Polymerizable composition for optical material, method for producing same, and method for producing optical material

Patent metadata

Field	Value
Publication number	US-9529117-B2
Application number	US-201314373718-A
Country	US
Kind code	B2
Filing date	Feb 13, 2013
Priority date	Feb 14, 2012
Publication date	Dec 27, 2016
Grant date	Dec 27, 2016

Abstract

By using a method for producing a composition for an optical material using (a) sulfur, (b) a compound having two intramolecular episulfide groups, (c) a compound having one or more (preferably two) SH groups, and (d) an amine compound having a specific structure, in which compound (a) and compound (c) are pre-polymerized in the presence of compound (b) using compound (d) as the pre-polymerization catalyst, the present invention provides a polymerizable composition for an optical material in which the viscosity elevation speed during pre-polymerization is slow and the reaction temperature is approximately room temperature, and that has a low viscosity and shows little increase in viscosity. By means of another embodiment of the present invention, it is possible to produce an optical material that has excellent mold release characteristics but has substantially no striae by polymerizing (a) sulfur, (b) a compound having two intramolecular episulfide groups, and (c) a compound having one or more SH groups in the presence of (d) a hindered amine catalyst having a specific structure.

First claim

The invention claimed is:

1. A polymerizable composition for optical materials, which comprises: a preliminary reaction solution obtained by subjecting 10 to 50 parts by mass of the below-described compound (a) and 1 to 20 parts by mass of the below-described compound (c) to a prepolymerization reaction in the presence of 50 to 90 parts by mass of the below-described compound (b) with the proviso that the total amount of the compound (a) and the compound (b) is 100 parts by mass, using 0.001 to 5 parts by mass of the below-described compound (d) as a prepolymerization catalyst; and a polymerization catalyst:
(a) sulfur (the compound (a));
(b) a compound having two intramolecular episulfide groups represented by the following formula (1) (the compound (b)):

wherein m represents an integer from 0 to 4, and n represents an integer from 0 to 1;
(c) a compound having one or more SH groups (the compound (c));
(d) a compound represented by the following formula (2) (the compound (d)):

wherein R represents an alkyl group having 1 to 4 carbon atoms, and X represents an organic group having 2 to 11 carbon atoms, which has any of a vinyl group, a vinylidene group and a vinylene group,
wherein said polymerizable composition has a viscosity of 63 mPa·s or less.

2. A method for producing a polymerizable composition for optical materials, according to claim 1 , which comprises the steps of:
subjecting 10 to 50 parts by mass of the below-described compound (a) and 1 to 20 parts by mass of the below-described compound (c) to a prepolymerization reaction in the presence of 50 to 90 parts by mass of the below-described compound (b) with the proviso that the total amount of the compound (a) and the compound (b) is 100 parts by mass, using 0.001 to 5 parts by mass of the below-described compound (d) as a prepolymerization catalyst, to obtain a preliminary reaction solution; and
adding a polymerization catalyst to the preliminary reaction solution:
(a) sulfur (the compound (a));
(b) a compound having two intramolecular episulfide groups represented by the following formula (1) (the compound (b)):

wherein m represents an integer from 0 to 4, and n represents an integer from 0 to 1;
(c) a compound having one or more SH groups (the compound (c));
(d) a compound represented by the following formula (2) (the compound (d)):

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

3. The polymerizable composition for optical materials according to claim 1 , wherein the polymerizable composition for optical materials is obtained by further adding the polymerization catalyst and the compound (c) to the preliminary reaction solution.

4. A method for producing an optical material, which comprises polymerizing and curing the polymerizable composition for optical materials according to claim 1 .

5. An optical material obtained by the production method according to claim 4 .

6. An optical lens comprising the optical material according to claim 5 .

7. A method for producing a polymerizable composition for optical materials, according to claim 1 , which comprises the steps of:
subjecting 10 to 50 parts by mass of the below-described compound (a) and 1 to 20 parts by mass of the below-described compound (c) to a prepolymerization reaction at a reaction temperature T 1 (wherein T 1 is 0 to 45° C.) in the presence of 50 to 90 parts by mass of the below-described compound (b) with the proviso that the total amount of the compound (a) and the compound (b) is 100 parts by mass, using 0.001 to 5 parts by mass of the below-described compound (d) as a prepolymerization catalyst, to obtain a preliminary reaction solution; and
adding a polymerization catalyst to the preliminary reaction solution with the temperature being set at T 2 with the proviso that T 2 is T 1 -15° C. to T 1 + 10 ° C. and 0 to 45° C.:
(a) sulfur (the compound (a));
(b) a compound having two intramolecular episulfide groups represented by the following formula (1) (the compound (b)):

wherein m represents an integer from 0 to 4, and n represents an integer from 0 to 1;
(c) a compound having one or more SH groups (the compound (c));
(d) a compound represented by the following formula (2) (the compound (d)):

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

8. A method for producing an optical material, which comprises polymerizing the polymerizable composition for optical materials produced by the production method according to claim 7 with the initial temperature of the polymerization being set at T 3 with the proviso that T 3 is T 2 -10° C. to T 2 + 10 ° C. and 0 to 40° C.

9. An optical material produced by the method according to claim 8 .

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Kamura Teruo
• SHIMODA Naotsugu
• NISHIMORI Yoshihiko
• Koshiishi Eiji
• Takeuchi Motoharu

Classifications

• G02B1/041 Primary

  Lenses · CPC title

• C08L81/02

  Polythioethers; Polythioether-ethers · CPC title

• G02B1/04

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

• C08G75/08

  from thiiranes · CPC title