FR2688419A1 - Surface-active base including a quaternary ammonium cationic compound and a compound as solvent and softening composition including such a base - Google Patents

Surface-active base including a quaternary ammonium cationic compound and a compound as solvent and softening composition including such a base Download PDF

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Publication number
FR2688419A1
FR2688419A1 FR9203199A FR9203199A FR2688419A1 FR 2688419 A1 FR2688419 A1 FR 2688419A1 FR 9203199 A FR9203199 A FR 9203199A FR 9203199 A FR9203199 A FR 9203199A FR 2688419 A1 FR2688419 A1 FR 2688419A1
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sep
equal
compound
base according
base
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FR2688419B1 (en
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Contet Jean-Pierre
Courdavault Duprat Stephane
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Stepan Europe SAS
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Stepan Europe SAS
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Priority to EP92420488A priority patent/EP0550361B1/en
Priority to AT92420488T priority patent/ATE144245T1/en
Priority to ES92420488T priority patent/ES2094893T3/en
Priority to DE69214618T priority patent/DE69214618T2/en
Publication of FR2688419A1 publication Critical patent/FR2688419A1/en
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Publication of FR2688419B1 publication Critical patent/FR2688419B1/en
Priority to US08/447,219 priority patent/US5637743A/en
Priority to US08/872,357 priority patent/US5750492A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/38—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/16—Amines or polyamines
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50—Modified hand or grip properties; Softening compositions

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Textile Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

A surface-active base including at least one quaternary ammonium cationic compound corresponding to the following formula I: in which: - each of Y1, Y1', Y2, Y2', Y3, Y3' is an oxy, N or NH group, - R1, R2, R3 and R4 are hydrocarbon chains and, as solvent, at least one compound corresponding to the following formula II: in which: - R5 is a hydrocarbon chain - E is a or functional group - m and j are integers - each of i and k is an integer or zero - d is equal to 0, 1 o etc..

Description

Base tensioactive comprenant un composé cationique
a |ammonium quaternaire et un composé titre de solvant
et composition assouplissante comprenant une telle base
L'invention relève du domaine des agents de surface à pouvoir d'adsorption élevé sur les fibres notamment fibres textiles, cheveux, et plus particulièrement des agents de surface cationiques de la classe des ammoniums quaternaires.Surfactant base comprising a cationic compound
a quaternary ammonium and a solvent title compound
and a softening composition comprising such a base
The invention relates to the field of surfactants with high adsorption capacity on fibers including textile fibers, hair, and more particularly cationic surfactants of the quaternary ammonium class.

L'invention s'intéresse plus spécifiquement à l'application de tels agents en tant qu'adoucissant textile, mais la portée de l'invention n'est nullement limitée à une telle application ; les produits décrits possédant un effet conditionnant vis-à-vis de la plupart des fibres naturelles telles que coton, laine, cheveux, ils sont utilisés dans différents domaines comme agent antistatique, adoucissant et/ou lubrifiant. The invention is more specifically concerned with the application of such agents as a textile softener, but the scope of the invention is in no way limited to such an application; the described products having a conditioning effect vis-à-vis most natural fibers such as cotton, wool, hair, they are used in different fields as antistatic agent, softener and / or lubricant.

Dans la demande de brevet français NO 91 16479 déposée au nom de la Demanderesse, on décrit un composé tensioactif cationique d'ammonium quaternaire répondant à la formule I suivante

Figure img00010001
In the French patent application No. 91 16479 filed in the name of the Applicant, there is described a quaternary ammonium cationic surfactant compound having the following formula I
Figure img00010001

dans laquelle - n, n' n" sont des nombres entiers non nuls - p, q, r, x, y, z sont des nombres entiers ou zéro - rapportée à une mole, la moyenne de la somme de n, n' et
n" est comprise statistiquement entre 4 et 12 - rapportée à une mole, la moyenne de la somme de p, q, r,
x, y et z est comprise statistiquement entre 1 et 4 - rapportée à une mole, la moyenne de la somme de p, q et
r est comprise statistiquement entre 1,85 et 1,40 - Y1, Yi., Y2, Y2', Y3, Y3g, sont des groupes fonctionnels
choisis chacun parmi les groupes oxy, N et NH - R1, R2, R3 sont respectivement une longue chaîne
hydrocarbonée alkyle ou alkényle, ayant de 5 à 23 atomes
de carbone - R4 est une courte chaîne alkyle ayant de 1 à 5 atomes de
carbone, et - X est un contre-ion choisi notamment parmi les
halogénures et les carbonates et sulfates d'alkyle.in which - n, n 'n "are non-zero integers - p, q, r, x, y, z are integers or zero - referred to one mole, the average of the sum of n, n' and
n "is included statistically between 4 and 12 - referred to a mole, the average of the sum of p, q, r,
x, y and z is statistically between 1 and 4 - referred to a mole, the average of the sum of p, q and
r is statistically between 1.85 and 1.40 - Y1, Y1, Y2, Y2 ', Y3, Y3g, are functional groups
each selected from oxy, N and NH - R 1, R 2, R 3 are respectively long chain
alkyl or alkenyl hydrocarbon having from 5 to 23 atoms
carbon - R4 is a short alkyl chain having 1 to 5 carbon atoms
carbon, and - X is a counter-ion chosen especially from
halides and alkyl carbonates and sulfates.

Ces composés présentent une viscosité et un point de fusion élevés les rendant difficilement utilisables en l'état. C'est pourquoi, ils ne peuvent pas être facilement incorporés directement dans une composition assouplissante en l'absence d'un solvant les ayant préalablement dissous, les compositions assouplissantes comprenant au demeurant et en plus des parfums, colorants, azurants, protecteurs... These compounds have a high viscosity and a high melting point rendering them difficult to use as they are. Therefore, they can not be easily incorporated directly into a softening composition in the absence of a solvent having previously dissolved, the softening compositions comprising in addition and in addition to perfumes, dyes, brighteners, protectors ...

Les solvants du composé I couramment utilisés sont choisis parmi les composés polaires ayant un ou plusieurs groupements hydroxyle et notamment parmi les alcools inférieurs tels que méthanol, éthanol, isopropanol, parmi les glycols tels que éthylène-glycol, propylène-glycol, diéthylène-glycol, butyl-, propyl-, éthyl-, méthyl-éther de diméthylène glycol, de diéthylène glycol, de dipropylène glycol, hexylène-glycol. The solvents of compound I currently used are chosen from polar compounds having one or more hydroxyl groups and especially from lower alcohols such as methanol, ethanol, isopropanol, among glycols such as ethylene glycol, propylene glycol, diethylene glycol, butyl-, propyl-, ethyl-, methyl-ether dimethylene glycol, diethylene glycol, dipropylene glycol, hexylene glycol.

Ces solvants présentent l'inconvénient d'abaisser le point éclair des bases assouplissantes rendant leur utilisation dangereuse pour des gammes de températures élevées. These solvents have the disadvantage of lowering the flash point of the softening bases making their use dangerous for high temperature ranges.

En outre, ces solvants n'ont qu'une action de dilution sur le composé I sans apporter de contribution ni au pouvoir adoucissant ou conditionnant du composé I puisqu'aucune interaction avec les fibres ne les retient sur ces dernières et qu'ils ne sont pas suffisamment hydrophobes, ni à son pouvoir antistatique puisqu'ils sont hydrosolubles, ni à son pouvoir lubrifiant puisque leur chaîne carbonée est trop courte. In addition, these solvents only have a dilution action on compound I without making any contribution to the softening or conditioning power of compound I, since no interaction with the fibers keeps them on the latter and they are not not sufficiently hydrophobic, neither its antistatic power since they are water-soluble, nor its lubricating power since their carbon chain is too short.

L'objet de la présente invention est une base tensioactive comprenant au moins un composé répondant à la formule I ci-dessus dans laquelle - Y1, Y1s, Y2, Y2a, Y3, Y3' et R1, R2, R3, R4 et X ont la même
signification que celle donnée ci-dessus, - n, n', n", p, q, r, x, y et z sont tels que définis ci
dessus, - la somme de n, n' et n" étant comprise entre 4 et 12, - la somme de p, q et r étant comprise entre 1 et 3, - et la somme de p, q, r, x, y, z étant comprise entre l
et 4
et au moins un autre composé, à titre de solvant, ce dernier permettant d'apporter en plus de son pouvoir dissolvant, un effet lubrifiant et un effet conditionnant complémentaires de ceux apportés par le composé I.The object of the present invention is a surfactant base comprising at least one compound of formula I above in which Y1, Y1s, Y2, Y2a, Y3, Y3 'and R1, R2, R3, R4 and X have the same
meaning as given above, - n, n ', n ", p, q, r, x, y and z are as defined herein
above, the sum of n, n 'and n "being between 4 and 12, the sum of p, q and r being between 1 and 3, and the sum of p, q, r, x, y z being between l
and 4
and at least one other compound, as a solvent, the latter making it possible to provide, in addition to its dissolving power, a lubricating effect and a conditioning effect complementary to those provided by the compound I.

Selon l'invention, le solvant comprend au moins un composé répondant à la formule II suivante
( - E)m~ Cj H2(j+1)-m-2d+i Ok+i (II)
dans laquelle - Rs est une longue chaîne hydrocarbonée saturée ou
insaturée, ayant de 5 à 23 atomes de carbone - E est une fonction

Figure img00030001

ou
Figure img00030002

- m est un nombre entier compris entre 1 et 8 - j est un nombre entier compris entre 1 et 36 - k est un nombre entier ou zéro - i est un nombre entier ou zéro - d est égal à 0, 1 ou 2.According to the invention, the solvent comprises at least one compound corresponding to the following formula II
(- E) m ~ Cj H2 (j + 1) -m-2d + i Ok + i (II)
in which - Rs is a long saturated hydrocarbon chain or
unsaturated, having 5 to 23 carbon atoms - E is a function
Figure img00030001

or
Figure img00030002

- m is an integer between 1 and 8 - j is an integer between 1 and 36 - k is an integer or zero - i is an integer or zero - d is 0, 1 or 2.

Dans la formule II ci-dessus - k représente le nombre de fonctions éther du composé - i représente le nombre de groupements hydroxyle libre du
composé - et d représente le nombre d'insaturations du composé,
non comprises celles de Rs.In formula II above - k represents the number of ether functions of the compound - i represents the number of free hydroxyl groups of
compound - and d represents the number of unsaturations of the compound,
not including those of Rs.

Selon l'invention, le composé II préférentiel ne comprend pas de groupements hydroxyle libre, c'est-à-dire i est égal à zéro. According to the invention, the preferential compound II does not comprise free hydroxyl groups, that is to say i is equal to zero.

Avantageusement, le composé répondant à la formule II est choisi parmi ceux pour lesquels m est égal à 1, j est compris entre 1 et 18 et de
préférence entre 1 et 4, et k, i et d sont égaux à 0,
c'est-à-dire notamment parmi les esters méthyliques,
éthyliques, propyliques, isopropyliques et butyliques;;
pour des valeurs de m et j égales à 1, R5 est une chaîne
hydrocarbonée ayant de préférence 7 à 17 atomes de
carbone - m est égal à 2, j est compris entre 2 et 12 et est de
préférence égal à 2 ou 3, et k, i et d sont égaux à 0,
c'est-à-dire notamment parmi les diesters d'éthylène
glycol et de propylène glycol - m est égal à 2, j est compris entre 4 et 12, k est égal
à 1, i et d sont égaux à O et Rs est une chaîne
hydrocarbonée ayant 7 ou 9 atomes de carbone, tels que
l'ester de diéthylèneglycol de l'acide caprique ou
caprylique m est égal à 3, j est égal à 3 ou 4, k, i et d sont
égaux à 0, et R5 est une chaîne hydrocarbonée ayant 7 ou
9 atomes de carbone, tels que le triester de glycérol de
l'acide caprique ou caprylique - m est égal à 3, j est égal à 6 et k, i et d sont égaux à
0, tels que le triester de triméthylol-propane - n est égal à 4, j est égal à 5, et k, i et d sont égaux
à 0, tels que le tétraester de pentaérythritol.Advantageously, the compound corresponding to formula II is chosen from those for which m is equal to 1, j is between 1 and 18 and
preferably between 1 and 4, and k, i and d are 0,
that is to say, especially among the methyl esters,
ethyl, propyl, isopropyl and butyl;
for values of m and j equal to 1, R5 is a string
hydrocarbon having preferably 7 to 17 carbon atoms
carbon - m is equal to 2, j is between 2 and 12 and is
preferably equal to 2 or 3, and k, i and d are equal to 0,
that is to say, especially among ethylene diesters
glycol and propylene glycol - m is equal to 2, j is between 4 and 12, k equals
at 1, i and d are equal to O and Rs is a string
hydrocarbon having 7 or 9 carbon atoms, such as
the diethylene glycol ester of capric acid or
caprylic m is equal to 3, j is equal to 3 or 4, k, i and d are
equal to 0, and R5 is a hydrocarbon chain having 7 or
9 carbon atoms, such as the glycerol triester of
capric or caprylic acid - m is equal to 3, j is equal to 6 and k, i and d are equal to
0, such that trimethylol-propane triester - n is equal to 4, j is equal to 5, and k, i and d are equal
at 0, such as pentaerythritol tetraester.

L'utilisation d'un solvant selon l'invention présente en outre les avantages suivants - les composés II ont un point éclair élevé permettant
d'élever celui de la base tensioactive résultante - les composés II sont biodégradables. The use of a solvent according to the invention also has the following advantages - the compounds II have a high flash point allowing
to raise that of the resulting surfactant base - compounds II are biodegradable.

Une base tensioactive de l'invention comprend avantageusement 60 à 99% en poids d'au moins un composé répondant à la formule I et 40 à 1% en poids d'au moins un composé de la formule II.  A surfactant base of the invention advantageously comprises 60 to 99% by weight of at least one compound of formula I and 40 to 1% by weight of at least one compound of formula II.

Un second objet de l'invention est une composition assouplissante qui comprend une base tensioactive de l'invention, c'est-à-dire au moins un composé I et son solvant
Des avantages du solvant de l'invention et notamment son effet sur la température de trouble de la base tensioactive permettant d'utiliser cette dernière à des températures suffisamment faibles, et son effet sur le point éclair de la base tensioactive, sont à présent exposés à l'appui des exemples 1 à 4 suivants.A second subject of the invention is a softening composition which comprises a surfactant base of the invention, that is to say at least one compound I and its solvent
Advantages of the solvent of the invention and in particular its effect on the cloud temperature of the surfactant base making it possible to use the latter at sufficiently low temperatures, and its effect on the flash point of the surfactant base, are now exposed to the support of the following examples 1 to 4.

EXEMPLE 1
Cet exemple donne les températures de trouble obtenues pour des bases tensioactives de l'invention comprenant - des composés de formule I dans laquelle,
statistiquement
n + n' + n" = 6, x + y + z = I
et p + q + r = 2
préparé par réaction de deux moles d'acide oléique
hydrogéné avec une mole de triéthanolamine puis réaction
sur le produit intermédiaire obtenu, d'une mole de
sulfate de diméthyle, et - un composé de formule II dans laquelle
* soit j = 1, m = 1, k = i = d = O et Rs a de 15 à 17 atomes de carbone et le composé II est l'ester méthylique d'acide gras de palme (EMAGP) (formulations 4 et 5)
* soit j = 3, m = 2, k = i = d = 0 et R5 a 7 ou 9 atomes de carbone et le composé II est le di(caprate/caprylate, 65/35, m/m) de propylène glycol
(DCCPG) (formulations 8 et 9)
* soit j = 3, m = 3, k = i = d = 0 et R5 a 7 ou 9 atomes de carbone et le composé II est le tri(caprate/caprylate, 65/35, m/m) de glycérol (TCCG)
(formulations 6 et 7).EXAMPLE 1
This example gives the cloud temperatures obtained for surfactant bases of the invention comprising - compounds of formula I wherein
statistically
n + n '+ n "= 6, x + y + z = I
and p + q + r = 2
prepared by reacting two moles of oleic acid
hydrogenated with one mole of triethanolamine and then reaction
on the intermediate product obtained, one mole of
dimethyl sulfate, and a compound of formula II in which
* where j = 1, m = 1, k = i = d = O and Rs has 15 to 17 carbon atoms and compound II is palm fatty acid methyl ester (PGME) (formulations 4 and 5 )
* is j = 3, m = 2, k = i = d = 0 and R5 has 7 or 9 carbon atoms and compound II is di (caprate / caprylate, 65/35, m / m) propylene glycol
(DCCPG) (formulations 8 and 9)
* is j = 3, m = 3, k = i = d = 0 and R5 has 7 or 9 carbon atoms and compound II is the tri (caprate / caprylate, 65/35, m / m) glycerol (CGCT) )
(formulations 6 and 7).

* soit j = 3, m = 3, k = i = d = 0 et R5 a de 5 à 17 atomes de carbone et le composé II est l'huile de coprah (HC) (formulations 2 et 3). * = j = 3, m = 3, k = i = d = 0 and R5 has from 5 to 17 carbon atoms and compound II is coconut oil (HC) (formulations 2 and 3).

Cet exemple permet de comparer ces températures de trouble avec celles obtenues avec une base tensioactive ne comprenant que le composé I ci-dessus (formulation 1). This example makes it possible to compare these cloud temperatures with those obtained with a surfactant base comprising only compound I above (formulation 1).

Le procédé de détermination de la température de trouble de bases tensioactives décrites dans les exemples 1 à 3, qui vise à déterminer la température correspondant au début de cristallisation du produit, est le suivant
Matériel
* bain marie
* thermomètre gradué au 1/2 OC
* verrerie usuelle de laboratoire
Mode opératoire
* on chauffe préalablement la base cationique dans son solvant jusqu'à sa température d'écoulement
* on transvase environ 10 g de produit dans un bécher de 50 ml
* on chauffe au bain marie en agitant jusqu'à une température supérieure de 100C environ au point de cristallisation supposé
* on transfère une petite partie dans un tube à essai sur 2 à 4 cm et on refroidit à 20C/mn en agitant lentement avec un thermomètre
* la température de cristallisation est relevée à l'apparition de trouble au centre de l'échantillon.The method for determining the surfactant base haze temperature described in Examples 1 to 3, which aims at determining the temperature corresponding to the beginning of crystallization of the product, is as follows
Equipment
* bain marie
* thermometer graduated to 1/2 OC
* usual laboratory glassware
Operating mode
the cationic base is heated beforehand in its solvent to its flow temperature
* Transfer 10 g of product into a 50 ml beaker
* is heated in a water bath stirring to a temperature of about 100C greater than the point of crystallization assumed
* Transfer a small portion into a test tube over 2 to 4 cm and cool to 20C / min by stirring slowly with a thermometer
* The crystallization temperature is recorded at the appearance of turbidity in the center of the sample.

Les résultats obtenus pour les formulations 1 à 9 apparaissent dans le Tableau 1 suivant, dans lequel les concentrations des composés I et II sont données en pourcentage pondéral. The results obtained for formulations 1 to 9 appear in the following Table 1, in which the concentrations of compounds I and II are given in weight percent.

TABLEAU 1

Figure img00070001
TABLE 1
Figure img00070001

<tb> fomulation <SEP> 1 <SEP> 2 <SEP> 3 <SEP> 4 <SEP> 5 <SEP> 7 <SEP> 8 <SEP> 9
<tb> Composé <SEP> I <SEP> 100 <SEP> 90 <SEP> 85 <SEP> 90 <SEP> 85 <SEP> 90 <SEP> 85 <SEP> 90 <SEP> 85
<tb> EMAGP <SEP> o <SEP> 0 <SEP> 0 <SEP> 10 <SEP> 15 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0
<tb> DCCPG <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 10 <SEP> 15
<tb> TCCG <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 10 <SEP> 15 <SEP> 0 <SEP> 0
<tb> HC <SEP> 0 <SEP> 10 <SEP> 15 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0
<tb> Température <SEP> de <SEP> > <SEP> 80 <SEP> 56 <SEP> 45 <SEP> 49 <SEP> 36 <SEP> 54 <SEP> 36 <SEP> 50 <SEP> 29
<tb> trouble <SEP> ("C) <SEP>
<tb>
EXEMPLE 2
Cet exemple donne les températures de trouble obtenues pour des bases tensioactives de l'invention comprenant - des composés de formule I dans laquelle,
statistiquement
n + n' + n" = 6, x + y + z = 1
et p + q + r = 2
préparé par réaction de deux moles d'acide gras de suif
partiellement hydrogéné (indice d'iode = 45g I2/100g)
avec une mole de triéthanolamine, puis réaction sur le
produit intermédiaire obtenu, d'une mole de sulfate de
diméthyle, et - un composé de formule II dans laquelle
* soit j = 1, m = 1, k = i = d = 0 et R5 a de 5 à 17 atomes de carbone et le composé II est l'ester méthylique des acides gras de coprah (EMC) (formulations 11 et 12)
* soit j = 3, m = 2, k = i = d = 0 et R5 a 7 ou 9 atomes de carbone et le composé II est le di(caprate/caprylate, 65/35, m/m) de propylène glycol (DCCPG) (formulation 13)
* soit j = 3, m = 3, k = i = d = 0 et R5 a de 5 à 17 atomes de carbone et le composé II est l'huile de coprah (HC) (formulation 16)
* soit j = 5, m = 4, k = i = d = 0 et R5 a 7 ou 9 atomes de carbone et le composé II est le tétra(caprate/caprylate, 65/35, m/m) de pentaérythritol (TCCPE) (formulation 14)
* soit j = 6, m = 3, k = i = d = O et R5 a 7 ou 9 atomes de carbone et le composé II est le tri(caprate/caprylate, 65/35, m/m) de triméthylol-propane (TCCT) (formulation 15).<tb> fomulation <SEP> 1 <SEP> 2 <SEP> 3 <SEP> 4 <SEP> 5 <SEP> 7 <SEP> 8 <SEP> 9
<tb> Compound <SEP> I <SEP> 100 <SEP> 90 <SEP> 85 <SEP> 90 <SEP> 85 <SEP> 90 <SEP> 85 <SEP> 90 <SEP> 85
<tb> EMAGP <SEP> o <SEP> 0 <SEP> 0 <SEP> 10 <SEP> 15 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0
<tb> DCCPG <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 10 <SEP> 15
<tb> TCCG <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 10 <SEP> 15 <SEP> 0 <SEP> 0
<tb> HC <SEP> 0 <SEP> 10 <SEP> 15 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0
<tb> Temperature <SEP> from <SEP>><SEP> 80 <SEP> 56 <SEP> 45 <SEP> 49 <SEP> 36 <SEP> 54 <SEP> 36 <SEP> 50 <SEP> 29
<tb> disorder <SEP>("C)<SEP>
<Tb>
EXAMPLE 2
This example gives the cloud temperatures obtained for surfactant bases of the invention comprising - compounds of formula I wherein
statistically
n + n '+ n "= 6, x + y + z = 1
and p + q + r = 2
prepared by reaction of two moles of tallow fatty acid
partially hydrogenated (iodine value = 45g I2 / 100g)
with one mole of triethanolamine and then reaction on the
intermediate product obtained, one mole of
dimethyl, and a compound of formula II in which
* where j = 1, m = 1, k = i = d = 0 and R5 has from 5 to 17 carbon atoms and compound II is the methyl ester of coconut fatty acids (EMC) (formulations 11 and 12)
* is j = 3, m = 2, k = i = d = 0 and R5 has 7 or 9 carbon atoms and compound II is di (caprate / caprylate, 65/35, m / m) of propylene glycol ( DCCPG) (formulation 13)
* is j = 3, m = 3, k = i = d = 0 and R5 has from 5 to 17 carbon atoms and compound II is coconut oil (HC) (formulation 16)
* is j = 5, m = 4, k = i = d = 0 and R5 has 7 or 9 carbon atoms and compound II is tetra (caprate / caprylate, 65/35, m / m) pentaerythritol (TCCPE ) (formulation 14)
* is j = 6, m = 3, k = i = d = O and R5 has 7 or 9 carbon atoms and compound II is tri (caprate / caprylate, 65/35, m / m) trimethylol propane (TCCT) (formulation 15).

Ces températures de trouble sont comparées à celles obtenues avec une base tensioactive ne comprenant que le composé I ci-dessus (formulation 10) et deux bases tensioactives classiques comprenant le composé I et, à titre de solvant, respectivement de l'isopropanol (formulation 17) et du dipropylène glycol monométhyléther (formulation 18). These clouding temperatures are compared with those obtained with a surfactant base comprising only compound I above (formulation 10) and two conventional surfactant bases comprising compound I and, as a solvent, respectively isopropanol (formulation 17). ) and dipropylene glycol monomethylether (formulation 18).

Les résultats obtenus pour les formulations 10 à 19 apparaissent dans le Tableau 2 suivant, dans lequel les concentrations des composés I et II sont données en pourcentage pondéral.  The results obtained for the formulations 10 to 19 appear in the following Table 2, in which the concentrations of the compounds I and II are given in percentage by weight.

TABLEAU 2

Figure img00100001
TABLE 2
Figure img00100001

Formulation <SEP> 10 <SEP> 11 <SEP> 12 <SEP> 13 <SEP> 14 <SEP> 15 <SEP> 16 <SEP> 17 <SEP> 18 <SEP> 19
<tb> Composé <SEP> I <SEP> 100 <SEP> 85 <SEP> 60 <SEP> 80 <SEP> 80 <SEP> 70 <SEP> 70 <SEP> 90 <SEP> 85 <SEP> 80
<tb> EMC <SEP> 0 <SEP> 15 <SEP> 40 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0
<tb> DCCPG <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 20 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0
<tb> TCCPE <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 20 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0
<tb> TCCT <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 30 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0
<tb> HC <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 30 <SEP> 0 <SEP> 0 <SEP> 0
<tb> Isopropanol <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 10 <SEP> 15 <SEP> 0
<tb> Dipropylène <SEP> glycol
<tb> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 20
<tb> monométhyléther
<tb> Température <SEP> de <SEP> > 80 <SEP> 58 <SEP> 39 <SEP> 42 <SEP> 66 <SEP> 51 <SEP> 57 <SEP> 41 <SEP> 30 <SEP> 34
<tb> trouble <SEP> ( C)
<tb>
EXEMPLE 3
Cet exemple donne les températures de trouble obtenues pour des bases tensioactives de l'invention comprenant - un composé de formule I dans laquelle
n + n' + n" = 7, x = y = z = 0
et p + q + r = 2
préparé par réaction de deux moles d'acide gras de suif
hydrogéné avec une mole de dihydroxy-1,2- diéthylamino
1-propane, puis réaction sur le produit intermédiaire
obtenu, d'une mole de sulfate de diméthyle, et - un composé de formule II dans laquelle
* soit j = 1, m = 1, k = i = d= O et R5 a 5 ou 17 atomes de carbone et le composé est l'ester méthylique des acides gras de coprah (EMC) (formulations 20, 21 et 22)
* soit j = 3, m = 2, k = i = d = 0 et R5 a 7 ou 9 atomes de carbone et le composé est le di(caprate/caprylate, 65/35, m/m) de propylène glycol (DCCPG) (formulations 23, 24, 25).Formulation <SEP> 10 <SEP> 11 <SEP> 12 <SEP> 13 <SEP> 14 <SEP> 15 <SEP> 16 <SEP> 17 <SEP> 18 <SEP> 19
<tb> Compound <SEP> I <SEP> 100 <SEP> 85 <SEP> 60 <SEP> 80 <SEP> 80 <SEP> 70 <SEP> 70 <SEP> 90 <SEP> 85 <SEP> 80
<tb> EMC <SEP> 0 <SEP> 15 <SEP> 40 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0
<tb> DCCPG <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 20 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0
<tb> TCCPE <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 20 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0
<tb> TCCT <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 30 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0
<tb> HC <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 30 <SEP> 0 <SEP> 0 <SEP> 0
<tb> Isopropanol <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 10 <SEP> 15 <SEP> 0
<tb> Dipropylene <SEP> Glycol
<tb> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 0 <SEP> 20
<tb> monomethylether
<tb> Temperature <SEP> of <SEP>> 80 <SEP> 58 <SEP> 39 <SEP> 42 <SEP> 66 <SEP> 51 <SEP> 57 <SEP> 41 <SEP> 30 <SEP> 34
<tb> disorder <SEP> (C)
<Tb>
EXAMPLE 3
This example gives the cloud temperatures obtained for surfactant bases of the invention comprising - a compound of formula I in which
n + n '+ n "= 7, x = y = z = 0
and p + q + r = 2
prepared by reaction of two moles of tallow fatty acid
hydrogenated with one mole of dihydroxy-1,2-diethylamino
1-propane, then reaction on the intermediate product
obtained from one mole of dimethyl sulphate and a compound of formula II in which
* where j = 1, m = 1, k = i = d = O and R5 has 5 or 17 carbon atoms and the compound is the methyl ester of coconut fatty acids (EMC) (formulations 20, 21 and 22)
* is j = 3, m = 2, k = i = d = 0 and R5 has 7 or 9 carbon atoms and the compound is di (caprate / caprylate, 65/35, m / m) propylene glycol (DCCPG ) (formulations 23, 24, 25).

Les résultats obtenus pour les formulations 20 à 25 apparaissent dans le Tableau 3 suivant, dans lequel les concentrations des composés I et II sont données en pourcentage pondéral.  The results obtained for formulations 20 to 25 appear in the following Table 3, in which the concentrations of compounds I and II are given in weight percent.

TABLEAU 3

Figure img00120001
TABLE 3
Figure img00120001

<tb> formulation <SEP> 20 <SEP> 21 <SEP> 22 <SEP> 23 <SEP> 24 <SEP> 25
<tb> ComposE <SEP> I <SEP> 90 <SEP> 80 <SEP> 70 <SEP> 90 <SEP> 80 <SEP> 70
<tb> EMC <SEP> 10 <SEP> 20 <SEP> 30 <SEP> - <SEP>
<tb> DCCPG <SEP> - <SEP> - <SEP> - <SEP> 10 <SEP> 20 <SEP> 30
<tb> Température <SEP> de <SEP> 65 <SEP> 57 <SEP> 53,5 <SEP> 63 <SEP> 54 <SEP> 52
<tb> trouble <SEP> ("C) <SEP>
<tb>
Les exemples 1 et 2 mettent en évidence l'efficacité du composé II sur l'abaissement de la température de trouble de la base tensioactive et notamment pour des concentrations pondérales comprises entre 15 et 40 % selon la nature du composé I.<tb> formulation <SEP> 20 <SEP> 21 <SEP> 22 <SEP> 23 <SEP> 24 <SEP> 25
<tb> Compound <SEP> I <SEP> 90 <SEP> 80 <SEP> 70 <SEP> 90 <SEP> 80 <SEP> 70
<tb> EMC <SEP> 10 <SEP> 20 <SEP> 30 <SEP> - <SEP>
<tb> DCCPG <SEP> - <SEP> - <SEP> - <SEP> 10 <SEP> 20 <SEP> 30
<tb> Temperature <SEP> of <SEP> 65 <SEP> 57 <SEP> 53.5 <SE> 63 <SE> 54 <SEP> 52
<tb> disorder <SEP>("C)<SEP>
<Tb>
Examples 1 and 2 demonstrate the effectiveness of the compound II on lowering the cloud temperature of the surfactant base and in particular for weight concentrations of between 15 and 40% depending on the nature of the compound I.

EXEMPLE 4
Chacune des formulations 1 à 25 des exemples 1 à 3 présente une point éclair supérieur à 65 C (déterminé selon la norme EN57, janvier 1984).EXAMPLE 4
Each of formulations 1 to 25 of Examples 1 to 3 has a flash point greater than 65 C (determined according to EN57, January 1984).

A titre de comparaison avec une base tensioactive classique, le point éclair des formulations 26 et 27 comprenant le composé I défini dans l'un quelconque des exemples 1 à 3 et de l'isopropanol en tant que solvant, a été déterminé selon la même norme que ci-dessus (Tableau 4).  As a comparison with a conventional surfactant base, the flash point of the formulations 26 and 27 comprising the compound I defined in any of Examples 1 to 3 and isopropanol as a solvent was determined according to the same standard than above (Table 4).

TABLEAU 4

Figure img00130001
TABLE 4
Figure img00130001

<tb> Formulation <SEP> 26 <SEP> 27
<tb> Composé <SEP> I <SEP> 90 <SEP> 85
<tb> Isopropanol <SEP> 10 <SEP> 15
<tb> Point <SEP> éclair <SEP> ( C) <SEP> 35 <SEP> 25
<tb> <tb> Formulation <SEP> 26 <SEP> 27
<tb> Compound <SEP> I <SEP> 90 <SEP> 85
<tb> Isopropanol <SEP> 10 <SEP> 15
<tb> Point <SEP> flash <SEP> (C) <SEP> 35 <SEP> 25
<Tb>

Claims (12)

REVENDICATIONS 1/ Base tensioactive comprenant au moins un composé cationique d'ammonium quaternaire répondant à la formule I suivante 1 / Surfactant base comprising at least one quaternary ammonium cationic compound corresponding to the following formula I
Figure img00140001
Figure img00140001
 - m est un nombre entier compris entre 1 et 8 - j est un nombre entier compris entre 1 et 36 - k est un nombre entier ou zéro - i est un nombre entier ou zéro - d est égal à 0, 1 ou 2.   - m is an integer between 1 and 8 - j is an integer between 1 and 36 - k is an integer or zero - i is an integer or zero - d is 0, 1 or 2.
Figure img00140003
Figure img00140003
 ou or
Figure img00140002
Figure img00140002
 insaturée, ayant de 5 à 23 atomes de carbone - E est une fonction unsaturated, having 5 to 23 carbon atoms - E is a function dans laquelle - Rs est une longue chaîne hydrocarbonée saturée ou in which - Rs is a long saturated hydrocarbon chain or (R5 - E)m- Cj H2(j+1)-m-2d+i Ok+i (II) (R5-E) m-Cj H2 (j + 1) -m-2d + i Ok + i (II) caractérisée en ce qu'elle comprend à titre de solvant, au moins un composé répondant à la formule II suivante: characterized in that it comprises, as solvent, at least one compound corresponding to the following formula II: halogénures et les carbonates et sulfates d'alkyle halides and alkyl carbonates and sulphates carbone, et - X est un contre-ion choisi notamment parmi les carbon, and - X is a counter-ion chosen especially from de carbone - R4 est une courte chaîne alkyle ayant de 1 à 5 atomes de carbon - R4 is a short alkyl chain having 1 to 5 carbon atoms hydrocarbonée alkyle ou alkényle, ayant de 5 à 23 atomes alkyl or alkenyl hydrocarbon having from 5 to 23 atoms choisis chacun parmi les groupes oxy, N et NH - R1, R2, R3 sont respectivement une longue chaîne each selected from oxy, N and NH - R 1, R 2, R 3 are respectively long chain dans laquelle - n, n' n" sont des nombres entiers non nuls - p, q, r, x, y, z sont des nombres entiers ou zéro - la somme de n, n' et n" est comprise entre 4 et 12 - la somme de p, q, r, x, y et z est comprise entre 1 et 4 - la somme de p, q et r est comprise entre 1 et 3 - Y1, Y1X, Yz, Yzz, Y3, Y3t, sont des groupes fonctionnels in which - n, n 'n "are non-zero integers - p, q, r, x, y, z are integers or zero - the sum of n, n' and n" is between 4 and 12 - the sum of p, q, r, x, y and z is between 1 and 4 - the sum of p, q and r is between 1 and 3 - Y1, Y1X, Yz, Yzz, Y3, Y3t, are functional groups 2/ Base selon la revendication 1, caractérisée en ce que i est égal à 0. 2 / base according to claim 1, characterized in that i is equal to 0. 3/ Base selon la revendication 2, caractérisée en ce que si m est égal à 1, j est compris entre 1 et 18 et k et d sont égaux à 0. 3 / base according to claim 2, characterized in that if m is equal to 1, j is between 1 and 18 and k and d are equal to 0. 4/ Base selon la revendication 3, caractérisée en ce que j est compris entre 1 et 4. 4 / base according to claim 3, characterized in that j is between 1 and 4. 5/ Base selon la revendication 4, caractérisée en ce que si j est égal à 1, R5 est une chaîne hydrocarbonée ayant de 7 à 17 atomes de carbone. 5 / base according to claim 4, characterized in that if j is equal to 1, R5 is a hydrocarbon chain having 7 to 17 carbon atoms. 6/ Base selon la revendication 2, caractérisée en ce que si m est égal à 2, k et d sont égaux à 0 et j est compris entre 2 et 12. 6 / base according to claim 2, characterized in that if m is equal to 2, k and d are equal to 0 and j is between 2 and 12. 7/ Base selon la revendication 2, caractérisée en ce que si m est égal à 2, k est égal à 1, j est compris entre 4 et 12, d est égal à 0, et R5 est une chaîne hydrocarbonée ayant 7 ou 9 atomes de carbone. 7 / base according to claim 2, characterized in that if m is equal to 2, k is equal to 1, j is between 4 and 12, d is 0, and R5 is a hydrocarbon chain having 7 or 9 atoms. of carbon. 8/ Base selon la revendication 2, caractérisée en ce que m est égal à 3, j est égal à 3 ou 4, k et d sont égaux à 0 et R5 est une chaîne hydrocarbonée ayant 7 ou 9 atomes de carbone. 8 / base according to claim 2, characterized in that m is equal to 3, j is equal to 3 or 4, k and d are equal to 0 and R5 is a hydrocarbon chain having 7 or 9 carbon atoms. 9/ Base selon la revendication 2, caractérisée en ce que si m est égal à 3, j est égal à 6 et k et d sont égaux à 0. 9 / base according to claim 2, characterized in that if m is equal to 3, j is equal to 6 and k and d are equal to 0. 10/ Base selon la revendication 2, caractérisée en ce que si m est égal à 4, j est égal à 5 et k et d sont égaux à 0. 10 / base according to claim 2, characterized in that if m is equal to 4, j is equal to 5 and k and d are equal to 0. 11/ Base selon l'une quelconque des revendications 1 à 10, caractérisée en ce qu'elle comprend 60 à 99 % en poids d'au moins un composé de la formule I et 40 à 1 % en poids d'au moins un composé de la formule II.  11 / Base according to any one of claims 1 to 10, characterized in that it comprises 60 to 99% by weight of at least one compound of formula I and 40 to 1% by weight of at least one compound of formula II. 12/ Composition assouplissante caractérisée en ce qu'elle comprend une base tensioactive selon l'une quelconque des revendications 1 à 11.  12 / softening composition characterized in that it comprises a surfactant base according to any one of claims 1 to 11.
FR9203199A 1991-12-31 1992-03-12 SURFACTANT BASE COMPRISING A CATIONIC QUATERNARY AMMONIUM COMPOUND AND A COMPOUND AS A SOLVENT AND SOFTENING COMPOSITION COMPRISING SUCH A BASE. Expired - Fee Related FR2688419B1 (en)

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AT92420488T ATE144245T1 (en) 1991-12-31 1992-12-31 QUATERNARY AMMONIUM SURFACTANTS, METHOD FOR THEIR PRODUCTION, BASES AND THEIR DISPENSIVE PLASTICIZERS
ES92420488T ES2094893T3 (en) 1991-12-31 1992-12-31 SURFACES BASED ON QUATERNARY AMMONIUM COMPOUNDS, PREPARATION PROCEDURES, BASES, AND DERIVED SOFTENING COMPOSITIONS.
DE69214618T DE69214618T2 (en) 1991-12-31 1992-12-31 Quaternary ammonium surfactants, processes for their preparation, bases and their plasticizers
EP92420488A EP0550361B1 (en) 1991-12-31 1992-12-31 Surface active quaternary ammonium compounds, processes for their preparation and softening compositions derived from them
US08/447,219 US5637743A (en) 1991-12-31 1995-05-22 Quaternary ammonium surfactants derived from tertiary amines and fabric softeners containing quaternary ammonium surfactants
US08/872,357 US5750492A (en) 1991-12-31 1997-06-10 Surfactants based on quaternary ammonium compounds preparation processes softening bases and compositions derived

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