TW201105754A - Coating composition, method of producing a coating and coated article - Google Patents

Abstract

The present invention relates to a coating composition comprising at least one (meth)acrylic polymer and at least one reactive diluent, where the reactive diluent has at least one octadienyl group and the (meth)acrylic polymer has units which are derived from (meth)acrylic monomers which in the alkyl radical have at least one double bond and 8 to 40 carbon atoms and units which are derived from hydroxyl-containing monomers. The present invention further relates to a method of producing a coating. The present invention also describes a coated article comprising a coating obtainable by the method.

Description

201105754 VI. Description of the Invention: TECHNICAL FIELD OF THE INVENTION The present invention relates to a coating composition. Further, the present invention relates to a method of producing a coating which is carried out using the coating composition and the coated article obtainable by the method. [Prior Art] The coating composition (especially the paint) has been manufactured synthetically for a long time. An important group of such compositions is based on an aqueous dispersion which in many cases comprises a (meth) acrylate polymer. For example, the publication DE-A-4 1 05 1 34 describes an aqueous dispersion comprising an alkyl methacrylate as a binder. Paints of this type are also known from US 5,750,75 1 , EP-A-1 044 993 and WO 2006/0 1 3 06 1 . Further, a solvent-based coating composition which can be crosslinked by polyisocyanate is known from the publication DE-A-27 3 2 693. In addition to the aqueous dispersion, the reactive paint constitutes another group of known coating compositions. Paints of this type are known, for example, from ΕΡ-0 6 93 5 07. Moreover, compositions comprising so-called reactive diluents are known. For example, the publication EP-A-546 4 1 7 describes a coating composition comprising in particular an octadiene ether. The above-mentioned certified coating compositions have a good range of properties. However, there is still a continuing need to improve this range of properties. For example, coatings obtainable from some of the coating materials described above exhibit resistance to chemicals, especially to polar solvents, which are still insufficient to meet higher demands. -4- 201105754 SUMMARY OF THE INVENTION In view of the prior art, the object of the present invention is therefore to provide a coating composition having significant properties. These properties include, inter alia, high chemical resistance to the portion of the coating that can be obtained from the coating composition. The goal here is to achieve high stability to many different solvents and also to bases and acids. Especially for methyl ethyl ketone (MEK) should have very good resistance. Further, the hardness of the coating which can be obtained from the coating composition should be varied within a wide range. In particular, it is possible to obtain a particularly hard and scratch-resistant coating from the coating composition. Moreover, the coating obtainable from the coating composition of the present invention should have a relatively low brittleness with respect to hardness. Accordingly, it is also an object of the present invention to provide a coating composition having a particularly long shelf life and durability. A further object is to provide a coating composition that results in a coating having a high gloss. The coatings obtainable from the coating composition should exhibit high weathering stability, especially high UV resistance. In addition, the coating composition should exhibit good processing properties over a wide range of temperatures and humidities. Regarding its properties, the coating composition should exhibit improved environmental compatibility. In particular, it should be released into the environment via evaporation with a minimum amount of organic solvent. A further object is the coating composition specification which can be obtained very inexpensively and on an industrial scale. * These and other objects, which are not expressly stated, but which may be readily derived or inferred from the context of the discussion, are achieved by coating compositions having all of the features of claim 1 of the patent application. Advantageous modifications of the coating composition of the present invention are protected in the subsidiary. Regarding the method of manufacturing the coated layer -5 - 201105754 layer and the coated article, the object of the patent application is to achieve its purpose. The invention therefore provides a coating composition comprising at least one (meth)acrylic polymer and at least one reactive diluent, characterized in that the reactive diluent has at least one octadienyl group and The acrylic polymer has a unit derived from a (meth)acrylic monomer having at least one double bond and 8 to 4 carbon atoms in the alkyl group and a unit derived from a hydroxyl group-containing monomer. Through the technical means of the present invention, the present invention can additionally obtain the advantages including the following: The coating which can be obtained from the coating composition of the present invention exhibits high chemical resistance. Among them, high stability to many different solvents and to alkalis and acids can be achieved. In many cases, in particular, excellent resistance to methyl ethyl ketone (MEK) is obtained. Excellent resistance to water can also be achieved. These coating compositions can therefore be used to make protective coatings. Further, the hardness of the coating which can be obtained from the coating composition can be varied within a wide range. In particular, a particularly hard and scratch-resistant coating can be obtained. Moreover, the coatings obtainable from the coating compositions of the present invention have a relatively low brittleness with respect to hardness and chemical resistance. In addition to this, the coating composition of the present invention has good processing properties over a wide range of temperatures and humidity. Regarding its properties, the coating composition exhibits improved environmental compatibility. Therefore, a very small amount of organic solvent is released into the environment by evaporation. In a particularly preferred embodiment, no organic solvent is released to the atmosphere. In this case, the coating composition may contain a high solid content. -6 - 201105754 Furthermore, the coating composition of the present invention results in a coating having a high gloss. The coating composition of the present invention exhibits particularly long shelf life and durability. The coatings obtainable from the coating composition exhibit high weathering stability, more particularly high UV resistance. Additionally, the coating compositions of the present invention can be obtained on an industrial scale and in a particularly cost effective manner.

The coating composition of the present invention comprises at least one reactive diluent having at least one octadiene group. The compounds thus comprise at least one group of the formula -R, wherein R represents a group having exactly 8 carbon atoms and containing two carbon-carbon double bonds. Preferred groups having exactly 8 carbon atoms and 2 double bonds include, in particular, oct-2,7-dienyl, oct-3,7-dienyl, oct-4,7-dienyl, octyl -5,7-dienyl, octane-2,4-dienyl, octane-2,5-dienyl, octane-• 2,6-dienyl, oct-3,5-dienyl, Oct-3,6-dienyl and octyl-4,6-dienyl. Preferred compounds for use as reactive diluents may be from 140 g/m to 2000 g/m, preferably from 140 g/m to 1 000 g/m, and most preferably 140 g/ Moor mass in the range of 500 gram/mole. The dynamic viscosity of the reactive diluent can have a wide range. It is generally advantageous to be in the range of from 1 to 5,000 millibass, preferably from 1 to 1 000 millibars per second, and preferably in the range of from 10 to 500 millibass per second. Viscosity, which is measured according to DIN EN ISO 25 5 5 at 25 ° C (Brookfield) ° Therefore, it is particularly advantageous to have 180 ° C less than atmospheric pressure (1 024 mbar) to 201105754 ' A reactive diluent having a boiling point of at least 25 ° C, more preferably at least 28 ° C. In a preferred embodiment, the reactive diluent may have a boiling point at atmospheric pressure ranging from 180 to 350 °C, more preferably from 250 to 300 °C. In a particular aspect of the invention, the reactive diluent having at least one octadienyl group is an alcohol, an amine, an ether or an ester. Preferred alcohols include, in particular, octane-2,7-diisopropanol, oct-3,7-dienol, oct-4,7-dienol, oct-5,7-dienol, octane-2 , 4-dienol, octane-2,5-dienol, octane-2,6-dienol, oct-3,5-dienol, oct-3,6-dienol and oct-4 , 6-dienol. Preferred ethers include, in particular, compounds having an ether group derived from a monool having preferably 1 to 1 carbon atoms. The monoalcohols may be linear, cyclic or branched. Alternatively, the ethers can be prepared using unsaturated, saturated or aromatic alcohols. These ethers include, in particular, the above-mentioned methyl ether of octanediol, diethyl ether, acetonide, dibutyl ether, pentyl ether and hexyl ether. Examples of such ethers are, in particular, methoxyoctane-2,7-diene (methyloctane-2,7-dienyl ether), ethoxyoctane-2,7-diene and propoxyoctane _ 2 , 7-diene. The preferred ether derived from a monool preferably having 1 to 1 carbon atom preferably has a molecular weight of up to 300 g/mole, more preferably 14 to 250 g/mole. In another embodiment of the present invention, an ether of an alcohol having two, three or more hydroxyl groups can be used. The polyols preferably have from 2 to 10 carbon atoms and the alcohols may be linear, branched, cyclic, saturated, unsaturated or aromatic. Such ethers include ethers, especially ethylene glycol, propylene glycol, glycerol, trimethylol propyl, pentaerythritol, dipentaerythritol, mannitol, sorbitol, sucrose or mixtures of such -8-201105754 alcohols. The ether of the above polyol having octanediol may have one, one, two or more octadiene groups. Preferred compounds include, in particular, monooctyl-4,6-dienyloxyethanol, iota, 2-dioctyl-4,6-dimethoxyethane, mono-octyl-4,6-dienyloxy Propylene glycol, dioctyl-4,6-dienyloxypropanol, trioxin_ 2,7-one anopropyloxypropyl, monooctyl-2,7-dioxyethanol, 1,2-dioxin_ 2,7-Dimethoxyethane, monooctyl-2,7-diallyoxypropanediol, dioctyl-2,7-diallyoxypropanol and trioctyl-2,7-dienyloxypropane. These ethers may be used singly or as a mixture of one or more acids. The preferred ether derived from a polyol having preferably 2 to 1 carbon atoms preferably has a molecular weight of 170 to 800 g/mole, more preferably 17 to 600 g/mole. In addition to ethers and alcohols, amines can also be used. In this case, a compound having one, two or more amine groups can be used. Preferred amines contain from 8 to 20 carbon atoms. Preferred amines include, in particular, octane-2,7-dienylamine, oct-3,7-diamine, octa-4,7-dienamine, oct-5,7-dienamine, octane-2. , 4-dienylamine, octane 2,5-dienylamine, octane-2,6-dienylamine, oct-3,5-dienylamine, oct-3,6-dienylamine, s- 4,6-dienylamine, (methyl(octyl-2,7-dienyl)amino)ethanol, (ethyl(octyl-2,7-dienyl)amino)ethanol, 2-octyl- 2,7-Dienyloxyethanol and (methyl(octyl-2,7-dienyl)amino)ethylamine. The molecular weight of the preferred amine is preferably from 140 to 800 g/mole, more preferably from 170 to 600 g/mole. In addition, esters having one or more octadienyl groups are also preferred reactive diluents for use. Suitable carboxylic acids from which the esters are derived may be linear, branched, cyclic, saturated or unsaturated. In addition to the aliphatic acid, an aromatic acid can also be used. Such esters include esters of the above octadienol derived, inter alia, from monocarboxylic acids. The preferred monocarboxylic acid has 1 to 20 carbon atoms, preferably 1 to 1 carbon -9 - 201105754 atoms, and more preferably 1 to 4 carbon atoms. Preferred single residual acids include, in particular, formic acid, acetic acid, propionic acid, butyric acid, acrylic acid and methacrylic acid. Preferably, the reactive diluents have exactly one octadienyl group. The preferred ester derived from a monocarboxylic acid preferably having 1 to 20 carbon atoms preferably has a molecular weight of 15 to 500 g/mole, more preferably 15 to 3 g/m. In addition, 'esters of carboxylic acids having two, three or more carboxylic acid groups can also be used, such as esters of oxalic acid, citric acid, terephthalic acid, trans-butyric acid, maleic acid or adipic acid. . Preferred polycarboxylic acids have from 1 to 2, more preferably from 1 to 10, and more preferably from 1 to 6 carbon atoms. Particularly advantageous esters here are especially esters of polycarboxylic acids having one, two or more octadiene groups. The preferred ester derived from a polycarboxylic acid preferably having 1 to 20 carbon atoms preferably has a molecular weight of from 200 to 1 gram per mole, more preferably from 300 to 6 gram per mole. The above alcohol 'amine, ether or ester can be obtained by a known method including short-chain polymerization of 1,3 -butadiene. The term "short-chain polymerized oxime represents a reaction of a compound having a conjugated double bond in the presence of a nucleophile. The methods set forth in the publications WO 2004/002931, WO 03/031379 and WO 02/100803 are incorporated herein by reference for the purpose of disclosure, in particular, for the catalyzed reaction and reaction conditions, such as pressure and temperature. The short-chain polymerization of 1,3 -butadiene is preferably carried out by using a metal compound containing a metal of Groups 8 to 10 of the periodic table as a catalyst, and a palladium compound, particularly palladium-carbon ene, is particularly preferred. The composition is detailed in the above publication. The nucleophiles which can be used are, in particular, water, ammonia, monoalcohols 'polyols (especially -10- 201105754 are diols such as ethylene glycol, 1,2-propanediol, 1,3-propanediol), diamines (such as B) Diamine, N-methylethylenediamine, N,N'-dimethylethylenediamine or hexamethylenediamine, aminoalkanol (such as amine ethanol, N-methylamine ethanol, N-B The base amine • ethanol, amine propanol, N-methylamine propanol or N-ethylamine propanol) or carboxylic acid (especially the monocarboxylic and polycarboxylic acids detailed above). The nucleophiles set forth in the publications WO 2004/00293 1, WO 0 3/0 3 1 3 7 9 and WO 0 2/1 0 0 0 0 3 are incorporated herein by reference.温度 The temperature at which the short chain polymerization is carried out is between 10 and 180 ° C, preferably between 30 and 120 ° C, more preferably between 40 and 100 ° C. The reaction pressure is from 1 to 300 bar, preferably from 1 to 120 bar, more preferably from 1 to 64 bar, and most preferably from 1 to 20 bar. An isomer of a compound having an octa-2,7-dienyl group can be produced by isomerization of a double bond present in a compound having a octane-2,7-dienyl group. Particularly suitable reactive diluents according to the invention are obtained by reacting an alcohol having an octadienyl group with a monocarboxylic or polycarboxylic acid and/or with a polycarboxylic anhydride in an ester formation reaction. Particularly suitable for such reactions are short chain polymers based on at least trihydric alcohols or mixtures of alcohols having a statistical average functionality of at least 3 and an average of at least one free hydroxyl group per molecule. Particularly suitable for the esterification reaction are short-chain polymerization products of glycerol and butadiene having a hydroxyl group content of from 5. 5 wt% to 17 wt% and/or tris-hydroxyl groups having a hydroxyl group content of from 4.9 wt% to 14.0 wt%. Short chain polymerization product of propane and butadiene. Moreover, a preferred reactive diluent having a octadiene group is described in the publication ΕΡ-Α-0 5 46 417, wherein the reactive diluent and the reactive diluent used in the preparation of -11 - 201105754 The method of the agent is incorporated into the present specification for the purpose of disclosure. An amazing advantage may especially be from 0% to 50% by weight, more preferably from 5% to 3% by weight 'and most preferably from 15% by weight, based on the total weight of the coating composition. A coating composition of up to 25% by weight of the reactive diluent was obtained. In addition to the reactive diluents set forth above, the coating composition of the present invention has at least one unit derived from a (meth)acrylic monomer having at least one double bond and 8 to 40 carbon atoms in the alkyl group. (meth)acrylic polymer. The (meth)acrylic monomer having at least one double bond and 8 to 40 carbon atoms in the alkyl group is an ester of (meth)acrylic acid or a decylamine having an alkyl group having at least one carbon-carbon double bond and 8 Up to 40 carbon atoms. (Meth)acrylic acid represents methacrylic acid and acrylic acid and a mixture thereof. The alkyl or alcohol or guanamine group may preferably have from 10 to 30 carbon atoms, and more preferably from 12 to 20 carbon atoms, and the group may contain a hetero atom, especially an oxygen, nitrogen or sulfur atom. The hospital base may have one, two, three or more carbon-carbon double bonds. The polymerization conditions for preparing the (meth)acrylic polymer are preferably selected such that the proportion of the alkyl double bond remaining in the polymerization reaction is maximized. This can be achieved, for example, by sterically hindering the double bonds present in the alcohol group. Moreover, at least some, and preferably all, of the double bonds present in the alkyl group of the (meth)acrylic monomer have a lower reactivity than the (meth) acrylonitrile group in the radical polymerization reaction, and thus Preferably no more (meth) acryloyl groups are present in the alkyl group. Iodine-12-201105754' of a (meth)acrylic monomer for preparing a (meth)acrylic polymer and having at least one double bond and 8 to 40 carbon atoms in the alkyl group is preferably at least 5 More preferably, at least 100, and most preferably at least 125 grams of iodine per 100 grams of (meth)acrylic monomer. This type of (meth)acrylic monomer generally corresponds to formula (1):

Η 〇 wherein R is hydrogen or methyl, and X is independently oxygen or a group of the formula NR', wherein R' 0 is hydrogen or a group having 1 to 6 carbon atoms, and R 1 is 8 to 40, preferably It is a linear or branched group of 10 to 30, and more preferably 12 to 20 carbon atoms and having at least one CC double bond. A (meth') acrylic monomer having at least one double bond and 8 to 40 carbon atoms in the alkyl group may have, for example, (meth)acrylic acid and having at least one. double bond and 8 to 4 carbon atoms The esterification of an alcohol, the reaction of a (meth) propylene fluorenyl halide with the alcohol or the transesterification of a (meth) acrylate with the alcohol. (Meth) acrylamide can be obtained by reacting with an amine accordingly. Such anti- ◎ should be described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 5th edition on CD-ROM or F.-B. Chen, G. Bufkin, "Crosslinkable Emulsion Polymers by Autooxidation I", Journal of Applied Polymer Science, Vol. 3 0, 457 1 - 4582 (1985). 'Alcohols suitable for this reaction include, in particular, octenol, terpene alcohol, oxime alcohol, undecenol, dodecenol, tridecenol, tetradecyl alcohol, fifteen carbon Enol, hexadecenol, heptadecenol, octadecyl sterol, hexadecenol, eicosyl alcohol, docosaenol, octanediol, decadienyl alcohol, Decadienol, undecadienyl alcohol, dodecadienol, thirteen-13- 201105754 carbon dienol, tetradecadienol, fifteen-dienol, hexadecadienol , heptadecadienol, octadecadienol, decadecadienol, eicosandienol and/or docosadienol. Such so-called fatty alcohols are commercially available or obtainable from fatty acids in some cases, as described, for example, in F.-B. Chen, G. Bufkin, Journal of Applied Polymer Science, Vol. 3 0, 45. 7 1 -4582 (1 98 5). Preferred (meth) acrylates obtainable by this method include, in particular, octadienyl (meth) acrylate, octadecadienyl (meth) acrylate, octadecyl (meth) acrylate. , hexadecyl (meth) acrylate, octadecyl (meth) acrylate and hexadecyl (meth) acrylate. Further, the (meth) acrylate having at least one double bond and 8 to 40 carbon atoms in the alkyl group may also have a reactive group in the alkyl group by an unsaturated fatty acid, more preferably an alcohol group ( Obtained by reaction of methyl) acrylate. Reactive groups include, in particular, hydroxyl groups and epoxy groups. In particular, for example, the following may be used as a reactant for preparing the aforementioned (meth) acrylate: (meth) hydroxyalkyl acrylate such as 3-hydroxypropyl (meth)acrylate or 3,4-di(meth)acrylate Hydroxybutyl ester, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2,5-dimethyl-1,6-hexanediol (meth) acrylate, 1, 1〇-nonanediol (meth) acrylate; or an epoxy group-containing (meth) acrylate such as glycidyl (meth) acrylate. Fatty acids suitable for reaction with the aforementioned (meth) acrylates are commercially available in many cases and are available from natural sources. The fatty acid includes, in particular, undecylenic acid, palmitoleic acid, oleic acid, elaidic acid, vaccenic acid, twenty carbon sulphuric acid, twenty-two carbonic acid, -14- 201105754 sinapic acid, tetracosenoic acid, linoleic acid, linoleic acid, peanut oleic acid, eicosapentaenoic acid, squid acid and/or cervonic acid 〇- Preferred (meth) acrylates obtained by this process include, inter alia, (meth) propylene oxy-2-hydroxypropyl-linolenic acid ester, (meth) propylene methoxy _ 2-hydroxypropyl - linolenate and (meth) propylene oxime-2-hydroxypropyl-oleate. The reaction of a deuterium unsaturated fatty acid with a (meth) acrylate having a reactive group in the alkyl group, more particularly an alcohol group, is a known reaction per se and is described, for example, in DE-A-41 05 1 34 ' DE -A-25 1 3 5 1 6 ' DE-A-26 3 8 544 and US 5,750,751. In a preferred embodiment, a (meth)propenoic acid monomer of the formula (II) can be used:

R

Wherein R is hydrogen or methyl 'X1 and X2 are independently oxygen or a group of formula NR, wherein R' is hydrogen or a group having from 1 to 6 carbon atoms, the prerequisite being at least one of χ1 and X2 groups Is a group of the formula NR' wherein R is hydrogen or a group having 1 to 6 carbon atoms, Z is a bonding group, and R2 is an unsaturated group having 9 to 25 carbon atoms. Moreover, the surprising advantages can be obtained by using a (meth)acrylic monomer of the formula (HI): -15- (III), 201105754 (III),

Wherein R is hydrogen or methyl, X is oxygen or a group of the formula NR' or a group having 1 to 6 carbon atoms, Z is a bonding group, a group of 1 to 6 carbon atoms, and R2 has 9 to 25 Saturated base. The term a has a group of 1 to 6 carbon atoms and represents a group of carbon atoms. It contains aromatic and heteroaromatic groups as well as alkoxy, cycloalkoxy, alkenyl, alkanoyl, alkoxy aliphatic groups. These groups may be straight or branched. Furthermore, it has a substituent, especially a halogen atom or a hydroxyl group. The R' group preferably represents an alkyl group. Preferred alkyl groups include propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropane Z groups preferably representing from 1 to 10, more than 1, and most preferably from 2 to A bond of three carbon atoms. These are linear or branched aliphatic or cycloaliphatic groups such as methyl propyl, exopropyl, n-butyl, isobutyl, and hexyl groups, particularly preferably ethyl. The R2 group in the formula (II) represents a 9 to 25 saturated group. Such groups specifically include alkenyl, cycloalkenyl, oxy, olefinic groups and heteroaliphatic groups. Further, the substituents are especially halogen atoms or hydroxyl groups. Preferred group groups, such as decenyl, nonenyl, undecenyl, and hexa-16-, wherein R' is hydrogen or R' is hydrogen or has one carbon atom and does not have 1 to 6 groups, a cycloalkyl group, a carbonyl group, and a hetero group, which may be a methyl group, an ethyl group, a group or a tributyl group, wherein the group has 1 to 5 groups including, in particular, an ethyl group, a butyl group or a ring carbon atom. The non-alkenyloxy group and the cycloalkenyl group may have an alkylene group including, in particular, an enedicarbyl group, a ten 201105754 tri-alkenyl group, a tetradecenyl group, a pentadecyl group, a hexadecenyl group, a heptadecene group. Alkenyl, octadecenyl, pentadecenyl, eicosyl, 21, hexenyl, behenyl, octadienyl, decadienyl, decadienyl •, -f-carbodiylidene, dodecyldidecyl, thirteen carbondione, tetradecadienyl, pentadecadienyl, hexadecadienyl, heptadecadiene Base, octadecyldicarbonate, nonadecyldicarbonate, eicosene, hexadecadienyl, docosadienyl, docosadienyl and/or ten Heptacarbon triene. Preferred (meth)acrylic monomers of the formulae (II) and (III) include, in particular, heptadecaenyloxy-2-ethyl-(meth) acrylamide, heptadecadiene oxime, respectively. Oxy-2-ethyl-(meth) acrylamide, heptadecatrienyloxy-2-ethyl'-(meth) acrylamide, heptadecene decyl-2-ethyl Base-(meth) acrylamide, (meth) propylene oxime-2-ethyl-palmitole amide, (meth) propylene oxime-2-ethyl oleylamine, (methyl ) propylene oxime-2-ethyl-eicosyl decylamine, (meth) propylene oxy-2-ethyl-cetyl decylamine, (methyl) propylene oxime oxime-2 -ethyl-erucamide, (meth)propenyloxy-2-ethyl-linolenic acid, (meth)acryloxy-2-ethyl-linolenic acid amide, (A) Base) propylene oxime-2-propyl-palmitole amide, (meth) propylene oxime-2-propyl oleylamine, (meth) propylene oxime-2-' propyl-di Decenolamine, (meth)propenyloxy-2-propyl-cetyl decylamine, (meth)acryloxy-2-propyl-erucamide, (meth) propylene醯-2-propyl - linseed Amides' and (meth) Bingxi Xi-propyl-2 - Amides views linseed oil. The (meth)acrylonitrile group represents an acryloyl group and a methacryl group, and a methacryl group is preferred. Particularly preferred monomers of formula (II) and (III) are methyl-17- 201105754 propylene oxime-2-ethyl-oleylamine, methacryloxy-2-ethyl-linolenic acid amide And methacryloxy-2-ethyl-linolenic acid decylamine. The (meth)acrylic monomers of the formulae (II) and (III) can be obtained in particular by a multistage process. In the first stage, for example, one or more unsaturated fatty acids or fatty acid esters can be reacted with, for example, an amine such as ethylenediamine, ethanolamine, propylenediamine or propylamine to form guanamine. In the second stage, an amine group of a hydroxyl group or an amine is reacted with a (meth) acrylate (e.g., methyl (meth) acrylate) to obtain a monomer of the formula (Π) or (III). With regard to the preparation of a monomer wherein X1 is a group of the formula NR' wherein R' is hydrogen or a group having 1 to 6 carbon atoms and X2 is oxygen, the alkyl (meth)acrylate may be correspondingly singulated (for example, Methyl (meth) acrylate is reacted with one of the aforementioned amines to form a (meth) acrylamide having a hydroxyl group in the alkyl group, which is then reacted with an unsaturated fatty acid to form a formula (Π) or ( ()) A (meth)acrylic monomer. The transesterification of an alcohol with a (meth) acrylate or the preparation of a (meth) acrylamide is described to include CN 1 3 5 5 1 6 1 , DE 21 29 425, DE 34 23 443 or ΕΡ-Α-0 In the disclosure of 534 666, the reaction conditions described in the publications and the catalysts also stated therein are incorporated herein by reference. Moreover, such reactions are described in J. Haken, "Synthesis of Acrylic Esters by Transesterification", 1967. The intermediate obtained in the reaction, such as carboxyguanamine having a hydroxyl group in the alkyl group, can be purified. In a particularly preferred embodiment of the invention, the resulting intermediate reaction can be carried out without extensive purification to form a (meth)acrylic monomer of formula (II) or (III). Further, the (meth)acrylic monomer having 8 to 40, preferably 10 to 30, and more preferably -18 to 201105754 is 12 to 20 carbon atoms and having at least one double bond in the alkyl group includes In particular, the monomer of the formula (IV):

Η 〇 wherein R is hydrogen or methyl, X is oxygen or a group of the formula NR', wherein R' is hydrogen or a group having 1 to 6 carbon atoms, and R3 is a Q alkyl group having 1 to 22 carbon atoms Y is an oxygen, sulfur or formula NR" group wherein R" is hydrogen or a group having from 1 to 6 carbon atoms, and R4 is an unsaturated group having at least 8 carbon atoms and at least two double bonds. In the formula (IV), the R3 group is a stretching group having 1 to 22 carbon atoms, preferably 'having 1 to 10', more preferably 2 to 6 carbon atoms. In a particular embodiment of the invention, the R3 group is an alkylene group having 2 to 4 carbon atoms, more preferably 2 carbon atoms. Extending bases having from 1 to 22 carbon atoms include, in particular, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl or cyclohexyl It is especially good to stretch ethyl. The R3 group contains at least two C-C double bonds which are not part of the aromatic system. The R4 group is preferably a group having exactly 8 carbon atoms and having exactly two double bonds. The R4 group is preferably a linear hydrocarbon group which does not contain a hetero atom. In a particular embodiment of the invention, the R4 group in formula (IV) may comprise a terminal double bond. In another modification of the invention, the R4 group in formula (IV) may not comprise a terminal double bond. The double bond present in the R4 group is preferably conjugated. In another preferred embodiment of the invention, the double bond present in the R4 group is unconjugated. Preferred r4 groups having at least two double bonds include, in particular, octyl 2,7_201105754 dilute, octa-3,7-dienyl, oct-4,7-dienyl, oct-5,7_ Dienyl, octane-2,4-dienyl, octane-2,5-dienyl, octyl 2,6-dienyl, oct-3-3,5-dilutyl, oct-3,6_ Dienyl and octyl-4,6-dienyl. The (meth)acrylic monomer of the formula (IV) comprises in particular 2-[(2-E)octyl-2,7-dienyl)methylamino]2-methyl-2-propenoic acid] Ester, 2-methylprop-2-enoic acid 2-[((2-2)octyl-2,7-dienyl)methylamino]ethyl ester, 2-methylprop-2-enoic acid 2 -[((3-£)octyl-3,7-dienyl)methylamino]ethyl ester, 2-methylprop-2-enoic acid 2-[((4-Z)oct-4,7 -dienyl)methylamino]ethyl ester, 2-methylprop-2-enoic acid 2-[(octo-2,6-dienyl)methylamino]ethyl ester, 2-methyl propyl 2-[(octyl-2,4-dienyl)methylamino]ethyl 2-enoate, 2-methylpropan-2-enoic acid 2-[(oct-3,5-dienyl) Methylamino]ethyl ester, 2-[((2- ugly) octyl-2,7-dienyl)methylamino]ethyl-(methyl) acrylamide, 2-[((2- Z) octyl-2,7-dienyl)methylamino]ethyl-(methyl)propanol, 2-[((3-E)octyl-3,7-dione)methyl Amino]ethyl-(methyl)propanamide, 2-[((4-Z)octyl-4,7-diphos)methylamino]ethyl-(methyl)acrylic acid amine , 2-[(octyl-2,6-disindolyl)methylamino]ethyl-(methyl)propanoid amide, 2-[(octyl-2,4-disindolyl)methylamino Ethyl-(meth) acrylamide, 2-[(xin -3,5-dienyl)methylamino]ethyl-(methyl)propanolamine, 2-methylpropan-2-dicarboxylic acid 2-[((2-E)oct-2,7 -disyl)ethylamino]ethyl ester, 2-methylpropan-2-carboxylic acid 2-[((2-Z)octyl-2,7-diphenyl)ethylamino]ethyl ester, 2-methylpropan-2-carboxylic acid 2-[((3-E)octyl-3,7-diyl) ethylamino]acetic acid, 2-methylpropan-2-isoacid 2-[ ((4-Z)octyl-4,7-dione) ethylamino]ethyl ester, 2-methylpropan-2-hydrochloric acid 2-[(octo-2,6-di-storage)ethyl Amino] vinegar, 2-methylpropan-2-dicarboxylic acid 2-[(octyl-2,4-diiso)ethylamino]ethyl ester, 2-methylprop-2-enoic acid 2- [(octyl-3,5-dienyl)ethylamino]ethyl-20- 201105754 vinegar, prop-2-ol acid 2_[((2·Ε) osin-2,7-dienyl)methyl Amino]ethyl ester, 2-((2-Z)octyl-2,7-dienyl)methylamino]ethyl acrylate, 2-nonanoic acid 2-[(( 3-E)octyl-3,7-dienyl)methylamino]ethyl ester, propan-2-enoic acid ' 2_[((4-Z)octyl-4,7'dienyl)methylamine Ethyl ester, prop-2-enoic acid 2-[(octyl-2,6-dienyl)methylamino]ethyl ester, prop-2-enoic acid 2-[(xin-2,4-di Alkenyl)methylamino]ethyl ester, prop-2-enoic acid 2-[(oct-3,5-dienyl)methylamine Ethyl ester, 2-methylprop-2-enoic acid 2-((2-E)octyl-2,7-dienyloxy)ethyl ester, 2-methylprop-2-enoic acid 2-( (2-Z)octyl-2,7-dienyloxy)ethyl 2-(2-E-octyl-3,7-dienyloxy)ethyl 2-methylprop-2-enoate 2-(2-Z)-octyl-4,7-dienyloxy) 2-methylprop-2-enoate 2-(Xin-2-ene) 6-dienyloxy)ethyl ester, 2-methyloctyl-2-enoic acid 2-(octyl-2,4-dienyloxy)ethyl ester, 2-methylprop-2-enoic acid 2-( Octyl-3,5-dienyloxy)ethyl ester, propyl-'2-enoic acid 2-((2-E)octyl-2,7-dienyloxy)ethyl ester, prop-2-enoic acid 2 -((2-Z)octyl-2,7-dienyloxy)ethyl ester, prop-2-enoic acid 2-((3-E)octyl-3,7-dienyloxy)ethyl ester, C _2_enoic acid 2-((4-Z)octyl-4,7-dienyloxy)ethyl ester, prop-2-enoic acid 2-(octo-2,6-dienyloxy)ethyl ester , 2-(octyl-2,4-dienyloxy)ethyl propionate and 2-(oct-3,5-dienyloxy)ethyl propionate. The (meth)acrylic monomer of the above formula (IV) can be specifically made by (meth)acrylic acid or (meth) acrylate (more particularly methyl (meth) acrylate or (meth) acrylate) The ester is obtained by a reaction with an alcohol and/or an amine. These reactions have been stated above. The reactant used for the reaction with (meth)acrylic acid or (meth) acrylate may advantageously conform to formula (V) = HX - R - Y - R4 (V), -21 - 201105754 where X is oxygen or Formula NR, a group wherein R' is hydrogen or a group having 1 to 6 carbon atoms, R3 is an alkylene group having from 1 to 22 carbon atoms, and Y is an oxygen, sulfur or NR" group, wherein R "It is hydrogen or a group having 1 to 6 carbon atoms" and R4 is at least a double unsaturated group having at least 8 carbon atoms. With regard to the definitions of preferred R', R", R3, Y and R4 groups, reference is made to the description of formula (IV). Preferred reactants according to formula (V) include (methyl (xin-2, 7-di) Alkenyl) amino)ethanol, (ethyl (octyl-2,7-dienyl)amino)ethanol, 2-octyl-2,7-dienyloxyethanol, (methyl (xin-2,7) -dienyl)amino)ethylamine, (methyl(octyl-3.7-dienyl)amino)ethanol, (ethyl(oct-3,7-dienyl)amino)ethanol, 2-octyl -3,7-dienyloxyethanol, (methyl(oct-3,7-dienyl)amino)ethylamine, (methyl(oct-4,7-dienyl)amino)ethanol, (ethyl (octyl-4,7-dienyl)amino)ethanol, 2-oct-4,7-dienyloxyethanol, (methyl(oct-4,7-dienyl)amino) Ethylamine, (methyl(oct-5,7-dienyl)amino)ethanol, (ethyl(octyl-5.7-dienyl)amino)ethanol, 2-oct-5,7-diene oxygen Ethyl alcohol, (methyl(oct-5,7-dienyl)amino)ethylamine, (methyl(octyl-2,6-dienyl)amino)ethanol, (ethyl (xin-2, 6-dienyl)amino)ethanol, 2-octyl-2,6-dienyloxyethanol, (methyl Octyl-2,6-dienyl)amino)ethylamine, (methyl(octyl-2,5-dienyl)amino)ethanol, (ethyl(octo-2,5-dienyl)amine Ethyl alcohol, 2-octane-2,5-dienyloxyethanol, (methyl(octo-2,5-dienyl)amino)ethylamine, (methyl(octyl-2,4-diene) Ethyl)ethanol, (ethyl (octyl-2,4-dienyl)amino)ethanol '2-octyl-2,4-dienyloxyethanol, (methyl(xin-2,4-) Dienyl)amino)ethylamine, (methyl(oct-3,6-dienyl)amino)ethanol, (ethyl (oct-3,6-di-22-201105754 alkenyl)amino) Ethanol, 2·octyl-3,6-dienyloxyethanol, (methyl(oct-3,6-dienyl)amino)ethylamine, (methyl(oct-3,5-dienyl)) Amino)ethanol, (ethyl (octyl-3,5-dienyl)amino)ethanol, 2-octa-3,5-dienyloxyethanol, (•methyl (xin-3,5-) Dienyl)amino)ethylamine, (methyl(oct-4,6-dienyl)amino)ethanol '(ethyl(oct-4,6-dienyl)amino)ethanol, 2- Oct-4,6-dienyloxyethanol and (methyl(oct-4,6-dienyl)amino)ethylamine.Reactant according to formula (V) Used singly or in a mixture. The reactant of the formula (V) can be obtained by a known method including short-chain polymerization of 1,3-butadiene. The term ~ short-chain polymer 〃 represents a conjugated double bond. The reaction of the compound in the presence of a nucleophile. The methods described in the publications WO 2004/002931, WO 03/031379 and WO 02/100803 are incorporated herein by reference for the purpose of disclosure, in particular Media and reaction conditions such as pressure and temperature. The short-chain polymerization of 1,3-butadiene may preferably be carried out using a metal compound containing a metal of Groups 8 to 10 of the Periodic Table of the Elements as a catalyst, and particularly preferably ◎ a palladium compound, particularly a palladium-carbon propylene, is preferably used. The composition, which is set forth in more detail in the above publication. In particular, diols such as ethylene glycol, 1,2-propylene glycol, 1,3-propanediol, diamines such as ethylenediamine, N-methylethylenediamine, hydrazine, Ν'-dimethylethylenediamine can be used. Or hexamethylenediamine; or an aminoalkanol such as amine ethanol, hydrazine-methylamine ethanol, hydrazine-ethylamine ethanol, amine propanol, hydrazine-methylamine propanol or hydrazine-ethylamine The alcohol acts as a nucleophile. When the nucleophilic agent used is (meth)acrylic acid, for example, octadienyl (meth)acrylate can be obtained, which is particularly suitable as (meth)acrylic acid having 8 to 40 carbon-23-201105754 atoms. Is a monomer. The preferred pressure and temperature for the implementation of short chain polymerizations are set forth above, so reference is made to such numbers. An isomer of a compound having an octa-2,7-dienyl group can be produced by isomerization of a double bond present in a compound having a octane-2,7-dienyl group. The (meth)acrylic polymer used in accordance with the present invention preferably comprises from 〇5 to 60% by weight, more preferably from 1% to 30% by weight, based on the weight of the (meth)acrylic polymer. Particularly preferred is 1.5% by weight f) to 20% by weight, and most preferably 2% by weight to 15% by weight of (meth)acrylic acid having at least one double bond and 8 to 40 carbon atoms in the alkyl group Monomer derived unit. The (meth)acrylic polymer is preferably obtainable by radical polymerization. The weight fraction of each unit contained in the polymers is provided correspondingly by the weight fraction of the corresponding monomers used to make the polymer, since the weight of the groups derived from the initiator or molecular weight regulator is typically ignored. The rate. There are at least one double bond and 8 to 40 carbon atoms in the alkyl group. The (meth)acrylic monomer may be used singly or as a mixture of two or more monomers. Further, the (meth)acrylic polymer used in the coating composition according to the present invention contains a unit derived from a hydroxyl group-containing monomer. The hydroxyl group-containing monomer is a compound having a carbon-carbon double bond and also having at least one hydroxyl group. The compounds preferably have from 3 to 30, more preferably from 4 to 20, and most preferably from 5 to 1 carbon atoms. The carbon groups of the compounds may be linear, branched or cyclic. Moreover, the compounds may have an aromatic or -24-201105754 heteroaromatic group. Like olefin alcohols, such as allyl alcohol, such compounds contain, in particular, unsaturated esters and ethers having a hydroxyl group. The compounds preferably comprise a (meth)propenoate having a hydroxyl group in the alkyl group, more particularly 2-hydroxyethyl (meth)acrylate (preferably 2-hydroxyethyl methacrylate). (HEMA)), hydroxypropyl (meth) acrylate, such as 2-hydroxypropyl (meth) acrylate and 3-hydroxypropyl (meth) acrylate (preferably hydroxypropyl methacrylate (HPMA)) , hydroxybutyl (meth) acrylate (preferably hydroxybutyl methacrylate (HBMA)), 3,4-dihydroxybutyl (meth) acrylate, 2,5 (meth) acrylate - dimethyl-1,6-hexanediol ester, 1,10-decane mono(meth)acrylate and glycerol mono(meth)acrylate. In a particular aspect of the invention, the (meth)acrylic polymer can have from 1% by weight to 70% by weight, more preferably 5% by weight, based on the weight of the (meth)acrylic polymer. 60% by weight, and most preferably from 10% to 40% by weight of units derived from hydroxyl-containing monomers. The (meth)acrylic polymer used in accordance with the present invention may be the same as the above (meth)acrylic monomer and hydroxyl group-containing monomer having at least one double bond and 8 to 40 carbon atoms in the alkyl group. It has units derived from other monomers. These co-monomers include, inter alia, (meth) acrylates having from 1 to 12 carbon atoms in the alkyl group and no double or heteroatoms in the alkyl group. Preferred herein are (meth) acrylates having 1 to 10 carbon atoms in the alkyl group and no double or hetero atom in the alkyl group. The (meth) acrylate having 1 to 12 carbon atoms in the alkyl group and having no double or hetero atom in the alkyl group includes, in particular, a (meth) acrylate having a linear or branched alkyl group, such as Methyl (meth) acrylate, (methyl) propyl-25- 201105754 ethyl enoate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, Isobutyl methacrylate, tert-butyl (meth)acrylate, amyl (meth)acrylate, hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, (methyl) Heptyl acrylate, octyl (meth) acrylate, 3-isopropyl heptyl (meth) acrylate, decyl (meth) acrylate, decyl (meth) acrylate, undecyl (meth) acrylate , 5-methylundecyl (meth)acrylate, dodecyl (meth)acrylate; and cycloalkyl (meth)acrylate such as cyclopentyl (meth)acrylate, (meth)acrylic acid Cyclohexyl ester, cyclohexyl (meth)acrylate having at least one substituent on the ring (such as (A) ) Tributylcyclohexyl acrylate and trimethylcyclohexyl (meth) acrylate, norbornyl (meth) acrylate, methyl decyl (meth) acrylate, dimethyl (meth) acrylate Base oxime ester, decyl (meth) acrylate, 1-adamantyl (meth) acrylate, 2-adamantyl (meth) acrylate, menthyl (meth) acrylate and isophthalic acid (meth) acrylate ester. The above (meth) acrylate having 1 to 12 carbon atoms in the alkyl group may be used singly or in a mixture. A surprising advantage is particularly revealed by a (meth)acrylic polymer having a weight of preferably from 5% by weight to 95% by weight, based on the weight of the (meth)acrylic polymer, more preferably from 1% by weight to 70% by weight, and most preferably 20% to 60% by weight of a unit derived from a (meth) acrylate having 1 to 12 carbon atoms in the alkyl group and no double or hetero atom in the alkyl group . In a particular aspect of the invention, the above (meth) acrylate having from 1 to 12 carbon atoms in the alkyl group and not containing a double bond or a hetero atom in the alkyl group may be selected such that it has The (meth)acrylic polymer composed of the (meth) acrylate of 1 to 12 carbon atoms, such as -26-201105754, has a melting point of at least 40 ° C, preferably at least 5 (TC, and more preferably at least 60). The glass transition temperature of °C is changed. • The glass transition temperature Tg of the polymer can be determined in a known manner by differential scanning calorimetry (DSC), in particular according to DIN EN ISO 1 1 3 57. The glass transition temperature is preferably The ground can be determined as the midpoint of the glass phase of the second heating curve at a heating rate of 1 per minute. In addition, the glass transition temperature 〇Tg can also be pre-calculated by the Fox equation. According to Fox TG, Bull. Am. Physics Soc. 1,3,p.1 23 (1 965), which is: _L = _£?_ +3- + ... +i Tg Tgt Tg2 Tgn . where xn is the mass fraction of monomer n (weight %/100) and Tgn are the glass transition temperatures of the homopolymer of monomer n in K. Further useful information can be obtained by those skilled in the art. Polymer Handbook, 2nd Edition, J. Wiley & Sons, New York (1 975), which is found to describe the Tg of most common homopolymers. According to this guide, for example, poly(methyl methacrylate) has 3 78K glass transition temperature, poly (butyl methacrylate) has a glass transition temperature of 297K, poly (isodecyl methacrylate) has a glass transition temperature of 383K, and poly(isodecyl acrylate) has a glass of 3 67K The conversion temperature and poly(cyclohexyl methacrylate) have a glass transition temperature of 3 56 K. - In order to determine the glass transition temperature, it has from 1 to 12 carbon atoms in the alkyl group and does not contain double bonds or impurities in the alkyl group. The polymer composed of the atomic (meth) acrylate may have a weight average molecular weight of at least 100,000 g/mole and a number average molecular weight of at least 80,000 g/mole. It has 1 to 12 carbon atoms in the alkyl group and The nature and amount of the above (meth) acrylate which does not contain a bis-27-201105754 bond or a hetero atom in the alkyl group can be selected by the above formula of Fox et al. Another preferred monomer group has an acid group. The acid group-containing monomer is a compound copolymerizable with the aforementioned (meth)acrylic monomer (preferably in a free radical mode). The compound includes, for example, a monomer having a sulfonic acid group such as vinylsulfonate. An acid; a monomer having a phosphonic acid group such as vinylphosphonic acid; and an unsaturated carboxylic acid such as methacrylic acid, acrylic acid 'fumaric acid, and maleic acid. It is especially good with methacrylic acid and acrylic acid. The monomer having an acid group may be used singly or as a mixture of two, three or more monomers containing an acid group. It is of particular interest to have a weight % to 10% by weight, preferably 0.5% to 8% by weight, and more preferably 1% to 5% by weight, based on the total weight of the (meth)acrylic polymer. % of a (meth)acrylic polymer derived from a unit derived from an acid group-containing monomer. Another class of co-monomers are (meth) acrylates having at least 13 carbon atoms in the alkyl group and derived from saturated alcohols, such as 2-methyldodecyl (meth)acrylate, (meth)acrylic acid. Tridecyl ester, 5-methyltridecyl (meth)acrylate, tetradecyl (meth)acrylate, pentadecyl (meth)acrylate, cetyl (meth)acrylate, (A) 2-methylhexadecane acrylate, heptadecyl (meth) acrylate, 5-isopropylheptadecane (meth) acrylate, 4-tert-butyl octa(meth) acrylate Alkyl ester, 5-ethyl octadecyl (meth) acrylate, 3-isopropyl octadecyl (meth) acrylate, octadecyl (meth) acrylate, hexadecane (meth) acrylate Ester, eicosanyl (meth)acrylate, cetyl eicosyl (meth)acrylate, (methyl) -28 201105754 stearyl amdecyl acrylate, tetradecane (meth) acrylate Ester and/or eicosyltridecyl (meth)acrylate; 'cycloalkyl (meth)acrylate, such as (meth)acrylic acid 2 , 4,5-tris-tert-butyl-3-vinylcyclohexyl ester, 2,3,4,5-tetra-t-butylcyclohexyl (meth)acrylate; (meth)acrylic acid Cyclic esters such as 2-(1-imidazolyl)ethyl (meth)acrylate, 2-(4-morpholinyl)ethyl (meth)acrylate, 1-(2-methylpropenyloxy) (meth)-2-pyrrolidone; nitriles of (meth)acrylic acid and other nitrogen-containing methacrylates, such as N-(methacryloxyethyl)diisobutyl ketone imine, N- (methacryloxyethyl)di-hexadecyl ketimine, methacryl fluorenyl amide acetonitrile, 2-methyl propylene methoxyethyl methyl cyanamide, cyano cyanoacrylate Esters: aryl (meth)acrylates, such as benzyl (meth)acrylate or phenyl (meth)acrylate, each aryl group may be unsubstituted or substituted up to four times; Θ (meth)acrylic acid a polyalkoxy derivative, especially a polypropylene glycol mono(meth)acrylate having 2 to 10, preferably 3 to 6 propylene oxide units (preferably a polypropylene glycol having about 5 propylene oxide units) Monomethacrylate (PPM5)), 2 to 10, preferably 3 to 6 ethylene oxide units of polyethylene glycol mono(meth)acrylate (preferably polyethylene glycol monomethyl group having about 5 ethylene oxide units) Acrylate (PEM5)), polybutylene glycol mono(meth)acrylate, polyethylene glycol polypropylene glycol mono(meth)acrylate; (meth)acrylamide, especially N-hydroxymethyl (A) Acrylamide, -29- 201105754 N,N-dimethylaminopropyl (meth) acrylamide, butyl butyl methacrylate, methacrylamide and acrylamide And (meth) acrylate derived from saturated fatty acid or fatty acid decylamine, such as (meth) propylene oxime 2-hydroxypropyl-palmitate, (meth) propylene oxime. oxy-2 -Hydroxypropyl-stearate and (meth)acryloxy-2-hydroxypropyl-laurate, pentadecyloxy-2-ethyl-(meth) acrylamide, ten Heptadecyloxy-2-ethyl-(meth) acrylamide, (meth) propylene oxime-2-ethyl-laurylamine, (meth) propylene oxime-2-ethyl - myristyl, (meth) propylene Oxy-2-ethyl-palmitoleamine, (meth)propenyloxy-2-ethyl-stearylamine, (meth)acryloxy-2-propyl-lauric acid, ( Methyl)propenyloxy-2-propyl-myristylamine, (meth)acryloxy-2-propyl-palmitoleamine and (meth)acryloxy-2-propyl- Stearylamine. The co-monomer further includes a vinyl ester such as vinyl acetate, vinyl chloride-, vinyl versatate, ethyl-ethyl acetate, ethylene-vinyl chloride; maleic acid derivatives such as cis Butic anhydride, maleic acid ester (such as dimethyl maleate), methyl maleic anhydride oxime; and fumaric acid derivative, such as dimethyl fumarate . Another group of comonomers are styrene monomers (such as styrene), substituted styrenes having alkyl substituents in the side chain (such as alpha-methyl styrene and alpha-ethyl styrene), Substituted styrenes having an alkyl substituent on the ring (such as vinyl toluene and p-methylstyrene) and halogenated styrene (such as monochlorostyrene, dichlorostyrene, tribromostyrene, and tetrabromostyrene) ). 'Heterocyclic vinyl compound' such as 2-vinylpyridine, 3-vinylpyridine, 2-methyl-5-vinylpyridine, 3-ethyl-4-vinylpyridine, 2,3-di-30 201105754 methyl_5_vinylpyridine, vinylpyrimidine, vinylpiperidine, 9-vinylcarbazole, 3-vinylcarbazole, 4-vinylcarbazole, 1-vinylimidazole, 2-methyl -Tetraimidazole, N-vinylpyrrolidone, 2-vinylpyrrolidone ketone 'N-vinylpyrrolidine, 3-vinylpyrrolidine, N-vinylcaprolactam, N-ethylpyramine Endo-amine, B. vinyi〇x〇iane, Ethylfuran, Vinylthiophene-thiol thiolane, Vinylthiazole and Hydrogenated Vinthiazole, Vinylcarbazole and Hydrogenation Vinyl carbazole; 顺 maleimide, methyl maleimide; vinyl ether and isobutyl ether: and vinyl halides such as vinyl chloride, vinyl fluoride, vinylidene chloride and partial Difluoroethylene represents an example of more co-monomers. In a particular modification of the invention, the (meth)acrylic polymer may have a weight % to 60% by weight, more preferably 5% to 50% by weight based on the total weight of the (meth)acrylic polymer % by weight, and most preferably from 1% by weight to 40% by weight of styrene monomer, more particularly from styrene, substituted styrene having an alkyl substituent in the side chain, having an alkyl group on the ring ^ A substituted styrene and/or halogenated styrene derived unit of a substituent. Preference is given to preparing a (meth)acrylic polymer having a very small fraction of two or more carbon-carbon double bonds (having the same reactivity as the (meth)acryl fluorenyl group) with a monomer mixture (meth) acrylate. In a particular modification of the invention, the fraction of the compound having two or more (meth)acrylinyl groups is preferably limited to not more than 5% by weight based on the total weight of the monomers, more particularly not exceeding 2% by weight, particularly preferably not more than 1% by weight 'more preferably not more than 5% by weight, and most preferably not more than 0.1% by weight. -31 - 201105754 The molecular weight of the (meth)acrylic polymer used in accordance with the present invention can be adapted to a wide range. Generally, the weight average molecular weight is typically at least 1 000 grams per mole, preferably at least 2000 grams per mole, and most preferably at least 5000 grams per mole. In the first aspect of the invention, for example, a (meth) propionic acid-based polymer having a relatively high molecular weight can be used. The (meth)acrylic polymers can be obtained in particular by emulsion polymerization, and the (meth)acrylic polymers can have, for example, in the range of, for example, from 1 Torr to 10,000,000 g/mole. More preferably, it has a weight average molecular weight in the range of from 200,000 to 500,000 g/mole. In another aspect of the invention, a (meth)acrylic polymer having a low molecular weight can also be used. The (meth)acrylic polymers may exhibit, for example, in the range of from 1000 to 150,000 g/mole, more particularly from 4000 to 100,000 g/mole, optimally in the range of from 5,000 to 50,000 g/mole. The weight average molecular weight inside. The number average molecular weight of the preferred (meth)acrylic polymer is in the range of from 1,000 to 10,000 g/m, more preferably from 1,500 to 50,000 g/m. Also of particular interest are (meth)acrylic polymers having a polydispersity index M W/Mn in the range from 1 to 5, more preferably in the range from 2 to 3. The molecular weight can be determined by means of gel permeation chromatography (GPC) relative to the PMMA standard. In a particular aspect of the invention, the (meth)acrylic polymer can have a molecular weight distribution of at least 2 maximal enthalpy, as measured by gel permeation chromatography.

The glass transition temperature of the (meth)acrylic polymer is preferably in the range of from 20 ° C to 32 to 201105754 to 90 ° C, more preferably in the range of from 25 to 80 ° C, and most preferably from 30 Up to 80 °C. The glass transition temperature can be affected by the nature and proportion of the monomers used to prepare the (meth)acrylic polymer. (Methyl) • The glass transition temperature Tg of the acrylic polymer can be determined in a known manner by differential scanning calorimetry (DSC), more particularly in accordance with DIN EN ISO 1 1 3 5 7 . The glass transition temperature can be preferentially determined as the midpoint of the glass phase of the second heating curve at a heating rate of 10 〇c per minute. Further, the glass transition temperature Tg can also be preliminarily calculated by the above-mentioned Fox equation. Preferably, the iodonium of the (meth)acrylic polymer is in the range of from 1 to 300 grams of iodine per 1 gram of polymer, preferably from 2 to 250 grams per 100 grams of polymer. More preferably, it is from 5 to 100 grams of iodine per 100 grams of polymer, and most preferably from 10 to 50 grams of iodine η 00 grams of polymer, as measured in accordance with DIN 53241-1. The oxindole of the polymer may preferably be in the range of from 3 to 300 mgKOH/g, more preferably from 20 to 200 mgKOH/g, and most preferably in the range of from 40 to 150 mgKOH/g. Hydroxyl hydrazine can be determined in accordance with DIN EN ISO 4629. The (meth)acrylic polymer used in accordance with the present invention can be obtained, in particular, by solution polymerization, bulk polymerization or emulsion polymerization, and a surprising advantage can be achieved by free radical polymerization. These polymerizations are described in the 6th edition of Ullmann, s Encyclopedia of Industrial Chemistry. 'As with conventional free radical polymerization methods, related methods of controlled free radical polymerization, such as ATRP (=Atom Transfer Radical Polymerization), NMP (Nitrogen Oxide Mediated Polymerization) or raft (also used) = Reversible -33 - 201105754 Formula Addition Fragmentation Chain Transfer) to prepare polymers. Typical free radical polymerizations are set forth in the references including the sixth edition of Ullmann's E n c y c 1 〇 p e d i a 〇 f I n d u s t r i a 1 C h e m i s t r y . In general, it is carried out by using a polymerization initiator and, if necessary, a molecular weight adjusting agent. Initiators which may be used include, in particular, azo initiators which are widely known in the art, such as AIBN and 1,1-azobiscyclohexanecarbonitrile, and also peroxy compounds such as methyl ethyl ketone peroxide. , acetonitrile peroxide, bismuth oxide, laurel, tert-butyl 2-ethylhexanoate, ketone peroxide, tert-butyl peroctoate, methyl isobutyl ketone, peroxide Ketone, benzamidine peroxide, tert-butyl peroxybenzoate, tert-butyl peroxyisopropyl carbonate, 2,5-bis(2-ethylhexylperoxy)-2,5 - dimethyl hexane, peroxy - · tert-butyl 2-ethylhexanoate, tert-butyl peroxy-3,5,5-trimethylhexanoate, - dicumyl peroxide, 1 , 1-bis(t-butylperoxy)cyclohexane, 1,1-bis.(t-butylperoxy)-3,3,5-trimethylcyclohexane, hydrogen peroxide a mixture of cumene, tert-butyl hydroperoxide, bis(4-tert-butylcyclohexyl)peroxydicarbonate, a mixture of two or more of the foregoing compounds, and the foregoing compounds which are not specified but can be formed A mixture of free radical compounds. The initiators may be used singly or in combination. These are preferably used in an amount of from 5% by weight to 10.0% by weight, more preferably from 5% by weight to 8% by weight, based on the total weight of the monomers. It is also preferred to carry out the polymerization using a mixture of polymerization initiators having different half-lives. 'Sulphur-free molecular weight regulators include, for example, (without any intention to impose any restrictions thereon) dipolymerizable α-methylstyrene (2,4~diphenyl-4-methyl-34- 201105754 -1- Pentene), enol ether of aliphatic and/or cycloaliphatic aldehyde, terpene, β-terpinene, terpinolene, 1,4-cyclohexadiene, 1,4-dihydronaphthalene, 1 , 4,5,8-tetrahydro'naphthalene, 2,5-dihydrofuran, 2,5-dimethylfuran and/or 3,6-dihydro-2?-pyridyl, pyridine, di-polymerizable α- Methyl styrene is preferred. A mercapto compound, a dialkyl sulfide, a dialkyl disulfide and/or a diaryl sulfide can be preferably used as the sulfur-containing molecular weight regulator. By way of example, the following polymerization regulators are indicated: di-n-butyl sulphide, di-n-octyl thioether, stilbene disulfide, thiodiethylene glycol, ethyl thioethanol, diisopropyl disulfide, two n-Butyl disulfide, di-n-hexyl disulfide, di-decyl disulfide, diethanol sulfide, di-tert-butyl trisulfide and dimethyl hydrazine. Preferred compounds for use as molecular weight regulators are mercapto compounds, dialkyl sulfides, dialkyl disulfides and/or diaryl sulfides. Examples of such compounds are ethyl phthalate, 2-ethylhexyl phthalate, cysteine, 2-mercaptoethanol, 3-mercaptopropanol, 3-mercaptopropene-1,2-di Alcohol, 1,4-mercaptobutanol, thioglycolic acid, 3-mercaptopropionic acid, mercapto succinic acid, thioglycerol, thioacetic acid, thiourea and thiol (such as n-butyl mercaptan) , n-hexyl mercaptan or n-thyl-based mercaptan). Polymerization regulators which are particularly preferably used are decyl alcohol and hydrazine carboxylic acid. The molecular weight modifier is preferably from 0. 5% by weight to 1% by weight, more preferably from 0.1% by weight to 5% by weight, and most preferably from 0.5% by weight, based on the monomers used in the polymerization. An amount in the range of up to 2% by weight is used. In the polymerization, it is of course also possible to use a mixture of polymerization regulators. 'Polymerization can be carried out at atmospheric pressure, subatmospheric pressure or superatmospheric pressure. The polymerization temperature is also not important. However, in general it is tied at -20. -200 ° C ' is preferably in the range of 50 ° - 150 ° C, and more preferably in the range of 80 ° - 130 ° C. -35- 201105754 The polymerization may or may not be carried out with a solvent. The term, solvent " should be interpreted broadly herein. Preferred solvents include, in particular, aromatic hydrocarbons such as toluene, xylene; esters, especially acetates, preferably butyl acetate, ethyl acetate, propyl acetate; ketones, preferably ethyl ketone. , acetone, methyl isobutyl ketone or cyclohexanone; alcohols, especially isopropanol, n-butanol, isobutanol; ethers' especially ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol Monobutyl ether; aliphatic, preferably pentane, hexane, cycloalkane and substituted cycloalkane, such as cyclohexane; a mixture of aliphatic and/or aromatic, preferably petroleum brain; petroleum ether, biomass Diesel; and a plasticizer such as low molecular weight polypropylene glycol or phthalate. It is of particular interest to include, in particular, preferably from 40% by weight to 80% by weight, more preferably from 50% by weight to 75% by weight, of at least one having from at least one double bond and from 8 to 40 carbon atoms in the alkyl group. A coating composition of a (meth)acrylic polymer of a unit derived from a (meth)acrylic monomer. - In a particular aspect of the invention, the weight ratio of reactive diluent to (meth)acrylic polymer may range from 10:90 to 90:10, more preferably from 20:80 to 40: Within the scope of 60. The coating composition of the present invention can be crosslinked, in particular, by a crosslinking agent capable of reacting with a hydroxyl group of a (meth)acrylic polymer used in accordance with the present invention. The polymer of the present invention having a hydroxyl group can be crosslinked using, for example, a compound having two or more N-hydroxymethylguanamine groups such as a polymer having a repeating unit derived from N-methylolmethacrylamide. . Usually at least 1 〇〇. Preferably, a temperature of at least 120 ° C is used for crosslinking. Further, the polymer of the present invention having a hydroxyl group may use a polyanhydride such as bis-36-201105754 anhydride, such as, in particular, pyromellitic dianhydride, or a polymer having two or more units derived from maleic anhydride. Cross-linking. Crosslinking with polyanhydride preferably occurs at an elevated temperature of, for example, at least 100 ° C, preferably at least 10 ° C. • Crosslinking of another class of crosslinkers to melamine or urea derivatives and melamine or urea derivatives preferably occurs at elevated temperatures of, for example, at least 1001, preferably at least 1 20 °C. Preferred crosslinking agents include, in particular, polyisocyanates or compounds which produce polyisocyanate. The polyisocyanate is a compound having at least 2 isocyanate groups. The polyisocyanates which can be used in accordance with the invention may comprise any desired aromatic 'aliphatic, cycloaliphatic and/or (cyclo)aliphatic polyisocyanates. Preferred aromatic polyisocyanates include 1,3- and 1,4-phenylenediesters of diisocyanate, 1,5-naphthalene diisocyanate, toluidine diisocyanate, diisocyanate 2,6-toluene diester, 2,4-toluene diisocyanate (2,4-TDI), 2,4'-diphenylmethane diisocyanate (2,4,-MDI), 4,4' - a mixture of diphenylmethane diisocyanate oxime, monomeric diphenylmethane diisocyanate (MDI) and oligomeric diphenylmethane diisocyanate (polymeric MDI), ditolyl diisocyanate, diisocyanate Tetramethylxyl ester and triisocyanatotoluene. Preferred aliphatic polyisocyanates have from 3 to 16 carbon atoms, preferably from 4 to 12 carbon atoms in a straight or branched alkylene group, and are suitable cycloaliphatic or (cyclo)aliphatic The isocyanate preferably has 4 to 18 carbon atoms, preferably 6 to 15 carbon atoms in the cycloalkyl group. It is well known to those skilled in the art from (cyclo)aliphatic diisocyanates to understand both NCO groups which are attached in a cyclic and aliphatic manner, as in, for example, isophorone diisocyanate. Conversely, 'cycloaliphatic-37-201105754 diisocyanate is considered to be those containing NCO groups which are only directly attached to the cycloaliphatic ring, such as H12MDI. Examples are cyclohexane diisocyanate, methylcyclohexane diisocyanate, ethylcyclohexane diisocyanate, propylcyclohexane diisocyanate, methyl diethylcyclohexane diisocyanate, propane diisocyanate, butane two Isocyanate, pentane diisocyanate, hexane diisocyanate, heptane diisocyanate, octane diisocyanate, decane diisocyanate, decane triisocyanate (such as 4-isocyanatomethyl-1,8-octane diisocyanate (TIN)), decane diisocyanate and triisocyanate, undecane diisocyanate and triisocyanate, and dodecane diisocyanate and triisocyanate. Preferred are isophorone diisocyanate (IP DI), hexamethylene diisocyanate (HDI), diisocyanatodicyclohexylmethane (H12MDI), 2-methylpentane diisocyanate (MPDI), 2, 2 4_trimethylhexamethylene diisocyanate/2,4,4-trimethylhexamethylene diiso(TMDI), norbornane diisocyanate (NBDI). Especially preferred to use IPDI, HDI, TMDI and H12MDI, isocyanurate can also be used. Also suitable are 4-methylcyclohexane 1,3-diisocyanate, 2-butyl-2-ethylpentamethylene diisocyanate, isocyanate 3(4)-isocyanatomethyl-1- Methylcyclohexyl ester, 2-isocyanatopropyl cyclohexyl isocyanate, 2,4'-methyl-bis(cyclohexyl) diisocyanate, 1,4-diisocyanato group -4-methylpentane. Preferred aliphatic, cycloaliphatic and araliphatic (i.e., aryl substituted aliphatic) monoisocyanates are described, for example, in Houben-Weyl, Methoden der organischen Chemie, Volume 14/2, pages 61-70 and W Siefken, Justus Liebigs Annalen der Chemie 562, 7 5- 1 3 6 201105754. It is of course also possible to use mixtures of polyisocyanates. In addition, it is preferred to use an oligo isocyanate or a polyisocyanate, which can be utilized by using urethane, urea, urea, biuret, uretdione, decylamine, isocyanurate, carbon. The diimine, uretonimine, indoletrione or imidoquinone trione structure is bonded and prepared from the diisocyanate or polyisocyanate or a mixture thereof. This preferred class of polyisocyanurate esters is prepared by simple diisomerization, tripolymerization, ureaformation, biuretization, and/or urethane ation of a diisocyanate and has more than one molecule per molecule. Examples of compounds of two isocyanates are the reaction of such simple diisocyanates (such as IPDI, TMDI, HDI and/or H12MDI) with polyols (for example, ', glycerol, trimethylolpropane, pentaerythritol) or polyfunctional polyamines. - a product, or a triisocyanurate obtained by a tertiary polymerization of a simple diisocyanate such as IPDI 'HDI and Hi 2 MDI. Therefore, it is particularly advantageous to contain a coating composition preferably having a crosslinking agent of 0.5% by weight to 10% by weight, more preferably 2% by weight to 7% by weight. When a polyisocyanate is used as a crosslinking agent, the reaction of the (meth)acrylic polymer with the organic polyisocyanate may in this case be 0.5 to 1.1 NCO groups per hydroxy group depending on the intended use of the reaction product. get on. The reaction is preferably carried out such that the amount of the organic polyisocyanate based on the total hydroxyl group content of the components present in the reaction mixture is present in an amount of from 0.7 to 1.0 isocyanate groups per hydroxy group. The coating composition of the present invention does not require any desiccant, although the desiccant may be present in the composition as a free component. Such desiccants include, in particular, -39-201105754 organometallic compounds, examples of which are metals such as transition metals (such as cobalt, bell, lead, zirconium, iron, cerium), alkali metals or alkaline earth metals (such as lithium, potassium and calcium). soap. Examples which may be mentioned include cobalt naphthalate and cobalt acetate. The desiccant may be used singly or as a mixture, and particularly preferably a mixture comprising a cobalt salt, a zirconium salt and a lithium salt. The proportion of the desiccant in the preferred coating composition may preferably range from more than 0% by weight to 5% by weight, more preferably from more than 3% by weight to 3% by weight, based on the weight of the polymer. Within the range and most desirably in the range from greater than 〇% by weight to 0.1% by weight. The coating composition of the present invention may contain a solvent in addition to the (meth)acrylic polymer of the present invention. Preferred examples of solvents have been described above for free radical polymerization, and reference is made to such solvents. The proportion of the solvent in the preferred coating composition may particularly be in the range of from 0 to 50, more preferably from 1 to 20. The coating composition of the present invention may further comprise a conventional adjuvant and an adjuvant such as a rheology modifier, a defoaming agent 'water scavenger (water removal additive, orthoester), a getter, and a pigment wetting agent. a dispersing additive, a substrate wetting agent, a lubricant, and a flow control additive, which in each case are preferably present in an amount from 0% by weight to 3% by weight based on the total formulation, and also as a water repellent, Plasticizers, diluents (especially more reactive diluents), UV stabilizers and adhesion promoters, which in each case are preferably from 0% to 20% by weight, based on the total formulation. presence. Further, the coating composition of the present invention may be blended with conventionally used materials and pigments in an amount of up to 50% by weight based on the total composition, such as talc, carbonated fishing, -40-201105754 titanium dioxide, carbon black, and the like. The coating compositions of the present invention are characterized by a range of properties which include, inter alia, significant processing properties and excellent quality of the resulting coating. A preferred coating composition can be processed over a wide temperature window, preferably at least 20 ° C, more particularly at least 30 ° C without damaging the coating quality, which is particularly resistant. Solvent and water resistance are distinguished. Therefore, the preferred coating composition can be processed at a temperature of 15 ° C, 20 ° C, 30 ° C or 40 ° C without any substantial measurable deterioration in quality. The dynamic viscosity of the coating composition depends on the solids content and the nature of the reactive diluent and can span a wide range. In the case of high polymer content, it can total more than 20,000 millibass seconds. It is generally advantageous to have a dynamic viscosity in the range of from 1 〇 to 10000 millibass, preferably from 100 to 8000 mbar to ska seconds, and most preferably from 1,000 to 6,000 millibass. It is measured according to DIN EN ISO 2555 at 25 °C (Brookfield). Further, surprisingly good processing properties are exhibited by a coating composition having a solid content of preferably at least 50% by weight, more preferably at least 60% by weight. The coating composition of the present invention can be processed in a substantially wider temperature range than the existing coating composition in terms of a given solid content. The coating composition of the present invention has an amazingly high solid content in terms of similar processing properties, so that the coating composition of the present invention is particularly resistant to the ecological environment. Further, the present invention provides a coating for the production of the coating. A method in which the coating composition of the present invention is applied to a substrate and pre-cured. The coating compositions of the present invention can be applied by conventional coating techniques such as dipping, rolling, flow coating and pouring, especially diffusion, roll coating and spraying (high pressure, low pressure, no air or static electricity) ESTA)). The coating composition is cured by drying and oxidative crosslinking with atmospheric oxygen. In a particular aspect of the invention, the crosslinking can be carried out with a crosslinking agent, more particularly with a polyisocyanate. Substrates preferably having a coating composition of the invention include, inter alia, metals, especially iron and steel, zinc and galvanized copper, and plastic and concrete substrates. Furthermore, the invention provides coated articles obtainable by the process of the invention. The coating of these articles is distinguished by a significant range of properties. The preferred coatings obtained from the coating compositions of the present invention exhibit high mechanical stability. The impact hardness is preferably at least 30 seconds, more preferably at least 50 seconds, and most preferably at least 100 seconds, as measured in accordance with DIN ISO 1 522. Furthermore, the preferred coatings obtainable from the coating compositions of the present invention have surprisingly strong adhesions, as measured, inter alia, in cross-cutting tests. In particular, a 0-1 classification, more preferably 0°, can be achieved in accordance with the standard DIN EN ISO 2409. The coatings obtainable from the coating compositions of the invention generally exhibit high solvent resistance, in particular only a small portion of the solvent is coated. Dissolution in the layer. Preferred coatings are particularly resistant to polar solvents, especially alcohols (such as 2-propanol) or ketones (such as methyl ethyl ketone (MEK)), and to non-polar solvents such as diesel fuels (alkanes). ). The preferred coating according to the invention has a tilt of at least 120 seconds, preferably at least 150 seconds, in accordance with din ISO 1522 after exposure to subsequent drying (24 hours at room temperature) from 1 5 to 42 to 201105754 minutes. hardness. In addition, the coating composition of the present invention can be formulated to exhibit high acid and alkali resistance. • In addition, the preferred coating exhibits surprisingly good indentation. In a particular modification of the invention, the coating exhibits adentality of at least 4.5 mm, more preferably at least 5.0 mm, as measured according to DIN 5 3 1 56 (Erichsen). [Embodiment] The present invention is hereinafter described with reference to the examples of the present invention and comparative examples, without any intention to be construed as limiting. - Preparation of a mixture of methacryloxy-2-ethyl-fatty acid decylamine (MUMA) 206.3 grams (0.70 mole) of fatty acid methyl ester mixture, 42.8 metric grams (0.70 moles) of ethanolamine and 〇27 Metric (0.26%) LiOH was charged into a four-necked round bottom flask equipped with a sabre stirrer with a stirring sleeve and a stirring motor, a nitrogen inlet, a liquid phase thermometer and a distillation bridge. The fatty acid methyl ester mixture comprises 6% by weight of saturated Ct 2 to C i 6 fatty acid methyl ester, 2.5% by weight of saturated C17 to C2 〇 fatty acid methyl ester, 52% by weight of monounsaturated C18 fatty acid methyl ester, 1.5% by weight Monounsaturated C2G to C24 fatty acid methyl ester, 36% by weight of polyunsaturated C18 fatty acid methyl ester and 2% by weight of polyunsaturated C2 oxime to C24 fatty acid methyl ester. The reaction mixture was heated to 150 ° C. 19.5 ml of methanol was removed by distillation at -43-201105754 over a period of 2 hours. The resulting reaction product contained 86.5% fatty acid ethanol decylamine. The reaction mixture obtained was processed without further purification. After cooling, 1919 grams (19.2 moles) of methyl methacrylate, 3.1 grams of LiOH, and an inhibitor mixture consisting of 500 ppm of hydroquinone monomethyl ether and 500 ppm of phenothiazine were added. The reaction apparatus was rinsed with nitrogen for 10 minutes with stirring. The reaction mixture is then heated to boiling. The methyl methacrylate/methanol azeotrope was separated and the temperature of the distillation head was then gradually increased to 100 °C. When the reaction was complete, the reaction mixture was cooled to about 70 ° C and filtered. Excess methyl methacrylate was separated on a rotary evaporator. This gave 3 70 grams of product. Inventive Example 1 30.0 g of a solvent (Solvesso 100) was charged into a reaction vessel and the initial charge was heated to 140 °C. The oxygen in the reaction vessel is removed by introducing nitrogen. Then, 17.37 grams of di-tert-butyl peroxide (DTBP), 46.64 grams of isodecyl methacrylate (IBOMA), 69.97 grams of hydroxyethyl methacrylate (HEMA)' 23.32 grams of methacrylic acid were added over a period of 4 hours. Ethylhexyl ester (EHMA), 23.32 grams of methacryloxy-2-ethyl-fatty acid decylamine (MUM A), a reaction mixture of 69.97 grams of styrene and 4.17 grams of 2-mercaptoethanol. The reaction was then stirred for 30 minutes. The mixture was then cooled to 80 °C. The reaction was carried out by adding a mixture containing 0.24 g of di-tert-butyl peroxide (DTBP) and 15 g of solvent (Solvesso 1) and then stirring at 8 °t for 2 hours. Then -44- 201105754 Stir without stirring for more than 30 minutes. The polymer content was adjusted to 65% by the addition of 18.75 grams of n-butyl acetate and 69.2 * grams of 2,7-octadienyl methyl ether. 'Investigate the properties of the resulting coating composition. For this purpose, a film of about 50 micron thickness is formed on the aluminum plate by adding polyisocyanate (hexamethylene diisocyanate, HDI, 50/60 NCO/OH) and dibutyltin dilaurate (DBTL). Crosslinked by 〇.〇1% by weight based on the weight of the polymer.硬度 The hardness and scratch resistance of the crosslinked polymer film are determined by measuring the pendulum hardness. Chemical resistance is investigated by treating the polymer film with methyl ethyl ketone. Next, the pendulum hardness of the film was measured. The criteria used herein are in particular any softening of the film due to solvent treatment. The brittleness of the film was investigated by Erichsen concave pressure test. In addition, the adhesion strength of the coating is determined by a cross-cut test. The results obtained are shown in Table 1. 〇 Comparative Example 1 50.01 g of a solvent (Solvesso 100) was charged into a reaction vessel and the initial charge was heated to 140 °C. The oxygen in the reaction vessel is removed by introducing nitrogen. Then, 1 5 · 3 3 g of di-tert-butyl peroxide (DTBP), 41.15 g of isodecyl methacrylate (IBOMA), 61.73 g of hydroxyethyl methacrylate (HEMA), 20.5 were added over a period of 4 hours. Reaction mixture of 8 grams of ethylhexyl methacrylate (EHMA), 20.58 grams of methacryloxy-2-ethyl-fatty acid decylamine (MUM A), 61.73 grams of styrene and 3.69 grams of 2-mercaptoethanol . The reaction was then stirred for 30 minutes -45 - 201105754. The mixture was then cooled to 8 °C. The reaction was carried out by adding a mixture comprising 0.21 g of di-tert-butyl peroxide (DTBP) and 15 g of solvent (S〇lvesso 100) and then stirring at 80 ° C for an additional 2 hours. Then, stirring was continued for 30 minutes or more without heating. The polymer content was adjusted to 65% by the addition of 46.16 grams of n-butyl acetate. The film system was fabricated from the resulting coating composition in accordance with the method set forth in Example 1 of the present invention. The properties of the coating obtained were determined using the study method stated above, and the results obtained are shown in Table 1. Comparative Example 2 100.02 g of a solvent (Solvesso 100) was charged into a reaction vessel and the initial feed was heated to 1 40 °C. The oxygen in the reaction vessel is removed by introducing nitrogen. Then, 30.66 grams of di-tert-butyl peroxide (DTBP), 82.31 grams of isodecyl methacrylate (IBOMA), 1 23.46 grams of methyl propionate by ethyl ester (HEMA), 82.31 were added over a period of 4 hours. ◎ grams of ethyl hexyl methacrylate (EHMA), 1 23.46 grams of styrene and 7.38 grams of 2-mercaptoethanol reaction mixture. The reaction was then stirred for 30 minutes. The mixture was then cooled to 80 °C. The reaction was carried out by adding a mixture containing 0.42 g of di-tert-butyl peroxide (DTBP) and 10 g of solvent (Solvesso 1 ) and then stirring at 80 ° C for 2 hours. Then, 40 g of a solvent (Solvesso 1 〇〇) was further added and stirring was continued for 30 minutes or more without heating. The polymer content was adjusted from -46 to 201105754 to 65% by adding 92.3 1 g of n-butyl acetate. The film system was fabricated from the resulting coating composition in accordance with the method set forth in Example 1 of the present invention. The properties of the coating obtained were determined using the study method stated above, and the results obtained are shown in Table 1.

Table 1: Properties of the coating composition investigated. Inventive Example 1 Comparative Example 1 Comparative Example 2 IBOMA [% by weight] 20 20 20 HEMA [% by weight] 30 30 30 EHMA [% by weight] 10 10 20 MUMA [ Weight %] 10 10 . Styrene [% by weight] 30 30 30 Solid content [% by weight] 65 65 65 Solvent [% by weight] 16.2 35 35 Reactive diluent [% by weight] 18.8 . Pendulum hardness [S] 189 192 186 Anti-MEK properties of pendulum hardness [s] 176 112 84 Indentation [mm] 5.1 5.4 5.3 Cross-cut [Gt] 0 0 0 The above samples show that the coating always has very good pendulum hardness, strong adhesion and relative Low brittleness (concave pressure test). The (meth)acrylic polymer containing MUMA surprisingly exhibits a slightly higher pendulum hardness, even though the number of carbon atoms in the alkyl group of the methacrylate is more than in the EHMA. Moreover, the (meth)acrylic polymer containing MUMA exhibits a markedly increased solvent resistance to polar solvents. This resistance can be increased to an astonishing extent when reactive diluents are used. -47-

Claims (1)

201105754 VII. Patent Application Range: 1. A coating composition comprising at least one (meth)acrylic polymer and at least one reactive diluent, characterized in that the reactive diluent has at least one octadiene group And the (meth)acrylic polymer has a unit derived from a (meth)acrylic monomer having at least one double bond and 8 to 4 carbon atoms in the alkyl group and derived from a hydroxyl group-containing monomer. unit. 2. The coating composition according to claim 1, wherein the reactive diluent has a molecular weight of from 140 g/m to 500 g/m. 3. The coating composition according to claim 1 or 2, wherein the reactive diluent has a boiling point of at least 1 800 〇C at atmospheric pressure (1024 mbar). 4. The coating composition according to claim 1, wherein the reactive diluent is an alcohol, an amine, an ester and/or an ether. 5. The coating composition according to claim 1, wherein the (meth)acrylic polymer has a weight average molecular weight of at least 2 000 g/mole, preferably from 4,000 to 100,000 g/mole. Within the scope. 6. The coating composition according to claim 1, wherein the (meth)acrylic polymer has iodine in a range from 5 to 100 grams of iodine per 100 grams of (meth)acrylic polymer. . The coating composition according to claim 1, wherein the (meth)acrylic polymer has oxindole in a range of from 3 to 300 mgKOH/g. The coating composition according to claim 1, wherein the (A-48-201105754-based) acrylic acid polymer has from 1% by weight to 20% by weight, and has at least one double in the alkyl group. A unit derived from a bond and a (meth)acrylic 'monomer' having 8 to 40 carbon atoms. The coating composition according to the first aspect of the invention, wherein the (meth)acrylic acid polymer comprises from i% by weight to 70% by weight of the unit derived from the hydroxyl group-containing monomer. 10. The coating composition according to claim 1, wherein the ((meth)acrylic polymer comprises from 5 to 95% by weight of from 1 to 12 carbon atoms in the alkyl group (A) A unit derived from an acrylate having no double or hetero atom in the alkyl group. 11. The coating composition of claim 1, wherein the 'coating composition comprises a crosslinking agent. The coating composition according to item 11 of the patent application, wherein the crosslinking agent comprises or releases a polyisocyanate. The coating composition according to the first aspect of the invention, wherein the ruthenium coating composition comprises from 5% by weight to 30% by weight of a reactive diluent. 14. The coating composition of claim 1, wherein the coating composition comprises a desiccant. 15. The coating composition of claim 14, wherein the coating composition comprises from 1% to 20% by weight of a solvent. A method of producing a coating characterized by coating a coating composition according to any one of the first to fifth aspects of the application of the patent application to a substrate and pre-curing. 17. The method of claim 16, wherein the substrate is a -49-201105754 metal substrate. 1 8 . A coated article obtainable by the method of claim 16 or 17. -50- 201105754 IV. Designated representative: (1) The representative representative of the case is: None. (2) A brief description of the symbol of the representative figure: none 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: no ❹ -3-