Epoxy resin composition comprising 2-(3-(aminomethyl)-3,5,5-trimethylcyclohexyl)propane-1,3-diamine (am-cpda) as hardener

Patent metadata

Field	Value
Publication number	US-2017355809-A1
Application number	US-201715602723-A
Country	US
Kind code	A1
Filing date	May 23, 2017
Priority date	Jun 10, 2016
Publication date	Dec 14, 2017
Grant date	—

Abstract

An epoxy resin composition including A) at least one epoxy compound and B) a hardener composition including B1) 0.1%-100% by weight of 2-(3-(aminomethyl)-3,5,5-trimethylcyclohexyl)propane-1,3-diamine, and B2) 99.9%-0% by weight of at least one further diamine and/or polyamine, where the stoichiometric ratio of the epoxy groups of A) and the number of active hydrogen atoms of the functional groups of B) varies from 1:2 to 2:1.

First claim

1 . An epoxy resin composition comprising:
A) at least one epoxy compound and B) a hardener composition comprising:
B1) from 0.1%400% by weight of 2-(3-(aminomethyl)-3,5,5-trimethylcyclohexyl)propane-1,3-diamine,
and
B2) from 99.9%-0% by weight of at least one further diamine and/or polyamine,
where the stoichiometric ratio of the epoxy groups of A) and the number of active hydrogen atoms of the functional groups of B) varies from 1:2 to 2:1, C) optionally from 0.1% to 10% by weight of at least one hardening accelerator, D) optionally at least one latent hardener, where the amounts of A)-D) add up to 100% by weight, E) optionally further additives.

2 . An epoxy resin composition consisting of:
A) at least one epoxy compound and B) a hardener composition comprising:
B1) from 0.1%400% by weight of 2-(3-(aminomethyl)-3,5,5-trimethylcyclohexyl)propane-1,3-diamine,
and
B2) from 99.9%-0% by weight of at least one further diamine and/or polyamine,
where the stoichiometric ratio of the epoxy groups of A) and the number of hydrogen atoms of the functional groups of B) varies from 1:2 to 2:1, C) optionally from 0.1% to 10% by weight of at least one hardening accelerator, D) optionally at least one latent hardener, where the amounts of A)-D) add up to 100% by weight, E) optionally further additives.

3 . The epoxy resin composition according to claim 1 , wherein epoxy compounds A) selected from saturated, unsaturated, aliphatic, cycloaliphatic, aromatic and heterocyclic epoxy compounds are present, and these may also have hydroxyl groups.

4 . The epoxy resin composition according to claim 1 , wherein epoxy compounds A) selected from glycidyl ethers, glycidyl esters, aliphatic epoxides, diglycidyl ethers based on bisphenol A and/or bisphenol F, glycidyl methacrylates are present.

5 . The epoxy resin composition according to claim 1 , wherein epoxy compounds A) selected from the group comprising epoxy resins based on bisphenol A diglycidyl ether, epoxy resins based on bisphenol F diglycidyl ether, 4,4′-methylenebis[N,N-bis(2,3-epoxypropyl)aniline], hexanediol diglycidyl ether, butanediol diglycidyl ether, trimethylolpropane triglycidyl ether, propane-1,2,3-triol triglycidyl ether, pentaerythritol tetraglycidyl ether, diglycidyl hexahydrophthalate, aliphatic or cycloaliphatic epoxy resin types are present.

6 . The epoxy resin composition according to claim 1 , wherein component B2) used comprises the following amines, alone or in mixtures:
aliphatic amines, such as the polyalkylenepolyamines, preferably selected from ethylene-1,2-diamine, propylene-1,2-diamine, propylene-1,3-diamine, butylene-1,2-diamine, butylene-1,3-diamine, butylene-1,4-diamine, 2-(ethylamino)ethylamine, 3-(methylamino)propylamine, diethylenetriamine, triethylenetetramine, pentaethylenehexamine, trimethylhexamethylenediamine, 2,2,4-trimethylhexamethylenediamine, 2,4,4-trimethylhexamethylenediamine, 2-methylpentanediamine, hexamethylenediamine, N-(2-aminoethyl)ethane-1,2-diamine, N-(3-aminopropyl)propane-1,3-diamine, N,N″-1,2-ethanediylbis(1,3-propanediamine), dipropylenetriamine, adipic dihydrazide, hydrazine; oxyalkylenepolyamines selected from polyoxypropylenediamine and polyoxypropylenetriamine (e.g. Jeffamine® D-230, Jeffamine® D-400, Jeffamine® T-403, Jeffamine® T-5000), 1,13-diamino-4,7,10-trioxatridecane, 4,7-dioxadecane-1,10-diamine; cycloaliphatic amines selected from isophoronediamine (3,5,5-trimethyl-3-aminomethylcyclohexylamine), 4,4′-diaminodicyclohexylmethane, 2,4′-diaminodicyclohexylmethane and 2,2′-diaminodicyclohexylmethane, alone or in mixtures of the isomers, 3,3′-dimethyl-4,4′-diaminodicyclohexylmethane, N-cyclohexyl-1,3-propanediamine, 1,2-diaminocyclohexane, 3-(cyclohexylamino)propylamine, piperazine, N-aminoethylpiperazine, TCD diamine (3(4),8(9)-bis(aminomethyl)tricyclo[5.2.1.0 2,6 ]decane), 4-methylcyclohexane-1,3-diamine araliphatic amines such as xylylenediamines; aromatic amines selected from phenylenediamines, phenylene-1,3-diamine, phenylene-1,4-diamine, 4,4′-diaminodiphenylmethane, 2,4′-diaminodiphenylmethane, 2,2′-diaminodiphenylmethane, alone or in mixtures of the isomers; adduct hardeners which are the reaction products of epoxy compounds, especially glycidyl ethers of bisphenol A and F, with excess amine; polyamidoamine hardeners which are obtained by condensation of mono- and polycarboxylic acids with polyamines, especially by condensation of dimer fatty acids with polyalkylenepolyamines; Mannich base hardeners which are obtained by reaction of mono- or polyhydric phenols with aldehydes, especially formaldehyde, and polyamines; Mannich bases, for example based on phenol and/or resorcinol, formaldehyde and m-xylylenediamine, and also N-aminoethylpiperazine and blends of N-aminoethylpiperazine with nonylphenol and/or benzyl alcohol, phenalkamines which are obtained in a Mannich reaction from cardanols, aldehydes and amines.

7 . The epoxy resin composition according to claim 1 , wherein di- and/or polyamines B2) selected from isophoronediamine, 4,4′-diaminodicyclohexylmethane, 2,4′-diaminodicyclohexylmethane, 2,2′-diaminodicyclohexylmethane, alone or in mixtures of the isomers, a mixture of the isomers of 2,2,4-trimethylhexamethylenediamine and 2,4,4-trimethylhexamethylenediamine, adduct hardeners based on the reaction products of epoxy compounds and di- and/or polyamines B2) or combination of the aforementioned di- and/or polyamines B2) are present.

8 . The epoxy resin composition according to claim 1 , wherein di- and/or polyamines B2) selected from
a) isophoronediamine (3,5,5-trimethyl-3-aminomethylcyclohexylamine, IPD), b) or a combination of
1. isophoronediamine and
2. a mixture of the isomers of 2,2,4-trimethylhexamethylenediamine and 2,4,4-trimethylhexamethylenediamine (TMD), alone or in mixtures of the isomers,
3. and/or a mixture of the isomers of 4,4′-diaminodicyclohexylmethane, 2,4′-diaminodicyclohexylmethane and 2,2′-diaminodicyclohexylmethane (also referred to as PACM), alone or in mixtures of the isomers,
c) or a combination of
1. a mixture of the isomers of 2,2,4-trimethylhexamethylenediamine and 2,4,4-trimethylhexamethylenediamine (TMD), alone or in mixtures of the isomers,
2. and/or a mixture of the isomers of 4,4′-diaminodicyclohexylmethane, 2,4′-diaminodicyclohexylmethane and 2,2′-diaminodicyclohexylmethane (also referred to as PACM), alone or in mixtures of the isomers,
d) and/or adduct hardeners based on the reaction products of epoxy compounds and the aforementioned amines B2) or combination of the aforementioned amines B2) are used.

9 . The epoxy resin composition according to claim 1 , wherein hardening accelerators C) present are imidazole and/or imidazole derivatives.

10 . The epoxy resin composition according to claim 1 , wherein latent hardeners D) selected from dicyandiamide, cyanoguanidines, aromatic amines, guanidines, modified polyamines, N-acylimidazoles, imidazoles, carbonyl hydrazides, triazine derivatives, melamine and derivatives thereof, N-cyanoacylamide compounds, acylthiopropylphenols are present.

11 . Use of the epoxy resin compositions according to claim 1 , comprising:
A) at least one epoxy compound and B) a hardener composition consisting of:
B1) 0.1%-100% by weight of 2-(3-(aminomethyl)-3,5,5-trimethylcyclohexyl)propane-1,3-diamine,
and
B2) 99.9%-0% by weight of at least one further diamine and/or polyamine,
where the stoichiometric ratio of the epoxy groups of A) and the number of hydrogen atoms of the functional groups of B) varies from 1:2 to 2:1, C) optionally 0.1% to 10% by weight of at least one hardening accelerator, D) optionally at least one latent hardener, where the amounts

Assignees

• Evonik Degussa Gmbh

Inventors

• Langkabel Eike
• Ortelt Martina
• Fuchsmann Dirk
• Balthasar Jaclyn
• Rüfer Alexander Martin
• Rittsteiger Anne
• Nitz Jörg-Joachim
• Kohlstruk Stephan

Classifications

• C08G59/063

  with epihalohydrins · CPC title

• C08G59/5026 Primary

  cycloaliphatic · CPC title

• C08L63/00

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title