Curing agent for low temperature cure applications

Patent metadata

Field	Value
Publication number	US-9334409-B2
Application number	US-201414265731-A
Country	US
Kind code	B2
Filing date	Apr 30, 2014
Priority date	Apr 9, 2008
Publication date	May 10, 2016
Grant date	May 10, 2016

Abstract

The present invention provides Mannich base derivatives of N,N′-dimethyl secondary diamine polymers including Mannich base derivatives of methylamine-terminated poly-(N-methylazetidine) and Mannich base derivatives of methylamine-terminated poly-(N-methylazacycloheptane). Amine curing agent compositions and amine-epoxy compositions containing Mannich base derivatives of N,N′-dimethyl secondary diamine polymers are also disclosed.

First claim

We claim:

1. A composition comprising a Mannich base reaction product of:
at least one aldehyde compound comprising formaldehyde;
at least one phenol compound comprising phenol, cresol, t-butyl phenol, nonyl phenol, cardanol, or a combination thereof; and
at least one N,N′-dimethyl secondary diamine polymer comprising methylamine-terminated poly-(N-methyl-azetidine), methylamine-terminated poly-(N-methyl-azacycloheptane), or a combination thereof.

2. An amine curing agent composition comprising:
(i) the composition of claim 1 ; and
(ii) at least one multifunctional amine having 3 or more active amine hydrogens.

3. A composition comprising a Mannich base reaction product comprising compounds having the formula:

wherein:
m is 1, 2, or 3;
R is a hydrogen atom or a C 1 -C 18 linear or branched alkyl or alkenyl group;
each R′ independently is a hydrogen atom or a moiety having the formula:

wherein:
R is defined as above;
t is 0, 1, or 2;
each R″ independently is a hydrogen atom or a moiety having the formula;

wherein:
R is defined as above;
u is 0, 1, or 2; and

each X independently is a moiety having the formula:

wherein:
R 1 is a C 2 -C 8 linear or branched alkanediyl; and
n is an integer in a range from 1 to 10, inclusive.

4. An amine curing agent composition comprising:
(i) the composition of claim 3 ; and
(ii) at least one multifunctional amine having 3 or more active amine hydrogens.

5. An amine-epoxy composition comprising:
(a) amine curing agent composition of claim 4 ; and
(b) an epoxy component comprising at least one multifunctional epoxy resin.

6. A method comprising curing the amine-epoxy composition of claim 5 .

7. A composition obtained by the method of claim 6 .

8. An article of manufacture comprising the composition of claim 7 .

9. The article of claim 8 , wherein the article is a coating, an adhesive, a construction product, a flooring product, or a composite product.

10. The composition of claim 3 , wherein R is a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a tert-butyl group, an octyl group, a nonyl group, a dodecyl group, a C 15 alkyl group, or a C 15 alkenyl group.

11. The composition of claim 3 , wherein each R′ is a hydrogen atom.

12. A composition comprising a Mannich base reaction product of
at least one di-substituted or tri-substituted Mannich base compound comprising bis-(dimethylaminomethyl)phenol, tris-(dimethylaminomethyl)phenol, or a combination thereof; and
at least one N,N′-dimethyl secondary diamine polymer comprising methylamine-terminated poly-(N-methyl-azetidine), methylamine-terminated poly-(N-methyl-azacycloheptane), or a combination thereof.

13. An amine curing agent composition comprising:
(i) the composition of claim 12 ; and
(ii) at least one multifunctional amine having 3 or more active amine hydrogens.

14. An amine-epoxy composition comprising:
(a) the amine curing agent composition of claim 13 ; and
(b) an epoxy component comprising at least one multifunctional epoxy resin.

15. A method comprising curing the amine-epoxy composition of claim 14 .

16. A composition obtained by the method of claim 15 .

17. An article of manufacture comprising the composition of claim 16 .

18. The article of claim 17 , wherein the article is a coating, an adhesive, a construction product, a flooring product, or a composite product.

Assignees

• Air Prod & Chem

Inventors

• Walker Frederick Herbert
• Cook Michael Ian
• Vedage Gamini Ananda
• Rasing Robert Marjo Theodoor

Classifications

• C08G59/504

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

• C07C215/50

  with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain · CPC title

• C08L63/00

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title

• C08G14/06

  and monomers containing hydrogen attached to nitrogen · CPC title

• C08G59/56

  together with other curing agents · CPC title