EP0437462A1 - Ethers de cellulose amphoteres et zwitterioniques utilises dans des produits capillaires - Google Patents

Ethers de cellulose amphoteres et zwitterioniques utilises dans des produits capillaires

Info

Publication number
EP0437462A1
EP0437462A1 EP89910861A EP89910861A EP0437462A1 EP 0437462 A1 EP0437462 A1 EP 0437462A1 EP 89910861 A EP89910861 A EP 89910861A EP 89910861 A EP89910861 A EP 89910861A EP 0437462 A1 EP0437462 A1 EP 0437462A1
Authority
EP
European Patent Office
Prior art keywords
hair
weight
groups
amphoteric
zwitterionic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP89910861A
Other languages
German (de)
English (en)
Inventor
Reinhard Müller
Brigitte Hase
Konrad Engelskirchen
Karl Giede
Klaus-Dieter Wisotzki
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0437462A1 publication Critical patent/EP0437462A1/fr
Pending legal-status Critical Current

Links

Classifications

    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • 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
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5428—Polymers characterized by specific structures/properties characterized by the charge amphoteric or zwitterionic

Definitions

  • the invention relates to the use of amphoteric and zwitterionic cellulose ethers in compositions for cleaning and care of the hair and hair care compositions which contain such polymers as additives which improve and combability.
  • Cationic surfactants are usually present as active ingredients in such preparations. It is also known to determine conventional shampoos based on anionic surfactants or on the basis of mixtures of surfactants of different ionicity. Add substances to achieve a certain conditioning effect at the same time as washing the hair. Such substances are e.g. B. water-soluble proteins or protein degradation products, polycationic polymers or also zwitterionic synthetic polymers, such as those used for. B. are described in DE OS 21 50 557 or DE OS 28 17 369.
  • the known polymeric cationic conditioning agents have numerous shortcomings.
  • Products with good water solubility and sufficient compatibility with anionic wash raw materials are usually too weakly effective, which makes a high dosage necessary.
  • Other, limited water-soluble products are too strong a noun, they absorb almost completely on the hair, lead to accumulation when the hair is treated several times and thereby reduce the fullness and fit of the dried hair.
  • the zwitterionic polymers known for hair treatment and hair setting agents have the disadvantage, particularly in formulations with anionic surfactants, that the hair-activating and hair-fixing properties are gradually lost in the course of longer storage times.
  • the invention relates to the use of amphoteric and zwitterionic, water-soluble cellulose ethers which, on average, contain at least 0.1 amino and / or ammonium groups and at least 0.1 carboxyl groups per anhydrogiucose unit in an arrangement of the formulas I and II
  • R 3 is a group - (CH - R ⁇ 2 or - (CH.) -
  • R is an alkyl group with 1-4 C atoms or a group —C H. COO, and optionally additionally a number of ether-linked alkyl or hydroxyalkyl groups with 1-4 that are at least necessary for their water solubility
  • C atoms contain, as a combable additive to improve
  • Groupings of the formula I result from the reaction of dialkylaminoalkyl groups introduced primarily into the celluloses with the aminoalkylating and / or carboxylalkylating agents.
  • additional cations and anions may be present for charge balancing, preferably e.g. Sodium ions or protons and chloride or sulfate ions.
  • the full water solubility of the cellulose ethers is preferably adjusted solely via the number of ionic groups of the formulas I and II, and it is therefore preferred that they contain an average of a total of 0.5 ionic groups in the arrangement of the formulas I and II per anhydroglucose unit.
  • the cellulose ethers to be used according to the invention are readily soluble in water and in aqueous solutions of anionic, cationic, ampholytic, zwitterionic and nonionic surfactants and retain their combability-improving, hair-activating and hair-fixing properties in aqueous solutions of such surfactants even over prolonged storage times at.
  • they are suitable according to the invention using cellulose ether as a setting and hair-activating component in aqueous preparations for cleaning and care of the hair.
  • Such preparations can e.g. B. Hair shampoos, hair rinsing agents, hair setting agents, hair blow-drying agents and aqueous colorants, permanent waving agents or permanent waving fixing agents.
  • amphoteric cellulose ethers to be used according to the invention
  • Carboxymethyl cellulose used.
  • the alkyl or hydroxyalkyl ether groups with 1 to 4 carbon atoms that may be required to achieve good water solubility are introduced in a conventional manner by etherification with alkyl halides with 1 to 4 carbon atoms or by etherification with diaikyl sulfate, eg. B. Dimethyl sulfate, or by the addition of epoxyalkanes such as ethylene oxide or propylene oxide or glycid according to procedures known from the literature.
  • the alkyl and hydroxyalkyl groups can be introduced before, simultaneously with or after the introduction of the cationic and / or anionic groups.
  • Alkyl groups with 1 to 4 carbon atoms can be obtained by alkylation
  • amphoteric and zwitterionic cellulose ethers to be used according to the invention are preferably added to the agents for cleaning and caring for the hair in amounts of 0.01-5% by weight.
  • the amphoteric and zwitterionic cellulose ethers work particularly well as additives to agents for washing or rinsing the hair, which are characterized by a content of surface-active substances, generally in an amount of 0.1-25% by weight.
  • a preferred embodiment of the invention is e.g. an aqueous-based hair shampoo which contains 0.1-5% by weight of the amphoteric or zwitterionic cellulose ether and 5-25% by weight of at least one anionic surfactant.
  • anionic surface-active substances suitable for use on the human body are suitable as anionic surfactants in hair treatment compositions according to the invention. These are characterized by a water-solubilizing, anionic group such as, for example, a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group having 10 to 22 carbon atoms.
  • anionic group such as, for example, a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group having 10 to 22 carbon atoms.
  • the molecule may contain glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups.
  • Acyisarcosines with 10 to 18 C atoms in the acyl group acyl taurides with 10 to 18 C atoms in the acyl group, acyl isethionates with 10 to 18 C atoms in the acyl group, sulfosuccinic acid and dialkyl esters with 8 to 18 C atoms in the alkyl group and sulfosuccinic acid monoalkyl polyoxyethyl esters with 8 to 18 carbon atoms in the alkyl group and 1 to 6 oxyethyl groups, linear alkanesulfonates with 12 to 18 carbon atoms, linear alpha-olefin sulfonates with 12 to 18 carbon atoms, alpha-sulfofatty acid methyl esters of fatty acids with 12 to 18 carbon atoms,
  • Alkyl sulfates and alkyl polyglycol ether sulfates of the form! R 6 -0 (CH 2 -CH 2 0) ⁇ -OS0 3 H, in which R 6 is a preferably linear alkyl group with 10 to 18 carbon atoms and x O or 1 to 12.
  • Alkyl sulfate and alkyl polyglycol ether sulfates having 10 to 18 carbon atoms in the alkyl group and up to 12 glycol ether groups in the molecule are preferred.
  • the hair shampoo formulations according to the invention can contain all auxiliaries and additives known for this purpose in the usual amounts. These are especially non-ionic, amphoteric and zwitterionic surfactants.
  • Nonionic surfactants are primarily the adducts of 2 to 20 moles of ethylene oxide with preferably linear alcohols with 12 to 18 C atoms, with alkylphenols with 8 to 15 C atoms in the alkyl group, with fatty acids with 12 to 18 C atoms, on fatty acid partial glycerides, on fatty acid sorbitan partial esters, on fatty acid alkanolamides and on methyl glucoside fatty acid esters.
  • nonionic surfactants are alkyl (oligo) glucosides, alkyl amine oxide surfactants and fatty acid alkanolamides.
  • Amphoteric surfactants are, for example, alkyl (Cp-C.) Trimethylammonio-glycinate or acyl- (C 0 -C 10 ) -aminopropyltrimethylammonio-glycinate.
  • a particularly preferred embodiment of the invention are means for rinsing the hair, e.g. after a shampoo treatment or after a dyeing or bleaching treatment.
  • Such products usually contain 0.1-10% by weight of a cationic surfactant to reduce the antistatic chargeability of the hair.
  • the combability of the hair and the fullness of the dry hairstyle is further improved by the addition according to the invention of 0.1-1% by weight of an amphoteric or zwitterionic water-soluble cellulose ether.
  • a content of 0.5-5% by weight of a cationic surfactant of the general formula IV is particularly useful
  • R is an alkyl or hydroxyalkyl group with 8-22 carbon atoms
  • R and R are an alkyl group with 1 - 4 C atoms or a group of the formula
  • R is a benzyl group or one of those for R, 8 9 (-)
  • R and R has the meanings indicated, and A is a chloride
  • Suitable cationic surfactants are e.g. Cetyltrimethylammonium chloride, lauryldimethyibenzylammonium chloride, stearyitrimethylammonium chloride, distearyldimethyammonium chloride, tallow alkyl tris (oligooxyethyI) ammonium phosphate, 2-hydroxyhexadecyl-2-hydroxyethyl-2-methyl-hydroxyethyl-2-dimethyl-hydroxyl-2-methyl-dimethyl-hydroxyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-
  • the hair rinses according to the invention additionally contain a fatty substance, e.g. contain a cosmetic oil, fat or wax component, a paraffin oil or paraffin wax, wool wax or a wool wax derivative.
  • a fatty substance e.g. contain a cosmetic oil, fat or wax component, a paraffin oil or paraffin wax, wool wax or a wool wax derivative.
  • Particularly fatty alcohols are fatty alcohols with 14-22 carbon atoms, e.g. Cetyl and / or stearyl alcohol as well as fatty acid monoglycerides and / or fatty acid diglycerides of fatty acids with 16-22 C atoms, e.g. of palmitin and / or stearic acid.
  • Such fatty substances are preferably present in amounts of 1-10% by weight, based on the entire preparation.
  • the hair rinsing agents according to the invention may also contain minor auxiliaries and additives, which are customary in hair rinsing agents, in up to about 5% by weight.
  • auxiliaries and additives are e.g. lower polyols, 1, 2-propylene glycol or glycerin, water-soluble non-ionic thickeners such as e.g. Hydroxyethyl cellulose, methyl hydroxypropyl cellulose, hydroxyethyl starch and
  • Hydroxypropyl guar also preservatives, fragrances, dyes, light stabilizers and hair cosmetic agents such as vitamins, plant extracts, balms, anti-dandruff agents (e.g. Zn- or Mg-pyridinthione) or sebostatics.
  • a further product was produced by the process described under 1.1.
  • the reaction product had the following key figures:
  • Example 1.1 0.5% by weight
  • Example 1.2 0.5% by weight
  • Example 1.1 0.5% by weight
  • Example 1.2 0.5% by weight
  • Example 1.4 0.5% by weight
  • the hair washed with the listed shampoos shows good wet combability and dry combability and no electrostatic charge when combing after drying.
  • Example 1.1 0.5% by weight
  • Genami n DSAC 12 1.0% by weight Cellulose ether
  • Example 1.2 0.5% by weight
  • Example 1.3 0.5% by weight
  • Genamin DSAC 12 1.0 Cew .-% cellulose ether
  • Example 1.4 0.5% by weight
  • the rinsing agents listed give the wet and dry hair very good combability and a pleasant feel. When combing dry hair with a hard rubber comb, there is no electrostatic charge.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Detergent Compositions (AREA)

Abstract

Ethers de cellulose amphotères et zwitterioniques solubles dans l'eau qui, par unité d'anhydroglucose, comportent en moyenne au moins 0,1 groupe amino et/ou ammonium et au moins 0,1 groupe carboxyle ainsi que, le cas échéant, des groupes alkyle ou hydroxyalkyle liés du type éther avec 1 à 4 atomes de C en quantité au moins suffisante pour les rendre solubles dans l'eau. Ces éthers conviennent comme additifs démêlants pour shampoings et baumes après-shampoing. De préférence, ces produits contiennent de 0,01 à 5 pour cent en poids des éthers de cellulose amphotères et zwitterioniques et de 0,1 à 25 pour cent en poids d'un tensio-actif.
EP89910861A 1988-10-04 1989-09-25 Ethers de cellulose amphoteres et zwitterioniques utilises dans des produits capillaires Pending EP0437462A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3833658 1988-10-04
DE3833658A DE3833658A1 (de) 1988-10-04 1988-10-04 Verwendung von amphoteren und zwitterionischen celluloseethern in haarpflegemitteln

Publications (1)

Publication Number Publication Date
EP0437462A1 true EP0437462A1 (fr) 1991-07-24

Family

ID=6364315

Family Applications (2)

Application Number Title Priority Date Filing Date
EP89910861A Pending EP0437462A1 (fr) 1988-10-04 1989-09-25 Ethers de cellulose amphoteres et zwitterioniques utilises dans des produits capillaires
EP89117701A Expired - Lifetime EP0365845B1 (fr) 1988-10-04 1989-09-25 Utilisation d'éthers cellulosiques amphothères et zwittérioniques dans des produits de traitement des cheveux

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP89117701A Expired - Lifetime EP0365845B1 (fr) 1988-10-04 1989-09-25 Utilisation d'éthers cellulosiques amphothères et zwittérioniques dans des produits de traitement des cheveux

Country Status (7)

Country Link
EP (2) EP0437462A1 (fr)
KR (1) KR900701243A (fr)
AT (1) ATE79017T1 (fr)
DE (2) DE3833658A1 (fr)
ES (1) ES2045328T3 (fr)
GR (1) GR3006129T3 (fr)
WO (1) WO1990003779A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2087176C (fr) * 1990-07-17 1997-07-01 Benjamin Weinstein Shampoing sans conditonneur
DE4401708A1 (de) * 1994-01-21 1995-07-27 Henkel Kgaa Polymerkonzentrat und Verwendung
DE4405127A1 (de) * 1994-02-18 1995-08-31 Henkel Kgaa Haarbehandlungsmittel
US6210689B1 (en) * 1998-03-18 2001-04-03 National Starch & Chemical Co. Investment Holding Corporation Keratin treating cosmetic compositions containing amphoteric polysaccharide derivatives
FR2819403B1 (fr) 2001-01-12 2004-10-15 Oreal Compositions cosmetiques contenant un fructane, un polysaccharide et un agent benefique et leurs utilisations
FR2833599B1 (fr) * 2001-12-18 2004-01-30 Oreal Polysaccharide amphotere, composition et utilisation
US7232561B2 (en) 2002-05-31 2007-06-19 L'oreal S.A. Washing compositions comprising at least one amphiphilic block copolymer and at least one cationic or amphoteric polymer
FR2874381B1 (fr) * 2004-08-19 2006-11-24 Oreal Nouveaux composes polysaccharidiques amphoteres a fonction(s) aldehyde, composition les comprenant et leur utilisation en cosmetique
FR2874318B1 (fr) * 2004-08-19 2006-11-24 Oreal Utilisation en cosmetique de composes polysaccharidiques amphoteres a chaine(s) polymerique(s) cationique(s)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2591748A (en) * 1949-12-23 1952-04-08 Hercules Powder Co Ltd Amphoteric cellulose derivatives
FR2110268B1 (fr) * 1970-10-07 1976-06-04 Minnesota Mining & Mfg
DE3044754C2 (de) * 1979-11-28 1995-06-01 Oreal Mittel und Verfahren zur Behandlung von Keratinfasern
DE3503618A1 (de) * 1985-02-02 1986-08-07 Henkel KGaA, 4000 Düsseldorf Mittel zum waschen oder spuelen der haare
LU86429A1 (fr) * 1986-05-16 1987-12-16 Oreal Compositions cosmetiques renfermant un polymere cationique et un polymere anionique comme agent epaississant

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9003779A1 *

Also Published As

Publication number Publication date
WO1990003779A1 (fr) 1990-04-19
DE58901987D1 (de) 1992-09-10
EP0365845A1 (fr) 1990-05-02
EP0365845B1 (fr) 1992-08-05
DE3833658A1 (de) 1990-04-05
GR3006129T3 (fr) 1993-06-21
ATE79017T1 (de) 1992-08-15
ES2045328T3 (es) 1994-01-16
KR900701243A (ko) 1990-12-01

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