IP Library Granted Patent US 9,133,373
Granted Patent B2
US 9,133,373 · App. 13/904,161 · Granted Sep 15, 2015

Elastic methacrylate compositions

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Quick Facts
Patent No.
US 9,133,373
App. No.
13/904,161
Granted
Sep 15, 2015
Kind
B2
Abstract

A two-part adhesive composition exhibiting improved elasticity wherein its composition includes one or more acrylate or methacrylate ester monomers, a sulfur bearing compound, preferably a sulfonyl chloride, an amine promoter, preferably, an amine aldehyde reaction product, and a thermoplastic block copolymer component selected from the group consisting of a. a linear styrene-butadiene-styrene copolymer b. a radial styrene-butadiene-styrene block copolymer with a plasticizer, c. a linear or radial styrene-isoprene-styrene block copolymer, and d. a linear or radial styrene-butadiene-isoprene-styrene block copolymer, and mixtures thereof.

Claims (19)

1. A two-part adhesive composition comprising a component A adhesive portion and a component B activator portion, which portions are capable of being mixed in a 1:1 ratio to form elastic or ductile adhesives with improved properties, wherein

component A comprises methyl methacrylate monomer and a free radical initiating species comprising a sulfur bearing compound selected from the group consisting of chlorosulfonated polymers, sulfonyl chloride and sulfimides, and a peroxide, wherein the peroxide is free of benzoyl peroxide, and

component B comprises methyl methacrylate monomer and an amine promoter selected from the group consisting of tertiary aromatic amines and amine-aldehyde promoters, wherein either component A or component B or both further comprise a thermoplastic block copolymer component selected from the group consisting of

a. a linear styrene-butadiene-styrene block copolymer,

b. a linear styrene-isoprene-styrene block copolymer,

c. a linear styrene-butadiene-isoprene-styrene block copolymer,

and mixtures thereof,

wherein either component A or component B or both further comprise an adhesion promoting polymer,

wherein component B does not include a chlorosulfonated polymer and wherein either component A or B or both further comprise a core shell impact modifier.

2. The two-part adhesive composition of claim 1 wherein the sulfur bearing compound is selected from the group consisting of sulfonyl chloride and sulfimide.

3. The two-part adhesive composition of claim 1 wherein the thermoplastic block polymer component of claim 1 further comprises an adhesion promoting polymer.

4. The two-part adhesive composition of claim 1 wherein the adhesion promoting polymer comprises a chlorinated polymer selected from the group consisting of chlorosulfonated polyethylene, chlorinated polyethylene, polychloroprene polymers and mixtures thereof.

5. The two-part adhesive composition of claim 1 further comprising an initiator selected from the group consisting of sulfur bearing compounds, peroxides and mixtures thereof.

6. The two-part adhesive composition of claim 1 , wherein the methyl methacrylate monomer comprises 20 to 90% by weight of the composition;

the sulfur bearing compound comprises 0.02 to 30% by weight of the composition; the amine promoter comprises 0.05 to 10% by weight the composition; and the thermoplastic block copolymer component comprises 5 to 50% by weight of the composition.

7. The two-part adhesive composition of claim 1 , wherein the sulfur bearing compound comprises a sulfonyl chloride.

8. The two-part adhesive composition of claim 1 , wherein the amine-aldehyde promoter comprises an amine aldehyde reaction product.

9. The two-part adhesive composition of claim 1 further comprising a cure initiation system selected from the group consisting of cumene hydroperoxide, methyl ethyl ketone peroxide, benzoate peresters, and mixtures thereof.

10. The two-part adhesive composition of claim 1 wherein the amine-aldehyde promoter comprises dihydropyridine.

Assignments (25)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 29, 2013
From: BRIGGS, PAUL C.; OSAE, SAMUEL B.
To: IPS CORPORATION
Reel/Frame 030501/0171 →