WO1998020853A1 - Utilisation de tensioactifs gemines anioniques dans des formulations pour agents de lavage, de nettoyage et de soins corporels - Google Patents

Utilisation de tensioactifs gemines anioniques dans des formulations pour agents de lavage, de nettoyage et de soins corporels Download PDF

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Publication number
WO1998020853A1
WO1998020853A1 PCT/EP1997/005892 EP9705892W WO9820853A1 WO 1998020853 A1 WO1998020853 A1 WO 1998020853A1 EP 9705892 W EP9705892 W EP 9705892W WO 9820853 A1 WO9820853 A1 WO 9820853A1
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general formula
fatty acid
compounds
alkyl
weight
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PCT/EP1997/005892
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German (de)
English (en)
Inventor
Michael Brock
Klaus Kwetkat
Herbert Koch
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RWE-DEA Aktiengesellschaft für Mineraloel und Chemie
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Publication of WO1998020853A1 publication Critical patent/WO1998020853A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/08—Sulfation or sulfonation products of fats, oils, waxes, or higher fatty acids or esters thereof with monovalent alcohols
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
    • C08G65/3344—Polymers modified by chemical after-treatment with organic compounds containing sulfur containing oxygen in addition to sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/02—Alkyl sulfonates or sulfuric acid ester salts derived from monohydric alcohols

Definitions

  • the invention relates to the use of salts of di- ⁇ -sulfodicarboxylic acid diesters in formulations for washing and cleaning textiles, cleaning hard surfaces and cleaning and washing skin and hair.
  • gemini or twin surfactants referred to as "New Generation of Surfactants” (MJ Rosen, Chemtech, No. 3 (1995) 30) are, provided their structure is optimally selected, surfactants with a significantly higher performance than their conventional equivalents and offer more In addition, when choosing the right structural variant, a high degree of multifunctionality and thus help to increase the washing or cleaning performance per unit mass of the formulation.
  • the gemini polyhydroxy fatty acid and ge inipolyether fatty acid amides described in the applications WO 95/19953 and WO 95/19955 are nonionic gemini surfactants.
  • anionic gemini surfactants as described in application P 19633 497 (formula I), are used, a significant increase in the efficiency of entire end formulations is achieved.
  • the di- ⁇ -sulfodicarboxylic acid diesters are significantly more efficient than conventional anionic surfactants with regard to, for example, the critical micelle formation concentration, interfacial tension, water solubility, hardness stability, solvent-imparting effect and detergency, and, due to their special structure, they are particularly mild on the skin and biodegradable.
  • the present invention relates to the use of anionic gemini surfactants of the formula I in washing, cleaning and personal care products in which they contain at least 0.1 n% are included.
  • anionic gemini surfactants of the formula I in washing, cleaning and personal care products in which they contain at least 0.1 n% are included.
  • the salts of the di- ⁇ -sulfodicarboxylic acid diesters are described in published patent application WO 96/25393 and in German patent application P 196 33497, which we hereby introduce as a reference.
  • R, R and R in formula I have the meanings described below:
  • R and R independently of one another represent an unbranched or branched, saturated or unsaturated hydrocarbon radical with 1 to
  • Tridecyl Tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadec cyl, n-nonadecyl, n-eicosyl, n-uneicosyl, n-docosyl and their branched-chain isomers and the corresponding mono-, di- or tri-unsaturated radicals.
  • R 2 represents a spacer consisting of an unbranched or branched, saturated or unsaturated chain with 2 to 100 carbon atoms, 0 to 20 oxygen and / or 0 to 20 nitrogen and / or 0 to 4 sulfur and / or 0 to 3 Phosphorus atoms.
  • the chain also has 0 to 20 functional side groups such as. B. hydroxyl, carbonyl, carboxyl, amino and / or acylamino groups and / or 0 to 4 cycles which are isolated or fused.
  • the spacer R means in particular
  • R are each independently H or C, - to C c -Al-
  • spacer R there are 0 to 20, preferably 1 to 12,
  • R 2 can also be derived from a methyl or ethyl ester of a polycarboxylic acid (MW 500 to 100000), the ⁇ -carbon atoms of which are sulfonated between 0 and 100%. However, the ⁇ -carbon atoms are preferably only between 10 and 60% sulfonated.
  • M, M ' alkali, ammonium, alkanolam onium or alkaline earth.
  • the di- ⁇ -sulfodicarboxylic acid diesters can also contain di- ⁇ -sulfodicarboxylic acid monoesters, mono- ⁇ -sulfodicarboxylic acid diesters and mono- ⁇ -sulfodicarboxylic acid monoesters.
  • Enzymes A whole series of enzymes can be contained in the formulations according to the invention, for example proteases, amylases, lipases, cellulases and peroxidases and mixtures of the respective enzymes. Other enzymes can also be incorporated into detergent formulations, where, like the aforementioned, they come from a wide variety of origins from bacteria, fungi, e.g. B. yeasts, and other plants, but can also be of animal origin.
  • Enzymes are weighed up to 50 mg, preferably 0.01 mg up to 3 mg of active enzyme used per gram of detergent formulation, d. H. 0.001% to about 5% in the detergent formulations according to the invention.
  • Enzyme stabilizers include water-soluble sources of calcium and / or magnesium ions, which must be added frequently so that the builder system does not also remove these central atoms of the enzymes and thus deactivate them. Calcium ions are generally more effective than magnesium ions. Additional stabilization can be achieved by adding borates (US 4,537,706, Severson). Typically, the formulations according to the invention contain 1 to 30, preferably 2 to 20, particularly preferably 5 to 15 and very particularly preferably 8 to 12 millimoles of calcium ions per liter of final formulation. Although the concentration in different formulations may vary depending on the enzymes used, there should always be enough calcium ions available after complexing by the builder system and soaps to keep the enzymes activated.
  • any water soluble calcium or Magnesium salt can be used.
  • the following examples may be mentioned here without restricting the formulations according to the invention: calcium chloride, formate, sulfate, hydroxide, malate, maleate, acetate and the corresponding magnesium salts.
  • the detergent formulations according to the invention contain 0.05% to 2% water-soluble calcium and / or magnesium salts.
  • Borate stabilizers are contained in the formulations according to the invention to 0.25% to 10%, preferably 0.5% to 5% and particularly preferably 0.75% to 3% - calculated as boric acid. The added borate stabilizers must be able to form boric acid.
  • boric acid is preferred here, but boron oxide, borax, other alkali borates and substituted boric acids, such as, for example, As phenyl, butyl and p-bromophenyl boric acid can be used.
  • bleaching systems for the formulations according to the invention, the use of a bleaching system, be it bleaching agent and activator or just a bleaching agent, is optional. If used, the bleaching agents are used in amounts of 1 to 30%, preferably 5 to 20%. If used, bleach activators are used in amounts of 0.1 to 60% of the bleach. 0.5 to 40% bleaching system, based on the formulation according to the invention, is preferably used. All bleaches suitable for cleaning textiles, hard surfaces (industrial and household cleaners, dishwashing detergents) or other cleaning tasks can be used. These include bleaches that work on an oxygen basis as well as other systems. Perborates, e.g. B.
  • sodium perborates be it as mono- or tetrahydrate, can be used, as can percarboxylic acid bleaches and their salts.
  • Suitable representatives of this class include magnesium peroxyphthalate hexahydrate, magnesium metachloroperbenzoate, 4-nonylamino-4-oxoperoxybutanoic acid, diperoxydodecanedioic acid and, particularly preferably, 6-nonylamino-6-oxoperoxycapric acid (US 4634551, Bums et al).
  • Peroxygen bleaches can also be used.
  • Suitable representatives of this class include sodium carbonate peroxohydrate and comparable percarbonates, sodium pyrophosphate peroxohydrate, urea peroxohydrate, sodium peroxide and persulfate bleach.
  • Mixtures of bleaching agents can also be used in the detergent and cleaning agent formulations according to the invention.
  • Peroxygen bleaches are preferably combined with bleach activators, which include, but are not limited to, the formulations according to the invention, nonanoyloxyphenylsulfonate, tetraacetylethylenediamine and mixtures thereof, and other combinations of bleaching agent and activators mentioned in US Pat. No. 4,634,551.
  • Amide derivatives of the formulas R 1 N (R 5 C (0) R 2 C (0) L or are very particularly preferred as bleach activators
  • R 1 C (0) N (R 5 ) R 2 C (0) L, where R 1 is an alkyl group with 6 to 12
  • R is an alkylene group having 1 to 6 carbon atoms
  • R is a hydrogen atom or alkyl
  • aryl or alkylaryl having 1 to 10 carbon atoms
  • L is any suitable for nucleophilic reactions
  • Phenylsulfonate means. The following compounds are mentioned as examples: (6-0ctanamido-caproyl) oxyphenylsulfonate,
  • Acyl lactam activators belong to another class of preferred bleach activators, here especially acyl caprolactam and acyl valerolactam with alkyl, aryl,
  • Alkoxyaryl and alkyl aryl acyl groups containing 1 to 16 carbon atoms are among the preferred systems.
  • the washing and cleaning agents according to the invention can also optionally contain builder systems (overall builders) which consist of water-softening silicates and / or other inorganic and / or organic builders. They are used in detergent formulations to help remove dirt and to control water hardness.
  • builder systems all builders which consist of water-softening silicates and / or other inorganic and / or organic builders. They are used in detergent formulations to help remove dirt and to control water hardness.
  • Liquid formulations contain from 0 to 50%, preferably 5 to 30% of total builders.
  • Granulated formulations contain 0 to 80%, preferably 15 to 50% of total builders. However, higher concentrations should not be excluded here.
  • Inorganic builders include in particular silicates and aluminosilicates.
  • SKS-6 aluminosilicates
  • aluminosilicates also useful in the formulations of the invention and particularly important in granular detergent formulations.
  • the usable aluminosilicate builders can be described with the empirical formula [M z (zA10 2 ) y ] xH 2 0, z and y assume values of at least 6, the molar ratio of z to y is in the range from 1.0 to 0, 5, x takes values from approx. 0 to 30. It can be crystalline as well as amorphous, synthetic or naturally occurring aluminosilicates.
  • the silicate builders can contain 0 to 60%.
  • the inorganic builders further include, without restricting the formulations according to the invention, alkali, ammonium and alkanolammonium salts of polyphosphates (e.g. tripolyphosphates, pyrophosphates and polymeric metaphosphates), phosphonates, carbonates (also bicarbonates and sesquicarbonates) and sulfates.
  • polyphosphates e.g. tripolyphosphates, pyrophosphates and polymeric metaphosphates
  • phosphonates e.g. tripolyphosphates, pyrophosphates and polymeric metaphosphates
  • carbonates also bicarbonates and sesquicarbonates
  • sulfates e.g. tripolyphosphates, pyrophosphates and polymeric metaphosphates
  • Organic builders also belong to the builders which can be used in the formulations according to the invention. These include polycarboxylates such as ether carboxylates (cyclic or acyclic), hydroxypolycarboxylates, copolymers of maleic anhydride and ethylene or vinyl methyl ether, 1,3,5-trihydroxybenzene-2,4,6-trisulfonic acid and carboxymethoxysuccinic acid, all in the form of the acid or its alkali , Ammonium or organoammonium salts can be used. Alkyl, ammonium or organoammonium salts of polyacetic acid are just as suitable as salts of citric acid or combinations of different builders. AI kenylsuccinic acids and salts are particularly preferred organic builders. Monocarboxylic acid salts can also be incorporated into the formulations according to the invention either alone or in combination with one of the abovementioned builders.
  • polycarboxylates such as ether carboxylates (cyclic or acyclic),
  • the inorganic (without silicates) and / or organic builders are 0 to 40% contained in the formulation.
  • dirt-release polymers belonging to the prior art can be used as ingredients in the formulations according to the invention.
  • soil release polymers contribute to easier removal of oil and grease dirt, especially during washing processes and in textile finishing.
  • Dirt release polymers are characterized by the fact that they are both hydrophilic and Have hydrophobic components.
  • the mode of action of soil release polymers is based on a modification of the fiber surface of polyester or cotton / polyester blended fabrics with the help of the hydrophilizing polymer.
  • the hydrophilic segment of the soil release polymer makes the surface easier to wet, while the hydrophobic segment acts as an anchor group.
  • Moisture transport water absorption and absorbency
  • the soil release polymer such as polyester or polyester / cotton blended fabrics. They also give the fabrics antistatic and gliding properties, which makes handling these fibers easier when cutting and sewing (textile processing).
  • the treatment of the fabric with the soil release polymer is to be understood as a kind of impregnation, i.e. the soil release polymer remains on the fiber for several wash cycles.
  • soil release polymers include polyesters or oligoesters based on terephthalic acid / polyoxyalkylene glycols / monomeric glycols. Dirt release polymers from this group have been marketed for several years.
  • the most important sales products include ZELCON (Du Pont), MILEASE T (ICI), ALKARIL QCF / QCJ (Alkaril Inc.) and REPEL-0-TEX (Rhone-Poulenc).
  • Preferred within the formulations claimed in this invention are soil release polymers which can be described by the following empirical empirical formula:
  • CAP represents so-called "capping groups” which close the polymer at the end.
  • the end group closure contributes to the stabilization of the polymers.
  • CAP stands for a large number of possible end groups.
  • Preferred end groups include sulfoaroyl groups such as the sulfobenzoyl group, which can be introduced in the form of a transesterification with alkyl sulfobenzoate.
  • the incorporation of end groups on the one hand has a regulating effect on the molecular weight, on the other hand it leads to the stabilization of the polymers obtained.
  • end groups are also poly (oxyethylene) monoalkyl ethers in which the alkyl group contains 1 to 30 carbon atoms and the polyoxyethylene group consists of 2-200 oxyethylene units. End groups of this type are described, for example, in WO 92/17523 and DE 4001 415.
  • EP 0 253 567 and EP 0357 280 describe in particular those end-capped polyesters (capped polyesters) which are, on the one hand, by nonionic groups such as, for example, C 1 -C 4 -alkyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -acyl and also by ionic groups Succinate groups are closed. In principle, mixtures of different end groups are also possible, where x assumes values from 0-2.
  • the group (EG / PG) stands for an oxyethyleneoxy, oxypropyleneoxy group or mixtures thereof, where y assumes numerical values from 0 to 80.
  • EG / PG stands for an oxyethyleneoxy, oxypropyleneoxy group or mixtures thereof, where y assumes numerical values from 0 to 80.
  • branched monomeric glycol building blocks e.g. 1,2-butylene, 3-methoxy-1,2-propylene glycols (EP 0241 985).
  • the group (T) is among others for a terephthaloyl group, which acts as an anchor group in the polymer between the soil release polymer and the substrate (fiber).
  • a terephthaloyl group acts as an anchor group in the polymer between the soil release polymer and the substrate (fiber).
  • aliphatic analogues can also be represented, e.g. Adipates that can be incorporated using adipic acid or adipic acid diesters.
  • DE 4403866 e.g. aphiphile polyester claimed, which contain aromatic as well as aliphatic dicarboxylic acids and are used as detergent additive or soil release polymer.
  • Z assumes values from 1 to 50.
  • anionic groups primarily sulfoisopthaloyl groups
  • the sulfoisophthaloyl groups stabilize the polymer and inhibit the transition from the desired amorphous form to the poorly soluble crystalline form of the polymer.
  • such anionic modifications of the above polyesters which contain the sodium salt of sulfoisophthalic acid as a further polymerization component.
  • the polymerized polyethylene glycols (PEG) have molar masses of 200-1000 and result after their polymerization with ethylene glycol and terephthalic acid polyester with molecular weights from 2000 to 10000.
  • the poly (oxyalkylene) oxy groups are poly (oxyethylene) oxy groups, although the molecular weights can vary considerably.
  • poly (oxypropylene) oxy groups and all conceivable mixtures can also be represented.
  • the soil release polymers based on poly or oligoester described by the empirical empirical formula above have molecular weights between 200 and 100,000. Usually preferred are molecular weights in the range from 500 to 25,000.
  • cellulose derivatives can also be used in the formulations claimed.
  • Such products are commercially available, for example, as hydroxyethers of cellulose under the product name METH0CEL (Dow).
  • Cellulose derivatives with C 1 -C 4 -alkyl and C 4 -hydroxyalkyl celluloses (US Pat. No. 4,000,093) are preferred.
  • Another group of soil release polymers can also Poly (vinyl ester) compounds are used. Graft polymers of polyvinyl acetate and polyoxyethylene glycol are particularly preferred. Products of this type are commercially available, such as SOKALAN HP 22 (BASF). If dirt release polymers are used in the formulations according to the invention, the content is 0.01 to 10.0% by weight.
  • a preferred biodegradable chelating agent is ethylenediamine disuccinate.
  • the above-mentioned agents are used in proportions of 0.1 to 10%, particularly preferably 0.1 to 3.0%, of the detergent formulation.
  • the formulations according to the invention can contain alkoxylated, preferably ethoxylated, amines, regardless of whether they are mono-, oligo- or polymeric amines.
  • the amount used for solid formulations is 0.01 to 10%, for liquid formulations 0.01 to 5% of the total formulation.
  • Other groups of compounds which have these properties are cationic compounds (EP 0 111 984), zwitterionic polymers (EP 0 112 592) or carboxymethyl cellulose, which are likewise capable of increasing the dirt-carrying capacity of a washing liquor.
  • Polymeric dispersion aids (cobuilders): These additives are used in amounts of 0.1 to 7.0% of the total formulation according to the invention, which are polycarboxylates or polyethylene glycols which both enhance the action of the builder used and also incrustations and resurfacing Prevent use and play a role in the detachment of particles of dirt.
  • the compounds which can be used here are obtained by polymerization or copolymerization of suitable unsaturated carboxylic acid or carboxylic anhydride monomers. Polyacrylates, but also maleic anhydride / acrylic acid copolymers are preferred here. moves.
  • the molecular weights of the former range from 2,000 to 10,000, preferably 4,000 to 7,000 and particularly preferably in the range from 4,000 to 5,000.
  • Suitable copolymers have molecular weights of 2,000 to 100,000, preferably 5,000 to 75,000 and particularly preferably 7,000 to 65000 on.
  • Polyethylene glycols which can be used have molecular weights in the range from 500 to 100,000, particularly preferably from 1,500 to 10,000.
  • Polyasparagates and glutamates can also be used together with zeolite builders, the polyasparagates that can be used having average molecular weights of approximately 10,000.
  • Optical brighteners All optical brighteners known from the prior art can be used in the formulations according to the invention. They are incorporated at 0.05 to 1.2%, based on the total formulation. Some non-limiting examples of suitable connecting groups are mentioned below: stilbene derivatives, pyrazolines, coumarin, carboxylic acids, methine cyanines, dibenzothiophene-5,5-dioxide, azoles and 5- and 6-membered heterocycles.
  • Foam inhibitors Depending on the precise composition (i.e. foaming power of the surfactants used) and the type of foam inhibitor, 0 to 5% (based on the total formulation) of these must be used. Monofatty acid salts are used in an amount of 0 to 5%, but preferably 0.5 to 3%, silicones are used in an amount of up to 2, preferably however 0.01 to 1% and particularly preferably from 0.25 to 0 , 5% used.
  • the compounds which can be used as foam inhibitors in the formulations according to the invention include monofatty acids and their salts with carbon chain lengths of 10 to 24, preferably 12 to 18, carbon atoms.
  • High molecular weight non-surface-active compounds such as paraffins, fatty acid esters (eg triglycerides), aliphatic ketones, N-alkylated amino triazines or di- to tetraalkyldiaminochlorotriazines, monostearyl phosphates and monostearyl alcohol phosphate esters can also be used.
  • Silicones can also be used as foam inhibitors in the present formulation, as can mixtures of silicones and silane-modified silicates. I. a. polyalkylene glycols can be used as solvents here.
  • Fabric softener Various fabric softeners that can be used in the washing process can be used here, but especially Smectit-Tone and other softening clays in amounts between 0.5 and 10% (based on the total formulation).
  • the above plasticizers can be used in combination with other plasticizers such as amines and the popular cationic plasticizers.
  • Surfactants In addition to the anionic gemini surfactants of the formula (I) (see also DE 19505367 and 19633497), combinations or individual surfactants mentioned below can be combined with the gemini surfactants in the formulations according to the invention. 0.1 to 70% of these surfactants are used: without restricting the formulations, examples of nonionic surfactants include fatty acid glycerides, fatty acid polyglycerides, fatty acid esters, alkoxylates of higher alcohols, alkoxylated fatty acid glycerides, polyoxyethyleneoxypropylene glycol fatty acid esters, polyoxyethylene sorboxy fatty acid fatty acid esters, polyoxyethylene sorboxy fatty acid fatty acid esters or hardened castor oil derivatives, polyoxyethylene lanolin derivatives, polyoxyethylene fatty acid amides, polyoxyethylene alkylamines, derivatives of alkanolamines, alkylamine oxides, derivatives of protein hydrolyzates, hydroxy mixed ethers, alkylpol
  • N-methylalkylglucamides N-methylalkylglucamides
  • non-ionic, non-ionic mixture Surfactants as described in WO 95/19951 (polyhydroxyamine compounds), WO 95/19953, WO 95/19954 and WO 95/19955 and WO 95/20026).
  • anionic surfactants that can be used for combinations include soaps, ether carboxylic acids and their salts, alkyl sulfonates, ⁇ -olefin sulfonates, sulfo fatty acid derivatives (including those described in WO 93/25646), sulfonates of higher fatty acid esters, higher alcohol sulfates (primary and secondary), alcohol ether sulfates, hydroxy mixed ether sulfates, sulfates of alkoxylated carboxylic acid alkanols, salts of phosphate esters, taurides, isethionates, linear alkylbenzenesulfonates, bridged alkylbenzenesulfonates (such as DOWFAX types from Dow), alkylarylsulfonate derivatives and sulfates of polyacids Acylamino acids, alkyl ether carboxylic acids, alkyl and dialkyl sulfosuccinates
  • Examples of common cationic surfactants that can be used for combinations include alkyltrimethylammonium salts, dialkyldimethylammonium salts, alkyldimethylbenzylammonium salts, imidazolini derivatives, alkylpyridinium salts, quaternized fatty acid esters of alkanolamines, alkyl isoquinolinium salts, benzethonium chlorides and cationic acylamino acid derivatives.
  • Examples of surface-active substances, A pholytes and betaines that can be used for combinations are carbobetaines, such as. B.
  • cocoacylamido propyldimethylbetaine acylamidopentanediethylbetaine, dimethylammoniohexanoate acylamidopropane (or -ethane) dimethyl (or - diethyl-) betaine - all with C chain lengths between 10 and 18, sulfobetaines, I idazoline derivatives, soybean lipids and lecithin.
  • the amine-N-oxides mentioned above can also be in polymeric form, a ratio of amine to amine-N-oxide of 10: 1 to 1: 1,000,000 being required.
  • the average molecular weight is 500 to 1 000 000, but particularly preferably 5 000 to 100 000.
  • Additional components can be incorporated into the washing, cleaning or personal care formulations. These are carriers, hydrotropes, processing aids, dyes or pigments, perfumes, solvents for liquid formulations (alcohols with 1 to 6 carbon atoms and 1 to 6 hydroxyl groups are particularly preferred), solid fillers for bar soap formulations, pearlescent agents, e.g. B. distearoylglycerides, preservatives, buffering systems and so on. Should a higher foaming power of the formulation such. B. may be required in some personal care products, this can e.g. B. by the addition of C 10 -C 16 alkanolamides (in concentrations of 1 to 10% of the total formulation). Other water-soluble magnesium salts can also be added in amounts of 0.1 to 2% to increase the foaming power and the fat-dissolving power.
  • carriers hydrotropes, processing aids, dyes or pigments, perfumes, solvents for liquid formulations (alcohols with 1 to 6 carbon atoms and 1 to 6 hydroxy
  • surfactant components can also be stabilized by adsorption on porous hydrophobic substances and sealed into the formulation with a further hydrophobic layer.
  • the formulations of the invention can be used in a wide variety of ways, such as. B. as a skin cleaner, bath additive, shower bath, denture cleaner, shampoo and care product, shaving soap, pre-shaving, disinfectant, dispersant, universal detergent and mild detergent, both in liquid form and as a powder or granulate, for textiles, hand and Dishwasher detergents, household cleaners and industrial cleaners.
  • ways such as. B. as a skin cleaner, bath additive, shower bath, denture cleaner, shampoo and care product, shaving soap, pre-shaving, disinfectant, dispersant, universal detergent and mild detergent, both in liquid form and as a powder or granulate, for textiles, hand and Dishwasher detergents, household cleaners and industrial cleaners.
  • the carrier strips were separated with a knife.
  • test strip each was then placed in the metal guide rail of a Dardner washability and abrasion tester (model M-105-A, Erichsen) and with a damp sponge, which was placed in a sled, with 16 ml of the surfactant-containing formulations to be examined (Surfactant content: 1 wt .-%) cleaned. This was done by moving the carriage back and forth ten times. After the test strips had dried, the PVC film was detached from the carrier strip and stuck on white cardboard with the cleaned side up.
  • a Dardner washability and abrasion tester model M-105-A, Erichsen
  • Example 1 (not according to the invention):
  • the cleaning performance of a standard all-purpose cleaner was determined to be 65% as the standard formulation.
  • anionic gemini surfactant 3.0% by weight C 13 alcohol with 8 E0 *: 1.0% by weight
  • the cleaning performance of the formulation containing compound 1 was determined to be 73% and is therefore higher than that mentioned in Example 1.
  • the cleaning performance of the formulation containing compound 2 was determined to be 80% and is therefore higher than that mentioned in Example 1.
  • the cleaning performance of compound 3 was determined to be 72% and is therefore higher than that mentioned in example 1.
  • the washing drum of a standard household washing machine was loaded with 4 kg (for the 95 ° and 60 ° C wash) or with 1 kg (for the 30 ° C wash) of soiled cotton balast fabric. Furthermore, test lobes of the WFK test fabric (laundry research, now Research Institute for Cleaning Technology eV, Krefeld) treated with skin fat pigment soiling were applied to a white cotton towel with the test soiled side up. sews. The cotton towel thus prepared was added to the ballast fabric in the drum of the household washing machine.
  • Anionic gemini surfactant 13.0% by weight
  • the amount of liquid heavy-duty detergent used was 25 g per wash. After washing, the WFK test fabrics were dried.
  • the detergency was determined spectrophotometrically by determining the remission using the datacolor 3890 spectrophotometer (white standard: 100% remission, test soiled tissue: 0% remission).

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Abstract

L'invention concerne l'utilisation de sels de diester d'acide di-α-disulfodicarboxylique correspondant à la formule (I), dans des formulations destinées au lavage et au nettoyage de textiles, au nettoyage de surfaces dures et au nettoyage et au lavage de la peau et des cheveux. Dans ladite formule (I): R1 et R3 représentent chacun un groupe hydrocarbure comportant 1 à 22 atomes de carbone; R2 représentent un espaceur constitué d'une chaîne présentant 2 à 100 atomes de carbone, qui peut contenir des atomes d'oxygène, d'azote et/ou de phosphore et présenter des groupes latéraux fonctionnels; et A et B représentent oxygène, des groupes alcoxylène ou azote dérivatisés.
PCT/EP1997/005892 1996-11-14 1997-10-24 Utilisation de tensioactifs gemines anioniques dans des formulations pour agents de lavage, de nettoyage et de soins corporels WO1998020853A1 (fr)

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DE19647060.9 1996-11-14
DE19647060A DE19647060A1 (de) 1996-11-14 1996-11-14 Verwendung von anionischen Geminitensiden in Formulierungen für Wasch-, Reinigungs- und Körperpflegemittel

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6183550B1 (en) 1998-04-22 2001-02-06 Hercules Incorporated Paper size dispersions
WO2001019945A1 (fr) * 1999-09-13 2001-03-22 Sasol Germany Gmbh Composition tensioactive contenant des tensioactifs gemini et des co-amphiphiles, sa production et son utilisation
WO2001019943A1 (fr) * 1999-09-13 2001-03-22 Sasol Germany Gmbh Composition tensioactive contenant des tensioactifs gemini et son utilisation pour le nettoyage de la peau et des cheveux
WO2016160407A1 (fr) * 2015-03-31 2016-10-06 Stepan Company Détergents à base de tensioactifs ester gras alpha-sulfonés

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CA2379036A1 (fr) * 1999-07-16 2001-01-25 Basf Aktiengesellschaft Polyetherpolyamines zwitterioniques et leur procede de production
US6673890B1 (en) 1999-07-16 2004-01-06 Basf Aktiengesellschaft Zwitterionic polyamines and process for their production
FR2967056B1 (fr) 2010-11-05 2012-11-09 Oreal Composition solaire fluide aqueuse a base d'un polymere superabsorbant et d'un copolymere reticule d'acide methacrylique et d'acrylate d'alkyle en c1-c4.
WO2012095786A2 (fr) 2011-01-11 2012-07-19 L'oreal Composition cosmétique anti-ultraviolet (uv)
WO2012105060A1 (fr) 2011-02-04 2012-08-09 L'oreal Pigment composite et son procédé de préparation
FR2971151B1 (fr) 2011-02-04 2013-07-12 Oreal Composition cosmetique contenant des particules filtrantes de materiau composite, des particules non filtrantes non-spheriques et au moins une huile polaire
FR2971149B1 (fr) 2011-02-04 2013-07-12 Oreal Composition cosmetique contenant un melange de particules filtrantes de materiau composite spheriques et non spheriques
WO2013010590A1 (fr) 2011-07-21 2013-01-24 L'oreal Composition cosmétique et/ou dermatologique contenant un dérivé de mérocyanine qui comprend des groupes polaires spécifiques constitués de fonctionnalités hydroxyle et éther
CN104394835B (zh) 2012-07-13 2018-09-07 莱雅公司 化妆品组合物
JP6100897B2 (ja) 2012-07-13 2017-03-22 ロレアル 複合顔料及びその調製方法

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US2028091A (en) * 1933-07-28 1936-01-14 American Cyanamid & Chem Corp Esters of sulphodicarboxylic acids
US3246023A (en) * 1962-05-03 1966-04-12 Petrolite Corp Ester of an alpha-sulfocarboxylic acid and a polyalkyleneoxide glycol ether
US3268563A (en) * 1962-05-03 1966-08-23 Petrolite Corp Esters of an alpha-sulfo carboxylic acid and a glycol
WO1995019955A1 (fr) * 1994-01-25 1995-07-27 The Procter & Gamble Company Amides jumeles de polyether d'acides gras
WO1996025393A1 (fr) * 1995-02-17 1996-08-22 HÜLS Aktiengesellschaft Composes amphiphiles, comportant au moins deux groupements hydrophiles et au moins deux groupements hydrophobes, a base de diesters d'acides dicarboxyliques
DE19633497A1 (de) * 1996-08-20 1998-02-26 Huels Chemische Werke Ag Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Dicarbonsäurediestern

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Publication number Priority date Publication date Assignee Title
US2028091A (en) * 1933-07-28 1936-01-14 American Cyanamid & Chem Corp Esters of sulphodicarboxylic acids
US3246023A (en) * 1962-05-03 1966-04-12 Petrolite Corp Ester of an alpha-sulfocarboxylic acid and a polyalkyleneoxide glycol ether
US3268563A (en) * 1962-05-03 1966-08-23 Petrolite Corp Esters of an alpha-sulfo carboxylic acid and a glycol
WO1995019955A1 (fr) * 1994-01-25 1995-07-27 The Procter & Gamble Company Amides jumeles de polyether d'acides gras
WO1996025393A1 (fr) * 1995-02-17 1996-08-22 HÜLS Aktiengesellschaft Composes amphiphiles, comportant au moins deux groupements hydrophiles et au moins deux groupements hydrophobes, a base de diesters d'acides dicarboxyliques
DE19633497A1 (de) * 1996-08-20 1998-02-26 Huels Chemische Werke Ag Amphiphile Verbindungen mit mindestens zwei hydrophilen und mindestens zwei hydrophoben Gruppen auf der Basis von Dicarbonsäurediestern

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CHEMICAL ABSTRACTS, vol. 122, no. 22, 29 May 1995, Columbus, Ohio, US; abstract no. 268708, XP002046203 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6183550B1 (en) 1998-04-22 2001-02-06 Hercules Incorporated Paper size dispersions
WO2001019945A1 (fr) * 1999-09-13 2001-03-22 Sasol Germany Gmbh Composition tensioactive contenant des tensioactifs gemini et des co-amphiphiles, sa production et son utilisation
WO2001019943A1 (fr) * 1999-09-13 2001-03-22 Sasol Germany Gmbh Composition tensioactive contenant des tensioactifs gemini et son utilisation pour le nettoyage de la peau et des cheveux
US6710022B1 (en) 1999-09-13 2004-03-23 Sasol Germany Gmbh Tenside composition containing gemini tensides and co-amphiphiles and production and use thereof
AU775006B2 (en) * 1999-09-13 2004-07-15 Sasol Germany Gmbh Tenside composition containing gemini tensides and co-amphiphiles and productionand use thereof
US7393817B2 (en) 1999-09-13 2008-07-01 Sasol Germany Gmbh Tenside composition containing gemini tensides and co-amphiphiles and production and use thereof
WO2016160407A1 (fr) * 2015-03-31 2016-10-06 Stepan Company Détergents à base de tensioactifs ester gras alpha-sulfonés

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