Process for production of optical material

Details Process for production of optical material Process for production of optical material

2001-01-11

2002-09-03

Dawson, Robert (Department: 1712)

Plastic and nonmetallic article shaping or treating: processes

Optical article shaping or treating

Light polarizing article or holographic article

C524S081000, C524S357000, C524S363000, C524S359000, C528S378000, C528S380000, C568S335000, C351S159000, C264S299000, C264S328100

Reexamination Certificate

active

06444146

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
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.
2. Description of the Prior Art
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).
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
Therefore, an object of the present invention is to improve the color tone of these high-refractive index optical materials.
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.
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):
wherein R
1
is C
1
-C
10
hydrocarbon group; R
2
, R
3
and R
4
are each independently C
1
-C
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
subjecting the resultant composition to polymerization and curing.
DETAILED DESCRIPTION OF THE INVENTION
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
1
is preferably methylene or ethylene, more preferably methylene; R
2
, R
3
and R
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.
Examples of the compound having the radical represented by the formula (I) are listed below while classified into the groups (A) to (E):
(A) Compounds having in one molecule at least one radical represented by the formula (I) wherein n is 0;
(B) Compounds (a) having in one molecule at least one radical represented by the formula (I) wherein Y is O;
(C) Compounds (a) having in one molecule at least one radical represented by the formula (I) wherein Y is S;
(D) Compounds (a) having in one molecule at least one radical represented by the formula (I) wherein Y is Se; and
(E) Compounds (a) having in one molecule at least one radical represented by the formula (I) wherein Y is Te.
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.
Examples of the group (A) compound include:
Organic compounds having a chain aliphatic backbone structure such as 1,1-bis(epithioethyl)methane, 1,1-bis(epidithioethyl)methane, 1-(epithioethyl)-1-(&bgr;-epithiopropyl)-methane, 1,1-bis(&bgr;-epithiopropyl)-methane, 1-(epithioethyl)-1-(&bgr;-epithiopropyl)ethane, 1,2-bis(&bgr;-epithiopropyl)ethane, 1,2-bis(&bgr;-epidithiopropyl)ethane, 1-(epithioethyl)-3-(&bgr;-epithiopropyl)butane, 1,3-bis(&bgr;-epithiopropyl)propane, 1-(epithioethyl)-4-(&bgr;-epithiopropyl)pentane, 1,4-bis(&bgr;-epithiopropyl)butane, 1-(epithioethyl)-5-(&bgr;-epithiopropyl)hexane, 1-(epithioethyl)-2-(&ggr;-epithiobutylthio)ethane, 1-(epithioethyl)-2-[2-(&ggr;-epithiobutylthio)ethylthio]ethane, tetrakis(&bgr;-epithiopropyl)methane, 1,1,1-tris(&bgr;-epithiopropyl)propane, 1,3-bis(&bgr;-epithiopropyl)-1-(&bgr;-epithiopropyl)-2-thiapropane and 1,5-bis(&bgr;-epithiopropyl)-2,4-bis(&bgr;-epithiopropyl)-3-thiapentane;
Compounds having an alicyclic backbone structure such as 1,3-bis(epithioethyl)cyclohexane, 1,4-bis(epithioethyl)cyclohexane, 1,3-bis(&bgr;-epithiopropyl)cyclohexane, 1,4-bis(&bgr;-epithiopropyl)cyclohexane, bis[4-(epithioethyl)cyclohexyl]methane, bis[4-(&bgr;-epithiopropyl)cyclohexyl]methane, 2,2-bis[4-(epithioethyl)cyclohexyl]propane, 2,2-bis[4-(&bgr;-epithiopropyl)cyclohexyl]propane, bis[4-(&bgr;-epithiopropyl)cyclohexyl] sulfide, bis[4-(epithioethyl)cyclohexyl] sulfide, 2,5-bis(epithioethyl)-1,4-dithiane, 2,5-bis(&bgr;-epithiopropyl)-1,4-dithiane, 4-epithioethyl-1,2-cyclohexene 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-thia-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-epithioethyl)selenophane, 3,4-bis(1,2-epithioethyl)selenophane, 2,3-bis(2,3-epithiopropyl)selenophane, 2,4-bis(2,3-epithiopropyl)selenophane, 2,5-bis(2,3-epithiopropyl)selenophane, 3,4-bis(2,3-epithiopropyl)selenophane, 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-ep

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