Fast-curing epoxy systems

Patent metadata

Field	Value
Publication number	US-11370877-B2
Application number	US-201916409907-A
Country	US
Kind code	B2
Filing date	May 13, 2019
Priority date	May 17, 2018
Publication date	Jun 28, 2022
Grant date	Jun 28, 2022

Abstract

The present invention relates to a composition comprising a) at least one epoxy resin, b) at least one amine having at least two secondary amino groups which are both part of an organic ring system, and c) at least one salt of a very strong Brønsted acid with a counterion selected from metal ions, metal-containing ions, phosphonium ions and ammonium ions, and to processes for production thereof and use thereof.

First claim

The invention claimed is:

1. A composition comprising:
a) an epoxy resin,
b) a cyclic amine having at least two secondary cyclic amino groups belonging to the same cycle of the cyclic amine,
c) a salt of a Brønsted acid,
d) a diamine or polyamine, which is not a cyclic amine having at least two secondary cyclic amino groups belonging to the same cycle of the cyclic amine, and
e) optional auxiliaries and/or additives;
wherein a) is present in an amount of from 30 to 95 wt %, based on the total weight of the composition;
wherein b) is present in an amount of from 1 to 50 wt %, based on the total weight of the composition;
wherein c) is present in an amount of from 0.001 to 5 wt %, based on the total weight of the composition, the Brønsted acid of the salt has a pKa of between −9.01 and -25, and the counterion of the salt is selected from a metal ion, a metal-containing ion, a phosphonium ion, and an ammonium ion;
wherein d) is present in an amount such that b) accounts for at least 70 wt % of the combined weight of b) and d) in the composition; and
wherein e) are optionally present in an amount of up to 48 wt %, based on the total weight of the composition.

2. The composition according to claim 1 , wherein
the epoxy resin a) is selected from the group consisting of bisphenol A diglycidyl ether, 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 and diglycidyl hexahydrophthalate.

3. The composition according to claim 1 , wherein the amine b) has the formula (I)

in which
R 1 to R 4 is H or an organic radical, and
wherein at least one of the R 1 , R 2 , R 3 , and R 4 radicals=H, and
X=—(Y 1 ) m -(A 1 ) n -(Y 2 ) o -(A 2 ) p -(Y 3 ) q -(A 3 ) r -(Y 4 ) s —  (II)

where, independently of one another,
m, n, o, p, q, r and s=0 or 1, provided that at least one of m, o, q, and s=1,
A 1 , A 2 , A 3 =alkylene or alkenylene radical and
Y 1 , Y 2 , Y 3 , Y 4 =NR 5 , PR 5 , O or S, where R 5 independently=organic radical,
wherein at least one of the radicals selected from Y 1 , Y 2 , Y 3 , Y 4 present is NR 5 where R 5 =H.

4. The composition according to claim 1 , wherein the amine b) is selected from the group consisting of 1H-octahydroimidazo[4,5-c]pyridine, 1,4,8-triazaspiro[4.5]decane, 1,4-diazaspiro[4.5]decane, pyrazolidine, 2,2-dimethylimidazolidine, 1,4,7-triazacyclononane, hexahydropyridazine, tetradecahydrophenazine, decahydroquinoxaline, octahydro-1H-cyclopentapyrazine, piperazine, 2-methylpiperazine, 2,2-dimethylpiperazine, 2,3-dimethylpiperazine, 2-ethylpiperazine, 2,5-dimethylpiperazine, 2,6-dimethylpiperazine, 2,3,5,6-tetramethylpiperazine, 2,3,5-trimethylpiperazine, 2-(2-piperidinyl)piperazine, homopiperazine, 2-methylhomopiperazine, and 6-methyl-1,4-diazepane.

5. The composition according to claim 1 , wherein
the counterion of the salt of the Brønsted acid c) is selected from an alkaline earth metal ion, lithium ion, aluminium ion, bismuth ion, zinc ion, europium ion, tetraphenylstibonium ion, phosphonium ion, or ammonium ion.

6. The composition according to claim 1 , wherein the Brønsted acid of the salt of a Brønsted acid c) is selected from perchloric acid, trifluoromethanesulfonic acid, hydrogen iodide, hexafluorophosphoric acid, and hexafluoroantimonic acid.

7. The composition according to claim 1 , wherein the diamine or the polyamine d) is selected from the group consisting of aliphatic diamines or polyamines, oxyalkylenepolyamines, cycloaliphatic diamines or polyamines, diamines or polyamines having a cyclic amino group and at least one acyclic primary or secondary amino group, araliphatic diamines or polyamines, aromatic diamines or polyamines, adduct hardeners of diamines or polyamines, polyamidoamine hardeners, Mannich base hardeners of diamines or polyamines, and Mannich bases of diamines or polyamines.

8. The composition according to claim 1 , wherein
optional auxiliaries and/or additives e) are present in an amount of up to 48 wt %, based on the total weight of the composition.

9. A process for producing a composition according to claim 1 , wherein a), b), c), d) and optionally e) are mixed with one another.

10. A composite comprising the composition according to claim 1 .

11. A casting resin comprising the composition according to claim 1 .

12. A coating composition comprising the composition according to claim 1 .

13. An adhesive comprising the composition according to claim 1 .

Assignees

• Evonik Operations Gmbh

Inventors

• Spyrou Emmanouil
• Kreischer Susanne
• Diesveld Andrea
• Loesch Holger

Classifications

• C08G59/682

  Alcoholates · CPC title

• C08G59/68

  characterised by the catalysts used · CPC title

• C08G59/245

  aromatic · CPC title

• C08G59/5046 Primary

  heterocyclic · CPC title

• C08G59/5073 Primary

  having two nitrogen atoms in the ring · CPC title