Classifications

• • 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
  • C11D1/94—Mixtures with anionic, cationic or non-ionic compounds
• • 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
• • 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
• • 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
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/02—Preparations for cleaning the hair
• • 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
  • C11D1/66—Non-ionic compounds
  • C11D1/75—Amino oxides
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/59—Mixtures
  • A61K2800/596—Mixtures of surface active compounds

Definitions

• the shampoo of this invention contains amine oxide and anionic detergent. In addition to cleaning the hair and producing copious suds, use of the shampoo reduces the static electrification of dry hair on combing or brushing and increases its manageability.
• the hair fibers repel each other giving the hair an unkempt, fuzzy, flighty appearance. This effect is often spoken of as hair fly for brevity and convenience. While the static charge will slowly dissipate from the hair fibers, recomb-ing will cause the same diificulty to arise again.
• shampoo preparation is designed to preserve much of the natural oil in the hair, the criticism can be voiced that it does an incomplete cleaning job.
• Some shampoos attempt to solve this problem by using a highly effective detergent and a hair conditioning agent which serves as a replacement for the oil removed from the hair.
• hair conditioning agents are polyglycols, fatty acid esters of glycols, natural or synthetic waxes, and lanolin derivatives.
• Use of formulations containing excessive amounts of hair conditioning agents of the oily type may cause the hair to have an unpleasant oily appearance and feel.
• Formulations containing certain hair conditioning agents suffer from the aditional difficulty that the oily material inhibits sudsing of the shampoo. Most people have come to expect copious lather from their shampoo and are dissatisfied if it is not formed.
• Among the objects of this invention are: (1) to provide a homogeneous shampoo which produces a copious lather, effectively cleans the hair, leaves the hair in a lustrous condition and additionally (2) to provide a shampoo which leaves the shampooed hair after drying in a manageable condition such that static electrification caused by combing or brushing is reduced or eliminated.
• formulations containing specified amine oxides and detergents with intermediate linkages including in this class ampholytic detergents, at pH values of from about 6.5 to about 8.5.
• Amine oxide is the ingredient which has the primary effect in reducing the static electrification of hair, and it is more effective at relatively low pH values of about 6.5 to about 8.5 than at higher pH values. Although it has sudsing and detergent properties, it is not suitable as the sole surface active ingredient of a shampoo. It should be combined with an anionic detergent to improve lather and mildness, and to lower cost. However, amine oxide and many conventional anionic detergents are incompatible, that is, do not form homogeneous solutions free from a precipitate of these components at these low pH values. Certain detergents characterized by an intermediate link are compatible in specified composition ranges.
• These detergents with intermediate links can be ampholytic or anionic detergents.
• Amine oxide can be combined with an ampholytic detergent or an anionic detergent with an intermediate linkage or with both.
• anionic detergents without 3,086,943 Patented Apr. 23, 1963 "ice intermediate links can also be dissolved in the shampoo formulation.
• Amine oxides are nonionic compounds of the general formula R R R N O.
• the arrow is a conventional representation of a semipolar bond. They are generally prepared by the direct oxidation of the appropriate tertiary amine.
• R is a much longer chain than R and R amine oxides have surface activity.
• R is an alkyl radical of from 10 to 16 carbon atoms. Desirable surface active and fly reducing properties are lost if R is substantially less than 10 carbon atoms, and solubility in the present formulation is too low if R is greater than 16 carbon atoms.
• R and R are each selected from the group consisting of methyl and ethyl radicals.
• R is a dodecyl radical or a mixture of dodecyl with decyl, tetradecyl and hexadecyl radicals such that at least 50% of the radicals are dodecyl radicals.
• R and R are preferably methyl radicals.
• the amine oxide will be used at from about 2% to about 15% of the total formula, preferably at from about 5% to about 10%. Too little amine oxide does not contribute sufiicient sudsing and hair control performance to the formulations. Too much amine oxide interferes with putting a sufiicient amount of anionic detergent in the formula while maintaining it as .a homogeneous liquid.
• the static electrification caused by combing or brushing dried shampooed hair is decreased. In other words, hair fly is decreased.
• Below about pH 8.5 the decrease in static electrification is significant; pH values of about 8 or lower are preferred for the decrease is greater.
• the pH is maintained above about 6.5 and high enough to keep the amine oxide and anionic detergent compatible. At too low a pH the amine oxide and anionic detergent interact to form a precipitate.
• a week acid such as citric acid is preferably used, because of its buffering effect, if it is necessary to lower the pH of the formula. Less than about 2% is employed. Other common acids can be employed.
• the minimum pH at which compatibility is maintained is, of course, affected by the concentrations and proportions of amine oxide and anionic detergent.
• R is an acyclic hydrophobic group containing from about 8 to about 18 carbon atoms
• Z is an intermediate group joined to R by a member of the group consisting of ether, polyether, ester, amide and amine linkages having some polar character derived from nitro-/ gen and/or oxygen atoms
• M is a cation to neutralize the charge of the anion. Classification according to, whether the detergent has an intermediate linkage or not is used in Surface Active Agents and Detergents, by A. M. Schwartz, J. W. Perry, and J. Berch, Interscience Publishers, New York, 1958, vol. II.
• the compatible detergents can be subdivided according to whether the intermediate linkage, Z, contains a basic nitrogen, or not, i.e., whether the detergent is an ampholytic detergent or not.
• a secondary or tertiary nitrogen is considered a basic nitrogen but a quaternary nitrogen, an amide nitrogen, or a substituted amide nitrogen is not.
• Detergents with intermediate links illustrative of the types suitable for use in the formulations of this invention include those listed in the following groups I and II. Additional ampholytic detergents suitable for use in this invention are included in those disclosed in Schwartz et al., as cited above, on pages 138444. R and M have the same meaning as before; R'C, in an acylradical, .has the same number of carbonatoms as R.
• ANIONIC Alkyl glyceryl ether sulfonate ROCH CHOHCH SO M, including mixtures of up to 40% alkyl diglyceryl ether.
• Alkyl monoglyceride sulfate Fatty acid ester of isethionic acid, R'COOC H SO M. N-methyl-N-alkyl taurate, -R'CON(CH )C I-I SO M.
• alkyl polyethenoxyether sulfate where x is about 3 is an especially preferred anionic detergent with an intermediate link because of its m-ildness and excellent performance.
• a long chain imidazole derivative having the general formula N CHz CHrCHrOGHzOOOM OH CHzC O OM The detergent with an intermediate l-inkage can be selected from either group I or group II or can be a mixture of detergents selected from both groups.
• the total of detergent with intermediate linkage is from about to about 20%.
• the upper limit is to insure an adequate temperature range ofhomogeneous solution; and the lower limit is to insure an adequate contribution towards the performance of the formulation.
• the anionic detergent with an intermediate linkage is used atfrom 0 to about and when used as the sole intermediate linkage-containing waterrsoluble detergent, this detergent constitutes at least 5% of the total composition; but preferably it is not present in more than a two-fold weight excess over the amine oxide. Greater excesses tend to inactivate the amine oxide in its control of hair fly.
• the ampholytic detergent is used at from 0 to about 10%, but when used as the sole intermediate linkagecontaining water-soluble detergent, this detergent is preferably employed in a quantity of at least about 5%.
• a preferred combination is from about 4% to about 8% anionio detergent with about 4% to about 6% ampholytic d te n
• anionic detergents are not compatible with amine oxide at the concentrations re-. quir'd.
• anionic detergents other than those'with an intermediate link. can be substituted in whole or in part for the anionic detergents typified by group I so long as more than about 4% of"an'arn'pholyt-ic detergent typified by group II is: also present.
• the total detergent exclusive of amine oxide does not exceed about Ampholytic detergents increase the compatibility of amine oxide with (1) anionics without intermediate linkages, or (2) anionics with intermediate linkages and art R which is not acyclic. Typical examples are listed below in group III.
• ampholytic detergent alkyl beta-iminodipropionate
• ampholytic detergent is especially useful for its solubilizing-efiect; and it is the ampholytic detergent preferred for use in the formulas of this invention to solubilize detergents from group III.
• R, R'C and M have the same meaning as before;
• R" is a hydrophobic radical which is not acyclic, -i.e., which contains a cyclic group.
• the alkyl radical, R, or the acyl'radical, RC(O)-, of the detergents preferably contains 12 carbon atoms or is a mixture of radicals containing from about 10 to about 18 carbon atoms such that at least about of the radicals contain 12 carbon atoms.
• Suitable mixtures are available from natural or synthetic sources.
• coconut oil is a source for coconut alcohol and coconut fatty acid which have chain-lengths suitable for use in this invention.
• typical middle cut coconut alcohol having the following composition: 2%Cm, 66%C 23 %-C and 9%C is a desirable source for alkyl radicals in-thedetergents of this invention; coconut fatty acids having the same chain length composition are a desirable source of acyl radicals.
• acyl radicals can also be used as a source of acyl radicals; an example of the chain length distribution of such material is CrC10 15%, C12-50%, C14-17%, and C -11%.
• alkyl benzene radicals, R" the alkyl radical preferably contains an average of about 8 carbon atoms.
• .M,.the cation to neutralizethe charge of the anionic detergennis one which produces a water-soluble detergent salt A variety of cations including ammonium, magnesium, and quaternary ammonium are suitable for part-icular formulas.
• the preferred cations for-use in the compositions of this invention are alkali metal (i.e., sodium, potassium) alkanolammonium (i.e., mono-, di-, and triethanolammonium), ammonium and mixtures thereof. Those especially preferred are sodium, potassium, 4 and triethanolammonium.
• these are: up to 0.5% color, up to 1% sequestering agent to clarify solutions made from hard waters, and up to 1% perfume.
• coconut diethauolamide may be added for its elfect on the feel of the hair, making it smooth but not oily feeling. None is required, but up to about can be used.
• Up to about 5% organic solvent for example ethyl alcohol, can be added to increase solubility or control viscosity.
• the water content is greater than about 60% to insure homogeneous solution over a satisfactory range of temperatures; preferably it is less than 90% to insure sufiicient active material per unit volume, and more than about 70%
• Example I Compositions consisting of coconut dimethylamine oxide, 10% detergent with an intermediate linkage and 80% water were prepared. Duplicate solutions except that 5% water was replaced by 5% disodium lauryl betaiminodipropionate were also prepared. The pH was adjusted up to about 9.5 and down to the value at which the solution lost its clarity, using sodium carbonate and citric acid. This minimum pH value at which the solution remained clear is noted below.
• cocoyl radicals have approximately the following chain length composition: 2%Ol(i, 55%-Cii, 22%O14, 0% Ciu, and 21%C1s.
• the alkyl or acyl radical is derived from middle cut coconut alcohol or fatty acid and has approximately the following chain length composition: 2%C o, 66%O12, 23%-C14, and 9%C15.
• compositions are well adapted for shampooing hair. They can be adjusted to any pH value from the minimum specified to about pH 8.5 and retain their performance. They suds and clean well, reduce the static electrification of dry shampooed hair on combing, and leave the air in a highly manageable condition.
• compositions were made up and tested as in A except that anionic detergents without intermediate linkages or with non-acyclic hydrophobic groups Were used.
• the results for compositions containing 5.0% disodium lauryl beta-iminodipropionate are as follows:
• Triethanolammonium coconut 2 soap 7.8 Triethanolammonium coconut 1 sulfate 7.9 Sodium coconut sulfate 8.3 Sodium tert-octylphenyl triethenoxy sulfonate 7.9 Sodium alkyl sulfonate 7.5 Ammonium alkyl sulfonate 3 7.1
• the alkyl radical is derived from middle cut coconut alcohol and has ap roxirnately the following chain len th composition: 2%- 1o, 66%-C12, 23 %C14. and 9% m.
• the alkyl radicals are a mixture of chains containing from form clear solutions with the amine oxide at low enough pH values; for example, triethanolammonium and sodium coconut sulfate formulations without ampholytic detergent were not clear below pH 8.8-9.
• Example II The following shampoo was prepared and found to be a clear homogeneous liquid at temperatures above 60 F.
• coconut 1 diethanolarnide 2.0 Denatured ethyl alcohol (formula SDA 40)- 7 .0 Tetrasodium ethylenediaminetetraacetate 0.5 Perfume 0.3 Citric acid to adjust pH to 8.0.
• Water Balance 1 The alkyl or acyl radical is derived from middle cut coconut alcohol or fatty acid and has approximately the following Sch7ain ength composition: 2%C1o, 66%-C12, 23 %-'C14 and This shampoo gave a good suds in laboratory tests and cleaned hair effectively.
• Methylethylcoconutamine oxide or diethyldodecylamine oxide can be substituted for the dimethylcoconutamine oxide in this formula Without substantially adversely afiecting the properties of performance of the formula.
• Percent 'Dimethyldodecylamine oxide 7.0 Sodium salt of sulfated condensation product of one mole of coconut 1 alcohol with about 3 moles of ethylene oxide 7.0
• Water Balance 'lhe alkyl radical is derived from middle cut coconut alcoholand has approximately the following chain length composition: 2%C1o, 66% C12, 23%-C14 and 9%Cm.
• b ZWholecut coconut typified by the analysis given hereine ore.
• a and -B,--identica-l switchesof human hair (2" x 12") were washed,--(A)-withawidely distributed commercial shampooand (B) with-the shampoo -ofExam-ple II.
• the switches were allowedto'dry in the air after rinsing; when dried, they were untangled by combing with the coarse teeth-of a hard rubber comb. Each switch was then combed with the fine. teeth of the comb using 10 strokes.
• At room temperature and a relative humidity of 34% the switch washed in product (A) spread out and became disarranged .due to the repulsion of the charges built up on the hair fibers.
• the appearance of the switch washed in composition (B) exhibited little, if any, indication of repulsive electric charges being on the hair fibers.
• a detergent composition especially adapted for I shampooinghair by its efiect in reducing the static electrification of combed dry hair consisting essentially of:
• Z is a polyether intermediate linking member and M is a cation to neutralize the charge of the anion.
• a detergent composition especially adapted for shampooing hair by its eifect in reducing static electrification of combed hair consisting essentially of:
• a detergent composition especially adapted for shampooing hair by its efiect in reducing the static electrification of combed hair consisting essentially of:
• a detergent composition especially adapted for shampooing 'hair by its effect in reducing the static electrification of combed dry hair consisting essentially of: from about 4% to about 8% of R(OC H SO M; from about 4% to about 6% of RN(C I-I COOM) from about to about of R(CH N O; and the balance substantially water, where R is an alkyl radical containing from 10 to 16 carbon atoms, at least about 50% of R 10 containing 12 carbon atoms, and M is selected from the group consisting of ammonium, triethanolammonium, sodium, potassium, and mixtures thereof, the pH of said detergent composition being between about 7 and 8.
• a detergent composition especially adapted for shampooing hair by its effect in reducing the static electrification of combed dry hair consisting essentially of: from about 4% to about 8% of RSO M; from about 4% to about 6% of RN(C H COOM) from about 5% to about 10% of R(CH N- O; and the balance substantially water, where R is an alkyl radical containing from 10 to 16 carbon atoms, at least about of R containing 12 carbon atoms, and M is selected from the group consisting of ammonium, triethanolammonium, sodium, potassium and mixtures thereof, the pH of said detergent composition being between about 7 and about 8.
• a detergent composition especially adapted for shampooing hair by its etfect in reducing the static electrification of combed dry hair consisting essentially of: from about 4% to about 8% of R(OC H SO M; from about 5% to about 10% of R(CH N O; and the balance substantially water, Where R is an alkyl radical containing from 10 to 16 carbon atoms at least 50% of R containing 12 carbon atoms and M is selected from the group consisting of ammonium, triethanolammonium, sodium, potassium and mixtures thereof, the pH of said detergent composition being between about 7 and about 8.

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Cited By (32)

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Citations (6)

• 0
  • NL NL252522D patent/NL252522A/xx unknown
  • BE BE622463D patent/BE622463A/xx unknown
• 1959
  • 1959-06-10 US US819247A patent/US3086943A/en not_active Expired - Lifetime
• 1960
  • 1960-06-01 DE DEP25108A patent/DE1150781B/de active Pending
  • 1960-06-07 GB GB20012/60A patent/GB942870A/en not_active Expired
  • 1960-06-09 FR FR829561A patent/FR1295911A/fr not_active Expired
  • 1960-06-10 NL NL60252522A patent/NL141776B/xx unknown

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