US3134711A - Halogenated salicylanilide-halogenated trifluoromethyldiphenyl urea synergistic composition - Google Patents

Halogenated salicylanilide-halogenated trifluoromethyldiphenyl urea synergistic composition Download PDF

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Publication number
US3134711A
US3134711A US94437A US9443761A US3134711A US 3134711 A US3134711 A US 3134711A US 94437 A US94437 A US 94437A US 9443761 A US9443761 A US 9443761A US 3134711 A US3134711 A US 3134711A
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United States
Prior art keywords
halogenated
bacterial
trifluoromethyldiphenyl
urea
trifluoromethyl
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Expired - Lifetime
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US94437A
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English (en)
Inventor
Herbert H Reller
William E Jordan
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Procter and Gamble Co
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Procter and Gamble Co
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Priority to NL120998D priority Critical patent/NL120998C/xx
Priority to NL275155D priority patent/NL275155A/xx
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to US94437A priority patent/US3134711A/en
Priority to DEP28856A priority patent/DE1158216B/de
Priority to GB9251/62A priority patent/GB994705A/en
Priority to US320598A priority patent/US3256200A/en
Application granted granted Critical
Publication of US3134711A publication Critical patent/US3134711A/en
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/60—Salicylic acid; Derivatives thereof
    • A61K31/618—Salicylic acid; Derivatives thereof having the carboxyl group in position 1 esterified, e.g. salsalate
    • A61K31/621—Salicylic acid; Derivatives thereof having the carboxyl group in position 1 esterified, e.g. salsalate having the hydroxy group in position 2 esterified, e.g. benorylate
    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/60—Salicylic acid; Derivatives thereof
    • 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

Definitions

  • This invention relates to improved anti-bacterial agents. More particularly, it relates to anti-bacterial agents which comprise in combination a halogenated salicylanilide and a halogenated trifluoromethyldiphenyl urea compound.
  • halogenated salicylanilide and trifluoromethyldiphenyl urea compounds as anti-bacterial agents individually has been disclosed in the art.
  • the brominated salicylanilides have been employed as antibacterial agents in detergent compositions such as deodorant toilet bars, and laundering detergent products.
  • Anti-bacterial agents which have heretofore been employed in detergent compositions including the said halogenated salicylanilides display certain inherent deficiencies which detract from their eificacy in such applications.
  • Gram-negative organisms are common contaminates of the skin and other surfaces upon which anti-bacterial detergent usage has been found desirable and it is therefore essential to reduce the population of these organisms as well as gram-positive organisms to obtain the maximum beneficial effect.
  • anti-bacterial agents which have been found satisfactory for use in detergent milieu otherwise, display only slight activity against gram-negative organisms.
  • Both the halogenated salicylanilide and halogenated trifluoromethyldiphenyl urea compounds are subject to this deficiency, neither compound displaying significant activity against gram-negative organisms at feasible use concentrations.
  • a disadvantageous characteristic of the widely used bisphenolic compounds is photo-sensitivity.
  • bis(3, 5,6-trichloro-2-hydroxyphenyl) methane and bis(3,4-dichloro-2-hydroxy phenyl) sulfide for example are incorporated in a toilet detergent bar in concentrations as low as 0.5%, exposure to ordinary daylight results in an unsightly discoloration of the bar.
  • the degree of discoloration of detergent bars containing this level of bisphenolic compounds is sufliciently great that gold or yellow coloring material must be incorporated in the formulation for masking purposes.
  • this invention comprises a synergistic com bination of a halogenated salicylanilide and a halogenated trifiuoromethyldiphenyl urea compound.
  • Synergistic combination as used herein refers to a mixture of two or 3,134,711 Patented May 26, 1964 X1 OHO Y wherein each X represents hydrogen or halogen, X represents a halogen, and Y represents hydrogen, halogen or trifluoromethyl.
  • halogenated salicylanilides which are encompassed by the above general formula include 3,5,4- tribromosalicylanilide, 5 bromosalicyl 3,5 di(trifluoromethyl) anilide, 5 -chlorosalicyl-3,5-di trifluoromethyl anilide, 3,5-dichlorosalicyl-3,4-dichloroanilide and 5-chlorosalicyl-3-trifluoromethyl-4-chloroanilide.
  • Other halogenated salicylanilides which come within the above general formula and display synergistic activity in conjunction with the urea derivatives of this invention are disclosed by Bindler and Model in US. Patent 2,703,332, granted March 1, 1955. This patent further discloses a method for their preparation.
  • X represents halogen or ethoxy
  • X represents hydrogenor halogen
  • Y represents hydrogen or trifiuoromethyl.
  • the preferred compounds of this group include 3-trifluoromethyl-4,4-dichlorocarbanilide, 3-trifluoromethyl-3 ,4,4'- trichlorocarbanilide, 3,3 -bis (trifiuoromethyl) -4-ethoxy-4'- 'chlorocarbanilide, and 3,5-bis(trifiuoromethyl)-4-chlorocarbanilide.
  • These and other operable halogenated tri fluoromethyldiphenyl urea compounds are more fully described in U.S.
  • Antibacterial activity is expressed herein in terms of the per cent reduction in number of viable microorganisms following exposure of a suspension of either Staphylococcus aureus as the representative gram-positive organism or Escherichia coli as the representative gram-negative or" ganism to a given concentration of the various anti bacterial combinations for 10 minutes at 37 C. The relative eifectiveness of the combinations is reflected in reduction of numbers of viable organisms.
  • the activity of the mixtures of the above examples was determined in accordance with the method referred to above, i.e., suificient anti-bacterial agent was added to a tube of FDA nutrient broth (US. Dept. of Agriculture Circular 198, December 1931, page 4) to attain the desired concentration.
  • the suspending fiuid and anti-bacterial agent were heated to 37 C. and inoculated with approximately five million cells of the test organisms. These mixtures were then incubated for minutes and an aliquot was removed, diluted in 0.1% peptone water diluent, and placed on B.B.L. trypticase soy agar (supplied by Baltimore Biological Laboratories, Baltimore, Maryland).
  • the mixtures of this invention have been found to significantly increase the anti-bacterial activity of non-soap synthetic detergent compositions including both anionic and nonionic and solid or liquid types. Although some of the detergents in the anionic group, for example, alkyl benzene sulfonate, have substantial anti-bacterial effect against gram-positive microorganisms, few have significant effect against gram-negative organisms.
  • the incorporation of a small amount of halogenated salicylanilide-halogenated trifluoromethyldiphenyl urea mixtures of this invention in synthetic detergent compositions will effect an increase in anti-bacterial activity against gram-positive organisms and will impart significant levels of antibacterial activity against gram-negative organisms.
  • the anionic synthetic detergent which can be employed with this invention is generally defined as a water-soluble salt of an organic sulfuric reaction product having in its noleeular structure an alkyl group containing from about 8 to about 22 carbon atoms and a radical selected from the group consisting of sulfonic acid and sulfuric acid ester radicals.
  • Important examples of the synthetics of this group which may be benefited through the incorporation therein of the mixtures of this invention, are the sodium or potassium alkyl sulfates, especially those derived by sulfation of higher alcohols produced by reduction of glycerides of tallow or coconut oil; sodium or potassium alkyl benzene sulfonates, especially those of the types described in US.
  • nonionie synthetic detergents hereinbefore described as beneficially affected by the antibacterial mixtures of this invention may be broadly defined as compounds produced by the condensation of alkylene oxide groups with an organic hydrophobic compound which may be aliphatic or alkyl aromatic in nature.
  • nonionics to which significant levels of anti-bacterial activity will be imparted through the incorporation of minor amounts of a halogenated salicylanilide-trilluoromethylcarbanilide mixture is marketed under the trade name Pluronic by the Wyandotte Chemical Co. of Wyandotte, Michigan. These compounds are formed by condensing ethylene oxide with a hydrophobic base formed by the condensation of propylene oxide with propylene glycol.
  • nonionics which are suitable for use with the mixtures of this invention include the polyethylene oxide condensates of alkyl phenols, e.g., the condensation prodnets of alkyl phenols having a straight or branched chain alkyl group containing from about 6 to 12 carbon atoms, with from about 10 to about 25 moles of ethylene oxide per mole of alkyl phenol.
  • the alkyl substituent in each compound can be conveniently derived from polymerized propylene diisobutylene, octane, or nonane or from any other natural or artificial source which will provide alkyl chains with the requisite number of carbon atoms as specified hereinbefore.
  • nonionics may be derived by the condensation of ethylene oxide with the product resulting from the reaction of propylene oxide and ethylene diamine.
  • a minor amount of a 1:1 mixture of 3,5,4'-tribromosalicylanilide and 3-trifluoromethyl-4,4-dichlorocarbanilide renders a composition containing any of the above detergents or mixtures thereof, antibacterially active against a broad range of microorganisms including some which are gram-negative.
  • Detergent compositions containing the anti-bacterial mixtures of this invention find utility in a variety of applications and physical forms as will be recognized by those skilled in the art.
  • Such products may be used as toilet detergent bars, for example, the anti-bacterial mixture being present in amounts varying from 0.1% to by weight of the total composition.
  • the bar would contain the said anti-bacterial mixtures in amount varying from .5% to 2% by weight of the total composition.
  • Middle-cut coconut alcohols having a chain length distribution substantially as follows: 2%C10, 66%C1.., 23%- C14, and 9%C1e.
  • 3,5,4- tribromosalicylanilide can be replaced by any of the other halogenated salicylanilides of this invention, such as 5-bromosalicyl-3,5-di(trifiuoromethyl) anilide, 5- chlorosalicyl-3,5-di(trifiuoromethyl) anilide, 3,5-dichlorosalicyl-3,4-dichloroanilide or 5-chlorosalicyl-3-trifluoromethyl-4-chloranilide without decreasing the deodorant efiicacy of the product.
  • halogenated salicylanilides of this invention such as 5-bromosalicyl-3,5-di(trifiuoromethyl) anilide, 5- chlorosalicyl-3,5-di(trifiuoromethyl) anilide, 3,5-dichlorosalicyl-3,4-dichloroanilide or 5-chlorosalicyl-3-trifluoromethyl-4-chlor
  • Example XI A granular built synthetic anionic laundry detergent composition having the following formulation was prepared by conventional means.
  • anti-bacterial compositions toilet and laundry detergents. It will be obvious to those skilled in the art, however, that the antibacterial mixtures can also be beneficially employed in such products as tooth powder, toothpaste, mouth-Wash, antiseptic ointment, foot powders and the like.
  • An anti-bacterial composition comprising in combination (1) 3,5,4-tribromosalicylanilide and (2) 3-trifluoromethyl-4,4-dichlorocarbanilide, and the ratio (1) to (2) being between 1:9 and 9: 1.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
US94437A 1961-03-09 1961-03-09 Halogenated salicylanilide-halogenated trifluoromethyldiphenyl urea synergistic composition Expired - Lifetime US3134711A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
NL120998D NL120998C (en)van) 1961-03-09
NL275155D NL275155A (en)van) 1961-03-09
US94437A US3134711A (en) 1961-03-09 1961-03-09 Halogenated salicylanilide-halogenated trifluoromethyldiphenyl urea synergistic composition
DEP28856A DE1158216B (de) 1961-03-09 1962-02-26 Bakterizides Mittel
GB9251/62A GB994705A (en) 1961-03-09 1962-03-09 Anti-bacterial compositions
US320598A US3256200A (en) 1961-03-09 1963-10-11 Anti-bacterial detergent composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US94437A US3134711A (en) 1961-03-09 1961-03-09 Halogenated salicylanilide-halogenated trifluoromethyldiphenyl urea synergistic composition
US320598A US3256200A (en) 1961-03-09 1963-10-11 Anti-bacterial detergent composition

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US320598A Expired - Lifetime US3256200A (en) 1961-03-09 1963-10-11 Anti-bacterial detergent composition

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NL (2) NL120998C (en)van)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3216944A (en) * 1961-09-11 1965-11-09 Procter & Gamble Stabilized fabric softener composition
US3244585A (en) * 1964-01-29 1966-04-05 Herbert C Stecker Stabilized halosalicylanilide germicides
US3303136A (en) * 1963-02-26 1967-02-07 Lever Brothers Ltd Detergent compositions
US4118332A (en) * 1965-10-22 1978-10-03 Colgate-Palmolive Company Synergistic antibacterial composition containing mixtures of certain halogenated diphenyl ethers and trichlorocarbanilides

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3989827A (en) * 1965-10-22 1976-11-02 Colgate-Palmolive Company Antibacterial composition
US3981814A (en) * 1973-09-18 1976-09-21 Givaudan Corporation Bacteriostatic substituted benzanilide compositions and methods for their use
EP0496434B1 (en) 1987-10-22 1999-02-03 The Procter & Gamble Company Photoprotection compositions comprising chelating agents
GB2243615B (en) * 1990-05-04 1993-03-31 Procter & Gamble Beta-phase soap bars including those containing low level of moisture and solubilized solid antibacterial agent
US6287577B1 (en) 1997-11-12 2001-09-11 The Procter & Gamble Company Leave-on antimicrobial compositions which provide improved residual benefit versus gram positive bacteria
US5968539A (en) * 1997-06-04 1999-10-19 Procter & Gamble Company Mild, rinse-off antimicrobial liquid cleansing compositions which provide residual benefit versus gram negative bacteria
US6210695B1 (en) 1997-06-04 2001-04-03 The Procter & Gamble Company Leave-on antimicrobial compositions
US6190674B1 (en) 1997-06-04 2001-02-20 Procter & Gamble Company Liquid antimicrobial cleansing compositions
US6190675B1 (en) 1997-06-04 2001-02-20 Procter & Gamble Company Mild, rinse-off antimicrobial liquid cleansing compositions which provide improved residual benefit versus gram positive bacteria
US6183763B1 (en) 1997-06-04 2001-02-06 Procter & Gamble Company Antimicrobial wipes which provide improved immediate germ reduction
US6284259B1 (en) 1997-11-12 2001-09-04 The Procter & Gamble Company Antimicrobial wipes which provide improved residual benefit versus Gram positive bacteria
US6183757B1 (en) 1997-06-04 2001-02-06 Procter & Gamble Company Mild, rinse-off antimicrobial cleansing compositions which provide improved immediate germ reduction during washing
US6214363B1 (en) 1997-11-12 2001-04-10 The Procter & Gamble Company Liquid antimicrobial cleansing compositions which provide residual benefit versus gram negative bacteria
US6197315B1 (en) 1997-06-04 2001-03-06 Procter & Gamble Company Antimicrobial wipes which provide improved residual benefit versus gram negative bacteria
US6287583B1 (en) 1997-11-12 2001-09-11 The Procter & Gamble Company Low-pH, acid-containing personal care compositions which exhibit reduced sting
US7319112B2 (en) * 2000-07-14 2008-01-15 The Procter & Gamble Co. Non-halogenated antibacterial agents and processes for making same
US20020014178A1 (en) * 2000-07-14 2002-02-07 Haught John Christian Biocide compositions and methods and systems employing same

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2703332A (en) * 1955-03-01 Poly halo-salicylanilioes
US2745874A (en) * 1953-06-18 1956-05-15 Geigy Ag J R Insecticidal derivatives of diphenyl urea
US2906711A (en) * 1958-04-25 1959-09-29 Herbert C Stecker Toilet detergent composition containing synergistic di- and tri-halo salicylanilide mixtures
US2951786A (en) * 1955-01-14 1960-09-06 Spencer Chem Co Bactericidal and fungicidal compositions comprising pentahalophenyl n-(phenyl) carbamates
US2965575A (en) * 1957-05-27 1960-12-20 Monsanto Chemicals Antiseptic detergent compositions
US2995488A (en) * 1955-03-24 1961-08-08 Fmc Corp Synergistic insecticidal compositions

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3057920A (en) * 1957-12-05 1962-10-09 Lever Brothers Ltd Process for preparing 3, 4', 5-tribromosalicylanilide in acetic acid
US3041236A (en) * 1959-09-18 1962-06-26 Herbert C Stecker Germicides containing trifluoromethyl halogenated salicylanilides

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2703332A (en) * 1955-03-01 Poly halo-salicylanilioes
US2745874A (en) * 1953-06-18 1956-05-15 Geigy Ag J R Insecticidal derivatives of diphenyl urea
US2951786A (en) * 1955-01-14 1960-09-06 Spencer Chem Co Bactericidal and fungicidal compositions comprising pentahalophenyl n-(phenyl) carbamates
US2995488A (en) * 1955-03-24 1961-08-08 Fmc Corp Synergistic insecticidal compositions
US2965575A (en) * 1957-05-27 1960-12-20 Monsanto Chemicals Antiseptic detergent compositions
US2906711A (en) * 1958-04-25 1959-09-29 Herbert C Stecker Toilet detergent composition containing synergistic di- and tri-halo salicylanilide mixtures

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3216944A (en) * 1961-09-11 1965-11-09 Procter & Gamble Stabilized fabric softener composition
US3303136A (en) * 1963-02-26 1967-02-07 Lever Brothers Ltd Detergent compositions
US3244585A (en) * 1964-01-29 1966-04-05 Herbert C Stecker Stabilized halosalicylanilide germicides
US4118332A (en) * 1965-10-22 1978-10-03 Colgate-Palmolive Company Synergistic antibacterial composition containing mixtures of certain halogenated diphenyl ethers and trichlorocarbanilides

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NL275155A (en)van)
US3256200A (en) 1966-06-14
NL120998C (en)van)
GB994705A (en) 1965-06-10
DE1158216B (de) 1963-11-28

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