WO2014095164A1 - Laque pour un maintien souple et durable - Google Patents

Laque pour un maintien souple et durable Download PDF

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Publication number
WO2014095164A1
WO2014095164A1 PCT/EP2013/073677 EP2013073677W WO2014095164A1 WO 2014095164 A1 WO2014095164 A1 WO 2014095164A1 EP 2013073677 W EP2013073677 W EP 2013073677W WO 2014095164 A1 WO2014095164 A1 WO 2014095164A1
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group
polyols
composition according
cosmetic composition
polyurethane
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PCT/EP2013/073677
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German (de)
English (en)
Inventor
Diane Metten
Bernd Richters
Rene Scheffler
Original Assignee
Henkel Ag & Co. Kgaa
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Publication of WO2014095164A1 publication Critical patent/WO2014095164A1/fr

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    • 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
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/87—Polyurethanes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/046—Aerosols; Foams
    • 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

Definitions

  • the invention is in the technical field of forming and fixing the shape of keratin-containing fibers, in particular human hair.
  • keratin-containing fibers in particular human hair.
  • all animal hairs e.g. Wool, horsehair, angora hair, furs, feathers and products or textiles made from them.
  • the keratin fibers are human hair.
  • polymers in various cosmetic products is widespread. They are found in skin treatment agents as well as in hair treatment agents, in agents that are washed off or washed off immediately after use, so-called rinse-off products, as well as in skin or skin care products Hair remains, so-called leave-on remedies.
  • the polymers are used for various reasons and in each case exploited certain properties of the polymers.
  • agents for skin treatment in shampoos, hair conditioners and hair treatments, the thickening or care properties of the polymers are often in the foreground.
  • styling agents in addition to these properties, above all film-forming and / or strengthening effects are required.
  • polymers also serve as an aid to improve the deposition and fixation of other active ingredients and ingredients on the skin or hair or make it possible.
  • rubbing fastness and the stability of the dyeing can be increased.
  • styling agents it is necessary for the polymers used to give the treated hair the strongest possible hold.
  • styling agents must meet a whole range of other requirements. These may be broadly subdivided into properties on the hair, properties of the particular formulation, eg properties of the foam, of the gel or of the sprayed aerosol, and of properties relating to the handling of the styling agent, the properties of the hair being of particular importance. Particularly noteworthy are moisture resistance, low tackiness and a balanced conditioning effect.
  • a styling agent should be universally applicable as possible for all hair types. Pump sprays contain a higher proportion of water than aerosol sprays.
  • the firming polymers applied by a pump spray often give a good initial hold, but in particular decreases at higher humidity.
  • carboxylate-based anionic polyester-polyurethane polymers increasingly used in pump sprays are in need of improvement in terms of durability and flexibility.
  • the object of the present invention was therefore to provide a cosmetic agent which gives keratin-containing fibers, especially human hair, very good support, without having to sacrifice flexibility and good moisture resistance - in particular sweat and water resistance.
  • a first subject of the invention is a cosmetic spraying agent containing in a cosmetically acceptable carrier
  • At least one polyurethane obtainable by reacting at least one isocyanate group-containing polyurethane prepolymer A) with at least one amino-containing compound B).
  • polyurethanes within the meaning of the invention are polymeric compounds which have at least two preferably at least three urethane-containing repeat units -NH-C (O) -O-. Also included according to the invention are polyurethanes which, owing to their production, also contain urea group-containing repeating units -NH-C (O) -NH-, as are formed, in particular, in the reaction of the isocyanate-terminated prepolymers A) with the amino-containing compounds B).
  • the polyurethane prepolymer A) used in this invention has terminal isocyanate groups, i. the isocyanate groups are at the chain ends of the prepolymer.
  • all chain ends of a prepolymer have isocyanate groups.
  • the polyurethane prepolymer A) used according to the invention preferably has essentially neither ionic nor ionogenic groups, ie the content of ionic and ionic groups is expediently below 15 milliequivalents per 100 g of polyurethane prepolymer A), preferably below 5 milliequivalents, more preferably below one milliequivalent and completely be particularly preferably below 0.1 milliequivalents per 100 g of polyurethane prepolymer A).
  • Hair treatment compositions which are preferred according to the invention are characterized in that at least one of the isocyanate group-containing polyurethane prepolymers A) has a proportion of ionic and / or ionogenic groups below 20 milliequivalents per 100 g polyurethane prepolymer, preferably below 5 milliequivalents per 100 g polyurethane prepolymer, more preferably below 1 milliequivalent per 100 g polyurethane prepolymer and especially below 0.1 milliequivalents per 100 g polyurethane prepolymer.
  • the prepolymers A) used to prepare the polyurethanes are preferably obtainable by the reaction of polyisocyanates and one or more polyols selected from the group consisting of polyether polyols, polycarbonate polyols, polyether polycarbonate polyols and / or polyester polyols.
  • Preferred polyurethanes to be used according to the invention are obtainable by
  • polymeric polyols preferably having number average molecular weights of 400 to 8000 g / mol (here and in the following molecular weight data determined by gel permeation chromatography over polystyrene standard in tetrahydrofuran at 23 ° C), more preferably 400 to 6000 g / mol and particularly preferably of 600 to 3000 g / mol, and OH functionalities of preferably 1, 5 to 6, more preferably 1, 8 to 3, particularly preferably from 1, 9 to 2.1,
  • amino-containing compounds B such as primary and / or secondary amines and / or diamines.
  • Suitable polyisocyanates of component A1) are, in particular, the aliphatic, aromatic or cycloaliphatic polyisocyanates known per se with an NCO functionality of greater than or equal to 2. Particular preference is given in A1) to hexamethylene diisocyanate, isophorone diisocyanate or the isomeric bis (4,4 '). - Isocyanatocyclohexyl) methanes and mixtures of the aforementioned diisocyanates used.
  • polymeric polyols are preferred.
  • the expression "polymeric" polyols means here in particular that said polyols have at least two, more preferably at least three, interconnected repeat units Polyester polyols known in polyurethane lacquer technology, polyacrylate polyols, polyurethane polyols, polycarbonate polyols, polyether polyols, polyester polyacrylate polyols, polyurethane polyacrylate polyols, polyurethane polyester polyols, polyurethane polyether polyols, polyurethane polycarbonate polyols, and polyester polycarbonate polyols. These can be used in A2) individually or in any mixtures with each other.
  • aliphatic polyester polyols based on aliphatic carboxylic acids and aliphatic polyols, in particular based on adipic acid and aliphatic alcohols, such as hexanediol and / or neopentyl glycol.
  • the number average molecular weight of these polyester polyols is preferably 600 to 3000 g / mol.
  • hydroxyl-containing polycarbonates preferably polycarbonatediols, with number-average molecular weights Mn of preferably 400 to 8000 g / mol, preferably 600 to 3000 g / mol.
  • carbonic acid derivatives such as diphenyl carbonate, dimethyl carbonate or phosgene
  • polyether-polycarbonate diols instead of or in addition to pure polycarbonate diols, it is also possible to use polyether-polycarbonate diols in A2). Hydroxyl-containing polycarbonates are preferably built linear.
  • component A2) may be polyether polyols.
  • polyether polyols known per se in polyurethane chemistry, such as are obtainable by polymerization of tetrahydrofuran by means of cationic ring opening, are particularly suitable.
  • suitable polyether polyols are the per se known addition products of styrene oxide, ethylene oxide, propylene oxide, butylene oxide and / or epichlorohydrin to di- or polyfunctional starter molecules.
  • polyalkylene glycols such as polyethylene, polypropylene and / or polybutylene glycols are applicable, in particular with the above-mentioned preferred molecular weights.
  • starter molecules it is possible to use all compounds known from the prior art, for example water, butyl diglycol, glycerol, diethylene glycol, trimethylolpropane, propylene glycol, sorbitol, ethylenediamine, triethanolamine, 1,4-butanediol.
  • Particularly preferred components in A2) are polytetramethylene glycol polyethers and polycarbonate polyols or mixtures thereof, and polytetramethylene glycol polyethers are particularly preferred.
  • component A2) is accordingly
  • Mixtures containing at least one polyether polyol and at least one polycarbonate polyol Mixtures containing more than one polyether polyol, or a mixture of several polyether polyols having different molecular weights, in particular poly (tetramethylene glycol) polyether polyols (such as (HO- (CH 2 -CH 2 -CH 2 -CH 2 - 0) xH),
  • polyester polyols having a number average molecular weight of 600 to 3000 g / mol, in particular aliphatic polyester polyols based on aliphatic carboxylic acids and aliphatic polyols, in particular based on adipic acid and aliphatic alcohols, such as hexanediol and / or neopentyl glycol.
  • polyols in particular non-polymeric polyols, of the preferred molecular weight range from 62 to 399 mol / g with up to 20 carbon atoms. Also suitable are ester diols of the stated molecular weight range.
  • component A4) one or more in particular isocyanate-reactive nonionic hydrophilicizing agents are optionally used to prepare the polyurethanes used according to the invention.
  • the hydrophilicizing agents used as component A4) are in particular different from components A2) and A3).
  • the amino-containing compounds B) are preferably selected from primary and / or secondary amines and / or diamines.
  • the amino-containing compounds B) comprise at least one diamine.
  • the amino-containing compounds B) are preferably selected from amino-containing compounds B2) which have ionic or ionogenic groups, and amino-containing compounds B1) which have no ionic or ionogenic group.
  • the amino-containing compounds B) comprise at least one amino-containing compound B2) which has ionic and / or ionogenic (ion-forming) groups.
  • the ionic and / or ionogenic group used is particularly preferably the sulfonate or sulfonic acid group, more preferably the sodium sulfonate group.
  • the amino-containing compounds B) comprise both amino-containing compounds B2) which have ionic and / or ionogenic groups, and also amino-containing compounds B1) which have no ionic or ionogenic group.
  • Component B) is preferably selected from primary or secondary amine and / or diamines. It includes in particular diamines.
  • component B it is possible in particular to use amines which have no ionic or ionogenic, such as anionic hydrophilicizing groups (hereinafter component B1)) and it is possible to use amines which have ionic or ionogenic, in particular anionic hydrophilicizing groups (cf. Following component B2)).
  • anionic hydrophilicizing groups hereinafter component B1
  • anionic hydrophilicizing groups hereinafter component B2
  • component B1 1, 2-ethylenediamine, bis (4-aminocyclohexyl) methane, 1, 4-diaminobutane, isophoronediamine, ethanolamine, diethanolamine and diethylenetriamine are preferably used as component B1).
  • the polyurethanes used according to the invention preferably contain a sulfonic acid or sulfonate group. These groups are introduced into the polyurethanes used according to the invention via the amine component B2).
  • component B) comprises at least one component B2).
  • Suitable anionic hydrophilic compounds as component B2) preferably contain a sulfonic acid or sulfonate group, more preferably a sodium sulfonate group.
  • Suitable anionic hydrophilic compounds as component B2) are, in particular, the alkali metal salts of mono- and diaminosulfonic acids.
  • anionic hydrophilicizing agents examples include salts of 2- (2-aminoethylamino) ethanesulfonic acid, ethylenediaminepropyl or butylsulfonic acid, 1, 2- or 1, 3-propylenediamine-ß-ethylsulfonic acid or taurine.
  • the salt of cyclohexylaminopropanesulfonic acid (CAPS) can be used as an anionic hydrophilicizing agent.
  • Particularly preferred anionic hydrophilicizing agents B2) are those which contain sulfonate groups as ionic groups and two amino groups (in particular the salts of 2- (2-aminoethylamino) ethylsulfonic acid or 1,3-propylenediamine- ⁇ -ethylsulfonic acid).
  • the polyurethanes used according to the invention contain at least one sulfonate group.
  • the anionic group in the component B2) may also be a carboxylate or carboxylic acid group.
  • Component B2) is then preferably selected from diaminocarboxylic acids.
  • this embodiment is less preferred since carboxylic acid-based components B2) must be used in higher concentrations.
  • hydrophilization it is also possible to use mixtures of anionic hydrophilicizing agents B2) and nonionic hydrophilicizing agents A4).
  • polyurethanes used according to the invention are those having the following INCI names: Polyurethane-32 (copolymer obtainable by reacting poly (tetramethylene glycol) polyether polyol with hexamethylene diisocyanate and isophorone diisocyanate and reacting the reaction product with ethylenediamine and N- (2-aminoethyl) -3-aminoethanesulfonic acid);
  • Polyurethane-34 (copolymer, obtainable by reacting an aliphatic polyester polyol based on adipic acid, hexanediol and neopentyl glycol with hexamethylene diisocyanates and reaction of the reaction product with ethylenediamine and N- (2-aminoethyl) -3-aminoethanesulfonic acid);
  • Polyurethane-35 (copolymer obtainable by reacting an aliphatic polyester polyol based on adipic acid, hexanediol and neopentyl glycol with dicyclohexylmethane diisocyanate and reacting the reaction product with ethylenediamine and N- (2-aminoethyl) -3-aminoethanesulfonic acid);
  • Polyurethane-48 is a very particularly preferably used in the inventive polyurethane.
  • the polyurethanes of the invention are preferably substantially linear molecules, but may also be branched, which is less preferred.
  • the number average molecular weight of the polyurethanes preferably used according to the invention is for example from about 1000 to 200,000, preferably from 5,000 to 150,000.
  • Preferred agents according to the invention are characterized in that, based on the total weight of the agent according to the invention, said polyurethane is present in a total amount of from 0.5 to 10% by weight, preferably from 2.0 to 8.0% by weight.
  • the cosmetic compositions according to the invention may contain, in addition to the previously described polyurethane, at least one further setting polymer which is different from the previously described polyurethane.
  • Firming polymers contribute to the retention of the imprinted shape of the fiber collective, e.g. the total hairstyle, at.
  • These polymers are at the same time also film-forming polymers and therefore generally typical substances for shaping hair treatment agents.
  • the film formation can be quite selective and connect only a few fibers.
  • Film-forming polymers are polymers which leave a continuous film on the skin, the hair or the nails when drying.
  • Such film formers can be used in a wide variety of cosmetic products, such as for example face masks, make-up, hair fixatives, hair sprays, hair gels, hair waxes, hair treatments, shampoos or nail varnishes.
  • Particular preference is given to those polymers which have a have sufficient solubility in water or water / alcohol mixtures to be present in the inventive agent in completely dissolved form.
  • the film-forming polymers may be of synthetic or natural origin.
  • film-forming polymers are understood as meaning polymers which, when used in 0.01 to 20% strength by weight aqueous, alcoholic or aqueous-alcoholic solution, are capable of depositing a transparent polymer film on the hair.
  • the additional setting polymers are preferably selected from nonionic setting polymers, amphoteric setting polymers, cationic setting polymers and anionic setting polymers, more preferably among nonionic setting polymers, anionic setting polymers, amphoteric setting polymers.
  • the agent according to the invention preferably additionally contains at least one consolidating nonionic polymer containing at least one structural unit selected from the group of the structural units of the formulas (M1) to (M6)
  • R is a hydrogen atom or a methyl group
  • R ' represents a hydrogen atom or a (C 1 to C 4 ) -acyl group
  • R "and" independently of one another represent a (C 1 to C 7 ) -alkyl group or a hydrogen atom
  • R '" represents a linear or branched (C- ⁇ -C 4) alkyl group or a (C 2 to C 4) - hydroxyalkyl group.
  • the additional strengthening nonionic polymers are preferably present in the composition according to the invention in an amount of from 0.1 to 20.0% by weight, more preferably from 0.2 to 10% by weight. % to 15.0 wt .-%, most preferably from 0.5 wt .-% to 10.0 wt .-%, each based on the weight of the inventive composition.
  • Preferred nonionic fixing polymers are homopolymers or copolymers which are synthesized from at least one of the following monomers: N-vinylpyrrolidone, N-vinylcaprolactam, vinyl esters (such as vinyl acetate, vinyl alcohol), acrylamide, methacrylamide, alkyl and dialkylacrylamide (in particular N-vinylpyrrolidone).
  • Nonionic polymers based on ethylenically unsaturated monomers which are particularly suitable for the compositions according to the invention comprise at least one of the following structural units wherein R 'represents a hydrogen atom or a (Cr to C 30 ) acyl group, in particular a
  • homopolymers of vinyl caprolactam or vinyl pyrrolidone such as Luviskol ® K 90 or Luviskol ® K 85 from BASF SE
  • copolymers of vinylpyrrolidone and vinyl acetate such as Luviskol ® K 90 or Luviskol ® K 85 from BASF SE
  • the molar ratio of the contained from the monomer N-vinyl pyrrolidone Structural units to the structural units of the polymer contained from the monomer vinyl acetate in the range of 20 to 80 to 80 to 20, in particular from 30 to 70 to 60 to 40, for example, sold under the trademark Luviskol ® VA 37, Luviskol ® VA 55, Luviskol ® VA 64 and Luviskol ® VA 73 (from the firm BASF SE), terpolymers of vinylpyrrolidone, vinyl acetate and vinyl propionate, polyacrylamides such as Akypomine ® P 191 (from the company CHEM-Y), polyvinyl alcohols, for example, under the
  • An agent which comprises, as a consolidating nonionic polymer, at least one polymer selected from the group formed
  • polyvinylpyrrolidone Copolymers of N-vinylpyrrolidone and vinyl esters of carboxylic acids having 2 to 18 carbon atoms, in particular N-vinylpyrrolidone and vinyl acetate,
  • composition according to the invention contains at least one strengthening anionic polymer as additional strengthening polymer.
  • the agent according to the invention contains as said setting polymer at least one anionic setting polymer comprising at least one structural unit of the formula (I) and at least one structural unit of the formula (Ii)
  • R and R independently of one another represent a hydrogen atom or a methyl group, with the proviso that R and R 2 do not simultaneously represent a methyl group,
  • R 3 is a hydrogen atom or a methyl group
  • R 4 represents a carbamoyl group, a linear or branched (C 4 d 2) - alkylaminocarbonyl group, a linear or branched (C 4 to C 2) alkyloxycarbonyl group, a linear or branched (C 2 to Ci 2) acyloxy , a (C 2 to C 4 ) hydroxyalkylcarbonyl group or a phenyl group,
  • A represents a hydroxy group or an organic radical having at least one sulfonic acid group which binds to the structural unit via an oxygen atom or a group NH.
  • the anionic fixing polymer contains at least one structural unit of the formula (I) which is selected from at least one structural unit of the formulas 1-1) to (I-5)
  • the anionic fixing polymer contains at least one structural unit of the formula (I 1) which is selected from at least one structural unit of the formulas (11-1) to (I I-7)
  • R 5 is a (C 2 to C 12 ) acyl group (in particular acetyl or neodecanoyl)
  • the strengthening polymer in addition to the above structural units of the formulas (I) and (I I) additionally contains at least one structural unit of the formula (II I)
  • R represents a hydrogen atom or a methyl group
  • R 6 is a (C 1 to C 3 ) -alkyl group (in particular a methyl group or an ethyl group).
  • preferred agents according to the invention additionally contain at least one alkanolamine.
  • the alkanolamines which can be used as alkalizing agents according to the invention are preferably selected from primary amines having a C 2 -C 6 -alkyl basic body which carries at least one hydroxyl group.
  • alkanolamines are selected from the group consisting of 2-aminoethane-1-ol (monoethanolamine), 3-aminopropan-1-ol, 4-aminobutan-1-ol, 5-aminopentan-1-ol, 1 Aminopropan-2-ol, 1-aminobutan-2-ol, 1-aminopentan-2-ol, 1-aminopentan-3-ol, 1-aminopentan-4-ol, 3-amino-2-methylpropan-1-ol, 1-amino-2-methylpropan-2-ol, 3-aminopropane-1, 2-diol, 2-amino-2-methylpropane-1,3-diol.
  • Very particularly preferred alkanolamines according to the invention are selected from the group consisting of 2-aminoethane-1-ol, 2-amino-2-methylpropan-1-ol and 2-amino-2-methyl-propane-1,3-diol.
  • the agent according to the invention comprises at least one anionic setting polymer which comprises at least one structural unit of the formula (I-2), at least one structural unit of the formula (II) and at least one structural unit of the formula (III),
  • R 3 and R 5 are each independently hydrogen or methyl
  • R 4 is branched (C 4 to C 8 ) alkyloxycarbonyl, linear (C 4 to C 8 ) alkyloxycarbonyl, branched (C 4 to C 8 ) -alkylaminocarbonyl group, a linear (C 4 to C 8 ) -alkylaminocarbonyl group or a phenyl group, and
  • R 6 is a (C 1 to C 3 ) -alkyl group (in particular a methyl group or an ethyl group).
  • Copolymers of methacrylic acid and ethyl acrylate and tert-butyl acrylate are particularly preferred. Such copolymers are available, for example, under the trade names Luvimer 100 P, Luvimer 30 E or Luvimer 36 D from BASF SE. It is particularly preferred if, for all embodiments of this first preferred embodiment, the structural unit of the formula (I-2) is completely or partially neutralized. Therefore preferred agents according to the invention additionally contain at least one alkanolamine. Preferred alkalizing agents according to the invention are those mentioned above (vide supra).
  • the agent according to the invention comprises at least one anionic setting polymer which comprises at least one structural unit of the formula (I-1), at least one structural unit of the formula (II) and at least one structural unit of the formula (III),
  • R 3 and R 5 independently of one another represent a hydrogen atom or a methyl group
  • R 4 is a branched (C 4 to C 8 ) -alkylaminocarbonyl group, a linear (C 4 to C 8 ) -
  • R 6 is a (C 1 to C 3 ) -alkyl group (in particular a methyl group or an ethyl group).
  • preferred agents according to the invention additionally contain at least one alkanolamine.
  • Preferred alkalizing agents according to the invention are those mentioned above (vide supra).
  • Copolymers of acrylic acid and ethyl acrylate and tert-butylacrylamide are particularly preferred. Such copolymers are available, for example, under the trade names Ultrahold Strang or Ultrahigh 8 from BASF SE.
  • such agents are preferred according to the invention which comprise at least one polymer as a solidifying anionic polymer which contain at least one structural unit of the formula (I-3) and at least one structural unit of the formula (II-5)
  • Preferred anionic setting polymers of this type are selected from at least one polymer of the group formed
  • a particularly preferred agent of this embodiment according to the invention is characterized in that it contains a copolymer (a1) as a solidifying anionic polymer.
  • copolymers (a1) can be defined by the general formula
  • indices m, n and o vary depending on the molecular weight of the polymer and should not mean that they are block copolymers. Rather, structural units can be present in the molecule in a statistically distributed manner.
  • the copolymer (b1) has a molecular weight of from 50 to 500 kDa, preferably from 100 to 450 kDa, more preferably from 150 to 400 kDa and in particular from 200 to 300 kDa.
  • preferred agents according to the invention additionally contain at least one alkanolamine.
  • Preferred alkalizing agents according to the invention are those mentioned above (vide supra).
  • Copolymers of acrylamide with methacrylic acid and acryloyldimethyltaurate are available for example under the trade name Acudyne ® SCP (Rohm & Haas).
  • those agents are preferred according to the invention which contain as anionic fixing polymer at least one polymer containing at least one structural unit of the formula (I-5) and at least one structural unit of the formula (II-7)
  • R 5 is a (C 2 to d 2 ) acyl group (in particular acetyl or neodecanoyl).
  • Particularly preferred polymers (b) of this type are selected from at least one polymer of the group formed
  • Such copolymers are, for example, from the company Clariant under the trade name Aristoflex A 60 (INCI name: VA / Crotonates copolymer) in an isopropanol-water mixture (60 wt .-% of active substance), from BASF under the trade name Luviset CA 66 (Vinyl acetate crotonic acid copolymer 90:10, INCI name VA Crotonates Copolymer) provided by National Starch under the tradenames Resyn 28-2942 and Resyn 28-2930 respectively (INCI name: VA / Crotonates / Vinyl Neodecanoate Copolymer) ,
  • preferred agents according to the invention additionally comprise at least one alkanolamine.
  • Preferred alkalizing agents according to the invention are those mentioned above (vide supra).
  • the agent according to the invention contains as said setting polymer at least one amphoteric setting polymer comprising at least one structural unit of the formula (I) and at least one structural unit of the formula
  • R and R 3 are independently a hydrogen atom or a methyl group
  • R 4 stands for a linear or branched (C 4 to Ci2) alkylaminoethyl-aminocarbonyl group, a linear or branched (C 4 to C 12) -Alkylaminopropylaminocarbonyl distr, a linear or branched (C 4 to C 12) -Alkylanriinoethyloxycarbonyl distr, a linear or branched (C 4 to C 2) -Alkylaminopropyloxycarbonyl distr.
  • preferred agents according to the invention additionally contain at least one alkanolamine.
  • Preferred alkalizing agents according to the invention are those mentioned above (vide supra).
  • the agent according to the invention contains at least one additional strengthening amphoteric polymer in addition to said polyurethane polymer.
  • At least one amphoteric setting polymer which in addition to each at least one of the above structural units of the formulas (I) and (II-a) additionally contains at least one structural unit of the formula (III)
  • R 8 represents a hydrogen atom or a methyl group
  • R 9 is a (C 1 to C 4 ) -alkyl group (in particular a methyl group or an ethyl group).
  • a particularly preferred amphoteric setting polymer contains as a preferred structural unit of the formula (II-a) at least one structural unit selected from at least one structural unit selected from the group consisting of structural units of the formulas (II-8) to (II-15).
  • X 3 represents an oxygen atom or a group NH. It is preferred according to the invention if X 3 according to formulas (II-8) to (11-15) represents an oxygen atom.
  • the agent according to the invention comprises at least one amphoteric setting polymer which comprises at least one structural unit of the formula (I-1), at least one structural unit of the formula (II-3) and at least one structural unit of the formula (II-II) (in particular, selected from the group formed from the above formulas (II-8) to (11-15) with the proviso that X 3 represents an oxygen atom),
  • X 3 is an oxygen atom or a group NH
  • R 6 represents a hydrogen atom or a methyl group
  • R 7 is an alkyl group having 4 carbon atoms (especially n-butyl, sec-butyl, iso-butyl or tert-butyl).
  • amphoteric fixing polymer in addition to the above structural units of the formulas (1-1), (II-3) and (11-16) additionally contains at least one structural unit of the formula (III)
  • R 8 represents a hydrogen atom or a methyl group
  • R 9 is a (C 1 to C 4 ) -alkyl group (in particular a methyl group or an ethyl group).
  • Preferred amphoteric setting polymers of this type are selected from the group consisting of:
  • amphoteric fixing polymer is that available under the trade name Amphomer ® 028-4910 from AKZO polymer having the INCI name
  • the additional amphoteric setting polymers are preferably used in the inventive cosmetic agent in teilneutraliserter or neutralized form.
  • at least one (C 2 -C 6 ) -alkanolamine is preferably used.
  • Alkanolamines which can be used according to the invention are preferably selected from primary amines having a C 2 -C 6 -alkyl basic body which carries at least one hydroxyl group.
  • alkanolamines are selected from the group formed from 2-aminoethan-1-ol (monoethanolamine), tris (2-hydroxyethyl) amine (triethanolamine), 3-aminopropan-1-ol, 4-aminobutane-1 -ol, 5-aminopentan-1-ol, 1-aminopropan-2-ol, 1-aminobutan-2-ol, 1-aminopentan-2-ol, 1-aminopentan-3-ol, 1-aminopentan-4-ol , 3-Amino-2-methylpropan-1-ol, 1-amino-2-methylpropan-2-ol, 3-aminopropane-1, 2-diol, 2-amino-2-methylpropane-1,3-diol.
  • Very particularly preferred alkanolamines according to the invention are selected from the group consisting of 2-aminoethane-1-ol, 2-amino-2-methylpropan-1-ol and 2-amino-2-methyl-propane-1,3-diol.
  • 2-amino-2-methylpropanol has proven to be a particularly suitable neutralizing agent.
  • Cosmetic agents preferred according to the invention therefore contain 2-amino-2-methylpropanol.
  • the 2-amino-2-methylpropanol is preferably used in the compositions according to the invention in an amount which does not exceed the amount needed to neutralize the additional amphoteric setting polymers.
  • the amounts of 2-amino-2-methylpropanol used in the compositions according to the invention are preferably from 80 to 100%, particularly preferably from 90 to 100% and in particular from 95 to 100% of the amount required for complete neutralization of the additional amphoteric setting polymers.
  • the agents according to the invention preferably additionally contain at least one surfactant, nonionic, anionic, cationic, ampholytic surfactants being suitable in principle. It is preferred according to the invention if the agent according to the invention additionally contains at least one surfactant selected from at least one compound from the group formed from anionic surfactants, nonionic surfactants and amphoteric surfactants.
  • the group of ampholytic or amphoteric surfactants includes zwitterionic surfactants and ampholytes.
  • the surfactants according to the invention may already have emulsifying activity.
  • the additional surfactants are in the inventive composition preferably in an amount of 0.01 wt .-% to 5 wt .-%, particularly preferably from 0.05 wt .-% to 0.5 wt .-%, each based on the Weight of the agent, included.
  • agents according to the invention additionally comprise at least one nonionic surfactant.
  • Nonionic surfactants contain, for example, a polyol group, a polyalkylene glycol ether group or a combination of polyol and polyglycol ether group as the hydrophilic group.
  • Such compounds are, for example Addition products of 2 to 100 moles of ethylene oxide and / or 1 to 5 moles of propylene oxide to linear and branched fatty alcohols having 8 to 30 carbon atoms, to fatty acids having 8 to 30 carbon atoms and to alkylphenols having 8 to 15 carbon atoms in the alkyl group .
  • R is CO for a linear or branched, saturated and / or unsaturated acyl radical having 6 to 22 carbon atoms
  • R 2 is hydrogen or methyl
  • R 3 is linear or branched alkyl radicals having 1 to 4 carbon atoms
  • w is a number from 1 to 20 .
  • Hydroxy mixed ethers as described, for example, in DE-OS 19738866, sorbitan fatty acid esters and addition products of ethylene oxide onto sorbitan fatty acid esters, for example the polysorbates,
  • R 4 is an alkyl or alkenyl radical having 4 to 22 carbon atoms
  • G is a sugar radical having 5 or 6 carbon atoms
  • p is a number from 1 to 10. They can be obtained by the relevant methods of preparative organic chemistry.
  • alkylene oxide addition products of saturated linear fatty alcohols and fatty acids with in each case 2 to 100 mol of ethylene oxide per mole of fatty alcohol or fatty acid have proven to be very particularly preferred nonionic surfactants. Preparations with excellent properties are also obtained when they as nonionic surfactants C 12 -C 30 - fatty acid remono- and diesters of addition products of 1 to 30 moles of ethylene oxide with glycerol and / or addition products of from 5 to 60 moles of ethylene oxide with castor oil and hydrogenated castor oil.
  • the agents according to the invention as surfactant very particularly preferably contain at least one addition product of from 15 to 100 mol of ethylene oxide, in particular from 15 to 50 mol of ethylene oxide, to a linear or branched (in particular linear) fatty alcohol having from 8 to 22 carbon atoms.
  • ethylene oxide in particular from 15 to 50 mol of ethylene oxide
  • linear or branched (in particular linear) fatty alcohol having from 8 to 22 carbon atoms.
  • ceteareth-15, ceteareth-25 or ceteareth-50 which are marketed as Eumulgin ® CS 15 (Cognis), Cremophor A25 (BASF SE) or Eumulgin ® CS 50 (Cognis).
  • Suitable anionic surfactants are in principle all anionic surfactants suitable for use on the human body. These are characterized by a water-solubilizing, anionic group such as. As a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic alkyl group having about 8 to 30 carbon atoms. In addition, glycol or polyglycol ether groups, ester, ether and amide groups and hydroxyl groups may be present in the molecule. Examples of suitable anionic surfactants are, in each case in the form of the sodium, potassium and ammonium as well as the mono-, di- and trialkanolammonium salts having 2 to 4 C atoms in the alkanol group,
  • Sulfosuccinic acid mono- and dialkyl esters having 8 to 24 C atoms in the alkyl group and sulfosuccinic acid monoalkylpolyoxyethyl esters having 8 to 24 C atoms in the alkyl group and 1 to 6 oxyethyl groups,
  • Alpha-sulfofatty acid methyl esters of fatty acids having 8 to 30 carbon atoms are alpha-sulfofatty acids having 8 to 30 carbon atoms.
  • esters of tartaric acid and citric acid with alcohols which are adducts of about 2-15 molecules of ethylene oxide and / or propylene oxide with fatty alcohols having 8 to 22 C atoms,
  • R 7 CO- for a linear or branched, aliphatic, saturated and / or unsaturated acyl radical having 6 to 22 carbon atoms, Alk for CH 2 CH 2 , CHCH 3 CH 2 and / or CH 2 CHCH 3 , n for numbers from 0.5 to 5 and M is a cation, as described in DE-OS 197 36 906,
  • Condensation products of C 8 - C 30 - fatty alcohols with protein hydrolysates and / or amino acids and their derivatives which are known to the skilled person as protein fatty acid condensates, such as Lamepon ® - types Gluadin ® - types Hostapon ® KCG or Amisoft ® - types,
  • Dimethicone copolyols are understood according to the invention as meaning preferably polyoxyalkylene-modified dimethylpolysiloxanes of the general formulas (Si-1) or (Si-2):
  • the radical R is a hydrogen atom, an alkyl group having 1 to 12 C atoms, a
  • radicals R 'and R denote alkyl groups having 1 to 12 C atoms
  • x is an integer from 1 to 100, preferably from 20 to 30,
  • y is an integer from 1 to 20, preferably from 2 to 10 and
  • a and b are integers from 0 to 50, preferably from 10 to 30.
  • Particularly preferred dimethicone copolyols according to the invention are, for example, the products sold commercially under the trade name SILWET (Union Carbide Corporation) and DOW CORNING (Dow).
  • dimethicone copolyols according to the invention are Dow Corning 190 (INCI name: PEG / PPG-18/18 dimethicone) and Dow Corning 193 (INCI name: PEG-12 dimethicone) (Dow).
  • the agents according to the invention necessarily comprise a cosmetically acceptable carrier.
  • Preferred cosmetically acceptable carriers are aqueous, alcoholic or aqueous-alcoholic media.
  • Preferred cosmetic agents contain, based on their total weight, a water content of 5.0 to 90 wt .-%, particularly preferably 20 to 80 wt .-%, most preferably from 25 to 70 wt .-% and in particular from 30 to 45 wt .-%.
  • compositions according to the invention comprise at least one solvent which is different from water and is liquid at 25 ° C. and 1013 mbar.
  • an additional solvent of the agent according to the invention it is preferred according to the invention as an additional solvent of the agent according to the invention to use at least one (C 2 to C 6 ) -alkyl alcohol having at least one hydroxyl group.
  • the agent contains as additional solvent at least one alcohol having 2 to 6 carbon atoms and 1 to 3 hydroxyl groups.
  • said solvent is selected from at least one compound of the group formed from ethanol, ethylene glycol, isopropanol, 1,2-propylene glycol, 1,3-propylene glycol, glycerol, n-butanol, 1,3-butylene glycol.
  • a most preferred solvent is ethanol.
  • particularly preferred solvents are polyethylene glycol and / or polypropylene glycol.
  • the addition of polyethylene glycol and / or polypropylene glycol increases the flexibility of the polymer film formed when the agent according to the invention is used. If, therefore, a flexible hold is desired, the agents according to the invention preferably contain from 0.01 to 30% by weight of polyethylene glycol and / or polypropylene glycol, based on the total agent.
  • Very particularly preferred agents according to the invention are characterized in that they contain said solvents (in particular those previously mentioned as preferred solvents), in each case based on the total weight of the agent according to the invention, in an amount of 10% by weight to 99% by weight, in particular of 25 wt .-% to 70 wt .-%, most preferably from 45 wt .-% to 60 wt .-%, contain.
  • solvents in particular those previously mentioned as preferred solvents
  • the cosmetic compositions preferably have a pH (25 ° C.) of 5.5 to 9.0, preferably 6.0 to 8.5, particularly preferably 6.5 to 7.5.
  • Corresponding formulations are suitable due to their pH value also for packaging in metallic aerosol cans, but also due to their performance as nonaerosol sprays.
  • the inventive agent contains at least one (C 2 to C 6 ) -alkyl alcohol having at least one hydroxy group as a water-different, at 25 ° C and 1013 mbar liquid solvent (especially ethanol), each based on the total weight of the inventive agent, in an amount of 10 Wt .-% to 80 wt .-%, particularly preferably from 25 wt .-% to 70 wt .-%, most preferably from 45 wt .-% to 60 wt .-%, and
  • the cosmetic compositions of the invention may contain further ingredients.
  • the group of these other ingredients include in particular the cosmetically active auxiliaries and additives.
  • auxiliaries and additives in particular additional care substances are mentioned.
  • a silicone oil and / or a silicone gum can be used as a care material.
  • Silicone oils or silicone gums which are suitable according to the invention are in particular dialkyl and alkylaryl siloxanes, for example dimethylpolysiloxane and methylphenylpolysiloxane, and also their alkoxylated, quaternized or else anionic derivatives. Preference is given to cyclic and linear polydialkylsiloxanes, their alkoxylated and / or aminated derivatives, dihydroxypoly-dimethylsiloxanes and polyphenylalkylsiloxanes.
  • the agent may contain, for example, at least one protein hydrolyzate and / or one of its derivatives.
  • Protein hydrolysates are product mixtures obtained by acid, alkaline or enzymatically catalyzed degradation of proteins (proteins).
  • the term protein hydrolyzates also means total hydrolyzates as well as individual amino acids and their derivatives as well as mixtures of different amino acids.
  • the molecular weight of the protein hydrolysates which can be used according to the invention is between 75, the molecular weight for glycine, and 200,000, preferably the molecular weight is 75 to 50,000 and very particularly preferably 75 to 20,000 daltons.
  • the agent according to the invention may further comprise at least one vitamin, a provitamin, a vitamin precursor and / or one of their derivatives.
  • vitamins, provitamins and vitamin precursors are preferred, which are usually assigned to groups A, B, C, E, F and H.
  • panthenol increases the flexibility of the polymer film formed using the composition of the present invention.
  • compositions according to the invention may further contain at least one plant extract, but also mono- or oligosaccharides and / or lipids.
  • oil bodies are suitable as a care substance.
  • the natural and synthetic cosmetic oil bodies include, for example, vegetable oils, liquid paraffin oils, isoparaffin oils and synthetic hydrocarbons and di-n-alkyl ethers having a total of between 12 and 36 carbon atoms, in particular 12 to 24 carbon atoms.
  • Esteröle that is, esters of C 6 - C 30 - fatty acids with C 2 - C 30 - fatty alcohols, preferably Monoester of fatty acids with alcohols having from 2 to 24 carbon atoms such as isopropyl myristate (IPM Rilanit ®), isononanoic acid C16-18- alkyl ester (Cetiol ® SN), 2-ethylhexyl palmitate (Cegesoft ® 24), stearic acid-2-ethylhexyl ester (Cetiol ® 868), cetyl oleate, glycerol tricaprylate, cocofatty alcohol-caprinatV caprylate (Cetiol ® LC), n-butyl stearate, oleyl erucate (Cetiol ® J (600), isopropyl palmitate (Rilanit ® IPP), oleyl Oleate (Ceti
  • a preferred cosmetic agent according to the invention is characterized in that the cosmetic agent, based on its total weight, 0.01 to 5.0 wt .-%, preferably 0.02 to 4.0 wt .-% and in particular 0.05 to 2 , 0 wt .-% of an oil body.
  • conditioners are dicarboxylic acid esters, symmetrical, unsymmetrical or cyclic esters of carbonic acid with fatty alcohols, triflic acid esters of saturated and / or unsaturated linear and / or branched fatty acids with glycerol or fatty acid partial glycerides, which are to be understood as meaning monoglycerides, diglycerides and their technical mixtures.
  • the formulation of the agents according to the invention is most preferably applied to the hair as a nonaerosol spray or aerosol spray (in particular nonaerosol spray). Consequently, the preferred agent according to the invention additionally contains at least one propellant.
  • the agents according to the invention are packaged as an aerosol spray in a dispensing device, which is an additional compressed gas container filled with a propellant ("aerosol container”)
  • a dispensing device which is an additional compressed gas container filled with a propellant
  • the pressurized gas containers with the aid of which a product is distributed by the internal gas pressure of the container via a valve one by definition as "aerosol container”.
  • the agents according to the invention are packaged as a nonaerosol spray in a non-aerosol container as a delivery device.
  • a nonaerosol container a container under normal pressure is defined in reverse to the aerosol definition, with the aid of which a product is distributed by means of mechanical action by a pumping or squeezing system as a spray mist.
  • the aerosol embodiment of the invention can be prepared in a conventional manner.
  • all constituents of the composition according to the invention, with the exception of the blowing agent are introduced into a suitable pressure-resistant container. This is then closed with a valve. By conventional techniques, finally, the desired amount of blowing agent is introduced.
  • compositions according to the invention which are in the form of an aerosol product, can be prepared in a customary manner.
  • all components of the composition according to the invention are introduced into a suitable pressure-resistant container. This is then closed with a valve.
  • the desired amount of blowing agent is introduced.
  • a second subject of the present invention is therefore a product comprising i) a dispenser in the form of an aerosol container, and
  • suitable blowing agents are for example selected from N 2 0, dimethyl ether, C0 2 , air, alkanes having 3 to 5 carbon atoms, such as propane, n-butane, iso-butane, n-pentane and iso-pentane, and their mixtures. Preference is given to dimethyl ether, propane, n-butane, isobutane and mixtures thereof. According to a preferred embodiment, said alkanes, mixtures of said alkanes or mixtures of said alkanes with dimethyl ether are used as sole blowing agent. However, the invention expressly also includes the concomitant use of propellants of the type of chlorofluorocarbons, but in particular of fluorocarbons.
  • the propellant (especially dimethyl ether) is in the inventive compositions of the embodiment as aerosol spray preferably in an amount of 30 to 60 wt .-% - based on the weight of the total composition - included.
  • dimethyl ether will be used as the sole blowing agent
  • the sizes of the aerosol droplets and the respective size distribution can be set for a given spraying device.
  • the spray rate of the sprays according to the invention is preferably 6.5 to 10.0 g / 10 s.
  • agents according to the invention are packaged in an aerosol container with a star valve with a bore of 0.27 to 0.35 mm diameter.
  • Such valves are sold, for example, as valves of the type KE or KEN from the company. Coster.
  • the spray formulations according to the invention can be applied in any propellant-free spray system, which has a dispensing container and a spray valve, so z. B. in a flexible pressure bottle with dip tube and spray valve (Squeeze Bottie), in a Balloon Nebulizer, which operates on the Venturi principle or in a pump spray bottle, the pump lever with the index finger or the whole hand in the manner of Trigger is operated.
  • the dispensing container has a manually operated spray pump.
  • a third object of the present invention is therefore a product comprising
  • a dispensing device in the form of a non-aerosol container with a spray valve, and ii) a cosmetic agent of the first subject of the invention located in the non-aerosol container.
  • the cosmetic agents of the first subject of the invention are in particular in the nonaerosol container
  • a fourth subject of the invention is a method for reshaping keratinous fibers, in particular human hair, characterized in that a cosmetic agent of the first subject of the invention is applied from an aerosol container or a non-aerosol container to the keratinic fibers.
  • the keratinic fibers are not rinsed after the action of the cosmetic product of the first subject of the invention and the agent is left on the fiber.
  • Cosmetic agent for spraying containing in a cosmetically acceptable carrier water and at least one polyurethane obtainable by reacting at least one isocyanate group-containing polyurethane prepolymer A) with at least one amino-containing compound B).
  • Cosmetic composition according to item 1 characterized in that the prepolymers A) used to prepare the polyurethanes are preferably obtainable by the reaction of polyisocyanates and one or more polyols selected from the group consisting of polyether polyols, polycarbonate polyols, polyether polycarbonate Polyols and / or polyester polyols.
  • Cosmetic composition according to one of the items 1 or 2 characterized in that the polyurethanes are obtainable by
  • polymeric polyols preferably having number average molecular weights of 400 to 8000 g / mol (here and in the following molecular weight data determined by gel permeation chromatography over polystyrene standard in tetrahydrofuran at 23 ° C), more preferably 400 to 6000 g / mol and particularly preferably of 600 to 3000 g / mol, and OH functionalities of preferably 1, 5 to 6, more preferably 1, 8 to 3, particularly preferably from 1, 9 to 2.1,
  • Cosmetic composition according to item 3 characterized in that as component A1) hexamethylene diisocyanate, isophorone diisocyanate, the isomeric bis (4,4'-isocyanatocyclohexyl) methanes and mixtures of the aforementioned diisocyanates are used.
  • Cosmetic agent according to item 3 or 4 characterized in that as component A2), aliphatic polyester polyols based on aliphatic carboxylic acids and aliphatic polyols (in particular based on adipic acid and aliphatic alcohols, such as hexanediol and / or neopentyl glycol) are used.
  • component A2 aliphatic polyester polyols based on aliphatic carboxylic acids and aliphatic polyols (in particular based on adipic acid and aliphatic alcohols, such as hexanediol and / or neopentyl glycol) are used.
  • Cosmetic agent according to one of the items 1 to 5, characterized in that the amino-containing compounds B) at least one amino-containing compound B2) which has ionic and / or ionogenic (ion-forming) groups (in particular as the ionic and / or ionic group, the sulfonate or the sulfonic acid group).
  • Cosmetic agent according to one of the items 1 to 8, characterized in that based on the total weight of the agent according to the invention said polyurethane in a total amount of 0.5 to 10 wt .-%, preferably from 2.0 to 8.0 wt. %, is included.
  • X 3 is an oxygen atom or a group NH
  • R 6 represents a hydrogen atom or a methyl group
  • R 7 is an alkyl group having 4 carbon atoms (in particular n-butyl, sec-butyl, isobutyl or tert-butyl).
  • Cosmetic composition according to one of the items 1 to 1 characterized in that as an additional component at least one of water, at 25 ° C and 1013 mbar liquid solvent (in particular at least one (C 2 to C 6 ) alkyl alcohol having at least one hydroxyl group).
  • Cosmetic composition according to item 12 characterized in that said solvents, in each case based on the total weight of the agent according to the invention, in an amount of 10 wt .-% to 99 wt .-%, in particular from 25 wt .-% to 70 wt. %, most preferably from 45 wt .-% to 60 wt .-%, are included.
  • a dispensing device in the form of a non-aerosol container with a spray valve, and ii) a cosmetic agent of the first subject of the invention located in the non-aerosol container.
  • compositions were prepared by mixing the specified raw materials (the amounts are understood - unless otherwise stated - in percent by weight):
  • Composition A from the above table was packaged in a conventional aerosol container.

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Abstract

Produits cosmétiques destinés à être pulvérisés et contenant, dans un excipient cosmétiquement acceptable, de l'eau et au moins un polyuréthanne obtenu par mise en réaction d'au moins un prépolymère polyuréthanne A) contenant des groupes amino avec au moins un composé B) contenant des groupes amino, ces produits cosmétiques étant particulièrement adaptés à la mise en oeuvre en atomiseurs pour conférer un bon maintien.
PCT/EP2013/073677 2012-12-21 2013-11-13 Laque pour un maintien souple et durable WO2014095164A1 (fr)

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WO2018112753A1 (fr) * 2016-12-20 2018-06-28 Dow Global Technologies Llc Composition de peinture multicolore
CN110214162A (zh) * 2016-12-20 2019-09-06 陶氏环球技术有限责任公司 多色涂料组合物
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CN110214162B (zh) * 2016-12-20 2022-05-13 陶氏环球技术有限责任公司 多色涂料组合物

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