Polyisocyanate-modified polycarboxylic acids
View Patent ↗A process for preparing polyisocyanate-modified polycarboxylic acids by conversion of anhydride-group-free polycarboxylic acids with isocyanate-functional compounds. The process includes reacting A) an anhydride-group-free polycarboxylic-acid component with B) an isocyanate-functional component having an (average) isocyanate functionality of at least 1.8, at an equivalent ratio of carboxylic acid groups to isocyanate groups of from 1.2:1 to 120:1. The polyisocyanate-modified polycarboxylic acids are solid below 40° C. and liquid above 130° C., and have an average carboxylic acid functionality of at least 1.8, a content of free carboxylic acid groups of from 4.0 wt. % to 80.0 wt. % and a content of amide groups of from 0.4 wt. % to 32.5 wt. %.
1. A process for preparing polyisocyanate-modified polycarboxylic acids comprising reacting
A) an anhydride-group-free polycarboxylic-acid component with
B) an isocyanate-functional component having an (average) isocyanate functionality of at least 1.8
at an equivalent ratio of carboxylic acid groups to isocyanate groups of from 2:1 to 50:1;
wherein the polyisocyanate-modified polycarboxylic acids are solid below 40° C. and liquid above 130° C., and have
a) an average carboxylic acid functionality of at least 1.8,
b) a content of free carboxylic acid groups (determined as —COOH; molecular weight=45) of from 4.0 wt. % to 80.0 wt. % and
c) a content of amide groups (determined as —CONH—; molecular weight=43) of from 0.4 wt. % to 32.5 wt. %.
2. The process according to claim 1 , wherein saturated aliphatic and/or cycloaliphatic dicarboxylic acids having from 4 to 20 carbon atoms or mixtures thereof are employed as polycarboxylic acid component A).
3. The process according to claim 1 , wherein saturated linear aliphatic dicarboxylic acids having from 5 to 12 carbon atoms or mixtures thereof are employed as polycarboxylic acid component A).
4. The process according to claim 1 , wherein the isocyanate-functional component B) comprises compounds having exclusively aliphatically and/or cycloaliphatically bound isocyanate groups.
5. The process according to claim 1 , wherein the isocyanate-functional component B) is selected from the group consisting of 1,6-hexamethylene diisocyanate, 1-isocyanato-3,5,5-trimethyl-5-isocyanatomethylcyclohexane, 4,4′-dilsocyanatodicyclohexyl-methane, polyisocyanates thereof, NCO prepolymers thereof, and mixtures thereof.
6. The process according to claim 1 carried out in a solvent-free manner in a melt.
7. The process according to claim 1 carried out in solvents or in solvent mixtures.
8. The process according to claim 7 , wherein the solvents are selected from the group consisting of ethyl acetate, butyl acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, 1-methoxypropyl-2-acetate, 2-butanone, 4-methyl-2-pentanone, cyclohexanone, toluene, acetone, propylene glycol diacetate, diethylene glycol dimethyl ether, diethylene glycol ethyl ether acetate and diethylene glycol butyl ether acetate, N-methylpyrrolidone, N-methylcaprolactam, N,N-dimethylformamide, N,N-dimethylacetamide, methylene chloride, and mixtures thereof.