DE102006017492A1 - Drug fixation on polymer surfaces - Google Patents

Abstract

The subject of the present invention are compounds according to the general formula 1, $ F1 where R <SUB> 1 </SUB>, R <SUB> 2 </SUB>, R <SUB> 3 </SUB>, R <SUB> 4 </SUB>, R <SUB> 5 </SUB>, R <SUB> 6 </SUB>, R <SUB> 7 </SUB>, R <SUB> 8 </SUB>, R <SUB> 9 </SUB> and R <SUB> 10 </SUB> are independently selected from the group containing hydrogen, alkyl groups with 1 to 20 carbon atoms, substituted alkyl groups with 1 to 20 carbon atoms, alkenyl groups with 1 to 20 carbon atoms and / or substituted alkenyl groups having 1 to 20 carbon atoms, with the condition that at least one of the groups R <SUB> 1 </SUB>, R <SUB> 2 </SUB>, R <SUB> 3 </SUB>, R <SUB > 4 </SUB>, R <SUB> 5 </SUB>, R <SUB> 6 </SUB>, R <SUB> 7 </SUB>, R <SUB> 8 </SUB>, R <SUB > 9 </SUB> and / or R <SUB> 10 </SUB> are independently of one another a group -SQ, where S is selected from the group containing (CH <SUB> 2 </SUB>) <SUB> a </SUB>, $ F2 and a is an integer from 0 to 100, and Q is selected from the group containing $ F3 where P each eils is selected from a group containing CH <SUB> 2 </SUB>, $ F4 alkylene, phenylene, substituted alkylene, substituted phenylene, n, m, o are each an integer from 1 to 20, b is each an integer is from 1 to 20, each c is an integer from 1 to 20, x is an integer from 1 to 20, y is an integer from 0 to 20, z is an integer from 1 to 20, R <SUB > 11 </SUB>, R <SUB> 12 </SUB>, R <SUB> 13 </SUB>, R <SUB> 14 </SUB>, R <SUB> 15 </SUB>, R <SUB > 16 </SUB>, R <SUB> 17 </SUB> and R <SUB> 18 </SUB> are independently selected from hydrogen, alkyl groups with 1 to 20 carbon atoms, substituted alkyl groups with 1 to 20 carbon atoms, alkylene groups with 1 to 20 carbon atoms and / or substituted ...

Description

The The present invention relates to a new class of compounds, have microbial and biocidal properties and modification of surfaces by means of the aforementioned compounds. Another object of the The present application relates to coated substrates compatible with the modified novel biocidal and antimicrobial compounds are.

It There is a growing need to increase the surface area of substrates such as e.g. B. plastic surfaces to protect against the infestation of germs. There are a variety of methods known in the art, such as such a modification of the surface of substrates are carried out can. A particularly intensely developed area recently lies in the modification of the surfaces after the so-called "lotus flower effect", in which the adhesion from contamination, germs or other undesirable deposits Modification of surface properties the one to be protected Substrates is achieved.

Of Furthermore, there is the way, by photochemical processes substances with appropriate properties to fix on surfaces. An often used one Starting material are benzophenone derivatives, since benzophenone under irradiation is converted into an active radical species, which is then chemically firmly on the surface binds to the substrate to be coated.

Especially There is a need in the art for the surfaces of Substrates, such. B. paint surfaces, woven or non-woven substrates, polymeric substrates or metal coatings so too change, that effectively prevents adhesion or growth of bacteria becomes.

The Technical object of the present invention is the provision new active compounds applied to substrate surfaces can and sustain the growth of bacteria or similar harmful ones Prevent germs. Another object of the present invention is the provision of a method for applying the substances with biodizer and / or antimicrobial activity as well as providing of such coated substrates.

wobei R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ und R₁₀ unabhängig voneinander ausgewählt sind aus der Gruppe enthaltend Wasserstoff, Alkylgruppen mit 1 bis 20 Kohlenstoffatomen, substituierte Alkylgruppen mit 1 bis 20 Kohlenstoffatomen, Alkenylgruppen mit 1 bis 20 Kohlenstoffatomen und/oder substituierte Alkenylgruppen mit 1 bis 20 Kohlenstoffatomen,
unter der Bedingung, dass wenigstens eine der Gruppen R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉ und/oder R₁₀ unabhängig voneinander eine Gruppe -S-Q ist,
wobei
S ausgewählt ist aus der Gruppe enthaltend (CH₂)_a,

und a eine ganze Zahl von 0 bis 100 ist, und
Q ausgewählt ist aus einer Gruppe enthaltend

wobei
P jeweils ausgewählt ist einer der Gruppe enthaltend CH₂,

Alkylen, Phenylen, substituiertes Alkylen, substituiertes Phenylen
n, m, o jeweils eine ganze Zahl von 1 bis 20 ist,
b jeweils eine ganze Zahl von 1 bis 20 ist,
c jeweils eine ganze Zahl von 1 bis 20 ist,
x eine ganze Zahl von 1 bis 20 ist,
y eine ganze Zahl von 0 bis 20 ist,
z eine ganze Zahl von 1 bis 20 ist,
R₁₁, R₁₂, R₁₃, R₁₄, R₁₅, R₁₆, R₁₇ und R₁₈ unabhängig voneinander ausgewählt sind aus Wasserstoff, Alkylgruppen mit 1 bis 20 Kohlenstoffatomen, substituierten Alkylgruppen mit 1 bis 20 Kohlenstoffatomen, Alkenylgruppen mit 1 bis 20 Kohlenstoffatomen und/oder substituierte Alkenylgruppen mit 1 bis 20 Kohlenstoffatomen und
X ein geeignetes Gegenion ist.The technical object of the present invention is achieved by a compound according to the general formula I.

wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ and R _{10 are} independently selected from the group consisting of hydrogen, alkyl groups having 1 to 20 carbon atoms, substituted alkyl groups with 1 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms and / or substituted alkenyl groups having 1 to 20 carbon atoms,
with the proviso that at least one of the groups R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ and / or R _{10 is} independently a group -SQ,
in which
S is selected from the group consisting of (CH ₂ ) _a ,

and a is an integer from 0 to 100, and
Q is selected from a group containing

in which
Each P is selected from one of the group containing CH ₂ ,

Alkylene, phenylene, substituted alkylene, substituted phenylene
n, m, o are each an integer from 1 to 20,
b is an integer from 1 to 20,
c is an integer from 1 to 20,
x is an integer from 1 to 20,
y is an integer from 0 to 20,
z is an integer from 1 to 20,
R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₁₇ and R _{18 are} independently selected from hydrogen, alkyl groups of 1 to 20 carbon atoms, substituted alkyl groups of 1 to 20 carbon atoms, alkenyl groups of 1 to 20 Carbon atoms and / or substituted alkenyl groups having 1 to 20 carbon atoms and
X is a suitable counterion.

In a preferred embodiment, the radicals R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ^{10 are} independently selected from linear or branched alkyl groups having 1, 2, 3 , 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms, linear or branched substituted alkyl groups with 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms, linear or branched alkenyl groups having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms and / or linear or branched, substituted alkenyl groups having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.

In a further preferred embodiment is a 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30.

Preferably, n, m, o are each selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20.

c is preferably each a number selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20.

Preferably x is a number selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20th

In a further preferred embodiment is y 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20.

Further preferably z is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20.

In a further preferred embodiment, R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₁₇ , R _{18 are} independently selected from hydrogen, linear or branched alkyl groups with 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms, linear or branched substituted ten alkyl groups with 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms, linear or branched alkenyl groups having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms and / or linear or branched substituted alkenyl groups having 1, 2, 3, 4, 5, 6, 7, 8, 9 , 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.

The Counterion X is preferably not further limited. In addition, points the counterion X preferably has a negative charge, preferably cationic charge of benzophenone derivative of the general Formula I corresponds or else there are several counterions X in the molecule, such that the compound of general formula I is electrically neutral is.

In a further preferred embodiment X can be selected being fluoride, chloride, bromide, iodide, sulphate, bisulphate, Carbonate, bicarbonate, nitrate, sulfonate, phosphate, phosphonate or mixtures thereof. For these anions, the stoichiometry is so to choose that the compound of general formula I electrically neutral is.

By the group -CH ₃ is meant a methyl group (-Me).

In a preferred embodiment, S is a methylene group (CH ₂ group) and Q is selected from the group

In a further preferred embodiment, the radical R _{3 is} the group -SQ and the radicals R ₁ , R ₂ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ and R ₁₀ are hydrogen.

Surprisingly the above compounds show a very high activity against the most diverse germs and especially against fungus cultures. The abovementioned compounds of general formula I can be used for Coating of substrates can be used.

Also shows the compound according to more general Formula I improved efficacy against germs. It is a very effective compound with antimicrobial and / or biocidal properties.

• a) ein Substrat und
• b) eine Beschichtung aufgebracht auf mindestens einer ersten Seite des Substrates, wobei die Beschichtung aus einer Beschichtungszusammensetzung enthaltend eine Verbindung gemäß der allgemeinen Formel I aufgebracht wurde und nachfolgend einer elektromagnetischen Strahlung ausgesetzt wurde.

A further subject of the present invention is a coated substrate comprising:

• a) a substrate and
• b) a coating applied to at least a first side of the substrate, wherein the coating has been applied from a coating composition containing a compound according to the general formula I and subsequently exposed to electromagnetic radiation.

Preferably is the coated substrate a) selected from the group containing Paint surfaces, Color surfaces, Nonwovens, woven substrates, non-woven substrates, paper, cardboard, towels, Conveyor belts, in particular plastic conveyor belts, polymeric substrates, metal coatings, plastic surfaces, in particular in the medical and / or nursing field, detergents, plastic cages, in particular in the sanitary Field, plastic cages for toilet stones, Packaging or mixtures thereof.

The Electromagnetic radiation in b) preferably has a wavelength of From 100 nm to 700 nm, more preferably from 150 nm to 500 nm, and in particular from 200 nm to 400 nm.

• a) Bereitstellen eines Substrates,
• b) Aufbringen einer Beschichtungszusammensetzung enthaltend mindestens eine Verbindung gemäß der allgemeinen Formel I auf mindestens einer ersten Seite des Substrates und nachfolgendes Aussetzen der aufgebrachten Beschichtungszusammensetzung einer elektromagnetischen Strahlung.

A further subject of the present invention is a process for coating substrates comprising the steps:

• a) providing a substrate,
• b) applying a coating composition containing at least one compound according to the general formula I on at least a first side of the substrate and subsequently exposing the applied coating composition to electromagnetic radiation.

The Substrates are not further limited. In particular, the substrate becomes selected in steps a) from the group containing paint surfaces, paint surfaces, nonwovens, woven substrates, non-woven substrates, paper, cardboard, cloths, conveyor belts, in particular Plastic conveyor belts, polymeric substrates, metal coatings, plastic surfaces, in particular in the medical and / or nursing field, detergents, plastic cages, in particular in the sanitary Field, plastic cages for toilet stones, Packaging or mixtures thereof.

The Application of the coating composition containing at least a compound of general formula I in step b) can with be carried out in any coating process, the specialist is known. In particular, the coating composition by means of a brush, a brush, an airbrush coater, a roller coater, a curtain coater, a Roller application unit, a spray gun or by immersion be applied in the coating composition.

The Coating composition preferably contains a solvent which is preferably selected is from organic solvents. Preferably, after application of the coating composition and before the irradiation with the electromagnetic radiation the Be dried coating composition. Again, each one is Method of drying applicable to those skilled in this context is known. In particular, the coating composition by means of an IR radiator, Hot air, Microwave radiation or dried by storage at elevated temperature become.

In a further preferred embodiment For example, the coating composition may be in at least two layers be applied to the substrate. It is further preferred that before applying the coating composition at least one additional coating was applied to the substrate. This coating can z. B. be a coating with which the surface of the Substrates is further smoothed.

Preferably the electrical radiation in step b) has a wavelength of From 100 nm to 700 nm, more preferably from 150 nm to 500 nm, and in particular from 200 nm to 400 nm. The electromagnetic radiation can be generated with any aggregate that is suitable for the person skilled in the art of radiation in this waveband is known. Especially the irradiation can be done by means of a belt system. Preferably is the electromagnetic radiation UV light, preferably produced with a UV belt system.

One Another object of the present invention is a coated Substrate, available according to the aforementioned method.

Surprisingly, it has been found that the coated substrates of the present invention have improved activity against the attachment of fungi and bacteria. The growth of such nuclei on the coated substrate is suppressed or prevented. Furthermore was Surprisingly found that the other surface properties of the substrate were not adversely affected. It is possible to continue to use the coated substrates according to their usual use, while maintaining the aforementioned advantages of the coated substrate.

The Electromagnetic radiation in step b) preferably acts for a duration from 30 seconds to 3 hours to that with the coating composition provided substrate. Preferably, the electromagnetic acts Radiation for a period of 1 minute to 1 hour and more preferably of 2 minutes to 40 minutes on the with the coating composition provided substrate.

The present invention is illustrated by way of example in the following examples: EXAMPLES Example 1 Preparation of the Compound II

1.8 g of 1,4-diazabicyclo [2.2.2] octane (0.016 mmol) are dissolved in 200 ml of acetonitrile. While stirring, 5.6 g of dodecyl bromide (0.023 mol) are added at room temperature in 4 equivalent portions (1.4 g) in each case after 45 minutes. The reaction solution is stirred for 24 hours under reflux (82 ° C). It is then cooled, forming a white precipitate. Subsequently, 4 g of 4- (bromomethyl) benzophenone (0.015 mol) are added and stirring is continued for a further 22 hours under reflux. Subsequently, the batch is concentrated in half and stored in the refrigerator. It precipitates a white precipitate, which is filtered off and washed with a little acetonitrile. The resulting reaction product is dried for 2 hours at 70 ° C in a vacuum oven. In this case, the product puffs up and results in a white granular product with a yield of 23.7 g. Example 2 Preparation of compound III

1 g 4- (bromomethyl) benzophenone (0.00363 mol) and 0.92 g of N, N-dimethyldodecylamine (0.00436 mole 1.2-fold excess) are weighed and submerged in 50 ml of acetonitrile for at least 24 hours backflow (82 ° C) touched. This forms a clear solution. The clear solution becomes concentrated on Rotati onsverdampfer, so that forms a colorless, clear oil, from the white Crystals crystallize. The white crystals were separated and washed with a little acetonitrile.

Applying the benzophenone compound to a substrate:
The above-mentioned benzophenone compounds of Example 1 or 2 are dissolved in ethanol. Particulate polystyrene is placed in a petri dish and the solution of benzophenone solution is added and the petri dish covered with a quartz lid. In a UV belt system is exposed for 30 minutes with UV light. Subsequently, the polystyrene is washed with ethanol and then dried at room temperature.

Investigation of the antimicrobial properties of the substrate coupled drugs:
The investigation of the antimicrobial properties is carried out by means of the Hemmhof test. The active ingredients are weighed into a centrally punched hole in agar plates. After coating the active ingredients with liquid agar, the plates are incubated at 25 ° C. Since the agar incorporates mold fungus spores of the culture Aspergillus niger, depending on the fungicity and diffusibility of the active ingredients, a zone of inhibition around the weighed-in substance is produced.

When Substances are the compounds of Example 1 (compound II) and 2 (Compound III) coated with these compounds Polystyrene and blank as uncoated polystyrene used.

It shows that both the compounds of Examples 1 and 2, as well as the hereby coated polystyrene a fungicidal action on Aspergillus niger, as is a very distinctive courtyard forms around the applied substances.

In contrast, shows Polystyrene alone does not inhibit and thus has no fungicidal Properties.

In summary let yourself Thus, it can be seen that both the benzophenone derivatives of the present Invention as well as hereby coated substrates significantly improved have antimicrobial and / or biocidal properties. The coated ones Substrates of the present invention can be used for a wide variety of applications be used. Furthermore, the method of manufacture this coated substrates very easy to do, so that this is a very efficient economic process is.

Example 3:

The subsequent compounds of the formula IV, V and VI are analogous the aforementioned examples prepared from the corresponding starting materials.

The investigation of the antimicrobial properties is carried out by means of a Hemmhoftests by the suspension method. This is a pre-breeding of the germ Staphylococcus aureus K 3212 on nutrient agar Plates preferred and created an overnight culture. In liquid agar, germs are incorporated (10 ³ cfu / ml). This agar is poured into petri dishes and allowed to harden the agar. Subsequently, a hole is punched in the center of the agar and the soil is wetted again with contaminated agar. Then the substance to be examined is applied and subsequently covered with further contaminated agar, so that the substance to be examined is enclosed by agar. The incubation is carried out aerobically in an incubator

The substances III, IV, V and VI show a Hemmhof with a diameter according to Table 1: Table 1:

at The above compounds in Table 1 show that no Growth of germs over the test substance is recognizable.

The Compound II prepared from Example 2 is as indicated above to particulate Polystyrene applied. This modified substrate will also like for the Compounds II, IV, V, VI are applied to an agar plate. This forms a 2 mm large Hemmhof and the modified Polystyrene was not overgrown by germs. A blank with particulate Polystyrene revealed that this has no antimicrobial properties and therefore the antimicrobial activity on the Modification of the polystyrene with the compound II is due.

Example 4:

According to the regulations for testing the efficacy of antimicrobial and / or biocidal substances suspension tests are carried out. A method to use is described, for example, in J. Gebel et al., "Standard Methods of DGHM for testing chemical disinfection process ", mhp Verlag GmbH, as of 1.9.2001, chapter 9 indicated.

Tabelle 3: Konzentration Verbindungen 2600 ppm

Compounds II, III, IV, V, VI were added at a concentration of 100 ppm and 2600 ppm to a sample containing Staphylococcus aureus. The survival rate is determined after 1 h and possibly 24 h. Table 2: Concentration compounds 100 ppm

Table 3: Concentration compounds 2600 ppm

The polystyrene-applied compound II (preparation see above) will also o.a. Subjected to suspension test. At a concentration of 100 ppm, a survival rate occurs after 1 h of 2.20E + 2 and after 24 h of 1.00E + 01. At a concentration of 2600 ppm, the microbial count was 1.00E + 01 after 1 h and 1.00E + 01 after 24 h.

Claims (14)

A compound according to the general formula I

wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ and R _{10 are} independently selected from the group consisting of hydrogen, alkyl groups having 1 to 20 carbon atoms, substituted alkyl groups with 1 to 20 carbon atoms, alkenyl groups having 1 to 20 carbon atoms and / or substituted alkenyl groups having 1 to 20 carbon atoms, under the condition that at least one of the groups R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ and / or R _{10 is,} independently of one another, a group -SQ, where S is selected from the group comprising (CH ₂ ) _a ,

and a is an integer of 0 to 100, and Q is selected from a group containing

wherein each P is selected from one of the group containing CH ₂ ,

Alkylene, phenylene, substituted alkylene, substituted phenylene n, m, o is an integer of 1 to 20, b is an integer of 1 to 20, c is an integer of 1 to 20, x is an integer from 1 to 20, y is an integer from 0 to 20, z is an integer from 1 to 20, R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₁₇ and R _{18 are} independently are selected from hydrogen, alkyl groups of 1 to 20 carbon atoms, substituted alkyl groups of 1 to 20 carbon atoms, alkenyl groups of 1 to 20 carbon atoms and / or substituted alkenyl groups of 1 to 20 carbon atoms and X is a suitable counterion. The compound according to claim 1, characterized in that S is a methylene group (CH ₂ group) and Q is selected from the group

The compound according to claim 1 or 2, characterized in that R _{3 is} the group -SQ and the radicals R ₁ , R ₂ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ and R _{10 are} hydrogen , Use of the compounds according to any one of claims 1 to 3 for coating substrates. The use according to any one of claims 1 to 3 as a biocidal and / or antimicrobial substance. A coated substrate comprising: a) a Substrate and b) a coating applied to at least a first side of the substrate, wherein the coating of a A coating composition containing a compound according to claims 1 to 3 was applied and subsequently an electromagnetic radiation was suspended. The coated substrate according to claim 6, characterized that the substrate a) selected is from the group containing lacquer surfaces, color surfaces, nonwovens, woven substrates, non-woven Substrates, paper, cardboard, cloths, Conveyor belts, in particular plastic conveyor belts, polymeric substrates, metal coatings, plastic surfaces, in particular in the medical and / or nursing field, detergents, plastic cages, in particular in the sanitary Field, plastic cages for toilet stones, Packaging or mixtures thereof. The coated substrate according to claim 6 or 7, characterized characterized in that the electromagnetic radiation in b) a wavelength from 100 nm to 700 nm, more preferably from 150 nm to 500 nm, and in particular from 200 nm to 400 nm. A method of coating substrates comprising the steps of: a) providing a substrate, b) applying a coating composition comprising at least one compound according to at least one of claims 1 to 3 on at least a first side of the substrate and subsequently exposing the applied coating composition to electromagnetic radiation. The method according to claim 9, characterized the substrate in step a) is selected from the group comprising Paint surfaces, Color surfaces, Nonwovens, woven substrates, non-woven Substrates, paper, cardboard, cloths, Conveyor belts, in particular plastic conveyor belts, polymeric substrates, metal coatings, plastic surfaces, in particular in the medical and / or nursing field, detergents, plastic cages, in particular in the sanitary Field, plastic cages for toilet stones, Packaging or mixtures thereof. The method according to claim 9 or 10, characterized characterized in that the electromagnetic radiation in step b) one wavelength from 100 nm to 700 nm, more preferably from 150 nm to 500 nm, and in particular from 200 nm to 400 nm. The method according to any one of claims 9 to 11, characterized in that the coating composition in step b) a solvent contains. The method according to any one of claims 9 to 12, characterized in that the coating composition in step b) before the irradiation with the electromagnetic radiation is dried. A coated substrate obtainable by the process according to at least one of the claims 9 to 13.