Epoxy resin amine curing agent of N,N′-dimethyl secondary diamine polymer
View Patent ↗The present invention provides N,N′-dimethyl secondary diamine polymers including methylamine-terminated poly-(N-methylazetidine) and methylamine-terminated poly-(N-methylazacycloheptane). Amine compositions and amine-epoxy compositions comprising N,N′-dimethyl secondary diamine polymers are also disclosed.
1. An amine-epoxy composition comprising the contact product of:
(a) an amine curing agent component comprising:
(i) 90% to 10% by weight, based on total amine curing agent component, of at least one N,N′-dimethyl secondary diamine polymer comprising a mixture of different size molecules having different numbers of repeating units, such polymer having the formula:
wherein X is a moiety having the formula:
wherein:
R 1 is a C 2 -C 8 linear or branched alkanediyl;
the at least one N,N′-dimethyl secondary diamine polymer has a number-average molecular weight (M n ) from about 140 to about 1000;
n comprises integers in the range from 1 to 50, the average of which is determined as a function of M n ; and
(ii) 10% to 90% by weight, based on total amine curing agent component, of at least one multifunctional amine having 3 or more active amine hydrogens; and
(b) an epoxy component comprising at least one multifunctional epoxy resin.
2. The composition of claim 1 , wherein R 1 is a C 3 -C 6 linear or branched alkanediyl.
3. The composition of claim 1 , wherein the at least one N,N′-dimethyl secondary diamine polymer has a M n from about 160 to about 500.
4. The composition of claim 1 , wherein the at least one N,N′-dimethyl secondary diamine polymer has a M n from about 180 to about 300.
5. The composition of claim 1 , wherein the at least one N,N′-dimethyl secondary diamine polymer is of formula A or B
or a combination thereof.
6. The composition of claim 1 , wherein the at least one N,N′-dimethyl secondary diamine polymer is of formula A
7. The composition of claim 1 , wherein the at least one N,N′-dimethyl secondary diamine polymer comprises a derivative thereof which is a polyamide derivative, an amidoamine derivative, an amine-epoxy adduct derivative, or any combination thereof.
8. The composition of claim 1 , wherein the at least one multifunctional amine has 6 or more carbon atoms.
9. The composition of claim 1 , wherein the at least one multifunctional amine is an aliphatic amine, a cycloaliphatic amine, an aromatic amine, a Mannich base derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine, a polyamide derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine, an amidoamine derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine, an amine adduct derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine, or any combination thereof.
10. The composition of claim 1 , wherein the at least one multifunctional amine is a mixture of methylene bridged poly(cyclohexyl-aromatic)amines.
11. The composition of claim 1 , wherein the total amine curing agent component comprises about 80% to about 20% by weight of at least one N,N′-dimethyl secondary diamine polymer.
12. The composition of claim 1 , wherein the stoichiometric ratio of epoxy groups in the epoxy component to amine hydrogens in the amine component ranges from about 1.5:1 to about 1:1.5.
13. The composition of claim 1 , wherein the stoichiometric ratio of epoxy groups in the epoxy component to amine hydrogens in the amine component ranges from about 1.3:1 to about 1:1.3.
14. The composition of claim 6 , wherein the total amine curing agent component comprises about 80% to about 20% by weight of the N,N′-dimethyl secondary diamine polymer.
15. The composition of claim 6 , wherein the at least one multifunctional amine has 6 or more carbon atoms.
16. The composition of claim 6 , wherein the at least one multifunctional amine is an aliphatic amine, a cycloaliphatic amine, an aromatic amine, a Mannich base derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine, a polyamide derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine, an amidoamine derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine, an amine adduct derivative of an aliphatic amine, a cycloaliphatic amine, or an aromatic amine, or any combination thereof.
17. The composition of claim 6 , wherein the at least one multifunctional amine is a mixture of methylene bridged poly(cyclohexyl-aromatic)amines.