IP Library Granted Patent US 7,816,453
Granted Patent B2
US 7,816,453 · App. 12/056,342 · Granted Oct 19, 2010

Adhesive compositions for bonding and filling large assemblies

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Quick Facts
Patent No.
US 7,816,453
App. No.
12/056,342
Granted
Oct 19, 2010
Kind
B2
Abstract

Adhesive composition for bonding and filling large assemblies, including a mixture of about 5 percent to about 75 percent by weight of a thermoplastic polymer, about 0.5 percent to about 35 percent by weight of a polyester resin or vinyl ester resin, and about 20 percent to about 80 percent by weight of an alkyl acrylate or methacrylate monomer.

Claims (25)

1. A polymerizable adhesive or filling composition for large assemblies comprising from about 5 to about 75 percent, by weight, of a thermoplastic or partially thermoplastic polymer or elastomer, from about 0.5 to about 35 percent, by weight, of a dicyclopentadiene resin and about 20 to about 80 percent of an alkyl acrylate or methacrylate monomer, wherein the thermoplastic or partially thermoplastic polymer or elastomer is crosslinked or partially crosslinked.

2. The polymerizable adhesive or filling composition of claim 1 wherein the thermoplastic or partially thermoplastic polymer comprises a core-shell polymer or impact modifier.

3. The polymerizable adhesive or filling composition of claim 1 wherein the thermoplastic or partially thermoplastic polymer comprises an elastomer or mixture of elastomers and a core-shell polymer or impact modifier.

4. The polymerizable adhesive or filling composition of claim 1 wherein the thermoplastic or partially thermoplastic polymer or elastomer is selected from the group consisting of a nitrile elastomer, a liquid nitrile polymer, a chlorinated polymer or elastomer, a polymer or copolymer of chloroprene, chlorinated polyethylene, chlorosulfonated polyethylene, epichlorohydrin polymers, polymers and copolymers of butadiene, isoprene and ethylene-propylene and ethylene-butylene with acrylonitrile and styrene, an acrylate or methacrylate polymer or copolymer, and mixtures of the above.

5. The polymerizable adhesive or filling composition of claim 1 wherein the alkyl acrylate or methacrylate monomers comprise a C1-C6 acrylate or methacrylate monomer selected from the group consisting of methyl methacrylate, ethyl methacrylate, hydroxyethyl methacrylate, propyl methacrylate, hydroxypropyl methacrylate, butyl methacrylate, hexamethyl methacrylate, hexyl methacrylate, cyclohexyl methacrylate, methyl, acrylate, ethyl acrylate hydroxyethyl acrylate, propyl acrylate, hydroxypropyl acrylate, butyl acrylate, hexyl acrylate, cyclohexyl methacrylate, or mixtures thereof.

6. The polymerizable adhesive or filling composition of claim 1 wherein the thermoplastic or partially thermoplastic polymer is selected from the group consisting of a blend of two or more thermoplastic or partially thermoplastic polymers, a blend of two or more elastomers, or at least one elastomer and at least one thermoplastic or partially thermoplastic polymer or mixtures thereof.

7. The polymerizable adhesive or filling composition of claim 2 wherein the core-shell polymer or impact modifier is selected from the group consisting of ABS, MABS, MBS, and or all-acrylic and mixtures thereof.

8. The polymerizable adhesive or filling composition of claim 1 wherein the thermoplastic polymer is selected from the group consisting of polystyrene and copolymers thereof, acrylic polymers and copolymers, polymers of acrylonitrile including styrene/acrylonitrile, ABS, and MABS, chlorinated polymers including polyvinyl chloride polymers and copolymers and mixtures of the above.

9. The polymerizable adhesive or filling composition of claim 3 wherein the elastomer or mixture of elastomers is selected from the group consisting of soluble or lightly crosslinked polychloroprene, chlorinated polyethylene, chlorosulfonated polyethylene, poly(epichlorohydrin), styrene-butadiene and styrene-isoprene polymers and block copolymers, soluble, lightly crosslinked or liquid polymers of acrylonitrile, butadiene and isoprene, acrylic elastomers, ethylene acrylic elastomers, and mixtures thereof.

10. The polymerizable adhesive or filling composition of claim 1 further comprising from about 0.01 to about 20 percent by weight of a polymerizable organic acid monomer or oligomer.

11. The polymerizable adhesive or filling composition of claim 10 wherein the polymerizable organic acid monomer comprises methacrylic acid or acrylic acid or mixtures thereof.

12. The polymerizable adhesive or filling composition of claim 10 wherein the polymerizable organic acid monomer is selected from the group consisting of maleic acid, fumaric acid, itaconic acid and mixtures thereof.

13. The polymerizable adhesive or filling composition of claim 10 wherein the polymerizable organic acid monomer or oligomer comprises a vinyl substituted phosphate ester.

14. The polymerizable adhesive or filling composition of claim 1 further comprising from about 0.1 to about 10 percent by weight of a viscosity control agent.

15. The polymerizable adhesive or filling composition of claim 1 further comprising one or more materials selected from the group consisting of catalysts, initiators, reducing agents, activators, and promoters and mixtures thereof.

16. The polymerizable adhesive or filling composition of claim 1 further comprising a chlorosulfonated polymer, an organic sulfonyl chloride and a dihydropyridine.

17. The polymerizable adhesive or filling composition of claim 1 further comprising a compound selected from the group consisting of a hydroperoxide, a dione or other chelator, an organometallic salt and an aromatic amine and combinations thereof.

18. The polymerizable adhesive or filling composition of claim 1 wherein the thermoplastic or partially thermoplastic polymer or elastomer is insoluble or only partially soluble in the monomer.

19. The polymerizable adhesive or filling composition of claim 1 wherein the thermoplastic or partially thermoplastic polymer or elastomer provides gel properties in the composition prior to curing.

20. The polymerizable adhesive or filling composition of claim 1 wherein the thermoplastic or partially thermoplastic polymer or elastomer is selected from the group consisting of diene polymers or copolymers, acrylic polymers or copolymers and chlorinated polymers and mixtures thereof.

21. A polymerizable adhesive or filling composition for large assemblies comprising from about 5 to about 75 percent, by weight, of a thermoplastic or partially thermoplastic polymer or elastomer, from about 0.5 to about 35 percent, by weight, of a dicyclopentadiene resin and about 20 to about 80 percent of an alkyl acrylate or methacrylate monomer, wherein the thermoplastic or partially thermoplastic polymer or elastomer is crosslinked or partially crosslinked, wherein at least one thermoplastic or partially thermoplastic polymer or elastomer is insoluble or only partially soluble in the monomer, wherein at least one thermoplastic or partially thermoplastic polymer or elastomer provides gel properties in the composition prior to curing, and wherein the thermoplastic or partially thermoplastic polymer or elastomer is selected from the group consisting of diene polymers or copolymers, acrylic polymers or copolymers and chlorinated polymers and mixtures thereof.

22. The polymerizable adhesive or filling composition of claim 21 further comprising at least 0.5 percent, by weight, of a polyester resins.

23. The polymerizable adhesive or filling Composition of claim 22 wherein the polyester resin is selected from the group consisting of orthophthalic, isophthalic, terephthalic, halogenated polyester resins and mixtures thereof.

24. The polymerizable adhesive or filling composition of claim 1 further comprising at least 0.5 percent, by weight, of a vinyl ester resin.

25. The polymerizable adhesive or filling composition of claim 1 further comprising at least 0.5 percent, by weight, of an orthophthalic resin.

Assignments (26)
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 →
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 →
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 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 →
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 →
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 →
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 →
RELEASE OF SECURITY INTEREST Recorded Dec 22, 2016
From: ANTARES CAPITAL LP, AS ADMINISTRATIVE AGENT
To: IPS CORPORATION
Reel/Frame 040744/0449 →
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 036842/0975 →
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 →
SECURITY AGREEMENT Recorded Aug 20, 2012
From: IPS CORPORATION
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS ADMINISTRATIVE AGENT
Reel/Frame 028810/0727 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 12, 2010
From: OSAE, SAMUEL B.; BRIGGS, PAUL C.
To: IPS CORPORATION
Reel/Frame 023765/0822 →