Classifications

• • 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
  • 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
  • C11D1/88—Ampholytes; Electroneutral compounds
  • C11D1/90—Betaines
• • 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
  • C11D3/16—Organic compounds
  • C11D3/20—Organic compounds containing oxygen
  • C11D3/2003—Alcohols; Phenols
  • C11D3/2006—Monohydric alcohols
  • C11D3/201—Monohydric alcohols linear

Definitions

• CO MP OS itions hydroalcoholic CONCENTRATED FLUIDS alkyl- AMID O R O PYLBETA ⁇ NES coconut or palm kernel oil.
• the invention relates to concentrated hydroalcoholic solutions of low viscosity, clear, little colored and stable in a temperature range between 5 and 50 ° C, and containing at least 50% by weight of al-yl-amidopropyl-betaine corresponding to the general formula (I):
• RI represents alkyl radical of a natural cut coconut type of fatty acid or palm kernel, which are approximately of saturated fatty acids, about 4 to 0 -5 0% lauric acid and 15-20% myristic acid (in the rest of the presentation, we simply say betaine).
• the solutions exhibit these qualities only if their composition is chosen precisely in a zone of the betaine / ethanol / water diagram normalized to 100 by weight after correction of the NaCl present.
• the betaines corresponding to the general formula (I) are amphoteric surfactants very well tolerated by the skin, having excellent cleaning and foaming characteristics, and which are entirely suitable for making a multitude of surfactant compositions, such as washing agents, cleaning agents (liquid products for washing dishes by hand) and compositions for hair care (shampoos) and body care (shower gels and bubble baths).
• HENKEL International application WO 95/12856 discloses and claims a process for manufacturing surfactants of betaine type with low salt content (0.98 to 1.01% residual NaCl) by quaternization of tertiary amines and / or tertiary amidoamines with sodium monochloroacetate in a hydroalcoholic mixture composed of 5 to 10% by weight of water and 35 to 50% by weight of ethanol and / or isopropanol, this reaction being followed by a elimination of the precipitated salt fraction, total elimination of the solvent and readjustment of the reaction medium in water in order to bring the solution to the desired concentration of active material, in this case 30%.
• alkylbetaine of copra or palm kernel which are as concentrated as possible, that is to say at least 50% by weight, clear and little colored, fluid and pumpable (viscosity less than 1000 mPa.s), stable between 5 and 50 ° C over extended periods of time, in order to reduce packaging, transport and storage costs, which are easy to handle and can be formulated in l 'state with other surfactants, for example alkyl ether sulfates, alkanolamides, or other basic raw materials used in particular in the formulations of liquid soaps, shampoos, shower gels, and other cosmetic preparations.
• surfactants for example alkyl ether sulfates, alkanolamides, or other basic raw materials used in particular in the formulations of liquid soaps, shampoos, shower gels, and other cosmetic preparations.
• the present invention provides a solution to this technical problem, which consists in preparing alkylbetaine in the presence of small amounts of ethanol, provided however to be limited to a very precise and narrow domain of the phase diagram such that defined now.
• ternary compositions betaine / water / ethanol, represented on the ternary diagram in reduced coordinates
• B * [betaine / (betaine + water + ethanol)].
• 10 2 W * [water / (betaine + water + ethanol)].
• 10 2 E * [ethanol / (betaine + water + ethanol)].
• the betaine taken into account is a crude betaine, that is to say made up of alkylamidobetaine as corresponding to formula I, with some reactive residues and some reaction by-products of not more than 3% by weight. (see example 1).
• compositions of the invention are those which obey relationships
• compositions of the invention NaCl is present at a maximum level of 4.5% by weight, a value beyond which these compositions become uncontrollable, if only by precipitation of the salt.
• the compositions according to the invention are suitable for prolonged storage over periods of at least three months, during which no gelling, no demixing, no precipitation of salts is observed, no significant change in color or clarity in the temperature range between 5 and 50 ° C.
• These solutions also have the advantage of being low foaming in the concentrated state which facilitates their handling. Another advantage is that these concentrated solutions are sufficiently resistant to microbial invasion, so that the addition of preservatives is unnecessary. These characteristics make these solutions particularly suitable for making cosmetic compositions.
• Another object of the present invention relates to the process for the manufacture of these concentrated solutions which consists in preparing the dimethylaminopropylamides of coconut or palm kernel intermediates and in quaternizing them with monochloroacetic acid in the presence of sodium hydroxide or the sodium monochloracetate directly in the chosen solvent medium, that is to say obeying the rule of composition
• Example 1 manufacture of a copra betaine containing approximately 59.2% by weight of betaine, ie 63.3% of dry extract, the reduced coordinates B * / W * / E * in the phase diagram are 61 , 7 / 15.4 / 22.9 (in% by weight).
• a concentrated betaine solution is thus obtained having the following main compositions:
• Active ingredient betaine dry extract - NaCl (including glycolate, free fatty acid and free amidoamine) _Q: Values B *, W * and E * in the ternary diagram, after correction of the content in NaCl then normalization to 100 by weight and the following additional characteristics: d: Rhéomat 180: Mobile 12; speed 231 (5 ° C) / 354
• a viscous non-Newtonian birefringent gel, of the liquid crystal type, is obtained which is difficult to handle and to formulate between 5 and 50 ° C.
• a fluid, clear and monophasic solution is obtained near ambient temperature (20 - 25 ° C) but which, between 5 and 15 ° C, undergoes a rapid evolution towards a biphasic mixture with a viscous gel phase. birefringent and a supernatant liquid phase. This heterogeneous product is difficult to use in the state.
• Counterexample 1 The same operating conditions are used as in step l / b of Example 1, with the exception of the raw material charges, which have been adjusted to obtain a copra betaine at approximately 57.5% of betaine, ie 61.6% of dry extract, whose triangular coordinates B * / W * / E * corrected for NaCl in the phase diagram are 60/25/15 (in% by weight).
• a viscous non-tonic birefringent gel, of the liquid crystal type, is obtained which is difficult to handle and to formulate between 5 and 50 ° C.
• Counterexample 4 The operating conditions of step l / b of Example 1 are repeated, with the exception of the raw material charges, which have been adjusted to obtain a copra betaine containing approximately 47.8% betaine. , ie 52.3% of dry extract, whose triangular coordinates B * / W * / E * corrected for NaCl in the phase diagram are 50/35/15 (in% by weight).
• a viscous non-Newtonian birefringent gel, of the liquid crystal type, is obtained, difficult to handle and to formulate between 5 and 50 ° C.
• Counterexample 5 The same operating conditions as in step l / b of Example 1 are repeated, with the exception of the raw material charges, which have been adjusted to obtain a copra betaine at approximately 58.2% of betaine, ie 60% of dry extract, whose triangular coordinates B * / W * / E * corrected for NaCl in the phase diagram are 58.5 / 13.5 / 28.0 (in% by weight).

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Health & Medical Sciences (AREA)
• Emergency Medicine (AREA)
• Cosmetics (AREA)
• Detergent Compositions (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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• 1997
  • 1997-11-07 FR FR9714034A patent/FR2770841B1/fr not_active Expired - Fee Related
• 1998
  • 1998-10-27 WO PCT/FR1998/002297 patent/WO1999024157A1/fr not_active Application Discontinuation
  • 1998-10-27 JP JP52556999A patent/JP2001507720A/ja active Pending
  • 1998-10-27 EP EP98952797A patent/EP0958042A1/de not_active Withdrawn
  • 1998-10-27 US US09/331,974 patent/US6335370B1/en not_active Expired - Fee Related
  • 1998-10-27 AU AU10368/99A patent/AU1036899A/en not_active Abandoned
• 1999
  • 1999-07-06 NO NO19993334A patent/NO313574B1/no not_active IP Right Cessation

Non-Patent Citations (1)

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