Use of oligo-N,N-bis(3-aminopropyl)methylamine as curing agent for epoxy resins

Patent metadata

Field	Value
Publication number	US-10544256-B2
Application number	US-201615741536-A
Country	US
Kind code	B2
Filing date	Jul 8, 2016
Priority date	Jul 13, 2015
Publication date	Jan 28, 2020
Grant date	Jan 28, 2020

Abstract

The present invention relates to the use of oligo-N,N-bis(3-aminopropyl)methylamine as hardener for epoxy resins, and also to a corresponding curable composition, curing thereof, and the cured epoxy resin obtainable therefrom.

First claim

The invention claimed is:

1. A curable composition, comprising:
a resin component comprising an epoxy resin; and
a hardener component comprising oligo-N,N-bis(3-aminopropyl)methylamine,
wherein the oligo-N,N-bis(3-aminopropyl)methylamine comprises at least 60 mol % of bis(3-aminopropyl)methylamine units, based on a total of amount of alkylenediamine structural elements.

2. The curable composition according to claim 1 , wherein the resin component further comprises a reactive diluent.

3. The curable composition according to claim 2 , wherein the reactive diluent is a low-molecular-weight organic compound having an epoxy group or is a cyclic carbonate having from 3 to 10 carbon atoms.

4. The curable composition according to claim 1 , wherein a number-average molar mass M of the oligo-N,N-bis(3-aminopropyl)methylamine is from 400 to 5000 g/mol.

5. The curable composition according to claim 1 , wherein a degree of branching DB HF of the oligo-N,N-bis(3-aminopropyl)methylamine is ≤0.3,
where DB HF =2D/(2D+L), and
where D is the content of tertiary amino groups excluding the methyl-substituted tertiary amino groups, and L is the content of secondary amino groups.

6. The curable composition according to claim 1 , wherein an amine number of the oligo-N,N-bis(3-aminopropyl)methylamine is from 10 to 1000 mg KOH/g for primary amines, from 50 to 1500 mg KOH/g for secondary amines, and from 50 to 1500 mg KOH/g for tertiary amines.

7. The curable composition according to claim 1 , wherein the oligo-N,N-bis(3-aminopropyl)methylamine is produced by catalytic polytransamination of N,N-bis(3-aminopropyl)methylamine.

8. The curable composition according to claim 1 , wherein the oligo-N,N-bis(3-aminopropyl)methylamine is composed solely of N,N-bis(3-aminopropyl)methylamine structural elements, where the N,N-bis(3-aminopropyl)methylamine-internal, N-bonded methyl group can, for a proportion of at most 10% of these groups, have been removed or transferred to other secondary or primary amine groups of the polymer.

9. The curable composition according to claim 1 , wherein the epoxy resins and any reactive diluents of the curable composition on the one hand, and a total amount of aminic hardeners, which are amines with NH-functionality ≥2, of the curable composition on the other hand are used in an approximately stoichiometric ratio, based on the reactive groups of the epoxy resins and on any reactive diluents and, respectively, the NH-functionality of the aminic hardeners.

10. The curable composition according to claim 1 , wherein the epoxy resin is 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.

11. A process for the production of cured epoxy resins, comprising curing a curable composition according to claim 1 .

12. A cured epoxy resin, obtained by the process according to claim 11 .

13. A molding, comprising a cured epoxy resin according to claim 12 .

14. A composite material, comprising a cured epoxy resin according to claim 12 and a reinforcement fiber.

15. A coating, comprising a cured epoxy resin according to claim 12 .

16. A cured epoxy resin, obtained by curing a curable composition according to claim 1 .

17. The curable composition according to claim 1 , wherein the oligo-N,N-bis(3-aminopropyl)methylamine comprises at least 70 mol % of the bis(3-aminopropyl)methylamine units, based on the total of amount of alkylenediamine structural elements.

Assignees

• Basf Se

Inventors

• Panchenko Alexander
• Charrak Monika
• Altenhoff Ansgar Gereon
• Reissner Thomas
• Krausche Christian

Classifications

• C08G59/245

  aromatic · CPC title

• C08G59/5013 Primary

  containing more than seven carbon atoms, e.g. fatty amines · CPC title

• C08K7/02

  Fibres or whiskers · CPC title

• C09D163/00

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

• C08G59/5006

  aliphatic · CPC title