Polyacrylate polymer

Abstract

The present invention relates to polymers comprising a polyacrylate homo- or copolymer backbone incorporating at least one benzyl derivative covalently bonded to at least one end of the homo- or copolymer backbone, and their uses as flow and leveling agents, additives, dispersants, etc.

Description

Technical Field

[0001] The present invention relates to a polymer comprising a polyacrylate homo- or copolymer backbone incorporating at least one benzyl derivative bonded to at least one end of the homo- or copolymer backbone, and its use as a flow and leveling agent, additive, dispersant, etc.

Background Art

[0002] Polymeric materials are known that are effective for dispersing pigments in organic solvents or in water and are used to form monochromatic pigment dispersions useful in formulating aqueous and solvent-based coating compositions. Such pigment dispersions are widely used, for example, in exterior coatings for automobiles and trucks.

[0003] EP2445944A1 discloses a pigment dispersant comprising a graft copolymer obtained from a monomer mixture consisting of a) 2 to 20% by weight of a vinylimidazole monomer, b) 55 to 85% by weight of a macromonomer, and c) an amine-functional monomer or an amide-functional monomer or an ammonium-functional monomer or a hydroxyl-functional monomer, and d) optionally a monomer containing no functional groups.

[0004] JP2009-52010 relates to a pigment dispersion containing a dispersant which, in one block, has 5 to 40 mol% of repeating units represented by poly(ethylene glycol) ethyl ether (meth)acrylate together with 1 to 5 repeating units of ethylene glycol, and the other block consists of repeating units represented by a (meth)acrylate having a tertiary amino group. The amino group is not quaternized. The block copolymer dispersant used in the preparation of these compositions has an amine value between 80 and 150 mgKOH / g.

[0005] Furthermore, low molecular weight acrylic polymers are known to be used in the coating industry as additives such as dispersants or leveling agents or as resin components. These low molecular weight acrylic or methacrylic polymers are technically produced by a free radical solution polymerization method in a high boiling aromatic solvent such as xylene. However, the polymers produced by this very economical process will exhibit some discoloration, typically a slightly yellowish hue, which is highly undesirable. To overcome these disadvantages, various measures have been proposed, such as changing the process conditions, adding stabilizers, or conducting the polymerization in a non-aromatic solvent. However, all of these measures have led to some disadvantages such as high costs and unwanted side effects such as bad odors caused by additional components such as stabilizers.

[0006] Therefore, even considering a wide range of various technical applications, the need for low molecular weight acrylic polymers remains high.

Prior Art Documents

Patent Documents

[0007]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0008] Therefore, the object of the invention described in the claims of the present application is to provide novel polyacrylate homopolymers and copolymers that can be efficiently used as leveling agents, dispersants or resin components while showing a low level of discoloration or no discoloration at all.

Means for Solving the Problems

[0009] Surprisingly, polyacrylate homopolymers and copolymers containing a moiety derived from benzyl alcohol and preferably bonded to at least one end of the polyacrylate homopolymer or copolymer have been found to be usable as leveling agents while showing an unexpectedly low level of discoloration.

[0010] Thus, in a first aspect, the invention described in the claims of the present application is a polyacrylate homo- or copolymer main chain and a general formula (I)

[0011]

Chemical formula

[0012] [wherein X, Y and Z are hydrogen, halogen, substituted or unsubstituted linear or branched C1-C 10 alkyl, OR and C(=O)-OR (wherein R is substituted or unsubstituted linear or branched C1-C 10 alkyl) independently selected from the group consisting of)] a polymer comprising at least one moiety derived from a compound of formula (I), wherein at least one moiety derived from a compound of formula (I) is covalently bonded to at least one of the ends of the polyacrylate backbone.

[0013] In a second aspect, the invention described in the claims of the present application is a method for preparing a polymer, a) at least one general formula (II)

[0014]

Chemical formula

[0015] [wherein R1 is selected from the group consisting of substituted or unsubstituted linear or branched C1-C 22 alkyl or substituted or unsubstituted aryl)] A mixture containing an acrylate monomer is polymerized in the presence of at least one free radical forming initiator and at least one compound of general formula (I)

[0016] [Chemical formula]

[0017] [wherein X, Y and Z are independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted linear or branched C1-C 10 alkyl, OR and C(=O)-OR (wherein R is a substituted or unsubstituted linear or branched C1-C 10 alkyl)] and at least includes the step of polymerizing in the presence of a compound of

[0018] In a third aspect, the invention described in the claims of the present application is directed to a liquid composition in the form of a dispersion, comprising a polymer according to the invention described in the claims of the present application, a particulate solid material selected from the group consisting of pigments and fillers, and a liquid diluent.

[0019] In a fourth aspect, the invention described in the claims of the present application is directed to the use of a polymer prepared according to the invention described in the claims of the present application as a dispersant for particulate solid materials selected from the group consisting of pigments and fillers, as a flow and leveling agent or surface additive in coatings, paints, inks and adhesives, and as a resin component in coatings, paints, inks and adhesives. [Embodiments for Carrying out the Invention]

[0020] Before describing the present invention, it should be understood that the terms used in this specification are not intended to be limiting, as the scope of the present invention will be limited only by the appended embodiments.

[0021] Hereinafter, when a group is defined to include at least a certain number of embodiments, this is intended to also include a preferred group consisting only of these embodiments. Further, the terms "first", "second", "third" or "a", "b", "c", etc. in the present specification and claims are used to distinguish between similar elements and are not necessarily used to describe sequential or chronological order. Such terms are interchangeable under appropriate circumstances, and it should be understood that the embodiments of the invention described in the claims of the present application can be operated in an order other than that described or illustrated herein. When the terms "first", "second", "third" or "(A)", "(B)", and "(C)" or "(a)", "(b)", "(c)", "(d)", "i", "ii", etc. relate to steps of a method or use or assay, there is no temporal coherence or time interval coherence between the steps, that is, the steps may be performed simultaneously or there may be a time interval of seconds, minutes, hours, days, weeks, months, or even years between such steps, unless otherwise indicated in the present application as specified above or below.

[0022] Furthermore, ranges defined throughout the specification include the end values, i.e., a range from 1 to 10 implies that both 1 and 10 are included within that range. To avoid misunderstanding, the applicant shall have the right to any equivalents in accordance with the applicable law.

[0023] In the following sections, various aspects of the invention described in the claims of the present application are defined in more detail. Each such aspect may be combined with any one or more other aspects, unless there is an express contrary indication. In particular, any feature indicated as being preferred or advantageous may be combined with any one or more other features indicated as being preferred or advantageous.

[0024] Throughout this specification, references 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 claimed invention. Thus, appearances of the phrases "in one embodiment" or "in an embodiment" in various places throughout this specification are not necessarily all referring to the same embodiment.

[0025] Furthermore, as will be apparent to those skilled in the art from this disclosure, in one or more embodiments, the particular features, structures, or characteristics may be combined in any suitable manner. Additionally, as will be understood by those skilled in the art, some of the embodiments described herein include some but not other features of other embodiments, and combinations of features of different embodiments are within the scope of the invention claimed in this application and are intended to form different embodiments. For example, in the appended claims, any of the claimed embodiments may be used in any combination.

[0026] In one embodiment, the invention claimed in the claims of this application is a polymer comprising a polyacrylate homo- or copolymer main chain and at least one moiety derived from a compound of general formula (I)

[0027]

Chemical formula

[0028] [wherein X, Y, and Z are independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted linear or branched C1-C 10 alkyl, OR, and C(=O)-OR (wherein R is substituted or unsubstituted linear or branched C1-C 10 alkyl)] and at least one moiety derived from a compound of general formula (I) is covalently bonded to at least one of the ends of the polyacrylate main chain, and the polymer is the subject.

[0029] In a preferred embodiment, the invention described in the claims of the present application is a polyacrylate homo- or copolymer main chain and a general formula (I)

[0030] [Chemical formula]

[0031] [wherein X, Y and Z are independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted linear or branched C1-C 10 alkyl and OR (wherein R is a substituted or unsubstituted linear or branched C1-C 10 alkyl)] A polymer comprising at least one moiety derived from a compound of formula (I), wherein at least one moiety derived from a compound of formula (I) is covalently bonded to at least one of the ends of the polyacrylate main chain, and the polymer is the subject of the invention.

[0032] In another preferred embodiment, the invention described in the claims of the present application is a polyacrylate homo- or copolymer main chain and a general formula (I)

[0033] [Chemical formula]

[0034] [wherein X, Y and Z are independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted linear or branched C1-C 10 alkyl)] A polymer comprising at least one moiety derived from a compound of formula (I), wherein at least one moiety derived from a compound of formula (I) is covalently bonded to at least one of the ends of the polyacrylate main chain, and the polymer is the subject of the invention.

[0035] In yet another preferred embodiment, the invention described in the claims of the present application is a polyacrylate homo- or copolymer main chain and a general formula (I)

[0036] [Chemical formula]

[0037] [Wherein, X, Y and Z are independently selected from the group consisting of hydrogen and halogen] A polymer comprising at least one moiety derived from a compound of general formula (I), wherein at least one moiety derived from a compound of general formula (I) is covalently bonded to at least one of the ends of the polyacrylate main chain, and the polymer is the subject.

[0038] In another preferred embodiment, the invention described in the claims of the present application is a polyacrylate copolymer main chain and a general formula (I)

[0039] [Chemical formula]

[0040] [Wherein, X, Y and Z are hydrogen] A polymer comprising at least one moiety derived from a compound of general formula (I), wherein at least one moiety derived from a compound of general formula (I) is covalently bonded to at least one of the ends of the polyacrylate main chain, and the polymer is the subject.

[0041] In a preferred embodiment, the compound of general formula (I) is

[0042] [Chemical formula]

[0043] [Wherein, X, Y and Z are hydrogen, halogen, substituted or unsubstituted linear or branched C1-C 10 alkyl, OR and C(=O)-OR (wherein R is substituted or unsubstituted linear or branched C1-C 10 alkyl) and are independently selected from the group consisting of] is.

[0044] In a preferred embodiment, X is hydrogen, halogen, substituted or unsubstituted linear or branched C1-C 10 alkyl, OR and C(=O)-OR (wherein R is substituted or unsubstituted linear or branched C1-C 10 alkyl), more preferably, X is hydrogen, halogen, substituted or unsubstituted linear or branched C1-C 10 alkyl and OR (wherein R is substituted or unsubstituted linear or branched C1-C 10 alkyl). Even more preferably, X is selected from the group consisting of hydrogen, halogen, substituted or unsubstituted linear or branched C1-C 10 alkyl. Most preferably, X is selected from the group consisting of hydrogen and halogen. In particular, X is hydrogen.

[0045] In a preferred embodiment, Y is hydrogen, halogen, substituted or unsubstituted linear or branched C1-C 10 alkyl, OR and C(=O)-OR (wherein R is substituted or unsubstituted linear or branched C1-C 10 alkyl), more preferably, Y is hydrogen, halogen, substituted or unsubstituted linear or branched C1-C 10 alkyl and OR (wherein R is substituted or unsubstituted linear or branched C1-C 10 alkyl). Even more preferably, Y is selected from the group consisting of hydrogen, halogen, and substituted or unsubstituted linear or branched C1-C 10 alkyl. Most preferably, Y is selected from the group consisting of hydrogen and halogen. In particular, Y is hydrogen.

[0046] In a preferred embodiment, Z is hydrogen, halogen, substituted or unsubstituted linear or branched C1-C 10 alkyl, OR and C(=O)-OR (wherein R is substituted or unsubstituted linear or branched C1-C 10selected from the group consisting of (being alkyl), more preferably, Z is hydrogen, halogen, and substituted or unsubstituted linear or branched C1-C 10 alkyl and OR (wherein R is substituted or unsubstituted linear or branched C1-C 10 alkyl). Even more preferably, Z is selected from the group consisting of hydrogen, halogen, and substituted or unsubstituted linear or branched C1-C 10 alkyl. Most preferably, Z is selected from the group consisting of hydrogen and halogen. In particular, Z is hydrogen.

[0047] In a preferred embodiment, X, Y and Z are each preferably a halogen selected from the group consisting of F, Cl, Br and I. More preferably, the halogen is selected from Cl and Br, and most preferably, the halogen is Cl.

[0048] Within the context of the invention recited in the claims of the present application, the term "alkyl", as used herein, generally refers to an acyclic saturated aliphatic group containing a linear or branched alkyl saturated hydrocarbon group represented by the formula C n H 2n+1 wherein n is the number of carbon atoms such as 1, 2, 3, 4, etc.

[0049] In a preferred embodiment, X, Y and Z are C1-C 10 alkyl, more preferably C1-C6 alkyl, even more preferably C1-C5 alkyl, most preferably C1-C3 alkyl, particularly preferably C1-C2 alkyl.

[0050] In a preferred embodiment, X, Y and Z are selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl, more preferably selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl and hexyl, even more preferably selected from the group consisting of methyl, ethyl, propyl, butyl and pentyl, most preferably selected from the group consisting of methyl, ethyl and propyl, particularly selected from methyl and ethyl, and are linear C1-C 10 alkyl.

[0051] In a preferred embodiment, X, Y and Z are selected from the group consisting of isopropyl, iso-butyl, neo-pentyl, 2-ethyl-hexyl, 2-propyl-heptyl, 2-butyl-octyl, 2-pentyl-nonyl, 2-hexyl-decyl, iso-hexyl, iso-heptyl, iso-octyl, iso-nonyl and iso-decyl, more preferably selected from the group consisting of isopropyl, iso-butyl, neo-pentyl and 2-ethyl-hexyl, most preferably selected from isopropyl and iso-butyl, and are branched C1-C 10 alkyl.

[0052] In a preferred embodiment, the substituted, linear or branched C1-C 10 alkyl is substituted with hydroxy, alkoxy, aryl, substituted aryl, where the substituent is selected from halogen, hydroxy, amine, alkyl, nitro, cyano, etc., and refers to a linear or branched saturated hydrocarbon group having C1-C 10 carbon atoms.

[0053] In a preferred embodiment, X, Y and Z are hydroxymethyl, hydroxyethyl, hydroxy, propyl, hydroxyisopropyl, hydroxybutyl, hydroxyisobutyl, hydroxytert-butyl, 2-hydroxy-hexyl, 2,3-dihydroxy-hexyl, 3-hydroxy-2-methoxyhexyl, 2-hydroxy-heptyl, 2,3-dihydroxy-heptyl, 3-hydroxy-2-methoxyheptyl, 2,3-dimethoxyheptyl, 2-ethoxy-3-methoxy-heptyl, 2-isopropoxy-3-methoxy-heptyl, 2,3-diisopropoxyheptyl, 3-hydroxy-2-methoxyoctyl, 2,3-dimethoxyoctyl, 2-ethoxy-3-methoxy-octyl, 2-isopropoxy-3-methoxy-octyl, 2,3-diisopropoxyoctyl, 3-hydroxy-5-methoxyoctyl, 2,5-dimethoxyoctyl, 5-ethoxy-3-methoxy-octyl, 5-isopropoxy-5-methoxy-octyl, 4,7-diisopropoxyoctyl, 3-hydroxy-2-methoxynonyl, 2,3-dimethoxynonyl, 2-ethoxy-3-methoxy-nonyl, 2-isopropoxy-3-methoxy-nonyl, 2,3-diisopropoxynonyl, 2-phenyl-hexyl, 2,3-diphenyl-hexyl, 3-hydroxy-2-phenylhexyl, 2-phenyl-heptyl and 2,3-diphenyl-heptyl, and are selected from the group consisting of substituted linear C1-C 10 alkyl.

[0054] In a preferred embodiment, X, Y and Z are OR, where R is a substituted or unsubstituted linear or branched C1-C 10 alkyl. In a preferred embodiment, OR is selected from the group consisting of methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, isobutoxy, tert-butoxy, isopentoxy, neopentoxy, methylhexyloxy, ethylhexyloxy, propylhexyloxy and isopropyl(isoproyl)methylnonyloxy.

[0055] In a preferred embodiment, X, Y and Z are C(=O)-OR, where R is a substituted or unsubstituted linear or branched C1-C 10 alkyl as defined above.

[0056] In a preferred embodiment, the compound of general formula (I) is selected from the group consisting of benzyl alcohol, o-tolylmethanol, m-tolylmethanol, p-tolylmethanol, (2,4-dimethylphenyl)methanol, (3,4-dimethylphenyl)methanol, (2,3-dimethylphenyl)methanol, (2,6-dimethylphenyl)methanol, [4-(hydroxymethyl)phenyl]methanol, [3-(hydroxymethyl)phenyl]methanol, [2-(hydroxymethyl)phenyl]methanol, (3-chlorophenyl)methanol, (4-chlorophenyl)methanol, (2-chlorophenyl)methanol, (3,5-dichlorophenyl)methanol, (2,3-dichlorophenyl)methanol, (3,6-dichlorophenyl)methanol, (4,5-dichlorophenyl)methanol, (2,6-dichlorophenyl)methanol, (3-chloro-5-methoxy-phenyl)methanol, (2-chloro-5-methoxy-phenyl)methanol, (3-chloro-4-methoxy-phenyl)methanol, (4-chloro-2-methoxy-phenyl)methanol, (3-methoxyphenyl)methanol, (2-methoxyphenyl)methanol, (4-methoxyphenyl)methanol, (2,3-dimethoxyphenyl)methanol, (2,4-dimethoxyphenyl)methanol, (2,5-dimethoxyphenyl)methanol, (2,6-dimethoxyphenyl)methanol, (3,4-dimethoxyphenyl)methanol, (3,5-dimethoxyphenyl)methanol and (3,6-dimethoxyphenyl)methanol.

[0057] More preferably, the compound of general formula (I) is selected from the group consisting of benzyl alcohol, o-tolylmethanol, p-tolylmethanol, [3-(hydroxymethyl)phenyl]methanol, (2-methoxyphenyl)methanol and (4-methoxyphenyl)methanol.

[0058] Most preferably, the compound of general formula (I) is benzyl alcohol.

[0059] In a particularly preferred embodiment, the invention described in the claims of the present application is a polymer comprising a polyacrylate homo- or copolymer main chain and at least one moiety derived from benzyl alcohol, wherein at least one moiety derived from benzyl alcohol is covalently bonded to at least one of the ends of the polyacrylate main chain.

[0060] In another preferred embodiment, the compound of general formula (I) is a compound having a melting point of less than 180 °C, more preferably the melting point of the compound of formula (I) is less than 150 °C, even more preferably the melting point of the compound of formula (I) is less than 100 °C, most preferably the melting point of the compound of formula (I) is less than 80 °C, and in particular the melting point of the compound of formula (I) is less than 40 °C.

[0061] In a preferred embodiment, the polyacrylate homopolymer main chain is at least one general formula (II)

[0062] [Chemical formula]

[0063] [wherein, R1 is selected from the group consisting of substituted or unsubstituted linear or branched C1-C 22 alkyl or substituted or unsubstituted aryl] obtained by polymerizing a mixture containing the acrylate monomer of.

[0064] In a preferred embodiment, R1 is C1-C 22 carbon atoms, more preferably C1-C 10 carbon atoms, even more preferably C1-C8 carbon atoms, most preferably C1-C5 carbon atoms, and in particular refers to a substituted or unsubstituted branched or linear saturated hydrocarbon group having C1-C4 carbon atoms.

[0065] In a preferred embodiment, R1 is selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, henicosyl and docosyl, more preferably, selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl and decyl, even more preferably, selected from the group consisting of methyl, ethyl, propyl, butyl and pentyl, most preferably, selected from the group consisting of methyl, ethyl and propyl, particularly, selected from methyl and ethyl, unsubstituted linear C1-C 22 alkyl.

[0066] In a preferred embodiment, R1 is selected from the group consisting of isopropyl, iso-butyl, neo-pentyl, 2-ethyl-hexyl, 2-propyl-heptyl, 2-butyl-octyl, 2-pentyl-nonyl, 2-hexyl-decyl, iso-hexyl, iso-heptyl, iso-octyl, iso-nonyl, iso-decyl, iso-dodecyl, iso-tetradecyl, iso-hexadecyl, iso-octadecyl and iso-eicosyl, more preferably, selected from the group consisting of isopropyl, iso-butyl, neo-pentyl, 2-ethyl-hexyl, 2-propyl-heptyl, 2-butyl-octyl, 2-pentyl-nonyl, 2-hexyl-decyl, iso-hexyl, iso-heptyl, iso-octyl, iso-nonyl and iso-decyl, most preferably, selected from isopropyl, iso-butyl, neo-pentyl and 2-ethyl-hexyl, unsubstituted branched C1-C 22 alkyl.

[0067] In a preferred embodiment, R1 is hydroxy, alkoxy, unsubstituted aryl, substituted by substituted aryl, wherein the substituent is selected from the group consisting of halogen, hydroxy, amine, alkyl, nitro and cyano, C1-C 22A branched or linear saturated hydrocarbon group having a carbon atom, more preferably, substituted with hydroxy, alkoxy, unsubstituted aryl, or substituted aryl, wherein the substituent is selected from the group consisting of halogen, hydroxy, amine, alkyl, nitro, and cyano, C1-C 10 A branched or linear saturated hydrocarbon group having a carbon atom, even more preferably, substituted with hydroxy, alkoxy, unsubstituted aryl, or substituted aryl, wherein the substituent is selected from the group consisting of halogen and hydroxy, a branched or linear saturated hydrocarbon group having 1 to 6 carbon atoms, most preferably (probably), substituted with hydroxy, unsubstituted aryl, or substituted aryl, wherein the substituent is selected from the group consisting of halogen and hydroxy, refers to a branched or linear saturated hydrocarbon group having 1 to 5 carbon atoms.

[0068] In a preferred embodiment, R1 is a substituted branched C1-C selected from the group consisting of 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 4-hydroxybutyl, 2-(2-ethoxyethoxy)ethyl, and 2-phenoxyethyl 22 alkyl.

[0069] In another preferred embodiment, at least one acrylate monomer of general formula (II) is selected from the group consisting of methyl acrylate, ethyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxyisopropyl acrylate, propyl acrylate, n-butyl acrylate, octyl acrylate, isobutyl acrylate, tert-butyl acrylate, 4-hydroxybutyl acrylate, octyl acrylate, 2-ethylhexyl acrylate, 2-methoxyethyl acrylate, 2-ethoxyethyl acrylate, 2-butoxyethyl acrylate, 2-(2-ethoxyethoxy)ethyl acrylate, 2-(2-butoxyethoxy)ethyl acrylate 2-phenoxyethyl acrylate, isobornyl acrylate, isodecyl acrylate, lauryl acrylate, stearyl acrylate, behenyl acrylate, tetrahydrofurfuryl acrylate, isophorone acrylate, 2-(dimethylamino)ethyl acrylate, 2-(diethylamino)ethyl acrylate and polyethoxylated acrylate.

[0070] In a preferred embodiment, at least one acrylate monomer of general formula (II) is not a benzyl acrylate monomer.

[0071] In a preferred embodiment, at least one acrylate monomer is selected from the group consisting of 2-(perfluorohexyl)ethyl acrylate, 2-(perfluoroethyl)ethyl methacrylate and 2-(perfluorobutyl)ethyl methacrylate.

[0072] In a preferred embodiment, at least one acrylate monomer is a silicone-modified acrylate.

[0073] In a preferred embodiment, the polyacrylate copolymer backbone is obtained by polymerizing a mixture comprising at least one acrylate monomer of general formula (II) and at least one ethylenically unsaturated monomer different from the acrylate monomer of general formula (II).

[0074] In a preferred embodiment, at least one ethylenically unsaturated monomer is selected from the group consisting of (meth)acrylic acid esters of general formula (IIIa), acrylamides of general formula (IIIb), acrylonitrile, methacrylonitrile, acrylic acid, methacrylic acid, vinylcaprolactam, N-acryloyl-N'-methylpiperazine, N-acryloyl-N'-ethylpiperazine, N-acryloyl-N'-propylpiperazine, styrene, substituted styrene, α-methylstyrene, vinyltoluene, vinyl esters, vinylidene halides, and α-olefins.

[0075] In a preferred embodiment, the compound of general formula (IIIa) is

[0076] [Chemical formula]

[0077] [wherein, R2 is selected from the group consisting of substituted or unsubstituted linear or branched C1-C 22 alkyl and substituted or unsubstituted aryl] is.

[0078] In another preferred embodiment, the compound of general formula (IIIb) is

[0079] [Chemical formula]

[0080] [wherein, R3, R4 and R5 are independently selected from the group consisting of hydrogen, substituted or unsubstituted linear or branched C1-C 22 alkyl and substituted or unsubstituted aryl] is.

[0081] In a preferred embodiment, R2 is substituted or unsubstituted linear or branched C1-C 22Selected from the group consisting of alkyl and substituted or unsubstituted aryl, more preferably, R2 is unsubstituted, linear or branched C1-C 22 alkyl and substituted or unsubstituted aryl, most preferably, unsubstituted, linear or branched C1-C 10 alkyl and substituted or unsubstituted aryl, particularly, unsubstituted, linear or branched C1-C 10 selected from the group consisting of alkyl.

[0082] In another preferred embodiment, the compound of formula (IIIa) is methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, tert-butyl (meth)acrylate, n-hexyl (meth)acrylate, isobutyl (meth)acrylate, isopentyl (meth)acrylate, lauryl (meth)acrylate, 2-ethylhexyl (meth)acrylate, stearyl (meth)acrylate, behenyl (meth)acrylate, isodecyl (meth)acrylate, 2-propylheptyl (meth)acrylate, 3,5,5-trimethyl-1-hexyl (meth)acrylate, nonanyl (meth)acrylate, 2-propylheptyl (meth)acrylate, 2-isopropyl-5-methyl-hexyl (meth)acrylate, tridecyl (meth)acrylate, heptadecyl (meth)acrylate and heneicosanyl (meth)acrylate; and aryl (meth)acrylic acid esters such as phenyl acrylate in which its aryl ring contains 5 to 12 carbon atoms without possible additional substituents; and aralkyl (meth)acrylic acid esters such as benzyl methacrylate in which its aralkyl group contains 6 to 12 carbon atoms, preferably 7 to 12 carbon atoms, without possible additional substituents on the aryl group, and is a (meth)acrylic acid ester of a linear alcohol having 1 to 22 carbon atoms selected from the group consisting of them.

[0083] The aryl groups of the aryl (meth)acrylate esters and the aralkyl (meth)acrylate esters can, in each case, be unsubstituted or, for example, be substituted up to four times, such as in 4-methylphenyl methacrylate; and the (meth)acrylate esters of monoether monoalcohols or polyether monoalcohols such as ethers, polyethylene glycols, polypropylene glycols, polybutylene glycols or mixed polyalkylene glycols have from 4 to 80 carbon atoms and, for example, have a statistical block or gradient distribution of different monomers along the chain such as in tetrahydrofurfuryl (meth)acrylate, di(ethylene glycol) methyl ether (meth)acrylate, furfuryl (meth)acrylate, 2-butoxyethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, allyloxyethyl (meth)acrylate, 1-ethoxybutyl (meth)acrylate, ethyl triglycol (meth)acrylate, butyl diglycol (meth)acrylate, poly(propylene glycol) methyl ether (meth)acrylate and poly(ethylene glycol) alkyl ether (meth)acrylate, where alkyl represents a straight-chain or branched alkyl residue having from 1 to 22, preferably from 1 to 15, more preferably from 1 to 13, even more preferably from 1 to 10, most preferably from 1 to 7 carbon atoms.

[0084] In a preferred embodiment, R3, R4 and R5 are independently selected from the group consisting of hydrogen, substituted or unsubstituted straight-chain or branched C1-C 22 alkyl and substituted or unsubstituted aryl, more preferably from the group consisting of hydrogen, unsubstituted, straight-chain or branched C1-C 22 alkyl and substituted or unsubstituted aryl, even more preferably from the group consisting of hydrogen, unsubstituted, straight-chain or branched C1-C 22 alkyl and unsubstituted aryl, most preferably from the group consisting of hydrogen, unsubstituted, straight-chain or branched C1-C 10 alkyl and unsubstituted aryl, and particularly preferably, R3, R4 and R5 are independently hydrogen and methyl.

[0085] Typical examples of the compound of formula (IIIb) include methacrylamide, N-ethylacrylamide, N,N'-methylethylacrylamide, N,N'-diethylacrylamide, N-dimethylaminopropylmethacrylamide, N-isopropylacrylamide, N-isopropylmethacrylamide, 2-carboxylisopropylacrylamide, N-methylisopropylacrylamide, N-propylacrylamide, N-propylmethacrylamide, and N-(L)-(1-hydroxymethyl)propylmethacrylamide.

[0086] In a preferred embodiment, at least one acrylate monomer is selected from the group consisting of 2-(perfluorohexyl)ethyl methacrylate, 2-(perfluoroethyl)ethyl methacrylate, and 2-(perfluorobutyl)ethyl methacrylate.

[0087] In a preferred embodiment, at least one acrylate monomer is a terminal-reactive polydimethylsiloxane methacrylate macromonomer. The terminal-reactive polysiloxane compound has at least one polymerizable unsaturated group such as an acryloxy group, a methacryloxy group, a vinyl group, a propenyl group, a styryl group, an ethynyl group, a maleate group, or an acrylamide group. The terminal-reactive polysiloxane can be prepared by known methods or is commercially available. Examples of commercial products are Silaplane FM-0711, FM-0721, FM-0725, FM-0511, FM-0521, FM-0525, TM-0701, and TM-0701T.

[0088] In a preferred embodiment, at least one moiety derived from the compound of general formula (I) is present in an amount in the range of 1.5% by mass or more to 30% by mass or less, more preferably in the range of 1.5% by mass or more to 20% by mass or less, still more preferably in the range of 1.5% by mass or more to 15% by mass or less, most preferably in the range of 2% by mass or more to 10% by mass or less, and particularly preferably in the range of 3% by mass or more to 10% by mass or less, based on the total mass of the polymer.

[0089] In a preferred embodiment, the polymer has a number average molecular weight M within the range of 500 g / mol or more to 100,000 g / mol or less as measured by GPC, more preferably within the range of 500 g / mol or more to 80,000 g / mol or less, even more preferably within the range of 1,000 g / mol or more to 50,000 g / mol or less, most preferably within the range of 1,000 g / mol or more to 30,000 g / mol or less, and in particular, within the range of 1,000 g / mol or more to 10,000 g / mol as measured by GPC -1 having a number average molecular weight M within the following range n thereof.

[0090] In a preferred embodiment, the polyacrylate copolymer main chain containing a moiety derived from the compound of formula (I) has a number average molecular weight within the range of 1,000 g / mol or more to 3,000 g / mol as measured by GPC and incorporating 9% by mass of benzyl alcohol based on the total mass of the polymer -1 and is a polyacrylate copolymer.

[0091] In a preferred embodiment, the polyacrylate copolymer main chain containing a moiety derived from the compound of formula (I) has a number average molecular weight within the range of 1,000 g / mol or more to 3,000 g / mol as measured by GPC and incorporating 8% by mass of benzyl alcohol based on the total mass of the polymer -1 and is a polyacrylate copolymer.

[0092] In a preferred embodiment, the polyacrylate copolymer main chain containing a moiety derived from the compound of formula (I) has a number average molecular weight within the range of 1,000 g / mol or more to 3,000 g / mol as measured by GPC and incorporating 7% by mass of benzyl alcohol based on the total mass of the polymer -1 and is a polyacrylate copolymer.

[0093] In a preferred embodiment, the polyacrylate copolymer main chain containing a moiety derived from the compound of formula (I) has a number average molecular weight measured by GPC of 1,000 g / mol or more to 3,000 g / mol, incorporating 6% by mass of benzyl alcohol based on the total mass of the polymer. -1 It is a polyacrylate copolymer having a number average molecular weight within the following range.

[0094] In a preferred embodiment, the polyacrylate copolymer main chain containing a moiety derived from the compound of formula (I) has a number average molecular weight measured by GPC of 1,000 g / mol or more to 3,000 g / mol, incorporating 5% by mass of benzyl alcohol based on the total mass of the polymer. -1 It is a polyacrylate copolymer having a number average molecular weight within the following range.

[0095] In another embodiment, the invention described in the claims of the present application is a method for preparing a polymer, a) a mixture containing at least one acrylate monomer of general formula (II)

[0096]

Chemical formula

[0097] [wherein, R1 is selected from the group consisting of substituted or unsubstituted linear or branched C1-C 10 alkyl or substituted or unsubstituted aryl] is mixed with at least one free radical forming initiator and at least one general formula (I)

[0098]

Chemical formula

[0099] [wherein, X, Y and Z are hydrogen, halogen, substituted or unsubstituted linear or branched C1-C 10 alkyl, OR and C(=O)-OR (wherein, R is substituted or unsubstituted linear or branched C1-C 10selected independently from the group consisting of (being alkyl)] and a method comprising at least a step of polymerizing in the presence of a compound of.

[0100] In certain embodiments, at least one acrylate monomer of general formula (II) is defined as described above.

[0101] In another preferred embodiment, the compound of formula (I) is defined as described above.

[0102] In certain embodiments, the polymerization reaction is carried out in the presence of at least one free radical forming initiator.

[0103] In preferred embodiments, at least one free radical forming initiator is selected from the group consisting of peroxides, azo compounds and peracid derivatives.

[0104] In preferred embodiments, at least one radical forming initiator is an azo compound. Representative examples of radical forming initiator azo compounds are 2,2'-azobis(isobutyronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(methylbutyronitrile) and 1,1'-azobis(cyanocyclohexane).

[0105] In preferred embodiments, at least one radical forming initiator is a peroxy compound. Representative examples of peroxy compounds are benzoyl peroxide, lauroyl peroxide, t-butylperoxypivalate, t-butylperoctoate, tert-butylperacetate, tert-amylperpivalate, per-2-ethylhexanoate, butylperpivalate tert-butylperneodecanoate, tert-butylperisononanoate, tert-amylperbenzoate, tert-butylperoxydicarbonate, 5-di-2-ethylhexylperoxydicarbonate, dicyclohexylperneodecanoate and cumyl tert-butylpermaleate.

[0106] In a preferred embodiment, at least one radical-forming initiator is a peracid derivative preferably selected from the group consisting of persulfates, perborates, peroxysuccinic acid and diisopropyl peroxydicarbonates.

[0107] In another preferred embodiment, the ratio of at least one compound of general formula (I) to at least one acrylate monomer of general formula (II) in the mixture is from 10:1 to 1:10, more preferably from 8:1 to 1:8, even more preferably from 6:1 to 1:6, most preferably from 5:1 to 1:5, especially from 5:2 to 2:5.

[0108] In another preferred embodiment, the mixture containing at least one acrylate monomer of general formula (II) is introduced into at least one compound of formula (I) at a temperature in the range of 80°C to 180°C, more preferably, the mixture containing at least one acrylate monomer of general formula (II) is introduced into at least one compound of formula (I) at a temperature in the range of 100°C to 180°C, even more preferably, the mixture containing at least one acrylate monomer of general formula (II) is introduced into at least one compound of formula (I) at a temperature in the range of 100°C to 160°C, most preferably, the mixture containing at least one acrylate monomer of general formula (II) is introduced into at least one compound of formula (I) at a temperature in the range of 100°C to 150°C, especially, the mixture containing at least one acrylate monomer of general formula (II) is introduced into at least one compound of formula (I) at a temperature in the range of 100°C to 140°C.

[0109] In another preferred embodiment, the mixture containing at least one acrylate monomer of general formula (II) is introduced into the compound of formula (II) over a period of 2 to 8 hours, more preferably, the mixture containing at least one acrylate monomer of general formula (II) is introduced into the compound of formula (II) over a period of 2 to 6 hours, most preferably, the mixture containing at least one acrylate monomer of general formula (II) is introduced into the compound of formula (II) over a period of 3 to 6 hours.

[0110] In another preferred embodiment, at least one free radical forming initiator is present in an amount of 0.1% to 5% by weight, more preferably 0.1% to 4% by weight, more preferably 0.5% to 3% by weight, most preferably 0.5% to 2% by weight, and particularly 0.5% to 1% by weight, based on the total weight of the mixture.

[0111] In a preferred embodiment, the polymerization is carried out in the presence of at least one solvent selected from the group consisting of alcohols, ketones, aromatics, esters, glycol ethers, n-hexane, octane, and dimethylformamide.

[0112] Representative examples of ester solvents are ethyl acetate, n-butyl acetate, and 1-methoxy-2-propyl acetate.

[0113] Representative examples of alcohol solvents are ethanol, 1-propanol, n-butanol, and 1-methoxy-2-propanol.

[0114] Representative examples of aromatic solvents are toluene, xylene, and high-boiling alkylbenzenes.

[0115] Representative examples of ketone solvents are methyl isobutyl ketone and methyl ethyl ketone.

[0116] In a preferred embodiment, at least one compound of general formula (I) is also used as a solvent. Thus, the polymerization is carried out in the absence of an additional solvent.

[0117] In another preferred embodiment, the reaction is carried out over a period of from 2 to 10 hours, more preferably from 2 to 8 hours, most preferably from 2 to 6 hours, and particularly from 2 to 5 hours.

[0118] In another preferred embodiment, step b) is carried out at a temperature in the range of 80°C or higher to 180°C or lower, more preferably at a temperature in the range of 100°C or higher to 180°C or lower, most preferably at a temperature in the range of 100°C or higher to 160°C or lower, and particularly preferably at a temperature in the range of 100°C or higher to 140°C or lower.

[0119] In a preferred embodiment, the polymer is isolated by distilling off at least one solvent and / or the compound of general formula (I).

[0120] In another preferred embodiment, the distillation of the mixture is carried out at a temperature in the range of 80°C or higher to 180°C or lower, more preferably at a temperature in the range of 100°C or higher to 180°C or lower, most preferably at a temperature in the range of 100°C or higher to 160°C or lower, and particularly at a temperature in the range of 100°C or higher to 140°C or lower.

[0121] In a preferred embodiment, a mixture containing n-butyl acrylate and ethylhexyl acrylate in a mass ratio of 4:1 is reacted at a temperature in the range of 130 to 135°C for 1 to 3 hours in the presence of tert-butyl-peroxy 2-ethylhexyl carbonate (0.5% by mass based on the total monomer content) and benzyl alcohol to obtain an n-butyl acrylate-ethylhexyl acrylate polyacrylate copolymer in which 7% by mass of benzyl alcohol is covalently incorporated based on the content of the polyacrylate polymer.

[0122] In another preferred embodiment, the method comprises at least the step of polymerizing a mixture comprising n-butyl acrylate, ethylhexyl acrylate and hydroxyethyl acrylate in a ratio by mass of 76:19:5 at a temperature in the range of 130 to 135 °C for 1 to 3 hours in the presence of tert-butyl-peroxy 2-ethylhexyl carbonate (0.5% by mass) and benzyl alcohol to obtain a polyacrylate copolymer of n-butyl acrylate-ethylhexyl acrylate-hydroxyethyl acrylate that covalently incorporates 5.1% by mass of benzyl alcohol.

[0123] In another preferred embodiment, the method comprises at least the step of polymerizing a mixture comprising n-butyl acrylate, ethylhexyl acrylate and hydroxyethyl acrylate in a ratio by mass of 36:9:5 at a temperature in the range of 130 to 135 °C for 1 to 3 hours in the presence of tert-butyl-peroxy 2-ethylhexyl carbonate (0.5% by mass) and benzyl alcohol to obtain a polyacrylate copolymer of n-butyl acrylate-ethylhexyl acrylate-hydroxyethyl acrylate that covalently incorporates 5.8% by mass of benzyl alcohol.

[0124] In another preferred embodiment, the method comprises at least the step of polymerizing a mixture comprising n-butyl acrylate, ethylhexyl acrylate and hydroxyethyl acrylate in a ratio by mass of 18:15:17 at a temperature in the range of 130 to 135 °C for 1 to 3 hours in the presence of tert-butyl-peroxy 2-ethylhexyl carbonate (0.5% by mass) and benzyl alcohol to obtain a polyacrylate copolymer of n-butyl acrylate-ethylhexyl acrylate-hydroxyethyl acrylate that covalently incorporates 9% by mass of benzyl alcohol.

[0125] In another preferred embodiment, the method comprises at least the step of polymerizing a mixture containing n-butyl acrylate, ethylhexyl acrylate and acrylic acid in a ratio of 72:18:10 by mass at a temperature in the range of 130 to 135 °C for 1 to 3 hours in the presence of tert-butyl-peroxy 2-ethylhexyl carbonate (0.5% by mass) and benzyl alcohol to obtain a polyacrylate copolymer of n-butyl acrylate-ethylhexyl acrylate-acrylic acid incorporating 5.8% by mass of benzyl alcohol covalently.

[0126] In another preferred embodiment, the method comprises at least the step of polymerizing a mixture containing n-butyl acrylate, ethylhexyl acrylate and styrene in a ratio of 68:17:15 by mass at a temperature in the range of 130 to 135 °C for 1 to 3 hours in the presence of tert-butyl-peroxy 2-ethylhexyl carbonate (0.5% by mass) and benzyl alcohol to obtain a polyacrylate copolymer of n-butyl acrylate-ethylhexyl acrylate-styrene incorporating benzyl alcohol covalently.

[0127] In one embodiment, the invention described in the claims of the present application is directed to a liquid composition in the form of a dispersion, comprising a polyacrylate polymer incorporating a benzyl-type alcohol, a particulate solid material selected from the group consisting of a pigment and a filler, and a liquid diluent.

[0128] In another preferred embodiment, the liquid composition has a mass ratio of the particulate solid material to the polyacrylate polymer incorporating benzyl alcohol in the range of 100:1 to 1:50.

[0129] In another preferred embodiment, the liquid composition a) at least one particulate solid material selected from the group consisting of a pigment and a filler, in an amount of 1% by mass or more to 70% by mass or less based on the total mass of the liquid composition, and b) From 0.5% by mass to 50% by mass, based on the total mass of the liquid composition, of an acrylate polymer incorporating a benzyl group according to the invention described in the claims of the present application or a polymer prepared according to the method described in the claims of the present application, and c) From 10% by mass to 98.5% by mass, based on the total mass of the liquid composition, of at least one liquid diluent and comprising.

[0130] In another preferred embodiment, the liquid composition is present in the form of a pigment paste, a mill base, a colorant, a coating composition or an ink.

[0131] In one embodiment, the invention described in the claims of the present application is directed to the use of a polymer according to the invention described in the claims of the present application as an additive in coatings, paints, inks and adhesives.

[0132] In another preferred embodiment, the invention described in the claims of the present application is directed to the use of a polymer according to the invention described in the claims of the present application as a dispersant for particulate solid materials selected from the group consisting of pigments and fillers.

[0133] In another preferred embodiment, the invention described in the claims of the present application is directed to the use of a polymer according to the invention described in the claims of the present application as a flow and leveling agent or a surface additive in coatings, paints, inks and adhesives.

[0134] In another preferred embodiment, the invention described in the claims of the present application is directed to the use of a polymer according to the invention described in the claims of the present application as a resin component in coatings, paints, inks and adhesives.

[0135] In the following, it is not intended to limit the present disclosure to the specific embodiments listed below, and a list of embodiments is provided to further illustrate the present disclosure.

[0136] 1. A polyacrylate homo- or copolymer main chain and the general formula (I)

[0137]

Chem.

[0138] [wherein, X, Y and Z are independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted linear or branched C1-C 10 alkyl, OR and C(=O)-OR (wherein, R is substituted or unsubstituted linear or branched C1-C 10 alkyl)] A polymer comprising at least one moiety derived from a compound of the general formula (I), wherein at least one moiety derived from a compound of the general formula (I) is covalently bonded to at least one of the ends of the polyacrylate main chain.

[0139] 2. The polymer according to Embodiment 1, wherein at least one moiety derived from a compound of the general formula (I) is bonded to the polyacrylate homo- or copolymer main chain via -C(=O)-O-.

[0140] 3. The polymer according to Embodiment 1, wherein the polyacrylate homopolymer main chain is obtained by polymerizing a mixture containing at least one acrylate monomer of the general formula (II)

[0141]

Chem.

[0142] [wherein, R1 is selected from the group consisting of substituted or unsubstituted linear or branched C1-C 22 alkyl or C1-C 22 cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl)] The polymer according to Embodiment 1, which is obtained by polymerizing a mixture containing at least one acrylate monomer of the general formula (II).

[0143] 4. The polymer according to Embodiment 3, wherein R1 is linear or branched C1-C 10 alkyl or substituted aryl.

[0144] 5. The polymer according to Embodiment 3, wherein at least one acrylate monomer of general formula (II) is selected from the group consisting of methyl acrylate, ethyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxyisopropyl acrylate, propyl acrylate, n-butyl acrylate, octyl acrylate, isobutyl acrylate, tert-butyl acrylate, 4-hydroxybutyl acrylate, octyl acrylate, 2-ethylhexyl acrylate, 2-methoxyethyl acrylate, 2-ethoxyethyl acrylate, 2-butoxyethyl acrylate, 2-(2-ethoxyethoxy)ethyl acrylate, 2-(2-butoxyethoxy)ethyl acrylate 2-phenoxyethyl acrylate, isobornyl acrylate, isodecyl acrylate, lauryl acrylate, stearyl acrylate, behenyl acrylate, tetrahydrofurfuryl acrylate, isophorone acrylate, 2-(dimethylamino)ethyl acrylate, 2-(diethylamino)ethyl acrylate, polyethoxylated acrylate, 2-(perfluorohexyl)ethyl acrylate, 2-(perfluoroethyl)ethyl methacrylate, 2-(perfluorobutyl)ethyl methacrylate, silicone-modified acrylate.

[0145] 6. The polymer according to Embodiment 5, wherein at least one acrylate monomer of general formula (II) is selected from the group consisting of methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, octyl acrylate and polyethoxylated acrylate.

[0146] 7. The polymer according to Embodiment 1, wherein the polyacrylate copolymer backbone is obtained by polymerizing a mixture comprising at least one acrylate monomer of general formula (II) and at least one ethylenically unsaturated monomer.

[0147] 8. A polymer according to embodiment 7, wherein at least one ethylenically unsaturated monomer is selected from the group consisting of (meth)acrylate esters of formula (IIIa), acrylamides of formula (IIIb), acrylonitrile, methacrylonitrile, acrylic acid, methacrylic acid, vinyl caprolactam, N-vinylpyrrolidone, N-acryloyl-N'-methylpiperazine, N-acryloyl-N'-ethylpiperazine, N-acryloyl-N'-propylpiperazine, styrene and substituted styrene, α-methylstyrene, vinyltoluene, vinyl esters, vinylidene halides, and α-olefins.

[0148] 9. The (meth)acrylate ester of formula (IIIa) is

[0149]

Chemical formula

[0150] [wherein, R2 is selected from the group consisting of substituted or unsubstituted linear or branched C1-C 22 alkyl, substituted or unsubstituted aryl] and is a polymer according to embodiment 8.

[0151] 10. A polymer according to embodiment 9, wherein at least one methacrylate monomer is selected from the group consisting of 2-(perfluorohexyl)ethyl methacrylate, 2-(perfluoroethyl)ethyl methacrylate, and 2-(perfluorobutyl)ethyl methacrylate.

[0152] 11. A polymer according to embodiment 9, wherein at least one methacrylate monomer is a silicone-modified methacrylate.

[0153] 12. A polymer according to embodiment 9, wherein at least one acrylate monomer is a terminal-reactive polydimethylsiloxane methacrylate macromonomer.

[0154] 13. The (meth)acrylamide of formula (IIIb) is

[0155] [Chemical formula]

[0156] [wherein, R3, R4 and R5 are independently selected from the group consisting of hydrogen, substituted or unsubstituted linear or branched C1-C 22 alkyl and substituted or unsubstituted aryl] A polymer according to Embodiment 8, which is as follows.

[0157] 14. A polymer according to Embodiment 1, wherein the compound of general formula (I) is selected from the group consisting of benzyl alcohol, o-tolylmethanol, m-tolylmethanol, p-tolylmethanol, (2,4-dimethylphenyl)methanol, (3,4-dimethylphenyl)methanol, (2,3-dimethylphenyl)methanol, (2,6-dimethylphenyl)methanol, [4-(hydroxymethyl)phenyl]methanol, [3-(hydroxymethyl)phenyl]methanol, [2-(hydroxymethyl)phenyl]methanol, (3-chlorophenyl)methanol, (4-chlorophenyl)methanol, (2-chlorophenyl)methanol, (3,5-dichlorophenyl)methanol, (2,3-dichlorophenyl)methanol, (3,6-dichlorophenyl)methanol, (4,5-dichlorophenyl)methanol, (2,6-dichlorophenyl)methanol, (3-chloro-5-methoxy-phenyl)methanol, (2-chloro-5-methoxy-phenyl)methanol, (3-chloro-4-methoxy-phenyl)methanol, (4-chloro-2-methoxy-phenyl)methanol, (3-methoxyphenylmethanol, (2-methoxyphenyl)methanol, (4-methoxyphenyl)methanol, (2,3-dimethoxyphenyl)methanol, (2,4-dimethoxyphenyl)methanol, (2,5-dimethoxyphenyl)methanol, (2,6-dimethoxyphenyl)methanol, (3,4-dimethoxyphenyl)methanol, (3,5-dimethoxyphenyl)methanol and (3,6-dimethoxyphenyl)methanol.

[0158] 15. A polymer according to embodiment 14, wherein the compound of general formula (I) is selected from the group consisting of benzyl alcohol, o - tolylmethanol, p - tolylmethanol, [3 - (hydroxymethyl)phenyl]methanol, (2 - methoxyphenyl)methanol, and (4 - methoxyphenyl)methanol.

[0159] 16. A polymer according to embodiment 1, wherein at least one moiety derived from the compound of general formula (I) is present in an amount in the range of 1.5% by mass or more to 30% by mass or less based on the total mass of the polymer.

[0160] 17. A polymer according to embodiment 1, wherein at least one moiety derived from the compound of general formula (I) is present in an amount in the range of 2% by mass or more to 10% by mass or less based on the total mass of the polymer.

[0161] 18. A polymer according to embodiment 1, having a number - average molecular weight M in the range of 500 g / mol -1 or more to 100,000 g / mol -1 as measured by GPC. n

[0162] 19. A polymer according to embodiment 1, having a number - average molecular weight M in the range of 500 g / mol -1 or more to 60,000 g / mol -1 as measured by GPC. n

[0163] 20. A method for preparing a polymer according to one or more of embodiments 1 to 19, comprising: a) at least one compound of general formula (II)

[0164]

Chemical formula

[0165] [wherein, R1 is selected from the group consisting of substituted or unsubstituted linear or branched C1 - C 22 alkyl, and substituted or unsubstituted aryl] A mixture containing an acrylate monomer is polymerized in the presence of at least one free radical-forming initiator and at least one compound of general formula (I)

[0166] [Chemical formula]

[0167] [wherein X, Y and Z are independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted linear or branched C1-C 10 alkyl, OR and C(=O)-OR (wherein R is substituted or unsubstituted linear or branched C1-C 10 alkyl)] The method comprises at least the step of polymerizing in the presence of a compound of.

[0168] 21. The method according to embodiment 20, wherein at least one acrylate monomer of general formula (II) is present in an amount in the range of 40% by mass or more to 80% by mass or less based on the total mass of the mixture.

[0169] 22. The method according to embodiment 20, wherein the mixture containing at least one acrylate monomer of general formula (II) is introduced into at least one compound of formula (I) at a temperature in the range of 80°C to 180°C.

[0170] 23. The method according to embodiment 20, wherein the mixture containing at least one acrylate monomer of general formula (II) is introduced into the compound of formula (II) over a period of 2 to 8 hours.

[0171] 24. The method according to embodiment 20, wherein at least one free radical-forming initiator is present in an amount of 0.1% by mass to 5% by mass based on the total mass of the mixture.

[0172] 25. The method according to embodiment 20, wherein at least one free radical-forming initiator is selected from the group consisting of peroxides, azo compounds and peracid derivatives.

[0173] 26. A method according to embodiment 25, wherein the peroxide is selected from the group consisting of hydrogen peroxide, dibenzoyl peroxide, dicumyl peroxide, t-butyl peroxypivalate, t-butyl peroxy-2-ethylhexanoate, t-butyl peroxybenzoate, acetyl peroxide, benzoyl hydroperoxide, t-butyl hydroperoxide, di-t-butyl peroxide, lauryl peroxide, butyryl peroxide, tert-butyl peroxy-2-ethylhexyl carbonate, tert-amyl peroxy-2-ethylhexyl carbonate, and 1,1-di-(tert-butylperoxy)-3,3,5-trimethylcyclohexane.

[0174] 27. A method according to embodiment 25, wherein the azo compound is azobisisobutyronitrile.

[0175] 28. A method according to embodiment 25, wherein the peracid derivative is selected from the group consisting of dibenzoyl peroxide, dicumyl peroxide, t-butyl peroxypivalate, t-butyl peroxy-2-ethylhexanoate, and t-butyl peroxybenzoate.

[0176] 29. A method according to embodiment 20, wherein the polymerization is carried out in the presence of at least one solvent selected from the group consisting of alcohols, ketones, aromatics, acetates, glycol ethers, n-hexane, octane, and dimethylformamide.

[0177] 30. A method according to embodiment 20, wherein the ratio of the compound of general formula (I) to at least one acrylate monomer of general formula (II) is in the range of 1:10 to 10:1.

[0178] 31. A method according to embodiment 20, wherein the reaction is carried out over a period of 2 to 10 hours.

[0179] 32. A method according to embodiment 20, further comprising step b) of isolating the polymer by distilling off at least one solvent and / or the compound of general formula (I).

[0180] 33. A method according to embodiment 32, wherein step b) is carried out at a temperature in the range of 80 °C or higher to 180 °C or lower.

[0181] 34. A liquid composition in the form of a dispersion, comprising a polymer according to one or more of embodiments 1 to 19 or a polymer obtained according to one or more of the methods of embodiments 20 to 33, a particulate solid material selected from the group consisting of a pigment and a filler, and a liquid diluent.

[0182] 35. A liquid composition according to embodiment 34, wherein the mass ratio of the particulate solid material to the polymer is in the range of 100:1 to 1:50.

[0183] 36. a) At least one particulate solid material selected from the group consisting of a pigment and a filler, in an amount of 1% by mass or more to 70% by mass or less based on the total mass of the liquid composition; b) A polymer according to one or more of embodiments 1 to 19 or a polymer obtained according to one or more of the methods of embodiments 20 to 33, in an amount of 0.5% by mass or more to 50% by mass or less based on the total mass of the liquid composition; c) At least one liquid diluent, in an amount of 10% by mass or more to 98.5% by mass or less based on the total mass of the liquid composition. A liquid composition according to embodiment 34 or 35.

[0184] 37. A liquid composition according to one or more of embodiments 34 to 36, in the form of a pigment paste, a mill base, a colorant, a coating composition or an ink.

[0185] 38. Use of a polymer according to one or more of embodiments 1 to 19 or a polymer obtained according to one or more of the methods of embodiments 20 to 33 as an additive in coatings, paints, inks and adhesives.

[0186] Use of a polymer according to one or more of embodiments 1 to 19 or a polymer obtained according to one or more of the methods of embodiments 20 to 33 as a dispersant for particulate solid materials selected from the group consisting of pigments and fillers.

[0187] 40. Use of a polymer according to one or more of embodiments 1 to 19 or a polymer obtained according to one or more of the methods of embodiments 20 to 33 as a flow and leveling agent or surface additive in coatings, paints, inks and adhesives.

[0188] 41. Use of a polymer according to one or more of embodiments 1 to 19 or a polymer obtained according to one or more of the methods of embodiments 20 to 33 as a resin component in coatings, paints, inks and adhesives.

[0189] The invention described in the claims of this application has been described from the perspective of its specific embodiments. However, 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 described in the claims of this application.

Examples

[0190] The invention described in the claims of this application will be illustrated in detail by the following non-limiting examples. More specifically, the test methods specified below are part of the general disclosure of this application and are not limited to specific embodiments.

[0191] Materials: n-Butyl acrylate (nBA) 2-Ethylhexyl acrylate (EHA) 2-Hydroxyethyl acrylate (HEA) Acrylic acid (AA), and Styrene (SY) are commercially available from BASF SE.

[0192] Benzyl alcohol is available from Sigma Aldrich.

[0193] Solvesso® 100 is available from Bernd Kraft.

[0194] Physical methods Method for determining the content of the aromatic moiety: 1 1H NMR spectroscopy, gravimetric analysis

[0195] M w , M n and method for determining PDI: Gel permeation chromatography (polystyrene standard)

[0196] General procedure for preparing the polymer The solvent benzyl alcohol was initially charged into the reactor and heated to 100 to 150 °C. The monomer mixture was added over 1 to 5 hours. The addition of the free radical initiator was started simultaneously with the monomer feed but added over 2 to 5 hours. The total amount of the solvent was in the range of 30% to 80% mainly depending on the target molecular weight of the polymer with respect to the amounts of the monomer and the initiator. The mixture was stirred at 120 to 150 °C separately for 1 to 10 hours, then the solvent was distilled off and the polymer was isolated with a solid content of 97 - 100%.

[0197]

Table 1

[0198] Detailed analysis of the NMR spectra revealed that benzyl alcohol is incorporated at the ends of the polymer chains by radical transfer reactions and in small amounts via ester linkages. The total amount of benzyl alcohol incorporated into the polymer is determined by the reaction conditions during polymerization and the distillation process.

[0199] The use of an acrylic polymer as a leveling agent was tested. The differences in the coating properties of the polymers prepared according to the invention described in the claims of the present application were compared with polymers having the same or similar chemical structures, the same or similar molecular weights and molecular weight distributions, obtained via state-of-the-art free radical solution polymerization, as well as with commercially available products regarded as benchmarks. It was found that the formulations containing the products described in the claims of the present application exhibited similar or better leveling performance and much better color indices compared to the polymers obtained via state-of-the-art free radical solution polymerization or commercially available products. The comparison is summarized in Table 2. From Table 2, it can be inferred that the acrylate polymer of the present invention incorporating a benzyl-type alcohol shows a reduction in discoloration compared to the corresponding polymer prepared via state-of-the-art free radical solution polymerization in the industrial aromatic hydrocarbon solvent Solvesso® 100, according to the measured Hazen color number.

[0200]

Table 2

[0201] The acrylate polymers of the present invention incorporating a benzyl-type alcohol (Example 1) were tested for their use as leveling agents in a standard 2KPU solvent-based clear coat at an addition level of 1% by weight (0.1% by weight of Byk 310 and 0.9% by weight of additives (Byk® 361N or Example 1)). Tables 3 (stock solution) and 4 (hardener solution) list the test formulations of the stock solution and the hardener.

[0202]

Table 3

[0203]

Table 4

[0204] The stock solution and the hardener solution were mixed in a ratio of 3:1.

[0205] The DIN4 cup viscosity was found to be in the range of 25 - 30 s.

[0206] Coating: Gravity cup manual needle (Fliessbecher Manuell Needle) approximately 1.3 mm and approximately 40 - 50 μm.

[0207] Drying: 10 minutes at room temperature, 30 minutes at 100 °C.

[0208] After cooling, the performance was evaluated by measuring the wetting limit.

[0209] During spray coating, paint droplets were formed that affected the substrate being coated. Only when a suitable wetting and leveling package was available did the droplets fuse to form a thin, defect - free coating film. As the wetting limit decreased, such a defect - free coating was formed earlier, and the amount of coating material required to protect the substrate decreased.

[0210] [Table 5]

[0211] The results demonstrate that the polymer of the present invention in Example 1 already enables a defect - free film with a film thickness smaller than 4 μm, while the reference additive would require a thicker film of 6 μm.

[0212] In addition, the additive was tested at 1% by weight in a coil coating system according to the following formulation (0.1% by weight of Byk 310 and 0.9% by weight of the additive).

[0213] [Table 6]

[0214] The formulation was applied with a wire bar and cured in a coil oven at 230 °C for 15 seconds.

[0215] After cooling, the performance was evaluated by measuring the leveling using a Byk wave scan.

[0216]

Table 7

[0217] Lower short and long wavelength values indicate better leveling performance. Comparing the blank sample (LW 34.8) with two mixtures (Byk 310 with Byk 361N or Example 1 added) (LW 3.1), a strong equivalent improvement is observed. The two mixtures functioned equally well with respect to the smoothness of the surface measured by long and short wavelengths, but the additive of the present invention in Example 1 results in a higher gloss and a lower haze. Generally, the additive of the present invention in Polymer 1 enables the improvement of the appearance of the cured coating.

[0218] One general advantage of polyacrylate polymers incorporating benzylic alcohols lies in their low discoloration, which is associated with excellent properties as flow and leveling agents or as dispersants.

Claims

1. 1. Use of a polymer as a flow and leveling agent in coatings, paints, inks and adhesives, comprising The polymer comprises an acrylate homo- or copolymer backbone and a copolymer having the general formula (I) [Formula 1] [In the formula, X, Y and Z are hydrogen, halogen, substituted or unsubstituted linear or branched C 1 ~C 10 Alkyl, OR, and C(═O)—OR (wherein R is a substituted or unsubstituted linear or branched C 1 ~C 10 alkyl). and at least one moiety derived from a compound of general formula (I) covalently bonded to at least one of the termini of the acrylate homo- or copolymer backbone, and wherein the at least one moiety derived from a compound of general formula (I) is present in an amount ranging from ≧1.5% by weight to ≦30% by weight based on the total weight of the polymer.

2. 2. The use according to claim 1, wherein in the polymer, the at least one moiety derived from a compound of general formula (I) is attached to the acrylate homo- or copolymer backbone via -C(=O)-O-.

3. In the polymer, the acrylate homopolymer backbone comprises at least one copolymer having the general formula (II): [Case 2] [In the formula, R 1 is a substituted or unsubstituted linear or branched C 1 ~C 22 Alkyl or C 1 ~C 22 cycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted aralkyl.

2. The use according to claim 1, obtained by polymerizing a mixture comprising an acrylate monomer of

4. In the polymer, the compound of general formula (I) is selected from the group consisting of benzyl alcohol, o - tolulylmethanol, m - tolulylmethanol, p - tolulylmethanol, (2,4 - dimethylphenyl)methanol, (3,4 - dimethylphenyl)methanol, (2,3 - dimethylphenyl)methanol, (2,6 - dimethylphenyl)methanol, [4 - (hydroxymethyl)phenyl]methanol, [3 - (hydroxymethyl)phenyl]methanol, [2 - (hydroxymethyl)phenyl]methanol, (3 - chlorophenyl)methanol, (4 - chlorophenyl)methanol, (2 - chlorophenyl)methanol, (3,5 - dichlorophenyl)methanol, (2,3 - dichlorophenyl)methanol, (3,6 - dichlorophenyl)methanol, (4,5 - dichlorophenyl)methanol, (2,6 - dichlorophenyl)methanol, (3 - chloro - 5 - methoxy - phenyl)methanol, (2 - chloro - 5 - methoxy - phenyl)methanol, (3 - chloro - 4 - methoxy - phenyl)methanol, (4 - chloro - 2 - methoxy - phenyl)methanol, (3 - methoxyphenyl)methanol, (2 - methoxyphenyl)methanol, (4 - methoxyphenyl)methanol, (2,3 - dimethoxyphenyl)methanol, (2,4 - dimethoxyphenyl)methanol, (2,5 - dimethoxyphenyl)methanol, (2,6 - dimethoxyphenyl)methanol, (3,4 - dimethoxyphenyl)methanol, (3,5 - dimethoxyphenyl)methanol and (3,6 - dimethoxyphenyl)methanol. The use according to claim 1.

5. The polymer has a number - average molecular weight M measured by gel permeation chromatography in the range of -1 500 g / mol or more to -1 100,000 g / mol or less. The use according to claim 1. n

6. A method for preparing a polymer as a flow and leveling agent in a coating, paint, ink and adhesive as defined in any one of claims 1 to 5, comprising: a) at least one general formula (II) 【Chemical Formula 3】 [In the formula, R 1 is selected from the group consisting of substituted or unsubstituted linear or branched C 1 to C 22 alkyl, and substituted or unsubstituted aryl] A mixture containing an acrylate monomer of is polymerized in the presence of at least one free radical-forming initiator and at least one compound of general formula (I) 【Chemical Formula 4】 [In the formula, X, Y, and Z are independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted linear or branched C 1 to C 10 alkyl, OR, and C(=O)-OR (wherein R is substituted or unsubstituted linear or branched C 1 to C 10 alkyl)] including at least the step of polymerizing in the presence of a compound of , The mixture containing at least one acrylate monomer of general formula (II) is introduced into the at least one compound of formula (I) at a temperature within the range of 100°C to 140°C, The at least one free radical-forming initiator is present in an amount in the range of 0.5% by mass to 1% by mass based on the total mass of the mixture.

7. The method according to claim 6, wherein at least one acrylate monomer of general formula (II) is present in an amount in the range of 40% by mass or more to 80% by mass or less based on the total mass of the mixture.

8. The method according to claim 6, wherein the mixture containing at least one acrylate monomer of general formula (II) is introduced into the compound of formula (I) over a period of 2 to 8 hours.

9. The method according to claim 6, wherein the at least one free radical-forming initiator is selected from the group consisting of peroxides, azo compounds, and peracid derivatives.

10. The method according to claim 6, wherein the mixture is stirred at 120 to 140 °C for 1 to 10 hours.

11. The method according to claim 6, further comprising step b) of isolating the polymer by distilling off at least one solvent and / or the compound of general formula (I).

12. The method according to claim 11, wherein step b) is carried out at a temperature in the range of 100 °C or higher to 140 °C or lower.

13. Use of a polymer as a flow and leveling agent in coatings, paints, inks and adhesives, wherein the polymer is obtained by the method according to any one of claims 6 to 12.

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