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Polymerizable composition for optical materials

By using a combination of thiocarbamate oligomers and pre-reaction catalysts in episulfide compounds, the problems of uneven refractive index, deformation and yellowing in optical materials are solved, and efficient manufacturing and performance improvement of optical materials are achieved .

Active Publication Date: 2014-11-05
MITSUBISHI GAS CHEM CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the effect of inhibiting yellowing under heating conditions is insufficient, and there is a problem that the optical material may become cloudy or the like.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0123] 75.0 parts by mass of bis(β-epithiopropyl) sulfide as compound (a), 11.3 parts by mass of tetramethyl metaxylylene diisocyanate as compound (b), and 13.7 parts by mass as compound (c) Mixture of metaxylylene dithiol and 0.025 parts by mass of pentamethylpiperidinyl methacrylate as compound (d), and perform thiocarbamation pre-reaction at 20°C for 16 hours, and pass through FT -IR confirmed that the consumption of the isocyanate group of the compound (b) was 80%. In addition, it was confirmed by FT-IR that the consumption of episulfide groups was less than 1%. In addition, the viscosity of the preliminary reaction liquid at 20°C was 50 cP. 0.025 parts by mass of tetrabutylphosphonium bromide as a polymerization catalyst, 0.01 parts by mass of dibutyltin dichloride as a polymerization regulator, and 1.0 parts by mass of 2-(2- Hydroxy-5-tert-octylphenyl) benzotriazole is made into a uniform polymerizable composition. The obtained polymerizable composition was subjected t...

Embodiment 2

[0126] 80.0 parts by mass of bis(β-epithiopropyl) sulfide as compound (a), 8.4 parts by mass of tetramethyl metaxylylene diisocyanate as compound (b), and 11.6 parts by mass as compound (c) M-xylylene dithiol, 0.025 parts by mass of pentamethylpiperidinyl methacrylate as compound (d), 1.0 parts by mass of 2-(2-hydroxy-5-tert-octyl as ultraviolet absorber) The phenyl)benzotriazole was mixed, and the thiocarbamation prereaction was performed at 25°C for 10 hours. It was confirmed by FT-IR that the consumption of the isocyanate group of the compound (b) was 76%. In addition, it was confirmed by FT-IR that the consumption of episulfide groups was less than 1%. In addition, the viscosity of the preliminary reaction liquid at 20°C was 45 cP. 0.020 parts by mass of tetrabutylphosphonium bromide as a polymerization catalyst was mixed with this preliminary reaction liquid to prepare a uniform polymerizable composition. The obtained polymerizable composition was subjected to degassing ...

Embodiment 3

[0129] 50.0 parts by mass of bis(β-epithiopropyl) sulfide as compound (a), 28.3 parts by mass of tetramethyl metaxylylene diisocyanate as compound (b), and 21.7 parts by mass as compound (c) M-xylylene dithiol, 0.050 parts by mass of pentamethylpiperidinyl methacrylate as compound (d), and 1.0 parts by mass of 2-(2-hydroxy-5-tert-octyl as ultraviolet absorber) The phenyl)benzotriazole was mixed, and the pre-reaction of thiocarbamation was performed at 30°C for 6 hours. It was confirmed by FT-IR that the consumption of the isocyanate group of the compound (b) was 70%. In addition, it was confirmed by FT-IR that the consumption of episulfide groups was less than 1%. In addition, the viscosity of the preliminary reaction liquid at 20°C was 80 cP. 0.025 parts by mass of tetrabutylphosphonium bromide as a polymerization catalyst and 0.02 parts by mass of dibutyltin dichloride as a polymerization regulator were mixed with this preliminary reaction solution to prepare a uniform polym...

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Abstract

The present invention addresses the problem of providing: a catalyst for preliminary reaction and a preliminary reaction method, which are suitable for a composition that is obtained by adding a thiol compound and an isocyanate compound to an episulfide compound; and a polymerizable composition for optical materials, which is capable of preventing yellowing of an optical material which contains a composition that is obtained by adding a thiol compound and an isocyanate compound to an episulfide compound. The above-mentioned problem can be solved by a polymerizable composition for optical materials, which contains a thiourethane oligomer that is obtained by preliminarily reacting the whole or a part of a thiol compound and an isocyanate compound in a composition that contains an episulfide compound, the thiol compound and the isocyanate compound, while using a compound represented by formula (2) as a catalyst for preliminary reaction. (In formula (2), R represents an alkyl group having 1-4 carbon atoms; and X represents an organic group which has 2-11 carbon atoms and contains a vinyl group, a vinylidene group or a vinylene group.)

Description

Technical field [0001] The present invention relates to a polymerizable composition for optical materials, and further relates to optical materials such as plastic lenses, prisms, optical fibers, information recording substrates, and optical filters using the same. Among them, the present invention is suitable for use as a plastic lens. Background technique [0002] Plastic materials are light in weight, rich in toughness, and easy to dye. Therefore, in recent years, they have been used for various optical materials, especially eyeglass lenses. Optical materials, especially spectacle lenses, particularly require properties such as low specific gravity, high transparency and low yellowness, high refractive index and high Abbe number as optical properties, high heat resistance, high strength, and the like. The high refractive index can realize the thinning of the lens, and the high Abbe number reduces the chromatic aberration of the lens. High strength facilitates secondary proce...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G75/08G02B1/04
CPCG02B1/041C08L75/04C08L81/00C08G75/08G02B1/04
Owner MITSUBISHI GAS CHEM CO INC