Polyether-based dispersant with light stabilization effect

Abstract

The invention claimed herein relates to a polymer obtainable by reacting a polyether with a hindered amine light stabilizer (HALS). The invention claimed herein relates to a process for preparing the polymer. The invention claimed herein also relates to a liquid composition comprising the polymer and the use of the polymer as a dispersant and a light stabilizer.

Description

Technical Field

[0001] The invention claimed herein relates to a polymer obtainable by reacting a polyether with a hindered amine light stabilizer (HALS). The invention claimed herein relates to a process for preparing the polymer. The invention claimed herein also relates to a liquid composition comprising the polymer and the use of the polymer as a dispersant and light stabilizer. Background Art

[0002] Liquid pigment compositions containing pigments and fillers as well as a liquid vehicle are commonly used in various industrial and consumer technical applications, in particular for the coloring of coating compositions, including solvent- and water-borne paints, heavy-duty coatings, automotive coatings, in printing inks, or for the coloring of cosmetics, plastics, etc.

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

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

[0005] The dispersant property is useful for uniformly dispersing particulate materials such as pigments and fillers in the liquid composition, and for the stability of the liquid composition; whereas the light stabilizer property provides weathering stability to the coating obtained from the liquid composition.

[0006] In the prior art, polymers or oligomers with light stabilizers are known and are described, for example, in the following references.

[0007] US 9394244 B2 discloses polyalophanate oligomers comprising ethylenically unsaturated groups and polymer stabilizer groups selected from hindered amine light stabilizers, ultraviolet light absorbers, antioxidants and dihydrocarbyl hydroxylamines.

[0008] The polymers or oligomers with light stabilizers disclosed in the prior art have limitations, such as having weak dispersant properties or weak light stabilizer properties or both.

[0009] It is therefore an object of the invention claimed herein to provide a polymer which can be used as a dispersant in a liquid composition and which has light stabilizer properties. It is an object to provide a polymer which has good dispersant properties in a liquid composition, such as improved viscosity and improved stability. Furthermore, it is desired that the polymer provide a good light stabilizer effect (good weathering stability) for the coating obtained from the liquid composition. Summary of the invention

[0010] It has surprisingly been found that the polymers of the invention claimed herein, obtainable by reacting polyethers with hindered amine light stabilizers (HALS), can be used as dispersants and light stabilizers.

[0011] Thus, one aspect of the invention claimed herein is a polymer P obtainable by reacting:

[0012] - at least one polyether A;

[0013] - at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6 or a mixture thereof; and

[0014] - at least one compound B having at least one functional group selected from the group consisting of ester, isocyanate, anhydride, carboxylic acid, or epoxide, and the at least one compound B is selected from B1, B2, B3, B4, B5, or a mixture thereof;

[0015] or

[0016] - at least one polyether A; and

[0017] - at least one hindered amine light stabilizer selected from H2, H4, H6 or a mixture thereof;

[0018] in,

[0019] The at least one polyether A is selected from at least one polyether having the general formula A(a), at least one polyether having the general formula A(b), or a mixture thereof;

[0020] in

[0021] (a) the at least one polyether having the general formula A(a) is

[0022]

[0023]

[0024] in

[0025] R 1 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkyl, linear or branched substituted or unsubstituted C1-C 22 Alkylene, substituted or unsubstituted C6-C 15 Alkyl aryl, or substituted or unsubstituted C6-C 14 Aryl,

[0026] R 2 Selected from linear or branched substituted or unsubstituted C1-C4 alkyl;

[0027] m is an integer ranging from 1 to 100;

[0028] n is an integer ranging from 0 to 100;

[0029] The m units and the n units are distributed to form a random copolymer, a block copolymer or a gradient copolymer; and

[0030] Z is selected from -OH, -NH2 or -NHR 3 , where R 3 Selected from linear or branched substituted or unsubstituted C1-C 22 alkyl;

[0031] and

[0032] (b) the at least one polyether having the general formula A(b) is obtained by making at least one polyether having the general formula A(a)

[0033]

[0034] Where R 1 , R 2 , m, n, and Z are as defined above;

[0035] With at least one compound of formula (E) obtainable

[0036]

[0037] in,

[0038] R 4 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkyl, linear or branched substituted or unsubstituted C1-C 22 Alkylene, substituted or unsubstituted C6-C 15 Alkyl aryl, or substituted or unsubstituted C6-C 14 Aryl, and

[0039] X is selected from O, S or CH2;

[0040] and wherein the molar ratio of the at least one polyether having the general formula A(a) to the at least one compound having the formula (E) is in the range of 1:0.8 to 1:5;

[0041] and

[0042] in,

[0043] a) Hindered amine light stabilizers (HALS) having the general formula H1 are

[0044]

[0045] in

[0046] R 5 and R 6 are independently selected from H, or substituted or unsubstituted C 1-4 alkyl;

[0047] R 7 Selected from -OH, -NH2, -NHR 9 , -R 10 -OH, -R 10 -NH2, or -R 10 -NHR 9 ;

[0048] R 8 Selected from -H, -O, linear or branched substituted or unsubstituted C1-C 22 Alkyl, linear or branched substituted or unsubstituted C3-C8 cycloalkyl, -OR 11 , -R 12 -OH, or -OR 12 -OH;

[0049] Where R 9 and R 11 independently selected from linear or branched substituted or unsubstituted C1-C 22 Alkyl; and

[0050] Where R 10 and R 12 independently selected from linear or branched substituted or unsubstituted C1-C 22 Alkylene;

[0051] b) Hindered amine light stabilizer (HALS) H2 is a HALS copolymer comprising

[0052] (i) 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinol; and

[0053] (ii) at least one dicarboxylic acid ester having the general formula

[0054]

[0055] in,

[0056] R 13 Selected from linear or branched substituted or unsubstituted C1-C 12 Alkyl; and

[0057] R 14 Selected from linear or branched substituted or unsubstituted C2-C 12 Alkylene;

[0058] c) Hindered amine light stabilizers (HALS) having the general formula H3 are triazine-based dimers having -NH or -OH functional groups.

[0059]

[0060] in,

[0061] R 5 , R 6 and R 8 As defined above;

[0062] R 15 Selected from H, or linear or branched substituted or unsubstituted C1-C6 alkyl;

[0063] R 16 Selected from H, or linear or branched substituted or unsubstituted C1-C6 alkyl;

[0064] R 17 Select from -H or -R 18 -OH, where R 18 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkylene;

[0065] d) Hindered amine light stabilizers (HALS) having the general formula H4 are diester or carbonate functionalized HALS compounds

[0066]

[0067] in,

[0068] R 5 , R 6 and R 8 As defined above;

[0069] L1 is

[0070] where * indicates the point of attachment to O, and

[0071] R 19 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkylene;

[0072] e) Hindered amine light stabilizer (HALS) H5 is a triazine-substituted alkylamine oligomer with NH functional groups: 1,5,8,12-tetrakis[4,6-bis(N-butyl-N-1,2,2,6,6-pentamethyl-4-piperidinylamino)-1,3,5-triazin-2-yl]-1,5,8,12-tetraazadodecane;

[0073] f) Hindered amine light stabilizer (HALS) H6 is a polyol polyester tetrakis (1,2,2,6,6-pentamethyl-4-piperidinyl) butane-1,2,3,4-tetracarboxylate;

[0074] and

[0075] in

[0076] B1 is at least one 20 (COOR 21 ) q Diesters or polyesters;

[0077] in

[0078] R 20 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkylene, or substituted or unsubstituted C6-C 10 arylene;

[0079] R 21 Selected from linear or branched substituted or unsubstituted C1-C 12 -alkyl; and

[0080] q is an integer ranging from 2 to 5;

[0081] B2 is at least one phthalic anhydride derivative having the general formula

[0082]

[0083] Where R 22 Selected from 4-COOH, 4-NO2, 4-F, 4-Cl or 4-Br;

[0084] B3 is at least one diisocyanate or polyisocyanate having the general formula

[0085] G(NCO) r

[0086] wherein G is selected from a linear or branched substituted or unsubstituted C2-C 22 Alkyl, linear or branched substituted or unsubstituted C3-C8 cycloalkyl, or substituted or unsubstituted C6-C 14 arylene, and

[0087] r is 2 or 3 or 4;

[0088] B4 is at least one epoxy polymer; and

[0089] B5 is at least one maleic anhydride polymer.

[0090] Another aspect of the invention claimed herein relates to a process for preparing polymer P.

[0091] Yet another aspect of the invention claimed herein relates to a liquid composition comprising a polymer (P).

[0092] Yet another aspect of the invention claimed herein relates to a coating composition comprising i. a polymer P of the invention claimed herein;

[0093] ii. at least one particulate solid material selected from a pigment, a filler or a mixture thereof;

[0094] iii. at least one liquid diluent, and

[0095] iv. at least one polymer binder

[0096] wherein the 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.

[0097] Yet another aspect of the invention claimed herein relates to the use of polymer P as dispersant.

[0098] Yet another aspect of the invention claimed herein relates to the use of polymer P as light stabilizer.

[0099] Yet another aspect of the invention claimed herein relates to the use of polymer P in a coating composition. DETAILED DESCRIPTION

[0100] Before describing the present compositions and formulations of the invention claimed herein, it should be understood that the invention is not limited to the specific compositions and formulations described, as such compositions and formulations may, of course, vary. It should also be understood that the terminology used herein is not intended to be limiting, as the scope of the invention claimed herein will be limited only by the appended claims.

[0101] If a group is defined as including at least a certain number of embodiments hereinafter, this means that it also includes a group preferably consisting only of these embodiments. In addition, the terms 'first', 'second', 'third' or 'a', 'b', 'c', etc. in the specification and claims are used to distinguish between similar elements, and are not necessarily used to describe a sequential order or a chronological order. It should be understood that the terms used in this way are interchangeable where appropriate, and the embodiments of the invention claimed herein described herein can operate in other sequences except as described or shown herein. In the case where the terms 'first', 'second', 'third' or '(A)', '(B)' and '(C)' or '(a)', '(b)', '(c)', '(d)', 'i', 'ii', etc. relate to a method or use or test step, unless otherwise indicated in the application as described above or below, there is no time or time interval coherence between these steps, that is, these steps can be performed simultaneously or there can be a time interval of seconds, minutes, hours, days, weeks, months or even years between such steps.

[0102] Furthermore, ranges defined throughout this specification also include the endpoints, ie, a range of 1 to 10 means that both 1 and 10 are included in the range. For the avoidance of doubt, applicants are entitled to any equivalents under applicable law.

[0103] In the following paragraphs, different aspects of the invention claimed herein are defined in more detail. Unless explicitly indicated to the contrary, each aspect so defined may be combined with any one or more other aspects. In particular, any feature indicated as preferred or advantageous may be combined with any one or more other features indicated as preferred or advantageous.

[0104] References throughout this specification to 'one embodiment' or 'an embodiment' mean that a particular feature, structure, or characteristic described in connection with the embodiment is included in at least one embodiment of the invention claimed herein. Thus, the appearances of the phrase 'in one embodiment' or 'in an embodiment' in various places throughout this specification do not necessarily all refer to the same embodiment, but may.

[0105] Furthermore, in one or more embodiments, specific features, structures, or characteristics may be combined in any suitable manner, as will be apparent to those skilled in the art from this disclosure. Furthermore, although some embodiments described herein include some but not others that are included in other embodiments, combinations of features of different embodiments are still intended to be within the scope of the invention claimed herein and to form different embodiments, as will be understood by those skilled in the art. For example, in the appended claims, any of the claimed embodiments may be used in any combination.

[0106] It has been unexpectedly discovered that the polymers of the invention claimed herein, obtainable by reacting a polyether with a hindered amine light stabilizer (HALS), can be used as dispersants and light stabilizers. When covalently bound to certain polyether polymers, certain HALS perform well as dispersants in liquid compositions and further perform well as light stabilizers. The polyether polymer and the HALS are bound directly by covalent bonds or via a multifunctional compound covalently bound to each of them.

[0107] The invention claimed herein is directed to polymers containing polyethers and hindered amine light stabilizers (HALS).

[0108] Thus, one aspect of the invention claimed herein relates to a polymer P obtainable by reacting:

[0109] - at least one polyether A;

[0110] - at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6 or a mixture thereof; and

[0111] - at least one compound B having at least one functional group selected from the group consisting of ester, isocyanate, anhydride, carboxylic acid, or epoxide, and the at least one compound B is selected from B1, B2, B3, B4, B5, or a mixture thereof;

[0112] or

[0113] - at least one polyether A; and

[0114] - at least one hindered amine light stabilizer selected from H2, H4, H6 or a mixture thereof;

[0115] in,

[0116] The at least one polyether A is selected from at least one polyether having the general formula A(a), at least one polyether having the general formula A(b), or a mixture thereof;

[0117] in

[0118] (a) the at least one polyether having the general formula A(a) is

[0119]

[0120] in

[0121] R 1 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkyl, linear or branched substituted or unsubstituted C1-C 22 Alkylene, substituted or unsubstituted C6-C 15 Alkyl aryl, or substituted or unsubstituted C6-C 14 Aryl,

[0122] R 2 Selected from linear or branched substituted or unsubstituted C1-C4 alkyl;

[0123] m is an integer ranging from 1 to 100;

[0124] n is an integer ranging from 0 to 100;

[0125] The m units and the n units are distributed to form a random copolymer, a block copolymer or a gradient copolymer; and

[0126] Z is selected from -OH, -NH2 or -NHR 3 , where R 3 Selected from linear or branched substituted or unsubstituted C1-C 22 alkyl;

[0127] and

[0128] (b) the at least one polyether having the general formula A(b) is obtained by making at least one polyether having the general formula A(a)

[0129]

[0130] Where R 1 , R 2 , m, n, and Z are as defined above;

[0131] With at least one compound of formula (E) obtainable

[0132]

[0133] in,

[0134] R 4 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkyl, linear or branched substituted or unsubstituted C1-C 22 Alkylene, substituted or unsubstituted C6-C15 Alkyl aryl, or substituted or unsubstituted C6-C 14 Aryl, and

[0135] X is selected from O, S or CH2;

[0136] and wherein the molar ratio of the at least one polyether having the general formula A(a) to the at least one compound having the formula (E) is in the range of 1:0.8 to 1:5;

[0137] and

[0138] in,

[0139] a) Hindered amine light stabilizers (HALS) having the general formula H1 are

[0140]

[0141] in

[0142] R 5 and R 6 are independently selected from H, or substituted or unsubstituted C 1-4 alkyl;

[0143] R 7 Selected from -OH, -NH2, -NHR 9 , -R 10 -OH, -R 10 -NH2, or -R 10 -NHR 9 ;

[0144] R 8 Selected from -H, -O, linear or branched substituted or unsubstituted C1-C 22 Alkyl, linear or branched substituted or unsubstituted C3-C8 cycloalkyl, -OR 11 , -R 12 -OH, or -OR 12 -OH;

[0145] Where R 9 and R 11 independently selected from linear or branched substituted or unsubstituted C1-C 22 Alkyl; and

[0146] Where R 10 and R 12 independently selected from linear or branched substituted or unsubstituted C1-C 22 Alkylene;

[0147] b) Hindered amine light stabilizer (HALS) H2 is a HALS copolymer comprising

[0148] (i) 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinol; and

[0149] (ii) at least one dicarboxylic acid ester having the general formula

[0150]

[0151] in,

[0152] R 13 Selected from linear or branched substituted or unsubstituted C1-C 12 Alkyl; and

[0153] R 14 Selected from linear or branched substituted or unsubstituted C2-C 12 Alkylene;

[0154] c) Hindered amine light stabilizers (HALS) having the general formula H3 are triazine-based dimers having -NH or -OH functional groups.

[0155]

[0156] in,

[0157] R 5 , R 6 and R 8 As defined above;

[0158] R 15 Selected from H, or linear or branched substituted or unsubstituted C1-C6 alkyl;

[0159] R 16 Selected from H, or linear or branched substituted or unsubstituted C1-C6 alkyl;

[0160] R 17 Select from -H or -R 18 -OH, where R 18 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkylene;

[0161] d) Hindered amine light stabilizers (HALS) having the general formula H4 are diester or carbonate functionalized HALS compounds

[0162]

[0163] in,

[0164] R 5 , R 6 and R 8 As defined above;

[0165] L1 is

[0166] where * indicates the point of attachment to O, and

[0167] R 19 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkylene;

[0168] e) Hindered amine light stabilizer (HALS) H5 is a triazine-substituted alkylamine oligomer with NH functional groups: 1,5,8,12-tetrakis[4,6-bis(N-butyl-N-1,2,2,6,6-pentamethyl-4-piperidinylamino)-1,3,5-triazin-2-yl]-1,5,8,12-tetraazadodecane;

[0169] f) Hindered amine light stabilizer (HALS) H6 is a polyol polyester tetrakis (1,2,2,6,6-pentamethyl-4-piperidinyl) butane-1,2,3,4-tetracarboxylate;

[0170] and

[0171] in

[0172] B1 is at least one 20 (COOR 21 ) q Diesters or polyesters;

[0173] in

[0174] R 20 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkylene, and substituted or unsubstituted C6-C 10 arylene;

[0175] R 21 Selected from linear or branched substituted or unsubstituted C1-C 12 -alkyl; and

[0176] q is an integer ranging from 2 to 5;

[0177] B2 is at least one phthalic anhydride derivative having the general formula

[0178]

[0179] Where R 22 Selected from 4-COOH, 4-NO2, 4-F, 4-Cl or 4-Br;

[0180] B3 is at least one diisocyanate or polyisocyanate having the general formula

[0181] G(NCO)r

[0182] wherein G is selected from a linear or branched substituted or unsubstituted C2-C 22 Alkyl, linear or branched substituted or unsubstituted C3-C8 cycloalkyl, or substituted or unsubstituted C6-C 14 arylene, and

[0183] r is 2 or 3 or 4;

[0184] B4 is at least one epoxy polymer; and

[0185] B5 is at least one maleic anhydride polymer.

[0186] In the context of the invention claimed herein, the term alkyl, as used herein, refers to a non-cyclic saturated aliphatic group, including a alkyl radical of the general formula C n H 2n+1 represents a straight chain or branched chain alkyl saturated hydrocarbon group, and wherein n is the number of carbon atoms 1, 2, 3, 4, etc.

[0187] Preferably, alkyl refers to a straight-chain unsubstituted C1 to C 22 a carbon atom 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, eicosyl, heneicosyl, and docosyl.

[0188] Preferably, alkyl refers to a branched unsubstituted C3 to C 22a carbon atom selected from the group consisting of 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, 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, 6-methyldecyl, 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, 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.

[0189] In the context of the invention claimed herein, the term alkenyl, as used herein, refers to a non-cyclic unsaturated aliphatic group having at least one double bond, including a group consisting of the general formula C n H 2n-1 represents a straight-chain ethylenically unsaturated hydrocarbon group, and wherein n is the number of carbon atoms 1, 2, 3, 4, etc.

[0190] Preferably, alkenyl refers to a straight-chain unsubstituted C1 to C 22a carbon atom selected from the group consisting of 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, 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-1 0-enyl, dodeca-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, 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, pentadeca-2-enyl, pentadeca-3-enyl, pentadeca-4-enyl, pentadeca-5-enyl, pentadeca-6-enyl, pentadeca-7-enyl, pentadeca-8-enyl, pentadeca-9-enyl, pentadeca-10-enyl, pentadeca-11-enyl, pentadeca-12-enyl, pentadeca-13-enyl, pentadeca-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,Hexadec-14-enyl, hexadec-15-enyl, heptadeca-1-enyl, heptadeca-2-enyl, heptadeca-3-enyl, heptadeca-4-enyl, heptadeca-5-enyl, heptadeca-6-enyl, heptadeca-7-enyl, heptadeca-8-enyl, heptadeca-9-enyl, heptadeca-10-enyl, heptadeca-11-enyl, heptadeca-12-enyl, heptadeca-13-enyl, heptadeca-14-enyl, heptadeca-15-enyl, heptadeca-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-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 1-enyl, 10-enyl, 11-enyl, 12-enyl, 13-enyl, 14-enyl, 15-enyl, 16-enyl, 17-enyl, 19-enyl, 20-enyl, 25-enyl, 26-enyl, 27-enyl, 28-enyl, 29-enyl, 30-enyl, 31-enyl, 32-enyl, 33-enyl, 34-enyl, 35-enyl, 36-enyl, 37-enyl, 38-enyl, 39-enyl, 40-enyl, 41-enyl, 42-enyl, 43-enyl, 44-enyl, 45-enyl, 46-enyl, 47-enyl, 48-enyl, 49-enyl, 50-enyl, 51-enyl, 52-enyl, 53-enyl, 54-enyl, 55-enyl, 56-enyl, 57-enyl, 58-enyl, 59-enyl, 60-enyl, 61-enyl, 62-enyl, 63-enyl, 64-enyl, 65-enyl, 66-enyl, 67-enyl, 68-enyl, 69-enyl, 70-enyl, 71-enyl, 72-enyl, 73-enyl, 74-enyl, 75-enyl, 76-enyl, 77-enyl, 78-enyl, 79-enyl, 80-enyl, 81-enyl, 82-enyl, 83-enyl, 84-enyl, 85-enyl, 86-enyl, 18-enyl, eicos-1-enyl, eicos-2-enyl, eicos-3-enyl, eicos-4-enyl, eicos-5-enyl, eicos-6-enyl, eicos-7-enyl, eicos-8-enyl, eicos-9-enyl, eicos-10-enyl, eicos-11-enyl, eicos-12-enyl, eicos-13-enyl, eicos-14-enyl, eicos-15-enyl, eicos-16-enyl, eicos-17-enyl, eicos-18-enyl, eicos-19-enyl, heneicos-1-enyl, heneicos-2-enyl, heneicos-3-enyl, heneicos-4-enyl, heneicos-5-enyl, heneicos-6-enyl, heneicos-7-enyl, unicos-7-enyl, heicos-8-enyl, heicos-9-enyl, heicos-10-enyl, heicos-11-enyl, heicos-12-enyl, heicos-13-enyl, heicos-14-enyl, heicos-15-enyl, heicos-16-enyl, heicos-17-enyl, heicos-18-enyl, heicos-19-enyl, heicos-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-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.

[0191] In the context of the invention claimed herein, the term alkylene as used herein refers to a saturated, divalent, straight or branched chain hydrocarbon group. Examples of such preferred alkylene groups 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.

[0192] In the context of the invention claimed herein, the term cycloalkyl as used herein refers to monocyclic and bicyclic 3- to 15-membered saturated alicyclic groups, including branched cycloalkyl saturated hydrocarbons.

[0193] Preferably, cycloalkyl refers to C3 to C 15 A carbon atom selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, cyclotridecyl, cyclotetradecyl and cyclopentadecyl.

[0194] In the context of the invention claimed herein, the term aryl as used herein refers to phenyl or naphthyl, preferably phenyl. The term substituted aryl refers to aryl in which some or all of the hydrogen atoms are replaced by substituents, preferably these substituents are selected from hydroxy, halogen, cyano, C1-C4-alkyl and C1-C4-alkoxy. Preferably aryl is unsubstituted or carries 1, 2 or 3 substituents.

[0195] In the context of the invention claimed herein, as used herein, the term "alkylaryl" refers to an alkyl-substituted aryl group in each case, wherein one hydrogen atom at any position of the alkyl carbon backbone is replaced by an aryl moiety. Preferably, arylalkyl is benzyl (-CH2-C6H5), ethylphenyl (-CH2-CH2-C6H5, -(CH3)CH-C6H5) and the like.

[0196] In the context of the invention claimed herein, the term "pigmentary material" includes both pigments and fillers and thus relates to pigments, fillers or mixtures of pigments and fillers.

[0197] In the context of the invention claimed herein, the term "D50" refers to the median particle size where 50% of the distribution has a smaller particle size and 50% of the distribution has a larger particle size.

[0198] In a preferred embodiment, the polymer P is obtainable by reacting:

[0199] a) at least one polyether A;

[0200] b) at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6 or a mixture thereof; and

[0201] 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, and the at least one compound B is selected from B1, B2, B3, B4, B5, or a mixture thereof.

[0202] In a preferred embodiment, the polymer P is obtainable by reacting:

[0203] a) at least one polyether A; and

[0204] b) at least one hindered amine light stabilizer selected from H2, H4, H6 or a mixture thereof.

[0205] In a preferred embodiment, the polymer P is obtainable by reacting:

[0206] a) at least one polyether A(a);

[0207] b) at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6 or a mixture thereof; and

[0208] 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, and the at least one compound B is selected from B1, B2, B3, B4, B5, or a mixture thereof.

[0209] In a preferred embodiment, the polymer P is obtainable by reacting:

[0210] a) at least one polyether A(b) in which X is O;

[0211] b) at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6 or a mixture thereof; and

[0212] 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, and the at least one compound B is selected from B1, B2, B3, B4, B5, or a mixture thereof.

[0213] In a preferred embodiment, the polymer P is obtainable by reacting:

[0214] a) at least one polyether A(b) in which X is CH2;

[0215] b) at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6 or a mixture thereof; and

[0216] 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, and the at least one compound B is selected from B1, B2, B3, B4, B5, or a mixture thereof.

[0217] In a preferred embodiment, the polymer P is obtainable by reacting:

[0218] a) at least one polyether A(a); and

[0219] b) at least one hindered amine light stabilizer selected from H2, H4, H6 or a mixture thereof.

[0220] In a preferred embodiment, the polymer P is obtainable by reacting:

[0221] a) at least one polyether A(b) in which X is O; and

[0222] b) at least one hindered amine light stabilizer selected from H2, H4, H6 or a mixture thereof.

[0223] In a preferred embodiment, the polymer is obtainable by reacting:

[0224] a) at least one polyether A(b) in which X is CH2; and

[0225] b) at least one hindered amine light stabilizer selected from H2, H4, H6 or a mixture thereof.

[0226] In a preferred embodiment,

[0227] m is an integer in the range of 1 to 50; and

[0228] n is an integer ranging from 1 to 50.

[0229] In a more preferred embodiment,

[0230] m is an integer in the range of 1 to 25; and

[0231] n is an integer ranging from 1 to 25.

[0232] In a preferred embodiment, the at least one polyether A is at least one polyether having the general formula A(a).

[0233]

[0234] In a preferred embodiment, R 1 It is -CH3.

[0235] In a preferred embodiment, the at least one polyether having formula A(a) is a copolymer comprising ethylene oxide and propylene oxide.

[0236] In a preferred embodiment, R 2 It is -CH3.

[0237] In a preferred embodiment, R 2 is -CH3 and Z is NH2.

[0238] In a preferred embodiment, the at least one polyether of the general formula A(a) is a block copolymer of ethylene oxide and propylene oxide having a weight-average molecular weight of 2000 g / mol according to DIN 55672-1.

[0239] In a preferred embodiment, R 2 is -CH3 and Z is OH.

[0240] In a preferred embodiment, the at least one polyether of the general formula A(a) is a block copolymer comprising ethylene oxide and propylene oxide and having a weight-average molecular weight of 1950 g / mol according to DIN 55672-1.

[0241] In a preferred embodiment, the at least one polyether A is a homopolymer comprising ethylene oxide.

[0242] In a preferred embodiment, m is an integer in the range of 1 to 100; and n is 0.

[0243] In a more preferred embodiment, m is an integer in the range of 1 to 50; and n is 0.

[0244] In the most preferred embodiment, m is an integer in the range of 1 to 25; and n is zero.

[0245] In a preferred embodiment, Z is -OH.

[0246] In a preferred embodiment, the at least one polyether of the general formula A(a) is a methoxypolyethylene glycol having a weight average molecular weight of 500 g / mol according to DIN 55672-1.

[0247] In a preferred embodiment, the at least one polyether A is at least one polyether having the general formula A(b), which is obtained by mixing at least one polyether having the general formula A(a) with

[0248]

[0249] Where R 1 , R 2 , m, n, and Z are as defined above;

[0250] Obtainable by reaction with at least one compound of formula (E).

[0251]

[0252] In preferred embodiments, the molar ratio of at least one polyether having general formula A(a) to at least one compound having formula (E) is in the range of 1:0.8 to 1:5; more preferably 1:0.8 to 1:3; and most preferably 1:0.8 to 1:2.

[0253] In a preferred embodiment, at least one polyether of the general formula A(b) is obtainable by reacting at least one polyether of the general formula A(a) with at least one compound of the formula (E), wherein R 4 is 2-ethylhexyl, and X═O; and the molar ratio of at least one polyether having the general formula A(a) to at least one compound having the formula (E) is in the range of 1:0.8 to 1:2.

[0254] In a preferred embodiment, at least one polyether of the general formula A(b) is obtainable by reacting at least one polyether of the general formula A(a) with at least one compound of the formula (E), wherein R 4 is hexadecyl, and X═O; and the molar ratio of the at least one polyether having the general formula A(a) to the at least one compound having the formula (E) is in the range of 1:0.8 to 1:2.

[0255] In a preferred embodiment, at least one HALS having formula H1 is selected from 4-hydroxy-2,2,6,6-tetramethylpiperidinyloxy, 4-amino-2,2,6,6-tetramethyl-piperidinyloxy, 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.

[0256] In a preferred embodiment, at least one HALS having formula H1 is 4-hydroxy-2,2,6,6-tetramethylpiperidinyloxy (H1-a).

[0257] In a preferred embodiment, at least one HALS having formula H1 is 4-amino-2,2,6,6-tetramethyl-piperidinyloxy (H1-b).

[0258] In a preferred embodiment, the at least one HALS having formula H1 is 4-hydroxy-2,2,6,6-tetramethylpiperidine (H1-c).

[0259] In a preferred embodiment, the at least one HALS having formula H1 is 4-amino-2,2,6,6-tetramethyl-piperidine (H1-d).

[0260] In a preferred embodiment, the at least one HALS having formula H1 is 4-hydroxy-1,2,2,6,6-pentamethyl-piperidine (H1-e).

[0261] In a preferred embodiment, the at least one HALS having formula H1 is 4-hydroxy-1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidine (H1-f).

[0262] In a preferred embodiment, at least one HALS H2 is a copolymer comprising a dimethyl succinate polymer and 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinylethanol, the copolymer having a weight average molecular weight according to DIN 55672-1 of 7000 g / mol.

[0263] In a preferred embodiment, at least one HALS having the general formula H3 is

[0264]

[0265] In a preferred embodiment, at least one HALS having the general formula H4 is a diester selected from the group consisting of

[0266]

[0267] or

[0268]

[0269] In a preferred embodiment, at least one HALS having formula H4 is a carbonate

[0270]

[0271] In a preferred embodiment, at least one HALS having formula H4 is

[0272]

[0273] In a preferred embodiment, at least one HALS having formula H4 is

[0274]

[0275] In a preferred embodiment, at least one HALS having formula H4 is

[0276]

[0277] In a preferred embodiment, at least one HALS H5 is 1,5,8,12-tetrakis[4,6-bis(N-butyl-N-1,2,2,6,6-pentamethyl-4-piperidinylamino)-1,3,5-triazin-2-yl]-1,5,8,12-tetraazadodecane.

[0278] In a preferred embodiment, the at least one HALS H6 is tetrakis(1,2,2,6,6-pentamethyl-4-piperidinyl)butane-1,2,3,4-tetracarboxylate.

[0279] Commercially available HALS include those sold under the trade names 622, 152. 119. 770, 292 and 123, can be used for the invention claimed herein.

[0280] In a preferred embodiment, the at least one diester or polyester B1 is selected from dimethyl succinate, diethyl succinate, or diisononyl-1,2-cyclohexanedicarboxylate.

[0281] In a more preferred embodiment, the at least one diester or polyester B1 is dimethyl succinate (B1-a).

[0282] In a preferred embodiment, the at least one phthalic anhydride derivative B2 is trimellitic anhydride (B2-a).

[0283] In a preferred embodiment, the 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.

[0284] In a more preferred embodiment, the at least one diisocyanate B3 is 2,4-toluene diisocyanate (B3-a).

[0285] In a more preferred embodiment, the at least one diisocyanate B3 is a mixture of 2,4-toluene diisocyanate and 2,6-toluene diisocyanate.

[0286] In a more preferred embodiment, the at least one diisocyanate B3 is selected from isophorone diisocyanate, hexamethylene diisocyanate, or dimers or trimers thereof.

[0287] Commercially available isocyanates include mixtures of monomeric forms of isocyanates as well as polymeric forms such as dimers and trimers. Mixtures may also be used in the invention claimed herein.

[0288] In a preferred embodiment, the at least one epoxy polymer B4 comprises monomers selected from trimethylolpropane triglycidyl ether or bisphenol A diglycidyl ether.

[0289] In a more preferred embodiment, the at least one epoxy polymer B4 comprises trimethylolpropane triglycidyl ether.

[0290] In a preferred embodiment, the at least one maleic anhydride polymer B5 is a styrene maleic anhydride copolymer.

[0291] 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 of 500 g / mol to 10,000 g / mol.

[0292] In a preferred embodiment, the polymer P is obtainable by reacting a polyether A and a hindered amine light stabilizer (HALS) H.

[0293] In a preferred embodiment, the polymer P is obtainable by reacting:

[0294] - a polyether A selected from A1, A2, A4 or A5; and

[0295] -Hindered amine light stabilizer (HALS) H2-a.

[0296] In a preferred embodiment, the polymer P is obtainable by reacting a polyether A, a hindered amine light stabilizer (HALS) H and a compound B.

[0297] In a preferred embodiment, the polymer P is obtainable by reacting:

[0298] - Compound B1-a;

[0299] - a polyether A selected from A1, A3, A4 or A5; and

[0300] - a 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.

[0301] In a preferred embodiment, the polymer P is obtainable by reacting:

[0302] - Compound B2-a;

[0303] - a polyether A selected from A3 or A4; and

[0304] - a hindered amine light stabilizer (HALS) H selected from H1-a, H1-c or H1-e.

[0305] In a preferred embodiment, the polymer P is obtainable by reacting:

[0306] - a compound B selected from B3-a or B3-b;

[0307] - a polyether A selected from A1, A2 or A5; and

[0308] - a hindered amine light stabilizer (HALS) H selected from H1-a, H1-c or H-3a.

[0309] In a preferred embodiment, the polymer P is obtainable by reacting:

[0310] - Compound B4-a;

[0311] - a polyether A selected from A1, A2, A3 or A5; and

[0312] - a hindered amine light stabilizer (HALS) H selected from H1-b, H1-d or H5-a.

[0313] In a preferred embodiment, the polymer P is obtainable by reacting:

[0314] - a compound B selected from B5-a or B-5b;

[0315] - polyether A1; and

[0316] - a hindered amine light stabilizer (HALS) H selected from H1-b or H1-d.

[0317] In a preferred embodiment, the polymer P is obtainable by reacting:

[0318] - Compound B1-a;

[0319] - a polyether A selected from A1, A3, A4 or A5; and

[0320] - a hindered amine light stabilizer (HALS) H selected from H1-b, H1-d, H1-f, H-3a or H-5.

[0321] In a preferred embodiment, polymer P is obtainable by reacting polyether A, two hindered amine light stabilizers (HALS) and compound B.

[0322] In a preferred embodiment, the polymer P is obtainable by reacting:

[0323] - Compound B1-a;

[0324] - a polyether A selected from A1, A3, A4 or A5; and

[0325] - a hindered amine light stabilizer (HALS) H selected from H-2a, H4-a or H4-b.

[0326] In a preferred embodiment, polymer P is obtainable by reacting polyether A, three hindered amine light stabilizers (HALS) and compound B.

[0327] In a preferred embodiment, the polymer P is obtainable by reacting:

[0328] - Compound B1-a;

[0329] - polyether A3; and

[0330] - Hindered amine light stabilizers (HALS) H H-2a, H4-a and H4-b.

[0331] Polymer P

[0332] In a preferred embodiment, the polymer P has a weight average molecular weight in the range of 200 g / mol to 100,000 g / mol according to DIN 55672-1.

[0333] In a preferred embodiment, the polymer P has a weight average molecular weight in the range of 500 g / mol to 50,000 g / mol according to DIN 55672-1.

[0334] In a preferred embodiment, the polymer P has a weight average molecular weight in the range of 2000 g / mol to 50,000 g / mol according to DIN 55672-1.

[0335] In a preferred embodiment, polymer P has a polydispersity index in accordance with DIN 55672-1 in the range from 1.1 to 4.0.

[0336] In a preferred embodiment, the polymer P has a HALS content of 0.1 to 3.5 mmol HASL / g.

[0337] In a preferred embodiment, polymer P has a HALS content of 0.2 to 3.0 mmol HASL / g.

[0338] Preparation method

[0339] Another aspect of the invention claimed herein relates to a process for preparing a polymer P, the process comprising

[0340] i. mixing at least one polyether A and at least one hindered amine light stabilizer H selected from H2, H4, H6 or a mixture thereof; and

[0341] ii. The mixture obtained in step (i) is heated at 80°C to 200°C.

[0342] The H2, H4 and H6 compounds are esters, and these esters react with the terminal amine or hydroxyl groups of at least one polyether to provide polymer P.

[0343] 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).

[0344] 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 amount of the reaction mixture.

[0345] 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 amount of the reaction mixture.

[0346] Another aspect of the invention claimed herein relates to a process for preparing a polymer P, the process comprising

[0347] i. mixing at least one polyether A, at least one hindered amine light stabilizer H selected from H1, H2, H3, H4, H5, H6 or a mixture thereof, and at least one compound B selected from B1, B2 or B5; and

[0348] ii. The mixture obtained in step (i) is heated at 80°C to 200°C.

[0349] The B1, B2 and B5 compounds carry functional groups selected from esters or anhydrides. These compounds react with the terminal amines or hydroxyl groups of at least one polyether P.

[0350] 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).

[0351] 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 amount of the reaction mixture.

[0352] 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 amount of the reaction mixture.

[0353] Another aspect of the invention claimed herein relates to a process for preparing a polymer P, the process comprising

[0354] (i) reacting at least one polyether A with at least one compound B selected from B3 or B4; and

[0355] (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 a mixture thereof.

[0356] The B3 and B4 compounds carry groups selected from isocyanates or epoxides. These compounds react with the terminal amines or hydroxyl groups of at least one polyether.

[0357] In a preferred embodiment, the method further comprises adding at least one solvent in step (i); wherein the at least one solvent is selected from ethyl acetate or methoxypropyl acetate.

[0358] 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 amount of the reaction mixture.

[0359] In a preferred embodiment, at least one catalyst is aluminum trichloride.

[0360] In a preferred embodiment, step (i) is performed at 40°C to 120°C.

[0361] In a preferred embodiment, step (ii) is performed at 50°C to 200°C.

[0362] Composition and application

[0363] Another aspect of the invention claimed herein relates to a liquid composition comprising a polymer (P).

[0364] Another aspect of the invention claimed herein relates to a liquid composition in the form of a dispersion comprising at least one finely divided solid material and at least one polymer P.

[0365] In a preferred embodiment, at least one fine particulate solid material has a particle size D in the range of 0.005 μm to 100 μm at a fixed scattering angle of 90° or 180° according to dynamic light scattering technology. 50 .

[0366] In a preferred embodiment, the at least one fine particulate solid material is at least one pigment.

[0367] In a preferred embodiment, the at least one particulate solid material is a mixture of at least one pigment and at least one filler.

[0368] In preferred embodiments, the liquid composition comprises a liquid diluent.

[0369] In a preferred embodiment, the liquid composition further comprises at least one additive selected from the group consisting of binders, wetting agents, rheology modifiers, UV filters, defoamers, levelers, slip agents, substrate wetting agents, antioxidants, free radical scavengers, biocides and coalescing agents.

[0370] In preferred embodiments, the liquid composition is in the form of a pigment paste, a mill base, a colorant, a coating composition, or an ink.

[0371] 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 invention claimed herein, at least one liquid diluent, and at least one defoaming agent.

[0372] In a preferred embodiment, the pigment paste contains no binder.

[0373] Pigment pastes (pigment concentrates or mill bases) prepared using polymer P as dispersant exhibit very good properties. The pigment pastes have a low mill base viscosity. The pigment pastes show excellent storage stability. The viscosity of the mill base does not increase during storage.

[0374] In a preferred embodiment, the coating composition comprises

[0375] i. The polymer P of the invention claimed herein;

[0376] ii. at least one particulate solid material selected from a pigment, a filler or a mixture thereof;

[0377] iii. at least one liquid diluent, and

[0378] iv. at least one polymer binder

[0379] wherein the 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.

[0380] In a preferred embodiment, the coating composition comprises

[0381] i. 0.1 to 50 wt.% of the polymer of the invention claimed herein, based on the total weight of the liquid composition;

[0382] ii. 1 to 70 wt.% of at least one fine particulate solid material, based on the total weight of the coating composition;

[0383] iii. 10 to 98 wt.% of at least one liquid diluent based on the total weight of the liquid composition; and

[0384] iv. 10 to 98 wt. % of at least one binder, based on the total weight of the liquid composition.

[0385] In a preferred embodiment, the coating composition is prepared by dispersing a fine particulate solid material in a liquid diluent in the presence of the inventive polymer P claimed herein. The coating composition further comprises an additive. Dispersion is achieved by using conventional techniques such as high speed mixing, ball milling, sand milling, attritor grinding, or two or three roll milling.

[0386] In a preferred embodiment, the liquid diluent is water.

[0387] 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 alcohol is selected from methanol, ethanol, isopropanol, propanol or n-butanol. The glycol ether is selected from butylene glycol or methoxypropylene glycol. The polyol is selected from glycerol, ethylene glycol, diethylene glycol, triethylene glycol or propylene glycol.

[0388] In a preferred embodiment, the adhesive is an acrylic adhesive.

[0389] The coating compositions prepared using polymer P show good weathering stability properties. The coatings prepared using the coating compositions comprising polymer P exhibit low ΔE values.

[0390] Another aspect of the invention claimed herein relates to the use of the polymer P of the invention claimed herein as a dispersant.

[0391] Another aspect of the invention claimed herein relates to the use of the polymer P of the invention claimed herein as light stabilizer.

[0392] Another aspect of the invention claimed herein relates to the use of a polymer P of the invention claimed herein in a coating composition.

[0393] The invention claimed herein provides one or more of the following advantages:

[0394] 1. The polymers of the invention claimed herein can be used as a dispersant as part of a liquid composition.

[0395] 2. Pigment pastes (pigment concentrates or mill bases) prepared using polymer P as dispersant exhibit very good properties with low mill base viscosities.

[0396] 3. The pigment paste exhibits excellent storage stability. The viscosity of the mill base does not increase during storage.

[0397] 4. The coating composition prepared using polymer P exhibits good weathering stability properties.

[0398] 5. Coatings prepared using coating compositions comprising polymer P exhibit excellent light stabilizer properties with low ΔE values.

[0399] 6. The polymers of the invention claimed herein do not interfere with the natural properties of the dyes / pigments.

[0400] 7. The polymers of the invention claimed herein, when used as dispersants, allow water-based processability of coating compositions, thereby improving their compliance with environmental and safety regulations.

[0401] In the following, a list of examples is provided to further illustrate the present disclosure without intending to limit the present disclosure to the specific examples listed below.

[0402] 1. A polymer P obtainable by reacting:

[0403] - at least one polyether A;

[0404] - at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6 or a mixture thereof; and

[0405] - at least one compound B having at least one functional group selected from the group consisting of ester, isocyanate, anhydride, carboxylic acid, or epoxide, and the at least one compound B is selected from B1, B2, B3, B4, B5, or a mixture thereof;

[0406] or

[0407] - at least one polyether A; and

[0408] - at least one hindered amine light stabilizer selected from H2, H4, H6 or a mixture thereof;

[0409] in,

[0410] The at least one polyether A is selected from at least one polyether having the general formula A(a), at least one polyether having the general formula A(b), or a mixture thereof;

[0411] in

[0412] (a) the at least one polyether having the general formula A(a) is

[0413]

[0414] in

[0415] R 1 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkyl, linear or branched substituted or unsubstituted C1-C 22 Alkylene, substituted or unsubstituted C6-C 15 Alkyl aryl, or substituted or unsubstituted C6-C 14 Aryl,

[0416] R 2 Selected from linear or branched substituted or unsubstituted C1-C4 alkyl;

[0417] m is an integer ranging from 1 to 100;

[0418] n is an integer ranging from 0 to 100;

[0419] The m units and the n units are distributed to form a random copolymer, a block copolymer or a gradient copolymer; and

[0420] Z is selected from -OH, -NH2 or -NHR 3 , where R 3 Selected from linear or branched substituted or unsubstituted C1-C 22 alkyl;

[0421] and

[0422] (b) the at least one polyether having the general formula A(b) is obtained by making at least one polyether having the general formula A(a)

[0423]

[0424] Where R 1 , R 2 , m, n, and Z are as defined above;

[0425] With at least one compound of formula (E) obtainable

[0426]

[0427] in,

[0428] R 4 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkyl, linear or branched substituted or unsubstituted C1-C 22 Alkylene, substituted or unsubstituted C6-C 15 Alkyl aryl, or substituted or unsubstituted C6-C 14 Aryl, and

[0429] X is selected from O, S or CH2;

[0430] and wherein the molar ratio of the at least one polyether having the general formula A(a) to the at least one compound having the formula (E) is in the range of 1:0.8 to 1:5;

[0431] and

[0432] in,

[0433] a) Hindered amine light stabilizers (HALS) having the general formula H1 are

[0434]

[0435] in

[0436] R 5 and R 6 are independently selected from H, or substituted or unsubstituted C 1-4 alkyl;

[0437] R 7 Selected from -OH, -NH2, -NHR 9 , -R 10 -OH, -R 10 -NH2, or -R 10 -NHR 9 ;

[0438] R 8 Selected from -H, -O, linear or branched substituted or unsubstituted C1-C 22 Alkyl, linear or branched substituted or unsubstituted C3-C8 cycloalkyl, -OR 11 ,

[0439] -R 12 -OH, or -OR 12 -OH;

[0440] Where R 9 and R 11independently selected from linear or branched substituted or unsubstituted C1-C 22 Alkyl; and

[0441] Where R 10 and R 12 independently selected from linear or branched substituted or unsubstituted C1-C 22 Alkylene;

[0442] b) Hindered amine light stabilizer (HALS) H2 is a HALS copolymer comprising

[0443] (i) 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinol; and

[0444] (ii) at least one dicarboxylic acid ester having the general formula

[0445]

[0446] in,

[0447] R 13 Selected from linear or branched substituted or unsubstituted C1-C 12 Alkyl; and

[0448] R 14 Selected from linear or branched substituted or unsubstituted C2-C 12 Alkylene;

[0449] c) Hindered amine light stabilizers (HALS) having the general formula H3 are triazine-based dimers having -NH or -OH functional groups.

[0450]

[0451] in,

[0452] R 5 , R 6 and R 8 As defined above;

[0453] R 15 Selected from H, or linear or branched substituted or unsubstituted C1-C6 alkyl;

[0454] R 16 Selected from H, or linear or branched substituted or unsubstituted C1-C6 alkyl;

[0455] R 17 Select from -H or -R 18 -OH, where R 18 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkylene;

[0456] d) Hindered amine light stabilizers (HALS) having the general formula H4 are diester or carbonate functionalized HALS compounds

[0457]

[0458] in,

[0459] R 5 , R 6 and R 8 As defined above;

[0460] L1 is

[0461] where * indicates the point of attachment to O, and

[0462] R 19 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkylene;

[0463] e) Hindered amine light stabilizer (HALS) H5 is a triazine-substituted alkylamine oligomer with NH functional groups: 1,5,8,12-tetrakis[4,6-bis(N-butyl-N-1,2,2,6,6-pentamethyl-4-piperidinylamino)-1,3,5-triazin-2-yl]-1,5,8,12-tetraazadodecane;

[0464] f) Hindered amine light stabilizer (HALS) H6 is a polyol polyester tetrakis (1,2,2,6,6-pentamethyl-4-piperidinyl) butane-1,2,3,4-tetracarboxylate;

[0465] and

[0466] in,

[0467] B1 is at least one 20 (COOR 21 ) q Diesters or polyesters;

[0468] in

[0469] R 20 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkylene, or substituted or unsubstituted C6-C 10 arylene;

[0470] R 21 Selected from linear or branched substituted or unsubstituted C1-C 12 -alkyl; and

[0471] q is an integer ranging from 2 to 5;

[0472] B2 is at least one phthalic anhydride derivative having the general formula

[0473]

[0474] Where R 22 Selected from 4-COOH, 4-NO2, 4-F, 4-Cl or 4-Br;

[0475] B3 is at least one diisocyanate or polyisocyanate having the general formula

[0476] G(NCO) r

[0477] wherein G is selected from a linear or branched substituted or unsubstituted C2-C 22 Alkyl, linear or branched substituted or unsubstituted C3-C8 cycloalkyl, or substituted or unsubstituted C6-C 14 arylene, and

[0478] r is 2 or 3 or 4;

[0479] B4 is at least one epoxy polymer; and

[0480] B5 is at least one maleic anhydride polymer.

[0481] 2. The polymer P according to embodiment 1, obtainable by reacting:

[0482] a) at least one polyether A(a);

[0483] b) at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6 or a mixture thereof; and

[0484] 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, and the at least one compound B is selected from B1, B2, B3, B4, B5, or a mixture thereof.

[0485] 3. The polymer P according to embodiment 1, obtainable by reacting:

[0486] a) at least one polyether A(b) in which X is O;

[0487] b) at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6 or a mixture thereof; and

[0488] 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, and the at least one compound B is selected from B1, B2, B3, B4, B5, or a mixture thereof.

[0489] 4. The polymer P according to embodiment 1, obtainable by reacting:

[0490] a) at least one polyether A(b) in which X is CH2;

[0491] b) at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6 or a mixture thereof; and

[0492] 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, and the at least one compound B is selected from B1, B2, B3, B4, B5, or a mixture thereof.

[0493] 5. The polymer P according to embodiment 1, obtainable by reacting:

[0494] a) at least one polyether A(a); and

[0495] b) at least one hindered amine light stabilizer selected from H2, H4, H6 or a mixture thereof.

[0496] 6. The polymer P according to embodiment 1, obtainable by reacting:

[0497] a) at least one polyether A(b) in which X is O; and

[0498] b) at least one hindered amine light stabilizer selected from H2, H4, H6 or a mixture thereof.

[0499] 7. The polymer P according to embodiment 1, obtainable by reacting:

[0500] a) at least one polyether A(b) in which X is CH2; and

[0501] b) at least one hindered amine light stabilizer selected from H2, H4, H6 or a mixture thereof.

[0502] 8. The polymer P according to any one of embodiments 1 to 7, wherein R 1 Selected from linear or branched substituted or unsubstituted C1-C 22 alkyl.

[0503] 9. The polymer P according to any one of embodiments 1 to 8, wherein R 1 It is -CH3.

[0504] 10. The polymer P according to any one of embodiments 1 to 9, wherein

[0505] m is an integer in the range of 1 to 50; and

[0506] n is an integer ranging from 1 to 50.

[0507] 11. The polymer P according to any one of embodiments 1 to 10, wherein R 2 It is -CH3.

[0508] 12. The polymer P according to any one of embodiments 1 to 11, wherein R 2 is -CH3, and Z is NH2.

[0509] 13. The polymer P according to embodiment 12, wherein the at least one polyether of the general formula A(a) is a block copolymer of ethylene oxide and propylene oxide having a weight average molecular weight of 2000 g / mol according to DIN 55672-1.

[0510] 14. The polymer P according to any one of embodiments 1 to 11, wherein R 2 is -CH3, and Z is OH.

[0511] 15. The polymer P according to embodiment 14, wherein the at least one polyether of the general formula A(a) is a block copolymer comprising ethylene oxide and propylene oxide and having a weight average molecular weight according to DIN 55672-1 of 1950 g / mol.

[0512] 16. The polymer P according to any one of embodiments 1 to 9, wherein

[0513] m is an integer in the range of 1 to 100; and

[0514] n is 0.

[0515] 17. The polymer P according to embodiment 16, wherein Z is -OH.

[0516] 18. The polymer P according to embodiment 17, wherein the at least one polyether of the general formula A(a) is a methoxypolyethylene glycol having a weight average molecular weight according to DIN 55672-1 of 500 g / mol.

[0517] 19. The polymer P according to any one of embodiments 1 to 18, wherein the at least one polyether of the general formula A(b) is obtainable by reacting the at least one polyether of the general formula A(a) with the at least one compound of formula (E), wherein R 4 is 2-ethylhexyl, and X═O; and the molar ratio of the at least one polyether having the general formula A(a) to the at least one compound having the formula (E) is in the range of 1:0.8 to 12.

[0518] 20. The polymer P according to any one of embodiments 1 to 18, wherein the at least one polyether of the general formula A(b) is obtainable by reacting the at least one polyether of the general formula A(a) with the at least one compound of formula (E), wherein R 4 is hexadecyl, and X═O; and the molar ratio of the at least one polyether having the general formula A(a) to the at least one compound having the formula (E) is in the range of 1:0.8 to 1:2.

[0519] 21. The polymer P according to any one of embodiments 1 to 20, wherein the at least one HALS having formula H1 is selected from 4-hydroxy-2,2,6,6-tetramethylpiperidinyloxy, 4-amino-2,2,6,6-tetramethyl-piperidinyloxy, 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.

[0520] 22. The polymer P according to any one of embodiments 1 to 21, wherein the at least one HALS H2 is a copolymer comprising a dimethyl succinate polymer and 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinylethanol, the copolymer having a weight average molecular weight according to DIN 55672-1 of 7000 g / mol.

[0521] 23. The polymer P according to any one of embodiments 1 to 22, wherein the at least one HALS having the general formula H3 is

[0522]

[0523] 24. The polymer P according to any one of embodiments 1 to 23, wherein the at least one HALS having the general formula H4 is a diester selected from the following

[0524]

[0525] or

[0526]

[0527] 25. The polymer P according to any one of embodiments 1 to 24, wherein the at least one HALS having formula H4 is a carbonate

[0528]

[0529] 26. The polymer P according to any one of embodiments 1 to 25, wherein 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-piperidinylamino)-1,3,5-triazin-2-yl]-1,5,8,12-tetraazadodecane.

[0530] 27. The polymer P according to any one of embodiments 1 to 26, wherein the at least one HALS H6 is tetrakis(1,2,2,6,6-pentamethyl-4-piperidinyl)butane-1,2,3,4-tetracarboxylate.

[0531] 28. The polymer P according to any one of embodiments 1 to 27, wherein the at least one diester or polyester B1 is selected from dimethyl succinate, diethyl succinate, or diisononyl-1,2-cyclohexanedicarboxylate.

[0532] 29. The polymer P according to any of embodiments 1 to 28, wherein the at least one phthalic anhydride derivative B2 is trimellitic anhydride.

[0533] 30. The polymer P according to any one of embodiments 1 to 29, wherein the 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.

[0534] 31. The polymer P according to any of embodiments 1 to 30, wherein the at least one epoxy polymer B4 comprises monomers selected from trimethylolpropane triglycidyl ether or bisphenol A diglycidyl ether.

[0535] 32. Polymer P according to any of embodiments 1 to 31, wherein the at least one maleic anhydride polymer B5 is a styrene maleic anhydride copolymer.

[0536] 33. The polymer P according to any one of embodiments 1 to 32, having a weight average molecular weight in the range of 200 g / mol to 100,000 g / mol according to DIN 55672-1.

[0537] 34. The polymer P according to any one of embodiments 1 to 33, having a weight average molecular weight in the range of 500 g / mol to 50,000 g / mol according to DIN 55672-1.

[0538] 35. The polymer P according to any one of embodiments 1 to 34, having a weight average molecular weight in the range of 2000 g / mol to 50,000 g / mol according to DIN 55672-1.

[0539] 36. The polymer P according to any of embodiments 1 to 35, having a polydispersity index in the range of 1.1 to 4.0 according to DIN 55672-1.

[0540] 37. The polymer P according to any one of embodiments 1 to 36, having a HALS content of 0.1 to 3.5 mmol HASL / g.

[0541] 38. The polymer P according to any one of embodiments 1 to 37, having a HALS content of 0.2 to 3.0 mmol HASL / g.

[0542] 39. A method for preparing a polymer P according to any one of embodiments 1 to 38, the method comprising

[0543] i. mixing at least one polyether A and at least one hindered amine light stabilizer H selected from H2, H4, H6 or a mixture thereof; and

[0544] ii. The mixture obtained in step (i) is heated at 80°C to 200°C.

[0545] 40. The method according to embodiment 39, further comprising adding at least one catalyst selected from tetrabutyl titanate or dibutyltin dilaurate to the mixture obtained in step (i).

[0546] 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 wt. % based on the total amount of the reaction mixture.

[0547] 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.

[0548] 43. A method for preparing a polymer P according to any one of embodiments 1 to 38, the method comprising

[0549] i. mixing at least one polyether A, at least one hindered amine light stabilizer H selected from H1, H2, H3, H4, H5, H6 or a mixture thereof, and at least one compound B selected from B1, B2 or B5; and

[0550] ii. The mixture obtained in step (i) is heated at 80°C to 200°C.

[0551] 44. The method according to embodiment 43, further comprising adding at least one catalyst selected from tetrabutyl titanate or dibutyltin dilaurate to the mixture obtained in step (i).

[0552] 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.

[0553] 46. ​​The method according to any one 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.

[0554] 47. A method for preparing a polymer P according to any one of embodiments 1 to 38, the method comprising

[0555] (i) reacting at least one polyether A with at least one compound B selected from B3 or B4; and

[0556] (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 a mixture thereof.

[0557] 48. The method according to embodiment 47, further comprising adding at least one solvent in step (i); wherein the at least one solvent is selected from ethyl acetate or methoxypropyl acetate.

[0558] 49. The method according to 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.

[0559] 50. The method of embodiment 49, wherein the at least one catalyst is selected from aluminum chloride.

[0560] 51. The method of any one of embodiments 47 to 50 wherein step (i) is performed at 40°C to 120°C.

[0561] 52. The method of any one of embodiments 47 to 51, wherein step (ii) is performed at 50°C to 200°C.

[0562] 53. A liquid composition comprising the polymer P according to any one of embodiments 1 to 38.

[0563] 54. A liquid composition in the form of a dispersion comprising at least one fine particulate solid material and at least one polymer P according to any one of embodiments 1 to 38.

[0564] 55. The liquid composition according to embodiment 54, wherein the at least one fine particulate solid material has a particle size D in the range of 0.005 μm to 100 μm at a fixed scattering angle of 90° or 180° according to dynamic light scattering technology. 50 .

[0565] 56. The liquid composition of any one of embodiments 54 or 55, wherein the at least one fine particulate solid material is at least one pigment.

[0566] 57. The liquid composition of any one of embodiments 54 to 56, further comprising at least one additive selected from fillers, binders, wetting agents, rheology modifiers, UV filters, defoamers, levelers, slip agents, substrate wetting agents, antioxidants, free radical scavengers, biocides, or coalescing agents.

[0567] 58. The liquid composition of any of embodiments 54 to 57 in the form of a pigment paste, a mill base, a colorant, a coating composition, or an ink.

[0568] 59. A coating composition comprising

[0569] i. a polymer P according to any one of embodiments 1 to 38;

[0570] ii. at least one particulate solid material selected from a pigment, a filler or a mixture thereof;

[0571] iii. at least one liquid diluent, and

[0572] iv. at least one polymer binder

[0573] wherein the 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.

[0574] 60. The coating composition according to embodiment 59, comprising

[0575] i. 0.1 to 50 wt.% of a polymer according to any one of embodiments 1 to 38, based on the total weight of the liquid composition;

[0576] ii. 1 to 70 wt.% of at least one fine particulate solid material, based on the total weight of the coating composition;

[0577] iii. 10 to 98 wt.% of at least one liquid diluent based on the total weight of the liquid composition; and

[0578] iv. 10 to 98 wt. % of at least one binder, based on the total weight of the liquid composition.

[0579] 61. Use of the polymer P according to any one of embodiments 1 to 38 as a dispersant.

[0580] 62. Use of the polymer P according to any one of embodiments 1 to 38 as a light stabilizer.

[0581] 63. Use of the polymer P according to any one of embodiments 1 to 38 in a coating composition.

[0582] While the invention claimed herein has been described in terms of 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 invention claimed herein.

[0583] Examples

[0584] The invention claimed herein is illustrated in detail by the following non-limiting working examples. More particularly, the test methods specified hereinafter are part of the general disclosure of the present application and are not limited to the specific working examples.

[0585] Material

[0586] The following materials are used in the examples:

[0587] A520E is a polyether (methyl polyethylene glycol) with a MW of 500 g / mol,

[0588] Red L 3670HD is an organic pigment.

[0589] SI 2250 is a defoamer for various water-based coating systems and pigment concentrates.

[0590] 8034 is a defoamer for emulsion coating.

[0591] CX4320 is a polymer dispersant for inorganic fillers and pigments.

[0592] A754 is an aqueous dispersion of a linear acrylic copolymer and

[0593] PU1216 is a non-ionic pseudoplastic rheology modifier for water-based coatings.

[0594] Available from BASF Se.

[0595] ultra IL BA is an aromatic polyisocyanate based on toluene diisocyanate and

[0596] Ultra T100 is 2,4-toluene diisocyanate.

[0597] Available from Coverstro.

[0598] M-2070 is a polyetheramine based on propylene oxide / ethylene oxide (PO / EO) copolymer with a weight average molecular weight of about 2,000. The PO / EO molar ratio is 10 / 31.

[0599] GE-30 is a low viscosity, high epoxy functional resin.

[0600] Available from Huntsman Corporation.

[0601] 1000P is a low MW poly(styrene-co-maleic anhydride) resin, and

[0602] 2000P is a low MW poly(styrene-co-maleic anhydride) resin.

[0603] Available from Cray Valley.

[0604] ADK STAB LA-81 is bis(1-undecyloxy-2,2,6,6-tetramethylpiperidin-4-yl) carbonate, and

[0605] ADK STAB LA-52 is tetrakis(1,2,2,6,6-pentamethyl-4-piperidinyl)butane-1,2,3,4-tetracarboxylate

[0606] Available from Adeka Polymer Additives.

[0607] LT is a rheological additive, an organically modified thickener based on refined hectorite clay for waterborne paints and waterborne coatings, and

[0608] Finntalc M15 is a medium-sized lamellar talc (magnesium silicate) for flotation.

[0609] Available from Elements Specialities.

[0610] 10 is a specialty mineral, a micronized functional filler and extender available from Sibelco Specialty Minerals.

[0611] N is a dispersant for emulsion paints, plasters and adhesives available from ICL Phosphate Specialty.

[0612] BS1306 is a solvent-free, water-dilutable emulsion of polysiloxane modified with a functional silicone resin.

[0613] Available from Wacker Chemie AG.

[0614] Dimethyl succinate, trimellitic anhydride, 4-hydroxy-2,2,6,6-tetramethylpiperidinyloxy, 4-amino-2,2,6,6-tetramethylpiperidinyloxy, 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-piperidinylamino)-1,3,5-triazin-2-yl]-1,5,8,12-tetraazadodecane were available from Sigma Aldrich.

[0615] method

[0616] Epoxy content: The epoxy content is determined according to DIN EN ISO 7142.

[0617] Molecular weight: weight average molecular weight (M w ), number average molecular weight (M n) and polydispersity index (PDI) were determined according to DIN 55672-1. The weight average molecular weight and number average molecular weight of the polymers were determined by gel permeation chromatography (GPC) using THF as eluent (1 mL / min) and polystyrene as standard resin according to DIN 55672-1.

[0618] Acid value: The acid value is determined according to DIN 53402:1990-09.

[0619] NCO number: The NCO number is determined according to DIN 53185.

[0620] HALS content: HALS content is calculated based on equivalent (mmol) HALS molecules per gram of solid polymer.

[0621] Viscosity: Viscosity was measured similar to DIN 53019-1:2008-09 using a Thermo-Haake RheoStress 600 device in CR mode at 22°C and 1 second. -1 The shear rate (spindle CP50) is used to determine the

[0622] ΔE: ΔE is determined according to DIN EN ISO 16474-2 cycle number 1 (2014).

[0623] A) Polyether A - Polyether A (a) and Polyether A (b)

[0624] Polyethers A1 and A2 are commercially available.

[0625] Polyether A1 is M2070, and polyether A2 is A520E. Polyethers A3-A5 are synthetic.

[0626] Preparation of polyether A3-A5

[0627] Example 1: Preparation of polyether A3

[0628] In a reaction vessel maintained under a nitrogen atmosphere, intermediate A1 (50 g, 25 mmol) and 2-ethylhexyl glycidyl ether (4.5 g, 24 mmol) were charged, 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 to obtain intermediate A3 as a pale yellow liquid. w The molecular weight is 2,500 g / mol and the PDI is 1.1.

[0629] Example 2: Preparation of polyether A4

[0630] In a reaction vessel maintained under a nitrogen atmosphere, intermediate A1 (50 g, 25 mmol) and glycidyl hexadecyl ether (7.5 g, 25 mmol) were charged, 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 to obtain intermediate A4 as a pale yellow liquid. w The molecular weight is 2,600 g / mol and the PDI is 1.1.

[0631] Example 3: Preparation of polyether A5

[0632] A 2 L autoclave equipped with a heating system, cooling coil, stirrer, connection to a vacuum pump and connection for an ethylene oxide or propylene oxide tank was charged with intermediate A2 (150 g) and potassium tert-butoxide (KO t Bu) (2g), the autoclave is subsequently purged with nitrogen. The contents of the autoclave are heated to 110°C and the contents are dehydrated under reduced pressure of 10 mbar for 1h. The resulting mixture is heated to 120°C, and ethylene oxide (300g) is introduced into the autoclave under pressure for 12h. The reaction mixture is heated at this temperature until the pressure decreases and becomes constant. The temperature of the reaction mixture is then raised to 130°C, and 200g of propylene oxide is introduced into the autoclave under pressure for 12h. The reaction mixture is heated at this temperature until the pressure decreases and becomes constant. All volatile by-products and residual monomers are removed under reduced pressure to obtain 640g of intermediate A5.

[0633] Intermediate A5 M W The molecular weight is 1950 g / mol and the PDI is 1.3.

[0634] B) Compound B - Compounds B1 to B7

[0635] [having at least one functional group selected from ester, isocyanate, anhydride, carboxylic acid and epoxide]

[0636] Compounds B1 to B7 are commercially available compounds.

[0637] Compound B1-a is dimethyl succinate,

[0638] Compound B2-a is trimellitic anhydride,

[0639] Compound B3-a is IL BA, an aromatic polyisocyanate based on toluene diisocyanate.

[0640] Compound B3-b is 2,4-toluene diisocyanate,

[0641] Compound B4-a is a low viscosity, highly epoxy functional resin, and

[0642] Compound B5-a and Compound B5-b are low MW poly(styrene-co-maleic anhydride) resins.

[0643] C) Hindered Amine Light Stabilizer (HALS)

[0644] The following hindered amine light stabilizers (HALS) are commercially available.

[0645] i) Hindered amine light stabilizer (HALS) having the general formula H1

[0646] HALS H1-a to HALS H1-f are as follows:

[0647] Code Compound H1-a 4-Hydroxy-2,2,6,6-tetramethylpiperidinyloxy H1-b 4-Amino-2,2,6,6-tetramethylpiperidinyloxy H1-c 4-Hydroxy-2,2,6,6-tetramethylpiperidine H1-d 4-Amino-2,2,6,6-tetramethylpiperidine H1-e 4-Hydroxy-1,2,2,6,6-pentamethyl-piperidine H1-f 4-Hydroxy-1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidine

[0648] ii) Hindered Amine Light Stabilizer (HALS) Copolymer H2

[0649] HALS H2-a is a copolymer of dimethyl succinate and 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinylethanol with M n =3500.

[0650]

[0651] iii) Hindered amine light stabilizer (HALS) - triazine-based dimer H3 with NH or OH functional groups

[0652] HALS H3-a is 2,4-bis[N-butyl-N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)amino]-6-(2-hydroxyethylamino)-1,3,5-triazine.

[0653]

[0654] iv) Hindered amine light stabilizer (HALS) having the general formula H4

[0655] HALS H4-a to HALS H4-d are as follows:

[0656] Code Compound H4-a Bis(1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate H4-b Bis(1-octyloxy-2,2,6,6-tetramethyl-4-piperidinyl) sebacate H4-c Bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate H4-d Bis(1-undecyloxy-2,2,6,6-tetramethylpiperidin-4-yl) carbonate

[0657] v) Hindered amine light stabilizer (HALS) H5 - oligomers based on triazine-substituted alkylamines with NH-functional groups

[0658] HALS-H5-a is 1,5,8,12-tetrakis[4,6-bis(N-butyl-N-1,2,2,6,6-pentamethyl-4-piperidinylamino)-1,3,5-triazine-2-yl]-1,5,8,12-tetraazadodecane

[0659] vi) Hindered Amine Light Stabilizer (HALS) H6-Polyol Polyester

[0660] HALS H6-a is tetrakis(1,2,2,6,6-pentamethyl-4-piperidinyl)butane-1,2,3,4-tetracarboxylate.

[0661] Polymer (P) synthesis

[0662] Example 1: Preparation of polymer P1

[0663] Polymer 1:

[0664] To a reaction vessel maintained under a nitrogen atmosphere, intermediate A1 (65 g), intermediate B1-a (15 g), and intermediate H1-f (20 g) were added. The reaction mixture was heated at 120° C. for 1 h. Tetrabutyl titanate (0.5 g) was added to the resulting mixture, followed by heating at 150° C. under reduced pressure until no distillate was formed. The product was cooled to obtain a product having M w The polymer P1 has a PDI of 1.9 and a HALS content of 4,500 g / mol. HALS content: 1.0 mmol HALS / g polymer.

[0665] Polymer 2-10

[0666] Polymers 2-10 were prepared by methods similar to those used to prepare Polymer 1. The starting materials and their amounts are provided in Table 1.

[0667] Table 1: Polymers 2-10

[0668]

[0669] Polymer 11:

[0670] Intermediate A2 (60 g), intermediate B2-a (20 g), and intermediate H1-f (20 g) were added to a reaction vessel maintained under a nitrogen atmosphere, and the mixture was heated at 120° C. for 1 h. Tetrabutyl titanate (0.5 g) was added to the reaction mixture, which was then heated at 170° C. under reduced pressure until the acid value of the reaction mixture reached a stable value, i.e., the acid value remained constant. The reaction mixture was cooled to obtain a polymer P11 having a Mw of 7,300 g / mol and a PDI of 1.7. HALS content: 1.0 mmol HALS / g polymer.

[0671] Polymer 12-14

[0672] Polymers 12-14 were prepared by methods similar to those used to prepare polymer 11. The starting materials and their corresponding amounts are provided in Table 2.

[0673] Table 2: Polymers 12-14

[0674]

[0675] Polymer 15:

[0676] 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 h. 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 was zero. Volatiles were removed under reduced pressure at 130° C. to obtain polymer 15 with a Mw of 9,700 g / mol and a PDI of 1.6. HALS content: 1.0 mmol HALS / g polymer.

[0677] Polymer 16-21

[0678] Polymers 16-21 were prepared by methods similar to those used to prepare polymer 15. The starting materials and their corresponding amounts are provided in Table 3.

[0679] Table 3: Polymers 16-21

[0680]

[0681] Polymer 22:

[0682] 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 h. Intermediate H1-b (6 g) was slowly added to the reaction mixture, and it was heated at 170°C until the epoxy content of the reaction mixture was zero. The Mw of the obtained polymer 22 was 6,700 g / mol and the PDI was 1.4. HALS content: 0.4 mmol HALS / g polymer.

[0683] Polymer 23-26

[0684] Polymers 23-26 were prepared by methods similar to those used to prepare polymer 22. The starting materials and their corresponding amounts are provided in Table 4.

[0685] Table 4: Polymers 23-26

[0686]

[0687] Polymer 27:

[0688] To a reaction vessel maintained under a nitrogen atmosphere, 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 was stable, i.e., the acid value did not change. The Mw of the obtained polymer 27 was 22,500 g / mol and the PDI was 2.5. HALS content: 0.3 mmol HALS / g polymer.

[0689] Polymer 28-30

[0690] Polymers 28-30 were prepared by methods similar to those used to prepare polymer 27. The starting materials and their corresponding amounts are provided in Table 5.

[0691] Table 5: Polymers 28-30

[0692]

[0693] Polymer 31:

[0694] Intermediate A1 (50 g) and intermediate H2-a (50 g) were added to a reaction vessel maintained under a nitrogen atmosphere, and the mixture was heated to 120° C. Tetrabutyl titanate (0.5 g) was added to the mixture and the resulting mixture was heated at 170° C. for 30 h to obtain polymer 31 having a Mw of 8,900 g / mol and a PDI of 2.9. HALS content: 1.8 mmol HALS / g polymer.

[0695] Polymer 32-49

[0696] Polymers 32-49 were prepared by methods similar to those for polymer 31. The starting materials and their corresponding amounts are provided in Table 6.

[0697] Table 6: Polymers 32-49

[0698]

[0699] Application testing:

[0700] A) Aqueous solution of polymer P

[0701] In order to evaluate the dispersant effect of the obtained polymer P, a concentrated aqueous solution of polymer P was prepared.

[0702] To prepare the aqueous solution, polymer P (40 g) was charged into a reactor and heated to 90° C. under stirring, followed by slow addition of warm water (60 g). The resulting aqueous solution was stirred for 3 h.

[0703] B) Grinding base preparation

[0704] Polymer P was used to prepare a resin-free pigment concentrate (mill base).

[0705] The components of the mill base are provided in the following Formulation 1. These components of Formulation 1 were dispersed in a Scandex shaker with the aid of glass beads for 4 h. Afterwards, the mill base was filtered and stored at room temperature overnight.

[0706] Formulation 1: Water-based pigment concentrate

[0707]

[0708] The performance of the dispersants was found to be generally very good with low mill base viscosity.

[0709] Table 7 shows data on the viscosity of the mill base after 24 hours at room temperature and after 14 days at 50°C.

[0710] Table 7. Viscosity of mill base before and after storage

[0711]

[0712]

[0713] C) Coating composition

[0714] The coating composition was prepared by mixing the mill base with the let-down composition. The let-down formulation is shown in Table 8.

[0715] The mill base (MB) (20 g) from the examples shown in Table 7 was stirred at 1000 rpm for 5 min using a Dispermat to 80 g of a diluted formulation.

[0716] Table 8: Dilution formulation

[0717]

[0718] D) Results

[0719] The coating compositions were applied to cold rolled steel panels using a 250 μm applicator bar. Each sample was applied to 3 panels. The wet films were allowed to stand at room temperature for 7 days.

[0720] The artificial weathering and artificial irradiation of the dried films were evaluated according to DIN EN ISO 16474-2 cycle number 1 (2014). The results are shown in Table 9.

[0721] The weathering test results (ΔE) clearly show that the coating composition containing the dispersant containing HALS groups exhibits good weathering stability properties.

[0722] Table 9: Artificial weathering test

[0723]

Claims

1. A polymer P obtainable by reacting: - at least one polyether A; - at least one hindered amine light stabilizer (HALS) H selected from H1, H2, H3, H4, H5, H6 or a mixture thereof; and - at least one compound B having at least one functional group selected from the group consisting of ester, isocyanate, anhydride, carboxylic acid, or epoxide, and the at least one compound B is selected from B1, B2, B3, B4, B5, or a mixture thereof; or - at least one polyether A; and - at least one hindered amine light stabilizer selected from H2, H4, H6 or a mixture thereof; in, The at least one polyether A is selected from at least one polyether having the general formula A(a), at least one polyether having the general formula A(b), or a mixture thereof; in (a) the at least one polyether having the general formula A(a) is in R 1 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkyl, linear or branched substituted or unsubstituted C1-C 22 Alkylene, substituted or unsubstituted C6-C 15 Alkyl aryl, or substituted or unsubstituted C6-C 14 Aryl, R 2 Selected from linear or branched 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 selected from -OH, -NH2 or -NHR 3 , where R 3 Selected from linear or branched substituted or unsubstituted C1-C 22 alkyl; and (b) the at least one polyether having the general formula A(b) is obtained by making at least one polyether having the general formula A(a) Where R 1 , R 2 , m, n, and Z are as defined above; With at least one compound of formula (E) obtainable in, R 4 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkyl, linear or branched substituted or unsubstituted C1-C 22 Alkylene, substituted or unsubstituted C6-C 15 Alkyl aryl, or substituted or unsubstituted C6-C 14 Aryl, and X is selected from O, S or CH2; and wherein the molar ratio of the at least one polyether having the general formula A(a) to the at least one compound having the formula (E) is in the range of 1:0.8 to 1:5; and in, a) The hindered amine light stabilizer (HALS) having the general formula H1 is in R 5 and R 6 are independently selected from H, or substituted or unsubstituted C 1-4 alkyl; R 7 Selected from -OH, -NH2, -NHR 9 , -R 10 -OH, -R 10 -NH2, or -R 10 -NHR 9 ; R 8 Selected from -H, -O, linear or branched substituted or unsubstituted C1-C 22 Alkyl, linear or branched substituted or unsubstituted C3-C8 cycloalkyl, -OR 11 , -R 12 -OH, or -OR 12 -OH; Where R 9 and R 11 independently selected from linear or branched substituted or unsubstituted C1-C 22 Alkyl; and Where R 10 and R 12 independently selected from linear or branched substituted or unsubstituted C1-C 22 Alkylene; b) The hindered amine light stabilizer (HALS) H2 is a HALS copolymer comprising (i) 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinol; and (ii) at least one dicarboxylic acid ester having the general formula in, R 13 Selected from linear or branched substituted or unsubstituted C1-C 12 Alkyl; and R 14 Selected from linear or branched substituted or unsubstituted C2-C 12 Alkylene; c) The hindered amine light stabilizer (HALS) having the general formula H3 is a triazine-based dimer having -NH or -OH functional groups in, R 5 , R 6 and R 8 As defined above; R 15 Selected from H, or linear or branched substituted or unsubstituted C1-C6 alkyl; R 16 Selected from H, or linear or branched substituted or unsubstituted C1-C6 alkyl; R 17 Select from -H or -R 18 -OH, where R 18 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkylene; d) The hindered amine light stabilizer (HALS) having the general formula H4 is a diester or carbonate functionalized HALS compound in, R 5 , R 6 and R 8 As defined above; L1 is where * indicates the point of attachment to O, and R 19 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkylene; e) The hindered amine light stabilizer (HALS) H5 is a triazine-substituted alkylamine oligomer with NH functional groups: 1,5,8,12-tetrakis[4,6-bis(N-butyl-N-1,2,2,6,6-pentamethyl-4-piperidinylamino)-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-piperidinyl) butane-1,2,3,4-tetracarboxylate; and in, B1 is at least one 20 (COOR 21 ) q Diesters or polyesters; in R 20 Selected from linear or branched substituted or unsubstituted C1-C 22 Alkylene, or substituted or unsubstituted C6-C 10 arylene; R 21 Selected from linear or branched substituted or unsubstituted C1-C 12 -alkyl; and q is an integer ranging from 2 to 5; B2 is at least one phthalic anhydride derivative having the general formula Where R 22 Selected from 4-COOH, 4-NO2, 4-F, 4-Cl or 4-Br; B3 is at least one diisocyanate or polyisocyanate having the general formula G(NCO) r wherein G is selected from a linear or branched substituted or unsubstituted C2-C 22 Alkyl, linear or branched substituted or unsubstituted C3-C8 cycloalkyl, or substituted or unsubstituted C6-C 14 arylene, and r is 2 or 3 or 4; B4 is at least one epoxy polymer; and B5 is at least one maleic anhydride polymer.

2. The polymer P according to claim 1, wherein R 1 Selected from linear or branched substituted or unsubstituted C1-C 22 alkyl.

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

4. The polymer P according to claim 1 or 2, wherein m is an integer in the range of 1 to 100; and n is 0.

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

2.

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

2.

7. The polymer P according to any one of claims 1 to 6, wherein The at least one HALS having formula H1 is selected from 4-hydroxy-2,2,6,6-tetramethylpiperidinyloxy, 4-amino-2,2,6,6-tetramethyl-piperidinyloxy, 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. The polymer P according to any one of claims 1 to 7, wherein The at least one HALS H2 is a copolymer comprising a dimethyl succinate polymer and 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinylethanol, the copolymer having a weight average molecular weight according to DIN 55672-1 of 7000 g / mol.

9. The polymer P according to any one of claims 1 to 8, wherein The at least one HALS having the general formula H3 is 10. The polymer P according to any one of claims 1 to 9, wherein The at least one HALS having the general formula H4 is a diester selected from the group consisting of or 11. The polymer P according to any one of claims 1 to 10, wherein The at least one HALS having formula H4 is a carbonate 12. The 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 diisononyl-1,2-cyclohexanedicarboxylate.

13. The polymer P according to any one of claims 1 to 12, wherein The 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.

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

15. The 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 . The polymer P according to claim 1 , having a weight average molecular weight in the range from 200 g / mol to 100,000 g / mol according to DIN 55672-1. 17 . The polymer P according to claim 1 , which has a polydispersity index in the range from 1.1 to 4.0 according to DIN 55672-1.

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

20. A process for preparing a polymer P according to any one of claims 1 to 18, the process comprising 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 a mixture thereof, and the at least one compound B selected from B1, B2 or B5; and ii. The mixture obtained in step (i) is heated at 80°C to 200°C.

21. A process for preparing a polymer P according to any one of claims 1 to 18, the process comprising (iii) reacting the at least one polyether A with the at least one compound B selected from B3 or B4; and (iv) 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 a mixture thereof.

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 fine particulate solid material and at least one polymer P according to any one of claims 1 to 18.

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

25. A liquid composition according to claim 23 or 24 in the form of a pigment paste, a mill base, a colorant, a coating composition or an ink.

26. A coating composition comprising 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; wherein the 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.

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

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

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

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