IP Library Granted Patent US 9,109,137
Granted Patent B2
US 9,109,137 · App. 14/372,383 · Granted Aug 18, 2015

Radiation curable (meth) acrylated compounds

Inventors: Luc Lindekens (Merchtem, BE); JoAnn Arceneaux (Marietta, GA); Ruben Cleymans (Halle, BE); Ichiro Nagakawa (Hiroshima, JP); Fumio Tanabiki (Hiroshima, JP); Hideo Hibiu (Hiroshima, JP)
Assignees: ALLNEX BELGIUM SA; DAICEL-ALLNEX LTD
C09D133/14C07C69/54C07D493/04C09D7/1216C08K3/36
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Quick Facts
Patent No.
US 9,109,137
App. No.
14/372,383
Granted
Aug 18, 2015
Kind
B2
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 (43)

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

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,

wherein if both compounds (b1) and (b2) are being used, compound (b1) forms a moiety that links the cyclic ether polyol (a) to the linking compound (b2) which attaches to the (meth)acrylating compound (c),

wherein at least one compound (b2) is being used, if a compound (b13) is being used, and

wherein the amounts of compounds (a), (b), and (c) sum up to 100%.

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 C 1 -C 4 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

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,

(c) a (at least one) (meth)acrylating compound,

wherein if both compounds (b1) and (b2) are being used, compound (b1) forms a moiety that links the cyclic ether polyol (a) to the linking compound (b2) which attaches to the (meth)acrylating compound (c).

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

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 optionally at least one linking compound (b2) selected from epihalohydrins or polyisocyanates,

(c) a (at least one) (meth)acrylating compound wherein if both compounds (b1) and (b2) are being used, compound (b1) forms a moiety that links the cyclic ether polyol (a) to the linking compound (b2) which attaches to the (meth)acrylating compound (c), and

wherein at least one compound (b2) is being used, if a compound (b13) is being used.

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.

Assignments (4)
CORRECTIVE ASSIGNMENT TO CORRECT THE NAME OF THE ASSIGNEE PREVIOUSLY RECORDED ON REEL 033555 FRAME 0338. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Sep 21, 2017
From: LINDEKENS, LUC; CLEYMANS, RUBEN; ARCENEAUX, JOANN
To: ALLNEX BELGIUM S.A.
Reel/Frame 044206/0160 →
CHANGE OF ADDRESS OF ASSIGNEE Recorded Sep 21, 2017
From: ALLNEX BELGIUM S.A.
To: ALLNEX BELGIUM S.A.
Reel/Frame 044168/0952 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 18, 2014
From: LINDEKENS, LUC; CLEYMANS, RUBEN; ARCENEAUX, JOANN
To: ALLNEX BELGIUM SA
Reel/Frame 033555/0338 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 18, 2014
From: NAGAKAWA, ICHIRO; TANABIKI, FUMIO; HIBIU, HIDEO
To: DAICEL-ALLNEX LTD
Reel/Frame 033555/0465 →
Priority Claims (1)
EP 12171575 · Jun 12, 2012 · regional
Continuity (3)
Provisional Application 61771233 · Mar 1, 2013
Provisional Application 61617870 · Mar 30, 2012
Related Publication 20150005408A1 · Jan 1, 2015