WO2006047800A1 - Biozid, insbesondere fungizid wirkendes mittel - Google Patents
Biozid, insbesondere fungizid wirkendes mittel Download PDFInfo
- Publication number
- WO2006047800A1 WO2006047800A1 PCT/AT2005/000433 AT2005000433W WO2006047800A1 WO 2006047800 A1 WO2006047800 A1 WO 2006047800A1 AT 2005000433 W AT2005000433 W AT 2005000433W WO 2006047800 A1 WO2006047800 A1 WO 2006047800A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- condensation product
- product according
- diamine
- oxyalkylenediamine
- alkylenediamine
- Prior art date
Links
Classifications
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/024—Polyamines containing oxygen in the form of ether bonds in the main chain
Definitions
- Biocide in particular fungicidal agent
- the invention relates to an antimicrobial or microbicidal, in particular fungicidal, polymeric condensation product which can be used as a crop protection agent.
- EP-A-0 439 698 and EP-A-0 439 699 describe solutions of polymeric guanidine salts with increased biocidal activity. These polymeric guanidine salts are obtained by reacting a diamine with cyanogen chloride and then polymerizing.
- WO 99/54291 discloses polyhexamethyleneguanidines which, because of their microbiocidal activity, can be used as disinfectants. These substances are prepared by polycondensation of guanidine with an alkylenediamine, especially hexamethylenediamine. The polycondensation is carried out by mixing hexamethylenediamine and guanidine hydrochloride in a molar ratio of 1: 1 and heating to 120 ° C. for 5 hours. Subsequently, the temperature is raised to 150 0 C and the mixture heated at this temperature for a further 10 hours. The obtained condensation product has a good biocidal effect, but the fungicidal effect is only weak.
- biocidal polymers which are prepared by condensation of guanidine and an oxyalkylenediamine. These substances are less toxic than the substances known from WO 99/54291, but they are not fungicidal.
- guanidinium hydrochloride in triethylene glycol diamine is dissolved at 50 ° C. to prepare this compound.
- the mixture is then heated to 120 0 C and stirred at this temperature for two hours. Thereafter, the temperature is maintained for 2 hours, then applied a vacuum (0.1 bar) and stirred for a further two hours under vacuum at 17O 0 C.
- the mixture is then vented to atmospheric pressure, allowed to cool to 120 0 C and diluted with demineralized water to about 50%.
- With phosphoric acid is adjusted to a pH of 6 neutralized, allowed to cool and diluted to the desired concentration.
- the molecular weight was determined to be 1000 D.
- the active ingredient poly (2- (2-ethoxy-ethoxy-ethyl) -guanidinium-hydrochloride) has low pharmacological and pharmacologically acceptable pharmacodynamic properties and can also be used as a remedy in antimicrobial therapy.
- the active ingredient exhibits excellent antimicrobial efficacy which has been demonstrated by studies on a variety of microorganisms such as multi-resistant bacteria (which are resistant to common antibiotics), fungi (yeasts, dermatophytes, molds) and viruses such as herpes simplex.
- multi-resistant bacteria which are resistant to common antibiotics
- fungi fungi
- viruses such as herpes simplex.
- development of resistance is hardly to be expected, as the studies on a larger number of bacterial strains have also shown.
- the object of the invention is to provide a novel biocidal active ingredient which in particular has pronounced fungicidal activity, at the same time as low toxicity.
- a polymeric condensation product obtainable by reacting guanidine or a salt thereof with an alkylenediamine and an oxyalkylenediamine.
- guanidine or a salt thereof are preferably used per mole of diamine (sum of alkylenediamine and oxyalkylenediamine).
- the alkylenediamine and the oxyalkylenediamine are used in particular in a molar ratio between 4: 1 and 1: 4.
- alkylene diamine is a compound of the general formula
- n is an integer between 2 and 10, in particular 6, and that as oxyalkylenediamine a compound of general formula
- n is an integer between 2 and 5, in particular 2.
- Triethylene glycol diamine (relative molecular mass: 148), polyoxypropylene diamine (relative molecular mass: 230) and polyoxyethylene diamine (relative molecular mass: 600) are also very suitable as oxyalkylenediamine.
- the average molecular mass of the condensation product according to the invention is preferably in the range between 500 and 3,000.
- the invention further relates to a biocide, in particular a fungicidally active agent, which contains the polymeric condensation product according to the invention.
- polymeric condensation product according to the invention can be used very well as a crop protection agent for the treatment of crops.
- the fungal disease Black Sigatoka pathogen: Mycosphaerella fijiensis var. Differmis (MFD)
- MFD Mycosphaerella fijiensis
- the active ingredient can be used alone or together with inorganic or organic adjuvants.
- inorganic or organic adjuvants The preparation of preferred representatives of the compounds used according to the invention is described below.
- the polymer resin is removed from the flask with the aid of a spatula and comminuted to powder in a mortar, which rapidly dissolves in the water.
- this polycondensate is low in toxicity (oral dose in rats LD 50 > 2000 mg / kg), thus having a substantially lower toxicity than PHMG (polyhexamethylene guanidine hydrochloride). Furthermore, it has been shown that it has a very high biocidal, in particular activity, wherein the fungicidal action has been demonstrated inter alia by tests with the fungus Candida albicans and Aspergillus niger.
- Example 1 If, in Example 1, the amount of hexamethylenediamine used is increased to 87 g (0.75 mol) and the amount of triethylene glycol diamine used is reduced to 37 g (0.25 mol), a slightly water-soluble polymer is obtained in the same procedure in an amount of 181g, this corresponds to 97% d. Th.
- a new polymeric product was obtained which in its composition corresponds to a co-polycondensate of guanidine hydrochloride and triethylene glycol diamine and hexamethylenediamine (in the ratio 1: 3). It has been found that this polycondensate is low in toxicity (oral dose in rats LD 50 > 2000 mg / kg), thus having a substantially lower toxicity than PHMG (polyhexamethylene guanidine hydrochloride). Furthermore, it has been shown that it has a very high biocidal, in particular activity, wherein the fungicidal action has been demonstrated inter alia by tests with the fungus Candida albicans and Aspergillus niger.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Pest Control & Pesticides (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05799623A EP1809687A1 (de) | 2004-11-05 | 2005-11-04 | Biozid, insbesondere fungizid wirkendes mittel |
US11/791,730 US20090130052A1 (en) | 2004-11-05 | 2005-11-04 | Biocide, in particular an agent with fungicidal activity |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ATA1847/2004 | 2004-11-05 | ||
AT0184704A AT505102B1 (de) | 2004-11-05 | 2004-11-05 | Biozid, insbesondere fungizid wirkendes mittel |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006047800A1 true WO2006047800A1 (de) | 2006-05-11 |
Family
ID=35482266
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/AT2005/000433 WO2006047800A1 (de) | 2004-11-05 | 2005-11-04 | Biozid, insbesondere fungizid wirkendes mittel |
Country Status (4)
Country | Link |
---|---|
US (1) | US20090130052A1 (de) |
EP (1) | EP1809687A1 (de) |
AT (1) | AT505102B1 (de) |
WO (1) | WO2006047800A1 (de) |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008080184A2 (de) * | 2006-12-29 | 2008-07-10 | Aka Technology Gmbh | Verwendung von polymeren guanidinen zum bekämpfen von mikroorganismen |
EP2071954A1 (de) | 2007-12-19 | 2009-06-24 | Bayer CropScience AG | Verwendung von polymeren Guanidin-Derivaten zum Bekämpfen von unerwünschten Mikro-organismen im Pflanzenschutz |
US20090182118A1 (en) * | 2006-09-29 | 2009-07-16 | Closed Joint-Stock Company "Scientific And Technological Center 'ukrvodbezpek | Method for producing polyguanidines |
WO2009092123A2 (de) * | 2008-01-24 | 2009-07-30 | Aka Central Research Laboratories Gmbh | Verfahren zur bekämpfung unerwünschter mikroorganismen an bananenpflanzen |
EP2230259A1 (de) | 2009-03-18 | 2010-09-22 | Mindinvest Holdings Ltd. | Mikrobiozid wirkendes Polymergemisch |
DE102009052725A1 (de) | 2009-11-12 | 2011-05-19 | B. Braun Melsungen Ag | Verwendung von Polyoxyalkylendiamin-basierten Polyguanidinderivaten für medizinische Artikel |
WO2011117389A1 (de) | 2010-03-26 | 2011-09-29 | B. Braun Melsungen Ag | Antimikrobielle öl in wasser emulsion |
WO2011117384A1 (de) | 2010-03-26 | 2011-09-29 | B. Braun Melsungen Ag | Antimikrobielle wundauflage |
AT505563B1 (de) * | 2007-07-16 | 2011-10-15 | Geopharma Produktions Gmbh | Dentalwerkstoff |
AT505514B1 (de) * | 2007-07-16 | 2011-10-15 | Aka Technology Gmbh | Silikatischer füllstoff |
WO2013064161A1 (de) | 2011-11-02 | 2013-05-10 | Mindinvest Holdings Ltd. | Polyguanidinsilikat und dessen verwendung |
WO2014113835A1 (de) | 2013-01-25 | 2014-07-31 | Sealife Pharma Gmbh | Neue bioaktive polymere |
EP3524055A1 (de) | 2018-02-08 | 2019-08-14 | BCSK Biocid GmbH | Antibakterielles und spermizides gleitmittel |
WO2020229903A1 (en) | 2019-05-16 | 2020-11-19 | Marwian GmbH | Novel active biocidal substances and production process thereof |
EP3886823A4 (de) * | 2018-11-30 | 2022-07-06 | UCAR Health GmbH | Maske, wundauflage, slip, bh, taschentuch, kissen, pad, wegwerfbares chirurgisches kleidungsstück, wegwerftücher mit antimikrobiellen eigenschaften aus gewebe, vlies, baumwolle, vlies-baumwoll-gemischtem polyethylen und polypropylen und polystyrol |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102009052667A1 (de) * | 2009-11-12 | 2011-05-19 | Philipps-Universität Marburg | Polymere oder oligomere Wirkstoffe mit biozider Wirkung, Verfahren zu deren Herstellung und Zusammensetzung umfassend einen polymeren oder oligomeren Wirkstoff |
DE102009052721A1 (de) * | 2009-11-12 | 2011-05-26 | B. Braun Melsungen Ag | Verwendung polymerer oder oligomerer Wirkstoffe für medizinische Artikel |
US9403944B2 (en) * | 2012-01-12 | 2016-08-02 | John L. Lombardi | Antipathogenic guanidinium copolymer |
CN103210948A (zh) * | 2013-05-07 | 2013-07-24 | 江苏辉丰农化股份有限公司 | 一种防治果树病害的杀菌剂 |
US9631052B2 (en) * | 2014-06-26 | 2017-04-25 | John L. Lombardi | Borate esters |
EP3381967A1 (de) * | 2017-03-28 | 2018-10-03 | Thomas Flechsig | Homogene poly(alkylen)guanidine und verfahren zu deren herstellung |
MX2020010993A (es) * | 2018-04-19 | 2020-12-09 | Ucar Health Gmbh | Propiedades antimicrobianas para superficies, aire, textiles, pinturas, plasticos, silicona, madera, polietileno, metales y sus derivados. |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2325586A (en) * | 1940-03-21 | 1943-08-03 | Du Pont | Polymeric guanidines and process for preparing the same |
RU1816769C (ru) * | 1990-12-28 | 1993-05-23 | Московский научно-исследовательский и проектно-изыскательский институт "МосводоканалНИИпроект" | Привитые сополимеры полиоксиалкилена на полиалкиленгуанидине в качестве поверхностно-активных веществ и катионного полиэлектролита |
US5741886A (en) * | 1995-09-19 | 1998-04-21 | Stockel; Richard F. | End-capped polymeric biguanides |
WO1998056366A1 (en) * | 1997-06-09 | 1998-12-17 | Dustin Investments Cc | A composition for use as a pharmaceutical and in specific agricultural and industrial applications |
WO2002030877A1 (fr) * | 2000-09-29 | 2002-04-18 | Regionalnaya Obschestvennaya Organizatsya-Institut Ekologo-Tekhnologicheskikh Problem | Procede de production d'un desinfectant |
-
2004
- 2004-11-05 AT AT0184704A patent/AT505102B1/de not_active IP Right Cessation
-
2005
- 2005-11-04 US US11/791,730 patent/US20090130052A1/en not_active Abandoned
- 2005-11-04 EP EP05799623A patent/EP1809687A1/de not_active Withdrawn
- 2005-11-04 WO PCT/AT2005/000433 patent/WO2006047800A1/de active Application Filing
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US2325586A (en) * | 1940-03-21 | 1943-08-03 | Du Pont | Polymeric guanidines and process for preparing the same |
RU1816769C (ru) * | 1990-12-28 | 1993-05-23 | Московский научно-исследовательский и проектно-изыскательский институт "МосводоканалНИИпроект" | Привитые сополимеры полиоксиалкилена на полиалкиленгуанидине в качестве поверхностно-активных веществ и катионного полиэлектролита |
US5741886A (en) * | 1995-09-19 | 1998-04-21 | Stockel; Richard F. | End-capped polymeric biguanides |
WO1998056366A1 (en) * | 1997-06-09 | 1998-12-17 | Dustin Investments Cc | A composition for use as a pharmaceutical and in specific agricultural and industrial applications |
WO2002030877A1 (fr) * | 2000-09-29 | 2002-04-18 | Regionalnaya Obschestvennaya Organizatsya-Institut Ekologo-Tekhnologicheskikh Problem | Procede de production d'un desinfectant |
Non-Patent Citations (2)
Title |
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DATABASE WPI Section Ch Week 199430, Derwent World Patents Index; Class A26, AN 1994-247737, XP002361610 * |
DATABASE WPI Section Ch Week 200251, Derwent World Patents Index; Class A26, AN 2002-479619, XP002361609 * |
Cited By (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20090182118A1 (en) * | 2006-09-29 | 2009-07-16 | Closed Joint-Stock Company "Scientific And Technological Center 'ukrvodbezpek | Method for producing polyguanidines |
WO2008080184A3 (de) * | 2006-12-29 | 2008-10-02 | Aka Technology Gmbh | Verwendung von polymeren guanidinen zum bekämpfen von mikroorganismen |
WO2008080184A2 (de) * | 2006-12-29 | 2008-07-10 | Aka Technology Gmbh | Verwendung von polymeren guanidinen zum bekämpfen von mikroorganismen |
AT505563B1 (de) * | 2007-07-16 | 2011-10-15 | Geopharma Produktions Gmbh | Dentalwerkstoff |
AT505514B1 (de) * | 2007-07-16 | 2011-10-15 | Aka Technology Gmbh | Silikatischer füllstoff |
EP2071954A1 (de) | 2007-12-19 | 2009-06-24 | Bayer CropScience AG | Verwendung von polymeren Guanidin-Derivaten zum Bekämpfen von unerwünschten Mikro-organismen im Pflanzenschutz |
WO2009077098A2 (de) * | 2007-12-19 | 2009-06-25 | Bayer Cropscience Aktiengesellschaft | Verwendung von polymeren guanidin-derivaten zum bekämpfen von unerwünschten mikro-organismen im pflanzenschutz |
WO2009077098A3 (de) * | 2007-12-19 | 2009-10-08 | Bayer Cropscience Aktiengesellschaft | Verwendung von polymeren guanidin-derivaten zum bekämpfen von unerwünschten mikro-organismen im pflanzenschutz |
EP2084967A1 (de) | 2008-01-24 | 2009-08-05 | Aka Central Research Laboratories GmbH | Verfahren zur Bekämpfung unerwünschter Mikroorganismen an Bananenpflanzen |
WO2009092123A3 (de) * | 2008-01-24 | 2010-04-22 | Aka Central Research Laboratories Gmbh | Verfahren zur bekämpfung unerwünschter mikroorganismen an bananenpflanzen |
WO2009092123A2 (de) * | 2008-01-24 | 2009-07-30 | Aka Central Research Laboratories Gmbh | Verfahren zur bekämpfung unerwünschter mikroorganismen an bananenpflanzen |
EP2230258A1 (de) | 2009-03-18 | 2010-09-22 | Mindinvest Holdings Ltd. | Mikrobiozid wirkendes Arzneimittel |
WO2010106006A1 (de) | 2009-03-18 | 2010-09-23 | Mindinvest Holdings Ltd. | Mikrobiozid wirkendes arzneimittel |
WO2010106002A1 (de) | 2009-03-18 | 2010-09-23 | Mindinvest Holdings Ltd. | Mikrobiozid wirkendes polymergemisch |
WO2010106007A1 (de) | 2009-03-18 | 2010-09-23 | Mindinvest Holdings Ltd. | Komplex enthaltend ein polymeres guanidin |
EP2230259A1 (de) | 2009-03-18 | 2010-09-22 | Mindinvest Holdings Ltd. | Mikrobiozid wirkendes Polymergemisch |
DE102009052725A1 (de) | 2009-11-12 | 2011-05-19 | B. Braun Melsungen Ag | Verwendung von Polyoxyalkylendiamin-basierten Polyguanidinderivaten für medizinische Artikel |
WO2011058145A1 (de) | 2009-11-12 | 2011-05-19 | B. Braun Melsungen Ag | Verwendung von polyoxyalkylendiamin-basierten polyguanidinderivaten für medizinische artikel |
WO2011117384A1 (de) | 2010-03-26 | 2011-09-29 | B. Braun Melsungen Ag | Antimikrobielle wundauflage |
WO2011117389A1 (de) | 2010-03-26 | 2011-09-29 | B. Braun Melsungen Ag | Antimikrobielle öl in wasser emulsion |
WO2013064161A1 (de) | 2011-11-02 | 2013-05-10 | Mindinvest Holdings Ltd. | Polyguanidinsilikat und dessen verwendung |
WO2014113835A1 (de) | 2013-01-25 | 2014-07-31 | Sealife Pharma Gmbh | Neue bioaktive polymere |
US9567294B2 (en) | 2013-01-25 | 2017-02-14 | Sealife Pharma Gmbh | Bioactive polymers |
EP3524055A1 (de) | 2018-02-08 | 2019-08-14 | BCSK Biocid GmbH | Antibakterielles und spermizides gleitmittel |
WO2019154983A1 (de) | 2018-02-08 | 2019-08-15 | Bcsk Biocid Gmbh | Antibakterielles und spermizides gleitmittel |
EP3886823A4 (de) * | 2018-11-30 | 2022-07-06 | UCAR Health GmbH | Maske, wundauflage, slip, bh, taschentuch, kissen, pad, wegwerfbares chirurgisches kleidungsstück, wegwerftücher mit antimikrobiellen eigenschaften aus gewebe, vlies, baumwolle, vlies-baumwoll-gemischtem polyethylen und polypropylen und polystyrol |
WO2020229903A1 (en) | 2019-05-16 | 2020-11-19 | Marwian GmbH | Novel active biocidal substances and production process thereof |
Also Published As
Publication number | Publication date |
---|---|
US20090130052A1 (en) | 2009-05-21 |
AT505102B1 (de) | 2010-05-15 |
EP1809687A1 (de) | 2007-07-25 |
AT505102A1 (de) | 2008-10-15 |
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