WO2012149591A1 - Utilisation de produits biocides par contact à base d'oxazolines poly(2-substitués) - Google Patents

Utilisation de produits biocides par contact à base d'oxazolines poly(2-substitués) Download PDF

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Publication number
WO2012149591A1
WO2012149591A1 PCT/AT2012/050059 AT2012050059W WO2012149591A1 WO 2012149591 A1 WO2012149591 A1 WO 2012149591A1 AT 2012050059 W AT2012050059 W AT 2012050059W WO 2012149591 A1 WO2012149591 A1 WO 2012149591A1
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WO
WIPO (PCT)
Prior art keywords
use according
organic radical
fragment
anion
aliphatic chain
Prior art date
Application number
PCT/AT2012/050059
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German (de)
English (en)
Inventor
Frank WIESBROCK
Franz Stelzer
Christian Slugovc
Nadja NOORMOFIDI
Verena KALTENHAUSER
Elisabeth KREUTZWIESNER
Karl Rametsteiner
Original Assignee
Ke-Kelit Kunststoffwerk Gesellschaft M.B.H.
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 Ke-Kelit Kunststoffwerk Gesellschaft M.B.H. filed Critical Ke-Kelit Kunststoffwerk Gesellschaft M.B.H.
Publication of WO2012149591A1 publication Critical patent/WO2012149591A1/fr

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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
    • 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

Definitions

  • biocides such as sulfonamides, cephalosporins, tetracyclines and the like, have a small molecular structure and are therefore usually water-soluble.
  • contact biocides By contact biocides, these disadvantages can be avoided.
  • Contact biocides usually form high molecular weight, protonatable chemical compounds that kill the protozoa by mere contact due to static charges and the resulting cell lysis, without going into aqueous solution or intervene in the internal metabolism.
  • the polymer is prepared from 2-oxazolines by means of cationic ring-opening polymerization, wherein the starting polymers may be loakylreste radicals at the 2 position of the oxazole ring substituted and unsubstituted C MS alkyl or alkylene groups or phenyl and Cyc-.
  • US 2005238825 A1 discloses a crosslinked polymer composition of hydrolyzed poly (2-alkyl-2-oxazolines) for coatings of ink jet printers.
  • the invention is thus based on the object of optimizing the known antibacterial properties of poly (2-oxazolines) in order to obtain advantageous contact biocides.
  • the invention solves the problem by the use of the compound according to the formula
  • A is a fragment that coordinates as a cation to the lone pair of a nitrogen atom
  • B is a fragment that reacts as an anion with a carbocation to form an uncharged product
  • R is an organic radical of a saturated aliphatic chain C 6 to C 30 , a saturated cycloaliphatic radical, a mono- or polyunsaturated aliphatic chain having at least 6 carbon atoms, an alkyl spacer to be crosslinked oligooxazolines, an aryl spacer to be crosslinked oligooxazolines, a phenyl, an alkylphenyl, heteroaryl or a copolymer thereof and
  • the amphiphilicity of the cytoplasmic membranes can be taken into account in an advantageous manner, since the amide content has a significant influence on the lipophilicity and the amine content on the hydrophilicity of the contact biocide. Due to a corresponding coordination of the amide and amine contents, it becomes possible to provide the hydrophilicity required for lysis of the lipid-dominated bacterial envelopes with a pronounced lipophilicity, despite only slight water solubility.
  • fragment A is preferably hydrogen, an alkyl Ci to CQ or a benzyl group.
  • fragment B can advantageously be used a hydroxy group or an amino group.
  • the organic radical R is intended to prevent water solubility of the amide moiety and therefore preferably forms longer chains, the required chain length depending on the mobility of the chain molecules.
  • saturated aliphatic chains require at least 6 carbon atoms for this purpose, and the desired effect can be assisted by substitution with a mercapto, hydroxy or amino group.
  • a saturated cycloaliphatic radical R is used, the number of carbon atoms can be reduced because of the lower molecular mobility. It may therefore be a cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl optionally substituted by a mercapto or a hydroxy group be used. Even lower molecular mobility is achieved by mono- or polyunsaturated aliphatic chains. Starting materials for such intermediates are advantageously available as unsaturated fatty acids of biological origin.
  • the at least substantial insolubility of the amide portion in water can also be achieved by an alkyl spacer to be crosslinked oligooxazolines or an aryl spacer to cross-linking oligooxazolines.
  • phenyl as the radical R which is optionally substituted by a hydroxy, amino, nitro, halogen, alkyl, and / or trifluoromethyl group
  • the basicity of the amide group and thus also the water solubility can be influenced.
  • a heteroaryl as the radical R, where preferably a pyridyl, a thienyl, a thiazolyl, a triazolyl, a pyrimidinyl or a thiadiazolyl find use.
  • the anion bound to the nitrogen cation of the amine group can be chosen differently.
  • a chloride, a bisulfate, a sulfate, a dihydrogen phosphate, a hydrogen phosphate, a phosphate, a nitrate, a bicarbonate, a carbonate and an alkanoate anion can be given.
  • the invention is not limited to polymers with chloride as counterion.
  • hydrolysis with hydrogen chloride
  • another hydrolysis medium can be used, for example sulfuric acid. But it can also be a subsequent protonation of a nitrate, phosphate, carbonate or the like. Be made.
  • hydrolysis can be carried out by means of organic mono-, di- or polycarboxylic acids as eonate.
  • a 2-oxazoline can be used in a simple manner, which is first polymerized in a cationic ring-opening manner, before the polymer obtained has undergone partial hydrogenation. is subjected to lyse.
  • a hydrogen chloride is suitable for the hydrolysis, the invention is of course not limited to this hydrolysis medium. Due to the partial hydrolysis of the poly (2-oxazoline), its amide content is partly converted into an amine fraction which can be adjusted via the degree of hydrolysis, thus opening up a simple possibility of matching hydrophobicity and hydrophilicity.
  • the reaction rate is only dependent on the particular concentration of amide.
  • the degree of hydrolysis is proportional to the water solubility of the contact biocide, the water solubility of which can thus also be adjusted via the degree of hydrolysis.
  • the preferred degree of hydrolysis is 20 to 75%, because at such a degree of hydrolysis, the water solubility at a suitable radical R of the amide generally plays no role.
  • the amine portion of the contact biocide according to the invention can be incorporated to increase the water insolubility in the polymer matrix.
  • the nitrogen atoms can be ionically bonded by means of polymeric or copolymeric carboxylic acids, for example poly [propylene-co-methacrylic or maleic acid].
  • polymeric or copolymeric carboxylic acids for example poly [propylene-co-methacrylic or maleic acid].
  • Another possibility is a partial addition reaction of the nitrogen atoms on polymeric epoxide structures, such as poly (bisphenol glycidyl ether) or polyolefin-co-glycidyl methacrylate.
  • polymeric epoxide structures such as poly (bisphenol glycidyl ether) or polyolefin-co-glycidyl methacrylate.
  • Arylspacer in this context can advantageously phenylene-1, 3-bis-2-oxazoline and phenyl-1, 3,5-tris-2-oxazoline and as the alkyl spacer tetramethylene-1, 4-bis-2-oxazoline and octamethylene-1 , 8-bis-2 oxazoline be used.
  • substituents can be incorporated into the polymer matrix, which at the organic remainder of the Amidanteils for R relies are available. Suitable for this are ester. Amide, urethane, thio-click bonds or oxirane additions.
  • the poly (2-nonyl-2-oxazoline) thus obtained (0.500 g, 2.53 mmol) was weighed into a microwave vial, added with 6 M HCl (2 mL, 0.01 mol), and kept in the microwave for different times Hydrolyzed to 160 ° C.
  • the resulting pale yellow solid, poly (2-nonyl-2-oxazoline-co- (aziridinium chloride), was washed with 5 ml of acetone, the product was filtered off and dried in vacuo, the degree of hydrolysis being dependent on the reaction time of the table below.
  • the contact biocide according to the invention obtained with a degree of hydrolysis of 75% was kneaded in an amount of 1% by weight into a polypropylene having a melt flow index MFR of 0.42 at a temperature between 170 and 180 ° C. and from the homogeneous polymer mass sample platelets of 60 x 60 x 2 mm sprayed.
  • These coupons were tested against E. coli, S. aureus and Listeria monocytogenes according to JIS Z 2801: 2000. Across from All mentioned gram-positive and gram-vegetarian germs were inhibited by more than 99.9%. This value remained the same even after one week storage of the sample plates in distilled water.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

L'invention concerne l'utilisation d'un compose de formule (I) en tant que produit biocide par contact, A étant un fragment entrant sous forme de cation en coordination avec la paire d'électrons libres d'un atome d'azote, B étant un fragment réagissant sous forme d'anion avec un carbocation pour ainsi former un produit sans charge électrique, R étant un radical organique d'une chaîne aliphatique saturée en C6 à C30, un radical cycloaliphatique saturé, une chaîne aliphatique mono- ou polyinsaturée renfermant au moins 6 atomes de carbone, un groupe alkyle espaceur destiné à des oligooxazolines subissant une réticulation, un groupe aryle espaceur destiné à des oligooxazolines subissant une réticulation, un phényle, un alkylphényle, un hétéroaryle ou leurs copolymères et X étant un anion sans activité biocide, et (n+m) > 10.
PCT/AT2012/050059 2011-05-03 2012-05-02 Utilisation de produits biocides par contact à base d'oxazolines poly(2-substitués) WO2012149591A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ATA620/2011 2011-05-03
AT6202011A AT511386B1 (de) 2011-05-03 2011-05-03 Kontaktbiozid

Publications (1)

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WO2012149591A1 true WO2012149591A1 (fr) 2012-11-08

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014174434A1 (fr) 2013-04-22 2014-10-30 Jansen Ag Matière plastique présentant une surface biocide et procédé pour sa production
EP2824139A1 (fr) 2013-07-12 2015-01-14 Jansen AG Matière synthétique ayant une surface biocide et son procédé de fabrication
DE102013016750A1 (de) 2013-10-02 2015-04-02 Friedrich-Schiller-Universität Jena Neue Poly(ethylenimin) basierte Copolymere zur Anbindung und Freisetzung von genetischem Material, insbesondere von DNA/RNA, sowie Verfahren zu deren Herstellung und Verwendung
WO2015058226A1 (fr) 2013-10-21 2015-04-30 Polymer Competence Center Leoben Biocide de contact à base de poly-(oxazine)s, de poly-(oxaszépine)s et de poly-(oxazozin)es
WO2016086012A1 (fr) 2014-11-26 2016-06-02 Microban Products Company Désinfectant de surface ayant une propriété biocide résiduelle
WO2017091251A1 (fr) * 2015-11-23 2017-06-01 Microban Products Company Désinfectant de surface ayant une propriété biocide résiduelle
WO2017091250A1 (fr) * 2015-11-23 2017-06-01 Microban Products Company Désinfectant de surface ayant une propriété biocide résiduelle
WO2017205244A1 (fr) 2016-05-23 2017-11-30 Microban Products Company Composition de nettoyage et de protection pour écran tactile
EP3462867A4 (fr) * 2016-05-23 2019-11-27 Microban Products Company Produit topique pour la peau ayant une propriété de rétention
US10842147B2 (en) 2014-11-26 2020-11-24 Microban Products Company Surface disinfectant with residual biocidal property
CN111979014A (zh) * 2019-05-24 2020-11-24 英菲诺姆国际有限公司 润滑油添加剂
US10925281B2 (en) 2014-11-26 2021-02-23 Microban Products Company Surface disinfectant with residual biocidal property
US11033023B2 (en) 2014-11-26 2021-06-15 Microban Products Company Surface disinfectant with residual biocidal property
RU2777991C2 (ru) * 2015-11-23 2022-08-12 Майкробан Продактс Компани Дезинфицирующее вещество поверхностного действия с остаточным биоцидным свойством

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US4153466A (en) 1977-10-25 1979-05-08 The Dow Chemical Company Compositions comprising phosphate salts of poly-2-oxazoline and fire retardant formulations
US20050238825A1 (en) 2004-04-26 2005-10-27 Isp Investments Inc. Crosslinked polymeric composition
WO2006117382A1 (fr) * 2005-05-04 2006-11-09 Basf Aktiengesellschaft Revetements biocides
WO2007085552A2 (fr) * 2006-01-27 2007-08-02 Ciba Holding Inc. Agents antimicrobiens polymères

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US4153466A (en) 1977-10-25 1979-05-08 The Dow Chemical Company Compositions comprising phosphate salts of poly-2-oxazoline and fire retardant formulations
US20050238825A1 (en) 2004-04-26 2005-10-27 Isp Investments Inc. Crosslinked polymeric composition
WO2006117382A1 (fr) * 2005-05-04 2006-11-09 Basf Aktiengesellschaft Revetements biocides
WO2007085552A2 (fr) * 2006-01-27 2007-08-02 Ciba Holding Inc. Agents antimicrobiens polymères

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HANNEKE M. L. LAMBERMONT-THIJS ET AL: "Selective partial hydrolysis of amphiphilic copoly(2-oxazoline)s as basis for temperature and pH responsive micelles", POLYMER CHEMISTRY, vol. 2, no. 2, 21 May 2010 (2010-05-21), pages 313 - 322, XP055033911, ISSN: 1759-9954, DOI: 10.1039/c0py00052c *
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Cited By (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014174434A1 (fr) 2013-04-22 2014-10-30 Jansen Ag Matière plastique présentant une surface biocide et procédé pour sa production
EP2824139A1 (fr) 2013-07-12 2015-01-14 Jansen AG Matière synthétique ayant une surface biocide et son procédé de fabrication
US10131747B2 (en) 2013-10-02 2018-11-20 Smartdyelivery Gmbh Poly(ethylene imine)-based copolymers for bonding to and releasing genetic material, in particular DNA/RNA, and method for the production and use of same
DE102013016750A1 (de) 2013-10-02 2015-04-02 Friedrich-Schiller-Universität Jena Neue Poly(ethylenimin) basierte Copolymere zur Anbindung und Freisetzung von genetischem Material, insbesondere von DNA/RNA, sowie Verfahren zu deren Herstellung und Verwendung
WO2015048940A1 (fr) 2013-10-02 2015-04-09 Friedrich-Schiller-Universität Jena Nouveaux copolymères à base de poly(éthylène-imine) pour la liaison et la libération de matériel génétique, en particulier d'adn/arn, procédé de préparation et utilisation de ces copolymères
WO2015058226A1 (fr) 2013-10-21 2015-04-30 Polymer Competence Center Leoben Biocide de contact à base de poly-(oxazine)s, de poly-(oxaszépine)s et de poly-(oxazozin)es
US10925281B2 (en) 2014-11-26 2021-02-23 Microban Products Company Surface disinfectant with residual biocidal property
RU2733134C2 (ru) * 2014-11-26 2020-09-29 Майкробан Продактс Компани Дезинфицирующее средство для поверхностей, обладающее остаточными биоцидными свойствами
CN107205383A (zh) * 2014-11-26 2017-09-26 美可帮产品公司 具有残余的杀生物性质的表面消毒剂
CN107231806A (zh) * 2014-11-26 2017-10-03 美可帮产品公司 具有残余的杀生物性质的表面消毒剂
US11134674B2 (en) 2014-11-26 2021-10-05 Microban Products Company Surface disinfectant with residual biocidal property
EP3224300A4 (fr) * 2014-11-26 2018-08-29 Microban Products Company Désinfectant de surface ayant une propriété biocide résiduelle
EP3223612A4 (fr) * 2014-11-26 2018-09-26 Microban Products Company Désinfectant de surface ayant une propriété biocide résiduelle
US11134678B2 (en) 2014-11-26 2021-10-05 Microban Products Company Surface disinfectant with residual biocidal property
US11033023B2 (en) 2014-11-26 2021-06-15 Microban Products Company Surface disinfectant with residual biocidal property
US11026418B2 (en) 2014-11-26 2021-06-08 Microban Products Company Surface disinfectant with residual biocidal property
EP3224300B1 (fr) 2014-11-26 2021-06-02 Microban Products Company Désinfectant de surface ayant une propriété biocide résiduelle
WO2016086012A1 (fr) 2014-11-26 2016-06-02 Microban Products Company Désinfectant de surface ayant une propriété biocide résiduelle
US10842147B2 (en) 2014-11-26 2020-11-24 Microban Products Company Surface disinfectant with residual biocidal property
US10834922B2 (en) 2014-11-26 2020-11-17 Microban Products Company Surface disinfectant with residual biocidal property
CN108697078A (zh) * 2015-11-23 2018-10-23 美可帮产品公司 具有残余杀生物性质的表面杀菌剂
CN108697082A (zh) * 2015-11-23 2018-10-23 美可帮产品公司 具有残余杀生物性质的表面杀菌剂
RU2778401C2 (ru) * 2015-11-23 2022-08-18 Майкробан Продактс Компани Дезинфицирующее вещество поверхностного действия с остаточным биоцидным свойством
RU2777991C2 (ru) * 2015-11-23 2022-08-12 Майкробан Продактс Компани Дезинфицирующее вещество поверхностного действия с остаточным биоцидным свойством
EP3379931A4 (fr) * 2015-11-23 2019-06-05 Microban Products Company Désinfectant de surface ayant une propriété biocide résiduelle
EP3379932A4 (fr) * 2015-11-23 2019-05-01 Microban Products Company Désinfectant de surface ayant une propriété biocide résiduelle
WO2017091251A1 (fr) * 2015-11-23 2017-06-01 Microban Products Company Désinfectant de surface ayant une propriété biocide résiduelle
WO2017091250A1 (fr) * 2015-11-23 2017-06-01 Microban Products Company Désinfectant de surface ayant une propriété biocide résiduelle
EP3463368A4 (fr) * 2016-05-23 2019-12-25 Microban Products Company Composition de nettoyage et de protection pour écran tactile
WO2017205244A1 (fr) 2016-05-23 2017-11-30 Microban Products Company Composition de nettoyage et de protection pour écran tactile
EP3462867A4 (fr) * 2016-05-23 2019-11-27 Microban Products Company Produit topique pour la peau ayant une propriété de rétention
US11503824B2 (en) 2016-05-23 2022-11-22 Microban Products Company Touch screen cleaning and protectant composition
CN111979014A (zh) * 2019-05-24 2020-11-24 英菲诺姆国际有限公司 润滑油添加剂
CN111979014B (zh) * 2019-05-24 2023-05-12 英菲诺姆国际有限公司 润滑油添加剂

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