TW201444796A - Aromatic dispersant composition - Google Patents

Abstract

The present invention relates to a composition containing a particulate solid, a polar or non-polar organic medium, and a polymer chain having at least one fused aromatic imide pendant group. The invention further provides compositions for coatings, inks, toners, plastic materials (such as thermoplastics), plasticisers, plastisols, crude grinding and flush.

Description

Aromatic dispersant composition

The present invention relates to a composition comprising a particulate solid, a polar or non-polar organic medium, and a polymer chain having at least one fused aromatic fluorene imine pendant. The present invention further provides a composition for a coating, an ink, a toner, a plastic material (e.g., a thermoplastic), a plasticizer, a plastisol, a coarse abrasive, and a granule.

Many formulations, such as inks, paints, abrasives, and plastic materials, require an effective dispersant to evenly disperse the particulate solid in a polar organic or non-polar organic medium. Regarding ink, ink manufacturers want to manufacture high-resolution and quality printed products. The printing method poses a great challenge to the suitability of a wide range of base substrates, resins and pigments that have never been seen before. The pigment dispersion should be compatible with the different formulations used to ensure good adhesion and resistance to the final coating. Poor pigment dispersion or stabilization can cause cohesion or settling in polar organic liquid media or non-polar organic liquid media (such as inks or coatings), reducing gloss and aesthetics.

U.S. Patent No. 7,265,197 discloses a dispersant of the following formula which disperses a pigment in an ink composition: Wherein R _{1 is} each selected from the group consisting of H and CH ₃ , and n is an integer from 4 to 400.

International Publication No. WO 2008/028954 discloses a quinone imine dispersant compound containing a terminal acidic group 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 C _1-50 - optionally substituted hydrocarbyl, or C _1-50 - optionally substituted hydrocarbyl; Y Is C _2-4 -alkyleneoxy; x is 2 to 90; and q is 1 or 2, provided that in the formula (1a), when q is 1, T is -(CH ₂ ) ₃ -, And when q is 2, T is -(CH ₂ ) ₃ - or -CH ₂ CH(CH ₃ )-.

U.S. Patent No. 5,688,312 discloses an ink composition comprising a colorant, and the imine or quinone imine, and having a viscosity of from about 1 centipoise to about 10 centipoise at a temperature of from about 125 to about 180 °C. The quinone imine or quinone imine can be prepared by reacting phthalic anhydride with a mono or diamine. The monoamine can be, for example, dodecylamine or stearylamine. The diamine can be 1,12-dodecanediamine.

International Patent Application No. WO 2007/139980 discloses the reaction product of at least one dianhydride and at least two mutually different reactants, each of which contains a primary or secondary amine, hydroxyl or thiol functional group, and the reaction At least one of the substances is polymerizable. The reaction product can be used in compositions such as inks and coatings.

U.S. Patent No. 6,440,207 discloses a method of preparing a dispersible dry organic pigment for an aqueous system by (a) grinding a mixture comprising: (1) one or more organic pigments, (2) relative to the organic pigment Is at least about 1 weight percent of one or more aromatic polyalkylene oxide dispersants, (3) from 0 to about 10 weight percent of the abrasive liquid relative to the organic pigment, wherein the organic pigment is substantially insoluble, (4) a grinding additive other than the dispersing agent (2) of from 0 to about 50% by weight of the organic pigment, and (5) one or more surface treatment additives of from 0 to about 20% by weight relative to the organic pigment; (b) optionally adding one or more liquids to the milled pigment (6), wherein the organic pigment is substantially insoluble when the total solid content is not reduced to less than about 10%, and (7) a Or a polyvalent metal salt and/or one or more quaternary ammonium salts; and (c) isolating the ground organic pigment. The aromatic polyalkylene oxide dispersant can be reacted by reacting 250 g of deionized water, 19.8 g (0.100 mol) of 1,8-naphthalic anhydride, and 105 g (0.105 mol) in an autoclave. Jeffamine ^TM XTJ-506 (83 wt% of ethylene oxide, 17 wt% of propylene) is prepared. The autoclave was sealed, heated to 150 ° C with stirring, and maintained at 150 ° C for 5 hours. After the reaction was cooled, the resulting brown liquid was discharged into a beaker, and then 15 g of decolorized charcoal was added. After stirring overnight, the suspension was filtered and the filter pad was washed with water to yield approximately 500 g of amber filtrate with a solid content of 23.63%. The dry pigment can be used in aqueous paint systems.

It is an object of the present invention to provide a compound which at least improves color strength and other coloring properties, increases the loading of particulate solids, forms an improved dispersion, improves brightness, produces a composition having reduced viscosity, and maintains stable dispersion. Reduce particle size and reduce particle size distribution (typically down to an average of 150 nm or less, such as in the range of 70-135 nm), reduce haze, improve gloss, and increase jetting (especially when the composition is black) . The composition of the present invention is stable under both ambient temperature storage and high temperature storage conditions.

Electron-based groups are well known to those skilled in the art of organic synthesis. Examples of electron withdrawing groups include, but are not limited to, halogen (e.g., -Cl, -Br or -F), nitrile, carbonyl, nitro, sulfonyl, sulfonate, hydroxy, or amine.

The electron withdrawing group can be an activating group or a passivating group.

The activating group may include a hydroxyl group, an amine group or a halogen. In general, the activating group can include a halogen such as -Cl.

The passivating group may include a nitrile, a carbonyl group, a carboxyl group, a nitro group, an amine sulfonyl group, or a sulfonic acid group. In general, the passivating group can include a nitro group, a carboxyl group, or a sulfonic acid group.

In general, the electron withdrawing group can be a passivating group.

In a specific embodiment, the present invention provides a polymer comprising a polymer chain having at least one fused aromatic quinone imine pendant, wherein the polymer can be represented by formula (1): Wherein each of the variables may be R ₁ which may be a substituent at any position in the Q ring which may be used to bond the substituent, and R ₁ may be one or more of -H, a pull electron group (eg, -NO ₂ , -SO, respectively) ₂ NR' ₂ , -C(O)R', -SO ₃ M, -C(O)OM, halo (eg -Cl or -Br), -NH ₂ , or -OR'), or electron-releasing group (e.g., an alkyl group, such as -CH ₃ ) means (generally, when R _{1 is} not -H, the number of non-H groups defined by a may be 0 to 2, 0 to 1, 0, or 1) . For example, R ₁ may be -H, -CH ₃ , -Cl, -NO ₂ , -SO ₃ M, -C(O)OM, or -CN (generally, R ₁ may be - when a is not zero) Cl, -SO ₃ M or -NO ₂ ); M can be H, a metal cation, -NR' ₄ ⁺ , or a mixture thereof; R' can be -H, typically 1 to 20, or 1 to 10 carbons The atom is optionally substituted with an alkyl group, and the substituent may be a hydroxyl group, a halogen group (generally Cl), or a mixture thereof; and R ₂ may be C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C. _a hydrocarbon group, or a C ₁ to C ₂₀ , a C ₁ to C ₁₂ , or a C ₁ to C ₆ hydrocarbon carbonyl group (when R ₂ contains more than 2 carbon atoms, the hydrocarbon group or the hydrocarbon carbonyl group may be linear or branched And R ₃ may be H or C _1-50 (or C _1-20 ) - optionally substituted hydrocarbyl, which bonds to the terminal oxygen atom of the polymer chain to form a terminal ether group or terminal ester group, And may or may not contain a polymerizable group, such as a vinyl group, or a C _1-50 (or C _1-20 )-hydrocarbon carbonyl group (ie, a hydrocarbon group containing a carbonyl group) which bonds to the oxygen atom of the polymer chain to form a terminal ester. a terminal or terminal urethane group, and may or may not contain a polymerizable group, such as a vinyl group, and the substituent may be a halogen group, an ether group, an ester group Or a mixture thereof; Pol may be a homopolymer chain or a copolymer chain, wherein the polymer chain may be selected from the group consisting essentially of poly(ether), poly(ester), poly(esteramine), poly(alkylene) a group consisting of poly(decylamine), or a mixture thereof; u may be 1 to 3, 1 to 2, or 1; v may be 1 to 2; w may be 1 to 3, 1 to 2 Or 1; v = 1 when W = oxygen, sulfur or >NG; G may be halogen or a hydrocarbon group containing 1 to 200, 1 to 100, or 1 to 30 carbon atoms; when W = nitrogen, v = 2; and Q may be a fused aromatic ring containing 4n+2 π electrons, wherein n=2 or more, generally 2 to 5, 2 to 4, 2 to 3, or 2, and Q may form 5 or 6 The quinone imine ring (generally a 6-membered ring) is bonded to the quinone imine group.

In a particular embodiment, Pol can be selected from the group consisting of poly(ether), poly(ester), and mixtures thereof.

In a specific embodiment, a method of obtaining a polymer of the present invention (generally represented by formula (1)) comprises forming an amine-terminated polymer with a fusion of an aromatic diacid or anhydride, or another acid to form a derivative (eg, Ester, diamine, diacid dichloride) react to form a fused aromatic having a polymer chain A quinone imine. The reaction to form the quinone imine can be carried out at a sufficiently high temperature known in the art to facilitate the formation of quinone imine, for example at least 100 ° C, or 150 ° C to 200 ° C.

In a specific embodiment, the polymer of the present invention (generally represented by formula (1)) can be obtained by the following method: Step (1): (i) amino acid, (ii) amino alcohol, ( Iii) an amino mercaptan, or (iv) a diamine or polyamine, which is fused with an aromatic diacid or anhydride, or other acid forming derivative (eg, diester, diamine, diacid dichloride), An acid functionalized fusion aromatic quinone imine, a hydroxy functionalized fusion aromatic quinone imine, a thiol functionalized fusion aromatic quinone imine, or an amine functionalized fusion aromatic quinone imine is formed, respectively. The first step of the reaction can be carried out at a sufficiently high temperature known in the art to facilitate the formation of quinone imine, for example at least 100 ° C, or 150 ° C to 200 ° C; step (2): functionalizing the acid to aroma a quinone imine, a hydroxy functionalized fusion aromatic quinone imine, a thiol functionalized fusion aromatic quinone imine, or an amine functionalized fusion aromatic quinone imine formed by polymer chain or polymerized to form the polymer chain Monomer reaction.

If the polymer chain has been previously formed before the reaction of the step (2), the product of the step (1) can be used as a polymerization terminator.

If the polymer chain can be grown from one or more monomers in step (2), the product of step (1) can be used as a polymerization initiator.

When the product of the step (1) can be further reacted in the alkoxylation reaction, the reaction temperature may be from 100 ° C to 200 ° C in the presence of a base catalyst such as potassium hydroxide or sodium hydroxide.

When the product of step (1) or step (2) can be further esterified In the reaction in the reaction, the reaction temperature may be from 50 ° C to 250 ° C, or from 150 ° C to 200 ° C, optionally in the presence of an esterification catalyst.

The esterification catalyst can be any of those known in the art and includes tin(II) octoate, tetraalkyl titanate (e.g., tetrabutyl titanate), zinc salts of organic acids (e.g., zinc acetate), aliphatic A zirconium salt of an alcohol (e.g., zirconium isopropoxide), a toluenesulfonic acid or a strong organic acid (e.g., trifluoroacetic acid), or phosphoric acid.

The polymer of formula (1) can be capped with an R ₃ group. The R ₃ group can be derived from a carboxylic acid, an acid derivative, an alcohol, a thiol, an amine, or an isocyanate. The acid, acid derivative, alcohol, thiol, and amine are as described below. The reaction conditions for capping the polymer chain with an acid, an acid derivative, an alcohol, an amine, or an isocyanate to form a polymer of the present invention are those known in the art.

The process can be carried out in any inert atmosphere of the periodic table, but is typically nitrogen.

In a specific embodiment, the present invention provides a composition comprising a particulate solid, a non-polar organic medium, and a polymer chain having at least one fused aromatic quinone imine pendant, wherein the polymer is as defined above The formula (1) is expressed. The composition can be abrasive, paint or ink.

In a specific embodiment, the present invention provides a composition comprising a particulate solid, a polar organic medium, and a polymer chain having at least one fused aromatic quinone imine pendant, wherein the polymer is as defined above Expressed by the formula (1). The composition can be abrasive, paint or ink.

In a specific embodiment, the present invention provides a granulated solid, a non-polar organic medium, and having at least one fused aromatic A composition of a polymer chain of a quinone imine group, wherein the polymer is represented by the formula (1) as defined above, and further comprising a binder. In a particular embodiment, the binder can be nitrocellulose, polyethylene oxide, polyurethane, alkyd, poly(meth)acrylate, polyester, or polyamine.

In a specific embodiment, the present invention provides a composition comprising a particulate solid, a polar organic medium, and a polymer chain having at least one fused aromatic quinone imine pendant, wherein the polymer is as defined above Formula (1) represents and further contains a binder. In a particular embodiment, the binder can be nitrocellulose, polyurethane, poly(meth)acrylate, polyester, or polyamine.

The present invention also provides a composition comprising a particulate solid (typically a pigment or filler), a non-polar organic medium, and a polymer chain having at least one fused aromatic quinone imine pendant, wherein the polymer is The defined formula (1) is represented. The composition can be abrasive, paint or ink.

The invention also provides a composition comprising a particulate solid (typically a pigment or filler), a polar organic medium, and a polymer chain having at least one fused aromatic quinone imine pendant, wherein the polymer is as defined above The formula (1) is expressed. The composition can be abrasive, paint or ink.

The particulate solids in the compositions of the invention disclosed herein may be pigments or fillers. In a particular embodiment, the pigment can be an organic pigment.

The non-polar organic medium can include, for example, mineral oil, fat A hydrocarbon, an aromatic hydrocarbon, a plastic material (generally a thermoplastic resin or a thermosetting resin), or a plasticizer.

The polar organic medium can, for example, include ketones, esters, glycol ethers and esters, or alcohols.

In a specific embodiment, the present invention also provides a polymer comprising a polymer chain having at least one fused aromatic quinone imine pendant, wherein the chain can directly combine the fused diacid or anhydride with one or more Prepared by reacting a polyalkyleneamine (derived from an olefin polymer with an amine). The polymer may also be used in place of the polymer represented by formula (1) in the compositions disclosed herein.

In a specific embodiment, the present invention provides a paint or ink comprising a particulate solid, a non-polar organic medium, a film-forming resin, and a polymer of the invention disclosed herein.

In a specific embodiment, the present invention provides a paint or ink comprising a particulate solid, a polar organic medium, a film forming resin, and a polymer of the present invention as disclosed herein.

The ink can be inkjet ink, flexographic ink, gravure ink, or lithographic ink. The ink can be a radiation curable ink.

In a specific embodiment, the compositions disclosed herein further comprise a binder.

In a specific embodiment, the present invention provides a polymer chain comprising at least one fused aromatic quinone imine pendant (wherein the polymer can be represented by formula (1) as defined above), an organic pigment, and a binder The composition of the agent. The binder may be selected from the group consisting of nitrocellulose, polyurethane and polyamido. The composition can be used, for example The printing method of the flexographic printing method uses ink, or inkjet ink, such as radiation hardenability, non-impact, and control of droplets.

In a specific embodiment, the present invention provides a polymer chain comprising at least one fused aromatic quinone imine pendant (wherein the polymer can be represented by formula (1) as defined above), carbon black, and bonding The composition of the agent. The binder may be selected from the group consisting of nitrocellulose, polyurethane and polyamido. This composition can be used for inks for printing methods such as flexographic printing.

In a specific embodiment, the present invention provides a polymer chain comprising at least one fused aromatic quinone imine pendant (wherein the polymer can be represented by formula (1) as defined above), a particulate solid (generally It is a pigment or a filler), and (i) a polar organic medium or (ii) a composition of a non-polar organic medium, wherein the organic medium may be a plastic material. The plastic material may be a thermoplastic resin or a thermosetting resin.

In the compositions disclosed herein, the amount of the polymer of the present invention may range from 0.1 weight percent to 79.6 weight percent, from 0.5 weight percent to 30 weight percent, or from 1 weight percent to 25 weight percent of the composition.

In a specific embodiment, the invention provides a polymer chain having at least one fused aromatic quinone imine pendant (wherein the polymer can be represented by formula (1) as defined above) at the compositions disclosed herein Used as a dispersant.

In a specific embodiment, the present invention provides a polymer chain having at least one fused aromatic quinone imine pendant group (wherein the polymer can be represented by the formula (1) defined above) as a dispersion in the ink composition Use of the agent. The ink composition can reduce particle size and reduce particle size distribution (generally to an average of 150 nm or less), reduce haze, improve gloss, and increase jetting (especially when the composition is black) at least one of And stable under both ambient temperature storage and high temperature storage conditions.

Without being bound by theory, it is believed that the fusion aromatic quinone imine pendant can serve as a anchor between the polymer of the present invention and a particulate solid such as a pigment.

The present invention provides the compositions and uses disclosed above.

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

The number average molecular weight can be determined by GPC analysis on previously prepared polymer chains. The number average molecular weight of the in situ prepared polymer (ie, the polymer chain other than the quinone imine group) can be calculated by measuring the degree of polymerization (DP), which is combined with the monomer [M] and the initiator [I] (initiated The ratio of the agent to the aromatic anhydride is proportional to and calculated from the formula DP = [M] / [I]. It is possible to determine the degree of polymerization using nuclear magnetic resonance (NMR), thus calculating the number average molecular weight of the polymerized groups or polymer segments of the molecule.

Examples of the hydrocarbon group defined by R ² may include a methylene group, an exoethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a decyl group, a decyl group, a decyl group, or Branching isomers. In a particular embodiment, the hydrocarbyl group defined by R ² can be (-CH ₂ -) ₃ , -CH ₂ CH(CH ₃ )- or -CH ₂ CH ₂ -.

R ₂ may be derived from an amino alcohol, an amino thiol, an amino carboxylic acid, or an amine having 1 to 3, 1 to 2, or 1 -NH ₂ groups. The amine group may or may not contain an additional alkyl group.

Examples of the diamine include 1,2-diaminoethane, propane-1,3-diamine, butane-1,4-diamine, pentane-1,5-diamine, hex-1,6-diamine , 癸-1,12-diamine, or a mixture thereof.

Examples of polyamines include N-(2-aminoethyl)-1,3-propanediamine, 3,3'-imidopropylamine, spermidine, hydrazine (hexamethylene)triamine, three Ethylenetriamine, N,N'-indole (3-aminopropyl)-1,3-ethylenediamine, N,N'-indole (2-aminoethyl)-1,3-propanediamine , spermine, ginseng (2-aminoethyl)amine, tetraamethyleneamine, triethylenetetramine, or diethylenetriamine, or a mixture thereof.

The amino alcohol can be a C _2-20 -amino alcohol and may or may not contain more than one hydroxyl group and may or may not contain more than one amine group. The amino alcohol may be ethanolamine, 3-amino-1-propanol, 4-aminobutanol, 2-aminobutanol, 2-amino-2-methyl-1-propanol, 5-amine Base-1-pentanol, 5-amino-2-pentanol, 2-amino-3-methyl-1-butanol, 6-amino-1-hexanol, 2-amino-1-hexanol Alcohol, silk alcohol, 4-aminocyclohexanol, 2-(2-aminoethoxy)ethanol, 3-amino-1,2-propanediol, 2-amino-2-ethyl-1, 3-propanediol, cis (hydroxymethyl) aminomethane, cis (hydroxypropyl) aminomethane, 1,3-diamino-2-hydroxypropane, or a mixture thereof.

The amino mercaptan may be a C _2-20 -amino mercaptan and may or may not contain more than one thiol group and may or may not contain more than one amine group. The amino mercaptan may include 2-aminoethanethiol, 3-aminopropan-1-thiol, 4-aminobutan-1-thiol, 5-aminopentan-1-thiol, 6- Aminohexan-1-thiol, or a mixture thereof.

The term "hydrocarbon carbonyl" as used herein is a hydrocarbon group containing a carbonyl group. In general, the hydrocarbon-forming carbonyl group defined by R ₂ may include -(CH ₂ ) ₅ -C(O)-, -(CH ₂ ) ₄ -C(O)-, -(CH ₂ ) ₃ -C ( O) -, or _{- (CH 2) 2 -C (} O) -.

The aminocarboxylic acid (or amino acid) can be an amine-C _{2-20 -alkylene} (alkenyl) carboxylic acid and may or may not contain more than one carboxylic acid group and may or may not contain more than one amine group. The aminocarboxylic acid may or may not contain other hetero atom-containing groups such as a hydroxyl group or a thiol group. The alkylene group may be linear or branched. The alkane (alkenyl) group of the aminocarboxylic acid contains no more than 12 carbon atoms. Specific examples include 11-aminoundecanoic acid, 12-aminododecanoic acid, 6-aminohexanoic acid, 4-aminobutyric acid, aspartic acid, glutamic acid, lysine, aspartate Acid, glutamic acid, threonine, serine, cysteine, beta-alanine, glycine, and sarcosine. It can use a mixture of aminocarboxylic acids.

The extended or extended hydrocarbon carbonyl group used herein may be linear or branched, and saturated or unsaturated.

Those skilled in the art can fully understand the technical characteristics of 4n+2 π electrons defined in Q by Hückel's law. In general, 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 embodiment, n can be equal to two.

Q can be based on naphthalene, anthracene, phenanthrene, or mixtures thereof. In a specific embodiment, Q can be based on naphthalene.

When the Q system is based on naphthalene, the polymer chain of the formula (1) may have a naphthoquinone imine group such as 1,2-naphthoquinone imido, 2,3-naphthylimine, 1,8-naphthoquinone. Imino groups, or mixtures thereof.

When the Q system is based on hydrazine, the polymer chain of the formula (1) may have a 1,2-quinone imine group, a 2,3-quinone imine group, a 1,9-fluorenylene group, or Its mixture.

When the Q system is based on phenanthrene, the polymer chain of the formula (1) may have a 2,3-phenanthrene group, an 8,9-phenanthrene group, or a mixture thereof.

In general, the Q system is based on 1,8-naphthalic anhydride, 1,2-naphthalic anhydride, or a mixture thereof.

Q may be based on naphthalic anhydride such as 1,8-naphthalic anhydride (when R ₁ = H), 4-nitro-1,8-naphthalene dicarboxylate or 3-nitro-1,8 - quinone diiminate (when R ₁ = NO ₂ ), 4-chloro-1,8-naphthalene dicarboxylate (when R ₁ = Cl), 4-thioanthryl-1, Eudecyl 8-naphthalene dicarboxylate or quinone imine of 3-thioindolyl-1,8-naphthalene dicarboxylate (when one R ₁ =SO ₃ H), or a mixture thereof.

In a particular embodiment, when R ₁ is not H, the number of the non-H group may be defined as a 1 or 2. When R ₁ is other than H, the group defined by R ₁ may be a pull electron group (e.g., -NO ₂ group, -SO ₃ M group or halo group, typically -Cl), typically a pull electron group. When R ₁ is an electron withdrawing group, R ₁ may be a meta or para substitution with respect to the quinone imine group, or a mixture thereof. In a particular embodiment, R ₁ can be meta-substituted with respect to the quinone imine group.

In a specific embodiment, when R _{1 is} not H, the number of non-H groups defined by a may be zero.

R ₁ can generally be hydrogen.

R' may be an alkyl group having a linear or branched alkyl group or an optionally substituted alkyl group.

The alkyl group defined by R' includes methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, 2-ethylhexyl, decyl, fluorenyl, Eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty, or a mixture thereof. In a particular embodiment, R' can be derived from an alkanol.

R ₃ may be H or C _1-50 (or C _1-20 ) - optionally substituted hydrocarbyl, which bonds to the terminal oxygen atom of the polymer chain to form a terminal ether group or terminal ester group, with or without a polymeric group, such as a vinyl group, or a C _1-50 (or C _1-20 )-hydrocarbon carbonyl group (ie, a hydrocarbon group containing a carbonyl group) that bonds to the oxygen atom of the polymer chain to form a terminal ester group or a terminal amine group The acid ester group may or may not contain a polymerizable group such as a vinyl group, and the substituent may be a halogen group, an ether group, an ester group, or a mixture thereof.

R ₃ may be derived from an alcohol, a thiol, an amine, a carboxylic acid, an acid derivative (such as an acid halide), an isocyanate, or a mixture thereof.

The term "alkylene" as used herein is intended to include alkyl and alkenyl groups.

The alcohol may be a C _1-20 alkane (alkenyl) alcohol, which may be linear or branched. Specific examples of the alcohol include methanol, ethanol, n-propanol, isopropanol, n-butanol, 1-methylpropanol, 2-methylpropanol, tert-butanol, n-pentanol, 1-methylbutyl Alcohol, 2-methylbutanol, 3-methylbutanol, 2,2-dimethylpropanol, n-hexanol, 1-methylpentanol, 2-methylpentanol, 3-methylpentanol, 4-methylpentanol, 1,1-dimethylbutanol, 2,2-dimethylbutanol, 3,3-dimethylbutanol, 1,2-dimethylbutanol, n-heptanol , 1-methylhexanol, 2-methylhexanol, 3-methylhexanol, 4-methylhexanol, 1,2-dimethylpentanol, 1,3-dimethylpentanol, 1 , 1-dimethylpentanol, 1,1,2,2-tetramethylpropanol, benzyl alcohol, n-octanol, 2-ethylhexanol, n-nonanol, 1-methyl octanol, 2- Methyl octanol, n-decyl alcohol, n-undecyl alcohol, 1-methyl decyl alcohol, 2-methyl decyl alcohol, n-dodecyl alcohol, 2,4-diethyl octanol, and the so-called Guerbet (Guerbet) alcohol, such as the market name of Isofol® (e.g., Sasol) alcohol, or a mixture thereof. Designated examples of Guerbet alcohols include Isofol® 12, 14T, 16, 18T, 18E, 20, 24, 28, 32, 32T, and 36.

The amine may be a C _1-20 alkane(en)ylamine which may be linear or branched. Specific examples of the amine include methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, heptylamine, octylamine, decylamine, decylamine, dodecylamine, tetradecylamine, pentaamine, and hexadecylamine. , octadecylamine, icosylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine, diamylamine, dihexylamine, diheptylamine, dioctylamine, diamine, diamine, di- Dodecylamine, di-tetradecylamine, di-pentadecylamine, di-hexadecylamine, di-octadecylamine, di-octaamine, or a mixture thereof.

The thiol may be a C _1-20 alkane (alkenyl) thiol which may be linear or branched. Specific examples of the thiol include ethanethiol, 1-propanethiol, 2-propanethiol, 1-butanethiol, 2-methyl-1-propanethiol, 1-methyl-1-propanethiol , 1-hexyl mercaptan, 1-octyl mercaptan, 1-dodecyl mercaptan, hexadecanol, octadecyl mercaptan, cyclohexyl mercaptan, or a mixture thereof.

The carboxylic acid may be a C _1-20 alkane (alkenyl) carboxylic acid, which may be linear or branched. Specific examples of the carboxylic acid include acetic acid, methoxyacetic acid, propionic acid, isobutyric acid, 2-methylbutyric acid, isovaleric acid, valeric acid, isohexanoic acid, caproic acid, heptanoic acid, octanoic acid, 2-ethyl Caproic acid, citric acid, dodecanoic acid, tetradecanoic acid, palmitic acid, octadecanoic acid, icosonic acid, or a mixture thereof.

The isocyanate may be an aromatic or C _2-20 alkyl alkene isocyanate which may be linear or branched. Specific examples thereof include 1-isocyanatoethane, 1-isocyanatopropane, 1-isocyanatobutane, 2-isocyanatobutane, 1-isocyanatopentane, 1- Isocyanate hexane, 1-isocyanatoheptane, 3-(isocyanatomethyl)heptane, 2-isocyanatoheptane, 2-isocyanato-2,4,4 -trimethylpentane, 1-isocyanatooctane, 2-isocyanatooctane, 1-isocyanatodecane, 2-isocyanatodecane, 1-isocyanatoyl Dioxane, 1-isocyanatotetradecane, 1-isocyanatoundecane, 1-isocyanatooctadecane, 1-isocyanatopentadecane, 1-isocyanatoyl Hexane, isocyanatocycloheptane, isocyanatocyclooctane, (isocyanatomethyl)cyclohexane, isocyanatocyclododecane, isocyanatocyclopentane, isocyanide Acid cyclohexane, 1-ethyl-4-(2-isocyanatoethyl)benzene, 1-isocyanato-4-methylbenzene, 1-tert-butyl-4-isocyanate Benzobenzene, 4-isocyanato-1,2-dimethylbenzene, 1-isocyanato-2,4-dimethylbenzene, 2-isocyanato-1,3,5-trimethyl Alkylbenzene, 1-ethyl-4-isocyanatobenzene, 1-isocyanato-4-isopropylbenzene, or a mixture thereof.

The isocyanate may be polymerizable, for example, by reacting an alkoxy polyalkylene glycol with a diisocyanate. The diisocyanate may include toluene-2,4-diisocyanate, toluene-2,6-diisocyanate, hexamethylene diisocyanate, methylene diphenyl diisocyanate, isophorone diisocyanate, or a mixture thereof.

The acid halide may be a C _1-20 alkyl alk(en) acid halide, which may be linear or branched. Specific examples of the acid chloride include formazan chloride, butyl phosphonium chloride, 3,3-dimethylbutylphosphonium chloride, 3-methylbutylphosphonium chloride, 2-methylbutylphosphonium chloride, pentamidine chloride, helium chloride, Chlorhexidine, 2-ethylbutylphosphonium chloride, hydrazine chloride, 2-ethylhexyl chloride, octyl chloride, 2-methylamyl chloride, 3,5,5-trimethylhexyl chloride, hydrazine Chlorine, or a mixture thereof.

In a particular embodiment, R ₃ can comprise a polymerizable group, such as a vinyl group. R ₃ may comprise a group such as a (meth) acrylate, a styryl group, a vinyl ether, or an allyl ether, and mixtures thereof. Examples of R ₃ may be derived from (meth)acrylic acid and its ester, hydroxyalkyl (meth)acrylate and polyether derivatives thereof, such as hydroxyethyl acrylate or polyethylene glycol monoacrylate, (meth)acrylic acid a methyl cyanate group, such as isocyanatoethyl methacrylate, or an isocyanatostyryl derivative such as 4-isopropenyl-α,α-dimethylbenzyl isocyanate, or mixture.

W may be oxygen, sulfur, nitrogen, >NH, or >NG, wherein G represents hydrogen, or a hydrocarbon group containing from 1 to 200, from 1 to 100, or from 1 to 30 carbon atoms. In general, W can be oxygen, sulfur or nitrogen. When W is sulfur, the structural group represented by the aromatic ring -R ₂ -W can be formed by reacting an anhydride of the fused aromatic ring with an amine thiol. When W is oxygen, the structural group represented by the aromatic ring -R ₂ -W can be formed by reacting an anhydride of the fused aromatic ring with an amino alcohol or an aminocarboxylic acid. When W is a nitrogen (or> NG), an aromatic ring structure group represented by -R ₂ -W may be fused by an aromatic ring of the anhydride to a diamine or polyamine to form.

It is possible to use all the mixtures, that is, the structural group represented by the aromatic ring -R ₂ -W can be obtained by using an aromatic ring anhydride as an amino alcohol, an aminocarboxylic acid, an aminothiol, a diamine, or A mixture of two, three, four, or all five of the polyamines is formed by reaction. The aromatic ring-R ₂ -W can be formed in a single vial reaction in the presence of all of the reactants. Alternatively, a blend of aromatic ring-R ₂ -W groups can be formed by mixing individual previously prepared quinazones.

The cation M can be a mono-, di- or trivalent metal. The metal can For example, it is an alkali metal, an alkaline earth metal or a transition metal. The metal can include lithium, sodium, potassium, calcium, magnesium, barium, zinc, or mixtures thereof.

The polymer chain Pol can be a homopolymer. The polymer chain Pol can be a copolymer. When Pol is a copolymer, the polymer chain can have a random or block structure. Pol may be a homopolymer chain or a copolymer chain, wherein the polymer chain may be selected from the group consisting essentially of poly(ether), poly(ester), poly(esteramine), poly(decylamine), poly(olefin). And a group of mixtures.

In a specific embodiment, the polymer chain (Pol) is based on poly(ether). The poly(ether) can be based on a polyalkylene glycol (typically a poly C ₂ -C ₄ -alkylene glycol) or a polyalkylene glycol (typically a poly C ₈ -diol). The polyether can be based on a polyalkylene oxide such as ethylene oxide, propylene oxide, butylene oxide, epoxyethylbenzene, or mixtures thereof. When the polymer chain is a polyether homopolymer, the polyether is not based on ethylene oxide.

In a specific embodiment, the polymer chain (Pol) is based on a poly(ester). The poly(ester) can be based on a hydroxy-C _{2-20 -alkylene} (carboxylic acid) carboxylic acid monomer or a lactone monomer.

Examples of the hydroxy-C _{2-20 -alkylene} (carboxylic acid) carboxylic acid include ricinoleic acid, 12-hydroxystearic acid, 6-hydroxycaproic acid, 5-hydroxyvaleric acid, 12-hydroxydodecanoic acid, 5 - Hydroxydodecanoic acid, 5-hydroxydecanoic acid, 4-hydroxydecanoic acid, 10-hydroxyundecanoic acid, lactic acid, glycolic acid, or a mixture thereof.

Examples of lactones include β-propiolactone, γ-butyrolactone, optionally an alkyl-substituted ε-caprolactone, and optionally an alkyl-substituted δ-valerolactone. The alkyl substituent in ε-caprolactone and δ-valerolactone may be a C _1-6 -alkyl group or a C _1-4 -alkyl group, and may be linear or branched. Examples of suitable lactones include ε-caprolactone and 7-methyl-, 2-methyl-, 3-methyl-, 5-methyl-, 6-methyl-, 4-methyl-, 5 Tributyl-, 4,4,6-trimethyl-, and 4,6,6-trimethyl-homolog, or mixtures thereof.

In a specific embodiment, the polymer chain (Pol) is based on a poly(ester). The poly(ester) can be based on the reaction of the diol represented by the formula (i) with the diacid represented by the formula (ii): HO-X ¹ -OH formula (i)

HO-CO-X ² -COOH formula (ii) wherein X ¹ is a linear comprising from 2 to 20 carbon atoms or branched alkylene, or removal of two hydroxyl groups of poly extending alkanediol residue; and X ² It is a linear or branched alkyl (alkenyl) group containing 2 to 20 carbon atoms, or Ph.

Specific examples of suitable diols include alkylene glycols such as ethylene glycol, propylene glycol, neopentyl glycol, 1,4-butanediol, 1,6-butanediol, 1,6-hexanediol, Ether-linked diols such as diethylene glycol, dipropylene glycol, tripropylene glycol, and triethylene glycol. Suitable examples of glycols include poly extending alkoxy polyethylene glycol, polypropylene glycol, polytetramethylene glycol, MW less than 1000 of polyethylene glycol and polypropylene glycol with a mixed block of a random copolymer (available from BASF's Pluronic ^TM trans Pluronic ^TM). Specific examples of the diacid and the anhydride include maleic anhydride, succinic anhydride, fumaric anhydride, malonic acid, adipic acid, sebacic acid, phthalic anhydride, oxalic acid, and cyclohexane dicarboxylic anhydride.

In a specific embodiment, the polymer chain (Pol) is based on poly(decylamine). The poly(decylamine) can be based on the reaction of a diamine represented by the formula (iii) with a diacid represented by the formula (ii): H ₂ NX ¹ -NH ₂ wherein, X ¹ is 2 to 2 a linear or branched alkyl group of 20 carbon atoms, or a polyalkylene glycol residue having 2 amine groups removed; or the polyamine is derived from an intrinsic amine, an aminocarboxylic acid, or a mixture thereof reaction.

Specific examples of the diamine include alkylene diamines such as ethylenediamine, 1,2-propylenediamine, 1,3-propanediamine, isobutylene diamine, pentamethylenediamine, hexamethylenediamine, heptanediamine, 1,12-Diaminododecane, with diaminocyclohexane, and a diamine having an ether linkage, such as 1,2-anthracene (2-aminoethoxy)ethane. Suitable examples of polyether diamines include Jeffamine ^TM commercially available from Huntsman diamines such as D230, D400, ED600. Specific examples of the indoleamine include dodecylamine and caprolactam, and the aminocarboxylic acid may be glycine, sarcosine, β-alanine, 4-aminobutyric acid, 6-amino group. Caproic acid, 11-aminoundecanoic acid, or 12-aminododecanoic acid.

In a specific embodiment, the polymer chain (Pol) is based on poly(esteramine). The poly(esteramine) may be based on one or more selected from the group consisting of a diol (formula (i)), a diacid/anhydride (formula (ii)), a lactone, and a hydroxy-C _{2-20 -alkylene} (alkenyl) a polyester moiety prepared by reacting a compound of the group consisting of carboxylic acids, and one or more selected from the group consisting of diamines (formula (iii)), aminocarboxylic acids, decylamines, and diacids/anhydrides ( The polyamine moiety is prepared by the reaction of a compound of the group consisting of formula (ii)). The reaction conditions and process steps for the formation of a polyester using a diol, polyester decylamine and polyamidamine are disclosed in columns 5-7 of U.S. Patent No. 5,760,257.

In a specific embodiment, the polymer chain (Pol) is based on poly(alkylene). It can be obtained that the polymer chain (Pol) is represented by poly(alkylene) The method of the quinone imine of the formula (1) comprises reacting a polyene-substituted amine with a fused aromatic diacid or anhydride. The polyalkylene substituted amine can be derived from an olefin polymer and an amine such as ammonia, a diamine, a polyamine, or a mixture thereof. It can be prepared by a variety of methods, as described below.

In a specific embodiment, the polymer chain (Pol) is based on poly(ether). In a specific embodiment, the poly(ether) polymer chain can be incorporated into the quinone imine structure represented by formula (2): Wherein each of the variables R ₁ may be, respectively, may be in the Q ring is a key junction substituent may be used at any position of a substituent group, and R ₁ respectively, by one or more -H, electron-withdrawing groups (such as -CN, -NO _2, -SO ₂ NR' ₂ , -C(O)R', -SO ₃ M, -C(O)OM, halo (eg -Cl or -Br), -NH ₂ , or -OR'), or electron A releasing group (such as an alkyl group such as -CH ₃ ) means (generally, when R _{1 is} not -H, the number of non-H groups defined by a may be 0 to 2, 0 to 1, 0, or 1); W may be oxygen; M may be H, a metal cation, -NR' ₄ ⁺ ; R' may be -H, optionally substituted alkyl having 1 to 20, or 1 to 10 carbon atoms And the substituent may be a hydroxyl group, a halogen group (generally Cl), or a mixture thereof; R ₂ may be a C ₁ to C ₂₀ , a C ₁ to C ₁₂ , or a C ₁ to C ₆ alkyl group, or a C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C ₆ extend a hydrocarbon carbonyl (when R ₂ contains more than 2 carbon atoms, the extended or extended hydrocarbon carbonyl group may be linear or branched), or a mixture thereof; R ₃ It may be H or C _1-50 (or C _1-20) - optionally substituted hydrocarbon group, an oxygen atom which is bonded to the terminal of the polymer chain to form a terminal or a terminal ether group, an ester group, and may or may not contain The polymerizable group, such as vinyl, or C _1-50 (or C _1-20) - hydrocarbon carbonyl group (i.e. the carbonyl-containing hydrocarbon group), an oxygen atom which is bonded to the polymer chains to form a terminal ester group or terminal group A ester group, and may or may not contain the polymerizable group, such as a vinyl group, and the substituent may be a halogen group, an ether group, an ester group, or mixtures thereof; Pol when the same element is a polymer, R ₄ can be Methyl, ethyl or phenyl, and when Pol is a copolymer, R ₄ is a mixture of H, methyl, ethyl, or phenyl, provided that when R ₄ is H, it is sufficient to provide no An amount of more than 60% by weight of the oxirane group is present in the copolymer chain; u may be 1 to 3, 1 to 2, or 1; w may be 1 to 3, 1 to 2, or 1; When R ₂ is a hydrocarbon group, u is 1 and w is 1; and m may be 1 to 110, 1 to 90, or 2 to 90.

In formula (2), the integer m is such that the polymer chain can have from 100 to 10,000, from 100 to 5,000, from 300 to 3,000, or from 400 to 2,500. The number average molecular weight.

The quinone imine of formula (2) can be prepared by two different methods. The polymer chain of formula (2) may refer to a polyether, and the polymer chain may have a random or block structure.

The polyether may contain from 0 to 60 weight percent, from 0 to 50 weight percent, from 0 to 30 weight percent, from 0 to 20 weight percent, from 0 to 15 weight percent of ethylene oxide. The polyether may have 40 to 100 weight percent, 50 to 100 weight percent, 70 to 100 weight percent, 80 to 100 weight percent, or 85 to 100 weight percent of carbon atoms having 3 or more (generally 3 or 4) An alkylene oxide having 3 or more carbon atoms, having 8 or more carbon atoms (generally 8 carbon atoms), or a mixture thereof.

The polyether may, for example, be a homopolymer containing propylene glycol, butylene glycol, ethyl benzene glycol, or may be a random or block copolymer, which generally contains ethylene glycol, butylene glycol and ethyl benzene. At least one of the alcohols is copolymerized with propylene glycol.

The polyether can be, for example, a copolymer of ethylene oxide and propylene oxide. The polyether can be derived from: 0 to 60 weight percent ethylene oxide, 40 to 100 weight percent propylene oxide, 0 to 50 weight percent ethylene oxide, and 50 to 100 weight percent propylene oxide 0 to 30 weight percent of ethylene oxide, 70 to 100 weight percent of propylene oxide, 0 to 20 weight percent of ethylene oxide, and 80 to 100 weight percent It is divided into propylene oxide, or 0 to 15 weight percent of ethylene oxide, and 85 to 100 weight percent of propylene oxide.

For example, the polyether may contain 8 weight percent ethylene oxide and 92 weight percent propylene oxide, or 14 weight percent ethylene oxide and 86 weight percent propylene oxide.

In a particular embodiment, the polymer chain can be (i) a polypropylene oxide homopolymer, or (ii) a poly(ether) of a copolymer of ethylene oxide and propylene oxide.

The first method comprises reacting a polyetheramine (typically a polyalkylene oxide monoalkyl ether monoamine) with an aromatic diacid or anhydride to form a product of formula (2). The reaction to form the quinone imine product of formula (2) can be carried out at a sufficiently high temperature known in the art to facilitate the formation of quinone imine, for example at least 100 ° C, or 150 ° C to 200 ° C.

The polyetheramine can form an alcohol-terminated polymer chain by reacting the monool initiator with only propylene oxide or a mixture of propylene oxide and ethylene oxide, and then converting the alcohol-terminated polymer chain to an amine. preparation. The polyether amine may be a commercially available Surfonamine ^® Huntsman Corporation amine. Examples of the amines specified as Surfonamine ^® B60 (ethylene oxide to propylene oxide ratio of from 1 to 9), B100 (propylene oxide), B200 (ethylene oxide to propylene oxide ratio of 6-29). The numbers in parentheses are approximately repeating units of propylene oxide and ethylene oxide, respectively. The polyetheramine can be obtained by alkoxylation of an amino alcohol as described in U.S. Patent No. 5,879,445 (especially the disclosure of column 2, line 50 to column 7, line 50).

The second method comprises reacting an amino acid with a fused aromatic diacid or anhydride to form an acid functional quinone imine, and can be carried out at a sufficiently high temperature known in the art to facilitate the formation of quinone imine, such as at least 100 ° C, or 150 ° C to 200 ° C; and the acid-functionalized quinone imine is esterified with a polyalkylene glycol monosubstituted C _1-20 alkane (alkenyl) ether, the reaction temperature can be 50 ° C to 250 ° C , or 150 ° C to 200 ° C, as appropriate in the presence of esterification catalyst.

The polyalkylene glycol monosubstituted C _1-20 alkane (alkenyl) ether may be a homopolymer containing propylene glycol, butylene glycol or benzenediol, or may be a random or block copolymer, which is generally It contains at least one of ethylene glycol, butanediol and benzenediol and is copolymerized with propylene glycol.

The polyalkylene glycol monosubstituted C _1-20 alkylene (alkenyl) ether may be methoxy polypropylene glycol, ethoxy polypropylene glycol, propoxy polypropylene glycol, butoxy polypropylene glycol, alkoxy (poly Ethylene glycol-co-polypropylene glycol), polypropylene glycol mono(meth)acrylate, or a mixture thereof.

In a specific embodiment, the polymer chain (Pol) is based on poly(ether). The poly(ether) can be based on a polyalkylene glycol (typically a poly C ₂ -C ₄ -alkylene glycol). In a particular embodiment, the poly(ether) polymer chain can be incorporated into the quinone imine structure represented by formula (3a): Each of the variables of formula (3a) may be that R ₁ may be a substituent at any position in the Q ring which may be used to bond a substituent, and R _{1 is} each one or more of -H, an electron-withdrawing group (eg, -CN, -NO ₂ , -SO ₂ NR' ₂ , -C(O)R', -SO ₃ M, -C(O)OM, halo (eg -Cl or -Br), -NH ₂ , or -OR' Or, an electron-releasing group (such as an alkyl group such as -CH ₃ ) means (generally, when R _{1 is} not -H, the number of non-H groups defined by a may be 0 to 2, 0 to 1 , 0, or 1). For example, R ₁ may be -H, -CH ₃ , -Cl, -NO ₂ , -SO ₃ M, or -C(O)OM (generally, when a is not zero, R ₁ may be -Cl, -SO ₃ M or -NO ₂ ); W can be sulfur, >NG, oxygen, or a mixture thereof (generally oxygen); G can be from 1 to 200, from 1 to 100, or from 1 to 30 carbon atoms a hydrocarbon group; M may be H, a metal cation, -NR' ₄ ⁺ ; R' may be -H, an optionally substituted alkyl group generally having 1 to 20, or 1 to 10 carbon atoms, and the substituent It may be a hydroxyl group, a halogen group (generally Cl), or a mixture thereof; R ₂ may be a C ₁ to C ₂₀ , a C ₁ to C ₁₂ , or a C ₁ to C ₆ alkyl group, or a C ₁ to C ₂₀ , C ₁ To a C ₁₂ or C ₁ to C ₆ hydrocarbon carbonyl group, or a mixture thereof; R ₃ may be H or a C _1-50 (or C _1-20 )-hydrocarbon carbonyl group (ie, a hydrocarbon group containing a carbonyl group), which is bonded to the polymerization. An oxygen atom of the chain to form a terminal ester group or a terminal urethane group, and may or may not contain a polymerizable group, such as a vinyl group, and the substituent may be a halogen group, an ether group, an ester group, or mixtures thereof; when R is Pol polymer ₄ At the same element may be a methyl, ethyl or phenyl, and when the copolymer is Pol, R ₄ is H, methyl, ethyl or phenyl Thereof, with the proviso that when R ₄ is H, which is sufficient to provide the system does not exceed 60 weight percent of the amount of ethylene oxide groups present in the copolymer chain; U can be 1 to 3, 1 to 2, or 1; w may be 1 to 3, 1 to 2, or 1; and m may be 1 to 110 or 2 to 90.

The polymers of the present invention can have a plurality of polymer chain-type attachment W groups. In a specific embodiment, the polymer chain (Pol) is based on poly(ether). The poly(ether) can be based on a polyalkylene glycol (typically a poly C ₂ -C ₄ -alkylene glycol). In a specific embodiment, the poly(ether) polymer chain can be incorporated into the quinone imine structure represented by formula (3b): Wherein W is N (formed when R ₂ of formula (1) is derived from a diamine or polyamine); R ₂ is a C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C ₆ alkyl; Is 2; and all other variables therein are as defined above.

In formulas (3a) and (3b), the integer m is such that the polymer chain is It has a number average molecular weight of 100 to 10,000, 100 to 5,000, 300 to 3,000, or 400 to 2,500.

The quinone imines of the formulae (3a) and (3b) can be prepared by different methods. The polymer chains of the formulae (3a) and (3b) may be referred to as polyethers.

The method for preparing the formula (3a) may comprise reacting an amino alcohol with a fused aromatic diacid or an anhydride to form a hydroxy-functionalized fusion aromatic quinone imine, and then functionalizing the hydroxy-functionalized aromatic quinone imine with an epoxy An alkane such as propylene oxide, butylene oxide, epoxidized ethylbenzene, or a mixture of propylene oxide and ethylene oxide, butylene oxide, ethylene oxide benzene, or a mixture thereof, or a carbonate ( The reaction is carried out, such as ethyl or ethyl propyl carbonate, to form a polymer of the formula (3a) of the present invention wherein R ₃ is -H. The first step of the reaction (formation of the quinone imine) can be carried out at a sufficiently high temperature known in the art to facilitate the formation of quinone imine, for example at least 100 ° C or 150 ° C to 200 ° C, or at least 100 ° C or 150 ° C. Up to 250 ° C. The second step of reacting the quinone imine with ethylene oxide in the reaction is carried out in the presence of a base catalyst at a sufficiently high temperature known to those skilled in the art, for example at least 100 ° C, or 150 ° C to 200 ° C. In general, a temperature in the range of 150 ° C to 250 ° C can be used when carbonate is used.

The method for preparing the formula (3a) may further comprise reacting the amino acid with a fusion aromatic diacid or an anhydride to form an acid functionalized fusion aromatic quinone imine, and then functionalizing the aromatic ruthenium complex with the acid. The imine is reacted with ethylene oxide (e.g., ethylene oxide, propylene oxide, butylene oxide, epoxyethylbenzene, or a mixture thereof) to form the formula (3a) wherein R ₃ is -H ) a polymer.

The method of preparing the formula (3a) may further comprise reacting an amine thiol with the above-described method to form a thiol-functionalized fusion aromatic quinone imine, and then functionalizing the thiol-functionalized aromatic quinone imine with ethylene oxide. (such as ethylene oxide, propylene oxide, butylene oxide, ethylene oxide benzene, or a mixture thereof), or a carbonate (such as ethyl or ethyl propylene carbonate), wherein R ₃ is -H of the polymer of the formula (3a) of the invention.

The method for preparing the formulas (3a) and (3b) may also comprise reacting the diamine with a fusion aromatic diacid or anhydride to form an amine functionalized fusion aromatic quinone imine, and then the amine functional group. Blending aromatic quinone imine with ethylene oxide (such as ethylene oxide, propylene oxide, butylene oxide, epoxy ethylbenzene, or mixtures thereof), or carbonate (such as ethyl or carbonic acid carbonate) The propyl ester is reacted to form a polymer of the formula (3a) and (3b) of the present invention wherein R ₃ is -H.

In the above process, a hydroxy functionalized fusion aromatic quinone imine, a thiol functionalized fusion aromatic quinone imine, an acid functionalized fusion aromatic quinone imine, or an amine functionalized fusion aromatic quinone imine is epoxy The ethane reaction can be carried out at a temperature of from 100 ° C to 200 ° C in the presence of a base such as potassium hydroxide or sodium hydroxide.

In a specific embodiment, the poly(ether) polymer chain of the quinone imine structure represented by the formulas (3a) and (3b) wherein R ₃ is -H may be C _1-50 (or C _{1- 20} )-Hydrocarbon carbonyl (i.e., a hydrocarbon group containing a carbonyl group) is blocked. R ₃ may be derived from a carboxylic acid, an acid derivative such as an acid halide, an isocyanate, or a mixture thereof. a reaction condition in which a polymer chain is blocked to form a polymer of the formulae (3a) and (3b), wherein R ₃ may be a C _1-50 (or C _1-20 )-hydrocarbon carbonyl group (ie, a hydrocarbon group containing a carbonyl group), It is a reaction known in the art.

In formulas (2) and (3), when the polyether contains at least 50 weight percent A polar organic medium dispersant is formed when the ratio is 100% by weight of propylene oxide.

In formulae (2) and (3), a polar organic medium dispersant is formed when the polyether contains at least 0 weight percent to 40 weight percent ethylene oxide. However, the amount of ethylene oxide can also be modified by the art of preparing a non-polar organic medium dispersant or a polar organic medium dispersant to produce a dispersant having up to 49.99 weight percent ethylene oxide.

In general, the formulas (2) and (3) and the polymer chain (Pol) contain 60% by weight to 100% by weight, 80% by weight to 100% by weight, or 100% by weight of propylene oxide, and 0% by weight to 40% by weight, or 0% by weight to 20% by weight, or 0% by weight of ethylene oxide.

In a particular embodiment, the polymer of the invention may be represented by formula (4a), ie the polymer may be a poly(ester), a poly(esteramine) or a poly(decylamine): Wherein each of the variables R ₁ may be, respectively, may be in the Q ring is bonded substituent may be used at any position of a substituent group, and R ₁ respectively, by one or more -H, electron-withdrawing groups (such as -CN, -NO _2, -SO ₂ NR' ₂ , -C(O)R', -SO ₃ M, -C(O)OM, halo (eg -Cl or -Br), -NH ₂ , or -OR'), or electron A releasing group (such as an alkyl group such as -CH ₃ ) means (generally, when R _{1 is} not -H, the number of non-H groups defined by a may be 0 to 2, 0 to 1, 0, or 1); W is oxygen or >NG; G may be hydrogen or a hydrocarbon group containing 1 to 200, 1 to 100, or 1 to 30 carbon atoms; M may be H, a metal cation, -NR' ₄ ⁺ ; R' may be -H, optionally substituted alkyl having from 1 to 20, or from 1 to 10 carbon atoms, and the substituent may be hydroxy, halo (typically Cl), or mixtures thereof; ₂ may be C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C _{6 to} extend a hydrocarbon carbonyl; R ₃ may be H or C _1-50 (or C ₁ - ₂₀ ) - optionally substituted hydrocarbyl group, Bonding a terminal oxygen atom to form a terminal ester group, and may or may not contain a polymerizable group, such as a vinyl group, and the substituent may be a halogen group, an ether group, an ester group, or a mixture thereof ; R ₅ may be C _1-19 - extending hydrocarbon group; the Y may be oxygen or>NG; p may be 2-120; u may be 1 to 3, 1 to 2, or 1; and w may be 1 to 3, 1 to 2, or 1.

In a particular embodiment, the polymer of the invention may be represented by formula (4b), ie the polymer may be a poly(ester), a poly(esteramine) or a poly(decylamine): Wherein each of the variables may be R ₁ which may be a substituent at any position in the Q ring which may be used to bond the substituent, and R ₁ respectively consists of one or more -H, a pull electron group (eg, -NO ₂ , -SO _{2 )} NR' ₂ , -C(O)R', -SO ₃ M, -C(O)OM, halo (eg -Cl or -Br), -NH ₂ , or -OR'), or electron-releasing group ( Such as an alkyl group, such as -CH ₃ ) means (generally, when R _{1 is} not -H, the number of non-H groups defined by a may be 0 to 2, 0 to 1, 0, or 1); W may be sulfur, >NG, or oxygen (generally oxygen); G may be hydrogen or a hydrocarbon group containing from 1 to 200, from 1 to 100, or from 1 to 30 carbon atoms; M may be H, a metal cation, -NR' ₄ ⁺ , or a mixture thereof; R' may be -H, optionally substituted alkyl having 1 to 20 or 1 to 10 carbon atoms, and the substituent may be a hydroxyl group or a halogen group ( Typically, Cl), or a mixture thereof; R ₂ may be C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C ₆ alkyl; R ₃ may be H or C _1-50 (or C _1-20) a hydrocarbon carbonyl (ie a hydrocarbon group containing a carbonyl group) which bonds to the oxygen atom of the polymer chain to form a terminal ester group or a terminal urethane group, and may or may not contain a polymerizable group such as ethylene And the substituent may be a halogen group, an ether group, an ester group, or mixtures thereof; R ₅ may be C _1-19 - extending hydrocarbon group; the Y may be oxygen or>NG; p may be 2-120; u may be 1 to 3, 1 to 2, or 1; and w may be 1 to 3, 1 to 2, or 1.

The polymer chain of formula (4a) or (4b) may have a number average molecular weight of from 200 to 10,000, from 300 to 5,000, from 500 to 3,000, or from 600 to 2,500. In general, the polymer chain of formula (4a) or (4b) may have a number average molecular weight of from 600 to 2500.

A process for preparing a quinone imine of formula (4a) wherein R ₃ is -H comprises reacting an amino acid with a fused aromatic diacid or anhydride to form an acid functionalized fused aromatic quinone imine, which is then functionalized The fused aromatic quinone imine is reacted with one or more hydroxy-C _{2-20 -alkylene} (carboxylic acid) carboxylic acids, lactones, aminocarboxylic acids, or mixtures thereof. The reaction of the acid functionalized fusion aromatic quinone with a hydroxy-C _{2-20 -alkylene} carboxylic acid, a lactone, an amino carboxylic acid, or a mixture thereof may be from 50 ° C to 250 ° C, or 150 ° C. The temperature to 200 ° C is carried out in the presence of a catalyst as appropriate.

In a specific embodiment, the quinone imine represented by the formula (4a) wherein R ³ is a C _1-50 (or C _1-20 )-hydrocarbyl group can be represented by the formula (4a) wherein R ₃ is -H The quinone imine is prepared by reacting an alcohol, an amine, a thiol, or a mixture thereof. The reaction conditions for capping the polymer chain with an alcohol, amine or thiol to form a polymer of the invention are known in the art.

Alternatively, a process for preparing a quinone imine of formula (4a) wherein R ³ may be a C _1-50 (or C _1-20 )-hydrocarbyl group comprises reacting an amino acid with a fused aromatic diacid or anhydride to form an acid function Blending an aromatic quinone imine, then functionalizing the acid-fused aromatic quinone imine with one or more hydroxy-functional polyesters, hydroxy-functional polyester decylamines, amine-functionalized polyester guanamines, or amines The polyfunctional amine reaction is carried out at a temperature of from 50 ° C to 250 ° C, or from 150 ° C to 200 ° C, optionally in the presence of a catalyst. The hydroxy-functional polyester may be derived from one or more hydroxy-C _{2-20 -alkylene} carboxylic acids, lactones, or mixtures thereof and C _1-50 (or C _1-20 )-optionally substituted hydrocarbyl groups The polymerization is carried out at a temperature of from 50 ° C to 250 ° C, or from 150 ° C to 200 ° C, optionally in the presence of an esterification catalyst, as disclosed in U.S. Patent No. 4,861,380.

The amine or hydroxy functional polyester decylamine may be derived from one or more hydroxy-C _{2-20 -alkylene} carboxylic acids, lactones, or mixtures thereof, with one or more aminocarboxylic acids and C _{1 -50} (or C _1-20 ) - optionally by polymerization of a hydrocarbyl group, and conveniently carried out at a temperature of from 50 ° C to 250 ° C, or from 150 ° C to 200 ° C, optionally in the presence of an esterification catalyst, such as U.S. Patent No. 5,760,257.

The amine functional poly (Amides) can be obtained from one or more amino acids with C _1-50 (or C _1-20) - optionally substituted hydrocarbon radical polymerization, the system and conveniently at 50 deg.] C to The temperature of 250 ° C, or 150 ° C to 200 ° C, is carried out in the presence of a catalyst, as disclosed in U.S. Patent No. 5,760,257.

A process for preparing a quinone imine of formula (4b) wherein R ₃ is -H comprises reacting an amino alcohol with a fused aromatic diacid or anhydride to form a hydroxy-functionalized fused aromatic quinone, and then functionalizing the hydroxy group The fused aromatic quinone imine is reacted with one or more hydroxy-C _{2-20 -alkylene} (carboxylic acid) carboxylic acids, lactones, aminocarboxylic acids, or mixtures thereof. The reaction of the hydroxy-functionalized fusion aromatic quinone with a hydroxy-C _{2-20 -alkylene} carboxylic acid, a lactone, an amino carboxylic acid, or a mixture thereof may be from 50 ° C to 250 ° C, or 150 ° C. The temperature to 200 ° C is carried out in the presence of a catalyst as appropriate.

A process for preparing a quinone imine of formula (4b) wherein R ₃ is -H comprises reacting an amine thiol with a fused aromatic diacid or anhydride to form a thiol functionalized fusion aromatic quinone imide, and then the sulphur The alcohol functionalized fusion aromatic quinone imine is reacted with one or more hydroxy-C _{2-20 -alkylene} (carboxylic acid) carboxylic acids, lactones, aminocarboxylic acids, or mixtures thereof. The reaction of the thiol-functionalized fusion aromatic quinone with a hydroxy-C _{2-20 -alkylene} carboxylic acid, a lactone, an amino carboxylic acid, or a mixture thereof may be from 50 ° C to 250 ° C, or 150 The temperature is from °C to 200 °C, as the case may be, in the presence of a catalyst.

A process for preparing a quinone imine of formula (4b) wherein R ₃ is -H comprises reacting a diamine or polyamine with a fused aromatic diacid or anhydride to form an amine functionalized fusion aromatic quinone imide, and then The amine functionalized fusion aromatic quinone imine is reacted with one or more hydroxy-C _{2-20 -alkylene} (carboxylic acid) carboxylic acids, lactones, aminocarboxylic acids, or mixtures thereof. The reaction of the amine functionalized fusion aromatic quinone with a hydroxy-C _{2-20 -alkylene} carboxylic acid, a lactone, an amino carboxylic acid, or a mixture thereof can be from 50 ° C to 250 ° C, or 150 The temperature is from °C to 200 °C, as the case may be, in the presence of a catalyst.

In a specific embodiment, the quinone imine represented by the formula (4b) wherein R ³ is a C _1-50 (or C _1-20 )-hydrocarbon carbonyl group (ie, a hydrocarbon group containing a carbonyl group) can be obtained by The quinone imine of the formula (4b) wherein ₃ is -H is prepared by reacting a carboxylic acid, an acid derivative (such as an acid halide), an isocyanate, or a mixture thereof. The reaction conditions for capping the polymer chain with an acid, acid derivative or isocyanate to form the polymer of the present invention are those known in the art.

Alternatively, a process for preparing a quinone imine of formula (4b) wherein R ³ may be a C _1-50 (or C _1-20 )-hydrocarbon carbonyl (ie, a carbonyl containing hydrocarbon group) comprises an amino alcohol, an amine thiol , a diamine, or a polyamine, which is fused to form an aromatic diacid or anhydride to form a hydroxy functionalized fused aromatic quinone imine, a thiol functionalized fused aromatic quinone imine, an amine functionalized fused aromatic quinone imine And then reacting the fused aromatic quinone imine with one or more acid functional polyesters, acid functional polyester decylamines, acid functional polyamides, or mixtures thereof, the reaction can be from 50 ° C to 250 ° C , or a temperature of 150 ° C to 200 ° C, as the case may be in the presence of a catalyst. The acid functional polyester, acid functional polyester decylamine, or acid functional polyamine can be derived from one or more hydroxy-C _2-20 -alkyl carboxylic acids, lactones, amino carboxylic acids, Or a mixture thereof, with C _1-50 (or C _1-20 ) - optionally substituted by a hydrocarbon carbonyl, and conveniently at a temperature of from 50 ° C to 250 ° C, or from 150 ° C to 200 ° C, as appropriate Executed in the presence of the medium, as disclosed in U.S. Patent No. 5,760,270.

Examples of the hydroxy-C _{2-20 -alkylene} (carboxylic acid) carboxylic acid include ricinoleic acid, 12-hydroxystearic acid, 6-hydroxycaproic acid, 5-hydroxyvaleric acid, 12-hydroxydodecanoic acid, 5 - Hydroxydodecanoic acid, 5-hydroxydecanoic acid, 4-hydroxydecanoic acid, 10-hydroxyundecanoic acid, lactic acid, glycolic acid, or a mixture thereof.

Examples of lactones include β-propiolactone, γ-butyrolactone, optionally an alkyl-substituted ε-caprolactone, and optionally an alkyl-substituted δ-valerolactone. The alkyl substituent in ε-caprolactone and δ-valerolactone may be a C _1-6 -alkyl group or a C _1-4 -alkyl group, and may be linear or branched. Examples of suitable lactones are ε-caprolactone and 7-methyl-, 2-methyl-, 3-methyl-, 5-methyl-, 6-methyl-, 4-methyl-, 5 Tributyl-, 4,4,6-trimethyl-, and 4,6,6-trimethyl-homolog, or mixtures thereof.

Examples of the aminocarboxylic acid include 11-aminoundecanoic acid, 12-aminododecanoic acid, 6-aminohexanoic acid, 4-aminobutyric acid, β-alanine, glycine, creatinine, Or a mixture thereof.

In a specific embodiment, the polymer of the present invention may be represented by formula (5) (ie, the polymer may be a poly(ester)-co-polyether, a poly(esteramine)-co-poly(ether), or Poly(decylamine)-co-poly(ether)): Wherein each of the variables R ₁ may be, respectively, may be in the Q ring is bonded substituent may be used at any position of a substituent group, and R ₁ respectively, by one or more -H, electron-withdrawing groups (such as -CN, -NO _2, -SO ₂ NR' ₂ , -C(O)R', -SO ₃ M, -C(O)OM, halo (eg -Cl or -Br), -NH ₂ , or -OR'), or electron A releasing group (such as an alkyl group such as -CH ₃ ) means (generally, when R _{1 is} not -H, the number of non-H groups defined by a may be 0 to 2, 0 to 1, 0, or 1); W may be oxygen or >NG; G may be hydrogen or a hydrocarbon group containing 1 to 200, 1 to 100, or 1 to 30 carbon atoms; M may be H, a metal cation, -NR' ₄ ⁺ R' may be -H, optionally substituted alkyl having from 1 to 20, or from 1 to 10 carbon atoms, and the substituent may be hydroxy, halo (typically Cl), or mixtures thereof; R ₂ may be C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C _{6 to} extend a hydrocarbon carbonyl; R ₃ may be C _1-50 (or C _1-20 )- optionally substituted hydrocarbyl, the bond junction terminal oxygen atom of the polymer chain to form an ester terminal group, and may or may not contain the polymerizable group, such as vinyl, or C _1-50 (or C _1-20) - hydrocarbon carbonyl group (i.e. the carbonyl-containing hydrocarbyl) ,its Bonding an oxygen atom of the polymer chain to form a terminal ester group or a terminal urethane group, and may or may not contain a polymerizable group, such as a vinyl group, and the substituent may be a halogen group, an ether group, or an ester group. Or a mixture thereof; R ₄ may be H, methyl, ethyl, phenyl, or a mixture thereof; R ₅ may be a C _1-19 -alkylene group; Y is oxygen or >NG; u may be 1 to 3, 1 to 2, or 1; w may be 1 to 3, 1 to 2, or 1; q may be 1 to 90; and m may be 1 to 90.

The polymer chain of formula (5) may have a number average molecular weight of from 200 to 10,000, from 300 to 5,000, from 500 to 3,000, or from 1,000 to 2,500. In general, the polymer chain of formula (5) may have from 1000 to 2500 The number average molecular weight.

The quinone imine of formula (5) can be prepared by a process comprising the steps of: (i) reacting an amino acid with a fused aromatic diacid or anhydride to form an acid functionalized fused aromatic quinone, and then the acid function The fused aromatic quinone imine is reacted with one or more hydroxy-C _{2-20 -alkylene} (carboxylic acid) carboxylic acids, lactones, aminocarboxylic acids, or mixtures thereof. The reaction of the acid functionalized fusion aromatic quinone with a hydroxy-C _{2-20 -alkylene} carboxylic acid, a lactone, an amino carboxylic acid, or a mixture thereof may be from 50 ° C to 250 ° C, or 150 a temperature of from ° C to 200 ° C, optionally in the presence of a catalyst; and (ii) optionally, in the presence of an esterification catalyst, the product of step (i) is monosubstituted with a polyalkylene glycol C _1-20 - The alk(en)yl ether is reacted.

Alternatively, the polymer of formula (5) can be obtained by reacting (i) a polyalkylene glycol monosubstituted C _{1-20 -alkylene} at a temperature of from 50 ° C to 250 ° C, or from 150 ° C to 200 ° C ( Alkyl ethers are reacted with one or more hydroxy-C _{2-20 -alkylene} carboxylic acids, lactones, aminocarboxylic acids, or mixtures thereof to form hydroxyl and/or amine terminated polymers And (ii) reacting the product of step (i) with an acid functionalized fusion aromatic quinone at a temperature of from 50 ° C to 250 ° C, or from 150 ° C to 200 ° C, optionally in the presence of a catalyst.

In a specific embodiment, the polymer chain (Pol) is based on a poly(ether)-co-poly(ester). The poly(ether)-co-poly(ester) can be based on a polyalkylene glycol (generally poly C ₂ -C ₄ -alkylene glycol) with a lactone, a hydroxy-C _{2-20 -alkylene} (alkene) a carboxylic acid, or a mixture thereof.

In a specific embodiment, the polymer of the present invention can be represented by formula (6a) (ie, the polymer can be poly(ether)-co-poly(ester), poly(ether)-co-poly(esteramine) Or poly(ether)-co-poly(decylamine)): Wherein each of the variables R ₁ may be, respectively, may be in the Q ring is bonded substituent may be used at any position of a substituent group, and R ₁ respectively, by one or more -H, electron-withdrawing groups (such as -CN, -NO _{2, -SO 2 NR '2, -C (} O) R', - SO 3 M, -C (O) OM, halo (e.g., -Cl or -Br), - NH _2, or -OR '), or an electronic A releasing group (such as an alkyl group such as -CH ₃ ) means (generally, when R _{1 is} not -H, the number of non-H groups defined by a may be 0 to 2, 0 to 1, 0, or 1); W may be sulfur, >NG, or oxygen (generally oxygen or >NG); M may be H, metal cation, -NR' ₄ ⁺ ; R' may be -H, generally containing 1 to 20, Or an alkyl group optionally substituted with 1 to 10 carbon atoms, and the substituent may be a hydroxyl group, a halogen group (generally Cl), or a mixture thereof; and R ₂ may be C ₁ to C ₂₀ , C ₁ to C ₁₂ Or a C ₁ to C ₆ alkyl group, or a C ₁ to C ₂₀ , a C ₁ to C ₁₂ , or a C ₁ to C ₆ hydrocarbon carbonyl group, or a mixture thereof; G may be hydrogen or contain 1 to 200, 1 to a hydrocarbon group of 100 or 1 to 30 carbon atoms; R ₃ may be H or a C _1-50 (or C _1-20 )-hydrocarbon carbonyl group (i.e., a hydrocarbon group containing a carbonyl group) which bonds an oxygen atom of a polymer chain Forming a terminal ester group or a terminal urethane group, which may or may not contain a polymerizable group, such as a vinyl group, and the substituent may be a halogen group, an ether group, an ester group, or a mixture thereof; R ₄ may be H, a methyl group, Ethyl, phenyl, or a mixture thereof; R ₅ may be a C _1-19 -hydrocarbyl group; Y is oxygen or >NG; u may be 1 to 3, 1 to 2, or 1; w may be 1 to 3, 1 to 2, or 1; q may be 1 to 90, and m may be 1 to 90.

In a specific embodiment, the polymer of the present invention may be represented by formula (6b) (ie, the polymer may be poly(ether)-co-poly(ester), poly(ether)-co-poly(esteramine) Or poly(ether)-co-poly(decylamine)): Wherein W is N (formed when R ₂ of formula (1) is derived from a diamine or polyamine); R ₂ is a C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C ₆ alkyl; Is 2; and all other variables therein are as defined above.

The polymer chain of formula (6a) or (6b) may have a number average molecular weight of from 200 to 10,000, from 300 to 5,000, from 500 to 3,000, or from 600 to 2,500. The polymer chain of the general formula (6a) or (6b) may have a number average molecular weight of from 1,000 to 2,500.

The process for preparing the formula (6a) comprises the imine of the formula (3a) wherein R ₃ is -H with one or more hydroxy-C _{2-20 -alkylene} carboxylic acids, lactones, amines The carboxylic acid, or a mixture thereof, is reacted. The reaction of the quinone imine of the formula (3a) wherein R ₃ is -H with a hydroxy-C _{2-20 -alkylene} carboxylic acid, a lactone, an aminocarboxylic acid, or a mixture thereof can be carried out at 50 ° C to The temperature of 250 ° C, or 150 ° C to 200 ° C, as the case may be in the presence of a catalyst.

The process for preparing the formula (6b) comprises the imine of the formula (3b) wherein R ₃ is -H with one or more hydroxy-C _{2-20 -alkylene} carboxylic acids, lactones, amines The carboxylic acid, or a mixture thereof, is reacted. The reaction of the quinone imine of the formula (3b) wherein R ₃ is -H with a hydroxy-C _{2-20 -alkylene} carboxylic acid, a lactone, an aminocarboxylic acid, or a mixture thereof can be carried out at 50 ° C to The temperature of 250 ° C, or 150 ° C to 200 ° C, as the case may be in the presence of a catalyst.

In a specific embodiment, the quinone imine represented by the formula (6a) or (6b) wherein R ₃ is a C _1-50 (or C _1-20 )-hydrocarbon carbonyl group (ie, a hydrocarbon group having a carbonyl group) may be borrowed. It is prepared by reacting a quinone imine of (6a) or (6b) wherein R ₃ is -H, respectively, with a carboxylic acid, an acid derivative such as an acid halide, an isocyanate, or a mixture thereof. The reaction conditions for capping the polymer chain with an acid, acid derivative or isocyanate to form the polymer of the present invention are those known in the art.

Alternatively, the quinone imine of the formula (6a) or (6b) wherein R ₃ may be a C _1-50 (or C _1-20 )-hydrocarbon carbonyl group (ie, a hydrocarbon group containing a carbonyl group) may be wherein R ₃ is - The ruthenium of formula (3a) or (3b) of H is prepared by reacting one or more acid-functional polyesters, acid-functionalized polyester guanamines, acid-functionalized polyamines, or mixtures thereof, respectively. It can be carried out at a temperature of from 50 ° C to 250 ° C or from 150 ° C to 200 ° C, optionally in the presence of a catalyst. The acid functional polyester, acid functional polyester decylamine, or acid functional polyamine can be derived from one or more hydroxy-C _2-20 -alkyl carboxylic acids, lactones, amino carboxylic acids, Or a mixture thereof, with C _1-50 (or C _1-20 ) - optionally substituted by a hydrocarbon carbonyl, and conveniently at a temperature of from 50 ° C to 250 ° C, or from 150 ° C to 200 ° C, as appropriate Executed in the presence of the medium, as disclosed in U.S. Patent No. 5,760,270.

In a specific embodiment, the polymer chain (Pol) is based on poly(alkylene). In a specific embodiment, the poly(alkylene) polymer chain can be incorporated into the quinone imine structure represented by formula (7): Each of the variables in formula (7) may be that R ₁ may be a substituent at any position in the Q ring which may be used to bond a substituent, and R _{1 is} each one or more of -H, an electron-withdrawing group (eg, -CN, -NO ₂ , -SO ₂ NR' ₂ , -C(O)R', -SO ₃ M, -C(O)OM, halo (eg -Cl or -Br), -NH ₂ , or -OR' Or, an electron-releasing group (such as an alkyl group such as -CH ₃ ) means (generally, when R _{1 is} not -H, the number of non-H groups defined by a may be 0 to 2, 0 to 1 , 0, or 1); W can be sulfur, nitrogen, >NH, >NG, or oxygen (generally oxygen, nitrogen or >NG); M can be H, metal cation, -NR' ₄ ⁺ , or a mixture thereof R' may be -H, optionally substituted alkyl having from 1 to 20, or from 1 to 10 carbon atoms, and the substituent may be hydroxy, halo (typically Cl), or mixtures thereof; R ₂ may be C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C ₆ alkyl, or C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C ₆ hydrocarbon carbonyl, or a mixture; G may be hydrogen or a hydrocarbon group having 1 to 200, 1 to 100, or 1 to 30 carbon atoms; R ₃ is H; u is 1; w is 1 to 3; and when W is >NG Pol is a polyisobutylene chain, or when W is N Pol forms a quinone imine attached to the polyisobutylene succinic anhydride of W, and forms a guanamine or ester when W is >NG or oxygen, respectively.

The polymer chain (Pol) of the formula (7) may have a number of 200 to 10,000, 300 to 5,000, 500 to 3,000, or 600 to 2,500. The average molecular weight. In general, the polymer chain (Pol) of formula (7) may have a number average molecular weight of from 1000 to 2500.

In a specific embodiment, the quinone imine represented by the formula (7) may be prepared by a method comprising the steps of: (i) reacting an amino acid with a fusion aromatic diacid or an anhydride to form an acid functionalized fusion aromatic The quinone imine, and (ii) the acid functionalized fusion aromatic quinone imine is then reacted with polyisobutylamine (available from an olefin polymer and an amine) or mixtures thereof.

The first step of the reaction (formation of the quinone imine) can be carried out at a sufficiently high temperature known in the art to facilitate the formation of quinone imine, for example at least 100 ° C, or 150 ° C to 200 ° C. The reaction of the acid functionalized fusion aromatic quinone imine with polyisobutylamine or a mixture thereof can be carried out at a temperature of from 50 ° C to 250 ° C, or from 150 ° C to 200 ° C, optionally in the presence of a catalyst.

In a specific embodiment, a method of preparing a quinone imine represented by formula (7) wherein W is oxygen may comprise reacting an amino alcohol with a fused aromatic diacid or anhydride to form a hydroxy-functionalized fused aromatic hydrazine. The imine is then reacted with the hydroxy-functionalized aromatic quinone imine as polyisobutylene succinic anhydride (PIBSA). The first step of the reaction (formation of the quinone imine) can be carried out at a sufficiently high temperature known in the art to facilitate the formation of quinone imine, for example at least 100 ° C or 150 ° C to 200 ° C, or at least 100 ° C or 150 ° C. Up to 250 ° C. The second step of the reaction of the quinone imine with PIBSA is carried out at a sufficiently high temperature known to those skilled in the art, for example at least 100 ° C, or 150 ° C to 200 ° C, optionally in the presence of a catalyst.

The method for preparing the formula (7) may further comprise reacting an amine thiol with the above-described method to form a thiol-functionalized fusion aromatic quinone imine, The thiol functionalized fusion aromatic quinone imine is then reacted with PIBSA.

The method of preparing the formula (7) may further comprise reacting the diamine with a fusion aromatic diacid or anhydride to form an amine functionalized fusion aromatic quinone imine, and then functionally fused to the aromatic group using the above method conditions. The quinone imine is reacted with PIBSA to form a polymer of the formula (7) of the present invention in which W is nitrogen or >NG.

The present invention also provides a polymer comprising a polymer chain having at least one fused aromatic quinone imine pendant, wherein the chain can be directly or in combination with one or more polyalkyleneamines by combining the aromatic diacid or anhydride It can be prepared by reacting (from an olefin polymer with an amine). The reaction of the fused aromatic diacid or anhydride with one or more polyalkyleneamines can be carried out at a sufficiently high temperature known in the art to facilitate the formation of quinone imine, for example at least 100 ° C or 150 ° C to 200 ° C, or At least 100 ° C or 150 ° C to 250 ° C. Examples of alkylamino include polyethylene stretched polyethylene commercially available from BASF isobutylamine FD-100 ^TM and Kerocom ^TM Piba03.

One method of preparing a polyalkylene substituted amine involves the reaction of a halogenated olefin polymer with an amine as disclosed in U.S. Patent Nos. 3,275,554, 3,438,757, 3,454,555, 3,565,804, 3,755,433, and 3,822,289.

Another method of preparing a polyalkylene-substituted amine involves the reaction of a hydroformylated olefin with a polyamine, and the hydrogenation of the reaction product, as disclosed in U.S. Patent Nos. 5,567,845 and 5,496,383.

Another method for preparing a polyalkylene substituted amine involves the conversion of a polyene to a corresponding epoxide with or without a catalyst, and the reaction of the amine or amine under reductive amination conditions. It is converted to a polyalkylene substituted amine as disclosed in U.S. Patent No. 5,350,429.

Another method of preparing a polyalkylene substituted amine involves the hydrogenation of a beta-amino nitrile, which is accomplished by the reaction of a nitrile, as disclosed in U.S. Patent No. 5,492,641.

And A process for preparing polyalkene-substituted amines of the method involves the presence of CO and H _2, at a high pressure and high temperature polybutene or polyisobutene in the catalyst (e.g. cobalt or rhodium) A acylated with hydrogen, as described in U.S. Patent No. 4,832,702 The number revealed.

The above preparation of the polyene substituted amines is for illustrative purposes only and is not an exclusive list. The range of the polyene-substituted amine of the present invention is not limited to the production method disclosed above.

In a specific embodiment, the olefin polymer used to make the polyalkyl substituted amines of the present invention is derived from an olefin polymer. The olefin polymer comprises from 2 to 16 carbon atoms, and in one embodiment 2 to 6 carbon atoms, and in one embodiment a homopolymer of a polymerizable olefin monomer of 2 to 4 carbon atoms. Polymers and interpolymers. The interpolymer is one in which two or more olefin monomers are mutually copolymerized in accordance with well-known conventional procedures to form a polyolefin having units derived from each of the two or more olefin monomers in its structure. Accordingly, the term "interpolymer" as used herein includes copolymers, terpolymers, and tetramers. The polyenes from which the polyalkylene substituted amines are derived are often referred to as "polyolefins" and are well known to those skilled in the art.

The olefin monomer from which the olefin polymer is derived includes a polymerizable olefin characterized by having one or more ethylenically unsaturated groups (ie, >C=C<) a hydrocarbon monomer, that is, it is a monoolefin monomer such as ethylene, propylene, 1-butene, isobutylene (2-methyl-1-butene), 1-octene; or a polyolefin monomer such as 1,3 - Butadiene and isoprene.

The olefin monomer is typically a polymeric terminal olefin; that is, an olefin characterized by a >C=CH ₂ group in its structure. However, it is also possible to use a polymerizable internal olefin monomer characterized by having the following groups in its structure: It can be used to form the polyolefin.

Specific examples of the terminal and internal olefin monomer which can be used to prepare the polyolefin according to well-known conventional polymerization techniques include ethylene, propylene, butylene (including 1-butene, 2-butene, and isobutylene), 1-pentene, 1-hexene, 1-heptene, 1-octene, 1-decene, 1-decene, 2-pentene, propylene tetramer, diisobutylene, isobutylene trimer, 1,2-butadiene , 1,3-butadiene, 1,2-pentadiene, 1,3-pentadiene, 1,4-pentadiene, isoprene, 1,5-hexadiene, 2-methyl 5-5-propyl-1-hexene, 3-pentene, 4-octene, and 3,3-dimethyl-1-pentene.

In one embodiment, the olefin polymer is polymerized to a butene content of 35 to 75 weight percent and an isobutylene content of 30 by the presence of a Lewis acid catalyst such as aluminum trichloride or boron trifluoride. Up to 60% by weight of the C ₄ refined stream. These polybutenes are generally predominantly (greater than 80% of all repeating units) containing isobutylene repeating units of the following configuration.

Amines which may be used include ammonia, diamines, polyamines, or mixtures thereof, including mixtures of different diamines, mixtures of different polyamines, and mixtures of diamines and polyamines. The amines include aliphatic, aromatic, heterocyclic, and carbocyclic amines.

The diamines and polyamines wherein at least two of the primary amine (e.g., H ₂ N-) group within its structure. The amine can be aliphatic, cycloaliphatic, aromatic, or heterocyclic.

The amine can also be a polyamine. The polyamine can be aliphatic, cycloaliphatic, heterocyclic, or aromatic. Examples of the polyamine include an alkylene polyamine, a hydroxyl group-containing polyamine, an extended aryl polyamine, and a heterocyclic polyamine.

The alkylene polyamine includes those represented by the following formula: Wherein n is from 1 to 10, in one embodiment from 2 to 7, and in a particular embodiment from 2 to 5, and the "alkylene" has from 1 to 10 carbon atoms, in a particular In the examples, it is 2 to 6 carbon atoms, and in one embodiment 2 to 4 carbon atoms. R ⁵ is independently hydrogen, aliphatic, or a hydroxyl group or an amine substituted aliphatic group of up to 30 carbon atoms. In general, R ⁶ is H or lower alkyl (alkyl of 1 to 5 carbon atoms), most often H. The alkylene polyamine includes ethylene polyamine, butyl polyamine, propylene polyamine, pentylene polyamine, hexamethylene polyamine, and heptane polyamine. Also includes the high carbon homologues of this amine and related amino-substituted alkyl substituted channels. .

The specified alkylene diamines and polyamines which can be used to prepare the polyalkylene substituted amines of the present invention include ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethyleneamine, propylenediamine, and propylene Amine, hexamethylenediamine, stilbene diamine, dioctylamine, di(heptyl)triamine, triexamine, pentaethyleneamine, bis(propylenetriamine), N-(2) -aminoethyl)peri And 1,4-anthracene (2-aminoethyl)per .

The above-mentioned extended polyethylene polyamine is particularly useful for cost and effect. This polyamine is described in detail in "Diamines and Higher Amines", Encyclopedia of Chemical Technology, Second Edition, Kirk and Othmer, Vol. 7, pages 27-39, Interscience Publishers, Division of John Wiley and Sons, 1965. This compound is most conveniently prepared by reacting a chloroalkylene group with ammonia or by reacting ethylene diimide with a ring opening reagent such as ammonia. These reactions result in the manufacture of slightly more complex alkylene polyamine mixtures, including cyclic condensation products such as piperidine. .

Other useful types of polyamine mixtures are those which are often referred to as "polyamine bottoms" as a residue by stripping the above polyamine mixture. Typically, the alkyl polyamine bottom product is characterized by a material having a boiling point below 200 ° C of less than 2%, often less than 1% by weight. A typical example of this B-polyamine bottom product, coded "E-100" from Dow Chemical Company of Freeport, Texas, has a specific gravity of 1.0168 at 15.6 ° C, a weight percent nitrogen of 33.15, and 121 at 40 ° C. The viscosity of centipoise. Gas chromatographic analysis of this sample contained 0.93% "light ends" (most likely DETA), 0.72% TETA, 21.74% tetraethylene pentamine, and 76.61% pentaethylene hexamine and higher Amine (weight ratio). These alkyl polyamine bottom products include cyclic condensation products such as piperidine And high-grade homologues such as diethylenetriamine and triamethylenetetramine.

Hydroxyl-containing polyamines include one or more of nitrogen A hydroxyalkyl-alkylalkylamine of a hydroxyalkyl substituent. The polyamine can be produced by reacting the above alkylene polyamine with one or more alkylene oxides such as ethylene oxide, propylene oxide and butylene oxide. A similar alkylene oxide-alkanolamine reaction product can also be used, such as a first, second or third alkanolamine in the range of 1:1 to 1:2 with ethylene oxide, propylene oxide or higher epoxide. The product produced by the molar reaction. The reaction ratio and temperature at which this reaction is carried out are known to those skilled in the art.

In a particular embodiment, the hydroxyalkyl substituted alkylene polyamine can be one wherein the hydroxyalkyl group is a lower hydroxyalkyl group, i.e., has less than 8 carbon atoms. Examples of the hydroxyalkyl-substituted alkylene polyamine include a monohydroxypropyl-substituted diethylenetriamine, a dihydroxypropyl-substituted tetra-ethylenepentamine, and an N-(3-hydroxybutyl)-butylene. Diamine.

An example of an aryl polyamine includes hydrazine (p-aminophenyl)methane.

The number average molecular weight of the polyene substituted amine may range from 500 to 5,000, from 500 to 3,000, and in a particular embodiment from 1000 to 2,500.

In a specific embodiment, the polymer chain (Pol) is based on poly(alkylene). The poly(alkylene) polymer chain can be based on a hydrocarbyl-substituted deuteration agent, and generally has a number average molecular weight in the range of 300 to 5000, 450 to 4000, 500 to 3000, or 550 to 2500 in many embodiments. Hydrocarbyl group. In many embodiments, the hydrocarbyl group has a number average molecular weight of from about 550, about 750, 950 to 1000, about 1600, or about 2300.

In a particular embodiment, the hydrocarbyl group comprises a polymer. Combined Examples of suitable polymers include polyolefins.

In a particular embodiment, the polymer can be obtained from a combination of at least one olefin or olefin.

In many embodiments, the polymer can be derived from an olefin having from 2 to 8 carbon atoms, or from 3 to 6 carbon atoms. Examples of suitable olefins include propylene, isobutylene, pentene, or hexene. In general, the polymer is derived from isobutylene to form polyisobutylene.

In a particular embodiment, the polymer has a terminal C=C double bond group, i.e., a vinylidene group. In general, the amount of vinylidene present is not critical since the polymer (especially polyisobutylene) can be prepared from BF ₃ or AlCl ₃ .

The vinylidene group is typically present in an amount of at least 2 weight percent, at least 40 weight percent, at least 50 weight percent, at least 60 weight percent, or at least 70 weight percent of the polymer molecule. The vinylidene group is often present in an amount of about 75%, about 80% or about 85% of the molecule.

The polymer is available from the trade name Glissopal® 1000 or Glissopal® 2300 (commercially available from BASF), TPC® 555, TPC® 575 or TPC® 595 (commercially available from Texas Petroleum Chemicals).

The oximation agent of the hydrocarbyl oximation agent can be a compound having one or more acid functional groups such as a carboxylic acid or an anhydride thereof. Examples of the oximation agent include α,β-unsaturated mono- or polycarboxylic acids, anhydride esters or derivatives thereof. Examples of the oximation agent include malonic acid, succinic acid, phthalic acid, glutaric anhydride, succinic anhydride, phthalic anhydride, (meth)acrylic acid, methyl (meth)acrylate, maleic acid or anhydride. , fumaric acid, itaconic acid or anhydride, or mixture.

Industrial Applications

The particulate solid present in the composition may be any inorganic or organic solid material which is substantially insoluble in the organic medium at the relevant temperature and which is desirably stabilized therein in a finely divided form. The particulate solid may be in the form of a particulate material, fiber, platelet, or powder, often a foamed powder. In a specific embodiment, the particulate solid is a pigment.

The particulate solid (typically a pigment or filler) may have a diameter of from 10 nanometers to 10 micrometers, or from 10 nanometers to 1, 2, 3, or 5 micrometers, or 20 nanometers, as measured by light scattering measurements. Average particle size of 1, 2, 3, or 5 microns.

Examples of suitable solids are pigments for solvent inks; pigments, extenders, fillers, foaming agents, and flame retardants for paints and plastic materials; dyes, especially disperse dyes; optical brighteners for solvent baths and Textile adjuvants; pigments for inks, toners and other solvent coating systems; solids for oil and demulsification drilling; dust and solid particles in dry cleaning fluids; metals; ceramics, piezoelectric printing, refractory, Abrasives, castings, capacitors, fuel cells, magnetic fluids, conductive inks, magnetic recording media, water treatment, granular ceramic materials and magnetic materials for hydrocarbon soil rejuvenation; organic and inorganic nano-dispersed solids; battery electrodes Metals, metal oxides and carbons; fibers for composite materials such as wood, paper, glass, steel, carbon, and boron; and biocides, pesticides, and pharmaceuticals coated with dispersions in organic media .

In a specific embodiment, the solid is an organic pigment obtained from any of the recognized classes of pigments, such as the Colour Index (1971) Third Edition and subsequent updates, and its supplements, entitled "Pigments." Examples of organic pigments are obtained from azo, diazo, trisazo, condensed azo, azo lake, naphthol pigment, anthanthrone, anthrapyrimidine, anthracene, benzo. Imidazolone, carbazole, diketopyrrolopyrrole, yellow ketone, indigo pigment, indanthrene, isodibenzanthrone, isoxanthin, isoindolinone, isoporphyrin, iso Purpurin, metal complex pigment, evil , 苝, perinone, pyranthrone, pyrazoloquinazolone, quinophthalone, quinoline yellow, thioindigo, triaryl carbocation pigment, tribenzodioxine (triphendioxazine), xanthene, and indigo series, especially copper indigo and its nuclear halogenated derivatives, as well as acid, alkali and mordant dye lakes. Although carbon black is strictly inorganic, its dispersing properties behave like organic pigments. In a specific embodiment, the organic pigments are indigo, especially copper indigo, monoazo, diazo, indanthrene, indole, quinophthalone, diketone Pyrrolylpyrroles, anthraquinones, and carbon blacks.

Examples of inorganic pigments include metal oxides such as titanium dioxide, rutile titanium dioxide and surface-coated titanium dioxide, titanium oxide of different colors (such as yellow and black), and oxidation of different colors (such as yellow, red, brown, and black). Iron, zinc oxide, zirconia, alumina, oxy metal compounds such as bismuth vanadate, cobalt aluminate, cobalt stannate, cobalt silicate, zinc chromate, and two or more of manganese, nickel, titanium, chromium Mixed metal oxides of ruthenium, magnesium, cobalt, iron, or aluminum, mozzarella blue, vermilion, ultramarine blue, zinc phosphate, zinc sulfide, calcium and zinc molybdate and chromate, metallic effect pigments such as aluminum flakes, Copper and copper/zinc alloy, pearlescent flakes, such as Lead carbonate and bismuth oxychloride.

Inorganic solids include extenders and fillers, such as ground and precipitated calcium carbonate, calcium sulfate, calcium oxide, calcium oxalate, calcium phosphate, calcium phosphonate, barium sulfate, barium carbonate, magnesium oxide, magnesium hydroxide, natural hydroxide Magnesium or brucite, precipitated magnesium hydroxide, magnesium carbonate, dolomite, aluminum trihydroxide, alumina or diaspore, calcium citrate and magnesium citrate, aluminosilicate (including nano-clay), kaolin , montmorillonite (including bentonite, hectorite and saponite), ball soil (including natural, synthetic and expansive), mica, talc (including muscovite, phlogopite, lithium mica, and chlorite), white peony, Synthesis and precipitation of vermiculite, fumed vermiculite, metal fibers and powders, zinc, aluminum, glass fibers, refractory fibers, carbon black (including single and multi-walled carbon nanotubes), strengthened and unreinforced carbon black, graphite, Buckminsterfullerene, asphaltene, graphene, diamond, alumina, quartz, perlite, pegmatite, silicone, wood flour, wood chips (including cork and hardwood), sawdust, powdered paper /fiber, cellulose fiber (such as kenaf, hemp, kenaf, linen, Cotton, cotton linters, jute, ramie, rice husk or rough, raffia, cattail, coconut fiber, coir, oil palm fiber, kapok, banana leaf, caro, curaua, Tequila (henequen) leaves, New Zealand flax (harakek) leaves, Manila hemp, sugar cane bagasse, wheat straw, bamboo flakes, flour, MDF, etc.), vermiculite, zeolite, hydrotalcite, fly ash from power plants Incinted sewage sludge ash, volcanic ash, blast furnace slag, asbestos, chrysotile, amphibole, blue asbestos, ash, magnesia, etc.; granular ceramic materials such as alumina, zirconia, titania, oxidation铈, tantalum nitride, aluminum nitride, nitrided, tantalum carbide, boron carbide, mixed tantalum nitride-aluminum, and metal titanate; granular magnetic materials, such as magnetic oxides of transition metals, often iron and Chromium, such as γ-Fe ₂ O ₃ , Fe ₃ O ₄ , iron oxide doped with cobalt, ferrous salts such as barium ferrite; and metal particles such as aluminum, iron, nickel, cobalt, copper, silver , gold, palladium, and platinum, and their alloys.

Other useful solid materials include flame retardants such as pentabromodiphenyl ether, octabromodiphenyl ether, decabromodiphenyl ether, hexabromocyclododecane, ammonium polyphosphate, melamine, melamine cyanuric acid Ester, cerium oxide and barium borate; biocides or industrial microbicides, such as Kirk-Othmer's Encyclopedia of Chemical Technology, Vol. 13, 1981, third edition of the chapter "Industrial Microbial Agents" Tables 2, 3, 4 , 5, 6, 7, 8, and 9, as mentioned, and pesticides such as fungicides flutiafen, carbendazim, chlorothalonil, and zinc-manganese Pu (mancozeb).

The organic medium present in the composition of the present invention is a plastic material in one embodiment, and an organic liquid in another embodiment. The organic liquid can be a non-polar or polar organic liquid. The term "polar" with respect to an organic liquid means an organic liquid which can form a medium to strong bond, as described in Crowley et al., Journal of Paint Technology, Vol. 38, 1966, p. 269, entitled "A Three Dimensional Approach to Solubility". This organic liquid typically has a hydrogen bond number of 5 or more, as defined in the above article.

Examples of suitable polar organic liquids are amines, ethers (especially lower alkyl ethers), organic acids, esters, ketones, glycols, glycol ethers, glycol esters, alcohols, And guanamines. A number of designated examples of this medium-strong hydrogen-bonded liquid are shown in the book by Ibert Mellan, entitled "Compatibility and Solubility" (published by Noyes Development Corporation in 1968), Tables 2.14 on pages 39-40, and these liquids all fall within the scope of the term polar organic liquid as used herein.

In a particular embodiment, the polar organic liquid is a dialkyl ketone, an alkyl ester of a paraffinic carboxylic acid and an alkanol, especially wherein the liquid contains up to and includes a total of 6 carbon atoms. Examples of the polar organic liquid include dialkyl and cycloalkyl ketones such as acetone, methyl ethyl ketone, diethyl ketone, diisopropyl ketone, methyl isobutyl ketone, diisobutyl 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 , methoxypropyl acetate, and ethyl butyrate; glycols and glycol esters, such as ethylene glycol, 2-ethoxyethanol, 3-methoxypropylpropanol, 3-ethoxyl Propyl propanol, 2-butoxyethyl acetate, 3-methoxypropyl acetate, 3-ethoxypropyl acetate, 2-ethoxyethyl acetate; alkanols such as methanol, ethanol , n-propanol, isopropanol, n-butanol, and isobutanol (also known as 2-methylpropanol), terpineol and dialkyl and cycloalkyl ethers, such as diethyl ether and tetrahydrofuran . In a specific embodiment, the solvent is an ester of an alkanol, a paraffinic carboxylic acid, and a paraffinic carboxylic acid. In a particular embodiment, the invention is suitable for organic liquids that are substantially insoluble in aqueous media. Furthermore, it will be understood by those skilled in the art that small amounts of aqueous media (eg, glycols, glycol ethers, glycol esters, and alcohols) may be present in the organic liquid, provided that all of the organic liquid is substantially insoluble in the organic liquid. In aqueous media.

Examples of organic liquids which can be used as polar organic liquids are film forming resins, such as those suitable for use in the preparation of inks, paints, and for use in various applications such as inks and paints. Examples of such resins include polyamide-based, such as Versamid ^{TM (TM)} and Wolfamid, and cellulose ethers, such as ethyl cellulose and ethyl hydroxyethyl cellulose, nitrocellulose, and cellulose acetate butyrate Ester resins, including mixtures thereof. Examples of the paint resin include short oil alkyd / melamine - formaldehyde, polyester / melamine - formaldehyde, thermosetting acrylic / melamine - formaldehyde, long oil alkyd, medium oil alkyd, short oil alkyd, polyether polyol, and Dielectric 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 particular embodiment, the polyol comprises an alpha, omega-diol or an alpha, omega-diol ethoxylate.

In a specific embodiment, the non-polar organic liquid is a compound containing an aliphatic group, an aromatic group, or a mixture thereof. The non-polar organic liquid includes non-halogenated aromatic hydrocarbons (such as toluene and xylene), halogenated aromatic hydrocarbons (such as chlorobenzene, dichlorobenzene, chlorotoluene), and non-halogenated aliphatic hydrocarbons (for example, 6 or more). Fully and partially saturated linear and branched aliphatic hydrocarbons of carbon atoms, halogenated aliphatic hydrocarbons (such as dichloromethane, carbon tetrachloride, chloroform, tetrachloroethane), and natural non-polar organic compounds (such as vegetable oils) , sunflower oil, rapeseed oil, linseed oil, terpenes, and glycerides).

In a specific embodiment, the organic liquid comprises at least 0.1 weight percent, or 1 weight percent or more, of a polar organic liquid, based on total organic liquid. The organic liquid further comprises water as the case may be. In a specific embodiment, the organic liquid is anhydrous.

The plastic material may be a thermosetting resin or a thermoplastic resin. The thermosetting resin which can be used in the present invention includes a resin which undergoes a chemical reaction when heated, catalyzed, or subjected to ultraviolet rays, laser light, infrared rays, cationic, electron beam, or microwave radiation and becomes quite refractory. Typical reactions for thermosetting resins include oxidation of unsaturated double bonds, reactions involving epoxy groups/amines, epoxy/carbonyl groups, epoxy groups/hydroxy groups, reaction of epoxy groups with Lewis acid or Lewis base, and polyisocyanates. /Hydroxyl group, amine resin / hydroxyl moiety, free radical reaction of polyacrylate, cationic polymerization of epoxy resin and vinyl ether, and condensation of sterol. Examples of the unsaturated resin include polyester resins produced by the reaction of one or more diacids or anhydrides with one or more diols. This resin is usually supplied as a mixture having a reactive monomer such as styrene or styrene, and is often referred to as a phthalic acid type resin and an isophthalic acid type resin. Further examples include resins in which dicyclopentadiene (DCPD) is used as a co-reactant in the polyester chain. Further examples also include the reaction product of bisphenol A diglycidyl ether with an unsaturated carboxylic acid such as methacrylic acid, which in turn is supplied as a solution in styrene, often referred to as a vinyl ester resin.

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

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

In a specific embodiment, the thermoplastic resin includes polyolefin, polyester, polyamide, polycarbonate, polyurethane, polystyrene, poly(meth)acrylate, cellulose, and cellulose. derivative. The composition can be prepared in a number of ways, but melt blending and dry solid blending are typical methods. Examples of suitable thermoplastics include (low density, linear low density or high density) polyethylene, polypropylene, polystyrene, polyethylene terephthalate (PET), polybutylene terephthalate ( PBT), nylon 6, nylon 6/6, nylon 4/6, nylon 6/12, nylon 11, nylon 12, polymethyl methacrylate, polyether oxime, polyfluorene, polycarbonate , polyvinyl chloride (PVC), thermoplastic polyurethane, ethylene vinyl acetate (EVA), Victrex PEEK ^TM polymer (such as oxy-1,4-phenoxy-1,4-phenylene) a carbonyl-1,4-phenylene polymer), an acrylonitrile butadiene styrene polymer (ABS); and various other polymer blends or combinations.

If necessary, the composition of the present invention may contain other components such as a resin (which does not constitute an organic medium), a binder, a cosolvent, a crosslinking agent, a fluidizing agent, a wetting agent, an anti-settling agent, a plasticizer. , surfactant, dispersant other than the compound of the invention, moisturizer, antifoaming agent, anti-cracking agent, rheology regulator, thermal stabilizer, light stabilizer, UV absorption Receptors, antioxidants, leveling agents, gloss modifiers, biocides, and preservatives.

If necessary, the composition containing the plastic material may contain other components, such as a dispersant other than the compound of the present invention, an antifogging agent, a nucleating agent, a foaming agent, a flame retardant, a process aid, and a surfactant. , plasticizers, heat stabilizers, UV absorbers, antioxidants, perfumes, mold release auxiliaries, antistatic agents, microbicides, biocides, coupling agents, lubricants (external and internal), impact modifiers, Slip agents, air release agents, and viscosity inhibitors.

The composition typically contains from 1 to 95 weight percent of particulate solids, depending on the nature of the solid and the relative density of the solid and polar organic liquid. For example, based on the total weight of the composition, the solid is a composition of an organic material (such as an organic pigment) containing 15 to 60% by weight of solids in a specific embodiment, and the solid in the composition is an inorganic material (such as inorganic The pigment, filler or extender), in one embodiment, contains from 40 to 90 weight percent solids.

The composition containing an organic liquid can be prepared by any conventional method known for preparing a dispersion. Therefore, the solid, organic medium and dispersant can be mixed in any order, and then the mixture is mechanically treated to reduce the solid particles to a suitable size, for example, by high-speed mixing, ball milling, basket milling, bead milling, stone grinding, sanding, machine Grinding, two-roll or three-roll grinding, plastic grinding until a dispersion is formed. Alternatively, the solid may be treated separately or mixed with an organic medium or a dispersing agent to reduce its particle size, and then the other ingredients are added and the mixture is agitated to provide a composition. The composition can also be ground or dried by grinding or grinding the dried solids and dispersing agent. It is produced by adding a liquid medium or mixing the solid with a dispersing agent in a liquid medium.

The composition containing the plastic material can be prepared by any conventional method known for preparing a thermoplastic compound. Thus, the solid, thermoplastic polymer and dispersant can be mixed in any order, and then the mixture is mechanically treated to reduce the solid particles to a suitable size, such as Banbury blending, ribbon blending, double helix extrusion , two-roll grinding, compounding in a Buss co-kneader or similar equipment.

The composition of the present invention is particularly suitable for liquid dispersions. In a specific embodiment, the dispersion composition comprises: (a) 0.5 to 80 parts of the particulate solid; (b) 0.1 to 79.6 parts of the polymer of the formula (1); and (c) 19.9 to 99.4 parts. The organic liquid and/or water; wherein all of the relative parts are by weight, and the amount (a) + (b) + (c) = 100.

In a specific embodiment, component a) comprises from 0.5 to 30 parts of pigment, and the dispersion can be used as (liquid) ink, paint and abrasive.

If a composition comprising a particulate solid and a dry form of a dispersant of formula (1) is desired, the organic liquid is generally volatile and can be easily removed from the particulate solid by simple means of separation such as evaporation. In a specific embodiment, the composition comprises an organic liquid.

If the dry composition consists essentially of a dispersant of formula (1) and a particulate solid, it generally contains at least 0.2%, at least 0.5%, or at least 1.0% by weight of the particulate solid (1) ) a dispersant. In a specific embodiment, the dry composition contains the weight of the granular solid The dispersant of the formula (1) is not more than 100, not more than 50, not more than 20, or not more than 10% by weight.

As disclosed previously, the compositions of the present invention are suitable for use in the preparation of abrasives wherein the particulate solid is ground in an organic liquid in the presence of a compound of formula (1).

Accordingly, still a further aspect of the present invention provides an abrasive comprising a particulate solid, an organic liquid, and a polymer of formula (1).

Generally, the abrasive contains from 20 to 70 weight percent of particulate solids based on the total weight of the abrasive. In a specific embodiment, the particulate solid is no less than 10 or less than 20 weight percent of the abrasive. The abrasive may optionally contain a binder which is added before or after grinding.

In one embodiment, the binder is a polymeric material that bonds the composition as the organic liquid evaporates.

Adhesives are polymeric materials including natural and synthetic materials. In a specific embodiment, the binder comprises poly(meth)acrylate, polystyrene, polyester, polyurethane, alkyd, polysaccharide (such as cellulose, nitrocellulose), and natural Protein (such as casein). The binder can be nitrocellulose. In a specific embodiment, the binder is present in the composition in an amount of more than 100%, more than 200%, more than 300%, or more than 400% by weight of the particulate solid.

The amount of binder selected for use in the abrasive can vary over a wide range of limits, but is generally not less than 10 of the continuous/liquid phase of the abrasive, and often no less than 20 weight percent. In one embodiment, the amount of binder is no greater than 50, or no greater than 40 weight percent of the continuous/liquid phase of the abrasive.

The amount of dispersant in the abrasive depends on the amount of particulate solids, but is generally from 0.5 to 5 weight percent of the abrasive.

The dispersions and abrasives produced from the compositions of the present invention are particularly suitable for use in non-aqueous and solvent-free formulations in which energy curable systems (ultraviolet light, laser light, infrared light, cationic, electron beam, microwave) are used, and The formulation contains monomers, oligomers, and the like, or a combination thereof. It is particularly suitable for use in coatings such as paints, varnishes, inks, other coating materials, and plastics. Suitable examples include low-, medium-, and high-solid paints, general industrial paints, including baking varnishes, two-component and metal-coated paints, such as coil and can coatings, powder coatings, UV-curable coatings, wood varnishes; Ink, such as flexographic, gravure, lithographic, lithography, letterpress or letterpress, screen printing, and printing inks for packaging printing, non-impact inks, such as inkjet inks, including continuous inkjet and controlled droplet inkjet (including thermal, piezoelectric and electrostatic), phase change inks and hot melt wax inks, inks for inkjet printers, and printing varnishes, such as overprint varnishes; polyols and plastisol dispersions; non-aqueous ceramics , in particular, blade forming, gel forming, doctor blade, extrusion and spray molding, further examples are preparation of dry ceramic powder for isostatic pressing; composites such as sheet molding and agglomerated molding compounds, resin transfer molding , pultrusion, hand lamination, and spray lamination, mold molding; construction materials (such as mold resin), cosmetics, personal care (such as nail polish), sunscreen lotion, adhesive, toner (such as liquid tone Agents, plastic materials and electronic materials (such as displays (including organic light-emitting diode (OLED) devices, liquid crystal displays and electrophoretic displays) for color filter systems), glass coatings (including fiber coatings, reflections) Paint or anti-reflective coating), Conductivity and magnetic inks and coatings. It can be used for surface modification of pigments and fillers to improve the dispersion of dry powders for the above applications. Further examples of coating materials are shown in Bodo Muller, Ulrich Poth, Lackformulierung, Lehrbuch fr Ausbildung und Praxis with Lackrezeptur, Vincentz Verlag, Hanover (2003), and Strahlenhartung, Vincentz Verlag, Hanover (1996) by P. G. Garrat. Examples of printing ink formulations are shown in E. W. Flick, Printing Ink and Overprint Varnish Formulations-Recent Developments, Noyes Publications, Park Ridge NJ, (1990), and subsequent editions.

In a particular embodiment, the compositions of the present invention further comprise one or more additional known dispersants.

The following examples provide an illustration of the invention. These examples are non-exclusive and are not intended to limit the scope of the invention.

[Examples]

Comparative Example 1 (CE1) : 1,2,4-benzenetricarboxylic anhydride (17.03 parts) was added to a stirred polyetheramine (constituted by reacting a C _12-15 alcohol with propylene oxide (MW 1800)), followed by The resulting polyether alcohol was added to acrylonitrile as a base catalyzed, followed by hydrogenation to give an amine (activity 85%) (200 parts). IR is consistent with quinone imine formation and the final product has an acid number of 26.97 mg KOH/g. This product is similar to the dispersant prepared in accordance with PREP2 of International Publication WO 2008/028954.

Comparative Example 2 (CE2) : 1,8-Naphthalic anhydride (14.46 parts) was added to a stirred polyetheramine (150 parts of Surfonamine L207 from Huntsman). The reaction was stirred at 100 ° C for 8 hours under nitrogen and then at 150 ° C for 12 hours. IR is consistent with quinone imine formation and the final product has an acid number of 5.46 mg KOH/g. This product is similar to the dispersant prepared in accordance with the disclosure of U.S. Patent No. 6,440,207.

Example 1: 3-Nitro-1,8-naphthalic anhydride (2.91 parts) was added to a stirred polyetheramine (27.09 parts, Surfonamine B200 from Huntsman). The reaction was stirred at 170 ° C for 5 hours under nitrogen. IR is consistent with quinone imine formation and the final product has an acid number of 1.19 mg KOH/g.

Example 2: 4-Nitro-1,8-naphthalic anhydride (4.82 parts) was added to a stirred polyetheramine (44.80 parts, Surfonamine B200 from Huntsman). The reaction was stirred at 170 ° C for 5 hours under nitrogen. IR is consistent with quinone imine formation and the final product has an acid number of 0.75 mg KOH/g.

Example 3: 4-Chloro-1,8-naphthalic anhydride (4.17 parts) was added to a stirred polyetheramine (35.83 parts, Surfonamine B200 from Huntsman). The reaction was stirred at 170 ° C for 25 hours under nitrogen. IR is consistent with quinone imine formation and the final product has an acid number of 1.24 mg KOH/g.

Example 4: 1,8-naphthalic anhydride (17.75 parts) was added to a stirred polyetheramine (constituted by reacting a C _12-15 alcohol with propylene oxide (MW 1800)), followed by formation of a polyether alcohol It was added to acrylonitrile by base catalysis, followed by hydrogenation to give an amine (activity 85%) (200 parts). The reaction was stirred at 170 ° C for 5 hours under nitrogen. IR is consistent with quinone imine formation and the final product has an acid number of 4.12 mg KOH/g.

Example 5: 1,2-Naphthalic anhydride (1.98 parts) was added to a stirred polyetheramine (constituted by reacting a C _12-15 alcohol with propylene oxide (MW 1800)), followed by formation of a polyether alcohol It was added to acrylonitrile by base catalysis, followed by hydrogenation to give an amine (activity 85%) (23.0 parts). The reaction was stirred at 100 ° C for 1 hour under nitrogen and then at 175 ° C for 2 hours. IR is consistent with quinone imine formation and the final product acid number is 2.10 mg KOH/g.

Dispersion Test 1

A dispersion was prepared by dissolving Examples 1-5 and CE1 and CE2 (0.5 parts) in ethanol/ethyl acetate (6.0 parts, 5:1 w/w). Then add nitrocellulose resin (1.0 parts, NC-DLX 3/5 (from Nobel NC), 20% solids in 5:1 ethanol/ethyl acetate), followed by 3 mm glass beads (25 parts) ) with black pigment (Printex® 35 from Degussa, 2.5 parts). The contents were ground for 16 hours with a horizontal shaker. The dispersion was coated on a black and white card, and after evaporation of the solvent, the gloss was measured using a Novogloss meter from Rhopoint instruments. In general, for example, a higher 60° gloss rating results in better results. The results obtained for each dispersion are:

Intermediate A : 2-(2-Aminoethoxy)ethanol (15.92 parts) was added to 1,8-naphthalic anhydride (30.00 parts), and stirred at 160 ° C for 9 hours under nitrogen. IR is consistent with quinone imine formation and the final product acid number is 4.83 mg KOH/g.

Intermediate B : 2-(2-Aminoethoxy)ethanol (30.27 parts) was added to 3-nitro-1,8-naphthalic anhydride (70.00 parts) and stirred at 180 ° C for 6 hours under nitrogen. . IR is consistent with quinone imine formation and the final product acid number is 2.07 mg KOH/g.

Intermediate C: Ethylene oxide (122.72 parts) was added to Intermediate A (99.35 parts) and potassium hydroxide (1.0 parts), and stirred at 155 ° C for 4 hours under nitrogen. The resulting product was a brown liquid and had a molecular weight of Mn = 414 and Mw = 519 as determined by GPC (THF solvent, PEG standard).

Intermediate D: Ethylene glycol (20 parts) was dissolved in water (80 parts) and a suspension of 1,8-naphthalic anhydride (10 parts) in water (60 parts) was added over 20 minutes. The mixture was heated at 70 ° C for 45 minutes and then filtered to remove impurities. The resulting solution was cooled to 5 ° C and the product precipitated as a yellow solid, and IR was consistent with the s.

Intermediate E: 1,8-naphthalic anhydride (10 parts) was added to the sulfuric acid at 0 ° C for 25 minutes (30 parts of 30% free SO ₃ and 30 parts of 20% free SO ₃ ). The mixture was heated at 95 ° C for 1 hour and then poured onto ice water (70 parts). The resulting precipitate was filtered and washed with glacial acetic acid (40 parts), hexane (40 parts), and hydrochloric acid (40 parts), and then dried. The resulting product contained 10.3% sulfur and the NMR was consistent with sulfonation.

Intermediate F: The same procedure and amount as listed in Preparation 2 of U.S. Patent No. 6,403,797, except that naphthalic anhydride is 3- Nitrophthalic anhydride (30.6 parts) was substituted. It gave a beige solid (35.4 parts) and NMR to the desired product, and the final product acid value was 18.9 mg KOH/g.

Example 6: 3-Nitro-1,8-naphthalic anhydride (21.56 parts) was added to a stirred polyetheramine (constituted by reacting a C _12-15 alcohol with propylene oxide (MW 1800)), followed by The resulting polyether alcohol was added to acrylonitrile as a base catalyzed, followed by hydrogenation to give an amine (activity 85%) (200 parts). The reaction was stirred at 160 ° C for 4 hours under nitrogen. IR is consistent with quinone imine formation and the final product acid number is 4.93 mg KOH/g.

Example 7: 1,8-Naphthalic anhydride (18.22 parts) was added to a stirred polyetheramine (46.02 parts, Surfonamine B200 from Huntsman). The reaction was stirred at 175 ° C for 4 hours under nitrogen. IR is consistent with quinone imine formation and the final product acid number is 4.47 mg KOH/g.

Example 8: 1,2-Naphthalic anhydride (3.98 parts) was added to a stirred polyetheramine (46.02 parts, Surfonamine B200 from Huntsman). The reaction was stirred at 100 ° C for 1 hour under nitrogen and then heated at 175 ° C for 5 hours under nitrogen. IR is consistent with quinone imine formation and the final product acid number is 4.31 mg KOH/g.

Example 9: 2,3-Naphthalic anhydride (7.96 parts) was added to a stirred polyetheramine (92.05 parts, available from Huntsman's Surfonamine B200). The reaction was stirred at 100 ° C for 1 hour under nitrogen and then heated at 175 ° C for 5 hours under nitrogen. IR is consistent with quinone imine formation and the final product acid number is 1.39 mg KOH/g.

Example 10: Propylene oxide (214.54 parts) was added to Intermediate C (98.15 parts) and potassium hydroxide (0.7 parts), and under nitrogen Stir at 155 ° C for 24 hours. The resulting product was a brown liquid and had a molecular weight of Mn = 1390 and Mw = 1956 as determined by gel permeation chromatography (GPC) (tetrahydrofuran (THF) solvent, polyethylene glycol (PEG) standard).

Example 11: 3-Nitro-1,8-naphthalic anhydride (38.69 parts) was added to a stirred polyetheramine (161.32 parts, Surfonamine B100 from Huntsman). The reaction was stirred at 100 ° C for 1 hour under nitrogen and then heated at 175 ° C for 2 hours under nitrogen. IR is consistent with quinone imine formation and the final product acid number is less than 1.0 mg KOH/g.

Example 12: 3-Nitro-1,8-naphthalic anhydride (26.74 parts) was added to a stirred polyetheramine (73.26 parts, obtained from Surfonamine B60 from Huntsman). The reaction was stirred at 100 ° C for 1 hour under nitrogen and then heated at 175 ° C for 4 hours under nitrogen. IR is consistent with quinone imine formation and the final product acid number is 2.46 mg KOH/g.

Example 13: Triethylamine (1.09 parts) was added to a stirred solution of Intermediate E (2.93 parts) dissolved in acetone (50 parts). The reaction mixture was stirred at room temperature for 30 minutes under nitrogen, then a polyetheramine (reaction of C _12-15 alcohol with propylene oxide (MW 1800) was added, and the resulting polyether alcohol was added to the base catalyzed to Acrylonitrile was then hydrogenated to give the amine (activity 85%) (25.97 parts). The reaction mixture was stirred at 70 ° C for 1 hour to remove acetone by distillation. The mixture was then heated at 100 ° C for 1 hour and at 175 ° C for 5 hours. IR is consistent with quinone imine formation and the final product acid number is 23.9 mg KOH/g.

Example 14: Intermediate A (10.00 parts), ε-caprolactone (31.30 g), and δ-valerolactone (35.70 g) were stirred at 90 ° C under nitrogen, and zirconium oxychloride (IV) (0.23) was added. g) and the mixture is at 180 Heat at °C for 6 hours. The resulting product was a dark brown liquid and had a molecular weight of Mn=1300 and Mw=1800 as determined by GPC (THF solvent, polystyrene standard).

Example 15: Intermediate B (3.28 parts), ε-caprolactone (9.61 parts), and δ-valerolactone (10.96 parts) were stirred at 90 ° C under nitrogen, and zirconium oxychloride (IV) (0.07) was added. And the mixture was heated at 180 ° C for 6 hours. The resulting product was a dark brown liquid and had a molecular weight of Mn=1320 and Mw=1800 as determined by GPC (THF solvent, polystyrene standard).

Example 16: Intermediate A (5.6 parts), ε-caprolactone (84.11 parts) were stirred at 90 ° C under nitrogen, zirconium oxychloride (IV) (0.24 parts) was added and the mixture was heated at 180 ° C for 6 hours. . The resulting product was a dark brown liquid and had a molecular weight of Mn=1800 and Mw=2200, as determined by GPC (THF solvent, polystyrene standard).

Example 17: Intermediate B (2.0 parts), ε-caprolactone (11.72 parts) was stirred at 90 ° C under nitrogen, zirconium oxychloride (IV) (0.04 parts) was added and the mixture was heated at 180 ° C for 6 hours. . The resulting product was a dark brown liquid and had a molecular weight of Mn = 1300 and Mw = 1,700, as determined by GPC (THF solvent, polystyrene standard).

Example 18: Intermediate C (10.86 parts) and ε-caprolactone (20 parts) were stirred at 90 ° C under nitrogen. Normal phosphoric acid (0.1 g) was added and the reaction mixture was heated at 120 °C for 6 hours. The resulting product was a waxy solid and had a molecular weight of Mn=1183 and Mw=1586 as determined by GPC (THF solvent, polycaprolactone standard).

Example 19: Intermediate A (5.02 parts), castor oil Acid (10.49 parts), ε-caprolactone (9.25 parts), and δ-valerolactone (5.98 parts) were stirred at 120 ° C under nitrogen, zirconium oxychloride (IV) (0.08 parts) was added and the mixture was at 180 Heat at °C for 48 hours. The product thus obtained was a waxy solid and had a molecular weight of Mn = 1268 and Mw = 1826, as determined by GPC (THF solvent, polystyrene standard).

Example 20: Intermediate A (4.74 parts), 12-hydroxystearic acid (25.03 parts) were stirred under nitrogen at 120 ° C, zirconium oxychloride (IV) (0.09 parts) was added and the mixture was heated at 180 ° C. hour. The resulting product was a waxy solid and had a molecular weight of Mn=1791 and Mw=2149 as determined by GPC (THF solvent, polystyrene standard).

Example 21: Intermediate A (5.16 parts), 12-hydroxystearic acid (16.32 parts), and ε-caprolactone (6.19 parts) were stirred under nitrogen at 120 ° C, and zirconium oxychloride (IV) was added ( 0.08 parts) and the mixture was heated at 180 ° C for 26 hours. The resulting product was a waxy solid and had a molecular weight of Mn=1429 and Mw=1766 as determined by GPC (THF solvent, polystyrene standard).

Example 22: 1,8-Naphthalic anhydride (18.57 parts) was added to a stirred poly(isobutylene)amine (152.99 parts, Mn = 1100, 65% in mineral oil). The reaction was stirred at 100 ° C for 2 hours under nitrogen and then at 170 ° C for 6 hours. IR is consistent with quinone imine formation and the final product acid number is 0.5 mg KOH/g.

Example 23: 3-Nitro-1,8-naphthalic anhydride (25.99 parts) was added to a stirred poly(isobutylene)amine (174.45 parts, Mn = 1100, 65% in mineral oil). The reaction was stirred at 100 ° C for 2 hours under nitrogen and then at 170 ° C for 13 hours. IR is consistent with quinone imine formation and ultimately The acid value of the product was 0.9 mg KOH/g.

Example 24: Intermediate D (5.0 parts) was added to stirred poly(isobutyl) succinic anhydride (16.61 parts, Mn = 750). The reaction was stirred at 120 ° C for 1 hour under nitrogen and then at 180 ° C for 33 hours. IR is consistent with quinone imine formation and the final product acid number is 6.0 mg KOH/g.

Example 25: Intermediate F (4.0 parts) was added to stirred caprolactone (19.77 parts). The reaction was stirred at 120 ° C under nitrogen, then zirconium oxychloride (80% in 1-butanol) (0.2 parts) was added. The reaction mixture was heated at 180 °C for 8 hours. The final product had an acid number of 32.4 mg KOH/g.

Example 26: 3-Nitrophthalic anhydride (10.0 parts) was added portionwise to a stirred 12-aminododecanoic acid (35.4 parts) at 190 ° C for 1 hour under nitrogen. IR is consistent with the formation of quinone imine. Caprolactone (32.86 parts) was slowly added to the mixture via an addition funnel, and finally methanesulfonic acid (0.2 parts) was added, and then the mixture was stirred at 180 ° C for 16 hours. The final product had an acid number of 31.9 mg KOH/g.

Dispersion Test 2

The Examples 4, 6 and 7 and CEl (0.5 parts) and polyamide resin (0.5 parts, available from Arizona Chemicals of Unirez ^TM 138) was dissolved in isopropanol / butyl acetate (7.0 parts, 7: 3 w / w). 3 mm glass beads (25 parts) and black pigment (Printex® 35 from Degussa, 2.0 parts) were added and the contents were ground for 16 hours with a horizontal shaker. And then the resultant abrasive (0.5 parts) was added to polyamide resin (0.5 parts, available from Arizona Chemicals of Unirez ^TM 138), and with 2-K bar No. painted in black and white card. After evaporation of the solvent, the gloss was measured using a Novogloss meter from Rhopoint instruments. The results are as follows:

Dispersion Test 3

The embodiment Examples 7-12 and CE1 (0.6 parts) and polyurethane resin (1.0 parts, available from DSM Neoresins of Neorez ^TM U-471, is at 2/1 w / w ethanol / ethyl acetate Activity 51%) was dissolved in isopropanol / butyl acetate (7.4 parts, 7:3 w/w). 3 mm glass beads (17 parts) and black pigment (Printex® 35 from Degussa, 1.0 parts) were added and the contents were ground for 16 hours with a horizontal shaker. And then the resultant abrasive fluid (0.5 parts) was added polyurethane resin (1.0 parts, available from DSM Neoresins of Neorez ^TM U-471, 34 active in 2/1 w / w ethanol / ethyl acetate %), and painted on a black and white card with a 3-K rod. After evaporation of the solvent, the gloss was measured using a Novogloss meter from Rhopoint instruments. The results are as follows:

Dispersion Test 4

A dispersion was prepared by dissolving Examples 13-16 (0.6 parts) in a mixture of methoxypropyl acetate (1.6 parts) and butyl acetate (4.8 parts). Then add acrylic resin (2.0 parts, obtained from Lubrizol's Doresco® TA96-6), followed by 3 mm glass beads (17 parts) and black pigment (1.0 parts, FW200 from Degussa), and shake the contents horizontally. The motive was ground for 16 hours. All resulting dispersions are fluids. The dispersion (0.5 parts) was dissolved in an acrylic resin (1.5 parts, available from Lubrizol, Doresco® TA96-6) and painted on a black and white card using a 3-K rod. The degree of stimulating crystallization was determined by visually evaluating the coating.

Dispersion Test 5

Examples 19, 20, 21, 22, and CE1 (1.0 parts, activity 100%) were dissolved in a solvent (7.0 parts) to prepare a dispersion, and then 3 mm glass beads (17 parts) and red pigment (2.0 parts, From Crobaphtal® red A2B) from Ciba, and the contents were ground for 16 hours with a horizontal shaker. The viscosity is evaluated by measuring the degree of freedom in which the glass beads move completely through the abrasive. In all cases except CE1, the pigment was wetted and formed a uniform dispersion. The results from the dispersion test 5 are:

Overall, the results presented above show that the polymers of the present invention at least improve color strength, increase particulate solid loading, form improved dispersions, improve brightness, and fabricate compositions having reduced viscosity in organic media.

In the context of the present invention, the term "hydrocarbyl" or "hydrocarbyl" means a radical in which the carbon atom directly attaches to the remainder of the molecule and which has a hydrocarbon or predominantly hydrocarbon character. This group includes the following: (1) a pure hydrocarbon group; that is, an aliphatic group (for example, an alkyl group or an alkenyl group), an alicyclic group (for example, a cycloalkyl group or a cycloalkenyl group), an aromatic group, an aliphatic group and an alicyclic group, and an aromatic group. An aromatic substituted aliphatic group and an alicyclic group, etc., and a cyclic group in which the ring is completely passed through other parts of the molecule (i.e., any two of the substituents shown may together form an alicyclic group). This base is known to those skilled in the art. Examples include methyl, ethyl, octyl, decyl, octadecyl, cyclohexyl, phenyl, and the like. (2) a substituted hydrocarbyl group; that is, a group containing a non-hydrocarbon substituent which does not change the characteristics of the main hydrocarbon. Suitable substituents will be understood by those skilled in the art. real Examples include a hydroxyl group, a nitro group, a cyano group, an alkoxy group, a decyl group and the like. (3) a hetero group; that is, although the main feature is a hydrocarbon, a chain or ring composed of carbon atoms contains a group of atoms other than carbon. Suitable heteroatoms are well known to those skilled in the art and include, for example, nitrogen, oxygen and sulfur.

As described below, the number average molecular weight of the polymer of the present invention is determined by a known method, such as GPC analysis, which uses a polystyrene standard for all polymer chains other than ethylene oxide. The number average molecular weight of the polymer chain containing ethylene oxide was determined using GPC (THF solvent, PEG standard).

Each of the above documents is incorporated herein by reference. Except in the examples or clearly indicated, it should be understood that the quantities of all specified materials, reaction conditions, molecular weights, number of carbon atoms, and the like in the description are modified by the word "about". Unless otherwise indicated, each chemical or composition indicated herein should be interpreted as a commercial grade material which may contain isomers, by-products, derivatives, and other such materials normally found in the commercial class. However, the amounts of each chemical component are excluded from any solvents or diluent oils customarily present in commercial grade materials, unless otherwise indicated. It should be understood that the above-described limits, amounts, and ratios can be independently combined. Similarly, the scope and amount of each element of the invention can be used with the scope or amount of any other element.

The term "hydrocarbyl" as used herein is used in the ordinary sense of the term and is intended to include any divalent radical formed by the removal of two hydrogen atoms from a hydrocarbon.

The term "alkylene" as used herein is used in the ordinary sense of the term and is intended to include any alkyl and/or alkenyl group.

While the invention has been described with respect to the preferred embodiments thereof, it will be understood that Therefore, it is to be understood that the invention disclosed herein is intended to cover such modifications within the scope of the appended claims.

Claims (25)

A polymer comprising a polymer chain having at least one fused aromatic quinone imine pendant, wherein the polymer is represented by formula (1): Wherein each variable is R ₁ is a substituent at any position in the Q ring that can be used to bond a substituent, and R ₁ is represented by one or more -H, a pull electron group, or an electron-releasing group; R' is -H, optionally substituted alkyl having 1 to 20, or 1 to 10 carbon atoms, and the substituent is a hydroxyl group, a halogen group (generally Cl), or a mixture thereof; R ₂ is C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C ₆ alkyl, or C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C ₆ hydrocarbon carbonyl (when R ₂ contains more than 2 carbon atoms When the hydrocarbon or extended hydrocarbon carbonyl is linear or branched), or a mixture thereof; R ₃ is H or C _1-50 (or C _1-20 ) - optionally substituted hydrocarbyl, which bonds the polymer chain a terminal oxygen atom to form a terminal ether group or a terminal ester group, and may or may not contain a polymerizable group such as a vinyl group, or a C _1-50 (or C _1-20 )-hydrocarbon carbonyl group (ie, a hydrocarbon group containing a carbonyl group), It is bonded to the oxygen atom of the polymer chain to form a terminal ester group or a terminal urethane group, and may or may not contain a polymerizable group; and Pol is a homopolymer chain or a copolymer chain, wherein the polymer The chain is selected from the group consisting essentially of poly(ether), a group consisting of poly(ester), poly(esteramine), poly(decylamine), poly(alkylene), or a mixture thereof; u is 1 to 3; v is 1 to 2; w is 1 to 3; v=2 when W is nitrogen; v=1 when W is oxygen, sulfur, >NG; G is hydrogen or a hydrocarbon group having 1 to 200, 1 to 100, or 1 to 30 carbon atoms; And Q is a fused aromatic ring containing 4n+2 π electrons, wherein n=2 or more (generally 2 to 5, 2 to 4, 2 to 3, or 2), and Q to form 5 or 6 醯The imine ring (generally a 6-membered ring) is bonded to the quinone imine group. The polymer of claim 1, which is obtained by the method comprising the steps of: (i) an amino acid, (ii) an amino alcohol, (iii) an amino thiol, or ( Iv) diamines or polyamines, which are fused with aromatic diacids or anhydrides, or other acid-forming derivatives (eg, diesters, diamines, acid chlorides) to form acid-functionalized fusion aromatic quinones a hydroxy functionalized fusion aromatic quinone imine, a thiol functionalized fusion aromatic quinone imine, or an amine functionalized fusion aromatic quinone imine; Step (2): the acid functionalized fusion aromatic quinone imine, hydroxy functionalized fusion aromatic quinone imine, thiol functionalized fusion aromatic quinone imine, or amine functionalized fusion aromatic quinone imine The polymer chain, or the monomer that polymerizes to form the polymer chain, reacts. The polymer of claim 1 or 2, wherein the fused aromatic ring, the fused aromatic diacid or anhydride, or other acid forming derivative is based on naphthalene, anthracene, phenanthrene, or a mixture thereof. The polymer according to claim 1 or 2, wherein the fused aromatic ring, the fused aromatic diacid or anhydride, or other acid forming derivative is based on 1,8-naphthylimine, 1,2- Naphthoquinone imine, or a mixture thereof. The polymer of claim 1 or 2, wherein the Q system is based on a naphthalic anhydride such as 1,8-naphthalic anhydride (when R ₁ = H), 3-nitro-1,8-naphthalene acid (PEI), 4-nitro-1,8-naphthalate (PEI) (when R ₁ = NO ₂ a), the 4-chloro-1,8-naphthalate (PEI) (R ₁ when a =Cl), 3-thiodecyl-1,8-naphthalene dicarboxylate imine (when R ₁ =SO ₃ H), or a mixture thereof. The polymer according to any one of claims 1 to 5, wherein the polymer chain is a poly(ether) represented by the formula (2): Wherein each variable is R ₁ is a substituent at any position in the Q ring that can be used to bond the substituent, and R ₁ is represented by one or more of -H, an electron withdrawing group, or an electron releasing group; W is oxygen R' is -H, optionally substituted alkyl having 1 to 20, or 1 to 10 carbon atoms, and the substituent is a hydroxyl group, a halogen group (generally Cl), or a mixture thereof; R ₂ C ₁ to C _20, C ₁ to C _12, or a C ₁ to C ₆ extends hydrocarbon, or a C ₁ to C _20, C ₁ to C _12, or a C ₁ to C ₆ extending hydrocarbon carbonyl group (when R ₂ contains more than When two carbon atoms, the extended or extended hydrocarbon carbonyl is linear or branched), or a mixture thereof; R ₃ is H or C _1-50 (or C _1-20 ) - optionally substituted hydrocarbyl, which is bonded The terminal oxygen atom of the polymer chain forms a terminal ether group or a terminal ester group, and may or may not contain a polymerizable group such as a vinyl group, or a C _1-50 (or C _1-20 )-hydrocarbon carbonyl group (ie, contains a carbonyl group) a hydrocarbon group which bonds to an oxygen atom of the polymer chain to form a terminal ester group or a terminal urethane group, and which may or may not contain a polymerizable group such as a vinyl group, and the substituent is a halogen group, Ether group, ester group, or a mixture thereof; when Pol At the same ternary polymer, R ₄ is methyl, ethyl or phenyl, and when the copolymer is Pol, R ₄ is H (sufficient to provide an amount of 0 weight percent to ethylene oxide of 60 weight percent of the group), And a mixture of at least one of methyl, ethyl, and phenyl or mixtures thereof; u is 1 to 3, 1 to 2, or 1; w is 1 to 3, 1 to 2, or 1; ₂ is a hydrocarbon group and u is 1 and w is 1; and m is 1 to 110 or 1 to 90. The polymer according to any one of claims 1 to 5, wherein the polymer chain is a poly(ether) polymer chain represented by the formula (3a): Wherein each variable is R ₁ is a substituent at any position in the Q ring that can be used to bond a substituent, and R ₁ is represented by one or more -H, an electron withdrawing group, or an electron releasing group; W is sulfur , oxygen, or >NG (generally oxygen); R' is -H, optionally substituted alkyl having 1 to 20, or 1 to 10 carbon atoms, and the substituent is a hydroxyl group, a halogen group ( Typically C1), or a mixture thereof; R ₂ is C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C ₆ alkyl, or C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C _{6 is a} hydrocarbon carbonyl group (when R ₂ contains more than 2 carbon atoms, the hydrocarbon or carbonyl group is linear or branched), or a mixture thereof; and G is 1 to 200, 1 to 100, or 1 to a hydrocarbon group of 30 carbon atoms; R ₃ is H or C _1-50 (or C _1-20 ) - optionally substituted hydrocarbyl, which bonds to the terminal oxygen atom of the polymer chain to form a terminal ether group or a terminal ester group And may or may not contain a polymerizable group, such as a vinyl group, or a C _1-50 (or C _1-20 )-hydrocarbon carbonyl group (ie, a hydrocarbon group containing a carbonyl group) which is bonded to an oxygen atom of the polymer chain to form Tertiary ester or terminal urethane groups, with or without The combined group, such as a vinyl group, and the substituent is a halo group, an ether group, an ester group, or mixtures thereof; Pol when the same element is a polymer, R ₄ is methyl, ethyl or phenyl, and R ₄ a mixture of H (sufficient to provide 0 to 60 weight percent of ethylene oxide groups), and at least one of methyl, ethyl, and phenyl or mixtures thereof; u is 1 to 3, 1 to 2 Or 1; w is 1 to 3, 1 to 2, or 1; and m is 1 to 110 or 1 to 90. The polymer according to any one of claims 1 to 5, wherein the polymer chain is a poly(ether) polymer chain represented by the formula (3b): Wherein each variable is R ₁ is a substituent in the Q ring which can be used at any position of the bonding substituent, and R _{1 is} represented by one or more electron withdrawing groups; W is nitrogen; R' is -H, generally contains 1 to 20, or 1 to 10 carbon atoms, optionally substituted alkyl, and the substituent is hydroxy, halo (generally Cl), or a mixture thereof; R ₂ is C ₁ to C ₂₀ , C ₁ To a C ₁₂ or C ₁ to C ₆ alkyl group, or a C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C ₆ hydrocarbon carbonyl group (when R ₂ contains more than 2 carbon atoms, the hydrocarbon group) Or a hydrocarbon carbonyl group is linear or branched), or a mixture thereof; R ₃ is H or C _1-50 (or C _1-20 )-hydrocarbon carbonyl (ie, a hydrocarbon group containing a carbonyl group) which bonds oxygen to the polymer chain a terminal to form a terminal ester group or a terminal urethane group, and may or may not contain a polymerizable group, such as a vinyl group, and the substituent is a halogen group, an ether group, an ester group, or a mixture thereof; In the case of a homopolymer, R ₄ is methyl, ethyl or phenyl, and R ₄ is H (enough to provide an amount of from 0 to 60 weight percent of the oxirane group), and methyl, ethyl, At least one of a phenyl group or a mixture thereof Thereof; U 1 to 3, 1 to 2, or 1; W is 1 to 3, 1 to 2, or 1; V 2; and m is 1 to 110 or 1 to 90. The polymer of any one of claims 1 to 8, wherein the polymer chain is a poly(ether) containing propylene oxide, which may or may not contain ethylene oxide, butylene oxide, epoxy Base benzene, or a mixture thereof. The polymer of any one of claims 1 to 9, wherein when the polymer chain is a poly(ether), the poly(ether) comprises: 0 to 60 weight percent of ethylene oxide, and 40 to 100% by weight of propylene oxide, 0 to 50% by weight of ethylene oxide, 50 to 100% by weight of propylene oxide, 0 to 30% by weight of ethylene oxide, and 70 to 100% by weight of epoxy Propane, 0 to 20 weight percent of ethylene oxide, and 80 to 100 weight percent of propylene oxide, or 0 to 15 weight percent of ethylene oxide, and 85 to 100 weight percent of propylene oxide. The polymer of any one of claims 1 to 5, wherein the polymer chain is represented by formula (4a): Wherein each variable is R ₁ is a substituent in the Q ring which can be used at any position of the bonding substituent, and R ₁ is represented by one or more -H, an electron withdrawing group, or an electron releasing group; W is oxygen; R' is -H, optionally substituted alkyl having 1 to 20, or 1 to 10 carbon atoms, and the substituent is hydroxy, halo (generally Cl), or a mixture thereof; R ₂ is C ₁ to C ₂₀ , C ₁ to C ₁₂ , C ₁ to C ₆ extend hydrocarbon carbonyl, or a mixture thereof; R ₃ is H or C _1-50 (or C _1-20 ) - optionally substituted hydrocarbon group, the bond The terminal oxygen atom of the polymer chain is formed to form a terminal ether group or a terminal ester group, and may or may not contain a polymerizable group such as a vinyl group, and the substituent is a halogen group, an ether group, an ester group, or a mixture thereof ; R ₅ is C _1-19 -alkylene; p is 2-120; u is 1 to 3, 1 to 2, or 1; and w is 1 to 3, 1 to 2, or 1. The polymer of any one of claims 1 to 5, wherein the polymer chain is represented by the formula (4b): Wherein each R ₁ is variables are available for the Q ring substituent bonded at any position of the substituent group, and R ₁ lines by one or more -H, an electron withdrawing group, or electron releasing group represented; W is oxygen , sulfur or >NG; G is hydrogen or a hydrocarbon group containing from 1 to 200, from 1 to 100, or from 1 to 30 carbon atoms; R' is -H, generally containing from 1 to 20, or from 1 to 10 carbons The atom is optionally substituted with an alkyl group, and the substituent is a hydroxyl group, a halogen group (generally Cl), or a mixture thereof; and R ₂ is a C ₁ to C ₂₀ , C ₁ to C ₁₂ , C ₁ to C ₆ alkyl group. (when R ₂ contains more than 2 carbon atoms, the hydrocarbon carbonyl group is linear or branched), or a mixture thereof; R ₃ is H or C _1-50 (or C _1-20 )-hydrocarbon carbonyl (ie, contains a carbonyl group) a hydrocarbon group which bonds to the oxygen atom of the polymer chain to form a terminal ester group or a terminal urethane group, and which may or may not contain a polymerizable group such as a vinyl group, and the substituent is a halogen group or an ether group a group, an ester group, or a mixture thereof; R ₅ is a C _1-19 -hydrocarbyl group; u is 1 to 3, 1 to 2, or 1; w is 1 to 3, 1 to 2, or 1; and p is 2 -120. The polymer of any one of claims 1 to 5, wherein the polymer chain is represented by formula (5): Wherein each variable is R ₁ is a substituent at any position in the Q ring that can be used to bond the substituent, and R ₁ is represented by one or more of -H, an electron withdrawing group, or an electron releasing group; W is oxygen Or >NG; G is hydrogen or a hydrocarbon group containing from 1 to 200, from 1 to 100, or from 1 to 30 carbon atoms; R' is -H, generally containing from 1 to 20, or from 1 to 10 carbon atoms Substituting an alkyl group as appropriate, and the substituent is a hydroxyl group, a halogen group (generally Cl), or a mixture thereof; and R ₂ is a C ₁ to C ₂₀ , a C ₁ to C ₁₂ , a C ₁ to C ₆ hydrocarbon carbonyl group ( When R ₂ contains more than 2 carbon atoms, the hydrocarbon carbonyl group is linear or branched), or a mixture thereof; R ₃ is -H or C _1-50 (or C _1-20 ) - optionally substituted hydrocarbyl group, Bonding a terminal oxygen atom of the polymer chain to form a terminal ether group or a terminal ester group, and may or may not contain a polymerizable group such as a vinyl group, or a C _1-50 (or C _1-20 )-hydrocarbon carbonyl group ( That is, a hydrocarbon group containing a carbonyl group, which bonds to an oxygen atom of the polymer chain to form a terminal ester group or a terminal urethane group, and may or may not contain a polymerizable group such as a vinyl group, and the substituent is Halo group, ether group, ester group, or a mixture thereof ; R ₄ is H, methyl, ethyl, phenyl, or mixtures thereof; R ₅ is C _1-19 - extending hydrocarbon group; Y is oxygen or>NG; u is 1 to 3, 1 to 2, or 1; w is 1 to 3, 1 to 2, or 1; q is 1 to 90; and m is 1 to 90. The polymer of any one of claims 1 to 5, wherein the polymer chain is represented by formula (6a): Wherein each variable is R ₁ is a substituent at any position in the Q ring that can be used to bond the substituent, and R ₁ is represented by one or more of -H, an electron withdrawing group, or an electron releasing group; W is oxygen , sulfur, >NG (generally oxygen); R' is -H or optionally substituted alkyl having 1 to 20 or 1 to 10 carbon atoms, and the substituent is a hydroxyl group, a halogen group (generally Is C1), or a mixture thereof; R ₂ is C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C ₆ alkyl, or C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C _{6 a} hydrocarbon carbonyl group (when R ₂ contains more than 2 carbon atoms, the hydrocarbon or carbonyl group is linear or branched), or a mixture thereof; R ₃ is H or C _1-50 (or C _1-20 )- a hydrocarbon carbonyl (ie, a hydrocarbon group containing a carbonyl group) which bonds to an oxygen atom of the polymer chain to form a terminal ester group or a terminal urethane group, and which may or may not contain a polymerizable group such as a vinyl group, and The substituent is halo, ether, ester, or a mixture thereof; R ₄ is H, methyl, ethyl, phenyl, or a mixture thereof; R ₅ is C _{1-19 -alkyl} ; Y is oxygen or >NG; u is 1 to 3, 1 to 2, or 1; w is 1 to 3, 1 to 2, or 1; q is 1 to 9 0; and m is 1 to 90. The polymer according to any one of claims 1 to 5, wherein the polymer chain is a poly(ether)-co-poly(ester) polymer chain represented by the formula (6b): Wherein each variable is R ₁ is a substituent at any position in the Q ring that can be used to bond a substituent, and R _{1 is} represented by one or more electron withdrawing groups or electron releasing groups, respectively; W is nitrogen; v is 2 R' is -H or an optionally substituted alkyl group generally having 1 to 20 or 1 to 10 carbon atoms, and the substituent is a hydroxyl group, a halogen group (generally Cl), or a mixture thereof; R ₂ a C ₁ to C ₂₀ , C ₁ to C ₁₂ , or C ₁ to C ₆ hydrocarbyl group (when R ₂ contains more than 2 carbon atoms, the hydrocarbyl group is linear or branched), or a mixture thereof; R ₃ is H Or a C _1-50 (or C _1-20 )-hydrocarbylcarbonyl group (ie, a hydrocarbyl group containing a carbonyl group) which bonds to the oxygen atom of the polymer chain to form a terminal ester group or a terminal urethane group, and is or Free of polymerizable groups, such as vinyl groups, and the substituents are halo, ether, ester, or mixtures thereof; R ₄ is H, methyl, ethyl, phenyl, or mixtures thereof; R ₅ is C _1-19 - a hydrocarbon group; Y is oxygen or >NG; G is hydrogen or a hydrocarbon group having 1 to 200, 1 to 100, or 1 to 30 carbon atoms; u is 1 to 3, 1 to 2 Or 1; w is 1 to 3, 1 to 2, or 1; q is 1 to 90; and m is 1 to 90. The polymer of claim 1 or 2, wherein the polymer chain is a poly(alkylene) polymer chain represented by formula (7): Wherein each variable is R ₁ is a substituent at any position in the Q ring that can be used to bond a substituent, and R ₁ is represented by one or more -H, an electron withdrawing group, or an electron releasing group; W is sulfur , nitrogen, >NG, or oxygen (generally oxygen, nitrogen or >NG);R' is -H, optionally substituted alkyl having from 1 to 20, or from 1 to 10 carbon atoms, and the substitution is hydroxy, halo (typically Cl), or mixtures thereof; R ₂ is a C ₁ to C _20, C ₁ to C _12, or a C ₁ to C ₆ hydrocarbyl extension, or a C ₁ to C _20, C ₁ to C ₁₂ or C ₁ to C _{6 is a} hydrocarbon carbonyl group (when R ₂ contains more than 2 carbon atoms, the hydrocarbon or carbonyl group is linear or branched), or a mixture thereof; G is hydrogen or contains 1 to 200 a hydrocarbon group of 1 to 100 or 1 to 30 carbon atoms; R ₃ is H; u is 1; w is 1 to 3; and Pol is a polyisobutylene chain when W is >NG, or when W is N Pol forms a quinone imine group by attaching polyisobutylene succinic anhydride of W, and forms a guanamine or ester group when W is >NG or oxygen, respectively. A composition comprising a particulate solid, a non-polar organic medium, and a polymer chain having at least one fused aromatic quinone imine pendant, wherein the polymer is according to any one of claims 1 to 16. The polymer is represented. A composition comprising a particulate solid, a polar organic medium, and a polymer chain having at least one fused aromatic quinone imine pendant, wherein the polymer is according to any one of claims 1 to 16. Polymer representation. The composition of claim 17 or 18, wherein the composition is abrasive, paint or ink. The composition of any one of claims 17 to 19, wherein the particulate solid is a pigment or a filler. The composition of any one of claims 17 to 20, further comprising a binder. a composition comprising a polymer chain having at least one fused aromatic quinone imine pendant, a particulate solid (typically a pigment or filler), and (i) a polar organic medium or (ii) a non-polar organic medium, Wherein the polymer is represented by any one of claims 1 to 21, and the organic medium is a plastic material. The composition of claim 22, wherein the plastic material is a thermoplastic resin. The composition according to any one of claims 17 to 23, wherein the amount of the polymer is in the range of 0.5% by weight to 30% by weight, or 1% by weight to 25% by weight of the composition. The use of a polymer chain having at least one fused aromatic quinone imine pendant, wherein the polymer of any one of claims 1 to 16 is as claimed in any one of claims 17 to 24. a dispersant in the composition.