IP Library Granted Patent US 10,280,252
Granted Patent B2
US 10,280,252 · App. 15/375,792 · Granted May 7, 2019

Latent epoxy resin formulations for liquid impregnation processes for production of fibre composite materials

Inventors: Martina Ortelt (Flein, DE); Dirk Fuchsmann (Haltern am See, DE); Eike Langkabel (Wegberg, DE); Britta Kohlstruk (Gladbeck, DE); Jaclyn Balthasar (Glinde, DE)
Assignee: Evonik Degussa GmbH
C08G59/506C08G59/226C08G59/504C08G59/5026C08G59/56C08J5/04C08J5/24C08J2363/00C08J2363/02F03D1/0675F05B2280/6003F05B2280/6015Y02E10/721
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Quick Facts
Patent No.
US 10,280,252
App. No.
15/375,792
Granted
May 7, 2019
Kind
B2
Abstract

Latent epoxy resin formulations are suitable for liquid impregnation processes for production of fiber composite materials.

Claims (85)

1. A composition, comprising:

an epoxy resin composition; and

optionally a further additive, wherein

said epoxy resin composition comprises:

A) at least one epoxy compound,

B) a hardener composition comprising:

B1) 5%-45% by weight of at least one polyamine based on triacetonediamine

and

B2) 55%-95% by weight of at least one further diamine and/or polyamine,

wherein the stoichiometric ratio of the epoxy groups of A) and the number of active hydrogen atoms of the functional groups of B) varies from 1:0.5 to 1:1.1,

and

C) optionally, at least one hardening accelerator,

wherein the amounts of A)-C) add up to 100% by weight of said epoxy resin composition.

2. The composition according to claim 1 , wherein epoxy compound A) is at least one member selected from the group consisting of

a saturated epoxy compound, an unsaturated epoxy compound, an aliphatic epoxy compound, a cycloaliphatic epoxy compound, an aromatic epoxy compound, and a heterocyclic epoxy compound,

wherein the epoxy compound optionally has a hydroxyl group.

3. The composition according to claim 1 , wherein

epoxy compound A) is at least one member selected from the group consisting of a glycidyl ether, a glycidyl ester, an aliphatic epoxide, a diglycidyl ether based on at least one of bisphenol A and bisphenol F, and a glycidyl methacrylate.

4. The composition according to claim 1 , wherein

the epoxy compound A) is at least one member selected from the group consisting of

an epoxy resin based on bisphenol A diglycidyl ether; an epoxy resin 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; an aliphatic epoxy resin; and a cycloaliphatic epoxy resin.

5. The composition according to claim 1 , wherein

component B1) is at least one member selected from the group consisting of 2,2,6,6-tetramethyl-4-aminopiperidine (TAD),

hexamethylenebis(4-amino-2,2,6,6-tetramethylpiperidine),

N-butyl-4-amino-2,2,6,6-tetramethylpiperidine,

N,N-dimethylaminopropyl-4-amino-2,2,6,6-tetramethylpiperidine,

N-propyl-4-amino-2,2,6,6-tetramethylpiperidine,

N-isopropyl-4-amino-2,2,6,6-tetramethylpiperidine,

N-hydroxyethyl-4-amino-2,2,6,6-tetramethylpiperidine,

N-methoxyethyl-4-amino-2,2,6,6-tetramethylpiperidine,

N-methoxyethyl-4-amino-2,2,6,6-tetramethylpiperidine,

N′,N′-dimethylaminoethyl-4-amino-2,2,6,6-tetramethylpiperidine,

N-morpholinoethyl-4-amino-2,2,6,6-tetramethylpiperidine,

N-piperazinoethyl-4-amino-2,2,6,6-tetramethylpiperidine, and

4-morpholino-2,2,6,6-tetramethylpiperidine.

6. The composition according to claim 1 , wherein

component B2) comprises at least one member selected from the group consisting of a primary diamine, a secondary diamine, a primary polyamine, and a secondary polyamine.

7. The composition according to claim 1 , wherein component B2) comprises at least one of:

a) an aliphatic amine;

b) at least one oxyalkylenepolyamine selected from the group consisting of polyoxypropylenediamine and polyoxypropylenetriamine, 1,13-diamino-4,7,10-trioxatridecane, and 4,7-dioxadecane-1,10-diamine;

c) at least one cycloaliphatic amine selected from the group consisting of 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), and 4-methylcyclohexane-1,3-diamine;

d) an araliphatic amine;

e) at least one aromatic amine selected from the group consisting of phenylenediamines, phenylene-1,3-diamine, phenylene-1,4-diamine, 4,4′-diaminodiphenylmethane, 2,4′-diaminodiphenylmethane, and 2,2′-diaminodiphenylmethane, alone or in mixtures of the isomers;

f) an adduct hardener which is the reaction product of an epoxy compound with excess amine;

g) a polyamidoamine hardener which is obtained by condensation of a mono- and/or polycarboxylic acid with a polyamine;

h) a Mannich base hardener which is obtained by reaction of a mono- and/or polyhydric phenol with an aldehyde and a polyamine;

i) a Mannich base.

8. The composition according to claim 7 , wherein said Mannich base is based on phenol and/or resorcinol, formaldehyde and m-xylylenediamine, 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.

9. The composition according to claim 1 , wherein

component B2) comprises at least one member selected from the group consisting of isophoronediamine;

4,4′-diaminodicyclohexylmethane;

2,4′-diaminodicyclohexylmethane;

2,2′-diaminodicyclohexylmethane;

a mixture of at least two of isophoronediamine, 4,4′-diaminodicyclohexylmethane, 2,4′-diaminodicyclohexylmethane, and 2,2′-diaminodicyclohexylmethane;

polyoxypropylenediamine;

polyoxypropylenetriamine;

a mixture of poly oxypropylenediamine and polyoxypropylenetriamine;

at least one adduct based on a reaction product of an epoxy compound and at least one member selected from the group consisting of isophoronediamine; 4,4′-diaminodicyclohexylmethane; 2,4′-diaminodicyclohexylmethane; 2,2′-diaminodicyclohexylmethane; a mixture of at least two of isophoronediamine, 4,4′-diaminodicyclohexylmethane, 2,4′-diaminodicyclohexylmethane, and 2,2′-diaminodicyclohexylmethane; polyoxypropylenediamine; polyoxypropylenetriamine; and a mixture of polyoxypropylenediamine and polyoxypropylenetriamine.

10. The composition according to claim 1 , wherein

component B2) comprises at least one member selected from the group consisting of isophoronediamine,

a mixture of at least two members selected from the group consisting of isophoronediamine, 2,2′-diaminodicyclohexylmethane, polyoxypropylenediamine, and polyoxypropylenetriamine, and

a hardener based on a reaction product of an epoxy compound and isophoronediamine or a mixture of at least two members selected from the group consisting of isophoronediamine, 2,2′-diaminodicyclohexylmethane, polyoxypropylenediamine, and polyoxypropylenetriamine.

11. The composition according to claim 1 , wherein

component B2) comprises at least one member selected from the group consisting of

a) isophoronediamine,

b) a combination of isophoronediamine and at least one of polyoxypropylenediamine and polyoxypropylenetriamine, and

c) an adduct hardener based on a reaction product of an epoxy compound and isophoronediamine or a combination of isophoronediamine and at least one of polyoxypropylenediamine and polyoxypropylenetriamine.

12. The composition according to claim 1 , wherein component B2) comprises a mixture of 3-aminomethyl-3,5,5-trimethylcyclohexylamine and polyoxypropylenediamine.

13. The composition according to claim 1 , wherein component B) is a mixture of:

B1) 35%-45% by weight of triacetonediamine; and

B2) 55%-65% by weight of a mixture of 3-aminomethyl-3,5,5-trimethylcyclohexylamine and polyoxypropylenediamine.

14. The composition according to claim 1 , wherein hardening accelerator C) is present and comprises a tertiary amine.

15. A composite, obtained from the composition according to claim 1 .

16. A composite, obtained from

1) at least one fibrous carrier and optionally a core material

and

2) a composition according to claim 1 .

17. A process for producing a composite according to claim 16 , said process comprising:

I providing a said epoxy resin composition which is a reactive composition;

II impregnating a structure comprising the fibrous carrier and optionally a further core material with the composition from I in a form or in a mould by a liquid resin impregnation method or impregnating said fibrous carrier and a gap on a mandrel;

III hardening the reactive composition to give a composite component; and

IV demoulding the composite component from the form or mould.

18. An article, comprising the composite according to claim 16 .

19. The article according to claim 18 , which is an article in boat- and shipbuilding, in aerospace technology, in automobile construction, for two-wheeled vehicles, in the automotive, construction, medical technology and sports sectors, the electrical and electronics industry, and in energy generation installations.

20. The article according to claim 18 , which is a rotor blade of a wind turbine.

Assignments (2)
CHANGE OF NAME Recorded Nov 18, 2019
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051045/0872 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 2, 2017
From: ORTELT, MARTINA; FUCHSMANN, DIRK; LANGKABEL, EIKE; KOHLSTRUK, BRITTA; BALTHASAR, JACLYN
To: EVONIK DEGUSSA GMBH
Reel/Frame 041431/0297 →
Priority Claims (1)
EP 15199599 · Dec 11, 2015 · regional
Continuity (1)
Related Publication 20180162991A1 · Jun 14, 2018