Radiation-curable water-dispersible polyurethane (meth)acrylates

Patent metadata

Field	Value
Publication number	US-2016200938-A1
Application number	US-201414914426-A
Country	US
Kind code	A1
Filing date	Aug 22, 2014
Priority date	Aug 26, 2013
Publication date	Jul 14, 2016
Grant date	—

Abstract

The present invention relates to radiation-curable, water-dispersible polyurethane(meth)acrylates, to coating compositions comprising the latter, to the use thereof and to the process for production thereof.

First claim

1 . A radiation-curable, water-dispersible urethane(meth)acrylate (A) essentially formed from
(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 polyester diol having a weight-average molar mass Mw of 700 to 2000. (c) at least one compound (c) having at least one isocyanate-reactive group and at least one free-radically polymerizable unsaturated group, (d) at least one compound having at least one isocyanate-reactive group and at least one acid group, (e) at least one base of an alkali metal for at least partial neutralization of the acid groups of component (d), (f) optionally at least one monoalcohol having exactly one hydroxyl function, or at least one mono- and di-C 1 -C 4 -alkylamine, (g) at least one monofunctional polyalkylene oxide polyether alcohol.

2 . The urethane(meth)acrylate according to claim 1 , wherein component (a) is a mixture of a cycloaliphatic or aliphatic monomeric diisocyanate (a1) and a polyisocyanate (a2) based on a cycloaliphatic or aliphatic monomeric diisocyanate.

3 . The urethane(meth)acrylate according to claim 2 , wherein component (a1) is selected from the group consisting of hexamethylene diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, isophorone diisocyanate, 2,4′-di(isocyanatocyclohexyl)methane, and 4,4′-di(isocyanatocyclohexyl)methane.

4 . The urethane(meth)acrylate according to claim 2 , wherein the polyisocyanate (a2) is a polyisocyanate having isocyanurate groups, uretdione diisocyanate, polyisocyanate having biuret groups, polyisocyanate having urethane or allophanate groups.

5 . The urethane(meth)acrylate according to any of claim 2 , wherein the polyisocyanate (a2) is a compound of the formula

in which
R 5 is a divalent alkylene radical which has 2 to 12 carbon atoms and may optionally be substituted by C 1 - to C 4 -alkyl groups and/or be interrupted by one or more oxygen atoms,
R 6 is a divalent alkylene radical or cycloalkylene radical which has 2 to 20 carbon atoms and may optionally be substituted by C 1 - to C 4 -alkyl groups and/or be interrupted by one or more oxygen atoms,
R 7 is hydrogen or methyl, preferably hydrogen, and
X is a positive number having a statistical average of 2 to 6.

6 . The urethane(meth)acrylate according to claim 1 , wherein component (b 1) is selected from the group consisting of ethylene glycol, propane-1,2-diol, propane-1,3-diol, butane-1,2-diol, butane-1,3-diol, butane-1,4-diol, butane-2,3-diol, pentane-1,2-diol, pentane-1,3-diol, pentane-1,4-diol, pentane-1,5-diol, pentane-2,3-diol, pentane-2,4-diol, hexane-1,2-diol, hexane-1,3-diol, hexane-1,4-diol, hexane-1,5-diol, hexane-1,6-diol, hexane-2,5-diol, heptane-1,2-diol, heptane-1,7-diol, octane-1,8-diol, octane-1,2-diol, nonane-1,9-diol, decane-1,2-diol, decane-1,10-diol, dodecane-1,2-diol, dodecane-1,12-diol, 1,5-hexadiene-3,4-diol, neopentyl glycol, 2-butyl-2-ethylpropane-1,3-diol, 2-methylpentane-2,4-diol, 2,4-dimethylpentane-2,4-diol, 2-ethylhexane-1,3-diol, 2,5-dimethylhexane-2,5-diol, 2,2,4-trimethylpentane-1,3-diol, pinacol, diethylene glycol, triethylene glycol, dipropylene glycol, and tripropylene glycol.

7 . The urethane(meth)acrylate according to any of the preceding claims claim 1 , wherein component (b2) is a polyester diol having a weight-average molar mass Mw of 700 to 2000 g/mol and an acid number to DIN 53240 of not more than 20 mg KOH/g.

8 . The urethane(meth)acrylate according to claim 1 , wherein component (c) is selected from the group consisting of 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2 hydroxypropyl acrylate, 3-hydroxypropyl acrylate, butane-1,4-diol monoacrylate, 1,2-diacrylate of glycerol, 1,3-diacrylate of glycerol, trimethylolpropane diacrylate, pentaerythrityl triacrylate, ditrimethylolpropane triacrylate and dipentaerythrityl pentaacrylate.

9 . The urethane(meth)acrylate according to claim 1 , wherein component (d) is dimethylolpropionic acid.

10 . The urethane(meth)acrylate according to claim 1 , wherein component (f) is present and is a mono-, di-C 1 -C 4 -alkylamine, mono- or dialkanolamine.

11 . The urethane(meth)acrylate according to claim 1 , wherein component (1) is present and is selected from the group consisting of diethylamine, di-n-butylamine, ethanolamine, propanolamine, N,N-dipropanolamine and N,N-diethanolamine.

12 . An aqueous coating composition comprising
the urethane(meth)acrylate according to claim 1 , optionally a low molecular weight (meth)acrylate (B) which is soluble or dispersible in an aqueous dispersion of the urethane(meth)acrylate (A), optionally a pigment, and optionally a photoinitiator.

13 . An article of wood, paper, textile, leather, fleece, plastics surfaces, glass, ceramic, mineral building materials, cement blocks, fiber cement boards, metals or coated metals, coated by the coating composition according to claim 12 .

14 . A printing ink comprising the coating composition according to claim 12 .

15 . A method for printing polycarbonate, polyethylene, polypropylene, polyamide, polyethylene terephthalate (PET) and paper with the printing ink according to claim 14 .

Assignees

• Basf Se

Inventors

• Berger Sebastian
• Thuery Peter
• Tranter Kenneth Shaun

Classifications

• C08G18/672 Primary

  Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen · CPC title

• C08G18/0823 Primary

  containing carboxylate salt groups or groups forming them · CPC title

• C08G18/2815

  Monohydroxy compounds · CPC title

• C08G18/8175

  with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen · CPC title

• C08G18/4216

  from mixtures or combinations of aromatic dicarboxylic acids and aliphatic dicarboxylic acids and dialcohols · CPC title