Epoxy systems and amine polymer systems and methods for making the same
View Patent ↗Compositions and methods for forming surfactants, aqueous dispersions, and curing agents are provided. In one aspect, the invention relates to improved epoxy functional surfactants prepared by reaction of an epoxy composition and an amidoamine composition formed from a blend of acid-terminated polyoxyalkylene polyols. The improved epoxy functional surfactants may be reacted with an excess of epoxy composition and water to result in an aqueous dispersion. The amidoamone composition may be a reaction mixture of a diamine compound and an acid terminated polyoxyalkylene composition formed from two or more polyoxyalkylene polyol compounds. The epoxy functional surfactant may be reacted with amine compounds to form a compound suitable as a curing agent.
1. An amidoamine composition, comprising a reactant product of:
an acid terminated polyoxyalkylene composition of two or more acid terminated polyoxyalkylene polyol compounds, wherein the acid terminated polyoxyalkylene composition having a polydispersity of 1.1 or greater and the two or more acid terminated polyoxyalkylene polyol compounds have from about 50% to about 100% of carboxylic end groups oxidized from hydroxyl end groups; and
a diamine compound comprising a first amine substituent group of a primary amine substituent group and a second amine substituent group of a primary amine substituent group or a secondary amine substituent group, wherein the reaction product comprises an amidoamine compound having the formula of:
wherein each of R 1 and R 2 comprises a hydrogen atom or a substituent group selected from the group consisting of a branched or linear aliphatic, a cycloaliphatic, an aromatic substituent group and combinations thereof, having 1 to 21 carbon atoms, with at least one of R 1 and R 2 comprising a hydrogen atom, R 3 is a divalent hydrocarbon substituent group selected from the group consisting of a branched or linear aliphatic, a cycloaliphatic, an aromatic substituent group, and combinations thereof, having 2 to 18 carbon atoms, n is an average number from about 18 to about 500, X is a hydrogen atom or a substituent group selected from the group consisting of a methyl substituent, an ethyl substituent, a hydroxymethyl substituent group, and combinations thereof, and Y is a hydrogen atom or a substituent group selected from the group consisting of a methyl substituent, an ethyl substituent, a hydroxymethyl substituent group, and combinations thereof.
2. The composition of claim 1 , wherein the amidoamine compound comprises an amine value from about 8 to about 30.
3. The composition of claim 1 , wherein the diamine compound comprises two primary amine substituent groups with the diamine having the formula:
H 2 N—R 3 —NH 2 ,
wherein R 3 is a divalent hydrocarbon substituent group selected from the group consisting of a branched or linear aliphatic, a cycloaliphatic, an aromatic substituent group, and combinations thereof, having 2 to 18 carbon atoms.
4. The composition of claim 3 , wherein the diamine compound is provided at a stoichiometric excess of amine substituent groups to carboxylic end groups of the acid terminated polyoxyalkylene composition.
5. The composition of claim 3 , wherein the reactant product further comprises a monoepoxy compound.
6. The composition of claim 1 , wherein the diamine compound comprises a primary amine substituent group and a secondary amine substituent group with the diamine having the formula:
R 1 —HN—R 3 —NH 2 ,
wherein R 1 is a branched or linear aliphatic, a cycloaliphatic, or an aromatic divalent substituent group having 1 to 21 carbon atoms and R 3 is a divalent hydrocarbon substituent group selected from the group consisting of a branched or linear aliphatic, a cycloaliphatic, an aromatic substituent group, and combinations thereof, having 2 to 18 carbon atoms.
7. The composition of claim 6 , wherein the R 1 substituent group further comprises an end group selected from the group consisting of a methyl group, a hydroxyl group, and combinations thereof, and the R 3 substituent group further comprises an end group selected from the group consisting of a methyl group, a hydroxyl group, and combinations thereof.
8. The composition of claim 7 , wherein the R 1 substituent group, the R 3 substituent group, or both, further comprises one or more non-reactive oxygen or nitrogen atoms in the backbone of the substituent group.
9. The composition of claim 1 , wherein each of the two or more polyoxyalkylene polyol compounds are reacted with the diamine compound separately and then combined to form the amidoamine composition.
10. A method for forming an amidoamine composition, comprising:
providing an acid terminated polyoxyalkylene composition of two or more acid terminated polyoxyalkylene polyol compounds, wherein the acid terminated polyoxyalkylene composition having a polydispersity of 1.1 or greater and the two or more acid terminated polyoxyalkylene polyol compounds have from about 50% to about 100% of carboxylic end groups oxidized from hydroxyl end groups;
providing a diamine compound comprising a first amine substituent group of a primary amine substituent group and a second amine substituent group of a primary amine substituent group or a secondary amine substituent group; and
reacting the acid terminated polyoxyalkylene composition and the first diamine compound to form a reactant product, wherein the reaction product comprises an amidoamine compound having the formula of:
wherein each of R 1 and R 2 comprises a hydrogen atom or a substituent group selected from the group consisting of a branched or linear aliphatic, a cycloaliphatic, an aromatic substituent group and combinations thereof, having 1 to 21 carbon atoms, with at least one of R 1 and R 2 comprising a hydrogen atom, R 3 is a divalent hydrocarbon substituent group selected from the group consisting of a branched or linear aliphatic, a cycloaliphatic, an aromatic substituent group, and combinations thereof, having 2 to 18 carbon atoms, n is an average number from about 18 to about 500, X is a hydrogen atom or a substituent group selected from the group consisting of a methyl substituent, an ethyl substituent, a hydroxymethyl substituent group, and combinations thereof, and Y is a hydrogen atom or a substituent group selected from the group consisting of a methyl substituent, an ethyl substituent, a hydroxymethyl substituent group, and combinations thereof.
11. The method of claim 10 , wherein the amidoamine compound comprises an amine value from about 8 to about 30.
12. The method of claim 10 , wherein the providing the diamine compound comprises providing a diamine compound having two primary amine substituent groups with the formula:
H 2 N—R 3 —NH 2 ,
wherein R 3 is a divalent hydrocarbon substituent group selected from the group consisting of a branched or linear aliphatic, a cycloaliphatic, an aromatic substituent group, and combinations thereof, having 2 to 18 carbon atoms.
13. The method of claim 12 , wherein the providing the diamine compound comprises providing the diamine compound at a stoichiometric excess of amine substituent groups to carboxylic end groups of the acid terminated polyoxyalkylene composition.
14. The method of claim 12 , further comprising reacting the reaction product with a monoepoxy-containing composition.
15. The method of claim 10 , wherein the providing the diamine compound comprises providing a diamine compound having a primary amine substituent group and a secondary amine substituent group with the diamine having the formula:
R 1 —HN—R 3 —NH 2 ,
wherein R 1 is a branched or linear aliphatic, a cycloaliphatic, or an aromatic substituent group having 1 to 21 carbon atoms and R 3 is a divalent hydrocarbon substituent group selected from the group consisting of a branched or linear aliphatic, a cycloaliphatic, an aromatic substituent group, and combinations thereof, having 2 to 18 carbon atoms.
16. The method of claim 15 , wherein the R 1 substituent group further comprises an end group selected from the group consisting of a methyl group, a hydroxyl group, and combinations thereof, and the R 3 substituent group further comprises an end group selected from the group consisting of a methyl group, a hydroxyl group, and combinations thereof.
17. The method of claim 16 , wherein the R 1 substituent group, the R 3 substituent group, or both, further comprises one or more non-reactive oxygen or nitrogen atoms in the backbone of the substituent group.
18. The method of claim 10 , wherein each of the two or more polyoxyalkylene polyol compounds are reacted with the diamine compound separately to form a first and second amidoamine compound, and further comprising intermixing the first and second amidoamine compounds.
19. The method of claim 10 , further comprising reacting the reactant product with an epoxy composition to form an epoxy functional amidoamine composition.
20. The method of claim 19 , wherein the epoxy composition comprises a di-epoxy component.
21. The method of claim 20 , wherein the di-epoxy component comprises a di-epoxy resin or a mixture of a di-epoxy resin and a phenolic compound.
22. The method of claim 19 , wherein the epoxy composition comprises at least one epoxy resin having a functionality of greater than 0.8 epoxide groups per molecule.
23. The method of claim 19 , wherein the epoxy composition comprises a stoichiometric excess of epoxy substituent groups to amine groups and water, and the epoxy functional amidoamine composition comprises an aqueous epoxy resin dispersion.
24. The method of claim 23 , wherein the epoxy-functional surfactant comprises from about 1 wt. % to about 20 wt. % of the dispersion.
25. The method of claim 19 , wherein the epoxy functional amidoamine composition comprises an epoxy-functional surfactant having the formula:
wherein m is from 1 to 11, n is from 1 to 3, q is from 0 to 8, each p is from about 18 to about 500, X is a hydrogen atom, a methyl substituent, an ethyl substituent, a hydroxymethyl substituent group, subsets thereof, or combinations thereof, each Y is a hydrogen atom, a methyl substituent, an ethyl substituent, a hydroxymethyl substituent group, or combinations thereof, and R 17 is an alkyl group, an aryl group, an acyl group, or combinations thereof.
26. The method of claim 19 , further comprising reacting the epoxy functional amidoamine composition with a polyamine compound.