WO2013094927A2 - Composé antimicrobien cationique et composition antimicrobienne le comprenant - Google Patents

Composé antimicrobien cationique et composition antimicrobienne le comprenant Download PDF

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Publication number
WO2013094927A2
WO2013094927A2 PCT/KR2012/010818 KR2012010818W WO2013094927A2 WO 2013094927 A2 WO2013094927 A2 WO 2013094927A2 KR 2012010818 W KR2012010818 W KR 2012010818W WO 2013094927 A2 WO2013094927 A2 WO 2013094927A2
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WO
WIPO (PCT)
Prior art keywords
antimicrobial
cationic
antimicrobial compound
composition
compound
Prior art date
Application number
PCT/KR2012/010818
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English (en)
Korean (ko)
Other versions
WO2013094927A3 (fr
WO2013094927A4 (fr
Inventor
이상호
김태효
Original Assignee
(주)삼보
(주)캠드로우
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 claimed from KR1020120143251A external-priority patent/KR20130072130A/ko
Application filed by (주)삼보, (주)캠드로우 filed Critical (주)삼보
Publication of WO2013094927A2 publication Critical patent/WO2013094927A2/fr
Publication of WO2013094927A3 publication Critical patent/WO2013094927A3/fr
Publication of WO2013094927A4 publication Critical patent/WO2013094927A4/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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/12—Quaternary ammonium compounds

Definitions

  • the present invention relates to a cationic antimicrobial compound and an antimicrobial composition containing the same, more specifically, an antimicrobial agent prepared by quaternary ammonium alkyldimethylamine with epichlorohydrin and exhibiting excellent antimicrobial activity against fungi including bacteria.
  • an antimicrobial agent prepared by quaternary ammonium alkyldimethylamine with epichlorohydrin and exhibiting excellent antimicrobial activity against fungi including bacteria.
  • a compound and an antimicrobial composition containing the same are examples of the same.
  • Antibacterial and bactericides are divided into oxidizing and non-oxidizing fungicides.
  • Halogenous compounds such as chlorine and bromine are mainly used as oxidizing fungicides, and they are widely used because of their strong oxidizing power and economical efficiency. However, they have a great effect on wood erosion and metal corrosion, and are easily released into the atmosphere, thereby reducing their efficacy. Since non-specific reactions occur in the biofilm formation state, they react with the polysaccharides secreted before reacting with the microorganisms that cause them, so that there is a disadvantage in that the effective bactericidal effect is lowered.
  • non-oxidizing fungicides include 3-isothiazolinone, quaternary ammonium compounds, formaldehyde releasing compounds, glutaraldehyde, etc., and these are mainly used alone, but US Patent No. 3,282,775, US Patent No. 4,107,312, EP 0217339 Hoh et al. Also illustrate sterilizing compositions in which glutaraldehyde and quaternary ammonium chlorides are combined to impart fast action and increase sterilizing power.
  • the hydrogen present in the quaternary ammonium compound is an ammonium (NH 4 +) refers to both substituted with an organic molecule (such as an alkyl group).
  • Quaternary ammonium compounds show good antibacterial performance over a wide temperature and pH range. Quaternary ammonium compounds form the main component of cationic surfactants, which are known to have weaker cleaning power but stronger antimicrobial performance than anionic surfactants.
  • Representative examples of quaternary ammonium compounds, which are cationic surfactants are benzalkonium chloride and benzethonium chloride, which are mainly used as disinfectants for hands and instruments because they are harmless to the human body and have no metal corrosion.
  • various quaternary ammonium compounds such as polyoxyethylene trimethyl ammonium chloride and polyoxyalkyl trialkyl ammonium chloride are used for antibacterial and deodorant processing of textile products.
  • Quaternary ammonium compounds are known to inactivate microorganisms by adsorbing quaternary ammonium compounds on the surface of microbial cells and then spreading antimicrobial substances through cell walls and disrupting cellular membranes, releasing K + ions and cellular components such as DNA and RNA. . This mechanism is presumed to be based on the fact that the microbial cell surface is negatively charged and is cation for quaternary ammonium compounds.
  • the problem of the present invention is to solve the problems of the conventional quaternary ammonium salt antimicrobial agent as described above and to provide an excellent antimicrobial agent with an excellent effect on not only bacteria but also fungi, and a simple manufacturing method.
  • the present inventors quaternized the alkyldimethylamine with epichlorohydrin to prepare a new type of cationic antimicrobial agent which is very economical and has excellent antibacterial performance.
  • the cationic antimicrobial compound of the present invention has a very simple and economical manufacturing method and excellent antimicrobial activity, and exhibits excellent antimicrobial activity against fungi.
  • the antimicrobial compound of the present invention is represented by the following formula (1).
  • R is a C 6 -C 18 linear or branched alkyl group, alkenyl group, or a group consisting of a mixture of one or more thereof
  • A is CHCH 2 (O), CHOHCH 2 OH, CH 2 CH: CHOH, CH 2 CHCH 2 (O), CH 2 CHOHCH 2 OH or a group consisting of one or more thereof.
  • the carbon number of R exhibits excellent antimicrobial functionality in the range of 6 to 18, and beyond this range, the antimicrobial function is lowered.
  • the inventors of the present invention prepared by quaternizing the antimicrobial compound of Formula 1 by reacting alkyldimethylamine with epichlorohydrin, but the antimicrobial compound of the present invention is not necessarily produced by this method.
  • the reaction uses water and at least one of an organic solvent, ie ethanol, isopropyl alcohol, ethyl acetate, acetone, benzene or toluene as a solvent.
  • an organic solvent ie ethanol, isopropyl alcohol, ethyl acetate, acetone, benzene or toluene as a solvent.
  • the reaction temperature is 0 to 90 ° C, preferably 60 to 70 ° C, and the reaction time is 1 to 15 hours. If the temperature and time are above or below the above range, the reaction may not occur properly or the reaction may proceed excessively and produce unwanted byproducts. In this case, the produced compound has a solid content of 10 to 80%, and this solid content is a cationic antimicrobial agent as a final product.
  • the cationic antimicrobial compound thus obtained may be included in various products such as hair products such as detergents, fabric softeners, shampoos, cosmetics, textile products or agrochemical compositions according to methods known to those skilled in the art. It is available.
  • the present invention includes the antimicrobial composition comprising the compound represented by the formula (1) as a right range.
  • the antimicrobial composition of the present invention may contain 0.001 to 99% by weight of one or more compounds represented by Chemical Formula 1 alone or an appropriately selected additive according to the purpose of use.
  • the present invention is not particularly limited to the selective use and content of these additives, and can be appropriately adjusted according to the method of use and the dosage form at the expert level in the art.
  • the additive of the present invention may be a material included in a conventional antimicrobial agent, for example, an excipient or a diluent, and examples thereof include saline solution, buffer solution, dextrose, isoparaffin, water, glycerol, and ethanol. It is by no means limited.
  • the formulation of the antimicrobial agent can be appropriately adjusted according to the method of use and use, such as liquids, suspensions, granules, fragrances, powders, syrups, aerosols, extracts, ointments, induction extracts, emulsions, whole preparations, eye drops, injections, It may be a pill, a capsule, a cream, or a pill.
  • the antimicrobial composition of the present invention is used to inhibit the production and growth of human pathogenic bacteria, phytopathogenic bacteria, fungi, and the like, and may be used as a fabric softener, detergent, detergent, pharmaceutical, food additive, fragrance, cosmetic and pesticide composition.
  • a cleaning agent it can be prepared by a spray, cleaning agent, shampoo, hair rinse, hair conditioner, soap, etc., wherein the antimicrobial composition may include 0.01 to 50% by weight, but is not limited thereto.
  • the dosage of the antimicrobial composition may be 1 to 1000 mg per day, but is not limited thereto.
  • the antimicrobial composition When used as a quasi-drug, it can be prepared as a hair regrowth, hair dye, hair removal agent, deodorant, anti-odor agent, toothpaste, and the like, wherein the antimicrobial composition may include 0.01 to 50% by weight, but is not limited thereto.
  • the antimicrobial composition When used as a food additive, the antimicrobial composition is preferably adjusted appropriately according to the type of food and the method of use, for example, it can be used in 0.0001 to 10% by weight relative to the food weight.
  • the antimicrobial composition When used as a fragrance, it may further include a volatile substance, the antimicrobial composition may be used in 0.0001 to 90% by weight.
  • the antimicrobial composition When used as a fabric softener, the antimicrobial composition may be used in 0.0001 to 30% by weight.
  • the antimicrobial composition When used as a cosmetic, the antimicrobial composition may be included in 0.0001 to 30% by weight. When used as a pesticide composition that inhibits the growth and growth of phytopathogenic bacteria or fungi, the antimicrobial composition may be included in 0.001 to 30% by weight.
  • antimicrobial compositions containing the antimicrobial compound of the present invention as an active ingredient can be easily prepared according to conventional methods and compositions by those skilled in the art to which the present invention pertains. It is not stated separately in the explanation.
  • benzalconium chloride which is widely used in medical and industrial applications, was selected as Comparative Sample 2.
  • Test bacteria are prepared by inoculating in a liquid medium at the appropriate time and incubating them, diluting the cultured test bacteria in a test medium, and placing them in an appropriate container in each prepared antiseptic test product for bacteria 1 ⁇ 10 6 cell / ml , Fungi were inoculated to 1 ⁇ 10 6 cells / ml.
  • the inoculated product is sampled over time from immediately after the inoculation to 2 weeks after the inoculation, followed by viable cell count test and cultured for 48 hours in a 37 ° C culture device for bacteria and 72 hours in a 25 ° C culture device for fungi. Afterwards, the viable cell count was measured.
  • Antifungal activity has hyomoryu of Candida albicans (Candida albicans; KCTC 7270) medium for fungi was used Merck (Germany)'s PDA (potato dextrose agar), PDB (potato dextrose broth).
  • Table 1 The results according to the antimicrobial activity test is shown in Table 1 below.
  • the figures in Table 1 are the minimum inhibitory concentrations (MIC concentrations) and are in ppm.
  • the two cationic antimicrobial agents prepared in Examples 1 and 2 were confirmed to be antimicrobial activity using a minimum inhibitory concentration (MIC) measurement method for various strains of Comparative Examples 1 to 3 which are commercial antimicrobials in all bacterial and fungal strains. It can be seen that it shows excellent antimicrobial activity compared to the samples, in particular compared to the conventional quaternary ammonium cationic antimicrobial agents Comparative Examples 1 and 2 it can be seen that the antimicrobial activity against fungi such as Candida albicans is very excellent. there was.
  • MIC minimum inhibitory concentration
  • the cationic antimicrobial compound of the present invention has a very simple and economical manufacturing method and excellent antimicrobial activity, and exhibits excellent antimicrobial activity against fungi. Therefore, the cationic antimicrobial compound of the present invention can be applied to various fields such as fabric softeners, detergents, detergents, pharmaceuticals, food additives, fragrances, cosmetics, quasi-drugs or pesticide compositions.

Abstract

La présente invention concerne un composé antimicrobien cationique et une composition antimicrobienne le comprenant. Plus particulièrement, la présente invention concerne un composé antimicrobien qui est préparé par un procédé qui quaternise une ammonium alkyldiméthylamine par de l'épichlorohydrine et qui peut présenter une activité antimicrobienne supérieure aux Eumycètes comprenant des virus. La présente invention concerne également une composition antimicrobienne comprenant le composé antimicrobien cationique.
PCT/KR2012/010818 2011-12-21 2012-12-13 Composé antimicrobien cationique et composition antimicrobienne le comprenant WO2013094927A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20110138949 2011-12-21
KR10-2011-0138949 2011-12-21
KR1020120143251A KR20130072130A (ko) 2011-12-21 2012-12-11 양이온계 항균제 화합물 및 이를 함유하는 항균제 조성물
KR10-2012-0143251 2012-12-11

Publications (3)

Publication Number Publication Date
WO2013094927A2 true WO2013094927A2 (fr) 2013-06-27
WO2013094927A3 WO2013094927A3 (fr) 2013-08-15
WO2013094927A4 WO2013094927A4 (fr) 2013-10-31

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PCT/KR2012/010818 WO2013094927A2 (fr) 2011-12-21 2012-12-13 Composé antimicrobien cationique et composition antimicrobienne le comprenant

Country Status (1)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4778813A (en) * 1981-07-07 1988-10-18 Buckman Laboratories International, Inc. Polymeric quaternary ammonium compounds, their preparation and use
CN1569846A (zh) * 2003-07-11 2005-01-26 北京化工大学 具有长效抗静电和一定杀菌性能的新型环氧季铵盐

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4778813A (en) * 1981-07-07 1988-10-18 Buckman Laboratories International, Inc. Polymeric quaternary ammonium compounds, their preparation and use
CN1569846A (zh) * 2003-07-11 2005-01-26 北京化工大学 具有长效抗静电和一定杀菌性能的新型环氧季铵盐

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
C. G. RICCI ET AL.: 'Micellar-improved synthesis of bis-quaternary ammonium salts by the epichlorohydrin route' J. SURFACTANTS DETERG. vol. 6, no. 3, July 2003, pages 231 - 237 *
HIDEKI SAKAI ET AL.: 'Catanionic mixtures forming gemini-like amphiphiles' J. OLEO SCI.. vol. 60, no. 11, 25 October 2011, pages 549 - 555 *

Also Published As

Publication number Publication date
WO2013094927A3 (fr) 2013-08-15
WO2013094927A4 (fr) 2013-10-31

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