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EP0165138B2 - Concentrated softening compositions based on quaterny ammonium-containing cationic surfactants - Google Patents
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EP0165138B2 - Concentrated softening compositions based on quaterny ammonium-containing cationic surfactants - Google Patents

Concentrated softening compositions based on quaterny ammonium-containing cationic surfactants Download PDF

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Publication number
EP0165138B2
EP0165138B2 EP19850400960 EP85400960A EP0165138B2 EP 0165138 B2 EP0165138 B2 EP 0165138B2 EP 19850400960 EP19850400960 EP 19850400960 EP 85400960 A EP85400960 A EP 85400960A EP 0165138 B2 EP0165138 B2 EP 0165138B2
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Prior art keywords
carbon atoms
salts
ether
chloride
alkyl
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EP19850400960
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German (de)
French (fr)
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EP0165138A2 (en
EP0165138A3 (en
EP0165138B1 (en
Inventor
Paul Nivollet
Vincent Parlongue
Lionel Godefroy
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Stepan Europe SAS
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Stepan Europe SAS
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Priority claimed from FR8407601A external-priority patent/FR2564495B1/en
Priority claimed from FR8503308A external-priority patent/FR2578559B2/en
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    • 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
    • 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

Definitions

  • the subject of the present invention is concentrated aqueous compositions or formulations based on compounds quaternary ammonium surfactants, intended in particular for softening textiles; it also concerns the preparation of these formulations.
  • Concentrated fabric softeners are products which are more and more sought after by both formulators only by users. Indeed, these products offer many advantages, for equal quality, compared ordinary fabric softeners that contain about 4 to 6% quaternary ammonium salts.
  • the formulations according to the invention may also contain nonionic surfactants as agents emulsifiers and stabilizers.
  • any type of cationic surfactant based on can be used.
  • Such surfactants are practically insoluble in water at weight concentrations of 5 to 20% or more.
  • these softening cationic surfactants for textiles are: dimethyl-di (hydrogenated tallow) ammonium chloride, dimethyl-di (tallow) ammonium chloride, methyl sulphate dimethyl-di (tallow) ammonium, dimethyl-di (palm) chloride ammonium, dimethyl-dihexadecylammonium chloride, dimethyl-di-octadecyl-ammonium chloride, diethyl-dihexadecyl-ammonium chloride, chloride dieicosyldimethylammonium, di (2-stearoyloxyethyl) methyl-2-hydroxyethylammonium methylsulfate, methylsulfate di (2-palmitoyloxyethyl) methyl-2-hydroxyethylammonium, di (2-alkyloyloxyethyl) methyl-2-hydroxyethyl ammonium methyl s
  • the imidazolinium compounds include in particular 1-methyl-1 methoxysulfate (alkyl (tallow) amido) ethyl-2-alkyl (tallow) -4.5 di-hydroimidazolinium, 2-methyl-1 chloride (alkyl palm-amido) ethyl-2-heptadecyl-4,5-dihydromidazolinium, 2-heptadecyl-1-methyl-1- (2-stearylamido) ethyl-imidazolinium chloride, 2-lauryl-1-hydroxyethyl-1 chloride oleyl imidazolinium.
  • One or more of these cationic surfactants are present in the formulation according to the invention at a concentration greater than or equal to 10% by weight. Below these concentrations, stable emulsions and little viscous with a viscosity of less than 300 millipascals-second are easy to prepare.
  • concentration cationic surfactants is determined based on practical considerations.
  • concentration of surfactants cationic can range from 10% to 25% or more, but is generally in the range of 15 to 20% by weight.
  • the other essential constituent of the formulations according to the invention is an agent which lowers the viscosity of the emulsions. concentrates based on cationic surfactants of quaternary ammonium type so as to obtain formulations easily pourable at room temperature.
  • the viscosity-reducing agents used in the formulations according to the invention are organic salts of which the particular structure assures them a great efficiency with respect to cationic surfactants, but also with regard to water (by their ability to create hydrogen bonds with water). These combined effects make it possible to obtain a surprising reduction in viscosity with good stability over time and without risk of breakage.
  • organic salts due to the presence of several atoms of electronegative character, chosen from oxygen, nitrogen, halogens and the like, which are capable of combining with molecules of water by hydrogen bonds.
  • These viscosity reducing agents include a) amine salts, b) quaternary ammonium salts, c) the salts of mono- or polycarboxylic acids of amines, and of alkali or alkaline-earth metals as defined above.
  • the other agents which can be used in the compositions according to the invention are surfactants nonionic, such as alkoxylated fatty alcohols, alkoxylated alkylphenols, alkoxylated carboxylic acids, alkoxylated ethanolamides.
  • surfactants nonionic such as alkoxylated fatty alcohols, alkoxylated alkylphenols, alkoxylated carboxylic acids, alkoxylated ethanolamides.
  • HLB hydrophilic-lipophilic
  • the cumulative content of organic salts and non-ionic agents must be less than the content cumulative cationic surfactants and preferably less than 30% of the cumulative weight content of or cationic surfactants.
  • the weight ratio of cationic surfactants to the weight of organic salts and nonionic agents is preferably between 10: 3 and 100: 1.
  • cationic surfactants In addition to cationic surfactants, viscosity-lowering organic salts and non-ionic agents present in the formulation, it is possible and even advisable to add functional and comfort additives, such as dispersants, complexing agents, bactericides, antistatics and dyes, optical brighteners, organic solvents, perfumes with or without solubilizer, depending on the desired effects, if these effects are not already provided by the cationic surfactant (s), the viscosity-reducing organic salt (s) and / or non-ionic agents.
  • functional and comfort additives such as dispersants, complexing agents, bactericides, antistatics and dyes, optical brighteners, organic solvents, perfumes with or without solubilizer, depending on the desired effects, if these effects are not already provided by the cationic surfactant (s), the viscosity-reducing organic salt (s) and / or non-ionic agents.
  • the preparation of concentrated formulations based on cationic surfactants according to the invention generally consists mixing the constituents by pouring, with stirring, hot water at around 30 to 60 ° C, into the surfactant (s) cationic fuses, or vice versa, to pour the cationic surfactants into hot water, the water containing or not the perfume (s) and the non-ionic agent (s), then to be added thereto, possibly after cooling to 20 to 30 ° C, the organic salt (s) reducing viscosity in sufficient quantity and possibly the other additives.
  • any type of cationic surfactant can be used based on quaternary ammonium having at least one higher alkyl chain. Such surfactants are practically insoluble in water at weight concentrations of 5 to 20% or more.
  • Cationic surfactants preferred are the quaternary ammonium salts and the alkylimidazolinium salts as defined above.
  • a stable fluid emulsion is obtained at 20 ° C., the viscosity of which is close to 50 millipascals-second. It is then possible to add to this fluid emulsion, containing 15% of cationic softening surfactant, the other additives such as colorants and perfumes.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)

Description

La présente invention a pour objet des compositions ou formulations aqueuses concentrées à base de composés d'ammonium quaternaire tensio-actifs, destinées en particulier à l'adoucissement des textiles; elle concerne également la préparation de ces formulations.The subject of the present invention is concentrated aqueous compositions or formulations based on compounds quaternary ammonium surfactants, intended in particular for softening textiles; it also concerns the preparation of these formulations.

Les adoucissants textiles concentrés sont des produits qui sont de plus en plus recherchés aussi bien par les formulateurs que par les utilisateurs. En effet, ces produits offrent de nombreux avantages, à qualité égale, par rapport aux adoucissants textiles ordinaires qui contiennent environ 4 à 6 % de sels d'ammonium quaternaire.Concentrated fabric softeners are products which are more and more sought after by both formulators only by users. Indeed, these products offer many advantages, for equal quality, compared ordinary fabric softeners that contain about 4 to 6% quaternary ammonium salts.

Pour l'utilisateur, ils sont généralement d'un prix intéressant, conditionnés dans des emballages plus petits (ils occupent donc moins de volume) et sont souvent plus économiques. Pour le fabricant, à matière active égale, les conditionnements sont plus réduits, c'est-à-dire que les frais de conditionnement et le coût des emballages sont moindres, les frais de stockage, de transport et de manutention sont également réduits et les capacités de fabrication sont accrues. Le seul défaut de ces formulations est qu'elles sont plus difficiles à réaliser, en particulier au point de vue stabilité et fluidité. En effet, ces formulations doivent rester suffisamment fluides pour s'écouler correctement dans les systèmes de distribution des machines à laver le linge bien que, bien sûr, une dilution de la formulation pour arriver à ce but, quoique plus contraignante, soit toujours possible.For the user, they are generally inexpensive, packaged in smaller packages (they therefore occupy less volume) and are often more economical. For the manufacturer, for the same active ingredient, the packaging is reduced, that is to say that the packaging costs and the cost of packaging are lower, storage, transport and handling costs are also reduced and manufacturing capacities are increased. The only defect of these formulations is that they are more difficult to produce, in particular from the point of view stability and fluidity. Indeed, these formulations must remain sufficiently fluid to flow correctly in the distribution systems of washing machines although, of course, a dilution of the formulation to arrive at this goal, although more restrictive, is still possible.

On a proposé selon l'art antérieur, de tels adoucissants textiles concentrés. On a notamment décrit :

  • dans le brevet US-A-3 681241, des formulations assouplissantes qui renferment deux composants essentiels, du type: :
    • un sel d'ammonium quaternaire ;
    • un alkylsulfate d'alkylaminoimidazolinium ;
  • dans la demande FR-A-2303 892, des agents assouplissants qui renferment quatre composants essentiels, du type:
    • un sel d'ammonium quaternaire ;
    • un éther oléylique de polyoxyéthylène ;
    • de l'urée ;
    • un sel d'ammonium hydrosoluble.
According to the prior art, such concentrated fabric softeners have been proposed. We have notably described:
  • in patent US-A-3 681241, softening formulations which contain two essential components, of the type:
    • a quaternary ammonium salt;
    • an alkylaminoimidazolinium alkyl sulfate;
  • in application FR-A-2303 892, softening agents which contain four essential components, of the type:
    • a quaternary ammonium salt;
    • a polyoxyethylene oleyl ether;
    • urea;
    • a water-soluble ammonium salt.

Les formulations adoucissantes aqueuses concentrées selon l'invention contiennent, en poids par rapport au poids total de la composition, 10 à 25 % d'au moins un agent tensio-actif cationique de type ammonium quaternaire choisi parmi:

  • a) les sels d'ammonium quaternaire de formule générale :
    Figure 00010001
    X-
       dans laquelle :
    • R1 et R2, identiques ou différents, représentent indépendamment l'un de l'autre des radicaux alkyle ou hydroxy alkyle ayant 1 à 4 atomes de carbone, éventuellement interrompus par un ou plusieurs groupes fonctionnels ester, éther, amido ou des chaínes polyalcoxylées contenant 1 à 5 fonctions éther,
    • R3 et R4, identiques ou différents, représentent chacun, indépendamment l'un de l'autre, des radicaux alkyle ou hydroxy alkyle à longue chaíne ayant de 10 à 24 atomes de carbone reliés ou non par une ou des doubles liaisons, lesdits radicaux étant interrompus par au moins un groupe fonctionnel ester, éther, amido ; et
    • X- représente un anion choisi parmi les chlorure, bromure, méthylsulfate, éthylsulfate, acétate, lactate, formiate, gluconate ou phosphate ;
  • b) les sels d'alkylimidazolinium ou leurs produits d'hydrolyse de formule :
    Figure 00020001
    Y-
    dans laquelle :
    • R5 est un radical alkyle contenant de 8 à 25 atomes de carbone reliés ou non par une ou des doubles liaisons,
    • R6 est un hydrogène ou un radical alkyle contenant de 1 à 4 -de préférence de 1 à 3- atomes de carbone substitués ou non par un ou des groupements hydroxy ou carboxy,
    • R7 est un hydrogène ou un radical alkyle contenant de 1 à 4 atomes de carbone,
    • R8 est un radical alkyle contenant de 9 à 25 atomes de carbone reliés ou non par une ou des doubles liaisons,
    • Y- est un anion du type chlorure, bromure, méthylsulfate, éthylsulfate, acétate, lactate, formiate, gluconate, phosphate ;
      • en combinaison avec un sel abaisseur de viscosité en quantité suffisante pour que la viscosité de ladite composition soit inférieure à 300 millipascals.seconde,
    • ledit sel organique abaisseur de viscosité étant choisi parmi :
  • a) les sels d'amine de poids moléculaire compris entre 150 et 450, de formule générale:
    Figure 00020002
    Z-
    dans laquelle :
    • R9, R10, R11, identiques ou différents représentent indépendamment l'un de l'autre l'hydrogène ou des radicaux alkyle contenant de 1 à 6 atomes de carbone substitués ou non par un ou des groupements hydroxy, carboxy ou carboxylate de sodium et interrompus ou non par des fonctions ester, éther, amide et Z- est un anion du type chlorure, bromure, sulfate, nitrate, phosphate, formiate, acétate, lactate, gluconate, glutamate ;
  • b) les sels d'ammonium quaternaire, de poids moléculaire compris entre 100 et 450, de formule générale :
    Figure 00020003
    A-
    dans laquelle :
    • R12 est un radical alkyle de 1 à 3 atomes de carbone,
    • R13, R14, R15 sont des radicaux alkyles de 1 à 5 atomes de carbone éventuellement substitués par un ou plusieurs groupements hydroxy, carboxy ou carboxylate de sodium, et interrompus ou non par des fonctions ester, éther, amide et A- est un anion de type chlorure, bromure, méthylsulfate, éthylsulfate ou phosphate ;
  • c) les sels de mono- ou de poly-acides carboxyliques d'amines, de métaux alcalins, ou alcalino-terreux contenant dans leur partie anionique de 5 à 8 atomes de carbone substitués ou non par une ou plusieurs fonctions hydroxyles et contenant une ou plusieurs fonctions carboxyliques, dont le poids moléculaire est compris entre 150 et 450 ;
    •  The concentrated aqueous softening formulations according to the invention contain, by weight relative to the total weight of the composition, 10 to 25% of at least one cationic surfactant of quaternary ammonium type chosen from:
  • a) the quaternary ammonium salts of general formula:
    Figure 00010001
    X -
    in which :
    • R 1 and R 2 , identical or different, independently of one another represent alkyl or hydroxy alkyl radicals having 1 to 4 carbon atoms, optionally interrupted by one or more functional groups ester, ether, amido or polyalkoxylated chains containing 1 to 5 ether functions,
    • R 3 and R 4 , which may be identical or different, each represent, independently of one another, long-chain alkyl or hydroxy alkyl radicals having from 10 to 24 carbon atoms which may or may not be linked by one or double bonds, the said groups radicals being interrupted by at least one ester, ether, amido functional group; and
    • X - represents an anion chosen from chloride, bromide, methylsulfate, ethylsulfate, acetate, lactate, formate, gluconate or phosphate;
  • b) alkylimidazolinium salts or their hydrolysis products of formula:
    Figure 00020001
    Y -
    in which :
    • R 5 is an alkyl radical containing from 8 to 25 carbon atoms linked or not linked by one or double bonds,
    • R6 is a hydrogen or an alkyl radical containing from 1 to 4 - preferably from 1 to 3 carbon atoms substituted or not by one or more hydroxy or carboxy groups,
    • R 7 is hydrogen or an alkyl radical containing from 1 to 4 carbon atoms,
    • R 8 is an alkyl radical containing from 9 to 25 carbon atoms which may or may not be linked by one or double bonds,
    • Y - is an anion of the chloride, bromide, methylsulfate, ethylsulfate, acetate, lactate, formate, gluconate, phosphate type;
      • in combination with a viscosity-reducing salt in an amount sufficient for the viscosity of said composition to be less than 300 millipascals.second,
    • said organic viscosity reducing salt being chosen from:
  • a) amine salts of molecular weight between 150 and 450, of general formula:
    Figure 00020002
    Z -
    in which :
    • R 9 , R 10 , R 11 , which are identical or different, independently of one another represent hydrogen or alkyl radicals containing from 1 to 6 carbon atoms substituted or not by one or more hydroxy, carboxy or carboxylate groups of sodium and interrupted or not by ester, ether, amide and Z functions - is an anion of the chloride, bromide, sulfate, nitrate, phosphate, formate, acetate, lactate, gluconate, glutamate type;
  • b) quaternary ammonium salts, of molecular weight between 100 and 450, of general formula:
    Figure 00020003
    A -
    in which :
    • R 12 is an alkyl radical of 1 to 3 carbon atoms,
    • R 13 , R 14 , R 15 are alkyl radicals of 1 to 5 carbon atoms optionally substituted by one or more hydroxy, carboxy or sodium carboxylate groups, and interrupted or not by ester, ether, amide and A - est functions a chloride, bromide, methylsulfate, ethylsulfate or phosphate type anion;
  • c) the salts of mono- or polycarboxylic acids of amines, alkali metals or alkaline-earth containing in their anionic part from 5 to 8 carbon atoms substituted or not by one or more hydroxyl functions and containing one or more several carboxylic functions, the molecular weight of which is between 150 and 450;

    • Les formulations selon l'invention peuvent contenir en outre des agents tensio-actifs non ioniques à titre d'agents émulsifiants et stabilisants.The formulations according to the invention may also contain nonionic surfactants as agents emulsifiers and stabilizers.

    Dans les formulations selon l'invention, on peut utiliser n'importe quel type d'agent tensio-actif cationique à base d'ammonium quaternaire ayant au moins une chaíne alkyle supérieure. De tels agents tensio-actifs sont pratiquement insolubles dans l'eau aux concentrations en poids de 5 à 20 % ou plus.In the formulations according to the invention, any type of cationic surfactant based on can be used. of quaternary ammonium having at least one higher alkyl chain. Such surfactants are practically insoluble in water at weight concentrations of 5 to 20% or more.

    Des exemples représentatifs de ces agents tensio-actifs cationiques adoucissants pour les textiles sont : le chlorure de diméthyl-di(suif hydrogéné)ammonium, le chlorure de diméthyl-di(suif)ammonium, le méthylsulfate de diméthyl-di(suif)ammonium, le chlorure de diméthyl-di(palme)ammonium, le chlorure de diméthyl-dihexadécylammonium, le chlorure de diméthyl-di-octadécyl-ammoniun, le chlorure de diéthyl-dihexadécyl-ammonium, le chlorure de dieicosyldiméthyl-ammonium, le méthylsulfate de di(2-stéaroyloxyéthyl)méthyl-2-hydroxyéthylammonium, le méthylsulfate de di(2-palmitoyloxyéthyl)méthyl-2-hydroxyéthylammonium, le méthylsulfate de di(2-alkyloyloxyéthyl)méthyl-2-hydroxyéthyl-ammonium, les lactate, gluconate ou acétate de N,N-bis(2-alkylamidoéthyl) N-(2-hydroxyéthyl)amine et les produits éthoxylés ou propoxylés en chaíne suif, oléine, palme, suif hydrogéné ou stéarique. Les lactate, gluconate ou acétate de N,N-bis(2-alkylamidoéthyl)-N (2-hydroxypropyl)amine et les produits éthoxylés ou propoxylés en chaíne suif, oléine, palme, suif hydrogéné ou stéarique. Le chlorure ou le méthylsulfate de N,N-bis-(2-alkylamidoéthyl)-N-(2-hydroxyéthyl)-N-méthyl-ammonium et les produits éthoxylés ou propoxylés en chaíne suif, oléine, suif hydrogéné, palme, stéarique. Le chlorure ou le méthylsulfate de N,N-bis(2-alkylamidoéthyl)-N-(2-hydroxypropyl)-N-méthyl-ammonium et les produits éthoxylés ou propoxylés en chaíne suif, oléine, palme, suif hydrogéné, stéarique. Le chlorure ou méthylsulfate de N,N-bis(alkyl)-N (2-hydroxypropyl)-N-méthylammonium en chaíne suif, oléine ou palme. Le chlorure ou le méthylsulfate de N-alkyl-N-(2-alkylacétate ester)-N,N-diméthylammonium en chaíne suif, palme, suif hydrogéné, oléine ou stéarique.Representative examples of these softening cationic surfactants for textiles are: dimethyl-di (hydrogenated tallow) ammonium chloride, dimethyl-di (tallow) ammonium chloride, methyl sulphate dimethyl-di (tallow) ammonium, dimethyl-di (palm) chloride ammonium, dimethyl-dihexadecylammonium chloride, dimethyl-di-octadecyl-ammonium chloride, diethyl-dihexadecyl-ammonium chloride, chloride dieicosyldimethylammonium, di (2-stearoyloxyethyl) methyl-2-hydroxyethylammonium methylsulfate, methylsulfate di (2-palmitoyloxyethyl) methyl-2-hydroxyethylammonium, di (2-alkyloyloxyethyl) methyl-2-hydroxyethyl ammonium methyl sulfate, N, N-bis (2-alkylamidoethyl) N- (2-hydroxyethyl) amine lactate, gluconate or acetate and ethoxylated or propoxylated products in tallow, olein, palm, hydrogenated or stearic tallow. Lactate, gluconate or N, N-bis (2-alkylamidoethyl) -N (2-hydroxypropyl) amine acetate and the ethoxylated or propoxylated products thereof tallow chain, olein, palm, hydrogenated or stearic tallow. N, N-bis- (2-alkylamidoethyl) -N- (2-hydroxyethyl) -N-methyl-ammonium chloride or methyl sulfate and ethoxylated or propoxylated products in tallow chain, olein, hydrogenated tallow, palm, stearic. N, N-bis (2-alkylamidoethyl) -N- (2-hydroxypropyl) -N-methyl-ammonium chloride or methyl sulfate and ethoxylated or propoxylated products in tallow chain, olein, palm, hydrogenated tallow, stearic. Chloride or N, N-bis (alkyl) -N (2-hydroxypropyl) -N-methylammonium methyl sulfate in tallow, olein or palm chain. Chloride or N-alkyl-N- (2-alkylacetate ester) -N, N-dimethylammonium methyl sulfate in tallow, palm, hydrogenated tallow chain, olein or stearic.

    Les composés d'imidazolinium comprennent en particulier le méthoxysulfate de 1-méthyl-1(alkyl(suif)amido)éthyl-2-alkyl(suif)-4,5 di-hydroimidazolinium, le chlorure de 2-méthyl-1(alkylpalme-amido)éthyl-2-heptadécyl-4,5-dihydromidazolinium, le chlorure de 2-heptadécyl-1-méthyl-1-(2-stéarylamido)éthyl-imidazolinium, le chlorure de 2-lauryl-1-hydroxyéthyl-1 oléyl-imidazolinium.The imidazolinium compounds include in particular 1-methyl-1 methoxysulfate (alkyl (tallow) amido) ethyl-2-alkyl (tallow) -4.5 di-hydroimidazolinium, 2-methyl-1 chloride (alkyl palm-amido) ethyl-2-heptadecyl-4,5-dihydromidazolinium, 2-heptadecyl-1-methyl-1- (2-stearylamido) ethyl-imidazolinium chloride, 2-lauryl-1-hydroxyethyl-1 chloride oleyl imidazolinium.

    Un ou plusieurs de ces agents tensio-actifs cationiques sont présents dans la formulation selon l'invention à une concentration supérieure ou égale à 10 % en poids. Au-dessous de ces concentrations, des émulsions stables et peu visqueuses dont la viscosité est inférieure à 300 millipascals-seconde sont faciles à préparer. Le choix de la concentration en tensio-actifs cationiques est déterminé en fonction de considérations pratiques. La concentration en tensio-actifs cationiques peut aller de 10 % à 25 % ou plus, mais elle est généralement de l'ordre de 15 à 20 % en poids.One or more of these cationic surfactants are present in the formulation according to the invention at a concentration greater than or equal to 10% by weight. Below these concentrations, stable emulsions and little viscous with a viscosity of less than 300 millipascals-second are easy to prepare. The choice of concentration cationic surfactants is determined based on practical considerations. The concentration of surfactants cationic can range from 10% to 25% or more, but is generally in the range of 15 to 20% by weight.

    L'autre constituant essentiel des formulations selon l'invention est un agent abaissant la viscosité des émulsions concentrées à base d'agents tensio-actifs cationiques de type ammonium quaternaire de manière à obtenir des formulations facilement coulables à température ordinaire.The other essential constituent of the formulations according to the invention is an agent which lowers the viscosity of the emulsions. concentrates based on cationic surfactants of quaternary ammonium type so as to obtain formulations easily pourable at room temperature.

    Il est bien connu que l'addition de sels généralement minéraux, dans des émulsions contenant au moins 4 % d'agents tensio-actifs cationiques, permet d'en réduire sensiblement la viscosité; mais par l'utilisation de ces sels, on se trouve très vite limité en concentration et par ailleurs les émulsions ainsi préparées évoluent assez rapidement en viscosité au cours du'stockage ou se séparent en deux phases, même à température ordinaire.It is well known that the addition of generally mineral salts, in emulsions containing at least 4% cationic surfactants, significantly reduces its viscosity; but by the use of these salts, is very quickly limited in concentration and moreover the emulsions thus prepared evolve fairly rapidly in viscosity during storage or separate into two phases, even at room temperature.

    Les agents abaisseurs de viscosité utilisés dans les formulations selon l'invention sont des sels organiques dont la structure particulière leur assure une grande efficacité vis-à-vis des agents tensio-actifs cationiques, mais aussi vis-à-vis de l'eau (par leur faculté de créer des liaisons hydrogène avec l'eau). Ces effets conjugués permettent d'obtenir un abaissement surprenant de la viscosité avec une bonne stabilité dans le temps et sans risque de rupture. The viscosity-reducing agents used in the formulations according to the invention are organic salts of which the particular structure assures them a great efficiency with respect to cationic surfactants, but also with regard to water (by their ability to create hydrogen bonds with water). These combined effects make it possible to obtain a surprising reduction in viscosity with good stability over time and without risk of breakage.

    La structure particulière de ces sels organiques est due à la présence de plusieurs atomes à caractère électronégatif, choisis parmi l'oxygène, l'azote, les halogènes et similaires, qui sont susceptibles de se combiner aux molécules d'eau par des liaisons hydrogène.The particular structure of these organic salts is due to the presence of several atoms of electronegative character, chosen from oxygen, nitrogen, halogens and the like, which are capable of combining with molecules of water by hydrogen bonds.

    Ces agents abaisseurs de viscosité comprennent les a) les sels d'amine, b) les sels d'ammonium quaternaire, c) les sels de mono- ou de polyacides carboxyliques d'amines, et de métaux alcalins ou alcaline-terreux tels que définis précédemment.These viscosity reducing agents include a) amine salts, b) quaternary ammonium salts, c) the salts of mono- or polycarboxylic acids of amines, and of alkali or alkaline-earth metals as defined above.

    A titre d'exemples de sels organiques particulièrement préférés aux fins de l'invention, on peut citer les gluconates, glutamates de monoéthanolamine, de diéthanolamine, de triéthanolamine; le chlorure ou le méthylsulfate de N,N,N-tris(2-hydroxyéthyl)-N-méthylammonium; le chlorure ou l'éthylsulfate de N,N,N-tris(2-hydroxyéthyl)-N-éthylammonium; le chlorure ou le méthylsulfate de N,N-bis(2-hydroxyéthyl)-N,N-diméthylammonium; le chlorure ou le méthylsulfate de N,N-bis(2-hydroxyéthyl)-N-éthyl-N-méthylammonium; le chlorure ou l'éthylsulfate de N,N-bis(2-hydroxyéthyl)-N,N-diéthylammonium; les acides gluconique et glutamique ainsi que leurs sels de sodium, potassium et ammonium.Mention may be made, as examples of organic salts which are particularly preferred for the purposes of the invention, of gluconates, monoethanolamine glutamates, diethanolamine, triethanolamine; N, N, N-N-tris (2-hydroxyethyl) -N-methylammonium chloride or methyl sulfate; N, N, N-N-tris (2-hydroxyethyl) -N-ethylammonium chloride or ethyl sulfate; N, N-bis (2-hydroxyethyl) -N, N-dimethylammonium chloride or methyl sulfate; chloride or methyl sulfate N, N-bis (2-hydroxyethyl) -N-ethyl-N-methylammonium; N, N-bis (2-hydroxyethyl) -N, N-diethylammonium chloride or ethyl sulfate; gluconic and glutamic acids and their sodium, potassium and ammonium salts.

    Les autres agents qui peuvent être utilisés dans les compositions selon l'invention sont des agents tensio-actifs non ioniques, tels que les alcools gras alcoxylés, les alkylphénols alcoxylés, les acides carboxyliques alcoxylés, les éthanolamides alcoxylés. Ces agents apportent un effet émulsifiant et stabilisant complémentaire mais ne sont pas toujours nécessaires et, selon la présente invention, ils ne sont jamais utilisés seuls mais uniquement en combinaison avec les sels organiques abaisseurs de viscosité. Ils ne servent qu'à compléter l'action de ces sels: leur balance hydrophile-lipophile (HLB) doit être comprise entre 6 et 15,5 et de préférence entre 8 et 15,5.The other agents which can be used in the compositions according to the invention are surfactants nonionic, such as alkoxylated fatty alcohols, alkoxylated alkylphenols, alkoxylated carboxylic acids, alkoxylated ethanolamides. These agents provide an additional emulsifying and stabilizing effect but are not always necessary and, according to the present invention, they are never used alone but only in combination with organic salts which reduce viscosity. They only serve to complement the action of these salts: their balance hydrophilic-lipophilic (HLB) must be between 6 and 15.5 and preferably between 8 and 15.5.

    Il est bien sûr possible d'utiliser une combinaison de ces sels et de ces non ioniques mais toujours en faible concentration. La teneur cumulée des sels organiques et des agents non ioniques doit être inférieure à la teneur cumulée en agents tensio-actifs cationiques et de préférence inférieure à 30 % de la teneur pondérale cumulée du ou des tensio-actifs cationiques. De préférence, le rapport pondéral des agents tensio-actifs cationiques au poids des sels organiques et des agents non ioniques est de préférence compris entre 10:3 et 100:1.It is of course possible to use a combination of these salts and these nonionic but always in weak concentration. The cumulative content of organic salts and non-ionic agents must be less than the content cumulative cationic surfactants and preferably less than 30% of the cumulative weight content of or cationic surfactants. Preferably, the weight ratio of cationic surfactants to the weight of organic salts and nonionic agents is preferably between 10: 3 and 100: 1.

    En plus des agents tensio-actifs cationiques, des sels organiques abaisseurs de viscosité et des agents non ioniques présents dans la formulation, il est possible et même conseillé d'ajouter des additifs fonctionnels et de confort, tels que des dispersants, des complexants, des bactéricides, des antistatiques et des colorants, des azurants optiques, des solvants organiques, des parfums avec ou sans solubilisant, selon les effets recherchés, si ces effets ne sont pas déjà apportés par le ou les agents tensio-actifs cationiques, le ou les sels organiques abaisseurs de viscosité et le ou les agents non ioniques.In addition to cationic surfactants, viscosity-lowering organic salts and non-ionic agents present in the formulation, it is possible and even advisable to add functional and comfort additives, such as dispersants, complexing agents, bactericides, antistatics and dyes, optical brighteners, organic solvents, perfumes with or without solubilizer, depending on the desired effects, if these effects are not already provided by the cationic surfactant (s), the viscosity-reducing organic salt (s) and / or non-ionic agents.

    La préparation des formulations concentrées à base de tensio-actifs cationiques selon l'invention consiste généralement à mélanger les constituants en versant, sous agitation, de l'eau chaude vers 30 à 60°C, dans le ou les tensio-actifs cationiques fondus, ou inversement, à verser les tensio-actifs cationiques dans l'eau chaude, l'eau contenant ou non le ou les parfums et le ou les agents non ioniques, puis à y ajouter, éventuellement après refroidissement vers 20 à 30°C, le ou les sels organiques abaisseurs de viscosité en quantité suffisante et éventuellement les autres additifs.The preparation of concentrated formulations based on cationic surfactants according to the invention generally consists mixing the constituents by pouring, with stirring, hot water at around 30 to 60 ° C, into the surfactant (s) cationic fuses, or vice versa, to pour the cationic surfactants into hot water, the water containing or not the perfume (s) and the non-ionic agent (s), then to be added thereto, possibly after cooling to 20 to 30 ° C, the organic salt (s) reducing viscosity in sufficient quantity and possibly the other additives.

    L'invention a également pour objet l'utilisation des sels organiques choisis parmi :

  • b) les sels d'ammonium quaternaire, de poids moléculaire compris entre 100 et 450, de formule générale :
    Figure 00040001
    A-
    dans laquelle :
    • R12 est un radical alkyle de 1 à 3 atomes de carbone,
    • R13, R14, R15 sont des radicaux alkyles de 1 à 5 atomes de carbone éventuellement substitués par un ou plusieurs groupements hydroxy, carboxy ou carboxylate de sodium, et interrompus ou non par des fonctions ester, éther, amide et
    • A- est un anion de type chlorure, bromure, méthylsulfate, éthylsulfate ou phosphate ;
    pour l'obtention de compositions adoucissantes aqueuses concentrées dont la viscosité est inférieure à 300 millipascals seconde; lesdites compositions contenant de 10 à 25 % en poids, par rapport au poids total de la composition, d'au moins un agent tensio-actif cationique de type ammonium quaternaire et éventuellement un agent tensio-actif non ionique à titre d'agent stabilisant et émulsifiant.
    • The invention also relates to the use of organic salts chosen from:
  • b) quaternary ammonium salts, of molecular weight between 100 and 450, of general formula:
    Figure 00040001
    A -
    in which :
    • R 12 is an alkyl radical of 1 to 3 carbon atoms,
    • R 13 , R 14 , R 15 are alkyl radicals of 1 to 5 carbon atoms optionally substituted by one or more hydroxy, carboxy or sodium carboxylate groups, and interrupted or not by ester, ether, amide and
    • A - is an anion of the chloride, bromide, methylsulfate, ethylsulfate or phosphate type;
    for obtaining concentrated aqueous softening compositions whose viscosity is less than 300 millipascals second; said compositions containing from 10 to 25% by weight, relative to the total weight of the composition, of at least one cationic surfactant of quaternary ammonium type and optionally a nonionic surfactant as stabilizing agent and emulsifier.

    • Dans les compositions adoucissantes ci-dessus, on peut utiliser n'importe quel type d'agent tensio-actif cationique à base d'ammonium quaternaire ayant au moins une chaíne alkyle supérieure. De tels agents tensio-actifs sont pratiquement insolubles dans l'eau aux concentrations en poids de 5 à 20 % ou plus. Les agents tensio-actifs cationiques préférés sont les sels d'ammonium quaternaire et les sels d'alkylimidazolinium tels que définis précédemment.In the above softening compositions, any type of cationic surfactant can be used based on quaternary ammonium having at least one higher alkyl chain. Such surfactants are practically insoluble in water at weight concentrations of 5 to 20% or more. Cationic surfactants preferred are the quaternary ammonium salts and the alkylimidazolinium salts as defined above.

    L'invention a aussi pour objet l'utilisation des sels organiques choisis parmi :

  • a) les sels d'amine de poids moléculaire compris entre 150 et 450, de formule générale :
    Figure 00050001
    Z-
    dans laquelle :
    • R9, R10, R11, identiques ou différents représentent indépendamment l'un de l'autre l'hydrogène ou des radicaux alkyle contenant de 1 à 6 atomes de carbone substitués ou non par un ou des groupements hydroxy, carboxy ou carboxylate de sodium et interrompus ou non par des fonctions ester, éther, amide et
    • Z- est un anion de type chlorure, bromure, sulfate, nitrate, phosphate, formiate, acétate, lactate, gluconate, glutamate;
  • b) les sels d'ammonium quaternaire, de poids moléculaire compris entre 100 et 450, de formule générale :
    Figure 00050002
    A-
    dans laquelle:
    • R12 est un radical alkyle de 1 à 3 atomes de carbone,
    • R13, R14, R15 sont des radicaux alkyles de 1 à 5 atomes de carbone éventuellement substitués par un ou plusieurs groupements hydroxy, carboxy ou carboxylate de sodium, et interrompus ou non par des fonctions ester, éther, amide et
    • A- est un anion de type chlorure, bromure, méthylsulfate, éthylsulfate ou phosphaté ; et
  • c) les sels de mono- ou de poly-acides carboxyliques d'amines, de métaux alcalins ou alcalino-terreux contenant dans leur partie anionique de 5 à 8 atomes de carbone substitués ou non par une ou plusieurs fonctions hydroxyles et contenant une ou plusieurs fonctions carboxyliques, dont le poids moléculaire est compris entre 150 et 450 ;
    • pour l'obtention de compositions contenant de 10 à 25 % en poids d'au moins un agent tensio-actif cationique de type ammonium quaternaire choisi parmi :
  • a) les sels d'ammonium quaternaire de formule générale :
    Figure 00060001
    X-
    dans laquelle :
    • R1 et R2, identiques ou différents, représentent indépendamment l'un de l'autre des radicaux alkyle ou hydroxy alkyle ayant 1 à 4 atomes de carbone, éventuellement interrompus par un ou plusieurs groupes fonctionnels ester, éther, amido ou des chaínes polyalcoxylées contenant 1 à 5 fonctions éther,
    • R3 et R4, identiques ou différents, représentent chacun, indépendamment l'un de l'autre, des radicaux alkyle ou hydroxy alkyle à longue chaíne ayant de 10 à 24 atomes de carbone reliés ou non par une ou des doubles liaisons, lesdits radicaux étant interrompus par au moins un groupe fonctionnel ester, éther, amido ; et
    • X- représente un anion choisi parmi les chlorure, bromure, méthylsulfate, éthylsulfate, acétate, lactate, formiate, gluconate ou phosphate ;
  • b) les sels d'alkylimidazolinium ou leurs produits d'hydrolyse de formule:
    Figure 00060002
    Y-
    dans laquelle :
    • R5 est un radical alkyle contenant de 8 à 25 atomes de carbone reliés ou non par une ou des doubles liaisons,
    • R6 est un hydrogène ou un radical alkyle contenant de 1 à 4 -de préférence de 1 à 3- atomes de carbone substitués ou non par un ou des groupements hydroxy ou carboxy,
    • R7 est un hydrogène ou un radical alkyle contenant de 1 à 4 atomes de carbone,
    • R8 est un radical alkyle contenant de 9 à 25 atomes de carbone reliés ou non par une ou des doubles liaisons,
    • Y- est un anion du type chlorure, bromure, méthylsulfate, éthylsulfate, acétate, lactate, formiate, gluconate, phosphate.
    •  The invention also relates to the use of organic salts chosen from:
  • a) amine salts of molecular weight between 150 and 450, of general formula:
    Figure 00050001
    Z -
    in which :
    • R 9 , R 10 , R 11 , which are identical or different, represent independently of one another hydrogen or alkyl radicals containing from 1 to 6 carbon atoms substituted or not substituted by one or more hydroxyl, carboxy or carboxylate groups of sodium and interrupted or not by ester, ether, amide and
    • Z- is a chloride, bromide, sulfate, nitrate, phosphate, formate, acetate, lactate, gluconate, glutamate type anion;
  • b) quaternary ammonium salts, of molecular weight between 100 and 450, of general formula:
    Figure 00050002
    A -
    in which:
    • R 12 is an alkyl radical of 1 to 3 carbon atoms,
    • R 13 , R 14 , R 15 are alkyl radicals of 1 to 5 carbon atoms optionally substituted by one or more hydroxy, carboxy or sodium carboxylate groups, and interrupted or not by ester, ether, amide and
    • A - is an anion of the chloride, bromide, methylsulfate, ethylsulfate or phosphate type; and
  • c) the salts of mono- or polycarboxylic acids of amines, of alkali or alkaline-earth metals containing in their anionic part from 5 to 8 carbon atoms substituted or not by one or more hydroxyl functions and containing one or more carboxylic functions, the molecular weight of which is between 150 and 450;
    • for obtaining compositions containing from 10 to 25% by weight of at least one cationic surfactant of quaternary ammonium type chosen from:
  • a) the quaternary ammonium salts of general formula:
    Figure 00060001
    X -
    in which :
    • R 1 and R 2 , identical or different, independently of one another represent alkyl or hydroxy alkyl radicals having 1 to 4 carbon atoms, optionally interrupted by one or more functional groups ester, ether, amido or polyalkoxylated chains containing 1 to 5 ether functions,
    • R 3 and R 4 , which may be identical or different, each represent, independently of one another, long-chain alkyl or hydroxy alkyl radicals having from 10 to 24 carbon atoms which may or may not be linked by one or double bonds, the said groups radicals being interrupted by at least one ester, ether, amido functional group; and
    • X - represents an anion chosen from chloride, bromide, methylsulfate, ethylsulfate, acetate, lactate, formate, gluconate or phosphate;
  • b) alkylimidazolinium salts or their hydrolysis products of formula:
    Figure 00060002
    Y -
    in which :
    • R 5 is an alkyl radical containing from 8 to 25 carbon atoms linked or not linked by one or double bonds,
    • R 6 is a hydrogen or an alkyl radical containing from 1 to 4 - preferably from 1 to 3 carbon atoms substituted or not by one or more hydroxy or carboxy groups,
    • R 7 is hydrogen or an alkyl radical containing from 1 to 4 carbon atoms,
    • R 8 is an alkyl radical containing from 9 to 25 carbon atoms which may or may not be linked by one or double bonds,
    • Y - is an anion of the chloride, bromide, methylsulfate, ethylsulfate, acetate, lactate, formate, gluconate, phosphate type.

    • Exemple 1Example 1

    On mélange 17,65 g d'une solution à 85 % de méthylsulfate de N-méthyl-N,N-di[2-(C14-C18-acyloxy)-éthyl]-N-(2-hydroxyéthyl)-ammonium à 40°C avec 81,30 g d'eau de ville à 40°C sous faible agitation. Après refroidissement à 20°C, on obtient une émulsion pseudoplastique présentant l'aspect d'un gel mobile dont la viscosité est de l'ordre de 500 millipascals-seconde. On ajoute alors à cette émulsion 0,5g de méthylsulfate de N-méthyl-N,N,N-tri(2-hydroxyéthyl)-ammonium. On obtient une émulsion fluide stable à 20°C dont la viscosité est voisine de 50 millipascals-seconde. Il est alors possible d'ajouter à cette émulsion fluide, contenant 15 % de tensio-actif cationique adoucissant, les autres additifs tels que colorants et parfums.17.65 g of an 85% solution of N-methyl-N, N-di [2- (C 14 -C 18 -acyloxy) -ethyl] -N- (2-hydroxyethyl) -ammonium solution are mixed at 40 ° C with 81.30 g of city water at 40 ° C with gentle stirring. After cooling to 20 ° C, a pseudoplastic emulsion with the appearance of a mobile gel is obtained, the viscosity of which is around 500 millipascals-second. 0.5 g of N-methyl-N, N, N-tri (2-hydroxyethyl) -ammonium methyl sulfate is then added to this emulsion. A stable fluid emulsion is obtained at 20 ° C., the viscosity of which is close to 50 millipascals-second. It is then possible to add to this fluid emulsion, containing 15% of cationic softening surfactant, the other additives such as colorants and perfumes.

    Exemple 2Example 2

    On mélange 18,65 g d'une solution alcoolique à 85 % de méthylsulfate de N-méthyl-N,N-di[2-(C14-C18-acyloxy)-éthyl]-N-2-hydroxyéthyl)-ammonium contenant 1g de nonylphénol éthoxylé avec 14 molécules d'oxyde d'éthylène, à 40°C, avec 80,35 g d'eau de ville à 40°C sous faible agitation. Après mélange, on ajoute 0,5 g de gluconate de sodium puis on laisse refroidir sous agitation. On obtient une émulsion fluide dont la viscosité est voisine de 50 millipascals-seconde.18.65 g of an 85% alcoholic solution of N-methyl-N, N-di [2- (C 14 -C 18 -acyloxy) -ethyl] -N-2-hydroxyethyl) -ammonium methyl chloride are mixed containing 1 g of ethoxylated nonylphenol with 14 molecules of ethylene oxide, at 40 ° C, with 80.35 g of city water at 40 ° C with gentle stirring. After mixing, 0.5 g of sodium gluconate is added and then allowed to cool with stirring. A fluid emulsion is obtained whose viscosity is close to 50 millipascals-second.

    Claims (9)

    1. Concentrated aqueous softening composition for textiles or fibres, characterized in that it contains:
      from 10 to 25% by weight, relative to the total weight of the composition, of at least one cationic surfactant of quaternary ammonium type chosen from:
      a) quaternary ammonium salts of general formula:
      Figure 00260001
      in which:
      R1 and R2, which may be identical or different, represent, independently of each other, alkyl or hydroxyalkyl radicals having 1 to 4 carbon atoms, optionally interrupted by one or more ester, ether or amido functional groups or polyalkoxylated chains containing 1 to 5 ether functions,
      R3 and R4, which may be identical or different, each represent, independently of each other, long-chain alkyl or hydroxyalkyl radicals having from 10 to 24 carbon atoms which may or may not be connected by one or more double bonds, the said radicals being interrupted by at least one ester, ether or amido functional group; and
      X- represents an anion chosen from chloride, bromide, methylsulphate, ethylsulphate, acetate, lactate, formate, gluconate and phosphate;
      b) alkylimidazolinium salts or hydrolysis products thereof, of formula:
      Figure 00260002
      in which:
      R5 is an alkyl radical containing from 8 to 25 carbon atoms which may or may not be connected by one or more double bonds,
      R6 is a hydrogen or an alkyl radical containing from 1 to 4, preferably from 1 to 3, carbon atoms which may or may not be substituted with one or more hydroxyl or carboxyl groups,
      R7 is a hydrogen or an alkyl radical containing from 1 to 4 carbon atoms,
      R8 is an alkyl radical containing from 9 to 25 carbon atoms which may or may not be connected by one or more double bonds,
      Y- is an anion of the chloride, bromide, methylsulphate, ethylsulphate, acetate, lactate, formate, gluconate or phosphate type;
      in combination with a viscosity-lowering salt in an amount which is sufficient for the viscosity of the said composition to be less than 300 millipascal seconds, the said organic viscosity-lowering salt being chosen from:
      a) amine salts of molecular weight between 150 and 450, of general formula:
      Figure 00270001
      in which:
      R9, R10 and R11, which may be identical or different, represent, independently of each other, hydrogen or alkyl radicals containing from 1 to 6 carbon atoms which may or may not be substituted with one or more hydroxyl, carboxyl or sodium carboxylate groups and which may or may not be interrupted by ester, ether or amide functions, and Z- is an anion of the chloride, bromide, sulphate, nitrate, phosphate, formate, acetate, lactate, gluconate or glutamate type;
      b) quaternary ammonium salts, of molecular weight between 100 and 450, of general formula:
      Figure 00280001
      in which:
      R12 is an alkyl radical of 1 to 3 carbon atoms,
      R13, R14 and R15 are alkyl radicals of 1 to 5 carbon atoms optionally substituted with one or more hydroxyl, carboxyl or sodium carboxylate groups and which may or may not be interrupted by ester, ether or amide functions, and A- is an anion of chloride, bromide, methylsulphate, ethylsulphate and phosphate type;
      c) salts of mono- or polycarboxylic acids of amines or of alkali metals or alkaline-earth metals, containing in their anionic part from 5 to 8 carbon atoms which may or may not be substituted with one or more hydroxyl functions and containing one or more carboxylic functions, the molecular weight of which is between 150 and 450.
    2. Composition according to Claim 1, characterized in that it also contains at least one nonionic surfactant as stabilizing and emulsifying agent.
    3. Composition according to Claim 2, characterized in that the said nonionic surfactant is chosen from alkoxylated fatty alcohols, alkoxylated alkylphenols, alkoxylated carboxylic acids and alkoxylated ethanolamides whose HLB is between 6 and 15.5, preferably between 8 and 15.5.
    4. Composition according to either of Claims 2 and 3, characterized in that the weight ratio of the cationic surfactants to the total weight of the stabilizing nonionic additives and of the organic viscosity-lowering salts is between 10:3 and 100:1.
    5. Composition according to any one of the preceding claims, characterized in that it contains one or more functional and convenience additives chosen from dispersing agents, complexing agents, bactericides, antistatic agents, dyes, optical brighteners and fragrances.
    6. Use of organic salts chosen from:
      b) quaternary ammonium salts, of molecular weight between 100 and 450, of general formula:
      Figure 00290001
      in which:
      R12 is an alkyl radical of 1 to 3 carbon atoms,
      R13, R14 and R15 are alkyl radicals of 1 to 5 carbon atoms optionally substituted with one or more hydroxyl, carboxyl or sodium carboxylate groups and which may or may not be interrupted by ester, ether or amide functions, and
      A- is an anion of chloride, bromide, methylsulphate, ethylsulphate or phosphate type; in order to obtain concentrated aqueous softening compositions whose viscosity is less than 300 millipascal seconds; the said compositions containing from 10 to 25% by weight, relative to the total weight of the composition, of at. least one cationic surfactant of quaternary ammonium type and optionally a nonionic surfactant as stabilizing and emulsifying agent.
    7. Use of organic salts chosen from
      a) amine salts of molecular weight between 150 and 450, of general formula:
      Figure 00300001
      in which:
      R9, R10 and R11, which may be identical or different, represent, independently of each other, hydrogen or alkyl radicals containing from 1 to 6 carbon atoms which may or may not be substituted with one or more hydroxyl, carboxyl or sodium carboxylate groups and which may or may not be interrupted by ester, ether or amide functions, and
      Z- is an anion of the chloride, bromide, sulphate, nitrate, phosphate, formate, acetate, lactate, gluconate or glutamate type;
      b) quaternary ammonium salts, of molecular weight between 100 and 450, of general formula:
      Figure 00310001
      in which:
      R12 is an alkyl radical of 1 to 3 carbon atoms,
      R13, R14 and R15 are alkyl radicals of 1 to 5 carbon atoms optionally substituted with one or more hydroxyl, carboxyl or sodium carboxylate groups and which may or may not be interrupted by ester, ether or amide functions, and
      A- is an anion of chloride, bromide, methylsulphate, ethylsulphate or phosphate type;
      c) salts of mono- or polycarboxylic acids of amines or of alkali metals or alkaline-earth metals, containing in their anionic part from 5 to 8 carbon atoms which may or may not be substituted with one or more hydroxyl functions and containing one or more carboxylic functions, the molecular weight of which is between 150 and 450; and
      in order to obtain compositions containing from 10 to 25% by weight of at least one cationic surfactant of quaternary ammonium type chosen from:
      a) quaternary ammonium salts of general formula:
      Figure 00320001
      in which:
      R1 and R2, which may be identical or different, represent, independently of each other, alkyl or hydroxyalkyl radicals having 1 to 4 carbon atoms, optionally interrupted by one or more ester, ether or amido functional groups or polyalkoxylated chains containing 1 to 5 ether functions,
      R3 and R4, which may be identical or different, each represent, independently of each other, long-chain alkyl or hydroxyalkyl radicals having from 10 to 24 carbon atoms which may or may not be connected by one or more double bonds, the said radicals being interrupted by at least one ester, ether or amido functional group; and
      X- represents an anion chosen from chloride, bromide, methylsulphate, ethylsulphate, acetate, lactate, formate, gluconate or phosphate;
      b) alkylimidazolinium salts or hydrolysis products thereof, of formula:
      Figure 00330001
      in which:
      R5 is an alkyl radical containing from 8 to 25 carbon atoms which may or may not be connected by one or more double bonds,
      R6 is a hydrogen or an alkyl radical containing from 1 to 4, preferably from 1 to 3, carbon atoms which may or may not be substituted with one or more hydroxyl or carboxyl groups,
      R7 is a hydrogen or an alkyl radical containing from 1 to 4 carbon atoms,
      R8 is an alkyl radical containing from 9 to 25 carbon atoms which may or may not be connected by one or more double bonds,
      Y- is an anion of the chloride, bromide, methylsulphate, ethylsulphate, acetate, lactate, formate, gluconate or phosphate type.
    8. Use according to either of Claims 6 and 7, in order to obtain compositions containing a nonionic surfactant chosen from alkoxylated fatty alcohols, alkoxylated carboxylic acids and alkoxylated ethanolamides whose HLB is between 6 and 15.5, preferably between 8 and 15.5.
    9. Use according to any one of Claims 6 to 8, in order to obtain compositions within which the weight ratio of the cationic surfactants to the total weight of the stabilizing nonionic additives and of the organic viscosity-lowering salts is between 10:3 and 100:1.
    EP19850400960 1984-05-16 1985-05-15 Concentrated softening compositions based on quaterny ammonium-containing cationic surfactants Expired - Lifetime EP0165138B2 (en)

    Applications Claiming Priority (4)

    Application Number Priority Date Filing Date Title
    FR8407601A FR2564495B1 (en) 1984-05-16 1984-05-16 CONCENTRATED SOFTENING COMPOSITIONS BASED ON CATIONIC QUATERNARY AMMONIUM SURFACTANTS
    FR8407601 1984-05-16
    FR8503308A FR2578559B2 (en) 1985-03-06 1985-03-06 CONCENTRATED SOFTENING COMPOSITIONS BASED ON CATIONIC QUATERNARY AMMONIUM SURFACTANTS
    FR8503308 1985-03-06

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    EP0165138A2 EP0165138A2 (en) 1985-12-18
    EP0165138A3 EP0165138A3 (en) 1987-05-06
    EP0165138B1 EP0165138B1 (en) 1996-08-07
    EP0165138B2 true EP0165138B2 (en) 2002-08-28

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    EP19850400960 Expired - Lifetime EP0165138B2 (en) 1984-05-16 1985-05-15 Concentrated softening compositions based on quaterny ammonium-containing cationic surfactants

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    JPH0742649B2 (en) * 1987-05-26 1995-05-10 花王株式会社 Softening agent
    EP0296995B1 (en) * 1987-06-16 1994-05-04 Cotelle S.A. Concentrated softening compositions
    GB8818593D0 (en) * 1988-08-04 1988-09-07 Albright & Wilson Fabric conditioners
    DE3926740C2 (en) * 1989-08-12 1997-05-15 Witco Surfactants Gmbh Aqueous fabric softener and its use
    DE4101251A1 (en) * 1991-01-17 1992-07-23 Huels Chemische Werke Ag AQUEOUS EMULSIONS CONTAINING FATTY ACID ESTERS OF N-METHYL-N, N, N-TRIHYDROXYETHYL-AMMONIUM-METHYL SULFATE
    DE4203489A1 (en) * 1992-02-07 1993-08-12 Henkel Kgaa METHOD FOR PRODUCING LOW-VISCUS AQUEOUS ESTERQUAT CONCENTRATES
    EP0648835A1 (en) * 1993-10-14 1995-04-19 The Procter & Gamble Company Use of alkaline polyammonium salts to increase cationic density in fabric softeners
    EP0802967B2 (en) * 1995-01-12 2003-05-21 The Procter & Gamble Company Stabilized liquid fabric softener compositions
    IL116638A0 (en) * 1995-01-12 1996-05-14 Procter & Gamble Method and compositions for laundering fabrics
    GB2313602A (en) * 1996-05-31 1997-12-03 Procter & Gamble Detergent compositions
    GB2313601A (en) * 1996-05-31 1997-12-03 Procter & Gamble Detergent compositions
    WO1998004238A1 (en) * 1996-07-31 1998-02-05 The Procter & Gamble Company Conditioning shampoo compositions comprising quaternary polyalkoxylated polyalkyleneamine
    DE69728778D1 (en) 1996-09-19 2004-05-27 Procter & Gamble SOFTENER WITH IMPROVED PERFORMANCE
    GB0002876D0 (en) * 2000-02-08 2000-03-29 Unilever Plc Fabric conditioning composition
    US7135451B2 (en) 2003-03-25 2006-11-14 The Procter & Gamble Company Fabric care compositions comprising cationic starch
    US10676694B2 (en) 2016-12-22 2020-06-09 The Procter & Gamble Company Fabric softener composition having improved detergent scavenger compatibility

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    US3681241A (en) * 1968-03-04 1972-08-01 Lever Brothers Ltd Fabric softening
    JPS51105500A (en) * 1975-03-12 1976-09-18 Kao Corp Orimonojunankazai
    DE2631114C3 (en) * 1975-07-14 1981-11-26 The Procter & Gamble Co., 45202 Cincinnati, Ohio Fabric softeners
    GB1599171A (en) * 1977-05-30 1981-09-30 Procter & Gamble Textile treatment composition
    EP0060003B1 (en) * 1981-03-07 1986-06-25 THE PROCTER & GAMBLE COMPANY Textile treatment compositions and preparation thereof

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    ES543216A0 (en) 1986-06-01
    ES8608080A1 (en) 1986-06-01
    EP0165138A2 (en) 1985-12-18
    EP0165138A3 (en) 1987-05-06
    EP0165138B1 (en) 1996-08-07
    DE3588115T3 (en) 2003-03-27
    DE3588115D1 (en) 1996-09-12
    DE3588115T2 (en) 1997-02-27

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