DE202015000811U1 - Curable composition containing Alkylaminoalkylalkoxy (meth) acrylates - Google Patents

Abstract

Curable compositions comprising a monomer mixture of a1) 1 to 90% by weight of one or more (meth) acrylic acid esters of the formula (I) H2C = CHR1-C (OO) -O- (CHR2-CHR3-O) x- (CH2 where R 1 = H or methyl R 2, R 3 = independently of one another H or methyl R 4, R 5 = independently of one another methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl x = an integer from 1 to 10 y = an integer from 1 to 4, and a2) from 10 to 99% by weight of one or more monomers copolymerizable with these, the sum of a1) and a2) being 100% by weight. % results.

Description

The invention relates to curable compositions containing a1) alkylaminoalkylalkoxy (meth) acrylates and a2) monomers copolymerizable with these. The invention further relates to curable compositions comprising copolymers a) of a1) alkylaminoalkylalkoxy (meth) acrylates and a2) further monomers copolymerizable with these and b) optionally further monomers.

Curable compositions, in particular for printing inks, printing inks and coatings in electronics, in the automotive industry, in the construction sector and in the industrial sector, containing copolymers based on (meth) acrylic acid monomers, are known. Nevertheless, there is still a need for alternative curable compositions having very good adhesion to surfaces, especially very good low temperature adhesion, and very good wettability of surfaces, especially plastic surfaces such as polyethylene, polypropylene or polyethylene terephthalate Glass or paper, and with high scratch resistance and good chemical resistance and weatherability in the cured state, for a variety of different applications, which are applicable in both solvent-based and water-based systems.

• a1) 1 bis 90 Gew.-% Alkylaminoalkylalkoxy(meth)acrylate der Formel (I) und
• a2) 10 bis 99 Gew.-% mit diesen copolymerisierbare weitere Monomere,

wobei die Summe aus a1) und a2) 100 Gew.-% ergibt.The present invention relates to curable compositions, in particular for adhesives, printing inks, printing inks and coatings for electronic components and in the automotive industry, comprising a monomer mixture

• a1) from 1 to 90% by weight of alkylaminoalkylalkoxy (meth) acrylates of the formula (I) and
• a2) from 10 to 99% by weight with these copolymerizable further monomers,

the sum of a1) and a2) being 100% by weight.

The monomer mixture of the curable composition contains at least 1% by weight and at most 90% by weight, preferably at most 70% by weight, of alkylaminoalkylalkoxy (meth) acrylates.

• a) Copolymere aus
• a1) 1 bis 90 Gew.-% eines oder mehrerer Alkylaminoalkylalkoxy(meth)acrylate und
• a2) 10 bis 99 Gew.-% eines oder mehrerer mit diesen copolymerisierbarer weiterer Monomere,

wobei die Summe aus a1) und a2) 100 Gew.-% ergibt,

• b) gegebenenfalls weitere Monomere.

The present invention furthermore relates to curable compositions, in particular for adhesives, printing inks, printing inks and for coatings for electronic components and in the automotive industry

• a) copolymers
• a1) from 1 to 90% by weight of one or more alkylaminoalkylalkoxy (meth) acrylates and
• a2) from 10 to 99% by weight of one or more monomers copolymerizable with these,

the sum of a1) and a2) being 100% by weight,

• b) optionally further monomers.

The alkylaminoalkylalkoxy (meth) acrylates are esters of acrylic acid or of methacrylic acid having the formula (I) H ₂ C = CHR ₁ -C (= O) -O- (CHR ₂ -CHR ₃ -O) _x - (CH ₂ ) _y -NR ₄ R ₅ (I) in which mean
R ₁ = H or methyl,
R ₂ , R ₃ = independently of one another H or methyl
R ₄ , R ₅ = independently of one another are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl
x = an integer from 1 to 10
y = an integer from 1 to 4.

The alkylaminoalkylalkoxy (meth) acrylates are preferably esters of acrylic acid or of methacrylic acid having the formula (II) H ₂ C = CHR ₁ -C (= O) -O- (CHR ₂ -CHR ₃ -O) _x - (CH ₂ ) _y -NR ₄ R ₅ (II) in which mean
R ₁ = H or methyl
R ₂ , R ₃ = independently of one another H or methyl
R ₄ , R ₅ = independently of one another are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl
x = an integer from 1 to 10
y = 2
is.

The alkylaminoalkylalkoxy (meth) acrylates are particularly preferably esters of acrylic acid or of methacrylic acid having the formula (III) H ₂ C = CHR ₁ -C (= O) -O- (CHR ₂ -CHR ₃ -O) _x - (CH ₂ ) _y -NR ₄ R ₅ (III) in which mean
R ₁ = H or methyl
R ₂ , R ₃ = independently of one another H or methyl
R ₄ , R ₅ = independently of one another are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl
x = 1
y = 2.

The alkylaminoalkylalkoxy (meth) acrylates are very particularly preferably esters of acrylic acid or of methacrylic acid having the formula (IV) H ₂ C = CHR ₁ -C (= O) -O- (CHR ₂ -CHR ₃ -O) _x - (CH ₂ ) _y -NR ₄ R ₅ (IV) in which mean
R ₁ = H or methyl
R ₂ , R ₃ = H
R ₄ , R ₅ = independently of one another are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl
x = 1
y = 2

The alkylaminoalkylalkoxy (meth) acrylates are, in particular, esters of acrylic acid or of methacrylic acid of the formula (V) H ₂ C = CHR ₁ -C (= O) -O- (CHR ₂ -CHR ₃ -O) _x - (CH ₂ ) _y -NR ₄ R ₅ (V) in which mean
R ₁ = H or methyl
R ₂ , R ₃ = H
R ₄ , R ₅ = methyl
x = 1
y = 2.

The alkylaminoalkylalkoxy (meth) acrylates are prepared by esterification of (meth) acrylic acid or by transesterification of (meth) acrylic acid esters, as in WO2006 / 012980 . US 7,528,278 and WO 2013/004767 described.

The Alkylaminoalkylalkoxy inventive (meth) acrylates are available for example from BASF SE, Ludwigshafen, commercially available under the product name "Lupragen ^® 107 MA".

The curable compositions of the invention are characterized by a very good adhesion to surfaces, especially a very good adhesion at low temperatures, and a very good wettability of surfaces, especially plastic surfaces, such as polyethylene, polypropylene or polyethylene terephthalate, glass or Made of paper, as well as by a high scratch resistance, good chemical resistance and weather resistance in the cured state, and are applicable in both solvent-based and water-based systems.

The curable compositions of the invention are characterized in particular by a high hydrolysis resistance.

According to the invention, the curable compositions based on the total composition contain at least 1% by weight, preferably at least 5% by weight, more preferably at least 10% by weight and generally at most 70% by weight, preferably at most 60% by weight. % and more preferably at most 50% by weight of alkylaminoalkylalkoxy (meth) acrylates a1) which are present in the monomer mixture of a1) and a2) or the copolymer a).

The copolymers a) or the monomer mixtures from a1) and a2) contain from 1 to 90% by weight, preferably from 5 to 70% by weight, particularly preferably from 10 to 60% by weight and in particular from 15 to 55% by weight Alkylaminoalkylalkoxy (meth) acrylates a1) and 10 to 99 wt .-%, preferably 30 to 95 wt .-%, particularly preferably 40 to 90 wt .-% and in particular 45 to 85 wt .-% of further monomers a2).

The other monomers a2) with which the alkylaminoalkylalkoxy (meth) acrylates are copolymerized according to the invention are in particular so-called main monomers a21), selected from other C ₁ - to C ₂₀ -alkyl (meth) acrylates, vinyl esters of up to 20 carbon atoms Carboxylic acids, vinyl aromatics having up to 20 carbon atoms, ethylenically unsaturated nitriles, vinyl halides, vinyl ethers of alcohols containing 1 to 10 carbon atoms, aliphatic hydrocarbons having 2 to 8 carbon atoms and one or two double bonds or mixtures of these monomers. To name a few are z. B. (meth) acrylic acid alkyl ester having a C ₁ -C ₁₀ alkyl radical, such as methyl methacrylate, methyl acrylate, n-butyl acrylate, ethyl acrylate and 2-ethylhexyl acrylate. In particular, mixtures of (meth) acrylic acid alkyl esters are also suitable. Vinyl esters of carboxylic acids having 1 to 20 carbon atoms are, for. As vinyl laurate, vinyl stearate, vinyl propionate, vinyl versatate and vinyl acetate. Suitable vinylaromatic compounds are vinyltoluene, ortho- and para-methylstyrene, ortho-butylstyrene, 4-n-butylstyrene, 4-n-decylstyrene and preferably styrene. Examples of nitriles are acrylonitrile and methacrylonitrile. The vinyl halides are chloro, fluoro or bromo substituted ethylenically unsaturated compounds, preferably vinyl chloride and vinylidene chloride. To name as vinyl ethers are, for. As vinyl methyl ether or vinyl isobutyl ether. Vinyl ether is preferably from 1 to 4 C-containing alcohols. As hydrocarbons having 2 to 8 carbon atoms and one or two olefinic double bonds may be mentioned ethylene, propylene, butadiene, isoprene and chloroprene. To C ₈ alkyl acrylates, C ₁ - - to C ₈ -alkyl methacrylates, vinylaromatics, especially styrene, and mixtures thereof Preferred principal monomers are in particular C _1. Very particular preference is given to methyl acrylate, methyl methacrylate, ethyl acrylate, n-butyl acrylate, n-hexyl acrylate, octyl acrylate and 2-ethylhexyl acrylate, styrene and mixtures of these monomers. Preferably, the copolymer is a polyacrylate. Polyacrylate is to be understood as meaning a copolymer which is composed of at least 50% by weight, preferably at least 70% by weight, of C ₁ -C ₂₀ -alkyl (meth) acrylates. The content of Alkylaminoalkylalkoxy (meth) acrylates in the copolymer is at least 1 wt .-%. The main monomers may be present in amounts of up to 99% by weight in the copolymers a) or the monomer mixtures from a1) and a2).

Suitable further monomers a2) with which the alkylaminoalkylalkoxy (meth) acrylates a1) can be copolymerized are the following secondary monomers a22): monomers having hydroxyl groups, in particular hydroxyalkyl (meth) acrylates, (meth) acrylamide, glycidyl (meth) acrylate or (meth) acrylonitrile. Mention may also be made of crosslinking monomers having at least two reactive groups, preferably ethylenically unsaturated, polymerizable groups, eg. Allyl (meth) acrylate, diacrylates such as butanediol diacrylate. Particular mention may be made of monomers having acid groups or acid anhydride groups, eg. As monomers with carboxylic acid, sulfonic acid or phosphonic acid groups. Preference is given to carboxylic acid groups or their anhydrides. Called z. For example, acrylic acid, methacrylic acid, itaconic acid, maleic acid, maleic anhydride or fumaric acid. Particular mention may be made of (meth) acrylate monomers having carbamate functions, e.g. Carbamate propyl acrylate, carbamate propyl methacrylate, carbamate ethyl acrylate and carbamate ethyl methacrylate. The further monomers a22) can be used in amounts of generally 0 to 10% by weight, preferably 0.1 to 10% by weight, more preferably 0.1 to 5% by weight, very particularly preferably 0.2 to 3 Wt .-%, based on the copolymer or the total amount of monomer, be contained.

Inventive compositions which already contain a copolymer of a1) and a2) may contain further monomers b). Further monomers b) are the other monomers a2) (main and secondary monomers).

The glass transition temperature of the copolymer is preferably -60 to 150 ° C, more preferably -60 to 100 ° C, and most preferably -60 to 50 ° C. The glass transition temperature can be determined by differential scanning calorimetry (see, eg. ASTM 3418/82 , so-called "midpoint temperature") determine.

The copolymer composed of alkylaminoalkylalkoxy (meth) acrylates a1) and further monomers a2) generally has an average weight-average molecular weight of at least 2400 g / mol, preferably of at least 3000 g / mol, more preferably of at least 3500 g / mol, and in particular of at least 4000 g / mol. Furthermore, the copolymer composed of alkylaminoalkylalkoxy (meth) acrylates a1) and further monomers a2) preferably has an average weight-average molecular weight of at most 500,000 g / mol, more preferably of at most 150,000 g / mol, and in particular of at most 50,000 g / mol.

The copolymers are preferably prepared by solution polymerization, emulsion polymerization or suspension polymerization. In the emulsion polymerization and suspension polymerization, ethylenically unsaturated compounds (monomers) are polymerized in water, with ionic and / or nonionic emulsifiers and / or protective colloids or stabilizers being used as surface-active compounds for stabilizing the monomer droplets or micelles and the polymer particles later formed from the monomers ,

The curable compositions according to the invention may contain, as further constituents c), also solvents, such as water or organic solvents. As organic solvents, it is possible to use ketones, esters, aprotic amides, aprotic sulfoxides, aromatic hydrocarbons or mixtures thereof. Examples of organic solvents which may be mentioned are methyl ethyl ketone, methyl isobutyl ketone, iso-amyl acetate, butyl acetate, ethylene glycol butyl ether acetate, propylene glycol monomethyl ether acetate, xylene, N-methylpyrrolidone or mixtures thereof. For the curable compositions according to the invention which are prepared with a synthetic copolymer, the copolymer being composed of alkylaminoalkylalkoxy (meth) acrylates and other monomers copolymerized therewith, water is preferably used as the solvent. The content of solvent in the curable compositions of the invention comprising copolymers of alkylaminoalkylalkoxy (meth) acrylates a1) and other monomers a2) copolymerized therewith is generally up to 50% by weight, based on the total weight of the curable composition. Preferably, the content of solvent is at least 15 wt .-%, based on the total weight of the curable composition, more preferably at least 20 wt .-%, and in particular at least 25 wt .-% The curable compositions according to the invention containing Alkylaminoalkylalkoxy (meth Acrylates a1) and copolymerizable further monomers a2) blended therewith generally have a solvent content of 0-50% by weight, preferably 0-20% by weight and more preferably 0-5% by weight, based on the total weight of the curable Composition.

In addition to the copolymers of a1) and a2) and / or the monomers a1), a2) and optionally b), the curable compositions according to the invention may also contain crosslinking agents d) which contain the (meth) acrylate-containing copolymers or the monomers upon application of the curable composition of the present invention to chemically react on a surface and thereby crosslink the copolymer. Crosslinkers can be monomeric, oligomeric or polymeric compounds. For example, aminoplasts are used as crosslinkers. When Aminoplast is preferably a monomeric, preferably partially alkylated, in particular partially methylated, melamine-formaldehyde resin. The content of crosslinker in the curable compositions of the invention is generally at least 5 wt .-%, based on the total weight of the curable composition, preferably at least 10 wt .-%, and particularly preferably at least 15 wt .-%. Further preferably, the content of crosslinker in the curable compositions of the invention is up to 40 wt .-%, based on the total weight of the curable composition, particularly preferably up to 35 wt .-%, and more preferably at most up to 30 wt. -%.

In addition to the copolymers and / or monomers, the curable compositions according to the invention may contain, as further constituents e), catalysts which accelerate the curing of the composition according to the invention. As suitable catalysts, alkylsulfonic acids, arylsulfonic acids, alkylarylsulfonic acids, phosphoric acid and phosphoric acid esters can be used. Preference is given to using methanesulfonic acid, para-toluenesulfonic acid, dinonylnaphthalenedisulfonic acid, dodecylbenzylsulfonic acid, phenyl phosphate and butyl phosphate. Also suitable are monobutyl maleate, boron trifluoride etherate and trimellitic acid.

The curable compositions according to the invention may, in addition to the copolymers a) of a1) and a2) and / or monomers a1) and a2) and optionally monomers b) as further constituents f) additives such as detergents, stabilizers, wetting agents, rheology modifiers, fillers, pigments, dyes , Fungicides, dispersing agents, adhesion promoters, UV absorbers and light stabilizers. The selection of suitable compounds is known to the person skilled in the art.

• a) 1 bis 100 Gew.-% eines Monomerengemischs aus
• a1) 1 bis 90 Gew.-% eines oder mehrerer Alkylaminoalkylalkoxy(meth)acrylaten und
• a2) 10 bis 99 Gew.-% eines oder mehrerer mit diesen copolymerisierbarer weiterer Monomere,

wobei die Summe aus a1) und a2) 100 Gew.-% ergibt,

• c) 0 bis 50 Gew.-% Lösemittel,
• d) 0 bis 40 Gew.-% Crosslinker,
• e) 0 bis 20 Gew.-% Katalysatoren,
• f) 0 bis 30 Gew.-% Additive,

wobei die Summe aus a), c), d), e) und f) 100 Gew.-% ergibt.The invention also relates to curable compositions containing

• a) 1 to 100 wt .-% of a monomer mixture of
• a1) from 1 to 90% by weight of one or more alkylaminoalkylalkoxy (meth) acrylates and
• a2) from 10 to 99% by weight of one or more monomers copolymerizable with these,

the sum of a1) and a2) being 100% by weight,

• c) 0 to 50% by weight of solvent,
• d) 0 to 40% by weight Crosslinker,
• e) 0 to 20% by weight of catalysts,
• f) 0 to 30% by weight of additives,

wherein the sum of a), c), d), e) and f) gives 100 wt .-%.

• a) 1 bis 100 Gew.-% Copolymere aus
• a1) 1 bis 90 Gew.-% eines oder mehrerer Alkylaminoalkylalkoxy(meth)acrylate und
• a2) 10 bis 99 Gew.-% eines oder mehrerer mit diesen copolymerisierbarer weiterer Monomere,

wobei die Summe aus a1) und a2) 100 Gew.-% ergibt,

• b) 0 bis 99 Gew.-% weitere Monomere
• c) 0 bis 50 Gew.-% Lösemittel,
• d) 0 bis 40 Gew.-% Crosslinker,
• e) 0 bis 20 Gew.-% Katalysatoren,
• f) 0 bis 30 Gew.-% Additive,

wobei die Summe aus a), b), c), d), e) und f) 100 Gew.-% ergibt.The invention also relates to curable compositions containing

• a) 1 to 100 wt .-% copolymers of
• a1) from 1 to 90% by weight of one or more alkylaminoalkylalkoxy (meth) acrylates and
• a2) from 10 to 99% by weight of one or more monomers copolymerizable with these,

the sum of a1) and a2) being 100% by weight,

• b) 0 to 99 wt .-% further monomers
• c) 0 to 50% by weight of solvent,
• d) 0 to 40% by weight Crosslinker,
• e) 0 to 20% by weight of catalysts,
• f) 0 to 30% by weight of additives,

wherein the sum of a), b), c), d), e) and f) gives 100 wt .-%.

The present invention also provides the use of the curable compositions for the production of printing inks, printing inks, coatings, paints and coatings.

The present invention further relates to the use of the curable compositions for the production of screen printing inks, facade paints, wall coatings, window coatings, furniture coatings, automotive finishes, automotive refinish coatings, wood finishes, floor coatings, parquet seals, tank interior coatings, circuit board coating, wire enamels, insulating coatings, coatings for LCD and LED displays , Coatings for glass bottles, coatings for plastic bottles, coating for thermal paper and coatings for reflective films.

The application of the curable composition according to the invention to a surface is carried out by methods known to the person skilled in the art, for example by spraying, dipping or brushing.

After applying the curable composition of the invention to a surface, the composition is cured by methods known to those skilled in the art. This can be done in the simplest case by evaporation of the solvent contained in the curable composition at room temperature or elevated temperatures.

The curable composition of the invention is preferably cured by heating to temperatures of 50 ° C to 180 ° C, preferably 80 ° C to 150 ° C, and more preferably from 100 ° C to 140 ° C, over a period of 1 to 60 minutes, preferably 5 to 30 minutes, more preferably 15 to 20 minutes.

Further preferably, the curable composition of the invention is cured by treatment with UV radiation. The UV radiation can be generated, for example, by means of a mercury vapor lamp with a power of 20 to 200 W / cm, preferably 50 to 150 W / cm, and particularly preferably 60 to 100 W / cm. The irradiation time is generally 1 to 60 minutes, preferably 5 to 30 minutes, and more preferably 15 to 20 minutes.

The curable compositions of the present invention may be applied to all types of solid surfaces, particularly plastic surfaces such as polyethylene, polypropylene or polyethylene terephthalate, glass or paper. The surfaces can be both hard and flexible.

The curable compositions of the invention are characterized by a very good adhesion to surfaces, especially a very good adhesion at low temperatures, and a very good wettability of surfaces, in particular surfaces of plastic, for example polyethylene, polypropylene and polyethylene terephthalate, glass and paper, and high scratch resistance and good chemical resistance and weatherability in the cured state, and are applicable to both solvent-based and water-based systems.

The curable compositions of the invention are characterized in particular by a high hydrolysis resistance.

The curable compositions according to the invention are particularly suitable for coatings in the automotive sector, in the transport sector, in electronic applications, in the construction sector, in the cosmetics and hygiene sector, in food applications and as a coating for clothing.

The curable compositions according to the invention are preferably used for printing inks, printing inks, paints, in particular for primers, for topcoats, basecoats or clearcoats, or for paints.

In a particularly preferred embodiment, the curable compositions according to the invention for screen printing inks, facade paints, wall coatings, window coatings, furniture coatings, automotive coatings, automotive refinish paints, wood finishes, floor coatings, parquet seals, tank coatings, board coatings, wire enamels, insulating coatings, coatings for LCD and LED displays, coatings for Glass bottles, especially beer bottles, coatings for plastic bottles, in particular used for shampoo bottles, coatings for thermal paper and coatings for reflective films.

QUOTES INCLUDE IN THE DESCRIPTION

This list of the documents listed by the applicant has been generated automatically and is included solely for the better information of the reader. The list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions.

Cited patent literature

• WO 2006/012980 [0011]
• US 7528278 [0011]
• WO 2013/004767 [0011]

Cited non-patent literature

• ASTM 3418/82 [0020]

Claims (16)

Curable compositions comprising a monomer mixture of a1) 1 to 90% by weight of one or more (meth) acrylic esters of the formula (I) H ₂ C = CHR ₁ -C (= O) -O- (CHR ₂ -CHR ₃ -O) _x - (CH ₂ ) _y -NR ₄ R ₅ wherein R ₁ = H or methyl R ₂ , R ₃ = independently of one another H or methyl R ₄ , R ₅ = independently of one another methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl x = an integer from 1 to 10 y = an integer from 1 to 4, and a2) from 10 to 99% by weight of one or more monomers copolymerizable with these, the sum of a1) and a2) being 100 wt. -% results. Curable compositions according to claim 1, characterized in that in formula (I) y = 2. Curable compositions according to claim 1 or 2, characterized in that in formula (I) x = 1. Curable compositions according to any one of claims 1 to 3, characterized in that in formula (I) R ₂ , R ₃ = H are. Curable compositions according to any one of claims 1 to 4, characterized in that in formula (I) R ₄ , R ₅ = methyl. Curable compositions according to any one of claims 1 to 5 containing a) 1 to 100 wt .-% of a monomer mixture of a1) from 1 to 90% by weight of one or more (meth) acrylic esters of the formula (I), and a2) from 10 to 99% by weight of one or more monomers copolymerizable with these, the sum of a1) and a2) being 100% by weight, c) 0 to 50% by weight of solvent, d) 0 to 40% by weight Crosslinker, e) 0 to 20% by weight of catalysts, f) 0 to 30% by weight of additives, wherein the sum of a), c), d), e) and f) gives 100 wt .-%. Use of curable compositions according to any one of claims 1 to 6 for the production of printing inks, printing inks, coatings, lacquers and paints. Use according to claim 7 for the production of screen printing inks, facade coatings, wall coatings, window coatings, furniture coatings, automotive coatings, automotive refinish coatings, wood coatings, floor coatings, parquet seals, tank interior coatings, board coatings, wire enamels, insulating coatings, coatings for LCD and LED displays, coatings for glass bottles, coatings for Plastic bottles, thermal paper coating and reflective film coatings. Curable compositions comprising a) copolymers of a1) from 1 to 90% by weight of one or more (meth) acrylic esters of the formula (I) H ₂ C = CHR ₁ -C (= O) -O- (CHR ₂ -CHR ₃ -O) _x - (CH ₂ ) _y -NR ₄ R ₅ wherein R ₁ = H or methyl R ₂ , R ₃ = independently of one another H or methyl R ₄ , R ₅ = independently of one another methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl x = an integer from 1 to 10 y = an integer from 1 to 4 and a2) from 10 to 99% by weight of one or more monomers copolymerizable with these, the sum of a1) and a2) being 100% by weight % and b) optionally other monomers. Curable compositions according to claim 9, characterized in that in formula (I) y = 2. Curable compositions according to claim 9 or 10, characterized in that in formula (I) x = 1. Curable compositions according to any one of claims 9 to 11, characterized in that in formula (I) R ₂ , R ₃ = H are. Curable compositions according to any one of claims 9 to 12, characterized in that in formula (I) R ₄ , R ₅ = methyl. Curable compositions according to any one of claims 9 to 13 comprising a) 1 to 100 wt .-% copolymers of a1) 1 to 90 wt .-% of one or more (meth) acrylic acid ester of the formula (I), and a2) 10 to 99 wt % of one or more other monomers copolymerizable therewith, the sum of a1) and a2) being 100% by weight, b) 0 to 99% by weight of other monomers, c) 0 to 50% by weight of solvent, d) 0 to 40% by weight of crosslinker, e) 0 to 20% by weight of catalysts, f) 0 to 30% by weight of additives, the sum of a) , b), c), d), e), and f) gives 100 wt .-%. Use of curable compositions according to any one of claims 9 to 14 for the production of printing inks, printing inks, coatings, varnishes and paints. Use according to Claim 15 for the production of screen printing inks, facade coatings, wall coatings, window coatings, furniture coatings, automotive coatings, automotive refinish coatings, wood coatings, floor coatings, parquet seals, tank interior coatings.