WO1999007331A1 - Systeme d'agents de conservation pour agents de soins pour le corps - Google Patents

Systeme d'agents de conservation pour agents de soins pour le corps Download PDF

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Publication number
WO1999007331A1
WO1999007331A1 PCT/EP1998/004762 EP9804762W WO9907331A1 WO 1999007331 A1 WO1999007331 A1 WO 1999007331A1 EP 9804762 W EP9804762 W EP 9804762W WO 9907331 A1 WO9907331 A1 WO 9907331A1
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WO
WIPO (PCT)
Prior art keywords
acid
preservative
use according
anionic
quaternary ammonium
Prior art date
Application number
PCT/EP1998/004762
Other languages
German (de)
English (en)
Inventor
Detlef Hollenberg
Kurt Seidel
Christian Priebe
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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
Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to SK149-2000A priority Critical patent/SK1492000A3/sk
Priority to KR1020007001201A priority patent/KR20010022607A/ko
Priority to EP98938713A priority patent/EP0993298A1/fr
Priority to CA002299340A priority patent/CA2299340A1/fr
Priority to AU87331/98A priority patent/AU8733198A/en
Priority to PL98338475A priority patent/PL338475A1/xx
Priority to JP2000506926A priority patent/JP2001513488A/ja
Priority to HU0100333A priority patent/HUP0100333A2/hu
Priority to BR9811843-9A priority patent/BR9811843A/pt
Publication of WO1999007331A1 publication Critical patent/WO1999007331A1/fr

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Classifications

    • 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
    • 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
    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • 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
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/524—Preservatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/08—Preparations for bleaching the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • the invention relates to the preservation of personal care products, in particular the preservation of hair care products using quaternary ammonium compounds and anionic preservatives and / or ⁇ -hydroxycarboxylic acids.
  • the invention also relates to a mixture of special quaternary ammonium compounds, the so-called ester quats, and sodium salicylate and its use as a preservative for body care products.
  • the human body in particular the human hair, is today treated in a variety of ways with cosmetic preparations (hair treatment agents). This includes, for example, cleaning the body and hair with shampoos and shower preparations, and bleaching, dyeing and shaping hair with waving agents, tinting agents and styling preparations.
  • Hair treatment agents that are formulated as a hair treatment or conditioner are usually aqueous emulsions of various water- or fat-soluble ingredients. Preserving such emulsions to maintain their usability, in particular after prolonged storage, is sometimes difficult. Quaternary ammonium compounds, which are used in many personal care products, especially in most hair treatment products, exert a certain microbicidal action in these, but this alone is not sufficient for preservation.
  • the invention therefore relates to the use of a mixture of at least one quaternary ammonium compound and at least one anionic preservative and / or at least one ⁇ -hydroxycarboxylic acid as a preservative system for personal care products.
  • the personal care product is preferably a hair care product.
  • the hair care products within the meaning of the invention also include those hair treatment products which only bring about a decorative change in the hair, for example hair colorants or permanent waving compositions.
  • polymers which can be used in the context of the invention are generally cationic polymers which have an ammonium group.
  • Preferred cationic polymers are, for example
  • quaternized cellulose derivatives as are commercially available under the names Celquat "and Polymer JR * ; the compounds Celquat * H 100, Celquat * L 200 and Polymer JR * 400 are preferred quaternized cellulose derivatives;
  • Vmylpyrrolidone-Memoimidazoliniumchlorid-Copolymers as they are offered under the name Luviquat ® , quaternized polyvinyl alcohol as well as those under the names Polyquaternium 2, Polyquaternium 17, Polyquaternium 18 and
  • Polyquaternium 27 known polymers with quaternary nitrogen atoms in the main polymer chain.
  • a compound from the group of the cationic surfactants is selected as the quaternary ammonium compound.
  • Quaternary ammonium compounds are preferred among the cationic surfactants.
  • ammonium halides especially chlorides and bromides, such as allyl trimethylammonium chlorides, dialkyldiethylammonium chlorides and triethyl methylammonium chlorides, e.g. Cetyltrimethylammonium chloride, cetyltrimethylammonium bromide, dicetyldimethylammonium chloride,
  • esters quats are quaternary ammonium compounds, so-called “ester quats”, which may be preferred because of their good biodegradability.
  • ester quats are the quaternized fatty acid triemanolamine ester salts of the general formula I
  • R'CO for an acyl radical with a total of 6 to 22 carbon atoms
  • R 2 and R 3 independently of one another for hydrogen or R'CO
  • R 4 for an alkyl radical with 1 to 4 carbon atoms or a (CH 2 CH 2 O-) q H group
  • m, n and p in total stands for 0 or numbers from 1 to 12, q for numbers from 1 to 12 and X " for halide, alkyl sulfate or alkyl phosphate.
  • quaternized fatty acid triethanolamine ester salts which can be used in the context of the invention are products based on caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, isostearic acid, stearic acid, oleic acid, elaidic acid, arachidic acid, behenic acid and erucic acid and also technical mixtures thereof as they occur, for example, in the pressure splitting of natural fats and oils.
  • the fatty acids and the triethanolamine can be used in a molar ratio of 1.1: 1 to 3: 1.
  • an application ratio of 1.2: 1 to 2.2: 1, preferably 1.5: 1 to 1.9: 1 has proven to be particularly advantageous.
  • the preferred quaternized fatty acid triethanolamine ester salts of the general formula I are technical mixtures of mono-, di- and triesters with an average degree of esterification of 1.5 to 1.9 and are derived from technical C 16/18 tallow or palm fatty acid (Iodine number 0 to 40).
  • quaternized fatty acid triethanolamine ester salts of the general formula I have proven to be particularly advantageous if R'CO for an acyl radical with 16 to 18 carbon atoms, R 2 for R'CO, R 3 for hydrogen, R 4 for a methyl group, m , n and p is 0 and X "is methyl sulfate.
  • quaternized ester salts of fatty acids with diethanolalkylamines of the formula II are also suitable as esterquats,
  • R 5 CO for an acyl radical with a total of 6 to 22 carbon atoms
  • R 6 for hydrogen or R 5 CO
  • R 7 and R 8 independently of one another for alkyl radicals with 1 to 4 carbon atoms
  • m and n in total for 0 or numbers from 1 to 12
  • X represents halide, alkyl sulfate or alkyl phosphate.
  • ester quats To name ester salts of fatty acids with 1,2-dihydroxypropyl dialkylamines of the formula HI,
  • R 9 CO represents an acyl radical with a total of 6 to 22 carbon atoms
  • R 10 represents hydrogen or R 9 CO
  • R 11 , R 12 and R 13 independently of one another for alkyl radicals having 1 to 4 carbon atoms, m and n in total for 0 or numbers from 1 to 12
  • X represents halide, alkyl sulfate or alkyl phosphate.
  • esterquats of the formulas ⁇ and DI usually come on the market in the form of 50 to 90% strength by weight alcoholic solutions, which can be diluted with water if required.
  • the substances described with the formulas I to IQ are naturally individual substances, and mixtures of these substances can generally also be considered for the use according to the invention. It is also possible to use the technical mixtures of substances that are available in changing compositions due to the manufacturing process.
  • the quaternary ammonium compounds are not esterquats, it is preferred in the sense according to the invention if the quaternary ammonium compound is cetyltrimethylammonium bromide or cetyltrimethylammonium chloride, or if it is a mixture of the two compounds mentioned.
  • An alkali metal salt is preferably used as the anionic preservative an organic acid or a mixture of alkali metal salts of one or more organic acids.
  • salts of the acids mentioned with lithium, sodium, potassium, rubidium or cesium are suitable as alkali metal salts.
  • the sodium or potassium salts of the acids mentioned are preferably used, particularly preferably the sodium salts.
  • anionic preservatives are the alkali metal salts of salicylic acid, in particular sodium salicylate.
  • At least one ⁇ -hydroxycarboxylic acid can be used according to the invention.
  • Preferred ⁇ -hydroxycarboxylic acids are lactic acid, tartaric acid, malic acid and citric acid; Lactic acid, malic acid and tartaric acid are particularly preferred.
  • the ⁇ -hydroxy carboxylic acids can also be used in the form of their physiologically tolerable salts, in particular the alkali metal, alkaline earth metal and aluminum salts.
  • a combination of a quaternary ammonium compound, an anionic preservative and an ⁇ -hydroxycarboxylic acid as the preservative system can be used according to the invention be preferred.
  • a binary mixture it may be preferred to use a quaternary ammonium compound in combination with an anionic solvent.
  • the weight ratio of quaternary ammonium compound to anionic preservative or ⁇ -hydroxycarboxylic acid is usually about 1:20 to 100: 1.
  • the quaternary ammonium compounds are generally used in a concentration of about 0.1 to about 10% by weight, based on the total agent according to the invention. Amounts of approximately 0.5 to 7, particularly preferably of approximately 0.8 to 5% by weight are particularly preferred.
  • the anionic preservatives are generally used in a concentration of about 0.1 to about 2% by weight, preferably about 0.5 to about 1% by weight, based on the total preparation containing the anionic preservative.
  • the ⁇ -hydroxycarboxylic acids are preferably used in amounts of about 0.1 to about 0.5% by weight, based on the preparation as a whole.
  • Ester quats in the sense of the invention are understood to mean the abovementioned quaternary ammonium compounds having the general formulas I, II and HI.
  • the combination of the ester quats with the alkali metal is particularly preferred.
  • tall salts of salicylic acid particularly preferred is the combination with sodium salicylate.
  • the invention thus relates to a preservative system comprising at least one quaternary ester compound (ester quat) and at least one alkali metal salicylate in a weight ratio of about 1:20 to about 100: 1 as active substances.
  • ester quat quaternary ester compound
  • alkali metal salicylate in a weight ratio of about 1:20 to about 100: 1 as active substances.
  • Sodium salicylate is preferably used as the alkali salicylate.
  • Another object of the invention is a preservative system as described above, wherein emylammmoniummethosulfat as quaternary Esterastic Distearoylethylhydroxy- (INCI name: Distearoylethyl hydroxy ethylmoniummethosulfate, for example marketed as Dehyquart ® F 75, manufacturer: Henkel KGaA, Dusseldorf) is used.
  • emylammmoniummethosulfat as quaternary Esterastic Distearoylethylhydroxy- (INCI name: Distearoylethyl hydroxy ethylmoniummethosulfate, for example marketed as Dehyquart ® F 75, manufacturer: Henkel KGaA, Dusseldorf) is used.
  • the invention also relates to the use of a preservative system containing, as active substances, at least one quaternary ester compound (ester quat) and at least one alkali metal salicylate in a weight ratio of 1:20 to 100: 1 in personal care products.
  • a preservative system containing, as active substances, at least one quaternary ester compound (ester quat) and at least one alkali metal salicylate in a weight ratio of 1:20 to 100: 1 in personal care products.
  • the active ingredient combination of quaternary ammonium compound and anionic preservative described above, which is suitable as a preservative system, can be used in a large number of preparations for body care, in particular for hair care.
  • hair care products such as shampoos, hair rinses, hair treatments, hair tip fluids, colorants, hair sprays or waving agents.
  • a number can further compounds are present in the final preparation, which have, for example, a cleaning, finishing, coloring or shaping effect.
  • preservative system according to the invention is to be used, for example, in shampoos, there is generally at least one anionic, zwitterionic, amphoteric or nonionic surfactant in addition to the preservative active ingredient combination.
  • anionic, surface-active substances suitable for use on the human body are in principle suitable for use together with the preservative active ingredient combination according to the invention, the preservative system, provided that they are not incompatible with the cationic component of the preservative system. Whether such intolerance is present for certain compounds is either known to the person skilled in the art or can be determined by simple experiments.
  • Such anionic, surface-active substances are characterized by a water-solubilizing anionic group such as. B. at least one carboxylate, sulfate, sulfonate or phosphate group and at least one hydrocarbon group, preferably at least one lipophilic alkyl group with about 10 to about 22 carbon atoms.
  • glycol or polyglycol ether groups, ester groups, ether, amide and hydroxyl groups can be contained in the molecule. Examples of suitable anionic surfactants are:
  • n for integers from 1 to 10
  • m for the Numbers 1 or 2
  • Z represents a cation from the group of the alkali or alkaline earth metals
  • Esters of tartaric acid and citric acid with alcohols which are adducts of about 2-15 molecules of ethylene oxide and / or propylene oxide with fatty alcohols with 8 to 22 carbon atoms,
  • alkali, alkaline earth and / or ammonium salts in each case in the form of the alkali, alkaline earth and / or ammonium salts, preferably in the form of their sodium, potassium, magnesium and / or ammonium salts and the mono-, di- and / or trialkanolammomium salts with 2 or 3 carbon atoms in the alkanol group.
  • Preferred anionic surfactants are alkyl sulfates, alkyl polyglycol ether sulfates and ether carboxylic acids with 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule, and sulfosuccinic acid mono- and dialkyl esters with 8 to 18 carbon atoms in the alkyl group and sulfoberstein Acid monoalkyl polyoxyethyl ester with 8 to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups.
  • nonionic surfactants can also be present in the preparations according to the invention containing the preservative system.
  • B a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether groups. Examples of such connections are:
  • alkyl polyglycosides of the general formula R 17 O (-Z) x as nonionic surfactants.
  • the alkyl radical R 17 contains 6 to 22 carbon atoms and can be either linear or branched. Primary linear or methyl branched methyl in the 2-position are preferred.
  • Such alkyl radicals R 17 are, for example, 1-octyl, 1-decyl, 1-lauryl, 1-myristyl, 1-cetyl and 1-stearyl radicals.
  • 1-Octyl, 1-decyl, 1-lauryl or 1-myristyl radicals are particularly preferred.
  • alkyl polyglycosides which can be used in the preparations according to the invention can contain, for example, only one specific alkyl radical R 17 .
  • the alkyl polyglycosides are produced from natural fats and oils or mineral oils.
  • alkyl radicals R 17 are mixtures corresponding to the starting compounds or corresponding to the respective working up of these compounds.
  • Any mono- or oligosaccharides can be used as sugar building block Z.
  • Sugar with 5 or 6 carbon atoms and the corresponding oligosaccharides are usually used.
  • sugars are glucose, fructose, galactose, arabinose, ribose, xylose, lyxose, allose, old rose, mannose, gulose, idose, talose and sucrose.
  • Preferred sugar units are glucose, fructose, galactose, arabinose and sucrose; Glucose is particularly preferred.
  • alkyl polyglycosides which can be used according to the invention contain an average of 1.1 to 5 sugar units. Alkyl polyglycosides in which x is from 1.1 to 1.6 are preferred. Alkyl polyglycosides in which x is 1.1 to 1.4 are very particularly preferred.
  • alkoxylated homologs of the alkyl polyglycosides mentioned can also be used according to the invention. These homologues can contain an average of up to 10 ethylene oxide and / or propylene oxide units per alkyl glycoside unit.
  • the compounds with alkyl groups used as surfactants can each be pure substances. However, it is generally preferred to start from natural vegetable or animal raw materials in the production of these substances, so that substance mixtures with a different number of carbon atoms in the alkyl chain, depending on the respective raw material, are obtained.
  • the surfactants which are addition products of ethylene and / or propylene oxide onto fatty alcohols or derivatives of these addition products, both products with a "normal" homolog distribution and those with a narrowed homolog distribution can be used.
  • Normal homolog distribution is understood to mean mixtures of homologues which are obtained as catalysts when fatty alcohol and alkylene oxide are reacted using alkali metals, alkali metal hydroxides or alkali metal alcoholates.
  • narrow homolog distributions are obtained if, for example, hydrotalcites, alkaline earth metal salts of ether carboxylic acids, alkaline earth metal oxides, hydroxides or alcoholates are used as catalysts. The use of products with a narrow homolog distribution can be preferred.
  • the preparations produced using the preservative system according to the invention preferably contain the zwitterionic, anionic and / or nonionic surfactants in amounts of 0.5 to 40% by weight, in particular 0.5 to 20% by weight and particularly preferably 1 to 5% by weight .%, based on the entire preparation.
  • the preparations containing the preservative system according to the invention are usually in the form of aqueous or aqueous-alcoholic solutions or dispersions.
  • Preferred are water-based formulations and formulations which contain less than 15% by weight, based on the preparation as a whole, of alcohol, in particular ethanol.
  • formulations based on alcohol, in particular based on ethanol may also be preferred for special applications.
  • the preparations can contain a vitamin and / or a vitamin derivative in addition to or instead of one or more of the other compounds already listed contain.
  • a vitamin and / or a vitamin derivative in addition to or instead of one or more of the other compounds already listed contain.
  • natural, synthetic, water-soluble or oil-soluble vitamins and vitamin derivatives are suitable.
  • vitamins and vitamin derivatives are, for example, vitamin A, vitamin E, vitamin E acetate, vitamin E nicotinate, vitamin F, vitamin B 3 , vitamin B 6 , nicotinamide, vitamin H, vitamin C, vitamin B 5 and its derivatives , in particular panthenol, panthotenic acid, calcium panthotenate, panthotenyl ethyl ether, panmenyl hydroxypropyl steardimonium chloride
  • panthetine and panthenyl triacetate panthetine and panthenyl triacetate.
  • Analog derivatives for example panthotenylpropyl ether, panthotenyl butyl ether and further branched or linear, saturated or unsaturated homologs, can of course also be used.
  • the salts of pantothenic acid the possible counterions of which are not only limited to calcium, but also include all physiologically acceptable metal cations, for example the alkali and alkaline earth metals, in particular magnesium, sodium or potassium.
  • the invention also encompasses the use of all possible stereoisomers of the different vitamins, it being possible in particular for vitamin B 5 and its derivatives to use both the D and L forms and all mixtures of the two forms according to the invention.
  • the vitamins or vitamin derivatives are used in the preparations according to the invention in amounts of 0.01 to 30% by weight, based on the entire preparation. Usually 0.02 to 15, in particular 0.02 to 8% by weight are particularly advantageous for the production of aqueous, ready-to-use preparations. In many cases, amounts between 0.05 and 5% by weight are sufficient. For concentrates, it can be advantageous to use vitamins and / or vitamin derivatives in amounts of 0.05 to 30% by weight, in particular 1 to 25% by weight and particularly preferably 3 to 20% by weight.
  • the preparations according to the invention can be used alone or together with one or more of those already listed Ingredients, including protein hydrolyzates.
  • Protein hydrolyzates are understood to be a mixture of amino acids, oligopeptides and polypeptides and their derivatives.
  • Amino acids which can be used according to the invention are, for example, arginine, lysine, cysteine, glutamine, asparagine and valine.
  • Amino acid mixtures which can be obtained by largely completely basic, acidic or enzymatic hydrolysis of animal or vegetable proteins have also proven suitable.
  • Oligopeptides and polypeptides which can be used according to the invention are, for example, animal or vegetable proteins or their (partial) hydrolysates obtained by acidic, basic or enzymatic means. Suitable proteins are, for example, keratin, collagen, elastin, soy protein, milk protein, casein, fibroine, sericin, wheat protein, silk protein and almond protein. Keratin and the vegetable proteins can be preferred according to the invention.
  • the hydrolysis produces mixtures of substances with average molecular weights in the range from approximately 400 to approximately 50,000 Daltons. Usual average molecular weights are in the range from about 500 to about 8000 daltons. Hydrolysates of keratin, silk protein and vegetable proteins are preferred according to the invention.
  • Derivatives of amino acids, oligopeptides and polypeptides are understood according to the invention to mean their cationic derivatives and their condensation products with fatty acids.
  • Cationic derivatives are obtained by reaction with compounds which usually carry quaternary ammonium groups or by reaction with corresponding amines and subsequent quaternization.
  • quaternary protein hydrolyzates are available as commercial products, for example: cationic collagen hydrolyzate, for example that under the name
  • Lamequat ® L product on the market (INCI name:
  • Croquat ® product on the market (CTFA name:
  • Croda the product available under the name Crotein ® Q, according to INCI
  • Hydroxypropyltrimonium Hydrolyzed Collagen (Croda) and the quaternized protein hydrolyzate available as Lexein ® QX 3000 (Inolex).
  • condensation products of protein hydrolyzates with fatty acids oleic acid, myristic acid, undecylenic acid, coconut fatty acid and abietic acid are preferably used as the acid component.
  • These condensation products can also be in the form of salts, in particular sodium, potassium and triethanolamine salts.
  • the condensation products based on collagen hydrolyzate also carry the CTFA names Oleoyl Hydrolyzed Collagen, Myristoyl Hydrolyzed Collagen, Oleoyl Hydrolyzed Animal Collagen, Potassium Coco Hydrolyzed Animal Protein, TEA Abietoyl Hydrolyzed Collagen, Potassium Undecylenoyl Hydrolyzed Collagen and TEA Coco Hydrolyzed Collagen.
  • Lamepon ® LPO Lamepon ® 4 SK
  • Lamepon ® UD Lamepon ® UD
  • Lamepon ® 460 Lamepon ® PA TR
  • Lamepon ® ST 40 Lamepon ® S (Grünau)
  • Lexein ® A 240 Lexein ® S 620 and Lexein ® A 520 (Inolex).
  • Condensation products of elastin hydrolyzates with fatty acids for example Lauric acid (CTFA name: Lauroyl Hydrolyzed Elastin) can also be used.
  • CFA name: Lauroyl Hydrolyzed Elastin Lauric acid
  • Crolastin ® AS (Croda) is a corresponding market product.
  • a Potassium Cocoyl Hydrolyzed Wheat Protein (Seiwa) is available under the name Promois EGCP.
  • Lexein ® A 200 Inolex
  • Lamepon ® PO-TR Lamepon ® PA-K
  • Lamepon ® S-MV Lamepon S ® TR
  • Crotein CCT ® Crotein CCT ®
  • the active ingredient combination of quaternary ammonium compound and anionic preservative according to the invention can be used not only in preparations for hair regeneration but also in products which bring about a purely decorative change in the hair, for example in hair colorants. If the active ingredient combination according to the invention is used in hair colorants, then in addition to the at least one quaternary ammonium compound and the at least one anionic preservative there is also at least one dye or dye precursor for dyeing keratin fibers. In order to achieve the coloring effect, oxidation coloring agents usually contain two groups of substances, which are called developers and couplers.
  • Preferred developer components according to the invention are p-phenylenediamine, p-toluenediamine, p-aminophenol, o-aminophenol, 1- (2'-hydroxyethyl) -2,5-diaminobenzene, N, N-bis (2-hydroxyethyl) -p -phenylenediamine, 2- (2.5-
  • Coupler components preferred according to the invention are 1-naphthol, pyrogallol, 1,5-, 2,7- and 1,7-dihydroxynaphthalene, o-aminophenol, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-Phe - nylenediamine, l-phenyl-3-methyl-pyrazolon-5, 2,4-dichloro-3-aminophenol, 1,3-bis (2,4-diaminophenoxy) propane, 4-chlororesorcinol, 2-chloro-6 -methyl-3-aminophenol, 2-methylresorcinol, 5-methylresorcinol, 2,5-dimethylresorcinol, 2,6-dihydroxypyridine, 2,6-diaminopyridine, 2-amino-3-hydroxypyridine, 2,6-dihydroxy-3 , 4-diaminopyridine, 3-amino-2-
  • Diaminophenoxyethanol 1-methoxy-2-amino-4- (2-hydroxyethylamino) -benzene, 2-methyl-4-chloro-5-aminophenol, 6-methyl-l, 2,3,4-tetrahydro- quinoxaline, 3,4-methylenedioxyphenol, 3,4-methylenedioxyaniline, 2,6-dimethyl-3-aminophenol, 3-amino-6-methoxy-2-methylaminophenol, 2-hydroxy-4-aminophenoxyethanol, 2-methyl 5- (2-hydroxyethylamino) phenol and 2,6-dihydroxy-3,4-dimethylpyridine.
  • the hair colorants contain both the developers and the couplers preferably in an amount of 0.005 to 20% by weight, preferably 0.1 to 5% by weight, in each case based on the total oxidation colorant.
  • Developers and couplers are generally used in approximately molar amounts to one another. If the molar use has also proven to be expedient, it is a certain excess of individual oxidation dye precursors is not disadvantageous, so that developers and couplers can be present in a molar ratio of 1: 0.5 to 1: 3, in particular 1: 1 to 1: 2.
  • the hair colorants can contain direct dyes either as the sole coloring component for further modification of the color shades in addition to the oxidation dye precursors.
  • Direct dyes are usually nitrophenylenediamines, nitroaminophenols, azo dyes, anthraquinones or indophenols.
  • Preferred direct dyes are those with the international names or trade names HC Yellow 2, HC Yellow 4, HC Yellow 5, HC Yellow 6, Basic Yellow 57, Disperse Orange 3, HC Red 3, HC Red BN, Basic Red 76, HC Blue 2, HC Blue 12, Disperse Blue 3, Basic Blue 99, HC Violet 1, Disperse Violet 1, Disperse Violet 4, Disperse Black 9, Basic Brown 16 and Basic Brown 17 known compounds and 4-amino-2-nitrodiphenylamine-2 ' -carboxylic acid, 6-nitro-l, 2,3,4-tetrahydroquinoxaline, hydroxyethyl-2-nitro-toluidine, picramic acid, 2-amino-6-chloro-4-nitrophenol 4-ethylamino-3-nitrobenzoic acid and 2-chloro 6-ethylamino-1-hydroxy-4-nitrobenzene
  • preparations according to the invention can also contain naturally occurring dyes such as, for example, henna red, henna neutral, henna black, chamomile flowers, sandalwood, black tea, rotten bark, sage, blue wood, madder root, catechu, sedre and alkanna root.
  • naturally occurring dyes such as, for example, henna red, henna neutral, henna black, chamomile flowers, sandalwood, black tea, rotten bark, sage, blue wood, madder root, catechu, sedre and alkanna root.
  • Further dye components contained in the colorants according to the invention can also be indoles and indolines, and also their physiologically tolerable salts.
  • Preferred examples are 5,6- Dihydroxyindole, N-methyl-5,6-dihydroxyindole, N-ethyl-5,6-dihydroxyindole, N-propy 1-5, 6-dihydroxy indole, N-butyl-5, 6-dihydroxy indole, 5, 6-dihydroxy indole-2-carboxylic acid, 6-hydroxy indole, 6-aminoindole and 4-aminoindole.
  • 5,6-dihydroxyindoline N-methyl-5,6-dihydroxyindoline, N-ethyl-5,6-dihydroxyindoline, N-propyl-5,6-dihydroxyindoline, N-butyl-5,6-dihydroxyindoline, 5 , 6-dihydroxyindoline-2-carboxylic acid, 6-hydroxyindoline, 6-aminoindoline and 4-aminoindoline.
  • oxidation dye precursors or the optional direct dyes each represent uniform compounds. Rather, in the hair colorants according to the invention, due to the production processes for the individual dyes, further components may also be present in minor amounts, provided that these do not adversely affect the coloring result or for other reasons, e.g. toxicological, must be excluded.
  • the oxidation dye precursors are incorporated into the preparation according to the invention, at least containing component A and component B.
  • the preparations according to the invention are, for example, as a cream, aerosol, emulsion, gel or else formulated as a surfactant-containing, foaming solution, for example as a shampoo, aerosol foam or in some other way, which are suitable for use on the hair.
  • the oxidative development of the coloring can take place with atmospheric oxygen.
  • a chemical oxidizing agent is preferably used, especially if, in addition to the coloring, a lightening effect on human hair is desired.
  • Persulfates, chlorites and in particular hydrogen peroxide or its adducts with urea, melamine and sodium borate are suitable as oxidizing agents. It is also possible to carry out the oxidation with the aid of enzymes.
  • the enzymes can be used to transfer atmospheric oxygen to the developer or to enhance the effect of small amounts of oxidizing agents present.
  • An example of an enzymatic process is the procedure to increase the effect of small amounts (e.g. 1% and less, based on the total agent) of hydrogen peroxide by peroxidases.
  • the preparation of the oxidizing agent is expediently mixed with the preparation from the oxidation dye precursors immediately before hair coloring.
  • the resulting ready-to-use hair dye should preferably have a pH in the range from 6 to 10. It is particularly preferred to use the hair dye in a weakly alkaline environment.
  • the application temperatures can range between 15 and 40 ° C. After an exposure time of approx. 30 minutes, the hair dye is removed from the hair to be colored by rinsing. Washing with a shampoo is not necessary if a carrier with a high tenside content, e.g. a coloring shampoo was used.
  • the preservative system according to the invention can also be used in the production of corrugating agents.
  • Waving agents are understood to mean agents which serve the permanent deformation of keratin fibers.
  • a Such deformation is usually achieved by mechanically deforming the fiber and fixing the deformation using suitable aids.
  • the fiber Before and / or after this deformation, the fiber is treated with the aqueous preparation of a keratin-reducing substance (waving agent) and rinsed with water or an aqueous solution after an exposure time.
  • the fiber is then treated with the aqueous preparation of an oxidizing agent (fixing agent). After an exposure time, this is also rinsed out and the fiber is freed of the mechanical deformation aids (curlers, papillots).
  • the waving agents contain mercaptans, for example thioglycolic acid, thiolactic acid, thio malic acid, mercaptoethanesulfonic acid and their salts and esters, cysteamine, cysteine, multicolored salts and alkali metal salts of sulfurous acid.
  • mercaptans for example thioglycolic acid, thiolactic acid, thio malic acid, mercaptoethanesulfonic acid and their salts and esters, cysteamine, cysteine, multicolored salts and alkali metal salts of sulfurous acid.
  • the alkali metal or ammonium salts of thioglycolic acid and / or thiolactic acid and the free acids are preferred. These are preferably used in the waving agents in concentrations of 0.5 to 1.0 mol / kg, based on the entire waving agent, at a pH of 5 to 10, in particular 7 to 8.5.
  • Oxidizing agents e.g. As sodium bromate, potassium bromate, or hydrogen peroxide, together with stabilizers customary for stabilizing aqueous hydrogen peroxide preparations, are used.
  • the pH of such aqueous H 2 O 2 preparations which usually contain about 0.5 to 3.0% by weight of H 2 O 2 , is preferably 2 to 4; it is adjusted by inorganic acids, preferably phosphoric acid.
  • Bromate-based fixatives usually contain the bromates in concentrations of 1 to 10 and the pH of the solutions is adjusted to 4 to 7.
  • Fixing agents based on enzymes (peroxidases) which contain no or only small amounts of oxidizing agents, in particular H 2 O 2 , are also suitable.
  • Both the waving agent and the fixing agent can be formulated as a cream, gel or liquid.
  • foam aerosols which are mixed with a liquefied gas such.
  • propane-butane mixtures, nitrogen, CO 2 , air, N 2 O, dimethyl ether, chlorofluorocarbon blowing agents or mixtures thereof are filled in aerosol containers with a foam valve.
  • the fixatives can also be formulated as solids.
  • the oxidizing agent in the form of a solid, for example potassium or sodium bromate. Only shortly before use, these agents are then mixed with water. It may also be preferred to formulate the oxidizing agent as a two-component system. The two components, one of which is preferably a hydrogen peroxide solution or an aqueous solution of another oxidizing agent and the other of which contains the other constituents, are likewise only mixed shortly before use.
  • the hair treatment compositions according to the invention can be both products which are rinsed out of the hair after a certain contact time, generally about 1 to 45 minutes, and products which remain on the hair.
  • the preservative system according to the invention can be used at different pH values.
  • Hair shampoos and conditioners as well as waving lotions preferably have a pH of 2.5 to 7.0, in particular 4.0 to 6.0.
  • the pH value of oxidation colorants is usually 6.0 to 10.0, in particular 7.0 to 9.0.
  • any acid or base that can be used for cosmetic purposes can be replaced.
  • an acid it may be preferred to use an acid from the group of the edible acids, for example acetic acid, ascorbic acid and gluconic acid.
  • the ⁇ - Hydroxy carboxylic acids such as lactic acid, tartaric acid, citric acid and malic acid, in addition to their property as part of the preservative system, serve to adjust the pH.
  • the preparations according to the invention can contain all the cosmetic additives customary for the particular intended use.
  • amphoteric surfactants for example N-alkylglycines, N-alkylpropionic acids,
  • N-alkylaminobutyric acids N-alkyliminodipropionic acids, N-hydroxyethyl
  • Atoms in the alkyl group zwitterionic surfactants, for example the so-called betaines and 2-
  • anionic polymers for example polyacrylic and polymethacrylic acids, their salts, their copolymers with acrylic and methacrylic acid esters and amides and their derivatives, which are obtained by crosslinking with polyfunctional agents ;
  • Compounds of this type are, for example, under the names Carbopof934, Carbopol * 934P,
  • nonionic polymers for example vinylpyrrolidone / vinyl acrylate copolymers, polyvinylpyrrolidone and vinylpyrrolidone / vinyl acetate copolymers,
  • Thickeners such as agar agar, guar gum, alginates, cellulose ethers,
  • Gelatin pectins and / or xanthan gum
  • Structurands such as glucose and maleic acid, hair-conditioning compounds such as phospholipids, for example
  • Solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerin and diethylene glycol,
  • Anti-dandruff active ingredients such as climbazole, piroctone oliana and zinc omadine, other substances for adjusting the pH value,
  • Active ingredients such as bisabolol, allantoin and plant extracts,
  • Fats and waxes such as walrus, beeswax, montan wax, paraffins,
  • Esters, glycerides and fatty alcohols are examples of esters, glycerides and fatty alcohols.
  • Swelling and penetration substances such as PCA, glycerol, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and primary, secondary and tertiary phosphates,
  • Opacifiers such as latex or styrene / acrylamide copolymers
  • Pearlescent agents such as ethylene glycol mono- and distearate or PEG-3 distearate,
  • Blowing agents such as propane-butane mixtures, N 2 O, dimethyl ether, CO 2 and air as well
  • pH value (both formulations): approx. 2.8
  • the bacterial cultures used for the investigation contained the following microorganisms:
  • Staphylococcus aureus ATCC 6538 Enterococcus faecium ATCC 6057 Escherichia coli ATCC 11229 Enterobacter aerogenes DSM 30053 Pseudomonas aeruginosa ATCC 15442
  • the fungal cultures used for the investigation contained the following microorganisms:
  • Standard microbial suspensions with 10 8 CFU / ml bacteria and 10 7 CFU / ml fungi were prepared from the above-mentioned microorganisms. Each 10 g of sample formulations 1 and 2 were then loaded in a sterile vessel with 0.1 ml of the bacterial and 0.1 ml of the fungal suspension. The germ suspensions were mixed in a glass homogemsator with at least 10 homogemsator strokes. Direct smears of 2 inoculation loops each on THL Standard I nutrient agar, THL wort agar, THL Standard I nutrient broth and THL wort broth were carried out from the sample formulations so loaded.

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Abstract

L'invention concerne l'utilisation d'un mélange comprenant au moins un composé ammonium quaternaire et au moins un agent de conservation anionique et/ou au moins un acide α-hydroxycarboxylique en tant que système d'agents de conservation pour des agents de soins pour le corps. L'invention concerne également un système d'agents de conservation contenant au moins un composé ester (composé quaternaire d'ester) et au moins un salicylate alcalin dans un rapport en poids de 1:20 à 100:1.
PCT/EP1998/004762 1997-08-04 1998-07-30 Systeme d'agents de conservation pour agents de soins pour le corps WO1999007331A1 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
SK149-2000A SK1492000A3 (en) 1997-08-04 1998-07-30 Application of a mixture and a preservative system
KR1020007001201A KR20010022607A (ko) 1997-08-04 1998-07-30 신체 위생 제품용 보존 시스템
EP98938713A EP0993298A1 (fr) 1997-08-04 1998-07-30 Systeme d'agents de conservation pour agents de soins pour le corps
CA002299340A CA2299340A1 (fr) 1997-08-04 1998-07-30 Systeme d'agents de conservation pour agents de soins pour le corps
AU87331/98A AU8733198A (en) 1997-08-04 1998-07-30 Preservative system for personal hygiene products
PL98338475A PL338475A1 (en) 1997-08-04 1998-07-30 System of preservatives constituting ingredients of body care agents
JP2000506926A JP2001513488A (ja) 1997-08-04 1998-07-30 個人衛生製品用の防腐剤システム
HU0100333A HUP0100333A2 (hu) 1997-08-04 1998-07-30 Tartósítószer rendszer testápolószer számára
BR9811843-9A BR9811843A (pt) 1997-08-04 1998-07-30 Sistema de agente de consevação para produtos de tratamento corporal

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19733684A DE19733684A1 (de) 1997-08-04 1997-08-04 Konservierungsmittelsystem für Körperpflegemittel
DE19733684.1 1997-08-04

Publications (1)

Publication Number Publication Date
WO1999007331A1 true WO1999007331A1 (fr) 1999-02-18

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EP (1) EP0993298A1 (fr)
JP (1) JP2001513488A (fr)
KR (1) KR20010022607A (fr)
CN (1) CN1268047A (fr)
AU (1) AU8733198A (fr)
BR (1) BR9811843A (fr)
CA (1) CA2299340A1 (fr)
DE (1) DE19733684A1 (fr)
HU (1) HUP0100333A2 (fr)
PL (1) PL338475A1 (fr)
SK (1) SK1492000A3 (fr)
TR (1) TR200000270T2 (fr)
WO (1) WO1999007331A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002009519A1 (fr) * 2000-07-20 2002-02-07 Cognis Iberia S. L. Utilisation d'esters quaternaires comme agents microbicides
WO2002069710A1 (fr) * 2001-03-01 2002-09-12 Lonza, Inc. Melanges conservateurs contenant des composes ammomium quaternaires
EP3496540A4 (fr) * 2016-08-11 2020-07-15 Ecolab USA Inc. Interaction entre des composés quaternaires antimicrobiens et des tensioactifs anioniques
US11406103B2 (en) 2016-03-01 2022-08-09 Ecolab Usa Inc. Sanitizing rinse based on quat-anionic surfactant synergy

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10223934B4 (de) * 2002-05-29 2009-04-09 Schülke & Mayr GmbH Verwendung eines Desinfektionsmittels zur Inaktivierung von Hepatitis B-Virus
US9028852B2 (en) * 2004-09-07 2015-05-12 3M Innovative Properties Company Cationic antiseptic compositions and methods of use
FR2992859B1 (fr) * 2012-07-09 2014-10-03 Fabre Pierre Dermo Cosmetique Utilisation de coceth sulfate de zinc comme agent antibacterien vis a vis de propionibacterium acnes
JP2014172894A (ja) * 2013-03-12 2014-09-22 Separator System Kogyo Kk エアゾール型可食性除菌剤
KR101506185B1 (ko) 2014-06-11 2015-03-26 주식회사 에스앤텍 4급 암모늄 화합물 내성균을 저해하는 방부조성물
KR101741981B1 (ko) * 2015-04-22 2017-06-01 코스맥스 주식회사 리브온 타입의 에어로졸 화장료 조성물
CN112702912A (zh) * 2018-09-27 2021-04-23 伦萨有限责任公司 颜色稳定的防腐剂组合物

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EP0273218A1 (fr) * 1986-12-24 1988-07-06 Wella Aktiengesellschaft Conservateur pour agents de nettoyage du corps et des cheveux ainsi que l'utilisation de cette composition de conservateur
EP0365825A1 (fr) * 1988-10-25 1990-05-02 Wella Aktiengesellschaft Composition de nettoyage des cheveux et de la peau contenant des conservateurs ainsi qu'utilisation d'une combinaison de conservateurs
EP0403303A2 (fr) * 1989-06-16 1990-12-19 Unilever Plc Composition pour le traitement des cheveux
EP0568307A1 (fr) * 1992-04-29 1993-11-03 Unilever Plc Composition cosmétique contenant des acides alpha-hydroxycarboxyliques comme agents de conservation
EP0636357A1 (fr) * 1993-07-31 1995-02-01 Wella Aktiengesellschaft Agent de soin capillaire et procédé d'utilisation

Patent Citations (5)

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Publication number Priority date Publication date Assignee Title
EP0273218A1 (fr) * 1986-12-24 1988-07-06 Wella Aktiengesellschaft Conservateur pour agents de nettoyage du corps et des cheveux ainsi que l'utilisation de cette composition de conservateur
EP0365825A1 (fr) * 1988-10-25 1990-05-02 Wella Aktiengesellschaft Composition de nettoyage des cheveux et de la peau contenant des conservateurs ainsi qu'utilisation d'une combinaison de conservateurs
EP0403303A2 (fr) * 1989-06-16 1990-12-19 Unilever Plc Composition pour le traitement des cheveux
EP0568307A1 (fr) * 1992-04-29 1993-11-03 Unilever Plc Composition cosmétique contenant des acides alpha-hydroxycarboxyliques comme agents de conservation
EP0636357A1 (fr) * 1993-07-31 1995-02-01 Wella Aktiengesellschaft Agent de soin capillaire et procédé d'utilisation

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002009519A1 (fr) * 2000-07-20 2002-02-07 Cognis Iberia S. L. Utilisation d'esters quaternaires comme agents microbicides
WO2002069710A1 (fr) * 2001-03-01 2002-09-12 Lonza, Inc. Melanges conservateurs contenant des composes ammomium quaternaires
EP1769678A2 (fr) * 2001-03-01 2007-04-04 Lonza, Inc. Mélanges conservateurs contenant des composés d'ammonium quaternaire
EP1769678A3 (fr) * 2001-03-01 2007-05-16 Lonza, Inc. Mélanges conservateurs contenant des composés d'ammonium quaternaire
AU2002255640B2 (en) * 2001-03-01 2007-12-13 Lonza, Inc. Preservative blends containing quaternary ammonium compounds
US7342044B2 (en) 2001-03-01 2008-03-11 Lonza Inc. Preservative blends containing quaternary ammonium compounds
US11406103B2 (en) 2016-03-01 2022-08-09 Ecolab Usa Inc. Sanitizing rinse based on quat-anionic surfactant synergy
EP3496540A4 (fr) * 2016-08-11 2020-07-15 Ecolab USA Inc. Interaction entre des composés quaternaires antimicrobiens et des tensioactifs anioniques
US11044907B2 (en) 2016-08-11 2021-06-29 Ecolab Usa Inc. Interaction between antimicrobial quaternary compounds and anionic surfactants
US11839209B2 (en) 2016-08-11 2023-12-12 Ecolab Usa Inc. Interaction between antimicrobial quaternary compounds and anionic surfactants

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AU8733198A (en) 1999-03-01
BR9811843A (pt) 2000-08-08
PL338475A1 (en) 2000-11-06
JP2001513488A (ja) 2001-09-04
DE19733684A1 (de) 1999-02-11
CN1268047A (zh) 2000-09-27
HUP0100333A2 (hu) 2001-06-28
SK1492000A3 (en) 2000-07-11
TR200000270T2 (tr) 2000-09-21
EP0993298A1 (fr) 2000-04-19
CA2299340A1 (fr) 1999-02-18
KR20010022607A (ko) 2001-03-26

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