Hydroxylamino polymer and method for the production thereof

Patent metadata

Field	Value
Publication number	US-9238711-B2
Application number	US-201214366336-A
Country	US
Kind code	B2
Filing date	Dec 17, 2012
Priority date	Dec 20, 2011
Publication date	Jan 19, 2016
Grant date	Jan 19, 2016

Abstract

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.

First claim

The invention claimed is:

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.

Assignees

• Bayer Ip Gmbh

Inventors

• Hofmann Jorg
• Lorenz Klaus
• Nefzger Hartmut

Classifications

• C08G18/4887 Primary

  containing carboxylic ester groups derived from carboxylic acids other than acids of higher fatty oils or other than resin acids · CPC title

• C08G63/6854

  derived from polycarboxylic acids and polyhydroxy compounds · CPC title

• C08G63/676 Primary

  in which at least one of the two components contains aliphatic unsaturation · CPC title

• C08G18/4615

  containing nitrogen · CPC title

• C08G18/4252

  derived from polyols containing polyether groups and polycarboxylic acids · CPC title