Amine for low-emission epoxy resin compositions

Patent metadata

Field	Value
Publication number	US-10662280-B2
Application number	US-201615746529-A
Country	US
Kind code	B2
Filing date	Aug 4, 2016
Priority date	Aug 7, 2015
Publication date	May 26, 2020
Grant date	May 26, 2020

Abstract

An amine of formula (I) in a curing agent for epoxy resins, a curing agent for epoxy resins containing the amine of formula (I) and resultant epoxy resin compositions which can be used particularly as low-emission room-temperature-curing epoxy resin coatings demonstrating good workability, rapid curing, a high degree of hardness and high surface quality. The amine of formula (I) is low-odour, can be handled well at room temperature even without dilution, and can be produced at high purity in a simple process.

First claim

The invention claimed is:

1. A method comprising hardening epoxy resins with an amine of formula (I),

where:
m is 0 to 3,
X is 1,2-propylene, and
Y is a monocyclic or polycyclic aromatic hydrocarbon radical.

2. The method as claimed in claim 1 , wherein the hardener is a nonaqueous hardener.

3. The method as claimed in claim 1 , wherein Y is an aromatic hydrocarbon radical selected from the group consisting of

where R is a hydrogen radical or methyl radical.

4. The method as claimed in claim 1 , wherein m is 0 to 1, Y is a radical of the formula

where R is a hydrogen radical or methyl radical.

5. An amine of formula (I),

where:
m is 0 to 1,
X is 1,2-propylene,
Y is a radical of formula

and
R is a hydrogen radical or methyl radical.

6. An amine of formula (I),

where:
m is 0 to 3,
X is 1,2-propylene, and
Y is a monocyclic or polycyclic aromatic hydrocarbon radical.

7. A reaction product produced from a reaction of at least 1,2-propylenediamine with at least one diglycidyl ether of formula (II):

the reaction product comprising the amine of formula (I) as claimed in claim 6 in a hardener for epoxy resins.

8. The product as claimed in claim 7 , wherein the ratio between the number of primary amino groups and the number of epoxide groups is at least 2.5:1 and excess diamine is removed by distillation after the reaction.

9. The product as claimed in claim 7 , wherein the reaction product contains less than 1 weight % of 1,2-propylenediamine.

10. A hardener for epoxy resins, comprising the amine of formula (I) as claimed in claim 6 and at least one further amine and/or at least one accelerator.

11. The hardener as claimed in claim 10 , wherein the further amine comprises N-benzyl-1,2-propanediamine.

12. The hardener as claimed in claim 10 , wherein 1 to 80 weight % of the amine of formula (I) is present.

13. An epoxy resin composition comprising
a resin component comprising at least one epoxy resin, and
a hardener component comprising the amine of formula (I) as claimed in claim 6 .

14. A coating comprising the epoxy resin composition as claimed in claim 13 .

15. A cured composition obtained by curing the epoxy resin composition as claimed in claim 13 .

Assignees

• Sika Tech Ag

Inventors

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

Classifications

• C07C217/34

  by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms · CPC title

• C07C217/32

  the six-membered aromatic ring or condensed ring system containing that ring being further substituted · CPC title

• C08G59/56

  together with other curing agents · CPC title

• C09D163/00

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

• C08G59/504 Primary

  containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen · CPC title