Curing agent for low temperature cure applications
View Patent ↗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.
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.