Alkoxylated dispersing agents

Patent metadata

Field	Value
Publication number	US-11078336-B2
Application number	US-201615772695-A
Country	US
Kind code	B2
Filing date	Nov 9, 2016
Priority date	Nov 10, 2015
Publication date	Aug 3, 2021
Grant date	Aug 3, 2021

Abstract

Described herein are alkoxylated polymers suitable for use in primers, inks or coating compositions. The alkoxylated polymers derive from a polyalkylene glycol polymer or copolymer backbone having one or more alkoxylated sites in a non-reactive form and at least one reactive terminal end, and one or more polyfunctional monomers or oligomers having two or more functional polar groups with an active hydrogen, or mixtures thereof, wherein the alkoxylated polymer is polymerized in a one step process. Primers, inks or coating compositions are further described.

First claim

What is claimed is:

1. An alkoxylated polymer deriving from components comprising:
a polyalkylene glycol polymer or copolymer backbone having one or more alkoxylated sites in a non-reactive form and at least one reactive terminal end; and
one or more polyfunctional monomers or oligomers having two or more functional polar groups with an active hydrogen, or mixtures thereof,

wherein the alkoxylated polymer is polymerized in a one step process, wherein the polyalkylene glycol component is selected from copolymers and terpolymers of polyethylene glycol, polypropylene glycol, and polybutylene glycol.

2. The alkoxylated polymer of claim 1 , wherein the at least one reactive terminal end is a site for an alkoxylation.

3. The alkoxylated polymer of claim 1 , wherein the one or more polyfunctional monomers or oligomers have functional polar groups independently selected from hydroxyl, carboxyl, anhydride, thiol, amino, epoxy, imino, isocyanate, amido, or ureido.

4. The alkoxylated polymer of claim 1 , wherein one or more polyfunctional monomers or oligomers have at least one hydroxyl group; and/or wherein one or more of the polyfunctional monomers and/or oligomers is a diol; and/or wherein one or more of the polyfunctional monomers and/or oligomers are two or more diols; and/or wherein one or more of the polyfunctional monomers and/or oligomers is a —COOH functionalized diol; and/or wherein one or more of the polyfunctional monomers and/or oligomers is a diacid, an acid anhydride, and/or mixtures thereof; and/or wherein one or more of the polyfunctional monomers and/or oligomers is a diisocyanate.

5. The alkoxylated polymer of claim 1 , wherein the one or more polyfunctional monomers or oligomers is selected from the group consisting of trimethylol propane, ethylene glycol, diethylene glycol, propylene glycol, 1,4-butanediol, 1,2-propanediol, 1,3-propanediol, pentanediol, hexanediol, 2-methyl-1,3-propanediol, cyclohexyldimethanol, diethylene glycol, triethylene glycol, neopentylglycol, trimethylolethane, pentaerythritol, glycerol, dimethylolbutanoic acid, dimethylolpropionic acid, 1,2,4-benzenetriol, 1,3,5-benzenetriol, 1,2,3-benzenetriol, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, maleic acid, succinic acid, malonic acid, diethyl malonic acid, monobutyl maleate, 1,3-acetonedicarboxylic acid, benzylmalonic acid, biphenyl-4,4′-dicarboxylic acid, 1,3,5-cyclohexanetricarboxylic acid, cyclohexylsuccinic acid, trimethylolpropane tris(3-mercaptopropionate); trimethylolpropane tris(2-mercaptoacetate); pentaerythritol tetrakis(2-mercaptoacetate); pentaerythritol tetrakis(3-mercaptopropionate); 2,2′-(ethylenedioxy) diethanethiol; 1,3-propanedithiol; 1,2-ethanedithiol; 1,4-butanedithiol; tris[2-(3-mercaptopropionyloxy)ethyl] isocyanurate; 3,4-ethylenedioxythiophene, m-phenylenediamine, p-phenylenediamine, 1,3,5-triaminobenzene, 1,3,4-triaminobenzene, 3,5-diaminobenzoic acid, 2,4-diaminotoluene, 2,4-diaminoanisole, xylylenediamine, ethylenediamine, propylenediamine, tris (2-diaminoethyl) amine, bis(imino)pyridine; 3,3′-iminodipropionitrile; [2,6-bis(1-phenylimino)ethyl]pyridine, norbornene diamide, methylene dianiline, hydrogenated methylene dianiline, durene diamine, 1,3-butadiene diepoxide, diepoxybutane, 1,6-diazacyclododecane-2,5-dione, dimethylbis(ureido)silane, ureidopyrimidinone tetrahydrophthalic anhydride, phthalic anhydride, isophthalic anhydride, hexahydrophthalic anhydride, maleic anhydride, succinic anhydride, dimethyl isophthalate, 1,4-cyclohexanedicarboxylic acid, dimethyl terephthalate, adipic acid, sebacic acid, fumaric acid, azelaic acid, toluene diisocyanate, isophorone diisocyanate, and hydrogenated dicyclohexyl methane diisocyanate.

6. The alkoxylated polymer of claim 1 , wherein the alkoxylated polymer is selected from the group consisting of alkoxylated polyester, alkoxylated polyurethane, and alkoxylated polyurethane-urea.

7. The alkoxylated polymer of claim 1 , wherein the alkoxylated polymer is:
an alkoxylated polyester comprising:
a) a polyalkylene glycol copolymer backbone selected from copolymers of polyethylene glycol, and polypropylene glycol;
b) one or more diols or polyols; and
c) one or more diacids or acid anhydrides, or mixtures thereof; or

an alkoxylated polyurethane comprising:
a) a polyalkylene glycol polymer or copolymer backbone selected from copolymers of polyethylene glycol, polypropylene glycol, and copolymers thereof;
b) one or more diisocyanates; and
c) one or more diols or polyols.

8. The alkoxylated polymer of claim 1 , wherein the polyalkylene glycol component is a block copolymer having two blocks of polyethylene glycol and one block of polypropylene glycol in a tri-block structure.

9. The alkoxylated polymer of claim 1 , wherein the polyalkylene glycol component is a block copolymer having two blocks of polypropylene glycol and one block of polyethylene glycol in a tri-block structure.

10. The alkoxylated polymer of claim 1 , wherein the polyalkylene glycol component is a copolymer having random sequences of polyethylene glycol and polypropylene glycol.

11. The alkoxylated polymer of claim 1 , wherein the polyalkylene glycol component is a copolymer having tapered sequences of polyethylene glycol and polypropylene glycol.

12. The alkoxylated polymer of claim 1 , wherein one or more of the polyfunctional monomers and/or oligomers is a —COOH functionalized diol.

13. The alkoxylated polymer of claim 1 wherein, when the one or more polyfunctional monomers or oligomers are
(a) one or more diol or polyol, and
(b) one or more diisocyanates,

wherein the polyalkylene glycol polymer or copolymer and the one or more diol or polyol together comprise an equimolar amount of hydroxyl groups relative to the isocyanate groups in the one or more diisocyanates.

14. The alkoxylated polymer of claim 1 wherein the one or more polyfunctional monomers or oligomers do not contain isocyanate groups.

15. The alkoxylated polymer of claim 1 , wherein the polyalkylene glycol component is a copolymer of polyethylene glycol and polypropylene glycol.

16. The alkoxylated polymer of claim 15 , wherein the copolymer has at least one reactive terminal end that is a site for alkoxylation.

17. A primer, ink, or coating composition comprising the alkoxylated polymer of claim 1 .

18. The primer, ink, or coating composition of claim 17 , wherein the alkoxylated polymer is a dispersing agent or a low tack binder.

19. The primer, ink, or coating composition of claim 17 , which is a gravure or flexographic primer, ink, or coating composition.

20. The primer, ink, or coating composition of claim 17 , wherein the alkoxylated polymer is present in an amount from about 0.1 to about 25 wt %.

21. The primer, ink, or coating composition of claim 17 , wherein the primer, ink, or coating composition exhibits an improvement in a property that is at least one of opacity, gloss, scratch resistance, and laydown, when compared to a primer, printing ink, or coating composition not including an alkoxylated polymer.

22. A method of forming an alkoxylated in one polymerization step, comprising:
polymerizing, in one step, a backbone-forming polyalkylene glycol polymer or copolymer having one or more alkoxylated sites in non-reactive form and at least one reactive terminal end with one or more polyfunctional monomers or oligomers having two or more functional polar groups with an active hydrogen, or mixtures thereof, wherein the polyalkylene glycol component is selected

Assignees

• Sun Chemical Corp

Inventors

• Jurek Michael J
• Parris Juanita

Classifications

• C08L71/02

  Polyalkylene oxides · CPC title

• C08G63/676

  in which at least one of the two components contains aliphatic unsaturation · CPC title

• C08K5/12

  of cyclic polycarboxylic acids · CPC title

• A61K6/65

  Dyes · CPC title

• C09D11/101

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