Polymerizable composition, optical article obtained therefrom and method for the production of said optical article

Patent metadata

Field	Value
Publication number	US-9527948-B2
Application number	US-201214358447-A
Country	US
Kind code	B2
Filing date	Nov 16, 2012
Priority date	Nov 18, 2011
Publication date	Dec 27, 2016
Grant date	Dec 27, 2016

Abstract

The present invention relates to a polymerizable composition comprising polyisocyanate(s) (A), polythiol(s) (B), thiol(s) (C) and catalyst(s) (D). The polyisocyanate(s) (A) is at least one bifunctional or higher functional alicyclic polyisocyanate; the polythiol(s) (B) is at least one compound selected from polythiols represented by the following general formula (B1); the thiol(s) (C) is at least one compound selected from thiols having general formula (3); and the catalyst(s) (D) is at least one polymerization catalyst selected from metal compounds, quaternary ammonium salts, organic sulfonic acids, tertiary amines and relative inorganic or organic salts.

First claim

The invention claimed is:

1. A polymerizable composition comprising polyisocyanate(s) (A), polythiol(s) (B), thiol(s) (C) and catalyst(s) (D),
wherein the polyisocyanate(s) (A) is at least one selected from 1,3-bis(isocyanatemethyl)cyclohexane, 1,4-bis(isocyanatemethyl)cyclohexane, bis(4-isocyanatecyclohexyl)methane, and bis(isocyanatemethyl)-bicyclo-[2.2.1]heptane,
the polythiol(s) (B) is at least one selected from ethylene glycol bis(3-mercaptopropionate) and 1,4-butanediol bis(3-mercaptopropionate), the thiol(s) (C) is at least one selected from 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, and 4,8-, 4,7-, or 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-tri-thiaundecane, and
the catalyst(s) (D) is at least one polymerization catalyst selected from metal compounds, quaternary ammonium salts, and organic sulfonic acids.

2. The polymerizable composition according to claim 1 , further comprising at least one compound selected from the thiols having general formula (B2)

wherein R represents alkylene groups, the same or different from each other, having from 1 to 6 carbon atoms; R1 represents alkyl groups, the same or different from each other, having from 1 to 10 carbon atoms; n is an integer ranging from 1 to 6; m is an integer ranging from 1 to 6; p is an integer ranging from 1 to 4; q is equal to 0 or 1 and p+q is equal to 4.

3. The polymerizable composition according to claim 1 , wherein the polyisocyanate(s) (A) is a combination of at least two compounds selected from bis(4-isocyanatecyclohexyl)methane, bis(isocyanate-methyl)-bicyclo[2.2.1]heptane, 1,3-bis(isocyanatemethyl)-cyclohexane, and 1,4-bis(isocyanatemethyl)cyclohexane.

4. The polymerizable composition according to claim 1 , further comprising a polyisocyanate (E) selected from a non-cyclic aliphatic polyisocyanate, an aromatic polyisocyanate, an aliphatic polyisocyanate containing sulfur atoms, and an aromatic polyisocyanate containing sulfur atoms.

5. The polymerizable composition according to claim 4 , wherein the polyisocyanate (E) is selected from m-xylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4′-diphenylmethane diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate, octamethylene diisocyanate or mixtures thereof.

6. The polymerizable composition according to claim 2 , wherein the molar ratio between the mercapto groups belonging to the polythiols (B), the thiol(s) (C) and the thiols (B2) with respect to the isocyanate groups of the polyisocyanate(s) (A) varies within the range of 0.8-1.2.

7. The polymerizable composition according to claim 1 , further comprising an internal releasing agent consisting of a diester monoacid phosphate represented by the following general formula (5):

wherein R 2 and R 4 , the same or different, represent a linear or branched aliphatic group containing from 1 to 20 carbon atoms, or a cyclo-aliphatic group containing from 3 to 20 carbon atoms; R 3 and R 5 , the same or different, represent an alkylene group containing from 1 to 3 carbon atoms and m and p, independently from each other, are 0, 1 or 2.

8. An optical article obtained through the polymerization of the polymerizable composition according to claim 1 .

9. An optical lens, in particular for eye-glasses, comprising the optical article according to claim 8 , a hard coat layer and an anti-reflective layer.

10. A method for manufacturing an optical article comprising the following phases:
injecting a polymerizable composition according to claim 1 into a mould and let it polymerize, forming an optical article;
depositing sequentially a hard coating layer and an anti-reflection layer in sequence on said optical article.

Assignees

• Mitsui Chemicals Inc

Inventors

• Renzi Fiorenzo
• Forestieri Roberto
• Vecchione Andrea
• Bos Willem

Classifications

• C08K5/521

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

• C08G18/3865

  containing groups having one sulfur atom between two carbon atoms · CPC title

• C08L75/00

  Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers · CPC title

• G02C7/10

  Filters, e.g. for facilitating adaptation of the eyes to the dark; Sunglasses · CPC title

• C08G18/3863 Primary

  containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms · CPC title