HUT77706A - Surface-active soap formulations - Google Patents

Description

The present invention relates to a surfactant composition and to its use for disinfecting and cleaning additional solid surfaces of the human skin and hands.

The need for hygiene arises not only in hospitals, restaurants or the food sector, but also in the private sector, such as households or travel, where the demand for disinfectants used is undoubtedly less stringent than in the former. These disinfectants should be effective as soon as possible, be economical and have good skin compatibility and ecological safety.

·· * · ·· »·

Surprisingly, it has been found that a composition containing a low concentration of a microbicidal active ingredient and other components, preferably surfactants, has these properties.

The surfactant composition of the present invention comprises (a) 0.01-0.2% by weight of a microbicidal active ingredient, (b) 0.1-7.5% by weight of one or more hydrotropic agents, (c) 0-2% by weight of one or more a plurality of synthetic surfactants or soaps or combinations thereof and / or a saturated and / or unsaturated C8-C22 fatty acid salt, (d) 0 to 10% by weight of a divalent alcohol, (e) 0 to 70% by weight of a monovalent alcohol, and (f) It contains 100% extra water.

The term "soap composition" refers to aqueous soap solutions which may be obtained as soap or in the form of a so-called syndet solution (synthetic detergent).

The antimicrobial activity of the new formulations relates to gram positive and gram negative bacteria, as well as to fungi, dermatophytes and similar microorganisms.

Suitable components (a) are preferably the 2-hydroxy diphenyl ethers, the 2-hydroxy diphenyl methanes and the 2-hydroxy diphenyl thioethers represented by the general formula (1)

X is oxygen or sulfur or -CH ₂ -,

Y is chlorine or bromine,

Z is SO ₂ H, NO ₂ or C 1-4 alkyl,

63.403 / SM • · ·

4 · · · «·» 4 »* ··« ··· »· * ····· r is 0-3, ο is 0-3, ρ is 0 or 1, m is 0 or 1 and n is 0 or 1.

Particularly preferred is the compound of formula (I) in which

X is oxygen, sulfur or -CH ₂ -,

Y is chlorine or bromine, m is 0, n is 0 or 1, o is 1 or 2, r is 1 or 2 and p is 0.

Particularly preferred are compounds of formula (I) wherein X is O,

Y is chlorine, m is 0, n is 0, o is 1, r is 2, and p is 0.

Particularly preferred is the compound of formula (2).

Preferably, the amount of compound (a) used in the novel composition is from 0.02 to 0.2% by weight.

· «·· ·· * · • · ···» · ·

The following compounds may be used as component (b):

(bd) sulfonates, preferably terpenoids or salts of mono- or double-ring aromatic compounds, in particular sulfonates of camphor, toluene, xylene, cumene or naphthene;

(b ₂ ): saturated or unsaturated C 3 -C 12 di- or polycarboxylic acids, in particular malonic acid, succinic acid, glutaric acid, adipic acid, pimelinic acid, suberic acid, azelaic acid, sebacic acid, undecanedicarboxylic acid and dodecane dicarboxylic, fumaric, maleic, tartaric and malic acids, and citric and aconitic acids;

(b ₃ ): - aliphatic saturated or unsaturated C 1 -C 11 monocarboxylic acids, in particular acetic acid, propionic acid, hexanoic acid, caproic acid and undecylenic acid;

saturated or unsaturated di- or polycarboxylic acids having from 3 to 12 carbon atoms, in particular malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid and sebacic acid, undecanecarboxylic acid and fumaric acid , maleic, tartaric, malic, citric and aconitic acids;

aminocarboxylic acids such as ethylenediaminetetraacetic acid, hydroxyethylethylenediaminetetraacetic acid and nitrilotriacetic acid;

cycloaliphatic carboxylic acids such as camphoric acid;

- aromatic carboxylic acids such as benzoic acid, phenylacetic acid, phenoxyacetic acid and cinnamic acid, as well as 2-, 3- and 4-hydroxybenzoic acid, aniline, and ο-, m- and p-chlorophenylacetic acid and ο-, m- and p-chlorophenoxyacetic acid;

- alkali metal salts and amines of inorganic acids, such as sodium and potassium salts and amine (R ₁ R ₂ R ₃ ) hydrochloric, sulfuric, phosphoric salts,

63403 / SM ···· ···· ·· alkyl phosphoric acids and boric acid salts, amine which R ,, R ₂ and R ₃ are as defined above salts;

- isethionic acid;

- tannic acid;

the acid amides of formula (3) wherein:

R! is hydrogen or (C 1 -C 12) alkyl; and R ₂ and R ₃ are each independently hydrogen, C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 1 -C 12 hydroxyalkenyl, C 2 -C 12 hydroxyalkyl, or a polyglycol ether chain which is 1-30 -CH ₂ -CH ₂ -O- or -CHY ^ CHY ^ O-, wherein Y is Y; or Y ₂ is hydrogen and the other methyl group such as N-methylacetamide;

- urea of formula (4) wherein ^{R1 is r} 2> ^r 3 and R 4 are each independently hydrogen, C 1 -C 8 alkyl, C 2 -C 28 alkenyl, C 1 -C 8 hydroxyalkyl, or C 2 -C 8 hydroxyalkenyl;

monovalent C4-C18 aliphatic and monocyclic alcohols such as C2-C18 alkanols, C2-C18 alkenols and terpenic alcohols such as ethanol, propanol, isopropanol, hexanol, cis-3-hexyl-1-ol, trans-2-hexin-1-ol, 1-octene-3-ol, heptanol, octanol, trans-2-cis-6-nonadienen-1-ol, decanol, linalol, geraniol, dihydrotterpineol, myrcenol, nopol and terpineol;

- aromatic alcohols of general formula (5) wherein X is - (CH ₂ ) ₁ . _6, -CH = CH-CH ₂ -, or

-O- (CH ₂ ) ₂ . ₆ groups and

63 403 / SM

- 6 ···· · · · ·

R _1f R ₂ and R ₃ are each independently hydrogen, hydroxy, halo or C 1-6 alkoxy, especially benzyl alcohol, 2,4-dichlorobenzyl alcohol, phenoxyethanol, 1-phenoxy-2-propanol (phenoxy). isopropanol) and cinnamic alcohol;

polyhydric alcohols and polyhydric alkoxylates, preferably ethoxylates and / or propoxylate alcohols, as well as ethers and and esters of formula (6), wherein

R 1 and R ₂ are each independently hydrogen or C 1 -C 12 alkyl, C 2 -C 12 alkenyl, C 1 -C 8 alkanoyl, C 3 -C 18 alkenoyl, a group represented by the formula R 4 -OCH-CH 2 Cl 6 wherein:

I

R4

R ₃ is hydrogen, C 1 -C 12 alkyl, or

C2-C12 alkenyl;

R 4 is hydrogen or methyl, and X is C 2 -C 10 alkylene or C 2 -C 10 alkenylene, or - (CH ₂ CH ₂ O / CH ₃ OCH _{2 -} CH ₂ or - (CH ₂ -CH-O) CH ₂ ). -CH-.

ch ₃ ch ₃

All of the organic acids of Compound (b) may also be prepared in the form of a water-soluble salt thereof, such as an alkali metal salt, preferably a sodium or potassium salt or an amine (NR ₁ R ₂ R ₃ ) salt, wherein

R 1, R ₂ and R ₃ are each independently hydrogen, C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 1 -C 8 hydroxyalkyl, C 5 -C 8 cycloalkyl, or polyalkenyloxy Or a C 1 -C 18 alkyl group

63 403 / SM

- R 7, R ₂ and R ₃ together with the nitrogen to which they are attached are unsubstituted or C 1 -C 4 alkyl-substituted morpholino.

Component (b) may comprise a single compound of subclass (bj) or one or more compounds of class (bj) together with components of other subclasses.

Preferred for use in the (b ^ subclass containing one or more than one compound of the combination, and (b ₂₎ or a subclass of compounds containing more than one combination.

Particularly preferred are combinations of cumene sulfonate and citric acid monohydrate.

Components (c) may be anionic, nonionic or zwitterionic and amphoteric synthetic surfactants.

Anionic surfactants include:

Sulfates, especially fatty alcohol sulfates having from 8 to 18 carbon atoms in alkyl chains, such as lauryl alcohol sulfonate;

Fatty alcohol ether sulfates, in particular acid esters or salts thereof, or polyadducts with 230 moles of ethylene oxide per mole of C8-C22 fatty alcohols;

Alkali metal salts, ammonium salts or amine salts of C8-C20 fatty acids, which are soaps, particularly coconut fatty acids;

Alkyl amide sulfates;

Alkylamine sulfates, especially monoethanolamine lauryl sulfate;

Alkyl amide ether sulfates;

Alkylaryl polyether sulfates;

• monoglyceride sulfates;

63.403 / SM ···· ····

Alkane sulfonates having from 8 to 20 carbon atoms in their alkyl chain, such as dodecyl sulfonate;

Alkyl amide sulfonates;

Alkylaryl sulfonates;

Α-olefin sulfonates;

Sulfosuccinic acid derivatives, in particular alkyl sulfosuccinates, alkyl ether sulfosuccinates or alkyl sulfosuccinamide derivatives;

• N- (alkylamidoalkyl) amino acids of formula (7) wherein

X is hydrogen, (C 1 -C 4) -alkyl or -COO'M ⁺ ;

Y is hydrogen or C 1-4 alkyl;

Z is - (CH ₂ ) _m i. ₁ - group;

m-ι is 1-5;

n is from 6 to 18; and

M is an alkali metal ion or an amine ion;

alkyl ether carboxylates of formula (8) and alkyl aryl ether carboxylates, wherein

R /

X is - (CH 2 - T 8 O -, a) or - (CH ₂ ) _{5 -} 19 -N

X;

R is hydrogen or C1-C4 alkyl;

Y is - (CHCHO3);

- 9 ···· ···· • · · · · * · ·

Ο Ο'Μ ⁺ en /

A is - (CH 2 - 3 -) - CH 2 O 'M or -P

O'M ⁺ group;

m ₂ is 1-6; and

M is an alkali metal cation or an amine cation.

Other suitable anionic surfactants include fatty acid methyl taurides, alkyl isothionates, fatty polypeptide condensates and fatty alcohol phosphoric acid esters. Preferably the alkyl group in these compounds has from 8 to 24 carbon atoms.

Anionic surfactants are generally prepared in the form of their water-soluble salts, such as their alkali metal salts, ammonium salts or amine salts. Preferred such salts are the lithium salt, the sodium salt, the potassium salt, the ammonium salt, the triethylamine salt, the ethanolamine salt, the diethanolamine salt or the triethanolamine salt. Preferred are the sodium or potassium salts or the ammonium (NR ₁ R ₂ R ₃ ) salts, wherein R _{1 (} R ₂ , R ₃ independently of one another are hydrogen, C 1 -C 4 alkyl or C 1 -C 4 hydroxy. alkyl.

Particularly preferred anionic surfactants in the composition of the present invention are monoethanolamine lauryl sulfate or alkali metal salts of fatty alcohol sulfates, preferably sodium lauryl sulfate and 2-4 moles of ethylene oxide and sodium lauryl ether sulfate. the reaction product.

Preferred zwitterionic and amphoteric surfactants include C8-C18 betaines, C8-C18 sulfobetaines, C8-C24 alkylamido-C1-C4 alkylene betaines, imidazoline carboxylate, alkyl amphocarboxycarboxylic acids , alkyl amphocarboxylic acids (such as lauramoglycoglycinate) and N-alkyl-β-aminopropionates or N-alkyl-1J-iminodipropionate 63.403 / SM ···· · · · ·. C 10 -C 20 alkylamido-C 1 -C 4 alkylene betaines are preferred, and cocoamidopropyl betaine is particularly preferred.

Nonionic surfactants are typically propylene oxide / ethylene oxide adduct derivatives having a molecular weight of 1000-15000 and (1-50 EO) fatty alcohol ethoxylates, (1-50 EO) alkylphenol polyglycol ethers, ethoxylated hydrocarbons, fatty acid glycol partial esters, preferably diethyl glycol monostearate, fatty acid alkanolamides and fatty acid dialkanolamides, fatty acid alkanolamide ethoxylates and fatty acid amine oxides.

Also useful as component (c) are salts of C8-C22 saturated or unsaturated fatty acids, either alone or in admixture with other surfactants described in component (c). Examples of such fatty acids include capric acid, lauric acid, myristylic acid, palmitic acid, stearic acid, arachinic acid, behenic acid, dodecanolic acid, tetradecenoic acid, octadecenoic acid, oleic acid, eicosanic acid and erucic acid; typically coconut is a fatty acid. These acids may also be conveniently prepared in the form of their salts as cations such as alkali metal cations such as sodium and potassium cations, metal atoms such as zinc and aluminum, or suitably alkaline nitrogenous organic compounds such as amines or ethoxylated amines. These salts may be prepared in situ.

Components (d) are divalent alcohols, preferably C 2 -C 6 alkylene chain alcohols, typically ethylene glycol, 1,2- or 1,3-propanediol, 1,3-, 1,4- or 2-propanediol. , 3-butanediol, 1,5-pentanediol and

1,6-hexanediol. 1,2-Propanediol (propylene glycol) is preferred.

63 403 / SM

-11 ···· ········································•

Component (e) is preferably ethanol, n-propanol and isopropanol, or a mixture of these alcohols.

Components (d) and (e) may also be mixed with each other.

The pH of the new composition is 3 to 10, preferably 3.5 to 5.5.

The compositions of the invention are obtained in the form of a soap or syndet solution and optionally further conventional additives, in particular sequestrant, coloring agents, perfume oils, thickeners or thickeners (consistency regulators), plasticizers, UV absorbents, skin protection agents, antioxidants, containing additives, additives such as dicarboxylic acids and / or aluminum, zinc, calcium, magnesium salts of C14-C22 fatty acids, and preservatives.

The soap composition of the present invention may be prepared by mixing components (a) and (b), which may optionally contain components (c), (d), (e) and (f) in any order such that the mixture is mixed with an appropriate amount of water. mix until homogeneous. The mixture is made up to 100% with water or deionized water. In this process, processes are physical methods. Accordingly, no chemical reaction occurs between the individual components.

For the disinfection and cleaning of additional solid surfaces of the human skin and hands, the new soap compositions may be used in diluted or undiluted form in an amount of at least 2 ml, preferably two disinfections in the undiluted form.

The invention is illustrated by the following examples. Parts and percentages are by weight.

63.403 / SM • · ···· • · · ·

-121. Example

0.075% 2,4,4'-trichloro-2'-hydroxydiphenyl ether, 0.5% mono-ethanolamine lauryl sulphate, 0.25% sodium cumene sulphonate powder, 0.4% citric acid monohydrate and 0.5% propylene glycol

The mixture of the above composition is homogenized and then 90% of the appropriate amount of water is added. The pH was adjusted to 4.0 with monoethanolamine. Deionized water is then added to complete the whole 100 parts. The pH is then re-tested and if necessary adjusted to pH 4.0 with monoethanolamine.

Example 2

0.25% 2,4,4'-trichloro-2'-hydroxydiphenyl ether, 1.0% mono-ethanolamine lauryl sulphate, 2.5% sodium cumene sulphonate powder, 1.5% citric acid monohydrate and 1.0% propylene glycol

The mixture of the above composition is homogenized and then 90% of the appropriate amount of water is added. The pH was adjusted to 4.0 with monoethanolamine. Deionized water is then added to complete the whole 100 parts. The pH is then re-tested and if necessary adjusted to pH 4.0 with monoethanolamine.

Example 3

0.15% 2,4,4'-trichloro-2'-hydroxy diphenyl ether,

1.0% monoethanolamine lauryl sulfate,

0.5% sodium cumene sulphonate powder,

63 403 / SM

-13 ···· ····

Citric acid monohydrate and 0.8%

5.0% propylene glycol

The mixture of the above composition is homogenized and then 90% of the appropriate amount of water is added. The pH was adjusted to 4.0 with monoethanolamine. Deionized water is then added to complete the whole 100 parts. The pH is then re-tested and if necessary adjusted to pH 4.0 with monoethanolamine.

Example 4

0.1% 2,4,4'-trichloro-2'-hydroxydiphenyl ether,

4.0% monoethanolamine lauryl sulfate,

0.5% sodium cumene sulfotane powder and

0.019% sodium hydroxide

The mixture of the above composition is homogenized and then 90% of the appropriate amount of water is added. The pH is adjusted to 9.1 with monoethanolamine. Deionized water is then added to complete the whole 100 parts. The pH is then re-tested and if necessary adjusted to pH 9.1 with monoethanolamine.

Example 5

Investigation of microbicidal activity of new formulations

1-4. The microbicidal activity of the novel formulations of Examples 1 to 5 is determined by a suspension test (log-10). The assay is used to test the bactericidal activity of water-soluble antiseptics, disinfectants and liquid soaps. During the assay, the test product is inoculated with test dilution bacilli at various dilutions. After some contact time, aliquots are taken and the number of surviving bacilli is determined. The dosed and the survivor

63.403 / SM ···· ···· · · · · · ·

The difference of -14bacillus is expressed as the bacillus reduction in logarithms to ten. The concentration is 90% and the contact time is 30 seconds.

The following test bacilli were used:

Example 1 2 3 4 Staph. aureus ATCC 9144 > 5.0 > 5.0 > 5.0 > 5.1 Strep. 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 Sarratia marcescens ATCC 13,880 * * ★ > 5.4 **

* not measured ** contact time is 5 minutes

The above 4 values show good antimicrobial activity.

Claims (19)

PATENT CLAIMS A surfactant composition comprising (a) 0.01-0.2% by weight of a microbicidal active ingredient, (b) 0.1-7.5% by weight of one or more hydrotropic agents, (c) 0-2% by weight of one or more more than one synthetic surfactant or soap or a combination thereof and / or a saturated and / or unsaturated C 8 -C 22 fatty acid salt, (d) 0 to 10% by weight of a divalent alcohol, (e) 0 to 70% by weight of a monohydric alcohol, and (f) ) Contains 100% extra water. A composition according to claim 1, wherein component (a) is 2-hydroxy-diphenyl ether, 2-hydroxy-diphenylmethane and 2-hydroxy-diphenyl-thioether, which compounds are represented by formula (I), wherein in the formula X is oxygen or sulfur or -CH ₂ -, Y is chlorine or bromine, Z is SO ₂ H, NO ₂ or C 1-4 alkyl, r is 0-3, o is 0-3, p is 0 or 1, m is 0 or 1 and n is 0 or 1. The composition of claim 2, wherein component (a) is a compound of formula (I) wherein: X is O, S, or -CH ₂ -, ···· ···· -16Y is chlorine or bromine, m is 0, n is 0 or 1, o is 1 or 2, r is 1 or 2 and p is 0. A composition according to any one of claims 2 or 3, wherein component (a) is a compound of formula (I) wherein X is oxygen, Y is chlorine, m is 0, n is 0, o is 1, r is 2, and p is 0. The composition of claim 4, wherein component (a) is a compound of formula (2). 6. A composition according to any one of claims 1 to 4, wherein component (a) is present in an amount of 0.02 to 0.2% by weight. 7. A composition according to any one of claims 1 to 6, wherein the component (bis) is a sulfonate, preferably a salt of a terpenoid or a monocyclic or bicyclic aromatic compound. The composition of claim 7, wherein the one or two ring aromatic compound is a sulfonate of camphor, toluene, xylene, cumene or naphthenic. 63 403 / SM -179. The composition of claim 7, wherein component (b) comprises only one compound of subclass (b) or a mixture of one or more compounds of subclass (b) and components of other subclasses. 10. A composition according to any one of claims 1 to 4, wherein component (b) is a combination of one or more compounds of subclass (b ₂ ) and one or more compounds of subclass (b ₂ ) 11. A composition according to claim 9, comprising a combination of cumene sulfonate and citric acid monohydrate. 12. A composition according to any one of claims 1 to 6, wherein the anionic surfactant is a fatty alcohol sulfate having from 8 to 18 carbon atoms in the chain. The composition of claim 12, wherein the anionic surfactant composition is a sulfated alkali metal salt of lauryl alcohol or monoethanamine lauryl sulfate. 14. A composition according to any one of claims 1 to 6, wherein component (b) is a C 10-20 alkylamido-C 1-4 alkylene betaine. 15. The composition according to any one of claims 1 to 6, wherein the saturated and / or unsaturated C 8 -C 22 fatty acid corresponds to component (c): lauric acid, myristic acid, palmitic acid, stearic acid, arachic acid, behenic acid, dodecanoic acid, tetradecenoic acid, octadecenoic acid, oleic acid . 16. A composition according to any one of claims 1 to 6, wherein component (d) is propylene glycol. The composition of any one of claims 16, wherein component (e) is ethanol, propanol, isopropanol, and mixtures thereof. 63.403 / SM ···· ···· -18 ··· The composition of claim 16 or 17, wherein component (d) and component (e) are mixed with each other. 19. Use of an antimicrobial soap composition according to any one of claims 1 to 4 for disinfecting and cleaning human skin, hands and solid surfaces. Use according to claim 19, characterized in that the antimicrobial soap composition is in diluted or undiluted form.