WO1995021602A1 - Produit de soins capillaires contenant des polymeres - Google Patents

Produit de soins capillaires contenant des polymeres Download PDF

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Publication number
WO1995021602A1
WO1995021602A1 PCT/EP1995/000309 EP9500309W WO9521602A1 WO 1995021602 A1 WO1995021602 A1 WO 1995021602A1 EP 9500309 W EP9500309 W EP 9500309W WO 9521602 A1 WO9521602 A1 WO 9521602A1
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WO
WIPO (PCT)
Prior art keywords
monomer units
hair treatment
hair
mol
composition according
Prior art date
Application number
PCT/EP1995/000309
Other languages
German (de)
English (en)
Inventor
Joachim Conradi
Ulrich Eicken
Winfried Emmerling
Annedore Niemann
Ludwig Schieferstein
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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 Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Publication of WO1995021602A1 publication Critical patent/WO1995021602A1/fr

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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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • 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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)

Definitions

  • the invention relates to hair treatment compositions with polyoxazolines.
  • These setting agents can be incorporated into conventional hair cleaners or conditioners. In many cases, however, it is advantageous to use them in the form of special agents such as hair fixers or hair sprays.
  • polymeric compounds such as, for example, polyvinylpyrrolidones and vinyl acetate-vinylpyrrole don copolymers, have proven successful as setting agents.
  • polyoxazolines are outstandingly suitable as active ingredients for hair treatment agents.
  • the polyoxazolines can be distributed very homogeneously.
  • the formulations are stable in storage and show good spray characteristics when sprayed.
  • the formulations show good setting properties with low residual tack and can also be used as finishing agents due to their antistatic effect. After all, they can easily be removed from the hair by washing or brushing.
  • the invention therefore relates to hair treatment compositions comprising conventional cosmetic ingredients which contain a polyoxazoline.
  • Polyoxazolines are known from the literature. They can be obtained by cationic polymerization of appropriate 4,5-dihydro-1,3-oxazoles with ring opening. Procedures in this regard can be found, for example, in German patent applications 12 06 585, 15 70 213 and 19 04 540. A further process for the production of polyoxazolines can be found in the German patent application P 44 03 953.0 filed on the same day, to which express reference is made.
  • Polyoxazolines which essentially consist of one another, have proven to be particularly advantageous
  • R 1 is hydrogen, an alkyl or alkenyl radical having 1 to 3 carbon atoms or a unit R3- [0-CH2-CH2] ⁇ -, in which R3 is a methyl, ethyl or propyl group and x is a number of 1 to 5, or a mixture of such residues,
  • R ⁇ represents a linear or branched alkyl or alkenyl radical, cycloalkyl or cycloalkenyl radical having 4 to 22 carbon atoms, an optionally alkyl or alkenyl-substituted, aromatic or heterocyclic radical having 5 to 22 carbon atoms or a mixture of such radicals, and
  • the term "essentially assemble” should be understood to mean that only the corresponding monomers are used. If the polymers have further building blocks, they are either impurities from the polymers or start or termination reagents.
  • R 1 can be hydrogen, a methyl, ethyl, n-propyl, iso-propyl or allyl group, or a mixture of these Groups stand. Monomer units in which R 1 represents a methyl or an ethyl group are particularly preferred. The monomer in which R * represents an ethyl group is very particularly preferred. Furthermore, Rl can be used for a Group R3- [0-CH2-CH2] ⁇ -, in which R ⁇ is a methyl, ethyl or propyl group, x is a number from 1 to 5.
  • R ⁇ Preferred groups for which R ⁇ can stand are nonyl, undecyl, tridecyl, pentadecyl, heptadecyl, heptadecenyl, cyclohexyl, phenyl and benzyl groups.
  • alkyl groups such as occur in the carboxylic acids of the fats and oils mentioned, can be preferred.
  • monomer units may be preferred which carry benzyl or phenyl groups as substituents R.sup.1.
  • Polyoxazolines which have only monomer units of type (A) and (B) are preferred according to the invention. However, it has been found that such polymers also have satisfactory properties according to the invention in which up to 50 mol%, in particular up to 20 mol%, of the monomers are of a different, nonionic type of monomer (C).
  • Preferred nonionic co-monomers are ethylene oxide, propylene oxide, vinyl ether, ⁇ -methylstyrene, isobutylene, ethylene, propylene and 2-C ⁇ _i8-alkyl-oxazines.
  • the monomer units (A), (B) and optionally (C) can occur in the polyoxazolines according to the invention both statistically distributed and in the form of blocks of the respective monomer units. While a statistical distribution has proven advantageous for units (A) and (B), it may be preferred to position units (C) in block form at the ends of the polymer chains.
  • the polyoxazolines which can be used according to the invention preferably have average molecular weights between 1,000 and 1,000,000. Polyoxazolines with average molecular weights between 2,000 and 50,000 have proven to be particularly suitable according to the invention.
  • the hair treatment compositions according to the invention contain the polyoxazoline, depending on the type of hair treatment composition which is not subject to any restrictions, preferably in amounts of 0.05 to 15% by weight, in particular 0.1 to 8% by weight, based on the total Medium.
  • polyoxazolines are preferably the only synthetic polymers in the hair treatment compositions according to the invention. If desired, however, these can also contain further nonionic, cationic, anionic, zwitterionic and ampholytic polymers.
  • the polyoxazolines are advantageous active ingredients for all known types of hair treatment compositions, such as Hair fixers, hair sprays, blow-dry waves, hair shampoos, hair rinses, hair conditioners, hair treatments, permanent waving agents, and hair colorants.
  • Aqueous basis in the sense of this application means that in addition to water other solvents only in amounts up to max. 40 wt .-%, based on the total agent, are included.
  • solvents such as lower alcohols, i.e. e.g. Ethanol or isopropanol, to be used only in amounts of less than 20% by weight, in particular less than 10% by weight, or not at all in the agents according to the invention.
  • agents which contain ethyl ether as a component in particular in amounts of 10% by weight and more.
  • Preferred hair treatment compositions according to the invention are those which remain on the hair after use. These are, in particular, hair fixers, hair sprays and blow dryer waves. Such agents can also be formulated with the aid of a propellant as a foam aerosol. Further components of the agents according to the invention can be, for example:
  • anionic surfactants such as, for example, fatty alkyl sulfates and ether sulfates
  • cationic surfactants such as, for example, quaternary ammonium compounds
  • zwitterionic surfactants such as, for example, betaines
  • ampholytic surfactants such as, for example, alkylpolyglycosides and ethoxylated fatty alcohols
  • cationic polymers such as quaternized cellulose ethers, polysiloxanes quaternary groups, dimethyldiallylammonium chloride polymers, acrylamide-dimethyldiallylammonium chloride copolymers, dimethylaminoethyl methacrylate-vinylpyrrolidone copolymers quaternized with diethyl sulfate, vinylpyrrolidone-methoimidazolinium chloride copolymers and quaternized polyvinyl alcohol-vinyl acrylate
  • Solubilizers such as ethanol, isopropanol, ethylene glycol, propylene glycol, glycerol and diethylene glycol, dyes, Anti-dandruff agents such as Piroctone Ola ine and Zink Omadine, other substances for adjusting the pH value,
  • Active ingredients such as panthenol, allantoin, pyrrolidone carboxylic acids and their salts, plant extracts and vitamins, light stabilizers,
  • Consistency enhancers such as sugar esters, polyol esters or polyol alkyl ethers, fats and waxes such as walrus, beeswax, montan wax, paraffins and fatty alcohols, fatty acid alkanolamides,
  • Swelling and penetration substances such as glycerol, propylene glycol monoethyl ether, carbonates, hydrogen carbonates, guanidines, ureas and also primary, secondary and tertiary phosphates, opacifiers such as latex,
  • Pearlescent agents such as ethylene glycol mono- and distearate, blowing agents such as propane-butane mixtures, N2O, CO2 and air as well as antioxidants, direct dyes, so-called coupler and developer components as oxidation dye precursors,
  • Reducing agents such as Thioglycolic acid and its derivatives, thiolactic acid, cysteamine, thio malic acid and ⁇ -mercaptoethanesulfonic acid, oxidizing agents such as hydrogen peroxide, potassium bromate and sodium bromate.
  • the invention also relates to the use of the compositions according to the invention for the treatment of keratin fibers, in particular hair.
  • Monomer 1 Monomer 2 molar mass [° C]
  • Luviskol ⁇ VA 64 a product of BASF, was investigated as comparative substance VI.
  • This substance is a vinyl acetate-vinyl pyrrolidone copolymer in a ratio of 40:60
  • Relative information such as “Good” or “medium” each refer to the subjective comparison with commonly used polymers.
  • Collagen hydrolyzate (approx. 39% active substance; CTFA name: hydrolyzed collagen) (HENKEL)

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Cosmetics (AREA)

Abstract

Les produits de soins capillaires contenant des polyoxazolines se caractérisent par un bon pouvoir de fixation, une viscosité résiduelle réduite et un effet antistatique prononcé. Ils se laissent en outre aisément pulvériser et peuvent être facilement enlevés à nouveau des cheveux par brossage et par lavage.
PCT/EP1995/000309 1994-02-08 1995-01-30 Produit de soins capillaires contenant des polymeres WO1995021602A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19944403952 DE4403952A1 (de) 1994-02-08 1994-02-08 Haarbehandlungsmittel mit Polymeren
DEP4403952.2 1994-02-08

Publications (1)

Publication Number Publication Date
WO1995021602A1 true WO1995021602A1 (fr) 1995-08-17

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/000309 WO1995021602A1 (fr) 1994-02-08 1995-01-30 Produit de soins capillaires contenant des polymeres

Country Status (2)

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DE (1) DE4403952A1 (fr)
WO (1) WO1995021602A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017205353A1 (fr) * 2016-05-23 2017-11-30 Microban Products Company Produit topique pour la peau ayant une propriété de rétention
US10834922B2 (en) 2014-11-26 2020-11-17 Microban Products Company Surface disinfectant with residual biocidal property
US10842147B2 (en) 2014-11-26 2020-11-24 Microban Products Company Surface disinfectant with residual biocidal property
US10925281B2 (en) 2014-11-26 2021-02-23 Microban Products Company Surface disinfectant with residual biocidal property
US11033023B2 (en) 2014-11-26 2021-06-15 Microban Products Company Surface disinfectant with residual biocidal property
US11503824B2 (en) 2016-05-23 2022-11-22 Microban Products Company Touch screen cleaning and protectant composition

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2836633B1 (fr) * 2002-03-04 2006-08-11 Oreal Utilisation de composes hybrides comme agents anti-polluants et anti-adherents, composition pour film souples

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1553988A (fr) * 1966-12-29 1969-01-17
DE1939669A1 (de) * 1969-08-05 1971-02-25 Huels Chemische Werke Ag Haarfestlegemittel
EP0330193A1 (fr) * 1988-02-25 1989-08-30 L'oreal Composition cosmétique pour le maintien de la coiffure contenant un polymère d'oxazoline et un acide 2-hydroxy 4-methoxy benzophénone 5-sulfonique salifié ou non
JPH02157213A (ja) * 1988-12-07 1990-06-18 Kao Corp 洗浄剤組成物
JPH0441415A (ja) * 1990-06-07 1992-02-12 Kao Corp ヘアコンディショナー組成物

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1553988A (fr) * 1966-12-29 1969-01-17
DE1939669A1 (de) * 1969-08-05 1971-02-25 Huels Chemische Werke Ag Haarfestlegemittel
EP0330193A1 (fr) * 1988-02-25 1989-08-30 L'oreal Composition cosmétique pour le maintien de la coiffure contenant un polymère d'oxazoline et un acide 2-hydroxy 4-methoxy benzophénone 5-sulfonique salifié ou non
JPH02157213A (ja) * 1988-12-07 1990-06-18 Kao Corp 洗浄剤組成物
JPH0441415A (ja) * 1990-06-07 1992-02-12 Kao Corp ヘアコンディショナー組成物

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 113, no. 2, 10 December 1990, Columbus, Ohio, US; abstract no. 217814, Y. YODA ET AL.: "Cleansing compositions containing polyethyleneimines for skin and hair" *
CHEMICAL ABSTRACTS, vol. 116, no. 26, 29 June 1992, Columbus, Ohio, US; abstract no. 262290, M. KONDO: "Hair conditioners containing polyethylenimines, cationic surfactants and oils" *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10834922B2 (en) 2014-11-26 2020-11-17 Microban Products Company Surface disinfectant with residual biocidal property
US10842147B2 (en) 2014-11-26 2020-11-24 Microban Products Company Surface disinfectant with residual biocidal property
US10925281B2 (en) 2014-11-26 2021-02-23 Microban Products Company Surface disinfectant with residual biocidal property
US11026418B2 (en) 2014-11-26 2021-06-08 Microban Products Company Surface disinfectant with residual biocidal property
US11033023B2 (en) 2014-11-26 2021-06-15 Microban Products Company Surface disinfectant with residual biocidal property
US11134678B2 (en) 2014-11-26 2021-10-05 Microban Products Company Surface disinfectant with residual biocidal property
US11134674B2 (en) 2014-11-26 2021-10-05 Microban Products Company Surface disinfectant with residual biocidal property
WO2017205353A1 (fr) * 2016-05-23 2017-11-30 Microban Products Company Produit topique pour la peau ayant une propriété de rétention
CN109152362A (zh) * 2016-05-23 2019-01-04 美可帮产品公司 具有保留性质的局部皮肤产品
US11503824B2 (en) 2016-05-23 2022-11-22 Microban Products Company Touch screen cleaning and protectant composition

Also Published As

Publication number Publication date
DE4403952A1 (de) 1995-08-10

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