Associative rheology modifier composition and methods for making thereof

Patent metadata

Field	Value
Publication number	US-12577415-B2
Application number	US-202217662674-A
Country	US
Kind code	B2
Filing date	May 10, 2022
Priority date	May 11, 2021
Publication date	Mar 17, 2026
Grant date	Mar 17, 2026

Abstract

An associative rheology modifier is obtained by coupling of a rheology modifier precursor with a coupling agent. The rheology modifier precursor is formed by reacting a rosin acid with a polyether at a mole ratio of the rosin acid to the polyether of >2:1, at a temperature from 180-350° C. and in the presence of an acid catalyst. The polyether has a molecular weight of 500-10,000 g/mol and the rheology modifier precursor has a water solubility of >10 wt. % concentration. The associative rheology modifier has a molecular weight (Mw) from 1500-25,000 g/mol. The associative rheology modifier shows a high shear thinning effect at low shear rate. A composition is also provided comprising the associative rheology modifier.

First claim

The invention claimed is:

1 . An associative rheology modifier obtained by coupling of a rheology modifier precursor with a coupling agent,
wherein the rheology modifier precursor is formed by reacting a rosin acid with a polyether at a mole ratio of the rosin acid to the polyether of >2:1, at a temperature from 180-350° C. and in the presence of an acid catalyst,
the polyether has a molecular weight (Mw) of 500-10,000 g/mol; and
the rheology modifier precursor has a water solubility of >10 wt. % concentration;
wherein the coupling agent is present in an amount of 0.1-15 wt. %, based on the total weight of the coupling agent and the rheology modifier precursor, wherein the coupling agent is reactive to carbon-carbon double bonds in the rheology modifier precursor and selected from the group consisting of sulfur-based agents, peroxide-based agents, acrylate-based agents, tellurium, selenium, polysulfide polymers, metallic oxides, di-isocyanates, and mixtures thereof; wherein the associative rheology modifier has
a molecular weight (Mw) of 1,500-25,000 g/mol; and
an apparent viscosity of 100,000-2,000 cP at a shear rate from 1,500-5,000 s −1 and an apparent viscosity of 2,000-100 cP at a shear rate from 5,000-20,000 s −1 , at a concentration of 25 wt. % in water and a temperature of 25° C.

2 . The associative rheology modifier of claim 1 , wherein the polyether has at least one functional group selected from a hydroxyl group and an amine group.

3 . The associative rheology modifier of claim 1 , wherein the polyether is selected from the group of polyether glycols, polyetheramine, and mixtures thereof.

4 . The associative rheology modifier of claim 3 , wherein the polyether glycols are selected from a polyethylene glycol, a polypropylene glycol, a polybutylene glycol, a polytetrahydrofuran, a polytetramethylene glycol, a polytetramethylene ether glycol, and mixtures thereof.

5 . The associative rheology modifier of claim 1 , wherein the polyether is a polyethylene glycol, and wherein the rosin acid is reacted with the polyethylene glycol to obtain a polyethylene glycol end-capped rosin with an ester linkage.

6 . The associative rheology modifier of claim 1 , wherein the polyether is a polyetheramine, and wherein the rosin acid is reacted with the polyetheramine, to obtain a polyetheramine end-capped rosin with an amide linkage.

7 . The associative rheology modifier of claim 1 , wherein the rosin acid is reacted with an adduction agent to obtain a rosin acid adduct through a Diels-Alder reaction, wherein the adduction agent is selected from the group consisting of unsaturated acids, anhydrides, and mixtures thereof.

8 . The associative rheology modifier of claim 7 , wherein the rosin acid adduct is reacted with the polyether to form a rheology modifier precursor.

9 . The associative rheology modifier of claim 1 , wherein the rheology modifier precursor has the water solubility of 20-100 wt. % concentration.

10 . The associative rheology modifier of claim 1 , wherein the mole ratio of the rosin acid to the polyether is from 2:1-4:1.

11 . The associative rheology modifier of claim 1 , wherein the acid catalyst is a Brønsted acid.

12 . The associative rheology modifier of claim 11 , wherein the Brønsted acid is at least one selected from the group consisting of mineral acids, organic acids, heteropolyacids, zeolites, acid clays, sulfated zirconia, and mixtures thereof.

13 . The associative rheology modifier of claim 11 , wherein the Brønsted acid is at least one selected from hydrochloric acid, nitric acid, phosphoric acid, hypophosphorous acid, sulfuric acid, boric acid, hydrofluoric acid, hydrobromic acid, hydroiodic acid, toluenesulfonic acid, formic acid, acetic acid, oxalic acid, trifluoroacetic acid, and mixtures thereof.

14 . The associative rheology modifier of claim 1 , wherein the associative rheology modifier has a water solubility of 10-100 wt. % concentration.

15 . The associative rheology modifier of claim 1 , wherein the rheology modifier precursor has an acid value of <30 mg KOH/g.

16 . The associative rheology modifier of claim 1 , wherein the coupling agent is selected from trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, 1,6-bishexanedioldiacrylate, divinylbenzene, 1,3-diisopropenylbenzene, trimethylallyl isocyanurate, triallyl isocyanurate, 1,3,5-triazine-2,4,6(1H,3H,5H)-trithione, pentaerythritol tetra(3-mercaptopropionate), tris[2-(3-mercaptopropionyloxy)ethyl] isocyanurate, 1,2-ethanedithiol, 2,4,6-triallyloxy-1,3,5-triazine, N,N-1,3-phenylenediamaleimide, and mixtures thereof.

17 . The associative rheology modifier of claim 1 , wherein the coupling agent is present in an amount of 0.3-12 wt. %, based on the total weight of the coupling agent and the rheology modifier precursor.

18 . A composition comprising the associative rheology modifier of claim 1 , wherein the composition is for use in coatings, paints, cosmetics, automotive finishes, printing inks, filler dispersions, adhesives, detergents, wax dispersions, food industries, and paper industries.

19 . A waterborne paint composition comprising:
5-15 wt. % of water; 15-30 wt. % of at least a pigment; 20-60 wt. % of at least a binder; 0.01-5 wt. % of the associative rheology modifier of claim 1 ; and 1-15 wt. % of at least an additive, based on the total weight of the waterborne paint composition.

20 . A process to prepare an associative rheology modifier comprising:
providing a rheology modifier precursor obtained by reacting a rosin acid with a polyether at a mole ratio of the rosin acid to the polyether of >2:1, at a temperature from 180-350° C. and in the presence of an acid catalyst, wherein the polyether has a molecular weight (Mw) of 500-10,000 g/mol, and the rheology modifier precursor has a water solubility of >10 wt. % concentration; reacting the rheology modifier precursor with a coupling agent present in an amount of 0.1-15 wt. %, based on the total weight of the coupling agent and the rheology modifier precursor, by heating the mixture at a temperature from 25-250° C. for 5 min.-60 min. to obtain the associative rheology modifier;
wherein the coupling agent is reactive to carbon-carbon double bonds in the rheology modifier precursor and selected from the group consisting of sulfur-based agents, peroxide-based agents, acrylate-based agents, tellurium, selenium, polysulfide polymers, metallic oxides, di-isocyanates, and mixtures thereof;
wherein the associative rheology modifier has:
a molecular weight (Mw) of 1,500-25,000 g/mol, and
an apparent viscosity of 100,000-2,000 cP at a shear rate from 1,500-5,000 s-1 and an apparent viscosity of 2,000-100 cP at a shear rate from 5,000-20,000 s-1, at a concentration of 25 wt. % in water and a temperature of 25° C.

Assignees

• Kraton Polymers Llc
• Kraton Corp

Inventors

• Tian Jason
• Ding Ruidong
• Rucker Donna
• Reiter Chad

Classifications

• C09D125/08

  Copolymers of styrene (C09D129/08, C09D135/06, C09D155/02 take precedence) · CPC title

• C08L93/04

  Rosin · CPC title

• C08L23/0846

  with unsaturated hydrocarbons containing atoms other than carbon or hydrogen · CPC title

• C08K5/0016

  Plasticisers · CPC title

• C09D171/02

  Polyalkylene oxides · CPC title