4,4'-bis(methacryloylthio)diphenylsulfide

Details 4,4'-bis(methacryloylthio)diphenylsulfide 4,4'-bis(methacryloylthio)diphenylsulfide

1990-06-20

1993-02-02

Henderson, Christopher

Organic compounds -- part of the class 532-570 series

Organic compounds

Esters having the thiocarboxylate group, -cx-, wherein the...

C07C32700, C07C32722

Patent

active

051839172

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION

4,4,-Bis(Methacryloylthio)Diphenylsulfide
1. TECHNICAL FIELD
The present invention relates to a novel bifunctional polymerizable monomer capable of producing a transparent cured product having a high heat resistance, low water absorption, and high refractive index, more particularly, to 4,4,-bis(methacryloylthio)diphenylsulfide suitable as the starting material for paints, adhesives, cast molding materials, photosensitive resins, and optical materials, most particularly as the starting material for an optical material.
Furthermore, the present invention relates to a curable composition containing a prepolymer having a polythioether skeleton useful in the industrial fields of optical materials, coating agents, sealing agents, paints, and adhesives, particularly the field of optical materials, and a method of producing same. More particularly, it relates to a curable composition containing a prepolymer having a polythioether skeleton which gives a superior cured product having a high refractive index, low water absorption, and a high optical uniformity during polymerization, and a method of producing same.
2. Background of Art
A large number of derivatives of monofunctional methacrylic acid esters and polyfunctional methacrylic acid esters are known, and some of these esters are commercially produced and used as the starting materials for adhesives, paints, cast molding materials, and photosensitive materials, utilizing the high polymerizability thereof.
On the other hand, few derivatives of thiomethacrylic acid esters are known. For example, although phenylthiomethacrylate and 4-chlorophenylmethacrylate were synthesized by Jean Samrel et al [Journal of American Chemical Society (J. Am. Chem. Soc.), 86, 2509 (1958)], almost none of these thiomethacrylic acid esters have been utilized commercially.
In the prior art, as organic optical materials, polystyrene resins, polymethyl methacrylate resins, polycarbonate resins, and polymers of diethylene glycol and diallylcarbonate have been utilized, and since these have a desirable light weight, safety, workability, and dyeability, the demand therefore has increased.
Organic optical materials of the prior art, however, for example, polymethacrylate resins, have a high hygroscopicity as the resin characteristic, are susceptible to changes in shape or refractive index, and are unstable as optical materials. On the other hand, polystyrene resins and polycarbonate resins have drawbacks such as an optical birefringence, generation of scattered light, and loss of transparency with time. Further, the application of polymers of diethylene glycol diallylcarbonate per se as the optical material is limited due to the low refractive index (refractive index =1.499) thereof.
To eliminate these drawbacks, various resins for optical materials have been proposed, and examples of these proposals include, for example, Japanese Unexamined Patent Publications (Kokai) Nos. 57-28115, 57-28116, 59-184210, 60-7314, 60-179406, 60-217301, 60-186514, 60-166307, 60-103301, 60-124607, 62-232414, 62-235901, 62-267316, 63-15811, 63-46213, 63-72707, 63-75022, 63-113012, 63-130614, 63-130615, 63-170401, 63-170404, 63-191813, 63-248811, 63-251408, 63-268707, and 64-54021, Japanese Examined Patent Publication (Kokoku) Nos. 63-45081 and 63-45082, and Japanese Unexamined Patent Publication (Kokai) Nos. 59-164501, 60-217299, 61-16901, 62-283109, 62-287316 and 63-162702. The cured products obtained by these prior arts, however, are not satisfactory as optical materials because they are optically nonuniform, suffer from a severe weathering coloration, and lack dimensional stability.
Also, curable compositions of polyene and polythiol are disclosed in Japanese Patent Publication (Kokoku) No. 53-28959, Japanese Unexamined Patent Publications (Kokai) Nos. 53-134096, 57-125025, 57-130572, 58-80317, but in these prior arts, due to the action of the mercapto groups as the chain transfer agent, a problem arises in that the polymerization tends to proceed even under storage in a dark place. Further, wh

REFERENCES:
patent: 4388450 (1983-06-01), Crivello
patent: 4810812 (1989-03-01), Matsuda

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