Composition for optical articles and optical articles made therewith

Patent metadata

Field	Value
Publication number	US-10407540-B2
Application number	US-201615258495-A
Country	US
Kind code	B2
Filing date	Sep 7, 2016
Priority date	Sep 8, 2015
Publication date	Sep 10, 2019
Grant date	Sep 10, 2019

Abstract

An exemplary polymerizable composition includes the reaction product of (a) diethyleneglycol bischloroformate; (b) allyl alcohol; (c) a cyclic polyol selected from the group consisting of a cycloaliphatic polyol having at least one secondary hydroxyl group, a heterocyclic polyol having primary and/or secondary hydroxyl groups, and mixtures thereof; (d) optionally, ethyleneglycol bischloroformate; and (e) optionally, at least one linear or branched aliphatic polyol having two to six hydroxyl groups. Another exemplary polymerizable composition includes the reaction product of (a) allyl alcohol; (b) a cyclic polyol selected from the group consisting of a cycloaliphatic polyol having at least one secondary hydroxyl group, a heterocyclic polyol having primary and/or secondary hydroxyl groups, and mixtures thereof; (c) ethyleneglycol bischloroformate; and (d) optionally, at least one linear or branched aliphatic polyol having two to six hydroxyl groups is also described. A reaction product, a polymerizate including the polymerizable composition, and an optical article including the polymerizable composition are also provided.

First claim

The invention claimed is:

1. A polymerizable thermosetting composition, comprising the reaction product of:
(a) diethyleneglycol bischloroformate;
(b) allyl alcohol;
(c) a cyclic polyol selected from the group consisting of a cycloaliphatic polyol having at least one secondary hydroxyl group, a heterocyclic polyol having primary and/or secondary hydroxyl groups, and mixtures thereof;
(d) optionally, ethyleneglycol bischloroformate; and
(e) optionally, at least one linear or branched aliphatic polyol having two to six hydroxyl groups,
wherein the allyl alcohol (b) is present in an amount of 0.4 to 1.99 equivalents of OH to 1 equivalent of chloroformate, and
wherein the cyclic polyol (c) is present in an amount of 0.01 to 0.6 equivalents of OH to 1 equivalent of chloroformate.

2. The polymerizable composition of claim 1 , wherein the aliphatic polyol (e) is present and comprises a C 2 -C 12 polyol with two to six hydroxyl groups.

3. The polymerizable composition of claim 1 , wherein the aliphatic polyol (e) is present and is selected from the group consisting of ethylene glycol, diethylene glycol, propylene glycol, 1,3-propanediol, 1,2-butanediol, 1,4-butanediol, neopentyl glycol, 2-methyl-1,3-propanediol, glycerol, trimethylolpropane, ditrimethylolpropane, pentaerythritol, dipentaerythritol, erythritol, meso-erythritol, xylitol, sorbitol, ethoxylates thereof, propoxylates thereof, and mixtures of any of the foregoing.

4. The polymerizable composition of claim 1 , wherein the heterocyclic polyol (c) is selected from the group consisting of isohexide, 1,3,5-tris(2-hydroxyethyl)isocyanurate, and mixtures thereof.

5. The polymerizable composition of claim 4 , wherein the heterocyclic polyol (c) is isohexide selected from the group consisting of isosorbide, isoidide, and isomannide.

6. The polymerizable composition of claim 1 , wherein an equivalents ratio of total equivalents of hydroxyls to total equivalents of chloroformate is 1 to 1.5:1.

7. The polymerizable composition of claim 1 , wherein the composition further comprises an additional component selected from the group consisting of triallylcyanurate, triallylisocyanurate, 1,3,5-tris(2-hydroxyethyl)isocyanurate tris(allyl carbonate), trimethylolpropane tris(allyl carbonate), pentaerythritol tetra(allyl carbonate), glycerol tris(allyl carbonate), ditrimethylolpropane tetra(allyl carbonate), diallylitaconate, dipentaerythritol hexa(allyl carbonate), and mixtures thereof.

8. The polymerizable composition of claim 1 , wherein the reaction product comprises at least one compound represented by:

where A represents a residue from the at least one cyclic polyol,
m′ is equal to 1 or 2, and
q is equal to the number of hydroxyl groups on the at least one cyclic polyol; and

where t is equal to 0 or 1.

9. The polymerizable composition of claim 1 , wherein the reaction product comprises at least one compound represented by:

where m and n are each independently 1 or 2; and

where t is equal to 0 or 1.

10. The polymerizable composition of claim 1 , wherein the reaction product comprises at least one compound represented by:

where A represents a residue from the at least one cyclic polyol,
m′ is equal to 1 or 2, and
q is equal to the number of hydroxyl groups on the at least one cyclic polyol; and

where B represents a residue from the at least one linear or branched aliphatic polyol,
m′ is equal to 1 or 2, and
s is equal to the number of hydroxyl groups on the at least one linear or branched aliphatic polyol; and

where t is equal to 0 or 1.

11. The polymerizable composition of claim 1 , wherein the reaction product comprises at least one compound represented by:

where m and n are each independently 1 or 2; and

where B represents a residue of the at least one linear or branched aliphatic polyol,
m′ is equal to 1 or 2, and
s is equal to the number of hydroxyl groups on the at least one linear or branched aliphatic polyol; and

where t is equal to 0 or 1.

12. A polymerizate, formed from the polymerizable composition of claim 1 .

13. An optical article, comprising the polymerizable composition of claim 1 .

14. A polymerizable composition of claim 1 , comprising a radically polymerizable monomer represented by:

where A represents a residue from at least one cyclic polyol,
m′ is equal to 1 or 2, and
q is equal to the number of hydroxyl groups on the at least one cyclic polyol.

15. The polymerizable composition of claim 1 , further comprising organic peroxide.

16. The polymerizable composition of claim 15 , wherein the organic peroxide is selected from the group consisting of peroxymonocarbonate ester, peroxydicarbonate ester, diacylperoxide, and peroxyester.

17. The polymerizable composition of claim 8 , wherein in Formula I, the at least one cyclic polyol is isohexide selected from the group consisting of isosorbide, isoidide, and isomannide, and q is 2.

18. The polymerizable composition of claim 8 wherein the at least one linear or branched aliphatic polyol is present.

Assignees

• Ppg Ind Ohio Inc

Inventors

• Herold Robert D
• Badarinarayana Vivek

Classifications

• C08F18/24 Primary

  Esters of carbonic or haloformic acids · CPC title

• C09D4/00 Primary

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title

• C08G64/0291 Primary

  unsaturated · CPC title

• G02B1/04

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