Polymerizable composition for optical material, optical material produced from same, and process for producing same

Patent metadata

Field	Value
Publication number	US-10196501-B2
Application number	US-201515305934-A
Country	US
Kind code	B2
Filing date	Apr 30, 2015
Priority date	May 2, 2014
Publication date	Feb 5, 2019
Grant date	Feb 5, 2019

Abstract

Provided is a polymerizable composition for an optical material including (A) isocyanates having two or more isocyanato groups, which include at least an isophorone diisocyanate, (B) at least one predetermined thiol having two or more mercapto groups, (C) an acidic phosphoric acid ester represented by General Formula (1), and (D) a tin compound represented by General Formula (2), in which the acidic phosphoric acid ester (C) is contained in an amount of 0.05 parts by weight to 0.9 parts by weight, with respect to a total of 100 parts by weight of the isocyanates (A) and the thiols (B), and the tin compound (D) is contained in such an amount that the content of tin is 0.05 parts by weight to 0.3 parts by weight, with respect to a total of 100 parts by weight of the isocyanates (A) and the thiols (B).

First claim

The invention claimed is:

1. A polymerizable composition for an optical material, comprising:
(A) isocyanates having two or more isocyanato groups, which include at least an isophorone diisocyanate;
(B) one or more thiols having two or more mercapto groups;
(C) an acidic phosphoric acid ester represented by General Formula (1);

wherein, in General Formula (1), m represents an integer of 1 or 2, n represents an integer of 0 to 18, R 1 represents an alkyl group having 1 to 20 carbon atoms, and R 2 and R 3 each independently represent a hydrogen atom, a methyl group, or an ethyl group; and
(D) a tin compound represented by General Formula (2);
(R 4 ) c —Sn—X 4-c   (2)

wherein, in General Formula (2), R 4 represents an alkyl group having 1 to 4 carbon atoms, X represents a fluorine atom, a chlorine atom, a bromine atom or —O—C(═O)—R 5 wherein R 5 represents an alkyl group having 1 to 11 carbon atoms, and c represents an integer of 1 to 3,
wherein the acidic phosphoric acid ester (C) is contained in an amount of 0.05 parts by weight to 0.9 parts by weight, with respect to a total of 100 parts by weight of the isocyanates (A) and the thiols (B),
the tin compound (D) is contained in such an amount that the content of tin is 0.08 parts by weight to 0.3 parts by weight, with respect to a total of 100 parts by weight of the isocyanates (A) and the thiols (B), and
the thiols (B) include at least one selected from bis(mercaptoethyl)sulfide, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, and 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithiethane.

2. The polymerizable composition for an optical material according to claim 1 , wherein the isocyanates (A) include at least one selected from an aliphatic isocyanate, an aromatic isocyanate, a heterocyclic isocyanate, and an alicyclic isocyanate, in addition to the isophorone diisocyanate.

3. The polymerizable composition for an optical material according to claim 1 , wherein the thiols (B) include at least one selected from 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane.

4. A molded product obtained by polymerizing and curing the polymerizable composition for an optical material according to claim 1 .

5. An optical material comprised of the molded product according to claim 4 .

6. A plastic eyeglass lens comprised of the molded product according to claim 4 .

7. A process for producing a polymerizable composition for an optical material, comprising:
a step of preparing a composition including
(A) isocyanates having two or more isocyanato groups, which include at least an isophorone diisocyanate,
(B) one or more thiols having two or more mercapto groups,
(C) an acidic phosphoric acid ester represented by General Formula (1) in an amount of 0.05 parts by weight to 0.9 parts by weight, with respect to a total of 100 parts by weight of the isocyanates (A) and the thiols (B),

wherein, in General Formula (1), m represents an integer of 1 or 2, n represents an integer of 0 to 18, R 1 represents an alkyl group having 1 to 20 carbon atoms, and R 2 and R 3 each independently represent a hydrogen atom, a methyl group, or an ethyl group, and
(D) a tin compound represented by General Formula (2) wherein an amount of tin is 0.08 parts by weight to 0.3 parts by weight, with respect to a total of 100 parts by weight of the isocyanates (A) and the thiols (B),
(R 4 ) c —Sn—X 4-c   (2)

wherein, in General Formula (2), R 4 represents an alkyl group having 1 to 4 carbon atoms, X represents a fluorine atom, a chlorine atom, a bromine atom or —O—C(═O)—R 5 wherein R 5 represents an alkyl group having 1 to 11 carbon atoms, and c represents an integer of 1 to 3, and
wherein the thiols (B) include at least one selected from bis(mercaptoethyl)sulfide, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, and 2-(2,2-bis(mercaptomethylthio)ethyl)-1,3-dithiethane.

8. The process for producing a polymerizable composition for an optical material according to claim 7 , wherein the step of preparing a composition includes
a step of mixing the isocyanates (A) and the tin compound (D) in the presence of 32 parts by weight or more of the acidic phosphoric acid ester (C), with respect to 100 parts by weight of tin contained in the tin compound (D), and
a step of mixing the resulting mixture with the remaining necessary amount of the acid phosphoric acid ester (C) if desired, and the thiols (B).

9. The process for producing a polymerizable composition for an optical material according to claim 7 , wherein the step of preparing a composition includes
a step of mixing the thiols (B) and the tin compound (D), and
a step of mixing the resulting mixture with the isocyanates (A), and the acidic phosphoric acid ester (C).

10. The process for producing a polymerizable composition for an optical material according to claim 7 , wherein the step of preparing a composition includes
a step of mixing the isocyanates (A) and the thiols (B), and
a step of mixing the resulting mixture with the acidic phosphoric acid ester (C), and the tin compound (D).

11. The process for producing a polymerizable composition for an optical material according to claim 7 , wherein the isocyanates (A) include at least one selected from an aliphatic isocyanate, an aromatic isocyanate, a heterocyclic isocyanate, and an alicyclic isocyanate, in addition to the isophorone diisocyanate.

12. The process for producing a polymerizable composition for an optical material according to claim 7 , wherein the thiols (B) include at least one selected from 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane.

13. A process for producing a plastic eyeglass lens, comprising:
a step of obtaining a polymerizable composition for an optical material by the method according to claim 7 ;
a step of injecting the polymerizable composition for an optical material into a lens casting mold; and
a step of polymerizing the polymerizable composition for an optical material.

Assignees

• Mitsui Chemicals Inc

Inventors

• Hanawa Takayuki
• Kuma Shigetoshi

Classifications

• C08G18/3876

  containing mercapto groups · CPC title

• C08G18/24

  of tin · CPC title

• C08G18/388

  having phosphorus bound to carbon and/or to hydrogen · CPC title

• C08K5/521 Primary

  Esters of phosphoric acids, e.g. of H3PO4 · CPC title

• G02B1/04

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