Polymerizable composition for optical articles

Patent metadata

Field	Value
Publication number	US-10294318-B2
Application number	US-201715677490-A
Country	US
Kind code	B2
Filing date	Aug 15, 2017
Priority date	Aug 16, 2016
Publication date	May 21, 2019
Grant date	May 21, 2019

Abstract

A polymerizable composition includes at least one first monomer and at least one second monomer, wherein the at least one first monomer includes an isohexide bis(allyl carbonate) monomer, and wherein the at least one second monomer includes one or more ethylenic unsaturations. Another polymerizable composition includes the reaction product of an isohexide bischloroformate; at least one polyol; allyl alcohol; and, optionally, at least one polychloroformate. An exemplary polymerizable composition includes the transesterification reaction product of an isohexide; diallyl carbonate; and at least one polyol. 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 composition, comprising at least one first monomer and at least one second monomer, wherein the at least one first monomer comprises an isohexide bis(allyl carbonate) monomer, and wherein the at least one second monomer is selected from the group consisting of ethyleneglycol bis(allyl carbonate), diethyleneglycol bis(allyl carbonate), 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.

2. The polymerizable composition of claim 1 , wherein the at least one isohexide bis(allyl carbonate) monomer is selected from the group consisting of isosorbide bis(allyl carbonate), isoidide bis(allyl carbonate), isomannide bis(allyl carbonate), and mixtures thereof.

3. The polymerizable composition of claim 1 , wherein the at least one second monomer is selected from the group consisting of ethyleneglycol bis(allyl carbonate), diethyleneglycol bis(allyl carbonate), and mixtures thereof.

4. The polymerizable composition of claim 1 , wherein the at least one second monomer comprises the reaction product of:
at least one of a bischloroformate or a trischloroformate;
allyl alcohol; and
at least one polyol.

5. The polymerizable composition of claim 4 , wherein the bischloroformate is selected from the group consisting of ethyleneglycol bischloroformate, diethyleneglycol bischloroformate, and mixtures thereof.

6. The polymerizable composition of claim 4 , wherein the trischloroformate comprises 1,3,5-tris(2-chloroformyloxyethyl)isocyanurate.

7. The polymerizable composition of claim 4 , wherein the at least one polyol comprises two to six hydroxyl groups.

8. The polymerizable composition of claim 4 , wherein the at least one polyol comprises a cyclic polyol.

9. The polymerizable composition of claim 8 , wherein the cyclic polyol comprises 1,3,5-tris(2-hydroxyethyl)isocyanurate.

10. The polymerizable composition of claim 4 , wherein the at least one polyol comprises a C 2 -C 12 diol.

11. The polymerizable composition of claim 4 , wherein the at least one polyol 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 thereof.

12. The polymerizable composition of claim 4 , further comprising at least one third monomer 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.

13. The polymerizable composition of claim 1 , wherein the at least one second monomer comprises the transesterification reaction product of:
diallyl carbonate; and
at least one polyol.

14. The polymerizable composition of claim 4 , wherein an equivalents ratio of total equivalents of hydroxyls to total equivalents of chloroformate is 1 to 1.5:1.

15. A polymerizable composition, comprising the reaction product of:
an isohexide bischloroformate;
at least one polyol comprising a cyclic polyol;
allyl alcohol; and
optionally, at least one polychloroformate.

16. The polymerizable composition of claim 15 , wherein the isohexide bischloroformate is selected from the group consisting of isosorbide bischloroformate, isoidide bischloroformate, isomannide bischloroformate, and mixtures thereof.

17. The polymerizable composition of claim 15 , wherein the at least one polyol comprises two to six hydroxyl groups.

18. The polymerizable composition of claim 15 , wherein the cyclic polyol comprises 1,3,5-tris(2-hydroxyethyl)isocyanurate.

19. The polymerizable composition of claim 15 , wherein the at least one polyol 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 thereof.

20. The polymerizable composition of claim 15 , wherein the at least one polychloroformate is present and is selected from the group consisting of ethyleneglycol bischloroformate and diethyleneglycol bischloroformate.

21. The polymerizable composition of claim 15 , wherein an equivalents ratio of total equivalents of hydroxyls to total equivalents of chloroformate is 1 to 1.5:1.

22. A polymerizable composition, comprising the transesterification reaction product of:
an isohexide;
diallyl carbonate;
at least one polyol; and
organic peroxide.

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

24. The polymerizable composition of claim 23 , wherein the organic peroxide is selected from the group consisting of peroxymonocarbonate ester, peroxydicarbonate ester, diacylperoxide, and peroxyester.

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

26. The polymerizable composition of claim 25 , wherein the organic peroxide is selected from the group consisting of peroxymonocarbonate ester, peroxydicarbonate ester, diacylperoxide, and peroxyester.

27. The polymerizable composition of claim 22 , wherein the organic peroxide is selected from the group consisting of peroxymonocarbonate ester, peroxydicarbonate ester, diacylperoxide, and peroxyester.

Assignees

• Ppg Ind Ohio Inc

Inventors

• Herold Robert D

Classifications

• C08F218/24

  Esters of carbonic or haloformic acids, e.g. allyl carbonate · CPC title

• G02B1/04

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

• C08L69/00

  Compositions of polycarbonates; Compositions of derivatives of polycarbonates · CPC title

• G02B1/041

  Lenses · CPC title

• C08F218/16 Primary

  with alcohols containing three or more carbon atoms · CPC title