WO2016028183A1 - Антисептический препарат и способ его использования - Google Patents

Антисептический препарат и способ его использования Download PDF

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Publication number
WO2016028183A1
WO2016028183A1 PCT/RU2014/000615 RU2014000615W WO2016028183A1 WO 2016028183 A1 WO2016028183 A1 WO 2016028183A1 RU 2014000615 W RU2014000615 W RU 2014000615W WO 2016028183 A1 WO2016028183 A1 WO 2016028183A1
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WO
WIPO (PCT)
Prior art keywords
type
cocoalkyl
silver
range
salts
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.)
Ceased
Application number
PCT/RU2014/000615
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English (en)
French (fr)
Russian (ru)
Inventor
Альберт Николаевич ДЕНИСОВ
Юрий Андреевич КРУТЯКОВ
Алексей Александрович КУДРИНСКИЙ
Павел Михайлович ЖЕРЕБИН
Алексей Игоревич КЛИМОВ
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.)
OBSHCHESTVO S OGRANICHENNOY OTVETSTVENNOSTYU "NANOBIOTEKH"
Original Assignee
OBSHCHESTVO S OGRANICHENNOY OTVETSTVENNOSTYU "NANOBIOTEKH"
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
Priority to EA201700110A priority Critical patent/EA038054B1/ru
Priority to US15/502,762 priority patent/US10717661B2/en
Priority to JP2017529966A priority patent/JP6783762B2/ja
Priority to CN201480081288.8A priority patent/CN107207294A/zh
Priority to PL14900041T priority patent/PL3184492T3/pl
Priority to CA2959466A priority patent/CA2959466C/en
Priority to PCT/RU2014/000615 priority patent/WO2016028183A1/ru
Priority to ES14900041T priority patent/ES2772182T3/es
Priority to KR1020177007044A priority patent/KR102131731B1/ko
Priority to KR1020197015449A priority patent/KR20190064670A/ko
Priority to MYPI2017700543A priority patent/MY182571A/en
Application filed by OBSHCHESTVO S OGRANICHENNOY OTVETSTVENNOSTYU "NANOBIOTEKH" filed Critical OBSHCHESTVO S OGRANICHENNOY OTVETSTVENNOSTYU "NANOBIOTEKH"
Priority to TN2017000030A priority patent/TN2017000030A1/en
Priority to UAA201702263A priority patent/UA120100C2/uk
Priority to MX2017002083A priority patent/MX385223B/es
Priority to BR112017003279-1A priority patent/BR112017003279A2/pt
Priority to AU2014403897A priority patent/AU2014403897B2/en
Priority to EP14900041.6A priority patent/EP3184492B1/en
Publication of WO2016028183A1 publication Critical patent/WO2016028183A1/ru
Priority to PH12017500274A priority patent/PH12017500274B1/en
Anticipated expiration legal-status Critical
Priority to ECIEPI201716787A priority patent/ECSP17016787A/es
Ceased legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C02TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02FTREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00Treatment of water, waste water, or sewage
    • C02F1/50Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
    • C02F1/505Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment by oligodynamic treatment
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00Medicinal preparations containing inorganic active ingredients
    • A61K33/24Heavy metals; Compounds thereof
    • A61K33/38Silver; Compounds thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2/00Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
    • A61L2/16Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
    • A61L2/18Liquid substances or solutions comprising solids or dissolved gases
    • CCHEMISTRY; METALLURGY
    • C02TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02FTREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00Treatment of water, waste water, or sewage
    • C02F1/50Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54Polymers characterized by specific structures/properties
    • A61K2800/542Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5428Polymers characterized by specific structures/properties characterized by the charge amphoteric or zwitterionic
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B82NANOTECHNOLOGY
    • B82YSPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00Nanotechnology for materials or surface science, e.g. nanocomposites
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B82NANOTECHNOLOGY
    • B82YSPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
    • CCHEMISTRY; METALLURGY
    • C02TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02FTREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2103/00Nature of the water, waste water, sewage or sludge to be treated
    • C02F2103/42Nature of the water, waste water, sewage or sludge to be treated from bathing facilities, e.g. swimming pools
    • CCHEMISTRY; METALLURGY
    • C02TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02FTREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2209/00Controlling or monitoring parameters in water treatment
    • C02F2209/06Controlling or monitoring parameters in water treatment pH
    • CCHEMISTRY; METALLURGY
    • C02TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02FTREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2303/00Specific treatment goals
    • C02F2303/08Corrosion inhibition

Definitions

  • the invention relates to the field of sanitation and hygiene, in particular, to antiseptic preparations, including disinfectants for disinfecting water in swimming pools and other artificial reservoirs, for sanitary-hygienic processing of premises, household equipment, furniture, household appliances and industrial equipment, and also for disinfection of washing and wastewater.
  • a disinfecting aqueous solution containing silver ions, distilled water, lactic acid and a 33% aqueous solution of hydrogen peroxide.
  • This invention is intended for use in healthcare, food and pharmaceutical industries, utilities, for disinfection and conservation of drinking water, for the disinfection of swimming pools.
  • the disadvantage of this drug is the short duration of the biocidal action.
  • the application for the grant of a patent of the Russian Federation jV ° 2010134589 discloses a method for additional prolonged fungicidal disinfection of the surfaces of bathtubs and auxiliary rooms of swimming pools, in which silver nanoparticles in a concentration of 167 rt are applied to the surface of ceramic tiles by treating the tiles with an aqueous-organic solution of nanosized silver particles for 40 -50 hours at a temperature of 16-20 ° C, followed by washing with a hydrocarbon, water-alcohol mixture and distilled water for 30 minutes at room temperature perature.
  • the disadvantage of this drug is the lack of severity of biocidal action.
  • such a multi-stage processing method is quite complicated. and time consuming.
  • a disinfectant for treating skin which contains colloidal silver, a salt of polyhexamethylene guanidine or a salt of polyhexamethylene biguanide.
  • This disinfectant exhibits high biocidal activity against Escherichia coli, Staphylococcus aureus, Leuconostoc mesenteroides, Aspergillus niger, Saccharomyces cerevisiae.
  • the minimum inhibitory concentration of a disinfectant disclosed in RF patent J 2427380 in relation to these strains is several times lower than the minimum inhibitory concentration of a similar disinfectant, which does not contain colloidal silver.
  • the disinfectant disclosed in RF patent JNTs 2427380 is the closest analogue of the claimed invention.
  • One of the main disadvantages of the known antimicrobial preparations based on colloidal silver and polyhexamethylene guanidine derivatives and the corresponding methods of using these preparations is that positively charged silver particles stabilized by polyhexamethylene guanidine derivatives are easily sorbed on water treatment filters, especially those made of materials containing silicon oxide and aluminosilicates, and on the pipes and walls of the pools.
  • water treatment filters especially those made of materials containing silicon oxide and aluminosilicates, and on the pipes and walls of the pools.
  • such preparations lose stability during freezing and subsequent thawing.
  • Silver ion generation rate responsible for the bactericidal action of colloidal silver preparations during oxidative dissolution of silver particles small enough, therefore, to maintain a sufficient concentration of silver ions in water, it is necessary to use large concentrations of colloidal silver.
  • nanosized particles including both silver and silver chloride including particles including a non-stoichiometric compound Ag x Cl, where x> 1, have a higher antibacterial activity, than similar nanosized particles of silver Ag and nanosized particles of silver chloride AgCl.
  • the surface area of the conglomerates of nanoparticles is significantly smaller than the total surface area of the particles forming conglomerate, therefore, during the aggregation of silver chloride nanoparticles, the rate of generation of silver ions upon dissolution of particles, which is directly proportional to the surface area of the particles, decreases significantly.
  • silver chloride under the influence of light easily undergoes photolytic decomposition under the action of light.
  • nanosized particles including silver and silver chloride, are characterized by: a) a high rate of generation of silver ions due to the presence of silver chloride in the composition, b) high aggregative stability characteristic of silver nanoparticles, and, as a consequence, c) pronounced antibacterial activity .
  • nanosized particles including both silver and silver chloride
  • preparations containing amphoteric surfactants for example, derivatives of aminocarboxylic acids and iminodicarboxylic acids, including ⁇ -alkyl substituted derivatives of aminoacetic acid, 3-aminopropionic acid, iminodiacetic acid lots and iminodipropionovoy acid.
  • nanoparticles exhibit pronounced biocidal activity against many prokaryotic and eukaryotic microorganisms, including against gram-positive and gram-negative bacteria, fungi. It was found that nanoparticles, including silver and silver chloride, stabilized by amphoteric surfactants, are stable in a wide pH range and are resistant to aggregation in the presence of electrolytes, which allows the use of dispersions of such nanoparticles as antiseptic preparations with a wide spectrum of action.
  • Nanoparticles including silver and silver chloride, stabilized by the tested amphoteric surfactants, are negatively charged, which significantly complicates the sorption of such nanoparticles on water treatment filters with the same charged surface, in particular on filters made from materials containing silicon oxide and aluminosilicates.
  • colloidal solutions of such nanoparticles retain aggregative stability upon repeated freezing followed by thawing.
  • Nanoparticles including both silver and silver chloride can be obtained, for example, by partial oxidation of nanosized silver particles in the presence of chloride ions.
  • the claimed invention relates to an antiseptic preparation comprising nanoscale particles, including both silver and silver chloride.
  • the antiseptic preparation further comprises at least one amphoteric surfactant.
  • the concentration of amphoteric surfactant in the antiseptic preparation is from 0.001 wt.% To 20 wt.%.
  • the concentration of nanosized silver particles in the antiseptic preparation is from 10 "4 wt.% To 0.5 wt.%.
  • the antiseptic preparation further comprises adjuvants.
  • the auxiliary additives are selected from the group comprising acidity correctors, corrosion inhibitors, thickeners.
  • At least one amphoteric surfactant is selected from the group including carboxylic acids and their derivatives with the General formula
  • substituents Mi and M 2 are selected from the group consisting of H, Na, K, NH 4 , while the number a is 1 or 2, the number b is 2 or 3, the number c is 1 or 2, the number m is 1 or 2 , the number and is 0 or greater than 0, the number p is 0 or greater than 0, the number q is greater than 0, and the substituent Ri is selected from the group consisting of branched and unbranched saturated and unsaturated linear and cyclic hydrocarbon radicals.
  • cocoalkyl means a mixture of saturated and unsaturated hydrocarbon radicals, mainly Sv-Crg, which is part of the products obtained from the chemical processing of coconut oil.
  • titanium alkyl is meant a mixture of saturated and unsaturated hydrocarbon radicals, mainly C 8 -C 24 , which is part of the products obtained from the chemical processing of tall oil.
  • the invention also relates to a method for disinfecting water, in which at least once nanosized particles are added to water, including both silver and silver chloride.
  • At least one amphoteric surfactant is added to water.
  • At least one amphoteric surfactant is selected from the group consisting of carboxylic acids and their derivatives with the general formula
  • substituents Mi and M 2 are selected from the group consisting of H, Na, K, NH 4 , wherein the number a is 1 or 2, the number b is 2 or 3, the number c is 1 or 2, the number m is 1 or 2 , the number n is 0 or greater than 0, the number p is 0 or greater than 0, the number q is greater than 0, and the substituent Ri is selected from the group including branched and unbranched saturated and unsaturated linear and cyclic hydrocarbon radicals.
  • auxiliary additives are additionally added to the water.
  • the auxiliary additives are selected from the group comprising acidity correctors, corrosion inhibitors, thickeners.
  • a solution resulting from the partial oxidation of silver nanoparticles in a colloidal solution containing 0.03 wt.% Amphoteric surfactant ⁇ -cocoalkyliminodipropionate sodium and 0.0025 wt.% Nanosized silver particles was used as an antiseptic preparation.
  • Colloidal a silver solution was obtained according to the procedure described in RF patent JVii 2 419 439 dated 05/27/2011 1 “Antibacterial preparation and method for its preparation”, and instead of a solution of cationic surfactant, a solution of amphoteric surfactant ⁇ - ⁇ -alklnminpinodippropionate sodium was used.
  • the obtained antiseptic preparation A-1 unlike colloidal solutions of silver chloride, is stable in the light and is also aggregatively stable for a long time. At the same time, the absorption spectrum of the obtained antiseptic preparation in the ultraviolet region and in the visible region differs significantly from the absorption spectrum of the initial nanosized silver particles.
  • the antiseptic drug A-1 was studied using transmission electron microscopy. Amorphous nanoparticles were found in the sample of the preparation, upon decomposition of which under the influence of an electron beam, silver particles were formed. The appearance of silver particles during the decomposition of the preparation was confirmed by the data of electron microscopy.
  • the antiseptic preparation A-1 contained water up to 100 wt.%.
  • control sample J4b an initial solution of silver nanoparticles stabilized with sodium cocoa alkaline plodnodroproponate
  • control sample J a 2 a colloidal solution of silver chloride containing 0.03 wt.% M-cocoalkyliminodipropionate and 0.0025 wt. % silver chloride.
  • a control sample No. 2 was obtained by mixing stoichiometric amounts of solutions of silver nitrate and sodium chloride, additionally containing sodium gleich-cocoaalklnmnnodpproponate.
  • an antiseptic preparation based on nanoparticles, including silver and silver chloride has a more pronounced bio-ccd activity than colloidal silver and colloidal silver chloride. It also means that when using nanoparticles, including silver and silver chloride, a synergistic effect of the mutual enhancement of the biocpd activity of silver and silver chloride is manifested. Thus, when using the proposed antiseptic drug, the claimed technical the result is an increase in the biocndal activity of the drug.
  • the obtained antiseptic preparation A-1 was used to process industrial and domestic equipment and inventory.
  • the effectiveness of the antiseptic effect of the drug was evaluated by bacterial contamination of the washings from the treated objects. It was shown that the resulting antiseptic drug can be used during disinfection in industry and at home. The resulting antiseptic drug can also be used to disinfect water. It was shown that the resulting antiseptic drug has low toxicity to humans, does not irritate the skin and mucous membranes, does not have a sensitizing, carcinogenic, mutagenic and teratogenic effect.
  • the resulting preparation was tested as an antiseptic for the disinfection of water in swimming pools.
  • a bath pool with a capacity of 10 m was selected.
  • the pool had a standard recirculation scheme, including draining water through a skimmer, filtering through a sand filter, returning filtered water to the pool.
  • Coagulation of suspended particles was carried out once a week by adding 60 g of aluminum sulfate. The frequency of visits to the pool was 30-70 people per day. Every day for a month, a liter of the obtained antiseptic preparation was added to the pool, which is 15 mg of nanoparticles, including both silver and silver chloride, per 1 m 3 of water.
  • the silver concentration in the pool water was determined daily by atomic absorption analysis using an Shimadzu AA-7000 atomic absorption spectrophotometer in accordance with the state standard of the Russian Federation GOST R 51309-99 “Drinking water. Determination of the content of elements by atomic spectrometry.
  • the average silver soder- zhanie in water was 4 mg / m ' ⁇ due to the partial coagulation chas- TPTs preparation and their adsorption on the filter Maintaining a silver concentration of SOM achieve and throughout the testing period to maintain the following values of the indicators of bacterial water seeding total microbial number (TBC) - not more than 40 colony forming units (CFU) per ml, total coliform bacteria of the OKB - absence, thermo-tolerant coliform bacteria of the TKB - absence, which indicates a high efficiency NOSTA water disinfection using the obtained antiseptic preparation.
  • TBC total microbial number
  • CFU colony forming units
  • R cocoalkyl
  • Mj and M 2 are Na
  • q is in the range from 5 to 10
  • p is in the range from 7 to 10.
  • the concentration of amphoteric surfactant was varied in in the range from 0.001 wt.% to 20 wt.%
  • the concentration of nanosized particles of silver varied in the range from 10 "4 wt.% to 0.5 wt.%.
  • nanosized particles containing silver and silver chloride, and reaction products occurring during the synthesis of the drug to Each obtained antiseptic preparation contained water up to 100 wt.%.
  • the obtained antiseptic preparations were used to process industrial and household equipment and inventory.
  • the effectiveness of the antiseptic effect of the preparations was evaluated by bacterial contamination of the washes from the treated objects. It was shown that the obtained antiseptic drugs can be used during disinfection in industry and at home.
  • the resulting antiseptic preparations can also be used to disinfect water.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Hydrology & Water Resources (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Organic Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Nanotechnology (AREA)
  • Inorganic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Composite Materials (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Apparatus For Disinfection Or Sterilisation (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
PCT/RU2014/000615 2014-08-19 2014-08-19 Антисептический препарат и способ его использования Ceased WO2016028183A1 (ru)

Priority Applications (19)

Application Number Priority Date Filing Date Title
MYPI2017700543A MY182571A (en) 2014-08-19 2014-08-19 Antiseptic formulation and its use
JP2017529966A JP6783762B2 (ja) 2014-08-19 2014-08-19 消毒配合物及びその使用
CN201480081288.8A CN107207294A (zh) 2014-08-19 2014-08-19 抗菌制剂及其用途
PL14900041T PL3184492T3 (pl) 2014-08-19 2014-08-19 Preparat antyseptyczny
CA2959466A CA2959466C (en) 2014-08-19 2014-08-19 Antiseptic formulation and its use
PCT/RU2014/000615 WO2016028183A1 (ru) 2014-08-19 2014-08-19 Антисептический препарат и способ его использования
TN2017000030A TN2017000030A1 (en) 2014-08-19 2014-08-19 Antiseptic formulation and its use.
US15/502,762 US10717661B2 (en) 2014-08-19 2014-08-19 Antiseptic formulation and its use
KR1020197015449A KR20190064670A (ko) 2014-08-19 2014-08-19 소독 제제 및 이의 사용 방법
EA201700110A EA038054B1 (ru) 2014-08-19 2014-08-19 Антисептический препарат и способ его использования
KR1020177007044A KR102131731B1 (ko) 2014-08-19 2014-08-19 소독 제제 및 이의 사용 방법
ES14900041T ES2772182T3 (es) 2014-08-19 2014-08-19 Formulación antiséptica
UAA201702263A UA120100C2 (uk) 2014-08-19 2014-08-19 Антисептичний препарат та спосіб його застосування
MX2017002083A MX385223B (es) 2014-08-19 2014-08-19 Formulación antiséptica y su uso.
BR112017003279-1A BR112017003279A2 (pt) 2014-08-19 2014-08-19 formulação antisséptica
AU2014403897A AU2014403897B2 (en) 2014-08-19 2014-08-19 Antiseptic formulation and its use
EP14900041.6A EP3184492B1 (en) 2014-08-19 2014-08-19 Antiseptic formulation
PH12017500274A PH12017500274B1 (en) 2014-08-19 2017-02-14 Antiseptic formulation and its use
ECIEPI201716787A ECSP17016787A (es) 2014-08-19 2017-03-20 Formulación antiséptica y su uso

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/RU2014/000615 WO2016028183A1 (ru) 2014-08-19 2014-08-19 Антисептический препарат и способ его использования

Publications (1)

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WO2016028183A1 true WO2016028183A1 (ru) 2016-02-25

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PCT/RU2014/000615 Ceased WO2016028183A1 (ru) 2014-08-19 2014-08-19 Антисептический препарат и способ его использования

Country Status (18)

Country Link
US (1) US10717661B2 (enExample)
EP (1) EP3184492B1 (enExample)
JP (1) JP6783762B2 (enExample)
KR (2) KR20190064670A (enExample)
CN (1) CN107207294A (enExample)
AU (1) AU2014403897B2 (enExample)
BR (1) BR112017003279A2 (enExample)
CA (1) CA2959466C (enExample)
EA (1) EA038054B1 (enExample)
EC (1) ECSP17016787A (enExample)
ES (1) ES2772182T3 (enExample)
MX (1) MX385223B (enExample)
MY (1) MY182571A (enExample)
PH (1) PH12017500274B1 (enExample)
PL (1) PL3184492T3 (enExample)
TN (1) TN2017000030A1 (enExample)
UA (1) UA120100C2 (enExample)
WO (1) WO2016028183A1 (enExample)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2670085C2 (ru) * 2016-10-27 2018-10-18 Общество с ограниченной ответственностью "Акватех" Способ получения антисептического препарата
WO2020101536A1 (ru) * 2018-11-14 2020-05-22 КРУТЯКОВ, Юрий Андреевич Стимулятор роста растений на основе серебра и хлорида серебра
EA037446B1 (ru) * 2018-11-14 2021-03-29 Юрий Андреевич КРУТЯКОВ Стимулятор роста растений на основе серебра и хлорида серебра
EA037437B1 (ru) * 2018-11-14 2021-03-29 Юрий Андреевич КРУТЯКОВ Способ стимуляции роста и развития растений

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Publication number Priority date Publication date Assignee Title
CN116019126B (zh) * 2022-12-09 2024-08-16 点金新型材料研究院(厦门)有限公司 一种复合抗菌剂及其制备方法

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RU2419439C1 (ru) * 2009-10-29 2011-05-27 Юрий Андреевич Крутяков Антибактериальный препарат и способ его получения
RU2465891C2 (ru) * 2007-05-04 2012-11-10 Дзе Проктер Энд Гэмбл Компани Антибактериальные композиции, продукты и способы их применения
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JP6783762B2 (ja) 2020-11-11
CN107207294A (zh) 2017-09-26
EP3184492A1 (en) 2017-06-28
CA2959466C (en) 2020-03-24
MY182571A (en) 2021-01-25
JP2017531030A (ja) 2017-10-19
ECSP17016787A (es) 2018-03-31
EA038054B1 (ru) 2021-06-29
KR20170042351A (ko) 2017-04-18
KR20190064670A (ko) 2019-06-10
EA201700110A1 (ru) 2017-07-31
PH12017500274A1 (en) 2017-07-03
CA2959466A1 (en) 2016-02-25
UA120100C2 (uk) 2019-10-10
PL3184492T3 (pl) 2020-08-24
ES2772182T3 (es) 2020-07-07
MX385223B (es) 2025-03-14
AU2014403897A1 (en) 2017-04-06
EP3184492A4 (en) 2018-04-11
TN2017000030A1 (en) 2018-07-04
AU2014403897B2 (en) 2020-09-10
US10717661B2 (en) 2020-07-21
EP3184492B1 (en) 2019-11-27
KR102131731B1 (ko) 2020-08-05
US20170260070A1 (en) 2017-09-14
PH12017500274B1 (en) 2017-07-03
MX2017002083A (es) 2017-06-21
BR112017003279A2 (pt) 2018-01-23

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