Hydroxylamino polymer and method for the production thereof
View Patent ↗The present invention relates to a process for the preparation of a hydroxy-amino polymer, comprising the steps: a) reacting an H-functional starter compound carrying at least one Zerewitinoff-active H atom with an unsaturated cyclic carboxylic acid anhydride to give a carboxyl-group-carrying prepolymer, b) reacting the carboxyl-group-carrying prepolymer with at least one epoxide compound to give a hydroxyl-group-carrying prepolymer, c) adding a primary amine and/or ammonia to the double bond of the hydroxyl-group-carrying prepolymer obtained according to step b) to give the hydroxy-amino polymer, wherein the ratio of the amount of carboxylic acid anhydride to the number of Zerewitinoff-active H atoms of the H-functional starter compound is so chosen that almost all the Zerewitinoff-active H atoms of the H-functional starter compound are reacted. The invention relates additionally to a hydroxy-amino polymer obtainable by the above-mentioned process, wherein the ratio of the amount of unsaturated cyclic carboxylic acid anhydride to the number of Zerewitinoff-active H atoms of the H-functional starter compound is at least approximately 0.9:1, and further to the use of this hydroxy-amino polymer in the preparation of a polyurethane urea polymer.
1. A process for the preparation of a hydroxy-amino polymer, comprising:
a) reacting an H-functional starter compound which has at least one Zerewitinoff-active H atom with an unsaturated cyclic carboxylic acid anhydride to form a carboxyl-group-containing prepolymer,
b) reacting the carboxyl-group-containing prepolymer with at least one epoxide compound to form a hydroxyl-group-containing prepolymer,
c) adding a primary amine and/or ammonia to the double bond of the hydroxyl-group-containing prepolymer formed in b) to yield the hydroxy-amino polymer,
wherein a catalyst is added to the reaction mixture at the same time as or prior to the reaction of the carboxyl-group-containing prepolymer with the epoxide compound, with the catalyst comprising one or more tertiary amines; and the ratio of the number of moles of carboxylic acid anhydride to the number of moles of Zerewitinoff-active H atoms of the H-functional starter compound is from at least 0.9:1 to 1.5:1.
2. The process according to claim 1 , wherein said H-functional starter compound contains from 1 to 35 Zerewitinoff-active H atoms.
3. The process according to claim 1 , wherein said H-functional starter compound is a polyhydroxy-functional polymer selected from the group consisting of straight-chained polyethers, branched polyethers, polyesters, polyether polyesters, polycarbonates, polyether polycarbonates and mixtures thereof.
4. The process according to claim 3 , wherein said polyether, said polyether polyester and/or said polyether polycarbonate contains ethylene oxide units, wherein the amount by weight of the ethylene oxide units in the polyether is at least 50 wt. %.
5. The process according to claim 1 , wherein said H-functional starter compound has a mean molar weight of from 200 to 10,000 g/mol.
6. The process according to claim 1 , wherein said unsaturated cyclic carboxylic acid anhydride is selected from unsaturated cyclic dicarboxylic acid anhydrides.
7. The process according to claim 1 , wherein said epoxide compound is selected from epoxides having from 2 to 24 carbon atoms.
8. The process according to claim 1 , wherein said ratio of the number of moles of carboxylic acid anhydride to the number of moles of Zerewitinoff-active H atoms of the H-functional starter compound is from 0.98:1 to 1.2:1.
9. The process according to claim 1 , wherein said primary amine is a monoamine or a diamine, contains at least one primary amino group and is selected from aliphatic amines, cycloaliphatic amines and/or araliphatic amines.
10. The process according to claim 1 , wherein said tertiary amine catalyst comprises diazabicyclooctane, N-methyldiethanolamine, dimethylethanolamine bis(2-(dimethylamino)ethyl)ether, diazabicyclo[5.4.0]undec-7-ene, dialkylbenzylamine, dimethylpiperazine, 2,2′-dimorpholinyl diethyl ether and pyridine or combinations thereof.
11. The process according to claim 1 , wherein said H-functional starter compound has a number average molecular weight of more than 600 g/mol.
12. The process according to claim 1 , wherein the ratio of hydroxyl functionalities to amine functionalities is from 1.2:1 to 1:1.2.
13. The process according to claim 1 , comprising the reaction of a polyisocyanate with said hydroxy-amino polymer to obtain a polyurethane.