,3- -diselenolane,
2,4-bis(2,4-epithiopropyl)-1,3-diselenolane,
4,5-bis(2,4-epithiopropyl)-1,3-diselenolane,
2,4-bis(1,2-epithioethyl)-1-- thia-3-selenolane,
2,5-bis(1,2-epithioethyl)-1-thia-3-selenolane,
4,5-bis(1,2-epithioethyl)-1-thia-3-selenolane,
2,4-bis(2,4-epithiopropyl)- -1-thia-3-selenolane,
2,5-bis(2,4-epithiopropyl)-1-thia-3-selenolane,
4,5-bis(2,4-epithiopropyl)-1-thia-3-selenolane,
2,3-bis(1,2-epithioethyl)- selenophane,
2,4-bis(1,2-epithioethyl)selenophane, 2,5-bis(1,2-epithioethy-
l)selenophane, 3,4-bis(1,2-epithioethyl)selenophane,
2,3-bis(2,3-epithiopropyl)selenophane,
2,4-bis(2,3-epithiopropyl)selenoph- ane,
2,5-bis(2,3-epithiopropyl)selenophane,
3,4-bis(2,3-epithiopropyl)sele- nophane,
2,3-bis(1,2-epithioethyl)-1,4-ditellurane,
2,5-bis(1,2-epithioethyl)-1,4-ditellurane,
2,6-bis(1,2-epithioethyl)-1,4-- ditellurane,
2,3-bis(2,3-epithiopropyl)-1,4-ditellurane,
2.5-bis(2,3-epithiopropyl)-1,4-ditellurane,
2,6-bis(2,3-epithiopropyl)-1,- 4-ditellurane,
2,4-bis(1,2-epithioethyl)-1,3-ditellurane,
2,5-bis(1,2-epithioethyl)-1,3-ditellurane,
2,6-bis(1,2-epithioethyl)-1,3-- ditellurane,
2,4-bis(2,4-epithiopropyl)-1,3-ditellurane,
2,5-bis(2,4-epithiopropyl)-1,3-ditellurane,
2,6-bis(2,4-epithiopropyl)-1,- 3-ditellurane,
2,3-bis(1,2-epithioethyl)-1-thia-4-tellurane,
2,5-bis(1,2-epithioethyl)-1-thia-4-tellurane,
2,6-bis(1,2-epithioethyl)-1- -thia-4-tellurane,
3,5-bis(1,2-epithioethyl)-1-thia-4-tellurane,
2,3-bis(2,3-epithiopropyl)-1-thia-4-tellurane,
2,5-bis(2,3-epithiopropyl)- -1-thia-4-tellurane,
2,6-bis(2,3-epithiopropyl)-1-thia-4-tellurane,
3,5-bis(2,3-epithiopropyl)-1-thia-4-tellurane,
2,4-bis(1,2-epithioethyl)-- 1,3-ditellurolane,
4,5-bis(1,2-epithioethyl)-1,3-ditellurolane,
2,4-bis(2,4-epithiopropyl)-1,3-ditellurolane,
4,5-bis(2,4-epithiopropyl)-- 1,3-ditellurolane,
2,4-bis(1,2-epithioethyl)-1-thia-3-tellurolane,
2,5-bis(1,2-epithioethyl)-1-thia-3-tellurolane,
4,5-bis(1,2-epithioethyl)- -1-thia-3-tellurolane,
2,4-bis(2,4-epithiopropyl)-1-thia-3-tellurolane,
2,5-bis(2,4-epithiopropyl)-1-thia-3-tellurolane,
4,5-bis(2,4-epithiopropy- l)-1-thia-3-tellurolane,
2,3-bis(1,2-epithioethyl)tellurophane,
2,4-bis(1,2-epithioethyl)tellurophane,
2,5-bis(1,2-epithioethyl)telluroph- ane,
3,4-bis(1,2-epithioethyl)tellurophane,
2,3-bis(2,3-epithiopropyl)tell- urophane,
2,4-bis(2,3-epithiopropyl)tellurophane, 2,5-bis(2,3-epithiopropy-
l)tellurophane and 3,4-bis(2,3-epithiopropyl)tellurophane;
[0022] Compounds having an aromatic backbone structure such as
1,3-bis(epithioethyl)benzene, 1,4-bis(epithioethyl)benzene,
1,3-bis(.beta. -epithiopropyl)benzene,
1,4-bis(.beta.-epithiopropyl)benze- ne,
bis[4-(epithioethyl)phenyl]methane,
bis[4-(.beta.-epithiopropyl)phenyl- ]methane,
2,2-bis[4-(epithioethyl)phenyl]propane, 2,2-bis[4-(.beta.-epithi-
opropyl)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)bipheny- l; and
[0023] Compounds obtained by replacing at least one hydrogen of the
epithio group in the above compounds with methyl.
[0024] Examples of the group (B) compound include:
[0025] Compounds having a chain aliphatic backbone structure such
as bis(.beta. -epithiopropyl) ether, bis(.beta.-epidithiopropyl)
ether, bis(.beta. -epithiopropyloxy)methane,
1,2-bis(.beta.-epithiopropyloxy)eth- ane,
1,3-bis(.beta.-epithiopropyloxy)propane,
1,2-bis(.beta.-epithiopropyl- oxy)propane, 1-(.beta.
-epithiopropyloxy)-2-(.beta.-epithiopropyloxymethyl- )propane,
1,4-bis(.beta.-epithiopropyloxy)butane, 1,3-bis(.beta.-epithiopr-
opyloxy)butane, 1-(.beta.
-epithiopropyloxy)-3-(.beta.-epithiopropyloxymet- hyl)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)oxyet- hyl]oxy]ethane,
bis(5,6-epithio-3-oxahexyl) selenide, bis(5,6-epithio-3-oxahexyl)
telluride, tetrakis(.beta.-epithiopropyloxyme- thyl)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.-epithiopr-
opyloxymethyl)-4-thiahexane, 1,5,6-tris(.beta.
-epithiopropyloxy)-4-(.beta-
.-epithiopropyloxymethyl)-3-thiahexane, 1,8-bis(.beta.
-epithiopropyloxy)-4-(.beta.-epithiopropyloxymethyl)-3,6-dithiaoctane,
1,8-bis(.beta.
-epithiopropyloxy)-4,5-bis(.beta.-epithiopropyloxymethyl)--
3,6-dithiaoctane, 1,8-bis(.beta.
-epithiopropyloxy)-4,4-bis(.beta.-epithio-
propyloxymethyl)-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.-epithiopropylo-
xymethyl)-5-[(2- .beta.
-epithiopropyloxyethyl)oxymethyl]-3,7-dithianonane- ,
1,10-bis(.beta.
-epithiopropyloxy)-5,6-bis[(2-.beta.-epithiopropyloxyeth-
yl)oxy]-3,6,9-trithiadecane,
1,11-bis(.beta.-epithiopropyloxy)-4,8-bis(.be-
ta.-epithiopropyloxymethyl)-3,6,9-trithiaundecane,
1,11-bis(.beta.-epithio- propyloxy)-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-b-
is(.beta.-epithiopropyloxymethyl)-3,6,9-trithiaundecane;
[0026] Compounds having an alicyclic backbone structure such as
1,3-bis(.beta. -epithiopropyloxy)cyclohexane,
1,4-bis(.beta.-epithiopropy- loxy)cyclohexane,
1,3-bis(.beta.-epithiopropyloxymethyl)cyclohexane, 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.-epithiopropyloxymet- hyl)-1,4-dithiane,
2,5-bis(.beta.-epithiopropyloxyethyloxymethyl)-1,4-dith- iane,
2,4-bis(3,4-epithio-1-oxabutyl)-1,3-diselenolane,
4,5-bis(3,4-epithio-1-oxabutyl)-1,3-diselenolane,
4,5-bis(4,5-epithio-2-o- xapentyl)-1,3-diselenolane,
2,4-bis(4,5-epithio-2-oxapentyl)-1,3-diselenol- ane,
2,4-bis(3,4-epithio-1-oxabutyl)-1-thia-3-selenolane,
2,5-bis(3,4-epithio-1-oxabutyl)-1-thia-3-selenolane,
4,5-bis(3,4-epithio-1-oxabutyl)-1-thia-3-selenolane,
2,4-bis(4,5-epithio-2-oxapentyl)-1-thia-3-selenolane,
2,5-bis(4,5-epithio-2-oxapentyl)-1-thia-3-selenolane,
4,5-bis(4,5-epithio-2-oxapentyl)-1-thia-3-selenolane,
bis(3,4-epithio-1-oxabutyl)tricycloselenaoctane,
bis(3,4-epithio-1-oxabut- yl)dicycloselenanonane,
2,3-bis(3,4-epithio-1-oxabutyl)selenophane,
2,4-bis(3,4-epithio-1-oxabutyl)selenophane,
2,5-bis(3,4-epithio-1-oxabuty- l)selenophane,
3,4-bis(3,4-epithio-1-oxabutyl)selenophane, 2,3-bis(4,
5-epithio-2-oxapentyl)selenophane,
2,4-bis(4,5-epithio-2-oxapenty)selenop- hane,
2,5-bis(4,5-epithio-2-oxapentyl)-selenophane,
3,4-bis(4,5-epithio-2-oxapentyl)selenophane,
2,3-bis(3,4-epithio-1-oxabut- yl)-1,4-diselenane,
2,5-bis(3,4-epithio-1-oxabutyl)-1,4-diselenane,
2,6-bis(3,4-epithio-1-oxabutyl)-1,4-diselenane,
2,3-bis(4,5-epithio-2-oxa- pentyl)-1,4-diselenane,
2,5-bis(4,5-epithio-2-oxapentyl)-1,4-diselenane,
2,6-bis(4,5-epithio-2-oxapentyl)-1,4-diselenane,
2,4-bis(3,4-epithio-1-ox- abutyl)-1,3-diselenane,
2,5-bis(3,4-epithio-1-oxabutyl)-1,3-diselenane,
2,6-bis(3,4-epithio-1-oxabutyl)-1,3-diselenane,
2,4-bis(4,5-epithio-2-oxa- pentyl)-1,3-diselenane,
2,5-bis(4,5-epithio-2-oxapentyl)-1,3-diselenane,
2,6-bis(4,5-epithio-2-oxapentyl)-1,3-diselenane,
2,3-bis(3,4-epithio-1-ox- abutyl)-1-thia-4-selenane,
2,5-bis(3,4-epithio-1-oxabutyl)-1-thia-4-selena- ne,
2,6-bis(3,4-epithio-1-oxabutyl)-1-thia-4-selenane,
3,5-bis(3,4-epithio-1-oxabutyl)-1-thia-4-selenane,
2,3-bis(4,5-epithio-2-oxapentyl)-1-thia-4-selenane,
2,5-bis(4,5-epithio-2-oxapentyl)-1-thia-4-selenane,
2,6-bis(4,5-epithio-2-oxapentyl)-1-thia-4-selenane,
3,5-bis(4,5-epithio-2-oxapentyl)-1-thia-4-selenane,
2,4-bis(3,4-epithio-1-oxabutyl)-1,3-ditellurolane,
4,5-bis(3,4-epithio-1-oxabutyl)-1,3-ditellurolane,
2,4-bis(4,5-epithio-2-oxapentyl)-1,3-ditellurolane,
4,5-bis(4,5-epithio-2-oxapentyl)-1,3-ditellurolane,
2,4-bis(3,4-epithio-1-oxabutyl)-1-thia-3-tellurolane,
2,5-bis(3,4-epithio-1-oxabutyl)-1-thia-3-tellurolane,
4,5-bis(3,4-epithio-1-oxabutyl)-1-thia-3-tellurolane,
2,4-bis(4,5-epithio-2-oxapentyl)-1-thia-3-tellurolane,
2,5-bis(4,5-epithio-2-oxapentyl)-1-thia-3-tellurolane,
4,5-bis(4,5-epithio-2-oxapentyl)-1-thia-3-tellurolane,
bis(3,4-epithio-1-oxabutyl)tricyclotelluraoctane,
bis(3,4-epithio-1-oxabu- tyl)dicyclotelluranonane,
2,3-bis(3,4-epithio-1-oxabutyl)tellurophane,
2,4-bis(3,4-epithio-1-oxabutyl)tellurophane,
2,5-bis(3,4-epithio-1-oxabut- yl)tellurophane,
3,4-bis(3,4-epithio-1-oxabutyl)tellurophane,
2,3-bis(4,5-epithio-2-oxapentyl)tellurophane,
2,4-bis(4,5-epithio-2-oxape- ntyl)-tellurophane,
2,5-bis(4,5-epithio-2-oxapentyl)tellurophane,
3,4-bis(4,5-epitho-2-oxapentyl)tellurophane,
2,3-bis(3,4-epithio-1-oxabut- yl)-1,4-ditellurane,
2,5-bis(3,4-epithio-1-oxabutyl)-1,4-ditellurane,
2,6-bis(3,4-epithio-1-oxabutyl)-1,4-ditellurane,
2,3-bis(4,5-epithio-2-ox- apentyl)-1,4-ditellurane,
2,5-bis(4,5-epithio-2-oxapentyl)-1,4-ditellurane- ,
2,6-bis(4,5-epithio-2-oxapentyl)-1,4-ditellurane,
2,4-bis(3,4-epithio-1-oxabutyl)-1,3-ditellurane,
2,5-bis(3,4-epithio-1-ox- abutyl)-1,3-ditellurane,
2,6-bis(3,4-epithio-1-oxabutyl)-1,3-ditellurane,
2,4-bis(4,5-epithio-2-oxapentyl)-1,3-ditellurane,
2,5-bis(4,5-epithio-2-o- xapentyl)-1,3-ditellurane,
2,6-bis(4,5-epithio-2-oxapentyl)-1,3-ditelluran- e,
2,3-bis(3,4-epithio-1-oxabutyl)-1-thia-4-tellurane,
2,5-bis(3,4-epithio-1-oxabutyl)-1-thia-4-tellurane,
2,6-bis(3,4-epithio-1-oxabutyl)-1-thia-4-tellurane,
3,5-bis(3,4-epithio-1-oxabutyl)-1-thia-4-tellurane,
2,3-bis(4,5-epithio-2-oxapentyl)-1-thia-4-tellurane,
2,5-bis(4,5-epithio-2-oxapentyl)-1-thia-4-tellurane,
2,6-bis(4,5-epithio-2-oxapentyl)-1-thia-4-tellurane and
3,5-bis(4,5-epithio-2-oxapentyl)-1-thia-4-tellurane;
[0027] Compounds having an aromatic backbone structure such as
1,3-bis(.beta. -epithiopropyloxy)benzene,
1,4-bis(.beta.-epithiopropyloxy- )benzene, 1,3-bis(.beta.
-epithiopropyloxymethyl)benzene,
1,4-bis(.beta.-epithiopropyloxymethyl)benzene,
bis[4-(.beta.-epithiopropy- l)phenyl]methane, 2,2-bis[4-(.beta.
-epithiopropylthio)phenyl]propane,
bis[4-(.beta.-epithiopropylthio)phenyl] sulfide,
bis[4-(.beta.-epithiopro- pylthio)phenyl] sulfone and
4,4'-bis(.beta. -epithiopropylthio)biphenyl; and
[0028] Compounds obtained by replacing at least one hydrogen of the
epithio group in the above compounds with methyl.
[0029] Examples of the group (C) compound include:
[0030] Organic compounds having a chain aliphatic backbone
structure such as bis(.beta. -epithiopropyl) sulfide,
bis(.beta.-epidithiopropyl) sulfide, bis(.beta.-epithiopropyl)
disulfide, bis(.beta.-epidithiopropyl) 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.-epithiopropylth-
io)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)b-
utane, 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]ethane,
1-(.beta.-epithiopropylthio)- -2-[[2-(2-.beta.
-epithiopropylthioethyl)thioethyl]thio]ethane,
tetrakis(.beta.-epithiopropyl-thiomethyl)methane,
1,1,1-tris(.beta.-epith- iopropylthiomethyl)propane, 1,5-bis(.beta.
-epithiopropylthio)-2-(.beta.-e-
pithiopropylthiomethyl)-3-thiapentane, 1,5-bis(.beta.
-epithiopropylthio)-2,4-bis(.beta.-epithiopropylthiomethyl)-3-thiapentane-
, 1-(.beta.
-epithiopropylthio)-2,2-bis(.beta.-epithiopropylthiomethyl)-4--
thiahexane,
1,5,6-tris(.beta.-epithiopropylthio)-4-(.beta.-epithiopropylth-
iomethyl)-3-thiahexane, 1,8-bis(.beta.
-epithiopropylthio)-4-(.beta.-epith-
iopropylthiomethyl)-3,6-dithiaoctane, 1,8-bis(.beta.
-epithiopropylthio)-4,5-bis(.beta.-epithiopropylthiomethyl)-3,6-dithiaoct-
ane,
1,8-bis(.beta.-epithiopropylthio)-4,4-bis(.beta.-epithiopropylthiomet-
hyl)-3,6-dithiaoctane, 1,8-bis(.beta.-epithiopropylthio)-2,4,5-tris
(.beta.-epithiopropylthiomethyl)-3,6-dithiaoctane,
1,8-bis(.beta.-epithiopropylthio)-2,5-bis(.beta.-epithiopropylthiomethyl)-
-3,6-dithiaoctane,
1,9-bis(.beta.-epithiopropylthio)-5-(.beta.-epithioprop-
ylthiomethyl)-5-[(2-.beta.-epithiopropylthioethyl)thiomethyl]-3,7-dithiano-
nane, 1,10-bis(.beta.
-epithiopropylthio)-5,6-bis[(2-.beta.-epithiopropylt-
hioethyl)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.
-epithiopropylthiomethy- l)-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.-epithiopropylthiomethy-
l)-3,6,9-trithiaundecane,
tetra[2-(.beta.-epithiopropylthio)acetylmethyl]m- ethane,
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-t-
hiaheptyl)-1-(3,4-thioepoxy-1-thiabutyl)propane,
1,1,3,3-tetrakis(4,5-thio- epoxy-2-thiapentyl)-2-selenapropane,
bis(4,5-thioepoxy-2-thiapentyl)-3,6,9-
-triselenaundecane-1,11-bis(3,4-thioepoxy-1-thiabutyl),
1,4-bis(3,4-thioepoxy-1-thiabutyl)-2,3-bis(6,7-thioepoxy-1-selena-4-thiah-
eptyl)butane,
tris(4,5-thioepoxy-2-thiapentyl)-3-selena-6-thiaoctane-1,8-b-
is(3,4-thioepoxy-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-thioep-
oxy-1-tellura-4-thiaheptyl)butane and
tris(4,5-thioepoxy-2-thiapentyl)-3-t-
ellura-6-thiaoctane-1,8-bis(3,4-thioepoxy-1-thiabutyl);
[0031] Compounds having an alicyclic backbone structure such as
1,3-bis(.beta. -epithiopropylthio)cyclohexane,
1,4-bis(.beta.-epithioprop- ylthio)cyclohexane,
1,3-bis(.beta.-epithiopropylthiomethyl)cyclohexane, 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-bis(3,4-epithio-1-thiabutyl)-1,4-diselenane,
2,5-bis(3,4-epithio-1-th- iabutyl)-1,4-diselenane,
2,6-bis(3,4-epithio-1-thiabutyl)-1,4-diselenane,
2,3-bis(4,5-epithio-2-thiapentyl)-1,4-diselenane,
2,5-bis(4,5-epithio-2-t- hiapentyl)-1,4-diselenane,
2,6-bis(4,5-epithio-2-thiapentyl)-1,4-diselenan- e,
2,4-bis(3,4-epithio-1-thiabutyl)-1,3-diselenane,
2,5-bis(3,4-epithio-1-thiabutyl)-1,3-diselenane,
5,6-bis(3,4-epithio-1-th- iabutyl)-1,3-diselenane,
2,4-bis(4,5-epithio-2-thiapentyl)-1,3-diselenane,
2,5-bis(4,5-epithio-2-thiapentyl)-1,3-diselenane,
5,6-bis(4,5-epithio-2-t- hiapentyl)-1,3-diselenane,
2,3-bis(3,4-epithio-1-thiabutyl)-1-thia-4-selen- ane,
2,5-bis(3,4-epithio-1-thiabutyl)-1-thia-4-selenane,
2,6-bis(3,4-epithio-1-thiabutyl)-1-thia-4-selenane,
3,5-bis(3,4-epithio-1-thiabutyl)-1-thia-4-selenane,
2,3-bis(4,5-epithio-2-thiapentyl)-1-thia-4-selenane,
2,5-bis(4,5-epithio-2-thiapentyl)-1-thia-4-selenane,
2,6-bis(4,5-epithio-2-thiapentyl)-1-thia-4-selenane,
3,5-bis(4,5-epithio-2-thiapentyl)-1-thia-4-selenane,
2,4-bis(3,4-epithio-1-thiabutyl)-1,3-diselenolane,
4,5-bis(3,4-epithio-1-thiabutyl)-1,3-diselenolane,
2,4-bis(4,5-epithio-2-thiapentyl)-1,3-diselenolane,
4,5-bis(4,5-epithio-2-thiapentyl)-1,3-diselenolane,
2,4-bis(3,4-epithio-1-thiabutyl)-1-thia-3-selenolane,
2,5-bis(3,4-epithio-1-thiabutyl)-1-thia-3-selenolane,
4,5-bis(3,4-epithio-1-thiabutyl)-1-thia-3-selenolane,
2,4-bis(4,5-epithio-2-thiapentyl)-1-thia-3-selenolane,
2,5-bis(4,5-epithio-2-thiapentyl)-1-thia-3-selenolane,
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-thiab- utyl)dicycloselenanonane,
2,3-bis(3,4-epithio-1-thiabutyl)selenophane,
2,4-bis(3,4-epithio-1-thiabutyl)selenophane,
2,5-bis(3,4-epithio-1-thiabu- tyl)selenophane,
3,4-bis(3,4-epithio-1-thiabutyl)selenophane,
2,3-bis(4,5-epithio-2-thiapentyl)selenophane,
2,4-bis(4,5-epithio-2-thiap- entyl)selenophane,
2,5-bis(4,5-epithio-2-thiapentyl)selenophane,
3,4-bis(4,5-epithio-2-thiapentyl)selenophane,
2-(4,5-thioepoxy-2-thiapent-
yl)-5-(3,4-thioepoxy-1-thiabutyl)-1-selenacyclohexane,
2,3-bis(3,4-thioepoxy-1-thiabutyl)-1-selenacyclohexane,
2,4-bis(3,4-thioepoxy-1-thiabutyl)-1-selenacyclohexane,
2,5-bis(3,4-thioepoxy-1-thiabutyl)-1-selenacyclohexane,
2,6-bis(3,4-thioepoxy-1-thiabutyl)-1-selenacyclohexane,
3,4-bis(3,4-thioepoxy-1-thiabutyl)-1-selenacyclohexane,
3,5-bis(3,4-epoxy-1-thiabutyl)-1-selenacyclohexane,
4,5-bis(3,4-epoxy-1-thiabutyl)-1-selenacyclohexane,
2,3-bis(4,5-thioepoxy-2-thiapentyl)-1-selenacyclohexane,
2,4-bis(4,5-thioepoxy-2-thiapentyl)-1-selenacyclohexane,
2,5-bis(4,5-thioepoxy-2-thiapentyl)-1-selenacyclohexane,
2,6-bis(4,5-thioepoxy-2-thiapentyl)-1-selenacyclohexane,
3,4-bis(4,5-thioepoxy-2-thiapentyl)-1-selenacyclohexane,
3,5-bis(4,5-thioepoxy-2-thiapentyl)-1-selenacyclohexane,
4,5-bis(4,5-thioepoxy-2-thiapentyl)-1-selenacyclohexane,
2,3-bis(4,5-thioepoxy-2-thiapentyl)-1-selenacyclohexane,
2,4-bis(4,5-thioepoxy-2-thiapentyl)-1-selenacyclohexane,
2,5-bis(4,5-thioepoxy-2-thiapentyl)-1-selenacyclohexane,
2,6-bis(4,5-thioepoxy-2-thiapentyl)-1-selenacyclohexane,
3,4-bis(4,5-thioepoxy-2-thiapentyl)-1-selenacyclohexane,
3,5-bis(4,5-thioepoxy-2-thiapentyl)-1-selenacyclohexane,
4,5-bis(4,5-thioepoxy-2-thiapentyl)-1-selenacyclohexane,
4,5-bis(4,5-thioepoxy-2-thiapentyl)-1-selenacyclohexane,
2,3-bis(3,4-epithio-1-thiabutyl)-1,4-ditellurane,
2,5-bis(3,4-epithio-1-t- hiabutyl)-1,4-ditellurane,
2,6-bis(3,4-epithio-1-thiabutyl)-1,4-ditelluran- e,
2,3-bis(4,5-epithio-2-thiapentyl)-1,4-ditellurane,
2,5-bis(4,5-epithio-2-thiapentyl)-1,4-ditellurane,
2,6-bis(4,5-epithio-2-thiapentyl)-1,4-ditellurane,
2,4-bis(3,4-epithio-1-thiabutyl)-1,3-ditellurane,
2,5-bis(3,4-epithio-1-t- hiabutyl)-1,3-ditellurane,
5,6-bis(3,4-epithio-1-thiabutyl)-1,3-ditelluran- e,
2,4-bis(4,5-epithio-2-thiapentyl)-1,3-ditellurane,
2,5-bis(4,5-epithio-2-thiapentyl)-1,3-ditellurane,
5,6-bis(4,5-epithio-2-thiapentyl)-1,3-ditellurane,
2,3-bis(3,4-epithio-1-thiabutyl)-1-thia-4-tellurane,
2,5-bis(3,4-epithio-1-thiabutyl)-1-thia-4-tellurane,
2,6-bis(3,4-epithio-1-thiabutyl)-1-thia-4-tellurane,
3,5-bis(3,4-epithio-1-thiabutyl)-1-thia-4-tellurane,
2,3-bis(4,5-epithio-2-thiapentyl)-1-thia-4-tellurane,
2,5-bis(4,5-epithio-2-thiapentyl)-1-thia-4-tellurane,
2,6-bis(4,5-epithio-2-thiapentyl)-1-thia-4-tellurane,
3,5-bis(4,5-epithio-2-thiapentyl)-1-thia-4-tellurane,
2,4-bis(3,4-epithio-1-thiabutyl)-1,3-ditellurolane,
4,5-bis(3,4-epithio-1-thiabutyl)-1,3-ditellurolane,
2,4-bis(4,5-epithio-2-thiapentyl)-1,3-ditellurolane,
4,5-bis(4,5-epithio-2-thiapentyl)-1,3-ditellurolane,
2,4-bis(3,4-epithio-1-thiabutyl)-1-thia-3-tellurolane,
2,5-bis(3,4-epithio-1-thiabutyl)-1-thia-3-tellurolane,
4,5-bis(3,4-epithio-1-thiabutyl)-1-thia-3-tellurolane,
2,4-bis(4,5-epithio-2-thiapentyl)-1-thia-3-tellurolane,
2,5-bis(4,5-epithio-2-thiapentyl)-1-thia-3-tellurolane,
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-bis(3,4-epithio-1-t- hiabutyl)tellurophane,
2,4-bis(3,4-epithio-1-thiabutyl)tellurophane,
2,5-bis(3,4-epithio-1-thiabutyl)tellurophane,
3,4-bis(3,4-epithio-1-thiab- utyl)tellurophane,
2,3-bis(4,5-epithio-2-thiapentyl)tellurophane,
2,4-bis(4,5-epithio-2-thiapentyl)tellurophane,
2,5-bis(4,5-epithio-2-thia- pentyl)tellurophane,
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-bis(3,4-thioepoxy-1-thiabutyl)-1-telluracyclohexane,
2,4-bis(3,4-thioepoxy-1-thiabutyl)-1-telluracyclohexane,
2,5-bis(3,4-thioepoxy-1-thiabutyl)-1-tellura-cyclohexane,
2,6-bis(3,4-thioepoxy-1-thiabutyl)-1-telluracyclohexane,
3,4-bis(3,4-thioepoxy-1-thiabutyl)-1-telluracyclohexane,
3,5-bis(3,4-thioepoxy-1-thiabutyl)-1-telluracyclohexane,
4,5-bis(3,4-thioepoxy-1-thiabutyl)-1-telluracyclohexane,
2,3-bis(3,4-thioepoxy-1-thiabutyl)-1-telluracyclohexane,
2,4-bis(3,4-thioepoxy-1-thiabutyl)-1-telluracycdohexane,
2,5-bis(3,4-thioepoxy-1-thiabuty)-1-telluracyclohexane,
2,6-bis(3,4-thioepoxy-1-thiabutyl)-1-telluracyclohexane,
3,4-bis(3,4-thioepoxy-1-thiabutyl)-1-telluracyclohexane,
3,5-bis(3,4-thioepoxy-1-thiabutyl)-1-telluracyclohexane,
4,5-bis(3,4-thioepoxy-1-thiabutyl)-1-telluracyclohexane,
2,3-bis(4,5-thioepoxy-2-thiapentyl)-1-telluracyclohexane,
2,4-bis(4,5-thioepoxy-2-thiapentyl)-1-teluracyclohexane,
2,5-bis(4,5-thioepoxy-2-thiapentyl)-1-telluracyclohexane,
2,6-bis(4,5-thioepoxy-2-thiapentyl)-1-telluracyclohexane,
3,4-bis(4,5-thioepoxy-2-thiapentyl)-1-telluracyclohexane,
3,5-bis(4,5-thioepoxy-2-thiapentyl)-1-telluracyclohexane and
4,5-bis(4,5-thioepoxy-2-thiapentyl)-1-telluracyclohexane;
[0032] Compounds having an aromatic backbone structure such as
1,3-bis(.beta. -epithiopropylthio)benzene,
1,4-bis(.beta.-epithiopropylth- io)benzene, 1,3-bis(.beta.
-epithiopropylthiomethyl)benzene,
1,4-bis(.beta.-epithiopropylthiomethyl)benzene,
bis[4-(.beta.-epithioprop- ylthio)phenyl]methane, 2,2-bis[4-(.beta.
-epithiopropylthio)phenyl]propane- ,
bis[4-(.beta.-epithiopropylthio)phenyl] sulfide,
bis[4-(.beta.-epithiopr- opylthio)phenyl] sulfone and
4,4'-bis(.beta. -epithiopropylthio)biphenyl; and
[0033] Compounds obtained by replacing at least one hydrogen atom
of the .beta.-epithiopropyl group in the above compounds with
methyl group.
[0034] Examples of the group (D) compound include:
[0035] Organic compounds having a chain aliphatic backbone
structure such as bis(.beta. -epithiopropyl) selenide,
bis(.beta.-epidithiopropyl) selenide, bis(.beta.-epithiopropyl)
diselenide, bis(.beta.-epidithiopropy- l) diselenide,
bis(.beta.-epithiopropyl) triselenide,
bis(.beta.-epithiopropylseleno)methane,
1,2-bis(.beta.-epithiopropylselen- o)ethane,
1,3-bis(.beta.-epithiopropylseleno)propane,
1,2-bis(.beta.-epithiopropylseleno)propane, bis(epithioethyl)
selenide, bis(epithioethyl) diselenide, 1-(.beta.
-epithiopropylseleno)-2-(.beta.-e-
pithiopropylselenomethyl)propane, 1,4-bis(.beta.
-epithiopropylseleno)buta- ne,
1,3-bis(.beta.-epithiopropylseleno)butane, 1-(.beta.
-epithiopropylseleno)-3-(.beta.-epithiopropylselenomethyl)butane,
1,5-bis(.beta. -epithiopropylseleno)pentane,
1-(.beta.-epithiopropylselen- o)-4-(.beta.
-epithiopropylselenomethyl)pentane, 1,6-bis(.beta.-epithiopro-
pylseleno)hexane, 1-(.beta.
-epithiopropylseleno)-5-(.beta.-epithiopropyls- elenomethyl)hexane,
1-(.beta. -epithiopropylseleno)-2-[(2-.beta.-epithiopr-
opylselenoethyl)thio]ethane, 1-(.beta.
-epithiopropylseleno)-2-[[2-(2-.bet- a.
-epithiopropylselenoethyl)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.-epithiop-
ropylselenomethyl)-4-thiahexane, 1,5,6-tris(.beta.
-epithiopropylseleno)-4-
-(.beta.-epithiopropylselenomethyl)-3-thiahexane, 1,8-bis(.beta.
-epithiopropylseleno)-4-(.beta.-epithiopropylselenomethyl)-3,6-dithiaocta-
ne,
1,8-bis(.beta.-epithiopropylseleno)-4,5-bis(.beta.-epithiopropylseleno-
methyl)-3,6-dithiaoctane,
1,8-bis(.beta.-epithiopropylseleno)-4,4-bis(.bet- a.
-epithiopropylselenomethyl)-3,6-dithiaoctane,
1,8-bis(.beta.-epithiopro-
pylseleno)-2,4,5-tris(.beta.-epithiopropylselenomethyl)-3,6-dithiaoctane,
1,8-bis(.beta.
-epithiopropylseleno)-2,5-bis(.beta.-epithiopropylselenome-
thyl)-3,6-ditbiaoctane,
1,9-bis(.beta.-epithiopropylseleno)-5-(.beta.-epit-
hiopropylselenomethyl)-5-[(2-.beta.
-epithiopropylselenoethyl)selenomethyl- ]-3,7-dithianonane,
1,10-bis(.beta. -epithiopropylseleno)-5,6-bis[(2-.beta-
.-epithiopropylselenoethyl)thio]-3,6,9-trithiadecane,
1,11-bis(.beta.-epithiopropylseleno)-4,8-bis(.beta.
-epithiopropylselenomethyl)-3,6,9-trithiaundecane, 1,11-bis(.beta.
-epithiopropylseleno)-5,7-bis(.beta.-epithiopropylselenomethyl)-3,6,9-tri-
thiaundecane, 1,11-bis(.beta.-epithiopropylseleno)-5,7-[(2-.beta.
-epithiopropylselenoethyl)selenomethyl]-3,6,9-trithiaundecane,
1,11-bis(.beta.
-epithiopropylseleno)-4,7-bis(.beta.-epithiopropylselenom-
ethyl)-3,6,9-trithiaundecane,
tetra[2-(.beta.-epithiopropylseleno)acetylnm- ethyl]methane,
1,1,1-tri[2-(.beta.-epithiopropylseleno)acetylmethyl]propan- e,
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-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-th-
ioepoxy-1-selenobutyl),
1,4-bis(3,4-thioepoxy-1-selenobutyl)-2,3-bis(6,7-t-
hioepoxy-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-tellura-4-selenoheptyl)-1-(3,4-thioepoxy-1-selenobutyl)prop-
ane,
1,1,3,3-tetrakis(4,5-thioepoxy-2-selenopentyl)-2-tellurapropane,
bis(4,5-thioepoxy-2-selenopentyl)-3,6,9-tritelleraundecane-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-selenoheptyl)butane and
tris(4,5-thiepoxy-2-selenope-
ntyl)-3-tellura-6-thiaoctane-1,8-bis(3,4-thioepoxy-1-selenobutyl);
[0036] Compounds having an alicyclic backbone structure such as
1,3-bis(.beta. -epithiopropylseleno)cyclohexane,
1,4-bis(.beta.-epithiopr- opylseleno)cyclohexane,
1,3-bis(.beta.-epithiopropylselenomethyl)cycdohexa- ne,
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.-epithiopropylsel- enomethyl)-1,4-dithiane,
2,5-bis(.beta.-epithiopropylselenoethylthiomethyl- )-1,4-dithiane,
2,3-bis(3,4-epithio-1-selenobutyl)-1,4-diselenane,
2,5-bis(3,4-epithio-1-selenobutyl)-1,4-diselenane,
2,6-bis(3,4-epithio-1-selenobutyl)-1,4-diselenane,
2,3-bis(4,5-epithio-2-selenopentyl)-1,4-diselenane,
2,5-bis(4,5-epithio-2-selenopentyl)-1,4-diselenane,
2,6-bis(4,5-epithio-2-selenopentyl)-1,4-diselenane,
2,4-bis(3,4-epithio-1-selenobutyl)-1,3-diselenane,
2,5-bis(3,4-epithio-1-selenobutyl)-1,3-diselenane,
5,6-bis(3,4-epithio-1-selenobutyl)-1,3-diselenane,
2,4-bis(4,5-epithio-2-selenopentyl)-1,3-diselenane,
2,5-bis(4,5-epithio-2-selenopentyl)-1,3-diselenane,
5,6-bis(4,5-epithio-2-selenopentyl)-1,3-diselenane,
2,3-bis(3,4-epithio-1-selenobutyl)-1-thia-4-selenane,
2,5-bis(3,4-epithio-1-selenobutyl)-1-thia-4-selenane,
2,6-bis(3,4-epithio-1-selenobutyl)-1-thia-4-selenane,
3,5-bis(3,4-epithio-1-selenobutyl)-1-thia-4-selenane,
2,3-bis(4,5-epithio-2-selenopentyl)-1-thia-4-selenane,
2,5-bis(4,5-epithio-2-selenopentyl)-1-thia-4-selenane,
2,6-bis(4,5-epithio-2-selenopentyl)-1-thia-4-selenane,
3,5-bis(4,5-epithio-2-selenopentyl)-1-thia-4-selenane,
2,4-bis(3,4-epithio-1-selenobutyl)-1,3-diselenolane,
4,5-bis(3,4-epithio-1-selenobutyl)-1,3-diselenolane,
2,4-bis(4,5-epithio-2-selenopentyl)-1,3-diselenolane,
4,5-bis(4,5-epithio-2-selenopentyl)-1,3-diselenolane,
2,4-bis(3,4-epithio-1-selenobutyl)-1-thia-3-selenolane,
2,5-bis(3,4-epithio-1-selenobutyl)-1-thia-3-selenolane,
4,5-bis(3,4-epithio-1-selenobutyl)-1-thia-3-selenolane,
2,4-bis(4,5-epithio-2-selenopentyl)-1-thia-3-selenolane,
2,5-bis(4,5-epithio-2-selenopentyl)-1-thia-3-selenolane,
4,5-bis(4,5-epithio-2-selenopentyl)-1-thia-3-selenolane,
2,6-bis(4,5-epithio-2-selenopentyl)-1,3,5-triselenane,
bis(3,4-epithio-1-selenobutyl)tricycloselenaoctane,
bis(3,4-epithio-1-selenobutyl)dicycloselenanonane,
2,3-bis(3,4-epithio-1-selenobutyl)selenophane,
2,4-bis(3,4-epithio-1-sele- nobutyl)selenophane,
2,5-bis(3,4-epithio-1-selenobutyl)selenophane,
3,4-bis(3,4-epithio-1-selenobutyl)selenophane,
2,3-bis(4,5-epithio-2-sele- nopentyl)selenophane,
2,4-bis(4,5-epithio-2-selenopentyl)selenophane,
2,5-bis(4,5-epithio-2-selenopentyl)selenophane,
3,4-bis(4,5-epithio-2-sel- enopentyl)selenophane,
2-(4,5-thioepoxy-2-selenopentyl)-5-(3,4-thioepoxy-1-
-selenobutyl)-1-selenacyclohexane, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-,
3,5- or 4,5-bis(3,4-thioepoxy-1-selenobutyl)-1-selenacyelohexane,
2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or
4,5-bis(4,5-thioepoxy-2-selenopentyl)-1-selenac- yclohexane, 2,3-,
2,5- or 2,6-bis(3,4-epithio-1-selenobutyl)-1,4-diteliura- ne, 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-epithio-1-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)triyclotelluraoctane,
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-selen-
opentyl)-5-(3,4-thioepoxy-1-selenobutyl)-1-telluracyclohexane,
2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or
4,5-bis(3,4-thioepoxy-1-selenobutyl)-1-tellurac- yclohexane, and
2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or
4,5-bis(4,5-thioepoxy-2-selenopentyl)-1-telluracyclohexane;
[0037] Compounds having an aromatic backbone structure such as 1,3-
or 1,4-bis(.beta. -epithiopropylseleno)benzene, 1,3- or
1,4-bis(.beta. -epithiopropylselenomethyl)benzene, bis[4-(.beta.
-epithiopropylseleno)ph- enyl]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
[0038] Compounds obtained by replacing at least one hydrogen of the
.beta.-epithiopropyl group in the above compounds with methyl.
[0039] Examples of the group (E) compound include:
[0040] Organic compounds having a chain aliphatic backbone
structure such as bis(.beta. -epithiopropyl) telluride,
bis(.beta.-epidithiopropyl) telluride, bis(.beta.-epithiopropyl)
ditelluride, bis(.beta.-epidithiopro- pyl) ditelluride,
bis(.beta.-epithiopropyl) tritelluride,
bis(.beta.-epithiopropyltelluro)methane,
1,2-bis(.beta.-epithiopropyltell- uro)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)propane, 1,4-bis(.beta.
-epithiopropyltelluro)butane,
1,3-bis(.beta.-epithiopropyltelluro)butane, 1-(.beta.
-epithiopropyltelluro)-3-(.beta.-epithiopropyltelluromethyl)-bu-
tane, 1,5-bis(.beta. -epithiopropyltelluro)pentane,
1-(.beta.-epithiopropyltelluro)-4-(.beta.
-epithiopropyltelluromethyl)pen- tane,
1,6-bis(.beta.-epithiopropyltelluro)hexane,
1-(.beta.-epithiopropylt-
elluro)-5-(.beta.-epithiopropyltelluromethyl)hexane, 1-(.beta.
-epithiopropyltelluro)-2-[(2-.beta.-epithiopropyltelluroethyl)thio]ethane-
, 1-(.beta. -epithiopropyltelluro)-2-[[2-(2-.beta.
-epithiopropyltelluroet- hyl)telluroethyl]thio]ethane,
tetrakis(.beta. -epithiopropyltelluromethyl)- methane,
1,1,1-tris(.beta. -epithiopropyltelluromethyl)propane,
1,5-bis(.beta.-epithiopropyltelluro)-2-(.beta.
-epithiopropyltelluromethy- l)-3-thiapentane,
1,5-bis(.beta.-epithiopropyltelluro)-2,4-bis(.beta.-epit-
hiopropyltelluromethyl)-3-thiapentane,
1-(.beta.-epithiopropyltelluro)-2,2-
-bis(.beta.-epithiopropyltelluromethyl)-4thiahexane,
1,5,6-tris(.beta.
-epithiopropylteliuro)-4-(.beta.-epithiopropyltelluromethyl)-3-thiahexane-
, 1,8-bis(.beta.
-epithiopropyltelluro)-4-(.beta.-epithiopropyltellurometh-
yl)-3,6-dithiaoctane,
1,8-bis(.beta.-epithiopropyltelluro)-4,5-bis(.beta.--
epithiopropyltelluromethyl)-3,6-dithiaoctane,
1,8-bis(.beta.-epithiopropyl- telluro)-4,4-bis(.beta.
-epithiopropyltelluromethyl)-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.-epithiopropyltelluromethyl)-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.-epithiopropyltel-
luroethyl)thio]-3,6,9-trithiadecane,
1,11-bis(.beta.-epithiopropyltelluro)- -4,8-bis(.beta.
-epithiopropyltelluromethyl)-3,6,9-trithiaundecane, 1,11-bis(.beta.
-epithiopropyltelluro)-5,7-bis(.beta.-epithiopropyltellur-
omethyl)-3,6,9-trithiaundecane,
1,11-bis(.beta.-epithiopropyltelluro)-5,7-- [(2-.beta.
-epithiopropyltelluroethyl)selenomethyl]-3,6,9-trithiaundecane,
1,11-bis(.beta.
-epithiopropyltelluro)-4,7-bis(.beta.-epithiopropyltellur- omethy
)-3,6,9-trithiaundecane,
tetra[2-(.beta.-epithiopropyltelluro)acety- lmethyl]methane,
1,1,1-tri[2-(.beta.-epithiopropyltelluro)acetylmethyl]pro- pane,
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-tellurobutyl)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-telluroheptyl)butane,
tris(4,5-thioepoxy-2-tellurop-
entyl)-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-tellur-
a-4-telluroheptyl)-1-(3,4-thioepoxy-1-tellurobutyl)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-telluroheptyl)butane and
tris(4,5-thiepoxy-2-tell-
uropentyl)-3-tellura-6-thiaoctane-1,8-bis(3,4-thioepoxy-1-tellurobutyl);
[0041] Compounds having an alicyclic backbone structure such as
1,3-bis(.beta. -epithiopropyltelluro)cyclohexane,
1,4-bis(.beta.-epithiop- ropyltelluro)cyclohexane,
1,3-bis(.beta.-epithiopropyltelluromethyl)cycloh- exane,
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.-epithiopropylte- lluromethyl)-1,4-dithiane,
2,5-bis(.beta.-epithiopropyltelluroethylthiomet- hyl)-1,4-dithiane,
2,3-, 2,5- or 2,6-bis(3,4-epithio-1-tellurobutyl)-1,4-d- iselenane,
2,3-bis(4,5-epithio-2-telluropentyl)-1,4-diselenane,
2,5-bis(4,5-epithio-2-telluropentyl)-1,4-diselenane,
2,6-bis(4,5-epithio-2-telluropentyl)-1,4-diselenane,
2,4-bis(3,4-epithio-1-tellurobutyl)-1,3-diselenane,
2,5-bis(3,4-epithio-1-tellurobutyl)-1,3-diselenane,
5,6-bis(3,4-epithio 1-tellurobutyl)-1,3-diselenane,
2,4-bis(4,5-epithio-2-telluropentyl)-1,3-- diselenane,
2,5-bis(4,5-epithio-2-telluropentyl)-1,3-diselenane,
5,6-bis(4,5-epithio-2-telluropentyl)-1,3-diselenane,
2,3-bis(3,4-epithio-1-tellurobutyl)-1-thia-4-selenane,
2,5-bis(3,4-epithio-1-tellurobutyl)-1-thia-4-selenane,
2,6-bis(3,4-epithio-1-tellurobutyl)-1-thia-4-selenane, 3,5-bis(3,
4-epithio-1-tellurobutyl)-1-thia-4-selenane,
2,3-bis(4,5-epithio-2-tellur- opentyl)-1-thia-4-selenane,
2,5-bis(4,5-epithio-2-telluropentyl)-1-thia-4-- selenane,
2,6-bis(4,5-epithio-2-telluropentyl)-1-thia-4-selenane,
3,5-bis(4,5-epithio-2-telluropentyl)-1-thia-4-selenolane,
2,4-bis(3,4-epithio-1-tellurobutyl)-1,3-diselenolane,
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-tellu-
ropentyl)-5-(3,4-thioepoxy-1-tellurobutyl)-1-selenacyclohexane,
2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or
4,5-bis(3,4-thioepoxy-1-tellurobutyl)-1-s- elenacyclohexane, 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-epitbio-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-tell-
uropentyl)-5-(3,4-thioepoxy-1-tellurobutyl)-1-telluracyclohexane,
2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or
4,5-bis(3,4-thioepoxy-1-tellurobutyl)-1te- lluracyclohexane, and
2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or
4,5-bis(4,5-thioepoxy-2-telluropentyl)-1-telluracyclohexane;
[0042] Compounds having an aromatic backbone structure such as 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
[0043] Compounds obtained by replacing at least one hydrogen of the
.beta.-epithiopropyl group in the above compounds with methyl.
[0044] Further examples of the group (A) to (E) compounds include
organic compounds having unsaturated groups. Specific examples of
such compounds include vinylphenyl thioglycidyl ether, vinylbenzyl
thioglycidyl ether, thioglycidyl methacrylate, thioglycidyl
acrylate and allyl thioglycidyl ether.
[0045] It should be noted that the compound having the radical
represented by the formula (I) is not limited to the above
examples.
[0046] Among the above compounds, preferred are the group (B)
compounds (Y of the formula (I) is O), the group (C) compound (Y of
the formula (I) is S) and the group (D) compound (Y of the formula
(I) is Se). More preferred are the group (C) and (D) compounds. The
group (C) and (D) compounds wherein m is 1 or 2 and n is 1 or 2 are
still more preferable, and particularly preferable when m is 1 and
n is 1 or 2. Examples of the particularly preferable compound
include bis(.beta.-epithiopropyl) sulfide,
bis(.beta.-epithiopropyl) disulfide, bis(.beta. -epithiopropyl)
selenide and bis(.beta.-epithiopropyl) diselenide. Other examples
are chain compounds, branched compounds, alicyclic compounds,
aromatic compounds and heterocyclic compounds which have at least
two .beta.-epithiopropylthio groups or .beta.-epithiopropylseleno
groups, which are described above as the examples. Among the
particularly preferable compounds, chain compounds and branched
compounds which have at least two .beta.-epithiopropylthio groups
or .beta.-epithiopropylselen- o groups, bis(.beta.-epithiopropyl)
sulfide, bis(.beta.-epithiopropyl) disulfide,
bis(.beta.-epithiopropyl) selenide and bis(.beta. -epithiopropyl)
diselenide are most preferable.
[0047] The compounds having the radical represented by the formula
(I) may be produced by the methods described in U.S. Pat. Nos.
5,807,975 and 5,945,504, and European Patent Publication
1024223.
[0048] The bluing agents usable in the present invention are
inorganic or organic pigments, preferably those pigments capable of
being homogeneously dissolved or dispersed in the composition for
optical materials, more preferably organic pigments capable of
being homogeneously dissolved in the composition for optical
materials. In accordance with the Color Index Classification,
examples of such organic pigments include azo compounds such as
C.I. Azoic Violet 2, C.I. Azoic Blue 6, C.I. Azoic Blue 7, etc.;
anthraquinone compounds such as C.I. Solvent Violet 33, C.I.
Solvent Violet 36, C.I. Solvent Blue 94, C.I. Solvent Blue 95, C.I.
Solvent Blue 78, etc.; and phthalocyanine compounds such as C.I.
Solvent Blue 55. Other examples include isoindolinone compounds,
quinacridone compounds and perylene compounds. Of these organic
pigments, most preferred are the anthraquinone compounds.
[0049] The bluing agents may be used alone or in combination of two
or more. The bluing agents generally include blue, violet and green
pigments.
[0050] Further, the composition may be added with another red,
orange or brown pigment to adjust the color tone of the optical
material. Examples of the red, orange and brown pigments include
azo compounds such as C.I. Pigment Yellowl2, C.I. Pigment Yellow
14, etc.; anthraquinone compounds such as C.I. Pigment Red 83, C.I.
Vat Yellow 3, C.I. Vat Yellow 20, C.I. Pigment Brown 7, etc.;
quinacridone compounds such as C.I. Quinacridone Yellow 2, etc.;
and perylene compounds. Of these pigments, especially preferred are
the red, orange and brown anthraquinone compounds.
[0051] The amount of the bluing agent to be added varies depending
upon kind of the bluing agent, kind of the monomer, kind and amount
of the additive such as ultraviolet light absorber and antioxidant,
polymerization temperature and time or the like, and usually is in
the range of 0.000001 to 0.5 part by weight based on 100 parts by
weight of the composition for optical materials. When the amount is
less than 0.000001 part by weight, no appreciable effect of adding
the bluing agent is obtained. When more than 0.5 part by weight,
the resin obtained after the polymerization and curing is
disadvantageously colored from blue to black.
[0052] The amount of the red, orange or brown pigment optionally
added for adjusting the color tone of the optical material is in
the range of 0.000001 to 0.0005 part by weight based on 100 parts
by weight of the composition for optical materials.
[0053] The composition may include a curing catalyst for producing
the optical materials. Examples of the curing catalyst include
amines, phosphines, quaternary ammonium salts, quaternary
phosphonium salts, tertiary sulfonium salts, secondary iodonium
salts, mineral acids, Lewis acids, organic acids, silicic acids,
tetrafluoroboric acid or the like, as described in European Patent
Publication 0978513.
[0054] The amount of the curing catalyst to be added is 0.001 to
10.0 parts by weight, preferably 0.005 to 5.0 parts by weight based
on 100 parts by weight of the composition comprising the compound
having the radical represented by the formula (I).
[0055] The compound having the radical represented by the formula
(I) may be polymerized with a compound having at least one
functional group capable of reacting with a
.beta.-epi(poly)thioalkyl group in the formula (I) and/or at least
one self-polymerizable functional group or a compound having at
least one self-polymerizable functional group which is also capable
of reacting with the .beta.-epi(poly)thioalkyl group. These
compounds may be used in an amount of 0.001 to 500 parts by weight
based on 100 parts by weight of the composition, and specific
examples thereof are described in U.S. Pat. No. 5,945,504.
[0056] When the compound having the radical represented by the
formula (I) is polymerized with a compound having an unsaturated
group, the polymerization is preferably conducted in the presence
of a radical polymerization initiator as polymerization promoter in
an amount of 0.001 to 5.0 parts by weight based on 100 parts by
weight of the composition for optical materials. Any compound may
be used as the radical polymerization initiator as long as the
compound produces radicals by heating or irradiation of ultraviolet
light or electron beam. Specific examples thereof are described in
U.S. Pat. No. 5,945,504.
[0057] To make the cured materials highly oxidation-resistant, a
compound having at least one SH group may be contained in the
composition as an antioxidant component either alone or in
combination with a another known antioxidant. The content thereof
is preferably 0.001 to 80% by weight based on the composition.
Example of the compounds having at least one SH group include
mercaptans and thiophenols which may have an unsaturated group such
as vinyl, aromatic vinyl, methacrylic group, acrylic group and
allyl. Specific examples thereof are described in U.S. Pat. No.
5,945,504.
[0058] To improve the properties of the optical materials such as
dyeability and mechanical strength, a compound having at least one
active hydrogen other than that of SH group may be contained in the
composition in an amount of 0.001 to 40% by weight based on the
composition. The "active hydrogen" referred to herein means, for
example, hydrogen of hydroxy, carboxyl and amide, and hydrogen at
2-position of 1,3-diketones, 1,3-dicarboxylic acids and esters
thereof, and 3-ketocarboxylic acids and esters thereof. Examples of
the compound having at least one active hydrogen per one molecule
include alcohols, phenols, mercaptoalcohols, hyroxythiophenols,
carboxylic acids, mercaptocarboxylic acids, hydroxycarboxylic
acids, amides, 1,3-diketones, 1,3-dicarboxylic acids and esters
thereof, 3-ketocarboxylic acids and esters thereof. These compounds
may have an unsaturated group such as vinyl, aromatic vinyl,
methacrylic group, acrylic group and allyl. Specific examples are
described in U.S. Pat. No. 5,945,504.
[0059] Further, a compound having at least one isocyanate group may
be contained in the composition in an amount of 0.001 to 80% by
weight based on the composition to enhance the mechanical strength
of the optical materials. Specific examples thereof are described
in U.S. Pat. No. 6,130,307 which is incorporated herein by
reference.
[0060] Furthermore, to enhance the refractive index, an inorganic
compound containing sulfur and/or selenium may be contained in the
composition for optical materials in an amount of 0.001 to 50% by
weight based on the composition. Specific examples thereof are
described in European Patent Publication 1046931 which is
incorporated herein by reference.
[0061] A known additive such as an antioxidant and an ultraviolet
light absorber may also be contained in the composition in a total
amount of 0.001 to 5.0% by weight based on the composition to
improve the utility of the optical materials. Further, the
composition for optical materials used in the present invention
tends to be separated from the surface of a mold cavity during the
polymerization operation. Therefore, if required, a known external
and/or internal adhesion modifiers are used or added to the
composition to effectively improve the adhesion between the cured
material and the surface to the mold cavity.
[0062] In the process for the production of the optical material
according to the present invention, the compound having at least
one radical represented by the formula (I) per one molecule is
mechanically mixed with the bluing agent together with the optional
additive such as catalyst, adhesion modifier, antioxidant,
ultraviolet light absorber, radical polymerization initiator and
various other modifiers to prepare a uniform composition. The
composition is injected into a mold made of glass or metal where
the composition is heated, thereby carrying out polymerization and
curing. Then, the resultant cured product is removed from the mold
to obtain the optical material.
[0063] Prior to injecting the composition into the mold, a part or
whole of the composition may be subjected to pre-polymerization at
-100 to 160.degree. C. for 0.1 to 288 hours in the presence or
absence of a catalyst with or without stirring, and then the
pre-polymerized composition may be injected into the mold. The
pre-polymerization is preferably conducted at -10 to 100.degree. C.
for 1 to 144 hours, more preferably at 0 to 60.degree. C. for 1 to
96 hours. The bluing agent may be added to the composition either
before or after the pre-polymerization.
[0064] The process of the present invention will explained below in
more detail. As described above, after the main and optional
starting materials are mixed together, the resultant composition is
injected into the mold and then cured therein. The composition is
prepared by mixing the compound having at least one radical
represented by the formula (I) per one molecule, the bluing agent
and the optional component such as the curing catalyst, the
compound having at least one functional group capable of reacting
with a .beta.-epi(poly)thioalkyl group in the formula (I) and/or at
least one self-polymerizable functional group, the compound having
at least one self-polymerizable functional group which is also
capable of reacting with the .beta.-epi(poly)thioalkyl group, the
antioxidant component, the modifier for improving dyeability and
mechanical strength, the refractive index modifier, the adhesion
improver, the stabilizer and the radical polymerization initiator,
all may be simultaneously mixed together in a common container
under stirring. The above ingredients are all mixed simultaneously
in a single vessel under stirring. Alternatively, the ingredients
may be sequentially added to the vessel, or the ingredients may be
divided into two or more groups which are separately mixed in
different vessels and then mixed combinedly in a single vessel. The
order of addition of the main and optional components is not
particularly restricted. The mixing temperature and the mixing time
are not particularly limited as long as the ingredients are
thoroughly mixed together. However, excessively high mixing
temperature and excessively long mixing time tends to cause
undesired reactions of the ingredients and increases the viscosity
of the resultant composition, this making the injection operation
of the composition into the mold difficult. Accordingly, the mixing
temperature is preferably about -50 to about 100.degree. C., more
preferably -30 to 50.degree. C., most preferably -5 to 30.degree.
C. The mixing time is preferably one minute to 5 hours, more
preferably from 5 minutes to 2 hours, particularly preferably 5 to
30 minutes, most preferably 5 to 15 minutes.
[0065] The respective ingredients may be suitably degassed under
reduced pressure before, during or after the mixing operation to
prevent generation of bubbles in the subsequent polymerizing/curing
operation in the mold. The reduced pressure for the degassing is
preferably about 0.1 to 700 mmHg, more preferably 10 to 300 mmHg.
Further, the ingredients before mixing or a mixture thereof is
preferably passed through a filter having a pore size of 0.05 to 3
.mu.m to purify the resultant composition by removing impurities,
thereby further enhancing the quality of the optical material of
the present invention.
[0066] The composition thus prepared is injected into the mold made
of glass or metal, and then subjected to polymerization/curing by
using an electric furnace or the like. The polymerization/curing
time is preferably 0.1 to 100 hours, more preferably 1 to 48 hours.
The polymerization/curing temperature is preferably -10 to
160.degree. C., more preferably -10 to 140.degree. C. The
polymerization/curing of the composition may be conducted by
holding the temperature at a predetermined level for a
predetermined period of time, by raising the temperature at a rate
of 0.1 to 100.degree. C./hr, by lowering the temperature at a rate
of 0.1 to 100.degree. C./hr, or by a combination thereof.
[0067] After completion of the polymerization/curing, the obtained
product is preferably annealed at 50 to 150.degree. C. for about 10
minutes to 5 hours to remove distortion. Further, if required, the
optical material of the present invention may be surface-treated
for dyeing, hard-coating, anti-reflection and anti-fogging.
[0068] As described above, a colorless and transparent optical
material having a high refractive index is produced by adding a
bluing agent to a composition for optical materials and then
subjecting the resultant composition to polymerization/curing.
[0069] The present invention will be described in more detail by
reference to the following examples. However, it should be noted
that the following examples are illustrative and not intended to
limit the invention thereto.
[0070] In the following Examples and Comparative Examples, the
appearance of lens was visually observed and the refractive index
(nD) and the Abbe's number were measured at 25.degree. C. using an
Abbe refractometer.
EXAMPLE 1
[0071] A homogeneous liquid composition was prepared by mixing 95
parts by weight of 1,2-bis(.beta.-epithiopropylthio)ethane, 5 parts
by weight of 2-mercaptoethanol, 0.0005 part by weight of Diaresin
Blue G (anthraquinone bluing agent produced by Mitsubishi Chemical
Corp.), 0.1 part by weight of tetrabromophosphonium bromide as a
catalyst and 0.1 part by weight of Sumisolve 340 as an ultraviolet
light absorber (produced by Sumitomo Chemical Corp.). The liquid
composition was injected into a mold for 2.5 mm-thick flat lens.
The mold filled with the liquid composition was placed in an oven
and heated from 30.degree. C. to 120.degree. C. over 20 hours to
polymerize and cure the composition, thereby obtaining a colorless
and transparent lens. The measured refractive index and Abbe's
number of the lens are shown in Table 1.
EXAMPLES 2-4
[0072] The same procedure as in Example 1 was repeated except that
the composition and bluing agent shown in Table 1 were used. The
appearance, the refractive index and the Abbe's number of the
obtained lens are shown in Table 1.
EXAMPLE 5
[0073] The same procedure as in Example 1 was repeated except that
the composition, the bluing agent and the red anthraquinone pigment
(Sumiplast HL5B produced by Sumitomo Chemical Corp.) shown in Table
1 were used. The appearance, the refractive index and the Abbe's
number of the obtained lens are shown in Table 1.
EXAMPLES 6-8 and COMPARATIVE EXAMPLES 1-5
[0074] The same procedure as in Example 1 was repeated except that
the composition and bluing agent shown in Table 1 were used. The
appearance, the refractive index and the Abbe's number of the
obtained lens are shown in Table 1.
1TABLE 1 Chemical Composition (part by weight) Examples 1
1,2-bis(.beta.-epithiopropylthio)ethane/2-me- rcaptoethanol = 95/5
2 1,2-bis(.beta.-epithiopropylthio)ethane = 100 3
1,2-bis(.beta.-epithiopropylthioethyl)sulfide = 100 4
bis(.beta.-epithiopropyl)sulfide/bis(2-mercaptoethylethyl)sulfide =
95/5 5 bis(.beta.-epithiopropyl)sulfide/bis(2-mercaptoethylethyl-
)sulfide/3- phenoxy-2-hydroxypropyl acrylate = 90/5/5 6
bis(.beta.-epithiopropyl)sulfide/sulfur = 90/10 7
bis(.beta.-epithiopropyl)sulfide/sulfur/selenium sulfide = 77/20/3
8 bis(.beta.-epithiopropyl)sulfide = 100 Com- parative Examples 1
1,2 -bis(.beta.-epithiopropylthio)ethane/2-mercaptoet- hanol = 95/5
2 1,2-bis(.beta.-epithiopropylthio)ethane/2-mercaptoet- hanol =
95/5 3 1,2-bis(.beta.-epithiopropylthio)ethane/2-mercaptoet- hanol
= 95/5 4 1,2-bis(.beta.-epithiopropylthioethyl)sulfide = 100 5
bis(.beta.-epithiopropyl)sulfide = 100 Bluing agent Appearance
Refractive Abbe's (part by weight) of lens index number Examples 1
BlueG (0.0005) colorless 1.70 36 transparency 2 BlueG (0.001)
colorless 1.70 36 transparency 3 BlueG (0.002) colorless 1.70 36
transparency 4 BlueG (0.0005) colorless 1.70 36 transparency 5
BlueG (0.0002) colorless 1.70 36 RedHL5B (0.00005) transparency 6
BlueG (0.01) colorless 1.72 34 transparency 7 BlueG (0.1) colorless
1.75 31 transparency 8 BlueA-D (0.00001) colorless 1.71 36
transparency Comparative Examples 1 -- light-yellowish 1.70 36
transparency 2 BlueG (0.0000008) light-yellowish 1.70 36
transparency 3 BlueG (0.7) bluish 1.70 36 transparency 4 --
yellowish 1.70 36 transparency 5 -- yellowish 1.71 36 transparency
BlueG: Diaresin Blue G (Anthraquinone pigment produced by
Mitsubishi Chemical Corp.) C.I. Solvent Violet 36 BlueA-D: Kayaset
Blue A-D (Anthraquinone pigment produced by Nippon Kayaku Co. Ltd.)
C.I. Solvent Violet 33 RedHL5B: Sumiplast HL5B (Anthraquinone
pigment produced by Sumitomo Chemical Corp.) C.I. Pigment Red
83
* * * * *