Photochromic composition with polyol and poly(anhydride)

Patent metadata

Field	Value
Publication number	US-12163045-B2
Application number	US-201917638349-A
Country	US
Kind code	B2
Filing date	Aug 30, 2019
Priority date	Aug 30, 2019
Publication date	Dec 10, 2024
Grant date	Dec 10, 2024

Abstract

Provided is a curable photochromic coating composition including (a) a polyol component, (b) a poly(anhydride) having at least three cyclic anhydride groups, (c) a secondary crosslinker, and (d) a photochromic material. The polyol component includes (i) a first polyol having two hydroxyl groups and a hydroxyl equivalent weight of at least 15,000 g/mol and (ii) a second polyol different from the first polyol having at least three hydroxyl groups and a hydroxyl equivalent weight of at least 300 g/mol. The secondary crosslinker is selected from a poly(carbodiimide), an oxazoline-functional material, or mixtures thereof. The present invention also provides an optical article prepared from the curable photochromic coating composition.

First claim

What is claimed is:

1. A curable photochromic coating composition comprising:
(a) a polyol component, wherein the polyol component comprises:
(i) a first polyol having two hydroxyl groups and a hydroxyl equivalent weight of at least 15,000 g/mol; and
(ii) a second polyol different from the first polyol, said second polyol having at least three hydroxyl groups and a hydroxyl equivalent weight of at least 300 g/mol;

(b) a polyanhydride having at least three cyclic anhydride groups;
(c) a secondary crosslinker, wherein the secondary crosslinker is selected from the group consisting of a polycarbodiimide, an oxazoline-functional material, and mixtures thereof; and
(d) a photochromic material.

2. The curable photochromic coating composition of claim 1 , wherein the first polyol (i) and the second polyol (ii) are each independently selected from the group consisting of a polyurethane polyol, a polyether polyol, a polyester polyol, a polycarbonate polyol, an acrylic polyol, a polysiloxane polyol, a poly(urea)urethane polyol, a polyamide polyol, copolymers thereof, and combinations thereof.

3. The curable photochromic coating composition of claim 1 , wherein the first polyol (i) has a hydroxyl equivalent weight of less than 75,000 g/mol.

4. The curable photochromic coating composition of claim 1 , wherein the first polyol (i) comprises a thermoplastic polyurethane diol.

5. The curable photochromic coating composition of claim 1 , wherein the second polyol (ii) has a hydroxyl equivalent weight of less than 8,000 g/mol.

6. The curable photochromic coating composition of claim 1 , wherein the second polyol (ii) comprises polycaprolactone triol, polycaprolactone tetraol, polycarbonate triol, polycarbonate tetraol, acrylic polyol, or mixtures thereof.

7. The curable photochromic coating composition of claim 1 , wherein the polyanhydride (b) comprises a copolymer selected from the group consisting of:
a copolymer of maleic anhydride and a C 2 -C 24 olefin,
a copolymer of maleic anhydride and (meth)acrylate,
a copolymer of maleic anhydride and styrene,
and mixtures thereof.

8. The curable photochromic coating composition of claim 1 , wherein the polyanhydride (b) has a number average molecular weight in the range of 500 to 100,000 g/mol.

9. The curable photochromic coating composition of claim 1 , wherein the secondary crosslinker (c) comprises an oxazoline-functional material with at least three oxazoline groups.

10. The curable photochromic coating composition of claim 1 , wherein the photochromic material (d) is selected from the group consisting of naphthopyrans, benzopyrans, indenonaphthopyrans, indolonaphthopyrans, phenanthropyrans, spiropyrans, spirooxazines, mercury dithiozonates, fulgides, fulgimides, and mixtures thereof.

11. The curable photochromic coating composition of claim 1 , wherein the ratio of equivalents of anhydride groups present in polyanhydride (b) to the equivalents of hydroxyl groups present in the polyol component (a) ranges from 1:3 to 5:1.

12. The curable photochromic coating composition of claim 1 , wherein the photochromic coating composition comprises:
(a) 25 to 79.9 weight percent polyol component;
(b) 10 to 55 weight percent polyanhydride;
(c) 10 to 30 weight percent secondary crosslinker; and
(d) 0.1 to 20 weight percent photochromic compound,
where weight percentages are based on total solids present in the photochromic composition.

13. An optical article comprising the curable photochromic coating composition of claim 1 .

14. The optical article of claim 13 , wherein the optical article is a lens.

Assignees

• Transitions Optical Ltd

Inventors

• Reddy Ramaiahgari
• Veldkamp Brad S
• Kumar Anil

Classifications

• G02B5/23

  Photochromic filters · CPC title

• C09D5/29

  for multicolour effects · CPC title

• C09D7/80

  Processes for incorporating ingredients · CPC title

• C09D7/63

  organic · CPC title

• C08G63/08

  Lactones or lactides · CPC title