IP Library Granted Patent US 7,795,351
Granted Patent B2
US 7,795,351 · App. 11/646,664 · Granted Sep 14, 2010

Adhesive compositions for bonding and filling large assemblies

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Quick Facts
Patent No.
US 7,795,351
App. No.
11/646,664
Granted
Sep 14, 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 (26)

1. A polymerizable adhesive or filling composition comprising

about 5 to about 75 percent, by weight, of a blend of

a) at least one crosslinked or partially crosslinked polymer or elastomer, and

b) at least one soluble thermoplastic polymer or elastomer,

about 0.5 to about 35 percent, by weight, of a vinyl ester resin derived from the reaction product of a polyepoxide and an unsaturated monocarboxylic acid and the subsequent addition of a styrene monomer, and

about 20 to about 80 percent of an alkyl acrylate or methacrylate monomer.

2. 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, hexyl methacrylate, cyclohexyl methacrylate, methyl acrylate, ethyl acrylate hydroxyethyl acrylate, propyl acrylate, hydroxypropyl acrylate, butyl acrylate, hexyl acrylate, cyclohexyl methacrylate, or mixtures thereof.

3. 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.

4. The polymerizable adhesive or filling composition of claim 3 wherein the polymerizable organic acid monomer comprises methacrylic acid or acrylic acid or mixtures thereof.

5. The polymerizable adhesive or filling composition of claim 3 wherein the polymerizable organic acid monomer is selected from the group consisting of maleic acid, fumaric acid, itaconic acid and mixtures thereof.

6. The polymerizable adhesive or filling composition of claim 3 wherein the polymerizable organic acid monomer or oligomer comprises a vinyl substituted phosphate ester.

7. 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.

8. 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.

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

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

11. The polymerizable adhesive or filling composition of claim 10 wherein the polyester resin is selected from the group consisting of orthophthalic, isophthalic, terephthalic, halogenated polyester resins and mixtures thereof.

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

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

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

15. The polymerizable adhesive or filling composition of claim 14 wherein the core-shell impact modifier is selected from the group consisting of methacrylate butadiene styrene (MBS), acrylonitrile butadiene styrene (ABS), and an acrylic based or ethylene propylene core-shell impact modifier.

16. The polymerizable adhesive or filling composition of claim 1 wherein the crosslinked or partially crosslinked polymer is selected from the group consisting of a crosslinked polychloroprene elastomer, a crosslinked butadiene acrylonitrile elastomer, and a crosslinked acrylate polymer or terpolymer and mixtures thereof.

17. The polymerizable adhesive or filling composition of claim 1 wherein the soluble thermoplastic polymer or elastomer comprises a diene based polymer comprising butadiene or isoprene, including liquid polymers and copolymers of butadiene.

18. The polymerizable adhesive or filling composition of claim 17 wherein the diene based polymer or elastomer comprises a copolymer of butadiene, isoprene, or a combination of butadiene or isoprene with styrene, acrylonitrile or an acrylic monomer.

19. The polymerizable adhesive or filling composition of claim 1 wherein the soluble thermoplastic polymer or elastomer comprises a block copolymer of butadiene, isoprene, or mixtures of butadiene and isoprene, ethylene-propylene or ethylene-butylene with styrene.

20. The polymerizable adhesive or filling composition of claim 1 wherein the monomer comprises a higher molecular weight monofunctional or polyfunctional monomer.

21. The polymerizable adhesive or filling composition of claim 20 wherein the monomer comprises lauryl methacrylate.

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 →