EP3172304A2 - Agents de soin textile transparents - Google Patents

Agents de soin textile transparents

Info

Publication number
EP3172304A2
EP3172304A2 EP15817764.2A EP15817764A EP3172304A2 EP 3172304 A2 EP3172304 A2 EP 3172304A2 EP 15817764 A EP15817764 A EP 15817764A EP 3172304 A2 EP3172304 A2 EP 3172304A2
Authority
EP
European Patent Office
Prior art keywords
acid
diyl
formula
composition
cationic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP15817764.2A
Other languages
German (de)
English (en)
Inventor
Tatiana Schymitzek
Simon PLUSZYNSKI
Ulrich PLATZBECKER
Peter Schmiedel
Roland Ettl
Silvia MARTINEZ BARRACHINA
Nuria Bonastre Gilabert
Maria ESCODA MARGENAT
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
BASF SE
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, BASF SE filed Critical Henkel AG and Co KGaA
Publication of EP3172304A2 publication Critical patent/EP3172304A2/fr
Withdrawn legal-status Critical Current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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/835—Mixtures of non-ionic with cationic compounds
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/003—Colloidal solutions, e.g. gels; Thixotropic solutions or pastes
    • 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
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • 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
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/222—Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin
    • 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
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/30—Amines; Substituted amines ; Quaternized amines
    • 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
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3769—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines
    • C11D3/3773—(Co)polymerised monomers containing nitrogen, e.g. carbonamides, nitriles or amines in liquid compositions
    • 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
    • C11D3/16—Organic compounds
    • C11D3/38—Products with no well-defined composition, e.g. natural products
    • C11D3/382—Vegetable products, e.g. soya meal, wood flour, sawdust
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
    • D06M15/03—Polysaccharides or derivatives thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
    • D06M15/03—Polysaccharides or derivatives thereof
    • D06M15/05—Cellulose or derivatives thereof
    • D06M15/09—Cellulose ethers
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/267—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof of unsaturated carboxylic esters having amino or quaternary ammonium groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/285—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/53—Polyethers
    • 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
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/12—Soft surfaces, e.g. textile
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50—Modified hand or grip properties; Softening compositions

Definitions

  • the present invention relates to compositions, especially to fabric care and fabric conditioning formulations, of clear, transparent optics and viscous consistency, to the use of these compositions as fabric care and fabric conditioning formulations, and to a fabric laundering process using these compositions, especially fabric care and fabric conditioning formulations.
  • the present invention relates to processes for the preparation of cationic compounds (EQ) and the resulting cationic compounds (EQ) and their use.
  • Esterquats which are generally understood to mean the quaternized fatty acid triethanolamine ester salts, are widely suitable for both fiber and hair care and have, in recent years, as a result of their improved ecotoxicological compatibility, become conventional quaternary ammonium compounds, e.g. the well-known Distearyldimethylammoniumchlorid displaced to a good extent from the market.
  • esterquats have very good performance properties and have a satisfactory biodegradability and a good skin-cosmetic compatibility
  • the known from the prior art formulations with esterquats have the disadvantage that they have turbidity.
  • specific unsaturated quaternary esterquats are available on the market to produce optically clear formulations, high concentrations of these esterquats and the use of solvents are required to provide clear softener formulations having the desired properties. This, in turn, is disadvantageous in terms of the cost of such formulations.
  • the present invention solves the problem of providing transparent, viscous compositions comprising esterquats which at least partially overcome the above-described disadvantages of known formulations.
  • the invention is based on the surprising finding of the inventors that the combination of specific esterquats with certain nonionic emulsifiers, in particular in combination with thickeners, wherein cationic thickeners are preferred, an optically clear, viscous, fragrant softener with at the same time
  • the present invention therefore relates to a liquid composition having a pH (25 ° C) between 1 and 4.5, in particular between 2 and 3.5
  • X is a saturated or unsaturated hydrocarbon radical having 1 to 8 carbon atoms
  • R is a saturated or unsaturated hydrocarbon radical having 5 to 21 carbon atoms
  • R ', R "and R'" independently of one another represent a (C 2 to C 6) -hydroxyalkyl group, in particular 2-hydroxyethyl,
  • At least one first emulsifier comprises a nonionic emulsifier having an HLB value of at least 12.0, in particular of at least 13.0, preferably of at least 14.0, most preferably of at least 15.0 , is.
  • cationic compound means that the cationic compound is an ester quat.
  • the compositions are preferably textile care agents, in particular softener formulations.
  • a process for the treatment of textiles in which at least one textile is brought into contact with the liquid composition according to the invention.
  • liquid composition according to the invention for the care and / or conditioning of textile fabrics.
  • Numeric ranges specified in the format "from x to y" include the above values. If multiple preferred numeric ranges are specified in this format, it is understood that all ranges resulting from the combination of the various endpoints, Furthermore, amounts referring to at least one ingredient always represent the total amount of that kind of ingredient contained in the composition, unless explicitly stated otherwise Relating to "at least one emulsifier", to the total amount of emulsifiers contained in the detergent.
  • At least one refers to 1 or more, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, or more, and does not refer to components of the compositions described herein
  • one or more different emulsifiers ie, at least one emulsifier
  • the quantities refer to the total amount of the corresponding designated type of ingredient as defined above.
  • HLB hydrophilic-lipophilic balance
  • Low HLB values describe lipophilic substances
  • high HLB values describe hydrophilic substances.
  • defoamers typically have HLB values in the range of 1.5 to 3 and are insoluble in water.
  • Emulsifiers for W / O emulsions typically have HLB values in the range of 3-8, whereas emulsifiers for O / W emulsions typically have HLB values in the range of 8-18.
  • Detergent-active substances typically have HLB values in the range of 13-15 and solubilizer values in the range of 12-18.
  • the HLB value of an emulsifier mixture of two nonionic emulsifiers can be calculated as follows:
  • the at least one nonionic emulsifier and the mixture of nonionic emulsifiers of the present invention preferably has an HLB value of 12.0-19.5, more preferably 13.0-19.5, preferably 14.0-19.5, more preferably from 15.0-19.5 to.
  • the at least one nonionic emulsifier and the mixture of nonionic emulsifiers of the present invention preferably has an HLB value of 12.0-18.0, more preferably of 13.0-18.0, preferably of 14.0-18, 0, more preferably from 15.0 to 18.0.
  • the at least one nonionic emulsifier and the mixture of nonionic emulsifiers of the present invention preferably has an HLB value of 12.0-17.0, in particular of 13.0-17.0, preferably of 14.0-17, 0, more preferably from 15.0 to 17.0.
  • the second and further nonionic emulsifier may have an HLB value which is below 12.0, below 13.0, below 14.0 or below 15.0, as long as the HLB value of the mixture of nonionic emulsifiers is at least 12.0, in particular at least 13.0, preferably at least 14.0, particularly preferably at least 15.0.
  • Liquid as used herein includes all flowable compositions at standard conditions (20 ° C, 1013 mbar), including appropriate pastes and gels.
  • the pH refers to the pH determined at 25 ° C, unless explicitly stated otherwise.
  • the pH is determined by means of pH meter Portamess 91 1 X pH. Standard for pH determination: DIN EN 1262.
  • the composition of the invention is particularly stable. Over long periods of storage, the composition remains clearer than comparative compositions, that is, it has a lower NTU value, a lower haze value. Also, the odor remains more pleasant than with comparative compositions. In terms of the pleasant odor, the focus here is particularly on a smell that smells less intensively or not at all of fatty acid. Without wishing to be bound by any particular theory, it is assumed that the hydrolysis of the esterquat is prevented by the pH value claimed and that it is advantageously stabilized thereby. The formation of free fatty acid by esterquat hydrolysis is avoided.
  • the proportion of the above-defined at least one cationic compound (EQ) (b) in the composition is preferably 0.1 to 30% by weight, preferably 2 to 10% by weight.
  • the cationic compounds used according to the invention are esterquats (EQ) and products of the reactions of the following educts:
  • X is a saturated or unsaturated hydrocarbon radical having 1 to 8 carbon atoms
  • R is a saturated or unsaturated hydrocarbon radical having 5 to 21 carbon atoms
  • R ', R "and R'" independently of one another represent a (C 2 to C 6) -hydroxyalkyl group, in particular 2-hydroxyethyl,
  • Typical examples include, without limitation, succinic acid, maleic acid, glutaric acid, and especially adipic acid.
  • X is preferably ethane-1,2-diyl, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, hexane-1,4-diyl or cyclohexane-1, 4- diyl, more preferably for butane-1, 4-diyl.
  • the dicarboxylic acid according to formula (II) is preferably adipic acid.
  • RCO is preferably an aliphatic, linear or branched acyl radical having 6 to 22 carbon atoms and 0 and / or 1, 2 or 3 double bonds.
  • Typical examples include, but are not limited to, caproic, caprylic, 2-ethylhexanoic, capric, lauric, isotridecanoic, myristic, palmitic, palmitic, stearic, isostearic, oleic, elaidic, petroselic, linoleic, linolenic, elaeostearic, arachidic, gadoleic, acids , Behenic acid and erucic acid and their technical mixtures, which are obtained, for example, in the pressure splitting of natural fats and oils, in the reduction of aldehydes from the Roelen oxo synthesis or the dimerization of unsaturated fatty acids.
  • R in formula (II) is particularly preferably a linear or branched Cs to C21 hydrocarbon radical having 0 to 3 double bonds.
  • the monocarboxylic acid of formula (II) is stearic acid.
  • Alkanolamines of the formula (III) which are suitable as central nitrogen compounds for the purposes of the invention contain a hydroxyalkane radical (alkanol radical) having 2 to 6 carbon atoms, preferably 2 to 4 carbon atoms.
  • hydroxyalkane radical alkanol radical
  • triethanolamine is used.
  • the at least one cationic compound (EQ) (b) comprises a compound of the formula (K1)
  • X is a saturated or unsaturated hydrocarbon radical having 1 to 10 carbon atoms, in particular butane-1, 4-diyl
  • A is a (C 2 to C 6) -alkanediyl group, in particular ethane-1, 2-diyl
  • R is a ( C 2 to C 4) hydroxyalkyl group or a (C 6 to C 22) acyloxy (C 2 to C 4) alkyl group, especially 2-hydroxyethyl or 2 - ((C 6 to C 22) acyloxy) ethyl
  • R 2 is methyl or ethyl
  • R 3 and R 4 are independently of one another a hydrogen atom or a (C 6 to C 22) acyl group
  • n is 1 or 2 and Z "is any anion, in particular methylsulfate, with the proviso that according to formula (K1) at least one of the groups R, R 3 or R 4 comprises a (C 6 to C 22) acyl radical.
  • esterquats used according to the invention are ideally liquid to pasty at temperatures around 20 ° C.
  • pasty as used in the present invention is intended to describe the state of a composition and means that the composition is not free-flowing at 20 ° C and atmospheric pressure under elevated pressure (> 1 bar) and / or At at least 85 ° C., the composition reaches a state in which it is in the form of a free-flowing mass It may therefore be necessary in practice to melt the pasty composition, for example the esterquat according to the invention, and into the free-flowing state of the present invention To incorporate the composition.
  • compositions according to the invention may contain the esterquats in amounts of from 2 to 60, preferably from 2 to 30,% by weight, based on the total amount of the liquid composition, in the end product.
  • the monocarboxylic acids (of formula II) and the dicarboxylic acids (of formula I) can be used in a molar ratio of 1:10 to 10: 1. However, it has proved to be advantageous to set a molar ratio of 1: 1 to 4: 1 and in particular 1, 5: 1 to 3: 1.
  • trialkanolamines (III) on the one hand and the acids - ie monocarboxylic acids (II) and dicarboxylic acids (I) taken together - can be used in a molar ratio of 1: 1, 2 to 1: 2.4.
  • esterification processes for providing the esterquats used according to the invention are generally known from the prior art.
  • the esterification can be carried out in a manner known per se, as described, for example, in International Patent Application WO 91/01295.
  • the esterification takes place at temperatures of 120 to 220 and in particular 130 to 170 ° C and pressures of 0.01 to 1 bar.
  • Hypophosphorous acids or their alkali metal salts, preferably sodium hypophosphite which can be used in amounts of from 0.01 to 0.1 and preferably from 0.05 to 0.07% by weight, based on the starting materials, have proven suitable catalysts.
  • alkali and / or alkaline earth boron hydrides such as, for example, potassium, magnesium and in particular sodium borohydride
  • the co-catalysts are usually used in amounts of 50 to 1000 and in particular 100 to 500 ppm - again based on the starting materials - a.
  • Corresponding methods are also the subject of the two German Patent DE 4308792 C1 and DE 4409322 C1, the teachings of which are hereby incorporated by reference. It is possible to use in the esterification mixtures of monocarboxylic acids and dicarboxylic acids or to carry out the esterification with the two components in succession.
  • the ester can be alkoxylated before the quaternization. This can be done in a conventional manner, ie in the presence of basic catalysts and at elevated temperatures.
  • suitable catalysts are alkali metal and alkaline earth metal hydroxides and alkoxides, preferably sodium hydroxide and in particular sodium methoxide; the amount used is usually 0.5 to 5 and preferably 1 to 3 wt .-% - based on the starting materials.
  • free hydroxyl groups are alkoxylated.
  • the catalysts used are calcined or hydrotalcites hydrophobized with fatty acids, insertion of the alkylene oxides into the ester bonds also occurs.
  • alkylene oxides ethylene and propylene oxide and mixtures thereof (random or block distribution) can be used.
  • the reaction is usually carried out at temperatures in the range of 100 to 180 ° C.
  • the hydrophilicity of the esterquats is increased, the solubility is improved and the reactivity towards anionic surfactants is reduced.
  • the quaternization of monocarboxylic acid / Dicarbonklaretrialkanolaminester can be carried out in a conventional manner.
  • reaction with the alkylating agents can also be carried out in the absence of solvents, the concomitant use of at least small amounts of water or lower alcohols, preferably isopropyl alcohol, for the preparation of concentrates having a solids content of at least 80 and in particular at least 90% by weight is recommended. exhibit.
  • Suitable alkylating agents are alkyl halides such as methyl chloride, dialkyl sulfates such as dimethyl sulfate or diethyl sulfate or dialkyl carbonates such as dimethyl carbonate or diethyl carbonate in question.
  • the esters and the alkylating agents in a molar ratio of 1: 0.95 to 1: 1, 05, that is used approximately stoichiometrically.
  • the reaction temperature is usually 40 to 80, and more preferably 50 to 60 ° C.
  • the quaternizing agent is dimethylsulfate.
  • oligomer within the meaning of the present invention comprises molecules from 2 to 20 inclusive monomer units.
  • a "monomer” is a structural unit of an oligomer or polymer / copolymer.
  • the above-described esterquats are combined with at least one nonionic emulsifier having an HLB value of at least 12.0, in particular of at least 13.0, preferably of at least 14.0, most preferably of at least 15.0.
  • the ester quats described above are combined with at least one nonionic emulsifier having an HLB of at least 14.0, most preferably at least 15.0.
  • Suitable nonionic emulsifiers for the formulations according to the invention are the following nonionic emulsifiers: - Addition products of 2 to 50 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide to linear fatty alcohols having 8 to 22 carbon atoms, to fatty acids having 8 to 22 carbon atoms, to alkylphenols having 8 to 15 carbon atoms in the alkyl group and Alkylamines having 8 to 22 carbon atoms in the alkyl radical; Alkyl and / or alkenyl oligoglycosides having 8 to 22 carbon atoms in the alk (en) ylrest and their ethoxylated analogs;
  • the addition products of ethylene oxide and / or of propylene oxide onto fatty alcohols, fatty acids, alkylphenols or castor oil are known, commercially available products. These are mixtures of homologues whose average degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate, with which the addition reaction is carried out corresponds.
  • C 12/18 fatty acid mono- and diesters of addition products of ethylene oxide with glycerol are known from DE 2024051 PS as refatting agents for cosmetic preparations.
  • Alkyl and / or alkenyl oligoglycosides their preparation and their use are known from the prior art. They are prepared in particular by reacting with glucose or Oligosaccharides with primary alcohols having 8 to 18 carbon atoms.
  • the glycoside radical both monoglycosides in which a cyclic sugar residue is glycosidically linked to the fatty alcohol and oligomeric glycosides having a degree of oligomerization of preferably approximately 8 are suitable.
  • the degree of oligomerization is a statistical mean, which is based on a homolog distribution typical for such technical products.
  • Suitable partial glycerides are hydroxystearic acid monoglyceride, hydroxystearic acid diglyceride, isostearic acid, Isostearinklarediglycerid, oleic acid monoglyceride, klarediglycerid oil, Ricinolklaremoglycerid, Ricinolklarediglycerid, Linolklaremonoglycerid, linoleic acid diglyceride, LinolenTalkremonoglycerid, LinolenLiterediglycerid, Erucaklaremonoglycerid, Erucaklarediglycerid, Weinklaremonoglycerid, Weinklarediglycerid, Citronenklamonoglycerid, Citronendiglycerid, ⁇ pfelklaklamonoglycerid, Apfelklakladiglycerid and their technical mixtures, which may be subordinated to the production process still contain small amounts of triglyceride. Also suitable are addition products of 1
  • polyglycerol esters are polyglyceryl-2 dipolyhydroxystearates (Dehymuls® PGPH), polyglycerol-3-diisostearates (Lameform® TGI), polyglyceryl-4 isostearates (Isolan® Gl 34), polyglyceryl-3 oleates, diisostearoyl polyglyceryl-3 diisostearates (Isolan ® PDI), Polyglyceryl-3 Methylglucose Distearate (Tego Care® 450), Polyglyceryl-3 Beeswax (Cera Bellina®), Polyglyceryl-4 Caprate (Polyglycerol Caprate T2010 / 90), Polyglyceryl-3 Cetyl Ether (Chimexane® NL), Polyglyceryl -3 distearates (Cremophor® GS 32) and polyglyceryl polyricinoleates (Admul® WOL 1403) polyglyceryl dim
  • polystyrene resin examples include the mono-, di- and triesters of trimethylolpropane or pentaerythritol with lauric acid, coconut fatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid and the like, which are optionally reacted with from 1 to 30 mol of ethylene oxide.
  • Particularly preferred according to the invention are the addition products of from 15 to 60 mol of ethylene oxide, in particular from 40 to 60 mol of ethylene oxide, to castor oil and / or hydrogenated castor oil, preferably with an HLB value of at least 14.0, more preferably of at least 15.0.
  • Preferred nonionic emulsifiers are Eumulgin CO 40, Eumulgin CO 60, Emulan ELH 60, Eumulgin 410, Eumulgin 455, Emulan 40 and Emulan EL (all from BASF). These Castor oil-based emulsifiers are advantageous in storage test over other non-ionic emulsifiers, such as Dehydol LT7.
  • Eumulgin CO 40, Eumulgin CO 60 and Emulan ELH 60 lead to particularly advantageous compositions having NTU values of 30 or less over 24 weeks in the Summer, Autumn and Winter programs (see examples). Thus, these compositions are clear over a long period of time and a wide temperature interval.
  • compositions according to the invention may contain the nonionic emulsifiers in amounts of from 0.1 to 50, preferably from 1 to 30 and in particular from 2 to 10,% by weight, based on the final concentration.
  • composition according to the invention which is selected from the nonionic emulsifiers defined in this application, and which has at least one, preferably at least two, ethylene oxide groups, is particularly preferred.
  • the at least one and all other nonionic emulsifiers are selected from the group of nonionic emulsifiers having at least one, preferably at least two ethylene oxide groups.
  • the at least one first nonionic emulsifier must have an HLB value of at least 12.0, in particular of at least 13.0, preferably of at least 14.0, most preferably of at least 15.0.
  • the composition comprises two or more nonionic emulsifiers, then all have at least one, preferably at least two ethylene oxide groups.
  • compositions according to the invention in particular fabric softening formulations, may also contain further emulsifiers, for example cationic and / or anionic emulsifiers.
  • the composition of the invention has no cationic emulsifier.
  • the composition of the invention has no anionic emulsifier.
  • the composition according to the invention has no cationic and no anionic emulsifier.
  • compositions according to the invention contain at least one nonionic emulsifier and at least one esterquat in a weight ratio of at least 0.5: 1, preferably at least 0.65: 1, more preferably at least 1: 1, even more preferably at least 2: 1.
  • Known cationic emulsifiers include fatty acid amidoamines and / or their quaternization products:
  • Fatty acid amidoamines which are suitable for cationic emulsifiers are condensation products of fatty acids with optionally ethoxylated di- or oligoamines, which preferably follow the formula (IV),
  • R is CO-NR 2 - [(A) -NR 3 ] n -R 4 (IV) where R CO is a linear or branched, saturated or unsaturated acyl radical having 6 to 22 carbon atoms, R 2 is hydrogen or an optionally hydroxy-substituted alkyl radical having 1 to 4 carbon atoms, R 3 and R 4 independently represent hydrogen, a (CH 2 CH 2 O) m H group or an optionally hydroxy-substituted alkyl radical of 1 to 4 carbon atoms, A represents a linear or branched alkylene group of 1 to 6 carbon atoms, n is a number from 1 to 4 and m stands for numbers from 1 to 30.
  • Typical examples are condensation products of caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures with ethylenediamine, propylenediamine, diethylenetriamine, dipropylenetriamine, triethylenetetramine, tripropylenetetramine and their adducts with 1 to 30, preferably 5 to 15 and especially 8 to 12 moles of ethylene oxide.
  • ethoxylated fatty acid amidoamines is preferred because in this way the hydrophilicity of the emulsifiers can be set exactly to the active ingredients to be emulsified.
  • fatty acid amidoamines can also their Quaternization be used, which is obtained by reacting the amidoamines with suitable alkylating agents such as methyl chloride or in particular dimethyl sulfate according to known methods.
  • suitable alkylating agents such as methyl chloride or in particular dimethyl sulfate according to known methods.
  • the quaternization products preferably follow the formula (V),
  • R CO is a linear or branched, saturated or unsaturated acyl radical having 6 to 22 carbon atoms
  • R 2 is hydrogen or an optionally hydroxy-substituted alkyl radical having 1 to 4 carbon atoms
  • R 3 is hydrogen, a (ChhChhOViH group or an optionally hydroxy-substituted alkyl radical having 1 to 4 carbon atoms
  • R 4 is R CO, hydrogen, a (ChhChhOViH group or an optionally hydroxy-substituted alkyl radical having 1 to 4 carbon atoms
  • R 6 is an alkyl radical having 1 to 4 carbon atoms
  • A is a linear or branched alkylene group having 1 to 6 carbon atoms
  • n is from 1 to 4
  • m is from 1 to 30
  • X is halide, especially chloride, or alkylsulfate
  • compositions according to the invention may contain the fatty acid amidoamines and / or their quaternization products in amounts of 0.1 to 50, preferably 1 to 30 and in particular 2 to 10,% by weight, based on the final concentration.
  • the known anionic emulsifiers include betaines.
  • Betaines which are suitable as anionic emulsifiers are known surfactants which are predominantly produced by carboxyalkylation, preferably carboxymethylation of aminic compounds.
  • the starting materials are condensed with halocarboxylic acids or their salts, in particular with sodium chloroacetate, wherein one mole of salt is formed per mole of betaine.
  • unsaturated carboxylic acids such as acrylic acid is possible
  • R 8 is hydrogen or alkyl radicals having 1 to 4 carbon atoms
  • R 9 is alkyl of 1 to 4 carbon atoms
  • p is 1 to 6
  • A is an alkali and / or alkaline earth metal or ammonium.
  • Typical examples are the carboxymethylation products of hexylmethylamine, hexyldimethylamine, octyldimethylamine, decyldimethylamine, dodecylmethylamine, dodecyldimethylamine, dodecylethylmethylamine, C 12/14 cocoalkyldimethylamine, myristyldimethylamine, cetyldimethylamine, stearyldimethylamine, stearylethylmethylamine, oleyldimethylamine, C 16/18 tallowalkyldimethylamine, and technical mixtures thereof.
  • Typical examples are reaction products of fatty acids having 6 to 22 carbon atoms, namely caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid, and their technical mixtures, with N, N-dimethylaminoethylamine, N, N-dimethylaminopropylamine, ⁇ , ⁇ -diethylaminoethylamine and ⁇ , ⁇ -Diethylaminopropylamin, which are condensed with sodium chloroacetate.
  • Preference is given to the use of a condensation product of Cs / is coconut fatty acid-N, N-dimethyl
  • R 5 is an alkyl radical having 5 to 21 carbon atoms
  • R 6 is a hydroxyl group
  • an OCOR 5 or NHCOR 5 radical and m is 2 or 3.
  • These substances are also known substances which can be obtained, for example, by cyclizing condensation of 1 or 2 moles of fatty acid with polyhydric amines, such as, for example, aminoethylethanolamine (AEEA) or diethylenetriamine.
  • AEEA aminoethylethanolamine
  • the corresponding carboxyalkylation products are mixtures of different open-chain betaines.
  • Typical examples are condensation products of the abovementioned fatty acids with AEEA, preferably imidazolines based on lauric acid or again C 12/14 coconut fatty acid, which are subsequently betainized with sodium chloroacetate.
  • compositions according to the invention may contain the betaines in amounts of from 0.1 to 50, preferably from 1 to 30, and in particular from 2 to 10,% by weight, based on the final concentration.
  • compositions according to the invention may contain combinations of nonionic emulsifiers with further nonionic emulsifiers, the HLB value of the emulsifier mixture of the (at least one) first and (at least one) second nonionic emulsifier being at least 12.0, in particular at least 13.0, preferably at least 14.0, most preferably at least 15.0.
  • the ratio of the first emulsifier to the second emulsifier is preferably 0.9-0.1 to 0.9-0.1.
  • the second emulsifier is likewise a nonionic emulsifier.
  • compositions according to the invention may further comprise in preferred embodiments a thickener, in particular selected from neutral thickeners, cationic thickeners and mixtures thereof.
  • the proportion of thickener in the composition may be 0.1-10% by weight, preferably 0.5-5% by weight.
  • the generally suitable thickeners include, for example, Aerosil types (hydrophilic silicic acids), polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, (eg Carbopole® from Goodrich or Synthalene® from Sigma), polyacrylamides, polyvinyl alcohol and polyvinylpyrrolidone, surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols such as pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with narrow homolog distribution or alkyl oligoglucosides and electrolytes such as saline and ammonium chloride.
  • Aerosil types hydrophilic silicic acids
  • Suitable cationic thickener polymers are, for example, cationic cellulose derivatives, such as, for example, a quaternized hydroxyethylcellulose which is obtainable under the name Polymer JR 400® from Amerchol, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers, such as, for example, Luviquat® (cf.
  • condensation products of polyglycols and amines condensation products of polyglycols and amines, quaternized collagen polypeptides such as lauryldimonium, hydroxypropyl hydrolyzed collagen (Lamequat®L / Grunau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers such as amidomethicones, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetriamine (Cartaretine® / Sandoz) , Copolymers of acrylic acid with dimethyldiallyl ammonium chloride (Merquat® 550 / Chemviron), polyaminopolyamides, as described, for example, in FR 2252840 A, and their crosslinked water-soluble polymers, cationic chitin derivatives such as quaternized Chitosan, optionally microcrystalline distributed, condensation products of dihaloalkylene, such as dibromobutane with bis-dialkylamines
  • anionic, zwitterionic, amphoteric and nonionic thickener polymers for example vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyl acetate / butyl maleate / isobornyl acrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and their esters, uncrosslinked polyols crosslinked with polyols, acrylamidopropyltrimethylammonium chloride / acrylate copolymers, octylacrylamide / methyl methacrylate / tert-butylaminoethyl methacrylate / 2-hydroxypropyl methacrylate copolymers, polyvinylpyrrolidone, vinylpyrrolidone / vinyl acetate copolymers, vinylpyrrolidone / dimethylaminoethy
  • the compositions contain at least one nonionic thickener.
  • Nonionic thickeners which are preferably used in the liquid compositions according to the invention are in particular selected from hydroxyethylcellulose (HEC), hydroxypropylcellulose (HPC), hydroxypropylmethylcellulose (HPMC) and methylcellulose (MC), guar, guar derivatives and mixtures of the abovementioned nonionic thickeners.
  • the nonionic thickener may be the 2-hydroxypropyl ether guar derivative Jaguar HP-105 from Rhodia.
  • compositions comprise at least one cationic thickener, for example as an alternative or in addition to those described above nonionic thickeners.
  • the cationic thickener comprises at least one copolymer of at least one monomer of the formula (M1) and at least one monomer of the formula (M2)
  • the liquid composition is characterized in that R 6 according to formula (M1) is a hydrogen atom and / or that R 5 according to formula (M1) is a hydrogen atom;
  • a in accordance with formula (M2) is ethane-1, 2-diyl or propane, 3-diyl.
  • Y is an anion selected from the group consisting of chloride and sulfate, especially methyl sulfate.
  • said cationic thickener copolymer based on the total weight of the polymer, to 95 to 100 wt .-% of the monomers of the formula (M1) and (M2) composed.
  • the cationic thickener copolymer is covalently crosslinked.
  • This covalent crosslinking is produced using at least one copolymerizable crosslinking agent.
  • Suitable copolymerizable crosslinking agents carry at least two ethylenically unsaturated groups, and are selected, for example, divinylbenzene, tetraallylammonium chloride, allyl acrylate, allyl methacrylate, diacrylate compounds of glycols, diacrylate compounds of polyglycols, dimethacrylate compounds of glycols, dimethacrylate compounds of polyglycols, butadiene, 1,7-octadiene, allylacrylamide, allylmethycrylamide , Bisacrylamidoacetic acid, ⁇ , ⁇ '-methylenebisacrylamide, polyol polyallyl ethers and mixtures of two or more of these compounds.
  • the cationic thickener copolymer can be obtained, for example, by emulsion polymerization. In preferred embodiments, it is in the form of beads, wherein the beads preferably have a mean particle diameter of 10 ⁇ to 1000 ⁇ , in particular from 50 ⁇ to 1000 ⁇ designate.
  • the cationic thickener copolymer is preferably contained in a total amount of 0.05 to 2.0 wt .-%, in particular from 0, 1 to 1, 0 wt .-% in the liquid compositions of the invention.
  • the cationic thickener copolymer has a structure of the formula
  • R 5 , R 6 and R 7 independently of one another represent a hydrogen atom or a methyl group
  • A represents ethane-1,2-diyl or propane-1,3-diyl
  • Y represents an anion
  • Y- is an anion which is selected from the group consisting of chloride and sulfate, in particular methylsulfate
  • the cationic thickener copolymer Rheovis CSP from BASF.
  • Solvents that can be used in the compositions according to the invention are derived, for example, from the group of monohydric or polyhydric alcohols. Alkanolamines or glycol ethers are also possible, provided that they are miscible with water in the concentration range indicated.
  • the solvents are preferably selected from ethanol, n- or i-propanol, butanols, glycol, propane- or butanediol, glycerol, diglycol, propyl- or butyldiglycol, ethylene glycol methyl ether, ethylene glycol ethyl ether, ethylene glycol propyl ether, etheylene glycol mono-n-butyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, propylene glycol methyl -, ethyl or -propyl ether, Dipropylenglykolmethyl- or ethyl ether, methoxy, ethoxy or Butoxytriglykol, 1-butoxyethoxy-2-propanol, 3-methyl-3-methoxybutanol, propylene glycol t-butyl ether, water, and Mixtures of these solvents.
  • the solvent used in the liquid compositions is water, and
  • the liquid composition has, in various embodiments, a viscosity of 100-300 mPas (20 ° C). It is measured with a Brookfiled Viscometer RV DV - II at 20 rpm and spindle 2.
  • the composition according to the invention has an NTU value of 30 or less after the batch, the determination taking place at 20 ° C. as explained in Example 4. In various embodiments, the composition still has an NTU of 30 or less after storage for 16 weeks at 40 ° C.
  • the compositions according to the invention may contain further ingredients which further improve the performance and / or aesthetic properties of the composition depending on the intended use, for example as a fabric care or fabric softener.
  • preferred compositions comprise one or more substances from the group of electrolytes, pH adjusters, fragrances, perfume carriers, fluorescers, dyes, hydrotopes, foam inhibitors, anti redeposition agents, enzymes, optical brighteners, grayness inhibitors , Anti-shrinkage agents, anti-wrinkling agents, color transfer inhibitors, wetting improvers, antimicrobial agents, germicides, fungicides, antioxidants, corrosion inhibitors, antistatic agents, ironing aids, repellents and impregnating agents, swelling and anti-slip agents and UV absorbers.
  • salts from the group of inorganic salts a wide number of different salts can be used.
  • Preferred cations are the alkali and alkaline earth metals, preferred anions are the halides and sulfates. From a manufacturing point of view, the use of NaCl or MgCk in the compositions according to the invention is preferred.
  • pH adjusting agents may be indicated.
  • Can be used here are all known acids or alkalis, unless their use is not for technical application or environmental reasons or for reasons of consumer protection prohibited.
  • the amount of these adjusting agents does not exceed 1% by weight of the total formulation.
  • Dyes and fragrances are added to the compositions according to the invention in order to improve the aesthetic impression of the products and to provide the consumer, in addition to the softness performance, with a visually and sensory "typical and unmistakable" product.
  • perfume oils or fragrances individual perfume compounds, for example the synthetic products of the ester type, ethers, aldehydes, ketones, alcohols and hydrocarbons can be used.
  • Fragrance compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinyl acetate, phenylethyl acetate, linalyl benzoate, benzylformate, ethylmethylphenylglycinate, allylcyclohexylpropionate, styrallylpropionate and benzylsalicylate.
  • the ethers include, for example, benzyl ethyl ether, to the aldehydes, for example, the linear alkanals with 8-18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, hydroxycitronellal, lilial and bourgeonal, to the ketones such as the ionone, ⁇ -lsomethylionon and methyl cedrylketone , to the alcohols anethole, citronellol, eugenol, geraniol, linalool, phenylethyl alcohol and terpineol, to the Hydrocarbons mainly include the terpenes such as limonene and pinene.
  • fragrance oils may also contain natural fragrance mixtures as are available from vegetable sources, eg pine, citrus, jasmine, patchouly, rose or ylang-ylang oil.
  • perfume oils may also contain natural fragrance mixtures as are available from vegetable sources, eg pine, citrus, jasmine, patchouly, rose or ylang-ylang oil.
  • Muskateller, sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, lime blossom oil, juniper berry oil, vetiver oil, olibanum oil, galbanum oil and labdanum oil as well as orange blossom oil, neroli oil, orange peel oil and sandalwood oil are also suitable.
  • the content of dyes is below 0.01 wt .-%, while fragrances can account for up to 2% by weight of the total formulation.
  • the fragrances can be incorporated directly into the compositions of the invention, but it may also be advantageous to apply the fragrances on carriers, which enhance the adhesion of the perfume on the laundry and provide by a slower release of fragrance for long-lasting fragrance of the textiles.
  • carrier materials for example, cyclodextrins have been proven, the cyclodextrin-perfume complexes can be additionally coated with other excipients.
  • perfume oils to be incorporated into the liquid formulations according to the invention are readily emulsifiable in order to be able to ensure the desired clear, transparent consistency of the formulation according to the invention.
  • compositions of the invention are advantageous over the prior art in that they are present as clear liquids over a broad temperature range and long shelf life. Furthermore, they have no or significantly lower fatty acid odor compared to known compositions. Therefore, the proportion of perfume oil can be reduced or dispensed entirely with perfume oils. For sensitive fabric care products, this is advantageous because they are preferably formulated without perfume oils. Also for cost reasons and production reasons, the waiver of perfume oils may be advantageous.
  • compositions comprise 0% by weight of perfume oil.
  • Suitable dyes In order to improve the aesthetic impression of the agents according to the invention, they can be dyed with suitable dyes.
  • Preferred dyes the selection of which presents no difficulty to the skilled person, have a high storage stability and insensitivity to the other ingredients of the agents and to light and no pronounced substantivity to textile fibers so as not to stain them.
  • Suitable foam inhibitors which can be used in the compositions according to the invention are, for example, soaps, paraffins or silicone oils, which may optionally be applied to support materials.
  • Suitable anti-redeposition agents which are also referred to as soil repellents, are, for example, nonionic cellulose ethers such as methylcellulose and methylhydroxypropylcellulose with a proportion of methoxy groups of 15 to 30% by weight and of hydroxypropyl groups of 1 to 15% by weight, based in each case on the nonionic cellulose ether as well as the known from the prior art polymers of phthalic acid and / or terephthalic acid or derivatives thereof, in particular polymers of ethylene terephthalates and / or polyethylene glycol terephthalates or anionic and / or nonionic modified derivatives thereof.
  • Especially preferred of these are the sulfonated derivatives of the phthalic and terephthalic acid polymers.
  • hydrotropes such as, for example, ethanol, isopropyl alcohol, or polyols can be used.
  • Polyols contemplated herein preferably have from 2 to 15 carbon atoms and at least two hydroxyl groups.
  • the polyols may contain other functional groups, in particular amino groups, or be modified with nitrogen. Typical examples are:
  • Alkylene glycols such as ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols having an average molecular weight of 100 to 1000 daltons,
  • Methylol compounds in particular trimethylolethane, trimethylolpropane, trimethylolbutane pentaerythritol and dipentaerythritol,
  • Lower alkyl glucosides in particular those having 1 to 8 carbons in the alkyl radical, such as, for example, methyl and butyl glucoside,
  • Sugar alcohols having 5 to 12 carbon atoms such as sorbitol or mannitol,
  • Sugar with 5 to 12 carbon atoms such as, for example, glucose or sucrose
  • Dialcoholamines such as diethanolamine or 2-amino-1,3-propanediol.
  • enzymes are in particular those from the classes of hydrolases such as proteases, esterases, lipases or lipolytic enzymes, amylases, cellulases or others Glykosylhydrolasen and mixtures of the enzymes mentioned in question. All of these hydrolases in the wash contribute to the removal of stains such as proteinaceous, greasy or starchy stains and graying.
  • cellulases and other glycosyl hydrolases may contribute to color retention and to enhancing the softness of the fabric by removing pilling and microfibrils. Oxireductases can also be used for bleaching or inhibiting color transfer.
  • Bacillus subtilis Bacillus licheniformis, Streptomyceus griseus and Humicola insolens derived enzymatic agents.
  • Bacillus subtilis Bacillus subtilis
  • Bacillus licheniformis Bacillus licheniformis
  • Streptomyceus griseus and Humicola insolens derived enzymatic agents.
  • subtilisin-type proteases and in particular proteases derived from Bacillus lentus are used.
  • enzyme mixtures for example from protease and amylase or protease and lipase or lipolytic enzymes or protease and cellulase or from cellulase and lipase or lipolytic enzymes or from protease, amylase and lipase or lipolytic enzymes or protease, lipase or lipolytic enzymes and cellulase, but in particular protease and / or lipase-containing mixtures or mixtures with lipolytic enzymes of particular interest.
  • lipolytic enzymes are the known cutinases. Peroxidases or oxidases have also proved suitable in some cases.
  • Suitable amylases include in particular a-amylases, iso-amylases, pullulanases and pectinases.
  • As cellulases are preferably cellobiohydrolases, endoglucanases and ß-glucosidases, which are also called cellobiases, or mixtures thereof used. Since different types of cellulases differ in their CMCase and avicelase activities, targeted mixtures of the cellulases can be used to set the desired activities.
  • the enzymes are usually provided as mixtures with preservatives and stabilizers.
  • the proportion of the enzyme mixture in the compositions may be, for example, about 0.01 to 5% by weight, preferably 0.12 to about 2% by weight.
  • compositions according to the invention stabilize enzymes particularly well.
  • the acidic and cationic compositions provide that the enzymes in the compositions exhibit significantly higher activity than those of known compositions even after 4 weeks of storage at 23 ° C and 40 ° C. Especially good cellulases are stabilized.
  • Compositions according to the invention which have cellulases are therefore particularly effective in preventing or slowing the graying of laundry.
  • Optical brighteners may be added to the compositions of the present invention to eliminate graying and yellowing of the treated fabrics, which will attract the fiber and cause lightening and fake bleaching action convert invisible ultraviolet radiation into visible longer wavelength light, wherein the ultraviolet light absorbed from the sunlight is emitted as a faint bluish fluorescence and yields pure white with the yellowness of the bruised or yellowed wash.
  • Suitable compounds are derived, for example, from the substance classes of 4,4'-diamino-2,2'-stilbenedisulfonic acids (flavone acids), 4,4'-distyrylbiphenyls, methylumbelliferones, coumarins, dihydroquinolinones, 1,3-diarylpyrazolines, naphthalimides, benzoxazole , Benzisoxazole and benzimidazole systems as well as heterocyclic substituted pyrene derivatives.
  • the optical brighteners are usually used in amounts between 0, 1 and 0.3 wt .-%, based on the finished composition.
  • Grayness inhibitors have the task of keeping the dirt detached from the fiber suspended in the liquor and thus preventing the dirt from being rebuilt.
  • Water-soluble colloids of mostly organic nature are suitable for this purpose, for example the water-soluble salts of polymeric carboxylic acids, glue, gelatin, salts of ether sulfonic acids or cellulose or salts of acidic sulfuric acid esters of cellulose or starch.
  • water-soluble polyamides containing acidic groups are suitable for this purpose.
  • soluble starch preparations and other than the above-mentioned starch products can be used, e.g. degraded starch, aldehyde levels, etc.
  • polyvinylpyrrolidone is useful.
  • preference is given to cellulose ethers such as carboxymethylcellulose (sodium salt), methylcellulose, hydroxyalkylcellulose and mixed ethers such as methylhydroxyethylcellulose, methylhydroxypropylcellulose,
  • compositions according to the invention can contain synthetic crease inhibitors.
  • the compositions of the invention may contain antimicrobial agents.
  • antimicrobial agents Depending on the antimicrobial spectrum and mechanism of action, a distinction is made between bacteriostats and bactericides, fungistatics and fungicides, etc. Important substances from these groups are, for example, benzalkonium chlorides.
  • Preferred compounds in the context of the present invention are, for example, alkylaryl sulfonates, halophenols and phenol mercuriacetate, it also being possible entirely to dispense with these compounds in the compositions according to the invention.
  • the agents may contain antioxidants. This class of compounds includes, for example, substituted phenols, hydroquinones, catechols and aromatic amines, as well as organic sulfides, polysulfides, dithiocarbamates, phosphites and phosphonates.
  • Antistatic agents increase the surface conductivity and thus allow an improved drainage of formed charges.
  • External antistatic agents are generally substances with at least one hydrophilic molecule ligand and give a more or less hygroscopic film on the surfaces. These mostly surface-active antistatic agents can be subdivided into nitrogen-containing (amines, amides, quaternary ammonium compounds), phosphorus-containing (phosphoric acid esters) and sulfur-containing (alkyl sulfonates, alkyl sulfates) antistatic agents.
  • External antistatics are described, for example, in patent applications FR 1, 156,513, GB 873,214 and GB 839,407.
  • the lauryl (or stearyl) dimethylbenzylammonium chlorides disclosed herein are useful as antistatics for textiles or as additives to laundry detergents, with the additional benefit of providing a softening effect.
  • silicone derivatives are, for example, polydialkyl or alkylaryl siloxanes in which the alkyl groups have one to five carbon atoms and are completely or partially fluorinated.
  • Preferred silicones are polydimethylsiloxanes, which may optionally be derivatized and are then amino-functional or quaternized or have Si-OH, Si-H and / or Si-Cl bonds.
  • the viscosities of the preferred silicones are in the range between 100 and 100,000 centistokes at 25 ° C, wherein the silicones in amounts between 0.05 and 5 wt .-%, based on the total agent can be used.
  • the agents according to the invention may also contain UV absorbers which are absorbed by the treated textiles and improve the light resistance of the fibers.
  • Compounds having these desired properties include, for example, the non-radiative deactivating compounds and derivatives of benzophenone having substituents in the 2- and / or 4-position.
  • preservatives In order to achieve optimal performance characteristics and to protect the products against germs, it may be advantageous to add preservatives to the products. Infestation of the fabric softeners according to the invention by microorganisms can be prevented by the use of commercially available preservatives.
  • the total proportion of the additives may be 1 to 50, preferably 5 to 40 wt .-% - based on the final product.
  • the preparation of the formulations described herein may be accomplished by techniques well known to those skilled in the art for the preparation of fabric care and fabric softeners. This can be done for example by mixing the raw materials, optionally using high-shear mixing equipment.
  • a further subject of the invention is a process for the preparation of the liquid clear compositions according to the invention, comprising the steps of a) preparing an aqueous solution containing the at least one first emulsifier at a temperature above 35 ° C, preferably above 40 ° C and at most preferably above 45 ° C,
  • step b) adding the inventive at least one cationic compound (EQ) to the solution prepared under step a), wherein the temperature of the at least one cationic compound (EQ) or a preparation containing the at least one cationic compound (EQ), in the addition between 30 and 65 ° C, preferably between 35 and 60 ° C and most preferably between 40 and 55 ° C.
  • the method for producing the liquid clear composition according to the invention comprises the steps of a) preparing an aqueous solution containing at least one thickener at a temperature above 40 ° C, preferably above 50 ° C, and most preferably above 55 ° C, and
  • step b) adding the at least one first emulsifier according to the invention to the aqueous solution prepared under step a), wherein the at least one first emulsifier or the composition containing the at least one first emulsifier, on a Temperature is preheated above 30 ° C, preferably above 35 ° C, and most preferably above 40 ° C,
  • step b) addition of the inventive at least one cationic compound (EQ) to the solution prepared under step b), wherein the temperature of the at least one cationic compound (EQ) or a preparation containing the at least one cationic compound (EQ), in the addition between 30 and 65 ° C, preferably between 35 and 60 ° C and most preferably between 40 and 55 ° C.
  • the inventive method ensures that the liquid compositions of the invention can be prepared in a clear form.
  • the liquid compositions of the present invention may be repeatedly prepared in clear form without purification of the equipment used in the process.
  • the aqueous solution in process step a) comprises 15 to 70% by weight, preferably 20 to 60% by weight, more preferably 25 to 50% by weight and most preferably 30 to 45% by weight. -% water, wt .-% based on the liquid clear composition.
  • the solution obtained in step b) of the process without thickener and in step c) of the process with thickener by addition of 30 to 85 wt .-%, preferably 40 to 80 wt .-%, on preferably 50 to 75% by weight, and most preferably 55 to 70% by weight, of water, by weight, based on the liquid clear composition, the water having a temperature of 10 to 29 ° C.
  • the at least one thickener in process step a) of the process with thickener is selected from the group consisting of neutral thickeners, cationic thickeners and mixtures thereof, with cationic thickeners being particularly preferred.
  • the at least one thickener is used in the process according to the invention in an amount of 0.1 to 10 wt .-%, wt .-% based on the liquid clear composition.
  • the invention also relates to processes for the treatment of textiles.
  • at least one textile is contacted with a liquid composition as described herein.
  • liquid compositions as described herein for the care and / or conditioning of fabrics.
  • the present invention relates to processes for the preparation of cationic compound (EQ), so-called esterquats, and compounds prepared by such processes and their use, in particular in compositions for the care and / or conditioning of textile fabrics.
  • EQ cationic compound
  • esterquats so-called esterquats
  • these compositions are preferably liquid.
  • X is a saturated or unsaturated hydrocarbon radical having 1 to 8 carbon atoms
  • R is a saturated or unsaturated hydrocarbon radical having 5 to 21 carbon atoms
  • R ', R "and R'" independently of one another represent a (C 2 to C 6) -hydroxyalkyl group, in particular 2-hydroxyethyl,
  • the process for preparing the cationic compound is characterized in that the cationic compound (EQ) contains a compound of the formula (K1),
  • X is a saturated or unsaturated hydrocarbon radical having 1 to 10
  • A is a (C 2 to C 6) -alkanediyl group, in particular ethane-1, 2-diyl,
  • R is a (C2 to C4) hydroxyalkyl group or a (C6 to C22) acyloxy (C2 to
  • alkyl group in particular 2-hydroxyethyl or 2 - ((C6 to C22) acyloxy) ethyl
  • R 2 is methyl or ethyl
  • R 3 and R 4 independently of one another represent a hydrogen atom or a (C 6 to C 22) acyl group
  • n 1 or 2
  • Z is an anion, in particular methylsulfate
  • At least one of the groups R, R 3 or R 4 comprises a (C6 to C22) acyl radical.
  • X in formula (I) is ethane-1,2-diyl, propane-1, 2-diyl, propane-1,3-diyl, butane-1, 4-diyl, hexane-1,4 -diyl or cyclohexane-1, 4-diyl, preferably for butane-1, 4-diyl.
  • R in formula (II) is a linear or branched C5 to C21 hydrocarbon radical having from 0 to 3 double bonds.
  • the resulting cationic compound (EQ) is liquid to pasty at 20 ° C.
  • Succinic acid maleic acid, glutaric acid, adipic acid or mixtures thereof. Most preferred is adipic acid.
  • the monocarboxylic acid of the formula (II) is N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethyl)-2-aminoethyl-N-(2-aminoethylic acid of the formula (II)
  • Stearic acid isostearic acid, palmitic acid, myristic acid, lauric acid, capric acid, Caprylic acid, 2-ethylhexanoic acid, 2-octyldodecanoic acid, caproic acid, oleic acid, linoleic acid, linolenic acid, partially cured coconut fatty acid, palm fatty acid, palm kernel fatty acid, tallow fatty acid, and mixtures of two or more of the foregoing acids. Most preferred is stearic acid.
  • dimethyl sulfate is used as the quaternizing agent in the process.
  • the present invention relates to cationic compounds (EQ) obtained by the methods described herein.
  • the present invention relates to the use of a cationic compound (EQ) as described herein in a composition, in particular a liquid composition, for the care and / or conditioning of textile fabrics.
  • a cationic compound (EQ) as described herein in a composition, in particular a liquid composition, for the care and / or conditioning of textile fabrics.
  • the batch was mixed with 300 ml of propylene glycol with stirring. Then, over a period of about 2.5 hours, an amount of 446 g of dimethyl sulfate was metered in such a manner that the temperature did not exceed 70 ° C. After the end of the addition, the reaction mixture was stirred for a further 2 hours at this temperature, and then cooled to room temperature. A product with a solids content of 80.5% was obtained.
  • compositions are usually prepared as follows:
  • Water is presented. Solids are added to the water in the molten state. For example, a pasty EQ is melted prior to adding to the composition and thus rendered flowable. As far as the compositions have thickeners, this is added as the first constituent at a temperature of for example 64 ° C in the water, wherein about 42 wt .-% of water are introduced, wt .-% based on the liquid clear compositions. This can be done, for example, with a Conti TDS machine (Ystral). Then the thickener is allowed to swell, e.g. for 30 to 120 minutes.
  • a Conti TDS machine Ystral
  • the emulsifier (s) is first added at a temperature of, for example, 55 ° C., then the esterquat is added at a temperature of, for example, 51 ° C., before the solution obtained is admixed with about 58% by weight of water, based on the liquid clear compositions, cooled and then mixed with solvent and preservative and homogenized by stirring. Subsequently, dyes, perfume oils and enzyme mixture are added.
  • the pH of the composition can be adjusted by means of citric acid.
  • Emulsifier (Eumulgin 2,500 2,500 2,500 2,500 3,250 3,250 4,000 4,000 CO40)
  • Emulsifier (Eumulgin 2,500 2,500 2,500 2,500 3,250 3,250 4,000 4,000 CO40)
  • Emulsifier (Dehydol 2,500 2,500 0 0
  • the pH of all compositions is 2.0 to 3.5.
  • Jaguar HP-105 a non-ionic thickener, can be obtained from Rhodia.
  • Rheovis CSP a cationic thickener
  • Eumulgin CO40 (100% AS), a nonionic emulsifier, can be obtained from BASF.
  • the HLB value is> 14 (according to Griffin, supra).
  • Dehydol LT5 (100% AS), a nonionic emulsifier, can be obtained from BASF.
  • the HLB value is 10 (according to Griffin, see above).
  • the inventive formulation 2 (see above) was prepared as described in Example 2. From formulation 2, viscosity, density, pH and NTU were determined. The NTU value was below 30. The density of formulation 2 was about 1.007 g / cm 3 , the viscosity about 230 mPas, the pH at about 3.25. Subsequently, about 200 ml of Formulation 2 were bottled in preserving jars (250 ml). In parallel, about 50 ml of Formulation 2 were filled into 100 ml screw-top glass jars. All jars were sealed and used in storage tests under the following five conditions. Summer, autumn or winter program (temperature controlled in climate cabinet) or constant storage at 40 ° C or 60 ° C (incubator). Storage took place for 24 weeks. The summer, autumn and winter programs were different, cyclic temperature programs. The following temperature profiles showed the programs.
  • the formulation was visually examined. For this a jar with formulation taken from the cabinet / incubator, stored for about 4-6 hours at about 23 ° C and then examined the formulation by eye for their transparency. Upon completion of the 24 week storage test, the turbidity of the formulation was determined by determining the NTU value of the compositions.
  • Formulation 2 of the invention exhibited NTU values of less than 30 even after more than 24 weeks storage in the Summer, Winter and Autumn programs.
  • Formulation 2 had an NTU of less than 30 for up to 16 to 20 weeks.
  • Formulation 2 had an NTU of less than 30 for up to 4 to 6 weeks.
  • Comparative composition 2 had an NTU value of at least 60 in the summer program after a maximum of 4 to 12 weeks.
  • Comparative composition 2 had an NTU value of at least 60 in the autumn and winter programs after a maximum of 8 to 12 weeks.
  • the comparative composition 2 had an NTU value of at least 60 when stored at 40 ° C after no later than 4 to 12 weeks. Comparative composition 2 had an NTU value of at least 60 when stored at 60 ° C after 2 weeks at the latest.
  • NTU nephelometric turbidity unit
  • the viscosities of the tested compositions were determined with a Brookfiled Viscometer RV DV - II at 20 rpm at 20 ° C and using spindle 2.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Emergency Medicine (AREA)
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  • Birds (AREA)
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  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
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  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)
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Abstract

La présente invention concerne des agents de soin textile et des formulations d'adoucissant optiquement claires et transparentes et de consistance visqueuse, contenant une combinaison d'esterquats particuliers avec des émulsifiants non ioniques et des épaississants cationiques, l'utilisation de ces agents de soin textile et de ces formulations d'adoucissant ainsi qu'un procédé de lavage textile employant ces agents de soin textile et ces formulations d'adoucissant. L'invention concerne également des procédés pour préparer les esterquats particuliers, les esterquats ainsi obtenus et leur utilisation.
EP15817764.2A 2014-07-25 2015-07-15 Agents de soin textile transparents Withdrawn EP3172304A2 (fr)

Applications Claiming Priority (2)

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DE102014010875.9A DE102014010875A1 (de) 2014-07-25 2014-07-25 Transparente Textilpflegemittel
PCT/EP2015/066172 WO2016012327A2 (fr) 2014-07-25 2015-07-15 Agents de soin textile transparents

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EP (1) EP3172304A2 (fr)
JP (1) JP2017528610A (fr)
KR (1) KR102401750B1 (fr)
CN (1) CN106661512A (fr)
DE (1) DE102014010875A1 (fr)
WO (1) WO2016012327A2 (fr)

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KR102379862B1 (ko) * 2020-10-28 2022-03-28 이난희 건조기용 섬유유연제 조성물 및 이의 제조방법
DE102021121537A1 (de) 2021-08-19 2023-02-23 Henkel Ag & Co. Kgaa Haarbehandlungsmittel, umfassend Haarkonditioniermittel auf Trimethylglycinbasis und ein Öl
DE102021121539A1 (de) 2021-08-19 2023-02-23 Henkel Ag & Co. Kgaa Haarbehandlungsmittel, umfassend Haarkonditioniermittel auf Trimethylglycinbasis und einen natürlichen Verdicker
DE102021121540A1 (de) 2021-08-19 2023-02-23 Henkel Ag & Co. Kgaa Haarbehandlungsmittel, umfassend Haarkonditioniermittel auf Trimethylglycinbasis und ein Protein oder Proteinhydrolysat
DE102021121538A1 (de) 2021-08-19 2023-02-23 Henkel Ag & Co. Kgaa Haarbehandlungsmittel, umfassend Haarkonditioniermittel auf Trimethylglycinbasis und ein Proteolipid
DE102021121541A1 (de) 2021-08-19 2023-02-23 Henkel Ag & Co. Kgaa Haarbehandlungsmittel, umfassend Haarkonditioniermittel auf Trimethylglycinbasis und einen Aktivstoff
DE102023201743A1 (de) 2023-02-27 2024-08-29 Henkel Ag & Co. Kgaa Gel zur oxidativen Farbveränderung keratinischer Fasern mit verbesserten Anwendungseigenschaften

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Publication number Publication date
CN106661512A (zh) 2017-05-10
WO2016012327A2 (fr) 2016-01-28
DE102014010875A1 (de) 2016-01-28
US20170218304A1 (en) 2017-08-03
US10941370B2 (en) 2021-03-09
WO2016012327A3 (fr) 2016-06-23
KR20170036737A (ko) 2017-04-03
KR102401750B1 (ko) 2022-05-26
JP2017528610A (ja) 2017-09-28

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