IP Library Granted Patent US 9,115,294
Granted Patent B2
US 9,115,294 · App. 12/312,140 · Granted Aug 25, 2015

Polyurethane adhesive

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Quick Facts
Patent No.
US 9,115,294
App. No.
12/312,140
Granted
Aug 25, 2015
Kind
B2
Abstract

The present invention relates to acrylic compositions capable of bonding directly with an isocyanate-containing composition, e.g. polyurethane, and methods for manufacturing the same. The acrylic compositions of the invention have multifunctional chain transfer agents and/or multifunctional crosslinkers with isocyanate-reactive groups.

Claims (24)

1. A method for manufacturing an article, comprising:

(a) formulating an acrylic composition having a multifunctional chain transfer agent, wherein said multifunctional chain transfer agent comprises at least one chain transfer moiety and an isocyanate-reactive group;

(b) curing the acrylic composition; and

(c) bonding the cured acrylic composition with an isocyanate-containing composition to form a bond by reacting at least a portion of the multifunctional chain transfer agent with the isocyanate-containing composition.

2. A method according to claim 1 , wherein said isocyanate-containing composition is polyurethane.

3. A method according to claim 1 , wherein said bonding occurs after applying a mixture of said isocyanate-containing composition onto said acrylic composition.

4. A method according to claim 1 , wherein said bonding occurs after coating said acrylic composition onto said isocyanate-containing composition.

5. A method according to claim 1 , wherein said isocyanate-reactive group and said isocyanate-containing composition react to produce a carbamate bond, a thiocarbamate bond, or a carbamide bond.

6. The method of claim 1 , wherein said multifunctional chain transfer agent is pentaerythritol tetra(3-mercaptopropionate).

7. A method for manufacturing an article, comprising:

(a) formulating an acrylic composition having:

i) a multifunctional crosslinker, comprising an isocyanate-reactive group; and/or

ii) a multifunctional chain transfer agent, comprising at least one chain transfer moiety and an isocyanate-reactive group;

(b) curing the acrylic composition; and

(c) reacting the cured acrylic composition with an isocyanate-containing composition to form a bond.

8. The method of claim 1 , wherein the bond formed between said acrylic composition and the isocyanate-containing composition comprises a residue of the multifunctional chain transfer agent within the acrylic composition and a residue of an isocyanate within the isocyanate-containing composition.

9. The method of claim 8 , wherein the bond comprises a carbamate bond, a thiocarbamate bond, or a carbamide bond.

10. The method of claim 1 , wherein said multifunctional chain transfer agent is selected from a group consisting of pentaerythritol tris(3-mercaptopropionate), pentaerythritol tris(2-mercaptoacetate), pentaerythritol tetra(2-mercaptoacetate), pentaerythritol tetra(3-mercaptopropionate), or trimethylolpropane tris(2-mercaptoacetate).

11. The method of claim 2 , wherein the bonding increases adhesive strength between the polyurethane and the acrylic composition, according to the chisel test.

12. The method of claim 11 , wherein the increased adhesive strength is provided by the method without a lamination step.

13. The method of claim 1 , wherein the acrylic composition comprises 0.01-10 wt. % of the multifunctional chain transfer agent.

14. The method of claim 1 , wherein the method is exclusive of a lamination step.

15. The method of claim 1 , wherein the method provides an acrylic substrate layer having a polyurethane material layer bonded thereto.

16. The method of claim 15 , wherein the provided acrylic substrate layer having a polyurethane material layer bonded thereto is prepared exclusive of a lamination step.

Assignments (11)
FIRST LIEN RELEASE OF SECURITY INTEREST IN PATENTS RECORDED ON DECEMBER 16, 2018 AT REEL 047789 FRAME 0354 Recorded Jun 12, 2025
From: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
To: PLASKOLITE MASSACHUSETTS, LLC; PLASKOLITE TENNESSEE, LLC; PLASKOLITE, LLC
Reel/Frame 071574/0264 →
RELEASE OF SECURITY INTEREST Recorded May 12, 2025
From: ARES CAPITAL CORPORATION
To: PLASKOLITE MASSACHUSETTS, LLC; PLASKOLITE TENNESSEE, LLC; PLASKOLITE, LLC
Reel/Frame 071091/0748 →
SECURITY INTEREST Recorded May 9, 2025
From: PLASKOLITE TENNESSEE, LLC
To: ARES CAPITAL CORPORATION, AS COLLATERAL AGENT
Reel/Frame 071073/0312 →
SECURITY INTEREST Recorded Feb 25, 2019
From: PLASKOLITE TENNESSEE, LLC
To: ARES CAPITAL CORPORATION, AS COLLATERAL AGENT
Reel/Frame 048423/0247 →
SECURITY INTEREST Recorded Dec 16, 2018
From: PLASKOLITE MASSACHUSETTS, LLC; PLASKOLITE TENNESSEE, LLC; PLASKOLITE, LLC
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 047789/0354 →
RELEASE OF SECURITY INTEREST Recorded Dec 16, 2018
From: ANTARES CAPITAL LP, AS AGENT
To: PLASKOLITE TENNESSEE, LLC
Reel/Frame 047789/0332 →
RELEASE OF SECURITY INTEREST Recorded Dec 16, 2018
From: U.S. BANK NATIONAL ASSOCIATION, AS AGENT
To: PLASKOLITE TENNESSEE, LLC
Reel/Frame 047789/0337 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 11, 2018
From: LUCITE INTERNATIONAL INC.
To: PLASKOLITE TENNESSEE, LLC
Reel/Frame 045501/0610 →
SECURITY INTEREST Recorded Apr 6, 2018
From: PLASKOLITE TENNESSEE, LLC
To: ANTARES CAPITAL LP, AS ADMINISTRATIVE AGENT
Reel/Frame 045458/0414 →
SECURITY INTEREST Recorded Apr 6, 2018
From: PLASKOLITE TENNESSEE, LLC
To: U.S. BANK NATIONAL ASSOCIATION
Reel/Frame 045462/0036 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 28, 2009
From: JANOWICZ, ANDREW; FAROOQ, FAREEDUDDIN
To: LUCITE INTERNATIONAL, INC.
Reel/Frame 022639/0689 →