EP1771497A1 - Compositions contenant des composes organosilicies polyquaternaires - Google Patents

Compositions contenant des composes organosilicies polyquaternaires

Info

Publication number
EP1771497A1
EP1771497A1 EP05774677A EP05774677A EP1771497A1 EP 1771497 A1 EP1771497 A1 EP 1771497A1 EP 05774677 A EP05774677 A EP 05774677A EP 05774677 A EP05774677 A EP 05774677A EP 1771497 A1 EP1771497 A1 EP 1771497A1
Authority
EP
European Patent Office
Prior art keywords
radical
optionally
sir
organosilicon compounds
composition according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP05774677A
Other languages
German (de)
English (en)
Inventor
Christian Ochs
Birgit Schwab
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wacker Chemie AG
Original Assignee
Wacker Chemie AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wacker Chemie AG filed Critical Wacker Chemie AG
Publication of EP1771497A1 publication Critical patent/EP1771497A1/fr
Withdrawn legal-status Critical Current

Links

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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
    • C08G77/54—Nitrogen-containing linkages
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/34—Organic impregnating agents
    • B27K3/343—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
    • C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
    • C03C17/30—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with silicon-containing compounds
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
    • C08G77/485—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms containing less than 25 silicon atoms
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/162—Organic compounds containing Si
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • C—CHEMISTRY; METALLURGY
    • C14—SKINS; HIDES; PELTS; LEATHER
    • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C11/00—Surface finishing of leather
    • C14C11/003—Surface finishing of leather using macromolecular compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
    • D06M13/51—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
    • D06M13/513—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond with at least one carbon-silicon bond
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/10—Processes in which the treating agent is dissolved or dispersed in organic solvents; Processes for the recovery of organic solvents thereof
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H19/00—Coated paper; Coating material
    • D21H19/10—Coatings without pigments
    • D21H19/14—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12
    • D21H19/24—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H19/32—Coatings without pigments applied in a form other than the aqueous solution defined in group D21H19/12 comprising macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming a linkage containing silicon in the main chain of the macromolecule
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/16—Sizing or water-repelling agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/16—Inorganic impregnating agents
    • B27K3/22—Compounds of zinc or copper
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/34—Organic impregnating agents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K3/00—Impregnating wood, e.g. impregnation pretreatment, for example puncturing; Wood impregnation aids not directly involved in the impregnation process
    • B27K3/52—Impregnating agents containing mixtures of inorganic and organic compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B27—WORKING OR PRESERVING WOOD OR SIMILAR MATERIAL; NAILING OR STAPLING MACHINES IN GENERAL
    • B27K—PROCESSES, APPARATUS OR SELECTION OF SUBSTANCES FOR IMPREGNATING, STAINING, DYEING, BLEACHING OF WOOD OR SIMILAR MATERIALS, OR TREATING OF WOOD OR SIMILAR MATERIALS WITH PERMEANT LIQUIDS, NOT OTHERWISE PROVIDED FOR; CHEMICAL OR PHYSICAL TREATMENT OF CORK, CANE, REED, STRAW OR SIMILAR MATERIALS
    • B27K7/00—Chemical or physical treatment of cork

Definitions

  • compositions containing polyquaternary organosilicon compounds are provided.
  • the invention relates to compositions containing polyquaternary organosilicon compounds, their preparation and their use for the antimicrobial finishing of surfaces.
  • biocides used hitherto Another fundamental problem of the biocides used hitherto is that they must have a certain water solubility in order to be effective, which is why the biocidal equipment is often only effective for a very limited time.
  • the active ingredients according to their applicational usually do not remain at the application, but the time fe in lauric more or less uncontrollably to the environment differ ⁇ and accumulate there, if necessary, which leads to problems in the long term ent.
  • Recent work is therefore aimed at anchoring the antimicrobially active group in a polymer matrix.
  • Such antimicrobially active polymers or their formulations should, owing to the greatly reduced ability of the active component to migrate, not only be sustainable in terms of environmental compatibility, but in the ideal case should even be non-toxic to higher organisms and permanently permanent.
  • Organopolysiloxanes with quaternary nitrogen groups have long been known from the literature. Their formulations are widely used, for example, as textile auxiliaries (WO 03/066708 A1), as an ingredient of cosmetic composition (WO 01/41719 A1, WO 41720 A1, WO 41721 A1), as an additive to Waschmit ⁇ telformultechniken (EP 1199350 Bl) and household cleaners (EP 1133545 Bl).
  • the antimicrobial effectiveness of quat phenomenon- containing polysiloxanes and their formulations has so far been little reported, with a close study of the data in al ⁇ len cases shows that the ostensible biocidal properties derived only from an antibacterial activity against ei ⁇ ner extremely small number of bacteria has been. Formulations of quat pupil stream ambience, such as fungi, bacteria, yeasts and algae, are therefore desirable.
  • US 6,384,254 Bl discloses quaternary nitrogen-containing polysiloxanes and their formulations for antibacterial finishing of fibers or fiber products.
  • the described compositions make it possible to impart bacteriocidal properties to fibers and textiles in combination with a soft touch typical for silicones.
  • the equipment has a certain permanence over a few wash cycles.
  • the investigations on antibacterial activity are limited to S. aureus as the only bacterial strain.
  • organopolysiloxanes with antibacterial action are exclusively those having pendant quat groups.
  • organopolysiloxanes having quaternary ammonium side groups can harbor a high toxicological potential. Investigations have shown in the past that the high toxicity of such systems is influenced in particular by the distance between two quaternary units.
  • R may be the same or different and a monovalent, optionally substituted, hydrocarbon radical having 1 to 18 carbon atoms, which may be interrupted by oxygen atoms
  • R 1 may be the same or different and represents a monovalent, optionally substituted hydrocarbon radical having 1 to 18 carbon atoms or may be part of a bridging alkylene radical
  • R 2 is a divalent hydrocarbon radical having at least 2 carbon atoms which contains at least one hydroxyl group and / or is interrupted by one or more oxygen atoms and / or is bonded to silicon via oxygen,
  • X represents an organic or inorganic anion
  • b is an integer of at least 1
  • n is an integer of at least 1
  • compositions according to the invention can be used as solutions or in the form of dispersions, such as e.g. Micro- or macroemulsion.
  • compositions of the invention contain at the Or ⁇ ganosiliciumtellen (A) in amounts of preferably from 10 "5 to 99 wt .-%, preferably 0.01 to 90 wt .-%, particularly preferably 0.01 to 50 wt .-%, in each based on the total weight of the compositions according to the invention.
  • the organosilicon compounds (A) used according to the invention may be any organosilicon compounds having at least one unit of the formula (I), these being both pure siloxanes, ie Si-O-Si ⁇ structures, and also silcarbanes,
  • ⁇ Si-R'-Si ⁇ structures with R ' may be a divalent, optionally substituted and / or interrupted with heteroatoms hydrocarbon radical, or belie ⁇ bigen organosilicon groups acting copolymers.
  • radicals R are alkyl radicals, such as the methyl, ethyl, n-propyl, iso-propyl, 1-n-butyl, 2-n-butyl, iso-butyl, tert. Butyl, n-pentyl, iso-pentyl, neo-pentyl, tert-penyl radical; Hexyl radicals, such as the n-hexyl radical; Heptyl radicals, such as the n-heptyl radical; Octyl radicals, such as the n-octyl radical and iso-octyl radical, such as the 2, 2, 4-trimethylpentyl radical; Nonyl radicals, such as the n-nonyl radical; Decyl radicals, such as the n-decyl radical; Dodecyl radicals, such as the n-dodecyl radical; Octadecyl radicals, such as the n-
  • substituted radicals R are methoxyethyl, ethoxyethyl and the (2-ethoxy) ethoxyethyl radical.
  • Radicals R are preferably hydrocarbon radicals having 1 to 12 carbon atoms which are optionally substituted by halogen atoms, amino groups, ether groups, ester groups, epoxy groups, mercapto groups, cyano groups or (poly) glycol radicals, the latter being selected from oxyethylene and / or or oxypropylene units are constructed, more preferably alkyl radicals having 1 to 6 carbon atoms, in particular the methyl radical.
  • radicals R 1 are the examples given for radical R.
  • Radicals R 1 are preferably hydrocarbon radicals having 1 to 18 carbon atoms, more preferably alkyl radicals having 1 to 8 carbon atoms and benzyl radicals. However, the radical R 1 may also be a bivalent radical derived therefrom, so that, for example, two radicals R 1 form a ring with the nitrogen atom. If the radical R 1 is substituted hydrocarbon radicals, hydroxyl groups are preferred as substituents.
  • anion X are organic anions, such as carboxylate ions, enolations and sulfonations, and also inorganic anions.
  • organic anions such as carboxylate ions, enolations and sulfonations
  • inorganic anions such as halide ions, such as fluoride ions, chloride ions, bromide ions and iodide ions, and sulfate ions.
  • Anion X " is preferably carboxylate ions and halide ions, particularly preferably chloride ions and acetates.
  • radical R 2 are divalent, linear, cyclic or branched, saturated or unsaturated Kohlenwasserst intro- te, which are substituted with hydroxyl groups and / or oxygen substituents are singly or repeatedly interrupted and / or bound via oxygen to silicon, such as the rest
  • B is preferably an integer from 1 to 5000, more preferably from 2 to 500.
  • n is an integer of 1 to 100, more preferably 1 to 75, especially 2 to 50.
  • organosilicon compounds (A) used according to the invention are preferably those of the general formula
  • D 1 may be identical or different and is hydrogen atom, hydroxyl radical, halide radical, epoxy-functional radical, a radical -NR * 2 or a monovalent organic radical, where R * may be identical or different and represents hydrogen atom or a monovalent, optionally substituted hydrocarbon radical and the radical -NR * 2 may also be present as ammonium salt, and D 2 is a group of the formula
  • D 1 and organic radical are alkyl radicals and alkoxy radicals, for halide radicals -Cl and -Br, for epoxy-functional radicals the radical
  • nitrogen-containing organic radicals such as amines, sulfur-containing organic radicals such as sulfonate radicals, and carbon-added organic or inorganic anions such as carboxylates and halohydrocarbon radicals.
  • An example of the radical -NR * 2 is the -N (CH 3 ) 2 radical.
  • the organosilicon compounds (A) used according to the invention are linear polymers of the formula (II) where a is 1, R 2 is - (CH 2 ) 3 OCH 2 -, - (CH 2 ) 3 OCH 2 -CH ( OH) -CH 2 - or - (CH 2 ) S OCH 2 -CHt-CH 2 (OH)] - and D 1
  • HC-CH 2 is equal to -Cl, -N (CH 3 ) 2 , -N [(CH 3 ) 2 H] + C 1 ⁇ or '
  • the organosilicon compounds (A) used according to the invention have a viscosity of preferably 10 3 to 10 8 mPas, more preferably 10 4 to 5 * 10 7 mPas, in each case at 25 ° C.
  • organosilicon compounds (A) used according to the invention are commercially available products or can be prepared by known processes, for example by reacting the corresponding epoxy-functional silanes and / or siloxanes with dialkylammonium salts such as dimethylammonium chloride or by reacting the corresponding amino compounds with Alkyl halides.
  • dialkylammonium salts such as dimethylammonium chloride
  • reacting the corresponding amino compounds with Alkyl halides for the purposes of the present invention, the term "solvent" does not mean that all components must dissolve in it.
  • the solvents (B) used according to the invention are preferably water (B1) or polar organic solvents (B3) with an electric dipole moment of> 1 dye (20 ° C.), particularly preferably water, on or value added effect ⁇ term alcohols.
  • solvent (B1) it is possible to use any water, whereby solvent (B1) contains further substances which naturally occur in water, such as e.g. Minerals, bacteria, Spu ⁇ renimplantation, dissolved gases, suspended matter, etc., or which can be typically added for water applications or to achieve special effects, may contain.
  • solvent (B1) contains further substances which naturally occur in water, such as e.g. Minerals, bacteria, Spu ⁇ renimplantation, dissolved gases, suspended matter, etc., or which can be typically added for water applications or to achieve special effects, may contain.
  • Solvents (B1) are preferably drinking water according to the German Drinking Water Ordinance, demineralized water, distilled water and purified water (Aqua Purificata), particularly preferably demineralized water, distilled water and purified water (Aqua Purificata).
  • Suitable organosiloxanes as solvent (B) are, for example, linear or cyclic organopolysiloxanes having alkyl radicals which are optionally substituted by amino, hydroxyl, polyether or carboxy groups, such as - cyclic siloxanes consisting of 3 to 8 diorganosiloxy units, such as octamethyltetracyclosiloxane,
  • siloxanes (B2) are liquid siloxanes, those having a viscosity of from 0.5 to 100,000 mm 2 / s are preferred, and those having a viscosity of from 0.5 to 1,000 mm 2 / s are particularly preferred preferably, each at 25 0 C.
  • polar organic solvents (B3) used according to the invention are monohydric or polyhydric alcohols, such as, for example, methanol, ethanol, n-propanol, i-propanol, 1,2-propanediol, 1,3-propanediol, 1-butanol, 2- Butanol, tert-butanol, 1, 4-butanediol, 1-pentanol, 2-pentanol, 3-pentanol, 1, 5-pentanediol, 1-hexanol, cyclohexanol, 1-heptanol, 1-octanol, 1-decanol, lauryl alcohol , Myristyl alcohol, stearyl alcohol, benzyl alcohol, diethylene glycol, triethylene glycol, dipropylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol mono
  • HMPT dimethyl sulfoxide
  • DMSO dimethyl sulfoxide
  • CO 2 sulfolane
  • orga ⁇ nische ionic liquids such as 1,3-dimethylimidazoliummethylsulfat or l-butyl-4-methylpyridiniumchlorid.
  • composition type I polar organic solvents (B3) are used as solvent (B)
  • component (A) dissolved in component (B) is preferably present in the compositions according to the invention (composition type I).
  • compositions according to the invention are preferably an aqueous solution or one aqueous dispersion.
  • composition III are preferably solutions or dispersions, in which latter case the siloxanes (B2) are preferably the continuous one Phase.
  • composition type IV is the inventive Entity ⁇ ratios (composition type IV) preferably dispersions, in the latter case preferably the siloxanes (B2) constitute the continuous phase.
  • compositions according to the invention contain solvent (B) in amounts of preferably from 1 to 99% by weight, more preferably from 10 to 90% by weight, based in each case on the total weight of the composition according to the invention.
  • Examples of surface active agents (C) which may optionally be used according to the invention are any surface-active agents, such as e.g. Emulsifiers, which have also been used hitherto, e.g. were used for the preparation of dispersions.
  • the component (C) can be used both in pure form, as well as solutions of one or more types of component (C) in water or organic solvents.
  • nonionic emulsifiers are Sor ⁇ bitanester of fatty acids having 10 to 22 carbon atoms, polyoxyethylensorbitanestern of fatty acids having 10 to 22 carbon atoms and up to 35 wt .-% ethylene oxide content, such as the ethylene oxide condensates of sorbitan monolaurate, sorbitan mo - nomyristats, sorbitan monostearate, sorbitan tristearate or sorbitan trioleate, polyoxyethylene derivatives of phenols having 6 to 20 carbon atoms in the aromatic and up to 95 wt .-% Ethy ⁇ lenoxidgehalt, such as the ethylene oxide condensates of Dodecylphenols, myristylphenol, octylphenol or stearylphenol, polyoxyethylene condensates of fatty acids or Fatty alcohols having 8 to 22 carbon atoms with up to 95 wt .-% Ethyl
  • Suitable anionic emulsifiers (C) are alkylarylsulfonates having 6 to 20 carbon atoms in the alkyl group, such as. Sodium or potassium dodecyl benzene sulphonate, fatty sulphates containing from 8 to 22 carbon atoms, e.g. Sodium, potassium or triethanolammonium dodecyl sulfate or stearyl sulfate, alkyl sulfonates having 10 to 22 carbon atoms, such as. Sodium or potassium dodecylsulfonate or stearylsulfonate, fatty acids having 8 to 22 carbon atoms, e.g.
  • Trimethyldodecylammonium chloride sodium laurate, sodium or potassium myristate, alkali metal salts of dialkyl sulfosuccinates, and alkali metal salts of carboxylated, ethoxylated alcohols having 10 to 22 carbon atoms and up to 95 percent ethylene oxide.
  • amphiphilic emulsifiers are fatty amino and amidobetaines having 10 to 22 carbon atoms, such as decylaminobetain, fatty amidosulfobetaines having 10 to 22 Kohlenstoffato ⁇ men, such as Cocoamidsulfobetain or Olylamidobetain, and fatty amine oxides having 10 to 22 carbon atoms, such as n -COCO- morpholine oxide, decyldiraethylamine oxide and cocoamidodimethylamine oxide.
  • the surface-active agents (C) used according to the invention are preferably nonionic, cationic or anionic emulsifiers or inorganic solid-state emulsifiers, with nonionic or anionic emulsifiers being particularly preferred.
  • compositions according to the invention contain surface-active agents (C), they are used in amounts of preferably 0.1 to 60 parts by weight, more preferably 1 to 40 parts by weight, in each case based on 100 parts by weight of organosilicon compound (A).
  • compositions according to the invention may contain as further substances (D) any auxiliaries or fillers, for example agents for adjusting the pH, such as basic substances or inorganic acids, catalysts, defoamers, foam stabilizers, rheology controllers, thickeners, dyes .
  • auxiliaries or fillers for example agents for adjusting the pH, such as basic substances or inorganic acids, catalysts, defoamers, foam stabilizers, rheology controllers, thickeners, dyes .
  • compositions according to the invention contain further substances (D), they are used in amounts of preferably 0.01 to 100 parts by weight, more preferably 1 to 50 parts by weight, in each case based on 100 parts by weight of organosilicon compound (A).
  • the components used according to the invention may each be one type of such a component as well as a mixture of at least two types of a respective component.
  • compositions according to the invention have a pH of preferably 2 to 12, particularly preferably 4 to 10, in each case at 25 ° C.
  • compositions according to the invention of type I are preferably those comprising
  • compositions of the invention of type II have a viscosity of preferably up to 10 000 mm 2 / s, particularly preferably from 1 to 1000 mm 2 / s, in each case at 25 ° C., in the case of dispersions.
  • compositions of the invention of type III are preferably those containing such
  • compositions according to the invention of type III have a viscosity of preferably 0.5 to 100,000 mm 2 / s, particularly preferably 1 to 10,000 mm 2 / s, in each case at 25 ° C., if they are solutions.
  • compositions according to the invention of type III have a viscosity of preferably up to 10,000 mm 2 / s, more preferably 1 to 2,000 mm 2 / s, in each case at 25 ° C., in the case of dispersions.
  • compositions according to the invention of type IV are preferably those containing such
  • compositions of the invention of type IV are particularly preferably those consisting of (A) organosilicon compounds of the formula (II) (B) nonpolar siloxanes,
  • compositions of the invention of type IV have a viscosity of preferably up to 10,000 mm 2 / s, particularly preferably from 1 to 1,000 mm 2 / s, in each case at 25 ° C., in the case of dispersions.
  • compositions according to the invention irrespective of the particular type, all constituents can in principle be mixed together in any order.
  • the mixing can be carried out at room temperature and under the pressure of the surrounding atmosphere, that is about 900 to 1100 hPa, according to any desired and heretofore known methods. If desired, however, the mixing can also be carried out at relatively high temperatures, for example at temperatures in the range from 30 to 200 ° C.
  • component (A) can also be prepared in situ during the preparation of the composition according to the invention and used without isolation or further work-up steps.
  • compositions according to the invention are:
  • compositions according to the invention have the advantage that they are easy to prepare, have a very high storage stability and give surface finishes which do not yellow and exhibit biocidal activity over a long period of time.
  • compositions according to the invention furthermore have the advantage that they have high antimicrobial activity.
  • compositions of the invention also have the advantage that they are not human toxic.
  • the compositions according to the invention can be formulated as highly antibacterially effective formulations with good environmental compatibility and low toxi ⁇ tic potential even in the lowest concentration.
  • organosilicon compounds (A) used in the compositions according to the invention can have, in addition to a hydroxy group, further different functional groups (for example epoxy, amino or chloroalkyl groups) which are used for permanent incorporation of the antimicrobially active polymer can be used in organic or silicon-based polymers.
  • further different functional groups for example epoxy, amino or chloroalkyl groups
  • compositions according to the invention can now be used for all purposes for which solutions or dispersions of organosilicon compounds have hitherto also been used.
  • the compositions according to the invention are suitable for all applications in which it is an antimicrobial treatment or equipment of industrial products, such as dispersions, emulsions and mixtures, in particular surface surfaces or silicon-typical surface effects are to be achieved.
  • Another object of the present invention is a process for the antimicrobial finishing of surfaces, characterized in that the composition according to the invention is applied to the surface to be treated.
  • the application according to the invention can be carried out by hitherto known methods, as have also heretofore been typically used for the finishing of surfaces of a respective substrate.
  • the surface to be treated with the compositions according to the invention is treated for a time sufficient for the equipment. This can be done, for example, by application, spraying, brushing, coating, padding, coating or setting the formulations according to the invention onto the substrate or by immersing the substrate in the compositions according to the invention and by coextrusion or blending, all of which Cases can connect further process steps.
  • the process according to the invention may also be carried out using formulations comprising the compositions according to the invention, as described, for example, in US Pat. in the case of household cleaner or shampoo formulations.
  • Suitable substrates which can be treated by the process according to the invention are those with hard or soft surfaces of all kinds. These are preferably natural or artificial fibers, textile fabrics and knitted fabrics, textile fabrics, tissue papers and fabrics, Paper, skin, hair, leather, painted surfaces or surfaces consisting of metal, glass, ceramic, glass-ceramic, enamel, mine Noise materials, wood, cork, plastics and artificial and natural elastomers.
  • the surfaces which are treated by the process according to the invention are particularly preferably textiles, tissue papers, skin, painted surfaces, metallic surfaces, glass, ceramics, mineral materials, wood, plastics and elastomers.
  • the method according to the invention can be used in all areas which involve antimicrobial treatment or finishing of surfaces, such as, for example, surfaces which are exposed to the weather, surfaces and objects in the household and food sector, as ⁇ floors eg walking, tiles, windows, refrigerators or freezers, stoves, toys, baby and children's products, packaging, pipelines, containers or filters, surfaces and objects (in the nursing field hospital, intensive care, Kleinst Weg- or care Alten ⁇ ) and clinical (hospital rooms for medi ⁇ ical treatments or interventions, isolation), medi ⁇ ical items or products such as wound dressings, tubing, sterile filter or transplants, surfaces and Ge genfound in the hygiene and sanitation such as toilets, toothbrushes, shower cubicles or curtains, medical applications, such as use as De disinfectant, as well as the antifouling area.
  • surfaces which are exposed to the weather, surfaces and objects in the household and food sector, as ⁇ floors eg walking, tiles, windows, refrigerators or freezers, stoves, toys, baby and children's products, packaging,
  • the inventive method for finishing surfaces is carried out at temperatures of preferably -100 to +300 0 C, more preferably -30 to +200 0 C, and the pressure of the surrounding Atmo ⁇ sphere, ie about 900 to 1100 hPa performed. However, if desired, higher or lower pressures may also be used.
  • the method according to the invention has the advantage that surfaces of any kind can be equipped antimicrobially, wherein the antimicrobial properties may possibly be permanent.
  • this is a true biocidal effect that extends over a very broad spectrum and to a variety of microorganisms such as gram + and gram bacteria, fungi, yeasts & algae.
  • the biocidal effect and the active limits can be controlled by simple variation of the siloxane component in the organosilicon compound (A) used according to the invention, wherein the active component is always polymer-bound and thus has low bioavailability for higher organisms.
  • the method according to the invention has the advantage that it can be combined with a large number of additional, e.g. permanent surface effects, which previously could only be achieved by the combination of several products.
  • the treated surfaces can uniquely have other beneficial properties, such as e.g. Soft grip, hydrophilicity, antistatic finish, improvement of substantivity in finishing processes, reduced combing power, accelerated surface drying, gloss, etc., are imparted.
  • beneficial properties such as e.g. Soft grip, hydrophilicity, antistatic finish, improvement of substantivity in finishing processes, reduced combing power, accelerated surface drying, gloss, etc.
  • a very good softening of cellulose-containing textile or tissue fabrics can be achieved with simultaneously high hydrophilicity and resistance to microbes.
  • the method of the present invention has the advantage of providing surface finish which does not yellow and exhibit biocidal activity over a long period of time.
  • Emulsifier A isotridecyl polyethylene oxide ether, about 10 ethylene oxide units, 85% in water available (commercially un- ter the name Lutensol ® TO 109 at BASF AG, Deutsch ⁇ country);
  • Emulsifier B ammonium lauryl sulfate, 40% in water (. Commercially available under the name Texapon ® A from the company Cognis, Germany); Emulsifier C: isotridecyl polyethylene oxide ether, about 5 ethylene oxide units (commercially available under the Bezeich ⁇ voltage Lutensol ® TO 5 from BASF AG, Germany).
  • the antimicrobial test was carried out as follows:
  • the test for antimicrobial activity was carried out with four gram + and three gram bacterial, six fungal and two yeast strains and one algae strain (Table 1). All microorganisms used are commercially available. The production of the required media, nutrient solutions and agar plates, or the cultivation and cultivation of the microorganisms were carried out according to standard microbiological procedures in the manner known to the person skilled in the art. The inventive compositions used were prior to examination by autoclaving at 120 0 C (30 minutes) sterilized to ei ⁇ ne cross-contamination to prevent with foreign organisms.
  • a single colony or a mycelium is removed from the "masterplate" of the microorganism concerned by sterile inoculation and applied to an agar plate in line form
  • the plates are incubated at the temperature typical for the respective test strain until a significant growth can be seen in that part of the inoculation trace which is not covered by the composition according to the invention
  • the extent of the microbial inhibition can be estimated optically from the difference between the growth of the exposed part and the part of the inoculation track located below or directly next to the composition according to the invention. example 1
  • the aqueous solution thus obtained has a solids content of about 60% by weight and a viscosity of 890 mm 2 / s (composition of example 1).
  • Example 1 has strong antimicrobial properties, which is still very pronounced even in high dilution, as the following study on the effectiveness of the antimicrobial inhibition shows.
  • Example 1 The composition of Example 1 prepared above was diluted to the solids content indicated in Table 3 by addition of further water (diluted composition from Example 1). Subsequently, the test for antimicrobial activity was carried out in the manner described above.
  • Example 3 the diluted compositions of Example 1 show a strong antimicrobial activity even in low concentrations.
  • the growth gram + bacteria is inhibited from a concentration of about 0.2 wt .-%, for gram bacteria and yeasts, the effective limit is about 0.5
  • the determination of the minimum inhibitory concentration (MIC) of the composition of Example 1 against E. coli (B) and M. luteus (F) was carried out in the manner known to the person skilled in the art in the classical liquid culture test.
  • the comparison control is a culture solution without addition of the composition from Example 1.
  • the minimum inhibitory concentration (MIC) relative to the respective microorganism can be derived.
  • the absolute MIC is 200 ppm by weight for E. coli and 20 ppm by weight for M. luteus.
  • the reaction product is a yellow, highly viscous oil having a viscosity of about 1 to 6-10 6 mPa-s.
  • the 1 H-NMR spectroscopic investigation confirmed the formation of a polyquaternary polysiloxane with approximately average 30 to 35 repeating units corresponding to the formula
  • the preparation is carried out analogously to the preparation of siloxane I), with 76 g of dimethyl ammonium chloride, 160 ml of water and 1100 g of a linear siloxane consisting of Dimethylsilo- xy- and 3-Glycidoxypropyldimethylsiloxy units, with a Epoxy content of 1.6 mmol / g and a viscosity of 20 mm 2 / s (25 0 C) are used.
  • the reaction product is a gel ⁇ bes, highly viscous oil having a viscosity of about 0.5 to 2.5-10 6 mPa ⁇ s.
  • the "" "H-NMR spectroscopy confirms the formation of a polyquaternary polysiloxane having about ist ⁇ average 5 to 15 repeat units corresponding to the formula
  • the preparation is carried out analogously to the preparation of siloxane I), with 22.2 g of dimethyl ammonium chloride, 1000 g of a linear siloxane consisting of dimethylsiloxy and 3-glycidoxypropyldimethylsiloxy units having an epoxy content of 1.6 mmol / g and a Viscosity of 80 mm 2 / s (25 0 C) and 140 ml of water and 350 g of i-propanol used as a solvent.
  • the reaction product is an almost colorless, viscous oil having a viscosity of about 1 to 3-10 6 mPa ⁇ s.
  • the 1 H NMR spectroscopic investigation confirmed the formation of a polyquaternary polysiloxane having an average of about 3 to 5 repeat units according to the formula
  • compositions according to the invention are mixed and dispersed with one another by means of an emulsifier, such as an "Ultra-Turrax” or dissolver Emulsions of the high molecular weight organopolysiloxanes with quaternary nitrogen groups can be further diluted with water and are stable at room temperature for more than 6 months.
  • an emulsifier such as an "Ultra-Turrax” or dissolver
  • the epoxysiloxanes used are a) a linear polysiloxane consisting of dimethylsiloxy and 3-glycidoxypropyldimethylsiloxy units, having an epoxy content of 2.4 mmol / g and a viscosity of 13 mm 2 / s b) a linear polysiloxane consisting of dimethylsiloxy and 3-glycidoxypropyldimethylsiloxy units having an epoxy content of 1.6 mmol / g and a viscosity of 20 mmVs c) a linear polysiloxane consisting of dimethylsiloxy and Glycidoxypropyldimethylsiloxy units, with an epoxy content of 0.5 mmol / g and a viscosity of 80 mm 2 / s.
  • a solution of dimethylammonium chloride and water is mixed with stirring with the epoxy siloxane, emulsifier and optionally cosolvent and heated to reflux temperature.
  • the mixture is stirred for 5 hours at 110 0 C, the cloudy starting mixture clears and slightly increases in viscosity.
  • the i-propanol is removed in vacuo and the mixture is adjusted to the desired solids content by dilution with water.
  • the aqueous emulsions so obtained of the ⁇ navalmolekula ren organopolysiloxanes with quaternary nitrogen groups are stable longer with water dilutable and further at room temperature for over 3 months.
  • the fabric samples were impregnated with the respective compositions of Example 5 and 6 adjusted with acetic acid to pH 4, squeezed in a two-roll pad on 60% (PES fabric) or 85% (PP nonwoven) liquor pickup, stretched and dried at 110 0 C for 3 minutes. Subsequently the product was air-conditioned at least 12 hours in a climatic chamber at 23 0 C and 50% humidity.
  • Example 5 In comparison to a commercially available fabric softener according to the prior art, the composition of Example 5 imparts excellent hydrophilicity to both PES fabric and PP nonwoven (compare Table 7). In the case of PES fabric, the equipment even has a clear wash permanence. The washing resistance on PP fleece is somewhat lower. Nevertheless, a significant residual hydrophilicity can also be seen on PP nonwoven fabric even after 5 washes, which is at least equal to the hydrophilicity of the standard fabric softener. Table 7:
  • composition thus obtained gives terry tissue a similar excellent soft feel as a commercial, classical textile amines based on aminosiloxane.
  • test fabrics terry toweling, 225 g each, smooth cotton fabric, each 20 x 160 cm, 50 g, smooth cotton / polyester (CO / PES 35/65) blended fabric, each 15 x 100 cm, 45 g
  • test fabrics were rinsed with a water hardness of 3 ° dH.
  • the rinsing cycle was carried out once completely, with 1.5 L of drinking water, 20 g of acetic acid (100%) and those prepared in Example 8 being introduced directly into the washing drum before the beginning of the last rinse.
  • the performance of the performance tests was carried out after drying the fabric and air conditioning at 23 ° C and 60% humidity overnight.
  • the handle evaluation of a pattern is thus calculated as the average of each te ent fallenen to this pattern ⁇ punk.
  • the ironing time is essentially determined by the number of ironing movements that are necessary in order to iron a fabric spot wrinkle-free. For the untreated cotton fabric, 13 ironing steps (100%) were necessary for this, but less for the finished goods. The percentage shortening of the ironing time calculated from this is given in Table 8.
  • Softening and Hydrophilization of Tissue Papers A commercially available, uncoated toilet paper ("bath tissue”) was used.
  • the compositions according to Examples 5, 6 and 7 were each applied to a rubber mat with the aid of a bar doctor and transferred from there by rolling on the tissue paper by means of a stainless steel roller, the application taking place on both sides.
  • an evaluation of the tissue papers with similar active ingredient application (silicone application) was carried out with regard to their softness.
  • the rough assessment was made by 10 subjects who score 0 points per paper pattern (softness of A is inferior to B), 0.5 points (softness of A is similar to that of B) or 1 point (softness of A is better than from B).
  • the results of the grip evaluation are shown in Table 9.
  • aqueous emulsion of a hydrophilic plasticizer based ei ⁇ nes polyether-aminosiloxane available under the name WETSOFT ® CTA from Wacker-Chemie GmbH, Germany.
  • aqueous mixture consisting of 0.6 parts of a 35% aqueous solution of a polyether-functional polysiloxane (available under the name PULPSIL ® S 950 from Wacker Chemie GmbH, Germany) and 0.4 parts of an aqueous Emul ⁇ sion of an amino-functional polysiloxane (available under the name WACKER ® FINISH CT 34 e from Wacker-Chemie GmbH, Germany).
  • compositions according to the invention have an excellent level of activity. They are clearly superior to the standard commercial products of the prior art.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Forests & Forestry (AREA)
  • General Health & Medical Sciences (AREA)
  • Geochemistry & Mineralogy (AREA)
  • Environmental Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Dispersion Chemistry (AREA)
  • Zoology (AREA)
  • Materials Engineering (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • Agronomy & Crop Science (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Silicon Polymers (AREA)
  • Cosmetics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des compositions contenant (A) des composés organosiliciés ayant au moins une unité de la formule -[R<SUP>2</SUP>(SiR<SUB>2</SUB>O)<SUB>b</SUB>-SiR<SUB>2</SUB>-R<SUP>2</SUP>-N<SUP>+</SUP>R<SUP>1</SUP> <SUB>2</SUB>]
EP05774677A 2004-07-29 2005-07-21 Compositions contenant des composes organosilicies polyquaternaires Withdrawn EP1771497A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004036717A DE102004036717A1 (de) 2004-07-29 2004-07-29 Polyquaternäre Organosiliciumverbindungen enthaltende Zusammensetzungen
PCT/EP2005/007965 WO2006013017A1 (fr) 2004-07-29 2005-07-21 Compositions contenant des composes organosilicies polyquaternaires

Publications (1)

Publication Number Publication Date
EP1771497A1 true EP1771497A1 (fr) 2007-04-11

Family

ID=35229652

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05774677A Withdrawn EP1771497A1 (fr) 2004-07-29 2005-07-21 Compositions contenant des composes organosilicies polyquaternaires

Country Status (7)

Country Link
US (1) US20070212326A1 (fr)
EP (1) EP1771497A1 (fr)
JP (1) JP2008508375A (fr)
KR (1) KR20070027730A (fr)
CN (1) CN1993403A (fr)
DE (1) DE102004036717A1 (fr)
WO (1) WO2006013017A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105816343A (zh) * 2016-04-07 2016-08-03 成都蓝孚科技有限公司 一种速干外科手消毒液及其制备方法

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4508794B2 (ja) * 2004-09-14 2010-07-21 信越化学工業株式会社 防汚性縮合硬化型オルガノポリシロキサン組成物及び水中構造物
DE102006023415A1 (de) 2006-05-17 2007-11-22 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Verwendung von aminmodifizierten Siloxanen als Schutzmittel in Beschichtungen und Werkstücken
DE102007047863A1 (de) * 2007-11-26 2009-05-28 Wacker Chemie Ag Quaternäre Ammoniumgruppen aufweisende Organopolysiloxane, deren Herstellung und Verwendung
DE102008001867A1 (de) * 2008-05-19 2009-11-26 Wacker Chemie Ag Verfahren zur Herstellung von quartäre Ammoniumgruppen aufweisenden Organopolysiloxanen
WO2010042935A2 (fr) * 2008-10-10 2010-04-15 Ndsu Research Foundation Compositions antimicrobiennes
WO2010042804A2 (fr) * 2008-10-10 2010-04-15 Ndsu Research Foundation Copolymères pentablocs zwittérioniques/amphiphiles et revêtements fabriqués à partir de ceux-ci
DE102009006586B4 (de) * 2009-01-29 2013-02-28 Neenah Gessner Gmbh Filtermedium sowie Filterelement für die Flüssigkeitsfiltration
US8202194B2 (en) * 2009-03-17 2012-06-19 GM Global Technology Operations LLC Clutch and gear arrangement for a front wheel drive vehicle
US20100318047A1 (en) * 2009-06-16 2010-12-16 Ducker Paul M Absorbent, nonwoven material exhibiting z-direction density gradient
ATE554128T1 (de) * 2009-08-06 2012-05-15 Siate S R L Polymere, träger mit den polymeren und verwendungen davon als farbaufnehmende und bakterizide wirkstoffe
US20110171279A1 (en) * 2009-11-02 2011-07-14 Ndsu Research Foundation Polyethylenimine biocides
EP2324984B1 (fr) 2009-11-12 2012-05-23 Quadrant Epp Ag Compositions de polyéthylène antisalissure à très fort poids moléculaire et leurs procédés d'utilisation
DE202009016240U1 (de) 2009-11-27 2010-04-29 Weihmann, Andreas, Dipl.-Designer Wassergewinnungssystemtechnologie
DE102011078382A1 (de) 2011-06-30 2013-01-03 Evonik Goldschmidt Gmbh Mikroemulsion von quaternären Ammoniumgruppen enthaltenden Polysiloxanen, derenHerstellung und Verwendung
US20200168331A1 (en) 2012-03-02 2020-05-28 Leonard Solie Clinician station for providing medical services remotely
US11978552B2 (en) * 2012-03-02 2024-05-07 Md Health Rx Solutions, Llc Medical services kiosk
US11984228B1 (en) 2012-03-02 2024-05-14 Md Health Rx Solutions, Llc Medical service kiosk having an integrated scale
DE102013206175A1 (de) * 2013-04-09 2014-10-09 Evonik Industries Ag Polysiloxan-Polyether-Copolymere mit Amino- und/oder quaternären Ammoniumgruppen im Polyetherteil und Verfahren zu deren Herstellung
KR102217762B1 (ko) * 2013-12-20 2021-02-22 새니타이즈드 아게 미생물의 직물에의 부착을 감소시키는 방법
CN115449952A (zh) * 2022-09-29 2022-12-09 董健 一种抑菌透气吸湿型纺织面料

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5326841A (en) * 1989-01-25 1994-07-05 Epitope, Inc. Germicidal barriers
TW243455B (fr) * 1993-02-09 1995-03-21 Ciba Geigy
US5954869A (en) * 1997-05-07 1999-09-21 Bioshield Technologies, Inc. Water-stabilized organosilane compounds and methods for using the same
DE19742761A1 (de) * 1997-09-27 1999-04-01 Gerd Dr Rossmy An ihrer Oberfläche anisotrop verteilte überwiegend hydrophile und überwiegend hydrophobe Domänen aufweisende amphiphile Teilchen oder Moleküle
ES2227271T3 (es) * 2000-07-27 2005-04-01 GE BAYER SILICONES GMBH &amp; CO. KG Compuestos de poliamonio-polisiloxano, procedimiento para su produccion y su uso.
US7041767B2 (en) * 2000-07-27 2006-05-09 Ge Bayer Silicones Gmbh & Co. Kg Polysiloxane polymers, method for their production and the use thereof
DE10139963A1 (de) * 2001-08-14 2003-03-06 Wacker Chemie Gmbh Quaternäre Ammoniumgruppen aufweisende Organopolysiloxane und Verfahren zu deren Herstellung
US6787603B2 (en) * 2002-11-27 2004-09-07 Dow Corning Corporation Method of making emulsion containing quaternary ammonium functional silanes and siloxanes

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2006013017A1 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105816343A (zh) * 2016-04-07 2016-08-03 成都蓝孚科技有限公司 一种速干外科手消毒液及其制备方法

Also Published As

Publication number Publication date
DE102004036717A1 (de) 2006-03-23
JP2008508375A (ja) 2008-03-21
CN1993403A (zh) 2007-07-04
KR20070027730A (ko) 2007-03-09
WO2006013017A1 (fr) 2006-02-09
US20070212326A1 (en) 2007-09-13

Similar Documents

Publication Publication Date Title
WO2006013017A1 (fr) Compositions contenant des composes organosilicies polyquaternaires
EP2308308B1 (fr) Solutions aqueuses stables de composés ammonium quaternaire silane
EP2444447B1 (fr) Polysiloxane doté de groupes contenant de l&#39;azote
EP2528660B1 (fr) Nouveaux copolymères linéaires de polyéther polydiméthylsiloxane comportant des groupes amino et/ou ammonium quaternaire et leur utilisation
US7851653B2 (en) Method of creating a solvent-free polymeric silicon-containing quaternary ammonium antimicrobial agent having superior sustained antimicrobial properties
WO2011032797A1 (fr) Nouveaux polysiloxanes comprenant des groupes ammonium quaternaire et leur utilisation
EP2726185A1 (fr) Microémulsion de polysiloxanes contenant des groupes ammonium quaternaire, production et utilisation de ladite microémulsion
DE102006035511A1 (de) Neuartige Polysiloxane mit quaternären Ammoniumgruppen, Verfahren zu deren Herstellung und deren Verwendung als Textilweichmacher
EP1887863A2 (fr) Procedes et compositions pour des traitements biocides
EP2363422A1 (fr) Copolymères greffés de silicium organique contenant de l&#39;azote
WO2008071681A1 (fr) Composition antimicrobienne pour l&#39;apprêt de textiles
CN101812086A (zh) 一种抗菌化合物及其制备方法
EP3853334B1 (fr) Contenants de stockage contenant du polysiloxane et leur utilisation dans des compositions préférées de soins textiles
CN111333862B (zh) 一种抗病毒乳液组合物及涂料及其制备方法
ES2921007T3 (es) Polímeros para el acabado textil hidrófobo y oleófobo
DE602004007717T2 (de) Silikon-modifiziertes antimikrobielles Polymer, antimikrobielles Mittel und antimikrobielle Harzzusammensetzung
KR101002901B1 (ko) 기재 처리용 폴리오르가노실록산 조성물
AU2011350928B2 (en) Durable antimicrobial composition
EP1595910A1 (fr) Dérivés d&#39;organopolysiloxanes linéaires ou ramifiés à fonctions amines, présentant des groupements amines quaternaires permanents
KR20150120656A (ko) 섬유용 비휘발성 항균 처리제 조성물
DE102014216380A1 (de) Emulsionen von Aminosiloxanen und Silicaten
EP3935116B1 (fr) Émulsions d&#39;aminosiloxanes et de silicates
EP4166710A1 (fr) Composition douce au toucher
WO2007131487A1 (fr) Utilisation de siloxanes modifiés par une amine comme agents protecteurs dans des revêtements et des pièces

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20070110

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): BE DE FR GB NL

17Q First examination report despatched

Effective date: 20070518

RIN1 Information on inventor provided before grant (corrected)

Inventor name: SCHWAB, BIRGIT

Inventor name: OCHS, CHRISTIAN

DAX Request for extension of the european patent (deleted)
RBV Designated contracting states (corrected)

Designated state(s): BE DE FR GB NL

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20080624