Polyester-modified amino adducts

Patent metadata

Field	Value
Publication number	US-10836857-B2
Application number	US-201716333847-A
Country	US
Kind code	B2
Filing date	Sep 11, 2017
Priority date	Sep 16, 2016
Publication date	Nov 17, 2020
Grant date	Nov 17, 2020

Abstract

The invention relates to processes for producing an amine adduct in which in a 1st step a polyamine (A) is reacted with a monomer (C) in the form of an epoxide, an oxetane or a cyclic carbonate to afford an (intermediate) product (AC) which in a subsequent 2nd step is reacted with a monomer (B) in the form of a lactone, an acyclic hydroxycarboxylic acid or a hydroxy-functional acyclic ester to afford a (descendant) product (ACB), wherein the polyamine (A) in each case comprises at least three amino groups (A+) selected from primary and secondary amino groups and each capable of reaction with the monomers (C) and (B), the monomer (C) contains no ester groups, no carboxyl groups and no primary or secondary amino groups and in the 1st step with ring opening and formation of a hydroxyl group (H+) reacts with one of the amino groups (A+) of the polyamine (A) with additional formation of either a carbon-nitrogen bond or a urethane bond, the monomer (B) contains no primary or secondary amino groups, has a molecular weight of 90-300 g/mol and in the 2nd step reacts in such a way that any amino groups (A+) not converted in the 1st step are converted into amide groups and hydroxyl groups (H+) formed in the 1st step are converted into ester groups, wherein the monomer (B) is chosen in such a way that either in the conversion thereof a terminal hydroxyl group (H++) is additionally formed or that the monomer (B) itself already has a terminal hydroxyl group (H++) and that via the terminal hydroxyl groups (H++) with formation of (poly)ester groups a further addition of the monomer (B) is effected, wherein the process parameters are chosen such that in the 1st step and in the 2nd step altogether at least 50 mol % of the amino groups (A+) are converted.

First claim

The invention claimed is:

1. A process for preparing an amine adduct, comprising reacting in a 1st step a polyamine (A) with a monomer (C), monomer (C) comprising one or more of an epoxide, an oxetane or a cyclic carbonate to form an intermediate product (AC) and reacting intermediate product (AC) in a subsequent 2nd step with a monomer (B), monomer (B) comprising one or more of a lactone, an acyclic hydroxycarboxylic acid or a hydroxy-functional acyclic ester, to form a downstream product (ACB), wherein
the polyamine (A) has in each case at least three amino groups (A+) which are selected from primary and secondary amino groups and which in each case are reactive with the monomers (C) and (B),
the monomer (C) contains no ester groups, no carboxyl groups, and no primary or secondary amino groups, and in the 1st step reacts with ring opening and also formation of a hydroxyl group (H+) with one of the amino groups (A+) of the polyamine (A), with additional formation of either a carbon-nitrogen bond or a urethane bond,
the monomer (B) contains no primary or secondary amino groups, has a molecular weight of 90-300 g/mol, and reacts in the 2nd step in such a way that any amino groups (A+) unreacted in the 1st step are converted into amide groups, and hydroxyl groups (H+) formed in the 1st step are converted into ester groups, wherein the monomer (B) is selected such that either reaction thereof is accompanied by additional formation of a terminal hydroxyl group (H++) or that the monomer (B) itself already possesses a terminal hydroxyl group (H++) and that via the terminal hydroxyl groups (H++), with formation of (poly)ester groups, there is further adduction of the monomer (B),
wherein the process parameters are selected such that in the 1st step and in the 2nd step in total at least 50 mol % of the amino groups (A+) are converted.

2. The process as claimed in claim 1 , wherein the monomer (C) is in the form of an epoxide, and wherein in the 1st step the monomer (C), with ring opening and with formation of a hydroxyl group (H+), reacts with one of the amino groups (A+) of the polyamine (A), with additional formation of a carbon-nitrogen bond.

3. The process as claimed in claim 1 , wherein the monomer (C) has exclusively the elements carbon, hydrogen, and oxygen, and contains no hydroxyl groups.

4. The process as claimed in claim 1 , wherein the monomer (C) has a maximum of three oxygen atoms and 6 to 70 carbon atoms.

5. The process as claimed in claim 1 , wherein the monomer (B) is present in the form of a lactone.

6. The process as claimed in claim 1 , wherein the polyamine (A) is used in relation to the monomer (C) in a weight ratio of 1:0.1 to 1:100.

7. The process as claimed in claim 1 , wherein monomer (B) is used relative to monomer (C) in a molar ratio such that after the end of the 2nd step a maximum of 5% of the hydroxyl groups present in the downstream product (ACB) are present in the form of hydroxyl groups (H+) formed in the 1st step.

8. The process as claimed in any of claim 1 wherein the monomer (B) is used in relation to the monomer (C) in a molar ratio of 500:1 to 1:1.

9. The process as claimed in claim 1 wherein the process parameters are selected such that at least 50 mol % of the amino groups (A+) are already converted by the 1st step and a total of at least 70 mol % of the amino groups (A+) are converted by the 1st and 2nd steps.

10. The process as claimed in claim 1 , wherein predominantly or exclusively the only reaction components used are polyamine (A), monomer (C), and monomer (B), so that the downstream product (ACB), based on its own mass, contains a total of at least 80 wt % of structural elements from the group of reacted polyamine (A), reacted monomer (C) and reacted monomer (B).

11. The process as claimed in claim 1 wherein the 1st step and the 2nd step are carried out in each case at temperatures below 175° C.

12. The process as claimed in claim 1 further comprising reacting the downstream product (ACB) with an acid comprising one or more of an aliphatic, cycloaliphatic and/or aromatic monocarboxylic acids each containing 1-30 carbon atoms in such a way as to form a downstream product (ACB) modified by salt formation and/or ester formation.

13. The process as claimed claim 1 further comprising neutralizing the downstream product (ACB) with one or more organic or inorganic acids or by quaternization.

14. An amine adduct preparable by the process as claimed in claim 1 .

15. A paint and/or plastic comprising an amine adduct preparable by the process as claimed in claim 1 .

16. The process as claimed in claim 4 , wherein the monomer (C) has precisely one oxygen atom and 6 to 32 carbon atoms.

17. The process as claimed in claim 5 , wherein the monomer (B) comprises one or more of caprolactone, valerolactone or butyrolactone.

18. The process as claimed in claim 7 , wherein monomer (B) is used relative to monomer (C) in a molar ratio such that after the end of the 2nd step a maximum of 1% of the hydroxyl groups present in the downstream product (ACB) are present in the form of hydroxyl groups (H+) formed in the 1st step.

19. The process as claimed in claim 10 , wherein the downstream product (ACB), based on its own mass, contains a total of at least 95 wt % of structural elements from the group of reacted polyamine (A), reacted monomer (C) and reacted monomer (B).

Assignees

• Byk Chemie Gmbh

Inventors

• Giebelhaus Irina
• Okkel Andreas
• Pritschins Wolfgang

Classifications

• C08G63/64

  Polyesters containing both carboxylic ester groups and carbonate groups · CPC title

• C08G63/6852 Primary

  derived from hydroxy carboxylic acids · CPC title

• C08G63/664

  derived from hydroxy carboxylic acids · CPC title

• C08L67/04

  Polyesters derived from hydroxycarboxylic acids, e.g. lactones (C08L67/06 takes precedence) · CPC title

• C08K5/17

  Amines; Quaternary ammonium compounds · CPC title