EP1368394A1 - Systemes de separation microbicides - Google Patents

Systemes de separation microbicides

Info

Publication number
EP1368394A1
EP1368394A1 EP02712827A EP02712827A EP1368394A1 EP 1368394 A1 EP1368394 A1 EP 1368394A1 EP 02712827 A EP02712827 A EP 02712827A EP 02712827 A EP02712827 A EP 02712827A EP 1368394 A1 EP1368394 A1 EP 1368394A1
Authority
EP
European Patent Office
Prior art keywords
antimicrobial
separation systems
systems according
polymer
separation
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Withdrawn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
EP02712827A
Other languages
German (de)
English (en)
Inventor
Peter Ottersbach
Friedrich Sosna
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.)
Evonik Operations GmbH
Original Assignee
CREAVIS GESELLSCHAFT fur TECHNOLOGIEUND INNOVATION MBH
CREAVIS GES fur TECHNOLOGIEUN
Creavis Gesellschaft fuer 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 fur TECHNOLOGIEUND INNOVATION MBH, CREAVIS GES fur TECHNOLOGIEUN, Creavis Gesellschaft fuer Technologie und Innovation mbH filed Critical CREAVIS GESELLSCHAFT fur TECHNOLOGIEUND INNOVATION MBH
Publication of EP1368394A1 publication Critical patent/EP1368394A1/fr
Withdrawn legal-status Critical Current

Links

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
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/52—Amides or imides
    • C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F20/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
    • 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
    • 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
    • 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
    • A01N37/18—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 —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/20—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 —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
    • 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
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate

Definitions

  • the invention relates to the use and use of antimicrobial polymers for the production of microbicidal separation systems.
  • 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 genital 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.
  • 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 their effect more or less quickly if the necessary “minimal inhibitory concentration” (MTK) is no longer achieved.
  • a large number of contact microbicidal polymers are known from the following patent applications: DE 100 24 270, DE 100 22 406, PCT / EP00 / 06501, DE 100 14 726, DE 100 08 177, PCT / EPOO / 06812, PCT / EP00 / 06487 , PCT / EP00 / 06506, 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 / 00,544th
  • These polymers do not contain any low molecular weight components; the antimicrobial properties are due to the contact of bacteria with the surface.
  • antimicrobial polymers Polymers which have a contact microbicidal action without the addition of low molecular weight biocides are referred to below as antimicrobial polymers.
  • biocides are forbidden on its own in many material separation systems, since in operation, e.g. B. in the filtration of foods such as beer, must not add substances that ultimately contaminate the product and in extreme cases can even poison. In these cases, it has been inevitable that the plants come to a standstill with all the associated high costs, since the biofilms can only be removed mechanically and optionally also chemically in a toxicologically harmless manner. Even with purely technical systems that do not come into direct contact with food, the use of low molecular weight biocides is often not possible, since these substances usually have to be disposed of after use.
  • separation systems which can largely prevent microbial infection itself.
  • these separation systems should not secrete toxic substances and should therefore be food-safe in extreme cases. It has been found that separation systems, ie membranes, sieves or filters made of or with antimicrobial polymers, can combine good separation performance with excellent antimicrobial effectiveness.
  • the present invention therefore relates to separation systems containing antimicrobial polymers.
  • Separation systems according to the invention can be membranes, filters, sieves or oxygenator modules with pore sizes from nano to millimeter range (below 1 nm to 2 mm).
  • the separation systems can be made entirely of the antimicrobial polymers, of a mixture (blend) of the antimicrobial polymers and at least one other polymer or of a prefabricated separation system with a coating of antimicrobial polymers or the above.
  • Polymer blend exist.
  • Prefabricated polymer-based separation systems can e.g. B. by a solution of the antimicrobial polymer in a suitable solvent, which can also be suitable as a swelling agent for the polymer base, impregnated near the surface.
  • the prefabricated, i.e. H. Non-antimicrobial separation systems can in turn consist of polymers, ceramics or metals.
  • At least one antimicrobial polymer is used. It can also be advantageous to use a polymer blend composed of various antimicrobial polymers.
  • Polymer membranes are preferably given an antimicrobial finish by additionally adding antimicrobial polymers to the membrane in the production process. This is generally done in such a way that the melt or the solution of the plastic from which the polymer membrane is to be made is additionally added and homogenized in this anti-microbial polymer. The mixture is then placed in a mold, dried and stretched at elevated temperature in order to obtain the desired pore sizes and distributions in the membrane. Alternatively, the pores can also be obtained in another way, in particular by using gamma or other high-energy electromagnetic radiation.
  • Nitrogen and phosphorus functionalized monomers are preferably used for the production of the antimicrobial polymers, in particular these polymers are produced from at least one of the following monomers:
  • Methacrylic acid-2-tert. -butylaminoethyl ester methacrylic acid-2-diethylaminoethyl ester, methacrylic acid-2-diethylaminomethyl ester, acrylic acid-2-tert.-butylaminoethyl ester, acrylic acid 3-dimethylaminopropyl ester, acrylic acid-2-diethylaminoethyl ester, acrylic acid-2-dimethylaminoethylamethyl methacrylate, dimethyl propyl methacrylate, dimethyl propyl methacrylate 3-dimethylaminopropylamide, 2-methacryloyloxyethyltrimethylammonium methosulfate, 2-diethylaminoethyl methacrylate, 2-
  • Methacryloyloxyethyltrimethylammonium chloride 3-methacryloylaminopropyltrimethylammonium chloride, 2-methacryloyloxyethyltrimethylammonium chloride, 2-
  • the proportion of the antimicrobial polymers in the separation systems can be 0.01 to 25% by weight, preferably 0.1 to 10, particularly preferably 0.1 to 5% by weight.
  • non-antimicrobial polymers can be used for all macromolecules commonly used for the production of polymer membranes, in particular polyethylene, polypropylene, polymethacrylates, polysulfones, polyacrylonitrile, cellulose, cellulose acetate or other cellulose derivatives.
  • polymer membranes in particular polyethylene, polypropylene, polymethacrylates, polysulfones, polyacrylonitrile, cellulose, cellulose acetate or other cellulose derivatives.
  • the cellulose derivatives have the advantage that no microdomain formation is to be expected with the often likewise hydrophilic antimicrobial polymers, which facilitates a uniform surface availability of the antimicrobial polymers.
  • microbicidal membranes produced according to the invention are the use of the microbicidal membranes produced according to the invention as part of filter systems or filter modules.
  • the separation systems according to the invention can be used for the filtration of beer, wine, fruit juices, milk or drinking water and as a liquid / gaseous separation system (oxygenator module).
  • the mixture is heated to 70 ° C. and stirred at this temperature for 6 hours. After expiration During this time, the solvent is removed from the reaction mixture by distillation and dried in vacuo at 50 ° C. for 24 hours. The product is then dissolved in 200 ml of acetone, after which the solvent is removed from the reaction mixture by distillation and dried in vacuo at 50 ° C. for 24 hours. The reaction product is then finely ground.
  • polypropylene 50 g of polypropylene are heated to 180 ° C. and mixed intimately with 3 g of the product from Example 1.
  • the still hot polymer mixture is processed with a laboratory calender so that an approximately 100 micrometer thick plastic film is formed.
  • the cooled film is heated again to 170 ° C. and stretched mechanically, which creates the pores in the membrane.
  • the membrane is then allowed to cool to room temperature.
  • Example lb A 3 x 3 cm piece of the plastic membrane from Example 1a 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.
  • tert-butylaminoethyl methacrylate (Aldrich) and 250 ml of ethanol are placed in a three-necked flask and heated to 65 ° C. under a stream of argon. Then 0.5 g of azobisisobutyronitrile dissolved in 20 ml of ethanol are slowly added dropwise with stirring. The mixture is heated to 70 ° C. and stirred at this temperature for 6 hours. After this time, the solvent is removed from the reaction mixture by distillation. The product is then dried in vacuo at 50 ° C. for 24 hours. The product is then dissolved in 200 ml of acetone, after which the solvent is removed from the reaction mixture by distillation and dried in vacuo at 50 ° C. for 24 hours.
  • polypropylene 50 g of polypropylene are heated to 180 ° C. and intimately with 3 g of the product from Example 2 mixed.
  • the still hot polymer mixture is processed with a laboratory calender so that an approximately 100 micrometer thick plastic film is formed.
  • the cooled film is heated again to 170 ° C. and stretched mechanically, which creates the pores in the membrane.
  • the membrane is then allowed to cool to room temperature.
  • a 3 x 3 cm piece of the plastic membrane from Example 2a 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 no more Pseudomonas aeruginosa germs can be detected.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)
  • Filtering Materials (AREA)

Abstract

L'invention concerne des systèmes de séparation microbicides utilisant des polymères antimicrobiens. L'invention concerne également leur production et leur utilisation.
EP02712827A 2001-03-07 2002-01-19 Systemes de separation microbicides Withdrawn EP1368394A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10110885A DE10110885A1 (de) 2001-03-07 2001-03-07 Mokrobizide Trennsysteme
DE10110885 2001-03-07
PCT/EP2002/000534 WO2002070573A1 (fr) 2001-03-07 2002-01-19 Systemes de separation microbicides

Publications (1)

Publication Number Publication Date
EP1368394A1 true EP1368394A1 (fr) 2003-12-10

Family

ID=7676566

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02712827A Withdrawn EP1368394A1 (fr) 2001-03-07 2002-01-19 Systemes de separation microbicides

Country Status (5)

Country Link
US (1) US20040084384A1 (fr)
EP (1) EP1368394A1 (fr)
JP (1) JP2004531374A (fr)
DE (1) DE10110885A1 (fr)
WO (1) WO2002070573A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070166344A1 (en) * 2006-01-18 2007-07-19 Xin Qu Non-leaching surface-active film compositions for microbial adhesion prevention
WO2015166725A1 (fr) * 2014-04-28 2015-11-05 シャープ株式会社 Filtre ayant une activité de stérilisation, et récipient

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19902942A1 (de) * 1999-01-26 2000-07-27 Creavis Tech & Innovation Gmbh Aminofunktionalisierte Polyoxyalkane
DE19921903A1 (de) * 1999-05-12 2000-11-16 Creavis Tech & Innovation Gmbh Mikrobizide Copolymere
DE19921902A1 (de) * 1999-05-12 2000-11-16 Creavis Tech & Innovation Gmbh Mikrobizide Copolymere
DE19921894A1 (de) * 1999-05-12 2000-11-16 Creavis Tech & Innovation Gmbh Verfahren zur Herstellung mikrobizider Oberflächen durch Immobilisierung inhärent mikrobizid wirksamer Makromoleküle
DE19921898A1 (de) * 1999-05-12 2000-11-16 Creavis Tech & Innovation Gmbh Verfahren zur Herstellung inhärent mikrobizider Polymeroberflächen
DE19921895A1 (de) * 1999-05-12 2000-11-16 Creavis Tech & Innovation Gmbh Antimikrobielle Copolymere
DE19921904A1 (de) * 1999-05-12 2000-11-16 Creavis Tech & Innovation Gmbh Verfahren zur Herstellung inhärent mikrobizider Polymeroberflächen
DE19921897A1 (de) * 1999-05-12 2000-11-16 Creavis Tech & Innovation Gmbh Verfahren zur Herstellung inhärent mikrobizider Polymeroberflächen
DE19921900A1 (de) * 1999-05-12 2000-11-16 Creavis Tech & Innovation Gmbh Verfahren zur Herstellung inhärent mikrobizider Polymeroberflächen
DE19921899A1 (de) * 1999-05-12 2000-11-16 Creavis Tech & Innovation Gmbh Mikrobizide Copolymere
DE19940023A1 (de) * 1999-08-24 2001-03-01 Creavis Tech & Innovation Gmbh Copolymere des Aminopropylvinylethers
DE10022453A1 (de) * 1999-09-09 2001-03-15 Creavis Tech & Innovation Gmbh Antimikrobielle Zusatzstoffe
CA2384427A1 (fr) * 1999-09-10 2001-03-22 Creavis Gesellschaft Fur Technologie Und Innovation Mbh Copolymeres de composes acryloylaminoalkyl
DE10008177A1 (de) * 2000-02-23 2001-08-30 Creavis Tech & Innovation Gmbh Copolymere von Allyltriphenylphosphoniumsalzen
DE10014726A1 (de) * 2000-03-24 2001-09-27 Creavis Tech & Innovation Gmbh Antimikrobielle Beschichtungen, enthaltend Polymere von acrylsubstituierten Alkylsulfonsäuren
DE10022406A1 (de) * 2000-05-09 2001-11-15 Creavis Tech & Innovation Gmbh Antimikrobielle, Aminofunktionalisierte Copolymere
DE10024270A1 (de) * 2000-05-17 2001-11-22 Creavis Tech & Innovation Gmbh Antimikrobielle Polymere und Polymerblends aus polymeren Alkylacrylamiden

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO02070573A1 *

Also Published As

Publication number Publication date
JP2004531374A (ja) 2004-10-14
DE10110885A1 (de) 2002-09-12
US20040084384A1 (en) 2004-05-06
WO2002070573A1 (fr) 2002-09-12

Similar Documents

Publication Publication Date Title
EP1218425A1 (fr) Additifs microbicides
DE10022406A1 (de) Antimikrobielle, Aminofunktionalisierte Copolymere
DE10145529A1 (de) Biozide Retardierungsformulierungen
EP1277882A2 (fr) Revêtements muraux microbicides
DE10024270A1 (de) Antimikrobielle Polymere und Polymerblends aus polymeren Alkylacrylamiden
DE10131484A1 (de) Antimikrobielle Polymerschäume mit Aminoalkoholen
EP1372387A1 (fr) Systemes de conservation antimicrobiens pour produits alimentaires
EP1368394A1 (fr) Systemes de separation microbicides
EP1339807A2 (fr) Procede de finition superficielle a visee antimicrobienne a assistance thermique
EP1277820A2 (fr) Adhésifs antimicrobiens
WO2002099181A1 (fr) Non-tisses antimicrobiens
DE10022453A1 (de) Antimikrobielle Zusatzstoffe
DE10132937A1 (de) Antimikrobielle Schaumstoffe
WO2002092336A1 (fr) Systemes d&#39;empilement de films microbicides
DE10136456A1 (de) Mikrobizide Tapeten mit Aminoalkoholen
WO2002092890A2 (fr) Fibres et tissu antimicrobiens
DE10048613A1 (de) Antimikrobiell wirksame Oligomere und deren Polymer-Formulierungen
EP1434739A2 (fr) Procede et dispositif de sterilisation de liquides en cours de debit
WO2002028928A1 (fr) Polymeres antimicrobiens produits au moyen d&#39;aldehydes ou de cetones
DE10043285A1 (de) Antimikrobielle Oligomere und deren Pulver-Formulierungen
WO2002017724A1 (fr) Formulations de depots a action bactericide
DE10256085A1 (de) Magnetische Mikrobizide
DE10102900A1 (de) Antimikrobielle Polymere in Reaktivformulierungen
WO2003096809A1 (fr) Charbon actif antimicrobien
DE10106230A1 (de) Verfahren zur Herstellung mikrobizider Oberflächen durch Immobilisierung von Aminoalkoholen

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: 20030725

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR

AX Request for extension of the european patent

Extension state: AL LT LV MK RO SI

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: DEGUSSA AG

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: 20050802