# US 11,078,336 B2 · Alkoxylated dispersing agents

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- Number: US 11,078,336 B2
- Document ID: US11078336B2
- Status: Granted
- Kind: B2
- Application number: 15/772,695
- Filed: 2016-11-09
- Published: 2019-10-24
- Granted: 2021-08-03
- Earliest claimed: 2015-11-10
- Assignees: Sun Chemical Corporation
- Applicants: Sun Chemical Corporation
- Inventors: Michael J. Jurek; Juanita Parris
- Web page: https://patentgrep.com/patent/US11078336B2

## CPC

- C08G 63/672: Dicarboxylic acids and dihydroxy compounds
- C08G 81/024: {Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G}
- A61K 6/20: Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish
- A61K 6/65: Dyes
- C08G 18/283: {Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds}
- C08G 63/676: in which at least one of the two components contains aliphatic unsaturation
- C08G 63/916: {Dicarboxylic acids and dihydroxy compounds}
- C08K 3/22: of metals
- C08K 5/12: of cyclic polycarboxylic acids
- C08L 67/025: {containing polyether sequences}
- C08L 71/02: Polyalkylene oxides
- C09D 11/101: Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
- C09D 11/104: Polyesters
- C09D 11/107: from unsaturated acids or derivatives thereof
- C09D 11/326: characterised by the pigment dispersant
- C09D 177/00: Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain (based on polyhydrazides C09D179/06; based on polyamide-imides C09D179/08); Coating compositions based on derivatives of such polymers
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)

## 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.

## Claims

### Claim 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.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

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.

### Claim 4 (depends on 1)

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.

### Claim 5 (depends on 1)

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.

### Claim 6 (depends on 1)

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.

### Claim 7 (depends on 1)

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.

### Claim 8 (depends on 1)

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.

### Claim 9 (depends on 1)

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.

### Claim 10 (depends on 1)

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

### Claim 11 (depends on 1)

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

### Claim 12 (depends on 1)

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

### Claim 13 (depends on 1)

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.

### Claim 14 (depends on 1)

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

### Claim 15 (depends on 1)

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

### Claim 16 (depends on 15)

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

### Claim 17 (depends on 1)

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

### Claim 18 (depends on 17)

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

### Claim 19 (depends on 17)

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

### Claim 20 (depends on 17)

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 %.

### Claim 21 (depends on 17)

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.

### Claim 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 from copolymers and terpolymers of polyethylene glycol, polypropylene glycol, and polybutylene glycol.

### Claim 23 (depends on 22)

The method of forming an alkoxylated polymer of claim 22, wherein at least one reactive terminal end is a site for an alkoxylation.

### Claim 24 (depends on 22)

The method of forming an alkoxylated polymer of claim 22, wherein the functional polar groups are independently selected from hydroxyl, carboxyl, anhydride, epoxy, thiol, amino, imino or isocyanate.

### Claim 25 (depends on 22)

The method of forming an alkoxylated polymer of claim 22, wherein the functional polar group is hydroxyl; 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 diol; and/or wherein one or more of the polyfunctional monomers and/or oligomers are two or more diols.

### Claim 26 (depends on 22)

The method of forming an alkoxylated polymer of claim 22, wherein the alkoxylated polymer is selected from alkoxylated polyester, alkoxylated polyurethane, and alkoxylated polyurethane-urea.

### Claim 27 (depends on 22)

The method of forming an alkoxylated polymer of claim 22, wherein the alkoxylated polymer is:
an alkoxylated polyester comprising:
a) a polyalkylene glycol copolymer backbone selected from copolymers of polyethylene glycol, 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.

### Claim 28 (depends on 22)

The method of claim 22 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.

### Claim 29 (depends on 22)

The method of claim 22 wherein the one or more polyfunctional monomers or oligomers do not contain isocyanate groups.

### Claim 30 (depends on 22)

The method of forming an alkoxylated polymer of claim 22, wherein the polyalkylene glycol polymer or copolymer is a copolymer of polyethylene glycol and polypropylene glycol, having two blocks of polyethylene glycol and one block of polypropylene glycol in a tri-block structure, or having two blocks of polyethylene glycol and one block of polypropylene glycol in a tri-block structure, or random sequences of polyethylene glycol and polypropylene glycol, or tapered sequences of polyethylene glycol and polypropylene glycol.

### Claim 31 (depends on 30)

The method of forming an alkoxylated polymer of claim 30, wherein the copolymer has at least one reactive terminal end that is a site for alkoxylation.