Amine for low-emission epoxy resin compositions

Patent metadata

Field	Value
Publication number	US-10287388-B2
Application number	US-201515501955-A
Country	US
Kind code	B2
Filing date	Aug 7, 2015
Priority date	Aug 13, 2014
Publication date	May 14, 2019
Grant date	May 14, 2019

Abstract

An amine of the formula (I) and a process for its preparation by reductive alkylation of 1,2-propylenediamine with a di- or trifunctional carbonyl compound and hydrogen. The amine of the formula (I) is low in viscosity and in odour, high in reactivity towards epoxides and outstanding in its compatibility with other amines and with epoxy resins. The amine of the formula (I) allows access to low-emission epoxy resin compositions which have good processing qualities, cure rapidly even at low temperatures and form high-quality, high-hardness plastics having an attractive surface.

First claim

The invention claimed is:

1. An amine of formula (I)

wherein
n is 2 or 3,
R is a hydrogen radical or is methyl or phenyl, and
A is a radical selected from the group consisting of:

 wherein
m is 0, 1, or 2,
X is a radical independently selected from the group consisting of alkyl and alkoxy having 1 to 4 carbon atoms, and
Z is an oxygen atom or a sulfur atom.

2. The amine of the formula (I) as claimed in claim 1 , wherein n is 2.

3. The amine of the formula (I) as claimed in claim 1 , wherein R is a hydrogen radical.

4. A process for preparing an amine of the formula (I) as claimed in claim 1 comprising subjecting 1,2-propylenediamine to reductive alkylation with at least one di- or trifunctional carbonyl compound of the formula (III) and hydrogen

5. The process as claimed in claim 4 , wherein 1,2-propylenediamine is used in stoichiometric excess over the carbonyl groups of the carbonyl compound of the formula (III).

6. A method comprising hardening epoxy resins with an amine of the formula (I) as claimed in claim 1 .

7. A hardener for epoxy resins comprising:
at least one amine of the formula (I) as claimed in claim 1 , and
at least one further amine and/or at least one accelerator.

8. The hardener as claimed in claim 7 , wherein the accelerator is salicylic acid or 2,4,6-tris(dimethylaminomethyl)phenol or a combination thereof.

9. The hardener as claimed in claim 7 , wherein the further amine comprises 1-(2-aminopropylaminomethyl)-4-(1-aminoprop-2-ylaminomethyl)benzene or 1,4-bis(1-aminoprop-2-ylaminomethyl)benzene or 1-(2-aminopropylaminomethyl)-4-(1-aminoprop-2-ylaminomethyl)cyclohexane or 1,4-bis(1-aminoprop-2-ylaminomethyl)cyclohexane.

10. The hardener as claimed in claim 7 , wherein the further amine comprises a partially styrenized polyamine or a product of the reductive alkylation of primary aliphatic polyamines with monofunctional aldehydes or ketones.

11. The hardener as claimed in claim 7 , wherein the hardener contains not more than 10 weight % of unincorporable diluents.

12. An epoxy resin composition comprising:
a resin component comprising at least one epoxy resin, and
a hardener component comprising at least one amine of the formula (I) as claimed in claim 1 .

13. A method comprising applying an epoxy resin composition as claimed in claim 12 as a fiber composite matrix for fiber composite materials, an adhesive, a coating, a covering, or a finish.

14. An amine that
is 1,4-bis(2-aminopropylaminomethyl)benzene or 1,4-bis(2-aminopropylaminomethyl)cyclohexane.

15. A method comprising hardening epoxy resins with an amine as claimed in claim 14 .

16. A hardener for epoxy resins comprising at least one amine as claimed in claim 14 , and
at least one further amine and/or at least one accelerator.

17. An epoxy resin composition comprising:
a resin component comprising at least one epoxy resin, and
a hardener component comprising at least one amine as claimed in claim 14 .

18. A method comprising applying an epoxy resin composition as claimed in claim 17 as a fiber composite matrix for fiber composite materials, an adhesive, a coating, a covering, or a finish.

Assignees

• Sika Tech Ag
• Sika Tech Agh

Inventors

• Kasemi Edis
• Kramer Andreas
• Stadelmann Ursula
• Burckhardt Urs

Classifications

• C08G59/5026

  cycloaliphatic · CPC title

• C08G59/223

  together with monoepoxy compounds · CPC title

• C07C211/27

  having amino groups linked to the six-membered aromatic ring by saturated carbon chains · CPC title

• C07C209/22

  by substitution of other functional groups · CPC title

• C07C2602/14

  All rings being cycloaliphatic · CPC title