IP Library Granted Patent US 9,081,130
Granted Patent B1
US 9,081,130 · App. 13/737,871 · Granted Jul 14, 2015

Photochromic polyurethane laminate

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Quick Facts
Patent No.
US 9,081,130
App. No.
13/737,871
Granted
Jul 14, 2015
Kind
B1
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.

Claims (36)

1. A photochromic polyurethane laminate for use in an optical article comprising:

a first resin sheet;

a second resin sheet;

a photochromic polyurethane layer disposed between said first and second resin sheet;

said photochromic polyurethane layer formed from a composition comprising a prepolymer, di(trimethylolpropane), and one or more photochromic compounds;

said prepolymer formed from a composition comprising:

a polycarbonate polyol having a number average molecular weight of about 800 gram per mole and an OH number of 138 milligrams KOH per gram;

a polyether polyol having a number average molecular weight of about 1,000 gram per mole and an OH number of 115 milligrams KOH per gram; and

an aliphatic diisocyanate.

2. A photochromic polyurethane laminate according to claim 1 wherein said 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. A photochromic polyurethane laminate according to claim 1 wherein said polyether polyol has a formula:

HO—[(CR1R2M) n O] x H

where R1 and R2 are a hydrogen or an alkyl group, where “n” is equal to an integer from 3 to 6, and “x” is an integer that makes the molecular weight of the said polyether polyol approximately equal to 1,000 and where “M” has a formula:

(CH2) y

where “y” is an integer from 1 to 6.

4. A photochromic polyurethane laminate according to claim 1 wherein said photochromic polyurethane layer is formed from a composition further comprising a chain extender.

5. A photochromic polyurethane laminate according to claim 4 wherein said chain extender is 1,4-butanediol.

6. The photochromic polyurethane according to claim 1 wherein said aliphatic diisocyanate comprises 4,4′-dicyclohexylmethanediisocyanate.

7. A photochromic polyurethane laminate for use in an optical article comprising:

a photochromic polyurethane layer disposed on a surface of a resin sheet;

said photochromic polyurethane layer formed from a composition comprising a prepolymer, a chain extender, di(trimethylolpropane) as a crosslinking agent, and one or more photochromic compounds;

said prepolymer formed from a composition comprising:

a polycarbonate polyol having a number average molecular weight of about 800 gram per mole and an OH number of 138 milligrams KOH per gram;

a polyether polyol having a number average molecular weight of about 1,000 gram per mole and an OH number of 115 milligrams KOH per gram; and

an aliphatic diisocyanate.

8. The photochromic polyurethane laminate according to claim 7 wherein the resin sheet is a polycarbonate resin sheet.

9. A photochromic polyurethane laminate according to claim 7 wherein said 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 said polycarbonate polyol approximately equal to 800.

10. A photochromic polyurethane laminate according to claim 7 wherein said polyether polyol has a formula:

HO—[(CR1R2M) n O] x H

where R1 and R2 are a hydrogen or an alkyl group, where “n” is equal to an integer from 3 to 6, and “x” is an integer that makes the molecular weight of the said polyether polyol approximately equal to 1,000 and where “M” has a formula:

(CH2) y

where “y” is an integer from 1 to 6.

11. The photochromic polyurethane according to claim 7 wherein said aliphatic diisocyanate comprises 4,4′-dicyclohexylmethanediisocyanate.

12. A photochromic polyurethane laminate according to claim 7 wherein said chain extender is 1,4-butanediol.

Assignments (7)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 29, 2022
From: VISION EASE, LP
To: HOYA OPTICAL LABS OF AMERICA, INC.
Reel/Frame 059825/0497 →
RELEASE OF SECURITY INTEREST Recorded Aug 1, 2017
From: ANTARES CAPITAL LP
To: VISION EASE, LP
Reel/Frame 043402/0306 →
CHANGE OF NAME Recorded Nov 23, 2015
From: INSIGHT EQUITY A.P. X, LP
To: VISION EASE, LP
Reel/Frame 037154/0842 →
RELEASE OF SECURITY INTEREST Recorded Oct 30, 2015
From: ANTARES CAPITAL LP, AS AGENT
To: VISION EASE, LP (F/N/A INSIGHT EQUITY A.P. X, LP)
Reel/Frame 037009/0180 →
SECURITY INTEREST Recorded Oct 27, 2015
From: VISION EASE, LP (D/B/A VISION-EASE LENS)
To: ANTARES CAPITAL LP, AS ADMINISTRATIVE AGENT
Reel/Frame 036981/0268 →
ASSIGNMENT OF INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Sep 15, 2015
From: GENERAL ELECTRIC CAPITAL CORPORATION, AS RETIRING AGENT
To: ANTARES CAPITAL LP, AS SUCCESSOR AGENT
Reel/Frame 036616/0161 →
SECURITY INTEREST Recorded Sep 23, 2014
From: INSIGHT EQUITY A.P. X, LP (D/B/A VISION-EASE LENS)
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS AGENT
Reel/Frame 033810/0209 →