Polyether dispersant with light stabilizing effect

Abstract

The present invention relates to a polymer obtained by reacting a polyether with a hindered amine light stabilizer (HALS). The present invention relates to a method for preparing the polymer. The present invention also relates to a liquid composition containing the polymer, and the use of the polymer as a dispersant and light stabilizer.

Description

[Technical Field]

[0001] The present invention relates to a polymer obtained by reacting a polyether with a hindered amine light stabilizer (HALS). The present invention relates to a method for preparing the polymer. The present invention also relates to a liquid composition containing the polymer, and to the use of the polymer as a dispersant and as a light stabilizer. [Background technology]

[0002] Liquid pigment compositions containing a pigment, a filler, and a liquid vehicle are commonly used in a variety of industrial and consumer technology applications, particularly for pigmenting coating compositions such as solvent-borne and water-borne coatings, heavy-duty coatings, automotive coatings, printing inks, or for pigmenting cosmetics, plastics, and the like.

[0003] Therefore, there is a continuing need for polymers that are suitable as dispersants for pigments and that provide high stability, reduced viscosity especially at high pigment loadings, and improved optical properties of the coating, such as gloss, color strength, reduced yellowing, rub-out properties or reduced cratering.

[0004] An important property of the dried coating is weathering stability, which is promoted by the addition of light stabilizers.

[0005] The dispersant properties are useful for uniformly dispersing particulate materials such as pigments and fillers in the liquid composition and for the stability of the liquid composition; while the light stabilizer properties provide weathering stability to coatings obtained from the liquid composition.

[0006] Polymers or oligomers with light stabilizers are known in the state of the art and are described, for example, in the following references:

[0007] US Pat. No. 9,394,244 B2 disclosed polyallophanate oligomers containing ethylenically unsaturated groups and polymeric stabilizer groups selected from hindered amine light stabilizers, ultraviolet absorbers, antioxidants, and dihydrocarbylhydroxylamines.

[0008] Polymers or oligomers with light stabilizers disclosed in the prior art have limitations such as poor dispersant properties, poor light stabilizer properties, or both. [Prior art documents] [Patent documents]

[0009] [Patent Document 1] U.S. Patent No. 9,394,244 B2 Summary of the Invention [Problem to be solved by the invention]

[0010] Therefore, an object of the present invention is to provide a polymer that is useful as a dispersant in a liquid composition and has light stabilizer properties. It is an object of the present invention to provide a polymer that has good dispersant properties in a liquid composition, such as improved viscosity and improved stability. Furthermore, it is desirable that the polymer provide good light stabilizer effects (good weatherability) to coatings obtained from the liquid composition. [Means for solving the problem]

[0011] It has surprisingly been found that the polymers of the present invention, obtained by reacting polyethers with hindered amine light stabilizers (HALS), are useful as dispersants and light stabilizers.

[0012] Thus, one aspect of the present invention is at least one polyether A, at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6, or mixtures thereof; at least one compound B having at least one functional group selected from the group consisting of ester, isocyanate, anhydride, carboxylic acid or epoxide, wherein the at least one compound B is selected from B1, B2, B3, B4, B5 or a mixture thereof, a polymer P obtained by reacting or at least one polyether A, at least one hindered amine light stabilizer selected from H2, H4, H6, or mixtures thereof; A polymer P obtained by reacting the at least one polyether A is selected from at least one polyether of general formula A(a), at least one polyether of general formula A(b), or a mixture thereof; (a) At least one polyether of general formula A(a) is [ka] Formula A(a) (In the formula, R 1 is a linear or branched, substituted or unsubstituted C1-C 22 Alkyl, straight or branched chain, substituted or unsubstituted C1-C 22 Alkylenyl, substituted or unsubstituted C6-C 15 Alkylaryl, or substituted or unsubstituted C6-C 14 aryl; R 2 is selected from straight or branched chain, substituted or unsubstituted C1-C4 alkyl; m is an integer ranging from 1 to 100; n is an integer ranging from 0 to 100; the m units and the n units are distributed to form a random copolymer, a block copolymer, or a gradient copolymer; and Z is -OH, -NH2, or -NHR 3 is selected from, where R3 is a linear or branched, substituted or unsubstituted C1-C 22 alkyl); (b) at least one polyether of general formula A(b) is at least one polyether of general formula A(a) [ka] Formula A(a) (In the formula, R 1 , R 2 , m, n, and Z are as defined above) At least one compound of formula (E) [ka] Formula (E) (In the formula, R 4 is a linear or branched, substituted or unsubstituted C1-C 22 Alkyl, straight or branched chain, substituted or unsubstituted C1-C 22 Alkylenyl, substituted or unsubstituted C6-C 15 Alkylaryl, or substituted or unsubstituted C6-C 14 aryl, and X is selected from O, S or CH2; the molar ratio of the at least one polyether of general formula A(a) to the at least one compound of formula (E) is in the range of 1:0.8 to 1:5; moreover a) Hindered amine light stabilizers (HALS) of general formula H1 are [ka] formula H1 (In the ceremony R 5 and R 6 are independently H or substituted or unsubstituted C 1~4 alkyl; R 7 -OH, -NH2, -NHR 9 , -R10 -OH, -R 10 -NH2, or -R 10 -NHR 9 Selected from; R 8 -H, -O·, straight or branched chain substituted or unsubstituted C1-C 22 Alkyl, straight or branched chain substituted or unsubstituted C3-C8 cycloalkyl, -OR 11 , -R 12 -OH, or -OR 12 -OH; where R 9 , and R 11 are independently straight or branched chain substituted or unsubstituted C1-C 22 alkyl; where R 10 and R 12 are independently straight or branched chain substituted or unsubstituted C1-C 22 alkylene); b) Hindered amine light stabilizer (HALS) H2 (i) 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol; and (ii) General formula: [ka] (In the formula, R 13 is a linear or branched, substituted or unsubstituted C1-C 12 alkyl; R 14 is a linear or branched, substituted or unsubstituted C2-C 12 at least one dicarboxylic acid ester of a HALS copolymer comprising: c) Hindered amine light stabilizers (HALS) of general formula H3 are triazine-based dimers containing -NH or -OH- functional groups: [ka] formula H3 (In the formula, R 5 , R 6 , and R 8 is as defined above; R 15 is selected from H or straight or branched chain substituted or unsubstituted C1-C6 alkyl; R 16 is selected from H or straight or branched chain substituted or unsubstituted C1-C6 alkyl; R 17 -H or -R 18 -OH, and R 18 is a linear or branched, substituted or unsubstituted C1-C 22 alkylene); d) Hindered amine light stabilizers (HALS) of general formula H4 are diester or carbonate functionalized HALS compounds: [ka] Formula H4 (In the formula, R 5 , R 6 , and R 8 is as defined above; L1 is [ka] or [ka] and; where * indicates the point of attachment to O, R 19 is a linear or branched, substituted or unsubstituted C1-C 22 alkylene); e) Hindered amine light stabilizer (HALS) H5 is a triazine-substituted alkylamine-based oligomer having an NH-functional group: 1,5,8,12-tetrakis[4,6-bis(N-butyl-N-1,2,2,6,6-pentamethyl-4-piperidylamino)-1,3,5-triazin-2-yl]-1,5,8,12-tetraazadodecane; f) Hindered amine light stabilizer (HALS) H6 is a polyol polyester: tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)butane-1,2,3,4-tetracarboxylate; moreover B1 is a group of general formula R 20 (COOR 21 ) q (In the formula, R 20 is a linear or branched, substituted or unsubstituted C1-C 22 -Alkylene, or substituted or unsubstituted C-C 10 arylene; R 21 is a linear or branched, substituted or unsubstituted C1-C 12 -alkyl; and q is an integer ranging from 2 to 5; B2 has the general formula: [ka] (In the formula, R 22 is at least one phthalic anhydride derivative selected from 4-COOH, 4-NO2, 4-F, 4-Cl, or 4-Br; B3 has the general formula: G(NCO) r (Wherein G is a linear or branched, substituted or unsubstituted C2-C 22 Alkyl, straight or branched chain substituted or unsubstituted C3-C8 cycloalkyl, or substituted or unsubstituted C6-C 14 arylene, and and r is 2 or 3 or 4; B4 is at least one epoxy polymer; and B5 relates to polymer P, which is at least one maleic anhydride polymer.

[0013] Another aspect of the present invention relates to a method for preparing polymer P.

[0014] Yet another aspect of the present invention relates to a liquid composition comprising polymer P.

[0015] Yet another aspect of the present invention is a method for producing a medicament comprising: i. a polymer P of the invention; ii. at least one particulate solid material selected from a pigment, a filler, or a mixture thereof; iii. at least one liquid diluent, and iv. at least one polymer binder 1. A coating composition comprising: The present invention relates to a coating composition in which at least one particulate solid material is dispersed in a liquid diluent selected from an organic solvent, water, a reactive diluent, or a mixture thereof.

[0016] Yet another aspect of the present invention relates to the use of polymer P as a dispersant.

[0017] Yet another aspect of the present invention relates to the use of polymer P as a light stabilizer.

[0018] Yet another aspect of the present invention relates to the use of polymer P in a coating composition. DETAILED DESCRIPTION OF THE INVENTION

[0019] Before describing the compositions and processes of the claimed invention, it is to be understood that the invention is not limited to the particular compositions and processes described, as such compositions and processes may, of course, vary. It is also to be understood that the terms used herein are not intended to be limiting, as the scope of the claimed invention will be limited only by the appended claims.

[0020] Hereinafter, when a group is defined as including at least some embodiments, this preferably also means that the group consists only of those embodiments. Furthermore, in the specification and claims, terms such as "first," "second," "third," or "a," "b," "c," etc. are used to distinguish between similar elements and do not necessarily describe a sequential or chronological order. Terms so used are interchangeable under appropriate circumstances, and it is understood that the embodiments of the invention described herein can be practiced in orders other than those described or illustrated herein. When the terms "first," "second," "third," "(A)," "(B)," and "(C)," "(a)," "(b)," "(c)," "(d)," "i," "ii," etc. refer to steps in a method, use, or assay, there is no consistency in time or time intervals between steps, unless otherwise indicated in the application set forth herein above or below. That is, steps may be performed simultaneously, or there may be time intervals of seconds, minutes, hours, days, weeks, months, or even years between such steps.

[0021] 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 within the range. For the avoidance of doubt, applicants reserve the right to equivalents pursuant to applicable law.

[0022] In the following sections, different aspects of the invention are defined in more detail. Each aspect so defined may be combined with any one or more other aspects, unless expressly indicated otherwise. In particular, any feature designated as being preferred or advantageous may be combined with any other feature designated as being preferred or advantageous.

[0023] References throughout this specification to "one embodiment" or "an embodiment" mean that a particular feature, structure, or characteristic described with respect to that embodiment is included in at least one embodiment of the invention. Thus, the appearances of the phrases "in one embodiment" or "in an embodiment" in various places throughout this specification are not necessarily all referring to the same embodiment, although they may.

[0024] 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. Furthermore, although some embodiments described herein may include some features but not other features included in other embodiments, it will be understood by those skilled in the art that combinations of features from different embodiments are within the scope of the present invention and constitute different embodiments. For example, in the appended claims, any of the embodiments related to the claims may be utilized in any combination.

[0025] Surprisingly, it has been found that the polymers of the present invention, obtained by reacting a polyether with a hindered amine light stabilizer (HALS), are useful as dispersants and light stabilizers. Certain HALS, when covalently bonded to certain polyether polymers, function well as dispersants in liquid compositions and also as light stabilizers. The polyether polymer and the HALS are bonded either directly by a covalent bond or via a polyfunctional compound covalently bonded to each of them.

[0026] The present invention relates to polymers containing polyethers and hindered amine light stabilizers (HALS).

[0027] Thus, one aspect of the present invention is at least one polyether A, at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6, or mixtures thereof; at least one compound B having at least one functional group selected from the group consisting of ester, isocyanate, anhydride, carboxylic acid or epoxide, said at least one compound B being selected from B1, B2, B3, B4, B5 or mixtures thereof; a polymer P obtained by reacting or at least one polyether A, at least one hindered amine light stabilizer selected from H2, H4, H6, or mixtures thereof; A polymer P obtained by reacting the at least one polyether A is selected from at least one polyether of general formula A(a), at least one polyether of general formula A(b), or a mixture thereof; (a) said at least one polyether of general formula A(a) [ka] Formula A(a) (In the formula, R 1 is a linear or branched, substituted or unsubstituted C1-C 22 Alkyl, straight or branched chain, substituted or unsubstituted C1-C 22 Alkylenyl, substituted or unsubstituted C6-C 15 Alkylaryl, or substituted or unsubstituted C6-C 14 aryl; R 2 is selected from straight or branched chain, substituted or unsubstituted C1-C4 alkyl; m is an integer ranging from 1 to 100; n is an integer ranging from 0 to 100; the m units and the n units are distributed to form a random copolymer, a block copolymer, or a gradient copolymer; and Z is -OH, -NH2, or -NHR 3 is selected from, where R 3 is a linear or branched, substituted or unsubstituted C1-C 22 alkyl); (b) said at least one polyether of general formula A(b) is at least one polyether of general formula A(a): [ka] Formula A(a) (In the formula, R 1 , R 2 , m, n, and Z are as defined above) At least one compound of formula (E): [ka] Formula (E) (In the formula, R 4 is a linear or branched, substituted or unsubstituted C1-C 22 Alkyl, straight or branched chain, substituted or unsubstituted C1-C 22 Alkylenyl, substituted or unsubstituted C6-C 15 Alkylaryl, or substituted or unsubstituted C6-C 14 aryl, and X is selected from O, S or CH2; the molar ratio of said at least one polyether of general formula A(a) to said at least one compound of formula (E) is in the range of 1:0.8 to 1:5; moreover a) The hindered amine light stabilizers (HALS) of general formula H1 are [ka] formula H1 (In the ceremony R 5 and R 6 are independently H or substituted or unsubstituted C 1~4 alkyl; R 7 -OH, -NH2, -NHR 9 , -R 10 -OH, -R 10 -NH2, or -R 10 -NHR 9 Selected from; R 8 -H, -O·, straight or branched chain substituted or unsubstituted C1-C 22 Alkyl, straight or branched chain substituted or unsubstituted C3-C8 cycloalkyl, -OR 11 , -R 12 -OH, or -OR 12 -OH; where R 9 , and R 11 are independently straight or branched chain substituted or unsubstituted C1-C 22 alkyl; where R 10 and R 12 are independently straight or branched chain substituted or unsubstituted C1-C 22 alkylene); b) The hindered amine light stabilizer (HALS) H2 is (i) 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol; and (ii) General formula [ka] (In the formula, R 13 is a linear or branched, substituted or unsubstituted C1-C 12 alkyl; R 14 is a linear or branched, substituted or unsubstituted C2-C 12 at least one dicarboxylic acid ester of a HALS copolymer comprising: c) The hindered amine light stabilizers (HALS) of general formula H3 are triazine-based dimers having —NH or —OH— functional groups: [ka] formula H3 (In the formula, R 5 , R 6 , and R 8 is as defined above; R 15 is selected from H or straight or branched chain substituted or unsubstituted C1-C6 alkyl; R 16 is selected from H or straight or branched chain substituted or unsubstituted C1-C6 alkyl; R 17 -H or -R 18 -OH, and R 18 is a linear or branched, substituted or unsubstituted C1-C 22 alkylene); d) The hindered amine light stabilizer (HALS) of general formula H4 is a diester or carbonate functionalized HALS compound: [ka] Formula H4 (In the formula, R 5 , R 6 , and R 8 is as defined above; L1 is [ka] or [ka] and; where * indicates the point of attachment to O, R 19 is a linear or branched, substituted or unsubstituted C1-C 22 alkylene); e) Hindered amine light stabilizer (HALS) H5 is a triazine-substituted alkylamine-based oligomer having an NH-functional group: 1,5,8,12-tetrakis[4,6-bis(N-butyl-N-1,2,2,6,6-pentamethyl-4-piperidylamino)-1,3,5-triazin-2-yl]-1,5,8,12-tetraazadodecane; f) the hindered amine light stabilizer (HALS) H6 is a polyol polyester: tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)butane-1,2,3,4-tetracarboxylate; moreover B1 is a group of general formula R 20 (COOR 21 ) q (In the formula, R 20 is a linear or branched, substituted or unsubstituted C1-C 22 -Alkylene, and substituted or unsubstituted C6-C 10 arylene; R 21 is a linear or branched, substituted or unsubstituted C1-C 12 -alkyl; and and q is an integer ranging from 2 to 5; B2 has the general formula: [ka] (In the formula, R 22 is at least one phthalic anhydride derivative selected from 4-COOH, 4-NO2, 4-F, 4-Cl, or 4-Br; B3 has the general formula: G(NCO) r (Wherein G is a linear or branched, substituted or unsubstituted C2-C 22 Alkyl, straight or branched chain substituted or unsubstituted C3-C8 cycloalkyl, or substituted or unsubstituted C6-C 14 arylene, and and r is 2 or 3 or 4; B4 is at least one epoxy polymer; and B5 relates to polymer P, which is at least one maleic anhydride polymer.

[0028] In the context of the present invention, the term "alkyl" as used herein refers to a group having the general formula C n H 2n+1 (n is the number of carbon atoms, 1, 2, 3, 4, etc.) refers to acyclic saturated aliphatic groups, including straight and branched chain alkyl saturated hydrocarbon radicals.

[0029] Preferably, alkyl is a straight-chain unsubstituted C1-C6 alkyl selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, and docosyl. 22 Refers to carbon atoms.

[0030] Preferably, alkyl is 1-methylethyl, 1-methylpropyl, 2-methylpropyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-methylheptyl, 2-methylheptyl, 3-methylheptyl, 4-methylheptyl, 5-methylheptyl, 6-methylheptyl, 1-methyloctyl, 2-methyloctyl, 3-methyloctyl, ethyl, 4-methyloctyl, 5-methyloctyl, 6-methyloctyl, 7-methyloctyl, 1-methylnonyl, 2-methylnonyl, 3-methylnonyl, 4-methylnonyl, 5-methylnonyl, 6-methylnonyl, 7-methylnonyl, 8-methylnonyl, 1-methyldecyl, 2-methyldecyl, 3-methyldecyl, 4-methyldecyl, 5-methyldecyl, 6-methyldecyl, 7-methyldecyl, 8-methyldecyl, 9-methyldecyl, 1-methylundecyl, 2-methylundecyl, 3-methylundecyl, 4-methylundecyl, 5-methylundecyl undecyl, 6-methylundecyl, 7-methylundecyl, 8-methylundecyl, 9-methylundecyl, 10-methylundecyl, 1-methyldodecyl, 2-methyldodecyl, 3-methyldodecyl, 4-methyldodecyl, 5-methyldodecyl, 6-methyldodecyl, 7-methyldodecyl, 8-methyldodecyl, 9-methyldodecyl, 10-methyldodecyl, 11-methyldodecyl, 1-methyltridecyl, 2-methyltridecyl, 3-methyltridecyl, 4-methyltridecyl, 5-methyltridecyl, 6-methyltridecyl, 7-methyltridecyl branched, unsubstituted C3-C tetradecyl, selected from the group consisting of decyl, 8-methyltridecyl, 9-methyltridecyl, 10-methyltridecyl, 11-methyltridecyl, 12-methyltridecyl, 1-methyltetradecyl, 2-methyltetradecyl, 3-methyltetradecyl, 4-methyltetradecyl, 5-methyltetradecyl, 6-methyltetradecyl, 7-methyltetradecyl, 8-methyltetradecyl, 9-methyltetradecyl, 10-methyltetradecyl, 11-methyltetradecyl, 12-methyltetradecyl, 13-methyltetradecyl, and the like; 22Refers to a carbon atom.

[0031] In the context of the present invention, the term "alkenyl" as used herein refers to a group of the general formula C n H 2n-1 (n is the number of carbon atoms, 1, 2, 3, 4, etc.) refers to acyclic unsaturated aliphatic groups having at least one double bond, including straight chain alkenyl unsaturated hydrocarbon radicals.

[0032] Preferably, alkenyl is prop-1-enyl, prop-2-enyl, but-1-enyl, but-2-enyl, but-3-enyl, pent-1-enyl, pent-2-enyl, pent-3-enyl, pent-4-enyl, hex-1-enyl, hex-2-enyl, hex-3-enyl, hex-4-enyl, hex-5-enyl, hept-1-enyl, hept-2-enyl, hept-3-enyl, hept-4-enyl, hept-5-enyl, hept-6-enyl, oct-1-enyl, oct-2-enyl, oct-3-enyl, oct-4-enyl. , oct-5-enyl, oct-6-enyl, oct-7-enyl, non-1-enyl, non-2-enyl, non-3-enyl, non-4-enyl, non-5-enyl, non-6-enyl, non-7-enyl, non-8-enyl, dec-1-enyl, dec-2-enyl, dec-3-enyl, dec-4-enyl, dec-5-enyl, dec-6-enyl, dec-7-enyl, dec-8-enyl, dec-9-enyl, undec-1-enyl, undec-2-enyl, undec-3-enyl, undec-4-enyl, undec-5-enyl, undec-6-enyl, Undec-7-enyl, undec-8-enyl, undec-9-enyl, undec-10-enyl, dodec-1-enyl, dodec-2-enyl, dodec-3-enyl, dodec-4-enyl, dodec-5-enyl, dodec-6-enyl, dodec-7-enyl, dodec-8-enyl, dodec-9-enyl, dodec-10-enyl, dodec-11-enyl, tridec-1-enyl, tridec-2-enyl, tridec-3-enyl, tridec-4-enyl, tridec-5-enyl, tridec-6-enyl, tridec-7-enyl, tridec-8-enyl, tridec- 9-enyl, tridec-10-enyl, tridec-11-enyl, tridec-12-enyl, tetradec-1-enyl, tetradec-2-enyl, tetradec-3-enyl, tetradec-4-enyl, tetradec-5-enyl, tetradec-6-enyl, tetradec-7-enyl, tetradec-8-enyl, tetradec-9-enyl, tetradec-10-enyl, tetradec-11-enyl, tetradec-12-enyl, tetradec-13-enyl, pentadec-1-enyl, pentadec-2-enyl, pentadec-3-enyl, pentadec-4-enyl,Pentadec-5-enyl, pentadec-6-enyl, pentadec-7-enyl, pentadec-8-enyl, pentadec-9-enyl, pentadec-10-enyl, pentadec-11-enyl, pentadec-12-enyl, pentadec-13-enyl, pentadec-14-enyl, hexadec-1-enyl, hexadec-2-enyl, hexadec-3-enyl, hexadec-4-enyl, hexadec-5-enyl, hexadec-6-enyl, hexadec-7-enyl, hexadec-8-enyl, hexadec-9-enyl, hexadec-10-enyl, hexadec-11-enyl, hexadec-12-enyl, hexadec-13-enyl, hexa ...4-enyl, hexadec-14-enyl, hexadec-14-enyl, hexadec-14-enyl, hexadec-14-enyl, hexadec-14-enyl, hexadec-14-enyl, hexadec-14-enyl, hexadec-14-enyl, hexadec-14-enyl, hexadec-14-enyl, hexadec- Hexadec-11-enyl, hexadec-12-enyl, hexadec-13-enyl, hexadec-14-enyl, hexadec-15-enyl, heptadec-1-enyl, heptadec-2-enyl, heptadec-3-enyl, heptadec-4-enyl, heptadec-5-enyl, heptadec-6-enyl, heptadec-7-enyl, heptadec-8-enyl, heptadec-9-enyl, heptadec-10-enyl, heptadec-11-enyl, heptadec-12-enyl, heptadec-13-enyl, heptadec-14-enyl, heptadec-15-enyl nyl, heptadec-16-enyl, octadec-1-enyl, octadec-2-enyl, octadec-3-enyl, octadec-4-enyl, octadec-5-enyl, octadec-6-enyl, octadec-7-enyl, octadec-8-enyl, octadec-9-enyl, octadec-10-enyl, octadec-11-enyl, octadec-12-enyl, octadec-13-enyl, octadec-14-enyl, octadec-15-enyl, octadec-16-enyl, octadec-17-enyl, nonadeca-1-enyl, nonadeca-2- enyl, nonadecanyl, nonadecanyl-3, nonadecanyl-4, nonadecanyl, nonadecanyl-5, nonadecanyl-6, nonadecanyl-7, nonadecanyl-8, nonadecanyl, nonadecanyl-9, nonadecanyl, nonadecanyl-10, nonadecanyl, nonadecanyl-11, nonadecanyl-12, nonadecanyl-13, nonadecanyl-14, nonadecanyl-15, nonadecanyl-16, nonadecanyl-17, nonadecanyl-18, icos-1-enyl, icos-2-enyl, icos-3-enyl, icos-4-enyl, icos-5-enyl, icos-6-enyl,Icos-7-enyl, Icos-8-enyl, Icos-9-enyl, Icos-10-enyl, Icos-11-enyl, Icos-12-enyl, Icos-13-enyl, Icos-14-enyl, Icos-15-enyl, Icos-16-enyl, Icos-17-enyl, Icos-18-enyl, Icos-19-enyl, Henicosa-1-enyl, Henicosa-2 -enyl, henicos-3-enyl, henicos-4-enyl, henicos-5-enyl, henicos-6-enyl, henicos-7-enyl, henicos-8-enyl, henicos-9-enyl, henicos-10-enyl, henicos-11-enyl, henicos-12-enyl, henicos-13-enyl, henicos-14-enyl, henicos- -15-enyl, henicos-16-enyl, henicos-17-enyl, henicos-18-enyl, henicos-19-enyl, henicos-20-enyl, docos-1-enyl, docos-2-enyl, docos-3-enyl, docos-4-enyl, docos-5-enyl, docos-6-enyl, docos-7-enyl, docos-8-enyl, docos-9- a straight-chain unsubstituted C1-C selected from the group consisting of enyl, docos-10-enyl, docos-11-enyl, docos-12-enyl, docos-13-enyl, docos-14-enyl, docos-15-enyl, docos-16-enyl, docos-17-enyl, docos-18-enyl, docos-19-enyl, docos-20-enyl and docos-21-enyl; 22 Refers to carbon atoms.

[0033] In the context of the present invention, the term alkylene as used herein refers to a saturated, divalent, straight or branched chain hydrocarbon radical. Examples of such preferred alkylene radicals include methylene, ethane-1,2-diyl, propane-1,3-diyl, propane-1,2-diyl, 2-methylpropane-1,2-diyl, 2,2-dimethylpropane-1,3-diyl, butane-1,4-diyl, butane-1,3-diyl (= 1-methyl-propane-1,3-diyl), butane-1,2-diyl, butane-2,3-diyl, 2-methyl-butane-1,3-diyl, 3-methyl-butane-1,3-diyl (= 1,1-dimethylpropane-1,3-diyl), pentane-1,4-diyl, pentane-1,5-diyl, pentane-2,5-diyl, 2-methylpentane-2,5-diyl (= 1,1-dimethylbutane-1,3-diyl) and hexane-1,6-diyl.

[0034] In the context of this invention, the term cycloalkyl as used herein refers to mono- and bicyclic 3- to 15-membered saturated alicyclic groups, including branched cycloalkyl saturated hydrocarbons.

[0035] Preferably, cycloalkyl is a C3-C4 alkyl group selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cycloeodecyl, cyclotridecyl, cyclotetradecyl, and cyclopentadecyl. 15 Refers to carbon atoms.

[0036] In the context of the present invention, the term aryl as used herein refers to phenyl or naphthyl, preferably phenyl. The term substituted aryl refers to an aryl radical in which some or all of the hydrogen atoms have been replaced by substituents, preferably the substituents being selected from hydroxy, halogen, cyano, C1-C4-alkyl and C1-C4-alkoxy. Preferably, the aryl is unsubstituted or has 1, 2 or 3 substituents.

[0037] In the context of the present invention, the term "alkylaryl" as used herein refers to an alkyl-substituted aryl radical in which one hydrogen atom at any position of the alkyl carbon backbone is replaced by an aryl moiety. Preferably, arylalkyl is benzyl (-CH-CH), ethylphenyl (-CH-CH-CH, -(CH)CH-CH), etc.

[0038] In the context of the present invention, the term "pigmentary material" includes both pigments and fillers and therefore relates to a pigment, a filler or a mixture of pigment and filler.

[0039] In the context of the present invention, the term "D50" refers to the median particle size below which 50% of the distribution has a smaller particle size and above which 50% of the distribution has a larger particle size.

[0040] In a preferred embodiment, the polymer P is a) at least one polyether A; b) at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6, or mixtures thereof; and c) at least one compound B having at least one functional group selected from the group consisting of ester, isocyanate, anhydride, carboxylic acid, or epoxide, wherein the at least one compound B is selected from B1, B2, B3, B4, B5, or a mixture thereof; It is obtained by reacting

[0041] In a preferred embodiment, the polymer P is a) at least one polyether A; and b) at least one hindered amine light stabilizer selected from H2, H4, H6, or mixtures thereof; It is obtained by reacting

[0042] In a preferred embodiment, the polymer P is a) at least one polyether A; b) at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6, or mixtures thereof; and c) at least one compound B having at least one functional group selected from the group consisting of ester, isocyanate, anhydride, carboxylic acid, or epoxide, wherein the at least one compound B is selected from B1, B2, B3, B4, B5, or a mixture thereof; It is obtained by reacting

[0043] In a preferred embodiment, the polymer P is a) at least one polyether A(b) in which X is O; b) at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6, or mixtures thereof; and c) at least one compound B having at least one functional group selected from the group consisting of ester, isocyanate, anhydride, carboxylic acid, or epoxide, wherein the at least one compound B is selected from B1, B2, B3, B4, B5, or a mixture thereof; It is obtained by reacting In a preferred embodiment, the polymer P is a) at least one polyether A(b) in which X is CH2; b) at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6, or mixtures thereof; and c) at least one compound B having at least one functional group selected from the group consisting of ester, isocyanate, anhydride, carboxylic acid, or epoxide, wherein the at least one compound B is selected from B1, B2, B3, B4, B5, or a mixture thereof; It is obtained by reacting

[0044] In a preferred embodiment, the polymer P is a) at least one polyether A(a); and b) at least one hindered amine light stabilizer selected from H2, H4, H6, or mixtures thereof; It is obtained by reacting

[0045] In a preferred embodiment, the polymer P is a) at least one polyether A(b) in which X is O; and b) at least one hindered amine light stabilizer selected from H2, H4, H6, or mixtures thereof; It is obtained by reacting

[0046] In a preferred embodiment, the polymer is a) at least one polyether A(b) in which X is CH2; and b) at least one hindered amine light stabilizer selected from H2, H4, H6, or mixtures thereof; It is obtained by reacting

[0047] In a preferred embodiment, m is an integer ranging from 1 to 50; and n is an integer ranging from 1 to 50.

[0048] In a more preferred embodiment, m is an integer ranging from 1 to 25; and n is an integer ranging from 1 to 25.

[0049] In a preferred embodiment, the at least one polyether A is at least one polyether of the general formula A(a). [ka] Formula A(a)

[0050] In a preferred embodiment, R1 is -CH3.

[0051] In a preferred embodiment, at least one polyether of Formula A(a) is a copolymer comprising ethylene oxide and propylene oxide.

[0052] In a preferred embodiment, R 2 is -CH3.

[0053] In a preferred embodiment, R 2 is -CH3 and Z is NH2.

[0054] In a preferred embodiment, the at least one polyether of general formula A(a) is a block copolymer of ethylene oxide and propylene oxide having a weight average molecular weight according to DIN 55672-1 of 2000 g / mol.

[0055] In a preferred embodiment, R 2 is -CH3 and Z is OH.

[0056] In a preferred embodiment, the at least one polyether of general formula A(a) is a block copolymer comprising ethylene oxide and propylene oxide having a weight average molecular weight according to DIN 55672-1 of 1950 g / mol.

[0057] In a preferred embodiment, at least one polyether A is a homopolymer comprising ethylene oxide.

[0058] In a preferred embodiment, m is an integer ranging from 1 to 100;

[0059] In a more preferred embodiment, m is an integer ranging from 1 to 50;

[0060] In the most preferred embodiment, m is an integer ranging from 1 to 25;

[0061] In a preferred embodiment, Z is —OH.

[0062] In a preferred embodiment, the at least one polyether of general formula A(a) is a methoxypolyethylene glycol having a weight average molecular weight according to DIN 55672-1 of 500 g / mol.

[0063] In a preferred embodiment, the at least one polyether A is at least one polyether of the general formula A(b) and at least one polyether of the general formula A(a) [ka] Formula A(a) (In the formula, R 1 , R 2 , m, n, and Z are as defined above) with at least one compound of formula (E): [ka] Formula (E)

[0064] In a preferred embodiment, the molar ratio of the at least one polyether of general formula A(a) to the at least one compound of formula (E) is in the range of 1:0.8 to 1:5; more preferably 1:0.8 to 1:3; most preferably 1:0.8 to 1:2.

[0065] In a preferred embodiment, at least one polyether of general formula A(b) is obtained by reacting at least one polyether of general formula A(a) with at least one compound of formula (E), wherein R 4 is 2-ethylhexyl, X=O, and the molar ratio of the at least one polyether of general formula A(a) to the at least one compound of formula (E) is in the range of 1:0.8 to 1:2.

[0066] In a preferred embodiment, at least one polyether of general formula A(b) is obtained by reacting at least one polyether of general formula A(a) with at least one compound of formula (E), wherein R 4 is hexadecyl, X=O, and the molar ratio of the at least one polyether of general formula A(a) to the at least one compound of formula (E) is in the range of 1:0.8 to 1:2.

[0067] In a preferred embodiment, the at least one HALS of formula H1 is selected from 4-hydroxy-2,2,6,6-tetramethylpiperidinyloxyl, 4-amino-2,2,6,6-tetramethyl-piperidinyloxyl, 4-hydroxy-2,2,6,6-tetramethylpiperidine, 4-amino-2,2,6,6-tetramethyl-piperidine, 4-hydroxy-1,2,2,6,6-pentamethyl-piperidine, or 4-hydroxy-1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidine.

[0068] In a preferred embodiment, at least one HALS of formula H1 is 4-hydroxy-2,2,6,6-tetramethylpiperidinyloxyl (H1-a).

[0069] In a preferred embodiment, at least one HALS of formula H1 is 4-amino-2,2,6,6-tetramethyl-piperidinyloxyl (H1-b).

[0070] In a preferred embodiment, at least one HALS of formula H1 is 4-hydroxy-2,2,6,6-tetramethylpiperidine (H1-c).

[0071] In a preferred embodiment, at least one HALS of formula H1 is 4-amino-2,2,6,6-tetramethyl-piperidine (H1-d).

[0072] In a preferred embodiment, the at least one HALS of formula H1 is 4-hydroxy-1,2,2,6,6-pentamethyl-piperidine (H1-e).

[0073] In a preferred embodiment, the at least one HALS of formula H1 is 4-hydroxy-1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidine (H1-f).

[0074] In a preferred embodiment, the at least one HALS H2 is a copolymer comprising dimethyl succinate polymer and 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol, with a weight average molecular weight according to DIN 55672-1 of 7000 g / mol.

[0075] In a preferred embodiment, at least one HALS of general formula H3 is [ka] (H3-a) is.

[0076] In a preferred embodiment, at least one HALS of general formula H4 is [ka] (H4-a) , [ka] (H4-b) , or [ka] (H4-c) is.

[0077] In a preferred embodiment, at least one HALS of formula H4 is a carbonate: [ka] (H4-d) is.

[0078] In a preferred embodiment, at least one HALS of formula H4 is [ka] (H4-a) is.

[0079] In a preferred embodiment, at least one HALS of formula H4 is [ka] (H4-b) is.

[0080] In a preferred embodiment, at least one HALS of formula H4 is [ka] (H4-c) is.

[0081] In a preferred embodiment, the at least one HALS H5 is 1,5,8,12-tetrakis[4,6-bis(N-butyl-N-1,2,2,6,6-pentamethyl-4-piperidylamino)-1,3,5-triazin-2-yl]-1,5,8,12-tetraazadodecane.

[0082] In a preferred embodiment, the at least one HALS H6 is tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)butane-1,2,3,4-tetracarboxylate.

[0083] Commercially available HALS, including those under the trade names Tinuvin® 622, Tinuvin® 152, Chimassorb® 119, Tinuvin® 770, Tinuvin® 292, and Tinuvin® 123, can be used in the present invention.

[0084] In a preferred embodiment, the at least one diester or polyester B1 is selected from dimethyl succinate, diethyl succinate, or 1,2-cyclohexanedicarboxylic acid diisononyl ester.

[0085] In a more preferred embodiment, the at least one diester or polyester B1 is dimethyl succinate (B1-a).

[0086] In a preferred embodiment, the at least one phthalic anhydride derivative B2 is trimellitic anhydride (B2-a).

[0087] In a preferred embodiment, the at least one di- or polyisocyanate B3 is selected from 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, or dimers or trimers thereof.

[0088] In a more preferred embodiment, the at least one diisocyanate B3 is 2,4-toluene diisocyanate (B3-a).

[0089] In a more preferred embodiment, the at least one diisocyanate B3 is a mixture of 2,4-toluene diisocyanate and 2,6-toluene diisocyanate.

[0090] In a more preferred embodiment, the at least one diisocyanate B3 is selected from isophorone diisocyanate, hexamethylene diisocyanate, or dimers or trimers thereof.

[0091] Commercially available isocyanates include mixtures of monomeric and polymeric forms, such as dimers and trimers, of isocyanates, which mixtures can also be used in the present invention.

[0092] In a preferred embodiment, the at least one epoxy polymer B4 comprises a monomer selected from trimethylolpropane triglycidyl ether or bisphenol A diglycidyl ether.

[0093] In a more preferred embodiment, the at least one epoxy polymer B4 comprises trimethylolpropane triglycidyl ether.

[0094] In a preferred embodiment, the at least one maleic anhydride polymer B5 is a styrene maleic anhydride copolymer.

[0095] In a preferred embodiment, the at least one maleic anhydride polymer B5 is selected from styrene maleic anhydride copolymers having a weight average molecular weight according to DIN 55672-1 in the range from 500 g / mol to 10,000 g / mol.

[0096] In a preferred embodiment, the polymer P is obtained by reacting one polyether A with one hindered amine light stabilizer (HALS) H.

[0097] In a preferred embodiment, the polymer P is one polyether A selected from A1, A2, A4 or A5; and -Hindered amine light stabilizer (HALS) H2-a It is obtained by reacting

[0098] In a preferred embodiment, the polymer P is obtained by reacting one polyether A, one hindered amine light stabilizer (HALS) H, and one compound B.

[0099] In a preferred embodiment, the polymer P is -Compound B1-a; one polyether A selected from A1, A3, A4 or A5; and one hindered amine light stabilizer (HALS) H selected from H1-b, H1-d, H1-f, H-2a, H-3a, H4-a, H-4b, H-4c, H-4d, H-5 or H-6 It is obtained by reacting

[0100] In a preferred embodiment, the polymer P is -Compound B2-a; one polyether A selected from A3 or A4; and - one hindered amine light stabilizer (HALS) H selected from H1-a, H1-c, or H1-e It is obtained by reacting

[0101] In a preferred embodiment, the polymer P is - one compound B selected from B3-a or B3-b; one polyether A selected from A1, A2 or A5; and - one hindered amine light stabilizer (HALS) H selected from H1-a, H1-c, or H-3a It is obtained by reacting

[0102] In a preferred embodiment, the polymer P is -Compound B4-a; one polyether A selected from A1, A2, A3 or A5; and - one hindered amine light stabilizer (HALS) H selected from H1-b, H1-d, or H5-a It is obtained by reacting

[0103] In a preferred embodiment, the polymer P is - one compound B selected from B5-a or B-5b; - Polyether A1; and - one hindered amine light stabilizer (HALS) H selected from H1-b, H1-c, or H1-d It is obtained by reacting

[0104] In a preferred embodiment, the polymer P is -Compound B1-a; one polyether A selected from A1, A3, A4 or A5; and - one hindered amine light stabilizer (HALS) H selected from H1-b, H1-d, H1-f, H-3a or H-5 It is obtained by reacting

[0105] In a preferred embodiment, the polymer P is obtained by reacting a polyether A, two hindered amine light stabilizers (HALS), and a compound B.

[0106] In a preferred embodiment, the polymer P is -Compound B1-a; one polyether A selected from A1, A3, A4 or A5; and - one hindered amine light stabilizer (HALS) H selected from H-2a, H4-a, or H4-b It is obtained by reacting

[0107] In a preferred embodiment, the polymer P is obtained by reacting a polyether A, three hindered amine light stabilizers (HALS), and a compound B.

[0108] In a preferred embodiment, the polymer P is -Compound B1-a; - Polyether A3; and -Hindered amine light stabilizers (HALS) H, H-2a, H4-a, and H4-b It is obtained by reacting

[0109] Polymer P In a preferred embodiment, the polymer P has a weight average molecular weight according to DIN 55672-1 in the range of 200 g / mol to 100,000 g / mol.

[0110] In a preferred embodiment, the polymer P has a weight average molecular weight according to DIN 55672-1 in the range of 500 g / mol to 50,000 g / mol.

[0111] In a preferred embodiment, the polymer P has a weight average molecular weight according to DIN 55672-1 in the range of 2000 g / mol to 50,000 g / mol.

[0112] In a preferred embodiment, the polymer P has a polydispersity index according to DIN 55672-1 in the range of 1.1 to 4.0.

[0113] In a preferred embodiment, the polymer P has a HALS content of 0.1 to 3.5 mmol HASL / g.

[0114] In a preferred embodiment, the polymer P has a HALS content of 0.2 to 3.0 mmol HASL / g.

[0115] Preparation method Another aspect of the present invention is a method for producing a i. mixing at least one polyether A with at least one hindered amine light stabilizer H selected from H2, H4, H6, or mixtures thereof; ii. heating the mixture obtained in step (i) at 80°C to 200°C; The present invention relates to a method for preparing a polymer P, comprising:

[0116] The H2, H4 and H6 compounds are esters which react with the terminal amine or hydroxy group of at least one polyether to yield the polymer P.

[0117] In a preferred embodiment, the method further comprises adding at least one catalyst selected from tetrabutyl titanate or dibutyltin dilaurate to the mixture obtained in step (i).

[0118] In a preferred embodiment, the amount of the at least one catalyst is in the range of 0.1 to 5.0 wt % based on the total weight of the reaction mixture.

[0119] In a preferred embodiment, the amount of the at least one catalyst is in the range of 0.25 to 1.0 wt % based on the total weight of the reaction mixture.

[0120] Another aspect of the present invention is a method for producing a i. mixing said at least one polyether A, said at least one hindered amine light stabilizer H selected from H1, H2, H3, H4, H5, H6 or mixtures thereof, and said at least one compound B selected from B1, B2, or B5; ii. heating the mixture obtained in step (i) at 80°C to 200°C; The present invention relates to a method for preparing a polymer P, comprising:

[0121] The B1, B2 and B5 compounds have functional groups selected from esters or anhydrides, which react with the terminal amine or hydroxyl groups of at least one polyether P.

[0122] In a preferred embodiment, the method further comprises adding at least one catalyst selected from tetrabutyl titanate or dibutyltin dilaurate to the mixture obtained in step (i).

[0123] In a preferred embodiment, the amount of the at least one catalyst is in the range of 0.1 to 5.0 wt % based on the total weight of the reaction mixture.

[0124] In a preferred embodiment, the amount of the at least one catalyst is in the range of 0.25 to 1.0 wt % based on the total weight of the reaction mixture.

[0125] Another aspect of the present invention is a method for producing a (i) reacting at least one polyether A with at least one compound B selected from B3 or B4; (ii) reacting the product obtained in step (i) with at least one hindered amine light stabilizer H selected from H1, H2, H3, H4, H5, H6 or mixtures thereof; The present invention relates to a method for preparing a polymer P, comprising:

[0126] The B3 and B4 compounds have a group selected from an isocyanate or an epoxide, which reacts with the terminal amine or hydroxy group of at least one polyether.

[0127] In a preferred embodiment, the method further comprises adding at least one solvent in step (i); the at least one solvent is selected from ethyl acetate, or methoxypropyl acetate.

[0128] In a preferred embodiment, the method further comprises adding at least one catalyst in an amount ranging from 0.1 to 5.0 wt % based on the total weight of the reaction mixture.

[0129] In a preferred embodiment, the at least one catalyst is aluminum trichloride.

[0130] In a preferred embodiment, step (i) is carried out at a temperature of 40°C to 120°C.

[0131] In a preferred embodiment, step (ii) is carried out at a temperature of 50°C to 200°C.

[0132] Composition and Uses Another aspect of the present invention relates to a liquid composition comprising polymer P.

[0133] Another aspect of the present invention relates to a liquid composition in the form of a dispersion comprising at least one particulate solid material and at least one polymer P.

[0134] In a preferred embodiment, the at least one particulate solid material has a particle size D in the range of 0.005 um to 100 um according to dynamic light scattering techniques using a fixed scattering angle of 90° or 180°. 50 It has.

[0135] In a preferred embodiment, the at least one particulate solid material is at least one pigment.

[0136] In a preferred embodiment, the at least one particulate solid material is a mixture of at least one pigment and at least one filler.

[0137] In a preferred embodiment, the liquid composition comprises a liquid diluent.

[0138] In a preferred embodiment, the liquid composition further comprises at least one additive selected from binders, wetting agents, rheology modifiers, UV filters, defoamers, leveling agents, slip agents, substrate wetting agents, antioxidants, radical scavengers, biocides, and coalescing agents.

[0139] In a preferred embodiment, the liquid composition is in the form of a pigment paste, millbase, colorant, coating composition or ink.

[0140] In a preferred embodiment, the liquid composition is formulated as a pigment paste. In a more preferred embodiment, the pigment paste comprises at least one particulate solid material, at least one polymer P of the present invention, at least one liquid diluent, and at least one defoaming agent.

[0141] In a preferred embodiment, the pigment paste is binder-free.

[0142] Pigment pastes (pigment concentrates or millbases) prepared using polymer P as dispersant show very good performance. The pigment pastes have low millbase viscosities. The pigment pastes show excellent storage stability. The viscosity of the millbase does not increase on storage.

[0143] In a preferred embodiment, the coating composition comprises: i. a polymer P of the invention; ii. at least one particulate solid material selected from a pigment, a filler, or a mixture thereof; iii. at least one liquid diluent, and iv. at least one polymer binder Including, At least one particulate solid material is dispersed in a liquid diluent selected from an organic solvent, water, a reactive diluent, or mixtures thereof.

[0144] In a preferred embodiment, the coating composition comprises: i. 0.1 to 50 wt. % of a polymer of the present invention, based on the total weight of the liquid composition; ii. 1 to 70 wt. %, based on the total weight of the coating composition, of at least one particulate solid material; iii. 10 to 98 wt. % of at least one liquid diluent, based on the total weight of the liquid composition; and iv. 10 to 98 wt. % of at least one binder, based on the total weight of the liquid composition. Includes:

[0145] In a preferred embodiment, the coating composition is prepared by dispersing a particulate solid material in a liquid diluent in the presence of the polymer P of the present invention. The coating composition further comprises an additive. Dispersion is accomplished using conventional techniques such as high speed mixing, ball milling, sand grinding, attritor milling, or two- or three-roll milling.

[0146] In a preferred embodiment, the liquid diluent is water.

[0147] In a preferred embodiment, the liquid diluent is a mixture of water and other diluents selected from C1-C4 alcohols, glycol ethers, and polyols. The C1-C4 alcohols are selected from methanol, ethanol, isopropanol, propanol, and n-butanol. The glycol ethers are selected from butyl glycol and methoxypropylene glycol. The polyols are selected from glycerol, ethylene glycol, diethylene glycol, triethylene glycol, and propylene glycol.

[0148] In a preferred embodiment, the binder is an acrylic binder.

[0149] Coating compositions prepared using Polymer P exhibit good weather resistance. Films prepared using coating compositions containing Polymer P exhibit low Delta E values.

[0150] Another aspect of the present invention relates to the use of the polymer P of the present invention as a dispersant.

[0151] Another aspect of the present invention relates to the use of the polymer P of the present invention as a light stabilizer.

[0152] Another aspect of the present invention relates to the use of the polymer P of the present invention in a coating composition.

[0153] The present invention provides one or more of the following advantages. 1. The polymers of the present invention can be used as part of a liquid composition as a dispersant. 2. Pigment pastes (pigment concentrates or millbases) prepared using polymer P as a dispersant perform very well at low millbase viscosities. 3. The pigment paste exhibits excellent storage stability: the viscosity of the millbase does not increase upon storage. 4. Coating compositions prepared using polymer P exhibit good weather resistance. 5. Films prepared using coating compositions containing polymer P exhibit excellent light stabilization properties with low Delta E values. 6. The polymers of the present invention do not interfere with the natural properties of the dyes / pigments. 7. The polymers of the present invention, when used as dispersants, allow for aqueous processability of coating compositions, thus improving compliance with environmental and safety standards.

[0154] Below, a list of embodiments is provided to further explain the present disclosure, but is not intended to limit the disclosure to the specific embodiments listed below.

[0155] 1. A polymer P, with at least one polyether A; - at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6, or mixtures thereof; at least one compound B having at least one functional group selected from the group consisting of ester, isocyanate, anhydride, carboxylic acid or epoxide, wherein the at least one compound B is selected from B1, B2, B3, B4, B5 or a mixture thereof; The polymer P is obtained by reacting or with at least one polyether A; at least one hindered amine light stabilizer selected from H2, H4, H6, or mixtures thereof; A polymer P obtained by reacting the at least one polyether A is selected from at least one polyether of general formula A(a), at least one polyether of general formula A(b), or a mixture thereof; (a) At least one polyether of general formula A(a) is [ka] Formula A(a) (In the formula, R 1 is a linear or branched, substituted or unsubstituted C1-C 22 Alkyl, straight or branched chain, substituted or unsubstituted C1-C 22 Alkylenyl, substituted or unsubstituted C6-C 15 Alkylaryl, or substituted or unsubstituted C6-C 14 aryl; R 2 is selected from straight or branched chain, substituted or unsubstituted C1-C4 alkyl; m is an integer ranging from 1 to 100; n is an integer ranging from 0 to 100; the m units and the n units are distributed to form a random copolymer, a block copolymer, or a gradient copolymer; and Z is -OH, -NH2, or -NHR 3 is selected from, where R 3 is a linear or branched, substituted or unsubstituted C1-C 22 alkyl); (b) The at least one polyether of general formula A(b) is at least one polyether of general formula A(a): [ka] Formula A(a) (In the formula, R 1 , R 2 , m, n, and Z are as defined above) At least one compound of formula (E) [ka] Formula (E) (In the formula, R 4 is a linear or branched, substituted or unsubstituted C1-C 22 Alkyl, straight or branched chain, substituted or unsubstituted C1-C 22 Alkylenyl, substituted or unsubstituted C6-C 15Alkylaryl, or substituted or unsubstituted C6-C 14 aryl, and X is selected from O, S or CH2, the molar ratio of the at least one polyether of general formula A(a) to the at least one compound of formula (E) is in the range of 1:0.8 to 1:5; moreover a) Hindered amine light stabilizers (HALS) of general formula H1 are [ka] formula H1 (In the ceremony R 5 and R 6 are independently H or substituted or unsubstituted C 1~4 alkyl; R 7 -OH, -NH2, -NHR 9 , -R 10 -OH, -R 10 -NH2, or -R 10 -NHR 9 Selected from; R 8 -H, -O·, straight or branched chain substituted or unsubstituted C1-C 22 Alkyl, straight or branched chain substituted or unsubstituted C3-C8 cycloalkyl, -OR 11 , -R 12 -OH, or -OR 12 -OH; where R 9 , and R 11 are independently straight or branched chain substituted or unsubstituted C1-C 22 alkyl; where R 10 and R 12 are independently straight or branched chain substituted or unsubstituted C1-C 22 alkylene); b) Hindered amine light stabilizer (HALS) H2 (i) 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol; and (ii) General formula: [ka] (In the formula, R 13 is a linear or branched, substituted or unsubstituted C1-C 12 alkyl; R 14 is a linear or branched, substituted or unsubstituted C2-C 12 at least one dicarboxylic acid ester of a HALS copolymer comprising: c) Hindered amine light stabilizers (HALS) of general formula H3 are triazine-based dimers containing -NH or -OH- functional groups: [ka] formula H3 (In the formula, R 5 , R 6 , and R 8 is as defined above; R 15 is selected from H or straight or branched chain, substituted or unsubstituted C1-C6 alkyl; R 16 is selected from H or straight or branched chain, substituted or unsubstituted C1-C6 alkyl; R 17 -H or -R 18 -OH, and R 18 is a linear or branched, substituted or unsubstituted C1-C 22 alkylene); d) Hindered amine light stabilizers (HALS) of general formula H4 are diester or carbonate functionalized HALS compounds: [ka] Formula H4 (In the formula, R 5 , R 6 , and R 8 is as defined above; L1 is [ka] or [ka] and; where * indicates the point of attachment to O, R 19 is a linear or branched, substituted or unsubstituted C1-C 22 alkylene); e) Hindered amine light stabilizer (HALS) H5 is a triazine-substituted alkylamine-based oligomer having an NH-functional group: 1,5,8,12-tetrakis[4,6-bis(N-butyl-N-1,2,2,6,6-pentamethyl-4-piperidylamino)-1,3,5-triazin-2-yl]-1,5,8,12-tetraazadodecane; f) Hindered amine light stabilizer (HALS) H6 is a polyol polyester: tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)butane-1,2,3,4-tetracarboxylate; moreover B1 is a group of general formula R 20 (COOR 21 ) q (In the formula, R 20 is a linear or branched, substituted or unsubstituted C1-C 22 -Alkylene, or substituted or unsubstituted C-C 10 arylene; R 21 is a linear or branched, substituted or unsubstituted C1-C 12 -alkyl; and and q is an integer ranging from 2 to 5; B2 has the general formula: [ka] (In the formula, R 22 is at least one phthalic anhydride derivative selected from 4-COOH, 4-NO2, 4-F, 4-Cl, or 4-Br; B3 has the general formula: G(NCO) r (Wherein G is a linear or branched, substituted or unsubstituted C2-C 22 Alkyl, straight or branched chain substituted or unsubstituted C3-C8 cycloalkyl, or substituted or unsubstituted C6-C 14 arylene, and and r is 2 or 3 or 4; B4 is at least one epoxy polymer; and B5 is at least one maleic anhydride polymer, polymer P.

[0156] 2. Polymer P according to embodiment 1, a) at least one polyether A(a); b) at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6, or mixtures thereof; and c) at least one compound B having at least one functional group selected from the group consisting of ester, isocyanate, anhydride, carboxylic acid, or epoxide, wherein the at least one compound B is selected from B1, B2, B3, B4, B5, or a mixture thereof; The polymer P is obtained by reacting

[0157] 3. Polymer P according to embodiment 1, a) at least one polyether A(b) in which X is O; b) at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6, or mixtures thereof; and c) at least one compound B having at least one functional group selected from the group consisting of ester, isocyanate, anhydride, carboxylic acid, or epoxide, wherein the at least one compound B is selected from B1, B2, B3, B4, B5, or a mixture thereof; The polymer P is obtained by reacting

[0158] 4. Polymer P according to embodiment 1, a) at least one polyether A(b) in which X is CH2; b) at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6, or mixtures thereof; and c) at least one compound B having at least one functional group selected from the group consisting of ester, isocyanate, anhydride, carboxylic acid, or epoxide, wherein the at least one compound B is selected from B1, B2, B3, B4, B5, or a mixture thereof; The polymer P is obtained by reacting

[0159] 5. Polymer P according to embodiment 1, a) at least one polyether A(a); and b) at least one hindered amine light stabilizer selected from H2, H4, H6, or mixtures thereof; The polymer P is obtained by reacting

[0160] 6. Polymer P according to embodiment 1, a) at least one polyether A(b) in which X is O; and b) at least one hindered amine light stabilizer selected from H2, H4, H6, or mixtures thereof; The polymer P is obtained by reacting

[0161] 7. Polymer P according to embodiment 1, a) at least one polyether A(b) in which X is CH2; and b) at least one hindered amine light stabilizer selected from H2, H4, H6, or mixtures thereof; The polymer P is obtained by reacting

[0162] 8. Polymer P according to any one of embodiments 1 to 7, wherein R 1 linear or branched, substituted or unsubstituted C1-C 22 The polymer P is selected from alkyl.

[0163] 9.R 1

[0023] Embodiment 9. Polymer P according to any one of embodiments 1 to 8, wherein is -CH3.

[0164] 10. Polymer P according to any one of embodiments 1 to 9, wherein m is an integer ranging from 1 to 50; A polymer P, wherein n is an integer in the range of 1 to 50.

[0165] 11.R 2 11. The polymer P of any of the preceding embodiments, wherein

[0166] 12.R 2 12. The polymer P of any of the preceding embodiments, wherein is —CH 3 and Z is NH 2 .

[0167] 13. Polymer P according to embodiment 12, in which at least one polyether of general formula A(a) is a block copolymer of ethylene oxide and propylene oxide having a weight-average molecular weight according to DIN 55672-1 of 2000 g / mol.

[0168] 14.R 2 12. The polymer P of any of the preceding embodiments, wherein is —CH 3 and Z is OH.

[0169] 15. Polymer P according to embodiment 14, in which at least one polyether of general formula A(a) is a block copolymer comprising ethylene oxide and propylene oxide having a weight average molecular weight according to DIN 55672-1 of 1950 g / mol.

[0170] 16. Polymer P according to any of embodiments 1 to 9, wherein m is an integer ranging from 1 to 100; Polymer P, wherein n is 0.

[0171] 17. The polymer P according to embodiment 16, wherein Z is —OH.

[0172] 18. Polymer P according to embodiment 17, in which at least one polyether of general formula A(a) is a methoxypolyethylene glycol having a weight-average molecular weight according to DIN 55672-1 of 500 g / mol.

[0173] 19. Polymer P according to any of the preceding embodiments, wherein at least one polyether of general formula A(b) is obtainable by reacting at least one polyether of general formula A(a) with at least one compound of formula (E), wherein R 4 is 2-ethylhexyl, X=O, and the molar ratio of at least one polyether of general formula A(a) to at least one compound of formula (E) is in the range of 1:0.8 to 1:2.

[0174] 20. Polymer P according to any of the preceding embodiments, wherein at least one polyether of general formula A(b) is obtainable by reacting at least one polyether of general formula A(a) with at least one compound of formula (E), wherein R 4 is hexadecyl, X=O, and the molar ratio of at least one polyether of general formula A(a) to at least one compound of formula (E) is in the range of 1:0.8 to 1:2.

[0175] 21. Polymer P according to any of the preceding embodiments, wherein at least one HALS of formula H1 is selected from 4-hydroxy-2,2,6,6-tetramethylpiperidinyloxyl, 4-amino-2,2,6,6-tetramethyl-piperidinyloxyl, 4-hydroxy-2,2,6,6-tetramethylpiperidine, 4-amino-2,2,6,6-tetramethyl-piperidine, 4-hydroxy-1,2,2,6,6-pentamethyl-piperidine, or 4-hydroxy-1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidine.

[0176] 22. Polymer P according to any of the preceding embodiments, wherein at least one HALS H2 is a copolymer comprising dimethyl succinate polymer and 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol, having a weight-average molecular weight according to DIN 55672-1 of 7000 g / mol.

[0177] 23. Polymer P according to any of the preceding embodiments, in which at least one HALS of general formula H3 is [ka] (H3-a) That is, polymer P.

[0178] 24. Polymer P according to any of the preceding embodiments, wherein at least one HALS of general formula H4 is [ka] (H4-a) [ka] (H4-b) or [ka] (H4-c) The polymer P is a diester selected from

[0179] 25. Polymer P according to any one of the preceding embodiments, wherein at least one HALS of formula H4 is a carbonate [ka] (H4-d) That is, polymer P.

[0180] 26. Polymer P according to any of the preceding embodiments, in which at least one HALS H5 is 1,5,8,12-tetrakis[4,6-bis(N-butyl-N-1,2,2,6,6-pentamethyl-4-piperidylamino)-1,3,5-triazin-2-yl]-1,5,8,12-tetraazadodecane.

[0181] 27. Polymer P according to any of the preceding embodiments, in which at least one HALS H6 is tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)butane-1,2,3,4-tetracarboxylate.

[0182] 28. Polymer P according to any of the preceding embodiments, in which at least one diester or polyester B1 is selected from dimethyl succinate, diethyl succinate, or 1,2-cyclohexanedicarboxylic acid diisononyl ester.

[0183] 29. Polymer P according to any of the preceding embodiments, in which at least one phthalic anhydride derivative B2 is trimellitic anhydride.

[0184] 30. Polymer P according to any of the preceding embodiments, in which at least one diisocyanate or polyisocyanate B3 is selected from 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, or dimers or trimers thereof.

[0185] 31. Polymer P according to any of the preceding embodiments, in which at least one epoxy polymer B4 comprises a monomer selected from trimethylolpropane triglycidyl ether or bisphenol A diglycidyl ether.

[0186] 32. Polymer P according to any of the preceding embodiments, in which at least one maleic anhydride polymer B5 is a styrene-maleic anhydride copolymer.

[0187] 33. Polymer P according to any of the preceding embodiments, having a weight average molecular weight according to DIN 55672-1 in the range of 200 g / mol to 100,000 g / mol.

[0188] 34. Polymer P according to any of the preceding embodiments, having a weight average molecular weight according to DIN 55672-1 in the range of 500 g / mol to 50,000 g / mol.

[0189] 35. Polymer P according to any of the preceding embodiments, having a weight average molecular weight according to DIN 55672-1 in the range of 2000 g / mol to 50,000 g / mol.

[0190] 36. Polymer P according to any of the preceding embodiments, having a polydispersity index according to DIN 55672-1 in the range of 1.1 to 4.0.

[0191] 37. Polymer P according to any one of embodiments 1 to 36, having a HALS content of 0.1 to 3.5 mmol HASL / g.

[0192] 38. Polymer P according to any of the preceding embodiments, having a HALS content of 0.2 to 3.0 mmol HASL / g.

[0193] 39. A method for preparing a polymer P according to any of embodiments 1 to 38, comprising: i. mixing said at least one polyether A with said at least one hindered amine light stabilizer H selected from H2, H4, H6, or mixtures thereof; ii. heating the mixture obtained in step (i) at 80°C to 200°C; A method comprising:

[0194] 40. The method of embodiment 39, further comprising adding at least one catalyst selected from tetrabutyl titanate or dibutyltin dilaurate to the mixture obtained in step (i).

[0195] 41. The method according to embodiment 40, wherein the amount of the at least one catalyst is in the range of 0.1 to 5.0% by weight, based on the total amount of the reaction mixture.

[0196] 42. The method according to embodiment 40 or 41, wherein the amount of the at least one catalyst is in the range of 0.25 to 1.0 wt. %, based on the total amount of the reaction mixture.

[0197] 43. A method for preparing a polymer P according to any of embodiments 1 to 38, comprising: i. mixing said at least one polyether A, said at least one hindered amine light stabilizer H selected from H1, H2, H3, H4, H5, H6 or mixtures thereof, and said at least one compound B selected from B1, B2, or B5; ii. heating the mixture obtained in step (i) at 80°C to 200°C; A method comprising:

[0198] 44. The method of embodiment 43, further comprising adding at least one catalyst selected from tetrabutyl titanate or dibutyltin dilaurate to the mixture obtained in step (i).

[0199] 45. The method according to embodiment 44, wherein the amount of the at least one catalyst is in the range of 0.1 to 5.0 wt. %, based on the total amount of the reaction mixture.

[0200] 46. The method according to any of embodiments 43 to 45, wherein the amount of the at least one catalyst is in the range of 0.25 to 1.0 wt. %, based on the total amount of the reaction mixture.

[0201] 47. A method for preparing a polymer P according to any of embodiments 1 to 38, comprising: (i) reacting at least one polyether A with at least one compound B selected from B3 or B4; (ii) reacting the product obtained in step (i) with at least one hindered amine light stabilizer H selected from H1, H2, H3, H4, H5, H6 or mixtures thereof; A method comprising:

[0202] 48. The method of embodiment 47, further comprising adding at least one solvent in step (i); the at least one solvent is selected from ethyl acetate, or methoxypropyl acetate.

[0203] 49. The method of embodiment 47 or 48, further comprising adding at least one catalyst in an amount ranging from 0.1 to 5.0 wt. %, based on the total amount of the reaction mixture.

[0204] 50. The method of embodiment 49, wherein at least one catalyst is selected from aluminum trichloride.

[0205] 51. The method of any of embodiments 47 to 50, wherein step (i) is carried out at 40°C to 120°C.

[0206] 52. The method of any one of embodiments 47 to 51, wherein step (ii) is carried out at 50°C to 200°C.

[0207] 53. A liquid composition comprising a polymer P according to any of embodiments 1 to 38.

[0208] 54. A liquid composition in the form of a dispersion comprising at least one particulate solid material and at least one polymer P according to any of the preceding embodiments.

[0209] 55. The liquid composition according to embodiment 54, wherein at least one particulate solid material has a particle size D in the range of 0.005 um to 100 um according to a dynamic light scattering technique using a fixed scattering angle of 90° or 180°. 50 A liquid composition comprising:

[0210] 56. A liquid composition according to any of embodiments 54 or 55, wherein the at least one particulate solid material is at least one pigment.

[0211] 57. The liquid composition of any of embodiments 54 to 56, further comprising at least one additive selected from a filler, a binder, a wetting agent, a rheology modifier, a UV filter, an antifoaming agent, a leveling agent, a slip agent, a substrate wetting agent, an antioxidant, a radical scavenger, a biocide, or a coalescing agent.

[0212] 58. The liquid composition according to any of embodiments 54 to 57, in the form of a pigment paste, millbase, colorant, coating composition or ink.

[0213] 59. A coating composition comprising: i. a polymer P according to any one of embodiments 1 to 38; ii. at least one particulate solid material selected from a pigment, a filler, or a mixture thereof; iii. at least one liquid diluent, and iv. at least one polymer binder Including, A coating composition in which at least one particulate solid material is dispersed in a liquid diluent selected from an organic solvent, water, a reactive diluent, or a mixture thereof.

[0214] 60. The coating composition of embodiment 59, i. 0.1 to 50 wt. % of the polymer of any of embodiments 1 to 38, based on the total weight of the liquid composition; ii. 1 to 70 wt. %, based on the total weight of the coating composition, of at least one particulate solid material; iii. 10 to 98 wt. % of at least one liquid diluent, based on the total weight of the liquid composition; and iv. 10 to 98 wt. % of at least one binder, based on the total weight of the liquid composition. 1. A coating composition comprising:

[0215] 61. Use of a polymer P according to any of embodiments 1 to 38 as a dispersant.

[0216] 62. Use of a polymer P according to any of embodiments 1 to 38 as a light stabilizer.

[0217] 63. Use of a polymer P according to any of embodiments 1 to 38 in a coating composition.

[0218] While the present invention has been described with respect to specific embodiments thereof, certain modifications and equivalents will be apparent to those skilled in the art and are intended to be included within the scope of the present invention. [Example]

[0219] Example The present invention is further illustrated by the following non-limiting examples, in particular the test methods specified below are part of the general disclosure of this application and are not limited to the specific examples.

[0220] material The following materials are used in the examples: Pluriol® A520E is a polyether (methyl polyethylene glycol) with a MW of 500 g / mol; Irgazin® Red L 3670 HD is an organic pigment, Foamstar® SI 2250 is a defoamer for a variety of water-based coating systems and pigment concentrates. Foamaster® 8034 is a defoamer for emulsion paints. Dispex® CX4320 is a polymeric dispersant for inorganic fillers and pigments. Acronal® A754 is an aqueous dispersion of a linear acrylic copolymer, Rheovis® PU1216 is a non-ionic medium pseudoplastic rheology modifier for waterborne coatings The above are available from BASF Se.

[0221] Desmodur® ultra IL BA is an aromatic polyisocyanate based on toluene diisocyanate, Desmodur® ultra T100 is 2,4-toluene diisocyanate; The above are available from Coverstro.

[0222] Jeffamine® M-2070 is a propylene oxide / ethylene oxide (PO / EO) copolymer-based polyetheramine with a weight average molecular weight of approximately 2,000. The PO / EO molar ratio is 10 / 31.

[0223] Erisys® GE-30 is a low viscosity, high epoxy functionality resin The above are available from Hunstman Corporation.

[0224] SMA® 1000P is a low MW poly(styrene-co-maleic anhydride) resin; SMA® 2000P is a low MW poly(styrene-co-maleic anhydride) resin; The above are available from Cray Valley.

[0225] ADK STAB LA-81 is bis(1-undecanoxy-2,2,6,6-tetramethylpiperidin-4-yl) carbonate, ADK STAB LA-52 is tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)butane-1,2,3,4-tetracarboxylate; The above are available from Adeka Polymer Additives.

[0226] Bentone® LT is an organically modified purified hectorite clay-based thickener for rheology additives, waterborne paints and coatings. Finntalc M15 is a floating, medium-sized layered talc (Mg-silicate) The above are available from Elementis specialities.

[0227] Minex® 10 is a specialty mineral, a finely divided functional filler and extender, Available from Sibelco specialty minerals.

[0228] Calgon® N is a dispersing agent for emulsion paints, plasters and adhesives. Available from ICL Phosphate Specialty.

[0229] Silres® BS 1306 is a solvent-free, water-dilutable emulsion of polysiloxane modified with a functional silicone resin. Available from Wacker Chemie AG.

[0230] Dimethyl succinate, trimellitic anhydride, 4-hydroxy-2,2,6,6-tetramethylpiperidinyloxyl, 4-amino-2,2,6,6-tetramethylpiperidinyloxyl, 4-hydroxy-2,2,6,6-tetramethylpiperidine, 4-amino-2,2,6,6-tetramethylpiperidine, 4-hydroxy-1,2,2,6,6-pentamethyl-piperidine, 4-hydroxy-1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidine, 4-hydroxy-1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidine, 1,5,8,12-tetrakis[4,6-bis(N-butyl-N-1,2,2,6,6-pentamethyl-4-piperidylamino)-1,3,5-triazin-2-yl]-1,5,8,12-tetraazadodecane were obtained from Sigma. It was available from Aldrich.

[0231] method Epoxy content: The epoxy content was determined according to DIN EN ISO 7142.

[0232] Molecular weight: Weight average molecular weight (M w ), number average molecular weight (M n ), and polydispersity index (PDI) were determined in accordance with DIN 55672-1. The weight-average and number-average molecular weights of the polymers were determined by gel permeation chromatography (GPC) in accordance with DIN 55672-1 using THF as eluent (1 mL / min) and polystyrene as the standard resin.

[0233] Acid number: The acid number was determined according to DIN 53402:1990-09.

[0234] NCO number: The NCO number was determined according to DIN 53185.

[0235] HALS Content: HALS content is calculated based on the equivalents (mmol) of HALS molecules per gram of solid polymer.

[0236] Viscosity: Viscosity measured according to DIN 53019-1:2008-09 using a Thermo-Haake RheoStress 600 device at 22°C and a shear rate of 1 sec -1 Measurements were taken in CR mode on a Spindle CP50.

[0237] Delta E: Delta E was determined according to DIN EN ISO 16474-2, cycle number 1 (2014).

[0238] A) Polyether A - Polyether A(a) and Polyether A(b) Polyethers A1 and A2 were commercially available.

[0239] Polyether A1 was Jeffamine® M2070, and polyether A2 was Pluriol® A520E. Polyethers A3 to A5 were synthesized.

[0240] Preparation of polyethers A3-A5 Example 1: Preparation of Polyether A3 A reaction vessel maintained under a nitrogen atmosphere was charged with Intermediate A1 (50 g, 25 mmol) and 2-ethylhexyl glycidyl ether (4.5 g, 24 mmol), and the reaction mixture was heated at 170° C. until the epoxy content of the mixture was zero. The product was cooled to room temperature and Intermediate A3 was purified by M w It was obtained as a yellowish liquid with 2,500 g / mol and a PDI of 1.1.

[0241] Example 2: Preparation of Polyether A4 A reaction vessel maintained under a nitrogen atmosphere was charged with Intermediate A1 (50 g, 25 mmol) and glycidyl hexadecyl ether (7.5 g, 25 mmol), and the reaction mixture was heated at 170° C. until the epoxy content of the mixture was zero. The product was cooled to room temperature and Intermediate A4 was obtained by HPLC. w It was obtained as a yellowish liquid with 2,600 g / mol and a PDI of 1.1.

[0242] Example 3: Preparation of Polyether A5 A 2 L autoclave equipped with a heating system, cooling coil, agitator, connection to a vacuum pump, and connection to an ethylene oxide or propylene oxide tank was charged with intermediate A2 (150 g) and potassium tert-butoxide (KO t Bu) (2 g) was charged, and the autoclave was then purged with nitrogen. The contents of the autoclave were heated to 110°C, and the contents were dehydrated under a reduced pressure of 10 mbar for 1 hour. The resultant was heated to 120°C, and ethylene oxide (300 g) was introduced into the autoclave under pressure over 12 hours. The reaction mixture was heated at this temperature until the pressure decreased and became constant. The temperature of the reaction mixture was then increased to 130°C, and 200 g of propylene oxide was introduced into the autoclave under pressure over 12 hours. The reaction mixture was heated at this temperature until the pressure decreased and became constant. All volatile by-products and residual monomers were removed under reduced pressure, yielding 640 g of intermediate A5.

[0243] M of intermediate A5 W The molecular weight was 1950 g / mol and the PDI was 1.3.

[0244] B) Compound B-Compounds B1~B7 [having at least one functional group selected from ester, isocyanate, anhydride, carboxylic acid, and epoxide] Compounds B1 to B7 were commercially available compounds.

[0245] Compound B1-a is dimethyl succinate, Compound B2-a is trimellitic anhydride, Compound B3-a was Desmodour® IL BA, an aromatic polyisocyanate based on toluene diisocyanate.

[0246] Compound B3-b is 2,4-toluene diisocyanate, Compound B4-a is a low viscosity high epoxy functionality resin, Compound B5-a and Compound B5-b were low MW poly(styrene-co-maleic anhydride) resins.

[0247] C) Hindered amine light stabilizers (HALS) The following hindered amine light stabilizers (HALS) were commercially available:

[0248] i) Hindered amine light stabilizers (HALS) of general formula H1 HALS H1-a to HALS H1-f were as follows:

[0249] [Table 1]

[0250] ii) Hindered Amine Light Stabilizer (HALS) Copolymer H2 HALS H2-a is a compound consisting of dimethyl succinate and M n =3500 and 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol.

[0251] [Table 2]

[0252] iii) Hindered Amine Light Stabilizers (HALS) - Triazine-based dimers with NH or OH functional groups H3 HALS H3-a was 2,4-bis[N-butyl-N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)amino]-6-(2-hydroxyethylamine)-1,3,5-triazine.

[0253] [Table 3]

[0254] iv) Hindered amine light stabilizers (HALS) of general formula H4 HALS H4-a to HALS H4-d were as follows:

[0255] [Table 4]

[0256] v) Hindered amine light stabilizers (HALS): Triazine-substituted alkylamine oligomers with H5-NH functional groups HALS-H5-a was 1,5,8,12-tetrakis[4,6-bis(N-butyl-N-1,2,2,6,6-pentamethyl-4-piperidylamino)-1,3,5-triazin-2-yl]-1,5,8,12-tetraazadodecane.

[0257] vi) Hindered Amine Light Stabilizer (HALS) H6-Polyol Polyester HALS H6-a was tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)butane-1,2,3,4-tetracarboxylate.

[0258] Polymer (P) synthesis Example 1: Preparation of polymer P1 Polymer 1: To a reaction vessel maintained under a nitrogen atmosphere were added Intermediate A1 (65 g), Intermediate B1-a (15 g), and Intermediate H1-f (20 g). The reaction mixture was heated at 120° C. for 1 hour. Tetrabutyl titanate (0.5 g) was added to the resulting mixture, which was then heated at 150° C. under reduced pressure until no more distillate was formed. The product was cooled and purified by M w Polymer P1 was obtained with a PDI of 1.9 and a 4,500 g / mol HALS content of 1.0 mmol HALS / g polymer.

[0259] Polymer 2-10 Polymers 2 to 10 were prepared by a process similar to that of polymer 1. The starting materials and their amounts are shown in Table 1.

[0260] [Table 5]

[0261] Polymer 11: To a reaction vessel maintained under a nitrogen atmosphere, Intermediate A2 (60 g), Intermediate B2-a (20 g), and Intermediate H1-f (20 g) were added, and the mixture was heated at 120°C for 1 hour. Tetrabutyl titanate (0.5 g) was added to the reaction mixture, which was then heated at 170°C under reduced pressure until the acid number of the reaction mixture reached a stable value, i.e., remained constant. The reaction mixture was cooled to give Polymer P11, with a Mw of 7,300 g / mol and a PDI of 1.7. HALS content: 1.0 mmol HALS / g polymer.

[0262] Polymer 12-14 Polymers 12 to 14 were prepared using a process similar to that for polymer 11. The starting materials and their respective amounts are shown in Table 2.

[0263] [Table 6]

[0264] Polymer 15: Ethyl acetate (50 g) and Intermediate B3-a (65 g) were added to a reaction vessel maintained under a nitrogen atmosphere and stirred at 30° C. Intermediate A1 (50 g) was slowly added to the reaction vessel, and the reaction mixture was heated at 40° C. for 3 hours. Intermediate H1-f (20 g) was slowly added to the reaction mixture, and the resulting mixture was stirred at 60° C. until the NCO number of the reaction mixture reached 0. Volatiles were removed under reduced pressure at 130° C. to give Polymer 15, with a Mw of 9,700 g / mol and a PDI of 1.6. HALS content: 1.0 mmol HALS / g polymer.

[0265] Polymer 16-21 Polymers 16 to 21 were prepared using a process similar to that used for preparing polymer 15. The starting materials and their respective amounts are listed in Table 3.

[0266] [Table 7]

[0267] Polymer 22: Intermediate B4-a (14 g) was added to a reaction vessel maintained under a nitrogen atmosphere and stirred at 50°C. Intermediate A1 (65 g) and AlCl3 (0.1 g) were slowly added to the reaction vessel, and the mixture was heated at 100°C for 5 hours. Intermediate H1-b (6 g) was slowly added to the reaction mixture, and the reaction mixture was heated at 170°C until the epoxy content of the reaction mixture was zero. The resulting polymer 22 had a Mw of 6,700 g / mol and a PDI of 1.4. HALS content: 0.4 mmol HALS / g polymer.

[0268] Polymer 23-26 Polymers 23 to 26 were prepared using a process similar to that used for preparing polymer 22. The starting materials and their respective amounts are listed in Table 4.

[0269] [Table 8]

[0270] Polymer 27: To a reaction vessel maintained under a nitrogen atmosphere, the solvent methoxypropyl acetate (15 g) and Intermediate B5-a (10 g) were added and the mixture was stirred until homogeneous. Intermediate A1 (50 g) and Intermediate H1-b (3.5 g) were added to the reaction vessel, and the resulting mixture was heated at 170°C under reduced pressure until the acid value stabilized, i.e., the acid value no longer changed. The resulting polymer 27 had a Mw of 22,500 g / mol and a PDI of 2.5. HALS content: 0.3 mmol HALS / g polymer.

[0271] Polymer 28-30 Polymers 28 to 30 were prepared by a process similar to that for polymer 27. The starting materials and their respective amounts are listed in Table 5.

[0272] [Table 9]

[0273] Polymer 31: To a reaction vessel maintained under a nitrogen atmosphere, Intermediate A1 (50 g) and Intermediate H2-a (50 g) were added, and the mixture was heated to 120° C. Tetrabutyl titanate (0.5 g) was added, and the resulting mixture was heated at 170° C. for 30 hours to yield Polymer 31 with a Mw of 8,900 g / mol and a PDI of 2.9. HALS content: 1.8 mmol HALS / g polymer.

[0274] Polymer 32-49 Polymers 32 to 49 were prepared by a process similar to that for polymer 31. The starting materials and their respective amounts are shown in Table 6.

[0275] [Table 10]

[0276] Applicable Tests: A) Aqueous solution of polymer P To evaluate the dispersant effect of the obtained polymer P, a concentrated aqueous solution was prepared using the polymer P.

[0277] To prepare the aqueous solution, polymer P (40 g) was charged into a reactor and heated to 90° C. with stirring, followed by slow addition of hot water (60 g). The resulting aqueous solution was stirred for 3 hours.

[0278] B) Millbase Preparation A resin-free pigment concentrate (millbase) was prepared using Polymer P.

[0279] The ingredients of the millbase are shown below in Formula 1. These ingredients in Formula 1 were dispersed in a Scandex Shaker with glass beads for 4 hours. The millbase was then filtered and stored at room temperature overnight.

[0280] [Table 11]

[0281] Dispersant performance was found to be generally very good with low millbase viscosities.

[0282] Table 7 shows the viscosity data for the millbases after 24 hours at room temperature and after 14 days at 50°C.

[0283] [Table 12]

[0284] C) Coating Composition The coating compositions were prepared by mixing the millbase with the letdown compositions shown in Table 8.

[0285] Millbase (MB) (20 g) of the example shown in Table 7 was mixed into 80 g letdown formulation using a Dispermat at 1000 rpm for 5 minutes.

[0286] [Table 13]

[0287] D) Result The coating compositions were applied to cold-rolled steel panels using a 250 μm applicator bar. Each sample was applied to three panels. The wet films were allowed to stand at room temperature for 7 days.

[0288] The artificial weathering and radiation resistance of the dried films was evaluated according to DIN EN ISO 16474-2, cycle-No. 1 (2014). The results are shown in Table 9.

[0289] The weathering test results (Delta E) clearly showed that coating compositions containing dispersants containing HALS exhibited good weathering resistance.

[0290] [Table 14]

Claims

1. at least one polyether A, at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6, or mixtures thereof; at least one compound B having at least one functional group selected from the group consisting of ester, isocyanate, anhydride, carboxylic acid, or epoxide, said at least one compound B being selected from B1, B2, B3, B4, B5, or a mixture thereof; a polymer P obtained by reacting or at least one polyether A, - at least one hindered amine light stabilizer selected from H2, H4, H6, or mixtures thereof; A polymer P obtained by reacting The at least one polyether A is selected from at least one polyether of general formula A(a), at least one polyether of general formula A(b), or a mixture thereof; (a) said at least one polyether of general formula A(a) 【Chemical 1】 Formula A(a) (In the formula, R １ is a linear or branched, substituted or unsubstituted C １ ~C ２２ Alkyl, straight or branched chain substituted or unsubstituted C １ ~C ２２ Alkylenyl, substituted or unsubstituted C ６ ~C １５ Alkylaryl, or substituted or unsubstituted C ６ ~C １４ aryl; R ２ is a linear or branched, substituted or unsubstituted C １ ~C ４ alkyl; m is an integer ranging from 1 to 100; n is an integer ranging from 0 to 100; The m units and the n units are distributed to form a random copolymer, a block copolymer, or a gradient copolymer; and Z is -OH, -NH ２ , or -NHR ３ where R ３ is a linear or branched, substituted or unsubstituted C １ ~C ２２ alkyl); (b) said at least one polyether of general formula A(b) is at least one polyether of general formula A(a): 【Chemistry 2】 Formula A(a) (In the formula, R １ , R ２ , m, n, and Z are as defined above) At least one compound of formula (E): 【Chemistry 3】 Formula (E) (In the formula, R ４ is a linear or branched, substituted or unsubstituted C １ ~C ２２ Alkyl, straight or branched chain substituted or unsubstituted C １ ~C ２２ Alkylenyl, substituted or unsubstituted C ６ ~C １５ Alkylaryl, or substituted or unsubstituted C ６ ~C １４ aryl, and X is O, S or CH ２ can be obtained by reacting the molar ratio of said at least one polyether of general formula A(a) to said at least one compound of formula (E) is in the range of 1:0.8 to 1:5; moreover a) The hindered amine light stabilizers (HALS) of general formula H1 are 【Chemistry 4】 Formula H1 (In the ceremony R ５ and R ６ are independently H or substituted or unsubstituted C １～４ alkyl; R ７ is -OH, -NH ２ , -NHR ９ , -R １０ -OH, -R １０ -NH ２ , or -R １０ -NHR ９ Selected from: R ８ is -H, -O, straight or branched chain substituted or unsubstituted C １ ~C ２２ Alkyl, straight or branched chain substituted or unsubstituted C ３ ~C ８ cycloalkyl, —OR １１ , -R １２ -OH or -O-R １２ -OH; Here, R ９ , and R １１ are independently straight or branched chain substituted or unsubstituted C １ ~C ２２ alkyl; Here, R １０ and R １２ are independently straight or branched chain substituted or unsubstituted C １ ~C ２２ alkylene); b) The hindered amine light stabilizer (HALS) H2 is (i) 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol; and (ii) General formula: 【Chemistry 5】 (In the formula, R １３ is a linear or branched, substituted or unsubstituted C １ ~C １２ alkyl; R １４ is a linear or branched, substituted or unsubstituted C ２ ~C １２ at least one dicarboxylic acid ester of a HALS copolymer comprising: c) The hindered amine light stabilizers (HALS) of general formula H3 are triazine-based dimers having —NH or —OH— functional groups: 【Chemistry 6】 Formula H3 (In the formula, R ５ , R ６ , and R ８ is as defined above; R １５ is H or a straight or branched chain substituted or unsubstituted C １ ~C ６ alkyl; R １６ is H or a straight or branched chain substituted or unsubstituted C １ ~C ６ alkyl; R １７ is -H or -R １８ —OH; R １８ is a linear or branched, substituted or unsubstituted C １ ~C ２２ alkylene); d) said hindered amine light stabilizer (HALS) of general formula H4 is a diester or carbonate functionalized HALS compound; 【Chemistry 7】 Formula H4 (In the formula, R ５ , R ６ , and R ８ is as defined above; L １ teeth, 【Chemistry 8】 or 【Chemistry 9】 and where * indicates the point of attachment to O R １９ is a linear or branched, substituted or unsubstituted C １ ~C ２２ alkylene); e) The hindered amine light stabilizer (HALS) H5 is a triazine-substituted alkylamine oligomer having an NH-functional group: 1,5,8,12-tetrakis[4,6-bis(N-butyl-N-1,2,2,6,6-pentamethyl-4-piperidylamino)-1,3,5-triazin-2-yl]-1,5,8,12-tetraazadodecane; f) The hindered amine light stabilizer (HALS) H6 is a polyol polyester: tetrakis(1,2,2,6,6-pentamethyl-4-piperidyl)butane-1,2,3,4-tetracarboxylate; moreover B1 is a group represented by the general formula R ２０ (COOR ２１ ) (In the formula, R ２０ is a linear or branched, substituted or unsubstituted C １ ~C ２２ - alkylene, or substituted or unsubstituted C ６ ~C １０ arylene; R ２１ is a linear or branched, substituted or unsubstituted C １ ~C １２ - alkyl; and and q is an integer ranging from 2 to 5; B2 has the general formula: 【Chemistry 10】 (In the formula, R ２２ is 4-COOH, 4-NO ２ , 4-F, 4-Cl, or 4-Br); B3 has the general formula: G(NCO) ｒ wherein G is a straight or branched chain, substituted or unsubstituted C ２ ~C ２２ Alkyl, straight or branched chain substituted or unsubstituted C ３ ~C ８ Cycloalkyl, or substituted or unsubstituted C ６ ~C １４ arylene, and and r is 2 or 3 or 4; B4 is at least one epoxy polymer; and B5 is polymer P, which is at least one maleic anhydride polymer.

2. 2. The polymer P according to claim 1, wherein R １ is a straight or branched chain substituted or unsubstituted C １ ~C ２２ The polymer P is selected from alkyl.

3. 3. The polymer P according to claim 1 or 2, m is an integer ranging from 1 to 50; A polymer P, wherein n is an integer in the range of 1 to 50.

4. 3. The polymer P according to claim 1 or 2, m is an integer ranging from 1 to 100; Polymer P, wherein n is 0.

5. 5. Polymer P according to any one of claims 1 to 4, wherein the at least one polyether of general formula A(b) is obtainable by reacting at least one polyether of general formula A(a) with at least one compound of formula (E), wherein R ４ is 2-ethylhexyl, X=O, and the molar ratio of said at least one polyether of general formula A(a) to said at least one compound of formula (E) is in the range of 1:0.8 to 1:

2.

6. 6. Polymer P according to any one of claims 1 to 5, wherein the at least one polyether of general formula A(b) is obtainable by reacting at least one polyether of general formula A(a) with at least one compound of formula (E), wherein R ４ is hexadecyl, X=O, and the molar ratio of said at least one polyether of general formula A(a) to said at least one compound of formula (E) is in the range of 1:0.8 to 1:

2.

7. 7. Polymer P according to any one of claims 1 to 6, wherein the at least one HALS of formula H1 is selected from 4-hydroxy-2,2,6,6-tetramethylpiperidinyloxyl, 4-amino-2,2,6,6-tetramethyl-piperidinyloxyl, 4-hydroxy-2,2,6,6-tetramethylpiperidine, 4-amino-2,2,6,6-tetramethyl-piperidine, 4-hydroxy-1,2,2,6,6-pentamethyl-piperidine, or 4-hydroxy-1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidine.

8. 8. Polymer P according to any one of claims 1 to 7, wherein the at least one HALS H2 is a copolymer comprising dimethyl succinate polymer and 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol, having a weight average molecular weight according to DIN 55672-1 of 7000 g / mol.

9. 9. Polymer P according to any one of claims 1 to 8, wherein said at least one HALS of general formula H3 is 【Chemistry 11】 (H3-a) Polymer P.

10. 10. Polymer P according to any one of claims 1 to 9, wherein said at least one HALS of general formula H4 is 【Chemistry 12】 (H4-a) 【Chemistry 13】 (H4-b) or 【Chemistry 14】 (H4-c) Polymer P is a diester selected from

11. 11. Polymer P according to any one of claims 1 to 10, wherein the at least one HALS of formula H4 is a carbonate 【Chemistry 15】 (H4-d) Polymer P.

12. 12. Polymer P according to any one of claims 1 to 11, wherein the at least one diester or polyester B1 is chosen from dimethyl succinate, diethyl succinate, or 1,2-cyclohexanedicarboxylic acid diisononyl ester.

13. 13. Polymer P according to any one of claims 1 to 12, wherein the at least one diisocyanate or polyisocyanate B3 is chosen from 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, or dimers or trimers thereof.

14. 14. Polymer P according to any one of claims 1 to 13, wherein the at least one epoxy polymer B4 comprises a monomer selected from trimethylolpropane triglycidyl ether or bisphenol A diglycidyl ether.

15. 15. Polymer P according to any one of claims 1 to 14, wherein the at least one maleic anhydride polymer B5 is a styrene-maleic anhydride copolymer.

16. 16. Polymer P according to any one of claims 1 to 15, having a weight average molecular weight according to DIN 55672-1 in the range from 200 g / mol to 100,000 g / mol.

17. 17. Polymer P according to any one of claims 1 to 16, having a polydispersity index according to DIN 55672-1 in the range from 1.1 to 4.

0.

18. 18. Polymer P according to any one of claims 1 to 17, having a HALS content of 0.1 to 3.5 mmol HASL / g.

19. 19. A process for preparing a polymer P according to any one of claims 1 to 18, comprising the steps of: i. mixing said at least one polyether A with said at least one hindered amine light stabilizer H selected from H2, H4, H6, or mixtures thereof; ii. Heating the mixture obtained in step (i) at 80°C to 200°C; A method comprising:

20. A process for preparing a polymer P according to any one of claims 1 to 18, i. mixing the at least one polyether A, the at least one hindered amine light stabilizer H selected from H1, H2, H3, H4, H5, H6 or mixtures thereof, and the at least one compound B selected from B1, B2, or B5; ii. Heating the mixture obtained in step (i) at 80°C to 200°C; A method comprising:

21. 19. A process for preparing a polymer P according to any one of claims 1 to 18, comprising the steps of: (iii) reacting said at least one polyether A with said at least one compound B selected from B3 or B4; (iv) reacting the product obtained in step (i) with said at least one hindered amine light stabilizer H selected from H1, H2, H3, H4, H5, H6 or mixtures thereof; A method comprising:

22. A liquid composition comprising a polymer P according to any one of claims 1 to 18.

23. A liquid composition in the form of a dispersion comprising at least one particulate solid material and at least one polymer P according to any one of claims 1 to 18.

24. 24. The liquid composition of claim 23, further comprising at least one additive selected from fillers, binders, wetting agents, rheology modifiers, UV filters, defoamers, leveling agents, slip agents, substrate wetting agents, antioxidants, radical scavengers, biocides, or coalescing agents.

25. 25. A liquid composition according to claim 23 or 24 in the form of a pigment paste, millbase, colourant, coating composition or ink.

26. i. a polymer P according to any one of claims 1 to 18; ii. at least one particulate solid material selected from a pigment, a filler, or a mixture thereof; iii. at least one liquid diluent, and iv. at least one polymer binder 1. A coating composition comprising: A coating composition wherein the at least one particulate solid material is dispersed in a liquid diluent selected from an organic solvent, water, a reactive diluent, or mixtures thereof.

27. 19. Use of a polymer P according to any one of claims 1 to 18 as a dispersant.

28. 19. Use of a polymer P according to any one of claims 1 to 18 as a light stabilizer.

29. 19. Use of a polymer P according to any one of claims 1 to 18 in a coating composition.

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