Antimicrobially active product

Abstract

The invention relates to an antimicrobially active product, having: - a carrier and - a dihydrotriazine compound, a tautomer thereof, or a salt thereof, wherein the dihydrotriazine compound, the tautomer thereof, or the salt thereof is bonded to the carrier, and the dihydrotriazine compound has the following general formula I: formula (I), where - R1 represents (i) a phenyl group or a phenylalkyl group, each of which is optionally substituted with 1 to 3 substituents, selected from the group consisting of a C1-6-alkoxy group, a hydroxy group, a halogen atom, a C1-6-alkyl halide group, a C1-6-alkyl group, a sulfonamido group, and a C1-6-alkoxy halide group, (ii) a naphthyl group or a naphthyl alkyl group, (iii) a heterocyclic group, a heterocyclic alkyl group, or a heterocyclic aminoalkyl group, (iv) an alkyl group with 1 to 16 carbon atoms, or (v) a cycloalkyl group or a cycloalkyl-alkyl group, - R1' represents a hydrogen atom, bonded with the nitrogen atom at position 1 or 3 of the dihydrotriazine ring, - R2 and R3, independently of one another, represent a hydrogen atom or a methyl group, - R4 represents an alkyl group with 7 to 16 carbon atoms, and - the dashed line indicates that the position of a double bond is either between positions 1 and 2 or positions 2 and 3 of the dihydrotriazine ring.

Description

[0001] Antimicrobial product

[0002] The invention relates to an antimicrobially active product.

[0003] FIELD OF APPLICATION AND STATE OF THE ART

[0004] The antimicrobial treatment of wound dressings, sheets, catheters, piercings, and the like is well known. Various substances can be considered for such antimicrobial treatment.

[0005] For example, chlorhexidine, in the form of its gluconate or acetate salt, is used for the antimicrobial treatment of skin dressings and surgical sutures. However, this compound has the fundamental disadvantage of limited stability and forms toxic by-products and degradation products upon prolonged storage, strong heating (e.g., during heat sterilization), or exposure to light. Furthermore, chlorhexidine's effectiveness against fungi, including yeasts, is only weak.

[0006] Polyhexamethylene biguanide is also known for coating catheters, as well as in wound dressings, gauzes, and bandage materials. Polyhexamethylene biguanide is an oligomer composed of several individual substances. The analytical characterization of polyhexamethylene biguanide is therefore not straightforward. Furthermore, its effectiveness against fungi, including yeasts, is also only weak. A biocompatible suture material containing polyhexamethylene biguanide is known, for example, from EP 2 359 874 B1.

[0007] Triclosan has also been established for the antimicrobial coating of surgical suture materials. Until recently, another application for triclosan was topical preparations. However, health concerns have since arisen regarding this use of triclosan.

[0008] Octenidine hydrochloride has established itself as a cationic active ingredient for antiseptic solutions and gels for application to skin, mucous membranes, and wounds. Corresponding products are available commercially under the names "Octenisept" and "Octenilin." A multi-layer wound dressing containing octenidine hydrochloride and hyaluronic acid is also known under the name "Sorelex." However, octenidine also has the disadvantage of being relatively weak against yeasts, including fungi. Furthermore, its relatively high cytotoxicity and moderate tissue tolerance limit its use in products with long-term contact with living tissue.

[0009] Dihydrotriazine compounds are known from EP 1 574 503 A1. These can be used for the production of various dosage forms, such as tablets, pills, capsules, powders, granules, suppositories, injections, pastes, ointments, creams, gels, gel-like creams, lotions, emulsions, suspensions, poultices, plasters, liniments, aerosols, syrups, oral preparations, eye drops, and nasal drops for the treatment and prevention of bacterial infectious diseases, as well as for disinfection and sterilization.

[0010] WO 2020 / 108880 A1 discloses a composition for the treatment of mucous membranes and wounds. In addition to femotaxidine, the composition contains a defoamer.

[0011] WO 2020 / 108881 A1 discloses a composition for the treatment of mucous membranes and wounds which contains a surfactant in addition to femotaxidine.

[0012] There is still a need for antimicrobial products.

[0013] TASK AND SOLUTION

[0014] The invention is based on the object of providing an antimicrobially effective product which, in particular, at least partially avoids the disadvantages mentioned in connection with the prior art.

[0015] This object is achieved according to the invention by an antimicrobially active product having the features of independent claim 1. Preferred embodiments of the antimicrobially active product are the subject of the dependent claims and the description. The wording of all claims is hereby incorporated into the description by express reference.

[0016] The invention relates to an antimicrobially active product comprising a carrier and a dihydrotriazine compound, a tautomer thereof or a salt thereof, wherein the dihydrotriazine compound, the tautomer thereof or the salt thereof is bound to the carrier.

[0017] The dihydrotriazine compound has the following general formula I:

[0018] Formula I where

[0019] R-, (i) a phenyl group or a phenylalkyl group, each of which is optionally substituted by 1 to 3 substituents selected from the group consisting of C 1-6 alkoxy group, hydroxy group, a halogen atom, C 1-6 haloalkyl group, C 1-6 alkyl group, a sulfonamido group and C 1-6 haloalkoxy group, (ii) a naphthyl group or a naphthylalkyl group, (iii) a heterocyclic group, a heterocyclic alkyl group or a heterocyclic aminoalkyl group, (iv) an alkyl group having 1 to 16 carbon atoms or (v) a cycloalkyl group or a cycloalkylalkyl group, a hydrogen atom bonded to the nitrogen atom at position 1 or 3 of the dihydrotriazine ring,

[0020] R2 and R3 independently represent a hydrogen atom or a methyl group,

[0021] R4 represents an alkyl group having 7 to 16 carbon atoms, and the dashed line indicates that the position of a double bond lies either between positions 1 and 2 or between positions 2 and 3 of the dihydrotriazine ring. For the purposes of the present invention, the term “dihydrotriazine compound” is understood to mean a compound with a six-membered triazine ring having only two double bonds, i.e. a so-called dihydrotriazine ring, wherein the triazine ring or dihydrotriazine ring has a ring nitrogen atom at each of positions 1, 3, and 5 and a ring carbon atom at each of positions 2, 4, and 6, and wherein the position of one double bond lies between positions 4 and 5 of the triazine or dihydrotriazine ring, and the position of the other, i.e. second or remaining, double bond lies either between positions 1 and 2 or between positions 2 and 3 of the triazine or dihydrotriazine ring.

[0022] The term “fungi” in the context of the present invention may mean unicellular or multicellular fungi.

[0023] For the purposes of the present invention, the term “yeasts” refers to single-celled fungi which reproduce by budding or division (splitting) (so-called yeast fungi).

[0024] For the purposes of the present invention, the term “phenyl group” is understood to mean a benzene residue, i.e. the atomic group -C6H5.

[0025] For the purposes of the present invention, the term “benzyl group” is understood to mean the phenylmethyl group -CH2-C6H5, formerly also referred to as a-tolyl group.

[0026] For the purposes of the present invention, the term "phenylalkyl group" means a group in which a linear, i.e., unbranched, or branched alkyl group or alkylene group, in particular having 1 to 6 carbon atoms, is bonded to a phenyl group. The alkyl group or alkylene group can be a substituted or unsubstituted alkyl group or alkylene group. The phenylalkyl group is preferably a benzyl group, methylbenzyl group, such as, in particular, 4-methylbenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylpropyl group, 2-phenylpropyl group, or 3-phenylpropyl group.

[0027] A benzene ring of the phenyl or phenylalkyl group can have one to three substituents, in particular selected from the group consisting of halogen atom, hydroxy group, C^-alkyl group, C-, C-haloalkyl group, C-, C-haloalkoxy group, C-, C-haloalkoxy group, and sulfonamido group. The term "halogen atom" in the context of the present invention can mean a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0028] For the purposes of the present invention, the term "C^C-alkyl group" can mean a corresponding, i.e., linear or branched alkyl group having 1 to 6 carbon atoms. The alkyl group can be a substituted or unsubstituted alkyl group. For example, the C^-alkyl group can be a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, sec-pentyl group, isopentyl group, neopentyl group, n-hexyl group, or isohexyl group.

[0029] The term “C^e-haloalkyl group” in the sense of the present invention can mean in particular a chloromethyl group, bromomethyl group, 1-chloroethyl group or trifluoromethyl group.

[0030] The term “C^-alkoxy group” in the sense of the present invention can mean in particular a methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group or isobutoxy group.

[0031] The term “Ci.6-haloalkoxy group” in the sense of the present invention can in particular mean a trifluoromethoxy group.

[0032] The term “naphthyl group” in the sense of the present invention can mean a 1-naphthyl group or a 2-naphthyl group.

[0033] For the purposes of the present invention, the term "naphthylalkyl group" means a group in which a linear, i.e., unbranched, or branched alkyl group, in particular having 1 to 6 carbon atoms, is bonded to a naphthyl group. The alkyl group can be a substituted or unsubstituted alkyl group. The naphthylalkyl group is preferably a 1-naphthylmethyl group, 2-naphthylmethyl group, 1-naphthylethyl group, or 2-naphthylethyl group.

[0034] The term “heterocyclic group” in the context of the present invention means a three- to six-membered heterocyclic group which contains one to three atoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom, wherein a benzene ring may be fused or condensed to the heterocyclic group. The heterocyclic group may, for example, be a pyridyl group, a pyrazinyl group, a thiazolyl group, a piperidyl group, a piperazyl group, a tetrahydrofuryl group, a thienyl group, a pyrrolyl group, a pyrrolidinyl group, an oxazolyl group, an imidazolyl group, an isooxazolyl group, an isothiazolyl group, a pyrazolyl group, a tetrahydropyranyl group, a 2-oxotetrahydropyranyl group, a pyrimidinyl group, a pyradizinyl group, a morpholinyl group, a 1,3,5-triazinyl group, a 1,2,4-triazinyl group, a quinolyl group or an isoquinolyl group.

[0035] In particular, the heterocyclic group in the sense of the present invention can be a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 2-furyl group, a 2-thiazolyl group, a 1-piperidyl group, a 1-piperazyl group, a 2-quinolyl group, a 3-quinolyl group, a 4-quinolyl group, a 5-quinolyl group, an 8-quinolyl group, a 1-isoquinolyl group, a 3-isoquinolyl group, a 4-isoquinolyl group or a 5-isoquinolyl group.

[0036] The term "heterocyclic alkyl group" in the sense of the present invention means a group in which a linear, i.e. unbranched, or branched alkyl group, in particular having 1 to 6 carbon atoms, is bonded to a heterocyclic group, in particular as defined or described in the previous paragraphs. The alkyl group can be a substituted or unsubstituted alkyl group. The heterocyclic alkyl group is preferably a 2-pyridylmethyl group, 3-pyridylmethyl group, 4-

[0037] Pyridylmethyl group, 2-pyridylethyl group, 3-pyridylethyl group, 4-pyridylethyl group,

[0038] Pyrazinylmethyl group, pyrazinylethyl group, 2-furylmethyl group, 2-furylethyl group, 2-

[0039] Thiazolylmethyl group, 2-thiazolylethyl group, 4-piperidylmethyl group, 2-

[0040] Quinolylmethyl group, 3-quinolylmethyl group, 4-quinolylmethyl group, 5-

[0041] Quinolylmethyl group, 8-quinolylmethyl group, 1-isoquinolylmethyl group 3-

[0042] Isoquinolylmethyl group, 4-isoquinolylmethyl group or 5-isoquinolylmethyl group.

[0043] For the purposes of the present invention, the term "heterocyclic aminoalkyl group" means a group in which a linear, i.e., unbranched, or branched alkyl group, in particular having 1 to 12 carbon atoms, is bonded to a heterocyclic amino group. The alkyl group can be a substituted or unsubstituted alkyl group. The heterocyclic aminoalkyl group is preferably a 4-amino-dihydro-1,3,5-triazin-2-ylamino group, a 4-alkylamino-dihydro-1,3,5-triazin-2-ylamino group, or a 4-phenylalkylamino-dihydro-1,3,5-triazin-2-ylamino group.

[0044] The term “alkyl group having 1 to 16 carbon atoms” in the context of this

[0045] In the invention, a linear, i.e., unbranched, or branched alkyl group having 1 to 16 carbon atoms. The alkyl group can be a substituted or unsubstituted alkyl group. The alkyl group having 1 to 16 carbon atoms is preferably a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-hexyl group, n-heptyl group, n-octyl group, tert-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, or n-hexadecyl group.

[0046] For the purposes of the present invention, the term "cycloalkyl group" refers in particular to a cycloalkyl group having 3 to 6 carbon atoms. For example, the cycloalkyl group can be a cyclopropyl group, cyclobutyl group, cyclopentyl group, or cyclohexyl group.

[0047] For the purposes of the present invention, the term "cycloalkylalkyl group" means, in particular, a group in which a linear, i.e., unbranched, or branched alkyl group, in particular having 1 to 6 carbon atoms, is bonded to a cycloalkyl group, in particular as defined or described in the previous paragraph. The alkyl group can be a substituted or unsubstituted alkyl group. The cycloalkylalkyl group is preferably a cyclohexylmethyl group, a 1-cyclohexylethyl group, or a 2-cyclohexylethyl group.

[0048] For the purposes of the present invention, the term "alkyl group having 7 to 16 carbon atoms" means a linear, i.e., unbranched, or branched alkyl group having 7 to 16 carbon atoms. The alkyl group can be a substituted or unsubstituted alkyl group. The alkyl group having 7 to 16 carbon atoms is preferably an n-heptyl group, n-octyl group, tert-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, or n-hexadecyl group.

[0049] The term "salt" used in connection with the dihydrotriazine compound of general formula I can, within the meaning of the present invention, mean, in particular, a salt with an organic acid, such as formic acid, acetic acid, propionic acid, lactic acid, butyric acid, isobutyric acid, malic acid, maleic acid, malonic acid, fumaric acid, succinic acid, succinic acid monoamide, glutaric acid, tartaric acid, oxalic acid, citric acid, glycolic acid, glucuronic acid, ascorbic acid, aspartic acid, glutamic acid, benzoic acid, phthalic acid, salicylic acid, anthranilic acid, benzenesulfonic acid, p-toluenesulfonic acid, or methanesulfonic acid. The invention advantageously provides antimicrobially treated products which, on the one hand, have good efficacy against bacteria and fungi and, on the other hand, exhibit good compatibility with living tissue, so that they can be used in particular on skin, mucous membranes, and wounds.It has also been found that, particularly during prolonged contact, no imitative reactions occur, for example due to toxic degradation or by-products.

[0050] In the embodiment of the invention,

[0051] R-, a phenyl group or a phenylalkyl group, each of which is optionally substituted by 1 to 3 substituents selected from the group consisting of fluorine atom, chlorine atom, hydroxy group, methyl group, tert-butyl group, trifluoromethyl group and methoxy group,

[0052] R^ is a hydrogen atom bonded to the nitrogen atom at position 1 or 3 of the dihydrotriazine ring,

[0053] R2 and R3 each represent a methyl group and

[0054] R4an n-octyl group, n-nonyl group or n-decyl group.

[0055] Preferred means / means

[0056] R-, a phenyl group, a benzyl group or a 2-phenylethyl group, each of which is optionally substituted by 1 to 3 substituents selected from the group consisting of fluorine atom, chlorine atom, hydroxy group, methyl group, tert-butyl group, trifluoromethyl group and methoxy group,

[0057] R^ is a hydrogen atom bonded to the nitrogen atom at position 1 or 3 of the dihydrotriazine ring,

[0058] R2 and R3 each represent a methyl group and

[0059] R4an n-octyl group, n-nonyl group or n-decyl group.

[0060] Particularly preferred means / means

[0061] R-, a benzyl group which is optionally substituted by 1 to 3 substituents selected from the group consisting of fluorine atom, chlorine atom, hydroxy group, methyl group, tert-butyl group, trifluoromethyl group and methoxy group, preferably by 1 to 3 methyl groups, particularly preferably by a methyl group,

[0062] R^ is a hydrogen atom bonded to the nitrogen atom at position 1 or 3 of the dihydrotriazine ring,

[0063] R2 and R3 each represent a methyl group and

[0064] R4 represents an n-octyl group, n-nonyl group or n-decyl group. In a further embodiment of the invention

[0065] R-, a phenyl group, 4-chlorophenyl group, 2,4-difluorophenyl group, 2,3,4-trifluorophenyl group, 4-tert-butylphenyl group, 4-methoxyphenyl group, 2-methoxy-4-tert-butylphenyl group, 4-trifluoromethoxyphenyl group, benzyl group, methylbenzyl group such as in particular 4-methylbenzyl group, 4-methoxybenzyl group, 3,4-dimethoxybenzyl group, 4-hydroxybenzyl group, 3,4-dichlorobenzyl group, 2,3,4-trichlorobenzyl group, 4-trifluoromethylbenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylpropyl group, 2-phenylpropyl group or 3-phenylpropyl group, preferably a methylbenzyl group, particularly preferably a 4-methylbenzyl group, a hydrogen atom which is at position 1 or 3 of the dihydrotriazine ring is bonded to the nitrogen atom,

[0066] R2 and R3 each represent a methyl group and

[0067] R4an n-octyl group, n-nonyl group or n-decyl group.

[0068] In a further embodiment of the invention, R- represents a methylbenzyl group, preferably a 4-methylbenzyl group, and / or R2 and R3 each represent a methyl group and / or R4 represents an n-octyl group. Preferably, R- represents a methylbenzyl group, preferably a 4-methylbenzyl group, R2 and R3 each represent a methyl group, and R4 represents an n-octyl group.

[0069] In a further embodiment of the invention, R- means / means a methylbenzyl group, preferably 4-methylbenzyl group, R^ means a hydrogen atom which is bonded to the nitrogen atom at position 1 or 3 of the dihydrotriazine ring, R2 and R3 each means a methyl group and R4 means an n-octyl group.

[0070] The dihydrotriazine compound particularly preferably has the following formula la: Formula la Alternatively, the dihydrotriazine compound may have the following formula Ib:

[0071] Formula Ib

[0072] In a further embodiment of the invention, the dihydrotriazine compound, the tautomer thereof or the salt thereof is 4-octylamino-1,6-dihydro-6,6-dimethyl-2-(4'-methylbenzylamino)-1,3,5-triazine gluconate, which can also be referred to as 6,6-dimethyl-N2-(4-methylbenzyl)-N4-octyl-1,6-dihydro-[1,3,5]triazine-2,4-diamine gluconate. Preferably, the dihydrotriazine compound, tautomer thereof, or salt thereof is 4-octylamino-1,6-dihydro-6,6-dimethyl-2-(4'-methylbenzylamino)-1,3,5-triazine-D-gluconate, which may also be referred to as 6,6-dimethyl-N2-(4-methylbenzyl)-N4-octyl-1,6-dihydro-[1,3,5]triazine-2,4-diamine-D-gluconate. The dihydrotriazine compound or dihydrotriazine compound salt disclosed in this paragraph has been found to be particularly effective in achieving the advantages of the invention.

[0073] The dihydrotriazine compound or the dihydrotriazine compound salt 4-octylamino-1,6-dihydro-6,6-dimethyl-2-(4'-methylbenzylamino)-1,3,5-triazine-D-gluconate mentioned in the previous paragraph is commercially available under the name “Femotaxidin” and can be represented by the following formula la # be shown: Formula la #

[0074] In a further embodiment of the invention, the dihydrotriazine compound, the tautomer thereof or the salt thereof is 4-octylamino-3,6-dihydro-6,6-dimethyl-2-(4'-methylbenzylamino)-1,3,5-triazine gluconate, in particular 4-octylamino-3,6-dihydro-6,6-dimethyl-2-(4'-methylbenzylamino)-1,3,5-triazine-D-gluconate.

[0075] Preferably, the concentration of the dihydrotriazine compound, the tautomer thereof or the salt thereof is selected such that the antimicrobially active product is antimicrobially active against bacteria, in particular against gram-positive bacteria and / or against gram-negative bacteria, preferably against both gram-positive bacteria and gram-negative bacteria.

[0076] In a further embodiment of the invention, the dihydrotriazine compound, the tautomer thereof or the salt thereof has a concentration of 0.001 mg to 20 mg, in particular 0.01 mg to 5 mg, preferably 0.01 mg to 2 mg, per gram of the carrier.

[0077] In a further embodiment of the invention, the dihydrotriazine compound, the tautomer thereof or the salt thereof is part of a composition.

[0078] In principle, the composition can be in the form of a solution (such as an aqueous solution), a suspension (such as an aqueous suspension), an emulsion (such as an aqueous emulsion), tablets, pills, capsules, a powder, granules, a suppository, an injection, a paste, an ointment, a cream, a gel (such as hydrogels), a gel-like cream, a lotion, a syrup or an aerosol.

[0079] The composition is preferably in the form of an aqueous, i.e., water-containing, composition. In particular, the composition may be in the form of a solution, in particular an aqueous solution, or a gel, in particular a hydrogel.

[0080] In a further embodiment of the invention, the composition further comprises at least one further component, in particular at least two further components. The at least one further component, in particular the at least two further components, is, in particular are, preferably selected from the group consisting of surface-active compound, complexing agent, film former and foam-inhibiting compound. The term “surface-active compound” in the sense of the present invention is to be understood as a compound which, through its presence in a liquid, in particular in water or an aqueous liquid, changes the surface tension and / or interfacial tension thereof, in particular between two phases. The surface-active compound in the sense of the present invention can in particular be a surfactant.

[0081] The surface-active compound can be selected from the group consisting of non-ionic surface-active compound, cationic surface-active compound, zwitterionic surface-active compound and combinations, in particular mixtures, of at least two of the aforementioned surface-active compounds.

[0082] For the purposes of the present invention, the term “nonionic surface-active compound” refers to a surface-active compound which does not contain any dissociable functional groups and therefore does not separate into ions in water or an aqueous liquid.

[0083] For the purposes of the present invention, the term “zwitterionic surface-active compound” refers to a compound which has both a negatively and a positively charged functional group (so-called amphoteric surface-active compound).

[0084] For the purposes of the present invention, the term “cationic surface-active compound” is to be understood as meaning a surface-active compound which has a positively charged functional group but not an additional negatively charged group.

[0085] A non-ionic or zwitterionic surfactant compound has the particular advantage that there are no or few interactions with the dihydrotriazine compound and that it is also very well tolerated by skin, mucous membranes and wounds.

[0086] The nonionic surfactant is preferably selected from the group consisting of poloxamer, fatty alcohol alkoxylate such as fatty alcohol ethoxylate, polyvinylpyrrolidone, alkyl polyglucoside, and combinations, in particular mixtures, of at least two of the aforementioned nonionic surfactants. The nonionic surfactants mentioned in this paragraph and described in more detail below have proven particularly suitable for reducing or avoiding the adverse irritation potential of the dihydrotriazine compound, its tautomer, or its salt, from a wound therapy perspective.

[0087] For the purposes of the present invention, the term “poloxamer” is understood to mean a block copolymer of ethylene oxide and propylene oxide (so-called EO / PO block copolymers).

[0088] The poloxamer preferably has 2 to 130 structural units -CH2-CH2-O- and / or 15 to 67 structural units -CHCH3-CH2-O- per molecule.

[0089] The poloxamer may in particular be poloxamer 407, poloxamer 188 or a combination, in particular a mixture, thereof.

[0090] The use of a poloxamer as a surface-active compound may be particularly preferred according to the invention, since poloxamers, in addition to surface-active properties, also possess foam-suppressing or foam-reducing properties and / or emulsifying properties. This allows foam formation attributable to the dihydrotriazine compound, its tautomer, or its salt to be dampened, mitigated, or suppressed with particular advantage.

[0091] The use of polyvinylpyrrolidone as a surface-active compound may also be particularly preferred according to the invention, since this compound possesses emulsifying properties in addition to its surface-active properties. The advantages mentioned in the previous paragraph apply accordingly. In addition, the use of polyvinylpyrrolidone has the advantage that it can bind water and thus act as a viscosity regulator.

[0092] For the purposes of the present invention, the term "fatty alcohol alkoxylate" is understood to mean a non-ionic surface-active compound whose lipophilic moiety comprises a fatty alcohol, consists of a fatty alcohol, or is derived from a fatty alcohol, and whose hydrophilic moiety comprises a polyalkylene glycol, in particular a short- or medium-chain polyalkylene glycol, or consists of a polyalkylene glycol, in particular a short- or medium-chain polyalkylene glycol, or is derived from a polyalkylene glycol, in particular a short- or medium-chain polyalkylene glycol. The fatty alcohol and the polyalkylene glycol can, independently of one another, have 8 to 22 carbon atoms. The fatty alcohol can, in particular, be an alcohol derived from caprylic, capric, lauric, palmitic, stearic, or oleic acid, or from branched isononyl, isundecyl, isotridecyl, isopentadecyl, or isononadecyl alcohols.In the context of the present invention, the fatty alcohol alkoxylate can also be referred to as polyalkylene glycol ether.

[0093] As already mentioned, the fatty alcohol alkoxylate can in particular be a fatty alcohol ethoxylate.

[0094] The fatty alcohol ethoxylate is preferably a polyoxyethylene ether of lauryl alcohol, a polyoxyethylene ether of myristyl alcohol, a polyoxyethylene ether of cetyl alcohol, a polyoxyethylene ether of cetylstearyl alcohol, a polyoxyethylene ether of stearyl alcohol, a polyoxyethylene ether of oleyl alcohol, a polyoxyethylene ether of isononane alcohol, a polyoxyethylene ether of isoundecane alcohol, a polyoxyethylene ether of isotridecane alcohol, a polyoxyethylene ether of isopentadecane alcohol, a polyoxyethylene ether of isoheptadecane alcohol, a polyoxyethylene ether of isononadecane alcohol or a combination, in particular a mixture, of at least two of the aforementioned polyoxyethylene ethers.

[0095] The fatty alcohol ethoxylate can in particular be selected from the group consisting of polyoxyethylene (4) lauryl ether, polyoxyethylene (7) lauryl ether, polyoxyethylene (9) lauryl ether, polyoxyethylene (23) lauryl ether, polyoxyethylene (2) cetyl ether, polyoxyethylene (10) cetyl ether, polyoxyethylene (20) cetyl ether, polyoxyethylene (6) cetyl stearyl ether, polyoxyethylene (20) cetyl stearyl ether, polyoxyethylene (25) cetyl stearyl ether, polyoxyethylene (2) stearyl ether, polyoxyethylene (10) stearyl ether, polyoxyethylene (20) stearyl ether, polyoxyethylene (2) oleyl ether, polyoxyethylene (10) oleyl ether, polyoxyethylene (20) oleyl ether, polyoxyethylene (10) monodecyl ether, Polyoxyethylene (10) tridecyl ether and combinations, in particular mixtures, of at least two of the aforementioned fatty alcohol ethoxylates.

[0096] In other words, the fatty alcohol ethoxylate can in particular be selected from the group consisting of Laureth-4, Laureth-7, Laureth-9, Laureth-23, Ceteth-2, Ceteth-10, Ceteth-20, Ceteareth-6, Ceteareth-20, Ceteareth-25, Steareth-2, Steareth-10, Steareth-20, Oleth-2, Oleth-10, Oleth-20, Deceth-10, Trideceth-10 and combinations, in particular mixtures, of at least two of the aforementioned fatty alcohol ethoxylates.

[0097] Fatty alcohol alkoxylates, especially fatty alcohol ethoxylates, have the advantage that they not only have surface-active properties but also act as emulsifiers. For the purposes of the present invention, the term "alkyl polyglucoside" refers to a nonionic sugar surfactant that contains one or more glucose units and an alkyl radical, particularly a long-chain alkyl radical, or consists of one or more glucose units and an alkyl radical, particularly a long-chain alkyl radical. The glucose unit(s) act as the hydrophilic component, while the alkyl radical represents the hydrophobic group.

[0098] The alkyl polyglucoside preferably has 1 to 5 glucose building blocks and / or an alkyl radical having 6 carbon atoms to 22 carbon atoms, preferably 6 carbon atoms to 20 carbon atoms, in particular 6 carbon atoms to 16 carbon atoms, in particular 8 carbon atoms to 14 carbon atoms.

[0099] The alkyl polyglucoside is preferably a C8 to C2o alkyl polyglucose, in particular C8 to C 16 -Alkylpolyglucose.

[0100] The alkyl polyglucoside is particularly preferably lauryl polyglucose, decyl polyglucose, cocoyl polyglucose, or a combination, in particular a mixture, of at least two of the aforementioned alkyl polyglucosides. The alkyl radical of decyl polyglucose preferably has 8 to 16 carbon atoms, in particular 10 carbon atoms. The alkyl radical of lauryl polyglucose preferably has 12 to 16 carbon atoms, in particular 12 carbon atoms. The alkyl radical of cocoyl polyglucose preferably has 8 to 16 carbon atoms.

[0101] Alkyl polyglucosides also have the advantage that they not only have surface-active properties, but also represent emulsifying compounds.

[0102] The zwitterionic surface-active compound is preferably an alkyl betaine and / or alkylamidoalkyl betaine, in particular an alkylamidoethyl betaine, alkylamidopropyl betaine or a combination, in particular a mixture, thereof.

[0103] The alkyl betaine may preferably have alkyl groups which independently of one another have 8 carbon atoms to 22 carbon atoms, in particular 8 to 18 carbon atoms.

[0104] The alkylamidoalkylbetaine particularly preferably has at least one fatty acid residue, in particular only one fatty acid residue, (only) two fatty acid residues, or three fatty acid residues. The at least one fatty acid residue preferably has 8 to 22 carbon atoms, in particular 8 to 18 carbon atoms. The fatty acid residue can in particular be a saturated or unsaturated fatty acid residue. The fatty acid residue is preferably a caprylic acid residue, capric acid residue, undecylenic acid residue (undec-10-enoic acid residue), undecylic acid residue (n-undecanoic acid residue), lauric acid residue, stearic acid residue, ricinoleic acid residue, or coconut fatty acid residue.

[0105] Preferably, the alkylamidoalkylbetaine is selected from the group consisting of caprylamidoalkylbetaine, caprimidoalkylbetaine, undecylenamidoalkylbetaine, undecylamidoalkylbetaine, lauramidoalkylbetaine, lauryldimethylaminoacetic acidbetaine, stearinamidoalkylbetaine, ricinolamidoalkylbetaine, cocamidoalkylbetaine and combinations, in particular mixtures, of at least two of the aforementioned alkylamidoalkylbetaines.

[0106] The alkylamidoethyl betaine is preferably an alkylamidoethyl betaine based on a fatty acid, in particular a fatty acid having 8 to 22 carbon atoms, especially 8 to 18 carbon atoms. The fatty acid can be, in particular, a saturated or unsaturated fatty acid. The fatty acid is preferably caprylic acid, capric acid, undecylenic acid (undec-10-enoic acid), undecylic acid (n-undecanoic acid), lauric acid, stearic acid, ricinoleic acid, or coconut fatty acid.

[0107] The alkylamidoethylbetaine is particularly preferably selected from the group consisting of caprylamidoethylbetaine, caprimidoethylbetaine, undecylenamidoethylbetaine, undecylamidoethylbetaine, lauramidoethylbetaine, cocamidoethylbetaine, stearinamidoethylbetaine, ricinolamidoethylbetaine and combinations, in particular mixtures, of at least two of the aforementioned alkylamidoethylbetaines.

[0108] The alkylamidopropyl betaine is preferably an alkylamidopropyl betaine based on a fatty acid, in particular a fatty acid having 8 to 22 carbon atoms, especially 8 to 18 carbon atoms. The fatty acid can be, in particular, a saturated or unsaturated fatty acid. The fatty acid is preferably caprylic acid, capric acid, undecylenic acid (undec-10-enoic acid), undecylic acid (n-undecanoic acid), lauric acid, stearic acid, ricinoleic acid, or coconut fatty acid.

[0109] Particularly preferably, the alkylamidopropyl betaine is selected from the group consisting of caprylamidopropyl betaine, caprimidopropyl betaine, undecylenamidopropyl betaine, undecylamidopropyl betaine, cocamidopropyl betaine, stearinamidopropyl betaine, ricinolamidopropyl betaine and combinations, in particular mixtures, of at least two of the aforementioned alkylamidopropyl betaines.

[0110] The cationic surface-active compound preferably has a saturated or unsaturated organic radical, in particular an alkyl group, having 8 to 22 carbon atoms.

[0111] The cationic surface-active compound can in particular be selected from the group consisting of distearyldimethylammonium chloride, didecyldimethylammonium chloride, cetyltrimethylammonium chloride, cetyltrimethylammonium bromide, cetylpyridinium chloride, mecetronium ethyl sulfate and combinations, in particular mixtures, thereof.

[0112] The surface-active compound preferably has a proportion of 0.001 wt.% to 50 wt.%, in particular 0.01 wt.% to 40 wt.%, preferably 0.1 wt.% to 30 wt.%, based on the total weight of the composition.

[0113] The complexing agent is preferably selected from the group consisting of citric acid, tartaric acid, succinic acid, methylglycine diacetate, ethyldiaminetetraacetate, N,N'-bis-(carboxymethyl)-L-glutamate, polyaspartic acid, iminodisuccinate, phosphonates, phosphonobutanetricarboxylic acid, lauryl alcohol diphosphonic acid, editronic acid, salts of the aforementioned complexing agents, and combinations, in particular mixtures, of at least two of the aforementioned complexing agents. Complexing agents can advantageously bind unwanted metal ions. Metal ions can be present in raw materials and / or the carrier and can have a negative impact on the stability of the product. Furthermore, complexing agents have the advantage of positively influencing stability against microorganisms.

[0114] The complexing agent preferably has a proportion of 0.001 wt.% to 10 wt.%, in particular 0.01 wt.% to 5 wt.%, preferably 0.01 wt.% to 1 wt.%, based on the total weight of the composition.

[0115] For the purposes of the present invention, the term “film former” is to be understood as meaning a macro- or low-molecular substance, preferably a polymer, in particular a long- or short-chain polymer, which ensures the formation of a coherent film in a coating material.

[0116] In principle, the film former can be a hydrophilic film former and / or a hydrophobic film former. The film former is preferably selected from the group consisting of polyvinylpyrrolidone, compounds derived from polyvinylpyrrolidone (e.g., styrene / vinylpyrrolidone copolymer, vinylpyrrolidone / eicosene copolymer, or vinylpyrrolidone / dimethylaminoethyl methacrylate copolymer), polyvinyl alcohol, polyethylene glycols, polysaccharides, chitosan, chitosan oligomers, chitosan derivatives, cellulose derivatives, hypromellose, polyacrylic acids, polyurethane, polyquaternium compounds, copolymers of vinylpyrrolidone and vinyl acetate, protein hydrolysates, proteins (such as sericin), natural resins, shellac, rosin, benzoin, or sandarac, and combinations, in particular mixtures, of at least two of the aforementioned film formers.

[0117] The film former preferably has a proportion of 0.001 wt.% to 10 wt.%, in particular 0.01 wt.% to 5 wt.%, preferably 0.01 wt.% to 2 wt.%, based on the total weight of the composition.

[0118] For the purposes of the present invention, the term “foam-inhibiting compound” or “defoamer” refers to a compound which slows down or attenuates, i.e. mitigates or reduces, or avoids, foam formation, in particular foam formation attributable to the dihydrotriazine compound, the tautomer thereof or the salt thereof.

[0119] The foam-inhibiting compound or defoamer is preferably a different compound from the surface-active compound. In other words, the foam-inhibiting compound or defoamer and the surface-active compound are selected to be different from one another, i.e., they represent different compounds.

[0120] The foam-inhibiting compound or defoamer can in particular be selected from the group consisting of alkylamide, silicone, poloxamer and combinations, in particular mixtures, of at least two of the aforementioned foam-inhibiting compounds or defoamers.

[0121] The alkylamide can in particular be an alkylamide of the formula R5-NH-R6, where R5 is n-octyl, iso-octyl, or 2-ethylhexyl and R6 is n- or iso-octane, n- or isononane, or n- or isodecane. According to the invention, the alkylamide can also be a combination, in particular a mixture, of at least two corresponding alkylamides.

[0122] The silicone may be a polydimethylsiloxane, polyether siloxane (siloxane-polyethylene glycol or siloxane-polypropylene glycol), 3D-modified siloxane, also called crosslink siloxane, or a combination, in particular a mixture, of at least two of the aforementioned silicones.

[0123] The poloxamer preferably has 2 to 130 structural units -CH2-CH2-O- and / or 15 to 67 structural units -CHCH3-CH2-O- per molecule.

[0124] In particular, the poloxamer may be poloxamer 407, poloxamer 188 or a combination, in particular a mixture, thereof.

[0125] The foam-inhibiting compound or defoamer is particularly preferably selected from the group consisting of N-(2-ethylhexyl)-isononanamide, polydimethylsiloxane, polyether-siloxane such as siloxane-polyethylene glycol or siloxane-polypropylene glycol, 3D-modified siloxane, EO / PO block copolymers, and combinations, in particular mixtures, of at least two of the aforementioned foam-inhibiting compounds or defoamers. A suitable foam-inhibiting compound is commercially available, for example, under the name "Aldo LF."

[0126] Furthermore, the foam-inhibiting compound or defoamer can be a combination, in particular a mixture, of an alkylamide and a silicone. Such a combination is particularly advantageous with regard to suppressing or weakening foam formation of the dihydrazine compound of the general formula I, the tautomer thereof, or the salt thereof. In this case, the alkylamide can have a proportion, in particular active proportion, of 0.0001 wt.% to 0.1 wt.%, in particular 0.0005 wt.% to 0.05 wt.%, preferably 0.001 wt.% to 0.05 wt.%, based on the total weight of the composition, and the silicone can have a proportion, in particular active proportion, of 0.00001 wt.% to 0.01 wt.%, in particular 0.00002 wt.% to 0.005 wt.%, preferably 0.00005 wt.% to 0.005 wt.%, based on the total weight of the composition.

[0127] The foam-inhibiting compound preferably has a proportion of 0.0001 wt.% to 2 wt.%, in particular 0.0005 wt.% to 1.5 wt.%, preferably 0.001 wt.% to 1 wt.%, based on the total weight of the composition.

[0128] In principle, the dihydrotriazine compound, the tautomer thereof or the salt thereof and / or the at least one further constituent, in particular the at least two further constituents, in particular independently of one another, can be bound to the support covalently and / or non-covalently, in particular by hydrogen bonds and / or electrostatic, in particular ionic, interactions and / or hydrophobic interactions and / or van der Waals interactions, and / or coordinate, i.e., donative, bonds. In particular, the dihydrotriazine compound, the tautomer thereof or the salt thereof and / or the at least one further constituent, in particular the at least two further constituents, in particular independently of one another, can be bound to the support by adsorption, in particular physisorption and / or chemisorption.

[0129] In a further embodiment of the invention, the dihydrotriazine compound, the tautomer thereof or the salt thereof and / or the at least one further component, in particular the at least two further components, are reversibly bound, in particular reversibly covalently, to the carrier, in particular independently of one another.

[0130] In a further embodiment of the invention, the dihydrotriazine compound, the tautomer thereof, or the salt thereof, or the composition or the at least one further constituent, in particular the at least two further constituents, forms a coating or part of a coating of the carrier. The coating can coat the carrier only partially or completely. Furthermore, the coating can have a uniform or non-uniform layer thickness. In particular, the coating can have a layer thickness of 0.1 μm to 1000 μm, in particular 1 μm to 100 μm, preferably 10 μm to 100 μm.

[0131] In a further embodiment of the invention, the dihydrotriazine compound, the tautomer thereof or the salt thereof or the composition is dispersed within the carrier.

[0132] Furthermore, the composition may further comprise a solvent, in particular an organic solvent, preferably selected from the group consisting of alcohol, ketone, ether, ester and combinations, in particular mixtures, of at least two of the aforementioned solvents. The alcohol may be a monohydric alcohol and / or dihydric alcohol and / or trihydric alcohol, in particular having two to ten carbon atoms, preferably two to eight carbon atoms. The alcohol is preferably selected from the group consisting of methanol, ethanol, propan-1-ol, propan-2-ol, propane-1,2-diol, propane-1,3-diol, propane-1,2,3-triol, butane-1,3-diol, pentane-1,2-diol, hexane-1,2-diol, octane-1,2-diol, decane-1,2-diol, hexane-1,2-diol, gentane-1,2-diol and combinations, in particular mixtures, of at least two of the aforementioned alcohols. The ketone can in particular have three to eight carbon atoms.For example, the ketone can be butan-2-one. The ether can be tetrahydrofuran, for example. The ester can be, in particular, a carbonic acid ester, such as diethyl carbonate, and / or a carboxylic acid ester, such as ethyl acetate.

[0133] The organic solvent can particularly advantageously serve as a processing aid for homogenizing and / or uniformly distributing the composition on the support. The organic solvent can have a proportion of 0.001 wt.% to 95 wt.%, in particular 0.01 wt.% to 90 wt.%, preferably 0.01 wt.% to 70 wt.%, based on the total weight of the composition.

[0134] Alternatively, the antimicrobially active product can be free or essentially free of a solvent, in particular organic solvents, preferably an alcohol and / or ketone and / or ether and / or ester. This can be the case in particular if the solvent has a boiling point of up to 120°C, so that it evaporates during the manufacturing process of the antimicrobially active product. The term “essentially free” in this context means that the antimicrobially active product has a solvent content of < 5 wt.% and > 0 wt.%, in particular < 4 wt.% and > 0 wt.%, preferably < 3 wt.% and > 0 wt.%, in particular < 2 wt.% and > 0 wt.%, in particular < 1 wt.% and > 0 wt.%, based on the total weight of the antimicrobially active product.

[0135] Furthermore, the composition may further comprise a polyethylene glycol, polypropylene glycol or a mixture containing or consisting of polyethylene glycol and polypropylene glycol.

[0136] The composition may further comprise an acid, in particular for adjusting the pH. The acid may be an inorganic acid and / or an organic acid. The acid is preferably selected from the group consisting of hydrochloric acid, formic acid, acetic acid, glycolic acid, lactic acid, gluconic acid, gluconodeltalactone, malic acid, tartaric acid, and combinations, in particular mixtures, of at least two of the aforementioned acids.

[0137] The acid may have a proportion of 0.001 wt% to 10 wt%, in particular 0.01 wt% to 5 wt%, preferably 0.01 wt% to 2 wt%, based on the total weight of the composition.

[0138] The composition may further comprise an alkali or base to adjust a pH value compatible with the skin, mucous membranes, or wounds. The alkali or base may be selected from the group consisting of sodium hydroxide, potassium hydroxide, calcium hydroxide, magnesium hydroxide, ammonium hydroxide, organic amines, and combinations, especially mixtures, of at least two of the aforementioned alkalis or bases.

[0139] The organic amines can in particular be selected from the group consisting of monoethanolamine, triethanolamine, 2-amino-2-methyl-1-propanol,

[0140] Tetrahydroxypropylethylenediamine, tromethamine, monoisopropanolamine, triisopropanolamine and combinations, in particular mixtures, of at least two of the aforementioned organic amines.

[0141] Furthermore, the composition may further comprise water, in particular purified water or water for injection purposes.

[0142] In particular, the water can have a proportion of 0.01 wt.% to 99.99 wt.%, in particular 0.1 wt.% to 99.9 wt.%, preferably 0.1 wt.% to 99.8 wt.%, based on the total weight of the composition. In particular, the components of the composition can be supplemented with water to 100 wt.%.

[0143] Furthermore, the composition and / or carrier may be manufactured under controlled hygienic conditions or aseptically in a clean room.

[0144] In particular, the composition and / or carrier may be in sterilized form. For example, the composition and / or carrier may be sterilized by gamma irradiation, beta irradiation, plasma sterilization, steam sterilization, or ethylene oxide sterilization.

[0145] In a further embodiment of the invention, the carrier has a carrier material or the carrier consists of a carrier material, wherein the carrier material is selected from the group consisting of cellulose, microbially produced cellulose, cellulose-derived compounds, alkylcellulose, hydroxyalkylcellulose, hydroxyalkylmethylcellulose, hydroxyalkylethylcellulose, carboxymethylcellulose, chitosan, chitosan hydrolysates, chitosan derivatives, collagens, collagen hydrolysates, collagen derivatives, polysaccharides, alginates, agar, locust bean gum, pectin, carrageenan, gelatin, partially hydrolyzed gelatin, polyethylene, polypropylene, polyacrylonitrile, viscose, polyamide, polyurethane, polyester, silicone, polyhydroxyethyl methacrylate, poly-2-hydroxyethyl methacrylate and combinations, in particular mixtures, of at least two of the aforementioned carrier materials. In a further embodiment of the invention, the carrier is textile, i.e. designed as a textile product.In particular, the carrier may comprise a woven, knitted, braided, nonwoven or nonwoven fabric or be designed in the form of a woven, knitted, braided, nonwoven or nonwoven fabric.

[0146] Preferably, the carrier is designed as a textile fabric, in particular a woven, warp-knitted, braided, nonwoven or nonwoven fabric.

[0147] Alternatively, the carrier may be in the form of a three-dimensional textile product, in particular in the form of a woven fabric, knitted fabric, braided fabric, nonwoven fabric or nonwoven material.

[0148] In a further embodiment of the invention, the carrier is non-textile, i.e., designed as a non-textile product. In particular, the carrier can be designed as a film, foam, hollow plastic body, in particular a tubular or hose-shaped hollow plastic body, or as a blow-molded part, in particular an extrusion blow-molded part, or as a piercing jewelry.

[0149] In a further embodiment of the invention, the antimicrobially effective product is a medical device. The medical device is in particular selected from the group consisting of skin pad, wound pad, wound dressing, sponge or gauze, nonwoven cloth for skin cleansing, fabric or nonwoven material for non-invasive wound therapy (NPWT), nonwoven cloth or pad with abrasive fibers or bristles for gentle wound debridement, foam for gentle wound debridement, catheters, in particular urethral catheters, urinary catheters, stoma plates, stoma bags, foams with suction devices for the drainage of secretions and / or body fluids, e.g. from the esophagus, from the gastrointestinal tract, from the natural or artificially created anus, or from the respiratory tract.

[0150] Further features and advantages of the invention will become apparent from the following description of preferred embodiments. Individual features may be implemented individually or in combination with one another. The described embodiments serve merely to further explain the invention without limiting it thereto.

[0151] 1. A cotton fabric was soaked with a solution of the following composition:

[0152] 200 mg of the solution was applied per gram of cotton fabric. In another version, 100 mg of the solution was applied per gram of cotton fabric. The impregnated cotton fabric was dried and sterilized using one of the established sterilization methods.

[0153] 2. A polyethylene gauze was soaked with a solution of the following composition:

[0154] 10 mg to 100 mg of the solution was applied per gram of polyethylene gauze. The material was then dried at room temperature for two hours and sterilized using one of the established sterilization methods. 3. A gel of the following composition was applied to a piece of polyethylene gauze:

[0155] 200 mg of gel was applied per gram of polyethylene gauze. The gel and the finished product were prepared under aseptic conditions.

[0156] 4. An ointment of the following composition was applied to a polyethylene gauze:

[0157] 100 mg of the ointment was applied per gram of polyethylene gauze. The material was sterilized using one of the established sterilization methods. 5. A viscous solution of the following composition was applied to a polyurethane foam:

[0158] 200 mg of the solution was applied per gram of polyurethane foam. The material was dried for 5 hours at 30°C and sterilized using one of the established sterilization methods.

[0159] In one embodiment, the foam treated with the composition was combined with a polyethylene tube to form a medical device for the drainage of secretions and body fluids.

[0160] 6. A solution of the following composition was applied to a polyurethane foam:

[0161] 50 mg of the solution was applied per gram of polyurethane foam. In another version, 100 mg of the solution was applied per gram of polyurethane foam. After drying, the polyurethane foam was combined with a transparent, skin-adherent silicone polymer film to form a wound dressing. The wound dressing was sterilized using one of the established sterilization methods.

[0162] 7. A solution of the following composition was applied to a polyurethane foam:

[0163] 50 mg of solution was applied per gram of polyurethane foam. In further versions, 100 mg, 200 mg, and 500 mg of the solution were applied per gram of polyurethane foam. After drying, the polyurethane foam was bonded to a transparent, skin-adherent silicone polymer film to form a skin patch. The skin patch was sterilized using one of the established sterilization methods.

[0164] Metallic piercing materials were placed in the above solution, then dried for 2 hours at 30 °C and stored for further use.

[0165] 8. A solution of the following composition was prepared: Ten percent by weight of the solution was mixed with 10 percent by weight of another solution consisting of 90 percent by weight water and 10 percent by weight of a polysaccharide mixture (agar and locust bean gum). 2 mm thick sheets were formed and dried. The sheets were sterilized using one of the established sterilization methods.

[0166] 9. A liquid mixture of the following composition was prepared:

[0167] The surface of a polyurethane catheter was evenly coated with the mixture, and the catheter was dried at 40 °C for five hours. The resulting product was packaged and sterilized using one of the established sterilization methods.

Claims

Patent claims 1. An antimicrobially active product comprising a carrier and a dihydrotriazine compound, a tautomer thereof or a salt thereof, wherein the dihydrotriazine compound, the tautomer thereof or the salt thereof is bound to the carrier and the dihydrotriazine compound has the following general formula I: Formula I where R-, (i) a phenyl group or a phenylalkyl group, each of which is optionally substituted with 1 to 3 substituents selected from the group consisting of C 1-6 alkoxy group, hydroxy group, a halogen atom, C 1-6 haloalkyl group, C 1-6 alkyl group, a sulfonamido group and C 1-6 haloalkoxy group, (ii) a naphthyl group or a naphthylalkyl group, (iii) a heterocyclic group, a heterocyclic alkyl group or a heterocyclic aminoalkyl group, (iv) an alkyl group having 1 to 16 carbon atoms or (v) a cycloalkyl group or a cycloalkylalkyl group, a hydrogen atom bonded to the nitrogen atom at position 1 or 3 of the dihydrotriazine ring, R2 and R3 independently represent a hydrogen atom or a methyl group, R4 represents an alkyl group having 7 to 16 carbon atoms and the dashed line indicates that the position of a double bond is either between positions 1 and 2 or between positions 2 and 3 of the dihydrotriazine ring.

2. Antimicrobially active product according to claim 1, characterized in that R- represents a phenyl group or a phenylalkyl group, in particular benzyl group, each of which is optionally substituted by 1 to 3 substituents selected from the group consisting of fluorine atom, chlorine atom, hydroxy group, methyl group, tert-butyl group, trifluoromethyl group and methoxy group, represents a hydrogen atom bonded to the nitrogen atom at position 1 or 3 of the dihydrotriazine ring, R2 and R3 each represent a methyl group and R4 represents an n-octyl group, n-nonyl group or n-decyl group.

3. Antimicrobially active product according to claim 1 or 2, characterized in that Ri is a phenyl group, 4-chlorophenyl group, 2,4-difluorophenyl group, 2,3,4-trifluorophenyl group, 4-tert-butylphenyl group, 4-methoxyphenyl group, 2-methoxy-4-tert-butylphenyl group, 4-trifluoromethoxyphenyl group, benzyl group, methylbenzyl group, 4-methylbenzyl group, 4-methoxybenzyl group, 3,4-dimethoxybenzyl group, 4-hydroxybenzyl group, 3,4-dichlorobenzyl group, 2,3,4-trichlorobenzyl group, 4-trifluoromethylbenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylpropyl group, 2-phenylpropyl group or 3-phenylpropyl group, preferably a 4-methylbenzyl group, R^ represents a hydrogen atom bonded to the nitrogen atom at position 1 or 3 of the dihydrotriazine ring, R2 and R3 each represent a methyl group and R4 represents an n-octyl group, n-nonyl group or n-decyl group.

4. Antimicrobially active product according to one of the preceding claims, characterized in that RT represents a methylbenzyl group, preferably 4-methylbenzyl group, and / or R2 and R3 each represent a methyl group and / or R4 represents an n-octyl group.

5. Antimicrobially active product according to one of the preceding claims, characterized in that RT represents a methylbenzyl group, preferably 4-methylbenzyl group, R^ represents a hydrogen atom bonded to the nitrogen atom at position 1 or 3 of the dihydrotriazine ring, R2 and R3 each represent a methyl group and R4 represents an n-octyl group.

6. Antimicrobially active product according to one of the preceding claims, characterized in that the dihydrotriazine compound of the general formula I or the salt thereof is 4-octylamino-1,6-dihydro-6,6-dimethyl-2-(4'-methylbenzylamino)-1,3,5-triazine gluconate, 4-octylamino-3,6-dihydro-6,6-dimethyl-2-(4'-methylbenzylamino)-1,3,5-triazine gluconate or a tautomer thereof.

7. Antimicrobially active product according to one of the preceding claims, characterized in that the dihydrotriazine compound, the tautomer thereof or the salt thereof has a concentration of 0.001 mg to 20 mg, in particular 0.1 mg to 10 mg, preferably 0.1 mg to 2 mg, per gram of the carrier.

8. Antimicrobially active product according to one of the preceding claims, characterized in that the dihydrotriazine compound, the tautomer thereof or the salt thereof is a component of a composition.

9. Antimicrobially active product according to claim 8, characterized in that the composition further comprises at least one further component, in particular at least two further components, selected from the group consisting of surface-active compound, complexing agent, film former and foam-inhibiting compound.

10. Antimicrobially active product according to one of the preceding claims, in particular according to claim 9, characterized in that the dihydrotriazine compound, the tautomer thereof or the salt thereof and / or the at least one further component, in particular the at least two further components, are not irreversibly bound to the carrier.

11. Antimicrobially active product according to one of the preceding claims, characterized in that the dihydrotriazine compound, the tautomer thereof or the salt thereof or the composition forms a coating of the carrier and / or is dispersed within the carrier.

12. Antimicrobially active product according to one of the preceding claims, characterized in that the carrier comprises or consists of a carrier material selected from the group consisting of Cellulose, microbially produced cellulose, cellulose-derived compounds, alkylcellulose, hydroxyalkylcellulose, hydroxyalkylmethylcellulose, Hydroxyalkylethylcellulose, carboxymethylcellulose, chitosan, chitosan hydrolysates, derivatives of chitosan, collagens, collagen hydrolysates, derivatives of collagen, polysaccharides, alginates, agar, locust bean gum, pectin, carrageenan, gelatin, partially hydrolyzed gelatin, polyethylene, polypropylene, polyacrylonitrile, viscose, polyamide, polyurethane, polyester, silicone, polyhydroxyethyl methacrylate and mixtures of at least two of the aforementioned carrier materials.

13. Antimicrobially active product according to one of the preceding claims, characterized in that the carrier is textile, in particular as a woven fabric, knitted fabric, braided fabric, nonwoven fabric or nonwoven material.

14. Antimicrobially active product according to one of claims 1 to 12, characterized in that the carrier is non-textile, in particular as a film, foam, hollow plastic body, in particular tubular or hose-shaped plastic hollow body, or piercing jewelry.

15. Antimicrobially active product according to one of the preceding claims, characterized in that the antimicrobially active product is a medical product, in particular selected from the group consisting of skin pad, wound pad, wound dressing, sponge or gauze, nonwoven cloth for skin cleansing, fabric or nonwoven material for suppressive wound therapy, nonwoven cloth or pad with abrasive fibers or bristles for gentle wound debridement, foam for gentle wound debridement, catheter, in particular urethral catheter or bladder catheter, stoma plate, stoma bag, foam with tubular suction device for drainage of secretions and / or body fluids.

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