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US-12624164-B2 - Synthetic thickeners incorporating non-reactive diluents

US12624164B2US 12624164 B2US12624164 B2US 12624164B2US-12624164-B2

Abstract

The presently disclosed and/or claimed inventive concept(s) relates to a method for preparing a reaction product, comprising (1) molten mixing a first active hydrogen containing component and a first alkali hydroxide to form a first mixture; (2) adding water into the first mixture to dissolve the first molten alkali hydroxide to form a second mixture; (3) reacting a first hydrophobic component with the second mixture to provide a Diluent; (4) molten mixing at least one second active hydrogen containing component, a second alkali hydroxide and the Diluent to form a third mixture; (5) adding water into the third mixture to dissolve the second molten alkali hydroxide to form a fourth mixture; and (6) reacting the fourth mixture with a gem-polyhalide compound or a sulfonate ester for a sufficient time to form the reaction product. Also, disclosed is a water soluble or dispersible composition comprising a diluent and a polymer.

Inventors

  • Kelly Anne Brush
  • Venkataram Krishnan
  • Zeena Kottukapally Cherian
  • Sowmitri Tarimala

Assignees

  • HERCULES LLC

Dates

Publication Date
20260512
Application Date
20200731

Claims (18)

  1. 1 . A method for preparing a reaction product, comprising: (1) molten mixing a first active hydrogen containing component and a first alkali hydroxide to form a first mixture; (2) adding water into the first mixture to dissolve the first molten alkali hydroxide to form a second mixture; (3) reacting a first hydrophobic component with the second mixture to provide a Diluent; (4) molten mixing at least one second active hydrogen containing component, a second alkali hydroxide and the Diluent to form a third mixture; (5) adding water into the third mixture to dissolve the second molten alkali hydroxide to form a fourth mixture; and (6) reacting the fourth mixture with a gem-polyhalide compound or a sulfonate ester for a sufficient time to form the reaction product.
  2. 2 . The method of claim 1 , further comprising a step (7) reacting a second hydrophobic component with the reaction product.
  3. 3 . The method of claim 1 , wherein the first and second active hydrogen containing components are identical or different and each independently comprises a single functional group of OH, SH, or NH 2 .
  4. 4 . The method of claim 3 , wherein the first and second active hydrogen containing components can each independently be represented by Formula (I), D-X Formula (I) where X is OH, SH or NH 2 and D is a substituted or unsubstituted, and/or alkoxylated or non-alkoxylated alkylene, alkyne, alkenyl, alkynyl, aryl, alkylaryl, arylalkylene, aryl alkyne, arylalkenyl, arylalkynyl, cyclic, cycloaliphatic, or polycyclic moiety.
  5. 5 . The method of claim 1 , wherein the first and second active hydrogen containing components are identical or different and each independently comprises at least two functional groups of OH, SH, or NH 2 .
  6. 6 . The method of claim 5 , wherein the first and second functional active hydrogen containing components can each independently be represented by Formula (II), (III) or (IV), where X is OH, SH, or NH 2 and D is a substituted or unsubstituted, and/or alkoxylated or non-alkoxylated alkylene, alkyne, alkenyl, alkynyl, aryl, alkylaryl, arylalkylene, aryl alkyne, arylalkenyl, arylalkynyl, cyclic, cycloaliphatic, or polycyclic moiety.
  7. 7 . The method of claim 6 , wherein the first and second active hydrogen containing components can each independently be represented by Formula (V), where X is OH, SH, or NH 2 , R is H or alkyl, n is an integer of 0 to 500 and m is an integer of 1 to 3.
  8. 8 . The method of claim 5 , wherein the first and second active hydrogen containing components are identical or different and each independently comprises a dihydric alcohol, a polyol or a polyetheramine.
  9. 9 . The method of claim 1 , wherein the first hydrophobic component is a sulfonate ester or represented by Formula (VI), Z-G Formula (VI) where Z is Br, Cl, I, or F; and G is a substituted or unsubstituted, and/or alkoxylated or non-alkoxylated alkylene, alkyne, alkenyl, alkynyl, aryl, alkylaryl, arylalkylene, aryl alkyne, arylalkenyl, arylalkynyl, cyclic, cycloaliphatic, or polycyclic moiety.
  10. 10 . The method of claim 2 , wherein the second hydrophobic component is a sulfonate ester or represented by Z-G or where Z is Br, Cl, I, or F; G is a substituted or unsubstituted, and/or alkoxylated or non-alkoxylated alkylene, alkyne, alkenyl, alkynyl, aryl, alkylaryl, arylalkylene, aryl alkyne, arylalkenyl, arylalkynyl, cyclic, cycloaliphatic, or polycyclic moiety; and AA is a substituted or unsubstituted, and/or alkoxylated or non-alkoxylated alkylene, alkyne, alkenyl, alkynyl, aryl, alkylaryl, arylalkylene, aryl alkyne, arylalkenyl, arylalkynyl, cyclic, cycloaliphatic, or polycyclic moiety.
  11. 11 . The method of claim 2 , wherein the first and second hydrophobic components are identical or different and can each independently be a sulfonate ester or represented by Formula (VII), (VIII) or (IX), where Z is Br, Cl, I, or F; and G is a substituted or unsubstituted, and/or alkoxylated or non-alkoxylated alkylene, alkyne, alkenyl, alkynyl, aryl, alkylaryl, arylalkylene, aryl alkyne, arylalkenyl, arylalkynyl, cyclic, cycloaliphatic, or polycyclic moiety.
  12. 12 . The method of claim 1 , wherein the sulfonate ester is selected from the group consisting of methane sulfonate, ethyl methane sulfonate, methyl trifluoromethanesulfonate, bromomethyl tosylate, chloromethyl tosylate, and methylene bis(toluene-4-sulfonate).
  13. 13 . A method for preparing a reaction product, comprising: (1) molten mixing a first polyglycidyl ether component and a first alkali hydroxide to form a first mixture; (2) adding water into the first mixture to dissolve the first molten alkali hydroxide to form a second mixture; (3) reacting a first active hydrogen containing component comprising a functional group of OH, SH, or NH 2 with the second mixture to form a third mixture; and (4) reacting a first hydrophobic component represented by Z-G (where Z is Br, Cl, I, F, O, or sulfonate ester and G is a substituted or unsubstituted, and/or alkoxylated or non-alkoxylated alkylene, alkyne, alkenyl, alkynyl, aryl, alkylaryl, arylalkylene, aryl alkyne, arylalkenyl, arylalkynyl, cyclic, cycloaliphatic, or polycyclic moiety(ies)) with the third mixture to provide a Diluent.
  14. 14 . The method of claim 13 , further comprising one or more steps of: (5) molten mixing a second active hydrogen component, a second alkali hydroxide, and the Diluent to form a fourth mixture, wherein the second active hydrogen component can be represented by Formula (I), (II), (III), or (IV); where X is OH, SH, or NH 2 and D is substituted or unsubstituted, and/or alkoxylated or non-alkoxylated alkylene, alkyne, alkenyl, alkynyl, aryl, alkylaryl, arylalkylene, aryl alkyne, arylalkenyl, arylalkynyl, cyclic, cycloaliphatic, or polycyclic moiety; (6) adding water into the fourth mixture to dissolve the second molten alkali hydroxide to form a fifth mixture; and/or (7) reacting the fifth mixture with a gem-polyhalide compound or a sulfonate ester for a sufficient time to form a reaction product.
  15. 15 . The method of claim 14 , further comprising a step (8) reacting a second hydrophobic component with the reaction product, wherein the second hydrophobic component is a sulfonate ester or represented by Z-G, or where Z is Br, Cl, I, or F; G is a substituted or unsubstituted, and/or alkoxylated or non-alkoxylated alkylene, alkyne, alkenyl, alkynyl, aryl, alkylaryl, arylalkylene, aryl alkyne, arylalkenyl, arylalkynyl, cyclic, cycloaliphatic, or polycyclic moiety; and AA is a substituted or unsubstituted, and/or alkoxylated or non-alkoxylated alkylene, alkyne, alkenyl, alkynyl, aryl, alkylaryl, arylalkylene, aryl alkyne, arylalkenyl, arylalkynyl, cyclic, cycloaliphatic, or polycyclic moiety.
  16. 16 . The method of claim 13 , further comprising one or more steps of: (5) molten mixing a second active hydrogen component, a second alkali hydroxide, a second polyglycidyl ether, and the Diluent to form a fourth mixture, wherein the second active hydrogen component is represented by Formula (I), (II), (III) or (IV): where X is OH, SH, or NH 2 and D is substituted or unsubstituted, and/or alkoxylated or non-alkoxylated alkylene, alkyne, alkenyl, alkynyl, aryl, alkylaryl, arylalkylene, aryl alkyne, arylalkenyl, arylalkynyl, cyclic, cycloaliphatic, or polycyclic moiety; (6) adding water into the fourth fifth mixture to dissolve the second molten alkali hydroxide to form a fourth mixture; and/or (7) reacting the fifth mixture to form the reaction product.
  17. 17 . The method of claim 16 , further comprising a step (8) reacting a second hydrophobic component with the reaction product, wherein the second hydrophobic component is represented by a sulfonate ester, Z-G, or where Z is Br, Cl, I, or F; G is a substituted or unsubstituted, and/or alkoxylated or non-alkoxylated alkylene, alkyne, alkenyl, alkynyl, aryl, alkylaryl, arylalkylene, aryl alkyne, arylalkenyl, arylalkynyl, cyclic, cycloaliphatic, or polycyclic moiety; and AA is a substituted or unsubstituted, and/or alkoxylated or non-alkoxylated alkylene, alkyne, alkenyl, alkynyl, aryl, alkylaryl, arylalkylene, aryl alkyne, arylalkenyl, arylalkynyl, cyclic, cycloaliphatic, or polycyclic moiety.
  18. 18 . The method of claim 16 , wherein the first and second polyglycidyl ether components are identical or different and each is independently represented by Formula (X), (XI), (XII), or (XIII), where A is a substituted or unsubstituted, and/or alkoxylated or non-alkoxylated alkylene, alkyne, alkenyl, alkynyl, aryl, alkylaryl, arylalkylene, aryl alkyne, arylalkenyl, arylalkynyl, cyclic, cycloaliphatic, or polycyclic moiety; and B is CH 2 OCH 2 .

Description

CROSS-REFERENCE TO RELATED APPLICATIONS This application is a U.S. National Phase filing under 35 U.S.C. § 371 of International Application No. PCT/US2020/044484, filed Jul. 31, 2020, and published as WO/2021/022153 on Feb. 4, 2021, which claims benefit of priority U.S. Provisional Patent Application No. 62/881,621, filed Aug. 1, 2019, and priority of U.S. Provisional Patent Application No. 62,881,521, filed Aug. 1, 2019. The entire contents of each of the prior applications are incorporated herein by reference in their entirety. FIELD The presently disclosed process(es), procedure(s), method(s), product(s), result(s), and/or concept(s) (collectively referred to hereinafter as the “present disclosure”) relates generally to a method for preparing a reaction product and an aqueous protective coating composition comprising the reaction products thereof. BACKGROUND Water-soluble polymers (also commonly referred to as “thickeners” or “rheology modifiers”) are widely used in many industrial water-borne systems as additives to modify the systems' flow behavior. Thickeners increase and maintain viscosity at required levels under specified processing conditions and end-use situations. Thickeners are useful, for example, in decorative and protective coatings, paper coatings, cosmetics and personal care products, detergents, pharmaceuticals, adhesives and sealants, agricultural formulations, and petroleum drilling fluids. Thickeners can be natural products, directly derived from natural products, or synthetically manufactured. Examples of natural thickeners may include, but are not limited to, casein, alginates, gum tragacanthins, guar, xanthan gum, locust and bean gum. Examples of naturally-derived thickeners may include, but are not limited to, cellulose ethers derived from cellulosics, such as hydroxyethyl cellulose (HEC), hydroxypropyl cellulose (HPC), and carboxymethyl cellulose (CMC). These natural and naturally-derived products (collectively, “natural products”) vary in their thickening efficiency. One drawback of the natural products is that they are susceptible to microbial attack and hence, may require the addition of antimicrobial agents to the formulation. Examples of synthetic thickeners (also called “associative thickeners” or “associative polymers”) may include, but are not limited to, various acrylic polymers, alkylene oxide polymers, amide polymers, and maleic anhydride polymers. Synthetic thickeners may also include non-ionic synthetic associative thickeners (NSAT) rheology modifiers, such as hydrophobically-modified ethoxylated urethane (HEUR), hydrophobically-modified polyethylene glycol (HmPEG) and hydrophobically-modified polyacetal-polyether (HmPAPE). These synthetic thickeners can be homopolymers or copolymers. Some of these polymers' hydrolytic stability depends on the pH of the solution and others are sensitive to various components normally found in aqueous coatings. In recent years, synthetic associative thickeners have been used in a variety of applications including adhesives and personal care, and in industrial applications such as construction, specialty coatings, waterborne coatings, and latex paints. Synthetic associative thickeners serve several roles in aqueous systems. For instance, in latex paints and waterborne coatings, the thickener can provide improved stability and pigment suspension, as well as improved rheological and application properties. Additionally, synthetic associative thickeners can be prepared with certain properties in mind because they are synthesized from basic chemicals. In other words, synthetic associative thickeners can be tailored for desired and/or targeted properties from the ground up. Typically, production of the NSAT polymers of either HEUR or HmPAPE chemistry is based upon starting with a commercial hydroxyl-terminated PEG, typically of MW ˜8,000, and randomly coupling the chains together to form a higher molecular weight polymer. Capping of the chains with hydrophobes serves to introduce associative behavior when the polymer is dissolved in water. Polymer molecular weight distribution, type of hydrophobe, and concentration all have a significant impact on solution rheology characteristics. The process of increasing molecular weight by random coupling of chains leads to well-prescribed final molecular weight distributions. However, the production of high molecular weight NSAT polymers is somewhat limited due at least in part to process conditions during synthesis, which can limit and/or reduce control over certain properties of the resulting NSAT, including, but not limited to, molecular weight and polydispersity and Brookfield, KU, and ICI viscosities. Accordingly, a need exists for a synthetic associative thickener that can provide flexibility in synthesis for targeting the specific properties and satisfy a wide range of rheology requirements for paints. DETAILED DESCRIPTION Before explaining at least one embodiment of the present disclosure in det