IP Library Granted Patent US 7,550,550
Granted Patent B2
US 7,550,550 · App. 10/524,247 · Granted Jun 23, 2009

Polyether polyamine agents and mixtures therefor

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Quick Facts
Patent No.
US 7,550,550
App. No.
10/524,247
Granted
Jun 23, 2009
Kind
B2
Abstract

Provided herein are polyamine precursors useful in the manufacture of epoxy resins. Use of a polyamine precursor according to the invention provides an epoxy resin formulation having an increased working time over prior art amines used for curing epoxies. Increased working times translate to the ability to manufacture composites which could not be made using conventional epoxy curing agents, such as composite blades for wind-driven turbines. Such polyamines are also useful in polyurea formulations for lengthening reaction time, thus allowing more flow of applied polyurea coatings prior to gellation.

Claims (24)

1. A polyamine composition having the structure:

wherein L is an oxyalkoxo group having the structure:

—O—R 1 —O—

in which R 1 comprises at least one of the following:

including mixtures of two or more of the foregoing polyamines; wherein the R 1 may further comprise a group selected from the group consisting of: C1 to C5 alkylene; 2-methyl propylene; 2,2-dimethyl propylene; —CH2CH2—O—CH2CH2— and —CH2CH2CH2—O—CH2CH2CH2—; including mixtures of two or more of the foregoing polyamines.

2. A process for preparing a cured epoxy (poly-(etheralkanolamine)) resin comprising the steps of:

a) providing a polyamine composition according to claim 1 ;

b) providing a polyfunctional epoxy precursor; and

c) contacting said polyfunctional epoxy precursor and said polyamine with one another.

3. A process for preparing a polyurea comprising the steps of:

a) providing an organic di-isocyanate;

b) providing at least one polyamine composition according to claim 1 ; and

c) contacting said organic di-isocyanate and said polyamine with one another.

4. A process for preparing a cured epoxy (poly-(etheralkanolamine)) resin comprising the steps of:

a) providing an amine mixture comprising a polyamine composition according to claim 1 , and one or more materials selected from the group consisting of: N-aminoethylpiperazine; diethylenetriamine; triethylenetetramine; tetraethylenepentamine; 2-methylpentamethylene;1,3-pentanediamine; trimethylhexamethylene diamine; a polyamide hardener; a polyamidoamine hardener; a Mannich-base hardener; bis(aminomethyl)cyclohexylamine; isophorone diamine; menthane diamine; bis(p-aminocyclohexyl)methane; 2,2′-dimethyl bis(p-aminocyclohexyl)methane; dimethyldicyclohexylmethane; 1,2-diaminocyclohexane; 1,4-diaminocyclohexane; meta-xylene diamine; norbornanediamine; meta-phenylene diamine; diaminodiphenylsulfone; methylene dianiline; JEFFAMINE® D-230 amine; JEFFAMINE® D-400 amine; JEFFAMINE® T-403 amine; and diethyltoluenediamine;

b) providing an polyfunctional epoxy; and

c) contacting said polyfunctional epoxy precursor and said polyamine with one another.

5. A process for preparing a polyurea comprising the steps of:

a) providing an organic di-isocyanate;

b) providing a polyamine according to claim 1 in admixture with at least one material selected from the group consisting of: N-aminoethylpiperazine; diethylenetriamine; triethylenetetramine; tetraethylenepentam; 2-methylpentamethylene diamine; 1,3-pentanediamine; trimethylhexamethylene diamine; polyamide hardeners; polyamidoamine hardeners; Mannich-base hardeners; bis(aminomethyl) cyclohexylamine; isophorone diamine; menthane diamine; bis(p-aminocyclohexyl)methane (“PACM”); 2,2′-dimethyl bis (p-aminocyclohexyl)methane; dimethyldicyclohexylmethane; 1,2-diaminocyclohexane; 1,4-diaminocyclohexane; meta-xylene; norbornanediamine; meta-phenylene diamine; diaminodiphenylsulfone; methylene dianiline; JEFFAMINE® D-230 amine; JEFFAMINE® D-400 amine; JEFFAMINE® T-403 amine; and diethyltoluenediamine; and

c) contacting said organic di-isocyanate and said polyamine with one another.

6. The polyamine composition of claim 1 , wherein the R 1 further comprises at least one of a C 1 to C 5 alkylene and mixtures thereof.

7. The polyamine composition of claim 1 , wherein the R 1 further comprises at least one of 2-methyl propylene; 2,2-dimethyl propylene; and mixtures thereof.

8. The polyamine composition of claim 1 , wherein the R 1 further comprises at least one of —CH 2 CH 2 —O—CH 2 CH 2 —; —CH 2 CH 2 CH 2 —O—CH 2 CH 2 CH 2 —; and mixtures thereof.

Assignments (6)
TERMINATION AND RELEASE OF SECURITY INTEREST IN UNITED STATES TRADEMARKS AND PATENTS Recorded Jun 13, 2018
From: JPMORGAN CHASE BANK, N.A.
To: HUNTSMAN PETROCHEMICAL CORPORATION (N/K/A HUNTSMAN PETROCHEMICAL LLC)
Reel/Frame 046356/0616 →
CORRECTIVE ASSIGNMENT TO CORRECT THE NATURE OF CONVEYANCE FROM AN ASSIGNMENT TO A SECURITY AGREEMENT PREVIOUSLY RECORDED ON REEL 025857 FRAME 0137. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 28, 2011
From: DEUTSCHE BANK TRUST AG NEW YORK BRANCH, AS RESIGNING ADMINISTRATIVE AGENT AND COLLATERAL AGENT
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 026515/0641 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 28, 2011
From: DEUTSCHE BANK TRUST AG NEW YORK BRANCH, AS RESIGNING ADMINISTRATIVE AGENT AND COLLATERAL AGENT
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 025857/0137 →
CHANGE OF NAME Recorded Mar 5, 2010
From: HUNTSMAN PETROCHEMICAL CORPORATION
To: HUNTSMAN PETROCHEMICAL LLC
Reel/Frame 024035/0550 →
SECURITY INTEREST Recorded Nov 17, 2005
From: HUNTSMAN PETROCHEMICAL CORPORATION
To: DEUTSCHE BANK AG NEW YORK BRANCH, AS COLLATERAL AGENT
Reel/Frame 016987/0496 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 10, 2005
From: KLEIN, HOWARD P.; BURTON, BRUCE L.; FORKNER, MATTHEW W.; ALEXANDER, DAVID C.; RENKEN, TERRY L.; GODINICH, CHRIS E.
To: HUNTSMAN PETROCHEMICAL CORPORATION
Reel/Frame 016747/0837 →