FR2639635A1 - AMPHOTERIC SURFACTANTS CONTAINING ALKYLENE OXIDE - Google Patents

Abstract

The invention relates to novel amphoteric compounds containing an alkylene oxide and their use as surfactants. The new amphoteric compounds are particularly useful in the fields of cosmetics and toiletries, for example as surfactants in shampoo compositions.

Description

This invention relates to a new class of surfactants. More

  in particular, it relates to certain amphoteric compounds containing an alkylene oxide and their use as surfactants in a wide range of fields of consumer products. Amphoteric compounds containing an alkylene oxide are particularly useful in the fields of cosmetics and cosmetic products.

  toilet, for example as surfactants in composites

shampoo.

  For someone outside the field, research

  of a surfactant usable in sham compositions

  pooing is relatively easy because new surfactants appear regularly in the bibliography. However,

  as the skilled person is well aware, the formulation of

  shampoo positions for human hair is a do-

  highly specialized, bringing into play many considerations, namely cleaning power, foaming action, softness, etc. Most often, a surfactant

  is chosen mainly on the basis of his net power-

  toyant, at the expense of serious compromises on behavior

of the overall product.

  In the past, sham compositions have been used.

  soap-based pooing. Unfortunately, they have the drawback of making the hair dull due to the fact that lime and magnesium soap or the like precipitates

  above, especially in hard water. In addition, these preci-

  pities considerably reduce the foaming action of the

  shampoo positions. Faced with the problems presented by shampoo & soap base compositions, the skilled person tried to overcome these drawbacks by replacing,

  in part, the soap by synthetic organic detergents

  ticks, for example sulfates and sulfonates. However

  in shampoo compositions based on mixtures

  synthetic detergents and soaps seem rather de-

  flawless and offer little interest to the demanding consumer. For example, when such mixtures are brought into contact with calcium ions in water, the lime soaps which necessarily form must be dispersed by the synthetic detergent. As a result, not only is some of the soap lost due to calcium binding,

  when these ions are present, but also part of the

  synthetic detergent is consumed as a dispersing agent for the lime soap formed and thus loses a certain degree

  of its cleaning action. In this regard, one must keep pre-

  feels & the mind that in washing human hair

  hands, even a professional hairdresser normally uses

tap water.

  More recently, we have seen the emergence of compositions by

  25. shampoo which contain, as a cleaning constituent es-

  sentiel, synthetic detergent or a mixture thereof only. However, although such compositions of

  shampoo have cleansing and soft properties

  acceptable health, the presence of synthetic detergent or

  of a mixture of these seems to increase the potential of ir-

  laughing shampoo compositions, thus making them unacceptable from a soft point of view. To strive to

  overcome the increased potential for irritation

  shampoo positions based on synthetic detergents,

  the skilled person has modified the synthetic detergent component

  tick, namely a higher alkyl ether sulfate of formula R (OCH2CH2) nOSO3M in which R is a C10-C15 alkyl group, .m is an integer from 1 to 3 and M is a cation, increasing the level of oxide d 'ethylene. However, such a modification, although somewhat improving the potential for irritation of the above-mentioned alkyl ether sulfates, has an adverse effect on the

  foaming properties of shampoo compositions.

  It is therefore an object of the present invention to provide a new class of surfactants which are useful in a wide variety of consumer product fields. Another object of the present invention is to provide certain amphoteric surfactants containing an alkylene oxide which are particularly useful in the fields of cosmetics and toiletries. Yet another object of the present invention is to provide certain amphoteric compounds containing an alkylene oxide which can be used as an essential surfactant in shampoo compositions, these compositions exhibiting exceptional cleaning and foaming properties. In addition, these amphoteric surfactants have a high degree

  salt tolerance, which allows to obtain

  high tifs of these compounds at lower viscosities.

  The above goals can be achieved through certain

  amphoteric compounds-containing an alkylene oxide, of-

mule I: 0 H _ Ri

XG I

  R0 --- (C3 H60). (C2 4 O0) n - CE2 - C-N-CH2CH2-eN \ 1 Xe, 1 Rz

": CH2CH20H

in which

  R is a straight or branched chain C6-C22 alkyl group

  or a group R3-C6H4, wherein R3 is a straight or branched chain C6-C16 alkyl group;

  R1 is -CH2COOM, in which M is hydrogen or ca-

  tion chosen from an alkali metal, an alkali metal

  earthy, an anmmonium, a mono-, a di- and a tri-alka-

  nol (C2-C4) ammonium and mono-, di-, tri and tetraalkyl (C1-C4) ammonium; R2 is hydrogen or -CH2COOM, in which M is as defined above; m is zero or is an integer from 1 to 10; n is an integer from 2 to 15; and XI is an anion,

or a mixture of these compounds.

  R1 09NX Xe, Regarding the ammonium salt I R | R2

CR2CH2OH

  formula I gives a possible ionic form. However, it is obvious that, in aqueous solution, the solvation

  ions would lead to an equilibrium condition which allows

  relates to the corresponding zwitterionic form of existing with the MC ions and the solvated Xe ions, according to the following reaction scheme: R2 Xe R2 I ______ e-N-CH2CO0e + M.X -ON-CH2COO9 M _ N-CH2COe -, +

CH2CH20HCH2CH20H

  When R is a straight or branched chain alkyl group

  trusted, said alkyl group preferably contains 8 to 20 carbon atoms, better still 10 & 20 carbon atoms,

  and more particularly 12 to 18 carbon atoms.

  When R is an R3-C6H4 group, the R3 part preferably contains 6 to 14 carbon atoms, better still 8 to 12 carbon atoms and more particularly 9 to 12 carbon atoms. The hydroxy group of a C2-C4 hydroxyalkyl group

  any one in M is on another atom than the atom of car-

  bone has it. When M has more than one C2- hydroxyalkyl group

  C4 or a C1-C4 alkyl group, these can be

  identical or different, but are preferably identi-

  ques. Preferably, M does not contain more than two t-butyl groups. The preferred alkali metals for M are li-

  thium, sodium and potassium and alkaline earth metals

  the preferred ones are magnesium, calcium, barium and strontium. The variable m is preferably zero or an integer of 1

  to 5, better still zero or an integer from 1 to 3, in particular

  link null or an integer equal to 1 or 2.

  The variable n is preferably an integer from 2 to 12, better still an integer from 3 to 10 and in particular an integer

from 4 to 9.

  The variables m and n, as well as p, q, r, t, u and v de-

  above, are average values. As is obvious, the variables m, n, p, q, r, t, u and v must be whole numbers in the individual compounds of

this invention.

  The anion X is preferably a halide, more preferably

  core a chloride or a bromide, more particularly a chloride. The preferred compounds of formula I are those of formula la 0 H ARIa RQ-O C3H6GO) p4-C2H40) q-CH2-C-N-CH2CH2-N xe a | R2a

CH2CH20H

in which

  Ra. is a straight or branched C8-C20 alkyl group

  or a group R3a-C6H4, in which R3a is a straight or branched chain C6C14 alkyl group; Rla is -CH2COOMa, in which Ma is hydrogen or

  cation chosen from an alkali metal, an alkali metal

  lineal and ammonium; R2a is hydrogen or a group -CH2COOMa, in which Ma is as defined above; p is zero or is an integer from 1 to 5; q is an integer from 2 to 12; and Xae is a halide,

or a mixture of these compounds.

  The particularly preferred compounds of formula I are those of formula Ib O HRlb Rb_-O- (C3H60) r (C2H40) t-CH2_-C-N-CH2CH2 - N Xbe Ib I R2b

CH2CH2OH

in which

  Rb is a straight chain or straight chain C10-C20 alkyl group

  mified or a group R3b-C6H4, wherein R3b is a straight or branched chain C8C12 alkyl group; Rlb is -CH2COOMb, wherein Mb is hydrogen or a cation selected from an alkali metal and ammonium; R2b is hydrogen or a group -CH2COOMb, in which Mb is as defined above; r is zero or is an integer from 1 to 3; t is an integer from 3 to 10; and Xba is a chloride or a bromide,

or a mixture of these compounds.

  The compounds of formula I very particularly preferred-

res are those of formula Ic

0 H Rj.

  il X- I = R-C) --- C3Hl60) .-- C2H40), V-CH2-C-N CHZCH2-éNs Xce Ic

CH2CH2 OH

in which

  Rc is a straight chain C12-Cl8 alkyl group or ra-

  mified or a group R3c-C6H4, wherein R3c is a straight or branched chain C9Cl2 alkyl group; Rlc is -CH2COOMc, where Mc is hydrogen or

  cation chosen from sodium, potassium and ammo-

  nium; R2c is hydrogen or a group -CH2COOMc, in which Mc is as defined above; u is zero or is an integer equal to 1 or 2; v is an integer from 4 to 9; and Xce is a chloride,

or a mixture of these compounds.

  Suitable alcohol precursors of ampho-

  ters containing an alkylene oxide of this invention are straight chain or branched chain primary alcohols having 6 to 22 carbon atoms. Typical examples of alcohols

  having a branched chain configuration are iso- alcohol

  decyl and isostearyl alcohol. A mixture of alcohols can be used and will generally be the case if commercial alcohols which are often available as mixtures of several alcohols are used. Specific examples are a mixture of C12-C15 straight chain alcohols commercially available from Union Carbide;

  a mixture of mainly straight chain alcohols in C12-

  C15 containing about 20% of ramifications, available on

  the market with Shell Chemical Co .; and a mixture of al-

  cools, of which at least 70% by moles are branched 1-decanols

  , commercially available from Exxon Chemical Co. When a mixture of alcohols is used, the number of carbon atoms in the alcohol is designated by an average number which can be determined by vapor chromatography and

by the hydroxyl number.

  Other suitable precursors of ampho-

  ters containing an alkylene oxide of this invention are straight or branched chain alkylphenols having from 6 to 16 carbon atoms in their alkyl moiety. Typical examples of alkylphenols having a & chain configuration

  right are n-hexanol, n-decylphenol, n-dodecylpheno-

  nol, n-tetradecylphenol, etc., while iso-octylphenol-

  nol and branched chain nonylphenol are examples of alkylphenols having a branched chain configuration. Compounds and mixtures of formula Z are produced

  by conventional methods. This is how we can pre-

  adorn amphoteric compounds containing an alkylene oxide

  of this invention by carboxyalkylation of the additive compound

  tion resulting from the propoxylation and / or ethoxylation of a straight or branched chain primary alcohol having 6 to 22 carbon atoms or of a straight or branched chain alkylph6nol having 6 & 16 carbon atoms

  in its alkyl part, reaction of the addition compound

  resulting boxyalkylated with an appropriate amine, by a

  condensation reaction, then carboxyalkylation of the inter-

  resulting amidoamine medium to obtain a compound of

  formula I in which R2 is hydrogen. A carboxyalky-

  further relationship of this compound leads to a compound of

  formula I in which R2 is -CH2COOM.

  The alkoxylation step can be carried out in advance.

  presence of an alkali catalyst, for example of alkali metal hydroxides, sodium ethylate, sodium methylate, alkali metal acetates and dimethylamine, and their

  mixtures, preferably sodium hydroxide or potassium-

  sium, in an amount of 0.2% to 1% for example, preferably

  rate of 0.3% to 0.75%, by weight of the reaction mixture to-

tal.

  Optionally, you can add alcohol, or

  alcohol swab, or alkoxylate alkylphenol, a small amount of a reducing agent to minimize change

  color of alcohol or polyalkoxylated alkylph6nol

  sultant. Suitable reducing agents which can be taken

  ployer include sodium borohydride, lithium aluminum hydride and diborane, preferably sodium borohydride. To prepare a polyoxyalkylated alcohol or alkylphenol in which the polyoxyalkylene chain contains a first

  propylene oxide block and a second ethylene oxide block

  lene, a calculated amount of propylene oxide is introduced to give the desired degree of propoxylation and the resulting mixture is allowed to react until the oxide

  propylene is consumed, which indicates a drop in pressure

  reaction reaction. A simple introduction and reaction

  milk of a calculated amount of ethylene oxide serves &

  provide the second block which completes alkoxylation. Habi-

  Finally, the alkoxylated product is finally treated with a weak acid, for example glacial acetic acid, to

  neutralize any basic catalytic residue.

  It is understood that each separate alkoxylation operation serves to introduce a desired average number of units

  of alkylene oxide per molecule of alcohol or of alkylphenol.

  Thus, for example, the initial treatment of an alcohol, or a mixture of alcohols, or an alkylphenol, with m moles of propylene oxide per mole of alcohol or alkylphenol serves to carry out the propoxylation of each alcohol or alkylphenol group with propylene oxide up to an average of m propylene oxide groups per alcohol group or

  alkylphenol, although some alcohol or alkyl-

  phenol will have combined with more than m propylene oxide groups and that some will have combined with less than m groups. In general, the maximum number of propyleneoxy units in a single molecule will not exceed 20 and the number of ethyleneoxy units in a single molecule will not exceed 25. The variation in the number of alkylene oxide groups is not critical, provided that the number

  patterns in each block either within the limits

  quées for the terms m and n in the formula I above, these terms, in average values, being in certain cases

different from whole numbers.

  Each alkoxylation is carried out at a high temperature.

  high pressure. Reaction temperatures

  suitable ones are 120 & about 220C, preferably

  rence from 130 & 180'C, and better still from 140 to 1600C. We ob-

  maintains a suitable reaction pressure when introducing,

  in the reactor, the required amount of propylene oxide

  lene or ethylene oxide, each having a pressure of

  high fear at the desired reaction temperature. The pressure is used to measure the degree of the reaction and each alkoxylation is considered to be complete when the

  pressure no longer decreases over time.

  For best results, it is desired to

  table to perform alkoxylation under relative conditions

  anhydrous and avoid side reactions which

  form water. To dry the reactor and connect them

  However, they should be swept with dry gas, without oxygen, for example nitrogen, before introducing the load. he

  the cataly-

  or the catalytic mixture. We should preferably

  rify propylene oxide and ethylene oxide to remove

  undermine humidity and any impurity capable of intervening in

  side reactions that produce water.

  Polyalkylalkyl or alkyl-

  aryl resulting are then carboxymethylated by the syn-

  Williamson's thesis, which involves a reaction with the a-

  suitable chloro- or bromocarboxylic acid, or a salt thereof, in the presence of a strong base, for example sodium hydroxide, sodium carbonate, etc., or by oxidation

  catalytic. This reaction is not usually understood

  flat; therefore, the reaction product often contains

  Wind minor amounts of alkyl polyalkoxide or

  of non-carboxylated alkylaryl. Although there are

  dice to separate the non-carboxymethylated substance as well as

  to provide essentially com- mon carboxymethylation

  flat, these are generally tedious and costly processes

  teux. Fortunately, it has been found that

  of this non-carboxymethylated substance are not

  particularly harmful, and may even be beneficial.

  geuses. Carboxymethylation involving a reaction with the appropriate chloro- or bromocarboxylic acid or one of

  its salts in the presence of a strong base is preferred for ob-

hold a full reaction.

  The amidoethylamine intermediates can be prepared by a condensation reaction comprising the reaction of alkyl- or alkylphenylpolyoxyalkylenecarboxylic acids and

  suitable amine, for example 2-aminoethylethanol-

  amine, in almost equimolar proportions, & high temperatures between 100 and 220 "C and under pressures

  while eliminating condensed water.

  Alternatively, the amidoethylamine intermediates may

  can be prepared by a condensation reaction involving the lower alkyl esters of corresponding alkyl- or alkylphenylpolyoxyalkylenecarboxylic acids, for example methyl, ethyl, isopropyl, etc., or the halides, and the appropriate amine, in almost proportions

  equimolar, at a temperature between 50 and 150C.

  For example, the amidoethyl intermediates can be prepared.

  amines by a condensation reaction involving the

  isopropyl ter of alkyl- or alkylphenyl-polyoxy- acid

  corresponding alkylene carboxylic acid and the appropriate amine,

  eliminating isopropyl alcohol. When using halo-

  corresponding carboxylic acid genide, the

  reaction with a 0.45-1.10 molar ratio of the halogen-

  amine carboxylic acid, the use of an ex-

  this amine is necessary to trap chlorhy-

  drique mistletoe forms during the reaction. Eventually,

  a basic amine can be added, for example triethyl-

  amine or pyridine, to the reaction mixture to trap hydrochloric acid. If this is done, the reagents can be used in almost equimolar proportions. The reaction is usually carried out in the presence of an inert organic solvent, for example an aliphatic hydrocarbon such as

  dichloromethane, at a temperature of 25 to 50C.

  The resulting amidoethylamine intermediates are also

  further carboxylated by formation of an ammonium salt by a nucleophilic displacement reaction. It is not necessary to add a base because of the basic / nucleophilic nature of the amine function. Therefore, when we react

  an amidoethylamine intermediate and the hydrochloric acid salt

  or bromocarboxylic in almost equimolar proportions, in

  presence of a common solvent, for example water or al-

  cool, at a temperature of 25 to 100'C, preferably com-

  taken between 50 and 90 @ C, a compound of formula I is prepared in which R2 is hydrogen. It is not necessary

  to use a solvent if the viscosity of the reaction mass-

  It allows efficient agitation and good mass transfer.

  one can realize, by the reaction of displacement precise

  tée, further carboxylation, i.e. to pre-

  counter the compounds of formula I in which R2 is

  -CH2COOM, including the presence of a strong base to de-

  protonate the ammonium ion and make it nucleophilic towards the chloro- or bromocarboxylic acid salt. Conditions

  are essentially identical & those

  above for the preparation of the compounds

  of formula I in which R2 is hydrogen.

  The compounds of formula I are useful as ten-

  sioactive, and are suitable as emulsifiers, dispersing agents

  health, detergents, wetting agents, leveling agents, and

  analogues, in the textiles, leather, pa-

  pier, hairspray, personal hygiene, for example

  toiletries, cosmetics, etc. and in the industry

  sorts rubber. For example, they can be used as wetting agents or as detergents in the treatment and

  the refinement of textiles and to transform substances

  those liquids or solids that are insoluble in water

  (such as hydrocarbons, higher alcohols, oils,

  , fats, waxes and resins) in creamy emulsions, in clear solutions or in fine dispersions and

stable.

* In addition, the compounds of formula I are emulsi-

  precious fiants for insecticide compositions and

  agricultural sprays like DDT, 2,4-D and ana-

  logues; they are useful as additives to petroleum products.

  liers, hydraulic fluids, lubricating oils,

  cutting oils and greases; they can be taken

  used as coating aids in coating compositions comprising a film-forming hydrophilic colloid; they can be used as sticky agents in the diaper

  adhesive tape and, for example, in the industry

  photographic sorting; and we can use them as agents

  foaming agents and as emulsifiers in a wide range of

food laughter.

  The amphoteric compounds of the present invention are particularly useful as a surfactant component in shampoo compositions. Their incorporation serves & improves not only the detergent and foaming properties of the shampoo compositions, but also their

  tactile properties. These shampoo compositions contain-

  from which normally about 5% to about 55% of a compound

  amphoteric of formula I, preferably about 10% to-

  about 45%, better still about 10% & about 40%. Good

  that the amphoteric compounds of the invention can be em-

  employed as the sole surfactant of these compounds, that is to say completely replace the conventional anionic surfactants such as polyethoxylated alkylsulfates, the particularly preferred characteristic of the present invention is to use the amphoteric compounds of this invention in combination with the conventional surfactants , that is, to partially replace them. In such shampoo compositions, the amphoteric surfactants of the present invention normally constitute between 20% and 50% by weight

  of the mixture, preferably between 30% and 45%.

  Shampoo compositions may contain other

  very ingredients that are commonly found in ingredients

  sitions of this type. For example, we can use, for fa-

  cilitate the stabilization of the foam, to strengthen the

  foam and to obtain a cosmetically acceptable viscosity

  table, a fatty alkanolamide, or a mixture thereof. We take

  generally uses a C8-C18 type 1: 1 mono- or di-alkanolamide (prepared by reaction of equimolar amounts of the methyl ester of the appropriate carboxylic acid and of the mono- or dialcanolamine). A suitable example of a monoalkanolamide is coconut monoethanolamide and typical examples of suitable dialcanolamides are

  lauric diethanolamide and coconut diethanolamide.

  Conditioners can also be used and they can be quaternary ammonium compounds such as

  dimethyldistearylammonium chloride and catalytic polymers

  such as Cartaretin F-23 (Sandoz Corporation) and Polymer JR (Union Carbide). These substances are used to improve combing and styling of damaged hair and to reduce the accumulation of static electricity on

dry hair.

  To improve the shine of the hair, an oil may be present in the shampoo compositions. he can

  be a silicone oil such as dimethylpoly-

  loxanne or other conventional polysiloxannes, oil

  olive or light mineral oil.

  The amount of water or aqueous vehicle to be included

  hangs from the desired consistency for the final product. It is possible to vary the amount of water present to formulate, for example, a thick flowing liquid, a lotion or a gel. Mineral salts can also be used

  like sodium chloride to adjust the viscosity.

  Other conventional additives typically used in shampoo compositions can be used. You can use fragrance oils, which mask the smell

  and offer cosmetic appeal. We can use, for co-

  according to wishes, the compositions, non-toxic and compatible dyes. We can use preservatives,

  such as methyl para-hydroxybenzoate, para-hydroxy-

  propyl benzoate and formaldehyde.

  One can also advantageously use other ingredients.

  dients for obtaining shampoo compositions for

  for a specific use. For example, one can use an ad-

  called sunscreen like octyldim6thyl-p-amino acid

  benzoic, to provide hair protection. Furthermore,

  we can formulate products designed to provide

  dandruff tection with agents like zinc-oma-

dinner (Olin).

  The following examples, in which all parts

  are by weight and all the temperatures in degrees centi-grades, illustrate the invention.

  Example 1: N- [2- (N'-carboxymethyl-N '- (2-hy-

  droxyethyl) ammonium) ethyl lauryl-tetraethoxyacetamide 0 CH2 COONa tilIlC C 25 H-2 -0 - CH40-) -CH2CNHCH2CHZ-C2 z-Cle

CHCH20OH

  a) Preparation of N- [2- (2-hydroxyethylamino) 6thyl] lauryl-

tetraethoxyacetamide

  282.6 parts of lauryltetraethoxyaceous acid are placed

  tick in a reactor, heated & 70 'under vacuum (pump & water) to remove residual water, bubbled with

  nitrogen and cooled to 250. Add to the

  actor, in direct current, while waving, under a circu-

  nitrogen nitrogen & 250, 52.07 parts of 2-aminoethylethanol-

  amine. The temperature of the reaction mixture is gradually raised to 49 °, over the course of an hour, after which

  heats the reaction mixture to 106- under a circu-

  nitrogen nitrogen. After collecting 10 parts of water, the heating is interrupted and the resulting product is allowed to cool to 250 to obtain a liquid product of formula 0o I!

C12H25-0-4C2H40) 4CH2CC2C: -

  CH2CH2zOH b) Preparation of the title compound

  102.15 parts of the compound prepared in la) are dissolved.

  above in 180.3 parts of distilled water and place the

  resulting lution in a reactor. 55 parts of sodium monochloroacetate are then added to the reactor 17, while stirring. The reaction mixture is then heated to 70 and this temperature is maintained for 5

  hours. The heating is then interrupted, which is done

  duit by obtaining the title compound in solution at 40% of active compound. After cooling, we obtain

  the title compound as a clear yellow gel.

  Example 2: N- [2- (N ', N'-bis (carboxymethyl) -N'- chloride

  (2-hydroxyethyl) anmonium) ethyl] -p-nonylphenoxy-nonaethoxy-

acetamide

/ ó2 ON

  H 9 Cs \ 0- (Cz H40O) 9 CHZ CNHC12 CH2 -e0N - i O 1 CH2COONa glc oCH) HZHC2HCie * J CHICOOtNa

CH2CH2OE

  a) Preparation of N- [2- (2-hydroxyethylamlno) ethyl] -p-no-

  nylphenoxy-nonaéthoxyacétamlde By following essentially the procedure of example la) above, and using, instead of lauryltetraethoxyacetic acid, an almost equivalent amount

  p-nonylphenoxynonaethoxyacetic acid, a compound is obtained

  posed with formula o H, óCt / - -O -; - C2H40-) t-CH2CNHCH2CH2NH

CH2CH2OH

  b) Preparation of the title compound

  218 parts of the compound prepared in 2a) are dissolved

  above in 416 parts of distilled water and the resulting solution is introduced into a reactor. After starting

  stirring, 30.2 parts of mo- are added to the reactor

  sodium nochloroacetate. The heated mixture is then heated.

  active up to 750 and this temperature is maintained for

  for 4 hours. The mixture is then cooled to 50 "

  and 20.8 parts of a sodium hydroxide solution are added

  50% dium. After stirring for 30 minutes, 30.2 parts of sodium monochloroacetate are added to the mixture. The resulting mixture is allowed to react overnight, while maintaining the temperature at 50. We then interrupt the

  heating, which leads to the title compound, which is obtained

  holds as a clear, colored aqueous solution

  yellow containing about 40% of active compound.

  Example 3: N- [2- (N ', N'-bis (carboxymethyl) -N'- chloride

  (2-hydroxyethyl) ammonium) ethyl] isodecyl-dipropoxyhexaethoxy-

  acetamide O CH2 COONa Ci 2 5 i so-C0oH2 -0- ± C3 ^ HO -)> 2 - (- C2H4O-) 6CH2CNHCHC2CHGN / C1G

-CH0COON &

CH2CH2 OH

  a) Preparation of N- [2- (2-hydroxyethylamino) iethyl] isode-

  cyldipropoxy-hexaethoxyacetamide - By essentially following the procedure of example la) above, and using, instead of lauryltetraethoxyacetic acid, an almost equivalent amount of isodecyl-dipropoxy-hexaethoxyacetic acid, a compound of formula o O Il iso-CoH2_O ._. C3HiO -) --- C2H40-) G-CH2CNBCH2CB CH: CHzOH b) Preparation of the title compound Essentially following the last step of the process for preparing the compound of Example 2, and using, instead of the compound prepared in Example 2a), an amount

  practically equivalent to the compound prepared in 3a) above

  above, the title compound is obtained in the form of a solution.

  Light yellow aqueous tion containing about 40% of active compound.

  Example 4: N- [2- (N ', N'-bis (carboxymethyl) -N'- chloride)

  (2-hydroxyethyl) ammonium) ethyl] lauryl-tetraethoxyacetamide O ..- CH2COONa C12H2s-O-4C2H40) 4CH2CNHCH2CH2-N <Cie l CH2COONa

C3: CH2OH

  By essentially following the last step of the process for preparing the compound of Example 2 and using, instead of the compound prepared in Example 2a), a practically equivalent amount of the compound prepared in Example

  la), the title compound is obtained in the form of a solution.

  Light yellow aqueous tion containing about 40% of active compound. It is understood that, in all of the above examples, the numbers of propyleneoxy units and of & thylneoxy units

  shown are average values.

Example 5

  To demonstrate the high degree of tolerance to the salts presented by the amphoteric compounds of the present invention, the compound of Example 3 is tested with respect to Miranol

  C2M (commercial amphoteric surfactant containing a hydro-

  copra phobe having an average chain length of 12 carbon atoms). Samples are prepared containing% of active surfactant and proportions of sodium chloride varying from 3% to 13%. We measure the Viscosities at

  using a Brookfield LVT viscometer & 60 rpm

  nutes. As clearly shown in Figure 1, the compound of Example 3 has a significantly lower viscosity for

  each salt level. In addition, when the salt level increases

  mente, the viscosity of the compound of Example 3 remains lower

  better than that of the Miranol C2M. Consequently, it can be concluded that the compound of Example 3 is better suited than Miranol C2M for formulating products which contain high proportions of ionic materials. Furthermore, it can also be concluded that the compound of Example 3 would be more

  effective than the.Miranol C2M to recover a ter-

  when the salt conditions are high.

  Example 6 The following presents typical useful formulations

as shampoo compositions.

Formulation

A B

  Ingredients% by weight Compound of Example 4 9.20 16.67

  Sodium myristylethersulfate 11.70 -

  Triethanolamine lauryl sulfate - 38.90 Lauric acid diethanolamide 3.00 3.30

  Sodium Laureth-l3-carboxylate 0.50 -

  Pareth (C12.15) -9-cetyl carboxylate 1.00

PEG 60001 distearate 0.50 -

  Polymer JR-4002 - 0.30 Germaben II3 1.00

Surfactant Dow 1934 1.00 -

  Water (citric acid) 72.10 40.83 Total 100.00 100.00 pH (adjusted with citric acid) 6.5 6.5 Total dry matter (Cenco5) 19.0 32.0 Viscosity (60 rpm; spindle 4; 4720 mPa.S 4760mPa.S Brookfield LVT) Height of foam (Ross-Miles; 0.1%; 172/172 152/150 mm 0/5 min) i Reaction product of polyethylene glycol (molar mass = 6000) with stearic acid (2 equivalents) 2 Reaction product of l hydroxyethylcellulose and epichlorohydrin which is then quaternized with trimethylamine, available commercially from Union Carbide Corp .; 3 Mixture of diazolidinylurea, methyl para-aminobenzoate and propyl paraaminobenzoate in propylene glycol, commercially available from Sutton Labs, Inc .; 4 Dimethicone copolyol, commercially available from Dow Corning; Type of moisture balance using an infrared lamp

red to remove moisture.

R E V E N D I CATIONS

1. Compound of formula I

0 H R1

  Il l XR1 9 RO + 4C3H60) _ 4C2H4 0), - CH2-C-N-CH2CH2N xe I | R2

CH2CH20H

in which

  R is a straight or branched chain C6-C22 alkyl group

  or a group R3-C6H4, wherein R3 is a straight or branched chain C6-C16 alkyl group;

  R1 is -CH2COOM, in which M is hydrogen or ca-

  tion chosen from an alkali metal, an alkali metal

  earthy, ammonium, mono-, di- and tri-alka-

  nol (C2-C4) ammonium and mono-, di-, tri and tetraalkyl (C1-C4) ammonium; R2 is hydrogen or -CH2COOM, in which M is as defined above; m is zero or is an integer from 1 to 10; n is an integer from 2 to 15; and xe is an anion,

or mixture of these compounds.

  2. Compound according to claim, characterized in that it corresponds to the formula Ia 0 H

IO H / R AT

  R-O- (C3 H6 O) p- (C2H4 O) q-CH -C-N-CH2CH2-AN _ Xe Ia I R2a

CH2CH20H

in which

  Ra is a straight or branched chain C8-C20 alkyl group

  or a group R3a-C6H4, in which R3a is a straight or branched chain C6C14 alkyl group; Rla is -CH2COOMa, in which Ma is hydrogen or

  cation chosen from an alkali metal, an alkali metal

  lineal and ammonium; R2a is hydrogen or a group -CH2COOMa, in which Ma is as defined above; p is zero or is an integer from 1 to 5; q is an integer from 2 to 12; and XaO is a halide,

or mixture of these compounds.

  3. Compound according to claim 2, characterized in that it corresponds to the formula Ib H / Rlb

  Rb-O- (C3H60) r-4-C2H40) t -CH2 - C-N-CH2CH2-

I R2b

CH2CH20H

in which

  Rb is a straight chain or straight chain C10-C20 alkyl group

  or a group R3b-C6H 4, wherein R3b is a straight or branched chain C8C12 alkyl group; Rlb is -CH2COOMb, in which Mb is hydrogen or a cation selected from an alkali metal and an armmonium; R2b is hydrogen or a group -CH2COOMb, in which Mb is as defined above; r is zero or is an integer from 1 to 3; t is an integer from 3 to 10; and Xbe is a chloride or a bromide,

or mixture of these compounds.

  4. Compound according to claim 3, characterized in that it corresponds to the formula Ic

0 H R1

  Rc-O- (C3H60) u- (C2zH40) v-CH2-C-N - CH2C2-N xce Ic

| R2 =

CH2CH20H

in which

  Rc is a straight chain C12-C18 alkyl group or ra-

  mified or a group R3c-C6H4, wherein R3c is a straight or branched chain C9C12 alkyl group; Rlc is -CH2COOMc, where Mc is hydrogen or

  cation chosen from sodium, potassium and ammo-

  nium; R2c is hydrogen or a group -CH2COOMc, in which Mc is as defined above; u is zero or is an integer equal to 1 or 2; v is an integer from 4 to 9; and Xc0 is a chloride,

or mixture of these compounds.

  5. Shampoo composition comprising, as essential surfactant, from approximately 5% to approximately 55% by weight of a compound

  according to any one of claims 1 to 4, or a method

diaper of these.

  6. Composition according to claim 5, characterized in that the essential surfactant constituent is present in

  an amount from about 10% to about 45% by weight.

  7. Shampoo composition comprising, as surfactant constituent, a mixture of an anionic surfactant and of a compound of formula I according to claim 1, the latter being present in an amount of from approximately 20% to approximately 50%.

weight of the mixture.

  8. Composition according to claim 7, characterized in that the compound of formula I is present in an amount

  from about 30% to about 45% by weight of the mixture.

  9.Composition characterized in that it contains a compound

  according to any one of claims 1 to 4 or a mixture of

  these. 10. Use of the composition according to claim 9

as a shampoo.