Novel polyamide rheology modifiers for aqueous coatings

Abstract

A novel rheology modifier for use in aqueous coatings, which comprises a polyamide containing a quaternary ammonium, and which can provide excellent pigment suspension and rheological properties to aqueous coatings without being affected by pH fluctuations.

Description

Technical Field

[0001] This invention relates to rheology modifier compositions, particularly rheology modifier compositions for use in water-based coatings. The invention also relates to methods for preparing rheology modifier compositions. Background Technology

[0002] To prevent pigments used in coatings from settling during storage, anti-settling agents can be added to the coating composition. These anti-settling agents can provide good pigment suspension and rheological properties to water-based coating compositions and overcome the settling problems that occur in coatings.

[0003] Due to the large particle size and density of pigments, aluminum or pearlescent pigments (such as mica) or corrosion-resistant pigments used in metallic and corrosion-resistant coatings may cause sedimentation in water-based coatings. In solvent-based coatings, amide wax-based or polyethylene oxide wax-based antisettling agents are used, but many of these are not suitable for water-based coatings.

[0004] Some existing products on the market (such as polyamide-based antisettling agents obtained by reacting diamines, diacids, and dimer acids) can provide improved antisettling properties, thixotropy, and orientation of metallic pigments. However, these products may perform poorly at high temperatures. Derivatives consisting of polyamides, diamides, and surfactants can form a hybrid that can improve heat resistance.

[0005] US Pat. No. 3,937,678 discloses that applying a mixture of amide waxes can improve the rheological and suspension properties of non-aqueous fluid systems containing finely dispersed solid particles. US Pat. No. 4,381,376 discloses a method for forming ionic copolymer salts from low molecular weight copolymer acids and discloses dispersions of finely dispersed inert materials (e.g., pigments) in various non-aqueous polymer compositions (including polypropylene and polyethylene). US Pat. No. 5,374,687 discloses an anti-settling agent, which is a liquid obtained by neutralization with a neutralizing agent. This may have operational advantages but is insufficient as an anti-settling agent for aluminum pigments or pearlescent pigments (e.g., mica) used in waterborne metallic coatings. US Pat. No. 5,994,494 discloses an anti-settling agent for waterborne coatings. The resulting composition is a polyamide. The polyamide is neutralized with a neutralizing alkali, and then the neutralized polyamide is dispersed in a medium primarily composed of water. US Pat. No. 8,809,429 discloses an aqueous pigment antisettling agent comprising a neutralized mixture containing polyamide, amide wax and / or hydrogenated castor oil, and exhibiting pigment antisettling effects even at high temperatures.

[0006] In recent years, due to the increasing importance of environmental issues, the demand for water-based coating additives (such as anti-settling agents) has also increased, in addition to the risk of fire. Water-based additives can reduce solvent waste and VOC pollution, and can also prevent fire hazards.

[0007] As mentioned above, acid-terminated polyamide antisettling agents are neutralized with alkali. The use of such antisettling agents can be affected by the pH of the application system, which can be undesirable. Summary of the Invention

[0008] This disclosure provides a rheology modifier comprising a quaternary ammonium polyamide. The rheology modifier of this invention addresses problems associated with existing rheology modifiers in coatings and inks, such as water-based coatings and ink compositions. Surprisingly, the rheology modifier of this disclosure exhibits favorable pigment anti-settling effects, particularly in water-based coating systems. These pigment anti-settling effects can be observed at high temperatures. Furthermore, the effect of pH fluctuations on the rheology modifier can be advantageously reduced.

[0009] In a first aspect, this disclosure provides a rheology modifier composition comprising a polyamide [B] containing quaternary ammonium.

[0010] Rheology modifiers may contain a mixture of polyamides [B] containing quaternary ammonium and amide waxes or polyamide waxes [A].

[0011] In a first aspect, the rheology modifier composition comprises a quaternary ammonium-containing polyamide [B] having formula (1): Equation (1) R4 is selected from the group consisting of: substituted or unsubstituted alkyl groups having 2 to 36 carbon atoms, either straight or branched; R5 is selected from the group consisting of: substituted or unsubstituted alkyl groups having 2 to 34 carbon atoms, either straight or branched; R6 is selected from the group consisting of: substituted or unsubstituted alkyl groups having 2 to 12 carbon atoms, either straight or branched; R7 is selected from the group consisting of: hydrogen, or alkyl, alkyl carboxylic acid esters or alkyl sulfonates having 1 to 18 carbon atoms, or combinations thereof; and m ranges from 1 to 10.

[0012] The rheology modifier composition may also contain amide wax or polyamide wax [A]. The amide wax or polyamide wax [A] can be defined by formula (2). Equation (2) R1 is selected from the group consisting of: substituted or unsubstituted alkyl groups with straight or branched chains having 2 to 36 carbon atoms; R2 is selected from the group consisting of: substituted or unsubstituted alkyl groups with straight or branched chains having 1 to 21 carbon atoms; R3 is selected from the group consisting of: substituted or unsubstituted alkyl groups with straight or branched chains having 2 to 34 carbon atoms; and n ranges from zero to 10.

[0013] In another aspect, this disclosure provides a method for preparing a rheology modifier comprising a quaternary ammonium-terminated polyamide, wherein the quaternary ammonium-terminated polyamide [B] is obtained by reacting a tertiary amine-terminated polyamide with a quaternizing agent. Preferably, the method comprises preparing a rheology modifier comprising a quaternary ammonium-terminated polyamide [B] according to formula (1).

[0014] In another aspect, a method for preparing a rheology modifier is disclosed, the method comprising mixing a quaternary ammonium-terminated polyamide [B] with a polyamide wax [A].

[0015] In another aspect, this disclosure provides an aqueous coating or ink comprising a rheology modifier composition as disclosed herein.

[0016] In another aspect, this disclosure provides the use of the rheology modifier compositions disclosed herein in water-based coatings or inks. Detailed Implementation

[0017] The following definitions apply to the disclosure herein, including all aspects of the invention and its embodiments.

[0018] The compounds and intermediates described herein may be named according to the IUPAC (International Union of Pure and Applied Chemistry) or CAS (Chemical Abstracts Service) nomenclature systems or by their commercial trade names. It should also be understood that any reference to the compounds described herein, such as polyurea, primary monoamine, diamine, or triamine, covers all stereoisomers (e.g., cis and trans isomers) and / or optical isomers (e.g., R and S enantiomers) of such compounds, substantially in their pure form and / or mixtures of the foregoing substances in any ratio.

[0019] As used alone or in combination with one or more other terms in this document, “substituted” means that the hydrogen atoms on a molecule have been replaced by different atoms or groups of atoms. The atom or group of atoms that replaces the hydrogen atom is a “substituent”. It should be understood that the terms “substituent,” “substituents,” “moiety,” “moieties,” “group,” or “groups” refer to substituents.

[0020] As used herein, the term "aliphatic" refers to a compound or group containing one or more saturated carbon atoms and / or two or more unsaturated carbon atoms, such as a side chain, but excluding aromatic groups or compounds. In other words, the term "aliphatic" excludes aromatic groups or substituents unless the context otherwise requires.

[0021] The hydrocarbon-containing portions provided in this article can be described using prefixes, which indicate the minimum and maximum number of carbon atoms in the portion, i.e., "C". a -C b For example, C a -C b Alkyl means an alkyl moiety having an integer number of carbon atoms from “a” to “b”, including the end value.

[0022] The term "alkylene" refers to a branched or unbranched (e.g., straight-chain) saturated hydrocarbon chain, unless otherwise specified. Alkylenes are typically unsubstituted, unless otherwise specified. Alkylenes typically have 1 to 12 carbon atoms, for example, 2 to 10 carbon atoms or 4 to 8 carbon atoms. Representative examples include, but are not limited to, methylene, ethylene (e.g., -CH(CH3)- and -CH2CH2-), propylene (e.g., -CH(CH3)CH2- and -CH2CH2CH2-), etc.

[0023] As used herein, the term "alkyl," whether used alone or in combination with another term, refers to a branched or unbranched saturated hydrocarbon chain, unless otherwise stated. Alkyl groups are generally unsubstituted unless otherwise stated. Alkyl groups can have, for example, 1 to 40 carbon atoms, for example 1 to 20 carbon atoms, for example 1 to 12 carbon atoms, and particularly 1 to 8 carbon atoms. Representative examples include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, isopropyl, tert-butyl, isobutyl, etc.

[0024] As used herein, the term "alkoxy" refers to the alkyl-oxy group, where the alkyl group is as defined above. Alkoxy groups are typically unsubstituted unless otherwise specified. Representative examples include -OMe, -OEt, and -O. n Pr, -O i Pr.

[0025] As used herein, the term "hydrocarbon group" refers to a branched or unbranched (e.g., straight-chain) saturated hydrocarbon chain, unless otherwise stated. A hydrocarbon group can be bonded to multiple adjacent groups by the same or different carbon atoms, as shown in the contents (e.g., the chemical formula including the hydrocarbon group). Hydrocarbon groups are generally unsubstituted unless otherwise stated. Hydrocarbon groups typically have 1 to 12 carbon atoms, for example, 2 to 10 carbon atoms or 4 to 8 carbon atoms.

[0026] As used herein, the term "quaternary ammonium" refers to a group in which the nitrogen atom in the ammonium group is directly bonded to four atoms other than hydrogen (e.g., directly bonded to four carbon atoms). The nitrogen atom carries a positive charge. Compounds containing quaternary ammonium groups, such as polyamides containing quaternary ammonium, may contain, for example, one or two quaternary ammonium groups.

[0027] As used herein, the term "polyamide" refers to a compound having two or more amide groups. In other words, the term "polyamide" includes compounds having two, three, four, or more amide groups.

[0028] As used herein, "direct bonding" or "direct connection" means that one group, part, or substituent is covalently bonded to an atom of another group, part, or substituent that is adjacent to (i.e., directly adjacent). In other words, there is no inserted atom, group, part, or substituent.

[0029] As used in this article, the term "room temperature" refers to a temperature of approximately 20°C.

[0030] As used in this article, at number-average molecular weight (M n ) and weight-average molecular weight (M w In the context of ), the term "average" refers to the average value. Number-average molecular weight (M0) n ) and weight-average molecular weight (M w It can be determined by conventional methods, such as gel permeation chromatography (GPC) using polystyrene as a standard.

[0031] As used in this disclosure, the term "rheology modifier" refers to a composition comprising or substantially composed of a polyamide containing quaternary ammonium as described herein. Rheology additives (i.e., rheology modifiers) may be included as an ingredient in another composition (e.g., a coating composition) to control its rheological properties. It may be necessary to activate the rheology additive before or after adding it as an ingredient to another composition to obtain the desired rheological properties.

[0032] The amount of material (e.g., compound, composition, or ingredient) is usually defined as wt% of the composition.

[0033] The term “about”, when used in conjunction with a measurable value (such as pH or temperature) in this document, covers reasonable variations in said value, for example, allowing for experimental error in the measurement of said value.

[0034] To avoid ambiguity, the expression "consistently composed of..." as used herein limits the scope of a feature to include the specific material as well as any other material or step that does not substantially affect the fundamental and novel properties of the feature, such as trace impurities. The expression "consistently composed of..." encompasses the expression "composed of...".

[0035] In a first aspect, this disclosure provides a rheology modifier comprising a quaternary ammonium-containing polyamide [B] having formula (1). Equation (1) R4 is selected from the group consisting of: substituted or unsubstituted alkyl groups, either straight-chain or branched, having 2 to 36 carbon atoms; R5 is selected from the group consisting of: substituted or unsubstituted alkyl groups, either straight-chain or branched, having 2 to 34 carbon atoms; R6 is selected from the group consisting of: substituted or unsubstituted alkyl groups, either straight-chain or branched, having 2 to 12 carbon atoms; and R7 is selected from the group consisting of: hydrogen, or alkyl, alkyl carboxylic acid esters, or alkyl sulfonates, or combinations thereof, having 1 to 18 carbon atoms; and m ranges from 1 to 10. Polyamides containing quaternary ammonium are quaternary ammonium-terminated polyamides.

[0036] In formula (1), each R4 is independently selected from the group consisting of straight-chain or branched substituted or unsubstituted alkyl groups having 2 to 36 carbon atoms. R4 is preferably selected from straight-chain or branched substituted or unsubstituted alkyl groups having 5 to 20 carbon atoms (e.g., 10 to 15 carbon atoms). R4 may be selected from straight-chain or branched substituted or unsubstituted alkyl groups having 2 to 12 carbon atoms. Preferably, R4 is an unsubstituted alkyl group. Preferably, R4 is a straight-chain alkyl group.

[0037] In formula (1), each R5 is independently selected from the group consisting of substituted or unsubstituted alkyl groups having 2 to 34 carbon atoms, either straight-chain or branched. R5 is preferably selected from the group consisting of substituted or unsubstituted alkyl groups having 4 to 20 carbon atoms (e.g., 5 to 10 carbon atoms), either straight-chain or branched. Preferably, R5 is an unsubstituted alkyl group. Preferably, R5 is a straight-chain alkyl group.

[0038] In formula (1), each R6 is independently selected from the group consisting of substituted or unsubstituted alkyl groups having 2 to 12 carbon atoms, either straight-chain or branched. R6 is preferably selected from the group consisting of substituted or unsubstituted alkyl groups having 4 to 10 carbon atoms (e.g., 3 to 6 carbon atoms), either straight-chain or branched. Preferably, R6 is an unsubstituted alkyl group. Preferably, R6 is a straight-chain alkyl group.

[0039] In formula (1), each R7 is independently selected from the group consisting of hydrogen, alkyl, alkyl carboxylic acid esters or alkyl sulfonates, or combinations thereof. When R7 is not hydrogen, R7 has 1 to 18 carbon atoms, preferably 4 to 12 carbon atoms, for example 6 to 10 carbon atoms. In one embodiment, R7 is hydrogen. In another embodiment, R7 is a straight-chain alkyl group having 1 to 18 carbon atoms, preferably 4 to 12 carbon atoms, for example 6 to 10 carbon atoms.

[0040] In equation (1), m ranges from 1 to 10. Preferably, m ranges from 2 to 8, for example from 4 to 6.

[0041] In one embodiment, in formula (1), R4 is an unsubstituted straight-chain alkyl group having 2 to 36 carbon atoms, R5 is an unsubstituted straight-chain alkyl group having 2 to 34 carbon atoms, R6 is an unsubstituted straight-chain alkyl group having 2 to 12 carbon atoms, R7 is an unsubstituted straight-chain alkyl group having 1 to 18 carbon atoms, and m is 1 to 10. In another embodiment, R4 is an unsubstituted straight-chain alkyl group having 2 to 12 carbon atoms, R5 is an unsubstituted straight-chain alkyl group having 4 to 34 carbon atoms, R6 is an unsubstituted straight-chain alkyl group having 2 to 6 carbon atoms, R7 is an unsubstituted straight-chain alkyl group having 1 to 18 carbon atoms, and m is 1 to 10.

[0042] Polyamides [B] containing quaternary ammonium can have an amine value ranging from 30 to 140 mg KOH / g. Preferably, the amine value ranges from 50 to 100 mg KOH / g, for example, 70 to 90 mg KOH / g. "Amine value" refers to a measure of the amine content of the polyamide, which can be determined by conventional methods (e.g., titration).

[0043] This disclosure provides a rheology modifier composition comprising a mixture of a quaternary ammonium-containing polyamide [B] as described above and an amide wax or polyamide wax [A] as described herein.

[0044] Advantageously, the weight ratio of [A] and [B] present in the rheology modifier composition can be in the range of 5:95 to 50:50; preferably in the range of 15:85 to 40:60; for example in the range of 20:80 to 30:70.

[0045] Amide wax or polyamide wax [A] can be defined according to formula (2): Equation (2) R1 is selected from the group consisting of: straight-chain or branched substituted or unsubstituted alkyl groups having 2 to 36 carbon atoms; R2 is selected from the group consisting of: straight-chain or branched substituted or unsubstituted alkyl groups having 1 to 21 carbon atoms; R3 is selected from the group consisting of: straight-chain or branched substituted or unsubstituted alkyl groups having 2 to 34 carbon atoms; and n ranges from zero to 10.

[0046] In formula (2), each R1 is independently selected from the group consisting of substituted or unsubstituted alkyl groups having a straight chain or branched structure having 2 to 36 carbon atoms. R1 is preferably selected from the group consisting of substituted or unsubstituted alkyl groups having a straight chain or branched structure having 2 to 12 carbon atoms (e.g., 4 to 8 carbon atoms). Preferably, R1 is unsubstituted. Preferably, R1 is a straight-chain alkyl group.

[0047] In formula (2), each R2 is independently selected from the group consisting of substituted or unsubstituted alkyl groups having a straight chain or branched structure having 1 to 21 carbon atoms. R2 is preferably selected from the group consisting of substituted or unsubstituted alkyl groups having a straight chain or branched structure having 3 to 17 carbon atoms (e.g., 5 to 10 carbon atoms). Preferably, R2 is unsubstituted. Preferably, R2 is a straight-chain alkyl group.

[0048] In formula (2), each R3 is independently selected from the group consisting of substituted or unsubstituted alkyl groups having 2 to 34 carbon atoms, either straight-chain or branched. R3 is preferably selected from the group consisting of substituted or unsubstituted alkyl groups having 4 to 30 carbon atoms (e.g., 10 to 20 carbon atoms), either straight-chain or branched. Preferably, R3 is unsubstituted. Preferably, R3 is a straight-chain alkyl group.

[0049] In equation (2), n ranges from 0 to 10. Preferably, n ranges from 1 to 8, for example, from 3 to 6.

[0050] In one embodiment, R1 is a straight-chain alkyl group having 2 to 36 carbon atoms, R2 is a straight-chain alkyl group having 1 to 21 carbon atoms, R3 is a straight-chain alkyl group having 2 to 34 carbon atoms, and n ranges from 0 to 10. In another embodiment, R1 is a straight-chain alkyl group having 2 to 12 carbon atoms, R2 is a straight-chain alkyl group having 1 to 17 carbon atoms, R3 is a straight-chain alkyl group having 4 to 34 carbon atoms, and n ranges from 0 to 10.

[0051] This document also discloses a rheology modifier composition comprising a mixture of a quaternary ammonium polyamide [B] and an amide wax or polyamide wax [A], wherein the amide wax or polyamide wax [A] is defined by formula (2) above, and wherein the quaternary ammonium polyamide [B] is defined by formula (1) above.

[0052] For example, a rheology modifier composition may comprise a quaternary ammonium-containing polyamide of formula (1) [B] and an amide wax or polyamide wax of formula (2) [A]: Equation (1) R4 is selected from the group consisting of: substituted or unsubstituted alkyl groups having 2 to 36 carbon atoms, either straight or branched; R5 is selected from the group consisting of: substituted or unsubstituted alkyl groups having 2 to 34 carbon atoms, either straight or branched; R6 is selected from the group consisting of: substituted or unsubstituted alkyl groups having 2 to 12 carbon atoms, either straight or branched; and R7 is selected from the group consisting of: hydrogen, or alkyl, alkyl carboxylic acid esters, or alkyl sulfonates having 1 to 18 carbon atoms, or combinations thereof; and m ranges from 1 to 10. Equation (2) R1 is selected from the group consisting of: straight-chain or branched substituted or unsubstituted alkyl groups having 2 to 36 carbon atoms; R2 is selected from the group consisting of: straight-chain or branched substituted or unsubstituted alkyl groups having 1 to 21 carbon atoms; R3 is selected from the group consisting of: straight-chain or branched substituted or unsubstituted alkyl groups having 2 to 34 carbon atoms; and n ranges from zero to 10.

[0053] Advantageously, the rheology modifier composition may comprise a quaternary ammonium-containing polyamide of formula (1) [B] and an amide wax or polyamide wax of formula (2) [A]: Equation (1) Wherein R4 is a straight-chain alkyl group having 2 to 36 carbon atoms, R5 is a straight-chain alkyl group having 2 to 34 carbon atoms, R6 is a straight-chain alkyl group having 2 to 12 carbon atoms, R7 is a straight-chain alkyl group having 1 to 18 carbon atoms, and m is 1 to 10. Equation (2) Wherein R1 is a straight-chain alkyl group having 2 to 36 carbon atoms, R2 is a straight-chain alkyl group having 1 to 21 carbon atoms, R3 is a straight-chain alkyl group having 2 to 34 carbon atoms, and n is zero to 10.

[0054] In another aspect, this disclosure provides a method for preparing a rheology modifier comprising a quaternary ammonium-terminated polyamide. The method may provide a rheology modifier comprising a quaternary ammonium-terminated polyamide [B] according to formula (1) as disclosed herein. The method includes obtaining the quaternary ammonium-terminated polyamide by reacting the tertiary amine-terminated polyamide with a quaternizing agent.

[0055] Any suitable quaternizing agent can be used in the methods disclosed herein. The quaternizing agent may comprise a haloalkane having 1 to 18 carbon atoms (preferably a haloalkane having 2 to 10 carbon atoms, such as a haloalkane having 3 to 5 carbon atoms), a sodium chloroalkylcarboxylate having 1 to 11 carbon atoms (e.g., a sodium chloroalkylcarboxylate having 2 to 4 carbon atoms), a cyclic sulfonate or sulpholactone having 3 to 6 carbon atoms, acetic acid, acrylic acid, hydrogen peroxide, or combinations thereof. The quaternizing agent may be selected from acetic acid, acrylic acid, hydrogen peroxide, sodium chloroacetate, dimethyl sulfonate, iodomethane, 1,3-propane sulpholactone, 1,4-butane sulpholactone, iodomethane, and combinations thereof.

[0056] Tertiary amine-terminated polyamides can be obtained by reacting one or more diamines having 2 to 34 carbon atoms, one or more dicarboxylic acids having 4 to 36 carbon atoms, and a tertiary amine of a dimethylaminoalkylamine having 2 to 12 carbon atoms. Preferably, an excess of dicarboxylic acid may be present relative to the diamine. An excess of dicarboxylic acid means that a certain amount of dicarboxylic acid is present after the reaction.

[0057] One or more diamines may be selected from the group consisting of ethylenediamine, 1,4-butanediane, hexanediamine, 1,10-decanediamine, 1,11-undecanediamine, 1,12-dodecanediamine, phenylenediamine, and 4,4'-diaminodiphenylmethane and mixtures thereof. In one example, the diamine is selected from ethylenediamine, hexanediamine, and 1,12-dodecanediamine. The diamine has 2 to 34 carbon atoms, preferably 5 to 25 carbon atoms, for example 10 to 15 carbon atoms.

[0058] One or more dicarboxylic acids may be selected from the group consisting of: malonic acid, succinic acid, glutamic acid, adipic acid, pimelic acid, octanoic acid, azelaic acid, sebacic acid, dodecanoic acid, isophthalic acid, dimer fatty acids (e.g., C36 dimer acids), and mixtures thereof. In one example, the dicarboxylic acid is selected from azelaic acid, azelaic acid, C36 dimer acids, and mixtures thereof. The dicarboxylic acid has 4 to 36 carbon atoms, preferably 6 to 25 carbon atoms, for example 10 to 20 carbon atoms.

[0059] The tertiary amines of dimethylaminoalkylamines have 2 to 12 carbon atoms, preferably 2 to 8 carbon atoms, for example 4 to 6 carbon atoms. Dimethylaminoalkylamines can be selected from the group consisting of: dimethylaminopropylamine (DMAPA), dimethylaminobutylamine, dimethylaminopentylamine, and dimethylaminohexylamine. In one example, the dimethylaminoalkylamine is dimethylaminopropylamine (DMAPA).

[0060] Preferably, the acid value of the tertiary amine-terminated polyamide is less than 10 mg KOH / g, more preferably less than 7 mg KOH / g, for example less than 5 mg KOH / g. The acid value can be determined by conventional methods, such as titration using a suitable indicator (e.g., basic blue).

[0061] The amine value of the tertiary amine-terminated polyamide ranges from 30 to 200 mg KOH / g, preferably from 50 to 150 mg KOH / g, for example from 80 to 120 mg KOH / g.

[0062] On the other hand, a method for preparing a rheology modifier is disclosed, comprising the step of mixing a quaternary ammonium-terminated polyamide [B] with an amide wax or a polyamide wax [A]. The quaternary ammonium-terminated polyamide [B] can be prepared as previously described; that is, by reacting a tertiary amine-terminated polyamide with a quaternizing agent. Typically, the quaternary ammonium-terminated polyamide [B] is defined by formula (1), and the amide wax or polyamide wax [A] is defined by formula (2).

[0063] Amide waxes or polyamide waxes [A] can be obtained by reacting a monocarboxylic acid having 2 to 22 carbon atoms and / or a dicarboxylic acid having 4 to 36 carbon atoms with a diamine having 2 to 12 carbon atoms. Advantageously, the wax can be obtained by reacting a monocarboxylic acid having 2 to 22 carbon atoms with a diamine having 2 to 12 carbon atoms. For example, the wax can be obtained by reacting a dicarboxylic acid having 4 to 36 carbon atoms with a diamine having 2 to 12 carbon atoms. In another example, the wax can be obtained by reacting a dicarboxylic acid having 4 to 36 carbon atoms, a monocarboxylic acid having 2 to 22 carbon atoms, and a diamine having 2 to 12 carbon atoms.

[0064] The diamine may be selected from the group consisting of ethylenediamine, 1,4-butane, hexanediamine, 1,10-decanediamine, 1,11-undecaneethylenediamine, 1,12-dodecanediamine, phenylenediamine, and 4,4'-diaminodiphenylmethane and mixtures thereof. For example, the diamine is selected from ethylenediamine, hexanediamine, and mixtures thereof. Typically, the diamine has 2 to 12 carbon atoms, preferably 4 to 10 carbon atoms, for example 6 to 8 carbon atoms.

[0065] The dicarboxylic acid may be selected from the group consisting of: malonic acid, succinic acid, glutamic acid, adipic acid, pimelic acid, octanoic acid, azelaic acid, sebacic acid, dodecanoic acid, isophthalic acid, and dimer fatty acids (e.g., C36 dimer acids) and mixtures thereof. In one example, the dicarboxylic acid is selected from azelaic acid, azelaic acid, C36 dimer acids, and mixtures thereof. Typically, the dicarboxylic acid has 4 to 36 carbon atoms, preferably 10 to 25 carbon atoms, for example 15 to 20 carbon atoms.

[0066] The monocarboxylic acid may be selected from the group consisting of: lauric acid, 12-hydroxystearic acid, stearic acid, fatty acids, butyric acid, caproic acid, palmitic acid, propionic acid, acetic acid, hexanoic acid, and oleic acid. In one example, the monocarboxylic acid is selected from acetic acid, propionic acid, propionic acid, hexanoic acid, and mixtures thereof. Typically, the monocarboxylic acid has 2 to 22 carbon atoms, preferably 5 to 20 carbon atoms, for example 10 to 15 carbon atoms.

[0067] The rheology modifier compositions described herein may also contain ionized polyamide esters [C]. Such ionized polyamide esters [C] may have an acid value of 40 to 230 mg KOH / g, preferably 100 to 200 mg KOH / g, for example 120 to 150 mg KOH / g.

[0068] Ionized acid-terminated polyamide esters [C] can be defined according to formula (3). Equation (3) R8 is selected from the group consisting of: straight-chain or branched substituted or unsubstituted alkyl groups having 2 to 36 carbon atoms; R9 is selected from the group consisting of: straight-chain or branched substituted or unsubstituted alkyl groups having 2 to 34 carbon atoms; R 10 Choose from the group consisting of: straight-chain or branched substituted or unsubstituted alkyl groups having 1 to 5 carbon atoms, where p ranges from 1 to 10, j ranges from 1 to 10, and k ranges from 1 to 10. To avoid ambiguity, the values ​​of p, j, and k are independent of each other.

[0069] In formula (3), R8 is selected from the group consisting of: straight-chain or branched substituted or unsubstituted alkyl groups having 2 to 36 carbon atoms, preferably 5 to 25 carbon atoms, for example 12 to 20 carbon atoms. Preferably, R8 is a straight-chain alkyl group. Preferably, R8 is unsubstituted.

[0070] In formula (3), R9 is selected from the group consisting of: straight-chain or branched substituted or unsubstituted alkyl groups having 2 to 34 carbon atoms, preferably 5 to 22 carbon atoms, for example 10 to 15 carbon atoms. Preferably, R9 is a straight-chain alkyl group. Preferably, R9 is unsubstituted.

[0071] In equation (3), R 10 Selected from the group consisting of: substituted or unsubstituted alkyl groups having 1 to 5 carbon atoms, preferably 3 to 4 carbon atoms, for example 3 carbon atoms, either straight-chain or branched. Preferably, R 10 It is an unsubstituted alkyl group. Preferably, R 10 It is a straight-chain alkyl group.

[0072] In equation (3), p ranges from 1 to 10, preferably from 2 to 8, for example from 4 to 6.

[0073] In equation (3), j ranges from 1 to 10, preferably from 2 to 8, for example from 4 to 6.

[0074] In equation (3), k ranges from 1 to 10, preferably from 2 to 8, for example from 4 to 6.

[0075] In one embodiment, in formula (3), R8 is a straight-chain alkyl group having 2 to 36 carbon atoms, R9 is a straight-chain alkyl group having 2 to 34 carbon atoms, and R 10 It is a straight-chain alkyl group having 1 to 5 carbon atoms, where p is 1 to 10, j is 1 to 10, and k is 1 to 10. Preferably, R8 is a straight-chain alkyl group having 2 to 12 carbon atoms, R9 is a straight-chain alkyl group having 4 to 34 carbon atoms, and R... 10 It is a straight-chain alkyl group having 3 to 5 carbon atoms.

[0076] The acid value of the ionized acid-terminated polyamide ester [C] can be from 30 to 230 mg KOH / g, preferably from 80 to 200 mg KOH / g, for example from 100 to 150 mg KOH / g.

[0077] Ionized polyamide ester [C] can be obtained by reacting a diamine having 2 to 34 carbon atoms with an excess of a dicarboxylic acid having 4 to 36 carbon atoms relative to the diamine to form an intermediate polyamide. The intermediate polyamide can then be reacted with a lactone having 2 to 6 carbon atoms and neutralized with a base to obtain ionized acid-terminated polyamide ester [C]. Preferably, the acid value of the ionized acid-terminated polyamide ester [C] is in the range of 30 to 230 mg KOH / g.

[0078] The dicarboxylic acid may be selected from the group consisting of: malonic acid, succinic acid, glutamic acid, adipic acid, pimelic acid, octanoic acid, azelaic acid, sebacic acid, dodecanoic acid, isophthalic acid, and dimer fatty acids (e.g., C36 dimer acids) or mixtures thereof. In one example, the dicarboxylic acid may be selected from azelaic acid, azelaic acid, C36 dimer acids, or mixtures thereof. Typically, the dicarboxylic acid has 4 to 36 carbon atoms, preferably 10 to 25 carbon atoms, for example 15 to 20 carbon atoms.

[0079] The diamine may be selected from the group consisting of ethylenediamine, 1,4-butane, hexanediamine, 1,10-decanediamine, 1,11-undecaneethylenediamine, 1,12-dodecanediamine, phenylenediamine, and 4,4'-diaminodiphenylmethane and mixtures thereof. In one example, the diamine may be selected from ethylenediamine, hexanediamine, and mixtures thereof. Typically, the diamine has 2 to 34 carbon atoms, preferably 10 to 25 carbon atoms, for example 5 to 15 carbon atoms.

[0080] The lactone may be selected from the group consisting of alpha-acetolactone, β-propiolactone, γ-butyrolactone, ε-caprolactone, and γ-valerolactone, and mixtures thereof. In one example, the lactone may be selected from ε-caprolactone, γ-valerolactone, and mixtures thereof. Typically, the lactone has 2 to 6 carbon atoms, preferably 3 to 5 carbon atoms, for example, 4 carbon atoms.

[0081] According to another aspect of the invention, a coating or ink comprising a rheology modifier composition as disclosed herein is provided. Preferably, the coating or ink is a water-based coating or ink.

[0082] The water-based coatings or inks typically contain about 0.1 wt% to about 20 wt%, preferably about 1.0 wt% to about 10 wt%, and more preferably about 2 wt% to about 5 wt% of a rheology modifier composition. Generally, the coatings or inks contain an effective amount of the rheology modifier composition.

[0083] Typically, the coating or ink contains the remainder water. The coating or ink may contain about 20 wt% to about 60 wt% water, preferably about 30 wt% to about 50 wt% water, for example about 20 wt% to 40 wt% water. The coating or ink may also contain additional solvents, particularly water-soluble solvents.

[0084] Exemplary coatings include water-based metallic coatings, pearlescent coatings, and water-based corrosion-resistant coatings. The coatings or inks contain pigments, which may be present in amounts from about 3 wt% to about 30 wt%, preferably from about 5 wt% to about 20 wt%, for example from about 10 wt% to about 15 wt%. The pigments are not particularly limited and may be selected from, for example, metallic pigments or pearlescent pigments (e.g., mica), or mixtures thereof. Preferably, the pigments may contain aluminum, for example, in the form of aluminum paste.

[0085] The coating or ink may optionally contain other additives, such as dispersants, wetting agents, defoamers, leveling agents, rheology modifiers, antisettling agents, amine neutralizers, and combinations thereof.

[0086] In another aspect, this disclosure provides the use of the rheology modifier compositions disclosed herein in water-based coatings or inks.

[0087] Example The invention is illustrated by the following non-limiting embodiments.

[0088] As described below, it has been observed that mixing amide waxes or polyamide waxes with quaternary ammonium-containing polyamides contained in waterborne coating materials (e.g., waterborne metallic coatings, waterborne corrosion-resistant coatings, and waterborne metallic inks) can reduce or prevent pigment precipitation at high temperatures. Furthermore, precipitation can be reduced or prevented over a wider pH range. It has also been observed that mixing amide waxes or polyamide waxes with polyamide esters can reduce or prevent pigment precipitation at high temperatures.

[0089] Example A1: Synthesis of diamide or polyamide wax In a 2L four-necked flask equipped with a stirrer, temperature controller, water trap, and nitrogen inlet, 84.41 parts (4.37 mol) of 12-hydroxystearic acid were weighed and melted, followed by the gradual addition of 15.44 parts (2.11 mol) of hexamethylenediamine. 0.44 parts (0.0058 mol) of 85% phosphoric acid was added as a catalyst. A dehydration reaction was then carried out at 185°C to obtain a diamide or polyamide wax.

[0090] Examples A2-A9: Synthesis of amides or polyamide waxes Other amide or polyamide wax synthesis examples were carried out according to the synthesis method of Example A1 with the compositions shown in Table 1 to obtain amide or polyamide wax examples A2 to A9.

[0091] Table 1: Composition of Synthesis Examples of Amides and Polyamide Waxes Example B1: Synthesis of polyamides containing quaternary ammonium 0.66 mol of dimer acid and 0.17 mol of azelaic acid were placed in a 1 L four-necked flask equipped with a stirrer, thermostat, splitter, and nitrogen supply. The mixture was then stirred and heated to 100 °C. 0.51 mol of hexamethylenediamine was gradually added, and the exothermic reaction was observed. Then, 0.65 mol of dimethylaminopropylamine was added. The mixture was stirred and gradually heated to 175 °C for dehydration. After 3 hours of reaction, a brown tertiary amine-terminated polyamide was obtained. The tertiary amine-terminated polyamide and 250 g of propylene glycol monomethyl ether (PM) were placed in a 1000 mL four-necked flask equipped with a stirrer, thermostat, splitter, and nitrogen supply. The mixture was then stirred and heated to 90 °C. 0.65 mol of lauryl bromide was gradually added. The mixture was stirred and gradually heated to 95 °C. After 6 hours of reaction, a brown quaternary ammonium-containing polyamide with an amine value of 2.8 mg KOH / g was obtained (Example B1).

[0092] Examples B2-B7: Synthesis of Polyamides Containing Quaternary Ammonium Other polyamide synthesis examples were carried out according to the synthesis method of Example 1 using the compositions shown in Table 2, resulting in polyamide examples B2 to B7 containing quaternary ammonium. Example B0 is a comparative example, wherein the polyamide was ionized by an amine neutralizing agent instead of a quaternizing agent.

[0093] Table 2: Composition of Synthetic Examples of Polyamides Containing Quaternary Ammonium Example L1: Synthesis of a polyamide rheology modifier containing quaternary ammonium In a 1 L four-necked flask equipped with a stirrer, cooling tube, and thermometer, 250.8 parts of distilled water were weighed and heated to 75°C. Simultaneously, 36 parts of polyamide (B1) as component [B] and 13.2 parts of propylene glycol monomethyl ether (PM) as solvent were mixed and dissolved at 115°C to form a liquid. Next, this liquid mixture was gradually added to the warm water. After addition, to ensure complete dispersion, stirring was continued for an additional 30 minutes at a temperature of 70 to 80°C to obtain a dispersion. After stirring, the dispersion was transferred to a container and allowed to stand at 35°C for 24 hours to obtain rheology modifier L1.

[0094] Examples L2-L5: Synthesis of polyamide rheology modifiers containing quaternary ammonium Other examples of polyamide rheology modifiers containing quaternary ammonium were synthesized using the same synthesis method as in Example L1, with the compositions shown in Table 3A, to obtain polyamide examples L2 to L5 containing quaternary ammonium. L0 is a comparative example of an ionized polyamide rheology modifier obtained from ionized polyamide B0.

[0095] Table 3A: Synthesis Examples: Pure quaternary ammonium-containing polyamide rheology modifier Example M1: Synthesis of a polyamide rheology modifier containing quaternary ammonium In a 1 L four-necked flask equipped with a stirrer, cooling tube, and thermometer, 240 parts of distilled water were weighed and heated to 75°C. Simultaneously, 6 parts of amide wax (A1) as component [A], 24 parts of polyamide (B1) as component [B], 9.0 parts of polyethylene oxide 2-ethylhexyl ether (EHE-205) with an HLB of 12.5 as a surfactant, and 16.5 parts of propylene glycol monomethyl ether (PM) as a solvent were mixed and dissolved at 120°C to form a liquid. Next, this liquid mixture was gradually added to the warm water. After addition, to ensure complete dispersion, stirring was continued for an additional 30 minutes at a temperature of 70 to 80°C to obtain a dispersion. After stirring, the dispersion was transferred to a container and allowed to stand at 50°C for 24 hours to obtain rheology modifier M1.

[0096] Examples M2-M8: Synthesis of polyamide rheology modifiers containing quaternary ammonium Other examples of synthesizing polyamide rheology modifiers containing quaternary ammonium were carried out according to the synthesis method of Example M1, which had the composition shown in Table 3B, resulting in polyamide examples M2 to M8 containing quaternary ammonium. M0 is a comparative example of an ionized polyamide rheology modifier obtained from ionized polyamide B0.

[0097] Table 3B: Synthesis Examples: Polyamide Rheology Modifiers Containing Quaternary Ammonium Example C1: Synthesis of acid-terminated polyamide ester In a 1L four-necked flask equipped with a stirrer, temperature controller, water separator, and nitrogen inlet pipe, 81.45 parts (0.66 mol) of dimer acid and 5.55 parts (0.14 mol) of adipic acid were weighed and melted according to the mixing ratio shown in Table 4. Then, 13.0 parts (0.51 mol) of hexamethylenediamine were gradually added, and a dehydration reaction was carried out at 175°C to obtain polyamide. The mixture was cooled to 120°C and 14 parts (0.58 mol) of γ-valerol were added. The mixture was then heated to 135°C, and 0.44 parts (0.0058 mol) of DBTDL were added as a catalyst. The mixture was then heated to 160°C and the reaction was continued until the non-volatile content was greater than 99%, yielding polyamide ester C1.

[0098] Examples C2-C10: Synthesis of acid-terminated polyamide esters According to the synthesis method of ionized polyamide ester synthesis example C1, the mixing ratios shown in Table 4 were used to synthesize acid-terminated polyamide esters in examples C2-C10.

[0099] Table 4: Composition of the Synthesis Examples of Acid-Terminated Polyamide Esters Example N1: Rheology modifier for ionized polyamide esters In a 1L four-necked flask equipped with a stirrer, temperature controller, water separator, and nitrogen inlet pipe, 8.0 parts of acid-terminated polyamide ester C1 and 2.0 parts of amine wax A1 were added according to the mixing ratio shown in Table 5. Then, 3.0 parts of surfactant EHE-205 and 5.5 parts of propylene glycol monomethyl ether (PM) were weighed and melted at 120°C. 1.5 parts of dimethylaminoethanol (DMAE) were added and neutralized at 120°C for 10 min to obtain ionized polyamide ester. It was then transferred to water for dispersion under high-speed stirring to obtain the rheology modifier of ionized polyamide ester synthesis example N1.

[0100] Examples N2-N9: Rheology modifiers for ionized polyamide esters The rheology modifiers for ionized polyamide ester synthesis examples N2-N9 were synthesized using the mixing ratios shown in Table 5, according to the synthesis method of the rheology modifier in example N1 of ionized polyamide ester synthesis.

[0101] Table 5: Synthesis Examples: Rheology Modifiers for Ionized Polyamide Esters Test case The performance of waterborne coating rheology modifiers was tested on waterborne styrene-acrylic resin coatings with the compositions listed in Tables 6-8.

[0102] Table 6A: Formulation of polyamide [B] pregel Table 6B: Composition of Waterborne Styrene Acrylic Resin Coatings (Transparent Coatings) Table 7: Composition of Waterborne Styrene Acrylic Resin Coating (Aluminum Powder Paste) Table 8 Composition of Waterborne Styrene Acrylic Resin Coatings (Aluminum Coatings) Methods for preparing water-based coatings: The transparent coating in Table 6: DI water, DB, BCS, DOWSIL67 additive, and DAPRO DF 677 were mixed under stirring to obtain the base coating for Part A. Then, AC-2524, DMAE, and Rheolate 150 (50% aqueous solution) were added to Part A under stirring to obtain the water-based coating.

[0103] Table 7 Aluminum Powder Paste: DI water, Nuosperse FA 196, Hydrolan 2156, DB and BCS were mixed under stirring to obtain the base coating resin coating.

[0104] Aluminum coatings in Table 8: The transparent coating, rheology modifier, DI water, and aluminum powder paste from Table 6 are mixed under stirring to obtain the base coating resin coating.

[0105] Evaluation of the viscosity of Brookfield waterborne coatings: Viscosity: Brookfield DVII+pro (cP) Brookfield viscosity (cPs) of waterborne coatings at 25°C and 10 to 100 rpm was measured using a DV-II viscometer with an LV3 rotor, and the ratio (viscosity at 10 rpm / viscosity at 100 rpm) was calculated.

[0106] pH tolerance tests were conducted by adding the rheology modifier at an active dose of 2% or 1.68% to stirred deionized water. Viscosity was measured, and the pH was adjusted to pH=10, pH=7, and pH=4 using dimethylaminoethanol (DMAE) and acetic acid. pH values ​​were measured using a pH meter.

[0107] Table 9A: Performance testing of the example (0.48% active dose) L0: Using a comparative example as a reference for the rheology modifier. Table 9B: Performance testing of the example (4.8% dose) M0: Using a comparative example as a reference for the rheology modifier. The performance test results of the polyamide rheology modifiers containing quaternary ammonium compounds, examples L0-L5 and M0-M6, for waterborne coatings are shown in Tables 9A and 9B. The results indicate that the rheology modifiers of this invention exhibit good thixotropic properties when used in waterborne coating systems, and maintain their thickening efficiency even under pH fluctuations.

[0108] Table 10: Performance testing of the example (4.8% dose) M0: Using a comparative example as a reference for the rheology modifier. The performance test results of examples N2-N9 of the ionized polyamide ester rheology modifiers for waterborne coatings are shown in Table 10. The results indicate that the compositions exhibit good performance and improved thixotropic properties when used in waterborne coating systems. Thermal stability was also demonstrated.

[0109] The entire publication of each cited reference is incorporated into this document by reference. All references cited in this publication are incorporated into this document by reference, just as each reference is incorporated into this document by reference in its entirety.

[0110] The citations and inclusion of patent literature in this article are for convenience only and do not reflect any view on the validity, patentability, and / or enforceability of such patent literature.

[0111] Several embodiments of this disclosure have been described. However, it should be understood that various modifications can be made without departing from the spirit and scope of this disclosure. Therefore, other embodiments are also within the scope of the preceding claims.

[0112] All headings and subheadings used herein are for convenience only and should not be construed as limiting the invention in any way.

[0113] The use of any and all instances or exemplary language (such as "such as") provided herein is merely intended to better illustrate the invention and not to limit its scope, unless otherwise paragraphed. The language in this specification should not be construed as indicating that any element not paragraphed is essential to the practice of the invention.

Claims

1. A rheology modifier composition comprising a quaternary ammonium-containing polyamide [B] having formula (1). Equation (1) R4 is selected from the group consisting of: substituted or unsubstituted alkyl groups with straight or branched chains having 2 to 36 carbon atoms; R5 is selected from the group consisting of: substituted or unsubstituted alkyl groups with straight or branched chains having 2 to 34 carbon atoms; R6 is selected from the group consisting of: substituted or unsubstituted alkyl groups with straight or branched chains having 2 to 12 carbon atoms; R7 is selected from the group consisting of: hydrogen, or alkyl, alkyl carboxylic acid esters or alkyl sulfonates having 1 to 18 carbon atoms, or combinations thereof; And m ranges from 1 to 10.

2. The rheology modifier composition according to claim 1, further comprising amide wax or polyamide wax [A].

3. The rheology modifier composition according to claim 2, wherein the amide wax or polyamide wax [A] has the formula (2). Equation (2) R1 is selected from the group consisting of: substituted or unsubstituted alkyl groups with straight or branched chains having 2 to 36 carbon atoms; R2 is selected from the group consisting of: substituted or unsubstituted alkyl groups with straight or branched chains having 1 to 21 carbon atoms; R3 is selected from the group consisting of: substituted or unsubstituted alkyl groups with straight or branched chains having 2 to 34 carbon atoms; And n ranges from zero to 10.

4. A rheology modifier composition comprising a mixture of a polyamide [B] containing quaternary ammonium and an amide wax or a polyamide wax [A].

5. The rheology modifier composition according to claim 4, wherein the quaternary ammonium-containing polyamide [B] has the formula (1). Equation (1) R4 is selected from the group consisting of: substituted or unsubstituted alkyl groups with straight or branched chains having 2 to 36 carbon atoms; R5 is selected from the group consisting of: substituted or unsubstituted alkyl groups with straight or branched chains having 2 to 34 carbon atoms; R6 is selected from the group consisting of: substituted or unsubstituted alkyl groups with straight or branched chains having 2 to 12 carbon atoms; R7 is selected from the group consisting of: hydrogen, or alkyl, alkyl carboxylic acid esters, or alkyl sulfonates having 1 to 18 carbon atoms, or combinations thereof; and The range of m is 1 to 10; And the amide wax or polyamide wax [A] therein has formula (2). Equation (2) R1 is selected from the group consisting of: substituted or unsubstituted alkyl groups with straight or branched chains having 2 to 36 carbon atoms; R2 is selected from the group consisting of: substituted or unsubstituted alkyl groups with straight or branched chains having 1 to 21 carbon atoms; R3 is selected from the group consisting of: substituted or unsubstituted alkyl groups with straight or branched chains having 2 to 34 carbon atoms; And n ranges from zero to 10.

6. A method for preparing a rheology modifier comprising a quaternary ammonium-terminated polyamide, wherein the quaternary ammonium-terminated polyamide [B] is obtained by reacting a tertiary amine-terminated polyamide with a quaternizing agent.

7. The method for preparing a rheology modifier according to claim 6, wherein the tertiary amine-terminated polyamide is obtained by reacting a diamine having 2 to 34 carbon atoms or a mixture of diamines having 2 to 34 carbon atoms with an excess of a dicarboxylic acid having 4 to 36 carbon atoms relative to the diamine; or a mixture of a dicarboxylic acid having 4 to 36 carbon atoms and a tertiary amine having 2 to 12 carbon atoms of a dimethylaminoalkylamine, wherein the tertiary amine-terminated polyamide has an acid value of less than 10 mg KOH / g and an amine value in the range of 30 to 200 mg KOH / g.

8. The method for preparing a rheology modifier according to claim 7, wherein the diamine is selected from the group consisting of: ethylenediamine, 1,4-butanediamine, hexanediamine, 1,10-decanediamine, 1,11-undecanediamine, 1,12-dodecanediamine, phenylenediamine, and 4,4'-diaminodiphenylmethane; wherein the tertiary amine is selected from the group consisting of: dimethylaminopropylamine, dimethylaminobutylamine, dimethylaminopentylamine, and dimethylaminohexylamine; and wherein the dicarboxylic acid is selected from the group consisting of: malonic acid, succinic acid, glutamic acid, adipic acid, pimelic acid, octanoic acid, azelaic acid, sebacic acid, dodecanoic acid, isophthalic acid, and dimer fatty acids.

9. The method for preparing a rheology modifier according to claim 6, wherein the quaternizing agent is selected from the group consisting of: haloalkanes having 1 to 18 carbon atoms, sodium chloroalkylcarboxylate having 1 to 11 carbon atoms, cyclic sulfonates or sulfonyl lactones having 3 to 6 carbon atoms, or combinations thereof.

10. The method for preparing a rheology modifier according to claim 9, wherein the quaternizing agent is selected from the group consisting of: acetic acid, acrylic acid, hydrogen peroxide, sodium chloroacetate, dimethyl sulfonate, iodomethane, 1,3-propane sulfonyl lactone and 1,4-butane sulfonyl lactone.

11. A method for preparing a rheology modifier, comprising mixing a quaternary ammonium-terminated polyamide [B] with a polyamide wax [A].

12. The method for preparing a rheology modifier according to claim 11, wherein the quaternary ammonium-terminated polyamide [B] is obtained by reacting a tertiary amine-terminated polyamide with a quaternizing agent.

13. The method for preparing a rheology modifier according to claim 12, wherein the tertiary amine-terminated polyamide is obtained by reacting a diamine having 2 to 34 carbon atoms or a mixture of diamines having 2 to 34 carbon atoms with an excess of a dicarboxylic acid having 4 to 36 carbon atoms or a mixture of a dicarboxylic acid having 4 to 36 carbon atoms and a tertiary amine having 2 to 12 carbon atoms, wherein the tertiary amine-terminated polyamide has an acid value of less than 10 mg KOH / g and an amine value in the range of 30 to 200 mg KOH / g.

14. The method for preparing a rheology modifier according to claim 13, wherein the diamine is selected from the group consisting of: ethylenediamine, 1,4-butanediamine, hexanediamine, 1,10-decanediamine, 1,11-undecanediamine, 1,12-dodecanediamine, phenylenediamine, and 4,4'-diaminodiphenylmethane; wherein the tertiary amine is selected from the group consisting of: dimethylaminopropylamine, dimethylaminobutylamine, dimethylaminopentylamine, and dimethylaminohexylamine; and wherein the dicarboxylic acid is selected from the group consisting of: malonic acid, succinic acid, glutamic acid, adipic acid, pimelic acid, octanoic acid, azelaic acid, sebacic acid, dodecanoic acid, isophthalic acid, and dimer fatty acids.

15. The method for preparing a rheology modifier according to claim 12, wherein the quaternizing agent is selected from the group consisting of: haloalkanes having 1 to 18 carbon atoms, sodium chloroalkylcarboxylate having 1 to 11 carbon atoms, cyclic sulfonates or sulfonyl lactones having 3 to 6 carbon atoms, or combinations thereof.

16. The method for preparing a rheology modifier according to claim 13, wherein the quaternizing agent is selected from the group consisting of: acetic acid, acrylic acid, hydrogen peroxide, sodium chloroacetate, dimethyl sulfonate, iodomethane, 1,3-propane sulfonyl lactone and 1,4-butane sulfonyl lactone.

17. The method for preparing a rheology modifier according to claim 11, wherein the amide wax or polyamide wax [A] is obtained by reacting a diamine having 2 to 12 carbon atoms with a monocarboxylic acid having 2 to 22 carbon atoms and / or a dicarboxylic acid having 4 to 36 carbon atoms.

18. The method for preparing a rheology modifier according to claim 17, wherein the diamine is selected from the group consisting of ethylenediamine, 1,4-butanediamine, hexanediamine, 1,10-decanediamine, 1,11-undecanediamine, 1,12-dodecanediamine, phenylenediamine, and 4,4'-diaminodiphenylmethane.

19. The method for preparing a rheology modifier according to any one of claims 17 or 18, wherein the dicarboxylic acid is selected from the group consisting of: malonic acid, succinic acid, glutamic acid, adipic acid, pimelic acid, octanoic acid, azelaic acid, sebacic acid, dodecanoic acid, isophthalic acid and dimer fatty acids, and wherein the monocarboxylic acid is selected from the group consisting of: lauric acid, 12-hydroxystearic acid, stearic acid, fatty acids, butyric acid, hexanoic acid, palmitic acid and oleic acid.

20. A coating or ink comprising a rheology modifier composition according to any one of claims 1 to 5.

21. The coating or ink according to claim 20, wherein the coating or ink is a water-based coating or ink.

22. The coating or ink according to claim 20 or 21, comprising the rheology modifier composition in an amount of about 0.1 wt% to about 20 wt%, preferably about 1.0 wt% to about 10 wt%, more preferably about 2 wt% to about 5 wt%.

Images