US2906711A - Toilet detergent composition containing synergistic di- and tri-halo salicylanilide mixtures - Google Patents

Toilet detergent composition containing synergistic di- and tri-halo salicylanilide mixtures Download PDF

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Publication number
US2906711A
US2906711A US730910A US73091058A US2906711A US 2906711 A US2906711 A US 2906711A US 730910 A US730910 A US 730910A US 73091058 A US73091058 A US 73091058A US 2906711 A US2906711 A US 2906711A
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mixtures
tri
detergent composition
composition containing
toilet
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Herbert C Stecker
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    • 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

  • the compounds employed with toilet detergent compositions of the present invention may be designated broadly by the following general chemical structural formulas, wherein the letter X denotes a halogen atom:
  • Example 1 Serial wash basin tests were conducted using the Cade method as described in Soap and Sanitary Chemicals, 26, 35 (1950), as follows:
  • Ivory brand soap which is a neutral white high grade toilet soap consisting of a mixture of 80% sodium soap and 20% potassium soap produced from a 70% tallow and 30% coconut oil glyceride blend (made in accordance with U.S. Patent 2,295,594).
  • a thick paste was prepared by the addition of water, and the soap was pressed into molds. Human subjects then washed their hands with this soap and the reduction of germicidal power (in the V 2,906,711 Patented Sept. 29, 1959 2 hand count) at the end of the testwas determined with the following results obtained: f
  • the effectiveness of the mixture is of the effectiveness of the pure tribromo compound. It also is noted that the shaded area C which includes mixtures containing 65% to 98% of the tribromo derivative are unexpectedly and unusually high in germicidal effect, having an etfectiveness of at least 144% of that of the pure tribromo derivative. It is this range which is being claimed in the present application.
  • Commercial toilet soaps generally consist of neutral high grade sodium and potassium salts of tallow fatty acids.
  • concentration of the present synergistic mixture used in such soaps may be 0.01% to 0.5% or to 1%, 2%, 5%, or even 10% by weight of the soap.
  • the aforesaid halosalicylanilides may be prepared by the method disclosed in US. Patent 2,731,386.
  • 5,4-dichloro SA can be prepared by heating 5- chlorosalol with 4-chloro-aniline to 180-220 C. and continuously distilling off the liberated phenol during the process. It is advantageous to use reduced pressure for this distillation and to carry out the procedure in a nitrogen atmosphere.
  • the crude reaction product is dissolved in alcohol to which an equivalent amount of sodium hydroxide is added in the form of approximately N aqueous solution.
  • the resulting solution of the sodium salt of 5,4'-dichloro SA then is discolorized with charcoal and neutralized with dilute hydrochloric acid.
  • the 5,4-dichloro SA thus precipitated is filtered and recrystallized from ethyl alcohol, ethyl acetate, or some other suitable solvent.
  • a further method involves condensation between the salicylic and aniline moieties in an organic solvent such as toluene, chlorobenzene, kerosene, etc., in presence of a dehydrating agent such as thionyl chloride.
  • the benzene nuclei may be halogenated prior to or after condensation by application of the proper halogen in a glacial acetic acid or acetic acid-water mixture containing the halogenatable materials.
  • Commercial synthetic toilet detergent compositions generally consist of neutral high grade sodium and potassium salts of tallow fatty acids, some of which may contain a small amount (110%), medium amount (10- 50%), or even a major amount (SO-100%) of non-soap synthetic organic detergents, particularly the anionic detergents such as the substituted amides and the alkyl aryl sulfonates.
  • the term detergent includes soap,
  • toilet detergen as used herein is employed to designate a composition employed for washing the skin.
  • toilet soap also is employed in its popular or ordinary meaning, that is, those compositions employed for cleansing the skin and prepared from an alkali metal compound such as potassium or sodium hydroxide and a fat or fatty acid, both saturated and unsaturated.
  • the compositions described herein also may include other antiseptic agents, emollients, water softeners, antioxidants, dyes, perfumes, cold cream additives and the like.
  • An antiseptic toilet detergent composition comprising a synthetic organic toilet detergent and 0.01% to 10% by weight based on the detergent of a germicide consisting of a synergistic mixture of to 98% by weight of 3,5,4'-trihalosalicylanilide and 35% to 2% of 5,4- dihalosalicylanilide, wherein the halo substituents are selected from the group consisting of chlorine, bromine and iodine.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
US730910A 1958-04-25 1958-04-25 Toilet detergent composition containing synergistic di- and tri-halo salicylanilide mixtures Expired - Lifetime US2906711A (en)

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US730910A US2906711A (en) 1958-04-25 1958-04-25 Toilet detergent composition containing synergistic di- and tri-halo salicylanilide mixtures

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3041236A (en) * 1959-09-18 1962-06-26 Herbert C Stecker Germicides containing trifluoromethyl halogenated salicylanilides
US3134711A (en) * 1961-03-09 1964-05-26 Procter & Gamble Halogenated salicylanilide-halogenated trifluoromethyldiphenyl urea synergistic composition
US3152039A (en) * 1960-11-23 1964-10-06 Dow Chemical Co Germicidal compositions
US3189645A (en) * 1961-08-08 1965-06-15 American Cyanamid Co N-hydroxycarbanilidies and their use as bactericides and fungicides
US3240710A (en) * 1962-06-15 1966-03-15 Swift & Co Lauryl pyridinium salt of 5-chloro-2-mercaptobenzothiazole and tri- and dibrominatedsalicylanilides bactericide composition
US3244585A (en) * 1964-01-29 1966-04-05 Herbert C Stecker Stabilized halosalicylanilide germicides
US3331874A (en) * 1962-05-29 1967-07-18 Herbert C Stecker Bistrifluoromethyl anilides
US3503885A (en) * 1965-11-27 1970-03-31 Henkel & Cie Gmbh Color stable washing,rinsing and cleaning composition
US3671630A (en) * 1970-08-17 1972-06-20 Lever Brothers Ltd Halogenated phenolic germicidal compositions containing terpene color stabilizers
US20020052343A1 (en) * 1999-12-15 2002-05-02 Allen Darin Arthur Salicylamides as serine protease inhibitors
US20040072908A1 (en) * 2000-07-14 2004-04-15 The Procter & Gamble Co. Non-halogenated antibacterial agents and processes for making same

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1066216A (fr) * 1951-08-17 1954-06-03 Basf Ag Procédé pour l'obtention d'anilides de l'acide salicylique à effet bactéricide
US2731386A (en) * 1951-09-06 1956-01-17 Wallace & Tiernan Company Inc Antifungal composition
GB760210A (en) * 1953-12-31 1956-10-31 Monsanto Chemicals Antiseptic detergent compositions
US2802029A (en) * 1951-10-17 1957-08-06 Knoll Ag Bromsalicyloyl-chloranilide

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1066216A (fr) * 1951-08-17 1954-06-03 Basf Ag Procédé pour l'obtention d'anilides de l'acide salicylique à effet bactéricide
US2731386A (en) * 1951-09-06 1956-01-17 Wallace & Tiernan Company Inc Antifungal composition
US2802029A (en) * 1951-10-17 1957-08-06 Knoll Ag Bromsalicyloyl-chloranilide
GB760210A (en) * 1953-12-31 1956-10-31 Monsanto Chemicals Antiseptic detergent compositions

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3041236A (en) * 1959-09-18 1962-06-26 Herbert C Stecker Germicides containing trifluoromethyl halogenated salicylanilides
US3152039A (en) * 1960-11-23 1964-10-06 Dow Chemical Co Germicidal compositions
US3134711A (en) * 1961-03-09 1964-05-26 Procter & Gamble Halogenated salicylanilide-halogenated trifluoromethyldiphenyl urea synergistic composition
US3189645A (en) * 1961-08-08 1965-06-15 American Cyanamid Co N-hydroxycarbanilidies and their use as bactericides and fungicides
US3331874A (en) * 1962-05-29 1967-07-18 Herbert C Stecker Bistrifluoromethyl anilides
US3240710A (en) * 1962-06-15 1966-03-15 Swift & Co Lauryl pyridinium salt of 5-chloro-2-mercaptobenzothiazole and tri- and dibrominatedsalicylanilides bactericide composition
US3244585A (en) * 1964-01-29 1966-04-05 Herbert C Stecker Stabilized halosalicylanilide germicides
US3503885A (en) * 1965-11-27 1970-03-31 Henkel & Cie Gmbh Color stable washing,rinsing and cleaning composition
US3671630A (en) * 1970-08-17 1972-06-20 Lever Brothers Ltd Halogenated phenolic germicidal compositions containing terpene color stabilizers
US20020052343A1 (en) * 1999-12-15 2002-05-02 Allen Darin Arthur Salicylamides as serine protease inhibitors
US20040072908A1 (en) * 2000-07-14 2004-04-15 The Procter & Gamble Co. Non-halogenated antibacterial agents and processes for making same
US7319112B2 (en) 2000-07-14 2008-01-15 The Procter & Gamble Co. Non-halogenated antibacterial agents and processes for making same

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