Polymerizable composition for optical materials

Patent metadata

Field	Value
Publication number	US-9518153-B2
Application number	US-201314380809-A
Country	US
Kind code	B2
Filing date	Feb 27, 2013
Priority date	Mar 1, 2012
Publication date	Dec 13, 2016
Grant date	Dec 13, 2016

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) below as a catalyst for preliminary reaction

In formula (2), R represents an alkyl group having 1 to 4 carbon atoms; and X represents an organic group which has 2 to 11 carbon atoms and contains a vinyl group, a vinylidene group or a vinylene group.

First claim

The invention claimed is:

1. A polymerizable composition for optical materials, which comprises:
1) a compound (a) below; and
2) a reaction solution, which contains a thiourethane oligomer that is obtained by preliminarily reacting a compound (b) below and a compound (c) below using a compound (d) below as a catalyst for a preliminary reaction, wherein, the preliminary reaction is conducted substantially in the absence of polymerization of an episulfide compound (a):
(a) a compound having two intramolecular episulfide groups represented by formula (1) below:

wherein m represents an integer from 0 to 4, and n represents an integer from 0 to 2;
(b) a compound having at least one isocyanate group in one molecule;
(c) a compound having at least two thiol groups in one molecule; and
(d) a compound represented by formula (2) below:

wherein R represents an alkyl group having 1 to 4 carbon atoms, and X represents an organic group which has 2 to 11 carbon atoms and contains a vinyl group, a vinylidene group or a vinylene group.

2. A polymerizable composition for optical materials of claim 1 , which comprises a reaction solution containing a thiourethane oligomer that is obtained by preliminarily reacting a compound (b) and a compound (c) in the presence of a compound (a), using a compound (d) as a catalyst for preliminary reaction:
(a) a compound having two intramolecular episulfide groups represented by formula (1).

3. The polymerizable composition for optical materials according to claim 1 , wherein with respect to the ratio in raw materials of the polymerizable composition for optical materials, the amount of the compound (d) is 0.005 to 5 parts by mass when the total amount of the compounds (a) to (c) is 100 parts by mass.

4. A method for producing the polymerizable composition for optical materials of claim 1 , comprising:
obtaining a reaction solution containing a thiourethane oligomer by preliminarily reacting a compound (b) below and a compound (c) below using a compound (d) below as a catalyst for preliminary reaction; and
mixing the reaction solution with a compound (a) below:
(a) a compound having two intramolecular episulfide groups represented by formula (1);

(b) a compound having at least one isocyanate group in one molecule;
(c) a compound having at least two thiol groups in one molecule; and
(d) a compound represented by formula (2)

5. A method for producing an optical material, comprising the step of polymerizing and curing the polymerizable composition according to claim 1 .

6. A cured product obtained by the production method according to claim 5 .

7. An optical material comprising the cured product according to claim 6 .

8. An optical lens comprising the optical material according to claim 7 .

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Koshiishi Eiji
• Okazaki Hitoshi
• Takeuchi Motoharu

Classifications

• G02B1/041 Primary

  Lenses · CPC title

• G02B1/04

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title

• C08L81/00

  Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers · CPC title

• C08L75/04

  Polyurethanes · CPC title

• C08G75/08 Primary

  from thiiranes · CPC title