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
  • A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
• • 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
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
  • A01N37/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof

Definitions

• the phenolic substances are anionic in nature, and as is well known, are effective at low concentrations against gram-positive bacteria. However, they show poor action against gram-negative bacteria and other microorganisms.
• the quaternary ammonium compounds which belong to the class of cationic germicides, in addition to being effective against gram-positive bacteria, also possess activity against gram-negative organisms. the outstanding features of phenolics, on the one hand, and quaternary ammonium compounds, on the other, cannot be combined. Mixtures of those two classes of germicides mutually inactivate each other and, in consequence, the mixtures are ineffectual as germicides.
• Cationic compounds which combine with gerrnicidally active anionic compounds to form the compositions of this invention that provide synergistic antimicrobial action are as follows:
• N-alkylated or alkenylated alkylene polyamines which possess at least one of said aliphatic hydrocarbon groups having from 6 to 20 carbon atoms joined to one of the amino nitrogen groups and having one to live alkylene groups interconnected by nitrogen atoms. They may be represented structurally in their simpler form as follows:
• R is an alkylene radical which may be the ethylene radical (--CH CH the isopropylene radical [CH Cl-I(CH the trimethylene radical or a mixture of such radicals and n may be Zero, in which case the parenthesized group is non-existent or It may be a whole number from *1 to 4; and X is an alkyl or alkenyl radical which may have from one to twenty carbon atoms, e.-g., in the alkyls in the range from methyl to eicosyl (C l-I and Y and Y are hydro- It is well known that.
• 3,1h8dl36 Patented Oct. 22, 1963 ice gen atoms or alkyl or alkenyl or carboxyalkyl or carboxy alkenyl groups having from 1 to 20 carbon atoms in the aliphatic hydrocarbon radical.
• n is zero or one, and the symbols n, X, R, Y and Y have the above defined significance.
• X, and Y and Y are the aliphatic hydrocarbon radicals present in the fatty alcohols and fatty acids, i.e., either saturated or 2,2 methylene bis (3,4,6 trichlorophenol) 2,2 methylene bis (4,6 d'ichlorophenol), 2,2 methylene bis (4 chlorophenol),
• Salicylanilide Monohalogenated salicylanilides
• Polyhalogenated salicylanilides Monohalogenated salicylanilides
• anionics are halogenated carbanilides and thiocarbanilides. These diphenyl ureas and thioureas, in consequence of possible enolizations and tautomerizations, possess the anionic properties of phenols akin to those of the phenols in the above classes 1 to 3.
• novel anionic-cationic germicidal compositions of this invention have other desirable features as follows:
• the cationic component has a solubilizing efiect on the anionic component which is generally water-insoluble. This is of practical importance because a concentrated solution of the germicides can be diluted with water to use-level without separation of the anionic fraction.
• Non-ionic and ampholytic detergents are compatible with the synergistic germicidal compositions and can be used as adjuncts for emulsification and cleansing purposes.
• the germicidal compositions described herein possess excellent wetting properties and permit thorough penetration and uniform distribution of the germicidal compositions onto the surfaces under treatment.
• the cationic component of the cationic-anionic germicidal composition inhibits darkening of phenolic anionic component when exposed to light.
• the instant cationic components and the anionic components interact chemically with each other to form the synergistic combinations. This is manifested, inter alia, by the fact that heat is evolved when the cationic substance is mixed with the anionic substance, a phenomenon indicative of an exothermic reaction. Furthermore, as mentioned in d, supra, the sensitivity of phenolics to light (manifested normally by phenolics when exposed to light) is absent in the instant phenolic-cationic combination.
• the synergistic action of the novel germicide mixtures is achieved over a wide range of weight ratios of the anionic-cationic components.
• the preferred range although it is not to be construed as restrictive, is 1 to 9 parts of the anionic component to 9 to 1 parts of the cationic component.
• Each of the stock solutions was added to water to give 0.1, 0.25 and 0.5 dilution levels to yield 50, 125 and 250 ppm. of active germicide.
• fabrics, particularly cottons, treated with the germicidal combinations embodied in my invention are resistant to mildew and other mold spoilage.
• Clzaetomium globosum, Aspergillus and Penicillium strains are prevented from attacking cottons, paper, paper board and other cellulosics, when the latter is given treatment with the novel germicidal mixtures.
• germicidal combinations manifest synergistic action on hard surfaces and show excellent kill activity under the conditions of the AOAC Use Dilution Confirmation Test, as described in the J. Assoc. Off. Agric. Chem. 36, 466 (1953).
• Germicidal preparations that satisfy the requirements of the test in accordance with governmental regulations are defined as disinfectants for use on hard surfaces (walls, floors, instruments, rubber goods, etc.).
• the test organisms employed are Salmonella choleraesuis and Staphylococcus aureus representative of enteric and of pyogenic bacteria, respectively.
• the test requires that at the recommended use-dilution of the germicide preparation, complete kill of the test organism in 10 minutes or less should occur. The higher the use-dilution achieving this requirement, the more potent is the germicidal preparation.
• Results given in Table II demonstrate that a 5% stock solution of a 1:1 mixture of lauryl diethylene triamine (LDT) and 3,3',4,5 itetrachlorosalicylanilide causes kill of S. choleraesuis at a dilution of 150 as compared to a dilution value of only 25 for the 5% stock solution of the tetrachlorosalicylanilide and a dilution value of for 5% LDT.
• LDT lauryl diethylene triamine
• EXAMPLE 3 Skin and Scalp Treatment the gram-negative test organism associated with certain skin disorders. Against these two organisms I have found that minimum effective concentration to produce bacteriostasis and/or bactericidal action is lowest for germicidal mixtures described herein as compared to the action of the anionic germicide component or eationic germicide component separately. The synergistic action is demonstrated in the standard toxic dilution test which measures the minimum effective concentration of a germicidal preparation in nutrient broth which would inhibit or kill the test organism.
• a composition comprising the combination of about 1 to 9 parts of lauryl diethylene triamine and about 9 to 1 parts of 2,2 methylene bis (3,4,6-trichlorophenol).
• a composition comprising the combination of about 1 to 9 parts of lauryl diethy-lenetriamine and about 9 to 1 parts of 4', 5 dibromosalicylanilide.
• a composition comprising the combination of about 9-1 parts of lauryl diethylene triamine and about 1-9 parts of polybrominated salicylanilide.
• a composition comprising the combination of about 9-l parts of lauryl diethylene triamine and about 1-9 parts of halogenated salicylanilide.
• Wadley The Evidence Required to Show Synergistic Action of Insecticides and a Short Cut in Analysis, US. Dept. of Agr., Bulletin ET-223, recd February 5, 1957, pp. 1-7.

Landscapes

• Life Sciences & Earth Sciences (AREA)
• Dentistry (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Agronomy & Crop Science (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
• Cosmetics (AREA)

Priority Applications (7)

Applications Claiming Priority (1)

Publications (1)

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Cited By (10)

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Citations (3)

• 0
  • NL NL257911D patent/NL257911A/xx unknown
  • NL NL133648D patent/NL133648C/xx active
• 1959
  • 1959-11-12 US US852172A patent/US3108036A/en not_active Expired - Lifetime
• 1960
  • 1960-11-10 GB GB38631/60A patent/GB963907A/en not_active Expired
  • 1960-11-11 SE SE10856/60A patent/SE313891B/xx unknown
  • 1960-11-14 CH CH1270960A patent/CH409250A/de unknown

Patent Citations (3)

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