IP Library Granted Patent US 9,018,326
Granted Patent B2
US 9,018,326 · App. 13/795,478 · Granted Apr 28, 2015

Adhesive composition for bonding low surface energy polyolefin substrates

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Quick Facts
Patent No.
US 9,018,326
App. No.
13/795,478
Granted
Apr 28, 2015
Kind
B2
Abstract

A two-part acrylic adhesive composition comprising at least one organoborane-amine complex initiator and at least one multifunctional maleimide crosslinker.

Claims (34)

1. A two-part acrylic adhesive composition comprising:

an acrylic oligomer or polymer,

at least one organoborane-amine complex initiator, and

at least one multifunctional maleimide crosslinker.

2. The two-part acrylic adhesive composition of claim 1 wherein the organoboraneamine complex initiator is a trialkylborane-amine complex.

3. The two-part acrylic adhesive composition of claim 2 wherein the trialkylboraneamine complex is triethylborane-1 ,3-diaminopropane.

4. The two-part acrylic adhesive composition of claim 1 wherein the multifunctional maleimide crosslinker comprises at least two maleimide end groups per molecule.

5. The two-part acrylic adhesive composition of claim 1 wherein the multifunctional maleimide crosslinker is a bismaleimide crosslinker.

6. The two-part acrylic adhesive composition of claim 5 wherein the bismaleimide crosslinker is selected from the group having the following general structure:

wherein n is 1 to 10; and

wherein n is 1 to 10.

7. The two-part acrylic adhesive composition of claim 1 wherein a first part that is an initiator part comprises at least one organoborane-amine complex initiator, and optionally at least one non-polymerizable plasticizer.

8. The two-part acrylic adhesive composition of claim 1 wherein a second part that is an activator part further comprises at least one activator which is an amine acceptor for decomplexing the organoborane-amine complex.

9. The two-part acrylic adhesive composition of claim 8 wherein the at least one activator comprises at least one organic acid.

10. The two-part acrylic adhesive composition of claim 9 wherein the at least one organic acid is a carboxylic acid.

11. The two-part acrylic adhesive composition of claim 10 wherein the carboxylic acid comprises at least one member selected from the group consisting of (meth)acrylic acid, acetic acid, benzoic acid, p-methoxybenzoic acid, maleic acid, succinic acid and mixtures thereof.

12. The two-part acrylic adhesive composition of claim 1 further comprising at least one polymerizable ethylenically unsaturated monomer, oligomer or a combination thereof.

13. The two-part acrylic adhesive composition of claim 12 wherein said at least one polymerizable ethylenically unsaturated monomer or oligomer is a (meth)acrylate monomer or (meth)acrylate-functionalized oligomer.

14. The two-part acrylic adhesive composition of claim 1 further comprises at least one thickener, elastomer or a combination thereof.

15. The two-part acrylic adhesive composition of claim 14 wherein said two-part acrylicadhesive composition comprises at least one elastomer that is a styrene-butadienestyrene block copolymer, an acrylonitrile-butadiene-styrene copolymer, or a combination thereof.

16. A two-part acrylic adhesive composition comprising:

a) an initiator part, the initiator part comprising at least one organoboraneamine complex; and

b) an activator part, the activator part comprising a compound that is reactive with the amine portion of the organoborane-amine complex to liberate organoborane from the complex;

wherein the two-part acrylic adhesive composition further comprising at least one multifunctional maleimide crosslinker and at least one polymerizable (meth)acrylate monomer, each of which is independently present in the initiator part, the activator part or both.

17. The two-part acrylic adhesive composition of claim 16 wherein the organoboraneamine complex is triethylborane-1,3-diaminopropane complex.

18. The two-part acrylic adhesive composition of claim 16 wherein said compound that is reactive with the amine portion of the organoborane-amine complex comprises maleic acid, 2-(methacryloyloxy)ethyl succinate or a combination thereof.

19. The two-part acrylic adhesive composition of claim 16 wherein the multifunctional maleimide crosslinker is selected from the group having the following general structure:

wherein n is 1 to 10; and

wherein n is 1 to 10.

20. A two-part acrylic adhesive composition comprising:

at least one organoborane-amine complex initiator; and

at least one compound having at least two polymerizable ethylenically unsaturated groups and an aliphatic hydrocarbon linking residue having at least 20 carbon atoms.

21. The two-part acrylic adhesive composition of claim 20 wherein said at least one compound having at least two polymerizable ethylenically unsaturated groups and an aliphatic hydrocarbon linking residue having at least 20 carbon atoms has the following general structure:

wherein n is 1 to 10.

Assignments (24)
SECURITY INTEREST Recorded Oct 28, 2025
From: WATERTITE PRODUCTS, INC.; IPS CORPORATION; T. CHRISTY ENTERPRISES, LLC; WELD-ON ADHESIVES, INC.
To: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 073378/0535 →
SECURITY INTEREST Recorded Oct 28, 2025
From: WATERTITE PRODUCTS, INC.; IPS CORPORATION; T. CHRISTY ENTERPRISES, LLC; WELD-ON ADHESIVES, INC.
To: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 073378/0575 →
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 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 →
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 →
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 →
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 →
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 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 →
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 →
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 →
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 →
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 →
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 →
RELEASE OF SECURITY INTEREST Recorded Dec 22, 2016
From: ANTARES CAPITAL LP, AS ADMINISTRATIVE AGENT
To: IPS CORPORATION
Reel/Frame 040744/0449 →
ASSIGNMENT OF INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Oct 13, 2015
From: GENERAL ELECTRIC CAPITAL CORPORATION
To: ANTARES CAPITAL LP
Reel/Frame 036842/0975 →
RELEASE OF SECURITY INTEREST Recorded Feb 13, 2015
From: GENERAL ELECTRIC CAPITAL CORPORATION, AS ADMINISTRATIVE AGENT
To: IPS CORPORATION
Reel/Frame 034960/0294 →
SECURITY INTEREST Recorded Feb 9, 2015
From: IPS CORPORATION
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS AGENT
Reel/Frame 034917/0461 →
SECURITY AGREEMENT Recorded Dec 6, 2013
From: IPS CORPORATION
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS ADMINISTRATIVE AGENT
Reel/Frame 031768/0633 →