Polymerizable compositions and optical articles prepared therefrom

Patent metadata

Field	Value
Publication number	US-9752025-B2
Application number	US-201314071849-A
Country	US
Kind code	B2
Filing date	Nov 5, 2013
Priority date	Nov 6, 2012
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

Abstract

Provided is a polymerizable non-aqueous dispersion, wherein the non-aqueous dispersion comprises:
(a) a polymerizable component; and (b) polymeric microparticles dispersed in a continuous phase, wherein the microparticles comprise a dispersion polymerization reaction product prepared from a reaction mixture comprising an ethylenically unsaturated monomer, and an acrylic polymer stabilizer, and wherein the continuous phase is the same as or different from the polymerizable component (a).

Also provided are optical articles prepared from the polymerizable non-aqueous dispersions.

First claim

What is claimed is:

1. A polymerizable non-aqueous dispersion, wherein the non-aqueous dispersion comprises:
(a) a polymerizable component as a continuous phase, wherein the polymerizable component (a) comprises at least one monomer, oligomer, and/or prepolymer having two or more allyl groups, and at least 95 percent by weight of said continuous phase comprises said polymerizable component; and
(b) polymeric microparticles dispersed in the continuous phase, wherein the microparticles comprise a dispersion polymerization reaction product prepared from a reaction mixture comprising an ethylenically unsaturated monomer, an acrylic polymer stabilizer, and an aliphatic polyester stabilizer, and wherein said polymeric microparticles have a particle size of less than 500 nm,
wherein the polymerizable component (a) further comprises at least one (meth)acrylate functional monomer and diethylene glycol bis(allylcarbonate).

2. The polymerizable non-aqueous dispersion of claim 1 , wherein the monomer having two or more allyl groups comprises diethylene glycol bis(allylcarbonate).

3. The polymerizable non-aqueous dispersion of claim 1 , wherein the non-aqueous dispersion further comprises a radical initiator.

4. The polymerizable non-aqueous dispersion of claim 3 , wherein the radical initiator comprises a peroxy initiator.

5. The polymerizable non-aqueous dispersion of claim 1 , wherein the polymerizable component (a) further comprises:
(a) at least one first (meth)acrylate functional monomer represented by the following Formula (I),

wherein,
L 1 is selected from, a multivalent optionally substituted hydrocarbyl group optionally interrupted with at least one of —C(O)—, —S—, —O—, and combinations thereof, and a divalent linking group represented by the following Formula (A),

wherein Y is O or S,
L 2 is independently for each n a divalent optionally substituted hydrocarbyl group optionally interrupted with at least one of —O— and —S—,
R 1 is independently selected for each n from hydrogen and methyl, and n is from 2 to 6;
(b) optionally, a polymerization moderator; and
(c) optionally, at least one monoethylenically unsaturated monomer.

6. The polymerizable non-aqueous dispersion of claim 1 , wherein the reaction mixture further comprises an aliphatic polyester stabilized seed polymer.

7. The polymerizable non-aqueous dispersion of claim 1 , wherein the aliphatic polyester has a carbon to oxygen ratio of 4:1 to 20:1.

8. The polymerizable non-aqueous dispersion of claim 1 , wherein the aliphatic polyester comprises poly-12-hydroxystearic acid.

9. The polymerizable non-aqueous dispersion of claim 1 , wherein the polyester has a weight average molecular weight of 10,000 to 30,000.

10. The polymerizable non-aqueous dispersion of claim 6 , wherein the aliphatic polyester has a carbon to oxygen ratio of 4:1 to 20:1.

11. The polymerizable non-aqueous dispersion of claim 6 , wherein the aliphatic polyester comprises poly-12-hydroxystearic acid.

12. The polymerizable non-aqueous dispersion of claim 6 , wherein the polyester has a weight average molecular weight of 10,000 to 30,000.

13. The polymerizable non-aqueous dispersion of claim 1 , wherein the acrylic polymer stabilizer comprises a nonlinear acrylic polymer.

14. The polymerizable non-aqueous dispersion of claim 1 , wherein at least 90 percent of the microparticles have an average particle size of up to 300 nanometers.

15. The polymerizable non-aqueous dispersion of claim 14 , wherein at least 90 percent of the microparticles have an average particle size of 180 nm or less.

16. The polymerizable non-aqueous dispersion of claim 1 , wherein the continuous phase is essentially free of non-polymerizable volatile organic compounds.

17. An optical article comprising a polymer prepared from the polymerizable non-aqueous dispersion of claim 1 .

18. The optical article of claim 17 , wherein the optical article is a lens, sheet product, scratch resistant lens, or scratch resistant sheet.

19. A polymerizable non-aqueous dispersion, wherein the non-aqueous dispersion comprises:
(a) a polymerizable component as a continuous phase, wherein the polymerizable component (a) comprises two or more ethylenic unsaturations; and
(b) polymeric microparticles dispersed in the continuous phase, wherein the microparticles comprise a dispersion polymerization reaction product prepared from a reaction mixture comprising an ethylenically unsaturated monomer, and an acrylic polymer stabilizer, and wherein said polymeric microparticles have a particle size of less than 500 nm,
wherein the polymerizable component (a) comprises:

(a) at least one first (meth)acrylate functional monomer represented by the following Formula (I),

wherein,
L 1 is selected from, a multivalent optionally substituted hydrocarbyl group optionally interrupted with at least one of —C(O)—, —S—, —O—, and combinations thereof, and a divalent linking group represented by the following Formula (A),

wherein Y is O or S,
L 2 is independently for each n a divalent optionally substituted hydrocarbyl group optionally interrupted with at least one of —O— and —S—,
R 1 is independently selected for each n from hydrogen and methyl, and n is from 2 to 6;
(b) optionally, a polymerization moderator; and
(c) optionally, at least one monoethylenically unsaturated monomer.

Assignees

• Ppg Ind Ohio Inc

Inventors

• Fenn David R
• Wang Wei
• Hickenboth Charles R
• Herold Robert D

Classifications

• C08F2/02 Primary

  Polymerisation in bulk · CPC title

• G02B1/041

  Lenses · CPC title

• C08L33/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title

• C08F2/14

  Organic medium · CPC title

• C08L33/08

  Homopolymers or copolymers of acrylic acid esters · CPC title