Classifications

• • 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
  • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
• • 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
• • 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

Definitions

• the present invention relates to surface-active formulations as well as to their use for the disinfection and cleansing of the human skin and hands and of hard objects.
• the surface-active formulations comprise
• Soap formulations will be understood as meaning aqueous soap solutions which may be obtained as soap or so-called syndet solutions (synthetic detergents).
• the antimicrobial activity of the novel formulation reaches gram-positive and gram-negative bacteria as well as yeasts, dermatophytes and the like.
• Suitable components (a) are preferably 2-hydroxydiphenyl ethers, 2-hydroxydiphenyl methanes and 2-hydroxydiphenyl thioethers of the general formula
• X is oxygen, sulfur or -CH ,
• Y is chloro or bromo
• z is S0 2 H, N0 2 or Cj -C 4 alkyl
• n O or 1.
• X is oxygen, sulfur or -CH 2 -
• Y is chloro or bromo
• r 1 is or 2
• Component (a) in the novel formulation is preferably used in amounts of 0.02 to 0.2% by weight.
• C 3 -C 12 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;
• amine salts Rj, R and R 3 have the meaning indicated above;
• Rj is hydrogen or C ⁇ -C 12 alkyl
• R 2 and R 3 are each independently of the other hydrogen, C r C 12 alkyl,
• Rj, R 2 , R 3 and R 4 are each independently of one another hydrogen, Ci-Cgalkyl,
• C 4 -C 18 aliphatic and monocyclic alcohols typically C -C 18 alkanols, C 2 -C 18 alkenols and teipene alcohols e.g. ethanol, propanol, isopropanol, hexanol, cis-3-hexene-l-ol, trans-2-hexene-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 2 and R 3 are each independently of one another hydrogen, hydroxy, halogen or C r C 6 alkoxy, typically benzyl alcohol, 2,4-dichlorobenzyl alcohol, phenoxyethanol, l-phenoxy-2-propanol (phenoxyisopropanol) and cinnamyl alcohol;
• Rj and R 2 are each independently of the other hydrogen, C r C 12 alkyl, C 2 -C 12 alkenyl, Cj-Cgalkanoyl, C 3 -C 18 alkenoyl, R 3 -(OCH-CH 2 -)jT 5 o-, wherein
• R 3 is hydrogen, C r C 1 alkyl or C ⁇ -C ⁇ alkenyl
• R 4 is hydrogen or -CH 3 , and -(CH 2 -CH-0) ⁇ 3 ⁇ -CH 2 -CH- .
• 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(NR ⁇ R 2 R 3 ) salts, wherein
• R j , R 2 and R 3 are each independently of one another hydrogen
• R j , R 2 and R 3 together with the linking nitrogen atom, are unsubstituted or
• Component (b) can consist of only one compound of subclass (bj) or also of mixtures of one or more than one compound of subclass (b ⁇ ), also together with components of further subclasses. Preferably a combination of one or more than one compound of subclass (bj) and one or more than one compound of subclass (b 2 ) is used.
• 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;
• - 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 8 -C 22 fatty alcohol;
• alkali metal salts, ammonium salts or amine salts of C 8 -C 20 f att y acids which are termed soaps, typically coconut fatty acid;
• alkylamine sulfates typically monoethanolamine lauryl sulfate
• alkane sulfonates containing 8 to 20 carbon atoms in the alkyl chain, e.g. dodecyl sulfonate;
• 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 - alkyl
• Z is -(CH 2 ) m 1 -
• ⁇ I 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 j - alkyl, Y i s -(CHCHO T30-,
• 0-M + A is -(CH ) — COO M + or " y O M + m 2 is 1 to 6, and
• M is an alkali metal cation or an 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 anionic surfactants arc 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, trie thy lamine, ethanolamine, diethanolamine or triethanolamine salts. It is preferred to use the sodium or potassium salts or the ammonium-(NR ] R 2 R 3 ) salts, wherein R j , R 2 and R 3 are each independently of one another hydrogen, C ⁇ -C 4 alkyl or C r C 4 hydroxyalkyl.
• 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 18 betaines, C 8 -C 18 sulfobetaines, C 8 -C 4 alkylamido-C 1 -C 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 1 -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 ethoxylates (1-50 EO), alkylphenol polyglycol ethers (1-50 EO), ethoxylated carbohydrates, fatty acid glycol partial esters, typically diethylene glycol monostearate, fatty acid alkanolamides and fatty acid dialkanolamides, fatty acid alkanolamide ethoxylates and fatty acid amine oxides.
• component (c) may furthermore be used the salts of saturated and unsaturated Cg- ⁇ fatty acids, either by themselves, in admixture with each other or in admixture with the other surface-active substances cited for component (c).
• Illustrative examples of these fatty acids are typically capric, 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.
• 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.
• Suitable components (d) 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 (e) is preferably ethanol, n-propanol and isopropanol, or a mixture of these alcohols. Components (d) and (e) may also be obtained in admixture with each other.
• the pH of the novel formulation is 3 to 10, preferably 3,5 to 5,5.
• 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 1 -C 2 fatty 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 1 -C 2 fatty acids and, if desired, preservatives.
• Soap formulations of the invention can be prepared by mixing components (a) and (b) and, optionally, (c), (d) and (e), in any order, with the requisite amount of water and stirring the mixture to homogeneity.
• the mixture is bulked to 100% with mains water or deinonised 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.
• 0.5 % propylene glycol are stirred to homogeneity and about 90% of the requisite water is then added.
• the pH is adjusted to 4.0 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.
• 1.0 % propylene glycol are stirred to homogeneity and about 90% of the requisite water is then added.
• the pH is adjusted to 4.0 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.
• 0.019 % NaOH are stirred to homogeneity and about 90% of the requisite water is then added.
• the pH is adjusted to 9.1 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 9.1.
• Example 5 Test of the microbicidal activitiv of the novel formulations The microbicidal activity (in decimal logarithms) of the novel formulations according to Examples 1 to 4 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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Cited By (32)

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Citations (10)

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• 1995
  • 1995-08-14 SK SK245-97A patent/SK24597A3/sk unknown
  • 1995-08-14 AU AU33451/95A patent/AU3345195A/en not_active Abandoned
  • 1995-08-14 WO PCT/EP1995/003210 patent/WO1996006152A2/en not_active Application Discontinuation
  • 1995-08-14 BR BR9508767A patent/BR9508767A/pt not_active Application Discontinuation
  • 1995-08-14 EP EP95929862A patent/EP0777716A2/de not_active Withdrawn
  • 1995-08-14 CZ CZ97555A patent/CZ55597A3/cs unknown
  • 1995-08-14 CA CA002196774A patent/CA2196774A1/en not_active Abandoned
  • 1995-08-14 MX MX9701417A patent/MX9701417A/es unknown
  • 1995-08-14 JP JP8507757A patent/JPH10504591A/ja active Pending
  • 1995-08-14 HU HU9800340A patent/HUT77706A/hu unknown
• 1997
  • 1997-02-21 FI FI970741A patent/FI970741A/fi unknown
  • 1997-03-11 BG BG101306A patent/BG101306A/xx unknown

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