Functionalized ketone-aldehyde condensation resins

Patent metadata

Field	Value
Publication number	US-10113025-B2
Application number	US-201615089745-A
Country	US
Kind code	B2
Filing date	Apr 4, 2016
Priority date	Apr 2, 2015
Publication date	Oct 30, 2018
Grant date	Oct 30, 2018

Abstract

A functionalized ketone-aldehyde condensation resin is produced by condensing a ketone and an aldehyde in the presence of at least one alcohol or alkoxylate thereof, wherein the alcohol comprises amino alcohols and derivatives thereof, hydroxybutyl vinyl ether, OH-functional acrylates, OH-functional terpenes, OH-functional halogen compounds, hydroxycarboxylic acids, sulphur-containing alcohols, hydroxyl-containing urea derivatives, carbohydrates, siloxanes, OH-functional phosphorus compounds or unsaturated alcohols.

First claim

The invention claimed is:

1. A process for preparing a functionalized resin, comprising:
condensing a ketone selected from the group consisting of: acetone; acetophenone; ortho-, meta- or para-phenylacetophenone; methyl ethyl ketone; 3-pentanone; 2-heptanone; 3-heptanone; 4-heptanone; 2-octanone; 3-octanone; 2-undecanone; 5-methylhexan-2-one; 4-methylpentan-2-one; cyclopentanone; cyclododecanone; mixtures of 2,2,4- and 2,4,4-trimethylcyclopentanone; cycloheptanone; cyclooctanone; cyclohexanone; o-, m- or p-methoxyacetophenone; o-, m- or p-[N,N-dialkylaminophenyl]ethanone; alkyl-substituted cyclohexanones or diones or mixtures thereof
and an aldehyde in the presence of at least one amino alcohol selected from the group consisting of: N,N-dimethylaminoethanol, trimethylaminoethylethanolamine, 3-dimethylaminopropan-1-ol, butyldiethanolamine, butylethanolamine, dibutylethanolamine, diethylethanolamine, ethylethanolamine, dimethylaminoethoxyethanol, methyldiethanolamine, N,N-dimethylisopropanolamine, N-methylethanolamine, diethanolamine, diisopropanolamine, triisopropanolamine, N-(2-hydroxyethyl)piperidine, diisopropanol-p-toluidine, N,N-di(2-hydroxyethyl)aniline, N-(2-hydroxyethyl)aniline, 2-(2-aminoethoxy)ethanol, 3-amino-1-propanol, 5-amino-1-pentanol, monoethanolamine, N-(2-aminoethyl)ethanolamine, isopropanolamine, 2,2′-(phenylamino)diethanol, 1-(2-hydroxyethyl)piperazine, 4-(2-hydroxyethyl)morpholine, or derivatives or mixtures thereof,
wherein said aldehyde used is a 20% to 40% by weight aqueous formaldehyde solution, said amino alcohol is incorporated covalently into said resin and said condensation is conducted in situ.

2. The process according to claim 1 , wherein a molar aldehyde to ketone ratio is in the range from 1:1 to 3.5:1.

3. The process according to claim 2 , wherein said amino alcohol further comprises at least one alcohol selected from the group consisting of methanol, ethanol and polyvalent alcohols having 2 to 6 carbon atoms and/or phenol.

4. The process according to claim 3 , wherein 0.1 to 10 mol of amino alcohol are used per mole of ketone.

5. The process according to claim 4 , wherein condensing is affected in the presence of an alkaline catalyst at a temperature between 40° C. and 120° C.

6. The process according to claim 1 , wherein the aldehyde used is 30% by weight of aqueous formaldehyde solution and the ketone used is methyl isobutyl ketone.

7. A functionalized resin, obtained by a process according to claim 1 .

8. The functionalized resin according to claim 7 , which has a glass transition temperature of −80° C. to +140° C., determined in accordance with DIN 53765.

9. A coating, comprising:
the functionalized resin according to claim 7 .

10. A paint, a varnish or a pigment paste, comprising:
the functionalized resin according to claim 7 .

11. The process according to claim 1 , wherein said ketone is an alkyl-substituted cyclohexanone selected from the group consisting of 4-tert-amylcyclohexanone, 2-sec-butylcyclohexanone, 2-tert-butylcyclohexanone, 4-tert-butylcyclohexanone, 2-methylcyclohexanone and 3,3,5-trimethylcyclohexanone or diones or mixtures thereof.

Assignees

• Evonik Degussa Gmbh

Inventors

• Duerr Christoph Juergen
• Burian Bettina
• Engelke Daniel
• Ewald Michael
• Joerres Tanja
• Retzlaff Erika

Classifications

• C09B67/009

  polymeric dispersing agent · CPC title

• C08G6/02 Primary

  of aldehydes with ketones · CPC title

• C09D161/22

  of aldehydes with acyclic or carbocyclic compounds · CPC title

• C08G4/00

  Condensation polymers of aldehydes or ketones with polyalcohols; Addition polymers of heterocyclic oxygen compounds containing in the ring at least once the grouping —O—C—O— (of cyclic oligomers of aldehydes C08G2/00) · CPC title

• C09D161/02

  Condensation polymers of aldehydes or ketones only · CPC title