EP0296995A1 - Concentrated softening compositions - Google Patents
Concentrated softening compositions Download PDFInfo
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- EP0296995A1 EP0296995A1 EP88420204A EP88420204A EP0296995A1 EP 0296995 A1 EP0296995 A1 EP 0296995A1 EP 88420204 A EP88420204 A EP 88420204A EP 88420204 A EP88420204 A EP 88420204A EP 0296995 A1 EP0296995 A1 EP 0296995A1
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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
- C11D1/645—Mixtures of compounds all of which are cationic
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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 fabric softener compositions, especially aqueous compositions containing relatively large amounts of cationic type softeners, intended for use in the rinsing cycle of laundering operations. More particularly, the invention relates to concentrated aqueous compositions of cationic softeners whose viscosity is adjustable and which are clear and dilutable with water, the viscosity of the diluted compositions obtained being adjustable.
- the concentrated compositions have a low viscosity, making it possible to pour them, and stable over time, and are capable of being diluted, in particular by tap water, this water being at any temperature.
- the diluted compositions thus obtained have a viscosity acceptable to the housewife and greater than that of the concentrated composition.
- compositions of cationic softeners are already known which can be diluted with water.
- Document FR-A-2 451 960 describes compositions containing a softening agent which is a dialkyldimethylammonium chloride or a dialkylmethylethoxyammonium chloride in admixture with a non-softening agent which is an alkyldimethylbenzylammonium chloride, isopropyl alcohol and 'water.
- a softening agent which is a dialkyldimethylammonium chloride or a dialkylmethylethoxyammonium chloride in admixture with a non-softening agent which is an alkyldimethylbenzylammonium chloride, isopropyl alcohol and 'water.
- This document specifies that the compositions contain the non-softening agent at a concentration greater than 33% by weight, and the softening agent at a concentration lower than the concentration of the non-softening agent.
- compositions described contain from 25% to 12.5% of dialkyldimethylammonium chloride or 12.5% of softening dialkylmethylethoxyammonium chloride and approximately from 33% to 50% of non-softening alkyldimethylbenzylammonium chloride.
- the aim of this publication is to obtain transparent compositions.
- compositions are expensive and of limited effectiveness, since they contain a large amount of non-softening cationic agent.
- Document FR-A-2 540 901 describes compositions containing - from 15 to 50% of dialkyldimethylammonium salts, - from 10 to 50% of hydrophilic solvents, the weight ratio between the solvents and the dialkyldimethylammonium salts being between 0.7 and 2.3.
- compositions may possibly contain aids which are for example hydrophilic nonionic surfactants.
- the compositions are intended to be diluted with water.
- compositions which can be diluted with cold or lukewarm water.
- compositions contain a nonionic hydrophilic solubilizing agent.
- Document FR-A-2 523 606 describes concentrated fabric softener compositions comprising 8 to 20% of a softener of the imidazolinium type and 0.5 to 5% of a quaternary ammonium compound, either conventional or dicationic. These compositions are presented as stable even at low or high temperatures. They can be supplemented, optionally, by secondary proportions, namely between 0.5 and 10%, of other ingredients among which are lower alkanols. Compositions of this type are not clear and have a viscosity which increases with time, during storage.
- Document EP-A-60 003 describes concentrated softening compositions for fabrics comprising 8 to 22% of a cationic softener 0.6 to 3% of at least one water-soluble polyalkoxylated ammonium salt and 0.2 to 5% of 'a fatty acid ester of a polyol.
- the objective is to obtain stable compositions, the viscosity of which does not vary appreciably, even at high temperature and over long storage periods.
- the compositions thus formed are not clear.
- Document EP-A-199 382 describes softening compositions which, in order not to lose their effectiveness when they are put in the presence of the anionic or nonionic detergents that the washing products contain, contain 3 to 35% of a mixture of: (a) 10-92% of the reaction product of higher fatty acids with a selected polyamine, (b) 8-90% of cationic nitrogen salts having a single long acipic C15 - C22 aliphatic chain, and (c ) 0-80% of cationic nitrogen salts having at least two chains of this type or a chain of this type and an arylalkyl ring.
- Document FR-A-2 295 122 describes concentrated softening compositions for fabrics, stable with respect to temperature, not gelling and having a disinfecting action. These compositions comprise 30 to 60% of a cationic softening agent, 5 to 20% of a include 30 to 60% of a cationic softening agent, 5 to 20% of a cationic disinfectant, 5 to 20% of a nonionic dispersant and 15 to 40% of lower alkanols. It is expressly stated that the presence of non-ionic dispersants is essential for the concentrated product to disperse well in cold water.
- Document EP-A-40 562 describes concentrated softener compositions containing a cationic softening agent and a nonionic agent in a ratio of between 10/1 and 3/2, alcohol and water; the objective is to obtain softener compositions, concentrated, dilutable with cold or lukewarm water.
- the invention aims to overcome these drawbacks.
- the present invention provides concentrated, clear, fabric softener compositions which can be diluted with cold water without forming particles or agglomerates capable of clogging small diameter pipes and which are stable in storage both in concentrated state than diluted state.
- compositions according to the invention are such that they contain from 20 to 50% of softening compound A, from 0.1% to 10% and more advantageously 0.1 to 3% of compound B, and from 10 to 30 % by weight of solvent C.
- Examples of the compound of formula (I) are dimyristyldimethylammonium chloride, distearyldimethylammonium chloride, distearyl-2-hydroxypropylmethylammonium methyl sulfate, oleylstearyl dimethylammonium ethyl sulfate; in which R5 and R8 are similar or different and are chosen from C8 to C22 alkyl and alkenyl groups, optionally branched, R6 is chosen from C alk to C4 alkyl groups, substituted or unsubstituted, R7 is chosen from hydrogen or a C1 - C4 substituted or unsubstituted alkyl group, X ⁇ is a quaternization anion.
- halides ethyl sulphate, methyl sulphate, acetate, phosphate, carbonate, lactate
- R9 and R12 are similar or different and are chosen from C8 to C22 alkyl or alkenyl groups, optionally branched
- R10 and R11 are similar or different and are chosen from substituted or unsubstituted, C1 - C4 alkyl groups
- X ⁇ is a quaternization anion.
- It can for example be chosen from the group of halides, methylsulfate, ethylsulfate, acetate, phosphate, carbonate, lactate.
- R13 and R15 are similar or different and are chosen from C8 to C22 alkyl or alkenyl groups, optionally branched
- R14 is chosen from hydrogen, methyl, ethyl groups and the group - (C n H 2n O) xH, in which n is equal to 2 or 3 and x is between 1 and 5, and
- X ⁇ is a quaternization anion chosen from the group of halides, methylsulfate, ethylsulfate, acetate, phosphate, carbonate, lactate, for example.
- Examples of compounds of formula (II) are 1-tallow-amidoethyl-2-tallow-imidazolinium methyl sulfate, 1-methyl-1 - oleylamidoethyl-2-oleyl-imidazolinium, 1-methyl-1-palmitoleylamidoethyl-2-palmitoleyl-imidazolinium, 1-methyl-1-tallow-amidoethyl-2-tallow-imidazolinium, 1-methyl-1-hydrogenated tallow-amidoethyl-2- tallow hydrogenimidazolinium.
- Examples of compounds of formula (III) are methyl sulphate 1-ethylene-bis (2-stearyl, 1-methylimidazolinium), 1-ethylene-bis (2-oleyl-1-methylimidazolinium), 1-ethylene-bis (2-tallow-1-methylimidazolinium).
- Examples of compounds of formula (IV) are: di (2-hydrogenated tallow-amidoethyl) -hydroxyethylammonium, di (2-hydrogenated tallow-amidoethyl) -di-methylammonium and methyl-di (2-palmitylamidoethyl) methyl sulfate -hydroxyethylammonium.
- agents B according to the invention are in practice chosen from quaternary ammonium salts and polyammonium salts, these compounds optionally containing a single long C8 - C22 alkyl chain.
- agents B are chosen from salts of mono- or poly-ammonium quaternary or imidazolinium compounds, optionally bactericidal or a mixture thereof.
- the cationic compounds B according to the invention can thus be chosen from the compounds having the following general formulas: in which R is a C1-C4 aliphatic or hydroxyalkoxy group, optionally polyoxyalkylated, R16 is chosen from alkyl or alkenyl groups having from 8 to 22 carbon atoms, preferably from 8 to 10 carbon atoms, optionally branched, optionally substituted by ether, ester or amide groups, R17 is chosen from alkyl or alkenyl groups having from 1 to 4 carbon atoms, optionally branched, R18 is chosen from alkyl or alkenyl groups having from 8 to 18 carbon atoms, preferably from 12 to 16 carbon atoms.
- R19 and R20 are chosen from hydrogen or halogen
- Y ⁇ is a quaternization anion. It can for example be chosen from the group of halides, methylsulfate, ethylsulfate, acetate, phosphonate, carbonate, lactate.
- agents B of formulas (V) or (VI) are: lauryldimethylbenzylammonium chloride, alkyldimethylbenzylammonium chloride in which the alkyl radical is C12 - C18, trimethyldodecylbenzylammonium chloride, methyl-bis (2-hydroxyethyl) -oleylammonium chloride, methyl-1-capryl-2 methysulfate -caprylamido-3-ethyl-imidazolinium.
- the cationic compounds B can also be chosen from the compounds having the following general formula: in which R21 is a Cip to C22 aliphatic group, optionally branched, optionally unsaturated, R22 is chosen from groups H, alkyl, hydroxyalkyl hydroxyalkoxy in C1 - C4, n is an integer from 1 to 6, m is an integer from 1 to 5, X ⁇ is a quaternization anion. It can for example be chosen from the group of halides, methylsulfate, ethylsulfate, acetate, phosphate, carbonate, lactate.
- agents B of formula (VII) are: N- (tallow derivative) dimethosulfate -N, N, N1, N1-tetramethyl-1,3-propanediammonium, N- (tallow derivative) dimethosulfate -N, N1, N1-trimethyl-1,3-propanediammonium, N-oleyl-N, N, N1, N1, N1-pentamethyl-1,3-propanediammonium dimethosulfate, N- (tallow derivative) dimethosulfate -N, N, N1, N1, N1-pentamethyl-1,3-propanediammonium, N-stearyl-N, N, N1, N1, N1-pentamethyl-1,3-propanediammonium dimethosulfate, N-stearyloxypropyl-N, N1, N1-tri (3-hydroxypropyl) -1,3-propane-diammonium diacetate.
- the preferred agents B according to the invention are coco-bis (2-hydroxyethyl) methylammonium chloride, for example ETHOQUAD O / 12, containing 25% isopropanol and manufactured by AKZO or oleylbis chloride (2- hydroxyethyl) methylammonium, for example ETHOQUAD 0/12, containing 25% isopropanol and manufactured by AKZO.
- the compounds B according to the invention can also be chosen from the compounds having the general formulas (II), (III) and (IV), mentioned above, in which R5 and R8, R9 and R12, R13 and R15 are chosen among the C6 - C14 alkyl or alkenyl groups, optionally branched.
- the solvents C according to the invention can be chosen from hydroxylated solvents or their mixtures, for example alcohols, polyols, polyol ethers, polyether polyols; the preferred solvents are isopropanol, isobutanol, n-propanol, methyl-2-pentanediol-2,4, 1,2-propylene glycol and the monomethyl ether of monopropylene glycol.
- the softening agent is 1-oleylamidoethyl-2-oleylimidazolinium methosulfate, for example in solution in isopropanol or in solution in 1,2-propylene glycol at 75% softener and 25% alcohol.
- REWOQUAT W 3690 REWOQUAT W 3690 / PG.
- Another preferred compound is disuif-2-hydroxypropylmethylammonium chloride sold under the name of PRAEPAGEN WKL by HOECHST.
- component B makes it possible, in combination with solvent C, to thin and make the composition clear; moreover, the addition of component B makes it possible to reduce the content of solvent C, but only to a certain extent, since too large a proportion of component B would exert an undesired effect of lowering the viscosity of the diluted composition.
- compositions according to the invention For the preparation of the compositions according to the invention, it is simply suitable: - in the case of ingredients that are liquid at room temperature, mix them cold in any order, - if one of the ingredients is not liquid at room temperature, heat this ingredient to make it melt and add the other ingredients to the resulting melt, observing the usual precautions, and preferably adding solvent C first and water last.
- the invention makes it possible to achieve the objectives mentioned above.
- the dilute, viscous and stable compositions which the present invention makes it possible to obtain can be prepared by dilution with tap water, even cold, of the above-mentioned concentrated compositions; the dilution ratio is preferably from 1: 2 to 1:10, advantageously from 1: 4 for a composition concentrated at around 20% of cationic softening active material A.
- compositions according to the invention used in appropriate quantities in the last rinsing cycle following the washing of loads of laundry in a domestic washing machine provide a completely suitable softening for the laundry.
- LDMBAC lauryldimethylbenzylammonium chloride.
- Agent A DSHPMAC (*) 18.35%
- Agent B ODHMAC (**) 1.65%
- Solvent C Isopropanol 15% Perfume 0.77%
- Dye 1% solution
- the composition obtained is fluid and clear. Its viscosity (measured with the Brookfield viscometer, mobile 1, at 6 revolutions / minute) is 35 mpa.s. After adding three times its volume of tap water to this composition, a diluted composition is obtained whose viscosity (measured under the same conditions) is 210 mpa.s after 1 week and 480 mpa.s after 2 months.
- the concentrated composition is stable at room temperature and at 40 ° C for more than a year. At -15 ° C the concentrated composition takes the consistency of a gel, but which is assex fluid and which disappears to give a completely fluid composition after returning to room temperature.
- composition is prepared by mixing: DSHPMAC 20% ODHMAC 2.04% Isopropanol 7.10% Dispropylene glycol 18% Perfume 0.97% Dye (1% solution) 0.6% Water qs 100%
- the composition thus obtained is fluid and clear. It is stable and has a viscosity (measured with a Brookfield viscometer, mobile 2, at 12 revolutions / minute) of 50 mpa.s after 1 day and the same again after 1 month.
- the viscosity (measured with a Brookfield viscometer, mobile 1, at 6 revolutions / minute) is 203 mpa.s after 1 day and 486 mpa.s after 1 month.
- composition is prepared by mixing: DSHPMAC 20% ODHMAC 2.04% Isopropanol 7.10% Monopropylene glycol monomethyl ether 14% Perfume 0.97% Dye (1% solution) 0.6% Water qs 100%
- the composition obtained is fluid and clear. It is stable and has a viscosity (measured with a Brookfield viscometer, mobile 2, at 12 revolutions / minute) of 40 mpa.s after 1 day and 30 mpa.s after 1 month.
- the viscosity (measured with a Brookfield viscometer, mobile 1, at 6 revolutions / minute) is 549 mpa.s after 1 day and 900 mpa.s after 1 month.
- composition is prepared by mixing: DOIMMS (*) 50% ODHMAC 10% Isopropanol 3.34% Perfume 0.97% Dye (1% solution) 0.8% Water qs 100%
- the composition obtained is fluid and clear. Its viscosity (measured with the Brookfield viscometer, mobile 2, at 12 revolutions / minute) is 30 mpa.s after 4 days. After adding nine times its volume of tap water to this solution, a dilute composition is obtained, the viscosity (measured with a Brookfield viscometer, mobile 1, at 6 revolutions / minute) is 132 mpa.s after 4 days.
- the influence of the temperature of the dilution water of a concentrated composition is studied on the viscosity of the diluted composition.
- DOIMMS 20% ODHMAC 2% Isopropanol 20% Perfume 1% Water qs 100%
- This concentrated composition is diluted with three times its volume of water.
- the viscosities are measured with a Brookfield viscometer, mobile 1, at 6 revolutions / minute.
- compositions according to the invention have a viscosity greater than 100 mPa.s for dilution water temperatures below 20 ° C.
- a viscosity greater than 100 mPa.s, preferably 100-200 mPa.s is a viscosity which is perceived by the housewife as the index of an effective product.
- compositions are diluted with water at 20 ° C. to obtain diluted compositions containing 5% by weight of softening agent A.
- the viscosities of the diluted compositions thus obtained are measured, with a Brookfield viscometer, mobile 1, speed 6 revolutions / minute .
- the viscosities of the diluted compositions containing 5% by weight of softener A are included between 100 and 160 mPa.s.
- the technical function of the non-softening cationic agent is different from the technical function of the nonionic agent.
- the viscosity of the diluted composition can be adjusted to a value acceptable to the housewife. (preferably between 50 and 900 mPa.s).
- Examples 3b and 4b show that, for a composition containing approximately 15% of softening agent A and 0.1% of non-softening agent B, the viscosity of the diluted composition is 160 mPa.s, while for a composition containing 4% of non-softening agent B, the viscosity of the diluted composition is 10 mPa.s.
- the diluted compositions 4a and 4b obtained from the concentrated compositions are dispersed in cold water, it is seen that the diluted composition 4a is very difficult to disperse and that it is necessary to shake by hand for several tens of seconds to obtain good dispersion in water. On the contrary, the diluted composition 4b disperses very easily in water at 10 ° C (in less than 5 seconds).
- composition 20% of DSHPM-AC, 2% ODHMAC, 13% of 1,2-propylene glycol, 11% isopropanol 1% perfume, qs 100% water
- This composition is diluted with three times its volume of water.
- the temperature of the dilution water is 10 ° C.
- a dilute, stable composition is obtained, the viscosity of which, measured in the same manner as in the previous examples, is 260 mPa.s.
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Abstract
Description
La présente invention concerne des compositions adoucissantes pour tissus, notamment des compositions aqueuses contenant des quantités relativement importantes d'adoucissants du type cationique, destinées à être utilisées dans le cycle de rincage des opérations de blanchissage. Plus particulièrement, l'invention concerne des compositions aqueuses concentrées d'adoucissants cationiques dont la viscosité est ajustable et qui sont limpides et diluables à l'eau, la viscosité des compositions diluées obtenues étant ajustable. Les compositions concentrées ont une viscosité faible, permettant de les verser, et stable dans le temps, et sont susceptibles d'être diluées, notamment par de l'eau du robinet, cette eau étant à température quelconque. Les compositions diluées ainsi obtenues ont une viscosité acceptable pour la ménagère et supérieure à celle de la composition concentrée.The present invention relates to fabric softener compositions, especially aqueous compositions containing relatively large amounts of cationic type softeners, intended for use in the rinsing cycle of laundering operations. More particularly, the invention relates to concentrated aqueous compositions of cationic softeners whose viscosity is adjustable and which are clear and dilutable with water, the viscosity of the diluted compositions obtained being adjustable. The concentrated compositions have a low viscosity, making it possible to pour them, and stable over time, and are capable of being diluted, in particular by tap water, this water being at any temperature. The diluted compositions thus obtained have a viscosity acceptable to the housewife and greater than that of the concentrated composition.
On connaît déjà des compositions concentrées d'adoucissants cationiques, diluables à l'eau.Concentrated compositions of cationic softeners are already known which can be diluted with water.
Le document FR-A-2 451 960 décrit des compositions contenant un agent adoucissant qui est un chlorure de dialkyldiméthylammonium ou un chlorure de dialkylméthyléthoxyammonium en mélange avec un agent non adoucissant qui est un chlorure d'alkyldiméthylbenzylammonium, de l'alcool isopropylique et de l'eau. Ce document précise que les compositions contiennent l'agent non adoucissant à une concentration supérieure à 33 % en poids, et l'agent adoucissant à une concentration inférieure à la concentration de l'agent non adoucissant. Les compositions décrites contiennent de 25 % à 12,5 % de chlorure de dialkyldiméthylammonium ou 12,5 % de chlorure de dialkylméthyléthoxyammonium adoucissant et environ de 33 % à 50 % de chlorure d'alkyldiméthylbenzylammonium non adoucissant. Le but poursuivi selon cette publication est d'obtenir des compositions transparentes.Document FR-A-2 451 960 describes compositions containing a softening agent which is a dialkyldimethylammonium chloride or a dialkylmethylethoxyammonium chloride in admixture with a non-softening agent which is an alkyldimethylbenzylammonium chloride, isopropyl alcohol and 'water. This document specifies that the compositions contain the non-softening agent at a concentration greater than 33% by weight, and the softening agent at a concentration lower than the concentration of the non-softening agent. The compositions described contain from 25% to 12.5% of dialkyldimethylammonium chloride or 12.5% of softening dialkylmethylethoxyammonium chloride and approximately from 33% to 50% of non-softening alkyldimethylbenzylammonium chloride. The aim of this publication is to obtain transparent compositions.
Cependant, de telles compositions sont chères et d'une efficacité limitée, puisqu'elles contiennent une quantité important d'agent cationique non adoucissant.However, such compositions are expensive and of limited effectiveness, since they contain a large amount of non-softening cationic agent.
Le document FR-A-2 540 901 décrit des compositions contenant
- de 15 à 50 % de sels de dialkyldiméthylammonium,
- de 10 à 50 % de solvants hydrophiles,
le rapport pondéral entre les solvants et les sels de dialkyldiméthylammonium étant compris entre 0,7 et 2,3.Document FR-A-2 540 901 describes compositions containing
- from 15 to 50% of dialkyldimethylammonium salts,
- from 10 to 50% of hydrophilic solvents,
the weight ratio between the solvents and the dialkyldimethylammonium salts being between 0.7 and 2.3.
Ces compositions peuvent contenir éventuellement des aides de solubilisation qui sont par exemple des agents de surface non ioniques hydrophiles. Les compositions sont destinées à être diluées à l'eau.These compositions may possibly contain aids which are for example hydrophilic nonionic surfactants. The compositions are intended to be diluted with water.
Le but visé selon ce document est l'obtention de compositions concentrées d'adoucissant, diluables à l'eau froide ou tiède. Dans les exemples, il est toujours mentionné que de telles compositions contiennent un agent de solubilisation hydrophile non ionique.The aim of this document is to obtain concentrated softener compositions which can be diluted with cold or lukewarm water. In the examples, it is always mentioned that such compositions contain a nonionic hydrophilic solubilizing agent.
Cependant, les compositions concentrées décrites dans ces publications ont pour inconvénient de donner par dilution des compositions très fluides et peu visqueuses.However, the concentrated compositions described in these publications have the drawback of giving very dilute, low-viscosity compositions by dilution.
Le document FR-A-2 523 606 décrit des compositions adoucissantes concentrées pour tissus comprenant 8 à 20 % d'un adoucissant de type imidazolinium et 0,5 à 5 % d'un composé d'ammonium quaternaire soit classique, soit dicationique. Ces compositions sont présentées comme stables même aux températures basses ou élevées. Elles peuvent être complétées, en option, par des proportions secondaires, à savoir entre 0,5 et 10 %, d'autres ingrédients parmi lesquels figurent des alcanols inférieurs. Les compositions de ce type ne sont pas limpides et ont une viscosité qui croît avec le temps, au cours du stockage.Document FR-A-2 523 606 describes concentrated fabric softener compositions comprising 8 to 20% of a softener of the imidazolinium type and 0.5 to 5% of a quaternary ammonium compound, either conventional or dicationic. These compositions are presented as stable even at low or high temperatures. They can be supplemented, optionally, by secondary proportions, namely between 0.5 and 10%, of other ingredients among which are lower alkanols. Compositions of this type are not clear and have a viscosity which increases with time, during storage.
Le document EP-A-60 003 décrit des compositions adoucissantes concentrées pour tissus comprenant 8 à 22 % d'un adoucissant cationique 0,6 à 3 % d'au moins un sel d'ammonium polyalcoxylé hydrosoluble et 0,2 à 5 % d'un ester d'acide gras d'un polyol. L'objectif visé est l'obtention de compositions stables et dont la viscosité ne varie sensiblement pas, même à température élevée et sur de longues durées de stockage. Les compositions ainsi formées ne sont pas limpides.Document EP-A-60 003 describes concentrated softening compositions for fabrics comprising 8 to 22% of a cationic softener 0.6 to 3% of at least one water-soluble polyalkoxylated ammonium salt and 0.2 to 5% of 'a fatty acid ester of a polyol. The objective is to obtain stable compositions, the viscosity of which does not vary appreciably, even at high temperature and over long storage periods. The compositions thus formed are not clear.
Le document EP-A-199 382 décrit des compositions adoucissantes qui, pour ne pas perdre de leur efficacité lorsqu'elles sont mises en présence des détergents anioniques ou non-ioniques que contiennent les produits de lavage, comportent 3 à 35 % d'un mélange de : (a) 10-92 % du produit de réaction d'acides gras supérieurs avec une polyamine sélectionnée, (b) 8-90 % de sels azotés cationiques ayant une seule longue chaîne aliphatique acyclique en C₁₅ - C₂₂, et (c) 0-80 % de sels azotés cationiques ayant au moins deux chaînes de ce type ou une chaîne de ce type et un cycle arylalkyle.Document EP-A-199 382 describes softening compositions which, in order not to lose their effectiveness when they are put in the presence of the anionic or nonionic detergents that the washing products contain, contain 3 to 35% of a mixture of: (a) 10-92% of the reaction product of higher fatty acids with a selected polyamine, (b) 8-90% of cationic nitrogen salts having a single long acipic C₁₅ - C₂₂ aliphatic chain, and (c ) 0-80% of cationic nitrogen salts having at least two chains of this type or a chain of this type and an arylalkyl ring.
Le document FR-A-2 295 122 décrit des compositions adoucissantes concentrées pour tissus, stables vis-à-vis de la température, ne se gélifiant pas et présentant une action désinfectante. Ces compositions comprennent 30 à 60 % d'un agent adoucissant cationique, 5 à 20 % d'un comprennent 30 à 60 % d'un agent adoucissant cationique, 5 à 20 % d'un désinfectant cationique, 5 à 20 % d'un dispersant non-ionique et 15 à 40 % d'alcanols inférieurs. Il est indiqué expressément que la présence de dispersants non-ioniques est essentielle pour que le produit concentré se disperse bien dans de l'eau froide.Document FR-A-2 295 122 describes concentrated softening compositions for fabrics, stable with respect to temperature, not gelling and having a disinfecting action. These compositions comprise 30 to 60% of a cationic softening agent, 5 to 20% of a include 30 to 60% of a cationic softening agent, 5 to 20% of a cationic disinfectant, 5 to 20% of a nonionic dispersant and 15 to 40% of lower alkanols. It is expressly stated that the presence of non-ionic dispersants is essential for the concentrated product to disperse well in cold water.
Le document EP-A-40 562 décrit des compositions concentrées d'adoucissants contenant un agent adoucissant cationique et un agent non ionique dans un rapport compris entre 10/1 et 3/2, de l'alcool et de l'eau ; l'objectif est l'obtention de compositions d'adoucissant, concentrées, diluables à l'eau froide ou tiède.Document EP-A-40 562 describes concentrated softener compositions containing a cationic softening agent and a nonionic agent in a ratio of between 10/1 and 3/2, alcohol and water; the objective is to obtain softener compositions, concentrated, dilutable with cold or lukewarm water.
Or, les ménagères qui diluent avec de l'eau du robinet de telles compositions, concentrées pour préparer des compositions diluées à stocker avant emploi, préfèrent obtenir des compositions diluées ayant un aspect visqueux. Mais la température de l'eau du robinet varie. Ainsi, elle peut varier entre +5 et +25°C. On a constaté que lorsque la température de l'eau est de l'ordre de +5°C, la viscosité des compositions diluées est alors trop élevée, et lorsque la ménagère verse la composition diluée dans un bac prévu à cet effet dans une machine automatique à laver le linge, la composition diluée, du fait de sa viscosité importante, et de sa tendance à former des floculats, peut boucher la canalisation d'amenée de la compositon adoucissante dans le bac de rinçage. En outre, la dispersion de la composition diluée dans l'eau de rinçage se fait plus difficilement quand la composition concentrée est diluée avec de l'eau froide, par exemple ayant une température de +5°C environ.However, housewives who dilute with tap water such compositions, concentrated to prepare diluted compositions to be stored before use, prefer to obtain diluted compositions having a viscous appearance. But the temperature of tap water varies. Thus, it can vary between +5 and + 25 ° C. It has been found that when the water temperature is of the order of + 5 ° C., the viscosity of the diluted compositions is then too high, and when the housewife pours the diluted composition into a container provided for this purpose in a machine. automatic washing machine, the diluted composition, because of its high viscosity, and its tendency to form flocculates, can clog the supply line of the softening composition in the rinsing tank. In addition, the dispersion of the composition diluted in rinsing water is more difficult when the concentrated composition is diluted with cold water, for example having a temperature of approximately + 5 ° C.
L'invention vise à pallier ces inconvénients.The invention aims to overcome these drawbacks.
Les problèmes à résoudre sont les suivants :
Obtention d'une composition adoucissante concentrée en agents adoucissants :
- limpide et stable au stockage entre -15 et +40°C,
- diluable à l'eau de ville, même froide,
- contenant une quantité d'alcool la plus faible possible,
- ayant une viscosité faible, permettant de la verser et stable dans le temps, et
- donnant une composition diluée, stable au stockage, et dont la viscosité soit acceptable pour la ménagère et supérieure à celle de la composition concentrée.The issues to be resolved are as follows:
Obtaining a softening composition concentrated in softening agents:
- clear and stable during storage between -15 and + 40 ° C,
- dilutable with tap water, even cold,
- containing as little alcohol as possible,
- having a low viscosity, making it possible to pour it and stable over time, and
- giving a diluted composition, stable in storage, and whose viscosity is acceptable to the housewife and greater than that of the concentrated composition.
Aucun des documents de la technique antérieure n'a décrit ou suggéré ce problème de viscosité des compositions diluées, suffisamment élevée pour être acceptée par l'utilisateur, mais suffisamment faible pour pouvoir s'écouler dans des conduites de machines à laver le linge, ces compositions ayant une structure physique homogène et ne formant pas d'agglomérats pouvant boucher les conduites et étant facilement dispersables dans l'eau de rinçage.None of the prior art documents has described or suggested this problem of viscosity of the diluted compositions, high enough to be accepted by the user, but low enough to be able to flow into the lines of washing machines, these compositions having a homogeneous physical structure and not forming agglomerates which can clog the pipes and which are easily dispersible in the rinsing water.
La présente invention fournit des compositions concentrées, limpides, d'adoucissants pour tissus qui peuvent être diluées par de l'eau froide sans former de particules ou agglomérats susceptibles de boucher les conduites de faible diamètre et qui sont stables au stockage, tant à l'état concentré qu'à l'état dilué.The present invention provides concentrated, clear, fabric softener compositions which can be diluted with cold water without forming particles or agglomerates capable of clogging small diameter pipes and which are stable in storage both in concentrated state than diluted state.
L'invention concerne une composition concentrée d'adoucissant pour textiles, diluable à l'eau, caractérisée en ce qu'elle contient :
- a) de 10 à 50 % en poids d'au moins un agent adoucissant A, choisi parmi les sels d'ammonium quaternaire ayant au moins deux chaînes alkyle longues en C₈-C₂₂, éventuellement interrompues par un groupe ester, éther ou amide ; les sels d'imidazolinium ; et les produits de réaction des acides gras avec des polyamines choisies dans le groupe des hydroxyalkylalkylènediamines et des dialkylènetriamines, dans lesquelles les groupes alkyle et alkylène contiennent de 1 à 3 atomes de carbone
- b) de 0,1 à 10 % en poids d'au moins un composé cationique B, choisi parmi les composés cationiques dont la solubilité en milieu aqueux ou hydroalcoolique est supérieure à la solubilité du composé adoucissant A,
- c) de 2 à 35 % en poids d'au moins un solvant C,
- d éventuellement des adjuvants et/ou d'autres additifs classiques, et
- e) de l'eau pour le complément,
- a) from 10 to 50% by weight of at least one softening agent A, chosen from quaternary ammonium salts having at least two long C₈-C₂₂ alkyl chains, optionally interrupted by an ester, ether or amide group; imidazolinium salts; and reaction products of fatty acids with polyamines selected from the group of hydroxyalkylalkylenediamines and dialkylenetriamines, in which the alkyl and alkylene groups contain from 1 to 3 carbon atoms
- b) from 0.1 to 10% by weight of at least one cationic compound B, chosen from cationic compounds whose solubility in aqueous or hydroalcoholic medium is greater than the solubility of the softening compound A,
- c) from 2 to 35% by weight of at least one solvent C,
- d optionally adjuvants and / or other conventional additives, and
- e) water for the complement,
Les compositions préférées selon l'invention sont telles qu'elles contiennent de 20 à 50 % de composé adoucissants A, de 0,1 % à 10 % et plus avantageusement encore 0,1 à 3 % de composé B, et de 10 à 30 % en poids de solvant C.The preferred compositions according to the invention are such that they contain from 20 to 50% of softening compound A, from 0.1% to 10% and more advantageously 0.1 to 3% of compound B, and from 10 to 30 % by weight of solvent C.
Les agents adoucissants cationiques A des compositions selon l'invention sont décrits notamment dans l'article "Cationic Surfactants in Laundry Detergents and Laundry Aftertreatment Aids" - J.A.O.C.S., Vol 61, no2 (February 1984), et peuvent être choisis parmi les composés ayant les formules générales suivantes :
Des exemples du composé de formule (I) sont le chlorure de dimyristyldiméthylammonium, le chlorure de distéaryldiméthylammonium, le méthylsulfate de distéaryl-2-hydroxypropylméthylammonium, l'éthylsulfate d'oléylstéaryldiméthylammonium ;
X⁻ est un anion de quaternisation. Il peut par exemple être choisi dans le groupe des halogénures, éthylsulfate, méthylsulfate, acétate, phosphate, carbonate, lactate ;
X⁻ est un anion de quaternisation. Il peut par exemple être choisi dans le groupe des halogénures, méthylsulfate, éthylsulfate, acétate, phosphate, carbonate, lactate.
et X⁻ est un anion de quaternisation choisi dans le groupe des halogénures, méthylsulfate, éthylsulfate, acétate, phosphate, carbonate, lactate, par exemple.Examples of the compound of formula (I) are dimyristyldimethylammonium chloride, distearyldimethylammonium chloride, distearyl-2-hydroxypropylmethylammonium methyl sulfate, oleylstearyl dimethylammonium ethyl sulfate;
X⁻ is a quaternization anion. It can, for example, be chosen from the group of halides, ethyl sulphate, methyl sulphate, acetate, phosphate, carbonate, lactate;
X⁻ is a quaternization anion. It can for example be chosen from the group of halides, methylsulfate, ethylsulfate, acetate, phosphate, carbonate, lactate.
and X⁻ is a quaternization anion chosen from the group of halides, methylsulfate, ethylsulfate, acetate, phosphate, carbonate, lactate, for example.
Des exemples de composés de formule (II) sont le méthylsulfate de 1-suif-amidoéthyl-2-suif-imidazolinium,
de 1-méthyl-1--oléylamidoéthyl-2-oléyl-imidazolinium,
1-méthyl-1-palmitoléylamidoéthyl-2-palmitoléyl-imidazolinium,
1-méthyl-1-suif-amidoéthyl-2-suif-imidazolinium,
1-méthyl-1-suif hydrogéné-amidoéthyl-2- suif hydrogénéimidazolinium.Examples of compounds of formula (II) are 1-tallow-amidoethyl-2-tallow-imidazolinium methyl sulfate,
1-methyl-1 - oleylamidoethyl-2-oleyl-imidazolinium,
1-methyl-1-palmitoleylamidoethyl-2-palmitoleyl-imidazolinium,
1-methyl-1-tallow-amidoethyl-2-tallow-imidazolinium,
1-methyl-1-hydrogenated tallow-amidoethyl-2- tallow hydrogenimidazolinium.
Des exemples de composés de formule (III) sont le méthylsulfate de
1-éthylène-bis (2-stéaryl, 1-méthylimidazolinium),
1-éthylène-bis (2-oléyl-1-méthylimidazolinium),
1-éthylène-bis (2-suif-1-méthylimidazolinium).Examples of compounds of formula (III) are methyl sulphate
1-ethylene-bis (2-stearyl, 1-methylimidazolinium),
1-ethylene-bis (2-oleyl-1-methylimidazolinium),
1-ethylene-bis (2-tallow-1-methylimidazolinium).
Des exemples de composés de formule (IV) sont : le méthylsulfate de di(2-suif hydrogéné-amidoéthyl)-hydroxyéthylammonium, de di(2-suif hydrogéné-amidoéthyl)-di-méthylammonium et de méthyl-di(2-palmitylamidoéthyl)-hydroxyéthylammonium.Examples of compounds of formula (IV) are: di (2-hydrogenated tallow-amidoethyl) -hydroxyethylammonium, di (2-hydrogenated tallow-amidoethyl) -di-methylammonium and methyl-di (2-palmitylamidoethyl) methyl sulfate -hydroxyethylammonium.
Les agents B selon l'invention sont en pratique choisis parmi les sels d'ammonium quaternaires et les sels de polyammonium, ces composés contenant éventuellement une seule chaîne alkyl longue en C₈ - C₂₂.The agents B according to the invention are in practice chosen from quaternary ammonium salts and polyammonium salts, these compounds optionally containing a single long C₈ - C₂₂ alkyl chain.
De préférence, les agents B sont choisis parmi des sels de composés mono- ou poly-ammonium quaternaire ou imidazolinium, éventuellement bactéricides ou leur mélange.Preferably, agents B are chosen from salts of mono- or poly-ammonium quaternary or imidazolinium compounds, optionally bactericidal or a mixture thereof.
Les composés cationiques B selon l'invention peuvent être ainsi choisis parmi les composés ayant les formules générales suivantes :
R₁₆ est choisi parmi les groupes alkyle ou alcényle ayant de 8 à 22 atomes de carbone, de préférence de 8 à 10 atomes de carbone, éventuellement ramifiés, éventuellement substitués par des groupes éther, ester ou amide,
R₁₇ est choisi parmi les groupes alkyle ou alcényle ayant de 1 à 4 atomes de carbone, éventuellement ramifiés,
R₁₈ est choisi parmi les groups alkyle ou alcényle ayant de 8 à 18 atomes de carbone, de préférence de 12 à 16 atomes de carbone.
R₁₉ et R₂₀ sont choisis parmi l'hydrogène ou un halogène,
Y⁻ est un anion de quaternisation. Il peut par exemple être choisi dans le groupe des halogénures, méthylsulfate, éthylsulfate, acétate, phosphonate, carbonate, lactate.The cationic compounds B according to the invention can thus be chosen from the compounds having the following general formulas:
R₁₆ is chosen from alkyl or alkenyl groups having from 8 to 22 carbon atoms, preferably from 8 to 10 carbon atoms, optionally branched, optionally substituted by ether, ester or amide groups,
R₁₇ is chosen from alkyl or alkenyl groups having from 1 to 4 carbon atoms, optionally branched,
R₁₈ is chosen from alkyl or alkenyl groups having from 8 to 18 carbon atoms, preferably from 12 to 16 carbon atoms.
R₁₉ and R₂₀ are chosen from hydrogen or halogen,
Y⁻ is a quaternization anion. It can for example be chosen from the group of halides, methylsulfate, ethylsulfate, acetate, phosphonate, carbonate, lactate.
Des exemples d'agents B de formules (V) ou (VI) sont :
le chlorure de lauryldiméthylbenzylammonium, le chlorure d'alkyldiméthylbenzylammonium dans lequel le radical alkyle est en C₁₂ - C₁₈, le chlorure de triméthyldodécylbenzylammonium, le chlorure de méthyl-bis(2-hydroxyéthyl)-oléylammonium, le méthysulfate de méthyl-1-capryl-2-caprylamido-3-éthyl-imidazolinium.Examples of agents B of formulas (V) or (VI) are:
lauryldimethylbenzylammonium chloride, alkyldimethylbenzylammonium chloride in which the alkyl radical is C₁₂ - C₁₈, trimethyldodecylbenzylammonium chloride, methyl-bis (2-hydroxyethyl) -oleylammonium chloride, methyl-1-capryl-2 methysulfate -caprylamido-3-ethyl-imidazolinium.
Les composés cationiques B peuvent aussi être choisis parmi les composés ayant la formule générale suivant :
R₂₂ est choisi parmi les groupes H, alkyle, hydroxyalkyle hydroxyalcoxy en C₁ - C₄,
n est un nombre entier de 1 à 6,
m est un nombre entier de 1 à 5,
X⁻ est un anion de quaternisation. Il peut par exemple être choisi dans le groupe des halogénures, méthylsulfate, éthylsulfate, acétate, phosphate, carbonate, lactate.The cationic compounds B can also be chosen from the compounds having the following general formula:
R₂₂ is chosen from groups H, alkyl, hydroxyalkyl hydroxyalkoxy in C₁ - C₄,
n is an integer from 1 to 6,
m is an integer from 1 to 5,
X⁻ is a quaternization anion. It can for example be chosen from the group of halides, methylsulfate, ethylsulfate, acetate, phosphate, carbonate, lactate.
Des exemples d'agents B de formule (VII) sont :
le diméthosulfate de N-(dérivé de suif)-N,N,N¹,N¹-tétraméthyl-1,3-propanediammonium,
le diméthosulfate de N-(dérivé de suif)-N,N¹,N¹-triméthyl-1,3-propanediammonium,
le diméthosulfate de N-oléyl-N,N,N¹,N¹,N¹-pentaméthyl-1,3-propanediammonium,
le diméthosulfate de N-(dérivé de suif)-N,N,N¹,N¹,N¹-pentaméthyl-1,3-propanediammonium,
le diméthosulfate de N-stéaryl-N,N,N¹,N¹,N¹-pentaméthyl-1,3-propanediammonium,
le diacétate de N-stéaryloxypropyl-N,N¹,N¹-tri(3-hydroxypropyl)-1,3- propane-diammonium.Examples of agents B of formula (VII) are:
N- (tallow derivative) dimethosulfate -N, N, N¹, N¹-tetramethyl-1,3-propanediammonium,
N- (tallow derivative) dimethosulfate -N, N¹, N¹-trimethyl-1,3-propanediammonium,
N-oleyl-N, N, N¹, N¹, N¹-pentamethyl-1,3-propanediammonium dimethosulfate,
N- (tallow derivative) dimethosulfate -N, N, N¹, N¹, N¹-pentamethyl-1,3-propanediammonium,
N-stearyl-N, N, N¹, N¹, N¹-pentamethyl-1,3-propanediammonium dimethosulfate,
N-stearyloxypropyl-N, N¹, N¹-tri (3-hydroxypropyl) -1,3-propane-diammonium diacetate.
Les agents B préférés selon l'invention sont le chlorure de coco-bis(2-hydroxyéthyl)méthylammonium, par exemple l'ETHOQUAD O/12, contenant 25 % d'isopropanol et fabriqué par AKZO ou le chlorure d'oléylbis(2-hydroxyéthyl)méthylammonium, par exemple l'ETHOQUAD 0/12, contenant 25 % d'isopropanol et fabriqué par AKZO.The preferred agents B according to the invention are coco-bis (2-hydroxyethyl) methylammonium chloride, for example ETHOQUAD O / 12, containing 25% isopropanol and manufactured by AKZO or oleylbis chloride (2- hydroxyethyl) methylammonium, for example ETHOQUAD 0/12, containing 25% isopropanol and manufactured by AKZO.
Les composés B selon l'invention peuvent aussi être choisis parmi les composés ayant les formules générales (II), (III) et (IV), mentionnées ci-dessus, dans lesquelles R₅ et R₈, R₉ et R₁₂, R₁₃ et R₁₅ sont choisis parmi les groupes alkyle ou alcényle en C₆ - C₁₄, éventuellement ramifiés.The compounds B according to the invention can also be chosen from the compounds having the general formulas (II), (III) and (IV), mentioned above, in which R₅ and R₈, R₉ and R₁₂, R₁₃ and R₁₅ are chosen among the C₆ - C₁₄ alkyl or alkenyl groups, optionally branched.
Les solvants C selon l'invention peuvent être choisis parmi les solvants hydroxylés ou leurs mélanges, par exemple les alcools, polyols, éthers de polyols, polyéthers de polyols ; les solvants préférés sont l'isopropanol, l'isobutanol, le n-propanol, le méthyl-2-pentanediol-2,4, le 1,2-propylèneglycol et l'éther monométhylique de monopropylèneglycol.The solvents C according to the invention can be chosen from hydroxylated solvents or their mixtures, for example alcohols, polyols, polyol ethers, polyether polyols; the preferred solvents are isopropanol, isobutanol, n-propanol, methyl-2-pentanediol-2,4, 1,2-propylene glycol and the monomethyl ether of monopropylene glycol.
Selon un mode de réalisation préféré de l'invention, l'agent adoucissant est le méthosulfate de l-oléylamidoéthyl-2-oléylimidazolinium, par exemple en solution dans l'isopropanol ou en solution dans le 1,2-propylèneglycol à 75 % d'adoucissant et 25 % d'alcool.According to a preferred embodiment of the invention, the softening agent is 1-oleylamidoethyl-2-oleylimidazolinium methosulfate, for example in solution in isopropanol or in solution in 1,2-propylene glycol at 75% softener and 25% alcohol.
De tels composés préférés sont mis sur le marché par REWO sous les dénominations commerciales REWOQUAT W 3690 et REWOQUAT W 3690/PG.Such preferred compounds are marketed by REWO under the trade names REWOQUAT W 3690 and REWOQUAT W 3690 / PG.
Un autre composé préféré est le chlorure de disuif-2-hydroxypropylméthylammonium vendu sous le nom de PRAEPAGEN WKL par HOECHST.Another preferred compound is disuif-2-hydroxypropylmethylammonium chloride sold under the name of PRAEPAGEN WKL by HOECHST.
Sans vouloir être lié par une quelconque théorie, on pense que le composant B permet, en combinaison avec le solvant C, de fluidifier et de rendre limpide la composition ; en outre l'apport de composant B permet de réduire la teneur en solvant C, mais dans une certaine mesure seulement, car une trop grande proportion de composant B exercerait un effet non souhaité d'abaissement de la viscosité de la composition diluée.Without wishing to be bound by any theory, it is believed that component B makes it possible, in combination with solvent C, to thin and make the composition clear; moreover, the addition of component B makes it possible to reduce the content of solvent C, but only to a certain extent, since too large a proportion of component B would exert an undesired effect of lowering the viscosity of the diluted composition.
Pour la préparation des compositions selon l'invention, il convient simplement :
- dans le cas d'ingrédients liquides à température ambiante, de mélanger ceux-ci à froid dans un ordre quelconque,
- dans le cas où l'un des ingrédients n'est pas liquide à la température ambiante, de chauffer cet ingrédient pour le faire fondre et d'ajouter à la masse fondue obtenue les autres ingrédients, en respectant les précautions d'usage, et en ajoutant de préférence en premier le solvant C et en dernier l'eau.For the preparation of the compositions according to the invention, it is simply suitable:
- in the case of ingredients that are liquid at room temperature, mix them cold in any order,
- if one of the ingredients is not liquid at room temperature, heat this ingredient to make it melt and add the other ingredients to the resulting melt, observing the usual precautions, and preferably adding solvent C first and water last.
L'invention permet de réaliser les objectifs évoqués plus haut.The invention makes it possible to achieve the objectives mentioned above.
Les compositions diluées, visqueuses et stables, que la présente invention permet d'obtenir peuvent être préparées par dilution avec de l'eau de ville, même froide, des compositions concentrées susdites ; le rapport de dilution est de préférence de 1:2 à 1:10, avantageusement de 1:4 pour une composition concentrée à environ 20 % de matière active cationique assouplissante A.The dilute, viscous and stable compositions which the present invention makes it possible to obtain can be prepared by dilution with tap water, even cold, of the above-mentioned concentrated compositions; the dilution ratio is preferably from 1: 2 to 1:10, advantageously from 1: 4 for a composition concentrated at around 20% of cationic softening active material A.
Les compositions selon l'invention, utilisées en des quantités appropriées dans le dernier cycle de rinçage suivant le lavage de charges de linge en machine à laver domestique procurent un assouplissement tout-à-fait convenable au linge.The compositions according to the invention, used in appropriate quantities in the last rinsing cycle following the washing of loads of laundry in a domestic washing machine provide a completely suitable softening for the laundry.
L'invention est décrite plus en détail dans les exemples ci-après, qui ne la limitent aucunement. Dans ces exemples, tous les pourcentages sont donnés en poids sur le poids de la composition totale. Les pourcentages indiqués se réfèrent à la matière active, sans tenir compte des solvants présents habituellement dans les produits commerciaux les contenant.The invention is described in more detail in the examples below, which do not limit it in any way. In these examples, all the percentages are given by weight on the weight of the total composition. The percentages indicated refer to the active ingredient, without taking into account the solvents usually present in the commercial products containing them.
On réalise la composition suivante :
DSIM-MS(*) 20 %
LDMBAC (**) 0 %
Isopropanol 14 %
Parfum 1 %
Eau q.s.p. 100 %
On obtient un gel instable.The following composition is produced:
DSIM-MS (*) 20%
LDMBAC (**) 0%
Isopropanol 14%
Perfume 1%
Water qs 100%
An unstable gel is obtained.
(*) DSIM-MS : méthylsulfate de 1-suif-amidoéthyl-2-suif-imidazolinium.(*) DSIM-MS: 1-tallow-amidoethyl-2-tallow-imidazolinium methyl sulfate.
(**) LDMBAC : chlorure de lauryldiméthylbenzylammonium.(**) LDMBAC: lauryldimethylbenzylammonium chloride.
On réalise par mélange la composition suivante :
Agent A : DSHPMAC (*) 18,35 %
Agent B : ODHMAC (**) 1,65 %
Solvant C : Isopropanol 15 %
Parfum 0,77 %
Colorant (solution à 1 %) 0,6 %
Eau q.s.p. 100 %The following composition is produced by mixing:
Agent A: DSHPMAC (*) 18.35%
Agent B: ODHMAC (**) 1.65%
Solvent C: Isopropanol 15%
Perfume 0.77%
Dye (1% solution) 0.6%
Water qs 100%
(*) chlorure de di-suif-2-hydroxypropylméthylammonium commercialisé sous la dénomination PRAEPAGEN WKL par la Société HOECHST.(*) di-tallow-2-hydroxypropylmethylammonium chloride marketed under the name PRAEPAGEN WKL by the company HOECHST.
(**) chlorure d'oléyl-bis(2-hydroxyéthyl)-méthylammonium, commercialisé sous la dénomination ETHOQUAD 0/12 par la Société AKZO.(**) oleyl-bis (2-hydroxyethyl) -methylammonium chloride, marketed under the name ETHOQUAD 0/12 by the company AKZO.
La composition obtenue est fluide et limpide. Sa viscosité (mesurée au viscosimètre Brookfield, mobile 1, à 6 tours/minute) est de 35 mpa.s. Après addition à cette composition de trois fois son volume d'eau du robinet, on obtient une composition diluée dont la viscosité (mesurée dans les mêmes conditions) est de 210 mpa.s après 1 semaine et de 480 mpa.s après 2 mois.The composition obtained is fluid and clear. Its viscosity (measured with the Brookfield viscometer, mobile 1, at 6 revolutions / minute) is 35 mpa.s. After adding three times its volume of tap water to this composition, a diluted composition is obtained whose viscosity (measured under the same conditions) is 210 mpa.s after 1 week and 480 mpa.s after 2 months.
La composition concentrée est stable à la température ambiante et à 40°C pendant plus d'un an. A-15°C la composition concentrée prend la consistance d'un gel, mais qui est assex fluide et qui disparaît pour redonner une composition complétement fluide après retour à la température ambiante.The concentrated composition is stable at room temperature and at 40 ° C for more than a year. At -15 ° C the concentrated composition takes the consistency of a gel, but which is assex fluid and which disappears to give a completely fluid composition after returning to room temperature.
On prépare par mélange la composition suivante :
DSHPMAC 20 %
ODHMAC 2,04 %
Isopropanol 7,10 %
Dispropylèneglycol 18 %
Parfum 0,97 %
Colorant (solution à 1%) 0,6 %
Eau q.s.p. 100 %
La composition ainsi obtenue est fluide et limpide. Elle est stable et présente une viscosité (mesurée au viscosimètre Brookfield, mobile 2, à 12 tours/minute) de 50 mpa.s après 1 jour et la même encore après 1 mois.The following composition is prepared by mixing:
DSHPMAC 20%
ODHMAC 2.04%
Isopropanol 7.10%
Dispropylene glycol 18%
Perfume 0.97%
Dye (1% solution) 0.6%
Water qs 100%
The composition thus obtained is fluid and clear. It is stable and has a viscosity (measured with a Brookfield viscometer, mobile 2, at 12 revolutions / minute) of 50 mpa.s after 1 day and the same again after 1 month.
Après addition à cette composition de trois fois son volume d'eau du robinet, on obtient une composition diluée, stable, dont la viscosité (mesurée au viscosimètre Brookfield, mobile 1, à 6 tours/minute) est de 203 mpa.s après 1 jour et de 486 mpa.s après 1 mois.After adding three times its volume of tap water to this composition, a dilute, stable composition is obtained, the viscosity (measured with a Brookfield viscometer, mobile 1, at 6 revolutions / minute) is 203 mpa.s after 1 day and 486 mpa.s after 1 month.
On prépare par mélange la composition suivante :
DSHPMAC 20 %
ODHMAC 2,04 %
Isopropanol 7,10 %
Ether monométhylique de monopropylèneglycol 14 %
Parfum 0,97 %
Colorant (solution à 1%) 0,6 %
Eau q.s.p. 100 %
La composition obtenue est fluide et limpide. Elle est stable et présente une viscosité (mesurée au viscosimètre Brookfield, mobile 2, à 12 tours/minute) de 40 mpa.s après 1 jour et de 30 mpa.s après 1 mois. Après addition à cette composition de trois fois son volume d'eau du robinet, on obtient une composition diluée stable, dont la viscosité (mesurée au viscosimètre Brookfield, mobile 1, à 6 tours/minute) est de 549 mpa.s après 1 jour et de 900 mpa.s après 1 mois.The following composition is prepared by mixing:
DSHPMAC 20%
ODHMAC 2.04%
Isopropanol 7.10%
Monopropylene glycol monomethyl ether 14%
Perfume 0.97%
Dye (1% solution) 0.6%
Water qs 100%
The composition obtained is fluid and clear. It is stable and has a viscosity (measured with a Brookfield viscometer, mobile 2, at 12 revolutions / minute) of 40 mpa.s after 1 day and 30 mpa.s after 1 month. After adding three times its volume of tap water to this composition, a stable dilute composition is obtained, the viscosity (measured with a Brookfield viscometer, mobile 1, at 6 revolutions / minute) is 549 mpa.s after 1 day and 900 mpa.s after 1 month.
On prépare par mélange la composition suivante :
DOIMMS (*) 50 %
ODHMAC 10 %
Isopropanol 3,34 %
Parfum 0,97 %
Colorant (solution à 1%) 0,8 %
Eau q.s.p. 100 %The following composition is prepared by mixing:
DOIMMS (*) 50%
ODHMAC 10%
Isopropanol 3.34%
Perfume 0.97%
Dye (1% solution) 0.8%
Water qs 100%
(*) méthosulfate de 1-oléylamidoéthyl-2-oléylimidazolinium commercialisé sous la dénomination REWOQUAT W-3690 par la Société REWO.(*) 1-oleylamidoethyl-2-oleylimidazolinium methosulfate sold under the name REWOQUAT W-3690 by the company REWO.
La composition obtenue est fluide et limpide. Sa viscosité (mesurée au viscosimètre Brookfield, mobile 2, à 12 tours/minute) est de 30 mpa.s après 4 jours. Après addition à cette solution de neuf fois son volume d'eau du robinet, on obtient une composition diluée dont la viscosité (mesurée au viscosimètre Brookfield, mobile 1, à 6 tours/minute) est de 132 mpa.s après 4 jours.The composition obtained is fluid and clear. Its viscosity (measured with the Brookfield viscometer, mobile 2, at 12 revolutions / minute) is 30 mpa.s after 4 days. After adding nine times its volume of tap water to this solution, a dilute composition is obtained, the viscosity (measured with a Brookfield viscometer, mobile 1, at 6 revolutions / minute) is 132 mpa.s after 4 days.
On étudie l'influence de la température de l'eau de dilution d'une composition concentrée, sur la viscosité de la composition diluée.The influence of the temperature of the dilution water of a concentrated composition is studied on the viscosity of the diluted composition.
On mélange les composés suivants :
DOIMMS 20 %
ODHMAC 2 %
Isopropanol 20 %
Parfum 1 %
Eau q.s.p. 100 %The following compounds are mixed:
DOIMMS 20%
ODHMAC 2%
Isopropanol 20%
Perfume 1%
Water qs 100%
On dilue cette composition concentrée avec trois fois son volume d'eau. On mesure les viscosités avec un viscosimètre Brookfield, mobile 1, à 6 tours/minute.This concentrated composition is diluted with three times its volume of water. The viscosities are measured with a Brookfield viscometer, mobile 1, at 6 revolutions / minute.
En fonction de la température de l'eau de dilution, on obtient des compositions diluées dont les viscosités sont données dans le tableau 1.
On voit donc que les compositions selon l'invention ont une viscosité supérieure à 100 mPa.s pour des températures d'eau de dilution inférieures à 20°C. Or, une viscosité supérieure à 100 mPa.s, de préférence 100-200 mPa.s, est une viscosité qui est perçue par la ménagère comme l'indice d'un produit efficace.It can therefore be seen that the compositions according to the invention have a viscosity greater than 100 mPa.s for dilution water temperatures below 20 ° C. However, a viscosity greater than 100 mPa.s, preferably 100-200 mPa.s, is a viscosity which is perceived by the housewife as the index of an effective product.
On étudie l'influence du rapport en poids de la quantité d'agent adoucissant A à la quantité de composé cationique non adoucissant B. On réalise les compositions suivantes :
- (A) DOIMMS
- (B) ODHMAC
- (C) Isopropanol
Parfum 1 %
Eau q.s.p. 100 %
- (A) DOIMMS
- (B) ODHMAC
- (C) Isopropanol
Perfume 1%
Water qs 100%
On dilue à l'eau à 20°C ces compositions pour obtenir des compositions diluées contenant 5 % en poids d'agent adoucissant A. On mesure les viscosités des compositions diluées ainsi obtenues, au viscosimètre Brookfield, mobile 1, vitesse 6 tours/minute. On obtient les résultats suivants (cf. tableau 2) :
On étudie, à concentrations égales, l'influence d'un agent non adoucissant cationique dans une composition aqueuse d'agent adoucissant, comparée à l'influence d'un agent non ionique.
- a) On réalise la composition concentrée suivante :
16 % de méthylsulfate de N-méthyl,N,Ndi(bêta-C₁₄-C₁₈ acyloxyéthyl) N-bêta-hydroxyéthylammonium commercialisé sous la dénomination STEPANTEX Q 185 par la société STEPAN EUROPE,
11 % d'alcool isopropylique,
4 % d'un mélange d'agent de surface non ionique et d'émulsifiant également non ionique,
1 % de parfum,
q.s.p. 100 % d'eau.
La composition obtenue a une viscosité lui permettant d'être versée. Cette composition est diluée avec trois fois son volume d'eau, l'eau étant à 10°C ou 20°C. On obtient alors une composition diluée qui forme des grumeaux et dont la viscosité est très élevée :
> 1000 mPa.s (mesurée au viscosimètre Brookfield, mobile no 1,6 tours/ minute). - b) On réalise la composition concentrée suivante :
16 % de DOIMMS,
4 % d'ODHMAC,
11 % d'isopropanol,
1 % de parfum,
q.s.p. 100 % d'eau. On dilue cette composition avec trois fois son volume d'eau, la température de l'eau de dilution étant de 10°C. La viscosité de la composition diluée est de 10 mPa.s (mesurée de la même manière que pour l'exemple 4a).
- a) The following concentrated composition is produced:
16% of N-methyl methylsulfate, N, Ndi (beta-C₁₄-C₁₈ acyloxyethyl) N-beta-hydroxyethylammonium sold under the name STEPANTEX Q 185 by the company STEPAN EUROPE,
11% isopropyl alcohol,
4% of a mixture of nonionic surfactant and also nonionic emulsifier,
1% perfume,
qs 100% water.
The composition obtained has a viscosity allowing it to be poured. This composition is diluted with three times its volume of water, the water being at 10 ° C or 20 ° C. A diluted composition is then obtained which forms lumps and whose viscosity is very high:
> 1000 mPa.s (measured using a Brookfield viscometer, No. mobile 1.6 revolutions / minute). - b) The following concentrated composition is produced:
16% of DOIMMS,
4% ODHMAC,
11% isopropanol,
1% perfume,
qs 100% water. This composition is diluted with three times its volume of water, the temperature of the dilution water being 10 ° C. The viscosity of the diluted composition is 10 mPa.s (measured in the same way as for Example 4a).
On voit donc que la fonction technique de l'agent cationique non adoucissant est différente de la fonction technique de l'agent non ionique. Selon la quantité d'agent cationique non adoucissant dans la composition concentrée, on peut régler la viscosité de la composition diluée à une valeur acceptable pour la ménagère. (comprise de préférence entre 50 et 900 mPa.s).It can therefore be seen that the technical function of the non-softening cationic agent is different from the technical function of the nonionic agent. Depending on the amount of non-softening cationic agent in the concentrated composition, the viscosity of the diluted composition can be adjusted to a value acceptable to the housewife. (preferably between 50 and 900 mPa.s).
En effet les exemples 3b et 4b montrent que, pour une composition contenant environ 15 % d'agent adoucissant A et 0,1 % d'agent non adoucissant B, la viscosité de la composition diluée est de 160 mPa.s, alors que pour une composition contenant 4 % d'agent non adoucissant B, la viscosité de la composition diluée est de 10 mPa.s.Indeed, Examples 3b and 4b show that, for a composition containing approximately 15% of softening agent A and 0.1% of non-softening agent B, the viscosity of the diluted composition is 160 mPa.s, while for a composition containing 4% of non-softening agent B, the viscosity of the diluted composition is 10 mPa.s.
En outre, lorsqu'on disperse dans de l'eau froide les compositions diluées 4a et 4b obtenues à partir des compositions concentrées, on voit que la composition diluée 4a se disperse très difficilement et qu'il faut agiter à la main pendant quelques dizaines de secondes pour obtenir une bonne dispersion dans l'eau. Au contraire, la composition diluée 4b se disperse très facilement dans de l'eau à 10°C (en moins de 5 secondes).In addition, when the diluted compositions 4a and 4b obtained from the concentrated compositions are dispersed in cold water, it is seen that the diluted composition 4a is very difficult to disperse and that it is necessary to shake by hand for several tens of seconds to obtain good dispersion in water. On the contrary, the diluted composition 4b disperses very easily in water at 10 ° C (in less than 5 seconds).
On prépare la composition suivante :
20 % de DSHPM-AC,
2 % de ODHMAC,
13 % de 1,2-propylèneglycol,
11 % d'isopropanol
1 % de parfum,
q.s.p. 100 % d'eau
On dilue cette composition avec trois fois son volume d'eau. La température de l'eau de dilution est de 10°C.
On obtient une composition diluée, stable, dont la viscosité, mesurée de la même manière que dans les exemples précédents, est de 260 mPa.s.The following composition is prepared:
20% of DSHPM-AC,
2% ODHMAC,
13% of 1,2-propylene glycol,
11% isopropanol
1% perfume,
qs 100% water
This composition is diluted with three times its volume of water. The temperature of the dilution water is 10 ° C.
A dilute, stable composition is obtained, the viscosity of which, measured in the same manner as in the previous examples, is 260 mPa.s.
Claims (14)
R₃ et R₄ peuvent être semblables ou différents et sont choisis parmi les groupes alkyle en C₁ à C₃, les groupes benzyle, éventuellement substitués, ou les groupes -(CnH2nO)x H dans lesquels n = 2 ou 3, x = 1 à 5, X⁻ étant un anion de quaternisation ;
X⁻ est un anion ayant la même signification que dans la formule (I),
X⁻ est un anion ayant la même signification que dans la formule (I),
R₁₄ est choisi dans le groupe formé par H, les radicaux méthyle, éthyle et -(CnH2nO)x H, dans lequel n est égal à 2 ou 3 et x est compris entre 1 et 5,
et X⁻ est un anion ayant la même signification que dans la formule (I).4 - Composition according to any one of claims 1 to 3, characterized in that the softening agents A are chosen from the compounds having the following general formulas:
R₃ and R₄ may be the same or different and are chosen from C₁ to C₃ alkyl groups, benzyl groups, optionally substituted, or - (C n H 2n O) x H groups in which n = 2 or 3, x = 1 to 5, X⁻ being a quaternization anion;
X⁻ is an anion having the same meaning as in formula (I),
X⁻ is an anion having the same meaning as in formula (I),
R₁₄ is chosen from the group formed by H, the methyl, ethyl and - (C n H 2n O) x H radicals, in which n is equal to 2 or 3 and x is between 1 and 5,
and X⁻ is an anion having the same meaning as in formula (I).
R₁₆ est choisi parmi les groupes alkyle ou alcényle ayant de 8 à 22 atomes de carbone, de préférence de 8 à 10 atomes de carbone, éventuellement ramifiés, éventuellement substitués par des groupes éther, ester ou amide,
R₁₇ est choisi parmi les groupes alkyle ou alcényle ayant de 1 à 4 atomes de carbone, éventuellement ramifiés,
R₁₈ est choisi parmi les groupe alkyle ou alcényle ayant de 8 à 12 atomes de carbone, de préférence de 12 à 16 atomes de carbone,
R₁₉ et R₂₀ sont choisis parmi l'hydrogène ou un halogène,
Y⁻ est un anion ayant la même signification que X⁻ dans la formule (I),
R₂₂ est choisi parmi les groupes H, alkyle, hydroxyalkyle, hydroxyalcoxy en C₁-C₄,
n est un nombre entier de 1 à 6,
m est un nombre entier de 1 à 5,
X⁻ est un anion ayant la même signification que dans la formule (I).9 - Composition according to any one of Claims 1 to 8, characterized in that the agent B is chosen from the compounds of the following general formulas:
R₁₆ is chosen from alkyl or alkenyl groups having from 8 to 22 carbon atoms, preferably from 8 to 10 carbon atoms, optionally branched, optionally substituted by ether, ester or amide groups,
R₁₇ is chosen from alkyl or alkenyl groups having from 1 to 4 carbon atoms, optionally branched,
R₁₈ is chosen from alkyl or alkenyl groups having from 8 to 12 carbon atoms, preferably from 12 to 16 carbon atoms,
R₁₉ and R₂₀ are chosen from hydrogen or halogen,
Y⁻ is an anion having the same meaning as X⁻ in formula (I),
R₂₂ is chosen from H, alkyl, hydroxyalkyl, C hydroxy-C₄ hydroxyalkoxy groups,
n is an integer from 1 to 6,
m is an integer from 1 to 5,
X⁻ is an anion having the same meaning as in formula (I).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT8888420204T ATE105331T1 (en) | 1987-06-16 | 1988-06-16 | CONCENTRATED PLASTICIZERS. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8708378 | 1987-06-16 | ||
| FR8708378 | 1987-06-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0296995A1 true EP0296995A1 (en) | 1988-12-28 |
| EP0296995B1 EP0296995B1 (en) | 1994-05-04 |
Family
ID=9352098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP88420204A Expired - Lifetime EP0296995B1 (en) | 1987-06-16 | 1988-06-16 | Concentrated softening compositions |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0296995B1 (en) |
| JP (1) | JPH01501492A (en) |
| AT (1) | ATE105331T1 (en) |
| AU (1) | AU623859B2 (en) |
| DE (1) | DE3889387D1 (en) |
| WO (1) | WO1988010294A1 (en) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0413249A1 (en) * | 1989-08-12 | 1991-02-20 | Witco Surfactants GmbH | Fabric softener |
| EP0503155A1 (en) * | 1991-03-13 | 1992-09-16 | Witco Surfactants GmbH | Fabric softener based on quaternary poly(oxyalkylene)-alkanolamine esters |
| EP0536444A1 (en) * | 1991-10-07 | 1993-04-14 | The Procter & Gamble Company | Stable concentrated perfume emulsion |
| EP0637625A1 (en) * | 1993-08-02 | 1995-02-08 | The Procter & Gamble Company | Super concentrate emulsions with fabric actives |
| EP0648835A1 (en) * | 1993-10-14 | 1995-04-19 | The Procter & Gamble Company | Use of alkaline polyammonium salts to increase cationic density in fabric softeners |
| WO1997003170A1 (en) * | 1995-07-11 | 1997-01-30 | The Procter & Gamble Company | Concentrated, water dispersible, stable, fabric softening compositions |
| WO1997003169A1 (en) * | 1995-07-11 | 1997-01-30 | The Procter & Gamble Company | Concentrated, stable fabric softening composition |
| WO1997034972A1 (en) * | 1996-03-22 | 1997-09-25 | The Procter & Gamble Company | Fabric softening compound/composition |
| WO1998002513A1 (en) * | 1996-07-11 | 1998-01-22 | The Procter & Gamble Company | Substantially odor-free polyhydroxyl solvents |
| WO1998003619A1 (en) * | 1996-07-19 | 1998-01-29 | The Procter & Gamble Company | Concentrated fabric softening composition and highly unsaturated fabric softener compound therefor |
| WO1998017756A1 (en) * | 1996-10-21 | 1998-04-30 | The Procter & Gamble Company | Concentrated fabric softening composition |
| WO1999006509A1 (en) * | 1997-07-29 | 1999-02-11 | The Procter & Gamble Company | Concentrated, stable, preferably clear, fabric softening composition containing amine fabric softener |
| US6323172B1 (en) * | 1996-03-22 | 2001-11-27 | The Procter & Gamble Company | Concentrated, stable fabric softening composition |
| EP1352948A1 (en) * | 1995-07-11 | 2003-10-15 | The Procter & Gamble Company | Concentrated, stable, fabric softening composition |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4203489A1 (en) * | 1992-02-07 | 1993-08-12 | Henkel Kgaa | METHOD FOR PRODUCING LOW-VISCUS AQUEOUS ESTERQUAT CONCENTRATES |
| GB9301811D0 (en) * | 1993-01-29 | 1993-03-17 | Unilever Plc | Fabric softener composition |
| US5492636A (en) * | 1994-09-23 | 1996-02-20 | Quest International Fragrances Company | Clear concentrated fabric softener |
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|---|---|---|---|---|
| GB1165007A (en) * | 1966-10-19 | 1969-09-24 | Millmaster Onyx Corp | Stabilized Quaternary Ammonium Compositions |
| FR2295122A1 (en) * | 1974-12-16 | 1976-07-16 | Hoechst Ag | COMPOSITION OF SOFTENERS FOR TEXTILE MATERIALS |
| EP0059502A1 (en) * | 1981-02-28 | 1982-09-08 | THE PROCTER & GAMBLE COMPANY | Textile treatment compositions |
| EP0060003A2 (en) * | 1981-03-07 | 1982-09-15 | THE PROCTER & GAMBLE COMPANY | Textile treatment compositions and preparation thereof |
| FR2523606A1 (en) * | 1982-03-22 | 1983-09-23 | Colgate Palmolive Co | CONCENTRATED SOFTENING COMPOSITIONS FOR FABRICS BASED ON QUATERNARY IMIDAZOLINE DERIVATIVES |
| EP0165138A2 (en) * | 1984-05-16 | 1985-12-18 | STEPAN EUROPE, Société anonyme dite: | Concentrated softening compositions based on quaterny ammonium-containing cationic surfactants |
| EP0199382A2 (en) * | 1985-03-28 | 1986-10-29 | The Procter & Gamble Company | Liquid fabric softener |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4442013A (en) * | 1982-03-22 | 1984-04-10 | Colgate-Palmolive Company | Concentrated fabric softening compositions |
-
1988
- 1988-06-16 JP JP63505451A patent/JPH01501492A/en active Pending
- 1988-06-16 AU AU19625/88A patent/AU623859B2/en not_active Ceased
- 1988-06-16 EP EP88420204A patent/EP0296995B1/en not_active Expired - Lifetime
- 1988-06-16 WO PCT/FR1988/000318 patent/WO1988010294A1/en unknown
- 1988-06-16 AT AT8888420204T patent/ATE105331T1/en not_active IP Right Cessation
- 1988-06-16 DE DE3889387T patent/DE3889387D1/en not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1165007A (en) * | 1966-10-19 | 1969-09-24 | Millmaster Onyx Corp | Stabilized Quaternary Ammonium Compositions |
| FR2295122A1 (en) * | 1974-12-16 | 1976-07-16 | Hoechst Ag | COMPOSITION OF SOFTENERS FOR TEXTILE MATERIALS |
| EP0059502A1 (en) * | 1981-02-28 | 1982-09-08 | THE PROCTER & GAMBLE COMPANY | Textile treatment compositions |
| EP0060003A2 (en) * | 1981-03-07 | 1982-09-15 | THE PROCTER & GAMBLE COMPANY | Textile treatment compositions and preparation thereof |
| FR2523606A1 (en) * | 1982-03-22 | 1983-09-23 | Colgate Palmolive Co | CONCENTRATED SOFTENING COMPOSITIONS FOR FABRICS BASED ON QUATERNARY IMIDAZOLINE DERIVATIVES |
| EP0165138A2 (en) * | 1984-05-16 | 1985-12-18 | STEPAN EUROPE, Société anonyme dite: | Concentrated softening compositions based on quaterny ammonium-containing cationic surfactants |
| EP0199382A2 (en) * | 1985-03-28 | 1986-10-29 | The Procter & Gamble Company | Liquid fabric softener |
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0413249A1 (en) * | 1989-08-12 | 1991-02-20 | Witco Surfactants GmbH | Fabric softener |
| US5180508A (en) * | 1989-08-12 | 1993-01-19 | Rewo Chemische Werke Gmbh | Fabric softener rinsing agents |
| US5364542A (en) * | 1989-08-12 | 1994-11-15 | Rewo Chemische Werke Gmbh | Fabric softener rinsing agents |
| EP0503155A1 (en) * | 1991-03-13 | 1992-09-16 | Witco Surfactants GmbH | Fabric softener based on quaternary poly(oxyalkylene)-alkanolamine esters |
| EP0536444A1 (en) * | 1991-10-07 | 1993-04-14 | The Procter & Gamble Company | Stable concentrated perfume emulsion |
| EP0637625A1 (en) * | 1993-08-02 | 1995-02-08 | The Procter & Gamble Company | Super concentrate emulsions with fabric actives |
| EP0648835A1 (en) * | 1993-10-14 | 1995-04-19 | The Procter & Gamble Company | Use of alkaline polyammonium salts to increase cationic density in fabric softeners |
| WO1997003170A1 (en) * | 1995-07-11 | 1997-01-30 | The Procter & Gamble Company | Concentrated, water dispersible, stable, fabric softening compositions |
| WO1997003169A1 (en) * | 1995-07-11 | 1997-01-30 | The Procter & Gamble Company | Concentrated, stable fabric softening composition |
| WO1997003172A1 (en) * | 1995-07-11 | 1997-01-30 | The Procter & Gamble Company | Concentrated, stable fabric softening compositions including chelants |
| US6369025B1 (en) | 1995-07-11 | 2002-04-09 | The Procter & Gamble Company | Concentrated, water dispersible, stable, fabric softening compositions |
| EP1352948A1 (en) * | 1995-07-11 | 2003-10-15 | The Procter & Gamble Company | Concentrated, stable, fabric softening composition |
| CN1110541C (en) * | 1995-07-11 | 2003-06-04 | 普罗格特-甘布尔公司 | Concentrated, water dispersible, stable, fabric softening compositions |
| WO1997034972A1 (en) * | 1996-03-22 | 1997-09-25 | The Procter & Gamble Company | Fabric softening compound/composition |
| US6323172B1 (en) * | 1996-03-22 | 2001-11-27 | The Procter & Gamble Company | Concentrated, stable fabric softening composition |
| WO1998002513A1 (en) * | 1996-07-11 | 1998-01-22 | The Procter & Gamble Company | Substantially odor-free polyhydroxyl solvents |
| WO1998003619A1 (en) * | 1996-07-19 | 1998-01-29 | The Procter & Gamble Company | Concentrated fabric softening composition and highly unsaturated fabric softener compound therefor |
| US6335315B1 (en) | 1996-10-21 | 2002-01-01 | The Procter & Gamble Company | Concentrated fabric softening composition |
| WO1998017756A1 (en) * | 1996-10-21 | 1998-04-30 | The Procter & Gamble Company | Concentrated fabric softening composition |
| US6686331B2 (en) | 1996-10-21 | 2004-02-03 | The Procter & Gamble Company | Concentrated, stable, preferably clear, fabric softening composition |
| WO1999006509A1 (en) * | 1997-07-29 | 1999-02-11 | The Procter & Gamble Company | Concentrated, stable, preferably clear, fabric softening composition containing amine fabric softener |
| US6630441B2 (en) | 1997-07-29 | 2003-10-07 | The Procter & Gamble Company | Concentrated, stable, preferably clear, fabric softening composition containing amine fabric softener |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE105331T1 (en) | 1994-05-15 |
| JPH01501492A (en) | 1989-05-25 |
| AU623859B2 (en) | 1992-05-28 |
| AU1962588A (en) | 1989-01-19 |
| WO1988010294A1 (en) | 1988-12-29 |
| EP0296995B1 (en) | 1994-05-04 |
| DE3889387D1 (en) | 1994-06-09 |
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