Radiation curable compositions with anti-stain properties

Patent metadata

Field	Value
Publication number	US-11359110-B2
Application number	US-201716334424-A
Country	US
Kind code	B2
Filing date	Sep 29, 2017
Priority date	Sep 30, 2016
Publication date	Jun 14, 2022
Grant date	Jun 14, 2022

Abstract

The radiation curable compositions (I) that comprise from 10 to 80 by weight of at least one silicone-modified urethane (meth) acrylate (A), from 0.5 to 60 by weight of at least one (meth) acrylated compound (B) bearing at least 5 (meth) acryloyl groups per molecule, and optionally, from 10 to 60% by weight of at least one compound (C) different from (A) or (B), wherein the weight percentages are on the total weight of the composition (I). These materials can be used for producing coatings, inks and overprint varnishes with excellent anti-stain properties, to their use and preparation. Materials of the invention are compatible with standard radiation curable materials. They allow to obtain excellent anti-stain properties for high gloss coatings as well as for matte coatings (II) with a gloss level at 60° of at most 15, even at most 10.

First claim

The invention claimed is:

1. A radiation curable composition (I) comprising:
from 10 to 80% by weight of at least one silicone-modified urethane (meth)acrylate (A),
from 0.5 to 60% by weight of at least one (meth)acrylated compound (B) bearing at least 5 (meth)acryloyl groups per molecule, and
optionally, from 0 to 60% by weight of at least one compound (C) different from (A) and (B),

wherein the weight percentages are based on the total weight of the composition (I),
wherein the silicone-modified urethane (meth)acrylate (A) is prepared by reacting:
(i) at least one polysiloxane having at least two isocyanate reactive groups,
(ii) at least one polyisocyanate, and
(iii) at least one compound having at least one (meth)acryloyl group and at least one isocyanate reactive group, and

wherein the silicone-modified urethane (meth)acrylate (A) is prepared by reacting, in a first step, the at least one polyisocyanate (ii) with the at least one compound having at least one (meth)acryloyl group and at least one isocyanate reactive group (iii), and then by reacting, in a further step, the reaction product of the first step with the at least one polysiloxane having at least two isocyanate reactive groups (i),
wherein, in the first step, the molar equivalent ratio of the isocyanate groups in the at least one polyisocyanate (ii) to the hydroxyl groups of the at least one compound having at least one (meth)acryloyl group and at least one isocyanate reactive group (iii) is from 2:1 to 1.1:1.

2. The radiation curable composition (I) according to claim 1 , wherein the molar equivalent ratio of the at least one compound having at least one (meth)acryloyl group and at least one isocyanate reactive group (iii) to the at least one polysiloxane having at least two isocyanate reactive groups (i) is from 2:1 to 10:1.

3. The radiation curable composition (I) according to claim 1 , wherein the at least one polysiloxane having at least two isocyanate reactive groups (i) comprises between 5 and 100 —SiO— units.

4. The radiation curable composition (I) according to claim 1 , wherein the at least one polysiloxane having at least two isocyanate reactive groups (i) is selected from the group consisting of polydialkyl siloxanes, polyalkylaryl siloxanes, polydiaryl siloxanes, and mixtures thereof.

5. The radiation curable composition (I) according to claim 1 , wherein the at least one polysiloxane having at least two isocyanate reactive groups (i) is a polydialkyl siloxane bearing terminal hydroxyl groups.

6. The radiation curable composition (I) according to claim 1 , wherein the at least one (meth)acrylated compound (B) bears from 6 to 15 (meth)acryloyl groups per molecule.

7. The radiation curable composition (I) according to claim 1 , wherein at least one (meth)acrylated compound (B) has a degree of unsaturation of at least 4 meq/g and at most 12 meq/g.

8. The radiation curable composition (I) according to claim 1 , wherein the at least one (meth)acrylated compound (B) is selected from the group consisting of urethane (meth)acrylates (B1), polyester (meth)acrylates (B2), (meth)acrylated poly(meth)acrylics (B3), and mixtures thereof.

9. A coating composition, an ink or an overprint varnish comprising the radiation curable composition (I) according to claim 1 .

10. A coating composition (II) comprising from 5 to 95% by weight of the radiation curable composition (I) according to claim 1 , and from 0.5 to 30% by weight of at least one organic and/or inorganic matting agent (D).

11. The coating composition (II) according to claim 10 , wherein, after curing, the coating composition (II) has a gloss level at 60° of at most 15.

12. An article or substrate coated, at least in part, with the coating composition (II) according to claim 10 .

13. A substrate coated, at least in part, with the coating composition (II) according to claim 10 , wherein the substrate is selected from the group consisting of fabric, glass, metal, metalloid, metal oxide, ceramic, wood, plastic, resin, rubber, stone, concrete, fittings in electronics, a semiconductor, a particle, and combinations thereof.

14. The radiation curable composition (I) according to claim 1 , wherein, in the first step, the molar equivalent ratio of the isocyanate groups in the at least one polyisocyanate (ii) to the hydroxyl groups of the at least one compound having at least one (meth)acryloyl group and at least one isocyanate reactive group (iii) is from 1.8:1 to 1.2:1.

Assignees

• ALLNEX Belgium SA
• Allnex Resins Shanghai Co Ltd

Inventors

• Cheng Xie
• Cappelle Steven
• Burie Peter
• Chen Dong
• Chen Rong

Classifications

• C08F222/1065

  of alcohol terminated (poly)urethanes, e.g. urethane(meth)acrylates · CPC title

• C09D11/54

  Inks based on two liquids, one liquid being the ink, the other liquid being a reaction solution, a fixer or a treatment solution for the ink · CPC title

• C09D175/16 Primary

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

• C08G18/61

  Polysiloxanes · CPC title

• C08G18/6725

  containing ester groups other than acrylate or alkylacrylate ester groups · CPC title