Radiation curable (meth) acrylated compounds

• US 9,109,137 B2
• Filed: 03/22/2013
• Issued: 08/18/2015
• Est. Priority Date: 03/30/2012
• Status: Active Grant

• Current Assignee: Allnex Belgium SA (Allnex Holding S.a r.l.), Daicel-Allnex Ltd. (Daicel Corporation)
• Original Assignee: Allnex Belgium SA (Allnex Holding S.a r.l.), Daicel-Allnex Ltd. (Daicel Corporation)
• Inventors: Lindekens, Luc, Arceneaux, JoAnn, Cleymans, Ruben, Nagakawa, Ichiro, Tanabiki, Fumio, Hibiu, Hideo
• Primary Examiner(s): Choi, Ling
• Assistant Examiner(s): WHITELEY, JESSICA
• Application Number:
  US14/372,383
• Publication Number:
  US 20150005408A1
• Time in Patent Office: 879 Days
• Field of Search: 522/170, 522/168, 522/1, 520/1
• US Class Current: 1/1
• CPC Class Codes: C07C 69/54 Acrylic acid esters; Methacrylic acid esters
• CPC Class Codes: C07D 493/04 Ortho-condensed systems
• CPC Class Codes: C08K 3/36 Silica
• CPC Class Codes: C09D 133/14 of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: C09D 7/61 inorganic

Abstract

The present invention relates to (meth)acrylated compounds (A) prepared from (a) at least one cyclic ether polyol, (b) at least one linking compound (b1) and/or (b2), wherein the linking compound (b1) is selected from cyclic compounds (b11) containing at least one (I) group in the cycle where X=O or NH, from hydroxy acids (b12) and/or from alkylene oxides (b13) containing from 2 to 4 carbon atoms and the linking compound (b2) is selected from epihalohydrins or polyisocyanates, (c) a (meth)acrylating compound; and to their use in radiation curable compositions for the coatings, inks, overprint varnishes, adhesives and composites.

Claims

1. A (meth)acrylated compound (A) prepared from

(a) at least one cyclic ether polyol,

(b) at least one linking compound (b1) and/or (b2), wherein the linking compound

(b1) is selected from cyclic compounds (b11) containing at least one

2. The compound according to claim 1, wherein the cyclic ether polyol is selected from dianhydrohexitols.

3. The compound according to claim 1, wherein the cyclic ether polyol is isosorbide.

4. The compound according to claim 1, wherein the linking compound (b11) is selected from lactones, lactides, lactams and mixtures thereof.

5. The compound according claim 1, wherein the linking compound (b12) is glycolic acid.

6. The compound according claim 1, wherein the linking compound (b13) is selected from ethylene oxide, propylene oxide and mixtures thereof.

7. The compound according to claim 1, wherein the epihalohydrin is epichlorhydrin.

8. The compound according to claim 1, wherein the polyisocyanate is selected from aliphatic polyisocyanates.

9. The compound according to claim 1, wherein the (meth)acrylating compound (c) is selected from an unsaturated acid, an acyl halide of the unsaturated acid, a corresponding anhydride of the unsaturated acid, a C₁-C₄ alkyl ester of the unsaturated acid (c1), or from compounds containing at least one reactive group capable to react with isocyanate groups as well as at least one (meth)acryloyl group (c2).

10. The compound according to claim 9, wherein the (meth)acrylating compound (c1) is selected from acrylic acid, methacrylic acid and mixtures thereof.

11. The compound according to claim 9, wherein the (meth)acrylating compound (c2) is selected from hydroxyethylacrylate, glycerol diacrylate, trimethylolpropane diacrylate and mixtures thereof.

12. The (meth)acrylated compound (A) according to claim 1 prepared from:

(a) at least one cyclic ether polyol,

(b) at least one linking compound (b2) selected from epihalohydrins or polyisocyanates and optionally at least one linking compound (b1) selected from cyclic compounds (b11) containing at least one

13. The (meth)acrylated compound (A) according to claim 1 prepared from:

(a) at least one cyclic ether polyol,

(b) at least one aliphatic linking compound (b1) selected from cyclic compounds (b11) containing at least one

14. A radiation curable composition comprising

at least 5% by weight relative to the total weight of the organic non-volatile content of the composition of at least one (meth)acrylated compound (A) according to claim 1,

optionally a reactive diluting monomer (B),

optionally at least one compound (C) selected from polyester (meth)acrylates, urethane (meth)acrylates, alkoxylated (meth)acrylated oligomers, epoxy (meth)acrylates, aminated (meth)acrylates, (meth)acrylated (meth)acrylics, (meth)acrylic (co)polymers and inert polyesters that optionally are chlorinated, and

optionally at least one photoinitiator (D).

15. The radiation curable composition according to claim 14 further comprising a nanoscale filler (E).

16. The radiation curable composition according to claim 15, wherein the nanoscale filler (E) is selected from silica, zirconia, titania, ceria, alumina, antimony oxide and is present in an amount of at least 10% by weight relative to the total weight of the organic non-volatile content of the composition.

17. The radiation curable composition according to claim 15, wherein the filler (E) is a nanoparticulate silica having a volume median diameter of from 1 to 100 nm.

18. The radiation curable composition according to claim 14 which is a coating, an ink, or an overprint varnish.

19. An article or substrate, having applied to at least part of one of its surfaces a composition of claim 14.

20. The radiation curable composition according to claim 14 comprising at least one photoinitiator (D).

21. The radiation curable composition according to claim 14 comprising at least one compound (C) selected from polyester (meth)acrylates, urethane (meth)acrylates, alkoxylated (meth)acrylated oligomers, epoxy (meth)acrylates, aminated (meth)acrylates, (meth)acrylated (meth)acrylics, (meth)acrylic (co)polymers and inert polyesters that optionally are chlorinated.