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
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C231/00—Preparation of carboxylic acid amides
  • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups

Definitions

• the subject of the present invention is acids or salts of ⁇ -amino-substituted acetic acids completely free of haloacetic acid and alkali halide, as well as a process for the preparation of said acids or salts and the use of said acids or salts. of acetic amino-substituted acids of very high purity as surfactants in cosmetic compositions.
• these are acids or salts of ⁇ - amino-substituted acetic acids of formula (I)
• R represents a hydrogen atom or an alkyl or alkoxyl group, linear or branched and optionally substituted, C *
• X represents a hydrogen atom, an alkali or alkaline-earth metal or ammonium residue, characterized in that they are completely free from haloacetic acid and from alkali halide.
• the present invention relates very particularly to the acid form of N-lauroyl N '- (2-hydroxyethyl) - N - (carboxymethyl) ethylenediamine and its salts.
• Many compounds of general formula (I) and more particularly their inorganic salts are widely used in the detergency and cosmetic industries as amphoteric agents. In addition to their surfactant qualities, these compounds also prove to have, due to their chemical structure, a highly appreciated biodegradable character.
• As a particularly interesting compound there may be mentioned in particular the sodium salt of N-lauroyl N '- (2-hydroxyethyl) - N'- (carboxymethyl) ethylenediamine.
• chloroacetic acid like its salts, has an irritant character which is well established today. For these reasons, it is desirable today to have compounds of formula (I) completely free of haloacetic acid and alkali halide.
• the acids or acid salts of the invention preferably do not contain more than 0.5% of their weight of glycolic acid.
• the compounds which are the subject of the invention are capable of being obtained by hot reaction of glyoxal or of a precursor of glyoxal, on a secondary amine or one of its salts of general formula (II).
• the secondary amine of general formula (II) can preferably be obtained by basic in-situ or extemporaneous hydrolysis in the reaction medium of an imidazoline of general formula (III)
• R represents a hydrogen atom or an alkyl or alkoxyl group, linear or branched and optionally substituted, at C *
• the hydrolysis of the imidazole of general formula (III) is carried out in a conventional manner in an aqueous medium and in the presence of a base. It is more especially soda. Those skilled in the art are able to share their technical skills in reproducing this hydrolysis.
• this process for preparing the compounds of formula (I) is relatively easy to carry out. Although the presence of an excess of glyoxal does not affect the course of the reaction, this compound is preferably used in an equimolar amount relative to the secondary amine. This eliminates any subsequent purification step.
• glycoxal precursor is intended to denote any compound capable of generating glyoxal in the reaction medium. Tetrahydroxy-4,4 ', 5,5'-bis (dioxolane -1, 3) -2.2 meets this definition in particular.
• the glyoxal used according to the invention is preferably in the form of aqueous solutions of 30 to 55% by weight of glyoxal.
• aqueous solutions of 30 to 55% by weight of glyoxal.
• other soluble forms of glyoxal are familiar to those skilled in the art and will therefore not be recalled here.
• organic solvent capable of being used according to the invention of water, alcohols such as ethanol, methanol and propanols as well as their mixtures. It is more particularly water.
• hot reaction is meant according to the invention, a reaction carried out at a temperature greater than or equal to 60 ° C.
• it is a temperature between 60 ° C and 100 ° C and preferably of the order of 80 ° C.
• the reaction time is a function of the temperature.
• a reaction carried out at 80 ° C. is completed in approximately 2 to 3 hours.
• This process is particularly useful for preparing the acid form of N-lauroyl N '- (2-hydroxyethyl) - N'- (carboxymethyl) ethylenediamine.
• This compound can be obtained for example by condensation reaction, hot, of glyoxal on N- (2-hydroxyethyl) laurylimidazoline or of tetrahydroxy-4,4 ', 5,5'-bis-
• the acid form of the compounds of general formula (I) can be subsequently converted into its alkaline, alkaline-earth or ammonium salts, by conventional neutralization procedures familiar to those skilled in the art and which will therefore not be repeated here. .
• neutralizing agent capable of being used there may be mentioned more specifically the hydroxides of alkali or alkaline earth metals and the amines such as ammonia and triethanolamine.
• the high purity compounds which are the subject of the invention can be used as amphoteric surfactants, for the preparation of cosmetic compositions such as shampoos, toilet milks, etc.
• Example 2 A solution of N- (hydroxyethyl-2) laurylimidazoline (5 g, 18.7 mmol) and sodium hydroxide pellets (40 mg) in water (1.06 g) is heated at 80 ° C for 1 hour. A mixture of 40% glyoxal in water (2.7 g, 18.7 mmol) and propanol-1 (5 g) is then added and the residual solution heated for 6 hours at 80 ° C. A capillary electrophoresis assay indicates a yield of 85% in N-lauroyl-N '- (2-hydroxyethyl) N'- (carboxymethyl) ethylenediamine.
• N- (hydroxyethyl-2) laurylimidazoline (10 g, 37.3 mmol), water (2 g) and sodium hydroxide pellets (80 mg) is heated for 1 hour at 80 ° C.
• Glyoxal bis- (sodium hydrogen sulfite) (10.6 g, monohydrate, 37.3 mmol) is then added and the mixture heated for 6 hours at 80 ° C.
• An assay by capillary electrophoresis indicates a yield of 75% in N-lauroyl-N '- (hydroxyethyl-2) -N'- (carboxymethyl) ethylenediamine.
• Example 5 A mixture of N-lauroyl-N '- (hydroxyethyl-2) ethylenediamine (7.28 g, 25.4 mmol) of tetrahydroxy-4,4', 5,5'-bis- (dioxolane-1, 3) - 2.2 'crystallized (1.783 g, 8.5 mmol), and propanol-1 (10 g) is heated. 12 hours at 80 ° C.
• a capillary electrophoresis assay indicates a yield of 19% in N-lauroyl-N '- (2-hydroxyethyl) -N' - (carboxymethyl) ethylenediamine.
• N- (hydroxyethyl-2) laurylimidazoline (20 g, 74.6 mmol), sodium hydroxide pellets (153 mg) and water (4.169 g) is heated for 1 hour at 80 ° C.
• Water (41.4 g) is then added and a 21% solution of glyoxal in water (21 g) is poured over two hours at 80 ° C.
• the reaction mixture is then heated for 6 hours at 80 ° C.
• An assay by capillary electrophoresis indicates a yield of 97% in N-lauroyl N '- (hydroxyethyl-2) -N' - (carboxymethyl) -ethylenediamine.
• the characteristics of impurity profile, foaming power and viscosity of the amphoteric surfactant prepared in Example 6 are as follows Impurities pH (aqueous solution dry extract NaCi glycolate at 10%) (% by weight) (% by weight) (% by weight) (% by weight)
• the foaming power was determined according to the modified Ross-Miles test (AFNOR standard T-73404) at room temperature, at a concentration of 0.1%. volume of foam (in ml) 310 Viscosity power This is measured using the following formulation
• the NaCI concentration varies from 0 to 5%; the addition of NaCl increases the viscosity of the medium.
• viscosity mPa.s.
• dry extract %) NaCI 0% NaCI 3% NaCI 5% 30 2 51 2000
• EXAMPLE 7 Shampoo The N-lauroyl-N '- (hydroxyethyl-2) -N' - (carboxymethyl) ethylenediamine obtained according to Example 4 is introduced into a shampoo formulation as follows:
• This shampoo formulation has a pH of 6.4 and a viscosity of
• the compound obtained according to Example 4 is also introduced into a formulation of baby toilet milk.
• Guar hydroxypropyl is introduced into water with vigorous stirring, then the pH is adjusted to 5-6 with citric acid.
• the guar solution is then introduced into the mixture of surfactants and N-lauroyl-N'- (hydroxyethyl-2) -N '- (carboxymethyl) ethylenediamine, the pH adjusted to 7 with citric acid.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Cosmetics (AREA)
• Detergent Compositions (AREA)

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• 1993
  • 1993-12-10 ES ES94902014T patent/ES2123751T3/es not_active Expired - Lifetime
  • 1993-12-10 US US08/454,311 patent/US5869712A/en not_active Expired - Fee Related
  • 1993-12-10 EP EP94902014A patent/EP0674616B1/fr not_active Expired - Lifetime
  • 1993-12-10 AT AT94902014T patent/ATE168990T1/de not_active IP Right Cessation
  • 1993-12-10 DE DE69320062T patent/DE69320062T2/de not_active Expired - Fee Related
  • 1993-12-10 WO PCT/FR1993/001223 patent/WO1994013621A1/fr not_active Ceased
  • 1993-12-16 IL IL108055A patent/IL108055A/en not_active IP Right Cessation
  • 1993-12-17 TW TW082110737A patent/TW266202B/zh active
  • 1993-12-17 CN CN93119878.XA patent/CN1095371A/zh active Pending

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