US3322676A - Shampoos - Google Patents

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Publication number
US3322676A
US3322676A US466061A US46606165A US3322676A US 3322676 A US3322676 A US 3322676A US 466061 A US466061 A US 466061A US 46606165 A US46606165 A US 46606165A US 3322676 A US3322676 A US 3322676A
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Prior art keywords
acid
ethylene oxide
carbon atoms
cationic
compound
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US466061A
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English (en)
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Hiestand Armin
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BASF Schweiz AG
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Ciba AG
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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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • 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
    • C11D1/835—Mixtures of non-ionic with cationic compounds
    • 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 present invention provides shampoos that contain (a) A cationic compound containing at least one aliphatic hydrocarbon residue with more than 7, preferably 11 to 18, carbon atoms, as well as at least one tertiary or quaternary nitrogen atom present in salt-like form, and
  • the outstanding lathering power of the new shampoos is all the more surprising as the above-mentioned cationic components (a) and the non-ionic components (b) by themselves either have a completely inadequate or no lathering power at all on hair.
  • Hair treated with one of the new shampoos has a soft, flufiy feel and a pleasing silky sheen, it has no electrostatic charge and is easy to brush and comb.
  • a hair shampoo preparation which contains (1)
  • As cation active component a member selected from the group consisting of (a) a tertiary amine salt of the compound of the formula R4 R,le lN R, N
  • R represents an aliphatic hydrocarbon radical with 11 to 18 carbon atoms
  • R represents a member selected from the group consistting of an alkylene radical containing 2 to 6 carbon atoms and the radical -CH CHOH-CH with a cosmetically acceptable acid
  • nonionic component a water-soluble reaction product of an alcohol which contains 6 to 11 carbon atoms, whose hydrocarbon radical is branched and whose main-chain contains at least carbon atoms, with at most 15 mols of ethylene oxide,
  • a cosmetically acceptable acid in an amount which is sufficient to effect in the aqueous shampoo preparation a pH-value of 3.0 to 7.0, and in which shampoo preparation the weight ratio of component (1) to component (2) ranges from 1:1 to 1:100.
  • those preparations of the invention deserve to be given preference which contain a compound obtained by reacting 5 to molecular proportions of ethylene oxide with 1 molecular proportion of the alcohol referred to above under (2).
  • those shampoos of the invention possess particularly good properties and are distinguished, for example, by the absence of an unpleasant odour of their own even when examined critically, which contain as the non-ionic ingredient an ethylene oxide adduct which, before being incorporated in the shampoo, has been subjected to a special purifying treatment, for example by expulsion of undesired substances by distillation.
  • a purification operation may consist, for example, in the distillative expulsion from a commercial ethylene oxide adduct under a very good water-jet vacuum at about 160 to 180 C. or in a fallingfilm distillation.
  • the amine compound on which the cationic ingredient (a) is based can be prepared by methods known in the art from the corresponding amine bases or their reaction products with fatty acids or derivatives thereof, hydroxyalkylation agents, for example ethylene oxide, alkylating and acylating agents, for example chloracetic acid or with derivatives thereof, and then converted in known manner by reaction with acids into the amine salts or with quaternating agents into the quaternary ammonium salts.
  • hydroxyalkylation agents for example ethylene oxide
  • alkylating and acylating agents for example chloracetic acid or with derivatives thereof
  • Suitable starting materials for the manufacture of the cationic ingredient to be used according to the invention are tertiary amines of the formula wherein R represents an alkyl with l2-l6 carbon atoms, for example, N-dimethyl-dodecylamine, N-dimethyl-hexadecylamine and their hydroxyalkylation products, also diamines, for example N-dodecyl-ethylenediamine, tetramethylenediamine and hexamethylenediamine, N-octadecyl-ethylenediamine, N-dodecyl-propylenediamine, N- hexadecyl-propylenediamine and N-octadecyl-propylenediamine; also reaction products of such N-alkylene-polyamines with an alkylene oxide, such as ethylene oxide or propylene oxide, for example N-dodecyl-N:N'-dihydroxyethyl
  • cationic ingredient (a) contamed in the new preparations there may be used as starting material for the cationic ingredient (a) contamed in the new preparations the following: mono-acylation products from 1 molecular proportion of a higher fatty acid (for example lauric, myristic, palmitic, stearic or oleic acid) and 1 molecular proportion of an alkylenepolyamine such as ethylenediamine or propylcnediamine and diethylenetriamine; likewise suitable are reaction products of these monoacyl derivatives with a halohydrin or alkylene oxide, such as N-lauroyl-N-hydroxyethylethylenediamine, N palmitoyl-N'-hydroxyethyl-ethylenediamine, N-stearoyl-N-hydroxyethyl-ethylenediamine, N- lauroyl-N'-hydroxyethyl-propylenediamine and N-lauroylhydroxyethyl-diethylenetriamine.
  • Those compounds of the general Formula 1, which are used in the form of their salts as cationic ingredient (a) of the new preparations and contain a radical of the formula (in which formula A and A have the above meanings) are accessible by reacting the amine concerned with chloracetic acid or with a compound of the general formula (in which A and A have the above meanings), more especially with chloracetamide or NzN-[di-(fi-hydroxyethyl) l-chloracetamide.
  • the conversion of the selected tertiary amines into salts used as cationic ingredient of the new preparations is achieved by the usual formation of salts with cosmetically acceptable acids which may be inorganic, such as hydrochloric acid, and phosphoric acid, or organic acids as acetic acid, adipic acid, tartaric acid, malic acid, nitriletriacetic acid, ethylenediamine-tetraacetic acid, citric acid, lactic acid, glycolic acid and mixtures of the above-mentioned acidsv Quite generally speaking, any acid may be used that furnishes with the harmless amine salts that are neither toxic nor irritate the scalp, more especially the salts mentioned specifically below, such as are used in the present invention to establish the desired pH range.
  • cosmetically acceptable acids which may be inorganic, such as hydrochloric acid, and phosphoric acid, or organic acids as acetic acid, adipic acid, tartaric acid, malic acid, nitriletriacetic acid, ethylenediamine-
  • quaternary ammonium compounds which may likewise and with special advantages be used as cationic ingredient of the new preparationsthey are reacted in known manner with a quaternating agent, for example methyl iodide, dimethyl sulfate, benzyl chloride or with ethylen hlorohydrin or with a polyglycol chloride.
  • a quaternating agent for example methyl iodide, dimethyl sulfate, benzyl chloride or with ethylen hlorohydrin or with a polyglycol chloride.
  • the above-mentioned valuable properties of the new shampoos are particularly evident in those preparations in which the ratio of the cationic ingredient (a) to the non-ionic ingredient (b) ranges from 1:1 to 1:30, preferably from 1:2 to 1:10. More especially at a ratio of (a) (b) of 1:3 it was found that t the new preparations had surprisingly advantageous properties insofar as their lathering power and the stability of the lather, good washing power, gentleness towards the skin and absence of the poissage-effect are concerned.
  • the new preparations have a particularly long shelf-life.
  • the preparations of the invention should have a moderately acidic to neutral reaction, for example ranging from pH 3.0 to 7.0.
  • the desired pH value may be adjusted with any inorganic or organic acidic compound acceptable for use in cosmetics, for example with acetic acid or phosphoric acid, or with acid phosphates, or adipic, tartaric, malic, nitrilotriacetic, ethylenediamine-tetra:
  • mixtures of inorganic and organic acids for example mixtures of phosphoric acid and citric acid.
  • the new shampoos containing the new combinations are obtained by simply mixing and dissolving the ingredients, if desired with further addition of compounds conventionally contained in shampoos, such as perfume, dyestuffs, bleaching agents or thickening agents.
  • fatty acid alkanol-amides for example coconut oil fatty acid hydroxyethy -amide.
  • the new preparations may be prepared in solid, pasty or liquid form. They are applied in the known hairdressing manner.
  • Parts in the following examples are parts by weight.
  • Example 1 (a) The non-ionic polyglycol ethers listed in the following Tables I to V were examined for their lathering power. The results are shown in the tables under Lather volume I.
  • the shampoo solutions listed in the following Tables I, II and V were prepared by dissolving the non-ionic compound and the cationic compound in water with addition of a sufiiciency of citric acid to establish a pH value of 4 to 4.5 of the individual solutions.
  • lather volume in the following Tables I to V refers to the amount of lather in cc. produced by twice washing 10 g. of homogeneously dirtied raw wool, moistened with g. water at C. with 2.7 cc. of the individual shampoo solution in each case.
  • the indices 1 and 2 underneath lather volume in Tables I to V refer to the first and second wash each performed in the method employed for determining the lather volume.
  • Non-ionic compounds I 2 ethylhexanol +5 mols ethylene oxide. 0
  • Lather volume Lather volume 0 Cationic compounds containing a in cc.
  • CH3 (EH 2 12 ---..d0 4 CmH3a-1IICH2CH2OH+CV 1 Tartaric acid (100%) 100 420 CH3 I i 3 i2 u do 4 C1aHaaIII-CH2CH2OH+CY 0.1 Phosphoric acid (85%)-.-. 160 320 CH: i 4 12 -..do 4 C1sHaaNCH2CHzOH+Cl 1 Ethylenediaminotetra- 380 I acetic acid (100%).
  • Non-ionic compounds I a quaternary nitrogen atom II I H C 2-ethylbutanol mol ethylene oxide O 0 CmH;5lliCzH4OH]+ Cl C Hz n-Octanol +5 mol ethylene oxide 0 0 C1tH351 lC2H OH]+ Cl 5 0 Ha Tert. nonylphenol +8 mol ethylene oxide 0 I 0 C sH I ICzH4OH]+ Cl 5 5 12+; 0 0 0
  • Example 2 case with the thickening agents shown in Tables VI and A shampoo was made of the composition of the product VII: l in Table I. This shampoo was further admixed in each TABLE VI Non-ionic compound Cationic compound Substance acting as thickening agent Viscosity,
  • Example 4 (a) The non-ionic polyglycol ether, listed in the following Tables VIII to X, was freed in a falling-film Example 3 evaporator from the unreacted alcohol and the monoglycol and diglycol ethers and then examined for its lathering The shampoos listed in Tables I to IV of Example 1 power. The results are shown in the Tables VIII t X were examined as to whether they displayed the s-o-called u d th h ading Lather volume I, pissage-etfect. As is known, this effect consists in the (b) The cationic compounds listed in the following following: When hair washed with a shampoo containing 10 Tables VIII to X were examined for their lathering power.
  • the mixture was made up to 100 parts with water and a shampoo obtained to which perfumes can be added, if desired.
  • a hair shampoo preparation which consists essentially of 1) the cationic compound of the formula (2) a nonionic water-soluble reaction product of a saturated branched-chain alcohol with 6 to 11 carbon atoms, Whose main-chain consists of at least 5 carbon atoms, with 5 to 15 mols of ethylene oxide,
  • a cosmetically acceptable acid selected from the group consisting of acetic acid, phosphoric acid, adipic acid, tartaric acid, malic acid, nitrilotriacetic acid, ethylenediamine-tetraa-cetic acid, citric acid, lactic acid, glycollic acid and mixtures thereof, in an amount which is sufiicient to effect in the aqueous shampoo preparation a pH-value of 3.0 to 7.0,
  • a hair shampoo preparation which consists essentially of (1) a cationic compound of the formula CH3 CH3 [C12 2P T( 2)n-I TC12 2s 2X CH3 CH3 wherein n represents a number from 2 to 6 and X- represents a halogen anion selected from the group consisting of chlorine and bromine,
  • a cosmetically acceptable acid selected from the group consisting of acetic acid, phosphoric acid, adipic acid, tartaric acid, malic acid, nitrilotriacetic acid, ethylenediamine-tetraacetic acid, citric acid, lactic acid, glycollic acid and mixtures thereof in an amount which is sufiicient to effect in the aqueous shampoo preparation a pH-value of 3.0 to 7.0,
  • the weight ratio of component (1) to component (2.) ranges from 1:1 to 1:100.
  • a hair preparation which consists essentially of (1) a tertiary amine salt of a cationic compound of the formula wherein R represents a-lkyl with 12 to 16 carbon atoms with a cosmetically acceptable acid selected from the group consisting of acetic acid, phosphoric acid, adipic acid, tartaric acid; malic acid, nitrilotriacetic acid, ethylenediamine-tetraacetic acid, citric acid, lactic acid, glycollic acid and mixtures thereof, (2) a nonionic water-souble reaction product of a saturated branched-chain alcohol with 6 to 11 carbon atoms, whose main-chain consists of at least 5 carbon atoms, with 5 to 15 mols of ethylene oxide, (3) water, and (4) a cosmetically acceptable acid selected from the group consisting of acetic acid, phosphoric acid, adipic acid, tartaric acid, malic acid, nitrilotriacetic acid, ethylenediamine-tetraacetic
  • a hair shampoo preparation which consists essentially of (1) a tertiary amine salt of the cationic compound of the formula with a cosmetically acceptable acid selected from the group consisting of acetic acid, phosphoric acid, adipic acid, tartaric acid, malic acid, nitrilotriacetic acid, ethylenediamine-tetraacetic acid, citric acid, lactic acid, glycollic acid and mixtures thereof, (2) a nonionic Water-soluble reaction product of a saturated branched-chain alcohol with 6 to 11 carbon atoms, whose main-chain consists of at least 5 carbon atoms, with 5 to 15 mols of ethylene oxide, (3) water, and (4) a cosmetically acceptable acid selected from the group consisting of acetic acid, phosphoric acid, adipic acid, tartaric acid, malic acid, nitrilotriacetic acid, citric acid, lactic acid, glycollic acid and mixtures thereof, in an amount which is sufficient to effect in the shampoo preparation a
  • a hair shampoo preparation which consists essentially of (1) a tertiary amine salt of the cationic compound of the formula with a cosmetically acceptable acid selected from the group consisting of acetic acid, phosphoric acid, adipic acid, tartaric acid, malic acid, nitrilotriacetic acid, ethylenediamine-tetraacetic acid, citric acid, lactic acid, glycollic acid and mixtures thereof,
  • a hair shampoo preparation which consists essentially of (1) a tertiary amine salt of the cationic compound of the formula with a cosmetically acceptable acid selected from the group consisting of acetic acid, phosphoric acid,
  • adipic acid tartaric acid, malic acid, nitrilotriacetic acid, ethylenediamine-tetraacetic acid, citric acid, lactic acid, glycollic acid and mixtures thereof,
  • a cosmetically acceptable acid selected from the group consisting of acetic acid, phosphoric acid, adipic acid, tartaric acid, malic acid, nitrilotriacetic acid, ethylenediamine-tetraacetic acid, citric acid, lactic acid, glycollic acid and mixtures thereof, in an amount which is sufficient to effect in the aqueous shampoo preparation a pH-value of 3.0 to 7.0,
  • a hair shampoo preparation which consists essentially of (1) a tertiary amine salt of the cationic compound of the formula with a cosmetically acceptable acid selected from the group consisting of acetic acid, phosphoric acid, adipic acid, tartaric acid, malic acid, nitrilotriacetic acid, ethylenediamine-tetraacetic acid, citric acid, lactic acid, glycollic acid and mixtures thereof, (2) a nonionic water-soluble reaction product of a saturated branched-chain alcohol with 6 to 11 car- 'bon atoms, whose main-chain consists of at least 5 carbon atoms, with 5 to 15 mols of ethylene oxide, (3) water, and (4) a cosmetically acceptable acid selected from the group consisting of acetic acid, phosphoric acid, adipic acid, tartaric acid, malic acid, nitrilotriacetic acid, ethylenediamine-tetraacetic acid, citric acid, lactic acid, glycollic acid and mixture
  • a hair shampoo preparation which consists essentially of (1) a tertiary amine salt of the cationic compound of the formula with a cosmetically acceptable acid selected from the group consisting of acetic acid, phosphoric acid, adipic acid, tartaric acid, malic acid, nitrilotriacetic acid, ethylenediamine-tetraacetic acid, citric acid, lactic acid, glycollic acid and mixtures thereof, (2) a nonionic water-soluble reaction product of a saturated branched-chain alcohol with 6 to 11 carbon atoms, whose main-chain consists of at least 5 carbon atoms, with 5 to 15 mols of ethylene oxide, (3) water, and (4) a cosmetically acceptable acid selected from the group consisting of acetic acid, phosphoric acid, adipic acid, tartaric acid, malic acid, nitrilotriacetic acid, ethylenediamine-tetraacetic acid, citric acid, lactic acid, glycollic acid and mixtures thereof, in
  • a hair shampoo preparation which consists essentially of (1) a tertiary amine salt of the cationic compound of the formula wherein n represents a whole number of at most 2, with a cosmetically acceptable acid selected from the group consisting of acetic acid, phosphoric acid, adipic acid, tartaric acid, malic acid, nitrilotriacetic acid, ethylenediamine-tetraacetic acid, citric acid, lactic acid, glycollic acid and mixtures thereof, (2) a nonionic water-soluble reaction product of a saturated branched-chain alcohol with 6 to 11 carbon atoms, whose main-chain consists of at least 5 carbon atoms, with 5 to 15 mols of ethylene oxide, (3) water, and (4) a cosmetically acceptable acid selected from the group consisting of acetic acid, phosphoric acid, adipic acid, tartaric acid, malic acid, nitrilotriacetic acid, ethylenediamine-tetraacetic acid, citric acid,
  • a hair shampoo preparation which consists essentially of (1) a cationic compound selected from the group consisting of (a) a tertiary amine salt of a compound of the formula R4 R, 6 N-Jh N in which n represents a number of at most 2, m represents a number of at most 3, R represents alkyl with 11 to 18 carbon atoms, R represents alkylene with 2 to 6 carbon atoms, R R and R each represent a member selected from the group consisting of hydrogen, alkyl with at most 2 carbon atoms, hydroxyalkyl with at most 3 carbon atoms,
  • a and A each represents a member selected from the group consisting of hydrogen, methyl and hydroxyethyl, with a cosmetically acceptable acid selected from the group consisting of acetic acid, phosphoric acid, adipic acid, tartaric acid, malic acid, nitrilotriacetic acid, ethylene-diamine-tetraacetic acid, citric acid, lactic acid, glycollic acid and mixtures thereof, and (b) a quaternary ammonium salt of a compound of the formula set forth above under (a) with a member selected from the group consisting of methyl iodide, dimethyl sulfate, benzyl chloride, a polyglycol chloride containing at most 6 carbon atoms and ethylenechlorohydrine, (2) a nonionic watersoluble reaction product of a saturated branched-chain alcohol with 6 to 11 carbon atoms, whose main-chain consists of at least 5 carbon atoms, with 5 to 15 mols of
  • a hair shampoo preparation which consists essentially of (1) a cationic quaternary ammonium salt of a compound of the formula atoms and R and R represents alkyl with at most 2 carbon atoms with ethylenechlorohydrine,
  • the weight ratio of component (1) to component (2) ranges from 1:1 to 1:100.
  • a preparation as claimed in claim 10 which contains as further component approximately 5% by weight of a mixture of coconut fatty acid diethanolamide and diethanolamine.
  • a preparation as claimed in claim 10 which contains as a further component an eifective amount of a mixture of coconut fatty acid diethanolamide and diethanolamine as a thickening agent.
  • a preparation as claimed in claim 10 which contains as a further component approximately 120% by weight of a thickening agent.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
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  • Chemical & Material Sciences (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)
US466061A 1961-10-25 1965-06-22 Shampoos Expired - Lifetime US3322676A (en)

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CH1233361A CH445023A (de) 1961-10-25 1961-10-25 Haarwaschmittel

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US (1) US3322676A (en(2012))
BE (1) BE624000A (en(2012))
CH (1) CH445023A (en(2012))
DE (1) DE1175390B (en(2012))
ES (1) ES281843A1 (en(2012))
GB (1) GB1014887A (en(2012))
IT (1) IT943005B (en(2012))
NL (2) NL284669A (en(2012))
SE (1) SE219426C1 (en(2012))

Cited By (18)

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US3969500A (en) * 1972-03-03 1976-07-13 Lever Brothers Company Shampoo containing a water-soluble linear carboxylic polymer
US3990991A (en) * 1974-02-01 1976-11-09 Revlon, Inc. Shampoo conditioner formulations
US4160823A (en) * 1976-03-29 1979-07-10 Kao Soap Co., Ltd. Transparent hair rinsing composition
US4165369A (en) * 1975-09-11 1979-08-21 Kao Soap Co., Ltd. Liquid hair rinse containing quaternary ammonium salts and a synthetic secondary alcohol
US4168302A (en) * 1976-03-29 1979-09-18 The Richardson Company Hair conditioning compositions containing a non-irritating cationic surfactant
US4217914A (en) * 1974-05-16 1980-08-19 L'oreal Quaternized polymer for use as a cosmetic agent in cosmetic compositions for the hair and skin
US4222905A (en) * 1978-06-26 1980-09-16 The Procter & Gamble Company Laundry detergent compositions having enhanced particulate soil removal performance
US4228044A (en) * 1978-06-26 1980-10-14 The Procter & Gamble Company Laundry detergent compositions having enhanced particulate soil removal and antiredeposition performance
US4259217A (en) * 1978-03-07 1981-03-31 The Procter & Gamble Company Laundry detergent compositions having enhanced greasy and oily soil removal performance
US4347168A (en) * 1977-11-17 1982-08-31 The Procter & Gamble Company Spray-dried granular detergent compositions for improved greasy soil removal
US4357141A (en) * 1977-09-07 1982-11-02 L'oreal Compositions for dyeing hair and their applications
US4422853A (en) * 1974-05-16 1983-12-27 L'oreal Hair dyeing compositions containing quaternized polymer
US4493773A (en) * 1982-05-10 1985-01-15 The Procter & Gamble Company Low phosphate, softening laundry detergent containing ethoxylated nonionic, alkylpolysaccharide and cationic surfactants
US4948579A (en) * 1974-05-16 1990-08-14 Societe Anonyme Dite: L'oreal Quaternized polymer for use as a cosmetic agent in cosmetic compositions for the hair and skin
US5196189A (en) * 1974-05-16 1993-03-23 Societe Anonyme Dite: L'oreal Quaternized polymer for use as a cosmetic agent in cosmetic compositions for the hair and skin
FR2735495A1 (fr) * 1995-06-14 1996-12-20 Rhone Poulenc Chimie Composition a caractere irritant reduit contenant des tensioactifs anioniques
US5858341A (en) * 1994-01-11 1999-01-12 L'oreal Detergent cosmetic compositions for hair use and use thereof
US6017860A (en) * 1996-04-15 2000-01-25 Stepan Company Cleaning, conditioning and styling hair care compositions

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7815011A (nl) * 1977-06-29 1979-09-28 Procter & Gamble Wasmiddel met laag fosfaatgehalte voor het wassen van weefsels.

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US5196189A (en) * 1974-05-16 1993-03-23 Societe Anonyme Dite: L'oreal Quaternized polymer for use as a cosmetic agent in cosmetic compositions for the hair and skin
US4948579A (en) * 1974-05-16 1990-08-14 Societe Anonyme Dite: L'oreal Quaternized polymer for use as a cosmetic agent in cosmetic compositions for the hair and skin
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Also Published As

Publication number Publication date
SE219426C1 (en(2012)) 1968-03-12
CH445023A (de) 1967-10-15
NL135441C (en(2012))
IT943005B (it) 1973-04-02
DE1175390B (de) 1964-08-06
BE624000A (en(2012))
ES281843A1 (es) 1963-05-01
NL284669A (en(2012))
GB1014887A (en) 1965-12-31

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