EP0777716A2 - Surface-active formulations - Google Patents
Surface-active formulationsInfo
- Publication number
- EP0777716A2 EP0777716A2 EP95929862A EP95929862A EP0777716A2 EP 0777716 A2 EP0777716 A2 EP 0777716A2 EP 95929862 A EP95929862 A EP 95929862A EP 95929862 A EP95929862 A EP 95929862A EP 0777716 A2 EP0777716 A2 EP 0777716A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- formulation according
- component
- weight
- formulation
- compound
- 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.)
- Withdrawn
Links
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.
Abstract
The invention relates to surface-active soap formulations, comprising (a) 0.01 to 0.2 % by weight of a microbicidal active substance, (b) 0.1 to 7.5 % by weight of one or more than one hydrotropic agent, (c) 0 to 2 % by weight of one or more than one synthetic surface-active substance or of a soap or of combinations of the cited substances and/or of a salt of a saturated and/or unsaturated C8-C22fatty acid, (d) 0 to 10 % by weight of a dihydric alcohol, (e) 0 to 70 % by weight of a monohydric alcohol, and (f) mains water or deionised water to make up 100 %. The formulation is used for the disinfection and cleansing of the human skin and hands and of hard objects.
Description
Surface-active formulations
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.
Special demands of hygiene are not only in hospitals, restaurants or in the food sector, but also in the private sector, as for example in private households or when travelling whereby the demands made upon the disinfectants employed are undoubtedly less stringent in these sectors than in the first-mentioned group. Nonetheless these disinfectants should act within as short a time as possible, and they should preferably be worth the money, have good skin compatibility and be ecologically safe.
Surprisingly, it has now been found that a formulation comprising an extremely low concentration of a microbicidal active substance as well as further components, typically surface-active components, has these properties.
The surface-active formulations comprise
(a) 0.01 to 0.2% by weight of a microbicidal active substance,
(b) 0.1 to 7.5% by weight of one or more than one hydrotropic agent,
(c) 0 to 2% by weight of one or more than one synthetic surface-active substance or of a soap or of combinations of the cited substances and/or of a salt of a saturated and/or unsaturated Cg-C^føtty acid,
(d) 0 to 10% by weight of a dihydric alcohol,
(e) 0 to 70% by weight of a monohydric alcohol, and
(f) mains water or deionised water to make up 100%.
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
wherein
X is oxygen, sulfur or -CH ,
Y is chloro or bromo, z is S02H, N02 or Cj -C4alkyl,
P is O or 1,
n is O or 1.
Of particular interest are compounds of formula (1), wherein
X is oxygen, sulfur or -CH2-, and
Y is chloro or bromo,
r 1 is or 2, and
Of very particular interest are compounds of formula (1), wherein X is oxygen, and Y is chloro, m is O, n is O, o is 1, r is 2, and
P is O.
The compound of formula
is very particularly preferred here.
Component (a) in the novel formulation is preferably used in amounts of 0.02 to 0.2% by weight.
The following compounds are suitable for use as component (b):
(bj): sulfonates, preferably the salts thereof of terpenoids, or mono- or binuclear aromatic compounds, typically sulfonates of camphor, toluene, xylene, cumene or naphthene; (b2): saturated or unsaturated C3-C12di- or polycarboxylic acids, typically malonic, succinic, glutaric, adipic, pimelic, suberic, azelaic and sebacic acid, unde- canedicarboxylic acid and dodecanedicarboxylic acid, fumaric, maleic, tartaric and malic acid as well as citric and aconitic acid; (b3): - aliphatic saturated or unsaturated C^Cnmonocarboxylic acids, typically acetic, propionic, hexanoic, capric or undecylenoic acid;
- saturated or unsaturated C3-C12di- 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;
- cycloaliphatic carboxylic acids such as camphoric 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 amineCRjR^) salts of hydrochloric, sulfuric, phosphoric, Cj-Cjoalkylphosphoric acid and boric acid, in which amine salts Rj, R and R3 have the meaning indicated above;
- isethionic acid;
- tannic acid;
- acid amides of formula
/ R2
(3) RrCO-N
X R3 wherein
Rj is hydrogen or Cι-C12alkyl, and
R2 and R3 are each independently of the other hydrogen, CrC12alkyl,
C -C12alkenyl, C1-C12hydroxyalkenyl, C2-C12hydroxyalkyl, or a polyglycol ether chain containing 1 to 30 -CH2-CH2-0- or -CHYrCHY2-O- groups, wherein one of the radicals of Yj or Y2 is hydrogen and the other is methyl, e.g.
N-methylacetamide;
- urea derivatives of formula
(4) N-CO-N
' \ D '
R2 R4
wherein
Rj, R2, R3 and R4 are each independently of one another hydrogen, Ci-Cgalkyl,
C -C8alkenyl, -Cghydroxyalkyl or C -C8hydroxyalkenyl;
- monohydric C4-C18aliphatic and monocyclic alcohols, typically C -C18alkanols, C2-C18alkenols 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;
- aromatic alcohols of formula
wherein
X is -(CHj),^, -CH=CH-CH2-, or -O- CH^^, and
Rj, R2 and R3 are each independently of one another hydrogen, hydroxy, halogen
or CrC6alkoxy, typically benzyl alcohol, 2,4-dichlorobenzyl alcohol, phenoxyethanol, l-phenoxy-2-propanol (phenoxyisopropanol) and cinnamyl alcohol;
- polyhydric alcohols and polyhydric alkoxylated, preferably ethoxylated and/or propoxylated alcohols as well as the ethers and esters thereof of the general formula
(6) RrO-X-0-R2,
wherein
Rj and R2 are each independently of the other hydrogen, CrC12alkyl, C2-C12alkenyl, Cj-Cgalkanoyl, C3-C18alkenoyl, R3-(OCH-CH2-)jT5o-, wherein
I
R4
R3 is hydrogen, CrC1 alkyl or C^-C^alkenyl, and R4 is hydrogen or -CH3, and
-(CH2-CH-0)τ3ό-CH2-CH- .
CH3 CH3
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(NRιR2R3) salts, wherein
Rj, R2 and R3 are each independently of one another hydrogen,
CrC8alkyl, C alkenyl, C1-C8hydroxyalkyl, C5-C8cycloalkyl or polyalkenylenoxy-
CrC18alkyl, or
Rj, R2 and R3, together with the linking nitrogen atom, are unsubstituted or
CrC4alkyl-substituted morpholino.
Component (b) can consist of only one compound of subclass (bj) or also of mixtures of one or more than one compound of subclass (bι ), 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 (b2) 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 C8-C22fatty alcohol;
- the alkali metal salts, ammonium salts or amine salts of C8-C20fatty acids, which are termed soaps, typically coconut fatty acid;
- alkylamide sulfates;
- alkylamine sulfates, typically monoethanolamine lauryl sulfate;
- alkylamide ether sulfates;
- alkylaryl polyether sulfates;
- monoglyceride sulfates;
- alkane sulfonates, containing 8 to 20 carbon atoms in the alkyl chain, e.g. dodecyl sulfonate;
- alkylamide sulfonates;
- alkylaryl sulfonates;
- α-olefin sulfonates;
- sulfosuccinic acid derivatives, typically alkyl sulfosuccinates, alkyl ether sulfosuccinates or alkyl sulfosuccinamide derivatives;
- N-[alkylamidoalkyl]amino acids of formula
/
CH3(CH2)n-CO-N (7) \
CH-Z-COO M+
I X
wherein
X is hydrogen, CrC4alkyl or -COO M+,
Y is hydrogen or - alkyl, Z is -(CH2) m 1 -
ΪΪI 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
(8) CH3-X-Y-A ,
wherein
X is a radical ,
R is hydrogen or Cj- alkyl, Y is -(CHCHO T30-,
? 0-M+ A is -(CH ) — COO M+ or " y O M+ m2 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]R2R3) salts, wherein Rj, R2 and R3 are each independently of one another hydrogen, Cι-C4alkyl or CrC4hydroxyalkyl.
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 -C18betaines, C8-C18sulfobetaines, C8-C 4alkylamido-C1-C alkylenebetaines, imidazoline carboxylates, alkylamphocarboxy carboxylic acids, alkylamphocarboxylic acids (e.g. lauroamphoglycinate) and N-alkyl-β- aminopropionates or N-alkyl-β-iminodipropionates. It is preferred to use the C1o-C2oalkylamido-C1-C4alkylenebetaines 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.
For 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. These 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. These salt can also be prepared in situ.
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.
The 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 C1 -C 2fatty 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.
For disinfection and cleansing of the human skin and hands and of hard objects, 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.
Example 1:
0.075 % 2,4,4,-trichloro-2'-hydroxydiphenyl ether,
0.5 % monoethanolamine laurylsulfate
0.25 % sodium cumene sulfonate powder,
0.4 % citric acid monohydrate, and
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.
Example 2:
0.25 % 2,4,4'-trichloro-2'-hydroxydiphenyl ether
1.0 % monoethanolamine lauryl sulfate
2.5 % sodium cumene sulfonate powder,
1.5 % citric acid monohydrate, and
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.
Example 3:
0.15 % 2,4,4'-trichloro-2'-hydroxydiphenyl ether
1.0 % monoethanolamine lauryl sulfate
0.5 % sodium cumene sulfonate powder,
0.8 % citric acid monohydrate, and
5.0 % 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.
Example 4:
0.1 % 2,4,4,-trichloro-2,-hydroxydiphenyl ether
4.0 % monoethanolamine lauryl sulfate
0.5 % sodium cumene sulfonate powder, and
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.
The following bacilli are used:
Example I 2 3 4
Staph. aureus ATCC 9144 >5.0 >5.0 >5.0 >5.1
Strept. faecalis ATCC 10,541 >5.2 >5.2 >5.2 >5.2
E. Coli ATCC 10,536 4.3 5.1 4.0 *
P. aeruginosa CIP A-22 5.4 >5.4 >5.4
Serratia marcescens ATCC 13,880 * * * >5.4**
* not measured
** contact time 5 minutes
Values above 4 indicate good antimicrobial activity.
Claims
1. A surface- active surfactant formulation, comprising
(a) 0.01 to 0.2% by weight of a microbicidal active substance,
(b) 0.1 to 7.5% by weight of one or more than one hydrotropic agent,
(c) 0 to 2% by weight of one or more than one synthetic surface- active substance or of a soap or of combinations of the cited substances and/or of a salt of a saturated and/or unsaturated C8-C22fatty acid,
(d) 0 to 10% by weight of a dihydric alcohol,
(e) 0 to 70% by weight of a monohydric alcohol, and
(f) mains water or deionised water to make up 100%.
2. A formulation according to claim 1, wherein component (a) is 2-hydroxydiphenyl ether, 2-hydroxydiphenylmethane and 2-hydroxydiphenyl thioether of the general formula
wherein
X is oxygen, sulfur or -CH2-,
Y is chloro or bromo,
Z is S02H, N02 or CrC4alkyl, r is 0 to 3, o is 0 to 3, p is O or l, m is 0 or 1, and n is O or l.
3. A formulation according to claim 2, wherein the compounds used for component (a) are those of formula (1), wherein
X is oxygen, sulfur or -CH2-, and
Y is chloro or bromo, m is O, n is O or l, o is 1 or 2, r is 1 or 2, and p is O.
4. A formulation according to claim 2 or 3, wherein the compounds used for component (a) are those of formula (1), wherein
X is oxygen, and
Y is chloro, m is O, n is O, o is 1, r is 2, and p is O.
5. A formulation according to claim 4, wherein the compound used for component (a) is that of formula
6. A formulation according to any one of claims 1 to 5, wherein component (a) is used in an amount of 0.02 to 0.2% by weight.
7. A formulation according to any one of claims 1 to 6, wherein component (bj) is a sulfonate, preferably a salt thereof of a terpenoid or of a mono- or binuclear aromatic compound.
8. A formulation according to claim 7, wherein the mono-or binuclear aromatic compound is a sulfonate of camphor, toluene, xylene, cumene or naphthene.
9. A formulation according to claim 7, wherein component (b) consists of only one compound of subclass (bj) or also of a mixture of one or more than one compound of subclass (bj), also with components of further subclasses.
10. A formulation according to any one of claims 1 to 7, wherein component (b) is a combination of one or more than one compound of subclass (bt) and one or more than one compound of subclass (b^.
11. A formulation according to claim 9, wherein a combination of cumene sulfonate and citric acid monohydrate is used.
12. A formulation of any one of claims 1 to 11 , wherein the anionic surfactant is a fatty alcohol sulfate, which contains 8 to 18 carbon atoms in the chain.
13. A formulation according to claim 12, wherein the anionic surfactant is the alkali metal salt of the sulfated lauryl alcohol or of the monoethanolamine lauryl sulfate.
14. A formulation according to any one of claims 1 to 11, wherein component (b) is C1o-C20alkylamido-Ci-C4alkylenebetaine.
15. A formulation according to any one of claims 1 to 14, wherein the salt of a saturated and/or unsaturated -C^fatty acid corresponding to component (c) is selected from the group consisting of lauric, myristic, palmitic, stearic, arachic, behenic, dodecenoic, tetradecenoic, octadecenoic, oleic, eicosanic and erucic acid.
16. A formulation according to any one of claims 1 to 15, wherein component (d) is propylene glycol.
17. A formulation according to any one of claims 1 to 16, wherein component (e) is selected from the group consisting of ethanol, propanol, isopropanol and mixtures of these alcohols.
18. A formulation according to either claim 16 or claim 17, wherein components (d) and (e) are used in admixture with each other.
19. Use of an antimicrobial soap formulation according to any one of claims 1 to 18 for the disinfection and cleansing of the human skin and hands and of hard objects.
20. Use according to claim 19, wherein the antimicrobial soap formulation is in dilute or undilute form.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH261094 | 1994-08-25 | ||
CH2610/94 | 1994-08-25 | ||
PCT/EP1995/003210 WO1996006152A2 (en) | 1994-08-25 | 1995-08-14 | Surface-active formulations |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0777716A2 true EP0777716A2 (en) | 1997-06-11 |
Family
ID=4237644
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP95929862A Withdrawn EP0777716A2 (en) | 1994-08-25 | 1995-08-14 | Surface-active formulations |
Country Status (12)
Country | Link |
---|---|
EP (1) | EP0777716A2 (en) |
JP (1) | JPH10504591A (en) |
AU (1) | AU3345195A (en) |
BG (1) | BG101306A (en) |
BR (1) | BR9508767A (en) |
CA (1) | CA2196774A1 (en) |
CZ (1) | CZ55597A3 (en) |
FI (1) | FI970741A (en) |
HU (1) | HUT77706A (en) |
MX (1) | MX9701417A (en) |
SK (1) | SK24597A3 (en) |
WO (1) | WO1996006152A2 (en) |
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ES2184119T3 (en) * | 1996-07-10 | 2003-04-01 | Steris Inc | TRICLOSAN-BASED SKIN CLEANING PRODUCT WITH IMPROVED EFFECTIVENESS. |
BR9603085A (en) * | 1996-07-12 | 1998-05-05 | Cosmeticos Natural Ind Com | Liquid antiseptic soap for skin care |
US6284259B1 (en) | 1997-11-12 | 2001-09-04 | The Procter & Gamble Company | Antimicrobial wipes 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 |
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 |
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 |
US6197315B1 (en) | 1997-06-04 | 2001-03-06 | Procter & Gamble Company | Antimicrobial wipes which provide improved residual benefit versus gram negative bacteria |
US6214363B1 (en) | 1997-11-12 | 2001-04-10 | The Procter & Gamble Company | Liquid antimicrobial cleansing compositions which provide residual benefit versus gram negative bacteria |
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 |
US6287583B1 (en) | 1997-11-12 | 2001-09-11 | The Procter & Gamble Company | Low-pH, acid-containing personal care compositions which exhibit reduced sting |
US6861397B2 (en) * | 1999-06-23 | 2005-03-01 | The Dial Corporation | Compositions having enhanced deposition of a topically active compound on a surface |
US6107261A (en) * | 1999-06-23 | 2000-08-22 | The Dial Corporation | Compositions containing a high percent saturation concentration of antibacterial agent |
WO2000078141A1 (en) * | 1999-06-23 | 2000-12-28 | The Dial Corporation | Antibacterial compositions |
BR0011860A (en) * | 1999-06-23 | 2002-04-30 | Dial Corp | Antibacterial compositions and process for reducing a population of bacteria on a surface |
DE19957739A1 (en) * | 1999-12-01 | 2001-06-28 | Henkel Ecolab Gmbh & Co Ohg | Hand wash lotion for refillable foam generator |
EP1167503B1 (en) * | 2000-06-21 | 2006-03-22 | Ciba SC Holding AG | Surface-active preparations |
US8329685B1 (en) | 2000-07-19 | 2012-12-11 | North West University | Enhancement of the action of anti-infective agents and of central and peripheral nervous system agents and transportation of nucleic acid substances |
EP1341886B1 (en) | 2000-12-14 | 2006-03-08 | Ciba SC Holding AG | Surface-active compositions |
US6616922B2 (en) | 2001-03-27 | 2003-09-09 | The Dial Corporation | Antibacterial compositions |
MXPA03008869A (en) * | 2001-03-29 | 2004-05-24 | Dial Corp | Antibacterial compositions for skin care. |
US6794351B2 (en) | 2001-04-06 | 2004-09-21 | Kimberly-Clark Worldwide, Inc. | Multi-purpose cleaning articles |
AU2002308579B2 (en) * | 2001-05-01 | 2004-07-15 | The Dial Corporation | Method for reducing malodors in hydrotropic compositions |
GB2393907A (en) * | 2002-10-12 | 2004-04-14 | Reckitt Benckiser Inc | Antimicrobial hard surface cleaner |
EP1830638A2 (en) * | 2004-12-09 | 2007-09-12 | The Dial Corporation | Compositions having a high antiviral and antibacterial efficacy |
KR20090018120A (en) | 2006-06-14 | 2009-02-19 | 시바 홀딩 인코포레이티드 | Antimicrobial compositions |
US20080026974A1 (en) | 2006-07-27 | 2008-01-31 | Barnhart Ronald A | Antimicrobial hand wash |
EP2708593A1 (en) | 2012-09-14 | 2014-03-19 | The Procter & Gamble Company | Fabric care composition |
EP2727991A1 (en) * | 2012-10-30 | 2014-05-07 | The Procter & Gamble Company | Cleaning and disinfecting liquid hand dishwashing detergent compositions |
WO2016172481A1 (en) | 2015-04-23 | 2016-10-27 | The Procter & Gamble Company | Concentrated personal cleansing compositions and methods |
CN107530248B (en) | 2015-04-23 | 2021-03-12 | 宝洁公司 | Concentrated personal cleansing compositions and methods |
EP3285725B1 (en) | 2015-04-23 | 2019-12-04 | The Procter and Gamble Company | Concentrated personal cleansing compositions |
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EP3528777B1 (en) | 2016-10-21 | 2021-09-01 | The Procter & Gamble Company | Skin cleansing compositions and methods |
US11185486B2 (en) | 2016-10-21 | 2021-11-30 | The Procter And Gamble Company | Personal cleansing compositions and methods |
US10806686B2 (en) | 2017-02-17 | 2020-10-20 | The Procter And Gamble Company | Packaged personal cleansing product |
US10675231B2 (en) | 2017-02-17 | 2020-06-09 | The Procter & Gamble Company | Packaged personal cleansing product |
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-
1995
- 1995-08-14 CZ CZ97555A patent/CZ55597A3/en unknown
- 1995-08-14 CA CA002196774A patent/CA2196774A1/en not_active Abandoned
- 1995-08-14 MX MX9701417A patent/MX9701417A/en unknown
- 1995-08-14 JP JP8507757A patent/JPH10504591A/en active Pending
- 1995-08-14 SK SK245-97A patent/SK24597A3/en unknown
- 1995-08-14 AU AU33451/95A patent/AU3345195A/en not_active Abandoned
- 1995-08-14 BR BR9508767A patent/BR9508767A/en not_active Application Discontinuation
- 1995-08-14 EP EP95929862A patent/EP0777716A2/en not_active Withdrawn
- 1995-08-14 WO PCT/EP1995/003210 patent/WO1996006152A2/en not_active Application Discontinuation
- 1995-08-14 HU HU9800340A patent/HUT77706A/en unknown
-
1997
- 1997-02-21 FI FI970741A patent/FI970741A/en unknown
- 1997-03-11 BG BG101306A patent/BG101306A/en unknown
Non-Patent Citations (1)
Title |
---|
See references of WO9606152A2 * |
Also Published As
Publication number | Publication date |
---|---|
CZ55597A3 (en) | 1997-06-11 |
SK24597A3 (en) | 1997-08-06 |
HUT77706A (en) | 1998-07-28 |
WO1996006152A3 (en) | 1996-05-02 |
MX9701417A (en) | 1997-05-31 |
FI970741A0 (en) | 1997-02-21 |
BG101306A (en) | 1997-09-30 |
WO1996006152A2 (en) | 1996-02-29 |
JPH10504591A (en) | 1998-05-06 |
FI970741A (en) | 1997-02-21 |
AU3345195A (en) | 1996-03-14 |
CA2196774A1 (en) | 1996-02-29 |
BR9508767A (en) | 1997-11-11 |
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