DE2032383A1 - Acrylic copolymers and coating compositions containing them - Google Patents

Description

The invention relates to new * acrylic polymers * and to new acrylic coatings of the type generally is referred to as acrylic varnishes. In particular, relates the invention to copolymers of methyl methacrylate and Glycidyl acrylate or methacrylate which by reaction modified with aliphatic acids and applied to coating compounds / which contain these modified copolymers.

Polymethyl methacrylate is used because of its special resistance widely used as a coating material against long-term outdoor exposure. Because of this quality, polyethylene methacrylate paints have proven to be special

009884/2100

valuable for the surface treatment of automobile bodies

and other metallic objects that are exposed frequently and for longer periods outdoors proven "Such coatings, however, a serious limitation subject insofar as si · not respond well to conventional primer coatings selchen '■ stick" which Ia generally below Alkydharzemaillien, amino aldehyde resin enamels and nitrocellulose lacquers are used

ψ - -, .--. "■ _ ■ - ■ .. den. Accordingly, if it is desired, it is necessary to apply a polymethylroethacrylate lacquer to a substrate which has previously been coated with a conventional primer lacquer, an intermediate coat of a Laying varnish to be applied between the primer coat and the upper overlay made of polyethylene.

The object of the invention is essentially the sheep "' fung of a new type of a film-forming acrylic polymer and a coating composition containing this, which has a ' good adhesion to common primers as well as a has good durability and a high permanent gloss when exposed outdoors.

Another object of the invention is the need avoid the application of an intermediate coat from a sealing jacket in the above circumstances. ■. · ■

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• t

The solution to this problem is described in detail below.

The new type of acrylic polymer according to the invention Generally speaking, it is the reaction product of (1) a copolymer of essentially methyl methacrylate and Glycidyl acrylate or methacrylate and (2) an aliphatic monocarboxylic acid. ·

The term "interpolymer of essentially Methyl methacrylate and glycidyl acrylate or methacrylate "as used in the present context means a mixed polymer consisting essentially of at least 75 parts by weight of methyl methacrylate and 0.5 to 25 parts by weight Glycidyl acrylate or methacrylate is derived, the total parts being 100. The mixed polymer can except the absolutely necessary monomer components mentioned contain proportions of other copolymerizable, ethylenically unsaturated monomers which do not react with the glyidyl methacrylate component. These mixed polymerizable monomers include, for example, the alkyl esters of acrylic acid and methacrylic acid, vinyl acetate, acrylonitrile and styrene. Preferred interpolymers are those composed of the ■ monomers methyl methacrylate and glycldyl acrylate or methacrylate in a weight ratio of 90 to 99:10 to 1 are derived, and it is particularly preferred that

00988W210Q

si of the monomers mentioned in a weight ratio

nis are derived from 95tS.

The acrylic polymers according to the invention are preferably prepared by first forming a copolymer / which is proportions of methyl methacrylate and Glycidyl acrylate or methacrylate in the proportions defined above and, if desired, a smaller amount of Contains proportions of a copolymerizable monomer and that the resulting copolymer is then esterified with an aliphatic monocarboxylic acid.

The interpolymer can be prepared by any of the known polymerization methods, namely by Granular, emulsion or solution polymerization of the mixed monomers. A preferred method of making the Mixed polymers consists in the fact that a suitable proportion of the mixed monomers together with a solvent, which can be a solvent both for the monomers and for the mixed polymer, and with a catalyst, such as one of the known organic peroxide catalysts, e.g. Bentoyl peroxide, introduced into a reaction vessel in which the mixture is heated with continuous stirring for a period of at least two hours, followed by cooling will. The interpolymer is in the form of a solution with about

009884/2100

501 solids obtained.

The interpolymer is then by any esterified suitable method. According to a preferred method, the 50% solution of the mixture obtained as above is polymer slightly diluted and reflux in the reaction vessel brought. Then an aliphatic monocarboxylic acid in In the form of a solution with a catalyst added and the Allow the reaction to proceed until the desired degree of esterification has been achieved. . ·

The resulting ester bond is of the type as it is generated by reacting a carboxyl group with an epoxy group in which the epoxy ring is opened not only for! creation of an ester bond on a carbon * material atom leads, but also to the generation of a hydroxyl, group on the adjacent carbon atom.

Es.ist every aliphatic monocarboxylic acid for ver j esterification, be it not substituted or preferred » wisely substituted with at least one polar group other than the hydroxyl group.

Typical polar groups and their approximate dipole moments are:

009884/2100

Dipolrooroent;

-ie ' (10 electrostatic unit)

4,5 -HR ₃ ⁺ , -SO ₃ ", -COO !, Betaine -R ₃ N ⁺ CK ₂ CO ₂ 4,0 -CN-, -NC, -RN« CO, -SN-CS, -

3.0 -COCl ₂ , -NO

Sulfones R sulfoxides

R R

Nitrites, nitrates, amine oxides, -

2.8 -Ketones -CR,
IS
O -C-II
H
O Oximes -C-NOH 2.5 -SO ₂ NH ₂ , -CF ₃ , - ^CC1 3 2.0
* -SO ₃ H, -COOR 1 * 5 halogen , -NHCOR 1.3 ^: -0R, -SR -MH ₂ , -NHR, -NR i ₂

CHCl ₂ , -

R denotes an alkyl or aryl group.

This list gives numerical values without reference to the direction.

Suitable acids include, for example, lauric acid, 4-aminobutyric acid, ll-antinoundecanoic acid * pyruvine * • acid and dimethoxyphenylacetic acid. Particularly preferred

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• ind the aliphatic monocarbonic acids which have an amino group as a sub-substituent.

As mentioned, the invention also includes a new one Type of coating compositions composed of the esterified copolymer described above.

The coating compositions according to the invention contain an organic solvent and as essential film-forming materials (1) at least 40 parts by weight of an acrylic polymer, consisting of (a) Mlschpolneren of essentially at least 75 parts by weight of methyl methacrylate and 0.5 to 25 parts by weight of glycidyl acrylate or methacrylate, where the. Total parts of the mixed polymer components -100 are μήά dl "mixed polymers are esterified with an aliphatic monocarboxylic acid, which is either unsubstituted or substituted with at least one polar group other than the hydroxyl groups, or (b) mixtures of the esterified mixed polymers" with homopolymers * made from methyl methacrylate or Old copolymers of methyl methacrylate and an ethylenically unsaturated monomer, which can be copolymerized with it and is inert to the esterified glycidyl content of the esterified copolymer; (2) up to 50 parts by weight of at least one compatible plasticizer and (3) up to 35 parts by weight of cellulose acetotbutyrate, the total parts by weight of the film-forming materials being 100 and also the glycicylacryate or

009884/2100

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«41 V> ♦ · · β -O αφ

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2632303

-methacrylate content of each copolymer Ca) ver tion makes up about 0.5 to about 25 wt .-% of the constituent of essential film-forming materials, "the essential feature of the paints or coating compositions of the invention is that the acrylic polymer, which © in © s the essential film-forming materials ä®x mass forms, must keep the esterified copolymers described above, and indeed in such a tateilen, ä <UEB dosaes promoting proportion d.lu "the GifcidylaeEylat- © & ®S crylatanteil before esterification about 0.5 to © tt-y® 2 %% _ff b © · = moved to the total weight of the® polymer t & sl as a ^ ssiaehfeo It has proven to be not essential? % mh% alo 25% by weight of glycidyl acrylate eäer -si @ feSiaesyl®t In ύλ <& polyroerkomponßte · the fllsibildesiöen Mafenrialisa remain, because it shines! © in another ¥ © g part. Yes, most of them

preferably about I to about

'or' methacrylate content

The copolymers from Methylmethaeryiafep ^ © iehü In mixing with the esterified "Mischpolyaeren, those copolymers are made. lat and ethylenically unsaturated monomers, which are essentially inert towards the esterified glyeidyl moiety of the esterified copolymer, examples of bi monomers are the acyl esters of acrylic acid and methacrylic acid,

Vinyl acetate, acrylonitrile and styrene.

The average viscosity molecular weight " of the film-forming polymeric acrylic material (including both the esterified copolymer and the methyl methacrylate homo- or copolymers) should be in the range of 40,000 to 150,000 and, in the case of automotive paints, preferably between 75,000 and 100,000 * By use of a forming polymer in these areas and especially in the latter it is possible to use sprayable paints to produce with a high solids content, for example paints having a non-volatile solids concentration of from about 12 to about 20 weight percent.

The lacquers can contain one or more plasticizers in an amount of up to 50% by weight, preferably 20 to 40% by weight Contain% by weight of the film-forming materials. In general, those for use in the coating compositions are Plasticizers suitable for the invention are those which are compatible, i.e. not, with the other film-forming materials react with or significantly separate from the other film-forming materials of the composite coatings. A preferred plasticizer is an oil-free one Polyester, which is particularly compatible with acrylic polymers and has a very low tendency to separate from acrylic polymers. The oil-free polyester, the duxh

00988472100

Implementation of Ncopontyiglycol, adipic acid, phthalic anhydride and butyl glycol in a pick ratio of 3: 2: 2: 2 each. known methods is obtained. The preferred Alkyd resins have an oil length (chain length) of 15 to 55% as a precaution 20 to 35 and 1 to 6%, preferably 3 to 5t unused hydroxyl groups .. Another preferred one AlkyciJha & rs is one which is made with coconut oil is modified.

other suitable plasticizers are benzyl butyl phthalate, diboty phthalate, triphenyl phosphate, 2-ethylhexylbeneyl phthalate and dicyeiohexyl phthalate. Each. specially used © Plasticizers or their amount are selected depending on the need for compatibility and other film-forming properties.

The paints of the invention can also be up to 35, preferably 10 to 25 part by weight «cellulose acetate butyrate, based on 'the weight of the film-forming materials' keep. 'd * s cellulose acetate butyrate can be any of the Materials with lacquer quality, which are usually in * the coating clinic. . ' ,

To prepare the paints, the fiIn-forming materials are dissolved in an organic solvent, which can be any of the known organic solvents,

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which are normally used in paint technology. Suitable solvents are, for example, toluene, xylenes, Acetone, methyl thy! Ketone, methyl isobutyl ketone, methyl isopropyl ketone, amyl alcohol, methyl thyroid chloride, cyclohexanone and aromatic hydrocarbon mixtures. While certain of these solvents for lack of solvent power One or more of the film-forming materials cannot be used alone, they can be mixed with used by others *

While a clear varnish can be applied for certain purposes, it is common practice to include pigments in it. Examples of pigments are metal oxides, hydroxides, Chromates, silicates, sulfides, sulfates, carbonates and soot, organic dyes and lacquers made therefrom, as well as metal flake pigments.

The surfactants of the invention may also contain any of the additives commonly used in known paints such as dispersants, flow control agents, and the like.

The paints of the invention have the very important one The advantage that they can be applied directly and very well on conventional metal protection and rust-inhibiting agents. Primer coatings adhere to which methyl methacrylate paints

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'of the known type typically do not adhere appreciably. do Metal primers on which the paints of the invention can be applied, include, for example, 'mittxocknenden oil modified alkyd resin ©, modified with rosin Alkyd resins, mixtures of alkyd and aminoplast resins » zen, Gemiseh from alkyd and epoxy harps, G @ misctte from Alkyd »s> Aminoplast and epoxy resins ^ mixtures of epoxy esters. higher fatty acids and amino resins and the like.

The paints can be applied to primed substrates by any of the known techniques, including spraying, brushing, dipping, coating, etc. ., etc. "The coating is then baked about the be at Aet .Approximately temperature of 93.3 ° C to about 149 ° C (200 ° to 30O ⁰ FJ © .. The higher the baking temperature is, the shorter the drying time . '

The invention is explained in more detail by the following examples: in which all parts are tezofen by weight, unless otherwise stated.

example 1

A mixed polymer of methylirethacrylate and GIyei » dyl methacrylate in the ratio 05/5 was made by polymerization of the following mixture:

'0098®4 / 210i ·.'. ■

ORtGiNAL INSPECTED

Parts

Methyl methacrylate. 1520 Glycidyl methacrylate 86

Toluene 1120 methyl! Sobuty! Ketone>, 480

Benzoyl peroxide 11.6

In this way a solution was produced containing about 50% by weight of the interpolymer.

The solution was reduced to a solids content of 35% diluted with methyl isobutyl ketone and then esterified by the following mixture was refluxed for 7.5 hours:

Parts

Mixed polymer solution (35%) 286 Nitrobenzene 47 Lauric acid 7th Whore ethyl-tert-amine 1

There was prepared a paint containing rat * the resulting esterified copolymers, Celluloseacetatbuty, with coconut oil modified alkyd resin, polymethyl methacrylate, and · "in pigment in a weight ^ratio of about 35.3: 21.9: 32.8: 4.2 * 1.8.

This lacquer was applied to a primed steel surface to which conventional lacquers do not adhere well

and then baked for 30 minutes at I49 ° C (300 ⁰ F),

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whereby a film with very good adhesion was sucked onto the primed steel surface.

Example 2

It became a mixed polymer of methyl methacrylate and glycidyl methacrylate in a ratio of 95/5 in a solution with 35% solids ^ obtained v / ie in Example 1, esterified with 4-aminobutyric acid by adding the following mixture 8.25 Refluxed for hours: '

Parts

Mixed polymer solution (35t) 286

4- * Ainobutyric acid 3.62

Formamide 30

Methyl isobutyl ketone 24.5 Dimethyl-tert-amine 1,5

The resulting esterified interpolymers became a varnish, corresponding to that described in example 1 "apart from you de" replacement of the esterified copolymer,

• -

set up.

. If; the paint is applied as in example i and

i '

was fired, it produced a film with very good adhesion on your own primer coat.

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Beliplel 3

A mixed polymer of methyl methacrylate and glycidyl methacrylate (95/5) in a solution with 35% solids, obtained as in Example 1, was with 11-Aminoundecynsltare esterified by the mixture below for 8.5 hours was held at reflux.

Parts

Mixed polymer solution (351) 286 ii-aminoundecanoic acid 7.1

Formamide 50

Acetone 10

Dimethyl-tert-amine 1,5 '

The resulting esterified copolymer was tu a varnish similar to that described in Example 1, apart from the nature of the esterified copolymer, set up.

When the paint is on a primed steel surface was applied as in Example 1 and stoved onto it, a dried film was formed which adheres very well to the Primer coating adhered.

Example 4

A mixed polymer of methyl methacrylate and glycldyl methacrylate (98/2) was polymerized

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standing mixture produced:

Parts

Methyl methacrylate 1176 Glycidyl methacrylate 24

Toluene 840

Methyl isobutyl ketone 360 Benzoy! Peroxide 11.3

"In this way a® solution was created> containing about 50 wt. «t of the copolymer.

The solution was reduced to a solids content of 40% diluted with methyl isobutyl ketone and esterified with pyruvic acid by the following mixture for 4 hours Was held at reflux:

Mixed polymer solution W%) 375.0 Methyl isobutyl ketone 52.5

* Diraethy1-tert-amine 1.5

Pyruvic acid l »@ €

Toluene 1.00

A lacquer was produced "containing the resulting esterified copolymer, cellulose acetate butyrate" (Sl-free polyester and a pigment in weight ratio the solids of about 52.3: 21/5: 23.8: 2.4.

When this paint is on a primed steel surface

009884/2106

2032313

- 17 -

was applied on which usual paints haiten not good, and 30 Hinuten long it (F ⁰ 310) was baked at 154 ° C, a film was made with very good adhesion to the primed steel surface.

Example 5

A mixed polymer of methyl methacrylate and glycidyl methacrylate (99/1) was prepared by polymerizing the following mixture:

• Parts

Methyl methacrylate 1584 'glycidyl methacrylate 16

Toluene. 1120 methyl isobutyl ketone 480

Benzoyl peroxide 11.6

In this way a solution was produced containing about 50% by weight of the interpolymer.

The solution was to a solids content of 40t diluted with methyl isobutyl ketone and esterified with 4-aminobutyric acid by using the following mixture for 9 hours

was held at reflux »·

009Θ8Α / 2Ί00

2032363

Parts

Mixed polymer (401) 250

4-faninobutyric acid 0.73

Formamide 5

Methyl isobutyl ketone 31 Dimethyl test * *> ω & 1η 1.5

The resulting® esterified copolymer became a lacquer, produced according to the geraä® example!, apart from the Srs & ta of the breathed'mischpolymeren.

When the paint is on a primed steel surface as applied and baked in Example I gave • r a dried filra with much improved adhesion in comparison with films made from conventional paints.

Example 6

A mixed polynage® au® methylraethacrylate and glyci * dyl methacrylate (90/10) tnsrd produced by polymerizing the following mixture:

Parts

lie thy litte theory] & t '45.0

Glycidyl methacrylate 5.0

Toluo)! 34.9

Methv msobutyl ketone 14.9 Benxoyjl peroxide 6.36

009894/2100

-19 - ■■■■■■ '

The neck was poured into a solution containing about 50% by weight of the mixed polymer,

The Lusung was applied to a Feet · toffgehalt of 401 old diluted Methyliftobutylketon and pyruvic acid esterified ver t Were you by the following mixture maintained leg Rücktlufl 7 hours

Molten polymer solution (401) 375.0 Methyl isobutyl ketone 52.5 Dimethyl tertiary amine 2.0 Pyruvic acid 9.3

Toluene 1 »0

A varnish was prepared containing the resulting esterified copolymer, cellulose acetate butyrate, benxyl butyl phthalate, polymethyl methacrylate and a Pigment in a weight ratio of the solids of about 5.1-21.5: 23.8-43.2: 2.4.

If this varnish was applied to a primed steel surface, common varnishes do not work well and baked for 30 minutes at 154 ° C (310 ° F) resulted in a film with particularly good adhesion to the primed steel surface.

009884/2100

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• β α ο *

Example ©! ,,,?

I. " ■■» "!» "■■""ι · ™ '■"".

A mixed polymer of methyl methacrylate and glycidyl methacrylate (75/25) was made by polymerizing the according to " standing mixture produced:

Parts

"Methyl methacrylate 1200

'Glycidyl methacrylate 400

Toluene 1120

Methyl isobutyl ketone 480 Benzoyl Peroxide 11.6

In this way a solution was produced containing about 50% by weight of the interpolymer.

The solution was reduced to a solids content of 40% diluted with methyl isobutyl ketone and esterified with dinothylphenyl acetic acid by refluxing the following mixture for 6 hours:

Parts

Mixed polymer solution (40%) 375.0 Methyl isobutyl ketone 52.5 Dimethyl-tert-amine 1,5 DiiMthoxypheny / acetic acid 51.8

A varnish was produced containing the resulting esterified copolymer, Ccllulose acetate butyrate,

009884/2100

oil-free polyester and a pigment in a weight ratio the solids of about 52.3: 21.5: 23.8: 2.4.

When this paint is on a primed steel surface was applied on which common paints do not work well and baked at 154 ° C (310 ° F) for 30 minutes, a film with good adhesion resulted primed steel surface.

Example 8

A copolymer of methyl methacrylate and glycidyl methacrylate (98/2) was obtained by polymerizing the following Mixture produced:

'· Parts

Methyl methacrylate '1176

Glycidyl methacrylate 24

Toluene 840

Methyl isobutyl ketone 360

Benzoyl peroxide 8.7

In this way a solution was produced containing about 50% by weight of the interpolymer.

* The solution was diluted to a solids content of 40% with methyl isobutyl ketone and esterified with dimethoxynneny! Acetic acid by refluxing the following mixture for 6 hours:

009804/2100

Parts

Mixed polymer solution C 40%) 375.0 methyl isobutylene ketone 52.5

Dimethyl-tert-amife 1.5 Dimethoxyphenylacetic acid 4.2

Toluene. 1.0

A varnish was produced. Contains the resulting, esterified mixed polymer® tr Cellulo @ acetate butyrate, benzyl butyl phth & lat,? olyiaethylinethaerylat and «in pigment in the weight ratio of the solids of about 9 ^ 1: 21.5: 23.8: 43.2: 2.4.

If this paint was applied to a primed steel surface on which conventional paints do not adhere well, and then 30 minutes (F 3IQ ⁰⁾ was baked at 154 ° c, a filet came with particularly good adhesion to the primed steel surface.

Example 9

A mixed polymer of methyl methacrylate and glycidyl acrylate (95/5) was prepared by polymerizing the following mixture:

Parts

Methyl methacrylate 1520 Glycidyl acrylate 80

Toluene 1120

Methyl isobutyl alcohol 430 Benzoylperojeyd 11.6

009884/2100 _ncoTPn

"■.. © BfGSNAL INSPECTED

- 23 - -

In this way a solution was created containing- »

tend about 50% by weight of the copolymer.

■ »

The solution was diluted to a solids content of 40t with methyl isobutyl ketone and with 4-alainobutyric acid esterified by the mixture below for 6 hours were held on the return flow.

. Parts

Mixed polymer solution (40%) 375.0 Methyl isobutyl ketone 40.0

Toluene x 1.0

Formamide 70.0

Dime thy l-tert.-aain 1.5

4-eelnobutyric acid - 6.04

A varnish was produced, containing the resulting esterified mixed polymer, Colluioseacetatbutyrat, oil-free polyester »Polymethylnethacrylat and a Pigment in the weight ratio of the solids of about 9.1: 21.5: 23.8: 43.2: 2.4. '

If this varnish was applied to a primed steel surface, conventional varnishes do not work well and baked for 30 minutes at 154 ° C (310 ° F) produced a film with very good adhesion the primed steel surface.

009884/2100

example 10

A mixed polymer of methyl methacrylate and glycol acrylate (75/25) was made by polymerizing the following Mixture produced:

) TeUe

MethyIm © thacrylet 1200

Glycidyl erylt. 400

Toluene - 1120

Methyliiobuty! Ketone 480

Benzoyl peroxide 11.6

In this way a solution containing about 50% by weight of the interpolymer.

The solution was Methyllsobutylketon to 40% f verdünnt'und with pimethoxyphany acid esterified by the following mixture was kept flufl 4 1/4 hours on the return ·!:

Parts

Mixed polymer solution (40%) 187.5

Methyl isobutyl ketone 26

Toluene 0.5

Dimethoxyphenylacetic acid 28

Dimethyl-tert-amine Q _s l%

. A lacquer was produced / containing ' 009884/2100

resulting esterified copolymers, cellulose acetate butyrate, oil-free polyester, polymethyl methacrylate and a Pigment in a weight ratio of solids of about 9.1: 21.5: 23.8: 43.2: 2.4. If this paint is applied to a primer * te steel surface was applied on which usual Paints do not adhere well and then for 30 minutes at 154 ° C (310 ° F) was baked, the result was a film with particularly good adhesion compared to films made from conventional paints.

009884/2100

Claims (14)

• Claims Acrylic polymer, characterized by the reaction product of (1) a copolymer of essentially methyl methacrylate and glycldyl acrylate or methacrylate and (2) an aliphatic monocarboxylic acid which is either unsubstituted or substituted by a polar group other than the hydroxyl group. 2. Acrylic polymer according to claim 1, characterized by the reaction product of (1) with einor aliphatic monocarboxylic acids which is substituted with an axaino group. 3. Acrylic polymer according to claim 1, characterized in ⁰ \ . by the reaction product of (1) with lauric acid, 4-aminobutyric acid ,! «- aminoundecanoic acid, pyruvic acid or dimethoxypheny / acetic acid. 4. Aery! Polymeres according to one of the preceding Claims, characterized by the reaction product of a Copolymers of at least 75 parts by weight of methyl methacrylate and 0.5 to 25 parts by weight of glycidyl acrylate or -inethacrylut, the total part being 100, with the aliphatic monocarboxylic acid according to (2) » 009884/2100 5. Aeryl polymer according to one of the preceding Claims, characterized by the reaction product of the mixed polymer from methyl methacrylate and glycidyl acrylate or methacrylate in a weight ratio of 90 to 99:10 to 1 with the aliphatic monocarboxylic acid according to (2). 6. Aery! Polymeres according to one of the preceding Claims, characterized by the reaction product of the Mixed polymars of methyl methacrylate and glycidyl acrylate or methacrylate in a weight ratio of 95 »5 bits of the aliphatic monocarboxylic acid (2). 7. Acrylic polymers according to one of the preceding Claims, characterized by the reaction product of the Copolymers of at least 75 parts by weight of methyl methacrylate, 0.5 to 25 parts by weight of glycidyl acrylate or methacrylate and smaller proportions of other »ischpolymerisleibaaeräthyleniech unsaturated monomers, which are not react with the glycidyl acrylate or methacrylate content of the copolymer, the total parts being 100, with the aliphatic monocarboxylic acid according to (2). 8. Coating composition using the acrylic polymer according to one of the preceding claims, characterized by a content of an organic solvent and as essential film-forming materials (U at least 009884/2100 40 parts by weight of an acrylic polymer, consisting of (a) Copolymers of essentially at least 75 weight points of methyl methacrylate and 0.5 to 25 parts by weight Glycldyl acrylate or methacrylate, the total of 11 of the interpolymer constituents are 100 and furthermore the interpolymers are esterified with an aliphatic monocarboxylic acid, which is either unsubstituted or substituted with at least one polar group which is not a hydroxy group, or (b) a mixture of the esterified copolymers with homopolymers of methyl methacrylate or with copolymers of methyl methacrylate and an ethylenically unsaturated monomer, which is copolymerizable with it and compared to the esterified one The glycidyl portion of the esterified copolymer is inert; (2) up to 50 parts by weight at least one compatible Plasticizer; and (3) up to 35 parts by weight of cellulose acetate butyrate, the total parts being based on weight of the film-forming materials, 100 and furthermore the glycidyl acrylate or methacrylate content of each copolymer (a) prior to esterification is about 0.5 to about 25% by weight of the Components (1) of the essential forming materials matters. 9. coating composition according to claim 8, characterized in that the copolymers rrit an aliphatic 009884/2100 Monocarboxylic acids are esterified with an araino group is substituted. -. 10. Coating composition according to claim 8 or 9 #, characterized in that the copolymers are esterified with lauric acid, 4-aminobutyric acid, II-aminoundecanoic acid, pyruvic acid or dimethoxyphenyl eeaetic acid. 11. Coating composition according to one of claims 8 to 10, characterized in that it is an oil-free polyester, a monocarboxylic acid modified alkyd resin with an oil length of 15 to 55 and with 1 to 6% unreacted hydroxyl groups / benzyl butyl phthalate, dibutyl phthalate, trypheny as plasticizer contains! phosphate, 2-ethylhexynbenzyl phthalate or dicyclohexyl phthalate. · 12. Coating composition according to one of claims 8 to 11, characterized in that it contains al3 plasticizer an oil-free polyester obtained by reacting neopentyl glycol, adipic acid, phthalic anhydride and butyl alcohol in a molar ratio of 3: 2: 2: 2 . 13. Coating composition according to one of claims 8 to 12, characterized in that they contain such pre-esterified copolymers contains, in which the glycidyl acrylate or methacrylate antfiil before veneering about 1 to about 10% by weight 00 ^ 1) 04/2100
ßAD RJGiNAL the component (1) of the essential film-forming material lien shut down. 14. Coating compound according to one of claims 8 to 13 / characterized in that it contains the plasticizer in an amount of about 20 to about 40 parts by weight and the cellulose acetate butyrate in an amount of about 10 to about 25 parts by weight. I) (I :) ü IH / 2 I Il 0