Sulfur compound and use thereof

Details Sulfur compound and use thereof Sulfur compound and use thereof

2002-01-25

2003-05-27

Rotman, Alan L. (Department: 1626)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S022000, C549S039000

Reexamination Certificate

active

06570025

ABSTRACT:

This application is a 371 of PCT/JP00/05368 with international filing date of Aug. 10, 2000.
TECHNICAL FIELD
This invention relates to a sulfur-containing (meth)acrylic ester compound. The present invention is also concerned with a polymerizable composition comprising the sulfur-containing (meth)acrylic ester compound, and also with an optical part obtained by polymerizing the polymerizable composition.
The sulfur-containing (meth)acrylic ester compound according to the present invention has a characteristic feature in molecular structure that contains a cyclic thioacetal structure in its molecule, and is useful as a monomer for a photocurable, polymerizable composition. The optical part obtained by curing the polymerizable composition is excellent in optical properties, thermal properties and mechanical properties, is good in productivity and has high refractive index, so that it is useful as various plastic lenses represented by correctional eyeglass lenses, substrates for optical information recording media, plastic substrates for liquid crystal cells, coating materials for optical fibers, and the like.
BACKGROUND ART
Inorganic glass is excellent in various physical properties as typified by excellent transparency and small optical anisotropy, and therefore, is used as a transparent optical material in a wide variety of fields. Nonetheless, it involves problems such as heavy weight, fragility and poor productivity, and in recent years, developments of optical resins as replacements for inorganic glass are actively under way.
As an optical resin, a fundamentally important property is transparency. Industrial optical resins known to date to have good transparency include polymethyl methacrylate (PMMA), bisphenol A polycarbonate (BPA-PC), polystyrene (PS), methyl methacrylate-styrene copolymer (MS), styrene-acrylonitrile copolymer (SAN), poly(4-methylpentene-1) (TPX), polycycloolefins (COPs), polydiethylene glycol bis(allyl carbonate) (EGAC), polythiourethanes (PTUs), and the like.
PMMA is excellent in transparency and weatherability and is also good in moldability. It, however, involves drawbacks in that it has a refractive index (nd) as low as 1.49 and high water absorption property.
BPA-PC has a large chromatic aberration so that a limitation is imposed on its application fields, although it is excellent in transparency, heat resistance, impact resistance and high refraction properties.
PS and MS are excellent in moldability, transparency, low water absorption property, and high refraction properties. They are, however, inferior in impact resistance, weatherability and heat resistance so that they have not found any substantial practical utility as optical resins.
SAN is relatively high in refractive index and its mechanical properties are considered to be well-balanced. However, SAN is somewhat defective in heat resistance (heat distortion temperature: 80 to 90° C.) and practically, is not used as an optical resin.
TPX and COPs are excellent in transparency and heat resistance, and have low water absorption property. They are, however, accompanied by problems in that they are low in refractive index (nd: 1.47 to 1.53) and are poor in impact resistance, gas barrier property and dyeability.
EGAC is a thermosetting resin available from diethylene glycol bis(allyl carbonate) as a monomer, and is used most widely for general-purpose eyeglass lenses. Although it is excellent in transparency and heat resistance and is extremely small in chromic aberration, it has drawbacks in that it is low in refractive index (nd=1.50) and is inferior in impact resistance.
PTUs are thermosetting resins each of which are obtained by a reaction between a diisocyanate compound and a polythiol compound, and are used most widely for eyeglass lenses of high refractive index. They are extremely good materials for their outstanding transparency, impact resistance, high refractive properties and their small chromic aberration. They are, however, deficient only in that they require long thermopolymerization molding time (1 to 3 days), and are still accompanied by an unsolved problem in productivity.
With a view to achieving polymerization and curing in a short time to increase their productivity, certain production processes have been proposed, including photopolymerization of a bromine- or sulfur-containing acrylic ester to obtain an optical lens (e.g., JP 4-161410 A, JP 3-217412 A) and use of a (meth)acrylic ester compound having a sulfur-containing alicyclic structure for the production of an optical lens (e.g., JP 3-215801 A).
These processes make it possible to achieve polymerization in a short time, but the resulting resins are by no means satisfactory for optical parts. Described specifically, when these resins are used as eyeglass lenses, for example, those having high refractive indexes involve problems in that they are brittle and susceptible to breakage and are high in specific gravity. There is, accordingly, a strong desire for the development of a material free of these problems.
As has been described above, it is the current circumstance that each of the conventional optical resins still has one or more drawbacks to be solved although it has certain excellent properties. Under the foregoing situation, it is the current circumstance that a keen desire exists for the development of an optical resin excellent in optical properties, mechanical properties and thermal properties and high in productivity and refractive index.
DISCLOSURE OF THE INVENTION
An object of the present invention is, therefore, to solve the above-described drawbacks of the conventional optical resins, and to provide a monomer as a raw material for an optical material excellent in optical properties, mechanical properties and thermal properties and high in productivity and refractive index and also to provide an intermediate for the monomer.
The present inventors have proceeded with an extensive investigation to achieve the above-described object and as a result, have reached the present invention. Specifically, the present invention relates to a sulfur-containing (meth)acrylic ester compound represented by the following formula (1):
wherein R
1
and R
2
each independently represent a hydrogen atom or an alkyl group or may be fused together to form a ring, R
3
represents a hydrogen atom or a methyl group, X
1
represents an oxygen atom or a sulfur atom, m stands for an integer of from 0 to 3, and n stands for an integer of from 1 to 4.
The present invention also relates to a polymerizable composition comprising the sulfur-containing (meth)acrylic ester compound represented by formula (1), a cured product obtained by polymerizing the polymerizable composition, and further, an optical part comprising the cured product.
BEST MODES FOR CARRYING OUT THE INVENTION
The present invention will hereinafter be described in detail.
The sulfur-containing (meth)acrylic ester compound according to the present invention, which is represented by formula (1), is a novel compound, and is a (meth)acrylic ester characterized by the possession of a cyclic thioacetal structure in the moiety of the ester group.
In formula (1), R
1
and R
2
each independently represent a hydrogen atom or an alkyl group. As an alternative, R
1
and R
2
may be fused together to form a ring.
Each of the substituents R
1
and R
2
may preferably be a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, with a hydrogen atom, a methyl group or an ethyl group being more preferred. When R
1
and R
2
are fused together to form a ring, the ring may be preferably a cycloalkane ring, more preferably a cycloalkane ring having 5 to 7 carbon atoms, still more preferably a cyclohexane ring.
In formula (1), m is an integer of from 0 to 3, preferably an integer of from 0 to 2, more preferably an integer of 0 or 1.
In formula (1), n is an integer of from 1 to 4, preferably an integer of from 1 to 3, more preferably an integer of 1 or 2.
In formula (1), X
1
represents an oxygen atom or a sulfur atom. In view of a high refractive index required upon using as a lens

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