IP Library Granted Patent US 6,852,801
Granted Patent B1
US 6,852,801 · App. 10/634,316 · Granted Feb 8, 2005

Adhesives for bonding composites

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Quick Facts
Patent No.
US 6,852,801
App. No.
10/634,316
Granted
Feb 8, 2005
Kind
B1
Abstract

An adhesive composition, including a mixture of about 1 percent to about 35 percent by weight of chlorinated polymer, about 1 percent to about 35 percent by weight of a nitrile elastomer, a rubber-modified acrylonitrile copolymer, or mixtures thereof, about 25 percent to about 90 percent by weight of an alkyl acrylate or methacrylate monomer and about 0.01 to about 30 weight percent of a core shell impact modifier.

Claims (36)

1. An adhesive composition comprising a mixture of about 1 percent to about 50 percent by weight of a chlorinated polymer, about 0.5 percent to about 45 percent by weight of a nitrile elastomer, a thermoplastic acrylonitrile copolymer or mixtures thereof, about 25 percent to about 90 percent by weight of an alkyl acrylate or methacrylate monomer, and about 0.01 to about 30 percent by weight of a core shell impact modifier.

2. An adhesive composition comprising a mixture of about 2 percent to about 40 percent by weight of a chlorinated elastomer polymer, about 0.5 percent to about 25 percent by weight of a nitrile elastomer, a thermoplastic acrylonitrile copolymer or mixtures thereof, about 40 percent to about 90 percent by weight of a C 1 to C 5 alkyl acrylate or methacrylate monomer, and about 0.01 to about 30 percent by weight of a core shell impact modifier.

3. An adhesive composition comprising a mixture of about 5 percent to about 30 percent by weight of a chlorinated elastomer polymer, about 0.5 percent to about 20 percent by weight of a nitrile elastomer, a thermoplastic acrylonitrile copolymer or mixtures thereof, and about 50 percent to about 85 percent by weight of a C 1 to C 5 alkyl acrylate or methacrylate monomer, and about 0.01 to about 30 percent by weight of a core shell impact modifier.

4. The composition of claim 1 , 2 or 3 in admixture with from about 0.01 up to about 25 percent by weight of a C 6 or higher acrylate or methacrylate monomer.

5. The composition of claim 1 , 2 or 3 in admixture with from about 0.01 to about 15 percent by weight of a polymerizable organic acid monomer.

6. The composition of claim 1 , 2 or 3 in admixture with a free radical generating catalyst system.

7. The composition of claim 1 , 2 or 3 in admixture with a catalyst promoter.

8. The composition of claim 1 , 2 or 3 in admixture with a C 6 or higher acrylate or methacrylate monomer and a polymerizable organic acid monomer.

9. The composition of claim 1 , 2 or 3 in admixture with a C 6 or higher acrylate or methacrylate monomer and a free radical generating catalyst system.

10. The composition of claim 1 , 2 or 3 in admixture with a free radical generating catalyst system and a catalyst promoter.

11. The adhesive composition of claim 1 wherein the chlorinated polymer comprises a polyvinyl chloride.

12. The adhesive composition of claim 1 wherein the chlorinated polymer comprises a polyvinyl chloride or a blend of a polyvinyl chloride and a nitrile elastomer.

13. The composition of claim 1 , 2 or 3 wherein the chlorinated polymer is selected from the group consisting of polychloroprene, chlorinated polyethylene, chlorinated rubber, epichlorohydrin polymers, and non-sulfur containing polymers containing 20 to 55 percent chlorine and mixtures thereof.

14. The composition of claim 1 , 2 , or 3 wherein the core shell impact modifier is selected from MBS polymer impact modifiers, ABS polymer impact modifiers and MABS polymer impact modifiers.

15. The composition of claim 1 , 2 , or 3 wherein the core shell impact modifier comprises from about 5 to about 20 percent of the adhesive composition by weight.

16. The composition of claim 1 , 2 , or 3 wherein the core shell impact modifier comprises from about 5 to about 10% of the adhesive composition by weight.

17. The composition of claim 1 , 2 or 3 wherein tensile elongation of the adhesive composition after curing for about 24 hours at ambient temperature followed by an additional curing of the composition for one hour at 82° C. is at least about 50 percent of tensile elongation of the adhesive composition after the initial 24 hour curing alone.

18. The composition of claim 1 , 2 or 3 wherein tensile elongation of the adhesive composition after curing for about 24 hours at ambient temperature is at least about 100 percent and wherein the tensile elongation is at least about 50 percent following additional curing for one hour at 82° C.

19. The composition of claim 1 , 2 or 3 wherein tensile elongation of the adhesive composition after curing for about 24 hours at ambient temperature is at least about 150 percent and wherein the tensile elongation is at least about 70 percent following additional curing for one hour at 82° C.

20. The composition of claim 1 , 2 or 3 wherein tensile elongation of the adhesive composition after curing for about 24 hours at ambient temperature is from about 100 percent to about 200 percent and wherein the tensile elongation is from about 50 percent to about 150 percent following additional curing for one hour at 82° C.

21. The composition of claim 1 , 2 or 3 wherein tensile elongation of the adhesive composition after curing for about 24 hours at ambient temperature is about 150 percent to about 250 percent and wherein the tensile elongation is about 75 percent to about 200 percent following additional curing for one hour at 82° C.

22. An adhesive composition comprising a mixture of about 1 percent to about 50 percent by weight of a non-sulfur containing chlorinated polymer, about 0.5 percent to about 45 percent by weight of a nitrile elastomer, a thermoplastic acrylonitrile copolymer or mixtures thereof, and about 25 percent to about 90 percent by weight of an alkyl acrylate or methacrylate monomer, wherein tensile elongation of the adhesive composition after curing for about 24 hours at ambient temperature followed by an additional curing of the composition for one hour at 82° C. is at least about 50 percent of tensile elongation of the adhesive composition after the initial 24 hour curing alone.

23. An adhesive composition comprising a mixture of about 1 percent to about 50 percent by weight of a non-sulfur containing chlorinated polymer, about 0.5 percent to about 45 percent by weight of a nitrile elastomer, a thermoplastic acrylonitrile copolymer or mixtures thereof, and about 25 percent to about 90 percent by weight of an alkyl acrylate or methacrylate monomer, wherein tensile elongation of the adhesive composition after curing for about 24 hours at ambient temperature is at least about 100 percent and wherein the tensile elongation is at least about 50 percent following additional curing for one hour at 82° C.

24. An adhesive composition comprising a mixture of about 1 percent to about 50 percent by weight of a non-sulfur containing chlorinated polymer, about 0.5 percent to about 45 percent by weight of a nitrile elastomer, a thermoplastic acrylonitrile copolymer or mixtures thereof, and about 25 percent to about 90 percent by weight of an alkyl acrylate or methacrylate monomer, wherein tensile elongation of the adhesive composition after curing for about 24 hours at ambient temperature is at least about 150 percent and wherein the tensile elongation is at least about 70 percent following additional curing for one hour at 82° C.

25. An adhesive composition comprising a mixture of about 1 percent to about 50 percent by weight of a non-sulfur containing chlorinated polymer, about 0.5 percent to about 45 percent by weight of a nitrile elastomer, a thermoplastic acrylonitrile copolymer or mixtures thereof, and about 25 percent to about 90 percent by weight of an alkyl acrylate or methacrylate monomer, wherein tensile elongation of the adhesive composition after curing for about 24 hours at ambient temperature is from about 100 percent to about 200 percent and wherein the tensile elongation is from about 50 percent to about 150 percent following additional curing for one hour at 82° C.

26. An adhesive composition comprising a mixture of about 1 percent to about 50 percent by weight of a non-sulfur containing chlorinated polymer, about 0.5 percent to about 45 percent by weight of a nitrile elastomer, a thermoplastic acrylonitrile copolymer or mixtures thereof, and about 25 percent to about 90 percent by weight of an alkyl acrylate or methacrylate monomer, wherein tensile elongation of the adhesive composition after curing for about 24 hours at ambient temperature is about 150 percent to about 250 percent and wherein the tensile elongation is about 75 percent to about 200 percent following additional curing for one hour at 82° C.

27. The adhesive composition of claim 22 comprising a mixture of about 2 percent to about 40 percent by weight of a non-sulfur containing chlorinated elastomer polymer, about 0.5 percent to about 25 percent by weight of a nitrile elastomer, a thermoplastic acrylonitrile copolymer or mixtures thereof, a thermoplastic acrylonitrile copolymer or mixtures thereof, and about 40 percent to about 90 percent by weight of a C 1 to C 5 alkyl acrylate or methacrylate monomer.

28. The adhesive composition of claim 23 comprising a mixture of about 2 percent to about 40 percent by weight of a non-sulfur containing chlorinated elastomer polymer, about 0.5 percent to about 25 percent by weight of a nitrile elastomer, a thermoplastic acrylonitrile copolymer or mixtures thereof, a thermoplastic acrylonitrile copolymer or mixtures thereof, and about 40 percent to about 90 percent by weight of a C 1 to C 5 alkyl acrylate or methacrylate monomer.

29. The adhesive composition of claim 24 comprising a mixture of about 2 percent to about 40 percent by weight of a non-sulfur containing chlorinated elastomer polymer, about 0.5 percent to about 25 percent by weight of a nitrile elastomer, a thermoplastic acrylonitrile copolymer or mixtures thereof, a thermoplastic acrylonitrile copolymer or mixtures thereof, and about 40 percent to about 90 percent by weight of a C 1 to C 5 alkyl acrylate or methacrylate monomer.

30. The adhesive composition of claim 25 comprising a mixture of about 2 percent to about 40 percent by weight of a non-sulfur containing chlorinated elastomer polymer, about 0.5 percent to about 25 percent by weight of a nitrile elastomer, a thermoplastic acrylonitrile copolymer or mixtures thereof, a thermoplastic acrylonitrile copolymer or mixtures thereof, and about 40 percent to about 90 percent by weight of a C 1 to C 5 alkyl acrylate or methacrylate monomer.

31. The adhesive composition of claim 26 comprising a mixture of about 2 percent to about 40 percent by weight of a non-sulfur containing chlorinated elastomer polymer, about 0.5 percent to about 25 percent by weight of a nitrile elastomer, a thermoplastic acrylonitrile copolymer or mixtures thereof, a thermoplastic acrylonitrile copolymer or mixtures thereof, and about 40 percent to about 90 percent by weight of a C 1 to C 5 alkyl acrylate or methacrylate monomer.

32. The adhesive composition of claim 22 comprising a mixture of about 5 percent to about 30 percent by weight of a non-sulfur containing chlorinated elastomer polymer, about 0.5 percent to about 20 percent by weight of a nitrile elastomer, a thermoplastic acrylonitrile copolymer or mixtures thereof, and about 50 percent to about 85 percent by weight of a C 1 to C 5 alkyl acrylate or methacrylate monomer.

33. The adhesive composition of claim 23 comprising a mixture of about 5 percent to about 30 percent by weight of a non-sulfur containing chlorinated elastomer polymer, about 0.5 percent to about 20 percent by weight of a nitrile elastomer, a thermoplastic acrylonitrile copolymer or mixtures thereof, and about 50 percent to about 85 percent by weight of a C 1 to C 5 alkyl acrylate or methacrylate monomer.

34. The adhesive composition of claim 24 comprising a mixture of about 5 percent to about 30 percent by weight of a non-sulfur containing chlorinated elastomer polymer, about 0.5 percent to about 20 percent by weight of a nitrile elastomer, a thermoplastic acrylonitrile copolymer or mixtures thereof, and about 50 percent to about 85 percent by weight of a C 1 to C 5 alkyl acrylate or methacrylate monomer.

35. The adhesive composition of claim 25 comprising a mixture of about 5 percent to about 30 percent by weight of a non-sulfur containing chlorinated elastomer polymer, about 0.5 percent to about 20 percent by weight of a nitrile elastomer, a thermoplastic acrylonitrile copolymer or mixtures thereof, and about 50 percent to about 85 percent by weight of a C 1 to C 5 alkyl acrylate or methacrylate monomer.

36. The adhesive composition of claim 26 comprising a mixture of about 5 percent to about 30 percent by weight of a non-sulfur containing chlorinated elastomer polymer, about 0.5 percent to about 20 percent by weight of a nitrile elastomer, a thermoplastic acrylonitrile copolymer or mixtures thereof, and about 50 percent to about 85 percent by weight of a C 1 to C 5 alkyl acrylate or methacrylate monomer.

Assignments (26)
RELEASE OF SECURITY INTEREST Recorded Oct 28, 2025
From: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
To: WATERTITE PRODUCTS, INC.; IPS CORPORATION; IPS STRUCTURAL ADHESIVES, INC.; T. CHRISTY ENTERPRISES, LLC
Reel/Frame 073378/0499 →
RELEASE OF PATENT SECURITY AGREEMENT Recorded Jun 11, 2024
From: JEFFERIES FINANCE LLC
To: WATERTITE PRODUCTS, INC.; IPS CORPORATION; T. CHRISTY ENTERPRISES, LLC; IPS STRUCTURAL ADHESIVES, INC.
Reel/Frame 067686/0340 →
RELEASE OF SECURITY INTEREST Recorded Oct 7, 2021
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
To: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
Reel/Frame 057750/0945 →
PATENT SECOND LIEN SECURITY AGREEMENT Recorded Oct 1, 2021
From: WATERTITE PRODUCTS, INC.; IPS CORPORATION; T. CHRISTY ENTERPRISES, LLC; IPS STRUCTURAL ADHESIVES, INC.
To: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 057681/0752 →
PATENT FIRST LIEN SECURITY AGREEMENT Recorded Oct 1, 2021
From: WATERTITE PRODUCTS, INC.; IPS CORPORATION; T. CHRISTY ENTERPRISES, LLC; IPS STRUCTURAL ADHESIVES, INC.
To: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 057681/0767 →
CORRECTIVE ASSIGNMENT TO CORRECT THE APPLICATION NUMBER SERIAL NUMBER PREVIOUSLY RECORDED AT REEL: 44444 FRAME: 0932. ASSIGNOR(S) HEREBY CONFIRMS THE SECOND LIEN SECURITY AGREEMENT. Recorded Aug 8, 2019
From: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS SECOND LIEN COLLATERAL AGENT
Reel/Frame 050021/0359 →
CORRECTIVE ASSIGNMENT TO CORRECT THE PROPERTY NUMBER PREVIOUSLY RECORDED AT REEL: 49891 FRAME: 807. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Aug 8, 2019
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS ADMINISTRATIVE AGENT
To: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
Reel/Frame 050003/0400 →
CORRECTIVE ASSIGNMENT TO CORRECT THE APPLICATION NUMBER SERIAL NUMBER PREVIOUSLY RECORDED AT REEL: 44444 FRAME: 0905. ASSIGNOR(S) HEREBY CONFIRMS THE FIRST LIEN SECURITY AGREEMENT. Recorded Aug 8, 2019
From: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS FIRST LIEN COLLATERAL AGENT
Reel/Frame 050021/0307 →
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Jul 1, 2019
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS ADMINISTRATIVE AGENT
To: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
Reel/Frame 049891/0807 →
TERMINATION AND RELEASE OF SECURITY INTEREST Recorded Nov 14, 2017
From: WELLS FARGO BANK, NATIONAL ASSOCIATION
To: IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; IPS ADHESIVES LLC
Reel/Frame 044752/0016 →
TERMINATION OF FIRST LIEN SECURITY INTEREST Recorded Nov 14, 2017
From: JEFFERIES FINANCE LLC
To: IPS ADHESIVES LLC; IPS CORPORATION; IPS STRUCTURAL ADHESIVES, INC.; WATERTITE PRODUCTS, INC.
Reel/Frame 044443/0487 →
TERMINATION OF SECOND LIEN SECURITY INTEREST Recorded Nov 14, 2017
From: JEFFERIES FINANCE LLC
To: IPS ADHESIVES LLC; IPS CORPORATION; IPS STRUCTURAL ADHESIVES, INC.; WATERTITE PRODUCTS, INC.
Reel/Frame 044444/0095 →
FIRST LIEN SECURITY AGREEMENT Recorded Nov 14, 2017
From: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS FIRST LIEN COLLATERAL AGENT
Reel/Frame 044444/0905 →
SECOND LIEN SECURITY AGREEMENT Recorded Nov 14, 2017
From: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS SECOND LIEN COLLATERAL AGENT
Reel/Frame 044444/0932 →
SECURITY INTEREST Recorded Dec 23, 2016
From: IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; IPS ADHESIVES LLC
To: WELLS FARGO BANK, NATIONAL ASSOCIATION
Reel/Frame 041187/0273 →
RELEASE OF SECURITY INTEREST Recorded Dec 22, 2016
From: ANTARES CAPITAL LP, AS ADMINISTRATIVE AGENT
To: IPS STRUCTURAL ADHESIVES, INC.
Reel/Frame 040744/0762 →
GRANT OF FIRST LIEN SECURITY INTEREST Recorded Dec 22, 2016
From: IPS ADHESIVES LLC; IPS CORPORATION; IPS STRUCTURAL ADHESIVES, INC.; WATERTITE PRODUCTS, INC.
To: JEFFERIES FINANCE LLC
Reel/Frame 041178/0452 →
GRANT OF SECOND LIEN SECURITY INTEREST Recorded Dec 22, 2016
From: IPS ADHESIVES LLC; IPS CORPORATION; IPS STRUCTURAL ADHESIVES, INC.; WATERTITE PRODUCTS, INC.
To: JEFFERIES FINANCE LLC
Reel/Frame 041179/0609 →
ASSIGNMENT OF INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Oct 13, 2015
From: GENERAL ELECTRIC CAPITAL CORPORATION
To: ANTARES CAPITAL LP
Reel/Frame 036842/0908 →
RELEASE OF SECURITY INTEREST Recorded Feb 13, 2015
From: GENERAL ELECTRIC CAPITAL CORPORATION, AS ADMINISTRATIVE AGENT
To: IPS STRUCTURAL ADHESIVES, INC.
Reel/Frame 034960/0907 →
SECURITY INTEREST Recorded Feb 9, 2015
From: IPS STRUCTURAL ADHESIVES, INC.
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS AGENT
Reel/Frame 034917/0147 →
SECURITY AGREEMENT Recorded Dec 6, 2013
From: IPS STRUCTURAL ADHESIVES, INC.
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS ADMINISTRATIVE AGENT
Reel/Frame 031768/0615 →
SECURITY AGREEMENT Recorded Aug 20, 2012
From: IPS STRUCTURAL ADHESIVES, INC.
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS ADMINISTRATIVE AGENT
Reel/Frame 028810/0918 →
RELEASE OF SECURITY INTEREST Recorded Aug 17, 2012
From: MORGAN STANLEY SENIOR FUNDING, INC.
To: IPS STRUCTURAL ADHESIVES, INC.
Reel/Frame 028807/0745 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 20, 2006
From: IPS CORPORATION; WELD-ON ADHESIVES, INC.
To: IPS STRUCTURAL ADHESIVES, INC.
Reel/Frame 018279/0768 →
SECURITY AGREEMENT Recorded Jul 20, 2006
From: IPS STRUCTURAL ADHESIVES, INC.
To: MORGAN STANLEY SENIOR FUNDING, INC., AS THE ADMINISTRATIVE AGENT
Reel/Frame 017957/0618 →