N,N′-diaminopropyl-2-methylcyclohexane-1,3-diamine and N,N′-diaminopropyl-4-methylcyclohexane-1,3-diamine and the use thereof as curing agents for epoxy resins

Patent metadata

Field	Value
Publication number	US-10889683-B2
Application number	US-201716463186-A
Country	US
Kind code	B2
Filing date	Dec 4, 2017
Priority date	Dec 5, 2016
Publication date	Jan 12, 2021
Grant date	Jan 12, 2021

Abstract

The present invention relates to the polyamines N,N′-diaminopropyl-2-methyl-cyclohexane-1,3-diamine and N,N′-diaminopropyl-4-methyl-cyclohexane-1,3-diamine and mixtures thereof, to the use thereof as curing agents for epoxy resin and to a curable composition comprising epoxy resin and these polyamines. Even at low temperatures this curing agent/the corresponding curable composition cures rapidly and is early-stage water resistant and is thus especially suitable for floor coatings. The invention further relates to the curing of this composition and the cured epoxy resin obtained by curing of this composition.

First claim

The invention claimed is:

1. A polyamine, selected from the group consisting of N,N′-diaminopropyl-2-methylcyclohexane-1,3-diamine and N,N′-diaminopropyl-4-methyl-cyclohexane-1,3-diamine.

2. A curing agent, comprising one or more polyamines of claim 1 .

3. A process for producing the polyamine of claim 1 or a mixture comprising the polyamine, the process comprising:
reacting 2-methyl-cyclohexane-1,3-diamine, 4-methyl-cyclohexane-1,3-diamine or a mixture of 2-methyl-cyclohexane-1,3-diamine and 4-methyl-cyclohexane-1,3-diamine with acrylonitrile to obtain a cyanoethylated intermediate, and
subjecting the cyanoethylated intermediate to catalytic hydrogenation with hydrogen to afford obtain N,N′-diaminopropyl-2-methyl-cyclohexane-1,3-diamine, N,N′-diaminopropyl-4-methyl-cyclohexane-1,3-diamine or a mixture of N′-diaminopropyl-2-methyl-cyclohexane-1,3-diamine and N,N′-diaminopropyl-4-methyl-cyclohexane-1,3-diamine.

4. The process of claim 3 , wherein the cyanoethylated intermediate is purified prior to the subjecting.

5. The process of claim 3 , further comprising purifying the N,N′-diaminopropyl-2-methylcyclohexane-1,3-diamine, the N,N′-diaminopropyl-4-methyl-cyclohexane-1,3-diamine or the mixture of N′-diaminopropyl-2-methyl-cyclohexane-1,3-diamine and N,N′-diaminopropyl-4-methyl-cyclohexane-1,3-diamine.

6. The process of claim 3 , wherein a Raney catalyst is used for the catalytic hydrogenation.

7. A curable composition, comprising
one or more epoxy resins and
one or more polyamines of claim 1 .

8. The curable composition of claim 7 , wherein the one or more epoxy resins are selected from the group consisting of diglycidyl ether of bisphenol A, diglycidyl ether of bisphenol F, diglycidyl ether of hydrogenated bisphenol A and diglycidyl ether of hydrogenated bisphenol F.

9. The curable composition of claim 7 , wherein said composition comprises one or more reactive diluents.

10. The curable composition of claim 7 , wherein in addition to the one or more polyamines, said composition also comprises one or more aminic curing agents.

11. The curable composition of claim 7 , wherein said composition also comprises one or more further additions.

12. A process for producing a cured epoxy resin, the process comprising providing and subsequently curing a curable composition of claim 7 .

13. The process of claim 12 , wherein the curing is carried out in the presence of atmospheric humidity.

14. A cured epoxy resin, obtainable by the process of claim 12 .

15. A cured epoxy resin, obtainable by curing the curable composition of claim 7 .

Assignees

• Basf Se

Inventors

• Gruenanger Christian
• Panchenko Alexander
• Gorman Irene
• Stegmann Veit
• Melder Johann-Peter
• Gutfrucht Norbert
• Ernst Martin
• Hofmann Marc

Classifications

• C08G59/5026 Primary

  cycloaliphatic · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C07C211/36 Primary

  containing at least two amino groups bound to the carbon skeleton · CPC title

• C07C209/84

  Purification · CPC title

• C07C209/26

  by reduction with hydrogen · CPC title