WO2002032978A1 - Polyurethannes cationiques a caractere elastique - Google Patents

Polyurethannes cationiques a caractere elastique Download PDF

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Publication number
WO2002032978A1
WO2002032978A1 PCT/FR2001/003157 FR0103157W WO0232978A1 WO 2002032978 A1 WO2002032978 A1 WO 2002032978A1 FR 0103157 W FR0103157 W FR 0103157W WO 0232978 A1 WO0232978 A1 WO 0232978A1
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WO
WIPO (PCT)
Prior art keywords
cationic
units
elastic nature
polyurethanes
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/FR2001/003157
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English (en)
French (fr)
Inventor
Nathalie Mougin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
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 LOreal SA filed Critical LOreal SA
Priority to DE60134252T priority Critical patent/DE60134252D1/de
Priority to EP01976410A priority patent/EP1326908B1/fr
Priority to JP2002536357A priority patent/JP4275941B2/ja
Priority to AU2001295692A priority patent/AU2001295692A1/en
Priority to US10/398,904 priority patent/US20040052753A1/en
Publication of WO2002032978A1 publication Critical patent/WO2002032978A1/fr
Anticipated expiration legal-status Critical
Priority to US11/905,236 priority patent/US20080025933A1/en
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0809—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups
    • C08G18/0814—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups containing ammonium groups or groups forming them
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
    • C08G18/6688—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3271

Definitions

  • the present invention relates to new cationic polyurethanes of elastic nature as well as their use in cosmetic compositions.
  • the polyurethanes disclosed in these documents however have glass transition temperatures (Tg) higher than room temperature (20 ° C), that is to say at room temperature they are in the glassy state and form brittle films unacceptable for cosmetic application.
  • Tg glass transition temperatures
  • physiologically acceptable polymers having low glass transition temperatures such as, for example, acrylic polymers, but these polymers generally form very sticky deposits, which has a drawback in most cosmetic applications.
  • the Applicant has surprisingly discovered a new group of physiologically acceptable polyurethanes forming non-sticky, non-brittle films capable of plastic and elastic deformation. These viscoelastic properties interesting are due to the presence, in the polymer, of long macromolecular units having a relatively low glassy transition temperature and which, therefore, at room temperature, are not found in the glassy state.
  • the subject of the present invention is therefore cationic polyurethanes of elastic nature, essentially consisting
  • a subject of the invention is also the use of the cationic polyurethanes of elastic nature above in cosmetic compositions with a view to improving the viscoelastic properties of the cosmetic deposits and films obtained from these compositions. It relates in particular to the use of these polyurethanes in lacquers and styling compositions, in nail varnishes and in makeup compositions.
  • the invention also relates to cosmetic compositions containing the cationic polyurethanes of elastic nature above.
  • the polyurethanes of elastic nature of the present invention thanks to their cationic charge, have the advantage to have an excellent affinity for keratinous substrates such as the hair, the nails and the horny layer of the epidermis to which keratin imparts a negative charge.
  • cationic polyurethanes of an elastic nature of the present invention makes it possible to improve the flexibility of the hairstyle, that is to say to obtain a more natural elastic hold of the hair than that obtained with usual fixing polymers.
  • These polyurethanes can be used to cover the nails with a shiny protective film resistant to mechanical attack. Their incorporation in nail varnishes improves their impact resistance and delays flaking.
  • the above cationic polyurethanes can also be used to improve the staying power of makeup compositions for the skin, the lips and the integuments. Indeed, the makeup products containing these polymers adhere well to the skin and the integuments and the deposits obtained follow the deformations of the keratinous substrates and do not pull the skin.
  • the cationic polyurethanes of elastic nature of the present invention consist essentially of three types of units which are
  • Tg glass transition temperature
  • Reactive functions with labile hydrogen are understood to mean functions capable, after leaving a hydrogen atom, of forming covalent bonds with the isocyanate functions of the compounds forming the units (b). Mention may be made, by way of example of such functions, of the hydroxyl, primary amine (-NH 2 ) or secondary amine (-NHR) groups, or alternatively the thiol groups (-SH).
  • polycondensation of compounds carrying these reactive functions with labile hydrogen with diisocyanates gives, depending on the nature of the reactive functions carrying labile hydrogen (-OH, -NH 2 , -NHR or -SH), respectively polyurethanes, polyureas or polythio urethanes. All these polymers are grouped together in the present application, for the sake of simplification, under the term polyurethanes.
  • the polyurethanes obtained have a branched structure.
  • the tertiary amines forming the cationic units (a1) have only two reactive functions containing labile hydrogen and the polyurethanes obtained by polycondensation therefore have an essentially linear structure.
  • the tertiary amines forming the cationic units (a1) are preferably chosen from the compounds corresponding to one of the following formulas: HX-R a -NR a -XH
  • each R a independently represents a C] alkylene group. 6 , linear or branched, C 3-6 cycloalkylene or arylene, all of which may be substituted by one or more halogen atoms and may contain one or more heteroatoms chosen from O, N, P and S
  • each R b independently represents a group C, _ 6 cycloalkyl, C 3. 6 or aryl, all of which may be substituted by one or more halogen atoms and comprise one or more heteroatoms chosen from O, N, P and S
  • each X independently represents an oxygen or sulfur atom or an NH group or NR C wherein R.reconstrusente alkyl, C, _ 6.
  • tertiary amines which are particularly preferred for obtaining cationic polyurethanes of elastic nature of the present invention, N-methyldiethanolamine and N-tert-butyldiethanolamine.
  • the tertiary amines forming the cationic units (a1) of the polyurethanes of the present invention can also be polymers with tertiary amine functions, carrying at their ends reactive functions with labile hydrogen.
  • the average molar mass in weight of these polymers with tertiary amine functions is preferably between 400 and 10,000.
  • polyesters resulting from the polycondensation of N-methyldiethanolamine and of adipic acid mention may be made of the polyesters resulting from the polycondensation of N-methyldiethanolamine and of adipic acid.
  • the tertiary amines forming the cationic units (a1) are partially or totally neutralized by an appropriate neutralizing agent, in particular mineral or organic acids such as hydrochloric acid, hydrobromic acid, carboxylic acids and in particular monocarboxylic acids such as acetic, propionic, benzoic, lactic, stearic and oleic acids, or polyacids.
  • an appropriate neutralizing agent in particular mineral or organic acids such as hydrochloric acid, hydrobromic acid, carboxylic acids and in particular monocarboxylic acids such as acetic, propionic, benzoic, lactic, stearic and oleic acids, or polyacids.
  • the organic acid can possibly carry other functions such as OH (citric acid, salicylic acid).
  • the second type of units forming the polyurethanes of the present invention are macromolecular units, called units (a2), derived from nonionic polymers carrying at their ends reactive functions with labile hydrogen and having a glass transition temperature (Tg), measured by differential enthalpy analysis., less than 10 ° C.
  • Tg glass transition temperature
  • the viscoelastic properties of polyurethanes are particularly advantageous when the units (a2) are derived from polymers having a glass transition temperature below 0 ° C and better still below -10 ° C.
  • the nonionic polymers capable of forming the nonionic units (a2) are chosen for example from polyethers, polyesters, polysiloxanes, copolymers of ethylene and butylene, polycarbonates and fluorinated polymers. Polyethers are particularly preferred, and among these poly (tetramethylene oxide).
  • the diisocyanates forming the units (b) include aliphatic, alicyclic or aromatic diisocyanates.
  • Preferred diisocyanates are chosen from methylenediphenyldiisocyanate, methylenecyclohexanediisocyanate, isophoronediisocyanate, toluenediisocyanate, naphthalene diisocyanate, butanediisocyanate and hexldiisocyanate. These diisocyanates can of course be used alone or in the form of a mixture of two or more diisocyanates. .
  • the cationic polyurethanes of an elastic nature of the present invention may contain, in addition to the units (a), (a2) and (b), necessarily present in the polyurethanes of the present invention, a certain fraction of units (a3) derived from monomeric nonionic compounds containing at least two functions containing labile hydrogen.
  • These units (a3) are derived for example from neopentylglycol, • from hexaethylene glycol or from aminoethanol.
  • the physical parameter characterizing the viscoelastic properties of the above cationic polyurethanes is their tensile recovery. This recovery is determined by tensile creep test consisting in rapidly stretching a test piece to a predetermined elongation rate, then releasing the stress and measuring the length of the test piece.
  • the creep test used for the characterization of cationic polyurethanes of elastic nature of the present invention is carried out as follows:
  • This copolymer film is obtained by drying, at a temperature of 22
  • Each strip is fixed between two jaws, 50 ⁇ 1 mm apart, and is stretched at a speed of 20 mm / minute (under the conditions of temperature and relative humidity above) until '' at an elongation of 50% ( ⁇ max ), i.e. up to 1.5 times its initial length.
  • ⁇ max 50%
  • the instant recovery (Rj) is calculated using the following formula: 0
  • the cationic polyurethanes of elastic nature of the present invention preferably have an instantaneous recovery (Rj), measured under the conditions indicated above, of between 5% and
  • the glass transition temperature (Tg) of the nonionic polymers forming the units (a2) and of the cationic polyurethanes of the present invention is measured by differential enthalpy analysis (DSC, differential scanning calorimetry) according to the standard.
  • the cationic polyurethanes of elastic nature of the present invention preferably have at least two glass transition temperatures, at least one of which is less than 10 ° C, preferably less than 0 ° C and more preferably less than
  • the instant recovery and, consequently, the viscoelastic properties of the polyurethanes of the present invention depend on the fractions of the different monomer units (a1), (a2), (a3) and (b).
  • the fraction of units (a1) must be sufficient to give the polymers their positive charge responsible for their good affinity for keratinous substrates.
  • the units (a2) must represent a fraction by weight sufficient for the polyurethanes to have at least a glass transition temperature below 10 ° C. and not to form brittle films.
  • the units (a1) represent from 1 to 90%, preferably from 5 to 60% by weight, the units (a2) from 10 to 80%, preferably from 40 to 70% by weight and the units ( a3) from 0 to 50% by weight, preferably from 0 to 30% by weight of the total polymer.
  • the patterns (b) are present in an essentially stoichiometric amount relative to the sum of the patterns (a1), (a2) and (a3).
  • obtaining polyurethanes having large molar masses presupposes a number of isocyanate functions practically identical to the number of functions containing labile hydrogen.
  • Those skilled in the art will know how to choose a possible molar excess of one or the other type of function to adjust the molar mass to the desired value.
  • the cationic polyurethanes of elastic nature can be incorporated into numerous cosmetic compositions whose cosmetic properties they improve.
  • the amount of polyurethane present in the various compositions depends of course on the type of composition and on the desired properties and can vary within a very wide range, generally between 0.5 and 90% by weight, preferably between 1 and 50% by weight, based on the final cosmetic composition.
  • the concentration is generally between 0.5 and 15% by weight.
  • nail varnishes they generally represent 0.5 and 40% by weight of the composition
  • makeup compositions for the skin, the lips and the integuments generally contain 0.5 to 20% by weight of the polyurethanes of the present invention. .
  • the following monomers and solvent are introduced into a thermostatically controlled reactor fitted with a mechanical stirring system and a condenser: - 1 mole of a mixture of diol type monomers, that is to say of a mixture of N-methyldiethanolamine and of poly (tetramethylene oxide) with a weight-average molar mass equal to 1400, the relative molar proportions of these two types of monomers being those indicated in Table 1 below, and - an amount of methyl ethyl ketone such that the concentration of diol type monomers is equal to 75% by weight.
  • the mixture is heated with stirring to a temperature of 70 ° C., then introduced dropwise with stirring, over a duration of approximately 2 hours, a small molar excess, i.e.
  • the reaction mixture is allowed to cool to ambient temperature, then it is diluted with acetone until at a polymer concentration of about 40% by weight.
  • a hydrochloric acid solution (2 mol / l) is added in an amount such that the amino groups are neutralized at the desired rate.
  • the various organic solvents are then removed (methyl ethyl ketone, acetone and ethanol) by vacuum distillation at a temperature of 40 ° C.
  • an amount of water sufficient to obtain a polymer concentration in water of about 25% by weight is added to the aqueous solution of the polymer.
  • PU1, PU2 and PU3 Three different polyurethanes (PU1, PU2 and PU3) are prepared in the manner described above, having respectively an N-methyldiethanolamine / poly (tetramethylene oxide) molar ratio equal to 2,
  • Table 1 shows the theoretical molar composition and the physicochemical characteristics of the three polymers obtained.
  • N-methyldiethanolamine 2 poly (tetramethylene oxide) having an average mass by weight of 1400, sold under the name Terathane® 1400 by the company DUPONT. ) isophoronediisocanate ) measured by gel permeation chromatography in THF, detection by refractometry.
  • Three hair compositions are prepared, each comprising, in an aerosol device, 65 g of dimethylether and 35 g of a water / ethanol mixture (1: 2) containing 3% by weight of one of the three cationic polyurethanes of elastic nature synthesized in 1 'Example 1.
  • compositions are easily applied to the hair.
  • the results obtained are collated in Table 2.
  • Polyurethane films are prepared from dispersions at

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Polymers & Plastics (AREA)
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  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Cosmetics (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
PCT/FR2001/003157 2000-10-17 2001-10-12 Polyurethannes cationiques a caractere elastique Ceased WO2002032978A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
DE60134252T DE60134252D1 (de) 2000-10-17 2001-10-12 Kationische polyurethane mit elastischem charakter
EP01976410A EP1326908B1 (fr) 2000-10-17 2001-10-12 Polyurethannes cationiques a caractere elastique
JP2002536357A JP4275941B2 (ja) 2000-10-17 2001-10-12 弾性カチオン性ポリウレタン
AU2001295692A AU2001295692A1 (en) 2000-10-17 2001-10-12 Cationic polyurethanes with elastic character
US10/398,904 US20040052753A1 (en) 2000-10-17 2001-10-12 Cationic polyurethanes with elastic character
US11/905,236 US20080025933A1 (en) 2000-10-17 2007-09-28 Elastic cationic polyurethanes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0013264A FR2815350B1 (fr) 2000-10-17 2000-10-17 Polyurethanes cationiques a caractere elastique
FR00/13264 2000-10-17

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US11/905,236 Division US20080025933A1 (en) 2000-10-17 2007-09-28 Elastic cationic polyurethanes

Publications (1)

Publication Number Publication Date
WO2002032978A1 true WO2002032978A1 (fr) 2002-04-25

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PCT/FR2001/003157 Ceased WO2002032978A1 (fr) 2000-10-17 2001-10-12 Polyurethannes cationiques a caractere elastique

Country Status (10)

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US (2) US20040052753A1 (enExample)
EP (1) EP1326908B1 (enExample)
JP (2) JP4275941B2 (enExample)
AR (1) AR030894A1 (enExample)
AT (1) ATE397027T1 (enExample)
AU (1) AU2001295692A1 (enExample)
DE (1) DE60134252D1 (enExample)
ES (1) ES2302749T3 (enExample)
FR (1) FR2815350B1 (enExample)
WO (1) WO2002032978A1 (enExample)

Cited By (3)

* Cited by examiner, † Cited by third party
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EP1645579A1 (fr) * 2004-09-21 2006-04-12 L'oreal Polyuréthane cationique ou cationisable à caractère élastique
US8449871B2 (en) 2006-03-20 2013-05-28 L'oreal Composition comprising novel polyurethanes and cosmetic treatment process
CN105120837A (zh) * 2013-03-29 2015-12-02 富士胶片株式会社 人工指甲组合物、人工指甲、人工指甲的形成方法和美甲套装

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FR2833960B1 (fr) * 2001-12-20 2007-04-13 Oreal Polyurethannes cationiques ou amphoteres auto-adhesifs
FR2863884B1 (fr) * 2003-12-19 2007-06-29 Oreal Composition coiffante comprenant, dans un milieu majoritairement aqueux, un polyurethane cationique elastique, procedes la mettant en oeuvre et utilisations
FR2872421B1 (fr) * 2004-07-01 2006-09-15 Oreal Procede de deformation permanente des cheveux mettant en oeuvre des polymeres filmogenes elastomeres
WO2006003027A1 (en) * 2004-07-01 2006-01-12 L'oreal Cosmetic composition comprising a tensioning agent and an elastomeric film-forming polymer
FR2872424B1 (fr) 2004-07-01 2006-12-29 Oreal Composition cosmetique non rincee comprenant des polymeres filmogenes elastomeriques, son utilisation pour le conditionnement des matieres keratiniques
FR2872410B1 (fr) * 2004-07-01 2006-12-15 Oreal Composition cosmetique comprenant un agent tenseur et un polymere filmogene elastomerique
FR2872425B1 (fr) * 2004-07-01 2006-12-22 Oreal Composition cosmetique rincee comprenant des polymeres filmogenes elastomeriques, son utilisation pour le conditionnement des matieres keratiniques
US20060000485A1 (en) * 2004-07-01 2006-01-05 Henri Samain Pressurized hair composition comprising at least one elastomeric film-forming polymer
US20060005326A1 (en) * 2004-07-01 2006-01-12 Isabelle Rollat-Corvol Dyeing composition comprising at least one elastomeric film-forming polymer and at least one dyestuff
US20060002882A1 (en) * 2004-07-01 2006-01-05 Isabelle Rollat-Corvol Rinse-out cosmetic composition comprising elastomeric film-forming polymers, use thereof for conditioning keratin materials
FR2872428B1 (fr) * 2004-07-01 2006-09-15 Oreal Composition capillaire pressurisee comprenant au moins un polymere filmogene elastomere
US20060005325A1 (en) * 2004-07-01 2006-01-12 Henri Samain Leave-in cosmetic composition comprising at least one elastomeric film-forming polymer and use thereof for conditioning keratin materials
US20060002877A1 (en) * 2004-07-01 2006-01-05 Isabelle Rollat-Corvol Compositions and methods for permanently reshaping hair using elastomeric film-forming polymers
US20060000033A1 (en) * 2004-07-01 2006-01-05 Isabelle Rollat-Corvol Dyeing composition comprising at least one elastomeric film-forming polymer and at least one oxidation dye precursor
FR2872427B1 (fr) * 2004-07-01 2006-10-13 Oreal Composition de coloration comprenant un polymere filmogene elastomere et une matiere colorante
FR2872426B1 (fr) 2004-07-01 2006-10-13 Oreal Composition de coloration comprenant un polymere filmogene elastomere et un precurseur de colorant d'oxydation
US20060067907A1 (en) * 2004-09-21 2006-03-30 Nathalie Mougin Cationic or cationizable polyurethane with elastic character
FR2894813B1 (fr) * 2005-12-16 2008-01-18 Oreal Composition cosmetique comprenant un copolymere (thio) urethane/(thio)uree capable de former au moins 3 liaisons hydrogene, et procede de traitement cosmetique
FR2894816B1 (fr) * 2005-12-16 2008-02-01 Oreal Composition cosmetique ou pharmaceutique comprenant un copolymere comportant au moins un groupe ionisable, et procede de traitement cosmetique
US8591923B2 (en) 2005-12-16 2013-11-26 L'oreal Cosmetic compositon comprising a (thio)urethane/(thio)urea copolymer capable of forming at least 3 hydrogen bonds, and a method of cosmetic treatment
CN101500536B (zh) * 2006-09-21 2011-12-28 狮王株式会社 毛发化妆品
FR2911274A1 (fr) * 2007-01-12 2008-07-18 Oreal Composition cosmetique comprenant un polyurethane cationique, un tensioactif, et un corps gras et applications de coiffage
FR2911276B1 (fr) * 2007-01-12 2009-03-06 Oreal Composition cosmetique comprenant un polyurethane cationique et un homo ou copolymere de vinylpyrrolidone et application au coiffage
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FR2930440B1 (fr) * 2008-04-28 2012-12-14 Oreal Composition cosmetique comprenant un polyurethane cationique et un polyacrylate particulier et utilisations en coiffage
FR2930441B1 (fr) 2008-04-28 2010-05-28 Oreal Compression cosmetique comprenant un polyrethane cationique et un derive de cellulose et utilisations en coiffage
FR2954151B1 (fr) 2009-12-17 2012-03-16 Oreal Utilisation d'une composition cosmetique comprenant au moins un polymere elastomere filmogene pour le traitement de la transpiration humaine
US10040893B2 (en) 2012-05-16 2018-08-07 Coloplast A/S Polymeric photoinitiators and photoinitiator monomers
EP3020454A1 (de) 2014-11-17 2016-05-18 Covestro Deutschland AG Polyurethanharnstoffe für Haarstyling-Zusammensetzungen
US11622929B2 (en) 2016-03-08 2023-04-11 Living Proof, Inc. Long lasting cosmetic compositions
ES2926991T3 (es) * 2017-08-09 2022-10-31 Medi Gmbh & Co Kg Un poliuretano con comportamiento de relajación retardado para productos de compresión
CN111133023B (zh) * 2017-09-13 2022-10-18 生活实验公司 持久化妆品组合物
EP3681921A2 (en) 2017-09-13 2020-07-22 Living Proof, Inc. Color protectant compositions
CN111356501A (zh) 2017-11-20 2020-06-30 生活实验公司 实现持久化妆品性能的属性
JP2021522260A (ja) 2018-04-27 2021-08-30 リビング プルーフ インコーポレイテッド 長持ちする化粧用組成物
KR20240009414A (ko) * 2021-05-17 2024-01-22 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 컬러 손실을 완화하기 위한 모발 색상 조성물

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US4110286A (en) * 1977-02-07 1978-08-29 Alcolac Inc. Stable polyurethane latices, emulsifiable prepolymers therefor and methods of making the same
GB2039930A (en) * 1979-01-19 1980-08-20 Minnesota Mining & Mfg Coating of fine particles in polyurethane binder
DE4241118A1 (de) * 1992-12-07 1994-06-09 Basf Ag Verwendung von kationischen Polyurethanen und Polyharnstoffen als Hilfsmittel in kosmetischen und pharmazeutischen Zubereitungen

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EP1645579A1 (fr) * 2004-09-21 2006-04-12 L'oreal Polyuréthane cationique ou cationisable à caractère élastique
KR100768825B1 (ko) * 2004-09-21 2007-10-19 로레알 탄성의 특징을 가진 양이온 또는 양이온성 폴리우레탄
US8449871B2 (en) 2006-03-20 2013-05-28 L'oreal Composition comprising novel polyurethanes and cosmetic treatment process
CN105120837A (zh) * 2013-03-29 2015-12-02 富士胶片株式会社 人工指甲组合物、人工指甲、人工指甲的形成方法和美甲套装

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JP4275941B2 (ja) 2009-06-10
FR2815350A1 (fr) 2002-04-19
JP2004511637A (ja) 2004-04-15
US20080025933A1 (en) 2008-01-31
DE60134252D1 (de) 2008-07-10
EP1326908A1 (fr) 2003-07-16
US20040052753A1 (en) 2004-03-18
FR2815350B1 (fr) 2006-12-29
ATE397027T1 (de) 2008-06-15
AU2001295692A1 (en) 2002-04-29
AR030894A1 (es) 2003-09-03
JP2008189938A (ja) 2008-08-21
EP1326908B1 (fr) 2008-05-28

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