DE2922347A1 - Antimicrobial surface treatment of materials - by covalent coupling with antimicrobial agent - Google Patents
Antimicrobial surface treatment of materials - by covalent coupling with antimicrobial agentInfo
- Publication number
- DE2922347A1 DE2922347A1 DE19792922347 DE2922347A DE2922347A1 DE 2922347 A1 DE2922347 A1 DE 2922347A1 DE 19792922347 DE19792922347 DE 19792922347 DE 2922347 A DE2922347 A DE 2922347A DE 2922347 A1 DE2922347 A1 DE 2922347A1
- Authority
- DE
- Germany
- Prior art keywords
- antimicrobial
- materials
- groups
- antimicrobial properties
- reactive
- 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- Withdrawn
Links
- 230000000845 anti-microbial effect Effects 0.000 title claims abstract description 49
- 239000000463 material Substances 0.000 title claims abstract description 28
- 230000008878 coupling Effects 0.000 title claims description 13
- 238000010168 coupling process Methods 0.000 title claims description 13
- 238000005859 coupling reaction Methods 0.000 title claims description 13
- 239000004599 antimicrobial Substances 0.000 title abstract description 7
- 238000004381 surface treatment Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 18
- 230000008569 process Effects 0.000 claims abstract description 10
- 230000000813 microbial effect Effects 0.000 claims abstract description 9
- 239000004744 fabric Substances 0.000 claims abstract description 4
- 239000004753 textile Substances 0.000 claims abstract description 3
- -1 containers Substances 0.000 claims abstract 2
- 239000012528 membrane Substances 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims description 33
- 239000007787 solid Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 230000007797 corrosion Effects 0.000 claims description 4
- 238000005260 corrosion Methods 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 2
- 230000000717 retained effect Effects 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 150000003573 thiols Chemical class 0.000 claims 2
- GVBHCMNXRKOJRH-UHFFFAOYSA-N 2,4,5,6-tetrachloropyrimidine Chemical compound ClC1=NC(Cl)=C(Cl)C(Cl)=N1 GVBHCMNXRKOJRH-UHFFFAOYSA-N 0.000 claims 1
- UOQYWMZLTNEIFI-UHFFFAOYSA-N 2-[3-aminopropyl(methyl)amino]ethanol Chemical compound OCCN(C)CCCN UOQYWMZLTNEIFI-UHFFFAOYSA-N 0.000 claims 1
- XKUCNBHFKJTDCM-UHFFFAOYSA-N 3-[dichloro(methyl)silyl]propan-1-amine Chemical compound C[Si](Cl)(Cl)CCCN XKUCNBHFKJTDCM-UHFFFAOYSA-N 0.000 claims 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 150000001718 carbodiimides Chemical class 0.000 claims 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims 1
- 229940106681 chloroacetic acid Drugs 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 125000005442 diisocyanate group Chemical group 0.000 claims 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical class C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 239000005003 food packaging material Substances 0.000 claims 1
- 239000011129 pharmaceutical packaging material Substances 0.000 claims 1
- 230000009257 reactivity Effects 0.000 claims 1
- 230000002441 reversible effect Effects 0.000 claims 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 239000012634 fragment Substances 0.000 abstract 1
- 239000005022 packaging material Substances 0.000 abstract 1
- 244000005700 microbiome Species 0.000 description 10
- 229920002678 cellulose Polymers 0.000 description 9
- 235000010980 cellulose Nutrition 0.000 description 9
- 239000001913 cellulose Substances 0.000 description 8
- 241000191938 Micrococcus luteus Species 0.000 description 7
- 125000003172 aldehyde group Chemical group 0.000 description 6
- 241000588724 Escherichia coli Species 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 4
- 244000052616 bacterial pathogen Species 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 230000003641 microbiacidal effect Effects 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000000645 desinfectant Substances 0.000 description 3
- 229940124561 microbicide Drugs 0.000 description 3
- 239000002855 microbicide agent Substances 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 206010048038 Wound infection Diseases 0.000 description 2
- 235000010419 agar Nutrition 0.000 description 2
- ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 2
- 238000004500 asepsis Methods 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000006916 nutrient agar Substances 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000009423 ventilation Methods 0.000 description 2
- GFLPSABXBDCMCN-UHFFFAOYSA-N 4,4-diethoxybutan-1-amine Chemical compound CCOC(OCC)CCCN GFLPSABXBDCMCN-UHFFFAOYSA-N 0.000 description 1
- DZQLQEYLEYWJIB-UHFFFAOYSA-N 4-aminobutanal Chemical compound NCCCC=O DZQLQEYLEYWJIB-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000005253 cladding Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002542 isoureas Chemical class 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D65/00—Accessories or auxiliary operations, in general, for separation processes or apparatus using semi-permeable membranes
- B01D65/02—Membrane cleaning or sterilisation ; Membrane regeneration
- B01D65/022—Membrane sterilisation
-
- 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
- A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D39/00—Filtering material for liquid or gaseous fluids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
- B01D67/0081—After-treatment of organic or inorganic membranes
- B01D67/0093—Chemical modification
- B01D67/00931—Chemical modification by introduction of specific groups after membrane formation, e.g. by grafting
-
- 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
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2321/00—Details relating to membrane cleaning, regeneration, sterilization or to the prevention of fouling
- B01D2321/16—Use of chemical agents
- B01D2321/168—Use of other chemical agents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2323/00—Details relating to membrane preparation
- B01D2323/38—Graft polymerization
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2325/00—Details relating to properties of membranes
- B01D2325/48—Antimicrobial properties
-
- 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
- D06M2400/00—Specific information on the treatment or the process itself not provided in D06M23/00-D06M23/18
- D06M2400/01—Creating covalent bondings between the treating agent and the fibre
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Inorganic Chemistry (AREA)
- Toxicology (AREA)
- Environmental Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Transplantation (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
Abstract
Description
Verfahren zur Herstellung von Materialien mit anti-Process for the production of materials with anti-
mikrobiellen Eigenschaften und die nach diesem Verfahren hergestellten Materialien bzw. Gegenstcinde.microbial properties and those produced by this process Materials or objects.
Die Erfindung betrifft ein Verfahren zur Herstellung von Materialien mit antimikrobiellen Eigenschaften.The invention relates to a method for producing materials with antimicrobial properties.
Die Anmeldung bezieht sich auch auf nach diesem Verfahren hergestellte Materialien bzw. Gegenstände.The application also relates to those produced by this process Materials or objects.
Es ist bekannt, daß Gegenstände verschiedenster Art, Konstruktionselemente und komplette Konstruktionen infolge Kinvirkung von Mikroorganismen wie Fäulnisbakterien oder Schimmelpilzen beschädigt und bis zur Unbrauchbarkeit zerstört werden können. Die durch diese mikrobielle Korrosion entstehenden Schäden gehen in nahezu unermeßliche Höhen. Als Beispiel seien der Befall von Holzkonstruktionen mit Pilzen in Form des Hausschwammes, die Zerstörung von Textilien durch Schimmelpilze und Fäulnisbakterien, der Befall elektronischer Bauteile durch Mikroorganismen etc. erwähnt.It is known that objects of various types, construction elements and complete constructions due to the action of microorganisms such as putrefactive bacteria or molds can be damaged and destroyed to the point of uselessness. The damage caused by this microbial corrosion is almost immeasurable Heights. An example is the infestation of wooden structures with fungi in the form of the Dry rot, the destruction of textiles by mold and putrefactive bacteria, the infestation of electronic components by microorganisms etc. mentioned.
Darüber hinaus ist bekannt, daß durch Mikroorganismen an Lebensmitteln und Kosmetika auerordentliche Verluste entstehen und außerdem gesundheitliche Schäden hervorgerufen werden können. Auch im klinischen Bereich bereitet die Gewährleistung einer weitgehenden Asepsis allergrößte Schwierigkeiten. Daß dieses Problem der Asepsis trotz modernster Technik bis heute nicht gelost ist, dokumentieren Angaben, wonach infolge von Wundinfektionen der durchqchnittliche Krankenhausaufenthalt von Patienten um etwa 50% verlängert sein soll. In vielen Fällen ist eine Wundinfektion Ursache letalen Ausgangs. Diese Tatsachen unterstreichen, daß moderne Technik wie Keimfilteranlagen für die Raumbelüftung, Sterilisation und alle Vorsichtsmaßnahmen nicht in der Lage sind, der latenten Gefahr der Keime zu begegnen.It is also known that microorganisms affect food and cosmetics cause extraordinary losses and also damage to health can be evoked. The warranty also prepares in the clinical area an extensive asepsis, the greatest difficulties. That this problem of asepsis has not been drawn to this day despite the latest technology, information shows what the average hospital stay of patients as a result of wound infections should be extended by about 50%. In many cases, wound infection is the cause lethal outcome. These Facts underline that modern technology such as germ filter systems for room ventilation, sterilization and all precautionary measures are unable to counter the latent danger posed by germs.
In der Praxis werden zur Bekämpfung von Mikroorganismen meist physikalische und chemische Methoden kombiniert, wie z.B. Ilitzebehandlung und Anwendung antimikrobiell wirkender Mittel. Nicht überalL ist Sterilisation möglich; man muß dann versuchen, pathogene Keime mit rein chemischen Mitteln zu bekämpfen. Diese als Desinfektionsmittel bekannten Stoffe sind jedoch nur zur äußeren Anwendung geeignet. Desinfektionsmittel sind deshalb von den chemotherapeutischen und antibiotischen Stoffen zur Bekämpfung von pathogenen Keimen zu unterscheiden. Von letzteren fordert man eine Verträglichkeit mit dem Wirtssystem.In practice, the control of microorganisms is mostly physical and chemical methods combined, such as ilite treatment and antimicrobial application effective means. Sterilization is not possible everywhere; then you have to try to fight pathogenic germs with purely chemical means. These as disinfectants known substances are only suitable for external use. Disinfectants are therefore of the chemotherapeutic and antibiotic substances to combat to distinguish from pathogenic germs. Compatibility is required of the latter with the host system.
Der Schutz von Werkstoffen vor mikrobiellem BeLall erfolgt derzeit durch Imprägnierung des zu schützenden Gegenstandes mit hochaktiven, antimikrobiell wirkenden Substanzen.The protection of materials from microbial attack is currently taking place by impregnating the object to be protected with highly active, antimicrobial acting substances.
Diese können einerseits jedoch herausgelöst und abgetragen werdentund andererseits üben sie auf höhere Organismen wie Mensch und Tier eine stark toxische Wirkung aus.On the one hand, however, these can be detached and removed on the other hand, they exert a highly toxic effect on higher organisms such as humans and animals Effect.
Besonders in geschlossenen Räumen und im Kontakt mit höheren Organismen stellen nach diesem Verfahren behandelte Gegenstände eine latente Gefahr dar.Especially in closed rooms and in contact with higher organisms objects treated according to this process represent a latent danger.
Wie bereits erwähnt, werden besonders hohe Anforderungen an Keimfreiheit bei der Belüftung von Räumen des kosmetischen, lebensmitteltechnischen und klinischen Bereiches gestellt. Zur Belüftung dieser Räume wird die zugeführte Luft in Keimfilteranlagen gereinigt. Eine besondere Bedeutung kommt dabei den Schwebstoffiltern zu, die neben mechanischen Verunreinigungen auch Mikroorganismen wie Bakterien, Pilze und Viren zurückhalten müssen. Die zurückgehaltenen Mikroorzanismen werden derzeit so unschädlich gemacht, daß man die Filter mit UV-Strahlung bestrahlt.As already mentioned, the requirements for sterility are particularly high in the ventilation of cosmetic, food and clinical spaces Area. To ventilate these rooms, the air supplied is used in germ filter systems cleaned. HEPA filters are of particular importance here, next to mechanical impurities also include microorganisms such as bacteria, fungi and viruses have to hold back. The retained micro-organisms are currently so harmless made that the filters are irradiated with UV radiation.
Nachteile dieses Verfahrens sind der regeltechnische Aufwand, die ständige Uberwacliung und <las Auswechseln der Filter. Bautechnisch wesentlich attraktivere Flächenfilter können bei dieser Methode nicht verwendet werden.Disadvantages of this procedure are the regulatory effort that Constant monitoring and replacement of the filters. Structurally essential more attractive area filters cannot be used with this method.
Es wurde gefunden, daß antimikrobiell wirkende Substanzen auf den Oberflächen von Materialien unter Ausbildung einer echten chemischen Bindung aufgepfropft werden können und vor allem, daß die aufgepfropften und chemisch fixiertentantimikrobiell wirkenden Substanzen ihre antimikrobielle Aktivität beibehalten.It has been found that antimicrobial substances act on the Surfaces of materials are grafted on to form a real chemical bond and above all that the grafted and chemically fixed antimicrobial active substances retain their antimicrobial activity.
Damit sind solche, durch kovalente chemische Bindungen fixierte, antimikrobiell wirkende Substanzen nicht nur vor einem Ablösen gesichert, sondern auch in der Lage, auftreffende Mikroorganismen abzutöten oder in ihrem Wachstum zu hemmen wld auf diese Weise ihre Umgebung keimfrei zu halten; außerdem sind sie in der Lage, die Substratmaterialien vor mikrobieller Korrosion zu schützen.This means that those fixed by covalent chemical bonds are antimicrobial active substances not only secured against detachment, but also able to killing microorganisms or inhibiting their growth this way to keep their surroundings aseptic; they are also able to use the Protect substrate materials from microbial corrosion.
Es wurde gefunden, daß zur Jierstellung von Materialien mit antimikrobiellen Eigenschaften, d.h. zur Fixierung antimikrobiell wirksamer Substanzen auf Feststoffen bzw. Feststoffoberflächen verschiedene Methoden möglich sind.It has been found that for making materials with antimicrobial Properties, i.e. for fixing antimicrobial substances on solids or solid surfaces different methods are possible.
1. Behandlung der Feststoffe zur Erzeugung reaktionsfähiger Oberflächengruppen, sofern sie diese nicht von Natur aus besitzen, wie z.B. 1. Treatment of the solids to generate reactive surface groups, as long as they do not have them by nature, e.g.
Cellulose in Form der Hydroxylgruppen, Fixierung einer Kopplungskomponente wie z.B. BrCN oder Cyanurchlorid Init mindestens zwei reaktionsfähigen funktionellen Gruppen. Ankoppeln einer antimikrobiell wirksamen Substanz, die neben ihrer (il) antimikrobiell wirksamen Gruppe(n) über mindestens eine reaktionsfihige Gruppe verfügen muß, an die nicht umgesetzte(n) funktionelle(n) Gruppe(n) der Kopplungskomponente. Als reaktionsfähige Gruppe einer antimikrobiellen Verbindung ist beispielsweise eine Aminogruppe geeignet. Cellulose in the form of hydroxyl groups, fixation of a coupling component such as BrCN or cyanuric chloride Init at least two reactive functional Groups. Coupling of an antimicrobial substance that, in addition to its (il) antimicrobial group (s) have at least one reactive group must, to the unreacted functional group (s) of the coupling component. as reactive group of an antimicrobial compound is, for example Amino group suitable.
2. Ausgehend von einer antimikrobiell wirkenden Substanz, die neben ihrer oder ihren antimikrobiell wirksamen Gruppe(n) eine weitere funktionelle Gruppe besitzen muß, wird durch Umsetzung mit einer bi- oder multifunktionellen Kopplungskomponente ein Reaktiv-Mikrobizid erzeugt. Dieses Reaktiv-Mikrobizid wird sodann auf der Festst<l1-oberfläche aufgepfropft derart, daß die freie(n) funktionelle(n) Gruppen) der Kopplungskoiiponente mit reaktiven Oberflächengruppen des Feststoffs unter Ausbildung einer chemischen Bindung reagieren. Als Reaktiv-Mikrobizid wird ein' kopplun-gsfähige' antimikrobielle Substanz verstanden, die Mikroorganismen sowohl abtöten als auch ihre Vermehrung hemmen kann 3. Bei Vorliegen geeigneter reaktiver Gruppen sowohl auf dem Feststoff als auch bei der antimimikrobiellen Substanz ist unter Umständen auch eine chemische Fixierung der antimikrobiell wirsamen Substanz ohne Kopplungskomponente möglich.2. Based on an antimicrobial substance that is next to her or her antimicrobial group (s) a further functional group must have, is by reaction with a bi- or multifunctional coupling component a reactive microbicide is generated. This reactive microbicide is then applied to the solid surface grafted in such a way that the free functional group (s) of the coupling component with reactive surface groups of the solid with the formation of a chemical Bond react. The reactive microbicide used is a 'coupling-capable' antimicrobial Understood substance that both kill microorganisms and their reproduction can inhibit 3. If suitable reactive groups are present, both on the solid as well as the antimimicrobial substance may also be a chemical one The antimicrobial substance can be fixed without a coupling component.
Als Beispiel eines geeigneten Feststoffs sei Cellulose erwähnt, die aufgrund einer speziellen Oxidationsbehandlung sehr reaktive Aldehydoberflächengruppen besitzt. In diesem Falle genügt die antimikrobielle Substanz mit zusätzlicher Aminogruppe, um eine chemische Fixierung zu erreichen. As an example of a suitable solid, cellulose may be mentioned which very reactive aldehyde surface groups due to a special oxidation treatment owns. In this case, the antimicrobial substance with an additional amino group is sufficient, to achieve chemical fixation.
4. Eine weitere, elegante Verfahrensvariante esteht darin, daß man durch spezielle chemische Behandlung von Feststoffen direkt antimikrobiell wirksame Oberflächengruppen erzeugt. Ein Beispiel für diese Variante stellt die Umwandlung der vicinalen Hydroxylgruppen der Collulose in Aldehydgruppen durch Perjodatoxidation das.4. Another elegant variant of the method is that one due to the special chemical treatment of solids, it has a direct antimicrobial effect Surface groups generated. An example of this variant is the conversion the vicinal hydroxyl groups of collulose in aldehyde groups by periodate oxidation the.
Aldehyde zti11len bekanntlich zu den zçirkungsvollsten Desinfektionsmitteln. Aldehydes are known to be among the most effective disinfectants.
Die einzelnen Verfahrensvarianten werden im Folgenden anhand von Beispielen erläutert. In diesen Beispielen wird vor allem dnmonstriert, daß die chemisch fixierten, antimikrobiell wirksamen Substanzen und die antimikrobiellen Oberflächengruppen auch tatsächlich ant imikrobielle Wirkungen besitzen, d.h., daß sie auftreffende Mikroorganismen abtöten bzw. an ihrer Vermehrung hindorn und damit t auch das Substratmaterial vor einer mikrobiellen Zerstörung schützen. Daraus ergeben sich vielfältige Anwendungen der Verfahren und der nach den Verfahren hergestellten Gegenstände. Als charakteristische Beispiele seien der Schutz von Naterialien, feinmechanischen, optischen und elektronischen Geräten verschiedener Art vor mikrobiellem Befall und mikrobieller Korrosion erwähnt. Weitere Anwendungsbeispiele sind im hygienischen Bereich gegeben, beispielsweise die Behandlung von OP-Kloldung, Abdecktüchern im OP-Bereich, Vorbandsmatorialien und nicht zuletzt in der Behandlung der Filtorstoffe in Keimfilteranlagen.The individual process variants are illustrated below using examples explained. In these examples it is demonstrated above all that the chemically fixed, antimicrobial substances and the antimicrobial surface groups actually have antimicrobial effects, i.e. that they occur Kill microorganisms or prevent them from multiplying and thus also the substrate material protect against microbial destruction. This results in a wide range of applications the process and the objects produced by the process. As characteristic Examples are the protection of materials, fine mechanical, optical and electronic Devices of various types against microbial infestation and microbial corrosion are mentioned. Further application examples are given in the hygienic area, for example the treatment of surgical cladding, drapes in the operating theater, pre-band materials and last but not least in the treatment of filter materials in germ filter systems.
Beispiel 1: Auf Cellulose in Form von Baumwollgewebewurde ohne jede weitere Vorbehandlung BrCN als Kopplungskomponente durch Reaktion mit jeweils zwei Hydroxvlgruppen der Cellulose unter Ausbildung oberflächonständiger Imidocarbonatgruppierungen rnngesetzt. Diese Umsetzung erfolgte unter HBr-Abspaltung. Die oberfl-ichenstü.ndigen Imidocarbonatgruppierungen wurden sodann mit 4-Aminobutyraldehyddiothylacetal als Ausgangsmolekül einer antimikrobiell wirksamen Substanz umgesetzt. Die erzielte Bindung kann in Form eines Isoharnstoff-Derivates, eines N-Imidocarbonat-Derivates und als N-Carbamat-Derivat vorliegen. 4-Aminobutyraldehyddiethylacetal wurde durch saure Hydrolyse in den Aldehyd als eigentlicll wirksame antimikrobielle Substanz übergeführt. Die Verwendung des Acetals war notwendig, wu die Aldeliydgruppe bei der Aufpfropfreaktion zu schützen.Example 1: On cellulose in the form of cotton fabric was made without any further pretreatment of BrCN as a coupling component by reacting with two in each case Hydroxyl groups of cellulose with the formation of superficial imidocarbonate groups rnnnetted. This conversion took place with elimination of HBr. The superficial Imidocarbonate groups were then with 4-aminobutyraldehyde diothylacetal as Starting molecule of an antimicrobial substance implemented. The scored Bonding can be in the form of an isourea derivative, an N-imidocarbonate derivative and as an N-carbamate derivative. 4-aminobutyraldehyde diethyl acetal was made by acid hydrolysis into the aldehyde as a matter of fact effective antimicrobial Substance transferred. The use of the acetal was necessary as the aldeliyd group knew to protect during the grafting reaction.
Unbehandelte Cellulose und entsprechend dem voranstehenden behandelte Cellulose wurden vergleiciiend auf ihre antimikrobielle Wirksamkeit unter Verwendung von Escherichia coli (E. coli) als Testorganismus auf Standard-I-Nähragar und Endo-C-Agar als Nährboden nnd von Micrococcus luteus (M. luteus) als Testorganismus auf Standard-I-Nähragar als Nährboden untersucht. Nach dem Beimpfen der Proben mit den Mikroorganismen betrug die Einwirkungszeit 3-12 Tage. Danach wurden die Proben auf die angegebenen Nähragars gegeben und bei 30 OC bis zu drei Tage bebrütet. Es zeigte sich, daß der Organismus E. coli auf unbehandelter und behandelter Probe abgestorben war.Untreated cellulose and treated as above Celluloses have been used comparatively for their antimicrobial effectiveness of Escherichia coli (E. coli) as test organism on standard I nutrient agar and Endo C agar as nutrient medium and of Micrococcus luteus (M. luteus) as test organism on standard I nutrient agar examined as a breeding ground. After inoculating the samples with the microorganisms was the exposure time 3-12 days. The samples were then put on the indicated nutrient agars given and incubated at 30 OC for up to three days. It turned out that the organism E. coli had died on the untreated and treated sample.
Im Falle des wesentlich resistenteren M. luteus war die unbehandelte Probe nach dem Bebrüten völlig überwachson.In the case of the much more resistant M. luteus, it was untreated Sample completely monitored after incubation.
Auf der behandelten Probe dagegen konnte kein M. luteus nachgewiesen werden.On the other hand, no M. luteus could be detected on the treated sample will.
Beispiel 2: Cellulose in Form von Baumwollgewebe wurde mit Hilfe von Natriumperjodat oxidierend behandelt. 1hierdurch gelang die Überfül1rung der vicinalen Hydroxylgruppen der Cellulose in wesentlich reaktivere Aldehydgruppen. Diese Aldehydgruppen konnten direkt mit Aminophonylessigsaure umgesetzt werden, wobei die Aminogruppe mit den Aldehydgruppen unter Ausbildung eines instabilen Garbinolamins reagiert. Das instabile Carbinolamin konnte durch Reduktion mit NaBJJ4 in ein stabiles Alkylamin übergeführt werden. Somit gelang die chemische Fixierung der Aminophenylessigsäure als antimikrobiell wirksame Substanz.Example 2: Cellulose in the form of cotton fabric was produced with the aid of Sodium periodate treated in an oxidizing manner. This succeeded in overflowing the vicinal Cellulose hydroxyl groups in much more reactive aldehyde groups. These aldehyde groups could be reacted directly with aminophonylacetic acid, with the amino group reacts with the aldehyde groups to form an unstable garbinolamine. The unstable carbinolamine could be converted into a stable alkylamine by reduction with NaBJJ4 be transferred. Thus, the chemical fixation of the aminophenylacetic acid succeeded as an antimicrobial substance.
Die Untersuchung auf antimikrobielle Wirkung der fixierten Aminophenylessigsäure erfolgte entsprechend BeispieL 1.The investigation of the antimicrobial effect of the fixed aminophenylacetic acid was carried out according to example 1.
Es wurde gefunden, daß der Organismus E. coli ebenfalls auf beiden Proben abgestorben ist. Das Waciistum von M. luteus wurde nur auf der behandelten Probe geiiemiit, während auf der unbeharldelten Probe keine Wachstunshemmung beobachtet wurde. Ein Abtöten von M. luteus konnte nicht mit Sicherheit festgestellt werden.It has been found that the E. coli organism is also based on both Specimen has died. The Waciistum of M. luteus was just on the treated sample corresponds to it, while there is no inhibition of growth on the untreated sample was observed. A killing of M. luteus could not be determined with certainty will.
Beispiel 3: Cellulose in Form von Ualllllwolle wurde erneut mit Na-l'(rjodat behandelt, wobei die vicinalen Hydroxylgruppen in Aldehydgruppen umgewandelt wurden. Wegen der bekannten antimikrobiellen Wirkung der Aldehydgruppen wurden die so behandelten Proben ohne weitere Bchandlung auf ihre antimikrobielle Wirkung untersucht. Die Untersuchung erfolgte erneut in Analogie zu Beispiel 1. Es wurde gefunden, daß die Keime von E. coli auf unbehandelter und behandelter Probe abgestorben sind. Im Gegensatz dazu verhält sich die behandelte Probe mit ihren Aldehydoberflächengruppen gegenüber dem M. luteus eindeutig mikrobistatisch.Example 3: Cellulose in the form of Ualllllwolle was again with Na-l '(rjodat treated, whereby the vicinal hydroxyl groups were converted into aldehyde groups. Because of the known antimicrobial effect of the aldehyde groups, those treated in this way were treated Samples examined for their antimicrobial effect without further treatment. the Investigation was carried out again in analogy to Example 1. It was found that the E. coli germs have died on untreated and treated samples. In contrast the treated sample behaves with its aldehyde surface groups the M. luteus clearly microbistatic.
Damit ist anhand dieser Beispiele gezeigt daß nicht nur eine chemische Fixierung von antimikrobiell wirksamen Substanzen auf Feststoffen möglich ist, sondern auch, daß diese Substanzen bzw. Gruppen auch mikrobistatisch bzw.With the help of these examples it is shown that not only one chemical Fixation of antimicrobial substances on solids is possible, rather also that these substances or groups are also microbistatic or
mikrobizid wirken.have a microbicidal effect.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19792922347 DE2922347A1 (en) | 1979-06-01 | 1979-06-01 | Antimicrobial surface treatment of materials - by covalent coupling with antimicrobial agent |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19792922347 DE2922347A1 (en) | 1979-06-01 | 1979-06-01 | Antimicrobial surface treatment of materials - by covalent coupling with antimicrobial agent |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2922347A1 true DE2922347A1 (en) | 1980-12-11 |
Family
ID=6072249
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19792922347 Withdrawn DE2922347A1 (en) | 1979-06-01 | 1979-06-01 | Antimicrobial surface treatment of materials - by covalent coupling with antimicrobial agent |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE2922347A1 (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0147618A2 (en) * | 1983-11-21 | 1985-07-10 | Uop Inc. | Antimicrobial fabrics |
WO1989005762A1 (en) * | 1987-12-18 | 1989-06-29 | Tiedemanns Johan H. Andresen | Control of biological characteristics of material |
DE3836828A1 (en) * | 1988-10-28 | 1990-05-03 | Pfrimmer Kabi Gmbh & Co Kg | LIABILITY FOR INTRAVENOESE PERIPHERE CANUELEN |
DE29719818U1 (en) * | 1997-11-07 | 1998-01-15 | Degussa AG, 40474 Düsseldorf | Device for coating catheters |
FR2802771A1 (en) * | 1999-12-24 | 2001-06-29 | Commissariat Energie Atomique | New isocyanate-, anhydride- or epoxy-functionalized biocidal compounds, useful for grafting onto substrates, e.g. wood, to provide biocidal, e.g. insecticidal or fungicidal, activity |
FR2843759A1 (en) * | 2002-08-20 | 2004-02-27 | Louis Rousseau | Process for the surface treatment of hydrophilic fibres in a natural or synthetic substrate, to impart hydrophobicity or bactericidal and/or fungicidal properties |
-
1979
- 1979-06-01 DE DE19792922347 patent/DE2922347A1/en not_active Withdrawn
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0147618A2 (en) * | 1983-11-21 | 1985-07-10 | Uop Inc. | Antimicrobial fabrics |
EP0147618A3 (en) * | 1983-11-21 | 1987-10-14 | Uop Inc. | Antimicrobial fabrics |
WO1989005762A1 (en) * | 1987-12-18 | 1989-06-29 | Tiedemanns Johan H. Andresen | Control of biological characteristics of material |
AU645242B2 (en) * | 1987-12-18 | 1994-01-13 | Repligen Corporation | Packaging for liquids having anti-microbial agents adhered thereto |
DE3836828A1 (en) * | 1988-10-28 | 1990-05-03 | Pfrimmer Kabi Gmbh & Co Kg | LIABILITY FOR INTRAVENOESE PERIPHERE CANUELEN |
DE29719818U1 (en) * | 1997-11-07 | 1998-01-15 | Degussa AG, 40474 Düsseldorf | Device for coating catheters |
FR2802771A1 (en) * | 1999-12-24 | 2001-06-29 | Commissariat Energie Atomique | New isocyanate-, anhydride- or epoxy-functionalized biocidal compounds, useful for grafting onto substrates, e.g. wood, to provide biocidal, e.g. insecticidal or fungicidal, activity |
FR2843759A1 (en) * | 2002-08-20 | 2004-02-27 | Louis Rousseau | Process for the surface treatment of hydrophilic fibres in a natural or synthetic substrate, to impart hydrophobicity or bactericidal and/or fungicidal properties |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE68904862T2 (en) | CARBAMIC ACID ESTER, USED AS A MICROBICIDE AND PRESERVATIVE. | |
EP0655002B1 (en) | Bactericidal and/or fungicidal plastic objects for medical uses | |
DE1492326A1 (en) | Sterilization solution and sterilization process | |
DE3751938T2 (en) | ACID DECRISTALLIZATION OF HIGH CRYSTALLINE CHITOSAN OR PARTIAL TACETYLATED CHITINE | |
DE4439527A1 (en) | Process for disinfecting and sterilizing contaminated material | |
DE102009043995A1 (en) | Antibacterial deodorant | |
DE3851533T2 (en) | AIR CONDITIONING TREATMENT. | |
EP0252310A2 (en) | Antimicrobial agents | |
DE2718244A1 (en) | DISINFECTING AND STERILIZING PREPARATIONS | |
DE69503603T2 (en) | SYNERGISTIC ANTIMICROBIAL COMPOSITIONS CONTAINING A HALOGENED ACETOPHENONE AND ORGANIC ACID | |
DE3319019C2 (en) | ||
DE69414521T2 (en) | METHOD FOR THE PRODUCTION OF IODIZED BIOPOLYMERS WITH DISINFECTING AND SCARF-PROMOTING EFFECT, AND THEREFORE PRODUCED IODATED BIOPOLYMERS | |
DE2922347A1 (en) | Antimicrobial surface treatment of materials - by covalent coupling with antimicrobial agent | |
DE69525938T2 (en) | ANTIMICROBIAL MATERIALS | |
DE1188764B (en) | Disinfectants | |
JPS62209001A (en) | Use of ester compound as temporary disinfectant | |
DE3850862T2 (en) | Protection against microorganisms in aqueous systems with 1-hydroxymethylpyrazoles. | |
DE69519106T2 (en) | FIBER STRUCTURE CONTAINING UREA PEROXIDES AND METHOD FOR THE PRODUCTION THEREOF | |
DE4241491C2 (en) | Use of bisbiguanide compounds | |
DD273776A1 (en) | CONTROL INDICATOR FOR GAS STERILIZATION | |
DE3124433A1 (en) | Method for the sterilisation of liquids | |
DE102008036520A1 (en) | New hydrogel-forming polymer with an antimicrobial effect for binding on a surface, where the hydrogel-forming polymer has a quaternary ammonium group for destroying a cell membrane of a microorganism | |
DE69712493T2 (en) | MICROBICIDAL COMPOSITION | |
DE947827C (en) | Process for the preservation of decomposable substances | |
DE1912711C (en) | Quaternary ammonium halides of diathers of 2,4 dihydroxy 6 chloro s tnazine with an N heterocyclic 2 hydroxy compound |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
8139 | Disposal/non-payment of the annual fee |