Phenalkamine epoxy curing agents from methylene bridged poly(cyclohexyl-aromatic) amines and epoxy resin compositions containing the same

Patent metadata

Field	Value
Publication number	US-11891476-B2
Application number	US-202017076866-A
Country	US
Kind code	B2
Filing date	Oct 22, 2020
Priority date	Nov 8, 2019
Publication date	Feb 6, 2024
Grant date	Feb 6, 2024

Abstract

The present invention relates to a new structural class of phenalkamine, phenalkamine curing agent compositions, methods of making such phenalkamine, and methods of making such compositions. The phenalkamine curing agent compositions of the present invention can be prepared by reacting cardanol with an aldehyde compound and a mixture of methylene bridged poly(cycloaliphatic-aromatic)amines. These curing-agent compositions may be used to cure, harden, and/or crosslink an epoxy resin.

First claim

The invention claimed is:

1. A curing agent composition comprising a phenalkamine mixture comprising six phenalkamines of formulas (VII), (VIII), (IX), (X), (XI), and (XII):

wherein n=0, 2, 4, or 6; and R′=H, C 1 -C 10 alkyl, Ph, a C 5 -C 6 cycloaliphatic group, or a C 5 -C 10 aromatic group and further comprising an additional amine having at least two amine functionalities selected from
diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), pentaethylenehexamine (PEHA), hexamethylenediamine (HMDA), 1,3-pentanediamine, 2-methyl-1,5-pentanediamine, triaminononane, N-(2-aminoethyl)-1,3-propanediamine (N 3 -Amine), N,N′-1,2-ethanediylbis-1,3-propanediamine (N 4 -amine), dipropylenetriamine; an arylaliphatic amine, m-xylylenediamine (mXDA), p-xylylenediamine, a cycloaliphatic amine, 1,3-bis(aminomethyl)cyclohexylamine (1,3-BAC), isophorone diamine (IPDA), 4,4′-methylenebiscyclohexanamine, 1,2-diaminocyclohexylamine (DCHA), aminopropylcyclohexylamine (APCHA), a methylene bridged poly (cycloaliphatic-aromatic) amine, an aromatic amine, m-phenylenediamine, diaminodiphenylmethane (DDM), diaminodiphenylsulfone (DDS); a polyalkoxyamine where the alkoxy group can be an oxyethylene, oxypropylene, oxy-1,2-butylene, oxy-1,4-butylene or co-polymers thereof, 4,7-dioxadecane-1,10-diamine, I-propanamine, 3,3′-(oxybis(2,1-ethanediyloxy))bis(diaminopropylated diethylene glycol), poly(oxy-(methyl-1,2-ethanediyl)), α-(2-aminomethylethyl) ω-(2-aminomethylethoxy), triethyleneglycoldiamine and oligomers, poly(oxy(methyl-1,2-ethanediyl)), αα′-(oxydi-2,1-ethanediyl)bis(ω-(aminomethylethoxy)), bis(3-amino-propyl)polytetrahydrofuran 350, bis(3-aminopropyl)polytetrahydrofuran 750, poly(oxy(methyl-1,2-ethanediyl)), α-hydro-ω-(2-aminomethylethoxy)ether with 2-ethyl-2-(hydroxymethyl)-1,3-propanediol (3:I), and diaminopropyldiaminopropyl dipropylene glycol,
amidoamine and polyamide curing agents and
Mannich bases of phenolic compounds with amines and formaldehyde.

2. An amine-epoxy composition comprising the reaction product of the curing agent composition according to claim 1 and an epoxy component.

3. An article of manufacture comprising the amine-epoxy composition as set forth in claim 2 .

4. The article of manufacture of claim 3 , wherein the article is a coating, an adhesive, a construction product, a flooring product, or a composite product.

5. A method for producing the curing agent composition of claim 1 comprising combining a phenalkamine mixture comprising six phenalkamines of formules (VII), (VIII), (IX), (X), (XI), and (XII):

wherein n=0, 2, 4, or 6; and R′=H, C 1 -C 10 alkyl, Ph, a C 5 -C 6 cycloaliphatic group, or a C 5 -C 10 aromatic group and an additional amine having at least two amine functionalities selected from the group consisting of
diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), pentaethylenehexamine (PEHA), hexamethylenediamine (HMDA), 1,3-pentanediamine, 2-methyl-1,5-pentanediamine, triaminononane, N(2-aminoethyl)-1,3-propanediamine (N 3 -Amine), N,N′-1,2-ethanediylbis-1,3-propanediamine (N 4 -amine), dipropylenetriamine; an arylaliphatic amine, m-xylylenediamine (mXDA), p-xylylenediamine, a cycloaliphatic amine, 1,3-bis(aminomethyl)cyclohexylamine (1,3-BAC), isophorone diamine (IPDA), 4,4′-methylenebiscyclohexanamine, 1,2-diaminocyclohexylamine (DCHA), aminopropylcyclohexylamine (APCHA), a methylene bridged poly (cycloaliphatic-aromatic) amine, an aromatic amine, m-phenylenediamine, diaminodiphenylmethane (DDM), diaminodiphenylsulfone (DDS); a polyalkoxyamine where the alkoxy group can be an oxyethylene, oxypropylene, oxy-1,2-butylene, oxy-1,4-butylene or co-polymers thereof, 4,7-dioxadecane-1,10-diamine, I-propanamine, 3,3′-(oxybix(2,1-ethanediyloxy))bis(diaminopropylated diethylene glycol), poly(oxy(methyl-1,2-ethanediyl)), α(2-aminomethylethyl) ω(2-aminomethylethoxy), triethyleneglycoldiamine and oligomers, poly(oxy(methyl-1,2-ethanediyl), α,α′-(oxydi-2,1-ethanediyl)bis(ω-(aminomethylethoxy)), bis(3-aminopropyl)polytetrahydrofuran 350, bis(3-aminopropyl)polytetrahydrofuran 750, poly(oxy(methyl-1,2-ethanediyl)), α-hydro-ω-(2-aminomethylethoxy)ether with 2-ethyl-2-(hydroxymethyl)-1,3-propanediol (3:I), and diaminopropyldiaminopropyl dipropylene glycol,
amidoamine and polyamide curing agents and
Mannich bases of phenolic compounds with amines and formaldehyde.

Assignees

• Evonik Operations Gmbh

Inventors

• Lal Gauri Sankar
• Cook Michael

Classifications

• C08G59/623 Primary

  Aminophenols · CPC title

• C08G59/4014

  Nitrogen containing compounds · CPC title

• C08G59/5033 Primary

  aromatic · CPC title

• C09D163/00

  Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins · CPC title

• C08G59/621 Primary

  Phenols · CPC title