Polymerizable composition for polythiourethane optical material

Patent metadata

Field	Value
Publication number	US-9290656-B2
Application number	US-28030007-A
Country	US
Kind code	B2
Filing date	Feb 15, 2007
Priority date	Feb 21, 2006
Publication date	Mar 22, 2016
Grant date	Mar 22, 2016

Abstract

A polymerizable composition for polythiourethane optical materials comprising a compound represented by the general formula (1),

M(L)n  (1)
wherein, in the formula, M is Al, Fe, Cu, Zn, Zr or Bi; L is a dithiocarbamic acid group, a sulfonic acid group, a mono- or di-alkyl phosphoric acid ester group, a substituted acetylacetonato group or a halogen; and n is an integer of 1 to 5, one or two or more isocyanates selected from the group consisting of isocyanate compounds and isothiocyanate compounds, and one or two or more active hydrogen compounds each having a mercapto group. The compounds represented by the general formula (1) exhibit catalytic activity equal to or superior to that of organotin catalysts having been employed as catalysts for the production of polythiourethane optical materials from the past, and have high safety. Further, the thus obtained polythiourethane resins satisfactorily meet the property requirements for optical materials, in particular, excelling in weather resistance. Therefore, the proposed catalysts are available as novel catalysts replacing the organotin catalysts.

First claim

The invention claimed is:

1. A polymerizable composition for polythiourethane optical materials comprising:
zinc di-n-butyldithiocarbamate or zinc dimethyldithiocarbamate,
m xylylene diisocyanate, and
4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane,
wherein the polymerizable composition does not contain an organotin catalyst.

2. The polymerizable composition for polythiourethane optical materials according to claim 1 , comprising zinc dimethyldithiocarbamate, m xylylene diisocyanate, and 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane.

3. A polythiourethane optical material obtained by curing the polymerizable composition for polythiourethane optical materials according to claim 2 .

4. A plastic lens comprising the polythiourethane optical material according to claim 3 .

5. A polythiourethane optical material obtained by curing the polymerizable composition for polythiourethane optical materials according to claim 1 .

6. A plastic lens comprising the polythiourethane optical material according to claim 5 .

7. A process for producing a polythiourethane optical material, wherein the polymerizable composition for polythiourethane optical materials according to claim 1 is subjected to casting polymerization.

8. A polymerizable composition for polythiourethane optical materials comprising:
zinc di-n-butyldithiocarbamate,
m xylylene diisocyanate, and
a mixture of 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,
wherein the polymerizable composition does not contain an organotin catalyst.

9. A polythiourethane optical material obtained by curing the polymerizable composition for polythiourethane optical materials according to claim 8 .

10. A plastic lens comprising the polythiourethane optical material according to claim 9 .

11. A polymerizable composition for polythiourethane optical materials comprising:
zinc di-n-butyldithiocarbamate,
a mixture of 2,5-bis(isocyanatomethyl)-bicyclo[2.2.1]heptane and 2,6-bis(isocyanatomethyl)-bicyclo[2.2.1]heptane and
a mixture of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane and pentaerythritol tetrakis(3-mercaptoproprionate),
wherein the polymerizable composition does not contain an organotin catalyst.

12. The polymerizable composition for polythiourethane optical materials according to claim 11 , further comprising tetrabutylammonium chloride.

13. The polymerizable composition for polythiourethane optical materials according to claim 11 , further comprising tetrabutylammonium bromide.

14. A polythiourethane optical material obtained by curing the polymerizable composition for polythiourethane optical materials according to claim 12 .

15. A plastic lens comprising the polythiourethane optical material according to claim 14 .

16. A polythiourethane optical material obtained by curing the polymerizable composition for polythiourethane optical materials according to claim 13 .

17. A plastic lens comprising the polythiourethane optical material according to claim 16 .

18. A polythiourethane optical material obtained by curing the polymerizable composition for polythiourethane optical materials according to claim 11 .

19. A plastic lens comprising the polythiourethane optical material according to claim 18 .

20. A polymerizable composition for polythiourethane optical materials comprising:
a catalyst which is zinc N-ethyl-N-phenyldithiocarbamate;
an isocyanate compound which is m-xylylene diisocyanate; and
an active hydrogen compound which is 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane,
wherein the polymerizable composition does not contain an organotin catalyst.

21. A polythiourethane optical material obtained by curing the polymerizable composition for polythiourethane optical materials according to claim 20 .

22. A plastic lens comprising the polythiourethane optical material according to claim 21 .

23. A process for producing a polythiourethane optical material, wherein the polymerizable composition for polythiourethane optical materials according to claim 8 is subjected to casting polymerization.

24. A process for producing a polythiourethane optical material, wherein the polymerizable composition for polythiourethane optical materials according to claim 11 is subjected to casting polymerization.

25. A process for producing a polythiourethane optical material, wherein the polymerizable composition for polythiourethane optical materials according to claim 12 is subjected to casting polymerization.

26. A process for producing a polythiourethane optical material, wherein the polymerizable composition for polythiourethane optical materials according to claim 13 is subjected to casting polymerization.

27. A process for producing a polythiourethane optical material, wherein the polymerizable composition for polythiourethane optical materials according to claim 20 is subjected to casting polymerization.

Assignees

• Hayashi Hidetoshi
• Kawato Nobuo
• Iwazumi Masanori
• Tanaka Mamoru
• Kobayashi Seiichi
• Mitsui Chemicals Inc

Inventors

• Hayashi Hidetoshi
• Kawato Nobuo
• Iwazumi Masanori
• Tanaka Mamoru
• Kobayashi Seiichi

Classifications

• C08G18/3876

  containing mercapto groups · CPC title

• G11B7/2533

  comprising resins · CPC title

• C08G18/7642

  containing at least two isocyanate or isothiocyanate groups linked to the aromatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate groups, e.g. xylylene diisocyanate or homologues substituted on the aromatic ring · CPC title

• G02B1/041

  Lenses · CPC title

• C08G18/757

  containing at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic group · CPC title