Composition for optical material, and method for producing same

Patent metadata

Field	Value
Publication number	US-9447226-B2
Application number	US-201314414585-A
Country	US
Kind code	B2
Filing date	Sep 6, 2013
Priority date	Sep 10, 2012
Publication date	Sep 20, 2016
Grant date	Sep 20, 2016

Abstract

A composition for an optical material includes (a) a compound having two β-epithiopropyl groups and having a specific structure, (b) a compound having one β-epithiopropyl group and one glycidyl group and having a specific structure, (c) polyisocyanate and (d) polythiol, enables the prevention of the occurrence of such a defect that peeling traces linger on a lens. In the composition for an optical material, an embodiment in which (e) sulfur is additionally contained is preferred. Another embodiment of the present invention is a method for producing an optical material, characterized by adding an onium salt as a polymerization catalyst to the composition for an optical material in an amount of 0.0001 to 10% by mass relative to the total amount of the compound (a), the compound (b), polyisocyanate (c) and polythiol (d) and then polymerizing and curing the resultant mixture.

First claim

The invention claimed is:

1. A composition for optical materials, which comprises (a) a compound described below, (b) a compound described below, (c) a polyisocyanate and (d) a polythiol:
the compound (a): a compound having the structure represented by the following formula (1):

wherein m represents an integer from 0 to 4, and n represents an integer from 0 to 2; and
the compound (b): a compound having the structure represented by the following formula (2):

wherein m represents an integer from 0 to 4, and n represents an integer from 0 to 2, and
wherein, when the total amount of the compound (a), the compound (b), the polyisocyanate (c) and the polythiol (d) is 100% by mass, the compound (a) is in an amount of 50 to 95% by mass; the compound (b) is in an amount of 0.05 to 20% by mass; the polyisocyanate (c) is in an amount of 1 to 25% by mass; and the polythiol (d) is in an amount of 1 to 25% by mass, and wherein the ratio of the SH groups in the polythiol (d) to the NCO groups in the polyisocyanate (c), [the number of the SH groups in the polythiol (d)/the number of the NCO groups in the polyisocyanate (c)] is 1.0 to 2.5.

2. The composition for optical materials according to claim 1 , wherein the polyisocyanate (c) is at least one compound selected from the group consisting of isophorone diisocyanate, tolylene diisocyanate, diphenylmethane diisocyanate, hexamethylene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, m-tetramethyl xylylene diisocyanate, p-tetramethyl xylylene diisocyanate, 1,3-bis(isocyanatemethyl)cyclohexane, 1,4-bis(isocyanatemethyl)cyclohexane, bis(isocyanatemethyl)norbornene and 2,5-diisocyanatemethyl-1,4-dithiane, and the polythiol (d) is at least one compound selected from the group consisting of bis(2-mercaptoethyl)sulfide, 2,5-dimercaptomethyl-1,4-dithiane, 1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl)benzene, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, pentaerythritol tetrakis-mercaptopropionate, pentaerythritol tetrakis-thioglycolate, trimethylolpropane tris(thioglycolate) and trimethylolpropane tris(mercapto propionate).

3. The composition for optical materials according to claim 1 , further comprising (e) a sulfur.

4. The composition for optical materials according to claim 3 , wherein, when the total amount of the compound (a), the compound (b), the polyisocyanate (c), the polythiol (d) and the sulfur (e) is 100% by mass, the compound (a) is in an amount of 50 to 95% by mass; the compound (b) is in an amount of 0.05 to 20% by mass; the polyisocyanate (c) is in an amount of 1 to 25% by mass; the polythiol (d) is in an amount of 1 to 25% by mass; and the sulfur (e) is in an amount of 0.1 to 15% by mass, and wherein the ratio of the SH groups in the polythiol (d) to the NCO groups in the polyisocyanate (c), [the number of the SH groups in the polythiol (d)/the number of the NCO groups in the polyisocyanate (c)] is 1.0 to 2.5.

5. A method for producing an optical material, which comprises the steps of:
adding an onium salt, as a polymerization catalyst, to the composition for optical materials according to claim 1 in an amount of 0.0001 to 10% by mass relative to the total amount of the compound (a), the compound (b), the polyisocyanate (c) and the polythiol (d); and
polymerizing and curing the resultant mixture.

6. A method for producing an optical material, which comprises the steps of:
adding an onium salt, as a polymerization catalyst, to the composition for optical materials according to claim 3 in an amount of 0.0001 to 10% by mass relative to the total amount of the compound (a), the compound (b), the polyisocyanate (c), the polythiol (d) and the sulfur (e); and
polymerizing and curing the resultant mixture.

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

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

9. A method for producing the composition for optical materials according to claim 1 , which comprises the steps of:
reacting an epoxy compound represented by formula (3) below with thiourea to obtain a mixture of the compound (a) and the compound (b); and
mixing the mixture with the polyisocyanate (c) and the polythiol (d):

wherein m represents an integer from 0 to 4, and n represents an integer from 0 to 2.

10. A method for producing the composition for optical materials according to claim 3 , which comprises the steps of:
reacting an epoxy compound represented by formula (3) below with thiourea to obtain a mixture of the compound (a) and the compound (b); and
mixing the mixture with the polyisocyanate (c), the polythiol (d) and the sulfur (e):

wherein m represents an integer from 0 to 4, and n represents an integer from 0 to 2.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Okada Hiroyuki
• Horikoshi Hiroshi
• Koshiishi Eiji
• Kamura Teruo

Classifications

• C08G18/3855 Primary

  having sulfur · CPC title

• C08G18/3876

  containing mercapto groups · CPC title

• C08G18/3874

  containing heterocyclic rings having at least one sulfur atom in the ring · CPC title

• C08G18/3868

  the sulfur atom belonging to a sulfide group · CPC title

• G02B1/041

  Lenses · CPC title