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WO1996006153A2 - Formulations tensioactives - Google Patents

Formulations tensioactives Download PDF

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Publication number
WO1996006153A2
WO1996006153A2 PCT/EP1995/003211 EP9503211W WO9606153A2 WO 1996006153 A2 WO1996006153 A2 WO 1996006153A2 EP 9503211 W EP9503211 W EP 9503211W WO 9606153 A2 WO9606153 A2 WO 9606153A2
Authority
WO
WIPO (PCT)
Prior art keywords
component
formulation according
weight
hydrogen
acid
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.)
Ceased
Application number
PCT/EP1995/003211
Other languages
English (en)
Other versions
WO1996006153A3 (fr
Inventor
Laszlo Moldovanyi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
BASF Schweiz AG
Original Assignee
Ciba Geigy AG
Ciba Spezialitaetenchemie Holding AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to JP8507758A priority Critical patent/JPH10504592A/ja
Priority to CA002196771A priority patent/CA2196771A1/fr
Priority to AU33452/95A priority patent/AU3345295A/en
Priority to MX9701416A priority patent/MX9701416A/es
Priority to EP95929863A priority patent/EP0777717A2/fr
Priority to BR9508775A priority patent/BR9508775A/pt
Priority to SK244-97A priority patent/SK24497A3/sk
Application filed by Ciba Geigy AG, Ciba Spezialitaetenchemie Holding AG filed Critical Ciba Geigy AG
Publication of WO1996006153A2 publication Critical patent/WO1996006153A2/fr
Publication of WO1996006153A3 publication Critical patent/WO1996006153A3/fr
Priority to FI970742A priority patent/FI970742A7/fi
Anticipated expiration legal-status Critical
Priority to BG101308A priority patent/BG101308A/xx
Ceased legal-status Critical Current

Links

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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0063—Photo- activating compounds
    • 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
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • 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
    • 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
    • A61K8/43—Guanidines
    • 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
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • 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
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations

Definitions

  • novel surface-active surfactant formulations comprise
  • the antimicrobial activity of the deblocked surfactant systems reaches upon gram-positive and gram-negative bacteria as well as yeasts, dermatophytes and the like.
  • the compounds of component (a j ) preferably correspond to the general formula
  • R j is hydrogen, hydroxy, C 1 -C 4 alkyl, chloro, nitro, phenyl oder benzyl,
  • R 2 is hydrogen, hydroxy, C 1 -C 6 alkyl or halogen
  • R 3 is hydrogen, C 1 -C 6 alkyl, hydroxy, chloro, nitro or a sulfo group in the form of the alkali metal salts or ammonium salts thereof, R 4 is hydrogen or methyl, R 5 is hydrogen or nitro.
  • Halogen is bromo or, preferably, chloro.
  • Such compounds are typically chlorophenols (o-, m-, p-chlorophenols), 2,4-dichlorophenol, p-nitrophenol, picric acid, xylenol, p-chloro-m-xylenol, cresols (o-, m-, p-cresols), p-chloro-m-cresol, pyrocatechin, resorcinol, orcinol, 4-n-hexylresorcinol, pyrogallol, phloroglucine, carvacrol, thymol, p-chlorothymol, o-phenylphenol, o-benzylphenol, p-chloro-o-benzylphenol and 4-phenolsulfonic acid.
  • the compounds of component (a 2 ) preferably correspond to the general formula
  • X is sulfur or the methylene group, Ri and R are hydroxy, and
  • R 3 , ' 3 , R , R'4, R 5 and R' 5 arc each independently of one another hydrogen or halogen.
  • Typical examples of compounds of formula (2) are hexachlorophene, tetrachlorophene, dichlorophene, 2,3-dihydroxy-5,5'-dichlorodiphenylsulfide, 2,2 ' -dihydroxy-3 ,3 ' ,5 ,5 ' -tetrachlorodiphenylsulf ⁇ de, 2,2 , -dihydroxy-3,3',5,5',6,6'-hexachlorodiphenylsulfide and 3,3'-dibromo-5,5'-dichloro-2,2'-dihydroxydiphenylamine.
  • the compounds of component (a 3 ) preferably correspond to the general formula
  • Rj, R 2 , R 3 , R 4 and R 5 arc each independently of one another hydrogen or chloro.
  • Illustrative examples of compounds of formula (3) are benzyl alcohol, 2,4-, 3,5- or 2,6-dichlorobenzyl alcohol and trichlorobenzyl alcohol.
  • Component (8 4 ) is chlorohexidine and salts thereof together with organic and inorganic acids, which type of compound may preferably be incorporated into syndet systems.
  • Component (& 5 ) is typically Cg-C ⁇ cocamidopropylbetaine.
  • Amphoteric surfactants corresponding to component (a $ ) are suitably C ⁇ alkylaminocarboxylic and Ci ⁇ alkanecarboxylic acids such as alkylaminoacetates or alkylaminopropionates.
  • the compounds of component (a 7 ) preferably correspond to the general formula
  • Hal is chloro or bromo, n and m are 1 or 2, and n + m are 3.
  • the quaternary ammonium salts of component (a 8 ) preferably correspond to formula
  • R , R 7 , R 8 and Ro arc each independently of one another Ci- galkyl, -Cx alkoxy or phenyl-lower alkyl, and
  • Hal is chloro or bromo.
  • n is an integer from 7 to 17, is very particularly preferred.
  • C 3 -Ci 2 di- or polycarboxylic acids typically malonic, succinic, glutaric, adipic, pimelic, suberic, azelaic and sebacic acid, undecanecarboxylic and dodecanedicarboxylic acid, fumaric, maleic, tartaric and malic acid as well as citric and aconitic acid;
  • aminocarboxylic acids typically ethylenediaminetetracetic acid, hydroxyethyl- ethylenediaminetetracetic acid and nitrilotriacetic acid;
  • aromatic carboxylic acids typically benzyl, phenylacetic, phenoxyacetic and cinnamic acid, 2-, 3- and 4-hydroxybenzoic acid, anilinic acid as well as o-, m- and p-chlorophenylacetic acid and o-, m- and p-chlorophenoxyacetic acid;
  • alkali metal salts and amine salts of inorganic acids typically the sodium or potassium salts and amine(R 1 R 2 R 3 ) salts of hydrochloric, sulfuric, phosphoric, C C 10 alkylphosphoric acid and boric acid, in which amine salts Rj, R 2 and R 3 have the meaning indicated above;
  • Rj is hydrogen or -C- ⁇ alkyl
  • R 2 and R 3 are each independently of the other hydrogen, C j -C ⁇ alkyl, C 2 -C 12 alkenyl, C 2 -Ci 2 hydroxyalkyl, or a polyglycol ether chain containing 1 to 30 -CH 2 -CH 2 -O- or -CHY r CHY 2 -O- groups, wherein Yj or Y 2 is a hydrogen radical and the other is methyl, e.g.N-methylacetamide;
  • R j , R 2 , R 3 and R 4 are each independently of one another hydrogen, C r C 8 alkyl,
  • C 4 -C 18 aliphatic and monocyclic alcohols typically C 2 -C 18 alkanols, C 2 -C 18 alkenols and terpene alcohols e.g. ethanol, propanol, isopropanol, hexanol, cis-3-hexen-l-ol, trans-2-hexen-l-ol, l-octen-3-ol, heptanol, octanol, trans-2-cis-6-nonadien-l-ol, decanol, linalol, geraniol, dihydroterpineol, myrcenol, nopol and terpineol;
  • Rj, R and R 3 arc each independently of one another hydrogen, hydroxy, halogen or C j - alkoxy, typically benzyl alcohol, 2,4-dichlorobenzyl alcohol, phenoxyethanol, l-phenoxy-2-propanol (phenoxyisopropanol) and cinnamyl alcohol;
  • R j and R 2 are each independently of the other hydrogen, C r C 12 alkyl, C 2 -C 12 alkenyl, C r C 8 alkanoyl, C 3 -C 18 alkenoyl, R 3 -(OCH-CH 2 - 7 5 7j-, wherein
  • R 3 is hydrogen, Cj-C 12 alkyl or C ⁇ -C ⁇ alkenyl, and R 4 is hydrogen or -CH 3 , and
  • X is C 2 -C 10 alkylene or -( H 2 CH O)f3fjCH 2 -CH2- or -(CH 2 -CH-O) ⁇ 3 ⁇ -CH 2 -CH- . CH 3 CH 3
  • All organic acids mentioned under (b) may also be obtained in the form of their water-soluble salts, such as the alkali metal salts, preferably the sodium or potassium salts or the amine(NRjR 2 R 3 ) salts, wherein
  • Ri, R 2 and R 3 are each independently of one another hydrogen
  • C r C 8 alkyl C ⁇ - alkenyl, C C 8 hydroxyalkyl, C 5 -C 8 cycloalkyl or polyalkenylenoxy- -Cigalkyl, or
  • Component (b) can consist of only one compound of subclass (b j ) or also of mixtures of one or more than one compound of subclass (b j ), also together with components of further subclasses.
  • a special antimicrobial activity is achieved with a combination of one or more than one compound of subclass (bj) and one or more than one compound of subclass b ⁇ ). Particularly preferred in this connection is a combination of cumene sulfonate and citric acid monohydrate.
  • Suitable components (c) are anionic, nonionic or zwitterionic and amphoteric synthetic, surface-active substances.
  • Suitable anionic surface-active substances are:
  • - sulfates typically fatty alcohol sulfates, which contain 8 to 18 carbon atoms in the alkyl chain, e.g. sulfated lauryl alcohol;
  • - C 8 -C 22 fatty alcohol ether sulfates typically the acid esters or the salts thereof of a polyadduct of 2 to 30 mol of ethylene oxide with 1 mol of a -C ⁇ fatty alcohol;
  • alkane sulfonates containing 8 to 20 carbon atoms in the alkyl chain, e.g. dodecyl sulfonate; alkylamide sulfonates; alkylaryl sulfonates; ⁇ -olefin sulfonates; sulfosuccinic acid derivatives, typically alkyl sulfosuccinates, alkyl ether sulfosuccinates or alkyl sulfosuccinamide derivatives;
  • X is hydrogen, C r C 4 alkyl or -COO M + ,
  • Y is hydrogen or C ⁇ -C alkyl
  • Z is -(CH 2 ) m 1 - m l is 1 to 5
  • n is an integer from 6 to 18, and
  • M is an alkali metal ion or an amine ion; alkyl ether carboxylates and alkylaryl ether carboxylates of formula
  • X is a radical
  • R is hydrogen or C ⁇ -C 4 alkyl
  • M is an alkali metal cation or amine cation.
  • the anionic surfactants used may furthermore be fatty acid methyl taurides, alkylisothionates, fatty acid polypeptide condensates and fatty alcohol phosphoric acid esters.
  • the alkyl radicals in these compounds preferably contain 8 to 24 carbon atoms.
  • the fatty alcohols which may be present in the above-mentioned surfactants are those containing 8 to 22, preferably 8 to 18 carbon atoms, typically octyl, decyl, lauryl, tridecyl, miristyl, cetyl, stearyl, oleyl, arachidyl or behenyl alcohol.
  • the anionic surfactants are usually obtained in the form of their water-soluble salts, such as the alkali metal, ammonium or amine salts.
  • Typical examples of such salts are lithium, sodium, potassium, ammonium, triethylamine, ethanolamine, diethanolamine or triethanolamine salts. It is preferred to use the sodium or potassium salts or the ammonium-(NR 1 R 2 R 3 ) salts, wherein R t , R 2 and R 3 are each independently of one another hydrogen, C ⁇ -C 4 alkyl or C Qhydroxyalkyl.
  • the anionic surfactants preferably used in the formulation of this invention are Cg-C ⁇ fatty acid alcohol ether sulfates, more particularly the alkali metal salts of lauryl ether sulfate.
  • Very particularly preferred anionic surfactants in the novel formulation are monoethanolamine lauryl sulfate or the alkali metal salts of fatty alcohol sulfates, preferably the sodium lauryl sulfate and the reaction product of 2 to 4 mol of ethylene oxide and sodium lauryl ether sulfate.
  • Suitable zwitterionic and amphoteric surfactants are C -C ⁇ 8 betaines, C 8 -C 18 sulfobetaines, C 8 -C 4 alkylamido-C 1 -C 4 alkylenebetaines, imidazoline carboxylates, alkylamphocarboxy carboxylic acids, alkylamphocarboxylic acids (e.g. lauroamphoglycinate) and N-alkyl- ⁇ - aminopropionates or N-alkyl- ⁇ -iminodipropionates. It is preferred to use the C 1 o-C 2 oalkylamido-C ⁇ -C 4 alkylenebetaines and, more particularly, cocoamidopropylbetaine.
  • Nonionic surfactants are typically derivatives of the adducts of propylene oxide/ethylene oxide having a molecular weight of 1000 to 15000, fatty alcohol ethoxylatcs (1-50 EO), alkylphenol polyglycol ethers (1-50 EO), ethoxylated carbohydrates, fatty acid glycol partial esters, typically diethylene glycol monstearate, fatty acid alkanolamides and fatty acid dialkanolamides, fatty acid alkanolamide ethoxylates and fatty acid amine oxides.
  • the fatty acid alkanolamides and fatty acid dialkanolamides and, preferably, cocodiethanolamide are to be particularly highlighted.
  • Suitable components (d) are the salts of saturated and unsaturated C 12 -C 22 fatty acids, typically lauric, myristic, palmitic, stearic, arachic, behenic, dodecenoic, tetradecenoic, octadecenoic, oleic, eicosanic and erucic acid, as well as the technical mixtures of such acids, typically coconut fatty acid which is preferably used in the novel formulation.
  • saturated and unsaturated C 12 -C 22 fatty acids typically lauric, myristic, palmitic, stearic, arachic, behenic, dodecenoic, tetradecenoic, octadecenoic, oleic, eicosanic and erucic acid, as well as the technical mixtures of such acids, typically coconut fatty acid which is preferably used in the novel formulation.
  • acids may be obtained in the form of salts, suitable cations being alkali metal cations such as sodium and potassium cations, metal atoms such as zinc atoms and aluminium atoms or nitrogen-containing organic compounds of sufficient alkalinity, typically amines or ethoxylated amines.
  • suitable cations being alkali metal cations such as sodium and potassium cations, metal atoms such as zinc atoms and aluminium atoms or nitrogen-containing organic compounds of sufficient alkalinity, typically amines or ethoxylated amines.
  • suitable cations being alkali metal cations such as sodium and potassium cations, metal atoms such as zinc atoms and aluminium atoms or nitrogen-containing organic compounds of sufficient alkalinity, typically amines or ethoxylated amines.
  • These salt can also be prepared in situ.
  • Component (d) can also be a mixture of the indicated salts.
  • Suitable components (e) are dihydric alcohols, preferably those containing 2 to 6 carbon atoms in the alkylene radical, typically ethylene glycol, 1,2- or 1,3-propanediol, 1,3-, 1,4- or 2,3-butanediol, 1,5-pentanediol and 1,6-hexanediol. 1,2-propanediol (propylene glycol) is preferred.
  • Component (f) is preferably ethanol, n-propanol and isopropanol or a mixture of these alcohols.
  • Preferred novel formulations are those comprising
  • Rj is hydrogen, hydroxy, Cj-Qalkyl, chloro, nitro, phenyl or benzyl,
  • R 2 is hydrogen, hydroxy, C j -C ⁇ alkyl or chloro
  • R 3 is hydrogen, Cj-Cgalkyl, hydroxy, chloro, nitro or a sulfo group in the form of the alkali metal salts or ammonium salts thereof,
  • R 4 is hydrogen or methyl
  • R 5 is hydrogen or nitro
  • the pH of the novel formulation is 3 to 10, preferably 4.5 to 6.
  • novel formulations obtained as soap or syndet solutions may additionally comprise customary additives, typically sequestrants, dyes, perfume oils, thickeners or solidifiers (consistency regulators), emollients, UV absorbers, skin-protection agents, antioxidants, additives which improve the mechanical properties, such as dicarboxylic acids and/or Al, Zn, Ca, Mg salts of C 14 -C 22 f tty acids and, if desired, preservatives.
  • customary additives typically sequestrants, dyes, perfume oils, thickeners or solidifiers (consistency regulators), emollients, UV absorbers, skin-protection agents, antioxidants, additives which improve the mechanical properties, such as dicarboxylic acids and/or Al, Zn, Ca, Mg salts of C 14 -C 22 f tty acids and, if desired, preservatives.
  • novel soap bars can be fabricated in per se known manner, typically by mixing the novel components (a) and (b) and, optionally, (c), (d), (e) and (f), as well as any additives in a jerk mixer at 18-25°C. After the composition obtained has been processed, it is extruded at 40 to 60°, preferably from 45 to 50°C, and then cut and stamped in moulds.
  • Soap formulations of the invention can be prepared by mixing components (a) and (b) and, optionally, (c), (d), (e) and (f), in any order, with the requisite amount of water and stirring the mixture to homogeneity.
  • the mixture is bulked to 100% with additional water. This procedure is a purely physical procedure. Accordingly, there is no chemical reaction of the individual components.
  • the novel soap formulations can be applied thereto in dilute or undilute form, suitably in an amount of at least 2 ml, preferably in the undilute form, for hand disinfection.
  • the invention is illustrated by the following Examples. Parts and percentages are by weight.
  • citric acid monohydrate 8.0 parts citric acid monohydrate, and water to make up 100 parts are stirred to homogeneity and about 90% of the requisite water is then added.
  • the pH is adjusted to 5.5 with monoethanolamine.
  • Deionised water is then added to the solution to make up a total of 100 parts.
  • the pH is checked again and, if necessary, monoethanolamine is added to adjust the pH to 4.0.
  • citric acid monohydrate 8.0 parts citric acid monohydrate, and water to make up 100 parts are stirred to homogeneity and about 90% of the requisite water is then added.
  • the pH is adjusted to 5.5 with monoethanolamine.
  • Deionised water is then added to the solution to make up a total of 100 parts.
  • the pH is checked again and, if necessary, monoethanolamine is added to adjust the pH to 4.0.
  • citric acid monohydrate 8.0 parts citric acid monohydrate, and water to make up 100 parts are stirred to homogeneity and about 90% of the requisite water is then added.
  • the pH is adjusted to 5.5 with monoethanolamine.
  • Deionised water is then added to the solution to make up a total of 100 parts.
  • the pH is checked again and, if necessary, monoethanolamine is added to adjust the pH to 4.0.
  • citric acid monohydrate 8.0 parts citric acid monohydrate, and water to make up 100 parts are stirred to homogeneity and about 90% of the requisite water is then added.
  • the pH is adjusted to 5.5 with monoethanolamine.
  • Deionised water is then added to the solution to make up a total of 100 parts.
  • the pH is checked again and, if necessary, monoethanolamine is added to adjust the pH to 4.0.
  • n is an integer from 7 to 17, 4.0 parts cocamidopropylbetaine,
  • Example 12 Test of the microbicidal activity of the novel formulations The microbicidal activity (in decimal logarithms) of the novel formulations according to Examples 1 to 11 is determined with a suspension test. This test is used to assess the bactericidal activity of water-soluble antiseptics, disinfectants and of liquid soaps.
  • the test consists in seeding the test product in selected dilutions with the test bacillus. After a certain contact time, aliquots is taken and the number of surviving bacilli is determined. The difference between the number of the bacilli added and the number of the surviving bacilli is expressed as bacilli reduction in decimal logarithms. The concentration is 90%, the contact time is 30 seconds.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Emergency Medicine (AREA)
  • Chemical & Material 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)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des formulations tensioactives de savon comprenant: (a) 0,01 à 5 % en poids d'une substance active microbicide choisie parmi le groupe consistant en (a1) dérivés phénol, (a2) composés diphényle, (a3) alcools benzyliques, (a4) chlorohexidine, (a5) alkylbétaïnes C12-C14 et amidoalkylbétaïnes d'acides gras C8-C18, (a6) tensioactifs amphotères, et (a7) trihalocarbanilides; (b) 0,1 à 25 % en poids d'un ou de plusieurs agent(s) hydrotrope(s); (c) 0 à 10 % en poids d'une ou de plusieurs substance(s) synthétique(s) tensioactive(s) ou d'un savon, ou de combinaisons des substances citées; (d) 0 à 8 % en poids d'un sel d'un acide gras C8-C22 saturé et/ou insaturé; (e) 0 à 50 % en poids d'alcool dihydrique; (f) 0 à 70 % en poids d'alcool monohydrique ou d'un mélange de plusieurs alcools monohydriques, et (g) de l'eau courante ou déminéralisée afin d'atteindre 100 % du poids de la composition, à condition que ces formulations contiennent au moins un des composants (c) et (d). On utilise ces formulations pour désinfecter et nettoyer la peau et les mains humaines ainsi que des objets durs.
PCT/EP1995/003211 1994-08-25 1995-08-14 Formulations tensioactives Ceased WO1996006153A2 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
CA002196771A CA2196771A1 (fr) 1994-08-25 1995-08-14 Formulations tensioactives
AU33452/95A AU3345295A (en) 1994-08-25 1995-08-14 Surface-active formulations
MX9701416A MX9701416A (es) 1994-08-25 1995-08-14 Formulaciones de actividad superficial.
EP95929863A EP0777717A2 (fr) 1994-08-25 1995-08-14 Formulations tensioactives
BR9508775A BR9508775A (pt) 1994-08-25 1995-08-14 Formulações tensoativas
JP8507758A JPH10504592A (ja) 1994-08-25 1995-08-14 界面活性組成物
SK244-97A SK24497A3 (en) 1994-08-25 1995-08-14 Surface-active formulations
FI970742A FI970742A7 (fi) 1994-08-25 1997-02-21 Pinta-aktiiviset valmisteet
BG101308A BG101308A (bg) 1994-08-25 1997-03-11 Повърхностноактивни състави

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH2611/94-8 1994-08-25
CH261194 1994-08-25

Publications (2)

Publication Number Publication Date
WO1996006153A2 true WO1996006153A2 (fr) 1996-02-29
WO1996006153A3 WO1996006153A3 (fr) 1996-05-02

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/003211 Ceased WO1996006153A2 (fr) 1994-08-25 1995-08-14 Formulations tensioactives

Country Status (12)

Country Link
EP (1) EP0777717A2 (fr)
JP (1) JPH10504592A (fr)
AU (1) AU3345295A (fr)
BG (1) BG101308A (fr)
BR (1) BR9508775A (fr)
CA (1) CA2196771A1 (fr)
CZ (1) CZ55697A3 (fr)
FI (1) FI970742A7 (fr)
HU (1) HUT76688A (fr)
MX (1) MX9701416A (fr)
SK (1) SK24497A3 (fr)
WO (1) WO1996006153A2 (fr)

Cited By (33)

* Cited by examiner, † Cited by third party
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EP0903401A1 (fr) * 1997-09-17 1999-03-24 Ciba SC Holding AG Additif antimicrobien pour détergents
WO1999028428A1 (fr) * 1997-11-28 1999-06-10 Reckitt Benckiser Inc. Nettoyant liquide concentre pour surfaces dures
JPH11189784A (ja) * 1997-12-26 1999-07-13 Kose Corp 洗浄剤組成物
US5955408A (en) * 1996-07-10 1999-09-21 Steris Inc. Triclosan skin wash with enhanced efficacy
WO1999046987A1 (fr) * 1998-03-19 1999-09-23 Bifodan A/S Composition desinfectante
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
TR199801841A3 (tr) * 1997-09-17 1999-10-21 Ciba Specialty Chemicals Holding Inc. Mikrop-önleyici deterjan katki maddesi.
US5977035A (en) * 1996-08-30 1999-11-02 Tomey Technology Corporation Liquid agent for contact lens containing carboxylated amine as a preservative or sterilizing component
US6075002A (en) * 1997-11-28 2000-06-13 Reckitt & Colman Inc. Biphenyl based solvents in blooming type germicidal hard surface cleaners
US6100231A (en) * 1997-11-28 2000-08-08 Reckitt & Colman Inc. Biphenyl based solvents in blooming type hard surface cleaners
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
US6183763B1 (en) 1997-06-04 2001-02-06 Procter & Gamble Company Antimicrobial wipes which provide improved immediate germ reduction
US6184195B1 (en) 1997-11-28 2001-02-06 Reckitt Benckiser Inc. Blooming type germicidal hard surface cleaners comprising biphenyl-based solvents
DE19937295A1 (de) * 1999-08-06 2001-02-15 Cognis Deutschland Gmbh Syndetseifen
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
US6190674B1 (en) 1997-06-04 2001-02-20 Procter & Gamble Company Liquid antimicrobial cleansing compositions
US6197315B1 (en) 1997-06-04 2001-03-06 Procter & Gamble Company Antimicrobial wipes which provide improved residual benefit versus gram negative bacteria
US6210695B1 (en) 1997-06-04 2001-04-03 The Procter & Gamble Company Leave-on antimicrobial compositions
US6214363B1 (en) 1997-11-12 2001-04-10 The Procter & Gamble Company Liquid antimicrobial cleansing compositions which provide residual benefit versus gram negative bacteria
US6284259B1 (en) 1997-11-12 2001-09-04 The Procter & Gamble Company Antimicrobial wipes which provide improved residual benefit versus Gram positive bacteria
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
US6287583B1 (en) 1997-11-12 2001-09-11 The Procter & Gamble Company Low-pH, acid-containing personal care compositions which exhibit reduced sting
WO2001074983A1 (fr) * 2000-04-04 2001-10-11 Becton, Dickinson And Company Formulation antimicrobienne moussante
US6451748B1 (en) 1999-06-23 2002-09-17 The Dial Corporation Compositions containing a high percent saturation concentration of antibacterial agent
WO2003044144A1 (fr) * 2001-11-16 2003-05-30 Becton, Dickinson And Company Preparation antimicrobienne expansible
US6861397B2 (en) 1999-06-23 2005-03-01 The Dial Corporation Compositions having enhanced deposition of a topically active compound on a surface
WO2006015725A3 (fr) * 2004-08-05 2006-04-27 Henkel Kgaa Utilisation d'ortho-phenylphenol et/ou de derives de celui-ci pour inhiber la reproduction asexuee de champignons
EP0904343B2 (fr) † 1995-10-25 2009-07-08 Reckitt Benckiser Inc. Composition acide germicide de nettoyage de surfaces dures
EP1987120B2 (fr) † 2006-02-24 2013-09-11 Unilever PLC Granules à libération rapide
US11564879B2 (en) 2016-11-23 2023-01-31 Gojo Industries, Inc. Sanitizer composition with probiotic/prebiotic active ingredient
US11633334B2 (en) 2017-05-01 2023-04-25 Gojo Industries, Inc. Alcohol containing non-antimicrobial cleansing composition
US11633451B2 (en) 2016-03-31 2023-04-25 Gojo Industries, Inc. Antimicrobial peptide stimulating cleansing composition
US11998575B2 (en) 2016-03-31 2024-06-04 Gojo Industries, Inc. Sanitizer composition with probiotic/prebiotic active ingredient

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JP2008106022A (ja) * 2006-10-27 2008-05-08 Miura Co Ltd 皮膚用殺菌剤
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JP5752220B2 (ja) * 2013-12-16 2015-07-22 花王株式会社 硬質表面用殺菌洗浄剤組成物
JP7219583B2 (ja) * 2018-10-19 2023-02-08 大日本除蟲菊株式会社 殺菌剤組成物

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EP0904343B2 (fr) † 1995-10-25 2009-07-08 Reckitt Benckiser Inc. Composition acide germicide de nettoyage de surfaces dures
US5955408A (en) * 1996-07-10 1999-09-21 Steris Inc. Triclosan skin wash with enhanced efficacy
US5977035A (en) * 1996-08-30 1999-11-02 Tomey Technology Corporation Liquid agent for contact lens containing carboxylated amine as a preservative or sterilizing component
US6197315B1 (en) 1997-06-04 2001-03-06 Procter & Gamble Company Antimicrobial wipes which provide improved residual benefit versus gram negative 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
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
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
US6183763B1 (en) 1997-06-04 2001-02-06 Procter & Gamble Company Antimicrobial wipes which provide improved immediate germ reduction
US6190674B1 (en) 1997-06-04 2001-02-20 Procter & Gamble Company Liquid antimicrobial cleansing compositions
EP0903401A1 (fr) * 1997-09-17 1999-03-24 Ciba SC Holding AG Additif antimicrobien pour détergents
TR199801841A3 (tr) * 1997-09-17 1999-10-21 Ciba Specialty Chemicals Holding Inc. Mikrop-önleyici deterjan katki maddesi.
US6365563B1 (en) 1997-09-17 2002-04-02 Ciba Specialty Chemicals Corporation Agglomerated antimicrobial detergent additive comprising swellable layered silicate and surfactant
US6284259B1 (en) 1997-11-12 2001-09-04 The Procter & Gamble Company Antimicrobial wipes which provide improved residual benefit versus Gram positive bacteria
US6287583B1 (en) 1997-11-12 2001-09-11 The Procter & Gamble Company Low-pH, acid-containing personal care compositions which exhibit reduced sting
US6214363B1 (en) 1997-11-12 2001-04-10 The Procter & Gamble Company Liquid antimicrobial cleansing compositions which provide residual benefit versus gram negative bacteria
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
US6184195B1 (en) 1997-11-28 2001-02-06 Reckitt Benckiser Inc. Blooming type germicidal hard surface cleaners comprising biphenyl-based solvents
US6100231A (en) * 1997-11-28 2000-08-08 Reckitt & Colman Inc. Biphenyl based solvents in blooming type hard surface cleaners
US6075002A (en) * 1997-11-28 2000-06-13 Reckitt & Colman Inc. Biphenyl based solvents in blooming type germicidal hard surface cleaners
WO1999028428A1 (fr) * 1997-11-28 1999-06-10 Reckitt Benckiser Inc. Nettoyant liquide concentre pour surfaces dures
JPH11189784A (ja) * 1997-12-26 1999-07-13 Kose Corp 洗浄剤組成物
WO1999046987A1 (fr) * 1998-03-19 1999-09-23 Bifodan A/S Composition desinfectante
LT4778B (lt) 1998-03-19 2001-04-25 Bifodan A/S Dezinfekavimo kompozicija
AU740138B2 (en) * 1998-03-19 2001-11-01 Bifodan A/S Disinfecting composition
US6414023B1 (en) 1998-03-19 2002-07-02 Bifodan A/S Disinfecting composition
US6451748B1 (en) 1999-06-23 2002-09-17 The Dial Corporation Compositions containing a high percent saturation concentration of antibacterial agent
US6861397B2 (en) 1999-06-23 2005-03-01 The Dial Corporation Compositions having enhanced deposition of a topically active compound on a surface
DE19937295A1 (de) * 1999-08-06 2001-02-15 Cognis Deutschland Gmbh Syndetseifen
DE19937295C2 (de) * 1999-08-06 2002-11-21 Cognis Deutschland Gmbh Syndetseifen
WO2001074983A1 (fr) * 2000-04-04 2001-10-11 Becton, Dickinson And Company Formulation antimicrobienne moussante
WO2003044144A1 (fr) * 2001-11-16 2003-05-30 Becton, Dickinson And Company Preparation antimicrobienne expansible
WO2006015725A3 (fr) * 2004-08-05 2006-04-27 Henkel Kgaa Utilisation d'ortho-phenylphenol et/ou de derives de celui-ci pour inhiber la reproduction asexuee de champignons
EP1987120B2 (fr) † 2006-02-24 2013-09-11 Unilever PLC Granules à libération rapide
US11633451B2 (en) 2016-03-31 2023-04-25 Gojo Industries, Inc. Antimicrobial peptide stimulating cleansing composition
US11998575B2 (en) 2016-03-31 2024-06-04 Gojo Industries, Inc. Sanitizer composition with probiotic/prebiotic active ingredient
US11564879B2 (en) 2016-11-23 2023-01-31 Gojo Industries, Inc. Sanitizer composition with probiotic/prebiotic active ingredient
US11633334B2 (en) 2017-05-01 2023-04-25 Gojo Industries, Inc. Alcohol containing non-antimicrobial cleansing composition
US11660258B2 (en) 2017-05-01 2023-05-30 Gojo Industries, Inc. Alcohol containing non-antimicrobial cleansing composition
US11712409B2 (en) 2017-05-01 2023-08-01 Gojo Industries, Inc. Alcohol containing low-water cleansing composition
US11998626B2 (en) 2017-05-01 2024-06-04 Gojo Industries, Inc. Alcohol containing non-antimicrobial cleansing composition

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AU3345295A (en) 1996-03-14
JPH10504592A (ja) 1998-05-06
BG101308A (bg) 1997-09-30
CA2196771A1 (fr) 1996-02-29
FI970742A0 (fi) 1997-02-21
HUT76688A (en) 1997-10-28
FI970742A7 (fi) 1997-02-21
SK24497A3 (en) 1997-07-09
EP0777717A2 (fr) 1997-06-11
CZ55697A3 (en) 1997-06-11
WO1996006153A3 (fr) 1996-05-02
BR9508775A (pt) 1997-12-23
MX9701416A (es) 1997-05-31

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