WO2021213954A1 - Polymère - Google Patents

Polymère Download PDF

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Publication number
WO2021213954A1
WO2021213954A1 PCT/EP2021/060024 EP2021060024W WO2021213954A1 WO 2021213954 A1 WO2021213954 A1 WO 2021213954A1 EP 2021060024 W EP2021060024 W EP 2021060024W WO 2021213954 A1 WO2021213954 A1 WO 2021213954A1
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WIPO (PCT)
Prior art keywords
weight
monomer
polymer
different
hair
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Application number
PCT/EP2021/060024
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English (en)
Inventor
David Graham
Volker Wendel
Christoph Tonhauser
Sandra Mack
Petra KEIE
Original Assignee
Basf Se
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.)
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Publication date
Application filed by Basf Se filed Critical Basf Se
Priority to BR112022021257A priority Critical patent/BR112022021257A2/pt
Priority to EP21718595.8A priority patent/EP4139372A1/fr
Publication of WO2021213954A1 publication Critical patent/WO2021213954A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
    • 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
    • A61K8/8141—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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • 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)
    • 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)
    • A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • 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 present invention relates to a polymer comprising repeating units derived from at least three different monomers, all of which are acrylic esters, methacrylic esters, acrylamides or methacrylamides, wherein this polymer has a calculated glass transition temperature of 29 to 44°C. Furthermore, the present invention relates to a composition suitable for use as a cosmetic formulation, wherein this composition comprises the said polymer, water and one or more further cosmetically acceptable ingredients. Furthermore, the present invention relates to the use of the said polymer or of the said composition for forming a film on human or animal hair or for styling human or animal hair.
  • WO 2011/112768 describes formulations containing water insoluble film forming polymers with hydrogen bonding groups for deposition on the surface of plants and/or wood to enhance the rain fastness or water resistance at the surface of the said substrates in order to improve the topical efficacy of the active ingredients included in such formulations , one of the drawbacks in the described approach is the limitation to completely water free formulations which mean only oil or solvent soluble active materials and formulation components can be used.
  • US 2005/0054532 describes using water soluble hydrogen bonding polymers to form a complex with active ingredients in order to enhance solubility and delivery to the surface of leaves/plants, however this approach although improving controlled release of actives to the plant, does not reference a water-resistant film which will increase contact time with foliage under wet conditions.
  • US 3/927/199 shows that terpolymers based on N-alkyl acrylamides or methacrylamides can be used in cosmetic applications, especially for hair cosmetic as good film-forming and setting agents
  • EP 1 694 728 B1 builds on the aforementioned work and describes the use of branched alkyl acrylate, especially those based upon tertiary butyl acrylate and/or methacrylate in combination with acrylamide or methacrylamide derivatives as long as a quaternisable or amiine functionalized acrylamide or methacrylamide monomer is also present.
  • the copolymers discussed also contained an additional linear alkyl acrylate such as ethyl acrylate or methacrylate.
  • EP 2 925799 B1 describes the synthesis and use of synthetic copolymers based on branched and linear acrylic esters combined with a cyclic N-Vinyl amide and further monomers which include non-quaternised acrylamides or methacrylamides. Such polymers appear to find use in applications as diverse as cosmetic hair and skin care, rheology modification in construction materials and emulsification in agricultural formulations. The importance of having a protonatable or quaternisable component to enhance interaction with with peptidic or proteic structures, however the discussion is limited to retaining solubility of the copolymers. The importance of glass transition temperature and its relevance for cosmetically acceptable performance are also discussed.
  • a “milder” non sensitizing method would be to employ keratin reducing agents such as N,N-disubstituted mercaptoacetamides, although these compounds are supposedly an improvement on harsher treatments in terms of sensitization and allergy potential, the mechanism still involves the reduction of bonds with in the hair fibre leading to inherent damage.
  • WO 2011/104282A2 describes semi-permanent straightening of frizzy, curly or wavy hair by treating the hair with glyoxylic acid in a buffer solution or formulation for 15 - 120 minutes, drying the hair before straightening with an iron between 150 - 250°C the results are hair chemically relaxed hair fibres which remain free of frizz for up to 5 washing cycles.
  • cystine/cysteine-residues of the keratinous fiber is well known for the perm treatment to create permanent waving.
  • cystine gets reduced by ammonium thioglycolate and after shaping of the hair cysteine gets re-oxidized to cystine by hydrogen peroxide to reform the disulfide bonds in the hair structure. It is a harsh process which damages the hair structure.
  • cystine/cysteine- residues in keratinous fibers for permanent modification of the hair.
  • Small organic molecules can be used to repair the hair structure by combining cysteine residues with each other (US 9,095,518 B2), use hydrophobic and cationic modified disulfides for conditioning of hair (WO 2013/050547) or use disulfide hair dyes to obtain a permanent hair color (EP 1 893694 B1).
  • EP 0 736 297 B1 describes a new material cysteine-silicon polymer for treatment of keratin substrates.
  • the low molecular weight allows penetration into hair and removal of water lead to further polymerization/crosslinking of the silicon and thus to strengthening of the hair.
  • DE 102004024509 B4 describes the strengthening of hair structure using polycondensation product of cystine & succinyl chloride in a perm treatment.
  • the problem underlying the present invention is to provide a substance that can form a film on human or animal hair that has some resistance to being washed out with water, so that the human or animal hair can be modified, e. g. modified by hair-styling or by coloring, wherein this modification has some resistance to being washed out with water, without strongly damaging the hair as strongly as it occurs with known methods, e. g. heat treatment methods used to curl hair.
  • This problem is solved by the polymer according to claim 1 of the present patent application as filed.
  • This polymer according to the present invention is one subject of the present invention. The following paragraphs describe the polymer according to the present invention, especially the monomers from which the repeating units are derived (by opening the polymerizable double bond of the monomer), in more detail.
  • Monomer A has formula (1) wherein Q is NH or O, R1 is H or CH 3 , R2 is selected from the group consisting of H, CH 3 , CH2CH3, CH2CH2CH3, CH2CH2CH2CH3, CH2CH2CH2CH3, and a C6 to C22 linear or branched alkyl chain, R3 is H or CH 3 , and R4 is H or CH 3 .
  • Monomer B must be different from monomer A and has formula (2) wherein R5 is H or CH 3 and R6 is selected from the group consisting of H, CH 3 , CH2CH 3 , CH2CH2CH3, CH2CH2CH2CH3, CH2CH2CH2CH2CH3, and a C6 to C22 linear or branched alkyl chain.
  • Monomer D must be different from monomer A and different from monomer B and different from monomer C and has formula (5) wherein R10 is H or CH3, R11 is selected from the group consisting of CH2CH2-N(CH3)2, CH 2 CH2-N(CH 2 CH3)2, CH 2 CH 2 CH2-N(CH3)2, and CH 2 CH 2 -N(H)C(CH 3 )3, Y is O or N, and R12, only present in case Y is N, is H or CH3.
  • Monomer E must be different from monomers A to D and is any monomer having an ethylenically unsaturated, polymerizable C-C-double-bond.
  • monomer E is selected from the group consisting of acrylic acid, methacrylic acid, 3,3,5-tri-methyl cyclohexyl methacrylate, styrene, vinyl neodecanoate, and vinyl neononaoate.
  • Repeating units derived from monomer A are present in the polymer according to the present invention in an amount of 30 - 65 % by weight, preferably in an amount of 40 - 55 % by weight, more preferably 45 - 55 % by weight.
  • Repeating units derived from monomer B are present in the polymer according to the present invention in an amount of 15 - 25 % by weight.
  • Repeating units derived from monomer C are present in the polymer according to the present invention in an amount of 0 - 15 % by weight. Repeating units derived from monomer C are optionally present. Preferably repeating units derived from monomer C are present in the polymer according to the present invention in an amount of 5 - 15 % by weight.
  • Repeating units derived from monomer D are present in the polymer according to the present invention in an amount of 10 - 30 % by weight, preferably in an amount of 15 - 30 % by weight, more preferably in an amount of 18 - 24 % by weight.
  • Repeating units derived from monomer E are present in the polymer according to the present invention in an amount of 0 - 5 % by weight, preferably in an amount of 0 - 3 % by weight, more preferably in an amount of 0 - 1.5 % by weight. Repeating units derived from monomer E are optionally present.
  • the polymer according to the present invention must have a calculated glass transition temperature between 29 and 44 °C better still from 30-40 °C as calculated using the Fox equation (T. G. Fox, Bull. Am. Phys. Soc. 1 (1956) 123.):
  • Tg,i glass transition temperature of homopolymer.
  • Tg,i glass transition temperatures
  • Tg,i-values can be found in literature resources known to the person skilled in the art, for example in the “Polymer Handbook” (editors: J. Brandrup et al, Wiley and Sons Ltd.).
  • the polymer according to the present invention offers mild electrostatic interaction with the hair surface as opposed to damaging chemical redox reactions with the hair structure. It provides a hydrophobic film after anchoring at the surface of the hair which prevents water or moisture from accessing the hair surface which is known to lead to frizz and loss of style, volume, or straightening. It enables the generation of reversible water-resistant films which can protect for example a hair style and/or ingredients applied at the surface of hair or skin,
  • the polymer according to the present invention can achieve permanent, semi-permanent or controlled reversible permanent effects when applied to hair or skin without using a chemical reaction e. g. redox mechanism to permanently damage or alter the structure of the surface. It can be formulated into water containing cosmetic formulations.
  • the application of the polymer according to the present invention to hair or skin to reach the desired cosmetic effect can be done with a cosmetically acceptable formulation, such as a cream, a gel, a mousse, a serum, or a spray.
  • One of the advantages of the polymer according to the present invention compared to existing cosmetic polymers is the enabling of longer lasting effects via resistance to moisture, washing and mechanical stress. This is presumably due to the finding that a self-orienting polymeric film can provide water/moisture resistance as well as resistance to mechanical stress modification of the surface that stays over a long period of time to create a long-lasting perceivable benefit for end-users while not damaging the surface or substrate in the way that current long lasting modifications such as perms do.
  • the polymer according to the present invention can be made by conventional polymerization techniques known to the person skilled in the art.
  • composition suitable for use as a cosmetic formulation wherein this composition comprises the polymer according to the present invention, water, and one or more further cosmetically acceptable ingredients different from the polymer and different from water
  • Suitable further cosmetically acceptable ingredients can be any cosmetically acceptable ingredient. These ingredients are known to the person skilled in the art and can be found in several publications, e. g. in the latest edition of the “International Cosmetic Ingredient Dictionary and Handbook” published by the Personal Care Products Council. Another well- known source of further suitable cosmetically acceptable ingredients is the cometic ingredient database Cosing. Cosing can be accessed on the internet pages of the European Commission.
  • Example Cream 1 Example Cream 2:
  • Phase A by adding the ingtredients (if necessary) to the water and allow to dissolve under stirring;
  • Phase B Combine the components of Phase B by adding the lactic acid to polymer p7 under stirring;
  • Phase A by combining the Ingredients and stir until homogeneous
  • Example Gel or Cream 1 Example Gel or Cream 1 :
  • the polymer according to the present invention can be comprised in a non-aerosol spray, typically at a concentration of 2.0 to 9.0 % by weight.
  • This spray can further comprise a solvent, typically at a concentration of 50.0 to 88.0 % by weight.
  • the solvent can be an alcohol e.g. ethanol; it can also be isopropanol or a volatile alkane such as n-pentane or mixtures thereof.
  • This spray can further comprise an additional solvent which is water, typically at a concentration of 5.0 to 45 % by weight.
  • the neutralizing agent can be a carboxylic acid e.g.
  • This spray can further comprise a humectant e.g. glycerol or propylene glycol typically at a concentration of 0.1 to 0.5 % by weight.
  • This spray can optionally comprise a second polymer chosen from the polyquaterniums e.g. PQ-37, PQ-4 typically at a concentration of 0.25 to 0.5 % by weight, or neutral polylactams e.g. polyvinyl caprolactam or polyvinyl pyrrolidone typically at a concentration of 0.0 to 3 % by weight.
  • This spray can optionally comprise a non-microbicidal additive e.g. triethyl citrate, typically in a concentration from 0.0 to 0.1 % by weight.
  • the polymer according to the present invention can be comprised in a non-aerosol mousse, typically at a concentration of 0.3 to 2.0 % by weight.
  • This mousse can further comprise a solvent, typically at a concentration of 0.5 to 3 % by weight.
  • the solvent can be an alcohol e.g. ethanol; it can also be isopropanol or a volatile alkane such as n-pentane or mixtures thereof.
  • This mousse can further comprise an additional solvent which is water, typically at a concentration of 90 to 95 % by weight.
  • the neutralizing agent can be a carboxylic acid e.g.
  • This mousse comprises an amphoteric surfactant e.g. cocamidopropyl betaine typically in a concentration of 1.5 to 15 % by weight.
  • This mousse also comprises an emulsifier e.g. PEG-40 hydrogenated castor oil, ceteareth-25, or combinations thereof, typically in a concentration of 0.1 to 0.5% by weight.
  • This mousse can optionally comprise a humectant e.g. glycerol or propylene glycol typically at a concentration of 0 to 5 % by weight.
  • This mousse can optionally comprise a second polymer chosen from the polyquaterniums e.g.
  • This mousse typically at a concentration of 0 to 0.5 % by weight.
  • This mousse can further comprise a natural oil e.g. hydrogenated rapeseed oil, moringa olifeira seed oil typically in a concentration of 0 to 3% by weight.
  • This mousse further comprises a preserving agent e.g. phenoxyethanol and ethylhexylglycerine typically at a concentration of 0.3 to 1.3 % by weight.
  • the polymer according to the present invention can be comprised in an aerosol mousse, typically at a concentration of 0.5 to 5.0 % by weight.
  • This mousse can further comprise a solvent, typically at a concentration of 1.5 to 15 % by weight.
  • the solvent can be an alcohol e.g. ethanol; it can also be isopropanol or a volatile alkane such as n-pentane or mixtures thereof.
  • This mousse can further comprise an additional solvent which is water, typically at a concentration of 82 to 92 % by weight.
  • the neutralizing agent can be a carboxylic acid e.g.
  • This mousse comprises at least one conditioning agent e.g. cetrimonium chloride typically in a concentration of 0.9 to 2.3 % by weight.
  • This mousse can further comprise a humectant e.g. panthenol, glycerol or propylene glycol typically at a concentration of 0 to 5 % by weight.
  • This mousse can optionally comprise a second polymer chosen from the polyquaterniums e.g.
  • PQ-37 typically at a concentration of 0.0 to 0.35 % by weight or alternatively from the neutral polylactams e.g polyvinylcaprolactam, polyvinylpyrrolidone, typically at a concentration of 0.0 to 2.5 % by weight.
  • This mousse further comprises a propellant which is a volatile gas e.g. propane or n-butane or isobutane or mixtures thereof typically at a concentration of 5 to 15 % by weight, alternatively a hydrofluorocarbon such as 1 ,1-difluoroethane or a volatile ether such as dimethylether also at concentrations of 5 to 15 % by weight.
  • This mousse can also comprise a preserving agent e.g. dimethyloldimethylhydantoin, 1,3-bis(hydroxymethyl)-5,5-demithylimidazolidin-2,4-dion, typically at a concentration of 0.0 to 0.25 % by weight.
  • the polymer according to the present invention can be comprised in a gel-creme, typically at a concentration of 0.3 to 3 % by weight.
  • This gel-creme can further comprise a solvent, typically at a concentration of 0.3 to 15 % by weight.
  • the solvent can be an alcohol e.g. ethanol; it can also be isopropanol or mixtures thereof.
  • This gel-creme can further comprise an additional solvent which is water, typically at a concentration of 83 to 99 % by weight.
  • the neutralizing agent can be a carboxylic acid e.g.
  • This gel-creme can further comprise a humectant e.g. panthenol, glycerol or propylene glycol typically at a concentration of 0.0 to 5.0 % by weight.
  • This gel-creme can comprise a second polymer chosen from neutral or cationically charged rheology modifying polymers e.g. dimethylacrylamide/ethyltrimonium chloride methacrylate copolymer, PQ-37, or combinations thereof, typically at a concentration of 0.3 to 5.0 % by weight.
  • This gel-creme further comprises an emollient or oil e.g.
  • This gel-creme can further comprise a preserving agent e.g. benzyl alcohol and methylchloroisothiazolinon and methylisothiazolinone typically in a concentration of 0.0 to 1.5 % by weight.
  • a preserving agent e.g. benzyl alcohol and methylchloroisothiazolinon and methylisothiazolinone typically in a concentration of 0.0 to 1.5 % by weight.
  • the polymer according to the present invention can be comprised in a gel, typically at a concentration of 0.3 to 3 % by weight.
  • This gel can further comprise a solvent, typically at a concentration of 0.3 to 15 % by weight.
  • the solvent can be an alcohol e.g. ethanol; it can also be isopropanol or mixtures thereof.
  • This gel can further comprise an additional solvent which is water, typically at a concentration of 60 to 95 % by weight.
  • the neutralizing agent can be a carboxylic acid e.g. lactic acid or other alpha hydroxy acids such as malic, citric, and tartaric acid.
  • This gel can further comprise a humectant e.g. panthenol, glycerol or propylene glycol typically at a concentration of 0.0 to 5.0 % by weight.
  • This gel can comprise a second polymer chosen from neutral or cationically charged rheology modifying polymers e.g. PQ-37, dimethylacrylamide/ethyltrimonium chloride methacrylate copolymer, typically at a concentration of 0.3 to 5.0 % by weight.
  • This gel further comprises a solubilizing agent e.g. PEG-40 Hydrogenated castor oil, typically in a concentration of 0.2 to 0.5 % by weight.
  • This gel can further comprise a preserving agent e.g. phenoxyethanol and ethylhexylglycerine typically in a concentration of 0.1 to 0.5 % by weight.
  • the synthesis of the polymer P7 was carried out as follows, the other polymers were synthesized accordingly: A solution in ethanol (462.5 kg) and water (284.62 kg) of monomer C (185 kg) was pre-charged into a suitable reaction vessel. The pre-charged reaction vessel was then purged three times with nitrogen and warmed to between 60 °C and 80 °C. The initiator 2,2’-azobis-(2-methylbutyronitrile) (5.89 kg) was dissolved in ethanol (111.91 kg) and delivered into a feed vessel (first initiator feed) which had been purged three times with nitrogen.
  • a shot making up 15.1 wt% of the first initiator feed was fed into the reaction vessel to initiate polymerization. After 10 minutes the remainder of the first initiator feed was fed into the reaction vessel at a constant rate over 6 hours until the feed was used up. The temperature was held constant during this process. Simultaneously, the addition of a monomer feed composed of monomer A (925 kg), monomer B (370 kg), monomer D (370 kg) and ethanol (185 kg) was started and continued at a constant rate until the feed was used up after three hours. The reaction-mixture was stirred for further 2 to 3 hours while maintaining the constant reaction temperature.
  • the Post polymerization process was carried out as follows, the reactor was heated to 10 degrees above the reaction temperature, and a feed containing initiator (9.25 kg) and ethanol (175.75 kg) was fed into the reactor over 30 minutes. After 2 hours of stirring a further amount of initiator (9.25 kg) in ethanol (175.75 kg) was introduced to the reactor over 30 minutes. The reaction-mixture was then stirred at 10 ° C above the reaction temperature for a further 8 hours. After this 8 hours post-polymerization-procedure the reaction mixture was cooled and diluted with ethanol (1850 kg) before filling into suitable containers. No further work-up was necessary.
  • **Hydrophobic component means the amount of hydrophobic monomers used. A solubility of less than 1.5 wt % in water at 20 °C is defined as hydrophobic).
  • VOC 50 solutions were composed of 3 % polymer, 50 % EtOH and 47 % H20.
  • VOC 90 solutions in the case of P2 and P4, were composed of 3 % polymer, 90 % EtOH and 7 % H20.
  • a polymer is according to the present invention if the following criteria are met:
  • Fig. 1 shows a series of polymers and comparative polymers organized with decending hydrophobic monomer content (here a solubility of less than 1.5 wt % in water at 20 °C is defined as hydrophobic).
  • TG curl retention
  • WR wash resistance
  • BS bending stiffness
  • inventive polymers P6, P7, P10, P11 and P15 fall into a selected area of the graphic. They possess a hydrophobic monomer content (HP) of 60-80 % and a glass transition temperature (TG) between 30 and 40 °C.
  • HP hydrophobic monomer content
  • TG glass transition temperature
  • Other polymers which display a good WR of 50 % where hydrophobic content lies above 80 % and TG lies outwith the 30-40 °C range display reduced performance in terms of the other necessary parameter BS. Many of them also have a poor CR value.
  • Fig. 2 further shows the effect of remaining in the above described areas (HP 60-80 %, TG 30- 40 °C) as polymers which lie outwith these areas e.g. comparison P6, P15, P16* and P17* at constant HP but reduced TG demonstrate rapid loss in cosmetic performance (BS, CR) whereas the best performance is observed at the outer limits of these ranges for P11 which displays the best water resistance despite having the lowest content of hydrophobic monomers.
  • solutions of the polymer with a 3 % polymer content were prepared with a neutralization of 30 wt-% of available amine functionality using lactic acid dilution with ethanol or water was necessary to reach the desired VOC content of the test solution.
  • Each hair strand was dipped into the polymer solution, upon removal from the solution each hair strand was re-formed into the rounded shape and any excess hairs were gathered together by running the strand between the fingers without exerting pressure. This process was repeated once more.
  • the strands were then dipped once again, the excess was then removed by pulling the hair strand (top to bottom) through a specially designed Teflon form, the hair strand was pulled through the Teflon form three times without any further dipping steps.
  • the formed hair strands were then hung vertically in a rack, where the hair strands were left to dry for at least 1 hour under normal laboratory conditions. After drying the rack and strands were placed in a climate chamber at 65 % relative humidity and 21 °C overnight.
  • the maximum force needed to break the hair strands was then measured in cN using a device such as a texture analyser with a 3 point bending stiffness test set-up described in the following photo or any one of a number of similar devices which can measure force required until breaking point e.g. a Diastron .
  • the process was repeated for the remaining hair strands in order to obtain a mean value of maximum force before breakage. This value is then converted to a percentage by the following equation
  • Fig. 3 shows an example of a 3 point bending stiffness test on a texture analyser where the treated hair strand is bent to breaking point by the probe which is connected to force measurement cell.
  • the wet hair strands were wound onto Teflon curlers with guides to ensure consistent curling over all strands.
  • the curlers with hair strands were then dried at 7 O0 C for at least 3 hours and are subsequently cooled overnight.
  • Each hair strand was unwound and attached to a lab stirrer, approximately 3 g of polymer solution was sprayed from a distance of 20 cm from a pump spray device while the hair strand was rotated at 70 rpm. Per polymer sample 5 such strands were prepared.
  • the strands were then allowed to dry for 1 hr under ambient conditions on filter paper before being hung on a rack with a scale into a climate chamber at 25 °C and 90 % rh the initial length of the strand and the length after 5 h and 24 h was recorded accordingly.
  • a 3 % polymer solution neutralized to 30 % (if containing amine functionality) was prepared to VOC50 (unless otherwise stated).
  • 3 ml of said solution were applied to a clean glass plate and distributed evenly with the end of a pipette, the resulting polymer film was left to dry for 2 h under ambient conditions (minimum 25 °C).
  • three individual droplets of de-ionized water were applied from a pipette to three different locations upon the surface of the dried polymer film, after 15 seconds the droplets were wiped from the surface of the polymer film using a gloved finger and the water resistance of the film rated as follows.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Birds (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne un polymère comprenant des motifs répétitifs dérivés d'au moins trois monomères différents, qui tous sont des esters acryliques, des esters méthacryliques, des acrylamides ou des méthacrylamides, ce polymère ayant une température de transition vitreuse calculée de 29 à 44 °C. En outre, la présente invention concerne une composition convenant à une utilisation comme formulation cosmétique, cette composition comprenant ledit polymère, de l'eau et un ou plusieurs ingrédients supplémentaires acceptables d'un point de vue cosmétique. La présente invention concerne en outre l'utilisation dudit polymère ou de ladite composition pour former un film sur les cheveux humains ou les poils animaux, ou pour coiffer des cheveux humains ou des poils d'animaux.
PCT/EP2021/060024 2020-04-23 2021-04-19 Polymère WO2021213954A1 (fr)

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GB2043077A (en) * 1979-02-06 1980-10-01 Mitsubishi Petrochemical Co Resins as hair dressing processes for making the resins and the hair dressings comprising them
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EP1694728B1 (fr) 2003-12-09 2008-08-13 Basf Se Copolymeres a base de tert.-butyl(meth)acrylate et leur utilisation dans laques a cheveux
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EP1893694B1 (fr) 2005-06-23 2010-11-17 Basf Se Colorants au soufre
WO2011104282A2 (fr) 2010-02-24 2011-09-01 Alderan S.A.S. Di D'ottavi Adele & C. Procédé de lissage semi-permanent de cheveux frisés, ondulés ou bouclés
WO2011112768A1 (fr) 2010-03-10 2011-09-15 Isp Investments Inc. Concentré préformé permettant l'administration de polymères filmogènes insolubles dans l'eau
WO2013050547A1 (fr) 2011-10-06 2013-04-11 L'oreal Composé sensible au ph, utilisation, composition et procédé de traitement mettant en œuvre ce composé
WO2014082904A1 (fr) * 2012-11-30 2014-06-05 Basf Se Moyen cationisable de modification de la rhéologie et de prise, composition correspondante et procédé de préparation de l'un et de l'autre
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