Functionalized ketone-aldehyde condensation resins

Patent metadata

Field	Value
Publication number	US-2016289366-A1
Application number	US-201615089745-A
Country	US
Kind code	A1
Filing date	Apr 4, 2016
Priority date	Apr 2, 2015
Publication date	Oct 6, 2016
Grant date	—

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

1 . A process for preparing a functionalized resin, comprising:
condensing a ketone and an aldehyde in the presence of at least one alcohol or the alkoxylate thereof, wherein the alcohol comprises a member selected from the group consisting of an amino alcohol, a compound which is obtained from an amino alcohol, hydroxybutyl vinyl ether, an OH-functional acrylate, an OH-functional terpene, an OH-functional halogen compound, a hydroxycarboxylic acid, a sulphur-containing alcohol, a compound which is obtained from a hydroxyl-containing urea, a carbohydrate, a siloxane, an OH-functional phosphorus compound, an unsaturated alcohol and mixtures thereof.

2 . The process according to claim 1 , wherein the amino alcohol is present and is 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, triethanolamine, 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 or 2,2′-(phenylamino)diethanol, 1-(2-hydroxyethyl)piperazine, 4-(2-hydroxyethyl)morpholine, compounds obtained from the above amino alcohols and mixtures thereof.

3 . The process according to claim 1 , wherein compound which is obtained from hydroxyl-containing urea is present and is selected from the group consisting of N-(2-hydroxyethyl)ethyleneurea, hydroxycarbamide and mixtures thereof.

4 . The process according to claim 1 , wherein the OH-functional acrylate is present and is selected from the group consisting of hydroxyethyl acrylate, hydroxyethyl methacrylate and mixtures thereof.

5 . The process according to claim 1 , wherein OH-functional is present and is selected from the group consisting of citronellol, dolichol, phytol, geraniol, farnesol, linalool, bisabolol, terpineols and mixtures thereof.

6 . The process according to claim 1 , wherein OH-functional halogen is present and is selected from the group consisting of ethylenechlorohydrin, 1-(pyrid-3-yl)-2-chloroethanol, 2-chloro-1-(3-chlorophenyl)-ethanol, 2-chloro-1-(3-hydroxyphenyl)ethanol, polyfluorinated alcohols and mixtures thereof.

7 . The process according to claim 1 , wherein sulphur-containing alcohol is present and is selected from the group consisting of 2,2′-thiobisethanol, mercaptoethanol and mixtures thereof.

8 . The process according to claim 1 , wherein unsaturated alcohols is present and is selected from the group consisting of allyl alcohol, vinyl alcohol, 2-allyloxyethanol, hexenols, prenol, 2-butene-1,4-diol, sorbic alcohol, propargyl alcohol, 2-butyne-1,4-diol, 3-hexyne-2,5-di ol, 1-ethynyl-1-cyclohexanol, 2-methyl-3-butyn-2-ol, 3-butyn-2-ol, 4-ethyl-1-octyn-3-ol and mixtures thereof.

9 . The process according to claim 1 , wherein carbohydrate is present and is selected from the group consisting of saccharides and polysaccharides and mixtures thereof.

10 . The process according to claim 1 , wherein OH-functional phosphorus compound is present and is selected from the group consisting of phosphoric esters having a further free OH functionality.

11 . The process according to claim 1 , wherein the hydroxycarboxylic acid is present and is selected from the group consisting of lactic acid, 2-hydroxymethylbutyric acid, 2-hydroxymethylhexanoic acid, 2-hydroxymethylpropanoic acid, mandelic acid, compounds obtained from mandelic acid, hydroxybenzoic acid, and mixtures thereof.

12 . The process according to claim 1 , wherein the siloxane is present and is selected from the group consisting of organofunctionalized siloxanes.

13 . The process according to claim 1 , wherein the ketone is 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 (methyl isoamyl ketone); 4-methylpentan-2-one (methyl isobutyl ketone); 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; rheosmin; 4-(4-hydroxy-3-methoxyphenyl)-2-butanone; levulinic acid; compounds obtained from levulinic acid, alkyl-substituted cyclohexanones; diones and mixtures thereof.

14 . The process according to claim 13 , wherein the aldehyde is selected from the group consisting of formaldehyde, paraformaldehyde, formaldehyde donor and mixtures thereof.

15 . The process according to claim 14 , wherein a molar aldehyde to ketone ratio is in the range from 1:1 to 3.5:1.

16 . The process according to claim 15 , wherein methanol, ethanol and polyvalent alcohols having 2 to 6 carbon atoms and/or phenol are not used as sole alcohols.

17 . The process according to claim 16 , wherein 0.1 to 10 mol of alcohol are used per mole of ketone.

18 . The process according to claim 17 , wherein condensing is effected in the presence of an alkaline catalyst at a temperature between 40° C. and 120° C.

19 . The process according to claim 18 , wherein the aldehyde used is 20% to 40% by weight aqueous formaldehyde solution.

20 . The process according to claim 19 , wherein the aldehyde used is 30% by weight of aqueous formaldehyde solution and the ketone used is methyl isobutyl ketone.

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

22 . The functionalized resin according to claim 21 , which has a glass transition temperature of −80° C. to +140° C., determined in accordance with DIN 53765.

23 . A coating, comprising:
the functionalized resin according to claim 21 .

24 . A paint, a varnish or a pigment paste, comprising:
the functionalized resin according to claim 21 .

Assignees

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

Inventors

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

Classifications

• C09D5/027

  Dispersing agents (anti-settling agents C09D7/45) · CPC title

• C09D175/04

  Polyurethanes · CPC title

• C08G12/06

  Amines · CPC title

• C08G18/548 Primary

  Polycondensates of aldehydes with ketones · 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