Photochromic polyurethane laminate

Patent metadata

Field	Value
Publication number	US-11427754-B2
Application number	US-201715667320-A
Country	US
Kind code	B2
Filing date	Aug 2, 2017
Priority date	Jan 9, 2013
Publication date	Aug 30, 2022
Grant date	Aug 30, 2022

Abstract

Photochromic polyurethane laminates and methods for the formation of same wherein the photochromic polyurethane layer of the laminate has been crosslinked with a isocyanate-active prepolymer using a crosslinking agent. The crosslinking agent is formulated to have at least three functional groups that are reactive with functional groups of the polyurethane or of the isocyanate-active prepolymer.

First claim

What is claimed is:

1. A spectacle lens comprising:
a lens base material; and
a laminate disposed within or on a surface of the lens base material, the laminate comprising:
a first resin sheet; and
a polyurethane adhesive layer attached directly to the first resin sheet, the polyurethane adhesive layer is formed from a reaction composition comprising a polyurethane prepolymer, a crosslinking agent consisting of di(trimethylolpropane), and a chain extender consisting of 1,4-butane diol, wherein a molar ratio of the crosslinking agent and the chain extender is in the range of 0.18 to 1.03, wherein the polyurethane prepolymer is formed from a composition comprising:
a polycarbonate polyol having a number average molecular weight of approximately 800 and a hydroxyl value of 141.1 mg KOH/g, wherein said polycarbonate polyol is formed from a composition consisting of a 1:1 molar ratio of 1,3-propane diol and 1,4-butane diol,
a polyether polyol having a number average molecular weight of about 1,000, and
an aliphatic diisocyanate.

2. The spectacle lens according to claim 1 wherein the polycarbonate polyol has a formula:

where “n” is equal to an integer from 3 to 6 or a combination thereof, and “x” is an integer that makes the molecular weight of the polycarbonate polyol approximately equal to 800.

3. The spectacle lens according to claim 1 wherein the polyether polyol having a formula:
OH—[CH 2 —CH 2 —CH 2 —CH 2 —O] n H

where n is an integer.

4. The spectacle lens according to claim 1 wherein the aliphatic diisocyanate comprises 4,4′-dicyclohexylmethane-diisocyanate.

5. The spectacle lens according to claim 1 wherein the first resin sheet comprises polycarbonate.

6. The spectacle lens according to claim 1 wherein the first resin sheet comprises cellulose acetate butyrate.

7. The spectacle lens according to claim 1 further comprising a second resin sheet, the polyurethane adhesive layer attached directly to the second resin sheet.

8. The spectacle lens according to claim 1 wherein the lens base material comprises polycarbonate.

9. An optical laminate comprising:
a first resin sheet; and
a polyurethane adhesive layer attached directly to the first resin sheet, the polyurethane adhesive layer is formed from a reaction composition comprising a polyurethane prepolymer, a crosslinking agent consisting of di(trimethylolpropane), and a chain extender consisting of 1,4-butane diol, wherein a molar ratio of the crosslinking agent and the chain extender is in the range of 0.18 to 1.03, wherein the polyurethane prepolymer is formed from a composition comprising:
a polycarbonate polyol having a number average molecular weight of approximately 800 and a hydroxyl value of 141.1 mg KOH/g, wherein said polycarbonate polyol is formed from a composition consisting of a 1:1 molar ratio of 1,3-propane diol and 1,4-butane diol,
a polyether polyol having a number average molecular weight of about 1,000, and
an aliphatic diisocyanate.

10. The optical laminate according to claim 9 wherein the polycarbonate polyol has a formula:

where “n” is equal to an integer from 3 to 6 or a combination thereof, and “x” is an integer that makes the molecular weight of the polycarbonate polyol approximately equal to 800.

11. The optical laminate according to claim 9 wherein the polyether polyol has a formula:
OH—[CH 2 —CH 2 —CH 2 —CH 2 —O] n H

where n is an integer.

12. The optical laminate according to claim 9 wherein the aliphatic diisocyanate comprises 4,4′-dicyclohexylmethane-diisocyanate.

13. The optical laminate according to claim 9 wherein the first resin sheet comprises polycarbonate.

14. The optical laminate according to claim 9 wherein the first resin sheet comprises cellulose acetate butyrate.

15. The optical laminate according to claim 9 further comprising a second resin sheet, the polyurethane adhesive layer attached directly to the second resin sheet.

16. A polyurethane adhesive for use in optical articles formed from a reaction composition comprising a prepolymer, a crosslinking agent consisting of di(trimethylolpropane), and a chain extender consisting of 1,4-butane diol, wherein a molar ratio of the crosslinking agent and the chain extender is in the range of 0.18 to 1.03;
wherein the prepolymer formed from a composition comprising:
a polycarbonate polyol having a number average molecular weight of approximately 800 and a hydroxyl value of 141.1 mg KOH/g, wherein said polycarbonate polyol is formed from a composition consisting of a 1:1 molar ratio of 1,3-propane diol and 1,4-butane diol,
a polyether polyol having a number average molecular weight of about 1,000, and
an aliphatic diisocyanate.

17. The polyurethane adhesive according to claim 16 wherein the polycarbonate polyol has a formula:

where “n” is equal to an integer from 3 to 6 or a combination thereof, and “x” is an integer that makes the molecular weight of the polycarbonate polyol approximately equal to 800.

18. The polyurethane adhesive according to claim 16 wherein the polyether polyol having a formula:
OH—[CH 2 —CH 2 —CH 2 —CH 2 —O] n H

where n is an integer.

19. The polyurethane adhesive according to claim 16 wherein the aliphatic diisocyanate comprises 4,4′-dicyclohexylmethane-diisocyanate.

Assignees

• Vision Ease Lp
• Hoya Optical Labs Of America Inc

Inventors

• Fan Ping
• Vu Hannah

Classifications

• C08G18/6677

  having at least three hydroxy groups · CPC title

• B32B2307/712

  Weather resistant · CPC title

• C08G18/44

  Polycarbonates · CPC title

• C08G18/758

  containing two or more cycloaliphatic rings · CPC title

• G02C7/102

  Photochromic filters · CPC title