EP0452408A1 - Melanges tensio-actifs - Google Patents

Melanges tensio-actifs

Info

Publication number
EP0452408A1
EP0452408A1 EP19900902183 EP90902183A EP0452408A1 EP 0452408 A1 EP0452408 A1 EP 0452408A1 EP 19900902183 EP19900902183 EP 19900902183 EP 90902183 A EP90902183 A EP 90902183A EP 0452408 A1 EP0452408 A1 EP 0452408A1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
alkyl
atoms
linear
mixtures according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
EP19900902183
Other languages
German (de)
English (en)
Inventor
Reinhard Müller
Gilbert Schenker
Karl Giede
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0452408A1 publication Critical patent/EP0452408A1/fr
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0094—High foaming compositions
    • 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
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • 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
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • 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
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/37—Mixtures of compounds all of which are anionic
    • 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
    • A61K2800/596—Mixtures of surface active compounds
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines

Definitions

  • the invention relates to surface-active mixtures with low skin stress.
  • magnesium ions in anionic surfactants such as fatty alcohol sulfates and fatty alcohol ether sulfates Products with improved skin tolerance can be obtained.
  • ampholytic and nonionic surfactants are often distinguished by improved skin tolerance compared to anionic surfactants.
  • these classes of surfactants cannot be used as a replacement for anionic surfactants for many areas of application because they do not achieve their properties in terms of their cleaning action.
  • the foam formation desired for shampoos is generally not guaranteed if amphoteric surfactants are used exclusively or predominantly.
  • the invention relates to surface-active aqueous mixtures comprising at least two different anionic surfactants, characterized in that the anionic surfactants a) sulfated hydroxyalkyl polyethylene and / or hydroxyalkyl polypropylene glycol ethers (A) of the general formula (I)
  • Rl for hydrogen or a linear alkyl radical
  • R2 for a linear or branched, saturated
  • M for hydrogen, ammonium, alkylammonium, alkanolammonium, in which the alkyl and alkanol radicals each have 1 to 4
  • the surface-active compounds of the formula (I) are the subject of German patent application P 37 23 354.8. These compounds can be prepared by reacting epoxides of the general formula (III) with alcohol alkoxylates of the general formula (IV),
  • the compounds of the formula (I) can have ethylene glycol and propylene glycol groups in any ratio and in any order in the molecular chain; Such mixed ethers are also encompassed by the general formula (I).
  • alkyl radicals R *, R 2 , R3 and R can be both uniform groups and mixtures with different chain lengths.
  • Compounds (A) or (B) in which the groups R 1 and / or R 2 or R have different chain lengths are present above all if the starting materials for the preparation of these compounds from native raw material sources, such as natural fats and oils, be won.
  • R 3 an alkyl group with 6 to 16 C atoms, in particular with 8 to 12 C atoms
  • R 2 is a linear alkyl chain with 4 to 19 C atoms ⁇ men, in particular with 6 to 16 carbon atoms
  • R and R ⁇ hydrogen, M sodium, potassium or magnesium and n represents an integer from 3 to 12, in particular from 3 to 9.
  • Compounds (A) according to formula (I) in which R * represents a decyl group and R 2 represents an octyl group have proven to be very particularly suitable.
  • the surface-active mixtures according to the invention preferably contain compounds (A) of the formula (I) in amounts of 1 to 99% by weight, based on the total amount of the anionic surfactants.
  • the surface-active mixtures according to the invention contain a total of about 2-50% by weight of anionic surfactants. A content of 5-30% by weight is preferred.
  • the surface-active mixtures according to the invention can additionally contain 0.5-20% by weight, in particular 1-10% by weight, of ampholytic and / or zwitterionic surfactants.
  • Ampholytic surfactants are understood to mean those surface-active compounds which, in addition to a Cg-Cig-alkyl or -acyl group, contain at least one free amino group and at least one -C00H or -S ⁇ 3H group in the molecule and are capable of forming internal salts .
  • ampholytic surfactants are N-alkylglycines, N-alkylpropionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl N-alkylamidopropylglycine, N-alkyltaurine, N-alkyl sarcosine, 2-alkyla inopropionic acid and alkylaminoacetic acid, each with about 8 to 18 carbon atoms in the alkyl group.
  • Zwitterionic surfactants are those surface-active compounds which carry at least one quaternary ammonium group and at least one -COCO ( ⁇ ) - or -S ⁇ 3 ( ⁇ ) group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the cocoalkyl-dimethylam onium glycinate, N-acylaminopropyl-N, N-dimethylam ⁇ .onium glycinate, for example the Ko - Kosacylaminopropyl-dimethylammonium glycinate, and 2-alkyl-3-car-boxylmethyl-3-hydroxyethyl-imidazolines each with 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
  • the skin-protecting properties of the agents according to the invention come into their own when they are formulated in such a way that they have a pH value in the vicinity of the neutral point. Agents with pH values in the range from 5.5 to 7.5, in particular from 6.5 to 7.5, are therefore preferred.
  • the agents according to the invention can be used in a variety of consumer products such as hair shampoo, bubble baths, shower baths, liquid soaps and manual dishwashing detergents.
  • these products contain the usual constituents such as emulsifiers, oil components, fats and waxes, solubilizers, thickeners, superfatting agents, biogenic active ingredients, film formers, fragrances, Dyes, pearlescent agents, foam stabilizers, preservatives and pH regulators.
  • emulsifiers oil components, fats and waxes, solubilizers, thickeners, superfatting agents, biogenic active ingredients, film formers, fragrances, Dyes, pearlescent agents, foam stabilizers, preservatives and pH regulators.
  • the substances customary in cosmetic preparations such as. B. fatty acid partial glycerides, fatty acid sorbitan partial esters and their ethoxylates, soaps, fatty alcohol polyglycol ethers, lanolin, wool fatty alcohols and alkyl phosphates can be used.
  • Usual oil components are substances such as paraffin oil, vegetable oils, fatty acid esters, squalane and 2-0ctyldodecanol, while the fats and waxes used are, for example, walnut, beeswax, montan wax, paraffin and cetylstearyl alcohol.
  • Low monohydric or polyhydric alcohols such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol, 1,3-butylene glycol and diethylene glycol are usually used as solubilizers.
  • Substances such as polyethoxylated lanolin derivatives, lecithin derivatives and fatty acid alkanolamides can be used as superfatting agents, the latter also serving as foam stabilizers at the same time.
  • Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar gum, agar agar, alginates and tylos, and also carboxymethyl cellulose and hydroxyethyl cellulose, furthermore higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, polyvinyl alcohol and polyvinylpyrrolidone and finally electrolytes such as cooking salt and ammonium chloride, if desired in combination with alkyl ether sulfates.
  • Biogenic active substances are to be understood as meaning plant extracts, protein breakdown products and vitamin complexes.
  • Common film formers are, for example, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives and similar compounds.
  • Suitable preservatives are the substances listed in the annex to the Cosmetics Ordinance and the 1st to 14th Ordinance amending the Cosmetics Ordinance. A further list of suitable preservatives can be found in the positive list of the Cosmetic and Detergent Industry Association (IKW), Appendix 6, 1st and 2nd part, from April 1988.
  • IKW Cosmetic and Detergent Industry Association
  • Particularly suitable pearlescent agents are glycol distearic acid esters such as ethylene glycol distearate, but also fatty acid monoglyco testers.
  • the dyes which can be used are the substances which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes” by the Dye Commission of the German Research Foundation, published in Ver ⁇ lag Chemie, Weinheim, 1984. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.
  • further components of the agents according to the invention are fragrances and substances which serve to adjust the pH of the agents.
  • the mixtures according to the invention are preferably used in products which are used for washing, dyeing, waving or rinsing hair.
  • the mixtures are particularly suitable for shampoos for washing hair.
  • the swelling of pig epidermis served as a measure of the skin tolerance of the surfactant mixtures.
  • the required epidermis was obtained immediately after young pigs were slaughtered and stored frozen.
  • the Q value of the water-treated skin is therefore by definition 0%; negative values indicate anti-swelling properties.
  • the compound was prepared starting from 1,2-epoxydodecane and the adduct of 4 moles Ethylene oxide on n-butanol analogous to the process described in Example 1 of German patent application P 37 23 354.8.
  • the results of the swelling measurements are summarized in the following table.
  • the amount given relates to the total amount of 2% anionic surfactant.
  • the foaming behavior of the surfactant mixtures was determined using a motorized blow-foam apparatus based on DIN 53902.
  • 340 ml of surfactant solution (2% by weight active substance in tap water from Düsseldorf-Holthausen at 18 ° dH) were prepared.
  • the foam was perforated at room temperature (Holes of 1 mm diameter, 10 impacts at a frequency of 50 impacts / min, 13 cm stroke) produced; it is very fine-pored and thus largely corresponds to a foam that forms on the head when shampooing.
  • the measurements were carried out as a duplicate determination without grease contamination of the surfactant solution.
  • This mixture was diluted with water and also used in the form of a solution with 2% by weight of active substance.
  • the following amounts of foam were measured: after 1 minute: 240 ml after 3 minutes: 210 ml after 5 minutes: 190 ml
  • the measured amounts of foam of the surfactant solutions according to the invention are given in the following table in percent based on the amount of foam of the comparison substance.
  • the hair had good wet combability and good dry combability after treatment with this shampoo.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)

Abstract

Les mélanges aqueux tensio-actifs contenant les constituants suivants en tant qu'agents de surface anioniques sont particulièrement bien supportés par la peau tout en ayant un bon pouvoir lavant et moussant: (a) hydroxyalkylpolyéthylène-glycoléther et/ou hydroxyalkylpolypropène-glycoléther sulfaté(s) (A) correspondant à la formule générale (I), où R1 représente hydrogène ou un résidu alkyle linéaire avec entre 1 et 16 atomes de C; R2 représente un résidu alkyle saturé linéaire ou ramifié avec entre 1 et 22 atomes de C; R3 représente hydrogène ou un résidu alkyle linéaire avec entre 1 et 16 atomes de C; M représente hydrogène, ammonium, alkylammonium, alcanolammonium, les résidus alkyle ou alcanol ayant chacun entre 1 et 4 atomes de C, ou un atome de métal alcalin, de métal alcalino-terreux ou d'aluminium; m représente le nombre 2 ou 3; n représente un chiffre compris entre 1 et 30; à condition que le nombre total des atomes de C contenus dans R1 et R3 soit compris entre 6 et 16; et (b) semiester d'acide sulfosuccinique (B) correspondant à la formule générale (II), où R est un résidu alkyle saturé ou oléfiniquement insaturé, linéaire ou ramifié, avec entre 8 et 22 atomes de C; m est 2 ou 3; w est 0 ou un chiffre compris entre 1 et 15; et Z et Z', indépendamment l'un de l'autre, représentent un métal alcalin, un métal alcalino-terreux, un groupe ammonium ou un groupe alkylammonium ou alkylolammonium avec entre 1 et 4 atomes de C dans chaque groupe alkyle ou alkylol.
EP19900902183 1989-01-16 1990-01-08 Melanges tensio-actifs Ceased EP0452408A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19893901067 DE3901067A1 (de) 1989-01-16 1989-01-16 Oberflaechenaktive mischungen
DE3901067 1989-01-16

Publications (1)

Publication Number Publication Date
EP0452408A1 true EP0452408A1 (fr) 1991-10-23

Family

ID=6372153

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19900902183 Ceased EP0452408A1 (fr) 1989-01-16 1990-01-08 Melanges tensio-actifs

Country Status (3)

Country Link
EP (1) EP0452408A1 (fr)
DE (1) DE3901067A1 (fr)
WO (1) WO1990007922A2 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8910373D0 (en) * 1989-05-05 1989-06-21 Ici Plc Hard surface cleaning and compositions therefor
DE4122200A1 (de) * 1991-07-04 1993-01-07 Henkel Kgaa Waessrige zubereitungen oberflaechenaktiver substanzen

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0639592B2 (ja) * 1985-11-06 1994-05-25 ライオン株式会社 毛髪用液体洗浄剤組成物
US4759875A (en) * 1986-01-14 1988-07-26 S. C. Johnson & Son, Inc. Oxo-derived mild surfactant blends
DE3723354A1 (de) * 1987-07-15 1989-01-26 Henkel Kgaa Sulfatierte hydroxy-mischether, verfahren zu ihrer herstellung und ihre verwendung

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9007922A2 *

Also Published As

Publication number Publication date
WO1990007922A3 (fr) 1990-10-18
WO1990007922A2 (fr) 1990-07-26
DE3901067A1 (de) 1990-07-26

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