Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
  • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
  • C08G73/0605—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
  • C08G73/0616—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only two nitrogen atoms in the ring
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/74—Synthetic polymeric materials
  • A61K31/785—Polymers containing nitrogen
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
  • C08G73/02—Polyamines
  • C08G73/0206—Polyalkylene(poly)amines
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
  • C08G73/02—Polyamines
  • C08G73/0206—Polyalkylene(poly)amines
  • C08G73/0213—Preparatory process
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
  • C08G73/02—Polyamines
  • C08G73/0273—Polyamines containing heterocyclic moieties in the main chain
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
  • C08L79/02—Polyamines

Definitions

• Polymeric or oligomeric active substances with biocidal activity, process for their preparation and composition comprising a polymeric or oligomeric active ingredient
• the invention relates to polymeric or oligomeric active substances with biocidal activity according to the preamble of claim 1, a process for their preparation according to claim 14, a composition comprising a polymeric or oligomeric active substance according to claim 15 and claim 21, a process for the preparation of a composition according to claim 22 and the use of the polymeric or oligomeric active ingredients and the composition according to the invention according to claims 29 and 30.
• Polymers and oligomeric active substances having a biocidal action for example polyguanidines, have been known for a long time. They can be used for a variety of applications.
• US 2,325,586 A describes the preparation of polyguanidines and their salts by means of a polycondensation process. This diamines are reacted with a cyanogen halide, forming a cyanamide. In the subsequent polymerization, the desired polyguanidines or salts thereof are obtained from this cyanamide.
• a special property of such polyguanidines is their biocidal activity.
• EP 0 439 699 A2 provides a solution containing polymers of guanidine salts with increased biocidal activity.
• the object of the invention is therefore to provide novel polymeric or oligomeric active ingredients which have a biocidal effect.
• the invention provides polymeric or oligomeric active agents having biocidal activity obtainable by polycondensation of a guanidine acid addition salt with an amine mixture containing at least one diamine and / or one triamine, wherein at least one amine is selected from the group consisting of i) Diamine having at least one cycloaliphatic radical, and ii) dialkylenetriamine.
• the polymeric or oligomeric active ingredients are the product of a polycondensation of a guanidine acid addition salt with an amine mixture containing at least one diamine and / or a triamine, wherein at least one amine is selected from 4,4'-methylene-bis ( cyclohexylamine) and diethylenetriamine. Both homopolymers and copolymers can be obtained from the amines mentioned.
• guanidine acid addition salt is guanidine hydrochloride.
• a polymeric or oligomeric active ingredient according to the invention is a homopolymer.
• the amine mixture then contains only a single amine compound.
• the polymeric or oligomeric active ingredient may be poly (diethylenetriamine-guanidine hydrochloride) (PDETAG) or polyiminoimidazole. It is advantageous if the amine mixture consists of the triamine diethylenetriamine.
• the homopolymer may also be poly (4,4'-methylenebis (cyclohexylamine) wherein the amine mixture of the diamine is 4,4'-methylenebis (cyclohexylamine).
• a polymeric or oligomeric active ingredient according to the invention is a copolymer, for example a polymeric guanidine derivative.
• the amine mixture then contains at least two different amines. In other words, the amine mixture contains a first component and at least one second component, wherein
• the first component is a diamine or a triamine selected from the group consisting of diamine having at least one cycloaliphatic radical and dialkylenetriamine, wherein
• the second component is a diamine or a triamine selected from the group consisting of diamine having at least one cycloaliphatic radical, dialkylenetriamine, alkylenediamine and oxyalkylenediamine, and
• copolymers result from the combinations of 4,4'-methylenebis (cyclohexylamine) with an amine from the group consisting of diethylenetriamine, hexamethylenediamine, triethyleneglycol diamine and from the combinations of diethylenetriamine with hexamethylenediamine or triethyleneglycol diamine. According to the invention it is therefore advantageous if
• the first component is a diamine or a triamine selected from the group consisting of 4,4'-methylenebis (cyclohexylamine), diethylenetriamine, and wherein
• the second component is also a diamine or a triamine selected from the group 4,4'-methylenebis (cyclohexylamine), diethylene triamine, hexamethylene diamine, triethylene glycol diamine, and
• the first component is 4,4'-methylenebis (cyclohexylamine) and the second component is selected from diethylenetriamine, hexamethylenediamine, triethyleneglycol diamine.
• the first component is diethylene triamine and the second component is selected from hexamethylene diamine and triethylene glycol diamine.
• the mixing ratio of the starting monomers plays an essential role.
• the monomers are present in an equimolar ratio up to a four-fold excess of one of the two monomers. That is, the first component and the second component are present in a molar ratio of 4: 1 to 1: 4, preferably 2: 1 to 1: 2.
• the embodiments of the polymeric or oligomeric active ingredient obtained under these conditions all have an antibacterial activity which can be described by means of the so-called minimum inhibitory concentration. This indicates the lowest bactericidal concentration that inhibits the growth of bacteria in a given solution. In this case, a minimal inhibitory concentration of less than 50 pg / ml is particularly favorable. In many of the embodiments, which are polymeric guanidine derivatives, the minimum inhibitory concentration is even significantly lower and is less than 10 pg / ml or even less than 5 pg / ml. The lower this concentration, the more effectively the corresponding active ingredient can be used as a biocide.
• the polymeric or oligomeric active compounds according to the invention that their minimum inhibitory concentration is 50 pg / ml or less, preferably less than 30 pg / ml, particularly preferably 10 g / ml or less and most preferably less than 5 g / ml.
• a further advantage of the polymeric or oligomeric active compounds according to the invention is the relatively simple production process. It includes the steps
• the process varies slightly, so it is favorable for the preparation of a homopolymer based on 4,4'-methylenebis (cyclohexylamine), for example, when the reaction temperature is 170 ° C.
• a homopolymer prepared on the basis of diethylenetriamine can be recovered at 150.degree.
• the copolymers according to the invention are again preferably produced at 170.degree.
• the invention also provides a composition comprising at least one polymeric or oligomeric active ingredient according to the invention, which is characterized in that the composition is a plastic granulate.
• plastic granules are advantageous in many ways. So it is not only easy to store, but also easy to dose and therefore quickly and easily processable. It can be used, for example, to produce plastic objects, which then have a corresponding biocidal effect by the active substance contained.
• Such articles can play a very advantageous role in many areas of daily life, such as (ex) water pipes, furniture, handles, sanitary ware, shower curtains, sealing material, food packaging, food spouts and spouts, food processing machines, flooring, cleaning wipes, cleaning fluids, agricultural and Feeding equipment, animal blankets, carpets, soles, dental cleaning utensils, drinking vessels, keyboards or other input devices and controls, telephones, antibacterial paints.
• a variety of other items is of course conceivable, for example, clothing textiles, functional textiles, antibacterial papers, technical filters, packaging materials for cosmetics and / or consumer items in the medical field.
• the composition further comprises at least one plastic, preferably at least one thermoplastic polymer, in particular selected from polyurethane, polyolefin, polyvinyl chloride, polypropylene, polycarbonate, polystyrene, polyethersulfone, silicone and polyamide.
• plastic preferably at least one thermoplastic polymer, in particular selected from polyurethane, polyolefin, polyvinyl chloride, polypropylene, polycarbonate, polystyrene, polyethersulfone, silicone and polyamide.
• thermoplastic polymer in particular selected from polyurethane, polyolefin, polyvinyl chloride, polypropylene, polycarbonate, polystyrene, polyethersulfone, silicone and polyamide.
• other polymers which can be selected according to the desired specific use are also conceivable.
• the plastic is a thermoplastic polymer, preferably a thermoplastic polymer selected from the group comprising thermoplastic aliphatic and aliphatic / aromatic polyurethanes, aliphatic and aliphatic / aromatic polyesters, aliphatic and aliphatic / aromatic polyamides, aliphatic and aliphatic / aromatic polycarbonates, aliphatic and aliphatic / aromatic polyureas, aliphatic and aliphatic / aromatic polyester amides, and wherein the polymeric or oligomeric agent has cyclic structures in the main chain.
• a thermoplastic polymer preferably a thermoplastic polymer selected from the group comprising thermoplastic aliphatic and aliphatic / aromatic polyurethanes, aliphatic and aliphatic / aromatic polyesters, aliphatic and aliphatic / aromatic polyamides, aliphatic and aliphatic / aromatic polycarbonates, aliphatic and aliphatic / aromatic polyureas,
• compositions which are present as the hydroxide salt, have a particularly good biocidal activity.
• they may be prepared by basic anion exchange from the corresponding halides, e.g. Chlorides are obtained.
• the polymeric or oligomeric active ingredient has a structure which comprises from the group
• HCl * means here that the HCl is not covalently bound
• n is a natural number, preferably from 1 to 20, more preferably from
• p, q and r are integers representing the preferred molar ratio of
• composition comprising at least one polymeric or oligomeric active ingredient according to one of the claims. 1 to 13, which is obtainable by reaction of
• polymeric or oligomeric drug is covalently bound to the plastic.
• thermoplastic polymer is a thermoplastic aliphatic polyurethane (TAPU) or a thermoplastic aliphatic / aromatic polyurethane (TAAPU) and when the polymeric or oligomeric agent has a cyclic structure selected from the group comprising
• HCl * here also means that the HCl is not covalently bound
• n is a natural number, preferably from 1 to 20, more preferably from 2 to 16 and in particular from 3 to 8, and
• p, q and r are integers representing the preferred molar ratio of
• a copolymer is formed from the components mixed during compounding, if the preparation is carried out under conditions in which a so-called "reactive processing.”
• the polymeric or oligomeric active ingredient is mixed with the thermoplastic polymer and the reaction conditions are selected such that a covalent attachment of the polymeric or oligomeric active ingredient to the thermoplastic polymer takes place, for example, by selecting the thermoplastic polymer such that it still carries reactive groups, such as, for example, isocyanate groups.
• connection can also take place under selected conditions in the context of a recondensation.
• Particularly suitable thermoplastic polymers for this purpose are aliphatic polyurethanes and / or aromatic and / or araliphatic polyurethanes.
• the polymeric or oligomeric active ingredient in liquid form preferably dissolved in a solvent, is reacted with the thermoplastic polymer. It has surprisingly been found that, in particular under these conditions, a covalent bond easily occurs.
• Suitable solvents are, for example, polar solvents such as alcohols, but water is also very suitable.
• thermoplastic polymer at a melt temperature of more than 120 ° C, preferably of more than 140 ° C, more preferably of more than 160 ° C, most preferably from 160 ° C to 300 ° C and very particularly is preferably extruded at 170 ° C and when the thermoplastic polymer with a 0.1 to 90 wt .-% aqueous solution, preferably a 20 to 80 wt .-% aqueous solution, more preferably a 30 to 50 wt .-% aqueous solution, and most preferably a 40 wt .-% aqueous solution of the polymeric or oligomeric active ingredient is added.
• the plastic granules according to the invention can also be provided in the form of a masterbatch. This is then diluted again before use. It is immaterial whether the plastic granulate is a physical mixture of polymeric or oligomeric active ingredient according to the invention or whether the polymeric or oligomeric active ingredient according to the invention is covalently bonded to the thermoplastic polymer.
• plastic granules according to the invention can also be produced in a very rapid and simple way.
• a method of making a plastic granule comprising the steps
• the polymeric or oligomeric active ingredient is preferably added to the thermoplastic polymer in liquid form and the mixing in step a) takes place in an extruder.
• the thermoplastic polymer is selected from the group comprising polyurethane, polyolefin, polyvinyl chloride, polypropylene, polycarbonate, polystyrene, polyethersulfone, silicone and polyamide.
• polymeric guanidine derivatives according to the invention advantageously for the production of clothing textiles, functional textiles, antibacterial papers, technical filters, packaging materials for Food and cosmetics and / or commodities in the medical field can be used.
• gowns, gloves, hoods or shoes that can be used in laboratories or clinical sterile areas, as well as functional textiles such as surgical masks, surgical blankets and bedding using the polymeric or oligomeric active ingredients or a plastic granules of the invention are manufactured.
• cleaning cloths, sterile filters, air filters and the surface of furniture or trays, as well as curtains in the hospital area can be advantageously prepared at least partially using the active compounds of the invention.
• Also advantageous is the use for the production of packaging materials for food or cosmetics.
• the polymeric or oligomeric actives of the invention are for use in the manufacture of (down) water pipes, furniture, handles, sanitary ware, shower curtains, gasketing materials, food packaging, food spouts and spouts, food processing machines, flooring, cleaning wipes, cleaning fluids, agricultural and fodder equipment, animal quilts Carpets, shoe soles, dental cleaning utensils, drinking vessels, keyboards or other input devices and controls, telephone sets, antibacterial paints may be beneficial.
• composition according to the invention for the production of clothing textiles, functional textiles, antibacterial papers, technical filters, packaging materials for food and cosmetics and / or consumer items in the medical field.
• Fig. 2 1 H 1 H COZY spectrum of an aqueous extract of another embodiment of a composition of the invention from a thermoplastic polymer and a polymeric or oligomeric active ingredient according to the invention.
• the flask is equipped with an internal thermometer and a threefold heated reflux condenser with non-return valve according to Stutz (in the following section cooler).
• reaction mixture In an oil bath, the reaction mixture is heated, starting from a temperature of 100 ° C, a slow evolution of gas begins. With further increase in temperature, the gas evolution is only slowly stronger. After a total of 85 minutes, a temperature of 170 ° C is reached.
• the melt is cooled to room temperature.
• the starting amounts used give under the conditions mentioned above 24.48 g of a transparent, colorless and brittle solid.
• the structure of the obtained polymer can be represented by the formula (I).
• N 1 to 8, predominantly 1 to 3.
• radicals R1 and R2 can originate both from the monomer used and from the guanidine hydrochloride used and are therefore defined as follows:
• R1 is selected from H or
• R2 is selected from NH 2 or
• the resulting product mixture thus contains polymeric compounds corresponding to the formulas (II), (III) and (IV):
• formulas (I), (II), (III) and (IV) can also be prepared in an alternative manner, as shown below by way of example for formula (VIII) or (VIII ').
• the positive charge of the guanidine unit is not localized, but is distributed mesomerically to all three nitrogen atoms.
• the melt is maintained at 150 ° C with stirring for five hours until gas evolution ceases.
• the melt Under ice-cooling and oil vacuum, the melt is cooled to room temperature.
• the starting amounts used give 11, 96 g of a white and brittle solid under the conditions mentioned above.
• n 1 to 12, predominantly 2 to 8.
• R3 is either NH 2 or and
• R4 is selected from
• the resulting product mixture thus contains polymeric compounds corresponding to the formulas (VI), (VII) and (VIII):
• HCl * means that the HCl is not covalently bound
• n is a natural number that has the meaning given above
• Example 2 can be represented in an analogous manner, wherein the positive charge mesomerically distributed to all three nitrogen atoms of the guanidine unit.
• the mixing ratio of the two monomers contained in the amine mixture is between 1: 1 and 1: 4 and between 4: 1 and 1: 1.
• the compounds prepared according to one of the preceding examples are prepared in a bacterial nutrient medium, preferably Tryptic Soy Broth, and diluted to various concentrations. These solutions of different concentrations are inoculated with a suspension of Escherichia coli and incubated for 24 h at 37 ° C.
• the minimum inhibitory concentration (MIC) is then understood as meaning the lowest concentration of the biocide to be investigated in the solution in which the growth of the bacteria is inhibited. In the case of the corresponding solution, no cloudiness due to the growth of the bacteria is then observable.
• control polymer As a control, a control polymer was used whose biocidal activity is known and whose minimum inhibitory concentration is usually 5 pg / ml.
• Example 5 Plastic granules with polymeric or oligomeric active ingredient covalently bound to a thermoplastic polymer
• thermoplastic polymers e.g. Polyurethanes come under certain conditions to a so-called Reactive processing.
• the polymeric or oligomeric active ingredients are covalently linked to the thermoplastic used.
• thermoplastic polycondensates namely the polymeric or oligomeric active compounds according to the invention are coextruded with melts of thermoplastic polycondensates or polyaddition products.
• new thermoplastics biocidal thermoplastics
• thermoplastics polycondensates or polyaddition products are used, which are processable by melt extrusion, z.
• polyesters such as polyethylene terephthalate, polybutylene terephthalate, polylactide, polycaprolactone; Polyamides such.
• Polyamide (PA) 6 PA 66, PA 610, PA11, PA12; Polyesteramides, aliphatic and aromatic polycarbonates, aliphatic and aromatic polyurethanes and polyureas.
• water-soluble polyguanidines are used, which are in particular those having the following structures: in which
• HCl * means that the HCl is not covalently bound
• n is a natural number, preferably from 1 to 20, more preferably from
• p, q and r are integers representing the preferred molar ratio of
• thermoplastic melt extrusion in a conventional extruder at extrusion temperatures of 70 - 300 ° C depending on the thermoplastic with an aqueous solution of biocidal or oligomeric active ingredient with concentrations of 0.1 to 90 wt.% Of the biocidal polymer oligomeric drug in water additiviert.
• the water is removed in the evaporation zone of the extruder.
• the new product obtained at the end of the extrusion of the biocidal thermoplastic containing 0.1 to 50% of the structures of the polymeric or oligomeric active ingredients relative to the thermoplastic used.
• the polymeric or oligomeric active ingredients are covalently bound to the thermoplastic by re-condensation. The recondensation takes place during the extrusion.
• thermoplastic polymer used after extrusion can be demonstrated both by NMR and by mass spectrometry.
• thermoplastic aliphatic polyurethane TAPU
• PG1 first polyguanidine
• HCl * means that the HCl is not covalently bound
• n is a natural number that has the meaning given above
• the additivation takes place in such a way that a compound with 10% by weight of the first polyguanidine (PG1) is formed in TAPU.
• the mass spectroscopic analysis shows that after extraction of the compound no active ingredient according to the invention, namely no first polyguanidine (PG1) can be found in the extract.
• the extraction was carried out with boiling water.
• thermoplastic aliphatic / aromatic polyurethane (TAAPU) is used as thermoplastic polymer instead of the thermoplastic aliphatic polyurethane (TAPU).
• TAAPU thermoplastic aliphatic / aromatic polyurethane
• the extrusion was also carried out here at a melt temperature of 170 ° C in a twin-screw extruder with the addition of a 40% aqueous solution of the first polyguanidine (PG1).
• thermoplastic aliphatic polyurethane (TAPU) was extruded as before at a melt temperature of 170 ° C in a twin-screw extruder and additized with a 40% aqueous solution of a second polyguanidine (PG2).
• TAPU thermoplastic aliphatic polyurethane
• PG2 second polyguanidine
• the second polyguanidine (PG2) has the following structure:
• HCl * means that the HCl is not covalently bound
• n is a natural number that has the meaning given above, and p and q are integers that define the preferred molar ratio of the structural fragments to one another in the formulas.
• FIG. 1 shows the 1 H- 1 H COZY spectrum of the extract of the exemplary embodiment.
• Fig. 2 also shows the 1 H- 1 H COZY spectrum of the extract.
• a thermoplastic aliphatic / aromatic polyurethane was used instead of the thermoplastic aliphatic polyurethane (TAPU) and extruded as previously with a 40% aqueous solution of the second polyguanidine (PG2) at a melt temperature of 170 ° C.
• Additization was carried out in such a way that a compound with 10% by weight of the second polyguanidine (PG2) is produced in TAAPU.
• no polymeric or oligomeric drug namely no second polyguanidine (PG2), detectable in the extract with boiling water.
• 1H-1 H-COZY NMR were measured on the Bruker Avance 300 B spectrometer (Dual 1 H - 13C Z-gradient probe), each at 25 ° C in a mixed solvent of hexafluoroisopropanol (ca 1 mL) and D 2 O (ca. 0.2 mL). Calibration was based on the protonated D 2 O peak as an internal standard (4.79 ppm at 25 ° C.). (The 2D spectra shown in the report are not calibrated because the 1 D spectra shift up and left thereby).
• the mass spectra were measured by atmospheric pressure chemical ionization (APCI) on a Thermo Fisher Scientific Finnigan LTQ-FT spectrometer in methanol as a solvent.
• APCI atmospheric pressure chemical ionization
• guanidine acid addition salt with an amine mixture which comprises at least one diamine and / or one triamine, where at least one amine is selected from among A group consisting of i) diamine having at least one cycloaliphatic radical and ii) dialkylenetriamine.
• at least one amine is selected from 4,4'-methylenebis (cyclohexylamine) and diethylenetriamine.
• the guanidine acid addition salt is guanidine hydrochloride.
• an alkylenediamine in particular a compound of the general formula NH 2 (CH 2) n NH 2
• a compound of the general formula NH 2 (CH 2) n NH 2 comprises, or when the amine mixture is a oxyalkylene, particularly a compound is the general Fromel NH 2 [(CH 2) 20] n (CH 2 ) 2 NH 2 , in which n is an integer between 2 and 5, in particular 2, comprises.
• a polymeric or oligomeric active ingredient according to the invention is a homopolymer. It is envisaged that the amine mixture consists of the triamine diethylenetriamine or that the amine mixture consists of the diamine 4,4'-methylenebis (cyclohexylamine).
• the amine mixture contains a first component and at least one second component, wherein
• the first component is a diamine or a triamine selected from the group consisting of diamine having at least one cycloaliphatic radical and dialkylenetriamine, and wherein
• the second component is a diamine or a triamine selected from the group consisting of diamine having at least one cycloaliphatic radical, dialkylenetriamine, alkylenediamine and oxyalkylenediamine, and
• the first component is a diamine or a triamine selected from the group consisting of 4,4'-methylenebis (cyclohexylamine), diethylenetriamine, and wherein
• the second component is a diamine or a triamine selected from the group consisting of 4,4'-methylenebis (cyclohexylamine), diethylenetriamine, hexamethylenediamine, triethyleneglycol diamine and
• polymeric or oligomeric agents in which the first component is 4,4'-methylenebis (cyclohexylamine) and the second component is selected from diethylenetriamine, hexamethylenediamine, triethyleneglycol diamine or the first Component is diethylenetriamine and the second component is selected from hexamethylenediamine and triethyleneglycol diamine, are particularly advantageous. Furthermore, it is favorable if the first component and the second component are present in a molar ratio of 4: 1 to 1: 4, preferably 2: 1 to 1: 2.
• step d) stirring the melt at the temperature set in step d), namely at 140 ° C to 180 ° C, preferably 145 ° C to 175 ° C, more preferably 150 ° C to 170 ° C, until the gas evolution is complete, at least but for 5 hours
• compositions according to the invention comprising at least one polymeric or oligomeric active ingredient according to the invention, wherein the composition is a plastic granulate. It is advantageous if the composition further comprises at least one plastic, preferably at least one thermal polymer, in particular selected from polyurethane, polyolefin, polyvinyl chloride, polypropylene, polycarbonate, polystyrene, polyethersulfone, silicone and polyamide.
• plastic preferably at least one thermal polymer, in particular selected from polyurethane, polyolefin, polyvinyl chloride, polypropylene, polycarbonate, polystyrene, polyethersulfone, silicone and polyamide.
• the plastic is a thermoplastic polymer, preferably a thermoplastic polymer selected from the group comprising thermoplastic aliphatic and aliphatic / aromatic polyurethanes, aliphatic and aliphatic / aromatic polyesters, aliphatic and aliphatic / aromatic polyamides, aliphatic and aliphatic / aromatic polycarbonates, aliphatic and aliphatic / aromatic polyureas, aliphatic and aliphatic / aromatic polyester amides, and wherein the polymeric or oligomeric active agent has cyclic structures in the main chain.
• a thermoplastic polymer preferably a thermoplastic polymer selected from the group comprising thermoplastic aliphatic and aliphatic / aromatic polyurethanes, aliphatic and aliphatic / aromatic polyesters, aliphatic and aliphatic / aromatic polyamides, aliphatic and aliphatic / aromatic polycarbonates, aliphatic and aliphatic / aromatic polyureas,
• the polymeric or oligomeric active ingredient has a structure which comprises from the group
• HCl * means that the HCl is not covalently bound
• n is a natural number, preferably from 1 to 20, more preferably from
• p, q and r are integers representing the preferred molar ratio of
• a process for producing a plastic granulate ie, a process for preparing a composition according to the above, comprising the steps a) combining and mixing a polymeric or oligomeric active substance according to the invention having a biocidal effect with a thermoplastic polymer,
• the polymeric or oligomeric active ingredient is supplied to the thermoplastic polymer in liquid form and the mixing in step a) takes place in an extruder.
• the thermoplastic polymer is selected from the group comprising polyurethane, polyolefin, polyvinyl chloride, polypropylene, polycarbonate, polystyrene, polyethersulfone, silicone and polymaid.
• thermoplastic polymer is a thermoplastic aliphatic polyurethane (TAPU) or a thermoplastic aliphatic / aromatic polyurethane (TAAPU) and when the polymeric or oligomeric active ingredient has a cyclic structure which is selected from the group comprising
• HCl * means that the HCl is not covalently bound
• n is a natural number, preferably from 1 to 20, more preferably from
• p, q and r are integers representing the preferred molar ratio of
• thermoplastic polymer is extruded at a melt temperature of more than 120 ° C, preferably of more than 140 ° C, more preferably of more than 160 ° C and most preferably 170 ° C and if the thermoplastic polymer with a 20 to 50% aqueous solution, preferably a 30 to 50% aqueous solution, more preferably a 40% aqueous solution of the polymeric or oligomeric active ingredient is added.
• composition according to the invention in particular a plastic granules, for the production of clothing textiles, functional textiles, antibacterial papers, technical filters, packaging materials for food and cosmetics and / or consumer items in the medical field.

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• 2009
  • 2009-11-12 DE DE102009052667A patent/DE102009052667A1/de not_active Ceased
• 2010
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