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WO2017020303A1 - Émulsions de silicone pour applications de soin capillaire - Google Patents

Émulsions de silicone pour applications de soin capillaire Download PDF

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Publication number
WO2017020303A1
WO2017020303A1 PCT/CN2015/086284 CN2015086284W WO2017020303A1 WO 2017020303 A1 WO2017020303 A1 WO 2017020303A1 CN 2015086284 W CN2015086284 W CN 2015086284W WO 2017020303 A1 WO2017020303 A1 WO 2017020303A1
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WIPO (PCT)
Prior art keywords
silicone
amino
emulsion composition
silicone emulsion
functionalized
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Ceased
Application number
PCT/CN2015/086284
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English (en)
Inventor
Li Ding
Xuefeng HUANG
Zhihua Liu
Ping Zhu
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Dow Shanghai Holding Co Ltd
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Dow Corning China Holding Co Ltd
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Priority to PCT/CN2015/086284 priority Critical patent/WO2017020303A1/fr
Publication of WO2017020303A1 publication Critical patent/WO2017020303A1/fr
Anticipated expiration legal-status Critical
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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
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • 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
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups

Definitions

  • the present invention is in the field of emulsions and methods for making emulsions. More particularly, the present invention is in the field of silicone emulsions and processes for making silicone emulsions for hair care comprisng a silicone gum, a silicone fluid and an amino-functionalized silicone.
  • the human hair necessitates cleaning and conditioning frequently.
  • the hair becomes soiled from contact with the atmosphere and from sebum secreted by the skin. Too much sebum makes hair dirty and unattractive.
  • Shampooing hair cleans by removing excess dirt and sebum.
  • Shampooing can leave hair wet, tangled and generally unmanageable.
  • Shampooing can also make hair dry or frizzy.
  • Shampooing hair can also result in a perceived loss of softness.
  • the present invention provides silicone emulsion compositions and hair care compositionscomprisingthe silicone emulsion compositions.
  • the hair care compositions may be used in hair care products.
  • the silicone emulsion compositions comprise a silicone oil blend comprising a silicone gum, a silicone fluid and an amino-functionalized silicone.
  • the present invention provides silicone emulsion compositions comprising a silicone oil blend, the blend comprising 0.01 to 50 weight percent of a silicone gum having a viscosity of greater than 1,000,000 centistokes; 0.01 to 80 weight percent of a silicone fluid having a viscosity of less than 100,000 centistokes; 11 to 40 weight percent of an amino-functionalized silicone having a nitrogen content greater than 0.5 percent weight of the amino-functionalized silicone; and a surfactant, wherein the weight percent of the silicone gum, silicone fluid and amino-functionalized siliconeis to the weight of the silicone oil blend.
  • the present invention provides methods of forming a shampoo, the methods comprise adding the silicone emulsion compositionsto a composition comprising a suspending agent, a cationic polymer and a surfactant.
  • the present invention provides methodsfor forming a conditioner, the method comprise adding the silicone emulsion compositions to a composition comprising a surfactant, a silicone oil, a cationic polymer, a fatty alcohol and water.
  • the present invention providesshampoos comprising the silicone emulsion compositions in an amount of 0.1 to 10 percent based on a total weight of the shampoos, a suspending agent in an amount of 0.1 to 5 percent based on the total weight of the shampoos, a cationic polymer in an amount of 0.1 to 5 percent based on the total weight of the shampoos, and a surfactant in an amount of 5 to 30 percent based on the total weight of the shampoos.
  • the present invention provides conditioners comprising the silicone emulsion compositions in an amount of 0.1 to 10 percent based on a total weight of the conditioners, a surfactant in an amount of 1 to 10 percent based on the total weight of the conditioners, a silicone oil in an amount of 1 to 10 percent based on the total weight of the conditioners, a cationic polymer in an amount of 0.1 to 5 percent based on the total weight of the conditioners, and a fatty alcohol in an amount of 0.5 to 10 percent based on the total weight of the conditioners.
  • Figure 1 shows a comparison of dry sensory testresults between conventional shampoos and an exemplary shampoo of the present invention.
  • Figure 2 shows a comparison of wet sensory test results between conventional shampoos and an exemplary shampoo of the present invention.
  • the silicone emulsion compositions of the present invention may be used in compositions for hair care applications.
  • the silicone emulsion compositions may provide certain advantages including, but not limited to, increased sensory performance compared to conventional hair care products, and increased dry and wet combing performance. Increased sensory performance and/or increased dry and wet combing performance may be exhibited when the silicone emulsion compositions are applied to hair, or when formulated into hair care products, such as shampoos and conditioners, that are applied to hair.
  • substituted as used in relation to another group, for example, a hydrocarbon group, means, unless indicated otherwise, one or more hydrogen atoms in the hydrocarbon group has been replaced with another substituent.
  • substituents include, for example, halogen atoms such as chlorine, fluorine, bromine, and iodine; halogen atom containing groups such as chloromethyl, perfluorobutyl, trifluoroethyl, and nonafluorohexyl; oxygen atoms; oxygen atom containing groups such as (meth) acrylic and carboxyl; nitrogen atoms; nitrogen atom containing groups such as amines, amino- functional groups, amido-functional groups, and cyano-functional groups; sulphur atoms; and sulphur atom containing groups such as mercapto groups.
  • alkyl, alkylaryl, aryl and alkenyl groups have the following definitions.
  • An alkyl group means a saturated moiety having 1 to 10 carbon atoms that maybe cyclic or linear or branched.
  • An alkylaryl group means a moiety wherein the alkyl moiety is as defined above and the aryl is a moiety with 6 to 20 carbon atoms that have an aromatic ring.
  • An aryl group means a moietyhaving 6 to 20 carbon atoms that has an aromatic ring.
  • An alkenylgroup means a moietywith an unsaturated double bond and having 2 to 10 carbon atomsthat maybe cyclic or linear or branched.
  • the silicone emulsion compositions comprise water and a silicone oil blend, wherein the blend comprises a silicone gum, a silicone fluid and an amino-functionalized silicone.
  • the present inventors surprisingly discovered that amino-functionalized silicones having terminal amino groups and alkoxy groups, particularly terminal amino groups and/or terminal alkoxy groups, exhibit dry and wet sensory improvement in shampoos and conditioners.
  • the inventors unexpectedly discovered that an amino-functionalized silicone with terminal amino groups and terminal alkoxy groups improved the wet combing, wet and dry smoothness, and wet and dry softness sensory properties of shampoos and conditioners.
  • a skilled person would not have expected any difference in sensory properties and manageability between different silicones having amino and alkoxy groups bonded to the siloxane polymer backone. But the present inventors has unexpectedly discovered that the placement of the amino and alkoxy groups on the siloxane polymer backbone does indeed confer certain advantageous properties.
  • amino and/or alkoxy groups when placed at a terminal position on the siloxane polymer, provide improved sensory and manageability properties to hair care compositions compared to compositions lacking amino-functionalized silicones or to compositions having amino and alkoxy groups in non-terminal positions.
  • the silicone emulsion compositions comprise the silicone oil blend in an amount of 40% to 70% based on the total weight of the silicone emulsion compositions. In another embodiment, the silicone emulsion compositionscomprise the silicone oil blend in an amount of 45% to 70%, 50% to 70%, 55%to 70%, 60% to 70%, 65% to 70%, 40% to 65%, 40% to 60%, 40% to 55%, 40% to 50%, 40%to 45%, 45% to 65%, 50% to 60%, or 55% to 60% based on the total weight of the silicone emulsion compositions.
  • Suitable silicone gums include, without limitation, polydiorganosiloxanes.
  • the silicone gum comprises a polydiorganosiloxane derived from suitable combinations of R 3 SiO 0.5 and R 2 SiO units wherein each R independently represents an alkyl, alkylaryl, aryl or alkenyl.
  • the silicone gum comprises a polydiorganosiloxane terminated with trimethylsiloxy, terminated with hydroxyl, or any combination thereof.
  • the silicone gum comprises a polydimethylsiloxane terminated with trimethylsiloxy, a polydimethylsiloxane terminated with hydroxyl, or a polydimethylsiloxane terminated with trimethylsiloxy and with hydroxyl.
  • the silicone gum has a viscosity of greater than 1 million centistokes (cSt) .
  • the silicone gum has a viscosity not greater than 1 billion cSt, or a viscosity from 1 million to 1 billion cSt, 1 million to 5 million cSt, 1 million to 10 million cSt, 1 million to 20 million cSt, 1 million to 50 million cSt, or 1 million to 100 million cSt.
  • the silicone oil blend comprises the silicone gum in an amount of 0.01% to 50% based on the total weight of the silicone oil blend.
  • the silicone oil blend comprises the silicone gum in an amount of 1% to 45%, 1% to 40%, 1% to 35%, 1% to 30%, 1% to 25%, 1% to 20%, 1%to 10%, 1% to 5%, 0.05% to 45%, 1% to 40%, 3% to 35%, 5% to 25%, or 10% to 20%, 5%to 50%, 15% to 50%, 20% to 50%, 25% to 50%, 30% to 50%, 35% to 50%, 40% to 50%, or 45% to 50% based on the total weight of the silicone oil blend.
  • Suitable silicone fluids include, without limitation, polydiorganosiloxanes.
  • the silicone fluid comprises a polydiorganosiloxane derived from suitable combinations of R 3 SiO 0.5 and R 2 SiO units wherein each R independently represents an alkyl, alkylaryl, aryl or alkenyl.
  • R is methyl.
  • the silicone fluid has a viscosity of lessthan 100,000 centistokes (cSt) .
  • the silicone fluid has a viscosity of greater than 100 cSt, or a viscosity from 100 to 100,000 cSt, 100 to 10,000 cSt, 100 to 1,000 cSt, 500 to 10,000 cSt, or 1,000 to 10,000 cSt.
  • the silicone oil blend comprises the silicone fluid in an amount of 0.01% to 80% based on the total weight of the silicone oil blend.
  • the silicone oil blend includes the silicone fluid in an amount of 1% to 80%, 5% to 80%, 10% to 80%, 15% to 80%, 20% to 80%, 25% to 80%, 30% to 80%, 35% to 80%, 40% to 80%, 45% to 80%, 50% to 80%, 55% to 80%, 60% to 80%, 65% to 80%, 70% to 80%, 75% to 80%, 0.05% to 75%, 1% to 70%, 5% to 65%, 10% to 60%, 15% to 55%, 20% to 50%, 25% to 45%, 30% to 40%, 35% to 40%, 1% to 75%, 1% to 70%, 1% to 65%, 1% to 60%, 1% to 55%, 1% to 50%, 1% to 45%, 1% to 40%, 1% to 1% to 40%, 1% to 50%, 1% to 45%, 1% to 40%, 1% to 1% to 40%, 1%
  • Suitable amino-functionalized silicones include, without limitation, amino-functionalized siliconeshaving terminal amino groups, amino-functionalized siliconeshaving pendent amino groups, amino-functionalized siliconeshaving pendant and terminal amino groups, amino-functionalized siliconeshaving alkoxy groups, amino-functionalized siliconeshaving pendant and/or terminal amino groups and/or pendant and/or terminal alkoxy groups, and any combination thereof.
  • the silicone emulsion compositions comprise an amino-functionalized silicone selected from the group comprising an amino-functionalized silicone with terminal amino groups, an amino-functionalized silicone with alkoxy groups, and any combination thereof.
  • the silicone emulsion compositions comprise an amino-functionalized silicone selected from the group consisting of an amino-functionalized silicone with pendant amino groups, an amino-functionalized silicone with alkoxy groups, and any combination thereof.
  • the amino-functionalized silicone is an amino-functionalized silicone with terminal amino groups and terminal alkoxy groups.
  • amino-functionalized silicone may be represented by formula (1):
  • R 1 and R 6 are independently aminoalkyl or alkyl groups wherein at least one of R 1 and R 6 is aminoalkyl;
  • R 2 and R 7 are independently alkoxy or alkyl groups;
  • R 3 and R 8 are selected from the group consisting of alkyl, alkylaryl, aryl, alkenyl andalkoxy;
  • R 4 and R 5 are selected from the group consisting of alkyl, alkylaryl, aryl, and alkenyl; and
  • x is 3 to 500.
  • amino-functionalized silicone may be represented by formula (2) :
  • R 9 is a nitrogen-free, substituted or unsubstituted, monovalent organic group of 1 to 20 carbon atoms;
  • R 10 is a monovalent organic group having at least one nitrogen atom;
  • R 11 is an organoxy group represented by -OR 9 , w is 0.7 to 1.3; x is 2 to 500; y is 0 to 10; z is 0.7 to 1.3, and w + z is at least 2.
  • R 10 is represented by the formula: -R 12 (NR 13 CH 2 CH 2 ) v NR 14 2 , wherein R 12 is a divalent hydrocarbon group of 1 to 6 carbon atoms, R 13 and R 14 are independently selected from the group consisting of hydrogen and unsubstituted or hydroxyl-substituted monovalent hydrocarbon groups of 1 to 50 carbon atoms which any two carbon atoms may be separated by an oxygen atom, and v is 0 to 4.
  • R 10 is selected from the group consisting of -C 3 H 6 NH 2 , -C 3 H 6 NHC 2 H 4 NH 2 , -C 3 H 6 NHC 2 H 4 NHC 2 H 4 NH 2 , -C 4 H 8 NH 2 , -C 4 H 8 NHC 2 H 4 NH 2 , and-C 4 H 8 NHC 2 H 4 NHC 2 H 4 NH 2 .
  • R 11 is selected from the group consisting of -OCH 3 and -OC 2 H 5 .
  • the amino-functionalized silicone may have a nitrogen content of greater than 0.5% by weight of the amino-functionalized silicone.
  • the silicone oil blend comprises the amino-functionalized silicone in an amount of 0.01% to 50% based on the total weight of the silicone oil blend. In another embodiment, the silicone oil blend comprises the amino-functionalized silicone in an amount of 11% to 40% based on the total weight of the silicone oil blend. In another embodiment, the silicone oil blend comprises the amino-functionalized silicone in an amount of 0.05% to 45%, 1% to 45%, 5% to 45%, 10% to 45%, or 10% to 40%based on the total weight of the silicone oil blend.
  • the silicone oil blend comprises the amino-functionalized silicone in an amount of 11% to 35%, 11% to 25%, 11% to 20%, 11% to 15%, 15% to 40%, 20% to 40%, 25% to 40%, 30% to 40%, or 35% to 40% based on the total weight of the silicone oil blend.
  • the silicone emulsion compositions may include at least one surfactant.
  • Suitable surfactants include, without limitation, anionic, cationic, nonionic, zwitterionic, amphoteric surfactants, and any combination thereof.
  • the silicone emulsion compositions may include the at least one surfactant in an amount of 0.5% to 15% based on the total weight of the silicone emulsion composition, or in an amount of 0.5% to 10%, 0.5% to 5%, 1% to 15%, 5% to 15%, or 10% to 15% based on the total weight of the silicone emulsion composition.
  • the silicone emulsion compositions may includeat least one preservative.
  • Suitable preservatives include, without limitation, any preservative that does not impede the desired effect of the compositions.
  • the silicone emulsion compositions may include the at least one preservative in an amount of 0.01% to 5% based on the total weight of the silicone emulsion composition.
  • the silicone emulsion compositions have an average volume particle size of less than 30 micrometers ( ⁇ m) .
  • the average volume particle size may vary from 0.02 to 30 ⁇ m, alternatively from 0.02 to 20 ⁇ m, alternatively from 0.02 to 10 ⁇ m, alternatively from 0.02 to 25 ⁇ m, alternatively from 0.02 to 15 ⁇ m, alternatively from 0.02 to 5 ⁇ m, alternatively from 0.02 to 1 ⁇ m, or alternatively from 0.02 to 0.1 ⁇ m.
  • Particle size measurements are made by laser diffraction technique using a “Mastersizer S” from Malvern Instruments Ltd., UK, and further information on the measuring particle sizes can be, for example, found in “Basic principles of particle size analytics” , Dr. Alan Rawle, Malvern Instruments Limited, WR14 1XZ, UK and the “Manual of Malvern Mastersizer S particle size analyzer” . All particle sizes indicated in the present application are mean average volume particle size according to D (v, 0.5) and are measured with a Malvern Mastersizer S, if nothing else is stated.
  • the particle size is obtained from a particle size distribution (PSD) .
  • PSD particle size distribution
  • the PSD can be determined on a volume, surface, length basis.
  • the volume particle size is equal to the diameter of the sphere that has the same volume as a given particle.
  • Dv represents the average volume particle size of the dispersed particles.
  • Dv90 is the particle size measured in volume corresponding to 90% of the cumulative particle population.
  • the present invention provides silicone emulsion compositionsconsisting of a silicone oil blend comprising 0.01 to 50 percent of a silicone gum having a viscosity of greater than 1,000,000 centistokes; 0.01 to 80 percent of a silicone fluid having a viscosity of less than 100,000 centistokes; and 11 to 40 percent of an amino-functionalized silicone having a nitrogen content greater than 0.5 percent by weight of the amino-functionalized silicone, wherein the percent is of the weight of the silicone oil blend.
  • the present invention provides silicone emulsion compositionsconsisting essentially of a silicone oil blend comprising 0.01 to 50 percent of a silicone gum having a viscosity of greater than 1,000,000 centistokes; 0.01 to 80 percent of a silicone fluid having a viscosity of less than 100,000 centistokes; and 11 to 40 percent of an amino-functionalized silicone having a nitrogen content greater than 0.5 percent by weight of the amino-functionalized silicone, wherein the percent is of the weight of the silicone oil blend.
  • the silicone emulsion of the present invention are water dilutable silicone emulsion.
  • the emulsions are such that water can be added or diluted with water.
  • silicone emulsion is a water continuous emulsion comprising a dispersed phase and a non-dispersed (continuous) phase in which the dispersed phase is the silicone (for example, the silicone oil blend) and the non-dispersed phase is water or an aqueous solution or mixture.
  • the silicone emulsion may be dilutable in non-aqueous solvents, for example, but not limited to, non-aqueous polar solvents.
  • the silicone emulsion compositions as described herein may be used in hair care applications and products. Suitable hair care applications and products include, without limitation, mousse, lotions, sprays, pomades, hair volumizers, shampoos, conditioners, hair gels, and hair waxes.
  • the silicone emulsion compositions having amino-functionalized siliconesaccording to the present invention provide increased sensory performance, for example, dry and wet combing performance.
  • Exemplary shampoosaccording to the present invention may comprises the silicone emulsion compositions.
  • the shampoo comprises the silicone emulsion compositions in an amount of 0.1% to 10% based on the total weight of the shampoo, a suspending agent in an amount of 0.1 to 5% based on the total weight of the shampoo, a cationic polymer in an amount of 0.1 to 5% based on the total weight of the shampoo and a surfactant in an amount of 5 to 30% based on the total weight of the shampoo.
  • Suitable suspending agents include, without limitation, polyacrylic acids, crosslinked polymers of acrylic acid, copolymers of acrylic acid with a hydrophobic monomer, copolymers of carboxylic acid containing monomers and acrylic esters, crosslinked copolymers of acrylic acid and acrylate esters, heteropolysaccharide gums and crystalline long chain acryl derivativesand any combination thereof.
  • the exemplary shampoos may comprise a cationic polymer.
  • Suitable cationic polymers contain quaternary ammonium or cationic protonated amino moieties andinclude, without limitation, quaternary cellulose derivatives, quaternary guar gum derivatives, quaternary starches, quaternary sugar derivatives and quaternized proteins.
  • the exemplary shampoos may comprise a surfactant.
  • Suitable surfactants include, without limitation, anionic, cationic, nonionic, zwitterionic and amphoteric surfactantsandcombinations thereof.
  • Exemplary conditionersaccording to the present invention may comprise the silicone emulsion compositions.
  • the conditioners comprises the silicone emulsion compositions in an amount of 0.1 to 10% based on the total weight of the conditioner, a surfactant in an amount of 1 to 10% based on the total weight of the conditioner, a silicone oil in an amount of 1 to 10% based on the total weight of the conditioner, a cationic polymer in an amount of 0.1 to 5% based on the total weight of the conditioner, a fatty alcohol in an amount of 0.5 to 10% based on the total weight of the conditioner, and water.
  • the exemplary conditioners may comprise a silicone oil.
  • Suitable silicone oils include, without limitation, volatile cyclomethicone, volatile linear polydimethicone, a non-volatile silicone, a silicone substantially free of amino groups, a silicone having a viscosity of 5 mm 2 s -1 to 60000 mm 2 s -1 , and an aminosilicone having a viscosity of 100 mm 2 s -1 to 50000 mm 2 s -1 .
  • the exemplary conditioners may comprise a cationic polymer.
  • Suitable cationic polymers include, without limitation, quaternary ammonium and cationic protonated amino moieties, quaternary cellulose derivatives, quaternary guar gum derivatives, quaternary starches, quaternary sugar derivatives and quaternized proteins.
  • the exemplary conditioners may comprise a fatty alcohol.
  • Suitable fatty alcohols include, without limitation, fatty alcohols having 8 to 22 carbon atoms, and more specifically fatty alcohols having 16 to 20carbon atoms, cetyl alcohol, stearyl alcohol and combinations thereof.
  • the conditioner is a rinse off conditioner.
  • the present invention provides methods for forming shampooscomprising adding the silicone emulsion compositions of the invention to a composition comprising a suspending agent, a cationic polymer and a surfactant.
  • the present invention provides methodsfor forming conditioners comprising adding the silicone emulsion compositions of the invention to a composition comprising a surfactant, a silicone oil, a cationic polymer, and a fatty alcohol.
  • the present invention may be further illustrated by the following nonlimiting embodiments.
  • Embodiment 1 A silicone emulsion composition comprising:
  • Embodiment 2 The silicone emulsion composition of Embodiment 1, wherein the amino-functionalized silicone is selected from the group consisting of an amino-functionalized silicone with terminal amino groups, an amino-functionalized silicone with pendent amino groups, an amino-functionalized silicone with pendant and terminal amino groups, an amino-functionalized silicone with alkoxy groups, and any combination thereof.
  • the amino-functionalized silicone is selected from the group consisting of an amino-functionalized silicone with terminal amino groups, an amino-functionalized silicone with pendent amino groups, an amino-functionalized silicone with pendant and terminal amino groups, an amino-functionalized silicone with alkoxy groups, and any combination thereof.
  • Embodiment3 The silicone emulsion composition of Embodiments 1 or 2, wherein the amino-functionalized silicone is an amino-functionalized silicone with terminal amino groups, or an amino-functionalized silicone with alkoxy groups, or an amino-functionalized silicone with terminal amino groups and terminal alkoxy groups.
  • Embodiment 4 The silicone emulsion composition of any of the preceding Embodiments 1 to 3, wherein the amino-functionalized silicone has a general formula:
  • R 1 and R 6 are independently aminoalkyl or alkyl groups wherein at least one of R 1 and R 6 is aminoalkyl;
  • R 2 and R 7 are independently alkoxy or alkyl groups;
  • R 3 and R 8 are selected from the group consisting of alkyl, alkylaryl, aryl, alkenyl andalkoxy;
  • R 4 and R 5 are selected from the group consisting of alkyl, alkylaryl, aryl, and alkenyl; and
  • x is 3 to 500.
  • Embodiment 5 The silicone emulsion composition of Embodiments 1 to 3, wherein the amino-functionalized silicone has a formula:
  • R 9 is a nitrogen-free, substituted or unsubstituted, monovalent organic group of 1 to 20 carbon atoms
  • R 10 is a monovalent organic group comprising at least one nitrogen atom
  • R 11 is an organoxy group represented by -OR 9
  • w is 0.7 to 1.3
  • x is 2 to 500
  • y is 0 to 10
  • z is 0.7 to 1.3
  • w + z is at least 2.
  • Embodiment6 The silicone emulsion composition of Embodiment5, wherein R 2 has a formula:
  • R 12 is a divalent hydrocarbon group of 1 to 6 carbon atoms
  • R 13 and R 14 are independently selected from the group consisting of hydrogen and unsubstituted or hydroxyl-substituted monovalent hydrocarbon groups of 1 to 50 carbon atoms
  • v is 0 to 4.
  • Embodiment 7 The silicone emulsion composition of Embodiment 5, wherein R 10 is selected from the group consisting of -C 3 H 6 NH 2 , -C 3 H 6 NHC 2 H 4 NH 2 , -C 3 H 6 NHC 2 H 4 NHC 2 H 4 NH 2 , -C 4 H 8 NH 2 , -C 4 H 8 NHC 2 H 4 NH 2 , and -C 4 H 8 NHC 2 H 4 NHC 2 H 4 NH 2 .
  • Embodiment 8 The silicone emulsion composition of Embodiment5, wherein R 11 is -OCH 3 or -OC 2 H 5 .
  • Embodiment9 The silicone emulsion composition of Embodiment5, wherein yis 0 and xis 5 to 100.
  • Embodiment 10 The silicone emulsion composition of any of the preceding Embodiments 1 to 9, wherein the silicone gum is a polydimethylsiloxane selected from the group consisting of a polydimethylsiloxane terminated with trimethylsiloxy, a polydimethylsiloxane terminated with hydroxyl, and any combination thereof.
  • the silicone gum is a polydimethylsiloxane selected from the group consisting of a polydimethylsiloxane terminated with trimethylsiloxy, a polydimethylsiloxane terminated with hydroxyl, and any combination thereof.
  • Embodiment 11 The silicone emulsion composition of any of the preceding Embodiments 1 to 10, wherein the silicone fluid is a polydiorganosiloxanes.
  • Embodiment 12 The silicone emulsion composition of Embodiment 12, wherein the at least one surfactant is selected from the group consisting of an anionic, cationic, nonionic, zwitterionic, amphoteric, and any combination thereof, and the at least one surfactant is in an amount from 0.5 to 15 percent based on a total weight of the silicone emulsion composition.
  • the at least one surfactant is selected from the group consisting of an anionic, cationic, nonionic, zwitterionic, amphoteric, and any combination thereof, and the at least one surfactant is in an amount from 0.5 to 15 percent based on a total weight of the silicone emulsion composition.
  • Embodiment 13 The silicone emulsion composition of any one of the preceding Embodiments 1 to 12, further comprising at least one preservative.
  • Embodiment 14 The silicone emulsion composition of Embodiment 14, wherein the at least one preservative is in an amount from 0.01 to 5 percent based on a total weight of the silicone emulsion composition.
  • Embodiment 15 The silicone emulsion composition of any of the preceding Embodiments 1 to 14, wherein the silicone oil blend is in an amount from 40 to 70 percent based on a total weight of the silicone emulsion composition.
  • Embodiment 16 The silicone emulsion composition of any of the preceding Embodiments 1 to 15, wherein the silicone emulsion has an average particle size less than 30 micrometers ( ⁇ m) .
  • Embodiment 17 A method of forming a shampoo, the method comprising adding the silicone emulsion composition of any one of Embodiments 1 to 16 to a composition comprising a suspending agent, a cationic polymer and a surfactant.
  • a method of forming a conditioner comprising adding the silicone emulsion composition of any one of Embodiments 1 to 16 to a composition comprising a surfactant, a silicone oil, a cationic polymer, a fatty alcohol and water.
  • Embodiment 19 A shampoo comprising the silicone emulsion composition of any one of Embodiments 1 to 16 in an amount of 0.1 to 10 percent based on a total weight of the shampoo, a suspending agent in an amount of 0.1 to 5 percent based on the total weight of the shampoo, a cationic polymer in an amount of 0.1 to 5 percent based on the total weight of the shampoo, and a surfactant in an amount of 5 to 30 percent based on the total weight of the shampoo.
  • Embodiment 20 A conditioner comprising the silicone emulsion composition of any one of Embodiments 1 to 16 in an amount of 0.1 to 10 percent based on a total weight of the conditioner, a surfactant in an amount of 1 to 10 percent based on the total weight of the conditioner, a silicone oil in an amount of 1 to 10 percent based on the total weight of the conditioner, a cationic polymer in an amount of 0.1 to 5 percent based on the total weight of the conditioner, and a fatty alcohol in an amount of 0.5 to 10 percent based on the total weight of the conditioner.
  • Embodiment 21 A hair care composition comprising the silicone emulsion composition of any one of Embodiments 1 to 16.
  • Embodiment22 The hair care composition of Embodiment21, wherein the hair care composition is a shampoo or conditioner.
  • Embodiment23 The silicone emulsion composition of Embodiments 1 or 2, wherein the amino-functionalized silicone is an amino-functionalized silicone with terminal amino groups and terminal alkoxy groups.
  • Example1 Formation of the Silicone Emulsion Composition.
  • Example 2 Formation of the Exemplary Shampoo.
  • a mixture of 25 parts of Texapon ALES 3-28, 25 parts of Texapon ALS 28, 1 part of Comperlan 100 and 0.1 part of EDTA was heated to 80°C and mixed well. Once the mixture was homogeneous, the mixture was cooled to 70°C and 5 parts of Dehyton K, 0.4 parts of Carbopol 980, 0.2 parts of Jaguar C13S and 35.3 parts of water were loaded to the mixture. After mixing well, the mixture was further cooled to 50°C and 4 parts of Euperlan PK 771, 0.4 parts of triethanolamine (TEA) , 3 parts of the exemplary silicone emulsion composition of Example 1, 0.4 of Glydant Plus Liquid and 0.2 parts of perfume were added to form the final shampoo formulation.
  • TAA triethanolamine
  • Each hair tress has a weight of 6 grams and a length of 25 centimeters and a width of 3.5 centimeters.
  • Each hair tress is made from Asian virgin hair and available from International Hair Importers and Products Inc. located in Glendale, New York, USA.
  • each hair tress was cleaned. Each hair tress was wet under 35°C to 45°C tap water for 15 seconds. Then 1.0 gram of 9% sodium lauryl sulfate (SLS) was applied to each hair tress. The hair tress was rubbed for 30 seconds and then rinsed under 35°C to 40°Ctap water for another 30 seconds. Finally, each hair tress was vertically hung to dry.
  • SLS sodium lauryl sulfate
  • Each cleaned hair tress sample was wet under 35°C to 40°C tap water for 15 seconds. Then 1.2 grams of test shampoo was applied to a hair tress. The hair tress was rubbed for 30 seconds and then rinsed under 35°C to 40°C tap water for 30 seconds. The hair tress was then hung vertically.
  • a group of twelve panelists were selected to evaluate the above treated hair tresses.
  • Dry performance The treated hair tresses were left to dry overnight. Then “dry smoothness” and “dry softness (ease to bend the dry hair) " were evaluated by hand and “ease of dry combining” were evaluated with a comb. Each attribute was scored by a panelist according to the same scoring method described above.
  • the panelist compared two hair tresses (for example, hair tress A and hair tress B) treated with different test shampoos. If the panelist felt that hair tress A was better than hair tress B for smoothness, combing or softness, then hair tress A scored a 2 and hair tress B scored a 1. After all comparisons were complete, a sum of all the scores for each hair tress was calculated. The final scores were calculated for each hair tress and the higher score the better the performance.
  • FIG. 1 shows a comparison of dry sensory test results between commercial benchmark shampoo 1, commercial benchmark shampoo 2 and an exemplary shampoo according to the present invention.
  • Figure 2 shows a comparison of wet sensory test results between commercial benchmark shampoo 1, commercial benchmark shampoo 2 and a exemplary shampoo according to the present invention.
  • the exemplary shampoo of the present invention when used in a shampoo formulation exhibited better sensory feel compared to the benchmark products. In particular, the exemplary shampoo of the present invention exhibited better wet sensory feel compared to the benchmark products.
  • the benchmark shampoo 1 does not contain any aminosilicone.
  • the benchmark shampoo 2 contains amodimethicone, a hydroxy-terminated aminosilicone.

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Abstract

La présente invention concerne des compositions de soin capillaire comprenant des compositions d'émulsion de silicone, comprenant un mélange d'huile de silicone comprenant une gomme de silicone, un fluide de silicone et une silicone à fonctionnalité amino.
PCT/CN2015/086284 2015-08-06 2015-08-06 Émulsions de silicone pour applications de soin capillaire Ceased WO2017020303A1 (fr)

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5302382A (en) * 1993-06-03 1994-04-12 Dow Corning Corporation Silicone containing personal care products
WO1998043599A1 (fr) * 1997-03-27 1998-10-08 Unilever Plc Compositions pour le traitement des cheveux
US20020182161A1 (en) * 2001-04-06 2002-12-05 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Hair treatment compositions
WO2003092638A1 (fr) * 2002-05-03 2003-11-13 Unilever Plc Compositions d'apres-shampooings ameliores contenant un melange a base de silicone
WO2009132881A1 (fr) * 2008-04-29 2009-11-05 Unilever Plc Composition revitalisante capillaire comportant trois types de silicone
US20120058973A1 (en) * 2010-09-02 2012-03-08 Saroja Narasimhan Compositions comprising a silicone water-in-oil emulsifier and a low nitrogen containing amino-functional silicone gum
KR20130068519A (ko) * 2011-12-15 2013-06-26 주식회사 케이씨씨 고기능성 실리콘 에멀젼 조성물 및 제조 방법
WO2013117490A1 (fr) * 2012-02-08 2013-08-15 Dow Corning Corporation Procédé de formation de silicone sous forme de poudre

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5302382A (en) * 1993-06-03 1994-04-12 Dow Corning Corporation Silicone containing personal care products
WO1998043599A1 (fr) * 1997-03-27 1998-10-08 Unilever Plc Compositions pour le traitement des cheveux
US20020182161A1 (en) * 2001-04-06 2002-12-05 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Hair treatment compositions
WO2003092638A1 (fr) * 2002-05-03 2003-11-13 Unilever Plc Compositions d'apres-shampooings ameliores contenant un melange a base de silicone
WO2009132881A1 (fr) * 2008-04-29 2009-11-05 Unilever Plc Composition revitalisante capillaire comportant trois types de silicone
US20120058973A1 (en) * 2010-09-02 2012-03-08 Saroja Narasimhan Compositions comprising a silicone water-in-oil emulsifier and a low nitrogen containing amino-functional silicone gum
KR20130068519A (ko) * 2011-12-15 2013-06-26 주식회사 케이씨씨 고기능성 실리콘 에멀젼 조성물 및 제조 방법
WO2013117490A1 (fr) * 2012-02-08 2013-08-15 Dow Corning Corporation Procédé de formation de silicone sous forme de poudre

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