Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/10—Preparations for permanently dyeing the hair
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
  • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
  • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
  • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
• • 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

Definitions

• compositions according to the invention comprise very valuable surface-active agents which may be used either alone or mixed with other cationic, anionic or non-ionic surface active agents, in many different fields, and particularly for shampooing the hair and in the preparation of hair dyeing solutions.
• alkylene diamines As an example of particularly suitable alkylene diamines the following may be mentioned:
• N- (.fl-aminopropylpiperidine) The following may, of course, also be used:
• N,N-dimethylor N,N-diethylbutylenediamines N,N-dimethylor N,N-diethylpentamethylenediamines.
• fatty amines As examples of particularly suitable fatty amines the following may be cited: decylamine, dodecylamine, the amines derived from the fatty acids of copra-0r tallow, etc.
• the new amphoteric chemical compositions according to the invention may be used in aqueous solutions at acid, neutral or alkaline pH values. In the first case they act as cationic surface active agents; in the last case, as anionic surface active agents.
• the invention thus also envisages, as a new article of manufacture, a surface active composition characterized by the fact that it contains a composition having the general Formula I as given above.
• Thenew composition according to the invention may naturally comprise other known cationic, anionic, or nonionic surface active agents. It is particularly valuable for use in sha-mpooing the hair.
• the cornea may be attacked in cases 5 and 6 either by the product itself or by the pathological conjunctival Apphcatmn ofasolutlon of secretion caused by the product.
• the corneal lesions being of two types, the numbers tion of the anhydride
• the length of h operfitioh is 2 corresponding to the most serious damage may also be hours 30 s, and the N,N-diethyl aminopropyl f ll wed b maleamic acid begins to precipitate several minutes before the end of this addition.
• (a) Which corresponds to a loss of brilliance (cornea
• the reaction mixture is allowed to stand, at ambient roughened), temperature, for a few hours.
• the maleamic acid which (b) Which corresponds to the more or less complete has formed is then separated by filtration. After washdestruction of the corneal epithelium withmore or less g with ethyl acetate, the Product is dried and re ov r d extensive ulceration and loss of corneal sensitivity.
• the yield is 100%.
• Example A-2 204 g. (2 moles) of N,N-dimethylaminopropylamine is dissolved in 800 g. of t-butyl alcohol, and the temperature of the solution thus obtained is brought to 50 C. 198 g. of powdered maleic anhydride is added with agitation. This operation is completed over one hour at a temperature of 50 C.
• the reaction mixture is allowed to stand for several hours.
• the dimethylaminopropyl maleamic acid forms a precipitate. It is separated by filtration. After washing with acetone, draining, and drying, the product is recovered in the form of a white powder.
• the yield is 98%.
• the choice of temperature is important: it should be less than 30 C. in order to avoid esterification, when an alcohol is the solvent, and hydrolysis, when water is the solvent.
• the yield of the amide is always greater than 90%.
• Example B-1 Preparatin of N-(morplzolinobutyD- maleamic acid CHz-OH:
• Example B-2 Preparation 0 N-(N,N'- diethylaminopentyl)-maleamic acid CH-CONH-(CHm-N I one-coon 02m 7
• N-(N',N'-diethylaminopentyl)-maleamic acid is ob- ,tained in a methanol solution starting with diethylamino- S-pentylamine and maleic anhydride.
• Example B-3 In the same manner as Example B-1, N-(piperidinopropyl)-maleamic acid in an ethanol solution is prepared, starting from piperidinopnopylarnine and maleic anhydride.
• Example B-4 Preparati0n of N,N-(diethylamin0- pr0pyl)-maleamic acid in water solution Milliequivalents/gram Acidity 4.54 Amino nitrogen 4.36
• Example B-5 Preparati0n of N,N-(dimethylamin0- pr0pyl)-maleamic acid in water solution Milliequivalents/ gram Acidity 5.39 Amine nitrogen 5
• the following examples illustrate Ways of preparing the new chemical compositions according to the invention.
• N-(N',N'-diethylaminopropyl)-maleamic acid is first prepared in the manner described in US. Patent No. 2,821,521, issued January 28, 1958.
• R alkyl residue derived from the fatty acids of copra.
• Example 2 The procedure is the same as in Example 1, but the primary amines deriving from the fatty acids of copra are used instead of dodecylamine. A product having the following formula and a purity of 95% is thus obtained, in the form of a viscous clear yellow mass, soluble in water at any pH. A 10% aqueous solution has a pH of 11.9.
• N-(N',N-diethylaminoethyl)-maleamic acid is first prepared in the same way as in Example 1 by reacting N,N-
• This asparagine derivative is obtained in a purity of 96%, in the form of a viscous clear yellow mass, soluble in water at all pH values.
• a aqueous solution has a pH of 11.1.
• R is an alkyl residue derived from the fatty acids of tallow.
• This product is obtained by following the procedure hereinbefore described, using N,N-diethyl-ethylene diamine and the fatty amines derived from the fatty acids of tallow. Its purity is 94%. A 10% aqueous solution has a pH of 11.7.
• Example 2 Proceeding as in Example 1, but replacing dodecylamine with the primary amine derived from the fatty acids of copra, the above-mentioned asparagine derivative is obtained in a purity of 98%.
• a 10% aqueous solution has a pH of 11.5.
• R being an alkyl residue derived from the fatty acids of copra.
• N-(morpholinoethyl)maleamic acid is first prepared in the same way as in Example 1, by reacting N-(fi-amino ethyl) morpholine with maleic anhydride.
• the product is in the form of a white solid having its melting point at 161-162 C.
• the primary amines derived from the fatty acids of copra are then reacted with the potassium salt of that acid.
• the desired product is obtained in a purity of in the form of a yellow-orange viscous mass, soluble in water at all pH values.
• a 10% aqueous solution has a pH of 11.6.
• N-(piperidinopropyl)-malearnic acid obtained in alcoholic solution is neutralized with 11.1 g. of 33. 8% sodium hydroxide solution after which 17.5 g. of dodecylamine are added.
• the mixture is then heated at 65 C. for 5 hours, and concentrated by the evaporation from the solution of 60 g. of alcohol, the temperature being maintained at 65 C. for another 3 hours.
• the alcohol and the water are removed under vacuum; a pasty product is obtained, which is soluble in water.
• R is an alkyl residue derived from the fatty acids of copra.
• N-(morpholinobutyl)-maleamic acid (0.2 mole) obtained in methanol solution above, is neutralized 'by a stoichiometric amount of a 33% aqueous solution of sodium hydroxide.
• 0.2 mole of primary amines derived from the fatty acids of copra is added, and themixture is heated to 65 C. for 12 hours. On evaporation to dryness, a white paste containing 90% of the product of the above formula is obtained.
• Example 10(a) The same procedureemployed in Example 10(a) is used, and N-(N,N'-diethy1aminopentyl)-maleamic acid is obtained in a methanol solution starting from diethylamino--pentylamine and maleic anhydride.
• R is an alkyl residue derived from the fatty acids of copra.
• N-(N,N'rdiethylaminopentyl)-maleamic acid obtained in part (a) above in methanol solution is neutralized by a stoichiometric amount of sodium hydroxide.
• the mixture is heated at 65 C. for8 hours, with the primary amine derivatives of the [fatty acids of copra.
• amic acid of the formula:
• the maleamic acid derivative is thereby obtained.
• R is an alkyl radical derived from the fatty acids of copra.
• Lactic acid in a quantity sufi'icient to bring the pH value Water, q.s.p., cc.
• Example 3A A solution is prepared which contains:
• Example 4A The shampoo thus obtained foams well and imparts great softness to the washed hair.
• Example 5A An aqueous solution is prepared which contains the following:
• This shampoo foams well and imparts great softness to the washed hair.
• Example 6A An aqueous solution is prepared which contains the following:
• This solution constitutes shampoo which is an effective detergent, foams well, and imparts great softness to the washed hair.
• Example 7A An aqueous solution is prepared which contains:
• This viscous shampoo is a good detergent and foams well. It imparts great softness to the hair which is washed with it.
• Example 8A An aqueous solution is prepared which contains:
• This solution constitutes an excellent shampoo which is an effective detergent, foams well and imparts great softness to the washed hair.
• Example 9A An aqueous solution is prepared which contains:
• This solution constitutes a shampoo having good foaming and detergent properties. It makes the hair supple and easy to comb.
• Example 10A An aqueous solution is prepared which contains:
• Example 11A An aqueous solution is prepared which contains:
• Lactic acid q.s.p., pH 7.5.
• This solution constitutes an excellent shampoo, which has good deter-gent and foaming properties, and gives the hair a brilliant sheen.
• the shampooing compositions have been adjusted to have a pH of 4 to approximately 8.6 by the addition of lactic acid, other acids may be used, and a higher pH may also be used.
• Example 12A A solution is prepared which contains:
• This solution gives a foamy shampoo and permits the hair to be easily combed.
• Example 13A A solution is prepared which contains:
• This solution gives a foamy shampoo and permits the hair to be easily combed.
• This solution constitutes a shampoo having foaming and detergent properties and making the hair supple and easy to comb.
• hair which has been shampooed with it does not have an accumulated electrostatic charge after drymg.
• This solution constitutes a shampoo having foaming and detergent properties and making the hair supple and easy to comb.
• hair which has been shampooed with it does not have an accumulated electrostatic charge after drying. 7
• Example 16A A solution is prepared which contains:
• Example 17A A solution is prepared which contains:
• Example 18A An aqueous solution is prepared which contains the following:
• Example 19A I An aqueous solution is prepared which contains the following:
• This shampoo foams well and imparts great softness to the washed hair.
• Example 20A An aqueous solution is prepared which contains the following:
• This solution constitutes .shampoo which is an effective detergent, foams well and imparts great softness to the washed hair.
• Example 21A An aqueous solution is prepared which contains: Potassium salt of N (morpholino-ethyl)-N alkyl (fatty) asparagine, 7 'g. Sufiicient citric acid to bring to a pH of 7.5. Sufiicient water to make cc.
• This solution constitutes an excellent shampoo which is an effective detergent, foams well and imparts great softness to the washed hair.
• a hair dyeing composition is prepared, which contains the following: 7
• This solution is diluted weight by weight with hydrogen peroxide to 20 volumes.
• the final pH is 9.9.
• the shade of dyeing which is obtained is chestnut.
• Example 2B A hair dyeing solution is prepared which contains: Sodium salt of N-(N',N'-diethylaminopropyl)-N dodecyl asparagine g 3 Sodium salt of N-(N,N-diethylaminoethyl)-N alkyl (tallow) asparagine g 1 Nonyl phenol+4 mols ethylene'oxide g 20 Nonyl phenol+8.75 mols ethylene oxide g 20 Diethylene glycol g 17 Ethyl alcohol g 3 Ammonia at 22 B. ml 12 Paratoluylene diamine g 0.2 Metadiaminoanisol sulfate g 0.01 Resorcine g 0.1 p- Aminophenol g 0.3 m-Aminophenol g 0.05
• Example 3B A hair dyeing solution is prepared which contains the Water, q.s.p., 100 cc.
• the shade of dyeing obtained is golden chestnut.
• Example 4B 7 A hair dyeing solutionis prepared which contains: Ammonium salt of N-(N,N-diethylaminopropyl)- N -alkyl (fatty.).aspa ragine, in .which .the fatty residues are composed of of the fattychain portion of thefatty acidsof copra and /3 of the fatty chain portion of the fatty acids .of tal- .low g 4 Nonyl phenol+4 mols ethylene oxide g 20 Nonyl phenol+8.75 mols ethylene oxide g 20 Diethylene glycol g 17 Ethyl alcohol g 3 Ammonia at 22 B. ml 12 Paratoluylene diamine g 0.6 Metadiaminoanisol sulfate g 0.15 Resorcine g.. 0.5 p-Aminophenol g 0.4 m -Aminophenol g 0.1
• This solution is diluted weight for weight with hydrogen peroxide to 20 volumes.
• the final pH is 9.5.
• the shade of dyeing obtained is chestnut brown.
• Example 5B Water, q.s.p., 1000 g.
• This solution is mixed with an equal volume of hydrogen peroxide and applied in the usual manner to the hair.
• the shade imparted to the hair is chestnut brown.
• Example 7B 7 The following composition is prepared:
• R and R are alkyl of up to four carbon atoms or together with the nitrogen atom to which they are attached form morpholino or piperidino, n is an integer having a value between 2 and 5 inclusive, R is a saturated aliphatic hydrocarbon having from 10 to 18 carbon atoms inclusive, and M is selected from the group consisting of sodium, hydrogen, potassium and ammonium.

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Citations (4)

• 0
  • NL NL288966D patent/NL288966A/xx unknown
  • BE BE628087D patent/BE628087A/xx unknown
  • NL NL123199D patent/NL123199C/xx active
• 1962
  • 1962-02-15 FR FR888177A patent/FR1344212A/fr not_active Expired
• 1963
  • 1963-02-13 CH CH176363A patent/CH401988A/fr unknown
  • 1963-02-14 DE DEO9241A patent/DE1223994B/de active Pending
  • 1963-02-15 GB GB6329/63A patent/GB1003345A/en not_active Expired
• 1965
  • 1965-02-13 CH CH392065A patent/CH404088A/fr unknown
  • 1965-09-13 US US487084A patent/US3303213A/en not_active Expired - Lifetime
  • 1965-12-21 NL NL6516650A patent/NL127053C/xx active
  • 1965-12-21 NL NL6516651A patent/NL6516651A/xx unknown
• 1966
  • 1966-01-20 BE BE675407D patent/BE675407A/xx unknown
  • 1966-01-27 GB GB26106/67A patent/GB1125919A/en not_active Expired
  • 1966-01-27 CH CH111366A patent/CH432541A/fr unknown
  • 1966-01-27 GB GB3788/66A patent/GB1094205A/en not_active Expired
  • 1966-02-27 IT IT01941/66A patent/IT1048991B/it active

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