Radiation-curing, water-dispersible polyurethane (meth)acrylates

Patent metadata

Field	Value
Publication number	US-9752056-B2
Application number	US-201314429456-A
Country	US
Kind code	B2
Filing date	Oct 9, 2013
Priority date	Oct 24, 2012
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

Abstract

The present invention describes radiation-curable, water-dispersible polyurethane acrylates which feature good grain highlighting, their use, and the method for producing them.

First claim

The invention claimed is:

1. A urethane (meth)acrylate (A) comprising a reaction product of:
(a) at least one (cyclo)aliphatic di- and/or polyisocyanate,
(b1) at least one (cyclo)aliphatic diol having a molar mass of less than 700 g/mol,
(b2) at least one polyesterdiol having a weight-average molar mass Mw of 700 to 2000 and optionally an acid number to DIN 53240 of not more than 20 mg KOH/g,
(c) at least one compound (c) having at least one isocyanate-reactive group and at least one radically polymerizable unsaturated group,
(d) at least one compound which has at least one isocyanate-reactive group and at least one acid group,
(e) at least one base for at least partial neutralization of at least one acid group of component (d), being different from components (h1) and (h2),
(f) optionally at least one monoalcohol, having precisely one hydroxyl function,
(g) optionally at least one monofunctional polyalkylene oxide polyether alcohol,
(h1) at least one monoamine which is substituted by one or two hydrocarbon radicals, in which the one or two hydrocarbon radicals together have at least 12 carbon atoms, and
(h2) optionally at least one compound having at least two primary and/or secondary amino groups,
wherein the urethane (meth)acrylate (A) is obtained by a process comprising reacting at least a portion of components (b1), (b2), and (c) with component (a).

2. The urethane (meth)acrylate according to claim 1 , wherein component (a) is a mixture of an aliphatic di- and/or polyisocyanate (a1) and a cycloaliphatic di- and/or polyisocyanate (a2).

3. The urethane (meth)acrylate according to claim 1 , wherein component (b1) is at least one selected from the group consisting of ethylene glycol, 1,2-propanediol, 1,3-propanediol, 2,2-dimethyl-1,2-ethanediol, 2,2-dimethyl-1,3-propanediol (neopentyl glycol), 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, and diethylene glycol.

4. The urethane (meth)acrylate according to claim 1 , wherein component (b2) is a polyesterdiol synthesized at least partly from aliphatic diol and/or dicarboxylic acid building blocks.

5. The urethane (meth)acrylate according to claim 1 , wherein component (c) is at least one selected from the group consisting of 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2- or 3-hydroxypropyl acrylate, 1,4-butanediol monoacrylate, glyceryl 1,2- or 1,3-diacrylate, trimethylolpropane diacrylate, pentaerythrityl triacrylate, ditrimethylolpropane triacrylate, and dipentaerythrityl pentaacrylate.

6. The urethane (meth)acrylate according to claim 1 ,
wherein compound (c) is an epoxy (meth)acrylate of the formula:

where
R 1 is hydrogen or methyl.

7. The urethane (meth)acrylate according to claim 1 , wherein component (d) is at least one selected from the group consisting of dimethylolpropionic acid and dimethylolbutyric acid.

8. The urethane (meth)acrylate according to claim 1 ,
wherein
the one or two hydrocarbon radicals of the compound (h1) are one or two alkyl radicals, and
both alkyl radicals each independently of one another comprise at least six carbon atoms.

9. The urethane (meth)acrylate (A) according to claim 1 , comprising a reaction product of
(a) at least one (cyclo)aliphatic di- and/or polyisocyanate,
(b1) at least one (cyclo)aliphatic diol having a molar mass of less than 700 g/mol,
(b2) at least one polyesterdiol having a weight-average molar mass Mw of 700 to 2000 and optionally an acid number to DIN 53240 of not more than 20 mg KOH/g,
(c) at least one compound (c) having at least one isocyanate-reactive group and at least one radically polymerizable unsaturated group,
(d) at least one compound which has at least one isocyanate-reactive group and at least one acid group,
(e) at least one base for at least partial neutralization of at least one acid group of component (d), being different from components (h1) and (h2),
(f) at least one monoalcohol, having precisely one hydroxyl function,
(g) at least one monofunctional polyalkylene oxide polyether alcohol,
(h1) at least one monoamine which is substituted by one or two hydrocarbon radicals, in which the one or two hydrocarbon radicals together have at least 12 carbon atoms, and
(h2) at least one compound having at least two primary and/or secondary amino groups.

10. The urethane (meth)acrylate (A) of claim 1 , obtained by a process that comprises reacting at least a portion of components (b1), (b2), and (c) with component (a) to obtain a reaction mixture, and then, after the reacting substantially consumes components of the reaction mixture, adding component (h1).

11. A coating material, comprising:
the urethane (meth)acrylate according to claim 1 .

12. A coating material comprising:
the urethane (meth)acrylate according to claim 1 and
a (meth)acrylate (B) which has at least two (meth)acrylate functions and an average molecular weight of up to 1000 g/mol.

13. The coating material according to claim 12 ,
wherein the (meth)acrylate (B) is a compound of the formula (VIIIa) to (VIIId):

where
R 7 and R 8 independently of one another are hydrogen or optionally aryl-, alkyl-, aryloxy-, alkyloxy-, heteroatom- and/or heterocycle-substituted C 1 -C 18 alkyl,
k, l, m, q independently of one another are each an integer from 1 to 10, and
each X i for i=1 to k, 1 to l, 1 to m, and 1 to q is optionally selected independently of one another from the group consisting of —CH 2 —CH 2 —O—, —CH 2 —CH(CH 3 )—O—, —CH(CH 3 )—CH 2 —O—, —CH 2 —C(CH 3 ) 2 —O—, —C(CH 3 ) 2 —CH 2 —O—, —CH 2 —CHVin-O—, —CHVin-CH 2 —O—, —CH 2 —CHPh-O—, and —CHPh-CH 2 —O—,
where Ph is phenyl and Vin is vinyl.

14. A substrate coated with the coating material according to claim 12 .

15. A method for coating a substrate, the method comprising:
applying the coating material of claim 12 to the substrate, thereby producing an applied substrate,
drying the applied substrate, thereby producing a dried substrate and
radiation-curing the dried product.

16. A substrate coated with the urethane (meth)acrylate according to claim 1 .

17. The substrate according to claim 16 , comprising: coated oak, spruce, pine, beech, maple, chestnut, plane, robinia, ash, birch, stone pine, elm, walnut, or macore.

18. The substrate according to claim 16 coated with the urethane (meth)acrylate, wherein the substrate is wood, paper, textile, leather, nonwoven, plastics surfaces, glass, ceramic, mineral building materials, metals, coated metals, paper, paperboard, or cardboard.

19. The substrate according to claim 16 coated with the urethane (meth)acrylate, wherein the substrate is oak, spruce, pine, beech, maple, chestnut, plane, robinia, ash, birch, stone pine, elm, walnut, macore, or cork.

20. A method for coating a substrate, the method comprising:
applying the urethane (meth)acrylate according to claim 1 to the substrate, thereby producing an applied substrate,
drying the applied substrate, thereby producing a dried substrate and
radiation-curing the dried product.

21. The method according to claim 20 , wherein the substrate comprises: coated oak, spruce, pine, beech, maple, chestnut, plane, robinia, ash, birch, stone pine, elm, walnut, or macore.

Assignees

• Basf Se

Inventors

• Berger Sebastian
• Thuery Peter
• Neumann Susanne
• Becker Tanja
• Becker Axel

Classifications

• C08G18/0823

  containing carboxylate salt groups or groups forming them · CPC title

• Y10T428/31551

  Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.] · CPC title

• C08G18/42

  Polycondensates having carboxylic or carbonic ester groups in the main chain · CPC title

• C08G18/675

  Low-molecular-weight compounds · CPC title

• C08G18/722

  Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates · CPC title