EP0165138A2 - Concentrated softening compositions based on quaterny ammonium-containing cationic surfactants - Google Patents
Concentrated softening compositions based on quaterny ammonium-containing cationic surfactants Download PDFInfo
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- EP0165138A2 EP0165138A2 EP85400960A EP85400960A EP0165138A2 EP 0165138 A2 EP0165138 A2 EP 0165138A2 EP 85400960 A EP85400960 A EP 85400960A EP 85400960 A EP85400960 A EP 85400960A EP 0165138 A2 EP0165138 A2 EP 0165138A2
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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
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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
- 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 present invention relates to concentrated aqueous compositions or formulations based on surface active quaternary ammonium compounds, intended in particular for softening textiles; it also relates to the preparation of these formulations.
- Concentrated fabric softeners are products which are more and more sought after by both formulators and users. Indeed, these products offer numerous advantages, for equal quality, compared to ordinary fabric softeners which contain approximately 4 to 6% of quaternary ammonium salts.
- 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 ammonium type quaternary in combination with a viscosity reducing agent in an amount sufficient for the viscosity of said formulation to be less than 300 millipascals-second.
- the formulations according to the invention can also contain nonionic surfactants as emulsifying and stabilizing agents.
- any type of cationic surfactant based on quaternary ammonium having at least one higher alkyl chain can be used.
- Such surfactants are practically insoluble in water at concentrations by weight of 5 to 20% or more.
- imidazolinium compounds include in particular 1-methyl-1 (alkyl (tallow) -amido) ethyl-2-alkyl (tallow) -4.5 dihydroimidazolinium methoxysulfate, 2-methyl-1 chloride (alkyl palm-amido ) ethyl-2-heptadecyl- 4,5-dihydroimidazo-linium, 2-heptadecyl-1-methyl-1- (2-stearylido) ethyl-imidazolinium chloride, 2-lauryl-1-hydroxyethyl-1 oleyl-imidazolinium chloride.
- 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, low-viscosity emulsions whose viscosity is less than 300 milli p ascals-second are easy to prepare.
- concentration of cationic surfactants is determined based on practical considerations. The concentration of cationic surfactants can range from 10% to 25% or more, but it is generally of the order 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 concentrated emulsions based on cationic surfactants of quaternary ammonium type so as to obtain formulations which are easily pourable at ordinary temperature.
- the viscosity-lowering agents used in the formulations according to the invention are organic salts, the particular structure of which provides them with high efficiency with respect to cationic surfactants but also with respect to water (for example their ability to create hydrogen bonds with water). These combined effects make it possible to obtain a lowering surprising viscosity with good stability over time and without risk of breakage.
- organic salts due to the presence of several atoms of an electronegative character, chosen from oxygen, nitrogen, halogens and the like, which are capable of combining with water molecules by hydrogen bonds.
- These viscosity-lowering agents include in particular organic salts, such as amine salts, quaternary ammonium or quaternary polyammonium salts, carboxylates, the molecular weight of which is between 50 and 500 and preferably between 100 and 450 .
- Their molecular weight is generally between 200 and 2000, preferably between 200 and 1200.
- Carboxylates are salts of amines, alkali or alkaline earth metals of mono- or polycarboxylic acids containing 5 to 8 carbon atoms, and one or more groups of carboxyl and / or hydroxyl type.
- gluconates glutamates of monoethanolamine, 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; N, N-bis (2-hydroxyethyl) -N-ethyl-N-methylammonium chloride or methyl sulfate; N, N-bis (2-hydroxyethyl) -N, N-diethylammonium chloride or ethyl sulfate; gluconic and glutamic acids and their sodium, potassium and
- quaternary polyammonium salts suitable for the purposes of the invention, mention may be made of dichloride or dimethyl sulfate of N, N, N ', N'-tetrakis (2-hydroxyethyl) -N, N'-dimethylethylene -diammonium of formula: in which A is the chloro group or the methyl sulphate group.
- the other agents which can be used in the compositions according to the invention are nonionic surfactants, such as alkoxylated fatty alcohols, alkoxylated alkylphenols, alkoxylated carboxylic acids, alkoxylated ethanolamides.
- nonionic surfactants such as alkoxylated fatty alcohols, alkoxylated alkylphenols, alkoxylated carboxylic acids, alkoxylated ethanolamides.
- HLB hydrophilic-lipophilic balance
- the cumulative content of organic salts and nonionic agents must be less than the cumulative content of cationic surfactants and preferably less than 30% of the cumulative content by weight of the cationic surfactant (s).
- the weight ratio of cationic surfactants to the weight of organic salts and nonionic agents is preferably between 10: 3 and 100: 1.
- viscosity-lowering organic salts and nonionic 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 colorants, optical brighteners, organic solvents, perfume s with or without solubilizer, depending on the desired effects, if such effects are not already provided by the cationic surfactants, the at least organic viscosity-lowering salts and non-ionic agent (s).
- functional and comfort additives such as dispersants, complexing agents, bactericides, antistatics and colorants, optical brighteners, organic solvents, perfume s with or without solubilizer, depending on the desired effects, if such effects are not already provided by the cationic surfactants, the at least organic viscosity-lowering salts and non-ionic agent (s).
- the preparation of the concentrated formulations based on cationic surfactants according to the invention generally consists in mixing the constituents by pouring, with stirring, hot water at around 30 to 60 ° C., into the molten cationic surfactant (s), or conversely, pour the cationic surfactants into hot water, the water containing or not containing the perfume (s) and the non-ionic agent (s), then adding thereto, possibly after cooling to around 20 to 30 ° C., the or sufficient viscosity reducing organic salts and possibly the other additives.
- 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.
Abstract
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 present invention relates to concentrated aqueous compositions or formulations based on surface active quaternary ammonium compounds, intended in particular for softening textiles; it also relates to 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 and users. Indeed, these products offer numerous advantages, for equal quality, compared to ordinary fabric softeners which contain approximately 4 to 6% of 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, a 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 a 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 equal active material, the packaging is reduced, that is to say that the packaging costs and the cost of packaging are lower, the storage, transport and handling costs are also reduced and the manufacturing capacities are increased. The only drawback of these formulations is that they are more difficult to produce, in particular from the point of view of 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 achieve this goal, although more restrictive, is always possible.
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 en combinaison avec un agent abaisseur de viscosité en quantité suffisante pour que la viscosité de ladite formulation soit inférieure à 300 millipascals-seconde.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 ammonium type quaternary in combination with a viscosity reducing agent in an amount sufficient for the viscosity of said formulation to be less than 300 millipascals-second.
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 can also contain nonionic surfactants as emulsifying and stabilizing agents.
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 chaîne alkyle supérieur. 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 quaternary ammonium having at least one higher alkyl chain can be used. Such surfactants are practically insoluble in water at concentrations by weight of 5 to 20% or more.
Parmi les agents tensio-actifs cationiques préférés aux fins de l'invention, on peut citer les composés de formule :
- - R1 et R2, identiques ou différents, représentent indépendamment l'un de l'autre, l'hydrogène ou des radicaux alkyle inférieur ayant de 1 à 4 atomes de carbone substitués ou non et interrompus ou non par un ou plusieurs groupements fonctionnels, tels que -OH, -0-,
- -CONH-, -COO-, etc. et/ou des chaînes polyalcoxylées contenant de 1 à 5 fonctions éther, telles que les chaînes polyéthoxylées ou polypropoxylées.
- - R3 et R4 représentent des radicaux à longue chaîne aliphatique à caractère lipophile, formés de 10 à environ 24 atomes de carbone, de préférence 12 à 20 atomes de carbone, reliés ou non par une ou des doubles liaisons, substitués ou non et interrompus ou non par au moins un groupement fonctionnel tel que -OH-, -0-, -CONH-, -COO-, etc.
- - X est un anion qui est de préférence un ion chlorure, bromure, méthylsulfate, éthylsulfate, acétate, lactate, formiate, gluconate, phosphate, etc.
- - R 1 and R 2 , identical or different, represent independently of one another, hydrogen or lower alkyl radicals having from 1 to 4 carbon atoms substituted or not and interrupted or not by one or more functional groups , such as -OH, -0-,
- -CONH-, -COO-, etc. and / or polyalkoxylated chains containing from 1 to 5 ether functions, such as polyethoxylated or polypropoxylated chains.
- - R 3 and R 4 represent radicals with a long aliphatic chain of lipophilic character, formed from 10 to about 24 carbon atoms, preferably 12 to 20 carbon atoms, linked or not by one or double bonds, substituted or not and interrupted or not by at least one functional group such as -OH-, -0-, -CONH-, -COO-, etc.
- - X is an anion which is preferably a chloride, bromide, methylsulfate, ethylsulfate, acetate, lactate, formate, gluconate, phosphate, etc. ion.
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 dimêthyl-di(suif)ammonium, le méthylsulfate de diméthyl-di(suif)ammonium, le chlorure de diméthyl-di(palme)ammonium, le chlorure de diméthyl- dihexadécyl-ammonium, le chlorure de diméthyl-di-octa- décyl-ammonium, 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-palmi-. toyloxyéthyl)méthyl-2 hydroxyéthylammonium, le méthylsulfate de di(2-alkyloyloxyéthyl)méthyl-2-hydroxy- éthyl-ammonium, les lactate, gluconate ou acétate de N,N-bis (2-alkylamidoéthyl) N-(2-hydroxyéthyl)amine et les produits éthoxylés ou propoxylés en chaîne 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 chaîne 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 chaîne 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 chaîne suif, oléine, palme, suif hydrogéné, stéarique. Le chlorure ou méthylsulfate de N,N-bis(alkyl)-N(2-hydroxypropyl)-N-méthyl-ammonium en chaîne suif, oléine ou palme. Le chlorure ou le méthylsulfate de N-alkyl-N-(2-alkyl acétate ester) N,N-diméthylammonium en chaîne suif, palme, suif hydro- géné, oléine ou stéarique.
- dimethyl-di (hydrogenated tallow) ammonium chloride, dimethyl-di (tallow) ammonium chloride, dimethyl-di (tallow) ammonium methyl sulfate, dimethyl-di (palm) ammonium chloride, dimethyl chloride dihexadecyl-ammonium, dimethyl-di-octadecyl-ammonium chloride, diethyl - dihexadecyl-ammonium chloride, dieicosyldimethyl-ammonium chloride, di (2-stearoyloxyethyl) methyl-2-hydroxyethylammonium methylsulfate, methylsulfate di (2-palmi-. toyloxyethyl) methyl-2 hydroxyethylammonium, di (2-alkyloyloxyethyl) methyl-2-hydroxyethyl ethyl ammonium sulfate, lactates, gluconate or acetate of N, N-bis (2-alkylamidoethyl ) N- (2-hydroxyethyl) amine and ethoxylated or propoxylated products in tallow, olein, palm, hydrogenated or stearic tallow chain. N, N-bis (2-alkylamidoethyl) -N (2-hydroxypropyl) amine lactate, gluconate or acetate and the ethoxylated or propoxylated products in tallow, olein, palm, hydrogenated or stearic tallow chain. N, N-bis- (2-alkylamidoethyl) -N- (2-hydroxyethyl) -N-methyl-ammonium chloride or methyl sulfate and the ethoxylated or propoxylated products in tallow, olein, hydrogenated tallow, palm, stearic chain. N, N-bis (2-alkylamidoethyl) -N- (2-hydroxypropyl) -N-methyl-ammonium chloride or methyl sulfate and the ethoxylated or propoxylated products in tallow, olein, palm, hydrogenated tallow, stearic chain. Chloride or methyl N, N-bis (alkyl) -N (2-hydroxypropyl) -N-methyl-ammonium sulfate in the tallow, olein or palm chain. The N-alkyl-N- (2-alkyl acetate ester) N, N-dimethylammonium chloride or methyl sulfate in the tallow, palm, hydrogenated tallow, olein or stearic chain.
Parmi les agents tensio-actifs on citera également les imidazoliniums ayant pour formule :
- R5 est un radical alkyle contenant 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 atomes de carbone, 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,
- de préférence de 12 à 20 atomes de carbone, reliés ou non par une ou des doubles liaisons;Y est un anion de préférence de type chlorure, bromure, méthylsulfate, éthylsulfate, acétate, lactate, formiate, gluconate, phosphate etc.
- R 5 is an alkyl radical containing 8 to 25 carbon atoms linked or not by one or double bonds, R 6 is a hydrogen or an alkyl radical containing from 1 to
- 4 carbon atoms, preferably from 1 to 3 carbon atoms, substituted or not by one or more hydroxy or carboxy groups, R 7 is a hydrogen or an alkyl radical containing from 1 to 4 carbon atoms, R 8 is a radical alkyl containing from 9 to 25 carbon atoms,
- preferably from 12 to 20 carbon atoms, linked or not by one or double bonds; Y is an anion preferably of the chloride, bromide, methylsulfate, ethylsulfate, acetate, lactate, formate, gluconate, phosphate, etc. type.
Ces composés d'imidazolinium comprennent en particulier le méthoxysulfate de 1-méthyl-l(alkyl(suif)-amido)éthyl-2-alkyl(suif)-4,5 dihydroimidazolinium, le chlorure de 2-méthyl-1(alkylpalme-amido)éthyl-2-heptadécyl-4,5-dihydroimidazo-linium, le chlorure de 2-heptadécyl-1-méthyl-1-(2-stéarylamido)éthyl-imidazolinium, le chlorure de 2-lauryl-1-hydroxyéthyl-1 oléyl-imidazolinium.These imidazolinium compounds include in particular 1-methyl-1 (alkyl (tallow) -amido) ethyl-2-alkyl (tallow) -4.5 dihydroimidazolinium methoxysulfate, 2-methyl-1 chloride (alkyl palm-amido ) ethyl-2-heptadecyl- 4,5-dihydroimidazo-linium, 2-heptadecyl-1-methyl-1- (2-stearylido) ethyl-imidazolinium chloride, 2-lauryl-1-hydroxyethyl-1 oleyl-imidazolinium chloride.
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, low-viscosity emulsions whose viscosity is less than 300 milli p ascals-second are easy to prepare. The choice of cationic surfactant concentration is determined based on practical considerations. The concentration of cationic surfactants can range from 10% to 25% or more, but it is generally of the order 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 concentrated emulsions based on cationic surfactants of quaternary ammonium type so as to obtain formulations which are easily pourable at ordinary 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% of cationic surfactants, makes it possible to substantially reduce its viscosity; but by the use of these salts, one quickly finds itself limited in concentration and moreover the emulsions thus prepared change fairly quickly in viscosity during storage or separate into two phases, even at ordinary 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-lowering agents used in the formulations according to the invention are organic salts, the particular structure of which provides them with high efficiency with respect to cationic surfactants but also with respect to water (for example their ability to create hydrogen bonds with water). These combined effects make it possible to obtain a lowering surprising 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 an electronegative character, chosen from oxygen, nitrogen, halogens and the like, which are capable of combining with water molecules by hydrogen bonds.
Ces agents abaisseurs de viscosité comprennent notamment les sels organiques, tels que les sels d'amines, les sels d'ammonium quaternaire ou de polyammonium quaternaire, les carboxylates, dont le poids moléculaire est compris entre 50 et 500 et de préférence entre 100 et 450.These viscosity-lowering agents include in particular organic salts, such as amine salts, quaternary ammonium or quaternary polyammonium salts, carboxylates, the molecular weight of which is between 50 and 500 and preferably between 100 and 450 .
Les sels d'amines sont de préférence des sels de formule :
- - R92 R10 et R11 sont l'hydrogène ou des radicaux contenant de 1 à 6 atomes de carbone, de préférence 1 à 5 atomes de carbone, substitués ou non et interrompus ou non par une ou des fonctions, telles que -OH, -COO-, -0-, -CONH-, -COOH, -COONa, etc.
- - Z est un anion choisi parmi des anions minéraux de type chlorure, bromure, sulfate,nitrate, phosphate, etc. ou des anions organiques, tels que par exemple les- gluconates, les glutamates et similaires. Ces sels ont en général un poids moléculaire compris entre 150 et 450. Les sels d'ammonium quaternaire sont de préférence des sels de formule :
- - R12 est de préférence un radical alkyle ayant de 1 à 3 atomes de carbone, R13, R14, R15 sont des radicaux ayant de 1 à 5 atomes de carbone, substitués ou non et interrompus ou non par des fonctions du type -OH, -0-, -COO-, -CONH-, -COOH, - COONa, etc.
- - A est un anion choisi de préférence parmi les chlorures, méthylsulfates, éthylsulfates,bromures, phosphates et similaires. Leur poids moléculaire est généralement compris entre 100 et 450.
- - R 92 R 10 and R 11 are hydrogen or radicals containing from 1 to 6 carbon atoms, preferably 1 to 5 carbon atoms, substituted or not and interrupted or not by one or more functions, such as -OH , -COO-, -0-, -CONH-, -COOH, -COONa, etc.
- - Z is an anion chosen from mineral anions of the chloride, bromide, sulfate, nitrate, phosphate type, etc. or organic anions, such as, for example, gluconates, glutamates and the like. These salts generally have a molecular weight of between 150 and 450. The quaternary ammonium salts are preferably salts of formula:
- - R 12 is preferably an alkyl radical having from 1 to 3 carbon atoms, R 13 , R 14 , R 15 are radicals having from 1 to 5 carbon atoms, substituted or not and interrupted or not by functions of the type -OH, -0-, -COO-, -CONH-, -COOH, - COONa, etc.
- - A is an anion preferably chosen from chlorides, methylsulphates, ethylsulphates, bromides, phosphates and the like. Their molecular weight is generally between 100 and 450.
Les sels de polyammonium quaternaire sont de préférence des sels de formule :
- - R16 est un atome d'hydrogène ou un radical alkyle contenant de préférence 1 à 3 atomes de carbone,
- - R17, R18, R , et R20 sont des radicaux ayant de 1 à 5 atomes de carbone, substitués ou non et interrompus ou non par des fonctions du type -OH, -O-, -COO-, -CONH-, -COOH, -COONa, etc.
- - A est un anion choisi de préférence parmi les chlorures, méthylsulfates, éthylsulfates, bromures, phosphates et similaires.
- - n est un nombre entier compris entre 1 et 6.
- - m est un nombre entier compris entre 1 et 12, la chaîne carbonée reliant les atomes d'azote pouvant éventuellement être interrompue par une ou plusieurs fonctions de type ester, éther ou amide.
- - R 16 is a hydrogen atom or an alkyl radical preferably containing 1 to 3 carbon atoms,
- - R 17 , R 18 , R, and R 20 are radicals having from 1 to 5 carbon atoms, substituted or not and interrupted or not by functions of the type -OH, -O-, -COO-, -CONH- , -COOH, -COONa, etc.
- - A is an anion preferably chosen from chlorides, methylsulphates, ethylsulphates, bromides, phosphates and the like.
- - n is an integer between 1 and 6.
- - m is an integer between 1 and 12, the carbon chain connecting the nitrogen atoms possibly being be interrupted by one or more functions of ester, ether or amide type.
Leur poids moléculaire est en général compris entre 200 et 2000, de préférence entre 200 et 1200.Their molecular weight is generally between 200 and 2000, preferably between 200 and 1200.
Les carboxylates sont des sels d'amines, de métaux alcalins ou alcalinoterreux de mono- ou poly-acides carboxyliques contenant 5 à 8 atomes de carbone, et un ou plusieurs groupes de type carboxyle et/ou hydroxyle.Carboxylates are salts of amines, alkali or alkaline earth metals of mono- or polycarboxylic acids containing 5 to 8 carbon atoms, and one or more groups of carboxyl and / or hydroxyl type.
A titre d'exemples de sels organiques particulièrement préférés aux fins de l'invention, on peut citer les gluconates, glutamates de monoéthanolamine, de diéthanol- amine, 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-hydroxy- éthyl)-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, glutamates of monoethanolamine, 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; N, N-bis (2-hydroxyethyl) -N-ethyl-N-methylammonium chloride or methyl sulfate; N, N-bis (2-hydroxyethyl) -N, N-diethylammonium chloride or ethyl sulfate; gluconic and glutamic acids and their sodium, potassium and ammonium salts.
A titre d'exemples de sels de polyammonium quaternaire appropriés aux fins de l'invention, on peut citer le dichlorure ou le diméthylsulfate de N,N,N',N'- tétrakis(2-hydroxyéthyl)-N,N'-diméthyléthylène-diammonium de formule :
Les autr.es 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 nonionic surfactants, 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 hydrophilic-lipophilic balance (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 nonionics but always in low concentration. The cumulative content of organic salts and nonionic agents must be less than the cumulative content of cationic surfactants and preferably less than 30% of the cumulative content by weight of the cationic surfactant (s). 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 parfumsavec 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 nonionic 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 colorants, optical brighteners, organic solvents, perfume s with or without solubilizer, depending on the desired effects, if such effects are not already provided by the cationic surfactants, the at least organic viscosity-lowering salts and non-ionic agent (s).
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 the concentrated formulations based on cationic surfactants according to the invention generally consists in mixing the constituents by pouring, with stirring, hot water at around 30 to 60 ° C., into the molten cationic surfactant (s), or conversely, pour the cationic surfactants into hot water, the water containing or not containing the perfume (s) and the non-ionic agent (s), then adding thereto, possibly after cooling to around 20 to 30 ° C., the or sufficient viscosity reducing organic salts and possibly the other additives.
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 0,5 g 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 having the appearance of a mobile gel whose viscosity is of the order of 500 millipascals-second is obtained. 0.5 g of N-methyl-N, 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.
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 1 g 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) methyl alcohol sulfate are mixed. ammonium 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 the mixture is allowed to cool with stirring. A fluid emulsion is obtained whose viscosity is close to 50 millipascals-second.
On mélange 13,33 g de chlorure de diméthyl- distéaryl-ammonium fondu à 75% de matière active en milieu hydroalcoolique avec 86,7 g d'eau vers 50°C; après mélange on ajoute vers 30-35°C 0,5 g de gluconate de sodium puis on laisse refroidir sous agitation; on obtient une émulsion fluide dont la viscosité est voisine de 60 millipascals-seconde.13.33 g of dimethyl-distearyl ammonium chloride, mixed with 75% of active material, in hydroalcoholic medium are mixed with 86.7 g of water at around 50 ° C .; after mixing, 0.5 g of sodium gluconate is added at around 30-35 ° C. and then allowed to cool with stirring; a fluid emulsion is obtained whose viscosity is close to 60 millipascals-second.
On ajoute sous agitation 80,3 g d'eau à 40°C à un mélange formé de 8 g de chlorure de distéaryl- diméthyl-ammonium à 85% de matière active, de 9,6 g de méthylsulfate de N-méthyl-N,N-di[2-(C14-C18-acyloxy)-éthyl]-N-(2-hydroxyéthyl)ammonium à 85% de matière active, de 1 g de nonylphénol éthoxylé avec 14 molécules d'oxyde d'éthylène et 0,6 g de parfum. Après homogénéisation on ajoute 0,5 g de N-méthyl-N,N,N-tri(2 -hydroxyéthyl)ammonium et on laisse refroidir sous agitation. On obtient une émulsion dont la viscosité est voisine de 50 millipascals-seconde.80.3 g of water at 40 ° C. are added with stirring to a mixture of 8 g of distearyl dimethyl ammonium chloride with 85% active material, 9.6 g of N-methyl-N methyl sulfate , N-di [2- (C 14 -C 18 -acyloxy) -ethyl] -N- (2-hydroxyethyl) ammonium with 85% active ingredient, 1 g of nonylphenol ethoxylated with 14 molecules of ethylene oxide and 0.6 g of perfume. After homogenization, 0.5 g of N-methyl-N, N, N-tri (2-hydroxyethyl) ammonium is added and the mixture is allowed to cool with stirring. An emulsion is obtained whose viscosity is close to 50 millipascals-second.
On ajoute sous agitation 78,9 g d'eau à 40°C à un mélange de 20 g d'une solution à 75% de matière active de lactate de N,N-di[2-(alkyl C14-C20)amidoéthyl]-N-(2-hydroxyéthyl)-N-hydrogénoammonium et de 0,6 g de parfum. Après homogénéisation on laisse refroidir à température ordinaire puis on ajoute toujours sous agitation 0,5 g de gluconate de sodium. On obtient une émulsion dont la viscosité est voisine de 130 millipascals-seconde.78.9 g of water at 40 ° C are added with stirring to a mixture of 20 g of a 75% solution of N, N-di [2- (C 14 -C 20 alkyl) lactate amidoethyl] -N- (2-hydroxyethyl) -N-hydrogenammonium and 0.6 g of perfume. After homogenization, the mixture is allowed to cool to ordinary temperature and then 0.5 g of sodium gluconate is always added with stirring. An emulsion is obtained whose viscosity is close to 130 millipascals-second.
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 mPa.s. On ajoute alors à cette émulstion 0,5 g de diméthylsulfate de N,N,N',N'-tétrakis(2-hydroxyéthyl)-N,N'-diméthyléthylène-diammonium. On obtient une émulsion fluide stable à 20°C dont la viscosité est voisine de 30 mPa.s. Il est alors possible d'ajouter à cette émulsion fluide, contenant 15 % de tensio-actif cationique adoucissant, des 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 mPa.s. 0.5 g of N, N, N ', N'-tetrakis (2-hydroxyethyl) -N, N'-dimethylethylene-diammonium dimethyl sulfate is then added to this emulsion. A stable fluid emulsion is obtained at 20 ° C., the viscosity of which is close to 30 mPa.s. It is then possible to add to this fluid emulsion, containing 15% of cationic softening surfactant, additives such as colorants and perfumes.
Claims (7)
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 |
Publications (4)
Publication Number | Publication Date |
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EP0165138A2 true EP0165138A2 (en) | 1985-12-18 |
EP0165138A3 EP0165138A3 (en) | 1987-05-06 |
EP0165138B1 EP0165138B1 (en) | 1996-08-07 |
EP0165138B2 EP0165138B2 (en) | 2002-08-28 |
Family
ID=26223964
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Application Number | Title | Priority Date | Filing Date |
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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 |
Country Status (3)
Country | Link |
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EP (1) | EP0165138B2 (en) |
DE (1) | DE3588115T3 (en) |
ES (1) | ES8608080A1 (en) |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0296995A1 (en) * | 1987-06-16 | 1988-12-28 | Cotelle S.A. | Concentrated softening compositions |
EP0299176A2 (en) * | 1987-05-26 | 1989-01-18 | Kao Corporation | Softener |
EP0354011A1 (en) * | 1988-08-04 | 1990-02-07 | Albright & Wilson Limited | Fabric conditioners |
EP0413249A1 (en) * | 1989-08-12 | 1991-02-20 | Witco Surfactants GmbH | Fabric softener |
WO1993016157A1 (en) * | 1992-02-07 | 1993-08-19 | Henkel Kommanditgeselschaft Auf Aktien | Process for producing low-viscosity 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 |
US5437801A (en) * | 1991-01-17 | 1995-08-01 | Huels Aktiengesellschaft | Aqueous emulsions containing fatty acid esters of N-methyl-N,N,N-trihydroxyethyl ammonium methyl sulfate |
US5686376A (en) * | 1995-01-12 | 1997-11-11 | The Procter & Gamble Company | Chelating agents for improved color fidelity |
GB2313601A (en) * | 1996-05-31 | 1997-12-03 | Procter & Gamble | Detergent compositions |
GB2313602A (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 |
US5767052A (en) * | 1995-01-12 | 1998-06-16 | The Procter & Gamble Company | Stabilized liquid fabric softener compositions |
WO2001059052A1 (en) * | 2000-02-08 | 2001-08-16 | Unilever Plc | Fabric conditioning compositions |
US6939844B2 (en) | 1996-09-19 | 2005-09-06 | The Procter & Gamble Company | Concentrated, preferably biodegradable, quaternary ammonium fabric softener compositions containing cationic polymers and process for preparation |
US7135451B2 (en) | 2003-03-25 | 2006-11-14 | The Procter & Gamble Company | Fabric care compositions comprising cationic starch |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
FR2303892A1 (en) * | 1975-03-12 | 1976-10-08 | Kao Corp | FABRIC SOFTENER |
FR2318267A1 (en) * | 1975-07-14 | 1977-02-11 | Procter & Gamble | TEXTILE SOFTENING COMPOSITIONS |
DE2822891A1 (en) * | 1977-05-30 | 1978-12-07 | Procter & Gamble Europ | TEXTILE TREATMENT PRODUCTS |
EP0060003A2 (en) * | 1981-03-07 | 1982-09-15 | THE PROCTER & GAMBLE COMPANY | Textile treatment compositions and preparation thereof |
-
1985
- 1985-05-15 DE DE19853588115 patent/DE3588115T3/en not_active Expired - Lifetime
- 1985-05-15 EP EP19850400960 patent/EP0165138B2/en not_active Expired - Lifetime
- 1985-05-16 ES ES543216A patent/ES8608080A1/en not_active Expired
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US3681241A (en) * | 1968-03-04 | 1972-08-01 | Lever Brothers Ltd | Fabric softening |
FR2303892A1 (en) * | 1975-03-12 | 1976-10-08 | Kao Corp | FABRIC SOFTENER |
FR2318267A1 (en) * | 1975-07-14 | 1977-02-11 | Procter & Gamble | TEXTILE SOFTENING COMPOSITIONS |
DE2822891A1 (en) * | 1977-05-30 | 1978-12-07 | Procter & Gamble Europ | TEXTILE TREATMENT PRODUCTS |
EP0060003A2 (en) * | 1981-03-07 | 1982-09-15 | THE PROCTER & GAMBLE COMPANY | Textile treatment compositions and preparation thereof |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0299176A2 (en) * | 1987-05-26 | 1989-01-18 | Kao Corporation | Softener |
EP0299176A3 (en) * | 1987-05-26 | 1990-03-21 | Kao Corporation | Softener |
EP0296995A1 (en) * | 1987-06-16 | 1988-12-28 | Cotelle S.A. | Concentrated softening compositions |
WO1988010294A1 (en) * | 1987-06-16 | 1988-12-29 | Cotelle S.A. | Concentrated softening compositions |
EP0354011A1 (en) * | 1988-08-04 | 1990-02-07 | Albright & Wilson Limited | Fabric conditioners |
US5364542A (en) * | 1989-08-12 | 1994-11-15 | Rewo Chemische Werke Gmbh | Fabric softener rinsing agents |
US5180508A (en) * | 1989-08-12 | 1993-01-19 | Rewo Chemische Werke Gmbh | Fabric softener rinsing agents |
EP0413249A1 (en) * | 1989-08-12 | 1991-02-20 | Witco Surfactants GmbH | Fabric softener |
US5437801A (en) * | 1991-01-17 | 1995-08-01 | Huels Aktiengesellschaft | Aqueous emulsions containing fatty acid esters of N-methyl-N,N,N-trihydroxyethyl ammonium methyl sulfate |
WO1993016157A1 (en) * | 1992-02-07 | 1993-08-19 | Henkel Kommanditgeselschaft Auf Aktien | Process for producing low-viscosity 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 |
US5767052A (en) * | 1995-01-12 | 1998-06-16 | The Procter & Gamble Company | Stabilized liquid fabric softener compositions |
US5686376A (en) * | 1995-01-12 | 1997-11-11 | The Procter & Gamble Company | Chelating agents for improved color fidelity |
GB2313601A (en) * | 1996-05-31 | 1997-12-03 | Procter & Gamble | Detergent compositions |
GB2313602A (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 |
US6939844B2 (en) | 1996-09-19 | 2005-09-06 | The Procter & Gamble Company | Concentrated, preferably biodegradable, quaternary ammonium fabric softener compositions containing cationic polymers and process for preparation |
WO2001059052A1 (en) * | 2000-02-08 | 2001-08-16 | Unilever Plc | Fabric conditioning compositions |
US7135451B2 (en) | 2003-03-25 | 2006-11-14 | The Procter & Gamble Company | Fabric care compositions comprising cationic starch |
Also Published As
Publication number | Publication date |
---|---|
DE3588115D1 (en) | 1996-09-12 |
DE3588115T3 (en) | 2003-03-27 |
ES543216A0 (en) | 1986-06-01 |
ES8608080A1 (en) | 1986-06-01 |
EP0165138B1 (en) | 1996-08-07 |
DE3588115T2 (en) | 1997-02-27 |
EP0165138B2 (en) | 2002-08-28 |
EP0165138A3 (en) | 1987-05-06 |
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