TW202108659A - Aromatic amide dispersant - Google Patents

Abstract

The present invention relates to a polymeric dispersant containing an tertiary amide linkage between the aromatic anchoring group and a solubilizing chain, and a composition containing a particulate solid, an aqueous or polar organic medium, and a polymeric aromatic amide dispersant having at least one tertiary amide linking group connecting through a carbonyl group of the amide to an aromatic ring having two or more residual carboxylic acid groups or a sulfonic acid group and a residual carboxylic acidic group thereon. The invention further provides compositions for millbases, dispersions, coatings and inks containing said dispersant.

Description

Aromatic Amine Dispersant

The present invention relates to a polymeric aromatic amine dispersant, and a composition comprising a particulate solid, an aqueous medium or a polar organic medium and a polymeric dispersant with an aromatic ring with acid functionality, wherein the aromatic ring passes through three The graded amide chain is chemically linked to a solubilizing polymer chain. The present invention further provides a composition including the dispersant for grinding base materials, dispersions, coatings (including coatings) and inks.

Many formulations such as inks, coatings, and abrasive bases require effective dispersants to uniformly distribute particulate solids in aqueous or polar organic media. For ink, ink manufacturers want to produce high-resolution and high-quality printed products. Printing methods pose a challenge to the adaptability of substrates, resins and pigments in an ever-expanding range. The pigment dispersion should be compatible with the different formulations used to ensure that the final coating has good adhesion and resistance. Poor pigment dispersion or stability can cause agglomeration or precipitation in the polar organic liquid medium or aqueous liquid medium.

其中T係-(CH₂ )₃ -或-CH₂ CH(CH₃ )-； R’係H、或選擇性經取代的C_1-50 烴基(hydrocarbyl)、或選擇性經取代的C_1-50 烴羰基(hydrocarbonyl)； Y係C_2-4 -伸烷氧基； x係2至90；及 q係1或2。PCT Patent Publication WO 2008/028954 discloses an imine dispersant compound including terminal acid groups in both polar and non-polar organic media, wherein the dispersant compound is represented by the following structure:

Wherein T is -(CH ₂ ) ₃ -or -CH ₂ CH(CH ₃ )-; R'is H, or optionally substituted C _1-50 hydrocarbon group (hydrocarbyl), or optionally substituted C _{1- 50} hydrocarbon carbonyl (hydrocarbonyl); Y is C _2-4 -alkoxy; x is 2 to 90; and q is 1 or 2.

US Patent No. 5,688,312 discloses an ink composition containing a colorant and an imine or bisimines, which has a viscosity of about 1 to 10 centipoise at a temperature of about 125 to 180°C. The imines or bisimines can be prepared by reacting phthalic anhydride with mono- or diamines. The monoamine may be, for example, dodecylamine or stearylamine. The diamine may be 1,12-dodecane diamine.

PCT Patent Publication WO 2007/139980 discloses the reaction product of at least one dianhydride and at least two different reactants, wherein each of the reactants includes a primary or secondary amine group, a hydroxyl group or a thiol functional group, and the At least one of the reactants is a polymeric type. The reaction product is useful in compositions such as inks and coatings.

U.S. Patent 6,440,207 discloses a method for preparing dispersed dry organic pigments for aqueous systems by: (a) grinding a mixture comprising: (1) one or more organic pigments, (2) relative to the organic Pigment, at least about 1% by weight of one or more aromatic poly(alkylene oxide) dispersants, (3) relative to the organic pigment, 0 to about 10 parts by weight of the grinding liquid, wherein the organic pigment is substantially insoluble in the Grinding liquid, (4) relative to the organic pigment, 0 to about 50% by weight of one or more grinding additives other than the dispersant (2), and (5) relative to the organic pigment, 0 to about 20% by weight One or more surface treatment additives; (b) Optionally, add the following to the ground pigment: (6) One or more liquids in which the organic pigment is substantially insoluble, in an amount such that the total solid content does not decrease More than about 10%, and (7) one or more polyvalent metal salts and/or one or more quaternary ammonium salts; and (c) separating the ground organic pigment. The aromatic polyalkylene oxide dispersant can be prepared by mixing 19.8 grams (0.100 mol) of 1,8-naphthalic anhydride and 105 grams (0.105 mol) of Jeffamine in a pressure cooker containing 250 grams of deionized water. ™ XTJ-506 (83% by weight ethylene oxide, 17% by weight propylene oxide) is prepared by reaction. The pressure cooker was sealed, heated to 150°C with stirring, and maintained at 150°C for five hours. After the reaction had cooled, the resulting brown liquid was discharged into a beaker, and then 15 grams of decolorized charcoal was added. After stirring overnight, the suspension was filtered and the filter cake was washed with water, resulting in approximately 500 grams of an amber filtrate with a solids content of 23.63%. The dry pigment can be used in water-based coating systems.

US Patent Publication 2008/0202382 describes the use of the Michael reaction of polyether methacrylate and polyamine for dispersion of ultrafine particles. The invention relates to an amine dispersant for organic dispersion and a coating composition including the dispersant.

其中R₁ 係在Q環之任何可得以鍵結至取代基的位置上之取代基，且其各自獨立地由至少一個吸電子基團表示；a係1或2。W係氧、硫、NH或NG。R₂ 係C_1-20 伸烴基或C_1-20 伸烴羰基(hydrocarbonylene)，其中R₂ 包括多於2個碳原子且可係線性或分枝。R₃ 係H、或鍵結至該聚合物鏈的終端氧原子而形成終端醚或酯之選擇性經取代的C_1-50 烴基。Pol係環氧乙烷的同元聚合物鏈或環氧乙烷的共聚物鏈，其中該環氧乙烷構成該由聚醚或聚酯組成的共聚物鏈之40重量%至99.99重量%。U.S. Patent Publication 2015/112020 describes the use of fused aromatic imidine pendant groups as anchors for pigment dispersants, which are represented by the following structure:

Wherein R ₁ is a substituent at any position of ring Q that can be bonded to a substituent, and each of them is independently represented by at least one electron withdrawing group; a is 1 or 2. W is oxygen, sulfur, NH or NG. R ₂ is a C _1-20 hydrocarbylene group or a C _1-20 hydrocarbonylene group, wherein R ₂ includes more than 2 carbon atoms and can be linear or branched. R ₃ is H, or is bonded to the terminal oxygen atom of the polymer chain to form a terminal ether or ester optionally substituted C _1-50 hydrocarbon group. Pol is a homopolymer chain of ethylene oxide or a copolymer chain of ethylene oxide, wherein the ethylene oxide constitutes 40% to 99.99% by weight of the copolymer chain composed of polyether or polyester.

An object of the present invention is to provide a dispersant which can provide a low-viscosity colloidal stable dispersion with inorganic and organic pigments. By providing greater colloidal stability, it can improve chromaticity, other coloring properties, increase particulate solid loading, form improved dispersions, have improved brightness, produce compositions with reduced viscosity, maintain stable dispersions, and reduce Particle size and reduction of particle size distribution, reduction of haze value, improvement of gloss, improvement of chroma and increase of jetness (especially when the composition includes inorganic pigments or fillers). The composition of the present invention can also be colloidally stable under ambient storage and high-temperature storage conditions.

We have recently discovered that it is beneficial to first react the primary amine-terminated solubilizing chain such as polyetheramine and acrylate, and then react with an acid-functionalized aromatic dicarboxylic acid or polycarboxylic acid anhydride, because this can only form amides. (And non-imine). The free carboxyl groups generated on the aromatic ring significantly improve the dispersibility of inorganic pigments except organic and carbon black pigments. Aromatic amine functional group dispersant

R₁ 各自獨立地係CO₂ H或SO₃ H，其中a係1至2或3； R₂ 係H、或選擇性經取代的C_1-50 烴基、或選擇性經取代的C_1-50 烴羰基； G係選擇性經雜原子諸如O或N取代的C_1-50 烴基，該O或N係表示如為醚、酯、醛、酮、醯胺、胺基甲酸酯、醇或羧酸基團、或G係選擇性經取代的(甲基)丙烯酸烷酯或(甲基)丙烯醯胺之殘基(所列舉的反應性物種之化學反應的預計反應及/或聚合產物)、或下式的環氧化物之開環產物：

其中在每個情況中，R₆ 可各別地係H、或CH₃ 、或C₂ H₅ 、或下列基團之一：

其中D係C_1-5 烷基、CN、OH、NO₂ 、NH₂ 、鹵素、CO₂ H、SO₃ H、CH₃ 或OCH₃ ；及p係0至4； R₃ 係線性或分枝的C_1-50 及較佳為C_1-20 烷基； 其中T係-C(O)-CH(R₄ )CH₂ 或C_1-5 烴基鏈； 當G係C_1-50 烴基時，T係-C(O)-CH(R₄ )CH₂ ； 當G係丙烯酸酯或環氧化物的殘基(所列舉的反應性物種之化學反應的預計反應及/或聚合產物)時，T係C_1-5 烴基鏈； R₄ 係H或Me，較佳為H； Y在每個重覆單元中各自獨立地係C_2-4 伸烷氧基； Q係包含一或多個芳香環(最高三或四個環)的伸烴基，其經R₁ 取代，若存在有二個芳香環時，其選擇性係稠合，其中該接附至Q的羧酸基團係接附至該Q的芳香環之碳原子； 其中在該式中的任何酸之氫可由金屬、胺或銨陽離子置換以讓該分散劑呈鹽形式；及 x係2至90。 在一個具體實例中，Q可以基於具有醯胺鏈結的苯環。在一個較佳的具體實例中，Q係衍生自1,2,4-苯三羧酸酐。該接附至Q的羧酸或磺酸基團係接附至Q的芳香環碳。A dispersant comprising a dispersant polymer having the following structure: Formula I

R _{1 is} each independently CO ₂ H or SO ₃ H, wherein a is 1 to 2 or 3; R ₂ is H, or an optionally substituted C _1-50 hydrocarbon group, or an optionally substituted C _{1-50 Hydrocarbon carbonyl group; G is a C 1-50} hydrocarbon group optionally substituted with heteroatoms such as O or N, the O or N is represented as ether, ester, aldehyde, ketone, amide, urethane, alcohol or carboxyl Acid group, or G-type optionally substituted alkyl (meth)acrylate or (meth)acrylamide residues (the expected reaction and/or polymerization product of the chemical reaction of the listed reactive species), Or the ring-opening product of epoxide of the following formula:

Wherein in each case, R ₆ can be H, or CH ₃ , or C ₂ H ₅ , or one of the following groups:

Wherein D is C _1-5 alkyl, CN, OH, NO ₂ , NH ₂ , halogen, CO ₂ H, SO ₃ H, CH ₃ or OCH ₃ ; and p is 0 to 4; R ₃ is linear or branched The C _1-50 and preferably a C _1-20 alkyl group; wherein T is -C(O)-CH(R ₄ )CH ₂ or a C _1-5 hydrocarbyl chain; when G is a C _1-50 hydrocarbyl group, T is -C(O)-CH(R ₄ )CH ₂ ; when G is the residue of acrylate or epoxide (the expected reaction and/or polymerization product of the chemical reaction of the listed reactive species), T It is a C _1-5 hydrocarbyl chain; R ₄ is H or Me, preferably H; Y is independently a C _2-4 alkylene group in each repeating unit; Q contains one or more aromatic rings (up to three or four ring) extending hydrocarbon group, which by R _1, if there is two aromatic rings which are fused selective system, where the Q is attached to the carboxylic acid group is attached to the system The carbon atom of the aromatic ring of Q; wherein the hydrogen of any acid in the formula can be replaced by a metal, amine or ammonium cation to make the dispersant in the form of a salt; and x is 2 to 90. In a specific example, Q may be based on a benzene ring with an amide linkage. In a preferred embodiment, Q is derived from 1,2,4-benzenetricarboxylic anhydride. The carboxylic acid or sulfonic acid group attached to Q is the aromatic ring carbon attached to Q.

The present invention provides a dispersant; and a composition comprising the dispersant, particulate solids (such as pigments or fillers), and an aqueous or polar organic medium; and the particulates, dispersant and continuous medium as a grinding base, ink, Use of coatings (paints), etc. If used as a coating, the composition may optionally include an adhesive.

The polymer chain may have a number average molecular weight of 100 to 10,000, or 100 to 5,000, or 300 to 3,000, or 400 to 2,500.

The number average molecular weight of the pre-prepared polymer chains can be determined by GPC analysis. The on-site preparation, that is, the number-average molecular weight of the polymer grown from the starting species (initiator) group of the polymer chain can be calculated by measuring the degree of polymerization (DP), where the degree of polymerization is It is proportional to the ratio of monomer [M] and initiator [I] (the initiator is an intermediate derived from the condensed aromatic anhydride), and by the formula DP=[M]/[I] To calculate. Analysis using nuclear magnetic resonance (NMR) can be used to determine the degree of polymerization, and therefore to calculate the number average molecular weight of the polymerized groups or polymer fragments of the molecule.

Definitions of hydrocarbyl and hydrocarbyl. As used herein, the term "hydrocarbyl" is used in the ordinary sense of the term and is intended to include any divalent group formed by removing two hydrogen atoms from a hydrocarbon. In the context of the present invention, the term "hydrocarbyl" or "hydrocarbyl" indicates a group having a carbon atom directly attached to the remainder of the molecule and having hydrocarbon or distinctive hydrocarbon characteristics. This group includes the following: (1) Pure hydrocarbon group, that is, aliphatic (for example, alkyl or alkenyl), alicyclic (for example, cycloalkyl or cycloalkenyl), aromatic, and aliphatic And alicyclic substituted aromatic, aromatic substituted aliphatic and alicyclic groups, and similar groups, and the cyclic group completed by another part of the molecule (that is, Any two of the indicated substituents may together form an alicyclic group). Examples thereof include methyl, ethyl, octyl, decyl, octadecyl, cyclohexyl, phenyl and the like. (2) A substituted hydrocarbon group, that is, a group including a non-hydrocarbon substituent that does not change the prominent hydrocarbon characteristics of the group. Those familiar with the technology will perceive suitable substituents. Examples thereof include hydroxyl, nitro, cyano, alkoxy, acyl and the like. (3) Heterogroup, that is, a chain or ring composed of carbon atoms in other aspects includes atoms other than carbon and hydrogen, and a group with significant hydrocarbon characteristics. Suitable heteroatoms will be understood by those skilled in the art and include, for example, nitrogen, oxygen and sulfur.

As used herein, the term "hydrocarbocarbylene" is intended to include any hydrocarbon group containing a carbonyl group (>C=O), for example, a hydrocarbon group including a ketone group or an aldehyde group. Typically, the alkylene carbonyl group may include -(CH ₂ ) ₅ -C(O)-, -(CH ₂ ) ₄ -C(O)-, -(CH ₂ ) ₃ -C(O)- or- (CH ₂ ) ₂ -C(O)-. As used herein, the reference alkylene or alkylene carbonyl can be linear or branched and saturated or unsaturated.

R₁ 各自獨立地係CO₂ H或SO₃ H，其中a係1至2或3； R₂ 係H、或選擇性經取代的C_1-50 烴基、或選擇性經取代的C_1-50 烴羰基； G係選擇性經雜原子諸如O或N取代的C_1-50 烴基，該O或N係顯現出如為/表示出如為醚、酯、醛、酮、醯胺、胺基甲酸酯、醇或羧酸基團、或G係選擇性經取代的(甲基)丙烯酸烷酯或(甲基)丙烯醯胺之殘基(所列舉的反應性物種之化學反應的預計反應及/或聚合產物)、或下式之環氧化物的開環產物：

； 其中在每個情況中，R₆ 可各別地係H、或CH₃ 、或C₂ H₅ 、或下列基團之一：

其中D係C_1-5 烷基、CN、OH、NO₂ 、NH₂ 、鹵素、CO₂ H、SO₃ H、CH₃ 或OCH₃ ；及p係0至4； R₃ 係線性或分枝的C_1-50 及較佳為C_1-20 烷基； T係-C(O)-CH(R₄ )CH₂ 或C_1-5 烴基鏈； 當G係C_1-50 烴基時，T係-C(O)-CH(R₄ )CH₂ ； 當G係丙烯酸酯或環氧化物的殘基(所列舉的反應性物種之化學反應的預計反應及/或聚合產物)時，T係C_1-5 烴基鏈； R₄ 係H或Me，較佳為H； Y在每個重覆單元中各自獨立地係C_2-4 伸烷氧基； Q係包含一或多個芳香環(最高三或四個環)的伸烴基，其係經R₁ 取代，若存在有二個芳香環時，其選擇性係稠合，其中該接附至Q的羧酸基團係接附至Q的芳香環之碳原子； 其中在該式中的任何酸之氫可由金屬、胺或銨陽離子置換以讓該分散劑呈鹽形式；及 x係2至90。 在一個具體實例中，Q可以基於具有醯胺鏈結的苯環。在一個較佳的具體實例中，Q係衍生自1,2,4-苯三羧酸酐的苯環。該接附至Q的羧酸基團及選擇性磺酸基團係接附至Q的芳香環之碳原子。具體實例 1a The disclosed dispersant comprises a dispersant polymer having the following structure: Formula I

R _{1 is} each independently CO ₂ H or SO ₃ H, wherein a is 1 to 2 or 3; R ₂ is H, or an optionally substituted C _1-50 hydrocarbon group, or an optionally substituted C _{1-50 Hydrocarbon carbonyl group; G is a C 1-50} hydrocarbon group optionally substituted with heteroatoms such as O or N, and the O or N system appears as/shows as ether, ester, aldehyde, ketone, amide, aminomethyl Acid ester, alcohol or carboxylic acid group, or G-type optionally substituted alkyl (meth)acrylate or (meth)acrylamide residues (predicted reactions and chemical reactions of the enumerated reactive species) / Or polymerization product), or the ring-opening product of the epoxide of the following formula:

; Wherein in each case, R ₆ can be H, or CH ₃ , or C ₂ H ₅ , or one of the following groups:

Wherein D is C _1-5 alkyl, CN, OH, NO ₂ , NH ₂ , halogen, CO ₂ H, SO ₃ H, CH ₃ or OCH ₃ ; and p is 0 to 4; R ₃ is linear or branched The C _1-50 and preferably a C _1-20 alkyl group; T is -C(O)-CH(R ₄ )CH ₂ or a C _1-5 hydrocarbyl chain; when G is a C _1-50 hydrocarbyl group, T Is -C(O)-CH(R ₄ )CH ₂ ; when G is the residue of acrylate or epoxide (the expected reaction and/or polymerization product of the chemical reaction of the listed reactive species), T is C _1-5 hydrocarbyl chain; R ₄ is H or Me, preferably H; Y is each independently a C _2-4 alkylene group in each repeating unit; Q contains one or more aromatic rings ( Up to three or four rings) alkylene group, which is _{substituted by R 1} , if there are two aromatic rings, the selectivity is fused, wherein the carboxylic acid group attached to Q is attached to Q The carbon atom of the aromatic ring; wherein the hydrogen of any acid in the formula can be replaced by a metal, amine or ammonium cation to make the dispersant in the form of a salt; and x is 2 to 90. In a specific example, Q may be based on a benzene ring with an amide linkage. In a preferred embodiment, Q is derived from the benzene ring of 1,2,4-benzenetricarboxylic acid anhydride. The carboxylic acid group and the optional sulfonic acid group attached to Q are the carbon atoms of the aromatic ring attached to Q. Specific example 1a

具體實例 2a Reaction between polyetheramine and (meth)acrylate

Specific example 2a

具體實例 3a Reaction between polyetheramine and epoxide

Specific example 3a

Reaction between alkylamine and polyether (meth)acrylate

The following is the structure of the unit added to the nitrogen atom of the amide linkage before the nitrogen system reacts with the carboxylic acid group of the aromatic ring to form the amide linkage. * Represents the point where the displayed structure is attached to the nitrogen atom. These structures are derived from unsaturated monomers (such as various acrylates) further shown below.

Z is -OH, -N(R ₇ ) ₂ (wherein in each case, R ₇ is C _1-5 alkyl), C _3-6 cycloalkyl, carbon and oxygen and/or nitrogen 5, 6 or 7-atom heterocycles, or acid groups such as CO ₂ H, SO ₃ H, OPO ₃ H ₂ ; U is O or NH; w is 1 to 20, preferably 1 to 10 and most preferably 1-5. D and p are as previously defined, and x ₁ is an integer from 1 to 50 and more desirably from 1 to 20. When the medium used to disperse the particles or includes a large amount of polar organic solvents, a value of 1 to 20 is preferable for w. When the medium for dispersing particles is water, a value of 1 to 5 is preferable for w.

Examples of the monomers that will form G are as follows, wherein U is O or NH; R ₂ is H, or an optionally substituted C _1-50 hydrocarbon group, or an optionally substituted C _1-50 hydrocarbon carbonyl group; R ₃ is linear or branched C _1-50 and preferably C _1-20 alkyl; R ₄ is H or CH ₃ ; R ₅ is H, or methyl, ethyl, propyl, butyl or benzene基; and x ₁ is 1-20. D is C _1-5 alkyl, CN, OH, NO ₂ , NH ₂ , halogen, CO ₂ H, SO ₃ H, CH ₃ and OCH ₃ ; and p is 0-4.

其中在每個情況中，R₆ 可各別地係H、CH₃ 、C₂ H₅ 或下列基團：

其中D係C_1-5 烷基、CN、OH、NO₂ 、NH₂ 、鹵素、CO₂ H、SO₃ H、CH₃ 或OCH₃ ；及p係0至4。Examples of the epoxides that will form G are as follows:

Wherein in each case, R ₆ can be H, CH ₃ , C ₂ H ₅ or the following groups respectively:

Wherein D is C _1-5 alkyl, CN, OH, NO ₂ , NH ₂ , halogen, CO ₂ H, SO ₃ H, CH ₃ or OCH ₃ ; and p is 0-4.

式IIb

式IIc

式IIIa

式IIIb

式IVa

式IVb

式V

The dispersant may have the following structure: Formula IIa

Formula IIb

Formula IIc

Formula IIIa

Formula IIIb

Formula IVa

Formula IVb

Formula V

Wherein R ₆ can be R ₂ , optionally substituted benzene ring, R ₃ -CO ₂ H group, ether linkage to optionally substituted benzene ring, or optionally substituted naphthalene fused aromatic ring The ether link of the structure.

Q is an organic structure with at least one and up to 3 or 4 aromatic rings (which can be selectively fused together), and can be based on benzene, phenyl, biphenyl, or fused aromatic rings such as naphthalene or anthracene. In a specific example, Q can be a single benzene ring derived from benzoic acid. Typically, Q-(R ₁ ) _a is derived from 1,2,4-benzenetricarboxylic acid anhydride.

Q may be based on benzene, naphthalene, anthracene, phenanthrene or mixtures thereof. In a specific example, Q may be based on naphthalene. When Q is based on naphthalene, the polymer chain of formula I can use a naphthalene amide group substituted _{with one or more R 1 at the position where the naphthalene ring gives substituents and amide linkages, such as in naphthalene} At least 1,2,2,3 or 1,8 position or a mixture of these positions.

When Q is based on biphenyl, the polymer chain of formula I can have single or multiple R ₁ substitutions on the biphenyl ring and use such as 4', 3, 4, 5', 3, 4, 3', 4 ',3 position or a mixture of these positions.

Examples of the anhydride that will form Q are as follows, where R ₁ is CO ₂ H or SO ₃ H. It should be noted that R ₁ can be present on any aromatic ring.

Typically, the Q series are derived from aromatic tricarboxylic acid anhydrides, such as tricarboxylic acid naphthalene anhydride, tricarboxylic acid biphenyl anhydride, tricarboxylic acid phthalic anhydride, or mixtures thereof.

The structure can be prepared by a method that involves reacting Michael acceptors such as (meth)acrylates or functional group-substituted (meth)acrylates with nucleophilic polymer chains such as polyetheramines. A secondary amine is formed, and then the secondary amine is reacted with an acid-functionalized aromatic diacid or anhydride such as the above-described including tricarboxylic acid phthalic anhydride and sulfonic acid-functionalized dicarboxylic acid phthalic anhydride to form the shown in the present invention Tertiary amide and structure. The first step Michael reaction can be carried out at a high temperature sufficient for activation, such as 0°C to 150°C, or 50°C to 200°C. The second step of the reaction to form the tertiary amide is carried out at a high temperature sufficient for amination, such as at least 50°C, or 50°C to 120°C.

The structure can be prepared by a method comprising reacting a polymeric acrylate such as MPEG acrylate, and then reacting with a nucleophilic aliphatic amine to form a secondary amine, and functionalizing the secondary amine with an acid Aromatic diacids or anhydrides such as tricarboxylic acid phthalic anhydride react to form the tertiary amines and structures shown in the present invention. The first step Michael reaction can be carried out at a high temperature sufficient for activation, such as 0°C to 150°C, or 50°C to 200°C. The second step of the reaction to form the tertiary amide is carried out at a high temperature sufficient for amination, such as at least 50°C, or 50°C to 120°C.

The structure can be prepared by a method comprising reacting a hydroxy acrylate such as hydroxyethyl acrylate, and then reacting with a nucleophilic aliphatic amine to form a secondary amine, and allowing the secondary amine to react with an acid-functional aromatic Group diacids or anhydrides react to form tertiary amides. Then, the product is reacted and polymerized with cyclic esters such as caprolactone to form polymer chains. The first step Michael reaction can be carried out at a high temperature sufficient for activation, such as 0°C to 150°C, or 50°C to 200°C. The second step of the reaction to form the tertiary amide is carried out at a high temperature sufficient for amination, such as at least 50°C, or 50°C to 120°C. The polymerization can be carried out at a high temperature sufficient for polymerization, for example, at least 100°C to 200°C. Specific example 1- Aromatic amine functional group dispersant containing polyether chain

In specific example 1, the polyether amine is reacted with (meth)acrylate (optionally substituted) via Michael reaction to produce a secondary amine, and then the secondary amine is reacted with an acid-functional aromatic anhydride. This system is covered by formulas IIa, IIb, IIc, IIIa, IIIb, IVa and IVb.

R ₃ is an optionally substituted C _1-50 (or C _1-20 ) hydrocarbon group, which is bonded to the terminal oxygen atom of the polymer chain to form a terminal ether; or C _1-50 (or C _1-20 ) A hydrocarbon carbonyl group (ie, a hydrocarbon group including a carbonyl group), which is bonded to the oxygen atom of the polymer chain to form a terminal ester group or a terminal urethane group, and the substituent may be a halogen group, an ether, or an ester Or a mixture thereof.

R ₅ may be H, or a mixture of H (in an amount sufficient to provide ethylene oxide groups, at 40% to 99.99% by weight) and at least one of methyl, ethyl, and phenyl. The optionally substituted (meth)acrylate may be any of those shown below, where the variables are as previously defined.

The reaction of polyetheramine with (meth)acrylic acid and then with acid-functional aromatic anhydride, for example, the reaction of Surfonamine® L207 with acrylic acid and then with tricarboxylic acid phthalic anhydride. The reaction of polyetheramine with tertiary aminoalkyl (meth)acrylate and then with acid-functional aromatic anhydride, for example, Surfonamine® L200 with dimethylaminoethyl acrylate and then with tricarboxylic acid phthalic anhydride.

The reaction of polyetheramine with alkyl (meth)acrylate and then with acid-functional aromatic anhydride, for example, the reaction of Surfonamine® L200 with butyl acrylate and then with tricarboxylic acid phthalic anhydride.

The polyether may have a number average molecular weight of 100 to 10,000, 100 to 5,000, or 300 to 3,000, or 400 to 2,500. The polyetheramine can be prepared by reacting the monoalcohol initiator only with ethylene oxide or with a mixture of ethylene oxide and propylene oxide to form an alcohol-terminated polymer chain, and then the alcohol-terminated polymer chain The polymer chains are converted into amines. The polyetheramine can be obtained by alkoxylation of amino alcohols, as described in US Patent No. 5,879,445 (especially disclosed in column 2, line 50 to column 7, line 50).

For aqueous dispersions (50-100% water), the polyether can be, for example, a copolymer of ethylene oxide and propylene oxide. The polyether can be derived from: 0 to 60% by weight of propylene oxide and 40 to 100% by weight of ethylene oxide; or 0 to 50% by weight of propylene oxide and 50 to 100% by weight of ethylene oxide; or 0 to 30% by weight of propylene oxide and 70 to 100% by weight of ethylene oxide; or 0 to 20% by weight of propylene oxide and 80 to 100% by weight of ethylene oxide; or 0 to 15% by weight of propylene oxide and 85 to 100% by weight of ethylene oxide.

The polyetheramine is commercially available, such as Surfonamine® amines from Huntsman Corporation. Specific examples of Surfonamine® amines include L-100 (propylene oxide to ethylene oxide mixing ratio 3/19), and L-207 (propylene oxide to ethylene oxide mixing ratio 10/33), L- 200 (propylene oxide to ethylene oxide mixing ratio 4/41), and L-300 (propylene oxide to ethylene oxide mixing ratio 8/58). The numbers in parentheses refer to the approximate repeating units of propylene oxide and ethylene oxide, respectively.

For dispersions of polar organic media substrates, the polyether can be derived from: 0 to 60% by weight ethylene oxide and 40 to 100% by weight propylene oxide; or 0 to 50% by weight ethylene oxide and 50 to 100% by weight of propylene oxide; or 0 to 30% by weight of ethylene oxide and 70 to 100% by weight of propylene oxide; or 0 to 20% by weight of ethylene oxide and 80 to 100% by weight of propylene oxide; or 0 to 15% by weight ethylene oxide and 85 to 100% by weight propylene oxide. Specific example 2- aromatic amine functional group dispersant containing polyether chain

In specific example 2, the polyalkylene glycol (meth)acrylate is reacted with a primary amine, and then reacted with an acid-functional aromatic anhydride. The primary amine reactant may be a polyetheramine having a number average molecular weight of 100 to 10,000, more desirably 400 to 2500, which includes alkylene oxide units such as ethylene oxide, propylene oxide, butylene oxide and phenyl Ethylene oxide (styrene oxide); Optionally, the primary amine can be a lower molecular weight non-polymeric amine, such as linear, branched, cyclic and even aromatic, including those with 1 to 50, more desirable It is a hydrocarbon group or a hydrocarbon carbonyl group of 1 to 20 carbon atoms, and includes one or two (more desirably only one) primary amine and up to one or two secondary amines or other nitrogen-containing groups such as amide linkages. Desirably, the primary amine reactant may include other heteroatoms such as oxygen and nitrogen (and selective sulfur) in amounts of up to 4 each of oxygen, nitrogen and selective sulfur per primary amine molecule. In a preferred embodiment, the primary amine-based polyetheramine, such as the Surfonamine® polyetheramine discussed previously. In another preferred embodiment, the primary amine is an alkylamine without heteroatoms except for the nitrogen of the primary amine. In another preferred embodiment, the primary amine includes C _1-20 amino carboxylic acid and may include other heteroatoms such as oxygen and nitrogen (and optionally sulfur). In another preferred embodiment, the primary amine includes C _1-20 amino alcohols and may include other heteroatoms such as oxygen and nitrogen (and optionally sulfur). In another preferred embodiment, the primary amine includes C _1-20 aromatic amines and may include other heteroatoms such as oxygen and nitrogen (and selective sulfur). An example is the reaction of butylamine with poly(ethylene glycol)(meth)acrylate of Mn 1000, followed by reaction with an acid-functionalized aromatic anhydride. Specific example 3- Aromatic amine functional group dispersant containing polyether chain

In specific example 3, the polyalkylene glycol (meth)acrylate is reacted with polyetheramine, and then reacted with an acid-functional aromatic anhydride. Example: Surfonamine® L100 is reacted with poly(ethylene glycol) acrylate of Mn 350, and then reacted with tricarboxylic acid phthalic anhydride. Specific example 4- aromatic amine functional group dispersant containing polyester chain

In specific example 4, the polyether amine is reacted with an epoxide (as previously defined) to produce a secondary amine, which is then reacted with an acid-functional aromatic anhydride. Example: Surfonamine® L207 is reacted with 1,2-epoxy-3-phenoxypropane, and then with tricarboxylic acid phthalic anhydride.

In a specific example, the present invention provides a polymer comprising at least one aromatic tertiary amide linking group attached to an aromatic group with pendant acid functionality, and a polyether group, and The polymer chain of the G group, wherein the polymer is represented by formula I.

In a specific example, the present invention provides a polymer comprising at least one aromatic tertiary amide linking group attached to an aromatic group with pendant carboxylic acid functionality, and a polyether group and A polymer chain of both polyester groups, wherein the polymer is represented by formula I.

Examples of lactones useful for polymerizing the aforementioned polyester groups include β-propiolactone, γ-butyrolactone, ε-caprolactone optionally substituted with alkyl groups, and δ-pentyl optionally substituted with alkyl groups Lactone. The alkyl substituents in ε-caprolactone and δ-valerolactone may be C _1-6 -alkyl or C _1-4 -alkyl, and may be linear or branched. Examples of suitable lactones are ε-caprolactone, and 7-methyl-, 2-methyl-, 3-methyl-, 5-methyl-, 6-methyl of caprolactone or valerolactone Base-, 4-methyl-, 5-tertiary butyl-, 4,4,6-trimethyl- and 4,6,6-trimethyl- analogs.

The esterification catalyst can be any known in the art and includes tin(II) octoate; tetraalkyl titanate, for example, tetrabutyl titanate; zinc salt of organic acid, for example, zinc acetate; aliphatic alcohol Zirconium salts, for example, zirconium isopropoxide; toluenesulfonic acid or strong organic acids such as trifluoroacetic acid or phosphoric acid.

The method can be carried out in an inert environment provided by any inert gas of the periodic table, but typically nitrogen. The method can be carried out under melting, or in the presence or absence of a solvent. The solvent may be a non-polar solvent (such as an aromatic or aliphatic compound), a polar organic solvent, or water. The solvent is well known in the art.

In a specific example, the polymer of the present invention (typically represented by formula I) is obtained/obtainable by a method comprising the following steps, step (1): let Michael acceptor such as (meth)acrylate or functionalize The (meth)acrylate reacts with a nucleophilic polymer chain such as the nitrogen atom of a polyetheramine to form a polyether secondary amine; Step (2): Let the polyether secondary amine react with an acid-functional aromatic A diacid or anhydride such as tricarboxylic acid phthalic anhydride reacts to form a tertiary amide linkage group between the aromatic acid and the polyether.

In the above specific example, the first step can be carried out at a temperature of about 0°C to 150°C, more desirably about 30°C to 80°C; and the second step of the reaction to form the tertiary amide can be carried out at a temperature of about It is carried out at 0°C to 120°C and more preferably about 30°C to 80°C.

In a specific example, the polymer of the present invention (typically represented by Formula I) is obtained/obtainable by a method comprising the following steps: Step (1): Make a polymerizable acrylate giant with unsaturated acrylate functionality Monomers such as MPEG acrylates react with nucleophilic aliphatic amines to form MPEG functionalized secondary amines; and

Step (2): Allow the MPEG-functionalized secondary amine from step (1) to react with an acid-functionalized aromatic diacid or anhydride such as tricarboxylic acid phthalic anhydride to remove the acid groups from the diacid or anhydride. One, the tertiary amide chain is formed, and the MPEG is connected to the acid-functionalized aromatic diacid is now acid/amide, where the first step Michael reaction can be at a temperature of about 0°C to 150°C, More desirably, it is carried out at about 30°C to 80°C; the reaction for forming the tertiary amide in the second step is about 0°C to 120°C, and more desirably about 30°C to 120°C. Performed at 80°C.

In a specific example, the present invention provides a composition comprising a particulate solid, an aqueous medium or a polar organic medium, and a dispersant of formula I having at least one tertiary amide suspension group, wherein the dispersant is composed of The formula I defined above is represented. The composition can be an abrasive base material, a coating material (paint) or an ink.

In a specific example, the present invention provides a composition comprising a particulate solid, an aqueous medium or a polar organic medium, a dispersant according to Formula I, and an adhesive. In a specific example, the adhesive may be polyepoxide, polyurethane, polyamide, poly(meth)acrylate, polyester, cellulose or alkyd resin.

In a specific example, the present invention provides a composition comprising a particulate solid, an aqueous medium or a polar organic medium, and a dispersant having at least one tertiary amide linking group, wherein the dispersant is represented by the above formula I ; Wherein the composition further comprises an adhesive. In a specific example, the adhesive may be cellulose (such as nitrocellulose), polyurethane, poly(meth)acrylate, polyester, or polyamide.

It is disclosed herein that the particulate solids in the composition of the present invention can be pigments or fillers. In a specific example, the pigment may be an organic pigment; in a specific example, the pigment may be an inorganic pigment; and in a specific example, the pigment may be carbon black. In the present disclosure, the inorganic type or carbon black particles are preferred.

In a specific example, the present invention provides a coating (coating) or ink comprising a particulate solid, an aqueous medium or a polar organic medium, a film-forming resin, and the dispersant disclosed herein.

In a specific example, the present invention provides a coating (paint) or ink, which comprises a particulate solid, a polar organic medium, a film-forming resin, and the dispersant disclosed herein.

When the composition is an ink, the ink may be an inkjet ink, an ink for flexographic printing, an ink for offset printing, or an ink for gravure printing. The ink may be radiation curable ink.

In a specific example, the present invention provides a composition comprising a dispersant represented by the above-defined formula I, an inorganic pigment (and/or carbon black), and a binder. The adhesive may be selected from the group consisting of cellulose, polyacrylic, polyester, polyether, polyurethane, alkyd resin and polyamide. The composition can be used in inks used in printing methods such as flexographic printing methods; or inkjet inks such as radiation curable, non-impact, and drop on demand.

The dispersant of the present invention can be present in the composition disclosed herein in an amount ranging from 0.1% by weight to 79.6% by weight, or 0.5% by weight to 30% by weight, or 1% by weight to 25% by weight based on the total weight of the composition In.

In a specific example, the present invention provides the use of a dispersant polymer, wherein the dispersant polymer is represented by Formula I as defined above and serves as a dispersant in the composition disclosed herein.

In a specific example, the present invention provides a use of the dispersant represented by the above-defined formula I, which is used as a dispersant in an ink composition using at least one of carbon black and inorganic pigments. The ink composition can have reduced particle size and reduced particle size distribution (typically reduced to an average of 150 nm or less), reduced haze value, improved gloss, and increased jetting properties (especially when the composition is When the material is black) and stable under ambient storage and high-temperature storage conditions.

Without being bound by theory, it is believed that the aromatic amine pendant group can act as an anchor group between the dispersant of the present invention and the particulate solid, such as a pigment selected from inorganic pigments and/or carbon black.

The amino carboxylic acid (or amino acid) may be an amino-C _{2-20 -alkane} (en) carboxylic acid and may or may not include more than one carboxylic acid group and may or may not include more than one amine base. The amino carboxylic acid may or may not include other heteroatom-containing groups such as hydroxyl or thiol groups. The alkylene group can be linear or branched. The alkylene (en) group of the amino carboxylic acid includes not more than 12 carbon atoms. Specific examples include 11-aminoundecanoic acid, 12-aminolauric acid, 6-aminocaproic acid, 4-aminobutyric acid, aspartic acid, glutamic acid, lysine acid, aspartic acid Amino acid, glutamic acid, threonine, serine, cysteine, β-alanine, glycine and creatine. Mixtures of amino carboxylic acids can be used.

The technical characteristics of 4n+2 π electrons defined in Q are well known by the skilled person as Hückel's law. Typically, n can be equal to 2 (ie, the number of π electrons is 10) or 3 (ie, the number of π electrons is 14). In a specific example, n may be equal to 2.

Typically, Q contains one or more aromatic rings derived from aromatic di- or tetracarboxylic acids or their anhydrides (optionally fused) or mixtures thereof. R _{1 is} each independently CO ₂ H or SO ₃ H, where a can be 1 to 3.

R ₂ may be an alkyl group or an optionally substituted alkyl group, where the alkyl group is linear or branched.

The alkyl group defined by R ₂ includes methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, 2-ethylhexyl, nonyl, decyl, undecyl, dodecyl , Tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl or mixtures thereof. In a specific example, R ₂ can be derived from an alkanol.

R ₃ may each independently be an optionally substituted C _1-50 , more desirably a C _1-20 hydrocarbon group, such as an alkyl group.

The polyetheramine is commercially available, such as Surfonamine® amines from Huntsman Corporation. Specific examples of Surfonamine® amines include L-100 (propylene oxide to ethylene oxide mixing ratio 3/19), and L-207 (propylene oxide to ethylene oxide mixing ratio 10/32), L- 200 (propylene oxide to ethylene oxide mixing ratio of 3/41), and L-300 (propylene oxide to ethylene oxide mixing ratio of 8/58). The numbers in parentheses refer to the approximate repeating units of propylene oxide and ethylene oxide, respectively.

In formula I, the integer x is such that the R ₂ -O-(Y) _x -TN chain may have a number average molecular weight of 100 to 10,000, or 100 to 5,000, or 300 to 3,000, or 400 to 2,500.

The above reaction system how to prepare the suspended polyether chain, wherein the ethylene oxide in the above method can be carried out at a temperature of 100°C to 200°C in the presence of a base such as potassium hydroxide or sodium hydroxide.

In formulas I and II, III, IV and IV and their subsets, the dispersant can be formed as a water-rich organic medium, wherein the polyether includes at least 60% to 100% by weight of ethylene oxide; optional Specifically, in the specific example of the dispersant system being used for polar organic media, the polyether includes at least 40% to 60% by weight of ethylene oxide.

Typically, for an aqueous medium dispersant, (Y) _{x of} the formula I includes 60% to 100% by weight, 70% to 100% by weight, or 80% to 100% by weight, or 100% by weight的ethylene oxide; and 0% by weight to 40% by weight, or 0% by weight to 30% by weight, or 0% by weight to 20% by weight, or 0% by weight of propylene oxide, based on the weight of _{(Y) x} Benchmark.

The polymer of the present invention may have multiple polymer chain types attached to the formulas IVa and IVb.

The polymer chain of Formula I or any sub-formula thereof may have a number average molecular weight of 200 to 10,000, or 300 to 5,000, or 500 to 3,000, or 600 to 2,500. Typically, the polymer chain of Formula I or any sub-formula thereof may have a number average molecular weight of 1,000 to 2,500. Industrial application

The particulate solid present in the composition can be any inorganic or organic solid material, which is substantially insoluble in the organic medium and/or insoluble in water at the temperature of interest, and is intended to be stabilized in a finely divided form. . The particulate solids may be in the form of granular materials, fibers, small plates, or in the form of powder, often blown powder. In a specific example, the particulate solid pigment.

The average particle size (diameter) of the particulate solid (typically a pigment or filler) that can be measured by light scattering measurement is 10 nanometers to 10 micrometers, or 10 nanometers to 1, 2, 3, or 5 micrometers, or 20nm to 1, 2, 3 or 5 microns.

Examples of suitable solids include pigments, extenders, fillers, blowing agents, and flame retardants used in coatings and plastic materials; dyes, especially disperse dyes; optical brighteners and textile auxiliaries; used in inks , Toner pigments; solids used for oil base and reverse emulsion drilling mud; dirt and solid particles in dry cleaning fluids; metals; used for ceramics, piezoelectric ceramics printing, refractory materials, abrasives, casting, capacitors , Fuel cells, ferromagnetic fluids, conductive inks, magnetic recording media, water treatment and hydrocarbon soil restoration of particulate ceramic materials and magnetic materials; organic and inorganic nano-dispersed solids; metals and metal oxides used in battery electrodes And carbon; fibers, such as wood, paper, glass, steel; carbon and boron used in composite materials; and disinfectants, agrochemicals, and medicines used as dispersions in organic media.

、苝、紫蘇酮(perinone)、皮蒽酮、吡唑并喹唑酮、喹吖酮、醌酞酮、硫靛、三芳

顏料、三苯二

(triphendioxazine)、

；及酞青系列，特別是酞青銅及其核經鹵化的衍生物；及亦有酸、鹼及媒染染料的沈澱色料。雖然嚴格來說碳黑係無機物，但其在分散性質上的表現更類似有機顏料。在一個具體實例中，該有機顏料有酞青類，特別是酞青銅類、單偶氮類、雙偶氮類、陰丹士林類、蒽嵌蒽醌類、喹吖酮類、二酮吡咯并吡咯類、苝類及碳黑類。In a specific example, the solid is an organic pigment from any recognized pigment type, for example, as described in the chapter title "Pigments" of the Third Edition of the Color Index (1971) and subsequent revisions and addenda. Examples of the organic pigments are those from the following: azo, bisazo, trisazo, condensed azo, azo lakes, naphthol pigment, anthraquinone, anthracene Pyrimidine, anthraquinone, benzimidazolone, carbazole, diketopyrrolopyrrole, flavone, indigo pigments, indanthrene, isobibenzanthrone, isoindanthrene, isoindolinone , Isoindoline, isoviolanthrone, metal complex pigments,

, Perylene, perinone, pyranthrone, pyrazoloquinazolone, quinacridone, quinonephthalone, thioindigo, triaryl

Pigment, Triphenyl

(triphendioxazine),

; And the phthalocyanine series, especially the phthalocyanine and its core halogenated derivatives; and there are also acid, alkali and mordant dye precipitation pigments. Although strictly speaking carbon black is an inorganic substance, its dispersion properties are more similar to organic pigments. In a specific example, the organic pigments are phthalocyanines, especially phthalocyanines, monoazo, bisazo, indanthrene, anthraquinone, quinacridone, diketopyrrole Pyrrole, perylene and carbon black.

Examples of the inorganic pigments include metal oxides such as titanium dioxide, rutile titanium dioxide, and surface-coated titanium dioxide, titanium oxide with different colors such as yellow and black; iron oxide with different colors such as yellow, red, brown, and black; zinc oxide , Zirconia, alumina; oxymetallic compounds, such as bismuth vanadate, cobalt aluminate, cobalt stannate, cobalt zincate, zinc chromate; and manganese, nickel, titanium, chromium, antimony, magnesium, Mixed metal oxides of two or more of cobalt, iron or aluminum; Prussian blue, red lead, ultramarine, zinc phosphate, zinc sulfide, calcium and zinc molybdates and chromates; metallic effect pigments, such as thin aluminum Flakes, copper and copper/zinc alloys; pearlescent flakes, such as lead carbonate and bismuth oxychloride.

The inorganic solids include extenders and fillers, such as heavy and precipitated calcium carbonate, calcium sulfate, calcium oxide, calcium oxalate, calcium phosphate, calcium phosphonate, barium sulfate, barium carbonate, magnesium oxide, magnesium hydroxide, natural hydrogen Magnesium oxide or brucite, precipitated magnesium hydroxide, magnesium carbonate, dolomite, aluminum trihydroxide, aluminum hydroxide or boehmite, calcium and magnesium silicate, aluminum silicate including nano clay, kaolin ; Montmorillonite, including bentonite, lithium bentonite and saponite; spherical clay, including natural, synthetic and expandable; mica; talc, including muscovite, phlogopite, lepidolite and green Mudstone; chalk, synthetic and deposited silica, fumed silica, metal fiber and powder, zinc, aluminum, glass fiber, refractory fiber; carbon black, including single and multi-wall carbon nanotubes, reinforcement and non- Reinforced carbon black; graphite, buckminster fullerenes, asphaltenes, graphene, diamond, alumina, quartz, perlite, pegmatite, silica gel, wood flour, wood chips including soft and hard wood, sawdust , Powdered paper/fiber; cellulose fiber, such as kenaf, hemp fiber, viburnum, flax, cotton, cotton lint, jute, ramie, rice bran or shell, raffia, cattail reed (typha reed) , Coconut fiber, coconut husk fiber, oil palm fiber, kapok, banana leaf, caro leaf (caro), pineapple leaf (curaua), sisal leaf, harakkee leaf, manila hemp, bagasse, wheat straw, Bamboo chips, flour, MDF and the like; vermiculite, zeolite, hydrotalcite, fly ash from power plants, incinerated sewage sludge ash, volcanic ash (pozzolanes), blast furnace slag, asbestos, serpentine, Anthophylite, crocidolite, wollastonite, Otepite and the like; particulate ceramic materials such as alumina, zirconia, titanium dioxide, ceria, silicon nitride, aluminum nitride, boron nitride , Silicon carbide, boron carbide, mixed silicon nitride-aluminum and metal titanate; particulate magnetic materials, such as transition metals are often magnetic oxides of iron and chromium, for example, γ-Fe ₂ O ₃ , Fe ₃ O ₄ , And cobalt-doped iron oxides; ferrites, such as barium ferrite; and metal particles, such as metal aluminum, iron, nickel, cobalt, copper, silver, gold, palladium, platinum and their alloys .

Other useful solid materials include flame retardants such as pentabromodiphenyl ether, octabromodiphenyl ether, decabromodiphenyl ether, hexabromocyclododecane, ammonium polyphosphate, melamine, melamine trimer Cyanate, antimony oxide and borate; sterilizing agent or industrial microbial agent, such as table 2 of the chapter titled "Industrial Microbial Agents" in Kirk-Othmer's Encyclopedia of Chemical Technology, Volume 13, 1981, 3rd edition Those mentioned in 3, 4, 5, 6, 7, 8 and 9; and agrochemicals, such as the fungicide flutriafen, carbendazim, chlorothalonil and Zinc-manganese is Pu (mancozeb).

In a specific example, the polar liquid medium is water, but may include up to 50% by weight (based on the combined weight of water and polar solvent) of a polar co-solvent soluble in water. Examples of co-solvents compatible with polar solvents include alcohols, such as ethanol, isopropanol, n-propanol or n-butanol; or water-miscible organic solvents, such as mono- or diethylene glycol or diethylene glycol. Dialkyl ethers; or polar solvents, such as diethylene glycol, glycerin, 2-pyrrolidone, N-methylpyrrolidone, cyclohexanol, caprolactone, caprolactone, pentane-1,5- Glycol, 2-(butoxyethoxy)ethanol and thiodiglycol, and ethylene glycol; including any mixtures of the alcohols or solvents previously listed. The term "polar" for this organic liquid means an organic liquid that can form a medium to strong bond, as in the name "A" published by Crowley et al. in Journal of Paint Technology, Vol. 38, 1966, page 269. "Three Dimensional Approach to Solubility" in the paper. Polar organic liquids generally have a dielectric constant of 5 or greater, as defined in the above-mentioned paper. Non-polar liquids typically have a dielectric constant of less than 5.

The abrasive base or dispersion system is useful for preparing water-based paints (coatings) and inks, which are resins and/or water compatible with a further amount of water and other conventionally incorporated water-based paints and inks. Mixing, such as preservatives, stabilizers, anti-foaming agents, water-miscible co-solvents and coalescing agents.

The water-compatible resin can be any water-soluble or water-insoluble polymer used in the water-based coating industry. Examples of polymers commonly used in emulsions or water-reducible coatings as the main film-forming adhesive resin include acrylic, vinyl ester, polyurethane, polyester, epoxy resin, and alkyd resin.

In a specific example, the organic medium present in the composition of the present invention is a plastic material, and in another specific example, it is an organic liquid. The organic liquid may be a polar organic liquid. The term "polar" for the organic liquid means an organic liquid that can form a medium to strong bond, as in the name "A" published by Crowley et al. in Journal of Paint Technology, Vol. 38, 1966, page 269. "Three Dimensional Approach to Solubility" in the paper. This organic liquid usually has a hydrogen bond number of 5 or more, as defined in the above-mentioned paper.

Examples of suitable polar organic liquids are amines, ethers, especially lower alkyl ethers, organic acids, esters, ketones, glycols, glycol ethers, glycol esters, alcohols and amides. Many specific examples of this moderately strong hydrogen-bonded liquid are provided in Table 2.14 on pages 39-40 of the book titled "Compatibility and Solubility" published by Ibert Mellan (published by Noyes Development Corporation in 1968), and These liquids all fall within the scope of the term polar organic liquid as used herein.

In a specific example, the polar organic liquid has alkyl esters of dialkyl ketones, alkane carboxylic acids, and alkanols. In particular, this liquid includes up to 6 carbon atoms in total. As for the examples of the polar organic liquid, it includes dialkyl and cycloalkyl ketones, such as acetone, methyl ethyl ketone, diethyl ketone, diisopropyl ketone, methyl isobutyl ketone, diisobutyl ketone, Methyl ketone, methyl isoamyl ketone, methyl n-amyl ketone and cyclohexanone; alkyl esters such as methyl acetate, ethyl acetate, isopropyl acetate, butyl acetate, ethyl formate, methyl propionate Ester, methoxy propyl acetate and ethyl butyrate; glycol and glycol esters and ethers, such as ethylene glycol, 2-ethoxyethanol, 3-methoxypropyl propanol, 3-ethoxy Propyl propanol, 2-butoxyethyl acetate, 3-methoxypropyl acetate, 3-ethoxypropyl acetate, and 2-ethoxyethyl acetate; alkanols, such as methanol , Ethanol, n-propanol, isopropanol, n-butanol and isobutanol (also known as 2-methylpropanol), terpineol; and dialkyl and cyclic ethers, such as diethyl ether and Tetrahydrofuran. In a specific example, the solvent is an alkanol, alkane carboxylic acid, and an ester of alkane carboxylic acid. In a specific example, the present invention is suitable for organic liquids that are substantially insoluble in aqueous media. Furthermore, those skilled in the art will recognize that a small amount of aqueous medium (such as glycols, glycol ethers, glycol esters, and alcohols) may be present in the organic liquid, as long as the overall organic liquid is substantially insoluble in the aqueous medium.

Examples of organic liquids that can be used as polar organic liquids include film-forming resins suitable for the preparation of inks, paints, and various applications such as paints and ink fragments. Examples of these resins include polyamides, such as Versamid™ and Wolfamid™; and cellulose ethers, such as ethyl cellulose and ethyl hydroxyethyl cellulose, nitrocellulose, and acetate butyrate cellulose resins , Including its mixture. Examples of the coating resin include short oil alkyd resin/melamine-formaldehyde, polyester/melamine-formaldehyde, thermosetting acrylic/melamine-formaldehyde, long oil alkyd resin, medium oil alkyd resin, short oil alkyd resin Resins, polyether polyols and multi-media resins such as acrylic and urea/aldehyde.

The organic liquid may be a polyol, that is, an organic liquid having two or more hydroxyl groups. In a specific example, the polyol includes α-ω diol or α-ω diol ethoxylate.

In a specific example, the organic liquid contains at least 0.1% by weight, or 1% by weight or more of polar organic liquid, based on the total organic liquid. The organic liquid optionally further contains water. In a specific example, the organic liquid system is anhydrous (typically less than 2% by weight of water, or less than 1% by weight of water, or less than 0.5% by weight of water, or less than 0.1% by weight).

The plastic material can be thermosetting resin. Thermosetting resins useful in the present invention include resins that undergo chemical reactions when heated, catalyzed, or receive ultraviolet light, laser light, infrared light, cations, electron beams or microwave radiation, and become quite refractory. Typical reactions in thermosetting resins include the oxidation of unsaturated double bonds; including the reaction of epoxy groups/amines, epoxy groups/carbonyl groups, epoxy groups/hydroxyl groups; epoxy groups with Lewis acid or Lewis base, polyisocyanates /Reaction of hydroxyl and amino resin/hydroxyl part; free radical reaction or polyacrylate; cationic polymerization of epoxy resin and vinyl ether; and condensation of silanol. Examples of unsaturated resins include polyester resins prepared by the reaction of one or more diacids or anhydrides with one or more diols. These resins are usually supplied as mixtures containing reactive monomers such as styrene or vinyl toluene, and are often referred to as phthalic acid resins and isophthalic acid resins. Further examples include the use of dicyclopentadiene (DCPD) as the resin for the co-reactant in the polyester chain. Further examples also include the reaction product of bisphenol A diglycidyl ether and an unsaturated carboxylic acid such as methacrylic acid, which is then supplied as a solution in styrene, usually referred to as a vinyl ester resin.

In a specific example, the thermosetting composite or thermosetting plastic can be polyester, polyvinyl acetate, polyester resin in styrene, polystyrene, or a mixture thereof.

Polymers with hydroxyl functionality (often polyols) are widely used in thermosetting systems to crosslink with amino resins or polyisocyanates. The polyols include acrylic polyols, alkyd resin polyols, polyester polyols, polyether polyols, and polyurethane polyols. Typical amine-based resins include melamine formaldehyde resin, benzoguanamine formaldehyde resin, urea formaldehyde resin and acetylene carbamide formaldehyde resin. The polyisocyanate is a resin having two or more isocyanate groups, which includes both monomeric aliphatic diisocyanates, monomeric aromatic diisocyanates, and polymers thereof. Typical aliphatic diisocyanates include hexamethylene diisocyanate, isophorone diisocyanate, and hydrogenated diphenylmethane diisocyanate. Typical aromatic isocyanates include toluene diisocyanate and biphenylmethane diisocyanate.

If desired, the composition of the present invention may include other ingredients, for example, resins (where these do not constitute the organic medium), adhesives, co-solvents, cross-linking agents, fluidizing agents, wetting agents, and anti-settling agents , Plasticizers, surfactants, dispersants, humectants, anti-foaming agents, anti-crater agents, rheology modifiers, heat stabilizers, light stabilizers, UV absorbers, anti-foaming agents other than the compounds of the present invention Oxidizing agent, leveling agent, gloss modifier, sterilizing agent and preservative.

If desired, the composition including thermosetting plastic materials may include other ingredients, for example, dispersants, blowing agents, flame retardants, process aids, surfactants, heat stabilizers, other than the compound of the present invention. UV absorbers, antioxidants, fragrances, release aids, antistatic agents, antimicrobial agents, sterilants, coupling agents, lubricants (external and internal), defoamers and viscosity suppressants.

The composition typically contains 1 to 95% by weight of particulate solids, the exact amount depends on the nature of the solid, and the amount depends on the nature of the solid and the relative density of the solid and the relative density of the polar organic liquid. set. For example, in a specific example, the composition of the solid-based organic material such as an organic pigment includes 15 to 60% by weight of solids; however, in a specific example, the solid-based inorganic material such as an inorganic pigment, filler or extender The composition includes 40 to 90% by weight of solids, based on the total weight of the composition.

The composition including the organic liquid can be prepared by any conventionally known method for preparing dispersions. Therefore, the solid, organic medium and dispersant can be mixed in any order, and then the mixture is subjected to mechanical treatment to reduce the solid particles to an appropriate size, for example, by high-speed mixing, ball milling, and basket milling. ), bead milling, gravel milling, sand milling, attritor milling, two-roll or three-roll milling, and plastic milling until the dispersion is formed. Optionally, the solids can be processed independently or mixed with the organic medium or dispersant to reduce the particle size, and then other ingredients are added and the mixture is stirred to provide the composition. The composition can also be prepared by crushing or grinding the dry solid and dispersant, and then adding the liquid medium; or mixing the solid and dispersant in the liquid medium by a pigment flushing process.

The composition including the plastic material can be prepared by any conventionally known method for preparing thermoplastic compounds. Therefore, the solid, thermoplastic polymer and dispersant can be mixed in any order, and then the mixture is subjected to mechanical treatment to reduce the solid particles to an appropriate size, for example, by Banbury mixing, ribbon blending, twin screw extrusion, Two-roll milling, mixing in a Buss co-kneader or similar equipment.

The composition of the present invention is particularly suitable for liquid dispersions. In a specific example, the dispersion composition includes: (a) 0.5 to 80 parts of particulate solid; (b) 0.1 to 79.6 parts of the polymer of formula I; and (c) 19.9-99.4 parts of organic liquid and/or water, all of which are relative parts by weight and the amount (a)+(b)+(c)=100.

In a specific example, the component a) contains 0.5 to 30 parts of pigment and this dispersion system is useful as (liquid) ink, coating (paint) and grinding base.

If the composition needs to contain the particulate solid in dry form and the dispersant of Formula I, the organic liquid is typically volatile so that it can be easily removed from the particulate solid by simple separation methods such as evaporation. In a specific example, the composition includes the organic liquid.

If the dry composition consists essentially of the dispersant of formula I and particulate solids, it typically includes at least 0.2%, at least 0.5%, or at least 1.0% of the dispersant of formula I, based on the weight of the particulate solids. In a specific example, the dry composition includes not more than 100%, not more than 50%, not more than 20%, or not more than 10% by weight of the dispersant of formula I, based on the weight of the particulate solid .

As disclosed above, the composition of the present invention is suitable for preparing a grinding base, wherein the particulate solid is ground in an organic liquid in the presence of the compound of formula I.

Therefore, according to a further aspect of the present invention, there is provided an abrasive base comprising particulate solids, organic liquids, and polymers of formula I.

Typically, the abrasive base contains 20 to 70% by weight of particulate solids, based on the total weight of the abrasive base. In a specific example, the particulate solid is not less than 10 or not less than 20% by weight of the grinding base material. The grinding base may optionally include an adhesive added before or after grinding.

In a specific example, the adhesive is a polymer material that can bond the composition when the organic liquid evaporates.

The adhesive is a polymer material, including natural and synthetic materials. In a specific example, the adhesive includes poly(meth)acrylate, polystyrene, polyester, polyurethane, alkyd resin; polysaccharides, such as cellulose and nitrocellulose; And natural proteins, such as casein. The adhesive can be nitrocellulose. In a specific example, based on the amount of particulate solids, the adhesive is present in the composition at more than 100%, more than 200%, more than 300%, or more than 400%.

The amount of selective adhesive in the abrasive base may vary within wide limits, but is typically not less than 10% and often not less than 20% by weight of the continuous/liquid phase of the abrasive base. In a specific example, the amount of the adhesive is not more than 50% or not more than 40% by weight of the continuous/liquid phase of the abrasive base.

The amount of dispersant in the grinding base depends on the amount of the particulate solids, but is typically 0.5 to 5% by weight of the grinding base.

The dispersions and grinding bases prepared from the composition of the present invention are particularly suitable for use in non-aqueous and solvent-free formulations, where it is possible to use it in combination with monomers, oligomers, etc. or combination with the formulations. Volume hardening system (ultraviolet light, laser light, infrared light, positive ion, electron beam, microwave). They are particularly suitable for use in coatings, such as paints, varnishes, inks, other coating materials and plastics. Suitable examples include its use in the following: low, medium and high solid coatings, general industrial coatings including baking, two-component and metal coating coatings such as coil and can coatings, powder coatings, UV Hardenable coatings, wood varnishes; inks, such as flexographic printing, gravure printing, offset printing, offset printing, type printing or letterpress printing, silk screen printing and printing inks for packaging printing; non-impact inks Liquid, such as inkjet ink, including continuous inkjet and drop-on-demand inkjet, including thermal, piezoelectric and electrostatic, phase change ink and hot melt wax ink, used for inkjet Printing inks; and printing varnishes, such as overprint varnishes; polyol and plastisol dispersions; non-aqueous ceramic methods, especially thin strip forming, gel casting, doctor blade, extrusion and injection molding methods, and further Examples will be the preparation of dry ceramic powder for isostatic pressing; composites, such as sheet molding and block molding compounds, resin injection molding, pultrusion molding, hand-laminated and spray-laminated processes, and mold molding; building materials , Such as casting resin; cosmetics; personal care, such as nail paint, sunscreen; adhesives; toners, such as liquid toners, plastic materials and electronic materials, such as coating formulations for color filter systems for displays , The display includes organic light-emitting diode (OLED) devices, liquid crystal displays and electrophoretic displays; glass coatings, including optical fiber coatings, reflective coatings or anti-reflective coatings; conductive and magnetic inks and coatings . They are useful in surface modification of pigments and fillers to improve the dispersibility of dry powders in the above-mentioned applications. Further examples of the coating material are provided in Bodo Muller, Ulrich Poth, Lackformulierung und Lackrezeptur, Lehrbuch fr Ausbildung und Praxis, Vincentz Verlag, Hanover (2003); and in PG Garrat, Strahlenhartung, Vincentz Verlag, Hanover (1996) in. Examples of the printing ink formulations are provided in E.W. Flick, Printing Ink and Overprint Varnish Formulations-Recent Developments, Noyes Publications, Park Ridge NJ, (1990) and subsequent editions.

The dispersions and abrasive bases prepared from the composition of the present invention are also useful for contact and non-contact (drop-on-demand) water-based printing methods, such as water-based flexographic printing, water-based inkjet, and water-based UV inkjet.

In a specific example, the composition of the present invention further includes one or more additional known dispersants.

The following examples provide an illustration of the invention. These examples are not exhaustive and are not intended to limit the scope of the invention. Examples Comparative Example 1 (CE1) -Reaction of polyetheramine with 1,2,4-benzenetricarboxylic anhydride.

A dispersant was prepared according to Example 1 of US Patent Publication 2005/0120911, except that Surfonamine® L207 was substituted for XJT-507. In a nitrogen environment, stir 1,2,4-benzenetricarboxylic anhydride (14.4 parts) and polyetheramine (150.0 parts, Surfonamine® L207, MW: 2000, from Huntsman) at 120°C for 1 hour, then 160°C 4 Hours until no anhydride remains, as determined by IR spectroscopy. The final product has an acid value of 27.4 mg KOH/g and an imine peak ^{at 1714.9 cm-1.} Example 1 (EX1) -Polyetheramine is reacted with 2-carboxyethyl acrylate and then with 1,2,4-benzenetricarboxylic anhydride.

In an air environment, stir polyetheramine (1023 parts, Surfonamine® L207, MW: 2000, from Huntsman) and 3,5-di-tertiary-4-butylhydroxytoluene (0.8 parts) at 50°C. To this mixture was added dropwise 2-carboxyethyl acrylate (73.66 parts) within 25 minutes, and kept at 50°C for 1 hour, then 80°C for 3 hours until there was no vinyl peak, as ^{determined by 1} H NMR spectroscopy . Then, the temperature was lowered to 55°C, after which 1,2,4-benzenetricarboxylic anhydride (98.12 parts) was added in a nitrogen environment. The reaction mixture was stirred until the anhydride was completely dissolved, and then it was heated for another 9 hours until no anhydride remained, as determined by IR spectroscopy. The final product has an acid value of 77 mg KOH/g and the IR spectrum shows a tertiary amide carbonyl peak ^{at 1638 cm-1.} Dispersion Test 1 -Preparation of Titanium Dioxide Pigment Dispersion.

The dispersion was prepared by dissolving the dispersants CE1 and EX1 (0.68 parts) into water (10.43 parts). To this, add defoamer (0.14 parts BYK® 024 from BYK-Chemie, Altana Group), 3 mm glass beads (120 parts) and white pigment (33.75 parts Kronos® 2360 from Kronos), and grind this on a Scandex shaker Wait for 1 hour. The dispersion produced using EX1 produced a fluid mill base, whereas CE1 produced a gel.

Overall, the results indicate that the polymer of the present invention provides at least one of improved particulate solid loading, improved dispersion formation, improved brightness, and production of a composition with reduced viscosity in an aqueous medium.

As described later, the number average molecular weight of the polymer of the present invention has been determined using a known method, such as gel permeation chromatography (GPC) analysis, and polystyrene standards are used for all polymer chains. Comparative Example 2 (CE2)-Reaction of polyetheramine with 1,2,4-benzenetricarboxylic anhydride.

A dispersant was prepared according to Example 1 of US Patent Publication 2005/0120911, except that Surfonamine® L100 was substituted for XJT-507. In a nitrogen environment, stir 1,2,4-benzenetricarboxylic anhydride (11.85 parts) and polyetheramine (64.77 parts, Surfonamine® L100, MW: 1000, from Huntsman) at 110°C for 1 hour, then at 170°C Continue for 5 hours until no anhydride remains, as determined by IR spectroscopy. The final product has an acid value of 48.16 mg KOH/g and an imine peak ^{at 1713 cm-1.} Example 2 (EX-2) -Polyetheramine is reacted with acrylic acid and then with 1,2,4-benzenetricarboxylic acid anhydride.

(0.026份)。對此混合物加入丙烯酸(3.07份)，將反應溫度增加至80℃及攪拌該混合物5.5小時直到無乙烯基波峰顯現，如藉由1H NMR光譜測定。然後，將溫度降低至50℃，在此之後，於氮環境中加入1,2,4-苯三羧酸酐(8.19份)。攪拌該反應混合物24小時直到酐溶解及無酐波峰餘留，如藉由IR光譜測定。最後產物具有酸值74.40毫克KOH/克及IR光譜顯示出在1637公分^-1 處的三級醯胺羰基波峰。實施例 3(EX3) -聚醚胺與丙烯酸2-羧基乙基酯然後與1,2,4-苯三羧酸酐反應。In an air environment, stir polyetheramine (85.91 parts, Surfonamine® L207, MW: 2000, from Huntsman) and phenanthrene at 50°C

(0.026 parts). Acrylic acid (3.07 parts) was added to this mixture, the reaction temperature was increased to 80°C and the mixture was stirred for 5.5 hours until no vinyl peaks appeared, as determined by 1H NMR spectroscopy. Then, the temperature was lowered to 50°C, after which 1,2,4-benzenetricarboxylic anhydride (8.19 parts) was added in a nitrogen environment. The reaction mixture was stirred for 24 hours until the anhydride was dissolved and no anhydride peak remained, as determined by IR spectroscopy. The final product has an acid value of 74.40 mg KOH/g and the IR spectrum shows a tertiary amide carbonyl peak ^{at 1637 cm-1.} Example 3 (EX3) -Polyetheramine is reacted with 2-carboxyethyl acrylate and then with 1,2,4-benzenetricarboxylic anhydride.

In an air environment, stir polyetheramine (212.93 parts, Surfonamine® L100, MW: 1000, from Huntsman) and 3,5-di-tertiary-4-butylhydroxytoluene (0.84 parts) at 50°C. To this mixture was added dropwise 2-carboxyethyl acrylate (28.85 parts) within 50 minutes, and left at 50°C for more than 30 minutes, and then at 80°C for 3 hours until no vinyl peaks appeared, such as by ¹ H NMR spectroscopy. Then, the temperature was lowered to 50°C, after which 1,2,4-benzenetricarboxylic anhydride (39.11 parts) was added in a nitrogen environment. The reaction mixture was stirred until the anhydride was completely dissolved, and then it was heated for another 10 hours until no anhydride peak remained, as determined by IR spectroscopy. The final product has an acid value of 117.71 mg KOH/g and the IR spectrum shows a tertiary amide carbonyl peak ^{at 1633 cm-1.} Example 4 (EX4) -Polyetheramine is reacted with 1,2-epoxy-3-phenoxypropane and then with 1,2,4-benzenetricarboxylic anhydride.

In an air environment, stir polyetheramine (101.64 parts, Surfonamine® L100, MW: 1000, from Huntsman) and 3,5-di-tertiary-4-butylhydroxytoluene (0.36 parts) at 50°C. To this mixture, 1,2-epoxy-3-phenoxypropane (15.17 parts) was added dropwise over 10 minutes, and the mixture was left at 50°C and stirred for 30 minutes. The reaction mixture was stirred at 50°C for another 18 hours until no epoxide peak appeared, as determined by IR or ¹ H NMR spectroscopy. After this time, 1,2,4-benzenetricarboxylic anhydride (19.47 parts) was added in a nitrogen environment. The reaction mixture was stirred until the anhydride was completely dissolved, and then another 10 hours until no anhydride remained, as determined by IR spectroscopy. The final product has an acid value of 81.79 mg KOH/g and the IR spectrum shows a tertiary amide carbonyl peak ^{at 1665 cm-1.} Dispersion Test 2 -Preparation of Titanium Dioxide Pigment Dispersion in Water

Dispersions were prepared by dissolving the dispersants (0.15 parts) of Comparative Examples (CE-1 and CE-2) and Examples (EX1-4) into water (3.32 parts). To this, add (0.03 parts BYK® 024 from BYK-Chemie, Altana Group), 3 mm glass beads (17 parts) and white pigment (6.50 parts Kronos® 2360 from Kronos), and grind these ingredients on a horizontal shaker 16 hours. Then, evaluate the fluidity of the resulting dispersion. Table 1-Pigment dispersion results from Dispersion Test 2 Dispersant fluidity Comparative example fluidity Example 1 (EX-1) Very flowing liquid Comparative Example 1 (CE-1) Very viscous liquid Example 2 (EX-2) Very flowing liquid Example 3 (EX-3) Very flowing liquid Comparative Example 2 (CE-2) Very viscous liquid Example 4 (EX-4) Very flowing liquid Dispersion Test 3 -Preparation of titanium dioxide pigment dispersion in 1-methoxy-2-propyl acetate.

Prepared by dissolving the dispersant (0.15 parts) of Comparative Examples (CE-1 and CE-2) and Examples (EX1-3) into 1-methoxy-2-propyl acetate (2.35 parts) Dispersions. To this, 3 mm glass beads (17 parts), white pigment (7.50 parts Kronos® 2360, from Kronos) were added, and the ingredients were ground on a horizontal shaker for 16 hours. The particle size (D50 and D90) of the resulting dispersion was measured by Microtrac DLS Nano-flex particle size analyzer. Table 2-Pigment dispersion results from Dispersion Test 3 Dispersant D50/nm D90/nm Example 1 (EX-1) 232.9 301.0 Example 2 (EX-2) 228.9 316.0 Comparative Example 1 (CE-1) 522.0 669.0 Example 3 (EX-3) 235.2 280.1 Comparative Example 2 (CE-2) 845.0 1206.0

Each document indicated above is incorporated into this article by reference. Unless otherwise indicated, each chemical substance or composition mentioned in this article should be interpreted as a commercial grade material, which can include isomers, by-products, derivatives, and it is generally understood that it will exist in the commercial grade Other such materials. However, unless otherwise indicated, the amount exhibited by each chemical component excludes any solvents or diluent oils that may be customarily present in the commercial material. It should be understood that the upper and lower amount, range, and ratio limits set forth in this article can be combined independently of each other. Similarly, the range and amount of each element used in the present invention can be used together with the range or amount of any other element.

Although the present invention has been explained with its related preferred specific examples, it should be understood that those who are familiar with the technology will understand various modifications after reading this patent specification. Therefore, it should be understood that the invention disclosed herein is intended to cover this modification as if it falls within the scope of the appended patent application.

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Claims (19)

A dispersant or a salt thereof, which comprises a dispersant polymer having the following structure: Formula I

R _{1 is} each independently CO ₂ H or SO ₃ H, wherein a is 1 to 2 or 3; R ₂ is H, or an optionally substituted C _1-50 hydrocarbon group, or an optionally substituted C _1-50 Hydrocarbon carbonyl; where T is -C(O)-CH(R ₄ )CH ₂ or C _1-5 hydrocarbon group; when G is C _1-50 hydrocarbon group, T is -C(O)-CH(R ₄ ) CH ₂ ; When G is the residue of an acrylate that reacts with nitrogen in the Michael addition reaction, or an epoxide opened by the polymerization of a ring-opening epoxy group, T is a C _1-5 hydrocarbyl chain; R ₄ is H or Me, preferably H; G is a C _1-50 hydrocarbon group optionally substituted with heteroatoms such as O or N, wherein the O or N is represented by ether, ester, aldehyde, ketone, amine, amine Carboxylate, alcohol or carboxylic acid group, or G series optionally substituted alkyl (meth)acrylate or (meth)acrylamide residue, or the ring-opening product of the epoxide of the following formula :

In each case, R ₆ can be H, or CH ₃ , or C ₂ H ₅ , or one of the following groups:

Wherein D is C _1-5 alkyl, CN, OH, NO ₂ , NH ₂ , halogen, CO ₂ H, SO ₃ H, CH ₃ or OCH ₃ ; p is 0 to 4; R ₃ is linear or branched C _1-50 and preferably C _1-20 alkyl; Y is independently C _2-4 alkoxy in each repeating unit; Q contains more than one aromatic ring (up to three or four rings) ) hydrocarbon of extension, selectively by R _1, if there is two aromatic rings which are fused by selective, wherein the Q is attached to the carboxylic acid group attached to a carbon-based aromatic ring of Q Atom; wherein the hydrogen of any acid in the formula can be replaced by a metal, amine or ammonium cation to make the dispersant in the form of a salt; and x is 2 to 90. The dispersant according to claim 1, wherein Q contains naphthalene, more desirably Q contains 1,2-naphthoic acid amide derived from acid functionalization (for example, carboxylic acid or sulfonic acid), acid functionalized 2,3 -Naphthamide or acid-functionalized 1,8-naphthamide, or a mixture of naphthalene. The dispersant according to claim 1, wherein Q contains biphenyl. The dispersant according to claim 1, wherein Q contains a phenyl group. The dispersant according to any one of claims 1 to 4 mentioned above is obtained/obtainable by a method comprising the following: Step (1): The Michael acceptor such as (meth)acrylate or functionalized (former) Yl)acrylate, which reacts with the nitrogen atom of a nucleophilic polymer chain such as a polyetheramine to form a polyether-functionalized secondary amine, wherein the (meth)acrylate or functionalized (meth)acrylate can be include:

The variables are as previously defined; wherein U is O or NH; x ₁ is 1 to 50, more desirably 1 to 20; and step (2): functionalize the polyether-functionalized secondary amine with acid (For example, carboxylic acid or sulfonic acid) of aromatic diacid or its anhydride, such as acid-functionalized 2,3-naphthalenedicarboxylic acid anhydride or such as 1,2,4-benzenetricarboxylic acid anhydride, to react with the aromatic acid A tertiary amide linking group is formed with the polyether. The dispersant according to claim 5, wherein the first step is carried out at a temperature of about 0°C to 150°C, more desirably about 30°C to 80°C; and the reaction for forming a tertiary amide in the second step is carried out at The temperature is about 50°C to 120°C, and more preferably about 30°C to 80°C. The dispersant of any one of claims 1 to 4 mentioned above, which is obtained/obtained by a method including the following: Step (1): Reacting (meth)acrylate monomers with unsaturated acrylate functional groups or functionalized (meth)acrylate monomers such as MPEG acrylates with nucleophilic aliphatic amines to form MPEG Functionalized secondary amine; and Step (2): The MPEG-functionalized secondary amine from step (1) is functionalized with an acid-functionalized aromatic diacid or its anhydride such as an acid (for example, carboxylic acid or sulfonic acid) functionalized 2,3- Naphthalic anhydride or anhydrides such as 1,2,4-benzenetricarboxylic acid react to form a tertiary amine link from one of the acid groups of the diacid or its anhydride, and link the MPEG to the aromatic The diacid is now an acid/amide, where the first step Michael reaction can be carried out at a temperature of about 0°C to 150°C, more desirably about 30°C to 80°C; the second step is a reaction to form a tertiary amide The temperature used for amination is about 0°C to 120°C, and more desirably about 30°C to 80°C. The dispersant of any one of claims 1 to 4 mentioned above, which is obtained/obtained by a method including the following: Step (1): reacting a hydroxy acrylate such as hydroxyethyl acrylate (selectively ethoxylated or polymerizing the hydroxy group) with a nucleophilic aliphatic amine to form an aliphatic secondary amine; Step (2): reacting the aliphatic secondary amine with an acid-functionalized aromatic diacid or tetraacid or its anhydride to form a tertiary amide; and Step (3): Selectively react the hydroxyl group of the aliphatic secondary amide with an epoxide or cyclic ester, wherein the cyclic ester is selectively caprolactone, and/or polymerize the epoxide or cyclic ester Ester to form a polymeric polyether chain or polyester chain, wherein the first step, that is, the Michael reaction, can be carried out at a temperature of about 0°C to 150°C, more desirably about 30°C to 80°C; the second step is formed The reaction of the tertiary amine is carried out at a temperature of about 50°C to 120°C, more desirably about 30°C to 80°C; and the third step of polymerizing the epoxide or cyclic ester is carried out at a temperature of about 100°C to 120°C. Performed at 200°C. The dispersant or the salt thereof according to any one of claims 1 to 4, wherein the dispersant is according to: Formula IIa

Formula IIb

Formula IIc

Wherein the hydrogen of any acid in the formula can be replaced by a metal, amine or ammonium cation, so that the dispersant is in the form of a salt; and U is O or NH; and Z is -OH, -N(R ₇ ) ₂ ( Wherein in this case, R _{7 is} each C _1-5 alkyl), C _3-6 cycloalkyl, 5, 6 or 7 atom heterocyclic ring of carbon and oxygen and/or nitrogen; or an acid group, Such as CO ₂ H, SO ₃ H, OPO ₃ H ₂ . The dispersant or the salt thereof according to any one of claims 1 to 4, wherein the dispersant is according to: Formula IIIa

Wherein D is C _1-5 alkyl, CN, OH, NO ₂ , NH ₂ , halogen, CO ₂ H, SO ₃ H, CH ₃ or OCH ₃ ; and p is 0 to 4; formula IIIb

Wherein the hydrogen of any acid in the formula can be replaced by a metal, amine or ammonium cation, so that the dispersant is in the form of a salt; and U is O or NH. The dispersant or the salt thereof according to any one of claims 1 to 4, wherein the dispersant is according to: Formula IVa

Formula IVb

Wherein the hydrogen of any acid in the formula can be replaced by a metal, amine or ammonium cation, so that the dispersant is in the form of a salt; and x ₁ is 1-20. The dispersant or the salt thereof according to any one of claims 1 to 4, wherein the dispersant is according to: Formula V

In each case, R ₆ can be H, CH ₃ , or C ₂ H ₅ , or the following groups:

Wherein D is C _1-5 alkyl, CN, OH, NO ₂ , NH ₂ , halogen, CO ₂ H, SO ₃ H, CH ₃ or OCH ₃ ; and p is 0 to 4; and in the formula The hydrogen of any acid can be replaced by metal, amine or ammonium cation to make the dispersant in the form of a salt. A composition comprising particulate solids (typically pigments or fillers), an aqueous medium or a polar organic solvent medium, and a polymer chain having at least one, wherein the polymer is polymerized by any one of claims 1 to 12 above物说。 Object representation. The composition of claim 13, wherein the medium comprises an aqueous medium. Such as the composition of claim 13, wherein the medium comprises a polar organic medium. Such as the composition of claim 13, 14 or 15, wherein the composition is an abrasive base, paint or ink. The composition according to any one of claims 13 to 16, wherein the particulate solid pigment or filler. The composition of any one of claims 13 to 17, which further contains an adhesive. The composition of any one of claims 13 to 18, wherein the dispersant is in an amount ranging from 0.1% by weight to 79.6% by weight, or 0.5% by weight to 30% by weight, or 1% by weight to 25% by weight Exist, based on the weight of the total composition.