Novel sulfur-containing compound and method for preparing the sa

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters

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568 57, 568 58, C07C 6952

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active

058346210

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to a novel sulfur-containing compound and a method for its preparation, more specifically to a novel sulfur-containing compound useful as a polymerization starting material for optical materials, such as plastic lenses for eyeglasses, Fresnel lenses, lenticular lenses, optical disc substrates, plastic optical fiber, prism sheets for LCD, photoconductive plates and diffusion sheets; paints; adhesives; sealants; and other materials, especially as a polymerization starting material (monomer) for optical materials, and a method for its preparation.


BACKGROUND ART

In recent years, resins for organic optical materials have been commonly used for various purposes, because they are lighter and easier to handle than glass etc.
Of such resins for organic optical materials, polystyrene resin, polymethyl methacrylate resin, polycarbonate resin, diethylene glycol diallylcarbonate resin, etc. have traditionally been used widely.
These conventional resins for organic optical materials are not always satisfactory, however, because they have some drawbacks, including low refractive index, great double refraction and high dispersive power, and because their heat resistance and impact resistance are poor.
Diethylene glycol diallylcarbonate resin (CR-39) etc. used as lens materials, in particular, are faulty in case that the lens made thereof has great edge thickness and center thickness due to the low refractive index (1.50), resulting in poor lens appearance and increased weight.
To resolve these problems, various methods have been proposed, mainly with the aim of increasing the refractive index. For example, Japanese Patent Examined Publication No. 5/4404 discloses a resin wherein a halogen is introduced to an aromatic ring. It should be noted, however, that the resin obtained by that method has a specific gravity of as high as 1.37, though having an increased refractive index of 1.60, and is unsatisfactory in terms of lens lightness, a major requirement for plastic lenses.
Japanese Patent Examined Publication No. 4/15249 and Japanese Patent Laid-Open No. 60/199016 disclose a technology for preparation of a resin by polymerization of an isocyanate compound and polythiol. However, said resin also has a specific gravity of not less than 1.30, though having an increased refractive index of 1.60. As another drawback, the resin's relatively low polymerization temperature and high polymerization rate hamper heat control during polymerization, resulting in significant optical strain.


DISCLOSURE OF THE INVENTION

The present invention was developed in view of the above circumstances. Accordingly, the object of the present invention is to provide a novel sulfur-containing compound as a monomer suitable for preparation of a resin having a high refractive index, and a method for its preparation.
Specifically, the gist of the present invention concerns: formula (I): ##STR2## wherein n is an integer from 0 to 2; R represents a hydrogen atom, a vinyl group, a methacryloyl group, a vinylbenzyl group, a glycidyl group, an acryloyl group or an allyl group; and the case where n is 0 and R is a hydrogen atom is not included; wherein R in the general formula (I) is a hydrogen atom, a vinyl group, a methacryloyl group, a vinylbenzyl group, or a glycidyl group; following general formula (Ia): ##STR3## wherein m is an integer of 1 or 2, characterized by reacting, in the presence of a base, a bis(4-halogenomethylphenyl) sulfide represented by the following general formula (II): ##STR4## wherein X is a chlorine atom, a bromine atom or an iodine atom with a dithiol represented by the following general formula (III): following general formula (Ia): ##STR5## wherein m is an integer of 1 or 2, characterized by reacting, in the presence of a base, a bis(4-halogenomethylphenyl) sulfide represented by the following general formula (II): ##STR6## wherein X is a chlorine atom, a bromine atom or an iodine atom with a mercaptoalcohol represented by the following general formula (IV): thiourea in the presenc

REFERENCES:
patent: 4605774 (1986-08-01), Baron et al.
patent: 4689387 (1987-08-01), Kajimoto et al.
patent: 4775733 (1988-10-01), Kanemura et al.
patent: 5077436 (1991-12-01), Yoshikawa et al.
Chem Abs 121: 134916 (1994).

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