WO2011135577A1 - Polyhexamethyleneguanidine and its salts based disinfectant. - Google Patents

Polyhexamethyleneguanidine and its salts based disinfectant. Download PDF

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Publication number
WO2011135577A1
WO2011135577A1 PCT/IN2010/000278 IN2010000278W WO2011135577A1 WO 2011135577 A1 WO2011135577 A1 WO 2011135577A1 IN 2010000278 W IN2010000278 W IN 2010000278W WO 2011135577 A1 WO2011135577 A1 WO 2011135577A1
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Prior art keywords
polyhexamethyleneguanidine
disinfectant
disinfection
salts based
cited
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Application number
PCT/IN2010/000278
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French (fr)
Inventor
Reijo Saunamaki
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Bios Agricorp Pvt. Ltd.
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Priority to PCT/IN2010/000278 priority Critical patent/WO2011135577A1/en
Publication of WO2011135577A1 publication Critical patent/WO2011135577A1/en

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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, 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
    • A01N47/40Biocides, 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
    • A01N47/42Biocides, 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
    • A01N47/44Guanidine; Derivatives thereof

Definitions

  • This invention relates to a composition and method for disinfecting and sterilizing matter contaminated with bacteria, fungi, spores, viruses, and the like.
  • the said invention discloses a method and a composition for disinfecting matter or materials such as medical instruments, operating rooms, examining tables, walls, windows, floors, solutions, porous substances and the like contaminated with bacteria, bacterial spores, fungi, or viruses.
  • the composition consists of a mixture of a peroxymonosulfate and a carbonyl- containing compound and reaction products thereof and is preferably dioxirane formed by in situ oxidation of a ketone or aldehyde by the peroxymonosulfate in aqueous solution.
  • Carbonyl-containing compounds that have been tested include acetone, 2-pentanone, 4- hydroxy-4-methyl-2-pentanone, and camphorsulfonic acid.
  • the method includes providing a solution containing the dioxirane reaction mixture and contacting the matter or materials with it at room temperature for a time sufficient to disinfect and sterilize the matter or material.
  • the inventive disinfectant comprises a disinfecting agent and water.
  • a first component in the form of polyhexamethylene guanidine hydrochloride or polyhexamethylene guanidine hydrophosphate and a second component in the form of alkyl dimethyl benzil ammonium chloride or a mixture thereof with quaternary ammonium salts of dimethylamine and/or of tertiary amine are used as disinfecting agents.
  • the mass ratio m between the first and second components ranges within an interval of 5:1 ⁇ m ⁇ 10:1 when the content thereof ranges from 1.5 to 6.0 mass % and from 0.15 to 1.2 mass %, respectively.
  • the said invention relates to a sterilizing agent that is little toxic to the body and non-corrosive to metal with superiority in the rapid action and persistency of germicidal activity, comprising polyhexamethyleneguanidine phosphate and 2-bromo-2-nitro- 1,3 -propanediol, represented by the following formulas I and II, respectively, at a weight ratio of 1 :1 to 20:1 polyhexamethyleneguanidine phosphate :2-bromo-2-nitro- 1,3 -propanediol, wherein m is an integer of 4 to 7 and n is an integer of 1 to 14relates to health, namely to means for disinfecting drinking water.
  • the inventive disinfectant comprises a disinfecting agent and water.
  • a first component in the form of polyhexamethylene guanidine hydrochloride or polyhexamethylene guanidine hydrophosphate and a second component in the form of alkyl dimethyl benzil ammonium chloride or a mixture thereof with quaternary ammonium salts of dimethylamine and/or of tertiary amine are used as disinfecting agents.
  • the mass ratio m between the first and second components ranges within an interval of 5:1 ⁇ m ⁇ 10:1 when the content thereof ranges from 1.5 to 6.0 mass % and from 0.15 to 1.2 mass %, respectively.
  • a virucidal disinfectant having broad-range activity includes an acidic phosphorus compound and/or salt thereof, an alcohol, and one or more polyalkylene glycols.
  • the disinfectant which may also kill bacteria and/or fungi, may be used for the hygienic disinfection of animate and inanimate surfaces.
  • the invention also provides a disinfection method and a product containing a disinfectant.
  • compositions which include one or more 1- or 2-(C r to C24-alkyl)glycerol ethers (glycerol monoalkyl ethers), one or more bispyridiniumalkanes and where appropriate one or more polyols and/or one or more surfactants selected from the group of cl) nonionic surfactant and c2) quaternary ammonium compound, and to the use of the compositions for hygienic hand disinfection or for disinfectant handwashing, and as skin antiseptic.
  • the compositions according to the invention have a particularly low surface tension and thus an improved wetting effect.
  • the said invention provides a disinfectant and/or bactericidal aqueous composition containing an olanexidine acid addition salt, and at least one polyoxyethylene-based nonionic surfactant selected from the group consisting of polyoxyethylene higher alkyl ethers and polyoxyethylene alkylphenyl ethers; a disinfectant and/or bactericidal aqueous composition containing an olanexidine acid addition salt at a concentration of 0.05 to 0.5 W/V%, and an alcohol at a concentration of 20 to 80 W/V%, and not containing any surfactants; and a disinfectant and/or bactericidal aqueous composition containing an olanexidine acid addition salt , and at least one member selected from the group consisting of ester-based nonionic surfactants and cyclic oligosaccharides.
  • a low pH disinfectant composition comprises an aqueous composition of a phenolic compound, an organic acid, and/or a dispersing surfactant and/or solvent.
  • the disinfectant solution can be concentrated, or more preferably diluted ready to use, and is very effective in eradicating fungi including Aspergillus niger.
  • Indian Patent Application No. 6214 DELNP/2006 wherein the said invention provides a low pH disinfectant composition comprises an aqueous composition of a phenolic compound, an organic acid, and/or a dispersing surfactant and/or solvent.
  • the disinfectant solution can be concentrated, or more preferably diluted ready to use, and is very effective in eradicating fungi including Aspergillus niger.
  • aqueous concentrated liquid disinfectant compositions which include: an anumicrobial compound other than a quaternary ammonium compound having germicidal properties; organic solvent constituent; binary co-solvent system comprising alkyl biphenyl solvent and a co-solvent; optionally but desirably at least one optional constituent.
  • the concentrate compositions feature excellent blooming characteristics
  • the known commercially available disinfectants are alcohol based preparations.
  • the mentioned alcohols and their mixtures as well as many commercially available preparations are able to inactivate enveloped viruses.
  • the alcohols as well as the preparations known to the skilled person have a number of drawbacks.
  • ethanol is effective against enveloped and non-enveloped viruses only in high concentrations.
  • propane- l-ol and propane-2-ol are only selectively effective; they are ineffective against most non-enveloped viruses, e.g., against the highly resistant picornaviruses, which include polioviruses and hepatitis A virus.
  • the present invention relates to polyhexamethyleneguanidine (PHMG) based disinfectant having broad-range activity, the use of said disinfectant fori the hygienic disinfection of animate and inanimate surfaces as well as for killing viruses, bacteria and fungi. Further, the invention relates to a disinfection method and to a product containing a disinfectant.
  • PHMG polyhexamethyleneguanidine
  • the inventor has invented a method and composition for disinfecting hand, matter or materials such as medical instruments, operating rooms, examining tables, laboratories, walls, windows, floors, solutions, porous substances, non porous substances, and the like contaminated with bacteria, bacterial spores, fungi, or viruses.
  • the composition consists of a polyhexamethyleneguanidine as the key ingredient.
  • this invention relates to a method and composition for disinfecting hand, matter or materials such as medical instruments, operating rooms, examining tables, laboratories, walls, windows, floors, solutions, porous substances, non porous substances, and the like contaminated with bacteria, bacterial spores, fungi, or viruses from polyhexamethyleneguanidine based composition.
  • Polyhexamethyleneguanidine (PHMG) and other polyguanidines are derivatives of nitrogenous base - guanidine.
  • PHMG is synthesized in the forms of linear and branched polymers. It's real MW can vary in a wide range of magnitudes
  • Low-molecular PHMG can be synthesised H2N-C-NH2 ⁇ 2 ⁇ -((3 ⁇ 4)6- ⁇ .2 by thermal polycondensation of GHC HMDA
  • HMDA hexamethylendiamine
  • guanidine hydrochloride at temperatures varying from 165 to 250°C.
  • High- molecular products can be synthesized by further polycondensation of low-molecular PHMG in aqueous solution at the presence of alkali. It has been shown, that after about 9 h
  • synthesized are water soluble and can be filtered and desiccated to desired constant weight.
  • PHMG shows very good and vide spectrum of microbiological activity making it excellent tool for disinfection and other antimicrobial needs, the bigger is the molecular weight the better activity can be reached.
  • This patent application is focused to use PHMG as a disinfectant, preservative and antimicrobial agent in the following fields of applications such as healthcare and public institutions, both for surface and skin disinfection; public areas disinfection, hand disinfection in schools, kindergartens etc; agriculture use, in farms and animal housing, animal production, post and pre harvest use; food and feed storing; as a preservative in food, pickles, Juices etc; aqua- culture disinfectant; drinking water and water supplies for both human and animals; wood preservative and anti mould agent for wood impregnation; paper, fibre and pulp manufacturing as disinfectant in the process and anti bacterial agent for ready to use products or semi products like packing material; industrial processing cooling and cutting oils and liquids and general disinfection; oil pumping and recovery disinfectant.
  • Preservative and disinfection of oil products and bio diesel etc textile industry disinfectant for preservation and disinfection in textile manufacturing and storing and transportation; antimicrobial and anti mould coating for buildings and building materials alone or mixed with other materials.

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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)

Abstract

A method and a composition for disinfecting hand, matter or materials such as medical instruments, operating rooms, examining tables, laboratories, walls, windows, floors, solutions, porous substances, non porous substances, and the like contaminated with bacteria, bacterial spores, fungi, or viruses is disclosed. The composition consists of a polyhexamethyleneguanidine as the key ingredient.

Description

TITLE - Polyhexamethyleneguanidine and its salts Based Disinfectant.
PREAMBLE OF INVENTION- This invention in particular describes the nature of the invention and the manner in which it is to be performed.
FIELD OF INVENTION - This invention relates to a composition and method for disinfecting and sterilizing matter contaminated with bacteria, fungi, spores, viruses, and the like.
PRIOR ART-
In the existing system as given in Unites States Patent Application No. 5403549, wherein, the said invention discloses a method and a composition for disinfecting matter or materials such as medical instruments, operating rooms, examining tables, walls, windows, floors, solutions, porous substances and the like contaminated with bacteria, bacterial spores, fungi, or viruses. The composition consists of a mixture of a peroxymonosulfate and a carbonyl- containing compound and reaction products thereof and is preferably dioxirane formed by in situ oxidation of a ketone or aldehyde by the peroxymonosulfate in aqueous solution. Carbonyl-containing compounds that have been tested include acetone, 2-pentanone, 4- hydroxy-4-methyl-2-pentanone, and camphorsulfonic acid. The method includes providing a solution containing the dioxirane reaction mixture and contacting the matter or materials with it at room temperature for a time sufficient to disinfect and sterilize the matter or material.
In the existing system as given in European Patent Application No. EP1394120, wherein the said invention relates to health, namely to means for disinfecting drinking water. The inventive disinfectant comprises a disinfecting agent and water. A first component in the form of polyhexamethylene guanidine hydrochloride or polyhexamethylene guanidine hydrophosphate and a second component in the form of alkyl dimethyl benzil ammonium chloride or a mixture thereof with quaternary ammonium salts of dimethylamine and/or of tertiary amine are used as disinfecting agents. The mass ratio m between the first and second components ranges within an interval of 5:1 < m < 10:1 when the content thereof ranges from 1.5 to 6.0 mass % and from 0.15 to 1.2 mass %, respectively.
In the existing system as given in United States Patent Application No. 20050101648, wherein the said invention relates to antibacterial and antifungal compositions having 3- isothiazolone and polyhexamethyleneguanidine phosphate. These new antiseptic compositions demonstrate a superior degree of effectiveness on a wide spectrum of pathogens. The present invention also relates to the use of these new antiseptic compositions to kill and/or restrain the growth of bacteria and fungi in a variety of applications.
In the existing system as given in European Patent Application No. EP0233731, wherein the said invention relates to a low molecular weight monoperoxyaliphatic acids such as peracetic acid that are useful as broad spectrum biocides. An even broader spectrum of activity is achieved by selecting monoperoxyaliphatic acids having a carbon chain length of 6 to 9 atoms, which act as sporicides and in a wider pH range. A preferred biocide is peroxyheptanoic acid. The process can be carried out on solid surfaces such as in place equipment, or containers or in liquid media such as process or recirculating waters.
In the existing system as given in European Patent Application No. EP1114585, wherein the said invention relates to a sterilizing agent that is little toxic to the body and non-corrosive to metal with superiority in the rapid action and persistency of germicidal activity, comprising polyhexamethyleneguanidine phosphate and 2-bromo-2-nitro- 1,3 -propanediol, represented by the following formulas I and II, respectively, at a weight ratio of 1 :1 to 20:1 polyhexamethyleneguanidine phosphate :2-bromo-2-nitro- 1,3 -propanediol, wherein m is an integer of 4 to 7 and n is an integer of 1 to 14relates to health, namely to means for disinfecting drinking water. The inventive disinfectant comprises a disinfecting agent and water. A first component in the form of polyhexamethylene guanidine hydrochloride or polyhexamethylene guanidine hydrophosphate and a second component in the form of alkyl dimethyl benzil ammonium chloride or a mixture thereof with quaternary ammonium salts of dimethylamine and/or of tertiary amine are used as disinfecting agents. The mass ratio m between the first and second components ranges within an interval of 5:1 < m < 10:1 when the content thereof ranges from 1.5 to 6.0 mass % and from 0.15 to 1.2 mass %, respectively.
In the existing system as given in United States Patent Application No. 20090252775, wherein the said invention relates to a virucidal disinfectant having broad-range activity includes an acidic phosphorus compound and/or salt thereof, an alcohol, and one or more polyalkylene glycols. The disinfectant, which may also kill bacteria and/or fungi, may be used for the hygienic disinfection of animate and inanimate surfaces. The invention also provides a disinfection method and a product containing a disinfectant. In the existing system as given in United States Patent Application No. 20060165612, wherein the said invention relates to disinfectant compositions which include one or more 1- or 2-(Cr to C24-alkyl)glycerol ethers (glycerol monoalkyl ethers), one or more bispyridiniumalkanes and where appropriate one or more polyols and/or one or more surfactants selected from the group of cl) nonionic surfactant and c2) quaternary ammonium compound, and to the use of the compositions for hygienic hand disinfection or for disinfectant handwashing, and as skin antiseptic. The compositions according to the invention have a particularly low surface tension and thus an improved wetting effect.
In the existing system as given in Indian Patent Application No. 5398/DELNP/2005, wherein the said invention provides a disinfectant and/or bactericidal aqueous composition containing an olanexidine acid addition salt, and at least one polyoxyethylene-based nonionic surfactant selected from the group consisting of polyoxyethylene higher alkyl ethers and polyoxyethylene alkylphenyl ethers; a disinfectant and/or bactericidal aqueous composition containing an olanexidine acid addition salt at a concentration of 0.05 to 0.5 W/V%, and an alcohol at a concentration of 20 to 80 W/V%, and not containing any surfactants; and a disinfectant and/or bactericidal aqueous composition containing an olanexidine acid addition salt , and at least one member selected from the group consisting of ester-based nonionic surfactants and cyclic oligosaccharides.
In the existing system as given in Indian Patent Application No. 6214 DELNP/2006, wherein the said invention provides a low pH disinfectant composition comprises an aqueous composition of a phenolic compound, an organic acid, and/or a dispersing surfactant and/or solvent. The disinfectant solution can be concentrated, or more preferably diluted ready to use, and is very effective in eradicating fungi including Aspergillus niger. In the existing system as given in Indian Patent Application No. IN PCT/2000/498/CHEA, where in the said invention relates to an aqueous concentrated liquid disinfectant compositions which include: an anumicrobial compound other than a quaternary ammonium compound having germicidal properties; organic solvent constituent; binary co-solvent system comprising alkyl biphenyl solvent and a co-solvent; optionally but desirably at least one optional constituent. The concentrate compositions feature excellent blooming characteristics
OBJECT OF THE INVENTION -
Traditionally the known commercially available disinfectants are alcohol based preparations. The mentioned alcohols and their mixtures as well as many commercially available preparations are able to inactivate enveloped viruses. However, if a comprehensive antiviral effectiveness is required, the alcohols as well as the preparations known to the skilled person have a number of drawbacks. Thus, it is known that ethanol is effective against enveloped and non-enveloped viruses only in high concentrations. In contrast, propane- l-ol and propane-2-ol are only selectively effective; they are ineffective against most non-enveloped viruses, e.g., against the highly resistant picornaviruses, which include polioviruses and hepatitis A virus. The present invention relates to polyhexamethyleneguanidine (PHMG) based disinfectant having broad-range activity, the use of said disinfectant fori the hygienic disinfection of animate and inanimate surfaces as well as for killing viruses, bacteria and fungi. Further, the invention relates to a disinfection method and to a product containing a disinfectant.
STATEMENT OF INVENTION- The inventor has invented a method and composition for disinfecting hand, matter or materials such as medical instruments, operating rooms, examining tables, laboratories, walls, windows, floors, solutions, porous substances, non porous substances, and the like contaminated with bacteria, bacterial spores, fungi, or viruses. The composition consists of a polyhexamethyleneguanidine as the key ingredient.
DETAILED DESCRIPTION OF INVENTION-
Accordingly, in one aspect, this invention relates to a method and composition for disinfecting hand, matter or materials such as medical instruments, operating rooms, examining tables, laboratories, walls, windows, floors, solutions, porous substances, non porous substances, and the like contaminated with bacteria, bacterial spores, fungi, or viruses from polyhexamethyleneguanidine based composition.
Polyhexamethyleneguanidine (PHMG) and other polyguanidines are derivatives of nitrogenous base - guanidine. The elementary
chains of polyguanides molecules have the
Figure imgf000008_0001
groups with delocalized electrons. In cations of
PHMG
guanidine the positive charge is distributed
symmetrically within the area of equivalent structural surroundings stabilizing the structure therefore, the protonation is energetically favourable process.
PHMG is synthesized in the forms of linear and branched polymers. It's real MW can vary in a wide range of magnitudes
depending on the conditions of synthesis. NH - HC1
Low-molecular PHMG can be synthesised H2N-C-NH2 Η2Ν-((¾)6-ΝΗ.2 by thermal polycondensation of GHC HMDA
hexamethylendiamine (HMDA) with
guanidine hydrochloride (GHC) at temperatures varying from 165 to 250°C. High- molecular products can be synthesized by further polycondensation of low-molecular PHMG in aqueous solution at the presence of alkali. It has been shown, that after about 9 h
the ammonia ceases to evolve from the m*a Ha (CHa)j H2
1/2H?NCNHCN — *- H?NCNHS . — P+NHj
" II 20Q°C 15O¾-20O°C 3 reaction mix sig °nalling ° the end of N'H N J !H:HC„,I
polycondensation reaction. The polymers
synthesized are water soluble and can be filtered and desiccated to desired constant weight.
PHMG shows very good and vide spectrum of microbiological activity making it excellent tool for disinfection and other antimicrobial needs, the bigger is the molecular weight the better activity can be reached.
This patent application is focused to use PHMG as a disinfectant, preservative and antimicrobial agent in the following fields of applications such as healthcare and public institutions, both for surface and skin disinfection; public areas disinfection, hand disinfection in schools, kindergartens etc; agriculture use, in farms and animal housing, animal production, post and pre harvest use; food and feed storing; as a preservative in food, pickles, Juices etc; aqua- culture disinfectant; drinking water and water supplies for both human and animals; wood preservative and anti mould agent for wood impregnation; paper, fibre and pulp manufacturing as disinfectant in the process and anti bacterial agent for ready to use products or semi products like packing material; industrial processing cooling and cutting oils and liquids and general disinfection; oil pumping and recovery disinfectant. Preservative and disinfection of oil products and bio diesel etc; textile industry disinfectant for preservation and disinfection in textile manufacturing and storing and transportation; antimicrobial and anti mould coating for buildings and building materials alone or mixed with other materials.

Claims

CLAIMS We claim,
1. A method and a composition containing polyhexamethyleneguanidine for disinfecting hand, matter or materials such as medical instruments, operating rooms, examining tables, laboratories, walls, windows, floors, solutions, porous substances, non porous substances, and the like contaminated with bacteria, bacterial spores, fungi, or viruses is disclosed.
2. A Polyhexamethyleneguanidine and its salts Based Disinfectant as cited in claim 1, wherein, the method involves synthesization of polyhexamethyleneguanidine in the forms of linear and branched polymers.
3. A Polyhexamethyleneguanidine and its salts Based Disinfectant as cited in claim 1, wherein, real MW can vary in a wide range of magnitudes depending on the conditions of synthesis.
4. A Polyhexamethyleneguanidine and its salts Based Disinfectant as cited in claim 1, wherein, low-molecular PHMG can be synthesised by thermal polycondensation of hexamethylendiamine (HMDA) with guanidine hydrochloride (GHC) at temperatures varying from 165 to 250°C. A Polyhexamethyleneguanidine and its salts Based Disinfectant as cited in claim 1, wherein, high-molecular products can be synthesized by further polycondensation of low-molecular PHMG in aqueous solution at the presence of alkali.
5. A Polyhexamethyleneguanidine and its salts Based Disinfectant as cited in claim 1, wherein, after about 9 hour, the ammonia ceases to evolve from the reaction mix signalling the end of polycondensation reaction.
6. A Polyhexamethyleneguanidine and its salts Based Disinfectant as cited in claim 1, wherein, Polyhexamethyleneguanidine and its salts Based Disinfectant shows very good and vide spectrum of microbiological activity making it excellent tool for disinfection and other antimicrobial needs, the bigger is the molecular weight the better activity can be reached. ,
7. A Polyhexamethyleneguanidine and its salts Based Disinfectant as cited in claim 1, which is used as a disinfectant, preservative and antimicrobial agent in the vide fields of applications such as healthcare and public institutions, both for surface and skin disinfection; public areas disinfection, hand disinfection in schools, kindergartens etc; agriculture use, in farms and animal housing, animal production, post and pre harvest use; food and feed storing; as a preservative in food, pickles, Juices etc; aqua- culture disinfectant; drinking water and water supplies for both human and animals; wood preservative and anti mould agent for wood impregnation; paper, fibre and pulp manufacturing as disinfectant in the process and anti bacterial agent for ready to use products or semi products like packing material; industrial processing cooling and cutting oils and liquids and general disinfection; oil pumping and recovery disinfectant. Preservative and disinfection of oil products and bio diesel etc; textile industry disinfectant for preservation and disinfection in textile manufacturing and storing and transportation; antimicrobial and anti mould coating for buildings and building materials alone or mixed with other materials.
PCT/IN2010/000278 2010-04-29 2010-04-29 Polyhexamethyleneguanidine and its salts based disinfectant. WO2011135577A1 (en)

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CN102524317A (en) * 2012-01-04 2012-07-04 刘钧 Sterilized solution for assay detection instrument
WO2013106863A1 (en) * 2012-01-12 2013-07-18 Lombardi John L Antipathogenic guanidinium copolymer
WO2015133928A1 (en) * 2014-03-07 2015-09-11 Римма Ильинична АШКИНАЗИ Antiviral agent
US10080728B2 (en) 2015-01-20 2018-09-25 Viktor Veniaminovich Tets Hemostatic agent
CN110123832A (en) * 2019-05-13 2019-08-16 东南大学 A kind of ophthalmic composition containing no drug resistance fungicide
WO2019178633A1 (en) * 2018-03-23 2019-09-26 Bcsk Biocid Gmbh Method and composition for combating viruses of the picornaviridae family
CN111607469A (en) * 2020-07-08 2020-09-01 青岛拜士特新材料有限公司 Instant antibacterial masterbatch and preparation method thereof
CN111690469A (en) * 2020-07-08 2020-09-22 青岛拜士特新材料有限公司 Degerming washing powder containing zinc pyrithione antibacterial agent and preparation method thereof
CN111733027A (en) * 2020-07-08 2020-10-02 青岛拜士特新材料有限公司 Instant washing antibacterial master batch and preparation method thereof
CN111733021A (en) * 2020-07-08 2020-10-02 青岛拜士特新材料有限公司 Sterilizing washing powder containing PCMX and preparation method thereof
US11285170B2 (en) 2017-05-24 2022-03-29 Viktor Veniaminovich Tets Fractionated antimicrobial compositions and use thereof

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Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102524317A (en) * 2012-01-04 2012-07-04 刘钧 Sterilized solution for assay detection instrument
WO2013106863A1 (en) * 2012-01-12 2013-07-18 Lombardi John L Antipathogenic guanidinium copolymer
US9403944B2 (en) 2012-01-12 2016-08-02 John L. Lombardi Antipathogenic guanidinium copolymer
WO2015133928A1 (en) * 2014-03-07 2015-09-11 Римма Ильинична АШКИНАЗИ Antiviral agent
US10299480B2 (en) 2014-03-07 2019-05-28 Viktor Veniaminovich Tets Antiviral agent
US10080728B2 (en) 2015-01-20 2018-09-25 Viktor Veniaminovich Tets Hemostatic agent
US11285170B2 (en) 2017-05-24 2022-03-29 Viktor Veniaminovich Tets Fractionated antimicrobial compositions and use thereof
AT521124A1 (en) * 2018-03-23 2019-10-15 Bcsk Biocid Gmbh Method and composition for controlling viruses of the family Picornaviridae
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CN110123832A (en) * 2019-05-13 2019-08-16 东南大学 A kind of ophthalmic composition containing no drug resistance fungicide
CN111607469A (en) * 2020-07-08 2020-09-01 青岛拜士特新材料有限公司 Instant antibacterial masterbatch and preparation method thereof
CN111690469A (en) * 2020-07-08 2020-09-22 青岛拜士特新材料有限公司 Degerming washing powder containing zinc pyrithione antibacterial agent and preparation method thereof
CN111733027A (en) * 2020-07-08 2020-10-02 青岛拜士特新材料有限公司 Instant washing antibacterial master batch and preparation method thereof
CN111733021A (en) * 2020-07-08 2020-10-02 青岛拜士特新材料有限公司 Sterilizing washing powder containing PCMX and preparation method thereof
CN111733027B (en) * 2020-07-08 2022-03-11 青岛拜士特新材料有限公司 Instant washing antibacterial master batch and preparation method thereof
CN111607469B (en) * 2020-07-08 2022-03-11 青岛拜士特新材料有限公司 Instant antibacterial masterbatch and preparation method thereof
CN111733021B (en) * 2020-07-08 2022-03-29 青岛拜士特新材料有限公司 Sterilizing washing powder containing PCMX and preparation method thereof

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