US3445398A - Synergistic antibacterial compositions - Google Patents
Synergistic antibacterial compositions Download PDFInfo
- Publication number
- US3445398A US3445398A US629067A US3445398DA US3445398A US 3445398 A US3445398 A US 3445398A US 629067 A US629067 A US 629067A US 3445398D A US3445398D A US 3445398DA US 3445398 A US3445398 A US 3445398A
- Authority
- US
- United States
- Prior art keywords
- antibacterial
- soap
- detergent
- synergistic
- compositions
- 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.)
- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title description 30
- 230000000844 anti-bacterial effect Effects 0.000 title description 29
- 230000002195 synergetic effect Effects 0.000 title description 15
- 239000000344 soap Substances 0.000 description 34
- 239000003599 detergent Substances 0.000 description 28
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 23
- -1 chlorohydroxyphenyl phenyl ether Chemical compound 0.000 description 17
- 235000014113 dietary fatty acids Nutrition 0.000 description 13
- 239000000194 fatty acid Substances 0.000 description 13
- 229930195729 fatty acid Natural products 0.000 description 13
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- ICUTUKXCWQYESQ-UHFFFAOYSA-N triclocarban Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 ICUTUKXCWQYESQ-UHFFFAOYSA-N 0.000 description 12
- 239000003242 anti bacterial agent Substances 0.000 description 11
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 9
- ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical group OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 description 6
- 229960004068 hexachlorophene Drugs 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 159000000001 potassium salts Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011885 synergistic combination Substances 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 230000002070 germicidal effect Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000271 synthetic detergent Substances 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- SEGHDRQYGSMHSJ-UHFFFAOYSA-N 2-(6-methylheptyl)phenol;oxirane Chemical compound C1CO1.CC(C)CCCCCC1=CC=CC=C1O SEGHDRQYGSMHSJ-UHFFFAOYSA-N 0.000 description 1
- KDTZBYPBMTXCSO-UHFFFAOYSA-N 2-phenoxyphenol Chemical compound OC1=CC=CC=C1OC1=CC=CC=C1 KDTZBYPBMTXCSO-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 238000009631 Broth culture Methods 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- HVWGGPRWKSHASF-UHFFFAOYSA-N Sulfuric acid, monooctadecyl ester Chemical class CCCCCCCCCCCCCCCCCCOS(O)(=O)=O HVWGGPRWKSHASF-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 125000003438 dodecyl group Chemical class [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- XVAWIRLUAWWDMF-UHFFFAOYSA-N octadecyl benzenesulfonate;potassium Chemical compound [K].CCCCCCCCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 XVAWIRLUAWWDMF-UHFFFAOYSA-N 0.000 description 1
- JNPYRMNRFKOYTQ-UHFFFAOYSA-N octyl naphthalene-1-sulfonate;potassium Chemical compound [K].C1=CC=C2C(S(=O)(=O)OCCCCCCCC)=CC=CC2=C1 JNPYRMNRFKOYTQ-UHFFFAOYSA-N 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002943 palmitic acids Chemical class 0.000 description 1
- 125000000913 palmityl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229940114930 potassium stearate Drugs 0.000 description 1
- HSJXWMZKBLUOLQ-UHFFFAOYSA-M potassium;2-dodecylbenzenesulfonate Chemical compound [K+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HSJXWMZKBLUOLQ-UHFFFAOYSA-M 0.000 description 1
- ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
- PYJBVGYZXWPIKK-UHFFFAOYSA-M potassium;tetradecanoate Chemical compound [K+].CCCCCCCCCCCCCC([O-])=O PYJBVGYZXWPIKK-UHFFFAOYSA-M 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
- 229940082004 sodium laurate Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- 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
- A01N47/00—Biocides, 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
- A01N47/08—Biocides, 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 one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/59—Mixtures
Definitions
- the present invention relates to antibacterial compositions which possess synergistic activity through the use of a mixture of antibacterial agents. More specifically the present invention relates to a mixture of 3,4,4-trichlorocarbanilide and a chlorohydroxyphenyl phenyl ether, 2,4,4 trichloro 2' hydroxydiphenyl ether having the formula:
- Patent 3,177,115 hexachlorophene and certain halogenated carbanilides possess synergistic activity, that is the degree of antibacterial activity of the halogenated carbanilides and hexachlorophene in combination is far greater than the antibacterial activity of these. agents when taken independently.
- the discovery of synergism between hexachlorophene and certain of the halogenated carbanilides was important in that it permitted soap manufacturers and others to provide detergent compositions which have a high level of antibacterial activity, but on the other hand have a greatly reduced concentration of antibacterial agents.
- the discovery was of further importance because one could then substantially decrease the amount of hexachlorophene employed in the antibacterial composition and thereby greatly reduce the tendency of such compositions to discolor upon prolonged exposure to light.
- antibacterial compositions which include as antibacterial agents a synergistic combination of 3,4,4'-trichlorocarbanilide and 2,4,4'-trichloro-2'-hydroxydiphenyl ether.
- our invention may be exemplified by a soap composition containing as the active antibacterial ingredient a synergistic mixture of (A) 3,4,4'-trichlorcarbanilide and (B) 2,4,4-trichloro-2'-hydroxydiphenyl ether wherein the ratio of A to B present in the soap is from about nine to forty parts of A to about one part of B.
- the invention relates to the synergistic cooperation of these two agents when used in minor proportions in various compositions, especially antibacterial detergent compositions such as soap, and the discovery that this synergistic phenomenon occurs even at the high pH conditions existing in soap and other detergent formulations provides one of the important aspects of this invention.
- the ratio of the preferred range of the carbanilide to the ehlorohydroxyphenyl phenyl ether is from about 9 to 40 parts of the carbanilide to about 1 part of the chlorohydroxyphenyl phenyl ether, the parts being by weight.
- the chlorohydroxyphenyl phenyl ether is preferably used in the proportion of 1 part of the chlorohydroxyphenyl phenyl ether to from 9 to 40 parts of the carbanilide.
- soap refers to the water-soluble ammonium, metallic, or organic base salts of various fatty acids, which are chiefly lauric, oleic, stearic, and palmitic acids. As used in this description, the term is intended to cover all products in which soap is a major constituent, for example, bar, flake, powdered, soft and liquid soaps; shaving creams, toothpaste, cleansing creams, etc.
- the anionic type and nonionic type synthetic detergents can be used in place of the soap.
- the anionic type synthetics suitable for use in the invention can be described as those detergents having pronounced cleansing power and including in their molecular structure an alkyl radical containing from 6 to 18 carbon atoms and a sulfonic acid or sulfuric acid ester radical. Either organic base, ammonium, sodium or potassium salts of the anionic type detergents can be used.
- alkyl-aryl sulfonates such as sodium or potassium dodecyl benzene sulfonate, sodium or potassium octadecyl benzene sulfonate, and sodium or potassium octyl naphthalene sulfonate
- the alkyl sulfates such as sodium or potassium salts of dodecyl, hexadecyl, and octadecyl sulfates
- the sulfonated fatty acid amides such as sodium or potassium salts of the oleic acid amide of methyl taurine
- the sulfonated monoglycerides such as the mono-coconut oil fatty acid ester of sodium 1,2-hydroxypropane-3-sulfonate.
- the nonionic type synthetic detergents suitable for use in the invention may be described as those detergents which do not ionize in solution but owe their watersolubility to un-ionized polar groups such as hydroxy or other linkages.
- the main types of detergents falling within this category are the polyoxyethylene ethers of the higher fatty alcohols and alkyl phenols; the polyethylene glycols of fatty acids; fatty alkylol amide condensation products; polymers of ethylene and propylene oxides; compounds formed by the addition of propylene oxide to ethylene diamine, followed by the addition of ethylene oxide; fatty acid ethylene oxide condensation products; condensation products of ethylene oxide and a fatty acid ester of a polyhydric alcohol or sugar; and the detergents prepared by heating together a higher fatty acid with a diethanolamine.
- Some examples of synthetic nonionics suitable for the purpose of this invention are ethylene oxide-tall oil fatty acid reaction products; isooctyl phenol-ethylene oxide reaction products; propylene oxide-ethylene oxide reaction products; and combinations of isooctyl phenolethylene oxide with coconut oil fatty acid ethylene oxide reaction products.
- synergistic combinations of the 3,4,4'-trichlorocarbanilide and the 2,4,4'-trichloro-2-hydroxydiphenyl ether can be added to the soap and other detergents by any suitable method which results in a uniform distribution of the agents throughout the entire mass.
- EXAMPLE I A convenient and meaningful method of measuring the effectiveness of antibacterial compositions is by means of a modified agar streak method utilizing varying amounts and ratios of the individual antibacterial agents in a toilet soap medium. Briefly the test consists of making serial dilutions of soap containing varying amounts and proportions of the antibacterial agents. All solutions are maintained at 60 C. until they are dispensed. Aliquots of the dilutions are dispensed into measured amounts of nutrient agar at 50 C. and thoroughly dispersed. Plates are poured, allowed to solidify and streaked with a standard 4 mm. loopful of a 24-hour broth culture of Staphylococcus aureus FDA 209.
- the bacteriostatic end point is determined.
- the bacteriostatic end point hereinafter called the minimum inhibitory concentration, represents the minimum concentration in p.p.m. (parts per million) of the bacteriostatic agent or combination of agents necessary to inhibit all growth of the inoculant organism. No particular minimum inhibitory concentration has been established to determine the usefulness of an antibacterial agent, although the lower the end point the better the antibacterial activity and the smaller will be the amount of the agent or agents necessary to maintain a particular degree of effectiveness.
- the soap utilized for these evaluations was a neutral white toilet soap containing about 20% by weight of sodium coco soap and about by weight of sodium tallow soap.
- Antibacterial compositions consisting essentially of a detergent selected from the group consisting of fatty acid water-soluble soaps, anionic and nonionic synthetic organic detergents, and from 0.3% to 2.5% by weight of said detergent of a synergistic combination of 3,4,4-trichlorocarbanilide and 2,4,4 triehloro 2 hydroxydiphenyl ether wherein the ratio of said carbanilide to said diphenyl ether in the detergent is from about nine to forty parts of said carbanilide to about one part of said diphenyl ether, said parts being by weight. 7
- Antibacterial compositions according to claim 1 wherein said detergent is a sodium soap of higher fatty acids and wherein the total concentration of said carbanilide and said diphenyl ether is about 1.1% by weight of said detergent.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Wood Science & Technology (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Dermatology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Emergency Medicine (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62906767A | 1967-04-07 | 1967-04-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3445398A true US3445398A (en) | 1969-05-20 |
Family
ID=24521442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US629067A Expired - Lifetime US3445398A (en) | 1967-04-07 | 1967-04-07 | Synergistic antibacterial compositions |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3445398A (enrdf_load_stackoverflow) |
| DE (1) | DE1925598A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2044388A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1244809A (enrdf_load_stackoverflow) |
| NL (1) | NL6907647A (enrdf_load_stackoverflow) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3764696A (en) * | 1967-08-01 | 1973-10-09 | Ciba Geigy Corp | Combatting bacteria with diphenyl thiocarbonates |
| US3947576A (en) * | 1973-09-27 | 1976-03-30 | Mortell Company | Synergistic biostatic composition |
| US3968210A (en) * | 1973-06-18 | 1976-07-06 | Ciba-Geigy Corporation | Synergistic germicidal compositions containing 3,5-dimethyl-4-chlorophenol |
| US4034097A (en) * | 1973-09-27 | 1977-07-05 | Mortell Company | Synergistic biostatic composition |
| US4115294A (en) * | 1976-01-10 | 1978-09-19 | Ciba-Geigy Corporation | Bactericidal soap bar |
| US4118332A (en) * | 1965-10-22 | 1978-10-03 | Colgate-Palmolive Company | Synergistic antibacterial composition containing mixtures of certain halogenated diphenyl ethers and trichlorocarbanilides |
| US5837274A (en) * | 1996-10-22 | 1998-11-17 | Kimberly Clark Corporation | Aqueous, antimicrobial liquid cleaning formulation |
| CN109730059A (zh) * | 2019-01-22 | 2019-05-10 | 宁波翔神生化有限公司 | 一种高效洗护抑菌剂及其制备方法 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2315257A1 (fr) * | 1975-06-27 | 1977-01-21 | Seppic Sa | Nouvelles preparations dentifrices |
| FR2458280A2 (fr) * | 1979-06-08 | 1981-01-02 | Oreal | Lotions non irritantes pour le demaquillage des yeux |
| EP0029805B1 (de) * | 1979-11-16 | 1982-10-20 | Ciba-Geigy Ag | Seifenstück mit antimikrobieller Wirkung und Verfahren zur Verminderung seiner Verfärbung |
| DE3532860C1 (de) * | 1985-09-14 | 1987-03-12 | Blendax Werke Schneider Co | Mittel zur oralen Hygiene |
| GB8526093D0 (en) * | 1985-10-22 | 1985-11-27 | Beecham Group Plc | Composition |
| GB8615534D0 (en) * | 1986-06-25 | 1986-07-30 | Beecham Group Plc | Composition |
| US5977049A (en) * | 1997-07-30 | 1999-11-02 | Colgate-Palmolilve Co. | Carbanilide antibacterial composition |
| WO2006097238A1 (en) * | 2005-03-16 | 2006-09-21 | Unilever Plc | A soap composition |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6401526A (enrdf_load_stackoverflow) * | 1963-02-22 | 1964-08-24 | ||
| US3177115A (en) * | 1962-04-03 | 1965-04-06 | Armour & Co | Antiseptic compositions |
| US3284362A (en) * | 1964-07-15 | 1966-11-08 | Geigy Chem Corp | Stabilization of soap compositions |
-
1967
- 1967-04-07 US US629067A patent/US3445398A/en not_active Expired - Lifetime
-
1969
- 1969-05-19 GB GB25312/69A patent/GB1244809A/en not_active Expired
- 1969-05-19 NL NL6907647A patent/NL6907647A/xx unknown
- 1969-05-19 FR FR6916171A patent/FR2044388A5/fr not_active Expired
- 1969-05-20 DE DE19691925598 patent/DE1925598A1/de active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3177115A (en) * | 1962-04-03 | 1965-04-06 | Armour & Co | Antiseptic compositions |
| NL6401526A (enrdf_load_stackoverflow) * | 1963-02-22 | 1964-08-24 | ||
| US3284362A (en) * | 1964-07-15 | 1966-11-08 | Geigy Chem Corp | Stabilization of soap compositions |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4118332A (en) * | 1965-10-22 | 1978-10-03 | Colgate-Palmolive Company | Synergistic antibacterial composition containing mixtures of certain halogenated diphenyl ethers and trichlorocarbanilides |
| US3764696A (en) * | 1967-08-01 | 1973-10-09 | Ciba Geigy Corp | Combatting bacteria with diphenyl thiocarbonates |
| US3968210A (en) * | 1973-06-18 | 1976-07-06 | Ciba-Geigy Corporation | Synergistic germicidal compositions containing 3,5-dimethyl-4-chlorophenol |
| US3947576A (en) * | 1973-09-27 | 1976-03-30 | Mortell Company | Synergistic biostatic composition |
| US4034097A (en) * | 1973-09-27 | 1977-07-05 | Mortell Company | Synergistic biostatic composition |
| US4115294A (en) * | 1976-01-10 | 1978-09-19 | Ciba-Geigy Corporation | Bactericidal soap bar |
| US5837274A (en) * | 1996-10-22 | 1998-11-17 | Kimberly Clark Corporation | Aqueous, antimicrobial liquid cleaning formulation |
| CN109730059A (zh) * | 2019-01-22 | 2019-05-10 | 宁波翔神生化有限公司 | 一种高效洗护抑菌剂及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2044388A5 (enrdf_load_stackoverflow) | 1971-02-19 |
| NL6907647A (enrdf_load_stackoverflow) | 1970-11-23 |
| DE1925598A1 (de) | 1970-12-17 |
| GB1244809A (en) | 1971-09-02 |
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