IP Library Granted Patent US 7,358,312
Granted Patent B2
US 7,358,312 · App. 10/487,318 · Granted Apr 15, 2008

Epoxy resin curing agent of epoxy resin-liquid amine adduct and polyamidoamine

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Quick Facts
Patent No.
US 7,358,312
App. No.
10/487,318
Granted
Apr 15, 2008
Kind
B2
Abstract

This invention describes epoxy-amine compositions that have low mix viscosity and a fast drying property at temperatures below freezing. The composition is useful for high solids coating applications, for adhesive and membrane applications, and for preparing impregnated substrates.

Claims (15)

1. A low viscosity curing agent composition for low temperature cure of epoxy resin compositions comprising a blend of: (a)(i) an amine adduct of an epoxy resin having at least 1.5 epoxy groups per molecule and (a)(ii) a liquid amine and (b) a liquid polyamidoamine prepared by reacting a long-chain carboxylic acid and an amine wherein the polyamidoamine is further reacted with an epoxy functional resin and a monoglycidyl ether or ester;

wherein the liquid amine is selected from the group consisting of cycloaliphatic, aliphatic and alkylaromatic polyamines.

2. The low viscosity curing composition of claim 1 , wherein the liquid amine used for reaction product (a) is selected from the group consisting of cycloaliphatic amines, aliphatic amines and alkylaromatic amines, having a hydrocarbyl backbone containing from 2 to 20 carbon atoms.

3. The low viscosity curing composition of claim 2 wherein the liquid amine used for reaction product (a) is a cycloaliphatic or aliphatic diamine containing from 6 to 16 carbon atoms and having either two primary amino groups or one primary and one secondary amino group.

4. The curing agent composition according to claim 3 , wherein the liquid amine is a mixture of amines wherein one amine comprises two primary amino groups and wherein another amine comprises one primary and one secondary amino group.

5. The curing agent composition according to claim 1 , wherein the curing agent is prepared in-situ from:

a) an amine, selected from the group consisting of cycloaliphatic amines, aliphatic amines and alkylaromatic amines having a hydrocarbyl backbone containing from 2 to 20 carbon atoms;

b) a substituted alkyl amidopolyamide prepared from a) and a long-chain monocarboxylic acid having from 6 to 50 carbon atoms, or a long-chain dicarboxylic acid having from 18 to 60 carbon atoms;

c) an epoxy resin derived from polyglycidyl ethers of polyhydric phenols; and

d) a mono functional epoxy ether or ester, linear or branched having from 4 to 36 carbon atoms.

6. A formulation to be used at low temperature containing the curing agent of claim 1 , an accelerator compatible with the curing agent derived from mineral or organic acids or salts, from phenol derivatives or a combination thereof, and an epoxy compatible accelerator derived from a product containing an acrylic ester group wherein the acrylic functionality is more than two.

7. The formulation of claim 6 , wherein the epoxy compatible accelerator comprises a blend of polyacrylate and an epoxy resin having a 1,2-epoxy equivalency greater than one epoxy group per molecule wherein the epoxy resin is saturated or unsaturated, linear or branched, aliphatic, cycloaliphatic, aromatic or heterocylic, and optionally has substituents which do not materially interfere with the curing reaction.

8. The formulation of claim 6 , wherein the epoxy compatible accelerator is an acrylic ester derived from an aryl.

9. A cured coating film comprising the formulation of claim 7 wherein the film is applied on a shaped carrier.

10. The cured coating film according to claim 9 wherein the shaped carrier is comprised of wood or polymers.

Assignments (29)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 17, 2022
From: HEXION INC.
To: WESTLAKE EPOXY INC.
Reel/Frame 061611/0876 →
PARTIAL TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS (TERM LOAN) Recorded Feb 1, 2022
From: JPMORGAN CHASE BANK, N.A.
To: HEXION INC.
Reel/Frame 058932/0923 →
PARTIAL TERMINATION AND RELEASE OF SECURITY INTEREST IN SPECIFIED PATENTS (ABL) Recorded Feb 1, 2022
From: JPMORGAN CHASE BANK, N.A.
To: HEXION INC.
Reel/Frame 058932/0915 →
PATENT SECURITY INTEREST (ABL) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049740/0770 →
PATENT SECURITY INTEREST (TERM LOAN) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049741/0425 →
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (030146/0970) Recorded Jul 9, 2019
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT AND COLLATERAL AGENT
To: HEXION INC. (FORMERLY KNOWN AS MOMENTIVE SPECIALTY CHEMICALS INC.)
Reel/Frame 049706/0264 →
PATENT SECURITY INTEREST ASSIGNMENT AGREEMENT Recorded Apr 3, 2019
From: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS THE PRIOR COLLATERAL AGENT
To: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS THE CURRENT COLLATERAL AGENT
Reel/Frame 048788/0617 →
RELEASE OF SECURITY INTEREST Recorded Feb 23, 2017
From: WILMINGTON TRUST, NATIONAL ASSOCIATION (SUCCESSOR BY MERGER TO WILMINGTON TRUST FSB), AS COLLATERAL AGENT
To: HEXION INC. (FORMERLY KNOWN AS HEXION SPECIALTY CHEMICALS INC.); BORDEN CHEMICAL FOUNDRY, LLC; HEXION INVESTMENTS INC. (FORMERLY KNOWN AS BORDEN CHEMICAL INVESTMENTS, INC.); HEXION U.S. FINANCE CORP.; HSC CAPITAL CORPORATION; LAWTER INTERNATIONAL INC.; HEXION INTERNATIONAL INC. (FORMERLY KNOWN AS BORDEN CHEMICAL INTERNATIONAL INC.); OILFIELD TECHNOLOGY GROUP, INC.; HEXION CI HOLDING COMPANY (CHINA) LLC
Reel/Frame 041793/0001 →
SECURITY INTEREST Recorded Feb 13, 2017
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 041693/0888 →
RELEASE OF SECURITY INTEREST Recorded Jul 15, 2016
From: WILMINGTON TRUST COMPANY
To: HEXION INC.
Reel/Frame 039360/0724 →
CHANGE OF NAME Recorded Feb 3, 2015
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: HEXION INC.
Reel/Frame 034882/0816 →
PATENT SECURITY AGREEMENT Recorded Apr 3, 2013
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 030146/0946 →
PATENT SECURITY AGREEMENT Recorded Apr 3, 2013
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 030146/0970 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Mar 28, 2013
From: JPMORGAN CHASE BANK, N.A.
To: MOMENTIVE SPECIALTY CHEMICALS INC. (F/K/A HEXION SPECIALTY CHEMICALS, INC.)
Reel/Frame 030111/0021 →
CORRECTIVE ASSIGNMENT TO CORRECT THE RECEIVING PARTY NAME PREVIOUSLY RECORDED ON REEL 027805, FRAME 0642. Recorded Apr 19, 2012
From: RESOLUTION PERFORMANCE PRODUCTS CORP
To: HEXION SPECIALTY CHEMICALS, INC.
Reel/Frame 028078/0190 →
CERTIFICATE OF CONVERSION Recorded Mar 5, 2012
From: RESOLUTION PERFORMANCE PRODUCTS LLC
To: RESOLUTION PERFORMANCE PRODUCTS CORP
Reel/Frame 027805/0621 →
MERGER Recorded Mar 5, 2012
From: RESOLUTION PERFORMANCE PRODUCTS CORP
To: N SPECIALTY CHEMICALS, INC.
Reel/Frame 027805/0642 →
CHANGE OF NAME Recorded Mar 5, 2012
From: HEXION SPECIALTY CHEMICALS, INC.
To: MOMENTIVE SPECIALTY CHEMICALS INC.
Reel/Frame 027805/0802 →
SECURITY AGREEMENT Recorded Feb 5, 2010
From: HEXION LLC; HEXION SPECIALTY CHEMICALS, INC.; BORDEN CHEMICAL FOUNDRY, LLC; BORDEN CHEMICAL INVESTMENTS, INC.; HEXION U.S. FINANCE CORP.; HSC CAPITAL CORPORATION; LAWTER INTERNATIONAL INC.; BORDEN CHEMICAL INTERNATIONAL, INC.; OILFIELD TECHNOLOGY GROUP, INC.; HEXION CI HOLDING COMPANY (CHINA) LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 023905/0451 →
SECURITY INTEREST Recorded Jan 29, 2010
From: HEXION SPECIALTY CHEMICALS, INC.; BORDEN CHEMICAL FOUNDRY, LLC; BORDEN CHEMICAL INVESTMENTS, INC.; HEXION U.S. FINANCE CORP.; HSC CAPITAL CORPORATION; LAWTER INTERNATIONAL INC.; BORDEN CHEMICAL INTERNATIONAL, INC.; OILFIELD TECHNOLOGY GROUP, INC.; HEXION CI HOLDING COMPANY (CHINA) LLC
To: WILMINGTON TRUST FSB, AS COLLATERAL AGENT
Reel/Frame 023963/0038 →
RELEASE OF SECURITY INTEREST Recorded Jan 28, 2010
From: GENERAL ELECTRIC CAPITAL CORPORATION
To: RESOLUTION PERFORMANCE PRODUCTS LLC
Reel/Frame 023861/0751 →
SECURITY AGREEMENT Recorded Nov 21, 2006
From: HEXION SPECIALTY CHEMICALS, INC.
To: WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT
Reel/Frame 018535/0701 →
SECURITY AGREEMENT Recorded Nov 21, 2006
From: HEXION SPECIALTY CHEMICALS, INC.
To: JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT
Reel/Frame 018535/0556 →
SECURITY AGREEMENT Recorded Jul 14, 2006
From: HEXION SPECIALTY CHEMICALS, INC.
To: JPMORGAN CHASE BANK, N.A. AS COLLATERAL AGENT
Reel/Frame 017946/0151 →
SECURITY AGREEMENT Recorded Aug 31, 2005
From: RESOLUTION PERFORMANCE PRODUCTS LLC; RESOLUTION SPECIALTY MATERIALS LLC; BORDEN CHEMICAL, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 016480/0648 →
SECURITY AGREEMENT Recorded Aug 31, 2005
From: RESOLUTION PERFORMANCE PRODUCTS LLC; RESOLUTION SPECIALTY MATERIALS LLC; BORDEN CHEMICAL, INC.
To: WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT
Reel/Frame 016522/0428 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 28, 2005
From: DE COCK, CHRISTIAN JEAN CHARLES; CLAEYS BOUUAERT, PASCALE CHARLOTTE A.M.G.; KINCAID, DEREK SCOTT; VAN POPPEL, KARIN; VANDENBERGHE, DOMINIQUE ELISABETH MARLE; WANG, PEN CHUNG
To: RESOLUTION PERFORMANCE PRODUCTS LLC
Reel/Frame 016426/0734 →
SECURITY AGREEMENT Recorded Jan 25, 2005
From: RESOLUTION PERFORMANCE PRODUCTS LLC
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS COLLATERAL AGENT
Reel/Frame 015596/0703 →
RELEASE OF PATENT SECURITY AGREEMENT Recorded Jan 25, 2005
From: MORGAN STANLEY & CO., INCORPORATED
To: RESOLUTION PERFORMANCE PRODUCTS LLC
Reel/Frame 015603/0117 →