Radiation curable (meth)acrylated compounds

• US 9,540,310 B2
• Filed: 03/22/2013
• Issued: 01/10/2017
• Est. Priority Date: 03/30/2012
• Status: Active Grant

• Current Assignee: Allnex Belgium SA (Allnex Holding S.a r.l.)
• Original Assignee: Allnex Belgium SA (Allnex Holding S.a r.l.)
• Inventors: Lindekens, Luc, Randoux, Thierry, Cleymans, Ruben, Gevaert, Paul
• Primary Examiner(s): MCCLENDON, SANZA L
• Application Number:
  US14/372,387
• Publication Number:
  US 20140364530A1
• Time in Patent Office: 1,390 Days
• US Class Current: 1/1
• CPC Class Codes: C07C 271/24 with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
• CPC Class Codes: C07C 69/604 Polycarboxylic acid esters, the acid moiety containing more than two carboxyl groups
• CPC Class Codes: C07D 493/04 Ortho-condensed systems
• CPC Class Codes: C08G 18/4244 containing oxygen in the form of ether groups
• CPC Class Codes: C08G 18/8175 with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen
• CPC Class Codes: C08G 63/47 by unsaturated monocarboxylic acids or unsaturated monohydric alcohols or reactive derivatives thereof
• CPC Class Codes: C09D 11/107 from unsaturated acids or derivatives thereof
• CPC Class Codes: C09D 133/08 Homopolymers or copolymers of acrylic acid esters
• CPC Class Codes: C09D 167/07 having terminal carbon-to-carbon unsaturated bonds
• CPC Class Codes: C09D 175/16 having terminal carbon-to-carbon unsaturated bonds

Abstract

The present invention relates to a (meth)acrylated compound (A) prepared from: (i) a polyol constituent, (ii) a polyacid constituent and (iii) one or more (meth)acrylating compounds, wherein the polyol constituent comprises at least 30% by weight of one or more cyclic ether polyols, relative to the total weight of the polyol constituent, and wherein the compound (A) optionally further contains one or more moieties selected from the group consisting of (poly)caprolactone-containing moieties (ai), (poly)lactide- and/or (poly)glycolide-containing moieties (aii), moieties providing epoxide groups (aiii) and moieties providing alkylene oxide groups containing from 2 to 4 carbon atoms (aiv). The compounds of the invention are in particular suited for the making of radiation curable coating compositions and inks less prone to migration.

Claims

1. A radiation curable composition comprising:

a) at least one (meth)acrylated compound (A) prepared from;

(i) a polyol constituent, (ii) a polyacid constituent and (iii) one or more (meth)acrylating compounds, wherein the polyol constituent comprises, relative to the total weight of the polyol constituent, at least 30% by weight of one or more dianhydrohexitols, and wherein the compound (A) optionally further contains one or more moieties selected from the group consisting of (poly)caprolactone-containing moieties (ai), (poly)lactide- and/or (poly)glycolide-containing moieties (aii), moieties providing epoxide groups (aiii) and moieties providing alkylene oxide groups containing from 2 to 4 carbon atoms (aiv), and

b) at least one compound (B3) represented by the general formula (VI);

Y—

X(A)_n′

—

Y′

wherein;

Y and Y′

independently are the residues of a (meth)acrylating compound;

X is the residue of a dianhydrohexitol;

A represents a residue of a (poly)caprolactone, a (poly)lactide, a (poly)glycolide, a compound providing epoxide groups, and/or of an alkylene oxide group containing from 2 to 4 carbon atoms; and

n′

is an integer from 0 to 10.

2. The radiation curable composition of claim 1, wherein the polyol constituent comprises from 40 to 100% by weight of dianhydrohexitols and, optionally, from 0 to 60% by weight of one or more polyols that are different from cyclic ether polyols.

3. The radiation curable composition of claim 1, wherein the dianhydrohexitol is isosorbide.

4. The radiation curable composition of claim 1, wherein the (meth)acrylating compounds (iii) are attached to the molecule'"'"'s backbone via ester groups and/or via carbamate groups.

5. The radiation curable composition of claim 1, wherein the at least one (meth)acrylated comound (A) is represented by the general formula (I):

Y-[Polyol(A)_n-Polyacid]_m-X(A)_n′

-Y′

wherein;

Y and Y′

independently are the residues of a (meth)acrylating compound;

X is the residue of a dianhydrohexitol;

A represents the residue of a (poly)caprolactone, a (poly)lactide, a (poly)glycolide, a compound providing epoxide groups, or of an alkylene oxide group containing from 2 to 4 carbon atoms;

n and n′

independently are integers from 0 to 10; and

m is an integer from 1 to 5.

6. The radiation curable composition of claim 5, wherein the (meth)acrylating compounds are selected from:

an unsaturated acid, an acyl halide of the unsaturated acid, and/or a C₁-C₄ alkyl ester of the unsaturated acid.

7. The radiation curable composition of claim 5, wherein the (meth)acrylating compound (iii) is (meth)acrylic acid.

8. The radiation curable composition of claim 5, wherein the (meth)acrylating compound (iii) is the reaction product of at least one polyisocyanate (iv) and at least one compound (v) containing at least one reactive group capable to react with isocyanate groups as well as at least one (meth)acryloyl group.

9. The radiation curable composition of claim 1 comprising at least 5% by weight of at least one compound (A).

10. The radiation curable composition of claim 1, further comprising at least one compound (B1) selected from polyester (meth)acrylates, epoxy (meth)acrylates, urethane (meth)acrylates and/or acrylic copolymers.

11. The radiation curable composition of claim 1 further comprising at least one photo-initiator.

12. The radiation curable composition of claim 1 which is a hard coat composition that after curing has a Persoz hardness of at least 300 sec as measured at 25°

C. on 40μ

films on glass.

13. The radiation curable composition of claim 1 which is an ink.

14. An article or substrate, having applied to a least one of its surfaces the radiation curable composition of claim 1.

15. The radiation curable composition of claim 1, wherein n′

is 0.

16. The radiation curable composition of claim 11, wherein the photo-initiator is a polymeric photo-initiator (B2).