CN1096921A - Bactericidal composition and contain the soap of said composition - Google Patents
Bactericidal composition and contain the soap of said composition Download PDFInfo
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- CN1096921A CN1096921A CN93120240A CN93120240A CN1096921A CN 1096921 A CN1096921 A CN 1096921A CN 93120240 A CN93120240 A CN 93120240A CN 93120240 A CN93120240 A CN 93120240A CN 1096921 A CN1096921 A CN 1096921A
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- China
- Prior art keywords
- composition
- soap
- bactericidal composition
- microorganism
- bactericidal
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D9/00—Compositions of detergents based essentially on soap
- C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/0047—Detergents in the form of bars or tablets
- C11D17/006—Detergents in the form of bars or tablets containing mainly surfactants, but no builders, e.g. syndet bar
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Detergent Compositions (AREA)
Abstract
The invention discloses a kind of bactericidal composition and contain the soap of this bactericidal composition.This bactericidal composition contains diiodomethyl-right-tolyl sulfone, with 5-amino-1, two (2-ethylhexyl)-5-methyl-hexahydro-pyrimidines of 3-and/or be selected from following compounds in suitable organic solvent: hibitane diacetin, hibitane digluconate or hibitane dihydrochloride.This bactericidal composition can prevent that with the soap that contains said composition commodity from polluting, and prevents the not infected property of human body infected by microbes, also has effective the sterilization and therapeutic action to infecting part, and it is safe to human body, animal and plant.In addition, the present composition is characterised in that it comprises that to various microorganisms eukaryotic and prokaryotic are all effective.And bactericidal composition of the present invention can prevent skin not by pathogenic microorganism infection with the soap that contains said composition, and the zone of having infected before treating.
Description
In general, the present invention relates to bactericidal composition and contain the soap of said composition, more particularly, the present invention relates to have various sterilization scopes, harmless composition, and contain the soap of said composition, thereby this soap can suppress to parasitize and causes various dermopathic growth of microorganism on the skin, and can kill these parasite.
Microorganism, its definition are little as to be difficult to the clear organism of seeing of human eye.They can oneself be grown down and breeding in appropriate condition (as nutrients, humidity, temperature etc.).The classification range of microorganism is wide, and they comprise metazoa, protozoa, many algae and fungis, bacterium and virus.
This microbial total is to exist everywhere, for example, and in people's skin, even in the slurries (magma erupts) of unexpected dermexanthesis.They have played important function in the recycled material of ecosystem.In addition, they can be used in the industrialization main production, as the production of medicine in short supply, food etc.Yet certain micro-organisms can make people, animal or plant infect, to give rise to diseases.Other microorganisms can make corruption such as timber, paper, fabric, food, thereby living environment quality is worsened.
On application on human skin, microorganism parasitic amount every square centimeter of skin approximately is 10
4Colony-forming units (hereinafter with " cfu " expression).This quasi-microorganism is called normal flora, and it is harmless to human body.On the contrary, it is useful, because it can prevent that skin from being infected by other harmful microorganism.The quantity of normal flora can keep constant by the relevant bacteriolyze characteristic of hydrolase (as lysozyme), and this hydrolase is distributed widely in the metabolite of biological tissue and secretion, transferase (also being a kind of secretion) and this microorganism self.Yet, if the immune system of human body (he or she) is very weak, or contact with pollutant, the particularly improper propagation of pathogenic microorganism, he or she can get bacterium or fungal disease.Being very easy to find timber, fabric, paper, food etc. in daily life is that microorganism is autoeciously desirable, and therefore, they are often contaminated.In addition, under extreme conditions limited, high temperature, drying condition etc. as nutrients, microorganism can generate the discernible hypopus of microscope (endospore), their very heat-resisting and drying conditions, they can survive up to extreme environment and improve as a result.Therefore, by the floor, fabric, wallpaper, basin, towel or the food that pollute, human body is always existed by the possibility of infected by microbes.
Known road most skin infectious disease (accounting for the 8-10% of hospital patient sum in the U.S.) gets by NSF such as hospital's (hospital's route infection).Can think that this class disease is utilized the instrument of medical worker and Chang and contact patients to make carrier and propagated in patient.And patient causes immunologic function to weaken owing to medication or operation, the anti-infection ability extreme difference, thus make PD arrive very serious degree.
In the process of making great efforts to address these problems, Korea patent disclosure NO90-2935 proposes to be the sterilizing cleaning agent of ointment or soap form.But the sterilization ability of this cleaning agent is doubtful.In addition, be not developed into bactericide no matter when, where all easy to use so far as yet.
As required, be necessary to develop a kind of bactericidal composition, it can prevent that commodity from polluting, and prevents the not infected property of human body infected by microbes, and can also effectively sterilize, and treats infecting part, and it is safe to human body, animal and plant.
In development during Fungicidal substance, the difficulty that runs into is the diversity of microorganism and to the safety of human body.
Have recognized that dichotomy is very important in the inhomogeneity microorganism relevant with the cell interior structure.There are two kinds of diverse cells in the current lived world.More complicated eukaryotic is the construction unit in metazoa, protozoa, fungi and all around bodies that belong to algae traditionally.Not too Fu Za prokaryotic is the construction unit of eubacteria and two kinds of microorganisms of indigenous bacteria.For prokaryotes, based on the structure of cell wall, this eubacteria can be divided into Gram-negative eubacteria and Gram-positive eubacteria again.In general, microorganism is to the reaction difference of Fungicidal substance.Fungicidal substance is invalid to Gram-negative bacteria usually, though it can kill Gram-positive bacteria.And usually the material that Gram-positive and Gram-negative bacteria are all had a potential sterilization ability is unaccommodated for eukaryotic microorganisms (as yeast and fungi).
For addressing the above problem, the inventor thinks, need a kind of bactericidal composition, all effective to various microorganisms, it can suppress microbial growth or kill them, and to human body, animal and plant is safe, contains the form that the preparation of this bactericidal composition can be easy to use and no matter when, where all can use.
Therefore, purpose of the present invention provides a kind of bactericidal composition, and it can kill various microorganisms.
Another object of the present invention provides a kind of bactericidal composition, and it is safe to human body and other organism as animal and plant.
The 3rd purpose of the present invention provides a kind of soap, and it has good inhibition effect and disinfecting power to microorganism.
By providing a kind of composition can realize above-mentioned purpose, said composition contains the compound that useful following formula I is represented:
The compound of representing with following formula II and III at least a or two
Wherein R is selected from diacetin, digluconate and dihydrochloride; With a kind of solvent.
The compound of following formula I, II and III is known harmless compound.
Those skilled in the art will come into plain view to above-mentioned these and other objects and other purpose of specifically not mentioning by following explanation.
To describe the present invention in detail below.
Diiodomethyl-right-tolyl sulfone of representing with the formula I as bactericidal composition composition of the present invention has potential sterilizing ability to Gram-positive bacteria, yeast and fungi, but very little to the Gram-negative bacteria effect.The another kind of active ingredient 5-amino of representing with the formula II-1, two (2-the ethylhexyl)-5-methyl-hexahydro-pyrimidines of 3-can kill Gram-negative bacteria.The compound that other is represented with the formula III, be selected from chlohexidine (1,1 '-hexa-methylene-two [5-(4-chlorphenyl) biguanides]) diacetin, chlohexidine digluconate or chlohexidine dihydrochloride, be effective, be better than formula II compound aspect Gram-positive bacteria and the fungi killing Gram-negative bacteria.
By the present invention, this bactericidal composition is the 5-amino-1 with the diiodomethyl of formula I-right-tolyl sulfone and formula II, the compound of two (2-ethylhexyl)-5-methyl-hexahydro-pyrimidines of 3-and/or formula III mixes mutually and prepares, thereby makes said composition can kill Gram-positive and Gram-negative bacteria and eucaryote such as yeast and fungi.
For example, the present composition is effectively to following bacterium, as hay bacillus, Escherichia coli, klepsiella pneumoniae, Mycobacterium tuberculosis, Micrococcus Multicida, proteus vulgaris, shigella dysenteriae, golden yellow bag staphylococcus, Staphylococcus epidermidis, excrement streptococcus etc.Bactericidal composition of the present invention can suppress yeast or fungi growth, belongs to as aspergillus, Aerobacidium Pullulans, candidiasis, Epidermophyton SP, sickle-like bacteria, Microsporon, Malassezia furfur, Penicillium chrysogenum, trichophyta etc.
Contain at this bactericidal composition under the situation of formula I and II compound or formula I and III compound, each component ratio is preferably 1: 1 by weight in the composition.When this bactericidal composition contained all formula I, II and III compound, each component ratio was preferably 1: 1: 1 by weight.
Being used for preferred solvent of the present invention is alcohols, is more preferably ethanol.
Bactericidal composition of the present invention becomes the useful form that contains other various materials.For example, bactericidal composition of the present invention can mix the soap of narrating below to make with the soap base material.Also bactericidal composition of the present invention can be added in organic solvent such as the ethanol to make effective surgery antiseptic solution.This bactericidal composition has the effect of fabulous inhibition growth of microorganism with the soap that contains said composition, thereby can be used for the cleaning or the sterilization of household goods hard part, as wall, floor, desk, plastic products etc., or is used for laundering of textile fabrics to carry out disinfection.
Specifically, bactericidal composition of the present invention and germicidal soap have tangible sterilization ability to yeast and antrophylic fungi, and it has very strong permeability to human body, as candida albicans, palpus trichophyta and Epidermophyton floccosum.These microorganisms that exemplified can cause fungi type skin disease as, eczema, dermatomycosis, trichophytosis etc.
Embodiment 1
The preparation of bactericidal composition
Earlier 20g diiodomethyl-right-tolyl sulfone is dissolved in the 1980ml199% straight alcohol.In this solution, add 20g5-amino-1, two (2-ethylhexyl)-5-methyl-hexahydro-pyrimidines of 3-and 20g chlohexidine digluconate, vigorous stirring 5 minutes is to make bactericidal composition.
The composition that makes contains three kinds of active ingredient 20000ppm respectively.
Though the concentration of active ingredient and ratio thereof can change according to application target.
Embodiment 2
The composition that makes among the mensuration embodiment 1 is to various microbial growth inhibitory action.Growth inhibition effect described here is the minimal inhibitory concentration value (hereinafter claiming " MIC ") of bactericidal composition, it is the microorganism by inoculation some in the suitable culture medium of the bactericidal composition that contains variable concentrations respectively, cultivate this microorganism certain hour under steady temperature, the medium of selecting this microorganism can not be grown that contains the said composition least concentration is measured.
The cultivation composition that is used for growth of microorganism is shown in following table 1 and table 2.
Table 1
The culture fluid that is used for bacterial growth
Yeast extract 3g
Tryptone 5g
Glucose 1g
Distilled water 1l (pH5.6)
Table 2
The culture fluid that is used for conk
Brewer's wort 40g
Peptone 10g
Chloramphenicol 10mg
Distilled water 1l (pH5.6)
* prepare a dish culture fluid, the agar amount of adding is 1.5%.
The component of culture fluid was sterilized 15 minutes at 121 ℃ by used usually method.
Prepare the microorganism stock solution as follows: with little by little bacterium and the yeast cells inoculation plate culture of taking on the platinum needle (carrying out disinfection with flame in advance), pass the culture surface fast and lightly by the general crossing method and draw several times, cultivate this microorganism 2-3 days until developing into separable bacterium colony at 30 ℃; Microbial cell in the separable bacterium colony is captured in the oese, and is suspended in 0.9%N
aIn the CL solution (hereinafter claiming " normal saline solution ").Under the fungi situation, they are seeded in the plate culture, 30 ℃ through 5-7 days to form spore.To contain 5%(weight approximately) the 10ml normal saline solution of Tween 80 injects this plate culture, scrapes the culture surface with the preparation spore suspension with oese then.
Measure the stock solution make like this with conventional method to calculate wherein contained microbial count, be seeded in respectively in the culture fluid that contains the variable concentrations bactericidal composition then.The inoculum amount must keep 10
4Cfu/ml.After the inoculation, make culture vessel 30 ℃ of speed rotations with 150rpm.Bacterium after 72 hours, is observed its growth to measure the MIC value after 48 hours or to fungi.
Embodiment 1 bactericidal composition is listed in the table below in 3 to the result of the tests of various microorganisms.
Embodiment 3
The bactericidal composition that mensuration embodiment 1 makes is to the sterilization functions of various microorganisms.Here said sterilization functions is minimum insecticide concentration (hereinafter claiming " the MBC ") value of this bactericidal composition, it is by inoculation some microorganisms in the suitable culture medium that contains the variable concentrations bactericidal composition respectively, make this microorganism insulation certain hour, selection contains the medium of least concentration composition, makes wherein cultured microorganism quantity be less than 0.1% of inoculum and records.By the total number calculating method of common survivaling cell, this value can be by the test of example 2, measures the residual micro organism quantity of surviving in the medium that microorganism can not grow and definite.
Example 1 bactericidal composition is as shown in table 3 below to the result of the test of various microorganisms.
Table 3
Bactericidal composition is to MIC and the MBC value of microorganism
Microorganism MIC (ppm) MBC (ppm)
Bacterium
Hay bacillus 50 50
Escherichia coli 100 200
Mycobacterium?tuberculosis 250 500
Golden yellow bag staphylococcus 200 300
Excrement streptococcus 200 300
Yeast
Candida?albicans 100 200
Fungi
Aspergillus 38 75
Epidermophyton?SP. 38 75
Trichophyton 38 75
Embodiment 4
The preparation of germicidal soap
The dilute strength of knowing each component of forming this soap when using this soap is important, because be the preparation soap, needs to determine each component concentrations.Here to mention EP0363215(A
2) middle disclosed method, it has analyzed each component to the soap Effect on Performance.That is, suppose diluted 100 times of the component of soap when using soap.
Add bactericidal composition that concentration is no less than 25% example 1 with the preparation soap, this soap all has effective sterilization ability to all microorganisms shown in the last table 3.
This soap composed as follows:
Soap base material or neat soap 97.5g
Bactericidal composition 25.0ml
Other additive
Spices 1.5ml
Colorant 0.01g
The soap base material is carried out 5 minutes milled processed, it is pulverized fully.Stirring powder minces, and adds bactericidal composition and other additive.So that ethanol evaporates fully, and make its water content be less than 5% the mixture drying that makes.Dried mixture was ground 15 minutes so that the composition that adds mixes fully again.Temperature is remained on 32-37 ℃, and this mixture of compacting is cast ribbon then in Stephen Beck screw extruder.With small-sized multiple pressure machine, the mixture that will cast is pressed into suitable soap shape.
When making germicidal soap, each active ingredient adds in 0.5% concentration (with soap base material weight), and need not contain the ethanolic solution of effective composition.
Embodiment 5
The germicidal soap that makes among the mensuration embodiment 4 is to various microbial growth inhibitory action.The growth inhibition effect here is with growth inhibition degree (%) expression, and its meaning is meant that the soap aqueous solution that contains bactericidal composition compares the relative extent that it suppresses growth of microorganism with the soap aqueous solution that does not contain bactericidal composition.
This Growth Inhibition assay method is as follows: the stock solution (its amount is 1000cfu/ml) that 0.5ml is contained various microorganisms mixes mutually with 2% soap solution (containing 2g soap and the 100ml suspension of sterilized distilled water), then the solution that obtains is injected plate culture, be incubated 48 hours (for bacteriums) down or be incubated 72 hours (for yeast and fungi) to develop into bacterium colony at 30 ℃.Calculate the clump count in this culture, will handle and do not contain bactericidal composition soap result and compare with containing the bactericidal composition soap.
This result is as shown in table 4.
Table 4 germicidal soap is to the microbial growth inhibitory action
| Soap | Staphylococcus epidermidis | Candida albicans | Trichophyton | |||
| Survival number (cfu) | IR* (%) | Survival number (cfu) | IR (%) | Survival number (cfu) | IR (%) | |
| A B | 1200 0 | - 100 | 760 4 | - 99 | 1070 0 | - 100 |
* growth inhibition ratio
* A: do not contain sterilization component
B: press embodiment 4 preparations
Embodiment 6
The soap that makes among the mensuration embodiment 4 is to the sterilization functions of various microorganisms.The sterilization functions here is with sterilization rate (%) expression, and its meaning is meant that the aqueous solution that contains the bactericidal composition soap compares the relative extent that suppresses growth of microorganism with the aqueous solution that does not contain the bactericidal composition soap.
The assay method of sterilization functions is as follows:
The stock solution that 0.5ml is contained various microorganisms (its amount is 1000cfu/ml) mixes in small-sized centrifuge tube with 0.5ml2% soap solution (containing 2g soap and the 100ml suspension of sterilized distilled water), places 10 minutes down at 30 ℃; With microbial inoculant in soap solution, under the 8000rpm rotating speed centrifugal 5 minutes then, remove supernatant carefully, the 1ml normal saline solution is poured in the remaining microorganism precipitation to wash this soap solution; Repeat back one step 2 to 3 times, then the 1ml normal saline solution is poured in the remaining microorganism precipitation, the solution that obtains is poured in the plate culture.Then on 48 hours (for bacterium) or 72 hours (for yeast and fungi) of 30 ℃ of insulations.Add up clump count in each culture relatively to contain the bactericidal composition soap and not contain the result of bactericidal composition soap.
This result is as shown in table 5.
Table 5 germicidal soap is to the sterilization functions of microorganism
| Soap | Staphylococcus epidermidis | Candida albicans | Trichophyton | |||
| Survival number (cfu) | SR* (%) | Survival number (cfu) | SR (%) | Survival number (cfu) | SR (%) | |
| A B | 700 7 | - 99 | 825 8 | - 99 | 730 204 | - 72 |
* sterilization rate
* A: do not contain sterilization component
B: press embodiment 4 preparations
Can obviously find out from the foregoing description, can expect that bactericidal composition of the present invention and the soap that contains said composition can prevent that skin from not infected by harmful microorganism, and the zone of being infected before treating.
Although the present invention is described, it will be understood by those skilled in the art that and to do many changes and modification and can not depart from the spirit or scope of the present invention of having made general description with reference to some preferred embodiment and embodiment.
Claims (7)
1, a kind of bactericidal composition, it contains a kind of compound that useful following formula I is represented:
At least a or two compounds of representing with following formula II and III:
Wherein R is selected from diacetin, digluconate and dihydrochloride and a kind of solvent that can dissolve described compound.
2, by a kind of bactericidal composition of claim 1, it is characterized by described solvent is ethanol.
3, by a kind of bactericidal composition of claim 1, it is characterized by this formula I compound that added and the weight rate of formula II or III compound is 1: 1, or this formula I that is added, II and III compound weight rate are 1: 1: 1.
4, a kind of germicidal soap contains a kind of composition, said composition contain a kind of compound that useful following formula I represents and
At least a or two compounds of representing with following formula II and III
Wherein R is selected from diacetin, digluconate and dihydrochloride.
5,, it is characterized by said composition directly is added in the soap base material by a kind of germicidal soap of claim 4.
6,, it is characterized by said composition is dissolved in and wait to be added in the alcohol of soap base material by a kind of germicidal soap of claim 4.
7, by a kind of germicidal soap of claim 6, it is characterized by this alcohol is ethanol.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019920019277A KR960004500B1 (en) | 1992-10-20 | 1992-10-20 | A sterilizing detergent composition |
| KR19277/92 | 1992-10-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1096921A true CN1096921A (en) | 1995-01-04 |
Family
ID=19341449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN93120240A Pending CN1096921A (en) | 1992-10-20 | 1993-10-20 | Bactericidal composition and contain the soap of said composition |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPH07101810A (en) |
| KR (1) | KR960004500B1 (en) |
| CN (1) | CN1096921A (en) |
| BR (1) | BR9304037A (en) |
| FR (1) | FR2696903B1 (en) |
| GB (1) | GB2271719B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101336637B (en) * | 2008-08-27 | 2011-12-07 | 广州中大药物开发有限公司 | Complex type broad-spectrum disinfectant and use thereof |
| CN114097815A (en) * | 2021-11-25 | 2022-03-01 | 兰州大学 | Application of medical compound with amidine skeleton in resisting plant pathogenic bacteria |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5829442A (en) * | 1996-06-12 | 1998-11-03 | Medical Concepts Development, Inc. | Antimicrobial containing solventless hot melt adhesive composition |
| FR2822070B1 (en) * | 2001-03-15 | 2006-01-06 | Andre Salkin | USE OF A BIGUANIDE DERIVATIVE AND A PYRIMIDINE FOR THE MANUFACTURE OF A COSMETIC CARE COMPOSITION |
| CN101111219A (en) * | 2005-01-28 | 2008-01-23 | 宝洁公司 | Diiodomethyl-p-tolylsulfone as a particulate dispersion in a liquid solvent |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4185120A (en) * | 1978-10-02 | 1980-01-22 | Abbott Laboratories | Topical treatment of fungal or yeast infections using p-tolyl diiodomethyl sulfone |
| US4326977A (en) * | 1980-11-10 | 1982-04-27 | Basf Wyandotte Corporation | Liquid antiseptic cleaners with improved foaming properties |
| JPS59163474A (en) * | 1983-03-04 | 1984-09-14 | 旭化成株式会社 | Production of anti-bacterial polyamide fiber |
| JPS59179877A (en) * | 1983-03-31 | 1984-10-12 | 旭化成株式会社 | Production of anti-bacterial polymer fiber having vinyl or vinylidene group |
| FR2552305B1 (en) * | 1983-09-22 | 1985-12-20 | Salkin Andre | HIGH BACTERICIDAL COMPOSITION CONTAINING BIGUANIDE AND PYRIMIDINE |
| GB8907298D0 (en) * | 1989-03-31 | 1989-05-17 | Ici Plc | Composition and use |
| GB9024133D0 (en) * | 1990-11-06 | 1990-12-19 | Ici Plc | Aqueous composition |
-
1992
- 1992-10-20 KR KR1019920019277A patent/KR960004500B1/en not_active IP Right Cessation
-
1993
- 1993-10-19 GB GB9321537A patent/GB2271719B/en not_active Expired - Fee Related
- 1993-10-20 CN CN93120240A patent/CN1096921A/en active Pending
- 1993-10-20 JP JP5286062A patent/JPH07101810A/en active Pending
- 1993-10-20 FR FR9312498A patent/FR2696903B1/en not_active Expired - Fee Related
- 1993-10-20 BR BR9304037A patent/BR9304037A/en not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101336637B (en) * | 2008-08-27 | 2011-12-07 | 广州中大药物开发有限公司 | Complex type broad-spectrum disinfectant and use thereof |
| CN114097815A (en) * | 2021-11-25 | 2022-03-01 | 兰州大学 | Application of medical compound with amidine skeleton in resisting plant pathogenic bacteria |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07101810A (en) | 1995-04-18 |
| FR2696903B1 (en) | 1995-11-03 |
| GB2271719B (en) | 1996-05-22 |
| KR960004500B1 (en) | 1996-04-06 |
| GB9321537D0 (en) | 1993-12-08 |
| FR2696903A1 (en) | 1994-04-22 |
| GB2271719A (en) | 1994-04-27 |
| KR940008673A (en) | 1994-05-16 |
| BR9304037A (en) | 1994-06-07 |
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