Composition for optical articles and optical articles made therewith
An exemplary polymerizable thermosetting 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. The allyl alcohol (a) is present in an amount of 0.4 to 1.99 equivalents of OH to 1 equivalent chloroformate, and the cyclic polyol (b) is present in an amount of 0.01 to 0.6 equivalents of OH to 1 equivalent of chloroformate. A reaction product, a polymerizate including the polymerizable thermosetting composition, and an optical article including the polymerizable thermosetting composition are also provided.
1. A polymerizable thermosetting composition, comprising 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,
wherein the allyl alcohol (a) is present in an amount of 0.4 to 1.99 equivalents of OH to 1 equivalent chloroformate, and
wherein the cyclic polyol (b) is present in an amount of 0.01 to 0.6 equivalents of OH to 1 equivalent of chloroformate.
2. The polymerizable thermosetting composition of claim 1 , wherein the aliphatic polyol (d) is present and comprises a C 2 -C 12 polyol with two to six hydroxyl groups.
3. The polymerizable thermosetting composition of claim 1 , wherein the aliphatic polyol (d) 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 thermosetting composition of claim 1 , wherein the heterocyclic polyol (b) is selected from the group consisting of isohexide, 1,3,5-tris(2-hydroxyethyl)isocyanurate, and mixtures thereof.
5. The polymerizable thermosetting composition of claim 4 , wherein the heterocyclic polyol (b) is isohexide selected from the group consisting of isosorbide, isoidide, and isomannide.
6. The polymerizable thermosetting 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 thermosetting 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 thermosetting 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, and
q is equal to the number of hydroxyl groups on the at least one cyclic polyol; and
(b) at least one of Formula II
where t is equal to 0.
9. The polymerizable thermosetting composition of claim 1 , wherein the reaction product comprises at least one compound represented by:
where m and n are each 1; and
(b) at least one of Formula II
where t is equal to 0.
10. The polymerizable thermosetting 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, 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, and
s is equal to the number of hydroxyl groups on the at least one linear or branched aliphatic polyol; and
(c) at least one of Formula II
where t is equal to 0.
11. The polymerizable thermosetting composition of claim 1 , wherein the reaction product comprises at least one compound represented by:
where m and n are each 1; and
where B represents a residue of the at least one linear or branched aliphatic polyol,
m′ is equal to 1, and
s is equal to the number of hydroxyl groups on the at least one linear or branched aliphatic polyol; and
(c) at least one of Formula II
where t is equal to 0.
12. A polymerizate, formed from the polymerizable thermosetting composition of claim 1 .
13. An optical article, comprising the polymerizable thermosetting composition of claim 1 .
14. The polymerizable thermosetting composition of claim 1 , further comprising organic peroxide.
15. The polymerizable thermosetting composition of claim 14 , wherein the organic peroxide is selected from the group consisting of peroxymonocarbonate ester, peroxydicarbonate ester, diacylperoxide, and peroxyester.