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
  • A61Q5/02—Preparations for cleaning 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
  • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
  • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/10—Washing or bathing preparations
• • 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

• a biodegradable surface active composition that does not irritate the eyes comprising an aqueous solution of a compound having the formula RCO-NH( CH CH O SO M in which R is an alkyl or alkenyl group and M is a cation.
• a first category of such known surface-active agents comprises the sulfates of fatty alcohols, in the form of the alkali salts, such as sodium, ammonium, etc., in which the fatty alkyl remainder, hereinafter designated by R, comprises 12-18 carbon atoms.
• These sulfates may respond to one of the two formulas ROSO M or according to whether the product is or is not oxyethylenated.
• ROSO M is a number from 1 to 4 and M is a cation, such as sodium, potassium, ammonium, etc.
• the products falling in this category have excellent detergent qualities, but they irritate the skin and mucous membranes, and their use makes the hair feel rough after shampooing.
• a second category of known surface-active agents comprises the sulfated amides, which have the great advantages that their use imparts an agreeable feel to the hair after shampooing and they are less irritating to the skin and mucous membranes.
• the sulfated amides heretofore known tend to hydrolyze after a few days in solution, so that it is necessary to prepare the solution containing them just before use. These sulfated amides are therefore suitable only for use in powders, and not for use in shampoos sold in solution form.
• the objects of the present invention is to avoid the disadvantages of the sulfate of fatty alcohols, i.e., the tendency to irritate the skin and the undesirable feel with which the hair is left after shampooing, without accepting the lack of stability in solution which is characteristic of the known sulfated amides.
• the present invention is therefore directed to the new article of manufacture which is an anionic surface-active agent in the form of an amide sulfate having the following formula:
• R is a linear or branched chain alkyl or alkenyl, having from 11 to 26 and preferably 11-17 carbon atoms
• M is an alkali metal, alkaline earth metal, ammonium, or a short-chain mono, di or tri alkyl-ammonium or alkylol ammonium.
• a further object of the present invention is to provide new cosmetic compositions containing, preferably in aqueous solution, at least one composition responding to Formula I, these compositions being especially useful for shampooing the hair. It is clear that these compositions may contain other products and additives conventionally used in cosmetics such as thickening agents, other ionic or nonionic surface active agents, etc.
• compositions containing the compounds of Formula I are particularly resistant to hydrolysis so that they may be used in the manufacture of shampoos to be sold as aqueous solutions. It should be noted that the hydrolysis stability of the amide sulfates of this invention cannot be predicted from the stability of the corresponding amide because an amide may be stable to hydrolysis even though its sulfates are unstable.
• the cosmetic compositions of this invention generally contain from 5 to 20%, and preferably about 10% by weight of the compounds of Formula I.
• the pH of these compositions may be between 6 and 9 and preferably about 7. These compositions at this concentration and pH range will not hydrolyze and will not irritate the skin and mucous membranes of the eyes.
• compositions of this invention when used in shampoos, impart an agreeable feel to the hair, and they do not irritate the mucous membranes, especially those of the eye, a fact which has been verified by tests on the eyes of live rabbits. These compositions are also readily bio-degradable.
• Another object of the present invention is to provide a method of preparing compositions containing the compounds of Formula I essentially characterized by the fact that a fatty acid, such as one derived from copra, having the formula R-COOH, in which formula R designates an alkyl or alkenyl group having 11-26 carbon atoms is reacted with di-glycolamine and the alcohol function of the amide thus obtained is sulfated.
• the sulfation step may be followed by salification or the salification may occur concurrently.
• This process may be carried out in several different ways.
• the first step of the process which consists in obtaining the amide itself may be carried out in any of the following illustrative ways:
• the second step of the process which consists of sulfating the amide obtained in the first step, may also be carried out in several different illustrative ways, particularly:
• EXAMPLE 2 The following mixture is prepared: Solution containing 26.8% of Sulfuric ester of the diglycol amide of copra acids, am-
• EXAMPLE 3 The following mixture is prepared: Solution containing 26.8% of- Sulfuric ester of the diglycolamide of copra acids, am-
• composition described in each of Examples 2-4 when used as a shampoo, have good detergent properties, and produce plenty of foam having an agreeable consistency. After shampooing with the product the hair is glossy, bright, and feels soft to the touch.
• the RCO group in Formula I may be derived from the following illustrative fatty acids caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, pelargonic acid, undecylic acid (10- undeceneoic acid).
• the RC0 group in Formula I may also be obtained from mixtures of fatty acids obtained from oils and fats of animal or plant origin such as palm, cabbage palm, tallow, etc.
• the RCO group may also be obtained from isoacids having the general formula:
• n is between 14 and 22 and 12 and 22 respectively.
• acids can be prepared in the form of a mixture for saponification from lanolin.
• neoacids as for example the neo-tridecanoic acid having the formula:
• R is hydrocarbon radical containing 9 carbon atoms.
• Illustrative salts include those in which M in Formula I is:
• alkaline ions such as Na, K, etc.
• Alkaline earth metal ions such as calcium and magnesium.
• Illustrative compounds of the invention include: 1 C H CONH(CH CI-l O) SO Na [C14H29CONH) 2503] 2C3. (3) C13H27CONH CH2CH20 SO NH 4) C H CONH(CH CH O) SO NH (5 C H CONH(CH CH O) SO NH C H (6) C13H27CONH(CH2CH2O)2SO3NH2(C2H3)2 (7) C H CONH (CH CH O SO NH (CH 3 (8) C H CONH(CH CH O) SO NH (CH CH OH) (9) C H CONH(CH CI-I O) SO NH (CH CHOHCH (10) C13H27CONH(CH2CH20)2SO3NH(CH2CH2OH) 3
• the compositions which contain lauric and myristic acid derivatives and mixtures containing at least 50% of these acids have the best foaming characteristics.
• Compound A was prepared by the aminolysis of methyl laurate using diglycolamine (H NCI-l CH OCH CH OH) in excess of the required, the reactive mixture being progressively heated 7 up to 160 C. to eliminate the methanol. The excess of diglycolamine was then evaporated under vacuum. The product thus obtained was recrystallized in the ethyl acetate.
• Compound B was prepared by condensing ethylene oxide on lauric monoethanolamide (C H CONHCH CH OH) which was obtained by aminolysis of methyl laurate with monoethanolamine. Its melting point after recrystallization was 85 C.
• the condensation product contains the compounds C H CONHCH CH OH and C H CONHCH CH OCH CH OH in approximately equal proportions.
• Compositions in which n is a variety of values but statistically equal to 2 tend to hydrolyze, irritate the eyes and do not produce desirable foams.
• EXAMPLE 6 Preparation of ammonium and magnesium sulfate salts of dodecanoyl amido ethoxy ethanol having the formula: C H CONHCH -CH -0CH CH OH
• the hydroxylated amide is prepared by aminolysis of methyl laurate with diglycolamine in excess of 100% required for a complete reaction, the mixture is progressively heated up to C. to eliminate the methanol. The excess diglycolamine is then evaporated under vacuum. The product is then recrystallized in ethyl acetate.
• This compound is then sulfated with sulfamic acid according to the conditions which were given in Example 1.
• the sulfatation product was neutralized in the following manner:
• Milk of magnesia was prepared by dispersing 8 g. of magnesia in 20 ml. of water. This dispersion of magnesia was added under agitation to the chloroform solution of the sulfatation product. After one and one-half hours, the mixture having then a very acid reaction, we added 2 g. of pulverized magnesium. The mixture was left for one night, then we filtered the excess magnesia. The chloroform and water were evaporated. The yield was 80%. The residue was put in acetone and the magnesium salt precipitated. It was separated easily by filtration. This compound, after drying, is a white solid that can be pulverized. It dissolves very easily in water to form a foaming solution.
• composition of the present invention contains conventional shampoo ingredients choosed among the following:
• carboxymethyl cellulose oxyethylated lauric alcohol (12 mol. ethylene oxide), glycerol mono stearate, etc.
• a surface active composition consisting essentially of an aqueous solution consisting essentially of a surface activating amount of an amide sulfate surface active agent having the formula RCONH(CH CH O -SO M in which R is selected from the group consisting of alkyl and alkenyl groups having 11 to 17 carbon atoms, and M is an ion selected from the group consisting of alkali metals, alkaline earth metals, ammonium, alkylammonium, and alkylolammonium, having a pH of about 6 to 9.
• a method for shampooing hair comprising shampooing the hair with an effective amount of the composition of claim 1.
• a shampoo composition comprising the composition of claim 1 which also contains a compound selected from the group consisting of cetyl trimethyl ammonium bromide, lactic acid, diethanolamide of copra, polyethylene glycol, stearylic alcohol, paraffin oil, glycerin, ammonium lauryl sulphate, lauric diethanolamide, triethanolamide lauryl sulphate, carboxymethyl cellulose, oxyethylated lauric alcohol (12 mol. ethylene oxide) and glycerol mono stearate.
• composition of claim 1 wherein the amide sulfate surface active agent is the only surface active agent present.
• composition of claim 4 wherein R is C H 6.
• composition of claim 4 which contains 5 to 20% by weight of said surface active agent.
• composition of claim 4 wherein M is NH 10.
• a method of shampooing hair comprising shampooing the hair with a shampooing amount of the composition of claim 4.

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• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• General Health & Medical Sciences (AREA)
• Public Health (AREA)
• Veterinary Medicine (AREA)
• Chemical & Material Sciences (AREA)
• Epidemiology (AREA)
• Birds (AREA)
• Dermatology (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Organic Chemistry (AREA)
• Cosmetics (AREA)
• Detergent Compositions (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=19724234

Family Applications (1)

Country Status (8)

Cited By (7)

Families Citing this family (2)

• 0
  • NL NL127604D patent/NL127604C/xx active
• 1965
  • 1965-03-30 LU LU48285A patent/LU48285A1/xx unknown
• 1966
  • 1966-02-18 BE BE676733D patent/BE676733A/xx unknown
  • 1966-03-14 AT AT241366A patent/AT262947B/de active
  • 1966-03-14 AT AT710267A patent/AT274244B/de active
  • 1966-03-29 DE DE19661617691D patent/DE1617691B1/de active Pending
  • 1966-03-29 DE DE1593215A patent/DE1593215B2/de not_active Withdrawn
  • 1966-03-29 NL NL6604104A patent/NL6604104A/xx unknown
  • 1966-03-30 CH CH460966A patent/CH457399A/fr unknown
  • 1966-03-30 CH CH460866A patent/CH459471A/fr unknown
  • 1966-03-30 GB GB14170/66A patent/GB1107441A/en not_active Expired
• 1969
  • 1969-01-13 US US790838A patent/US3562170A/en not_active Expired - Lifetime

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