IP Library Granted Patent US 9,909,043
Granted Patent B2
US 9,909,043 · App. 14/800,325 · Granted Mar 6, 2018

Polyurethane adhesive

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Quick Facts
Patent No.
US 9,909,043
App. No.
14/800,325
Granted
Mar 6, 2018
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 (40)

1. An article, comprising a cured acrylic composition directly bound to an isocyanate-containing composition;

wherein:

i) the cured acrylic composition comprises:

a) an acrylic polymer formed by polymerization of a monomer or mixture of monomers selected from the group consisting of: methyl methacrylate; ethyl methacrylate; propyl methacrylate; isopropyl methacrylate; n-butyl methacrylate; iso-butyl methacrylate; t-butyl methacrylate; pentyl methacrylate; 2-ethylhexyl methacrylate; heptyl methacrylate; octyl methacrylate; isooctyl methacrylate; nonyl methacrylate; decyl methacrylate; isodecyl methacrylate; dodecyl methacrylate; tridecyl methacrylate; undecyl methacrylate; cyclohexyl methacrylate; isobornyl methacrylate; bornyl methacrylate; tricyclodecanyl methacrylate; dicyclopentanyl methacrylate; dicyclopentenyl methacrylate; cyclohexyl methacrylate; benzyl methacrylate; 4-butylcyclohexyl methacrylate; dicyclopentenyl methacrylate; methacrylic acid; methyl acrylate; ethyl acrylate; propyl acrylate; butyl acrylate; pentyl acrylate; hexyl acrylate; octyl acrylate; nonyl acrylate; isodecyl acrylate; lauryl acrylate; isobutyl acrylate; t-butyl acrylate; 2-ethylhexyl acrylate; cyclohexyl acrylate; methylcyclohexyl acrylate; trimethylcyclohexyl acrylate; tertiarybutylcyclohexyl acrylate; isobornyl acrylate; and acrylic acid; and

b) at least one residue of a multifunctional chain transfer agent, said multifunctional chain transfer agent residue comprising a reacted isocyanate-reactive group that has reacted with an isocyanate in the isocyanate-containing composition; and

ii) the direct bond is between the multifunctional chain transfer agent residue within the cured acrylic composition and the isocyanate within the isocyanate-containing composition.

2. The article of claim 1 , wherein said direct bond is between the reacted isocyanate-reactive group of the multifunctional chain transfer agent residue within the cured acrylic composition and the reacted isocyanate within the isocyanate-containing composition.

3. The article of claim 1 , wherein the multifunctional chain transfer agent residue is derived from a multifunctional chain transfer agent comprising:

a) an isocyanate-reactive group; and

b) at least one chain transfer moiety.

4. The article of claim 3 , wherein the 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).

5. The article of claim 3 , wherein the multifunctional chain transfer agent is pentaerythritol tetra(3-mercaptopropionate).

6. The article of claim 3 , wherein the direct bond is a carbamate bond, a thiocarbamate bond, or a carbamide bond.

7. The article of claim 1 , wherein the cured acrylic composition comprises 0.01-10 wt. % of the multifunctional chain transfer agent prior to binding to the isocyanate-containing composition.

8. The article of claim 1 , wherein the cured acrylic composition further comprises one or more multifunctional crosslinking agents, or residues thereof.

9. The article of claim 8 , wherein the one or more multifunctional crosslinking agents, or residues thereof is directly bound to the isocyanate-containing composition.

10. The article of claim 1 , wherein the isocyanate-containing composition is polyurethane.

11. The article of claim 10 , wherein the direct bond between the cured acrylic composition and the polyurethane provides increased adhesive strength, according to the chisel test.

12. The article of claim 1 , wherein the direct bond between the cured acrylic composition and the polyurethane is exclusive of a lamination layer.

13. The article of claim 1 , wherein the article comprises an acrylic substrate layer having a polyurethane material layer directly bonded thereto.

14. The article of claim 1 , wherein the article comprises an acrylic substrate layer having a polyurethane material layer directly bonded thereto, exclusive of a lamination layer there between.

15. The article of claim 1 , wherein the article is formed by:

i) 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;

ii) curing the acrylic composition; and

iii) 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.

16. The article of claim 15 , wherein said bonding occurs after applying a mixture of said isocyanate-containing composition onto said cured acrylic composition.

17. The article of claim 15 , wherein said bonding occurs after coating said isocyanate-containing composition onto said cured acrylic composition.

18. The article of claim 1 , wherein the article is formed by:

i) formulating an acrylic composition having:

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

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

ii) curing the acrylic composition; and

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

19. The article of claim 18 , wherein said bonding occurs after applying a mixture of said isocyanate-containing composition onto cured said acrylic composition.

20. The article of claim 18 , wherein said bonding occurs after coating said isocyanate-containing composition onto said cured acrylic composition.

21. The article of claim 1 , wherein the one or more monomers selected from the group consisting of: methyl methacrylate, ethyl methacrylate, 2-ethylhexyl methacrylate, n-butyl methacrylate, methyl acrylate, ethyl acrylate, and n-butyl acrylate.

22. The article of claim 1 , wherein the cured acrylic composition is a cured acrylic sheet.

23. The article of claim 22 , wherein the one or more monomers selected from the group consisting of: methyl methacrylate, ethyl methacrylate, 2-ethylhexyl methacrylate, n-butyl methacrylate, methyl acrylate, ethyl acrylate, and n-butyl acrylate.

24. The article of claim 15 , wherein the cured acrylic composition is a cured acrylic sheet.

25. The article of claim 18 , wherein the cured acrylic composition is a cured acrylic sheet.

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 Sep 29, 2015
From: JANOWICZ, ANDREW; FAROOQ, FAREEDUDDIN
To: LUCITE INTERNATIONAL, INC.
Reel/Frame 036683/0964 →