Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
  • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
  • C08F290/14—Polymers provided for in subclass C08G
  • C08F290/147—Polyurethanes; Polyureas
• • 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
  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
  • A01N25/10—Macromolecular compounds
• • 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
  • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
  • A01N25/24—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients to enhance the sticking of the active ingredients
• • 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
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
  • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
  • A61L27/28—Materials for coating prostheses
  • A61L27/34—Macromolecular materials
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
  • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
  • A61L29/08—Materials for coatings
  • A61L29/085—Macromolecular materials

Definitions

• the present invention relates to a process for manufacturing bactericidal polymers, as well as the products obtained by this process.
• binders consist of the combination of a chlorinated vinylyque polymer with 10 to 20% by weight of a quaternary ammonium salt of which at least one substituent is chosen from the group comprising a hydrocarbon derivative with a long linear chain, aryl or alkyl .
• the present invention makes it possible to obtain a plastic material which can be used for producing probes, catheters, or other instruments for medical use.
• This product has biocidal properties whose role is to inhibit the formation of bacterial biofilm. Due to its low manufacturing cost and its ecological process (no solvent), it is easy to make this research industrializable.
• the originality of the concept lies in the fact that the bactericidal agent enters directly into the final composition of the basic formulations.
• the method according to the invention is based on the formation of a coating which has a covalent bond between a bactericidal agent and a three-dimensional network itself adhering to the base material consisting of a synthetic resin, said bond being obtained by exposure to energetic radiation, for example ultraviolet, gamma rays or electronic bombardments, of a formulation comprising three essential components consisting of at least one photoinitiator, at least one crosslinkable oligomer and at least one mono or multifunctional monomer, as well as various additives giving specific properties to the final product.
• energetic radiation for example ultraviolet, gamma rays or electronic bombardments
• One of the originalities comes from the synthesis of a monomer capable of acting as an antiseptic and of reacting with a polymer or an oligomer which is particularly active under energetic activation.
• One of the processes used is that of photocrosslinking under ultraviolet radiation to create a coating having quaternary ammonium bonds, the basic formulation consisting of a mixture of photoinitiator (s), oligomers and monomer (s) mono or multifunctional (s).
• the crosslinkable formulation by radical route is a mixture of compounds comprising at least one bactericidal agent with an unsaturated structure consisting of a multifunctional monomer formed of molecules having the following structure: 0
• This molecule has the following peculiarities
• the bactericidal effect is maximum, if and only if, the quaternary ammonium has an alkyl chain structure (R7) in C8hl7 ⁇ and a counterion X ⁇ .
• This counterion is a bromide ion because the iodide ion would be too bulky and the divalent anion would induce conformation constraints and therefore a decrease in antimicrobial activity.
• the reaction principle is based on a reaction between a tertiary amine and an alkyl halide in an acetone / dichloromethane mixture.
• the quaternary ammonium monomer is cold precipitated in pentane, filtered and rinsed several times with pentane and dried under vacuum over phosphoric anhydride (P205).
• the product thus obtained is a white salt which is characterized by infrared (IR), by (P205).
• the product thus obtained is a white salt which is characterized by infrared (IR), by nuclear magnetic resonance (NMR 200 Mhz) and by elemental analysis (determination of nitrogen, oxygen and bromine).
• the reaction resulting from the process according to the invention is that of a radical polymerization.
• the polymerization rate will depend on the light intensity, the efficiency of the photoinitiator, the reactivity of the functional group and the viscosity of the medium.
• the final polymerization rate and the physico-chemical properties of the photocrosslinked polymer will depend on the chemical structure and the functionality of the monomer and of the oligomer.
• Crosslinkable oligomers are polymers or copolymers which are particularly active under energy radiation.
• the subject of the present invention is a polymer material for medical use which is characterized in that it is based at least on a resin or a mixture of resins resulting from the combination of diol, diisocyanate and ether vinyl.
• the mono or multifunctional monomers are for example reactive diluent monomers such as TGPDA, HDDA or HEA These compounds carrying two reactive functions chosen from epoxy, vinyl or hydroxy ether functions, combined or not, will affect the speed of polymerization, on the conversion rate and therefore on the physicochemical properties of the crosslinked polymer.
• the basic formulation could have the following composition:
• the material has a more or less significant antibacterial effect.
• the basic formulation includes three essential components, namely one or more photoinitiator (s), one or more crosslinkable oligomer (s) and one or more mono or multifunctional monomer (s), as well as various additives intended to give the final product well-defined properties.
• additives are in particular stabilizers, wetting agents, spreading agents, fillers, pigments, etc., provided that they are not themselves inhibitors of the polymerization.
• the photocrosslinking process can be considered as the transition from an unactivated basic system to an activated system, then crosslinked.
• the bactericidal product incorporated into the basic formulation resin (s) acrylate (s), photoinitiator (s), monomer (s) and additive (s) constitutes a more or less viscous mixture which is used to coat a synthetic material preferably made up a polyvinyl chloride, a polyurethane or a polycarbonate previously activated on the surface chemically and / or mechanically, the synthetic material once coated having passed under ultraviolet radiation.
• the compositions thus formulated can be applied according to any known technique, for example spray gun, hardened or defiled.
• the photoinitiator is not necessary for formulation, and activation of the material is then unnecessary.
• Another more recent system consists of photo or cationic electropolymerization.
• the monomers capable of reacting with such a system are vinyl ethers, epoxides but also derivatives of aromatic compounds such as styrene.
• the photoinitiators used are very different from the previous ones, in the sense that these products decompose under ultraviolet radiation, forming Lewis acids. This will allow the polymerization, inter alia, of epoxides, vinyl ethers or other monomers and polymer (s) capable of reacting under radiative / cationic crosslinking.
• the diaryliodonium salts [(Ar2I + , X ") j or bis (diodecylphenyl) iodonium [(C12H25Ar2r * * , X
• X represents in all these compounds an anion of type PF6 “, BF4", AsF6 “ , SbF6 “ , FeC14 “ , SbC16 ⁇ , ...
• aryl radicals are generally phenyl radicals. These aryl radicals are optionally substituted by a linear or branched alkyl radical having from 1 to 12 carbon atoms.
• the bactericidal agent is introduced into the formulation as a reactive diluting agent.
• the positioning of the various constituent elements gives the object of the invention a maximum of useful effects which had not, to date, been obtained by similar devices.

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• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• General Health & Medical Sciences (AREA)
• Environmental Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Agronomy & Crop Science (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• Animal Behavior & Ethology (AREA)
• Medicinal Chemistry (AREA)
• Toxicology (AREA)
• Veterinary Medicine (AREA)
• Public Health (AREA)
• Epidemiology (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Transplantation (AREA)
• Materials For Medical Uses (AREA)
• Dermatology (AREA)
• Oral & Maxillofacial Surgery (AREA)
• Organic Chemistry (AREA)
• Paints Or Removers (AREA)
• Polymers & Plastics (AREA)

Applications Claiming Priority (3)

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• 1996
  • 1996-06-13 FR FR9607579A patent/FR2749854A1/fr not_active Withdrawn
• 1997
  • 1997-06-13 WO PCT/FR1997/001072 patent/WO1997047696A1/fr not_active Application Discontinuation
  • 1997-06-13 EP EP97929350A patent/EP0858486A1/de not_active Withdrawn

Non-Patent Citations (1)

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