Radiation curable coating composition based on chain-extended and cross-linked polyurethanes

Patent metadata

Field	Value
Publication number	US-10584262-B2
Application number	US-201515537103-A
Country	US
Kind code	B2
Filing date	Dec 7, 2015
Priority date	Dec 17, 2014
Publication date	Mar 10, 2020
Grant date	Mar 10, 2020

Abstract

The invention relates to aqueous polyurethane dispersions that are curable with UV radiation. The polyurethanes are chain-extended with aromatic, cycloaliphatic or aliphatic diamine compound and cross-linked with aliphatic triamine compound. The polyurethanes are useful dispersions for coating various substrates. The use of the invented dispersions results in high hardness, very good flexibility and good chemical resistance in both clear coats and pigmented coatings before and after UV curing combined with very good adhesion to different substrates.

First claim

The invention claimed is:

1. An aqueous, radiation curable coating composition, comprising:
A) at least one water-dispersible polyurethane component consisting of the constituents:
A1) at least one aromatic, cycloaliphatic or aliphatic diisocyanate or polyisocyanate compound in an amount suitable for effecting polymerization;
A2) at least one ethylenically unsaturated compound that contains at least two reactive groups capable of reacting with isocyanate groups;
A3) at least one hydrophilic carboxylic acid that contains at least one reactive group capable of reacting with isocyanate groups and effecting dispersion of the polyurethane component A) in the aqueous phase;
A4) at least one high molecular weight polyester polyol compound;
A5) at least one low molecular weight alcohol that has at least two hydroxy functions;
A6) at least one polyfunctional diamine compound; and
A7) at least one polyfunctional polyamine compound that has at least three amino groups; and

B) water.

2. The composition according to claim 1 , wherein the A) at least one water-dispersible polyurethane component consists of the constituents:
at least one cycloaliphatic diisocyanate or polyisocyanate compound in an amount suitable for effecting polymerization as the at least one aromatic, cycloaliphatic or aliphatic diisocyanate or polyisocyanate compound of the constituent A1);
at least one reaction product of glycidyl ethers with (meth)acrylic acid as the at least one ethylenically unsaturated compound of the constituent A2);
at least one hydrophilic carboxylic acid that contains at least two hydroxy groups as the at least one hydrophilic carboxylic acid of the constituent A3);
at least one high molecular weight polyester polyol compound obtained by condensation of aliphatic alcohols having two hydroxy functions and aliphatic dicarboxylic acids as the at least one high molecular weight polyester polyol compound of constituent A4);
at least one aliphatic straight chained or branched chained diol compound as the at least one low molecular weight alcohol of the constituent A5);
at least one aromatic, cycloaliphatic or aliphatic diamine compound as the at least one polyfunctional diamine compound of the constituent A6); and
at least one aliphatic triamine compound as the at least one polyfunctional polyamine compound of the constituent A7).

3. The composition according to claim 2 , wherein the A) at least one water-dispersible polyurethane component consists of the constituents:
isophorone diisocyanate in an amount suitable for effecting polymerization as least one cycloaliphatic diisocyanate or polyisocyanate compound of the constituent A1);
at least one diacrylate ester of bisphenol A diglycidylether as the at least one reaction product of glycidyl ethers with (meth)acrylic acid of the constituent A3);
at least one selected from the group consisting of glycolic acid and dimethylolpropionic acid as the at least one hydrophilic carboxylic acid that contains at least two hydroxy groups of the constituent A3);
the at least one high molecular weight polyester polyol compound obtained by condensation of aliphatic alcohols having two hydroxy functions and aliphatic dicarboxylic acids as the at least one high molecular weight polyester diol compound of constituent A4);
at least one C 2 -C 4 alkanediol as the at least one aliphatic straight chained or branched chained diol compound of the constituent A5);
isophorone diamine (IPDA) as the at least one aromatic, cycloaliphatic or aliphatic diamine compound of the constituent A6); and
diethylene triamine (DETA) as the at least one aliphatic triamine compound of the constituent A7).

4. The coating composition according to claim 1 , further comprising one or more additional additives selected from the group consisting of agents for effecting neutral or approximately neutral conditions, reactive diluents and other customary coating additives.

5. A substrate coated with the coating composition according to claim 1 .

6. A water-dispersible polyurethane A) consisting of constituents A1) to A7), which is obtained by polymerization of the constituents A1) to A7):
A1) at least one aromatic, cycloaliphatic or aliphatic diisocyanate or polyisocyanate compound in an amount suitable for effecting polymerization;
A2) at least one ethylenically unsaturated compound that contains at least two reactive groups capable of reacting with isocyanate groups;
A3) at least one hydrophilic carboxylic acid that contains at least one reactive group capable of reacting with isocyanate groups and effecting dispersion of the polyurethane component A) in the aqueous phase;
A4) at least one high molecular weight polyester polyol compound;
A5) at least one low molecular weight alcohol that has at least two hydroxy functions;
A6) at least one polyfunctional diamine compound; and
A7) at least one polyfunctional polyamine compound that has at least three amino groups.

7. A process for preparing a chain-extended and cross linked water-dispersible polyurethane A) consisting of constituents A1) to A7), the process comprising:
polymerizing in solution the constituents:
A1) at least one aromatic, cycloaliphatic or aliphatic diisocyanate or polyisocyanate compound in an amount suitable for effecting polymerization;
A2) at least one ethylenically unsaturated compound that contains at least two reactive groups capable of reacting with isocyanate groups;
A3) at least one hydrophilic carboxylic acid that contains at least one reactive group capable of reacting with isocyanate groups and effecting dispersion of the polyurethane component A) in the aqueous phase;
A4) at least one high molecular weight polyester polyol compound; and
A5) at least one low molecular weight alcohol that has at least two hydroxy functions; and

dispersing the polyurethane obtained with a mixture of
A6) at least one aromatic, cycloaliphatic or aliphatic diamine compound; and
A7) at least one aliphatic triamine compound;

with the optional addition of one or more additives selected from the group consisting of agents for effecting neutral or approximately neutral conditions, reactive diluents and other customary coating additives.

8. The process according to claim 7 , which comprises polymerizing the constituents A1)-A5) in a solvent and dispersing the polyurethane A) obtained with a mixture of
A6) at least one aromatic, cycloaliphatic or aliphatic diamine compound; and
A7) at least one aliphatic triamine compound.

9. The process according to claim 8 , which comprises polymerizing in a solvent the constituents A1)-A5) and dispersing the polyurethane obtained in water with a mixture of
A6) isophorone diamine (IPDA); and
A7) diethylene triamine (DETA).

10. A method for coating a substrate, wherein the aqueous coating composition according to claim 1 is applied to a substrate, subsequently dried and/or radiation-cured.

11. The method according to claim 10 , wherein the aqueous coating composition is applied to a substrate, subsequently dried and/or cured under exposure to UV-light energy radiation.

12. A process comprising coating a lignin-containing substrate or a plastic-containing substrate with the water-dispersible polyurethane A) according to claim 6 .

13. A process comprising coating a substrate with the water-dispersible polyurethane A) according to claim 6 , wherein the substrate is one or more selected from the group consisting of metals and metallic surfaces, polymers and polymer surfaces, wood, wood-base materials, wood-containing substrates, cellulose fibres and paper raw materials wood.

14. A process comprising adhesion priming a

Assignees

• Basf Se

Inventors

• Berger Sebastian
• Thuery Peter
• Neumann Susanne
• Roesch Christine
• Burkhardt Uwe
• Andes Katharina
• Wahl Stefan
• Biehler Manfred
• Roller Sebastian

Classifications

• C08G18/0823

  containing carboxylate salt groups or groups forming them · CPC title

• C08G18/325

  containing secondary or tertiary amino groups (C08G18/3228, C08G18/3234, C08G18/3246 take precedence) · CPC title

• C08G18/3206

  aliphatic · CPC title

• C08G18/348

  Hydroxycarboxylic acids · CPC title

• C08G18/6659

  with compounds of group C08G18/34 · CPC title