Acrylate-based monomers for use as reactive diluents in printing formulations

Patent metadata

Field	Value
Publication number	US-10745576-B2
Application number	US-201816484896-A
Country	US
Kind code	B2
Filing date	Feb 9, 2018
Priority date	Feb 10, 2017
Publication date	Aug 18, 2020
Grant date	Aug 18, 2020

Abstract

The invention relates to compositions, comprising. a) 1.00 to 65.00% by weight of at least one compound of formula (I), wherein R 1 , R 2 , R 3 , R 4 are each independently H, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, or C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl; R is H or C 1 -C 6 -alkyl; X is CR 6 R 7 , O, or NR 8 ; R 6 R 7 are each independently H, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, or C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl; R8 is H, C 1 -C 6 -alkyl, or C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl; k is 1, 2, 3, 4 or 5, as component A; b) 1.00 to 60.00% by weight of at least one monomer having two (meth)acrylate groups and having a molecular weight of no more than 500 Dalton, as component B; c) 0 to 25% by weight of at least one monomer having at least three (meth)acrylate groups and having a molecular weight of no more than 600 Dalton, as component C; and d) 1.00 to 30.00% by weight of at least one polymer having at least two (meth)acrylate groups and having a molecular weight of at least 700 Dalton, as component D; with the proviso that the amount of components A+B is at least 50% by weight, as well as the use of these compositions as printing inks, in particular inkjet printing inks.

First claim

The invention claimed is:

1. A composition, comprising
a) 1.00 to 65.00% by weight of at least one compound of formula (I),

wherein
R 1 , R 2 , R 3 , R 4 are each independently H, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, or C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl;
R 5 is H or C 1 -C 6 -alkyl;
X is CR 6 R 7 ;
R 6 , R 7 are each independently H, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, or C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl;
k is 1, 2, 3, 4 or 5,
as component A;
b) 1.00 to 60.00% by weight of at least one monomer having two (meth)acrylate groups and having a molecular weight M w no more than 500 Dalton, as component B;
c) 0 to 25% by weight of at least one monomer having at least three (meth)acrylate groups and having a molecular weight M w of no more than 600 Dalton, as component C;
d) 1.00 to 30.00% by weight of at least one polymer having at least two (meth)acrylate groups and having a molecular weight M w of at least 700 Dalton, as component D;
e) 0 to 20.00% by weight of one or more photoinitiators, as component E;
f) 0 to 10.00% by weight of one or more colorants, as component F;
g) 0 to 2.00% by weight of one or more stabilizers, as component G;
h) 0 to 50.00% by weight of one or more further monomers, as component H;
j) 0 to 10.00% by weight of one or more further additives, as component J;
with the proviso that the amount of components A) plus B) is at least 50% by weight, based on the total composition, and that in all cases the amounts of components A to J add up to 100% by weight.

2. The composition according to claim 1 , wherein the at least one compound of formula (I) is the compound of formula (Ia)

3. The composition according to claim 1 , consisting of
a) from 3.00% by weight to 50% by weight of component A;
b) from 5.00% by weight to 55% by weight of component B;
c) from 0.50% by weight to 22.50% by weight of component C;
d) from 3.00% by weight to 25.00% by weight of component D;
e) from 3.00% by weight to 15.00% by weight of component E;
f) from 0.10% by weight to 7.50% by weight of component F;
g) from 0.01% by weight to 1.50% by weight of component G;
h) from 0.00% by weight or from 1.00% by weight to 40.00% by weight of component H;
i) from 0.10% by weight to 7.50% by weight of component J;
wherein in all cases, the amount of components A+B is at least 50% by weight, and the amounts of components A to J add up to 100% by weight.

4. The composition according to claim 1 , wherein the at least one monomer having two (meth)acrylate groups of component B has a molecular weight in the range of 150 to 400 Dalton and a dynamic viscosity at 23° C. in the range of from 3 to 150 mPas, measured at a shear rate of 100 s −1 .

5. The composition according to claim 1 , wherein the at least one monomer having at least three (meth)acrylate groups of component C, has a molecular weight in the range of 200 to 550 Dalton and a dynamic viscosity at 23° C. in the range of from 10 to 200 mPas, measured at a shear rate of 100 s −1 .

6. The composition according to claim 1 , wherein the at least one polymer having at least two (meth)acrylate groups of component D has a molecular weight in the range of 1000 to 2000 Dalton and a dynamic viscosity at 23° C. in the range of from 100 to 2500 mPas, measured at a shear rate of 100 s −1 .

7. The composition according to claim 1 , wherein the at least one monomer having two (meth)acrylate groups of component B is selected from the group consisting of monomers of formula (B-1)

wherein
each R B1 is independently H or CH 3 ;
each Y B1 is independently ethylene, propylene, or butylene;
p is a number from 1 to 15,
and monomers of formula (B-2)

wherein
T is C 1 -C 10 -alkylene;
each R B2 is independently H or CH 3 ;
each Y B2 is independently ethylene, propylene, or butylene and
e and f are numbers, with the proviso that e+f is a number from 1 to 10.

8. The composition according to claim 1 , wherein the at least one monomer having at least three (meth)acrylate groups of component C, is selected from compounds of formula (C-1),

wherein
each R C1 is independently H or CH 3 ;
each R C1 is independently ethylene, propylene, or butylene;
a, b, c, and d are numbers, with the proviso that a+b+c+d is a number from 1 to 15.

9. The composition according to claim 1 , wherein the at least one polymer having at least two (meth)acrylate groups of component D is selected from the groups consisting of
a) amine modified polyether acrylate,
b) polyether acrylates which are not amine modified,
c) polyester acrylates and
d) urethane acrylates.

10. A method for printing, comprising the steps of:
a) applying the composition as claimed in claim 1 onto a substrate;
b) curing the composition.

11. The method according to claim 10 , which is a method for inkjet printing.

12. The composition according to claim 1 , wherein the composition is used as an ink jet ink and has a viscosity from 25-50 mPas at 23° C.

13. The composition according to claim 1 , wherein component D is present from 3.00% by weight to 20.00% by weight and has a molecular weight in the range of from 1500 to 2000 Dalton.

14. The composition according to claim 1 , wherein component B is present from 20 to 35% by weight and has a molecular weight in the range of from 150 to 350 Dalton.

15. The composition according to claim 1 , consisting of
a) from 5.00% by weight to 30% by weight of component A;
b) from 20% by weight to 35% by weight of component B which are monomers having two (meth)acrylate groups and have a molecular weight in the range of from 150 to 350 Dalton;
c) from 5.00% by weight to 15% by weight of component C;
d) from 7.50% by weight to 15.00% by weight of component D at least one polymer having at least two (meth)acrylate groups and have a molecular weight in the range of from 1500 to 2000 Dalton;
e) from 7.50% by weight to 12.00% by weight of component E;
f) from 1.00% by weight to 5.00% by weight of component F;
g) from 0.05% by weight to 0.50% by weight of component G;
h) from 0.00% by weight or from 1.00% by weight to 25.00% by weight of component H;
i) from 0.00% by weight or from 0.10% by weight to 3.00% by weight of component J;
wherein in all cases, the amount of components A+B is at least 50% by weight, and the amounts of components A to J add up to 100% by weight.

16. The composition according to claim 13 , wherein component B is present from 20 to 35% by weight and has a molecular weight in the range of from 150 to 350 Dalton.

Assignees

• Basf Se

Inventors

• Fleckenstein Christoph
• Baro Juergen
• Beck Erich
• Kaller Martin
• Misske Andrea
• Fleischhaker Friederike

Classifications

• C09D11/30

  Inkjet printing inks · CPC title

• C09D11/107 Primary

  from unsaturated acids or derivatives thereof · CPC title

• C09D11/101 Primary

  Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing · CPC title

• B41J11/002

  Curing or drying the ink on the copy materials, e.g. by heating or irradiating · CPC title

• C09D4/00 Primary

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title