Polar functional non-aqueous acrylic dispersions

Patent metadata

Field	Value
Publication number	US-11767395-B2
Application number	US-201716082628-A
Country	US
Kind code	B2
Filing date	Mar 13, 2017
Priority date	Mar 18, 2016
Publication date	Sep 26, 2023
Grant date	Sep 26, 2023

Abstract

Described herein is a polar non-aqueous dispersion comprising polar polymeric microparticles in a polar non-aqueous medium, the polar polymeric microparticles being insoluble in the medium and being produced by dispersion polymerization of vinyl monomers such as acrylate monomers in the medium in the presence of a polymeric acrylic stabilizer. Inks, coatings and overprint varnishes are formulated that employ the polar non-aqueous dispersion. Such inks, etc., exhibit superior chemical resistance properties, for example in one-part and two-part systems.

First claim

What is claimed is:

1. A polar non-aqueous dispersion comprising:
(a) polar polymeric microparticles having one or more polar functional groups, wherein the one or more polar functional groups are selected from the group consisting of hydroxyl groups, carbonyl groups, ether groups, ester groups, amide groups, amino groups, halogenated hydrocarbon groups, nitrile groups, and combinations thereof, wherein the polar polymeric particles contain no carboxylic acid functionality; and
(b) a polar non-aqueous medium;
wherein:
(i) the polar polymeric microparticles are insoluble in the polar non-aqueous medium;
(ii) the polar polymeric microparticles are produced by dispersion polymerization of one or more vinyl monomers in the polar non-aqueous medium in the presence of a polymeric acrylic stabilizer, wherein:
at least one vinyl monomer is a hydroxyalkyl ester of αβ-unsaturated carboxylic acids with primary or secondary hydroxyl groups; and
the sum of the amount of vinyl monomers selected from the group consisting of, betacarboxyethylacrylate, 2-hydroxyethyl acrylate, and acrylonitrile, and mixtures thereof is less than 50 wt %, based on the total weight of all the vinyl monomers;
wherein no unsaturated carboxylic acids are included in the dispersion polymerization of one or more vinyl monomers.

2. The polar non-aqueous dispersion of claim 1 , wherein the polar non-aqueous medium is comprised of esters, ketones, and mixtures thereof, wherein the vinyl monomers are soluble in the medium.

3. The polar non-aqueous dispersion of claim 1 , wherein the polar non-aqueous medium is selected from n-propyl acetate, ethyl acetate, n-butyl acetate, n-hexyl acetate, methyl ethyl ketone; methyl isobutyl ketone, and mixtures thereof.

4. The polar non-aqueous dispersion of claim 1 , wherein the vinyl monomer component comprising hydroxyalkyl esters of αβ-unsaturated carboxylic acids with primary or secondary hydroxyl groups is selected from hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxylbutyl acrylate, hydroxyamyl acrylate, hydroxylhexyl acrylate, hydroxyoctyl acrylate, the corresponding (meth)acrylates thereof; 2-hydroxypropyl acrylate, 2-hydroxybutyl acrylate, 3-hydroxybutyl acrylate, the corresponding (meth)acrylates thereof; and mixtures of the above.

5. The polar non-aqueous dispersion of claim 1 , wherein the vinyl monomer component comprising one or more other vinyl monomers are selected from functional or non-functional vinyl monomers selected from acetoacetoxyethyl (meth)acrylate, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, isopropyl (meth)acrylate, isobutyl (meth)acrylate, pentyl (meth)acrylate, isoamyl (meth)acrylate, hexyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, octyl (meth)acrylate, 3,5,5-trimethylhexyl (meth)acrylate, decyl (meth)acrylate, dodecyl (meth)acrylate, hexadecyl (meth)acrylate, octadecyl (meth)acrylate, octadecenyl (meth)acrylate, maleic acid esters thereof, fumaric acid esters thereof, crotonic acid esters thereof, isocrotonic acid esters thereof, vinylacetic acid esters thereof, itaconic acid esters thereof; alkoxyethyl acrylates, aryloxyethyl acrylates, corresponding (meth)acrylates thereof; unsaturated compounds with tertiary amino groups; acrylonitrile, methacrylonitrile, acrolein, methacrolein; and mixtures of the above.

6. The polar non-aqueous dispersion of claim 1 , wherein the polymeric acrylic stabilizer comprises a polymerization product comprised of vinyl monomers selected from non-functional vinyl monomers; hydroxyl-functional vinyl monomers; glycidyl-functional vinyl monomers; amino-functional vinyl monomers; silane-functional vinyl monomers; N-alkoxyalkyl functional vinyl monomers, and mixtures thereof.

7. The polar non-aqueous dispersion of claim 1 , wherein the dispersion polymerization of one or more vinyl monomers in the polar non-aqueous medium takes place in the presence of a polymerization initiator.

8. The polar non-aqueous dispersion of claim 7 , wherein the polymerization initiator is selected from the group consisting of a peroxy initiator, a persulfate initiator, a perborate initiator, a percarbonate initiator, an azo compound initiator, and mixtures thereof.

9. The polar non-aqueous dispersion of claim 1 , wherein the polar polymeric microparticles comprise crosslinked polymer chains.

10. The non-aqueous dispersion of claim 1 , wherein the particle size of the polar polymeric microparticles is about 0.1 microns to about 5 microns.

11. The polar non-aqueous dispersion of claim 1 , wherein the particle size of the polar polymeric microparticles is about 0.3 microns to about 0.9 microns.

12. The polar non-aqueous dispersion of claim 1 , wherein the dispersion has a number average molecular weight (Mn) of at least 1,000 Dalton.

13. The polar non-aqueous dispersion of claim 1 , wherein the dispersion has a number average molecular weight (Mn) greater than about 33,000 Daltons.

14. A polar non-aqueous dispersion comprising the polar polymeric microparticles of the polar non-aqueous dispersion of claim 1 , transferred to a second polar non-aqueous medium that is different from the polar non-aqueous medium of claim 1 .

15. An ink, coating, primer, or overprint varnish composition, comprising the polar non-aqueous dispersion of claim 1 .

16. The ink, coating, primer, or overprint varnish composition of claim 15 , comprising, by weight, about 1% to about 90% of the polar non-aqueous dispersion.

17. A process of coating a substrate to improve wear resistance, comprising applying the ink, coating, primer, or overprint varnish composition of claim 15 to a substrate.

18. The process of claim 17 , wherein the ink, coating, primer, or overprint varnish is applied by a deposition method selected from flexo, litho offset, gravure, screen, digital, rod, curtain, cascade, roll, slot, spray, and a combination thereof.

19. A multilayer structure comprising:
a substrate, optionally having a primer layer applied thereto;
a plurality of ink layers;
optionally, an overprint varnish layer, wherein one or more of the layers comprises the polar non-aqueous dispersion of claim 1 .

20. A multilayer structure comprising:
a substrate, optionally having a primer layer applied thereto;
a plurality of ink layers;
optionally, an overprint varnish layer, wherein one or more of the layers comprises the polar non-aqueous dispersion of claim 9 .

21. The polar non-aqueous dispersion of claim 1 , wherein the amount of (a) betacarboxyethylacrylate, 2-hydroxyethyl acrylate, acrylonitrile, and mixtures thereof is less than 50 wt %; and the amount of vinyl monomer other than those in (a) is greater than 50 wt %.

Assignees

• Sun Chemical Corp

Inventors

• Parris Juanita M
• Omizu Soichiro
• Weisbecker Carl S
• Rosen Josie M
• Arcurio Ralph
• Krishnan Ramasamy
• Chudolij Alex

Classifications

• C08G18/6233 Primary

  the monomers or polymers being esterified with carboxylic acids or lactones · CPC title

• C08F2/08

  with the aid of dispersing agents for the polymer · CPC title

• C08F220/06

  Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof · CPC title

• C08F220/1804

  C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate · CPC title

• C08F220/283

  and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate · CPC title