Curing agent of N,N′-dimethyl-meta-xylylenediamine and multifunctional amin(s)
View Patent ↗The present invention discloses both amine compositions and amine-epoxy compositions containing N,N′-dimethyl-meta-xylylenediamine. A novel process for producing amines such as N,N′-dimethyl-meta-xylylenediamine, and structurally similar amines, is also disclosed.
1. An amine curing agent composition for epoxy containing compositions comprising:
(i) N,N′-dimethyl-meta-xylylenediamine (DM-MXDA);
(ii) at least one multifunctional amine comprising at least one member selected from the group consisting of N-monomethyl-meta-xylylenediamine (MM-MXDA), phenalkamine; 1,3-bis(aminomethyl)cyclohexane; a mixture of methylene bridged poly(cyclohexyl-aromatic)amines (MPCA); and any combination thereof;
wherein the ratio of DM-MXDA to the at least one multifunctional amine ranges from about 95:5 to about 5:95; and
(iii) at least one plasticizer or solvent.
2. The amine curing agent composition of claim 1 , wherein the at least one plasticizer or solvent comprises benzyl alcohol, n-butanol, xylene, methyl ethyl ketone, nonyl phenol, dodecyl phenol, cardanol, an ester of phthalic acid, or any combination thereof.
3. The amine curing agent composition of claim 1 , wherein the weight ratio of DM-MXDA to the at least one multifunctional amine is in a range from about 55:45 to about 90:10.
4. The amine curing agent composition of claim 1 , wherein the at least one multifunctional amine comprises N-monomethyl-meta-xylylenediamine (MM-MXDA).
5. An amine-epoxy composition comprising:
(a) the amine curing agent composition of claim 1 ; and
(b) an epoxy component comprising at least one multifunctional epoxy resin.
6. The amine-epoxy composition of claim 5 , wherein a stoichiometric ratio of epoxy groups in the epoxy component to amine hydrogens in the amine composition ranges from about 2:1 to about 1:1.2.
7. A process comprising curing the amine-epoxy composition of claim 5 .
8. An article of manufacture obtained by the process of claim 7 .
9. The article of manufacture of claim 8 which is a coating, construction product, flooring product or a composite product.
10. The curing agent composition of claim 5 wherein the composition cures the epoxy containing compositions at a temperature of less than about 25C.
11. The composition of claim 5 wherein the at least one multifunctional epoxy resin comprises DGEBA.
12. The composition of claim l wherein the DM-MXDA comprises a mixture of amines and the mixture of amines is produced by a process comprising:
(a) contacting 1,3-dicyanobenzene with mono-methylamine in the presence of hydrogen and a catalyst at a hydrogen pressure of about 100 to about 500 psi to form at least one intermediate product; and,
(b) contacting the at least one intermediate product with hydrogen in the presence of a hydrogenation catalyst at a hydrogen pressure of about 400 to about 1500 psi to form the mixture of amines comprising DM-MXDA.
13. The composition of claim 1 wherein the composition comprises DM-MXDA, MM-MXDA and at least one other multifunctional amine.
14. The composition of claim 13 wherein the at least one other multifunctional amine comprises MPCA.
15. The composition of claim 1 wherein the composition comprises DM-MXDA, MM-MXDA and at least one phenalkamine.
16. The composition of claim 1 wherein the composition comprises DM-MXDA, MM-MXDA and meta-xylylene diamine (MXDA).
17. The composition of claim 1 wherein composition comprises DM-MXDA, MM-MXDA and 1,3-bis(aminomethyl)cyclohexane.
18. The composition of claim 1 wherein the composition comprises DM-MXDA, MM-MXDA and a mixture of methylene bridged poly(cyclohexyl-aromatic) amines(MPCA).