Radiation curable aqueous coating compositions

Patent metadata

Field	Value
Publication number	US-10400111-B2
Application number	US-201113581906-A
Country	US
Kind code	B2
Filing date	Mar 4, 2011
Priority date	Mar 12, 2010
Publication date	Sep 3, 2019
Grant date	Sep 3, 2019

Abstract

This invention relates to a radiation curable aqueous coating composition comprising: —from 1 to 99% by weight, relative to the total weight of (1) and (2), of at least one radiation curable aqueously dispersed polyester resin composition (1) comprising an emulsifier D and the reaction product AC of a hydroxy functional polyester resin A and an olefinically unsaturated compound C which can be radically polymerized and which is attached to the polyester resin backbone by an ester linkage or a urethane linkage, and—from 1 to 99% by weight, relative to the total weight of (1) and (2), of at least one other olefinically unsaturated compound (2) selected from the group of: water-dispersible compounds (21); water-soluble compounds (22); and/or water-compatible compounds (23) that have a weight average molecular weight of at least 450 Dalton and are different from the reaction product AC.

First claim

The invention claimed is:

1. A radiation curable aqueous coating composition comprising:
from 1 to 99% by weight, relative to a total weight of (1) and (2), of at least one radiation curable aqueously dispersed polyester resin composition (1) comprising an emulsifier D and a reaction product AC of a hydroxy functional polyester resin A and an olefinically unsaturated compound C which can be radically polymerised and which is attached to the polyester resin backbone by an ester linkage or a urethane linkage, wherein the emulsifier D is compatible with the reaction product AC and is the polyesterification product of a fatty acid D1, a polyhydric alcohol D2 having at least three hydroxyl groups per molecule, a carboxylic acid D3 or its anhydride, and a monoalkoxy polyalkylene glycol D4, and
from 1 to 99% by weight, relative to the total weight of (1) and (2), of at least one other olefinically unsaturated compound (2) selected from the group consisting of (meth)acrylated (poly)urethanes, (meth)acrylated epoxies, (meth)acrylated polyesters, (meth)acrylated polyethers, partially esterified styrene/maleic anhydride copolymers, and mixtures or copolymers thereof that have a weight average molecular weight of at least 450 Dalton and are different from the reaction product AC.

2. The composition of claim 1 , wherein a mass fraction of solids of the polyester resin composition (1) to the at least one other olefinically unsaturated compound (2) ranges from 95/5 to 50/50.

3. The composition of claim 1 , wherein the polyester resin composition (1) additionally comprises at least one olefinically unsaturated compound B which can be radically polymerized.

4. The composition of claim 3 , wherein the compound B is a reaction product of a polyol B1 and an olefinically unsaturated compound C which can be radically polymerized.

5. The composition of claim 1 , wherein the olefinically unsaturated compound (2) has a weight average molecular weight of at least 600 Dalton.

6. The composition of claim 1 , wherein compound C which can be radically polymerised is attached to the polyester resin backbone by an ester linkage.

7. The composition of claim 1 , wherein compound C which can be radically polymerised is attached to the polyester resin backbone by a urethane linkage.

8. The composition of claim 1 , wherein compound C is a (meth)acrylated compound.

9. The composition of claim 1 comprising, relative to the total weight of AC and D, from 3 to 30% by weight of the emulsifier D and from 70 to 97% by weight of the reaction product AC.

10. A process for preparing the composition of claim 1 , said process comprising adding to
at least one radiation curable aqueously dispersed polyester resin composition (1) comprising an emulsifier D and a reaction product AC of a hydroxy functional polyester resin A and an olefinically unsaturated compound C which can be radically polymerised and which is attached to the polyester resin backbone by an ester linkage or a urethane linkage, which composition (1), optionally contains an olefinically unsaturated compound B which can be radically polymerised, wherein the emulsifier D is compatible with the reaction product AC and where present, the olefinically unsaturated compound B, and wherein the emulsifier D is the polyesterification product of a fatty acid D1, a polyhydric alcohol D2 having at least three hydroxyl groups per molecule, a carboxylic acid D3 or its anhydride, and a monoalkoxy polyalkylene glycol D4;
at least one other olefinically unsaturated compound (2) selected from the group consisting of (meth)acrylated (poly)urethanes, (meth)acrylated epoxies, (meth)acrylated polyesters, (meth)acrylated polyethers, partially esterified styrene/maleic anhydride copolymers, and mixtures or copolymers thereof that have a weight average molecular weight of at least 450 Dalton and are different from the reaction product AC.

11. The process of claim 10 , comprising blending
the polyester resin composition (1) with
the olefinically unsaturated compound (2).

12. The process of claim 11 , comprising a step of diluting the polyester resin composition (1) in water prior to blending with the olefinically unsaturated compound (2).

13. The process of claim 11 , comprising a step of adjusting pH so that a difference in pH between the polyester resin composition (1) and the olefinically unsaturated compound (2) is at most 5 units prior to blending.

14. The process of claim 10 , comprising
a) mixing the reaction product AC of a hydroxy functional polyester resin A and an olefinically unsaturated compound C which can be radically polymerised and which is attached to the polyester resin backbone by an ester linkage or a urethane linkage, and, optionally the olefinically unsaturated compound B, with the olefinically unsaturated compound (2),
b) adding thereto at least one emulsifier D under stirring until a homogeneous mixture is obtained, followed by
c) dispersing in water to obtain a stable emulsion.

15. The process of claim 14 , wherein the reaction product AC is obtained by
a1) mixing in a reaction vessel, as starting materials, a fatty acid A1 having from 8 to 24 carbon atoms, a polyhydric aliphatic alcohol A3 having at least three hydroxyl groups, and an aromatic, cycloaliphatic or linear or branched aliphatic carboxylic acid A4 having at least two carboxyl groups, or an anhydride thereof, and optionally, an aliphatic or aromatic monocarboxylic acid A2 having at least two carbon atoms and not more than seven carbon atoms, and optionally, an oil A5, wherein the starting materials and amounts thereof are chosen in a way to ensure a stoichiometric excess of hydroxyl groups in a resulting mixture of the starting materials,
a2) heating the mixture of the starting materials to a temperature of from 140° C. to 250° C. under removal of water, to provide a hydroxy functional polyester resin A,
a3) adding the olefinically unsaturated compound C that is reactive with hydroxyl groups of A for formation of a chemical bond comprising a group which is an ester group or a urethane group, and heating a resulting mixture of A and C to effect a reaction and formation of the said chemical bonds.

16. The process of claim 15 , wherein the polyester resin A is mixed with a polyol B1 before reaction of step a3) with the olefinically unsaturated compound C.

17. The process according to claim 15 , wherein the oil A5 is an unsaturated oil.

18. A paint, coating, adhesive or ink prepared from the composition of claim 1 .

19. A method of use of the composition of claim 1 comprising:
adding one or more of additives selected from the group consisting of photoinitiators, pigments, colourants, dispersing agents, flow additives, thickening agents, matting agents, and adhesion promoters, to the coating composition of claim 1 ,
mixing and homogenising a resulting mixture to obtain a paint, adhesive, coating or ink,
coating a surface of a substrate by applying the paint, adhesive, coating or ink to the surface of the substrate in the form of a wet film,
drying or flushing off at least a part of water comprised in the film, and
exposing the coated substrate to high energy radiation to cure the film.

20. The method of claim 19 wherein in addition to the one or more additives, siccatives are added as a further additive, and wherein the coated substrate is concurrently with, or after, the irradiation, subjected to air oxidation to provide air drying.

21. A radiation curable aqueous coating composition comprising:
from 1 to 9

Assignees

• Peeters Stephan
• De Micheli Philippe
• Urbano Edmund
• Tielemans Michel
• ALLNEX Belgium SA

Inventors

• Peeters Stephan
• De Micheli Philippe
• Urbano Edmund
• Tielemans Michel

Classifications

• C09J167/07

  having terminal carbon-to-carbon unsaturated bonds · CPC title

• C09D175/14

  Polyurethanes having carbon-to-carbon unsaturated bonds · CPC title

• C09D167/07 Primary

  having terminal carbon-to-carbon unsaturated bonds · CPC title

• C09D135/00

  Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers · CPC title

• C09D133/14

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title