WO2002064642A1 - Procede de production de surfaces microbicides par immobilisation d'amino-alcools - Google Patents

Procede de production de surfaces microbicides par immobilisation d'amino-alcools Download PDF

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Publication number
WO2002064642A1
WO2002064642A1 PCT/EP2002/000456 EP0200456W WO02064642A1 WO 2002064642 A1 WO2002064642 A1 WO 2002064642A1 EP 0200456 W EP0200456 W EP 0200456W WO 02064642 A1 WO02064642 A1 WO 02064642A1
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WO
WIPO (PCT)
Prior art keywords
branched
carbon atoms
aromatic hydrocarbon
unbranched aliphatic
reaction
Prior art date
Application number
PCT/EP2002/000456
Other languages
German (de)
English (en)
Inventor
Peter Ottersbach
Beate Kossmann
Original Assignee
Creavis Gesellschaft Für Technologie Und Innovation Mbh
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 Creavis Gesellschaft Für Technologie Und Innovation Mbh filed Critical Creavis Gesellschaft Für Technologie Und Innovation Mbh
Publication of WO2002064642A1 publication Critical patent/WO2002064642A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C30/00—Coating with metallic material characterised only by the composition of the metallic material, i.e. not characterised by the coating process
    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
    • 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
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/12—Chemical modification
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C26/00—Coating not provided for in groups C23C2/00 - C23C24/00
    • C23C26/02—Coating not provided for in groups C23C2/00 - C23C24/00 applying molten material to the substrate
    • 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
    • C03C2204/00—Glasses, glazes or enamels with special properties
    • C03C2204/02—Antibacterial glass, glaze or enamel

Definitions

  • the invention relates to the use and use of amino alcohols for the production of microbicidal plastic surfaces.
  • Mucus layers often form, which cause microbial populations to rise extremely, which have a lasting impact on the quality of water, beverages and food, and can even lead to product spoilage and consumer health damage.
  • Bacteria must be kept away from all areas of life where hygiene is important. This affects textiles for direct body contact, especially for the intimate area and for nursing and elderly care. In addition, bacteria must be kept away from furniture and device surfaces in care stations, in particular in the area of intensive care and the care of small children, in hospitals, in particular in rooms for medical interventions and in isolation stations for critical infections and in toilets.
  • Another way of preventing surface bacteria from spreading is to incorporate antimicrobial substances into a matrix.
  • the copolymer produced with aminomethacrylates is only a matrix or carrier substance for added microbicidal active substances which can diffuse or migrate from the carrier substance. Polymers of this type lose theirs more or less quickly
  • MIK surface
  • This terpolymer exhibits so-called contact microbicidity without the addition of a microbicidal active ingredient.
  • a large number of contact microbicidal polymers are known from the following patent applications: DE 100 24 270, DE 100 22 406, PCT / EP00 / O6501, DE 100 14 726, DE 100 08 177, PCT / EP00 / 06812, PCT / EP00 / 06487 , PCT / EP00 / O6506, PCT / EP00 / 02813, PCT / EP00 / 02819, PCT / EP00 / 02818, PCT / EP00 / 02780, PCT / EP00 / 02781, PCT / EP00 / 02783, PCT / EP00 / 02782, PCT / EP00 / 02799, PCT / EP00 / 02798, PCT / EP00 / 00545, PCT / EP00 / 00544.
  • These polymers do not contain any low molecular weight components; the antimicrobial properties are due to the contact of bacteria with the surface.
  • the present invention therefore relates to a process for producing microbicidal surfaces by reacting substrate surfaces with amino alcohols of the formula I.
  • Rl branched or unbranched aliphatic or aromatic
  • R2 H, branched or unbranched aliphatic or aromatic
  • R3 H, branched or unbranched aliphatic or aromatic
  • the method according to the invention is suitable for surfaces such as e.g. Glass, ceramics, wood, metal and plastics can be used with and without functional groups.
  • a primer layer with reactive functional groups can be applied in advance to the surfaces to be protected.
  • the polymers mentioned below can be used as primers.
  • Preferred amino alcohols of the formula (I) are tert-butylaminoethanol, tert-butylaminomethanol, tert-butylaminopropanol, 2-butylaminoethanol, 2-butylaminomethanol, 2-butylaminopropanol, 2-diethylaminoethanol, 2-diethylaminomethanol, 2-diethylamino propanol, 2- Dimethylaminoethanol, 2-dimethylaminomethanol and / or 2-dimethylami- nopropanol used.
  • the substrate surfaces can contain functional groups such as hydroxy, carboxylic acid, sulfonic acid, amino, cyano, ester, ether and / or amide residues.
  • the surfaces can consist of or contain polyacrylates, polymethacrylates, polyesters, polyamides, cellulose and its derivatives and / or silk.
  • the method of the invention is such that the amino alcohol to be immobilized on the surface either directly in liquid form or dissolved in a suitable solvent, e.g. B. alcohols such as methanol, ethanol or ketones such as acetone, MEK, cyclohexane, THF is applied to the surface to be impregnated, e.g. by dipping or spraying.
  • a suitable solvent e.g. B. alcohols such as methanol, ethanol or ketones such as acetone, MEK, cyclohexane, THF
  • an immobilization reaction of the amino alcohol with the functional groups of the surface which are generally carried out by supplying heat and / or high-energy electromagnetic radiation and, if appropriate, adding catalysts, such as. B. acids or bases is induced.
  • the surface of excess, non-immobilized starting materials is washed off with the abovementioned. Free solvents.
  • a heat treatment of 20 to 200 ° C., in particular 50 to 120 ° C., is preferably carried out.
  • Polymethyl methacrylate and other polymethacrylic acid esters are preferred substrates for the process according to the invention.
  • Another object of the invention is therefore an antimicrobial surface, polymethacrylate with amino alcohols of the formula I.
  • Rl branched or unbranched aliphatic or aromatic hydrocarbon radical with 1 to 15 carbon atoms.
  • R2 H, branched or unbranched aliphatic or aromatic
  • R3 H, branched or unbranched aliphatic or aromatic
  • Hydrocarbon residue with 1 to 15 carbon atoms is implemented.
  • antimicrobial products can now either be used directly, e.g. B. in form hardened polymethyl methacrylate plates, or by a subsequent physical treatment, such as. B. grinding, prepare for further treatment steps.
  • the correspondingly ground products can e.g. B. directly as an aqueous solution, e.g. B. for the disinfection of cooling water circuits or indirectly z. B. be used by working in paints or other coatings.
  • Use of the compounds or polymer formulations e.g. B. directly as an aqueous solution, e.g. B. for the disinfection of cooling water circuits or indirectly z. B. be used by working in paints or other coatings.
  • microbicidal surfaces produced according to the invention for the production of antimicrobially active products and the products thus produced as such.
  • Such products are preferably based on polyamides, polyurethanes, polyether block amides, polyester amides, polyester imides, PVC, polyolefins, silicones, polysiloxanes, polymethacrylate or polyterephthalates, metals, glasses, woods and ceramics, which have surfaces coated with the methods according to the invention.
  • Antimicrobial products of this type are, for example, and in particular machine parts for food processing, components for air conditioning systems, polymer membranes, coated pipes, semi-finished products, roofing, bathroom and toilet articles, kitchen articles, components for sanitary facilities, components for animal cages and housings, toys, components in water systems , Food packaging, controls (touch panel) of devices and contact lenses.
  • the compounds and methods according to the invention can be used wherever there is a need for bacteria-free, algae and fungus-free, i.e. H. microbicidal surfaces or surfaces with non-stick properties.
  • bacteria-free, algae and fungus-free i.e. H. microbicidal surfaces or surfaces with non-stick properties.
  • examples of use for the compounds or polymer formulations according to the invention can be found in the following areas:
  • Marine hulls, port facilities, buoys, drilling platforms, ballast water tanks.
  • House roofs, cellars, walls, facades, greenhouses, sun protection, garden fences, wood protection
  • Food machines, kitchen, kitchen items, sponges, toys, food packaging, milk processing, drinking water systems, cosmetics - machine parts: air conditioners, ion exchangers, process water, solar systems, heat exchangers, bioreactors, membranes, cooling water treatment Medical technology: contact lenses, diapers, membranes, implants Articles of daily use: car seats, clothing (stockings, sports clothing), hospital facilities, door handles, telephone receivers, public transport, animal cages, cash registers, carpeting, wallpapers.
  • objects of the present invention are the use with hygiene products or medical technology articles produced with coatings or processes produced according to the invention.
  • hygiene products include toothbrushes, toilet seats, combs and packaging materials.
  • hygiene articles also includes other objects that may U. come into contact with many people, such as telephone receivers, handrails of stairs, door and window handles as well as holding belts and handles in public transport.
  • Medical technology articles are e.g. B. catheters, tubes, cover sheets or surgical cutlery.
  • the compounds according to the invention or the surfaces produced by the process according to the invention are used as a biofouling inhibitor, in particular in cooling circuits.
  • a biofouling inhibitor in particular in cooling circuits.
  • microbicidal substances such as formalin is not possible with open cooling systems, as are common in power plants or chemical plants.
  • microbicidal substances are often highly corrosive or foam-forming, which prevents use in such systems.
  • the preferred dispersed form is polymer particles. These can even z. B. by emulsion polymerization, precipitation or suspension polymerization or subsequently by grinding z. B. obtained in a jet mill and then microbicidal according to the invention.
  • the particles are preferably used in a size distribution of 0.001 to 3 mm (as a spherical diameter), so that on the one hand a large surface is available for killing the bacteria or algae, and on the other hand where necessary, the separation from the cooling water, for. B. is easily possible by filtration.
  • the method can e.g. B. be exercised so that part (5-10%) of the particles used are continuously removed from the system and replaced by an appropriate amount of fresh material.
  • additional antimicrobial particles can be added if required by checking the bacterial count of the water. Depending on the water quality, 0.1-100 g antimicrobial polymer formulation per m 3 of cooling water is sufficient.
  • Example la A 4 by 3 cm piece of the film from Example 1 is placed on the bottom of a beaker containing 10 mL of a test microbial suspension of Pseudomonas aeruginosa. The system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time the number of germs decreased from 10 7 to 10 3 germs per mL.
  • a 4 by 3 cm piece of the film from Example 1 is placed on the bottom of a beaker containing 10 mL of a test germ suspension of Staphylococcus aureus.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time, the number of germs dropped from 10 7 to 10 2 germs per mL.
  • a 4 by 3 cm piece of the film from Example 2 is placed on the bottom of a beaker containing 10 mL of a test microbial suspension of Pseudomonas aeruginosa.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time the number of germs decreased from 10 7 to 10 4 germs per mL.
  • Example 2b A 4 by 3 cm piece of the film from Example 2 is placed on the bottom of a beaker containing 10 mL of a test germ suspension of Staphylococcus aureus. The system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time, the number of germs dropped from 10 7 to 10 2 germs per mL.
  • a 4 by 3 cm piece of the film from Example 3 is placed on the bottom of a beaker containing 10 mL of a test microbial suspension of Pseudomonas aeruginosa.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time the number of germs decreased from 10 7 to 10 4 germs per mL.
  • a 4 by 3 cm piece of the film from Example 3 is placed on the bottom of a beaker containing 10 mL of a test germ suspension of Staphylococcus aureus.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time the number of germs decreased from 10 7 to 10 3 germs per mL.
  • Example 4 50 mL 2-dimethylaminoethanol (Aldrich) is dissolved in a mixture of 20 g demineralized water and 30 g methanol. 2 mL of this solution are finely distributed on a 4 x 6 cm PMMA film using an atomizer. The film treated in this way is then heated in a drying cabinet at 80 ° C. for 2 hours. After the time has elapsed, the film is allowed to cool to room temperature, then it is rinsed with 200 ml of a 1% by weight solution of methanol in demineralized water.
  • a 4 by 3 cm piece of the film from Example 4 is placed on the bottom of a beaker containing 10 mL of a test microbial suspension of Pseudomonas aeruginosa.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time the number of germs decreased from 10 7 to 10 4 germs per mL.
  • a 4 by 3 cm piece of the film from Example 4 is placed on the bottom of a beaker containing 10 mL of a test germ suspension of Staphylococcus aureus.
  • the system prepared in this way is now shaken for a period of 4 hours. Then 1 mL of the test microbial suspension is removed. After this time the number of germs decreased from 10 7 to 10 3 germs per mL.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Metallurgy (AREA)
  • Mechanical Engineering (AREA)
  • Pest Control & Pesticides (AREA)
  • Geochemistry & Mineralogy (AREA)
  • Hydrology & Water Resources (AREA)
  • Water Supply & Treatment (AREA)
  • Agronomy & Crop Science (AREA)
  • Environmental & Geological Engineering (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne un procédé permettant de produire des surfaces microbicides par immobilisation d'amino-alcools.
PCT/EP2002/000456 2001-02-10 2002-01-18 Procede de production de surfaces microbicides par immobilisation d'amino-alcools WO2002064642A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2001106230 DE10106230A1 (de) 2001-02-10 2001-02-10 Verfahren zur Herstellung mikrobizider Oberflächen durch Immobilisierung von Aminoalkoholen
DE10106230.3 2001-02-10

Publications (1)

Publication Number Publication Date
WO2002064642A1 true WO2002064642A1 (fr) 2002-08-22

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ID=7673613

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/000456 WO2002064642A1 (fr) 2001-02-10 2002-01-18 Procede de production de surfaces microbicides par immobilisation d'amino-alcools

Country Status (2)

Country Link
DE (1) DE10106230A1 (fr)
WO (1) WO2002064642A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10136456A1 (de) * 2001-07-26 2003-02-20 Creavis Tech & Innovation Gmbh Mikrobizide Tapeten mit Aminoalkoholen
WO2010096654A1 (fr) 2009-02-21 2010-08-26 Tyco Healthcare Group Lp Dispositifs médicaux présentant des surfaces activées
EP2398523B1 (fr) * 2009-02-21 2018-04-04 Covidien LP Dispositifs médicaux présentant des surfaces activées

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2109877A (en) * 1935-11-20 1938-03-01 Du Pont Ester interchange process
US2915481A (en) * 1951-12-04 1959-12-01 Pure Oil Co Acrylic resins modified with alkanolamines
SU985018A1 (ru) * 1981-06-05 1982-12-30 Институт Химии Башкирского Филиала Ан Ссср Бактерицид дл буровых растворов
EP0102093A1 (fr) * 1982-07-13 1984-03-07 Société Industrielle et Salines de Bayonne Compositions pesticides pour le traitement du bois
EP0124851A2 (fr) * 1983-05-07 1984-11-14 Henkel Kommanditgesellschaft auf Aktien Composition et procédé pour le nettoyage et la passivation de métaux par pulvérisation
CA1225002A (fr) * 1984-04-24 1987-08-04 Colin S. Jolly Sols de silice lavable a l'eau, et leur emploi a titre d'agents antiderapage
WO1998025649A1 (fr) * 1996-12-13 1998-06-18 Alcon Laboratories, Inc. Utilisation d'amino-alcools de faible poids moleculaire dans des compositions ophtalmiques
WO1999015012A1 (fr) * 1997-09-25 1999-04-01 Henkel-Ecolab Gmbh & Co. Ohg Procede pour le nettoyage et la desinfection d'instruments medicaux

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2109877A (en) * 1935-11-20 1938-03-01 Du Pont Ester interchange process
US2915481A (en) * 1951-12-04 1959-12-01 Pure Oil Co Acrylic resins modified with alkanolamines
SU985018A1 (ru) * 1981-06-05 1982-12-30 Институт Химии Башкирского Филиала Ан Ссср Бактерицид дл буровых растворов
EP0102093A1 (fr) * 1982-07-13 1984-03-07 Société Industrielle et Salines de Bayonne Compositions pesticides pour le traitement du bois
EP0124851A2 (fr) * 1983-05-07 1984-11-14 Henkel Kommanditgesellschaft auf Aktien Composition et procédé pour le nettoyage et la passivation de métaux par pulvérisation
CA1225002A (fr) * 1984-04-24 1987-08-04 Colin S. Jolly Sols de silice lavable a l'eau, et leur emploi a titre d'agents antiderapage
WO1998025649A1 (fr) * 1996-12-13 1998-06-18 Alcon Laboratories, Inc. Utilisation d'amino-alcools de faible poids moleculaire dans des compositions ophtalmiques
WO1999015012A1 (fr) * 1997-09-25 1999-04-01 Henkel-Ecolab Gmbh & Co. Ohg Procede pour le nettoyage et la desinfection d'instruments medicaux

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 198343, Derwent World Patents Index; AN 1983-800162, XP002206363, 1 *

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Publication number Publication date
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