IP Library Granted Patent US 9,163,108
Granted Patent B2
US 9,163,108 · App. 13/563,236 · Granted Oct 20, 2015

Photochromic polyurethane laminate

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Quick Facts
Patent No.
US 9,163,108
App. No.
13/563,236
Granted
Oct 20, 2015
Kind
B2
Abstract

A photochromic polyurethane laminate 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. A method of making the photochromic polyurethane laminate includes steps of causing the crosslinking.

Claims (30)

1. A method of making a photochromic polyurethane laminate comprising:

providing a polyurethane;

preparing a solution from said polyurethane;

adding an isocyanate prepolymer into said solution;

introducing di(trimethylolpropane) as a crosslinking agent into said solution;

introducing at least one photochromic dye into said solution;

forming a crosslinked photochromic polyurethane layer from said solution;

placing said crosslinked photochromic polyurethane layer between a first and a second resin sheet to form a multilayer laminate; and

curing said laminate.

2. A method according to claim 1 wherein said step of forming a crosslinked photochromic polyurethane layer from said solution comprises reacting at least three functional groups of said crosslinking agent with functional isocyanate groups of said isocyanate prepolymer.

3. A method according to claim 1 , wherein said step of forming a crosslinked photochromic polyurethane layer from said solution comprises reacting at least three functional groups of said crosslinking agent with functional hydroxyl groups of said polyurethane.

4. A method according to claim 1 , wherein the step of providing a polyurethane comprises providing a thermoplastic polyurethane.

5. A method according to claim 1 , wherein the step of providing a polyurethane comprises providing a polyurethane formed from polyester polyols.

6. A method according to claim 1 , wherein the step of adding an isocyanate prepolymer comprises providing an isocyanate prepolymer formed from an aliphatic diisocyanate.

7. A method according to claim 1 , further comprising placing said crosslinked photochromic polyurethane layer between a first polycarbonate sheet and a second polycarbonate sheet.

8. A method according to claim 1 , wherein the step of forming a crosslinked photochromic polyurethane layer from said solution comprises casting said solution on a surface of a substrate to form a film.

9. A method of making a photochromic polyurethane laminate comprising:

forming a polyurethane by reaction of a prepolymer with a chain extender;

preparing a solution of said polyurethane;

adding an isocyanate prepolymer to said solution;

adding di(trimethylolpropane) as a crosslinking agent to said solution;

adding at least one photochromic dye into said solution;

forming a crosslinked photochromic polyurethane layer from said solution;

interposing said crosslinked photochromic polyurethane layer between a first and a second resin layer to form a multilayer laminate; and

curing said laminate.

10. A method according to claim 9 , wherein said step of forming a crosslinked photochromic polyurethane layer from said solution comprises reacting at least three functional groups of said crosslinking agent with functional isocyanate groups of said isocyanate prepolymer.

11. A method according to claim 9 , wherein said step of forming a crosslinked photochromic polyurethane layer from said solution comprises reacting at least three functional groups of said crosslinking agent with functional hydroxyl groups of said polyurethane.

12. A method according to claim 9 , wherein the step of forming a polyurethane by reaction of a prepolymer with a chain extender comprises forming said polyurethane from a mixture comprising a polyester polyol.

13. A method according to claim 9 , wherein the step of interposing said crosslinked photochromic polyurethane layer between a first and second resin layer to form a multilayer laminate comprises interposing said crosslinked photochromic polyurethane layer between a first polycarbonate sheet and a second polycarbonate sheet.

14. A method according to claim 9 , wherein the step of forming a crosslinked photochromic polyurethane layer from said solution comprises casting said solution on a surface of a substrate to form a film.

Assignments (14)
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 Jun 14, 2017
From: INSIGHT EQUITY A.P.X, L.P.
To: VISION EASE, LP
Reel/Frame 042706/0151 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE OF STATE OF INCORPORATION PREVIOUSLY RECORDED AT REEL: 028777 FRAME: 0829. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Feb 3, 2017
From: VU, HANNAH; SUGIMURA, HIDEYO; FAN, PING; VU, HAO
To: INSIGHT EQUITY A.P.X, L.P.
Reel/Frame 041625/0648 →
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 →
RELEASE OF SECURITY INTEREST Recorded Sep 23, 2014
From: PNC BANK, NATIONAL ASSOCIATION, AS TERM LOAN AGENT
To: INSIGHT EQUITY A.P. X, LP
Reel/Frame 033810/0143 →
RELEASE OF SECURITY INTEREST Recorded Sep 23, 2014
From: PNC BANK, NATIONAL ASSOCIATION, AS REVOLVING AGENT
To: INSIGHT EQUITY A.P. X, LP
Reel/Frame 033810/0185 →
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 →
SECURITY AGREEMENT Recorded Nov 8, 2012
From: INSIGHT EQUITY A.P. X, LP (D/B/A VISION-EASE LENS)
To: PNC BANK, NATIONAL ASSOCIATION, AS REVOLVING AGENT
Reel/Frame 029261/0832 →
SECURITY AGREEMENT Recorded Nov 8, 2012
From: INSIGHT EQUITY A.P. X, LP (D/B/A VISION-EASE LENS)
To: PNC BANK, NATIONAL ASSOCIATION, AS TERM LOAN AGENT
Reel/Frame 029261/0912 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 13, 2012
From: VU, HANNAH; SUGIMURA, HIDEYO; FAN, PING; VU, HAO
To: INSIGHT EQUITY A.P.X., L..P.
Reel/Frame 028777/0829 →