Radiation-curable compounds containing polyester acrylate

Patent metadata

Field	Value
Publication number	US-10844229-B2
Application number	US-201716341196-A
Country	US
Kind code	B2
Filing date	Oct 2, 2017
Priority date	Oct 13, 2016
Publication date	Nov 24, 2020
Grant date	Nov 24, 2020

Abstract

Radiation-curable, polyester acrylate-containing compositions (I) obtainable by reacting 0.5 to 20 mol % of a polyester polyol (A) and 0.5 to 30 mol % of a polyester diol (B) with 1 to 10 mol % of phthalic anhydride (C) and 65 to 75 mol % of (meth)acrylic acid (D) in the presence of an acidic esterification catalyst, a hydrocarbon (L), and a polymerization inhibitor. Reaction temperatures range from 60 to 140° C. The hydrocarbon (L) functions as solvent, forms an azeotropic mixture with water, and is removed distillatively after esterification. Water formed in the reaction is removed azeotropically. After neutralization of the esterification catalyst, free (meth)acrylic acid is reacted with an epoxide compound (E) in an amount equivalent to the acid number of the reaction mixture. The compound (E) has at least two epoxide groups per molecule. The compositions are suitable for coating the surfaces of solid substrates.

First claim

The invention claimed is:

1. A radiation-curable, polyester acrylate-containing composition (I) obtainable by reacting
0.5 to 20 mol % of at least one polyester polyol (A), prepared by reaction of the reactants adipic acid, phthalic anhydride, oleic acid and trimethylolpropane, where the polyester polyol has an OH functionality in the range from 3.0 to 3.9, and
0.5 to 30 mol % of at least one polyester diol (B), prepared by reaction of the reactants adipic acid, isophthalic acid, and 2-butyl-2-ethyl-1,3-propanediol,

in the presence of an acidic esterification catalyst and in the presence of at least one hydrocarbon (L) which functions as solvent and forms an azeotropic mixture with water, and also in the presence of at least one polymerization inhibitor, with azeotropic removal of water formed in the reaction, at temperatures in the range from 60 to 140° C., with
1 to 10 mol % of phthalic anhydride (C) and
65 to 75 mol % of (meth)acrylic acid (D)

in an esterification removing the hydrocarbon (L) distillatively after the esterification, and, after neutralization of the esterification catalyst, reacting free (meth)acrylic acid with an epoxide compound (E) in an amount equivalent to the acid number of the reaction mixture, the compound (E) having at least two epoxide groups per molecule, reaction taking place to an acid number of 5 or fewer mg KOH/g,
wherein:
the mol % figures are based on the total amount of the compounds (A), (B), (C) and (D) used for the reaction; and
the molar ratio of the compounds (A) and (B) is in the range from 10:1 to 1:40.

2. A radiation-curable composition (II) comprising 60 to 100 wt % of a polyester acrylate-containing composition (I) according to claim 1 and 0 to 40 wt % of dipropylene glycol di-acrylate (F)—wt % based in each case on the overall radiation-curable composition (II).

3. A coating compound comprising one or more than one composition (I) according to claim 1 .

4. A coating compound comprising one or more than one composition (II) according to claim 2 .

5. A method of coating solid substrates, the method comprising using the composition (I) according to claim 1 to coat solid substrates.

6. The method according to claim 5 , wherein the solid substrates comprise PVC.

7. The method according to claim 5 , wherein the solid substrates comprise cork.

8. A method of coating solid substrates, the method comprising using the composition (II) according to claim 2 to coat solid substrates.

9. The method according to claim 8 , wherein the solid substrates comprise PVC.

10. The method according to claim 8 , wherein the solid substrates comprise cork.

Assignees

• Basf Se

Inventors

• Kimpel Delphine
• Tranter Kenneth Shaun
• Kunz Daniel
• Cohen Kathrin
• Thuery Peter
• Roesch Christine
• Wahl Stefan

Classifications

• C08F290/061

  Polyesters; Polycarbonates · CPC title

• C08J7/043 Primary

  Improving the adhesiveness of the coatings per se, e.g. forming primers (adhesives in the form of films or foils characterised by the primer layers between the polymer carriers and the adhesives C09J7/50) · CPC title

• C09D4/06 Primary

  {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00 · CPC title

• C08J7/0427

  with only one layer of a composition containing a polymer binder (with more layers C08J7/042) · CPC title

• C08G63/47

  by unsaturated monocarboxylic acids or unsaturated monohydric alcohols or reactive derivatives thereof · CPC title