Dispersants

Abstract

The claimed invention is a polymer (D) obtainable by reacting a) at least one epoxide (E) having an average functionality of 3.0 or more and a number average molar mass in the range of 250 to 25000 g / mol, determined by GPC using THF as solvent, with b) at least one compound (P) having at least one pigment-affinitive group, said pigment-affinitive group having at least one active hydrogen reactive towards the epoxide group, and c) at least one compound (S) having at least one polyalkylene oxide chain, said compound having at least one active hydrogen reactive towards the epoxide group. The invention further discloses the use of the polymer (D) as an aqueous dispersant for pigments.

Description

[Technical field]

[0001] The claimed invention is a polymer (D) obtainable by reacting a) at least one epoxide (E) having an average functionality of 3.0 or more and a number average molar mass in the range of 250 to 25000 g / mol, determined by GPC using THF as solvent, with b) at least one compound (P) having at least one pigment-affinitive group, said pigment-affinitive group having at least one active hydrogen reactive towards the epoxide group, and c) at least one compound (S) having at least one polyalkylene oxide chain, said compound having at least one active hydrogen reactive towards the epoxide group. The invention further discloses the use of the polymer (D) as an aqueous dispersant for pigments. [Background technology]

[0002] Pigmented coating compositions are widely used in the automotive industry as corrosion-resistant primers and decorative topcoats. Since color is a major factor in the vehicle merchandising segment of the automotive industry, high transparency and rich chroma are the trends required in the automotive market. High transparency and rich chroma are generally achieved by stable fine dispersion of organic pigments reaching submicron size in basecoats and clearcoats. However, aggregation of small size pigment particles, e.g., less than 100 nm, during application in coatings and during long-term storage in coating compositions is a major challenge in the coatings industry. It is desirable for the pigment dispersion to remain substantially stable in a finely dispersed form with minimal pigment retention and viscosity changes.

[0003] Generally, random copolymers are used as dispersants in pigment dispersion compositions. These copolymers contain multiple anchor and stabilizing segments. However, their application as dispersants does not provide sufficient stabilization, especially when the pigment particle size is very small. In addition, commercially available hyperdispersants for stabilizing finely dispersed organic pigments have controlled structures derived from special controlled polymerization techniques, and their synthesis has several limitations, such as specific manufacturing settings and harsh process conditions. Therefore, there is a need for continued development of pigment dispersants that can be manufactured in conventional simple polymerization settings and relatively robust processing conditions, yet perform equal to or better than hyperdispersants prepared by controlled polymerization techniques.

[0004] US 2016 / 257774 A1 describes polymeric dispersant compositions comprising an acrylic backbone having at least one pendant imide group attached thereto, the carbonyl of the imide being chemically bonded to a fused aromatic ring.

[0005] US6,037,414A describes a polymeric pigment dispersant comprising a graft polymer having an acrylic backbone, a polyester side chain, a cyclic imide group and a quaternary ammonium group.US8,129,466B2 describes a nanoparticle dispersion comprising a dispersant comprising a triblock polymer having a first block comprising glycidyl (meth)acrylate reacted with naphthoic acid, a second block comprising an alkyl (meth)acrylate ester, and a third block comprising an alkyl (meth)acrylate ester, the third block being different from the second block.

[0006] US 7,723,425 B2 describes compositions containing modified block copolymer dispersants prepared by atom transfer radical polymerization (ATRP) and modified with salt-forming groups selected from certain monocyclic or polycyclic sulfonic acids, or monocyclic or polycyclic carboxylic and phosphonic acids, or alkyl halides containing monocyclic or polycyclic groups, or esters of monocyclic or polycyclic sulfonic acids. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] US2016 / 257774A1 [Patent Document 2] US6,037,414A [Patent Document 3] US8,129,466B2 [Patent Document 4] US7,723,425B2 Summary of the Invention [Problem to be solved by the invention]

[0008] The methods and compositions disclosed in the prior art have limitations. The above-mentioned prior art compositions do not provide efficient pigment dispersants that provide effective deagglomeration and strong interaction with pigment particles to achieve fine dispersion of pigment particles reaching submicron size. The lack of strong interaction with pigment particles affects the transparency and color desired in the market. Due to the increasing demand for niche color spaces with high saturation in the coatings market, there is a need for the synthesis of new dispersants for pigments that can overcome the above drawbacks and provide more stable pigment dispersions, especially with submicron particle size.

[0009] It is therefore an object of the claimed invention to provide polymers that can act as dispersants for pigments, particularly organic pigments, and that can provide pigment dispersions having submicron particle size. [Means for solving the problem]

[0010] Surprisingly, a. at least one epoxide (E) having an average functionality of 3.0 or more and a number average molar mass in the range of 250 to 25000 g / mol, determined by GPC using THF as solvent; b. at least one compound (P) having at least one pigment affinity group, the pigment affinity group having at least one active hydrogen reactive with an epoxide group; c. at least one compound (S) having at least one polyalkylene oxide unit and at least one active hydrogen reactive with an epoxide group; It has been found that the polymer (D) obtained by reacting the above is capable of functioning as a dispersant having desirable properties.

[0011] Thus, in a first aspect, the claimed invention provides: a. at least one epoxide (E) having an average functionality of 3.0 or more and a number average molar mass in the range of 250 to 25000 g / mol, determined by GPC using THF as solvent; b. at least one compound (P) having at least one pigment affinity group, the pigment affinity group having at least one active hydrogen reactive with an epoxide group; c. Formula (I) [ka] (wherein Y is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2~C 30 Alkenyl, or substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C 6 ~C 10 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl; Z is C 1 ~C 6 Alkyl or C 6 ~C 10 aryl; m is 5 to 500; n is 0 to 100; X is -OC(O)-RC(O)OH, -NR 1 C(O)-RC(O)OH, -ORC(O)OH, -OC(O)-R-SH, -NHR 1 or -OR-SH, In the formula, R is a linear or branched, substituted or unsubstituted C 1 ~C 10 Alkylene, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenylene, substituted or unsubstituted C 6 ~C 10 Cycloalkylene, or substituted or unsubstituted C 6 ~C 10 arylene, and R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 6 ~C 10 Aryl, or substituted or unsubstituted C 6 ~C 10 arylalkyl) and at least one compound (S) of The present invention relates to a polymer (D) obtained by reacting

[0012] A second aspect of the invention claimed relates to a method for preparing a polymer (D) according to the first aspect, said method comprising the steps of: a. providing at least one epoxide (E) having an average functionality of 3.0 or more and a number average molar mass in the range of 250 to 25000 g / mol, determined by GPC using THF as solvent; b. Formula (I) [ka] (wherein Y is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, or substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C 6 ~C 10 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl; Z is C 1 ~C 6 Alkyl or C 6 ~C 10 aryl; m is 5 to 500; n is 0 to 100; X is -OC(O)-RC(O)OH, -NR 1 C(O)-RC(O)OH, -ORC(O)OH, -OC(O)-R-SH, -NHR 1 or -OR-SH, In the formula, R is a linear or branched, substituted or unsubstituted C 1 ~C10 Alkylene, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenylene, substituted or unsubstituted C 6 ~C 10 Cycloalkylene, or substituted or unsubstituted C 6 ~C 10 arylene, and R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 6 ~C 10 Aryl, or substituted or unsubstituted C 6 ~C 10 arylalkyl) to obtain a mixture; and c. providing at least one compound (P) having at least one pigment-affinitive group having at least one active hydrogen to obtain a ternary mixture; d. heating the mixture obtained in step c. to a desired temperature to obtain a product. Includes.

[0013] A third aspect of the claimed invention relates to the use of a polymer (D) according to the first and / or second aspect as a dispersant for particulate solid material.

[0014] A fourth aspect of the invention is a method for producing a gypsum-based gypsum comprising the steps of: a. a polymer (D) according to the first aspect, and b. at least one particulate solid material selected from a pigment or a filler; c. at least one liquid diluent, and d. at least one polymeric binder The present invention relates to a composition in the form of a dispersion comprising: The particulate solid material is dispersed in a liquid diluent selected from an organic solvent or water or a mixture of both. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0015] Before describing the compositions and formulations of the claimed invention, it is to be understood that the invention is not limited to the particular compositions and formulations described, as such compositions and formulations may, of course, vary. It is also to be understood that the terms used herein are not intended to be limiting, since the scope of the invention as claimed will be limited only by the appended claims.

[0016] Hereinafter, when a group is defined as including at least a certain number of embodiments, this is meant to include a group consisting of only these embodiments, preferably. Furthermore, the terms "first", "second", "third" or "a", "b", "c", etc. in this specification and claims are used to distinguish between similar elements and are not necessarily used to describe a sequential or chronological order. The terms so used are interchangeable under appropriate circumstances, and it is to be understood that the embodiments of the invention described and claimed herein can operate in other sequences than those described or illustrated herein. The terms "first", "second", "third", or "(A)", "(B)" and "(C)", or "(a)", "(b)", "(c)", "(d)", "i", "ii", etc., when referring to steps of a method or use or assay, unless otherwise stated in this application herein above or below, there is no consistency of time or time interval between the steps, i.e., the steps may be performed simultaneously or there may be a time interval of seconds, minutes, hours, days, weeks, months or even years between such steps.

[0017] As used herein, the term "pigment-affinity group" or "anchor group" of a compound refers to a chemical moiety that has an inherently strong affinity for the pigment surface. The "pigment-affinity group" or "anchor group" of a compound adsorbs to the pigment surface, thereby stabilizing the pigment by opposing any re-aggregation of the pigment. The "pigment-affinity group" or "anchor group" can be classified into the following categories based on the nature of the chemical moiety: a) Acidic pigment-affinity groups are carboxyl moieties (-CO 2 H), a phosphonic acid moiety (-PO 3 H 2 ) and sulfonic acids (-SO 3 H) moieties, including neutralized and derivatized forms thereof; b) Electrically neutral pigment-affinitive groups include polyethers, substituted or unsubstituted aliphatic rings, substituted or unsubstituted aromatic rings (e.g., phenyl and naphthyl), and substituted or unsubstituted heterocyclic derivatives thereof; c) Amine-based pigment-affinity groups include alkaline nitrogen-containing moieties such as aniline, indole, imidazole, imide, morpholine, oxazoline, piperazine, polyethyleneimine, pyridine, trialkylamine, triazole; d) The quaternary amine pigment-affinity group comprises a quaternary amine moiety.

[0018] Furthermore, ranges defined throughout this specification are inclusive of the endpoints, i.e., a range of 1 to 10 means that both 1 and 10 are included in the range. For the avoidance of doubt, Applicant reserves the right to any equivalents under applicable law.

[0019] In the following passages, the different aspects of the claimed invention are defined in more detail. Each aspect thus defined may be combined with any other aspect or aspects, unless expressly indicated to the contrary. In particular, any feature indicated as being preferred or advantageous may be combined with any other feature or features indicated as being preferred or advantageous.

[0020] The phrase "one embodiment" or "an embodiment" used throughout this specification means that a particular feature, structure, or characteristic described in connection with an embodiment is included in at least one embodiment of the claimed invention. Thus, the appearances of the phrase "in one embodiment" or "in an embodiment" in various places throughout this specification are not necessarily all referring to the same embodiment, and may be.

[0021] Furthermore, particular features, structures or characteristics may be combined in any suitable manner in one or more embodiments, as would be apparent to one of ordinary skill in the art from this disclosure. Moreover, although some embodiments described herein include some features and not other features included in other embodiments, combinations of features from different embodiments are meant to form different embodiments within the scope of the claimed invention, as would be understood by one of ordinary skill in the art. For example, in the appended claims, any of the claimed embodiments may be used in any combination.

[0022] In a first aspect, the claimed invention comprises: a. at least one epoxide (E) having an average functionality of 3.0 or more and a number average molar mass in the range of 250 to 25000 g / mol, determined by GPC using THF as solvent; b. at least one compound (P) having at least one pigment affinity group, the pigment affinity group having at least one active hydrogen reactive with an epoxide group; c. Formula (I) [ka] (wherein Y is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, or substituted or unsubstituted C 6 ~C10 Cycloalkyl, substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C 6 ~C 10 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl; Z is C 1 ~C 6 Alkyl or C 6 ~C 10 aryl; m is 5 to 500; n is 0 to 100; X is -OC(O)-RC(O)OH, -NR 1 C(O)-RC(O)OH, -ORC(O)OH, -OC(O)-R-SH, -NHR 1 or -OR-SH, In the formula, R is a linear or branched, substituted or unsubstituted C 1 ~C 10 Alkylene, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenylene, substituted or unsubstituted C 6 ~C 10 Cycloalkylene, or substituted or unsubstituted C 6 ~C 10 arylene, and R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 6 ~C 10 Aryl, or substituted or unsubstituted C 6 ~C 10 arylalkyl) and at least one compound (S) of The present invention relates to a polymer (D) obtained by reacting

[0023] More preferably, the polymer (D) is: a. at least one epoxide (E) having an average functionality of ≥3.0 and ≤10 and a number average molar mass, determined by GPC using THF as solvent, in the range of 250-20000 g / mol; b. at least one compound (P) having at least one pigment affinity group, the pigment affinity group having at least one active hydrogen reactive with an epoxide group; c. Formula (I) [ka] (wherein Y is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, or substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C 6 ~C 10 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl; Z is C 1 ~C 6 Alkyl or C 6 ~C 10 aryl; m is 5 to 500; n is 0 to 100; X is -OC(O)-RC(O)OH, -NR 1 C(O)-RC(O)OH, -ORC(O)OH, -OC(O)-R-SH, -NHR 1 or -OR-SH, In the formula, R is a linear or branched, substituted or unsubstituted C 1 ~C 10 Alkylene, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenylene, substituted or unsubstituted C 6 ~C 10 Cycloalkylene, or substituted or unsubstituted C 6 ~C 10 arylene, and R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 6 ~C 10 Aryl, or substituted or unsubstituted C 6 ~C 10 arylalkyl) and at least one compound (S) of It can be obtained by reacting

[0024] Even more preferably, the polymer (D) is: a. at least one epoxide (E) having an average functionality of ≥3.0 and ≤10 and a number average molar mass, determined by GPC using THF as solvent, in the range of 250-20000 g / mol; b. at least one compound (P) having at least one pigment affinity group, the pigment affinity group having at least one active hydrogen reactive with an epoxide group; c. Formula (I) [ka] (wherein Y is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, or substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C 6 ~C 10 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl; Z is C 1 ~C 6 Alkyl or C 6 ~C 10 aryl; m is 5 to 300; n is 0 to 50; X is -OC(O)-RC(O)OH, -NR 1 C(O)-RC(O)OH, -ORC(O)OH, -OC(O)-R-SH, -NHR 1 or -OR-SH, In the formula, R is a linear or branched, substituted or unsubstituted C 1 ~C 10 Alkylene, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenylene, substituted or unsubstituted C 6 ~C 10 Cycloalkylene, or substituted or unsubstituted C 6 ~C 10 arylene, and R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 6 ~C 10 Aryl, or substituted or unsubstituted C 6~C 10 arylalkyl) and at least one compound (S) of It can be obtained by reacting

[0025] Most preferably, the polymer (D) is: a. at least one epoxide (E) having an average functionality of 3.0 to 6.0 and a number average molar mass determined by GPC using THF as solvent in the range of 250 to 10,000 g / mol; b. at least one compound (P) having at least one pigment affinity group, the pigment affinity group having at least one active hydrogen reactive with an epoxide group; c. Formula (I) [ka] (wherein Y is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, or substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C 6 ~C 10 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl; Z is C 1 ~C 6 Alkyl or C 6 ~C 10 aryl; m is 5 to 100; n is 0 to 30; X is -OC(O)-RC(O)OH, -NR 1 C(O)-RC(O)OH, or -ORC(O)OH; In the formula, R is a linear or branched, substituted or unsubstituted C 1 ~C 10Alkylene, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenylene, substituted or unsubstituted C 6 ~C 10 Cycloalkylene, or substituted or unsubstituted C 6 ~C 10 arylene, and R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 6 ~C 10 Aryl, or substituted or unsubstituted C 6 ~C 10 arylalkyl) and at least one compound (S) of It can be obtained by reacting

[0026] In particular, the polymer (D) is: a. at least one epoxide (E) having an average functionality of 3.0 to 6.0 and a number average molar mass determined by GPC using THF as solvent in the range of 250 to 10,000 g / mol; b. at least one compound (P) having at least one pigment affinity group, the pigment affinity group having at least one active hydrogen reactive with an epoxide group; c. Formula (I) [ka] (Wherein, Y is hydrogen, C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl, or C 7 ~C 15 arylalkyl; Z is -CH 3 , -C 2 H 5 , -C 3 H 7 , or -C 6 H 6 are independently selected from m is 5 to 100; n is 0 to 20; X is selected from -OC(O)-RC(O)OH, -NHC(O)-RC(O)OH or -ORC(O)OH, R is C 1 ~C 4 Alkyl, C 2 ~C 4 Alkenyl, C 6 Alicyclic or C 6 aromatic) and at least one compound (S) of It can be obtained by reacting

[0027] In another preferred embodiment, the epoxide (E) according to the claimed invention has an average functionality in the range of 3 to 10, more preferably the epoxide (E) has an average functionality in the range of 3 to 8, even more preferably the epoxide (E) has an average functionality in the range of 3 to 6, most preferably the epoxide (E) has an average functionality in the range of 3 to 5, and in particular the epoxide (E) has an average functionality in the range of 3 to 5.

[0028] In another preferred embodiment, the epoxide (E) according to the claimed invention has a number average molecular weight in the range of 250 to 25000 g / mol, determined by GPC using THF as solvent, more preferably the epoxide (E) has a number average molecular weight in the range of 500 to 20000 g / mol, determined by GPC using THF as solvent, even more preferably the epoxide (E) has a number average molecular weight in the range of 500 to 10000 g / mol, determined by GPC using THF as solvent, most preferably the epoxide (E) has a number average molecular weight in the range of 500 to 8000 g / mol, determined by GPC using THF as solvent, and in particular the epoxide (E) has a number average molecular weight in the range of 500 to 5000 g / mol, determined by GPC using THF as solvent.

[0029] In another preferred embodiment, the at least one epoxide (E) according to the claimed invention is selected from the group consisting of [ka] TIFF2025501230000009.tif232164 TIFF2025501230000010.tif112113 These polymer forms, or a mixture of two or more of these, are selected.

[0030] More preferably, the at least one epoxide (E) is selected from the group consisting of [ka] TIFF2025501230000012.tif152153 These polymer forms, or a mixture of two or more of these, are selected.

[0031] Even more preferably, the at least one epoxide (E) is [ka] TIFF2025501230000014.tif96112 These polymer forms, or a mixture of two or more of these, are selected.

[0032] Most preferably, at least one epoxide (E) is selected from the group consisting of [ka] The polymeric form may be selected from any of these, or a mixture of two or more of these.

[0033] In particular, at least one epoxide (E) is selected from the group consisting of [ka] The polymeric form may be selected from any of these, or a mixture of two or more of these.

[0034] In another preferred embodiment, the polymeric forms of the epoxide (E) include dimers, trimers, oligomers, and higher homologs.

[0035] When multiple epoxides (E) are used, the polymer may be in the form of a mixed polymer containing different epoxides (E) in any amount.

[0036] Polymeric dispersants typically contain multiple pigment-affinity groups, also known as anchor groups in the state of the art, which have a specific structure for easy adsorption to the pigment surface, exhibit high affinity to the pigment surface, and provide durable adsorption on the surface of the pigment to be dispersed.

[0037] In another preferred embodiment, the at least one compound (P) having at least one pigment-affinity group having at least one active hydrogen reactive towards epoxide groups is selected from the group consisting of diphenolic acid, 3-hydroxynaphthalene-2-carboxylic acid, dialkanolamines, dialkylamines, dibenzylamines, or (B1) or (B2). [ka] (Wherein, G is -NH- or -CH 2 - selected from The dotted lines represent optional bonds; R 5 , R 6 , R 7 , R 8 , R 9 and R 10 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 5 ~C 24 Cycloalkyl, substituted or unsubstituted C 5 ~C 24 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C 6 ~C 10 aryl, or R 5 , and R 6 together with the carbon atom to which they are attached, or R 9 , and R 10 together with the carbon atom to which they are attached, or R 6 , and R 7 form together with the carbon atom to which they are attached a substituted or unsubstituted, unsaturated or aromatic 5-20 membered carbocyclic ring optionally containing as ring member(s) 1, 2 or 3 heteroatom(s) selected from O, N or S; However, R 5 , R 6 , R 7 , R 8 , R 9 , or R 10 At least one of the following is at least one -OH, -NHR 11 - or -SH, R 11is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 5 ~C 24 Cycloalkyl, substituted or unsubstituted C 5 ~C 24 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl) and at least one compound of formula (B) selected from C(1), C(2), C(3) or C(4) [ka] (In the formula, R 20 and R 21 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 5 ~C 24 Cycloalkyl, substituted or unsubstituted C 5 ~C 24 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl, R 20 and R 21 form together with the carbon atom to which they are attached a substituted or unsubstituted, unsaturated or aromatic 5-20 membered carbocyclic ring optionally containing as ring member(s) 1, 2 or 3 heteroatom(s) selected from O, N or S; The dotted lines represent optional bonds, and p is selected from 0, 1 or 2; [ka] (wherein the dotted lines represent optional bonds), [ka] (In the formula, R 22 is a linear or branched, substituted or unsubstituted C 1 ~C 20 Alkylene, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenylene, linear or branched, substituted or unsubstituted C 1 ~C 20 Heteroalkylene, substituted or unsubstituted C 6 ~C 10 Cycloalkylene, or linear or branched, substituted or unsubstituted C 6 ~C 10 arylene, The dotted lines represent optional bonds), and [ka] (In the formula, R 23 and R 24 is hydrogen, halogen, -NO 2 , or SO 3 H, and the dotted lines represent optional bonds; with at least one anhydride (C) of formula selected from:

[0038] More preferably, the at least one compound (P) having at least one pigment-affinitive group having at least one active hydrogen reactive towards an epoxide group is selected from the group consisting of diphenolic acid, 3-hydroxynaphthalene-2-carboxylic acid, dialkanolamines, dialkylamines, dibenzylamines, or (B1) or (B2). [ka] (Wherein, G is -NH- or -CH 2 - selected from The dotted lines represent optional bonds; R 5 , R 6 , R 7 , R 8 , R 9 and R 10 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 5 ~C 24 Cycloalkyl, substituted or unsubstituted C 5 ~C 24 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C 6 ~C 10 aryl, or R 5 , and R 6 together with the carbon atom to which they are attached, or R 9 , and R 10 together with the carbon atom to which they are attached, or R 6 , and R 7 form together with the carbon atom to which they are attached a substituted or unsubstituted, unsaturated or aromatic 5-20 membered carbocyclic ring optionally containing as ring member(s) 1, 2 or 3 heteroatom(s) selected from O, N or S; However, R 5 , R 6 , R 7 , R 8 , R 9 , or R 10 At least one of the following is at least one -OH, -NHR 11 - or -SH, R 11is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 5 ~C 24 Cycloalkyl, substituted or unsubstituted C 5 ~C 24 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl) and at least one compound of formula (B) selected from Formula C(1) [ka] (In the formula, R 20 and R 21 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 5 ~C 24 Cycloalkyl, substituted or unsubstituted C 5 ~C 24 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl, or R 20 and R 21 form together with the carbon atom to which they are attached a substituted or unsubstituted, unsaturated or aromatic 5-20 membered carbocyclic ring optionally containing as ring member(s) 1, 2 or 3 heteroatom(s) selected from O, N or S; The dotted lines represent optional bonds, and p is selected from 0, 1 or 2. with at least one anhydride of, or a mixture of two or more thereof.

[0039] Even more preferably, the at least one compound (P) having at least one pigment-affinity group having at least one active hydrogen reactive towards an epoxide group is a diphenolic acid, a 3-hydroxynaphthalene-2-carboxylic acid, a dialkanolamine, a dialkylamine, a dibenzylamine, or (B1) or (B2). [ka] (Wherein, G is -NH- or -CH 2 - selected from The dotted lines represent optional bonds; R 5 , R 6 , R 7 , R 8 , R 9 and R 10 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 5 ~C 24 Cycloalkyl, substituted or unsubstituted C 5 ~C 24 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C 6 ~C 10 aryl, or R 5 , and R 6 together with the carbon atom to which they are attached, or R 9 , and R 10 together with the carbon atom to which they are attached, or R 6 , and R7 form together with the carbon atom to which they are attached a substituted or unsubstituted, unsaturated or aromatic 5-20 membered carbocyclic ring optionally containing as ring member(s) 1, 2 or 3 heteroatom(s) selected from O, N or S; However, R 5 , R 6 , R 7 , R 8 , R 9 , or R 10 At least one of the following is at least one -OH, -NHR 11 - or -SH, R 11 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 5 ~C 24 Cycloalkyl, substituted or unsubstituted C 5 ~C 24 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl) and at least one compound of formula (B) selected from Formula (C1) [ka] (In the formula, R 20 and R 21 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 7 ~C 15 Arylalkyl, or substituted or unsubstituted C 6 ~C 10aryl, or R 20 and R 21 form together with the carbon atom to which they are attached a substituted or unsubstituted, unsaturated or aromatic 5-10 membered carbocyclic ring optionally containing 1, 2 or 3 heteroatom(s) selected from O, N or S as ring member(s); The dotted lines represent optional bonds, and p is selected from 0, 1 or 2. with at least one anhydride of, or a mixture of two or more thereof.

[0040] Most preferably, the at least one compound (P) having at least one pigment-affinity group having at least one active hydrogen reactive towards an epoxide group is a diphenolic acid, a 3-hydroxynaphthalene-2-carboxylic acid, a dialkanolamine, a dialkylamine, a dibenzylamine, or (B1) or (B2). [ka] (Wherein, G is -NH- or -CH 2 - selected from The dotted lines represent optional bonds; R 5 , R 6 , R 7 , R 8 , R 9 and R 10 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 5 ~C 24 Cycloalkyl, substituted or unsubstituted C 5 ~C 24 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C6 ~C 10 aryl, or R 5 , and R 6 together with the carbon atom to which they are attached, or R 9 , and R 10 together with the carbon atom to which they are attached, or R 6 , and R 7 form together with the carbon atom to which they are attached a substituted or unsubstituted, unsaturated or aromatic 5-10 membered carbocyclic ring optionally containing 1, 2 or 3 heteroatom(s) selected from O, N or S as ring member(s); However, R 5 , R 6 , R 7 , R 8 , R 9 , or R 10 At least one of the following is at least one -OH or -NHR: 11 - is substituted, R 11 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 5 ~C 24 Cycloalkyl, substituted or unsubstituted C 5 ~C 24 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl) and at least one compound of formula (B) selected from Formula C(1) [ka] (In the formula, R 20 and R21 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 7 ~C 15 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl, or R 20 and R 21 form together with the carbon atom to which they are attached a substituted or unsubstituted, unsaturated or aromatic 5-10 membered carbocyclic ring optionally containing 1, 2 or 3 heteroatom(s) selected from O, N or S as ring member(s); The dotted lines represent optional bonds, and p is selected from 0, 1 or 2. with at least one anhydride of, or a mixture of two or more thereof.

[0041] Particularly preferably, the at least one compound (P) having at least one pigment-affinity group having at least one active hydrogen reactive towards epoxide groups is a diphenolic acid, a 3-hydroxynaphthalene-2-carboxylic acid, a dialkanolamine, a dialkylamine, a dibenzylamine, or (B1) or (B2). [ka] (Wherein, G is -NH- or -CH 2 - selected from The dotted lines represent optional bonds; R 5 , R 6 , R 7 , R 8 , R 9 and R 10 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 15Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 16 Alkenyl, substituted or unsubstituted C 5 ~C 10 Cycloalkyl, substituted or unsubstituted C 5 ~C 10 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C 6 ~C 7 aryl, or R 5 , and R 6 together with the carbon atom to which they are attached, or R 9 , and R 10 together with the carbon atom to which they are attached, or R 6 , and R 7 form together with the carbon atom to which they are attached a substituted or unsubstituted, unsaturated or aromatic 5-10 membered carbocyclic ring optionally containing 1, 2 or 3 heteroatom(s) selected from O or N as ring member(s); However, R 5 , R 6 , R 7 , R 8 , R 9 , or R 10 At least one of the following is at least one -OH or -NHR: 11 - is substituted, R 11 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 5 ~C 24 Cycloalkyl, substituted or unsubstituted C 5 ~C 24 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C15 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl) and at least one compound of formula (B) selected from Formula C(1) [ka] (In the formula, R 20 and R 21 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 7 ~C 15 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl, or R 20 and R 21 form together with the carbon atom to which they are attached a substituted or unsubstituted, unsaturated or aromatic 5-10 membered carbocyclic ring optionally containing 1, 2 or 3 heteroatom(s) selected from O, N or S as ring member(s); The dotted lines represent optional bonds, and p is selected from 0, 1 or 2. with at least one anhydride of, or a mixture of two or more thereof.

[0042] In another preferred embodiment, the at least one compound (P) having at least one pigment-affinity group having at least one active hydrogen is a compound represented by the formula C(1): [ka] (In the formula, R 20 and R 21 is hydrogen, linear or branched, substituted or unsubstituted C1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 5 ~C 24 Cycloalkyl, substituted or unsubstituted C 5 ~C 24 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl, or R 20 and R 21 form together with the carbon atom to which they are attached a substituted or unsubstituted, unsaturated or aromatic 5-20 membered carbocyclic ring optionally containing as ring member(s) 1, 2 or 3 heteroatom(s) selected from O, N or S; The dotted lines represent optional bonds, and p is selected from 0, 1 or 2. with at least one anhydride of

[0043] More preferably, the at least one compound (P) having at least one pigment-affinitive group having at least one active hydrogen is a compound represented by the formula C(1): [ka] (In the formula, R 20 and R 21 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 20 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 20 Alkenyl, substituted or unsubstituted C 5 ~C 14 Cycloalkyl, substituted or unsubstituted C 5 ~C 14Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl, or R 20 and R 21 form together with the carbon atom to which they are attached a substituted or unsubstituted, unsaturated or aromatic 5-20 membered carbocyclic ring optionally containing as ring member(s) 1, 2 or 3 heteroatom(s) selected from O, N or S; The dotted lines represent optional bonds, and p is selected from 0, 1 or 2; with at least one anhydride of

[0044] Even more preferably, the at least one compound (P) having at least one pigment-affinity group having at least one active hydrogen is a compound represented by the formula C(1) [ka] (In the formula, R 20 and R 21 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 16 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 20 Alkenyl, substituted or unsubstituted C 5 ~C 10 Cycloalkyl, substituted or unsubstituted C 5 ~C 10 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, or substituted or unsubstituted C 6 ~C 8 aryl, or R 20 and R 21form together with the carbon atom to which they are attached a substituted or unsubstituted, unsaturated or aromatic 5-10 membered carbocyclic ring optionally containing 1, 2 or 3 heteroatom(s) selected from O, N or S as ring member(s); The dotted lines represent optional bonds, and p is selected from 0, 1 or 2. with at least one anhydride of

[0045] Most preferably, the at least one compound (P) having at least one pigment-affinity group having at least one active hydrogen is a compound represented by the formula C(1): [ka] (In the formula, R 20 and R 21 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 16 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 16 Alkenyl, substituted or unsubstituted C 5 ~C 8 Cycloalkyl, substituted or unsubstituted C 5 ~C 8 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, or substituted or unsubstituted C 6 ~C 8 aryl, or R 20 and R 21 form together with the carbon atom to which they are attached a substituted or unsubstituted, unsaturated or aromatic 5-8 membered carbocyclic ring optionally containing 1, 2 or 3 heteroatom(s) selected from O, N or S as ring member(s); The dotted lines represent optional bonds, and p is selected from 0, 1 or 2. with at least one anhydride of

[0046] In particular, the at least one compound (P) having at least one pigment-affinity group having at least one active hydrogen is a compound represented by the formula C(1): [ka] (In the formula, R 20 and R 21 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 16 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 16 Alkenyl, substituted or unsubstituted C 5 ~C 6 Cycloalkyl, substituted or unsubstituted C 5 ~C 6 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 10 Arylalkyl, or substituted or unsubstituted C 6 aryl, or R 20 and R 21 form together with the carbon atom to which they are attached a substituted or unsubstituted, unsaturated or aromatic 5-6 membered carbocyclic ring optionally containing as ring member(s) 1 or 2 heteroatom(s) selected from O, or N; The dotted lines represent optional bonds, and p is selected from 0 or 1. with at least one anhydride of

[0047] In another preferred embodiment, the at least one anhydride according to the claimed invention is [ka] TIFF2025501230000036.tif228158 TIFF2025501230000037.tif212159 TIFF2025501230000038.tif232159 TIFF2025501230000039.tif220158 TIFF2025501230000040.tif126157 or a mixture of two or more thereof.

[0048] More preferably, the at least one anhydride according to the claimed invention is [ka] TIFF2025501230000042.tif229159 TIFF2025501230000043.tif250159 TIFF2025501230000044.tif212160 TIFF2025501230000045.tif180156 or a mixture of two or more thereof.

[0049] Even more preferably, at least one anhydride according to the claimed invention is [ka] TIFF2025501230000047.tif233160 TIFF2025501230000048.tif249158 TIFF2025501230000049.tif141156 or a mixture of two or more thereof.

[0050] Most preferably, at least one anhydride according to the claimed invention is selected from the group consisting of: [ka] TIFF2025501230000051.tif250158 TIFF2025501230000052.tif143157 or a mixture of two or more thereof.

[0051] In particular, at least one anhydride according to the invention is claimed which is [ka] TIFF2025501230000054.tif248160 or a mixture of two or more thereof.

[0052] In another preferred embodiment, according to the claimed invention, at least one compound of formula (I) [ka] and In the formula, Y is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, or substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C 6 ~C 10 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl; Z is C 1 ~C 6 Alkyl or C 6 ~C 10 aryl; m is 5 to 500; n is 0 to 100; X is -OC(O)-RC(O)OH, -NR 1C(O)-RC(O)OH, -ORC(O)OH, -OC(O)-R-SH, -NHR 1 or -OR-SH, In the formula, R is a linear or branched, substituted or unsubstituted C 1 ~C 10 Alkylene, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenylene, substituted or unsubstituted C 6 ~C 10 Cycloalkylene, or substituted or unsubstituted C 6 ~C 10 arylene, and R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 6 ~C 10 Aryl, or substituted or unsubstituted C 6 ~C 10 arylalkyl; More preferably, Y is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 20 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 20 Alkenyl, or linear or branched, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C 6 ~C 10 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl; Z is C 1 ~C 6 Alkyl or C 6 ~C10 aryl; m is 5 to 200; n is 0 to 50; X is -OC(O)-RC(O)OH, -NR 1 C(O)-RC(O)OH, -ORC(O)OH, -OC(O)-R-SH, -NHR 1 or -OR-SH, In the formula, R is a linear or branched, substituted or unsubstituted C 1 ~C 10 Alkylene, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenylene, substituted or unsubstituted C 6 ~C 10 Cycloalkylene, or substituted or unsubstituted C 6 ~C 10 arylene, and R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 6 ~C 10 Aryl, or substituted or unsubstituted C 6 ~C 10 arylalkyl, and even more preferably Y is selected from hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 16 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 16 Alkenyl, or substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 7 ~C 15 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl; Z is C1 ~C 6 Alkyl or C 6 ~C 10 aryl; m is 5 to 100; n is 0 to 25; X is -OC(O)-RC(O)OH, -NR 1 C(O)-RC(O)OH, -ORC(O)OH, -OC(O)-R-SH, -NHR 1 or -OR-SH, In the formula, R is a linear or branched, substituted or unsubstituted C 1 ~C 10 Alkylene, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenylene, substituted or unsubstituted C 6 ~C 10 Cycloalkylene, or substituted or unsubstituted C 6 ~C 10 arylene, and R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 6 ~C 10 Aryl, or substituted or unsubstituted C 6 ~C 10 arylalkyl, and most preferably Y is selected from hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, or substituted or unsubstituted C 6 ~C 7 Cycloalkyl, substituted or unsubstituted C 7 ~C 10 Arylalkyl, or substituted or unsubstituted C6 aryl; Z is C 1 ~C 3 Alkyl or C 6 aryl; m is 5 to 100; n is 0 to 20; X is -OC(O)-RC(O)OH, -NR 1 C(O)-RC(O)OH, or -ORC(O)OH; In the formula, R is a linear or branched, substituted or unsubstituted C 1 ~C 10 Alkylene, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenylene, substituted or unsubstituted C 6 ~C 10 Cycloalkylene, or substituted or unsubstituted C 6 ~C 10 arylene, and R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 6 ~C 10 Aryl, or substituted or unsubstituted C 6 ~C 10 arylalkyl, and in particular Y is selected from hydrogen, C 1 ~C 18 Alkyl, C 2 ~C 18 Alkenyl or C 7 ~C 15 arylalkyl; Z is selected from -CH 3 , -C 2 H 5 , -C 3 H 7 , or -C 6 H 6 are independently selected from m is 5 to 100; n is 0 to 20; X is selected from -OC(O)-RC(O)OH, -NHC(O)-RC(O)OH or -ORC(O)OH, R is C 1 ~C 10 Alkyl, C 2 ~C 10 Alkenyl, C 6 ~C 10 Alicyclic or C 6 selected from aromatic R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, or substituted or unsubstituted C 6 ~C 10 aryl.

[0053] In another preferred embodiment, the compound of formula (I) is a random or block copolymer and comprises at least 50% by weight of ethylene oxide in polymerized form relative to the total weight of the compound of formula (I), more preferably the compound of formula (I) is a random or block copolymer and comprises at least 70% by weight of ethylene oxide in polymerized form relative to the total weight of the compound of formula (I), furthermore the compound of formula (I) is a random or block copolymer and comprises at least 75% by weight of ethylene oxide in polymerized form relative to the total weight of the compound of formula (I), most preferably the compound of formula (I) is a random or block copolymer and comprises at least 90% by weight of ethylene oxide in polymerized form relative to the total weight of the compound of formula (I), and in particular the compound of formula (I) is a random or block copolymer and comprises 100% by weight of ethylene oxide in polymerized form relative to the total weight of the compound of formula (I).

[0054] In another preferred embodiment, the compound of formula (I) is a random or block copolymer and contains from 50 to 100% by weight of ethylene oxide in polymerized form relative to the total weight of the compound of formula (I).

[0055] In another preferred embodiment, the compound of formula (I) according to the claimed invention is a random or block copolymer comprising 50-100% by weight of ethylene oxide in polymerized form and 0-50% by weight of propylene oxide in polymerized form, respectively, relative to the total weight of the compound of formula (I), more preferably the compound of formula (I) is a random or block copolymer comprising 60-100% by weight of ethylene oxide in polymerized form and 0-40% by weight of propylene oxide in polymerized form, respectively, relative to the total weight of the compound of formula (I), even more preferably the compound of formula (I) is It is a random or block copolymer containing 75 to 100% by weight of ethylene oxide in polymerized form and 0 to 25% by weight of propylene oxide in polymerized form, respectively, relative to the total weight of the compound of formula (I), most preferably the compound of formula (I) is a random or block copolymer containing 90 to 100% by weight of ethylene oxide in polymerized form and 0 to 10% by weight of propylene oxide in polymerized form, respectively, relative to the total weight of the compound of formula (I), and in particular the compound of formula (I) is a polymer containing 100% by weight of ethylene oxide, relative to the total weight of the compound of formula (I).

[0056] In another preferred embodiment, the ratio of the total molar eq of epoxides (E) to the total molar eq of compounds (P) in the dispersant is in the range of 1:0.25 to 1:0.90, more preferably the ratio of the total molar eq of epoxides (E) to the total molar eq of compounds (P) in the dispersant is in the range of 1:0.35 to 1:0.80, even more preferably the ratio of the total molar eq of epoxides (E) to the total molar eq of compounds (P) in the dispersant is in the range of 1:0.4 to 1:0.80, most preferably the ratio of the total molar eq of epoxides (E) to the total molar eq of compounds (P) in the dispersant is in the range of 1:0.40 to 1:0.75, and in particular the ratio of the total molar eq of epoxides (E) to the total molar eq of compounds (P) in the dispersant is in the range of 0.55 to 0.75.

[0057] In another preferred embodiment, the ratio of the total molar eq of epoxides (E) in the dispersant to the total molar eq of compounds of formula (I) is in the range of 1:0.10 to 1:0.75, more preferably the ratio of the total molar eq of epoxides (E) in the dispersant to the total molar eq of compounds of formula (I) is in the range of 1:0.10 to 1:0.65, even more preferably the ratio of the total molar eq of epoxides (E) in the dispersant to the total molar eq of compounds of formula (I) is in the range of 1:0.20 to 1:0.50, most preferably the ratio of the total molar eq of epoxides (E) in the dispersant to the total molar eq of compounds of formula (I) is in the range of 1:0.20 to 1:0.45, and in particular the ratio of the total molar eq of epoxides (E) in the dispersant to the total molar eq of compounds of formula (I) is in the range of 1:0.25 to 1:0.40.

[0058] In another preferred embodiment, the ratio of the molar eq of the epoxide (E) to the sum of the molar eq of the compound of formula (I) and the compound of formula (P) is in the range of 1:0.50 to 1:1.75, more preferably the ratio of the molar eq of the epoxide (E) to the sum of the molar eq of the compound of formula (I) and the compound of formula (P) is in the range of 1:0.70 to 1:1.5, even more preferably the ratio of the molar eq of the epoxide (E) to the sum of the molar eq of the compound of formula (I) and the compound of formula (P) is in the range of 1:0.80 to 1:1.2, most preferably the ratio of the molar eq of the epoxide (E) to the sum of the molar eq of the compound of formula (I) and the compound of formula (P) is in the range of 1:0.90 to 1:1.1, and in particular the ratio of the molar eq of the epoxide (E) to the sum of the molar eq of the compound of formula (I) and the compound of formula (P) is in the range of 1:0.95 to 1:1.

[0059] In another preferred embodiment, the polymer (D) according to the claimed invention has a hyperbranched polymer structure. The term "hyperbranched" in the context of the claimed invention means a polymer with multiple branching points and multifunctional branches. Hyperbranched polymers form polydisperse systems with various degrees of branching.

[0060] In another preferred embodiment, the polymer (D) according to the invention claimed has a number average molecular weight in the range of 1000-100000 g / mol, measured by GPC using 1 mol / L acetic acid in THF as eluent, more preferably the polymer (D) has a number average molecular weight in the range of 1000-80000 g / mol, measured by GPC using 1 mol / L acetic acid in THF as eluent, even more preferably the polymer (D) according to the invention claimed has a number average molecular weight in the range of 1000-60000 g / mol, measured by GPC using 1 mol / L acetic acid in THF as eluent, and most preferably the polymer (D) according to the invention claimed has a number average molecular weight in the range of 1000-50000 g / mol, measured by GPC using 1 mol / L acetic acid in THF as eluent. The column used was a PSS SDV 10e6+10e5+10e3, 8×300 mm, 5 μm, maintained at 35° C. The instrument was calibrated with polymethylmethacrylate and the eluent flow rate was 1 mL / min.

[0061] In another embodiment, the claimed invention relates to a method for preparing a polymer (D), comprising the steps of: a. providing at least one epoxide (E) having an average functionality of 3.0 or more and a number average molar mass in the range of 250 to 25000 g / mol, determined by GPC using THF as solvent; b. Formula (I) [ka] (wherein Y is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, or substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C 6 ~C10 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl; Z is C 1 ~C 6 Alkyl or C 6 ~C 10 aryl; m is 5 to 500; n is 0 to 100; X is -OC(O)-RC(O)OH, -NR 1 C(O)-RC(O)OH, -ORC(O)OH, -OC(O)-R-SH, -NHR 1 or -OR-SH, In the formula, R is a linear or branched, substituted or unsubstituted C 1 ~C 10 Alkylene, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenylene, substituted or unsubstituted C 6 ~C 10 Cycloalkylene, or substituted or unsubstituted C 6 ~C 10 arylene, and R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 6 ~C 10 Aryl, or substituted or unsubstituted C 6 ~C 10 arylalkyl) to obtain a mixture; and c. providing at least one compound (P) having at least one pigment-affinitive group having at least one active hydrogen to obtain a ternary mixture; d. heating the mixture obtained in step c. to a desired temperature to obtain a product. Includes.

[0062] More preferably, the claimed invention relates to a method for preparing a polymer (D), said method comprising the following steps: a. providing at least one epoxide (E) having an average functionality of 3.0 or more and a number average molar mass in the range of 250 to 25000 g / mol, determined by GPC using THF as solvent; b. Formula (I) [ka] (wherein Y is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, or substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C 6 ~C 10 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl; Z is C 1 ~C 6 Alkyl or C 6 ~C 10 aryl; m is 5 to 300; n is 0 to 50; X is -OC(O)-RC(O)OH, -NR 1 C(O)-RC(O)OH, -ORC(O)OH, -OC(O)-R-SH, -NHR 1 or -OR-SH, In the formula, R is a linear or branched, substituted or unsubstituted C 1 ~C 10 Alkylene, linear or branched, substituted or unsubstituted C2 ~C 10 Alkenylene, substituted or unsubstituted C 6 ~C 10 Cycloalkylene, or substituted or unsubstituted C 6 ~C 10 arylene, and R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 6 ~C 10 Aryl, or substituted or unsubstituted C 6 ~C 10 arylalkyl) providing at least one compound of c. providing at least one compound (P) having at least one pigment-affinitive group having at least one active hydrogen to obtain a ternary mixture; d. heating the mixture obtained in step c. to a desired temperature to obtain a product. Includes.

[0063] Even more preferably, the claimed invention relates to a method for the preparation of polymer (D), said method comprising the following steps: a. providing at least one epoxide (E) having an average functionality of 3.0 or more and a number average molar mass in the range of 250 to 25000 g / mol, determined by GPC using THF as solvent; b. Formula (I) [ka] (wherein Y is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30Alkenyl, or substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C 6 ~C 10 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl; Z is C 1 ~C 6 Alkyl or C 6 ~C 10 aryl; m is 5 to 100; n is 0 to 30; X is -OC(O)-RC(O)OH, -NR 1 C(O)-RC(O)OH, or -ORC(O)OH; In the formula, R is a linear or branched, substituted or unsubstituted C 1 ~C 10 Alkylene, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenylene, substituted or unsubstituted C 6 ~C 10 Cycloalkylene, or substituted or unsubstituted C 6 ~C 10 arylene, and R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 6 ~C 10 Aryl, or substituted or unsubstituted C 6 ~C 10 arylalkyl) providing at least one compound of c. providing at least one compound (P) having at least one pigment-affinitive group having at least one active hydrogen to obtain a ternary mixture; d. heating the mixture obtained in step c. to a desired temperature to obtain a product. Includes.

[0064] Most preferably, the claimed invention relates to a method for the preparation of polymer (D), said method comprising the following steps: a. providing at least one epoxide (E) having an average functionality of 3.0 or more and a number average molar mass in the range of 250 to 25000 g / mol, determined by GPC using THF as solvent; b. Formula (I) [ka] (Wherein, X is C 1 ~C 18 Alkyl, C 2 ~C 18 Alkenyl or C 7 ~C 15 arylalkyl; Z is -CH 3 , -C 2 H 5 , -C 3 H 7 , or -C 6 H 6 are independently selected from m is 5 to 100; n is 0 to 20; X is selected from -OC(O)-RC(O)OH, -NHC(O)-RC(O)OH or -ORC(O)OH, R is C 1 ~C 10 Alkyl, C 2 ~C 10 Alkenyl, C 6 ~C 10 Alicyclic or C 6 selected from aromatic R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, or substituted or unsubstituted C 6 ~C 10 aryl) providing at least one compound of c. providing at least one compound (P) having at least one pigment-affinitive group having at least one active hydrogen to obtain a ternary mixture; d. heating the mixture obtained in step c. to a desired temperature to obtain a product. Includes.

[0065] In particular, the claimed invention relates to a method for the preparation of a polymer (D), said method comprising the following steps: a. Below, [ka] TIFF2025501230000061.tif227163 Providing at least one epoxide (E) selected from these polymeric forms, or a mixture of two or more of these; b. Formula (I) [ka] (Wherein, X is C 1 ~C 18 Alkyl, C 2 ~C 18 Alkenyl or C 7 ~C 15 arylalkyl; Z is -CH 3 , -C 2 H 5 , -C 3 H 7 , or -C 6 H 6are independently selected from m is 5 to 100; n is 0 to 20; X is selected from -OC(O)-RC(O)OH, -NHC(O)-RC(O)OH or -ORC(O)OH, R is C 1 ~C 10 Alkyl, C 2 ~C 10 Alkenyl, C 6 ~C 10 Alicyclic or C 6 selected from aromatic R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, or substituted or unsubstituted C 6 ~C 10 aryl) providing at least one compound of c. providing at least one compound (P) having at least one pigment-affinitive group having at least one active hydrogen to obtain a ternary mixture; d. heating the mixture obtained in step c. to a desired temperature to obtain a product. Includes.

[0066] In another preferred embodiment, the claimed invention relates to a method for preparing a polymer (D), comprising the steps of: a. The following: [ka] TIFF2025501230000065.tif234164 Providing at least one epoxide (E) selected from these polymeric forms, or a mixture of two or more of these; b. Formula (I) [ka] (Wherein, X is C 1 ~C 18 Alkyl, C 2 ~C 18 Alkenyl or C 7 ~C 15 arylalkyl; Z is -CH 3 , -C 2 H 5 , -C 3 H 7 , or -C 6 H 6 are independently selected from m is 5 to 100; n is 0 to 20; X is selected from -OC(O)-RC(O)OH, -NHC(O)-RC(O)OH or -ORC(O)OH, R is C 1 ~C 10 Alkyl, C 2 ~C 10 Alkenyl, C 6 ~C 10 Alicyclic or C 6 selected from aromatic R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, or substituted or unsubstituted C 6 ~C 10 aryl) providing at least one compound of c. providing at least two compounds (P) having at least one pigment-affinity group having at least one active hydrogen reactive with an epoxide group to obtain a ternary mixture, the compounds (P) being selected from the group consisting of diphenolic acid, 3-hydroxynaphthalene-2-carboxylic acid, dialkanolamines, dialkylamines, dibenzylamines, or (B1) or (B2); [ka] (Wherein, G is -NH- or -CH 2 - selected from The dotted lines represent optional bonds; R 5 , R 6 , R 7 , R 8 , R 9 and R 10 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 5 ~C 24 Cycloalkyl, substituted or unsubstituted C 5 ~C 24 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C 6 ~C 10 aryl, or R 5 , and R 6 together with the carbon atom to which they are attached, or R 9 , and R 10 together with the carbon atom to which they are attached, or R 6 , and R 7form together with the carbon atom to which they are attached a substituted or unsubstituted, unsaturated or aromatic 5-20 membered carbocyclic ring optionally containing as ring member(s) 1, 2 or 3 heteroatom(s) selected from O, N or S; However, R 5 , R 6 , R 7 , R 8 , R 9 , or R 10 At least one of the following is at least one -OH, -NHR 11 - or -SH, R 11 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 5 ~C 24 Cycloalkyl, substituted or unsubstituted C 5 ~C 24 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl) and at least one compound of formula (B) selected from C(1), C(2), C(3) or C(4), [ka] (In the formula, R 20 and R 21 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 5 ~C 24 Cycloalkyl, substituted or unsubstituted C 5 ~C 24Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl, R 20 and R 21 form together with the carbon atom to which they are attached a substituted or unsubstituted, unsaturated or aromatic 5-20 membered carbocyclic ring optionally containing as ring member(s) 1, 2 or 3 heteroatom(s) selected from O, N or S; The dotted lines represent optional bonds, and p is selected from 0, 1 or 2; [ka] (wherein the dotted lines represent optional bonds), [ka] (In the formula, R 22 is a linear or branched, substituted or unsubstituted C 1 ~C 20 Alkylene, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenylene, linear or branched, substituted or unsubstituted C 1 ~C 20 Heteroalkylene, substituted or unsubstituted C 6 ~C 10 Cycloalkylene, or linear or branched, substituted or unsubstituted C 6 ~C 10 arylene, The dotted lines represent optional bonds), and [ka] (In the formula, R 23 and R 24 is hydrogen, halogen, -NO 2 , or SO 3 H, or -COOH, and the dotted lines represent optional bonds. or a mixture thereof; and d. heating the mixture obtained in step c. to a desired temperature to obtain a product. Includes.

[0067] In another embodiment, a person skilled in the art can exchange the addition process of each reaction component. In the claimed invention, it is also envisioned that the epoxide (E) is first reacted with at least one compound of formula (I) to obtain an intermediate, and the intermediate is further reacted with at least one compound (P) having at least one pigment affinity group having at least one active hydrogen to obtain a dispersant. Similarly, a person skilled in the art can first react the epoxide (P) with at least one compound (P) having at least one pigment affinity group having at least one active hydrogen to obtain an intermediate. The intermediate is further reacted with at least one compound of formula (I) to obtain a dispersant.

[0068] In another preferred embodiment, the process further comprises the step of adding a catalyst.

[0069] In another preferred embodiment, the catalyst is (triethanolatoamine)Ti—OR 20 (In the formula, R 20 is a linear or branched (C 1~12 ) alkyl, preferably linear or branched (C 1~6) alkyl), such as triethanolatoamine titanium isopropanolate (CAS number 74665-17-1), zirconium tetrabutanolate (CAS number 1071-76-7), tris(diethylphosphinato)aluminum (CAS number 225789-38-8), aluminum distearate (CAS number 300-92-5), dioctyltin dilaurate (CAS number 3648-18-81), titanium tristearate monoisopropanolate, zinc(II) acetylacetonate, copper(II) acetylacetonate (CAS number: 13395-16-9), titanium diacetylacetonate diisopropanolate (CAS number: 2785 8-32-8), titanium(IV) butoxide (CAS No. 5593-70-4), titanium diisopropoxide bis(acetylacetonate) (CAS No. 17927-72-9), titanium isopropoxide(4) (CAS No. 546-68-9), tetrakis(2-ethylhexyl)orthotitanate (CAS No. 1070-10-6), tetrakis(triethanolaminato)zirconium(IV) (CAS No. 101033-44-7), zinc stearate (CAS No. 557-05-1), or boron trifluoride ethylamine complex (CAS No. 75-23-0), and most preferably the catalyst is zinc(II) acetylacetonate.

[0070] The types of catalysts used in acid-epoxy reactions are known to those skilled in the art and are described in the literature (see, for example, waterborne and solvent based epoxies and their end use applications, John Wiley and Sons and SITA technology Ltd. (ISBN0947798498)).

[0071] In the acid-epoxy reaction, an alkaline substance such as a tertiary amine, trialkylphosphine, triphenylphosphine, a quaternary ammonium compound, a quaternary phosphonium compound, potassium hydroxide, or sodium hydroxide can be used as a catalyst. Other catalysts that can be used include organometallic compounds such as zinc acetylacetonate, zirconium acetylacetonate, Zr octoate, zinc octoate, Li stearate, and stannous octoate. In the case of amine epoxy or thiol epoxy, a tertiary amine catalyst is selected as the catalyst.

[0072] In another preferred embodiment, according to the method, the step d. reaction is carried out at a temperature in the range of 20 to 250°C, more preferably, the step d. reaction is carried out at a temperature in the range of 50 to 200°C, even more preferably, the step d. reaction is carried out at a temperature in the range of 80 to 180°C, most preferably, the step d. reaction is carried out at a temperature in the range of 80 to 150°C, and particularly the step d. reaction is carried out at a temperature in the range of 100 to 140°C.

[0073] In another preferred embodiment, steps a. to d. are carried out in the presence of at least one solvent or in the absence of a solvent.

[0074] In another preferred embodiment, the at least one solvent is selected from an alcohol, a ketone, an ester, an aromatic solvent, an aliphatic solvent, a cyclic ether, an ether, an ether alcohol, or a mixture of two or more thereof, more preferably the at least one solvent is selected from a ketone, an ester, an aromatic solvent, an aliphatic solvent, a cyclic ether, an ether, or a mixture of two or more thereof, even more preferably the at least one solvent is selected from a ketone, an ester, a cyclic ether, an ether, or a mixture of two or more thereof, most preferably the at least one solvent is selected from a ketone, an ester, a cyclic ether, or a mixture of two or more thereof, and in particular the at least one solvent is selected from a ketone, an ester, or a mixture of two or more thereof.

[0075] In another preferred embodiment, the reaction of step d. is carried out for a time in the range of 10 minutes to 10 hours, more preferably, the reaction of step d. is carried out for a time in the range of 10 minutes to 8 hours, even more preferably, the reaction of step d. is carried out for a time in the range of 30 minutes to 5 hours, most preferably, the reaction of step d. is carried out for a time in the range of 30 minutes to 3 hours, and in particular, the reaction of step d. is carried out for a time in the range of 30 minutes to 2 hours.

[0076] In another preferred embodiment, the claimed invention relates to the use of the above-mentioned polymer (D) as a dispersant for particulate solid materials.

[0077] In another preferred embodiment, the particulate solid material is a pigment, more preferably an organic pigment.

[0078] In another embodiment, the claimed invention provides: The above polymer (D), and at least one particulate solid material selected from a pigment or a filler, and at least one liquid diluent; The present invention relates to a composition in the form of a dispersion comprising: More preferably, the claimed invention comprises: The above polymer (D), and at least one particulate solid material selected from a pigment or a filler; at least one liquid diluent, and At least one polymeric binder The present invention relates to a composition in the form of a dispersion comprising: The particulate solid material is dispersed in a liquid diluent selected from an organic solvent or water or a mixture of both.

[0079] In another preferred embodiment, the binder is selected from a paint, a filler, an additive, or a mixture of two or more thereof. Representative examples of additives include, but are not limited to, surfactants, light stabilizers, UV absorbers, defoamers, dyes, plasticizers, leveling agents, anti-skinning agents, or a mixture of two or more thereof. More preferably, the at least one binder is preferably selected from poly(meth)acrylates, polystyrenes, polyesters, alkyds, polysaccharides, polyurethanes, or a mixture of two or more thereof.

[0080] In another preferred embodiment, said composition has a weight ratio of particulate solid material to polymer (D) according to the claimed invention in the range of 20:1 to 1:20, more preferably a weight ratio of particulate solid material to dispersant according to the claimed invention in the range of 20:1 to 1:10, and most preferably a weight ratio of particulate solid material to dispersant according to the claimed invention in the range of 20:1 to 1:5.0.

[0081] In another preferred embodiment, the composition comprises: ≧1 to ≦70% by weight, based on the total weight of the composition, of particulate solid material selected from pigments or fillers, ≧0.5 to ≦50% by weight, based on the total weight of the composition, of the polymer (D) as defined above, and ≧10 to ≦98.5% by mass of a liquid diluent based on the total mass of the composition Includes.

[0082] In another preferred embodiment, the composition is in the form of a millbase, or a coating composition.

[0083] In another preferred embodiment, the composition has a particle size (D) in the range of 10 to 500 nm as measured using dynamic light scattering techniques. 50 ), and more preferably the composition has a particle size (D 50), and even more preferably, the composition has a particle size (D 50 ), and most preferably the composition has a particle size (D) in the range of 50 to 200 nm as measured using dynamic light scattering techniques. 50 ) and in particular the composition has a particle size (D) in the range of 80 to 175 nm as measured using dynamic light scattering techniques. 50 ).

[0084] The invention as claimed relates to at least one of the following advantages: Pigment dispersions with submicron particle sizes can be achieved; By varying the type of pigment-affining group and the number and length of the compound of formula 1, it is possible to tune the properties of the dispersant.

[0085] Embodiment Below, a list of embodiments is provided to further illustrate the present disclosure, without intending to limit the disclosure to the specific embodiments listed below.

[0086] 1. a. at least one epoxide (E) having an average functionality of 3.0 or more and a number average molar mass in the range of 250 to 25000 g / mol, determined by GPC using THF as solvent; b. at least one compound (P) having at least one pigment affinity group, the pigment affinity group having at least one active hydrogen reactive with an epoxide group; c. Formula (I) [ka] (wherein Y is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, or substituted or unsubstituted C 6 ~C 10Cycloalkyl, substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C 6 ~C 10 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl; Z is C 1 ~C 6 Alkyl or C 6 ~C 10 aryl; m is 5 to 500; n is 0 to 100; X is -OC(O)-RC(O)OH, -NR 1 C(O)-RC(O)OH, -ORC(O)OH, -OC(O)-R-SH, -NHR 1 or -OR-SH, In the formula, R is a linear or branched, substituted or unsubstituted C 1 ~C 10 Alkylene, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenylene, substituted or unsubstituted C 6 ~C 10 Cycloalkylene, or substituted or unsubstituted C 6 ~C 10 arylene, and R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 6 ~C 10 Aryl, or substituted or unsubstituted C 6 ~C 10 arylalkyl) and at least one compound of A polymer (D) obtained by reacting

[0087] 2. The polymer (D) according to embodiment 1, wherein the epoxide (E) has an average functionality in the range of 3 to 10.

[0088] 3. The polymer (D) according to any one of embodiments 1 to 2, wherein the epoxide (E) has a number average molecular weight in the range of 500 to 10,000 g / mol, as determined by GPC using THF as solvent.

[0089] 4. At least one epoxide (E) is selected from the group consisting of: [ka] TIFF2025501230000075.tif229163 TIFF2025501230000076.tif116117 A polymer (D) according to any one of embodiments 1 to 3 selected from these polymer forms, or a mixture of two or more of these.

[0090] 5. Polymer (D) according to embodiment 4, in which at least one epoxide (E) is selected from E1, E2, E3, polymeric forms thereof or mixtures of two or more thereof.

[0091] 6. At least one compound (P) having at least one pigment-affinity group having at least one active hydrogen reactive towards an epoxide group is selected from the group consisting of diphenolic acid, 3-hydroxynaphthalene-2-carboxylic acid, dialkanolamine, dialkylamine, dibenzylamine, or (B1) or (B2). [ka] (Wherein, G is -NH- or -CH 2 - selected from The dotted lines represent optional bonds; R 5 , R 6 , R 7 , R 8 , R9 and R 10 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 5 ~C 24 Cycloalkyl, substituted or unsubstituted C 5 ~C 24 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C 6 ~C 10 aryl, or R 5 , and R 6 together with the carbon atom to which they are attached, or R 9 , and R 10 together with the carbon atom to which they are attached, or R 6 , and R 7 form together with the carbon atom to which they are attached a substituted or unsubstituted, unsaturated or aromatic 5-20 membered carbocyclic ring optionally containing as ring member(s) 1, 2 or 3 heteroatom(s) selected from O, N or S; However, R 5 , R 6 , R 7 , R 8 , R 9 , or R 10 At least one of the following is at least one -OH, -NHR 11 - or -SH, R 11 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 5 ~C 24Cycloalkyl, substituted or unsubstituted C 5 ~C 24 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl) and at least one compound of formula (B) selected from C(1), C(2), C(3) or C(4), [ka] (In the formula, R 20 and R 21 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, substituted or unsubstituted C 5 ~C 24 Cycloalkyl, substituted or unsubstituted C 5 ~C 24 Cycloalkenyl, linear or branched, substituted or unsubstituted C 7 ~C 15 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl, R 20 and R 21 form together with the carbon atom to which they are attached a substituted or unsubstituted, unsaturated or aromatic 5-20 membered carbocyclic ring optionally containing as ring member(s) 1, 2 or 3 heteroatom(s) selected from O, N or S; The dotted lines represent optional bonds, and p is selected from 0, 1 or 2; [ka] (wherein the dotted lines represent optional bonds), [ka] (In the formula, R 22 is a linear or branched, substituted or unsubstituted C 1 ~C 20 Alkylene, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenylene, linear or branched, substituted or unsubstituted C 1 ~C 20 Heteroalkylene, substituted or unsubstituted C 6 ~C 10 Cycloalkylene, or linear or branched, substituted or unsubstituted C 6 ~C 10 arylene, The dotted lines represent optional bonds), and [ka] (In the formula, R 23 and R 24 is hydrogen, halogen, -NO 2 , S.O. 3 H, or -COOH; and (Dotted lines represent optional bonds) with at least one anhydride of formula (C) selected from:

[0092] 7. Polymer (D) according to embodiment 6, in which the at least one compound (P) having at least one pigment-affinity group having at least one active hydrogen is a reaction product obtained by reacting N-(2-hydroxyethyl)ethylene urea with at least one anhydride of formula (C1).

[0093] 8. At least one anhydride is [ka] TIFF2025501230000083.tif236158 TIFF2025501230000084.tif214157 TIFF2025501230000085.tif245158 TIFF2025501230000086.tif221157 or a mixture of two or more thereof.

[0094] 9. At least one compound of formula (I) [ka] and In the formula, X is C 1 ~C 18 Alkyl, C 2 ~C 18 Alkenyl or C 7 ~C 15 arylalkyl; Z is -CH 3 , -C 2 H 5 , -C 3 H 7 , or -C 6 H 6 are independently selected from m is 5 to 100; n is 0 to 20; X is selected from -OC(O)-RC(O)OH, -NHC(O)-RC(O)OH or -ORC(O)OH, R is C 1 ~C 10 Alkyl, C 2 ~C 10 Alkenyl, C 6 ~C 10 Alicyclic or C 6 selected from aromatic R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C10 Cycloalkyl, or substituted or unsubstituted C 6 ~C 10 The polymer (D) according to any one of the preceding embodiments, wherein the aryl is selected from aryl.

[0095] 10. Polymer (D) according to any one of the preceding embodiments, wherein the compound of formula (I) is a random or block copolymer and comprises at least 50% by weight of ethylene oxide in polymerized form, relative to the total weight of the compound of formula (I).

[0096] 11. Polymer (D) according to embodiment 10, in which the compound of formula (I) is a random or block copolymer and contains ethylene oxide in polymerized form in the range of 50 to 100% by weight relative to the total weight of the compound of formula (I).

[0097] 12. Polymer (D) according to embodiment 10, in which the compound of formula (I) is a random or block copolymer and has an ethylene oxide content in the range of 50 to 100% by weight and an propylene oxide content in the range of 0 to 50% by weight, relative to the total weight of the compound of formula (I).

[0098] 13. The polymer (D) according to any one of the preceding embodiments, wherein the molar ratio of the at least one epoxide (E) to the at least one compound (P) is in the range of 0.25 to 0.90.

[0099] 14. The polymer (D) according to any one of the preceding embodiments, wherein the molar ratio of the at least one epoxide (E) to the compound of formula (I) is in the range of 0.10 to 0.75.

[0100] 15. Polymer (D) according to any one of the preceding embodiments, having a number average molecular weight in the range of 2000 to 100000 g / mol, as measured by GPC using THF or chloroform as a solvent.

[0101] 16. Polymer (D) according to embodiment 15, having a number average molecular weight in the range of 10,000 to 50,000 g / mol, as measured by GPC using THF as the solvent.

[0102] 17. A method for preparing a polymer (D) according to any one of the preceding embodiments, comprising the steps of: a. providing at least one epoxide (E) having an average functionality of 3.0 or more and a number average molar mass in the range of 250 to 25000 g / mol, determined by GPC using THF as solvent; b. Formula (I) [ka] (wherein Y is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 30 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 30 Alkenyl, or substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 7 ~C 15 Arylalkyl, substituted or unsubstituted C 6 ~C 10 Arylalkyl, or substituted or unsubstituted C 6 ~C 10 aryl; Z is C 1 ~C 6 Alkyl or C 6 ~C 10 aryl; m is 5 to 500; n is 0 to 100; X is -OC(O)-RC(O)OH, -NR 1 C(O)-RC(O)OH, -ORC(O)OH, -OC(O)-R-SH, -NHR 1 or -OR-SH, In the formula, R is a linear or branched, substituted or unsubstituted C 1 ~C 10Alkylene, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenylene, substituted or unsubstituted C 6 ~C 10 Cycloalkylene, or substituted or unsubstituted C 6 ~C 10 arylene, and R 1 is hydrogen, linear or branched, substituted or unsubstituted C 1 ~C 10 Alkyl, linear or branched, substituted or unsubstituted C 2 ~C 10 Alkenyl, substituted or unsubstituted C 6 ~C 10 Cycloalkyl, substituted or unsubstituted C 6 ~C 10 Aryl, or substituted or unsubstituted C 6 ~C 10 arylalkyl) to obtain a mixture; and c. providing at least one compound (P) having at least one pigment-affinitive group having at least one active hydrogen to obtain a ternary mixture; d. heating the mixture obtained in step c. to a desired temperature to obtain a product. The method includes:

[0103] 18. The process according to embodiment 17, wherein in step d., the reaction is carried out at a temperature in the range of 20 to 250° C. (preferably 100 to 140° C.).

[0104] 19. The method according to any one of embodiments 17 to 18, wherein steps a. to d. are carried out in the presence of at least one solvent or in the absence of a solvent.

[0105] 20. The method according to embodiment 19, wherein the at least one solvent is selected from an alcohol, a ketone, an ester, an aromatic solvent, an aliphatic solvent, a cyclic ether, an ether, an ether alcohol, or a mixture of two or more thereof.

[0106] 21. The method according to any one of embodiments 16 to 20, wherein the reaction in step d. is carried out for a time ranging from 10 minutes to 10 hours.

[0107] 22. Use of a polymer (D) according to any one of embodiments 1 to 16 as a dispersant for particulate solid materials.

[0108] 23. The use according to embodiment 22, wherein the particulate solid material is a pigment.

[0109] 24. a. a polymer (D) according to any one of embodiments 1 to 16, and b. at least one particulate solid material selected from a pigment or a filler; c. at least one liquid diluent; and d. at least one polymeric binder Including, A composition in the form of a dispersion, wherein said particulate solid material is dispersed in a liquid diluent selected from an organic solvent or water or a mixture of both.

[0110] 25. The composition according to embodiment 24, wherein the weight ratio of the particulate solid material to the polymer (D) according to any one of embodiments 1 to 16 is in the range of 20:1 to 1:20 ((100 parts pigment to 5 parts dispersant) to (100 parts pigment to 500 parts dispersant).

[0111] 26. A composition according to embodiment 24 or 25, comprising: a) ≧1 to ≦70% by weight, based on the total weight of the composition, of particulate solid material selected from pigments or fillers; b) ≧0.5 to ≦50% by weight, based on the total weight of the composition, of a polymer (D) according to any one of the preceding embodiments 1 to 16, and c) ≧10 to ≦98.5% by mass of a liquid diluent based on the total mass of the composition A composition comprising:

[0112] 27. The composition according to any one of embodiments 24 to 26, in the form of a millbase, or a coating composition.

[0113] 28. Particle size (D) in the range of 10-500 nm measured using dynamic light scattering technique 50 28. The composition according to any one of embodiments 24 to 27, having EXAMPLES

[0114] The claimed invention is further described in the following non-limiting examples. More specifically, the test methods identified below are part of the general disclosure of this application and are not limited to the specific examples.

[0115] material and method 1-(2-hydroxyethyl)-2-imidazolidinone, available from Sartomer USA as SR512. Succinic anhydride is available from Sigma Aldrich. Poly(ethylene glycol) methyl ether (MPEG-2K) was obtained from Clariant (Polyglykol M2000). The glycidyl ether of 1,1,2,2-tetrakis(p-hydroxyphenyl)ethane is available from Kukdo Chemical Company as Epokukdo KDT-4400. 4,4-Bis(4-hydroxyphenyl)valeric acid is available from Sigma Aldrich. Paliogen® Maroon L3920, BASF Perrindo® Maroon 179 229-8801, Sun Chemicals.

[0116] Preparation of intermediate 1 (P): Molten 1-(2-hydroxyethyl)-2-imidazolidinone (38.64 g) was charged to a three-neck flask equipped with a stirrer, thermocouple, and nitrogen inlet flask, to which succinic anhydride (29.71 g) was charged. The mixture was reacted at 100-105° C. while being monitored by FTIR until the anhydride was completely reacted to give the compound pigment affinity group (P).

[0117] Preparation of intermediate 2 (compound of formula I): Poly(ethylene glycol) methyl ether (447.5 g) having an average molecular weight (Mw) of 2000 was reacted with succinic anhydride (25.92 g) at 120° C. for 2.5 hours to obtain intermediate 2.

[0118] Synthesis example 2 (C51) A four-neck flask equipped with a stirrer, water-cooled condenser and nitrogen inlet was charged with molten intermediate 2 (167.6 g) and 1.66 g of zinc acetylacetonate, and under stirring, glycidyl ether of 1,1,2,2-tetrakis(p-hydroxyphenyl)ethane (KDT-4400 (47.6 g)) and 25 g of methyl isobutyl ketone were added and heated to 115°C. Next, intermediate 1 (6.66 g) was charged and reacted at 110-111°C for 40 minutes, followed by the addition of 4,4-bis(4-hydroxyphenyl)valeric acid (23.2 g) and methyl ethyl ketone (5 g). The reaction was carried out at a temperature of 120-125°C to the desired reaction completion as confirmed by monitoring the epoxy equivalent weight to be greater than 13000 g / eq. The process solvent was distilled off during this process. Heating was stopped and the polymer was diluted with methyl ethyl ketone (80 g) and propylene glycol n-propyl ether (20 g) to give a homogeneous solution. The product was obtained as a clear, medium viscosity, deep yellowish amber solution with a non-volatile content of 70.0% (110° C., 1 hr).

[0119] Synthesis example 3 (C78) A four-neck flask equipped with a stirrer, water-cooled condenser and nitrogen inlet was charged with molten intermediate 2 (215.1 g) and KDT-4400 (47.58 g) and heated to 85°C, followed by the addition of 1.96 g of benzyltrimethylammonium hydroxide solution (40% in methanol) and further heating to 120°C. After 1 hour at 120°C, 4,4-bis(4-hydroxyphenyl)valeric acid (40.4 g) and methyl ethyl ketone (10 g) were charged. The reaction was carried out at a temperature of 120-125°C until completion, which was confirmed by monitoring the epoxy equivalent weight to be greater than 20000 g / eq. The process solvent was distilled off during this process. Heating was stopped and the polymer was diluted with methyl ethyl ketone (104 g) and propylene glycol n-propyl ether (26 g) to a homogeneous solution. The product was obtained as a clear, medium viscosity, deep yellowish amber solution with 69.9% non-volatiles (110° C., 1 hour).

[0120] Synthesis Example 4 (C79) A four-neck flask equipped with a stirrer, water-cooled condenser and nitrogen inlet was charged with molten intermediate 2 (175.7 g) and KDT-4400 (48.8 g) and heated to 85°C, followed by the addition of 1.4 g of benzyltrimethylammonium hydroxide solution (40% in methanol) and further heating to 120°C. After 20 minutes, intermediate 1 (26.5 g) was charged. The reaction was further run at a temperature of 120-125°C until the desired reaction completion was reached as confirmed by monitoring the epoxy equivalent weight to be greater than 20000 g / eq. The process solvent was distilled off during this process. Heating was stopped and the polymer was diluted with methyl ethyl ketone (104 g) and propylene glycol n-propyl ether (26 g) to a homogeneous solution. The product was obtained as a clear, medium viscosity, deep yellowish amber solution with a non-volatile content of 69.7% (110°C, 1 hr).

[0121] Synthesis Example 5 (C80) A four-neck flask equipped with a stirrer, water-cooled condenser, and nitrogen inlet was charged with molten intermediate 2 (217.7 g) and KDT-4400 (59.4 g) and heated to 85°C, after which 1.85 g of benzyltrimethylammonium hydroxide solution (40% in methanol) was added, further heated to 120°C, and intermediate 1 (17.1 g) was charged. After 30 minutes at 125°C, 4,4-bis(4-hydroxyphenyl)valeric acid (21.3 g) was charged and the reaction was further run at a temperature of 125-127°C to the desired reaction completion as confirmed by monitoring that the epoxy equivalent was greater than 20000 g / eq. Heating was stopped and the polymer was diluted with methyl ethyl ketone (104 g) and propylene glycol n-propyl ether (26 g) to give a homogeneous solution. The product was obtained as a clear, medium viscosity, deep yellowish amber solution with a non-volatile content of 69.2% (110° C. for 1 hour).

[0122] Synthesis Example 6 (C87) A four-neck flask equipped with stirrer, water-cooled condenser and nitrogen inlet was charged with molten intermediate 1 (43.1 g) and intermediate 2 (164.5 g) and heated to 85°C, after which 1.4 g of benzyltrimethylammonium hydroxide solution (40% in methanol) was added and further heated to 105°C. KDT-4400 (59.4 g) was charged and the reaction mass was further heated to 125°C. The reaction was further carried out at a temperature of 125-127°C until the desired reaction completion as confirmed by monitoring that the epoxy equivalent was greater than 20000 g / eq. Heating was stopped and the polymer was diluted with methyl ethyl ketone (152 g) and propylene glycol n-propyl ether (26 g) to obtain a homogeneous solution. The product was obtained as a clear solution of medium viscosity, deep yellowish amber color with non-volatile content of 62.2% (1 hr at 110°C).

[0123] Preparation of pigment dispersion Pigment Red 179 (PR179) and Pigment Violet 29 (PR29) were separately dispersed in deionized water using a Vibroshaker as the grinding device with the inventive dispersant (C51) and comparative dispersant D1. The dispersion process was carried out in two stages using different types of grinding media, 0.8 mm yttria stabilized zirconia beads for 4 hours and then 0.3 mm yttria stabilized zirconia beads for 4 hours. The ratio of grinding media to mill base was 2:1 (w / w). The composition of the mill base is disclosed in Table 1. The dispersant was filtered after each stage and the grinding media was replaced. The pigment loading was 10% by weight in the total formulation. The particle size (D50) of the resulting pigment dispersion is shown in Table 2.

[0124] Crushing The aqueous pigment pastes were milled in a model DAS H-TP200-K (LAU GmbH, Hemer, Germany) equipped with a Lau Disperser-cooling system, unless otherwise stated. To mill the pigments, 0.3 mm yttria-stabilized zirconia beads (Fox Industries, Fairfield, New Jersey, USA) were added to each formulation shaken in the Lau Disperser. For aqueous systems, the beads were approximately 200% of the total formulation mass, e.g., 100 g of formulation was added with 200 g of beads for a total of 300 g. The pretreated samples were then placed in a model DAS H-TP200-K (LAU GmbH, Hemer, Germany) equipped with a Lau Disperser-cooling system and shaken by a fan for 540 min or 9 h. After the run, the samples were filtered to remove the beads and stored in aluminum paint cans. The filtered beads were washed with solvent and reused. All formulation examples used 40% resin solids by weight relative to pigment solids, and all formulations were prepared at 10% pigment by weight. Example 9 was prepared by milling a pigment paste in a DCP-12 Superflow mill (Draiswerke GmbH, Mannheim, Germany) using commercial grinding resin 350CD0001 (BASF Corp., 26701 Telegraph Rd. Southfield, MI 48033) and Parodur EL48.6 (BASF) milled with 0.3 mm yttria-stabilized zirconia beads (Fox Industries, Fairfield, New Jersey, USA). The compositions of the millbases are disclosed in Tables 3 and 4.

[0125] Color evaluation Aqueous pigment dispersions of Perylene Red Paliogen Maroon L3920 (BASF SE) and Perrindo Maroon 229-8801 (Sun Chemical) were evaluated for color performance in unpigmented and pigmented formulations prepared according to customer formulation guidelines for General Motors (GM) water-based basecoat, a one-component basecoat available from BASF Corp., 26701 Telegraph Rd. Southfield, MI 48033. The pigments were added to the unpigmented or pigmented basecoat under stirring, and the pH of the basecoat was adjusted to 8.1 with a 20% by weight aqueous solution of N,N-dimethylethanolamine (BASF, Geismar, Louisiana, USA). The pH was measured using a Starter 300 pH portable pH meter (Ohaus Corporation, Parsippany, New Jersey, USA). Films were formed on Melinex drawdown sheets (Puetz GmbH+C0.Folien KG, Taunusstein, Germany) using a 100 μm gap on a Byk drawdown bar (Byk-Chemie GmbH, Wesel, Germany) and allowed to flash for approximately 20 minutes. Samples were then baked at 270° F. for 30 minutes.

[0126] Once the samples had cooled, the color spectra were measured using a Byk Mac i spectrophotometer (Byk-Chemie GmbH, Wesel, Germany). The Melinex card with the basecoat drawdown was placed on a reflector. The basecoat drawdown was adjacent to the mirror. The Byk Mac i was then placed on top of the Melinex card and mirror and the color data of the basecoat was measured in off-specular 15°, 25°, 45°, 75° and 110° d65 light through the Melinex film using GM CieLab weighting. Measurements were taken five times for each sample. These measurement data are shown in Table 5.

[0127] The sprayed panels were prepared by spraying stainless steel panels, which had been precoated with a primer layer, with a pigmented water-based basecoat, then going through a flash step, and finally spraying with a commercial two-part clearcoat (BASF Corp., 26701 Telegraph Rd. Southfield, MI 48033) and baking for approximately 25 minutes at 265° F. A color analysis of the sprayed panels is shown in Table 6.

[0128] This method is used because the larger the pigment aggregate particle size, the more light is scattered, resulting in a higher lightness measurement for the film. The 110° angle has the longest film path length and is therefore the most sensitive to detect increased scattering. Therefore, the L value (lightness) at the 110° angle was used for evaluation. Dispersions that yield lower values ​​are more transparent and better.

[0129] [Table 1]

[0130] The particle size of the above compositions was measured using digital light scattering techniques (Desia nano C particle size distribution analyzer).

[0131] [Table 2]

[0132] As is evident from Table 2, the dispersants according to the claimed invention are capable of producing smaller submicron particle size pigment dispersions at lower loadings than the comparative examples.

[0133] [Table 3]

[0134] [Table 4]

[0135] *Maintained 40% resin solids to pigment solids. Solids content may vary depending on resin batch.

[0136] [Table 5]

[0137] C1 is a comparison of A1, A2, A3 and A4. C3 is a comparison of A6 and A7.

[0138] [Table 6]

[0139] As can be seen from Tables 5 and 6, the dispersants according to the claimed invention showed superior values ​​on Melinex drawdown and on sprayed panels in formulations with a WB basecoat.

Claims

1. a. at least one epoxide (E) having an average functionality equal to or greater than 3.0 and a number average molar mass in the range of 250 to 25000 g / mol, as determined by GPC using THF as solvent; b. at least one compound (P) having at least one pigment affinity group, the pigment affinity group having at least one active hydrogen reactive with an epoxide group; c. Formula (I) 【Chemistry 1】 (wherein Y is hydrogen, linear or branched, substituted or unsubstituted C １ ~C ３０ Alkyl, linear or branched, substituted or unsubstituted C ２ ~C ３０ Alkenyl, or substituted or unsubstituted C ６ ~C １０ Cycloalkyl, substituted or unsubstituted C ７ ~C １５ Arylalkyl, substituted or unsubstituted C ６ ~C １０ Arylalkyl, or substituted or unsubstituted C ６ ~C １０ aryl; Z is C １ ~C ６ Alkyl or C ６ ~C １０ aryl; m is 5 to 500; n is 0 to 100; X is -OC(O)-R-C(O)OH, -NR １ C(O)-R-C(O)OH, -ORC(O)OH, -OC(O)-R-SH, -NHR １ or -O-R-SH, In the formula, R is a linear or branched, substituted or unsubstituted C １ ~C １０ Alkylene, linear or branched, substituted or unsubstituted C ２ ~C １０ Alkenylene, substituted or unsubstituted C ６ ~C １０ Cycloalkylene, or substituted or unsubstituted C ６ ~C １０ arylene, and R １ is hydrogen, linear or branched, substituted or unsubstituted C １ ~C １０ Alkyl, linear or branched, substituted or unsubstituted C ２ ~C １０ Alkenyl, substituted or unsubstituted C ６ ~C １０ Cycloalkyl, substituted or unsubstituted C ６ ~C １０ Aryl, or substituted or unsubstituted C ６ ~C １０ arylalkyl) and at least one compound of The polymer (D) is obtained by reacting

2. 2. The polymer (D) of claim 1, wherein the epoxide (E) has an average functionality in the range of 3 to 10.

3. At least one epoxide (E) is selected from the group consisting of 【Chemistry 2】 【change】 【change】 The polymer (D) according to claim 1 or 2, selected from these polymer forms or a mixture of two or more of these.

4. At least one compound (P) having at least one pigment-affinity group having at least one active hydrogen reactive towards epoxide groups is selected from the group consisting of diphenolic acid, 3-hydroxynaphthalene-2-carboxylic acid, dialkanolamine, dialkylamine, dibenzylamine, or (B1) or (B2). 【Chemistry 3】 (Wherein, G is -NH- or -CH ２ - selected from The dotted lines represent optional bonds; R ５ , R ６ , R ７ , R ８ , R ９ and R １０ is hydrogen, linear or branched, substituted or unsubstituted C １ ~C ３０ Alkyl, linear or branched, substituted or unsubstituted C ２ ~C ３０ Alkenyl, substituted or unsubstituted C ５ ~C ２４ Cycloalkyl, substituted or unsubstituted C ５ ~C ２４ Cycloalkenyl, linear or branched, substituted or unsubstituted C ７ ~C １５ Arylalkyl, substituted or unsubstituted C ６ ~C １０ aryl, or R ５ , and R ６ together with the carbon atom to which they are attached, or R ９ , and R １０ together with the carbon atom to which they are attached, or R ６ , and R ７ together with the carbon atoms to which they are attached form a substituted or unsubstituted, unsaturated or aromatic 5-20 membered carbocyclic ring optionally containing 1, 2 or 3 heteroatoms selected from O, N or S as ring members; R １１ is hydrogen, linear or branched, substituted or unsubstituted C １ ~C ３０ Alkyl, linear or branched, substituted or unsubstituted C ２ ~C ３０ Alkenyl, substituted or unsubstituted C ５ ~C ２４ Cycloalkyl, substituted or unsubstituted C ５ ~C ２４ Cycloalkenyl, linear or branched, substituted or unsubstituted C ７ ~C １５ Arylalkyl, or substituted or unsubstituted C ６ ~C １０ aryl; However, R ５ , R ６ , R ７ , R ８ , R ９ , or R １０ At least one of the groups is at least one of -OH, -NHR １１ - or -SH, R １１ is hydrogen, linear or branched, substituted or unsubstituted C １ ~C ３０ Alkyl, linear or branched, substituted or unsubstituted C ２ ~C ３０ Alkenyl, substituted or unsubstituted C ５ ~C ２４ Cycloalkyl, substituted or unsubstituted C ５ ~C ２４ Cycloalkenyl, linear or branched, substituted or unsubstituted C ７ ~C １５ Arylalkyl, or substituted or unsubstituted C ６ ~C １０ aryl) and at least one compound of formula (B) selected from C(1), C(2), C(3) or C(4), 【Chemistry 4】 (In the formula, R ２０ and R ２１ is hydrogen, linear or branched, substituted or unsubstituted C １ ~C ３０ Alkyl, linear or branched, substituted or unsubstituted C ２ ~C ３０ Alkenyl, substituted or unsubstituted C ５ ~C ２４ Cycloalkyl, substituted or unsubstituted C ５ ~C ２４ Cycloalkenyl, linear or branched, substituted or unsubstituted C ７ ~C １５ Arylalkyl, or substituted or unsubstituted C ６ ~C １０ aryl, R ２０ and R ２１ together with the carbon atoms to which they are attached form a substituted or unsubstituted, unsaturated or aromatic 5-20 membered carbocyclic ring optionally containing 1, 2 or 3 heteroatoms selected from O, N or S as ring members; The dotted lines represent optional bonds, and p is selected from 0, 1 or 2; 【Chemistry 5】 (wherein the dotted lines represent optional bonds), 【Chemistry 6】 (In the formula, R ２２ is a linear or branched, substituted or unsubstituted C １ ~C ２０ Alkylene, linear or branched, substituted or unsubstituted C ２ ~C ３０ Alkenylene, linear or branched, substituted or unsubstituted C １ ~C ２０ Heteroalkylene, substituted or unsubstituted C ６ ~C １０ Cycloalkylene, or linear or branched, substituted or unsubstituted C ６ ~C １０ arylene, the dotted lines represent optional bonds), and 【Chemistry 7】 (In the formula, R ２３ and R ２４ is hydrogen, halogen, -NO ２ , or S.O. ３ H, or —COOH; and The dotted lines represent optional bonds. or a mixture of two or more of these.

5. The at least one anhydride is 【Chemistry 8】 【change】 【change】 【change】 【change】 or a mixture of two or more thereof.

6. At least one compound of formula (I) 【Chemistry 9】 and In the formula, X is C １ ~C １８ Alkyl, C ２ ~C １８ Alkenyl or C ７ ~C １５ arylalkyl; Z is -CH ３ , -C ２ H ５ , -C ３ H ７ , or -C ６ H ６ are independently selected from m is 5 to 100; n is 0 to 20; X is selected from -OC(O)-R-C(O)OH, -NHC(O)-R-C(O)OH or -ORC(O)OH, wherein R is C １ ~C １０ Alkyl, C ２ ~C １０ Alkenyl, C ６ ~C １０ Alicyclic or C ６ selected from aromatic R １ is hydrogen, linear or branched, substituted or unsubstituted C １ ~C １０ Alkyl, linear or branched, substituted or unsubstituted C ２ ~C １０ Alkenyl, substituted or unsubstituted C ６ ~C １０ Cycloalkyl, or substituted or unsubstituted C ６ ~C １０ 3. The polymer (D) according to claim 1 or 2, wherein the aryl is selected from the group consisting of aryl and aryl.

7. 3. Polymer (D) according to claim 1 or 2, in which the compound of formula (I) is a random or block copolymer and comprises at least 50% by weight of ethylene oxide in polymerized form, relative to the total weight of the compound of formula (I).

8. 3. Polymer (D) according to claim 1 or 2, wherein the compound of formula (I) is a random or block copolymer and has a content of ethylene oxide in the range of 50 to 100% by weight and propylene oxide in the range of 0 to 50% by weight, respectively, relative to the total weight of the compound of formula (I).

9. 3. Polymer (D) according to claim 1 or 2, having a number average molecular weight in the range of 2000 to 100000 g / mol, as measured by GPC using THF or chloroform as solvent.

10. A process for preparing polymer (D), comprising the following steps: a. providing at least one epoxide (E) having an average functionality of 3.0 or greater and a number average molar mass in the range of 250-25000 g / mol, as determined by GPC using THF as solvent; b. Formula (I) 【Chemistry 10】 (wherein Y is hydrogen, linear or branched, substituted or unsubstituted C １ ~C ３０ Alkyl, linear or branched, substituted or unsubstituted C ２ ~C ３０ Alkenyl, or substituted or unsubstituted C ６ ~C １０ Cycloalkyl, substituted or unsubstituted C ７ ~C １５ Arylalkyl, substituted or unsubstituted C ６ ~C １０ Arylalkyl, or substituted or unsubstituted C ６ ~C １０ aryl; Z is C １ ~C ６ Alkyl or C ６ ~C １０ aryl; m is 5 to 500; n is 0 to 100; X is -OC(O)-R-C(O)OH, -NR １ C(O)-R-C(O)OH, -ORC(O)OH, -OC(O)-R-SH, -NHR １ or -O-R-SH, In the formula, R is a linear or branched, substituted or unsubstituted C １ ~C １０ Alkylene, linear or branched, substituted or unsubstituted C ２ ~C １０ Alkenylene, substituted or unsubstituted C ６ ~C １０ Cycloalkylene, or substituted or unsubstituted C ６ ~C １０ arylene, and R １ is hydrogen, linear or branched, substituted or unsubstituted C １ ~C １０ Alkyl, linear or branched, substituted or unsubstituted C ２ ~C １０ Alkenyl, substituted or unsubstituted C ６ ~C １０ Cycloalkyl, substituted or unsubstituted C ６ ~C １０ Aryl, or substituted or unsubstituted C ６ ~C １０ arylalkyl) to obtain a mixture; and c. providing at least one compound (P) having at least one pigment-affinitive group having at least one active hydrogen to obtain a ternary mixture; d. Heating the mixture obtained in step c. to a desired temperature to obtain product (D); The method includes:

11. 3. Use of a polymer (D) according to claim 1 or 2 as a dispersant for particulate solid materials.

12. 12. The use according to claim 11, wherein the particulate solid material is a pigment.

13. a. the polymer (D) of claim 1, and b. at least one particulate solid material selected from a pigment or a filler; c. at least one liquid diluent, and d. at least one polymeric binder Including, A composition in the form of a dispersion, wherein said particulate solid material is dispersed in a liquid diluent selected from an organic solvent or water or a mixture of both.

14. a) ≧1 to ≦70% by weight, based on the total weight of the composition, of a particulate solid material selected from a pigment or a filler; b) ≧0.5 to ≦50% by weight, based on the total weight of the composition, of the polymer (D) according to claim 1, and c) ≧10 to ≦98.5% by weight of a liquid diluent, based on the total weight of the composition The composition of claim 13 comprising:

15. Particle size (D) in the range of 10-500 nm as measured using dynamic light scattering technique ５０ 14. The composition of claim 13 having the formula:

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