WO2024090246A1 - Agent filmogène de type application sur les lèvres et méthode d'utilisation dudit agent filmogène - Google Patents

Agent filmogène de type application sur les lèvres et méthode d'utilisation dudit agent filmogène Download PDF

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Publication number
WO2024090246A1
WO2024090246A1 PCT/JP2023/037212 JP2023037212W WO2024090246A1 WO 2024090246 A1 WO2024090246 A1 WO 2024090246A1 JP 2023037212 W JP2023037212 W JP 2023037212W WO 2024090246 A1 WO2024090246 A1 WO 2024090246A1
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Prior art keywords
agent
hydride
film
less
terminated
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PCT/JP2023/037212
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English (en)
Japanese (ja)
Inventor
尚義 山下
啓佑 林田
志織 岩下
恭平 小坂
明希子 福井
恵美 安東
倭伽那 近藤
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株式会社 資生堂
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Publication of WO2024090246A1 publication Critical patent/WO2024090246A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • 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
    • A61K8/892—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a hydroxy group, e.g. dimethiconol
    • 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
    • A61K8/895—Polysiloxanes containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
    • 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
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips

Definitions

  • This disclosure relates to a coating-type film-forming agent for lips and a method for using said agent.
  • a topical film-forming agent is known that can be applied to the body surface to form a film that can correct wrinkles, scars, etc.
  • Patent document 1 discloses a composition for in situ formation of a layer on the skin surface of a subject, the composition comprising one or more crosslinkable polymers, and an artificial skin comprising a layer formed from the composition.
  • Patent Document 2 discloses, as a conventional technique, the use of film-forming agents in the field of lipstick and the like to improve makeup durability and prevent color transfer to cups, etc.
  • JP 2019-503396 A Japanese Patent Application Laid-Open No. 07-033622
  • Patent Document 1 is typically intended for body correction (improvement of wrinkles, sagging, etc.), and is a technology that is applied to areas such as under-eye bags and corners of the eyes where wrinkles, sagging, etc. are easily noticeable.
  • the eye bags and corners of the eyes are relatively static parts of the face.
  • the lips are relatively dynamic, so when the technology described in Patent Document 1 is applied to the lips, which are very active, problems such as peeling of the coating can occur.
  • Patent Document 2 in the field of lip cosmetics such as lipstick, there has been a demand for improved makeup durability and prevention of color transfer onto cups, etc.
  • the subject of this disclosure is therefore to provide a lip-applied film-forming agent that can form a film that is resistant to peeling and has excellent durability, such as makeup retention, on lips that are very active.
  • a coating-type film-forming agent for lips comprising a first agent containing a crosslinkable reactive component that forms a film, and a second agent containing a catalyst that crosslinks the crosslinkable reactive component, the first agent comprises at least one selected from the group consisting of a first unsaturated organopolysiloxane and a first hydride-functionalized polysiloxane;
  • the first agent contains only the first unsaturated organopolysiloxane among the first unsaturated organopolysiloxane and the first hydride-functionalized polysiloxane
  • the second agent contains the second hydride-functionalized polysiloxane;
  • the second agent contains the second unsaturated organopolysiloxane; the molar ratio of the total m
  • first unsaturated organopolysiloxane and the second unsaturated organopolysiloxane are at least one member selected from the group consisting of vinyl terminated polydimethylsiloxane, vinyl terminated diphenylsiloxane-dimethylsiloxane copolymer, vinyl terminated polyphenylmethylsiloxane, vinylphenylmethyl terminated vinylphenylsiloxane-phenylmethylsiloxane copolymer, vinyl terminated trifluoropropylmethylsiloxane-dimethylsiloxane copolymer, vinyl terminated diethylsiloxane-dimethylsiloxane copolymer, vinylmethylsiloxane-dimethylsiloxane copolymer, trimethylsiloxy terminated vinylmethylsiloxane-dimethylsiloxane copolymer, silanol terminated vinylmethylsiloxane-d
  • first hydride-functionalized polysiloxane and the second hydride-functionalized polysiloxane are at least one selected from the group consisting of hydride-terminated polydimethylsiloxane, hydride-terminated polyphenyl-(dimethylhydrosiloxy)siloxane, hydride-terminated methylhydrosiloxane-phenylmethylsiloxane copolymer, trimethylsiloxy-terminated methylhydrosiloxane-dimethylsiloxane copolymer, polymethylhydrosiloxane, trimethylsiloxy-terminated polyethylhydrosiloxane, triethylsiloxane, methylhydrosiloxane-phenyloctylmethylsiloxane copolymer, and methylhydrosiloxane-phenyloctylmethylsiloxane terpolymer.
  • Aspect 7 The forming agent of any of the preceding claims, wherein the first hydride-functionalized polysiloxane and the second hydride-functionalized polysiloxane have a viscosity of 2 to 500,000 cst at 25°C.
  • the catalyst is at least one selected from the group consisting of platinum catalysts, rhodium catalysts, and tin catalysts.
  • Aspect 10 A forming agent according to any one of Aspects 1 to 9, wherein at least one of the first agent and the second agent contains at least one selected from the group consisting of a coloring material, a pearl agent, a matting agent, cloth, a rubber material, and beads.
  • ⁇ Aspect 14> Applying the first agent to the formed coating to form a first agent layer, and then applying a second agent onto the first agent layer to further form a coating; or The method according to aspect 13, further comprising the steps of: applying the second agent to the formed coating to form a second agent layer, and then applying the first agent onto the second agent layer to further form a coating; or mixing the first agent and the second agent to prepare a mixture, and then applying the mixture to the formed coating to further form a coating, one or more times.
  • ⁇ Aspect 15> 15 The method according to claim 13 or 14, further comprising applying a layer different from the formed coating to the coating.
  • ⁇ Aspect 16> 16 16. The method of claim 15, wherein the different layers are comprised of at least one selected from the group consisting of pearlescent agents, matte agents, beads, fabrics, rubber materials, lipsticks, and glosses.
  • the present disclosure provides a lip-applied film-forming agent that can form a film that is resistant to peeling and has excellent durability, such as makeup retention, on lips that are very active.
  • FIG. 1(a) the upper figure is a photograph of a film formed by applying the applied-type film-forming agent for lips of the present disclosure to paper, and the lower figure is a photograph of the surface of the tissue after pressing a tissue against the formed film and peeling it off.
  • FIG. 1(b) the upper figure is a photograph of a conventional lipstick containing a film-forming agent after being applied to paper, and the lower figure is a photograph of the surface of the tissue after pressing a tissue against the lipstick and peeling it off.
  • FIG. 2 is a photograph showing a film formed on the lips one or more times using the applied film-forming agent for lips of the present disclosure.
  • FIG. 3 is a photograph of a film having a bead layer prepared by applying beads before the film is completely crosslinked when the lip-applied film-forming agent of the present disclosure is applied to the lips to form a film.
  • the presently disclosed applied film-forming agent for lips comprises a first agent containing a crosslinkable reactive component that constitutes a film, and a second agent containing a catalyst that crosslinks the crosslinkable reactive component, and the first agent contains at least one selected from the group consisting of a first unsaturated organopolysiloxane and a first hydride-functionalized polysiloxane, and when the first agent contains only the first unsaturated organopolysiloxane among the first unsaturated organopolysiloxane and the first hydride-functionalized polysiloxane, the second agent contains a second hydride-functionalized polysiloxane.
  • the second agent contains a second unsaturated organopolysiloxane
  • the molar ratio of the total molar amount of hydride-functionalized moieties in the hydride-functionalized polysiloxane contained in the first agent and the second agent to the total molar amount of unsaturated moieties in the unsaturated organopolysiloxane contained in the first agent and the second agent is 1.2 to 50.0.
  • the principle of action of the presently disclosed applied film-forming agent for lips that can form a film on the lips that is less likely to peel off and has excellent durability for makeup, etc., on the lips, which are very active, is believed to be as follows.
  • the film-forming agent described in Patent Document 1 is typically intended for body correction (improvement of wrinkles, sagging, etc.), so the film formed needs to be one that maintains a taut state on the skin after crosslinking. Therefore, in order to ensure this state, the hydride-functionalized polysiloxane, one of the components that makes up the film, is blended in a relatively high concentration.
  • conventional lipsticks that are said to have good color retention contain a film-forming agent that is a polymer component that has already been polymerized.
  • the oil or polymerized polymer is applied in a state where it is simply attached to the lips, so the film that is formed is weak in strength and has insufficient adhesion to the lips.
  • lipsticks containing conventional film-forming agents do not provide sufficient makeup retention.
  • the film prepared by the applied film-forming agent for lips of the present disclosure is a film formed by a crosslinking reaction on the lips, so the film has high film strength, and the obtained film is a film that is more flexible than the film described in Patent Document 1, and is more likely to follow the movement of the lips and to penetrate into wrinkles on the surface of the lips to provide an anchor effect, so it is thought that the adhesion to the lips is improved compared to films made by conventional film-forming agents.
  • the applied film-forming agent for lips of the present disclosure the film that has been strengthened by crosslinking is firmly fixed on the lips, so it is thought that the makeup retention is improved compared to lipsticks containing conventional film-forming agents.
  • film durability can also be referred to as lasting property, and refers to the ability of the film applied to the lips to maintain the desired performance (e.g., cosmetic durability such as color retention, gloss retention, etc.) for a long period of time, compared to films obtained with conventional, general lipsticks, etc.
  • desired performance e.g., cosmetic durability such as color retention, gloss retention, etc.
  • the film obtained with the applied film-forming agent for lips of this disclosure is transparent and capable of exhibiting gloss, it is intended to have the ability to maintain gloss retention compared to conventional, general gloss lipsticks, etc.
  • the film obtained has color
  • it is intended to have the ability to at least maintain color retention compared to conventional, general lipsticks, etc.
  • viscosity refers to a measure of the resistance of a fluid to being deformed by either shear or tensile stress.
  • the viscosity of the first and second parts of a lip-applied film former affects the thickness, spreadability, and uniformity and/or uniformity of the layer formed on a substrate.
  • Viscosity can be reported as either dynamic viscosity (also known as absolute viscosity, typical units are Pa ⁇ s, poise, P, cP) or kinematic viscosity (typical units are cm 2 /s, stokes, St, cst), which is the dynamic viscosity divided by the density of the measured fluid.
  • the viscosity ranges of the components disclosed herein are generally provided by the suppliers of each component in units of kinematic viscosity (e.g., cst) measured using a rheometer or a Cannon-Fenske tube viscometer, although the viscosity of a fluid can also be measured using, for example, a rheometer (e.g., a linear shear rheometer or a dynamic shear rheometer) or a viscometer (a viscometric meter, also called, for example, a capillary viscometer or a rotational viscometer).
  • a rheometer e.g., a linear shear rheometer or a dynamic shear rheometer
  • a viscometer a viscometric meter, also called, for example, a capillary viscometer or a rotational viscometer.
  • crosslinking also includes the concept commonly referred to as “curing.”
  • the paint-on-lip film-forming agent of the present disclosure (which may be simply referred to as a "former”) comprises a first agent containing a crosslinkable component that constitutes a film, and a second agent containing a catalyst that crosslinks this crosslinkable component, and the molar ratio of the total molar amount of hydride-functionalized moieties in the hydride-functionalized polysiloxane contained in the first agent and the second agent to the total molar amount of unsaturated moieties in the unsaturated organopolysiloxane contained in the first agent and the second agent (which may be simply referred to as the "molar ratio of hydride-functionalized moieties to unsaturated moieties”) is 1.2 to 50.0.
  • the application performance of the applied film-forming agent for lips can be evaluated by viscosity using a B-type viscometer (Shibaura Systems Co., Ltd., Vismetron).
  • the viscosity of the first and second agents in the applied film-forming agent for lips of the present disclosure immediately after preparation, measured under conditions of 25°C and 60 rpm (rotor No. 3 or No. 4), is, for example, 100 mPa ⁇ s or more, 500 mPa ⁇ s or more, 1,000 mPa ⁇ s or more, 2,000 mPa ⁇ s or more, 5,000 mPa ⁇ s or more, 7,500 mPa ⁇ s or more, 10,000 mPa ⁇ s or more, or 15,000 mPa ⁇ s or more.
  • the viscosity can be 1,000,000 mPa ⁇ s or more, and can be 1,000,000 mPa ⁇ s or less, 750,000 mPa ⁇ s or less, 500,000 mPa ⁇ s or less, 250,000 mPa ⁇ s or less, 200,000 mPa ⁇ s or less, 175,000 mPa ⁇ s or less, 150,000 mPa ⁇ s or less, 125,000 mPa ⁇ s or less, 100,000 mPa ⁇ s or less, or 80,000 mPa ⁇ s or less.
  • the first and second agents of the applied film-forming agent for lips preferably have a viscosity of 20,000 mPa ⁇ s or less, 15,000 mPa ⁇ s or less, or 10,000 mPa ⁇ s or less immediately after preparation, and preferably have a viscosity of 3,000 mPa ⁇ s or more, 5,000 mPa ⁇ s or more, or 7,000 mPa ⁇ s or more.
  • the viscosity of the first and second agents in the presently disclosed applied film-forming agent for lips after two weeks, measured at 25°C and 60 rpm (rotor No. 3), is preferably 50,000 mPa ⁇ s or less, 30,000 mPa ⁇ s or less, or 15,000 mPa ⁇ s or less, and is preferably 5,000 mPa ⁇ s or more, 7,000 mPa ⁇ s or more, or 10,000 mPa ⁇ s or more, from the viewpoints of smooth application performance and prevention of dripping from the skin.
  • the applied film-forming agent for lips of the present disclosure includes a first agent containing a crosslinking reactive component that constitutes a film.
  • the first agent contains at least one selected from the group consisting of a first unsaturated organopolysiloxane and a first hydride-functionalized polysiloxane as the crosslinking reactive component.
  • the second agent in the forming agent of the present disclosure contains a second hydride-functionalized polysiloxane
  • the first agent contains only the first hydride-functionalized polysiloxane among the first unsaturated organopolysiloxane and the first hydride-functionalized polysiloxane
  • the second agent contains a second unsaturated organopolysiloxane
  • the dosage form of the first agent is not particularly limited, and may be, for example, a single-phase system composed of an oil phase, a non-emulsified oil-in-water or water-in-oil two-phase system, or a two-phase system composed of an oil-in-water emulsion composition or a water-in-oil emulsion composition.
  • a single-phase system composed of an oil phase is typically an anhydrous form.
  • “anhydrous” not only means that the composition does not contain water, but also means that the water content is low, i.e., 10% by mass or less, 5% by mass or less, 2% by mass or less, 1% by mass or less, or 0.1% by mass or less.
  • a non-emulsified two-phase system may include a water-in-oil composition in which water droplets are forcibly dispersed in a dispersion medium containing oil by shaking a liquid in a state in which the water and oil are separated, or an oil-in-water composition in which oil droplets are forcibly dispersed in a dispersion medium containing water.
  • Each of these formulations can be prepared appropriately by conventional methods using a crosslinking reactive component and, optionally, known materials such as oils, emulsifiers, and water, as described below.
  • the first agent is applied to the lips by painting or the like, so from the viewpoint of application performance, it preferably has a glass transition temperature below body temperature.
  • the glass transition temperature can be 37°C or lower, 25°C or lower, 10°C or lower, or 0°C or lower.
  • There is no particular restriction on the lower limit of the glass transition temperature but it can be, for example, -30°C or higher, -20°C or higher, or -10°C or higher.
  • glass transition temperature refers to the temperature at which a transition from a solid state to a liquid state occurs, and can be measured, for example, using a differential scanning calorimeter (DSC) in accordance with ASTM D3418-03.
  • DSC differential scanning calorimeter
  • the first unsaturated organopolysiloxane is not particularly limited, and may be an organopolysiloxane having an unsaturated portion, for example, one or more organopolysiloxanes having at least two carbon-carbon double bonds or at least one carbon-carbon triple bond in the molecule.
  • an unsaturated organopolysiloxane preferably, one or more organopolysiloxanes having at least two alkenyl functional groups (e.g., vinyl functional groups) on average and having a viscosity of 1,000 to 2,000,000 cst at 25°C may be mentioned.
  • the "unsaturated portion” in the present disclosure means a portion having a "carbon-carbon double bond” and a “carbon-carbon triple bond", which may be simply referred to as a "double bond” and a “triple bond".
  • the first unsaturated organopolysiloxane may be used alone or in combination of two or more kinds.
  • Such organopolysiloxanes may contain unsaturated portions (double bond portions or triple bond portions) in the terminal units of the polymer, in the non-terminal monomer units of the polymer, or in a combination of these, and it is particularly preferred that they are contained in the non-terminal monomer units of the polymer.
  • the double bond-containing monomer units in the organopolysiloxane may be spaced apart, on average, by 40 monomer units or more, 200 monomer units or more, 400 monomer units or more, 1,000 monomer units or more, or 2,000 monomer units or more.
  • the content of unsaturated moieties in the unsaturated organopolysiloxane can be 0.001 mmol/g or more, 0.005 mmol/g or more, 0.010 mmol/g or more, 0.050 mmol/g or more, or 0.10 mmol/g or more, and can be 5.0 mmol/g or less, 3.0 mmol/g or less, 1.0 mmol/g or less, 0.50 mmol/g or less, 0.40 mmol/g or less, 0.30 mmol/g or less, 0.25 mmol/g or less, 0.20 mmol/g or less, or 0.15 mmol/g or less.
  • the approximate molar amount of unsaturated moieties in the organopolysiloxane can be calculated based on the average molecular weight of the organopolysiloxane.
  • the first unsaturated organopolysiloxane can have a viscosity of 1,000 to 2,000,000 cst at 25° C.
  • the lower limit of such a viscosity is preferably 5,000 cst or more, 10,000 cst or more, 20,000 cst or more, 40,000 cst or more, 60,000 cst or more, 80,000 cst or more, or 100,000 cst or more, and more preferably 125,000 cst or more or 150,000 cst or more.
  • the upper limit of the viscosity is preferably 1,000,000 cst or less, 500,000 cst or less, 450,000 cst or less, 400,000 cst or less, 350,000 cst or less, 300,000 cst or less, or 250,000 cst or less, more preferably 200,000 cst or less or 180,000 cst or less, and even more preferably 165,000 cst or less.
  • the first unsaturated organopolysiloxane can have an average molecular weight of 30,000 Da to 500,000 Da.
  • the lower limit of the average molecular weight is preferably 35,000 Da or more, 40,000 Da or more, 50,000 Da or more, 60,000 Da or more, 72,000 Da or more, 84,000 Da or more, 96,000 Da or more, or 100,000 Da or more, and more preferably 140,000 Da or more or 150,000 Da or more.
  • the upper limit of the average molecular weight is preferably 200,000 Da or less, 190,000 Da or less, 180,000 Da or less, or 170,000 Da or less, more preferably 160,000 Da or less, and even more preferably 155,000 Da or less.
  • the average molecular weight in this disclosure can be determined by gel permeation chromatography (GPC).
  • the first unsaturated organopolysiloxane for example, at least one unsaturated organopolysiloxane selected from the group consisting of organopolysiloxanes having vinyl groups, vinyl-terminated organopolysiloxanes, and vinylated branched organopolysiloxanes can be used.
  • vinyl-terminated polydimethylsiloxane vinyl-terminated diphenylsiloxane-dimethylsiloxane copolymer
  • vinyl-terminated polyphenylmethylsiloxane vinylphenylmethyl-terminated vinylphenylsiloxane-phenylmethylsiloxane copolymer
  • vinyl-terminated trifluoropropylmethylsiloxane-dimethylsiloxane copolymer vinyl-terminated diethylsiloxane-dimethylsiloxane copolymer, vinylmethylsiloxane-dimethylsiloxane copolymer, trimethylsiloxy-terminated vinylmethylsiloxane-dimethylsiloxane copolymer, silanol-terminated vinylmethylsiloxane-dimethylsiloxane copolymer, vinylmethylsiloxane homopolymer, vinyl T-structure polymer, vinyl Q-structure polymer, monovin
  • the first unsaturated organopolysiloxane can be used alone or in combination of two or more. Among these, vinyl-terminated polydimethylsiloxane is preferred, and vinyl dimethicone (divinyl dimethicone) is more preferred.
  • terminal refers to either one terminal or both terminals. When distinguishing between these, it can be written as "vinyl one terminal” or “vinyl both terminals", for example.
  • the amount of the first unsaturated organopolysiloxane in the first agent is not particularly limited, and may be appropriately adjusted so that the molar ratio of the hydride functionalized portion to the unsaturated portion falls within a predetermined range.
  • the amount of the first unsaturated organopolysiloxane may be 5.0% by mass or more, 10% by mass or more, 20% by mass or more, 25% by mass or more, 30% by mass or more, 35% by mass or more, or 40% by mass or more, and may be 90% by mass or less, 85% by mass or less, 80% by mass or less, 75% by mass or less, 70% by mass or less, 65% by mass or less, 60% by mass or less, 55% by mass or less, 50% by mass or less, or 45% by mass or less, based on the entire first agent.
  • the first hydride-functionalized polysiloxane is not particularly limited, and may be a polysiloxane having a hydride-functionalized moiety, such as a compound of the following formula 1.
  • the first hydride-functionalized polysiloxane may be used alone or in combination of two or more kinds.
  • the "hydride-functionalized moiety" in the present disclosure means a moiety having a Si-H unit:
  • R 1b , R 2b , R 3b , R 4b , R 5b , R 6b , R 7b , R 8b , R 9b and R 10b are each independently selected from hydrogen, C 1-20 alkyl, C 2-20 alkenyl, C 5-10 aryl, hydroxyl, or C 1-20 alkoxy, and m and n are each independently an integer from 10 to 6,000, provided that at least one of R 1b , R 2b , R 3b , R 4b , R 5b , R 6b , R 7b , R 8b , R 9b and R 10b is hydrogen.
  • At least one of R 1b , R 2b , R 3b , R 4b , R 5b , R 6b , R 7b , R 8b , R 9b and R 10b is hydrogen, and the remainder are C 1-20 alkyl.
  • R 1b , R 2b , R 3b , R 4b , R 5b , R 6b , R 7b , R 8b , R 9b and R 10b are hydrogen (e.g., two Si—H units per functionalized hydridopolysiloxane molecule).
  • R 1b , R 2b , R 3b , R 4b , R 5b , R 6b , R 7b , R 8b , R 9b and R 10b are hydrogen (e.g., three Si—H units per functionalized hydridopolysiloxane molecule).
  • R 1b , R 2b , R 3b , R 4b , R 5b , R 6b , R 7b , R 8b , R 9b and R 10b are hydrogen (e.g., two Si—H units per functionalized hydridopolysiloxane molecule), and the remainder are C 1-20 alkyl.
  • R 1b , R 2b , R 3b , R 4b , R 5b , R 6b , R 7b , R 8b , R 9b and R 10b are hydrogen (e.g., three Si—H units per functionalized hydridopolysiloxane molecule), and the remainder are C 1-20 alkyl.
  • At least two of R 4b , R 5b , R 9b and R 10b are hydrogen (eg, two Si—H units per functionalized hydridopolysiloxane molecule), and the remainder are C 1-20 alkyl.
  • R 4b , R 5b , R 9b and R 10b are hydrogen (eg, three Si—H units per functionalized hydridopolysiloxane molecule), and the remainder are C 1-20 alkyl.
  • the sum of m and n is an integer between 10 and 1,300, between 10 and 1,100, between 10 and 600, between 15 and 500, between 15 and 400, between 20 and 300, between 20 and 200, between 25 and 100, between 25 and 75, between 30 and 50, or between 40 and 45.
  • the first hydride-functionalized polysiloxane can be a non-terminally and/or terminally hydrogenated organopolysiloxane, which is composed of one or more organopolysiloxanes having at least two Si-H units in the molecule, preferably one or more organopolysiloxanes having an average of at least two Si-H units and having a viscosity of 2 to 100,000 cst at 25°C.
  • the organopolysiloxane having hydride-functionalized Si—H units may include such Si—H units in terminal units of the polymer, in non-terminal monomer units of the polymer, or in a combination thereof. Of these, it is preferred that the Si—H units are included in non-terminal monomer units of the polymer.
  • the first hydride-functionalized polysiloxane may be alkyl-terminated. For example, in Formula 1, one or both of R 2b and R 7b may be C 1-20 alkyl.
  • one, two, three, four, five or six of R 1b , R 2b , R 3b , R 6b , R 7b and R 8b may be C 1-20 alkyl.
  • R 1b , R 2b , R 3b , R 4b , R 5b , R 6b , R 7b , R 8b and R 10b are each C 1-20 alkyl, for example C 1 alkyl (for example methyl), and R 9b may be hydrogen.
  • R 1b , R 2b , R 3b , R 4b , R 5b , R 6b , R 7b , R 8b and R 9b are each C 1-20 alkyl, for example C 1 alkyl (for example methyl), and R 10b may be hydrogen.
  • the Si-H containing monomer units in the organopolysiloxane may be spaced apart, on average, by 1 monomer unit or more, 2 monomer units or more, 5 monomer units or more, 10 monomer units or more, 20 monomer units or more, 40 monomer units or more, 200 monomer units or more, 400 monomer units or more, 1,000 monomer units or more, or 2,000 monomer units or more.
  • the Si-H content of the organopolysiloxane having Si-H units can be 0.10 mmol/g or more, 0.50 mmol/g or more, 1.0 mmol/g or more, 2.0 mmol/g or more, 3.0 mmol/g or more, or 4.0 mmol/g or more, and can be 20 mmol/g or less, 10 mmol/g or less, 9.0 mmol/g or less, 8.0 mmol/g or less, 7.0 mmol/g or less, 6.0 mmol/g or less, or 5.0 mmol/g or less.
  • the approximate molar amount of Si-H units in the organopolysiloxane can be calculated based on the average molecular weight of the organopolysiloxane.
  • the first hydride-functionalized polysiloxane can have a viscosity of 2 to 500,000 cst at 25° C.
  • the lower limit of the viscosity is preferably 3 cst or more, 4 cst or more, 5 cst or more, 10 cst or more, 12 cst or more, 15 cst or more, 20 cst or more, 25 cst or more, or 30 cst or more, and more preferably 40 cst or more.
  • the upper limit of the viscosity is preferably 200,000 cst or less, 100,000 cst or less, 50,000 cst or less, 20,000 cst or less, 10,000 cst or less, 5,000 cst or less, 2,000 cst or less, or 1,000 cst or less, and more preferably 500 cst or less.
  • the viscosity of the hydride-functionalized polysiloxane is particularly preferably in the range of 45 to 100 cst or 45 to 50 cst at 25°C.
  • the hydride-functionalized polysiloxane can have an average molecular weight of 400 to 500,000 Da.
  • the lower limit of such average molecular weight is preferably 500 Da or more, 800 Da or more, 900 Da or more, 1,000 Da or more, 1,200 Da or more, 1,400 Da or more, 1,600 Da or more, 1,800 Da or more, 2,000 Da or more, or 2,200 Da or more, and more preferably 2,300 Da or more.
  • the upper limit of the average molecular weight is preferably 250,000 Da or less, 140,000 Da or less, 100,000 Da or less, 72,000 Da or less, 62,700 Da or less, 60,000 Da or less, 50,000 Da or less, 49,500 Da or less, 36,000 Da or less, 28,000 Da or less, 25,000 Da or less, 20,000 Da or less, 15,000 Da or less, 10,000 Da or less, 5,000 Da or less, or 4,000 Da or less, and more preferably 2,500 Da or less.
  • the first hydride-functionalized polysiloxane may be, but is not limited to, at least one selected from the group consisting of hydride-terminated polydimethylsiloxane, hydride-terminated polyphenyl-(dimethylhydrosiloxy)siloxane, hydride-terminated methylhydrosiloxane-phenylmethylsiloxane copolymer, trimethylsiloxy-terminated methylhydrosiloxane-dimethylsiloxane copolymer, polymethylhydrosiloxane, trimethylsiloxy-terminated polyethylhydrosiloxane, triethylsiloxane, methylhydrosiloxane-phenyloctylmethylsiloxane copolymer, and methylhydrosiloxane-phenyloctylmethylsiloxane terpolymer.
  • hydride-terminated polydimethylsiloxane is
  • the amount of the first hydride-functionalized polysiloxane in the first agent is not particularly limited, and may be appropriately adjusted so that the molar ratio of the hydride-functionalized portion to the unsaturated portion falls within a predetermined range.
  • the amount of the first hydride-functionalized polysiloxane may be 1.0% by mass or more, 3.0% by mass or more, or 5.0% by mass or more, and may be 50% by mass or less, 40% by mass or less, 30% by mass or less, 20% by mass or less, 15% by mass or less, 10% by mass or less, or 8.0% by mass or less, relative to the entire first agent.
  • the second agent constituting the paint-on-lip film-forming agent of the present disclosure contains a catalyst that crosslinks the crosslinking reactive component in the first agent described above.
  • the catalyst is not particularly limited, and may be, for example, any substance capable of causing, promoting, or initiating a physical and/or chemical crosslinking reaction of the unsaturated organopolysiloxane and hydride-functionalized polysiloxane, which are crosslinking reactive components constituting the coating.
  • the catalyst may or may not undergo permanent physical and/or chemical changes during or at the end of the process.
  • the catalyst may be, but is not limited to, a metal catalyst capable of initiating and/or promoting crosslinking at or below body temperature, such as Group VIII metal catalysts, for example, platinum catalysts, rhodium catalysts, palladium catalysts, cobalt catalysts, nickel catalysts, ruthenium catalysts, osmium catalysts, and iridium catalysts, and Group IVA metal catalysts, for example, germanium catalysts and tin catalysts. Of these, platinum catalysts, rhodium catalysts, and tin catalysts are preferred.
  • the catalysts may be used alone or in combination of two or more.
  • Platinum catalysts include, for example, platinum carbonylcyclovinylmethylsiloxane complexes, platinum divinyltetramethyldisiloxane complexes, platinum cyclovinylmethylsiloxane complexes, platinum octanaldehyde/octanol complexes, and other Pt(0) catalysts, such as Karstedt's catalyst, platinum-alcohol complexes, platinum-alkoxide complexes, platinum-ether complexes, platinum-aldehyde complexes, platinum-ketone complexes, platinum-halogen complexes, platinum-sulfur complexes, platinum-nitrogen complexes, platinum-phosphorus complexes, platinum-phosphorus complexes, platinum-carbon double bond complexes, platinum-carbon triple bond complexes, platinum-imido complexes, platinum-amide complexes, platinum-ester complexes, platinum-phosphate ester complexes, platinum-thiol ester complexes, platinum lone
  • At least one selected from the group consisting of platinum carbonylcyclovinylmethylsiloxane complex, platinum divinyltetramethyldisiloxane complex, platinum cyclovinylmethylsiloxane complex, and platinum octanaldehyde/octanol complex is preferred.
  • Rhodium catalysts include, for example, tris(dibutylsulfide)rhodium trichloride and rhodium trichloride hydrate.
  • tin catalysts include tin(II) octanoate, tin(II) neodecanoate, dibutyltin diisooctylmaleate, di-n-butyl bis(2,4-pentanedionate)tin, di-n-butylbutoxychlorotin, dibutyltin dilaurate, dimethyltin dineodecanoate, dimethylhydroxy(oleate)tin, and tin(II) oleate.
  • platinum catalysts are more preferred, with platinum divinyltetramethyldisiloxane complexes being particularly preferred.
  • the amount of catalyst in the second agent may be adjusted appropriately according to the required film performance, etc., and is not particularly limited.
  • the amount of catalyst may be 0.001 mass% or more, 0.005 mass% or more, or 0.010 mass% or more, and 5.0 mass% or less, 3.0 mass% or less, 1.0 mass% or less, 0.10 mass% or less, or 0.050 mass% or less, relative to the total amount of the second agent.
  • the formulation of the second agent of the present disclosure is not particularly limited, and may be, for example, a single-phase system composed of an oil phase in an anhydrous form, a non-emulsified oil-in-water or water-in-oil two-phase system, or a two-phase system composed of an oil-in-water emulsion composition or a water-in-oil emulsion composition.
  • Each of these formulations can be prepared appropriately by conventional methods using a catalyst and, optionally, known materials such as oil, emulsifier, and water, as described below.
  • Silicone oil can be used as the oil, and the first unsaturated organopolysiloxane and the first hydride-functionalized polysiloxane that can be used in the first agent described above can also be used as this silicone oil.
  • the unsaturated organopolysiloxane and the hydride-functionalized polysiloxane in the second agent can be called the second unsaturated organopolysiloxane and the second hydride-functionalized polysiloxane to distinguish them from the first unsaturated organopolysiloxane and the first hydride-functionalized polysiloxane in the first agent.
  • the applied-type film-forming agent for lips of the present disclosure contains an unsaturated organopolysiloxane and a hydride-functionalized polysiloxane such that the molar ratio of the total molar amount of hydride-functionalized moieties in the hydride-functionalized polysiloxane contained in the first and second agents to the total molar amount of unsaturated moieties in the unsaturated organopolysiloxane contained in the first and second agents is 1.2 to 50.0.
  • a film that is resistant to peeling and has excellent film durability, such as cosmetic wear can be obtained on active lips.
  • the total molar amount of unsaturated moieties in the organopolysiloxane having unsaturated moieties in the applied film-forming agent for lips can be 1.0 mmol or more, 1.5 mmol or more, 2.0 mmol or more, 2.5 mmol or more, 3.0 mmol or more, 3.5 mmol or more, 4.0 mmol or more, 4.5 mmol or more, or 5.0 mmol or more, and can be 20 mmol or less, 15 mmol or less, 10 mmol or less, 9.5 mmol or less, or 9.0 mmol or less, from the viewpoints of film peel resistance, film durability, etc.
  • the total molar amount of the hydride-functionalized portion of the hydride-functionalized polysiloxane in the applied film-forming agent for lips can be 6.0 mmol or more, 8.0 mmol or more, 10 mmol or more, 20 mmol or more, 30 mmol or more, 40 mmol or more, 50 mmol or more, 60 mmol or more, 70 mmol or more, or 80 mmol or more, and can be 150 mmol or less, 130 mmol or less, 100 mmol or less, 90 mmol or less, 80 mmol or less, 70 mmol or less, 60 mmol or less, or 50 mmol or less, from the viewpoint of the peeling resistance of the film, the durability of the film, and the like.
  • the molar ratio of the hydride functionalized portion to the unsaturated portion is preferably 1.2 or more, 1.5 or more, 1.8 or more, 2.0 or more, 2.5 or more, 3.0 or more, 3.5 or more, 4.0 or more, 4.5 or more, or 5.0 or more, and is preferably 50.0 or less, 45.0 or less, 40.0 or less, 35.0 or less, 30.0 or less, 25.0 or less, 20.0 or less, 15.0 or less, less than 15.0, 14.5 or less, 14.0 or less, 13.5 or less, 13.0 or less, 12.5 or less, 12.0 or less, 11.5 or less, 11.0 or less, 10.5 or less, or 10.0 or less.
  • ⁇ Optional ingredients> In the applied film-forming agent for lips of the present disclosure, various ingredients can be appropriately blended into the first agent and/or the second agent within a range that does not adversely affect the effects of the present disclosure.
  • the optional components are not particularly limited, but examples include feel modifiers, adhesion modifiers, spreadability promoters, diluents, adhesion modifiers, oils, emulsifiers (surfactants), water, humectants, preservatives, coloring materials (e.g., pigments, dyes, colorants), pearling agents, matting agents, beads, cloth, rubber materials (e.g., rubber sheets made of silicone rubber, etc.), components that thicken the water phase or oil phase (thickeners), protective colloids, reinforcing materials (fillers), skin permeation enhancers, optical modifiers, scattering agents, adsorbents, magnetic materials, gas transport modifiers, liquid transport modifiers, pH modifiers, sensitization modifiers, and aesthetic modifiers.
  • Optional components can be used alone or in combination of two or more.
  • cosmetic agents include moisturizers, UV absorbers, skin protectants, skin soothing agents, skin whitening agents, skin glossing agents, skin softeners, skin smoothing agents, skin bleaching agents, skin exfoliating agents, skin tightening agents, beauty agents, vitamins, antioxidants, cell signaling agents, cell regulating agents, cell interacting agents, skin tanning agents, anti-aging agents, anti-wrinkle agents, spot reducers, alpha-hydroxy acids, beta-hydroxy acids, and ceramides; and also include, for example, pain relieving agents, analgesics, anti-pruritic agents, anti-acne agents (e.g., beta-hydroxy acids, salicylic acid, benzoyl peroxide), and anti-inflammatory agents.
  • analgesics e.g., analgesics, anti-pruritic agents, anti-acne agents (e.g., beta-hydroxy acids, salicylic acid, benzoyl peroxide), and anti-inflammatory agents.
  • the therapeutic agents may include, for example, antihistamines, corticosteroids, NSAIDs (nonsteroidal anti-inflammatory drugs), antiseptics, antibiotics, antibacterials, antifungals, antivirals, antiallergy agents, anti-irritants, insect repellents, phototherapy agents, blood clotting agents, antineoplastic agents, immune system enhancers, immune system suppressants, coal tar, anthralin, fluocinonide, methotrexate, cyclosporine, pimecrolimus, tacrolimus, azathioprine, fluorouracil, ceramides, counterirritants, and skin cooling compounds; and may include, for example, antioxidants, vitamins, vitamin D3 analogs, retinoids, minerals, mineral oil, petrolatum, fatty acids, plant extracts, polypeptides, antibodies, proteins, sugars, humectants, and emollients.
  • NSAIDs nonsteroidal anti-inflammatory drugs
  • antiseptics antibiotics
  • the oil may be, for example, liquid oil, solid oil, wax, hydrocarbon oil, silicone oil, or polar oil.
  • the oil may be a non-volatile oil or a volatile oil.
  • the oil may be used alone or in combination of two or more.
  • volatile refers to an oil that exhibits a volatile content of more than 5% when left at atmospheric pressure and 105°C for 3 hours. Such a volatile content may be specified as 10% or more, 20% or more, 40% or more, 50% or more, 60% or more, 80% or more, or 100%.
  • the boiling point at 1 atmosphere (101.325 kPa) may be used as an indicator of volatility.
  • non-volatile refers to a material that exhibits a volatile content of 5% or less when left at 105°C for 3 hours.
  • silicone oils that can be used include chain silicones such as dimethylpolysiloxane (dimethicone), methylphenylpolysiloxane, and methylhydrogenpolysiloxane; and cyclic silicones such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane.
  • chain silicones such as dimethylpolysiloxane (dimethicone), methylphenylpolysiloxane, and methylhydrogenpolysiloxane
  • cyclic silicones such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane.
  • the amount of volatile oil in the first agent of the present disclosure is preferably 30% by mass or less, 20% by mass or less, 10% by mass or less, 5.0% by mass or less, 3.0% by mass or less, 1.0% by mass or less, 0.1% by mass or less, or 0.05% by mass or less relative to the total amount of the first agent, and it is more preferable that no volatile oil is contained in the first agent.
  • the emulsifier for example, anionic, cationic, amphoteric, or nonionic emulsifiers can be used.
  • the emulsifiers can be used alone or in combination of two or more.
  • the emulsifier in this disclosure refers to an agent having an emulsifying function (surface activity), and can also include agents generally referred to as surfactants.
  • emulsifier examples include at least one selected from the group consisting of hydrocarbon surfactants, silicone surfactants, and amphiphilic powders.
  • hydrocarbon surfactants include polyoxyethylene alkyl ethers, polyoxyethylene steryl ethers, polyoxyethylene fatty acid esters, polyoxyethylene polyhydric alcohol fatty acid esters, polyoxyethylene hydrogenated castor oil, polyoxyethylene sorbitan fatty acid esters, glycol fatty acid esters, glycerin fatty acid esters, sorbitan fatty acid esters, sucrose fatty acid esters, and polyglycerin fatty acid esters.
  • silicone surfactants include polyether-modified silicone and alkyl-co-modified polyether-modified silicone.
  • the amount of emulsifier used can be 0.01% by mass or more, 0.05% by mass or more, 0.1% by mass or more, or 0.2% by mass or more relative to the total amount of the first agent or the second agent.
  • the upper limit of the amount of emulsifier used can be, for example, 5.0% by mass or less, 4.0% by mass or less, 3.0% by mass or less, 2.0% by mass or less, or 1.0% by mass or less.
  • water used in cosmetics or quasi-drugs can be used.
  • water used in cosmetics or quasi-drugs can be used.
  • ion-exchanged water, distilled water, ultrapure water, and tap water can be used.
  • coloring materials there are no particular limitations on the coloring materials, and materials generally referred to as inorganic pigments, organic pigments, dyes, and colorants can be used. Coloring materials can be used alone or in combination of two or more. Note that coloring materials do not include pearling agents, matte agents, and beads.
  • inorganic pigments include inorganic red pigments (e.g., iron oxide (red oxide), iron titanate, etc.); inorganic brown pigments (e.g., gamma-iron oxide, etc.); inorganic yellow pigments (e.g., yellow iron oxide, yellow ocher, etc.); inorganic black pigments (e.g., black iron oxide, low-order titanium oxide, etc.); inorganic purple pigments (e.g., manganese violet, cobalt violet, etc.); inorganic green pigments (e.g., chromium oxide, chromium hydroxide, cobalt titanate, etc.); inorganic blue pigments (e.g., ultramarine, Prussian blue, etc.); inorganic white pigments (e.g., titanium dioxide, zinc oxide, etc.); metal powders (e.g., aluminum, gold, silver, copper, etc.), etc.
  • inorganic red pigments e.g., iron oxide (red oxide), iron titanate,
  • organic pigments or dyes for example, organic pigments or dyes such as zirconium, barium or aluminum lake, for example, Red No. 2, Red No. 3, Red No. 102, Red No. 104, Red No. 105, Red No. 106, Red No. 201, Red No. 202, Red No. 203, Red No. 204, Red No. 205, Red No. 206, Red No. 207, Red No. 208, Red No. 213, Red No. 214, Red No. 215, Red No. 218, Red No. 219, Red No. 220, Red No. 221, Red No. 223, Red No. 225, Red No. 226, Red No. 227, Red No. 228, Red No. 230, Red No. 231, Red No.
  • dyes that can be used include No. 2, Red 401, Red 404, Red 405, Red 501, Red 502, Red 503, Red 504, Red 505, Red 506, Orange 201, Orange 205, Orange 401, Yellow 4, Yellow 5, Yellow 201, Yellow 202, Yellow 203, Yellow 204, Yellow 205, Yellow 401, Yellow 402, Yellow 403 (1), Yellow 404, Yellow 405, Yellow 406, Yellow 407, Blue 1, Blue 404, Green 3, Green 201, Green 202, Green 204, Purple 201, etc.
  • dyes such as Eosin Y can also be used.
  • pigments examples include natural pigments such as ⁇ -carotene, cochineal pigment, red cabbage pigment, riboflavin, crocin, anthraquinone, canthaxanthin, and safflower pigment.
  • pearlescent agent there are no particular limitations on the pearlescent agent, and for example, materials generally known as luster pigments can be used. Pearlescent agents can be used alone or in combination of two or more types.
  • Examples of luster pigments which are a type of pearling agent, include titanium mica, iron oxide-coated titanium mica, carmine-coated titanium mica, carmine- and malt-coated titanium mica, iron oxide- and carmine-treated titanium mica, malt-coated titanium mica, iron oxide- and malt-coated titanium mica, chromium oxide-treated titanium mica, black titanium oxide-treated titanium mica, acrylic resin-coated aluminum powder, silica-coated aluminum powder, titanium oxide-coated mica, titanium oxide-coated bismuth oxychloride, titanium oxide-coated talc, colored titanium oxide-coated mica, titanium oxide-coated synthetic mica, titanium oxide-coated silica, titanium oxide-coated alumina, titanium oxide-coated glass powder, polyethylene terephthalate-polymethyl methacrylate laminated film powder, bismuth oxychloride, fish scale foil, iron oxide-coated titanium oxide-coated mica such as red ocher titanium oxide-coated mica, which is mica coated with iron oxide and titanium oxide,
  • colorless luster pigments known transparent luster pigments can be used.
  • luster pigments are made of glass particles as a base material, and a coating made of a high refractive index material such as titanium dioxide is formed on the surface of the base material.
  • photoluminescent pigment does not include the color materials described above, and refers to a pigment that exhibits photoluminescence. Additionally, “colored photoluminescent pigment” refers to a photoluminescent pigment that exhibits a color other than colorless or white. Additionally, photoluminescent pigments typically exhibit a flat, flake-like or scaly form.
  • the matting agent there are no particular limitations on the matting agent, so long as it is a material (e.g., a particulate or powdered material) that can make the surface of the film applied to the lips matte and suppress so-called "shininess.”
  • matting agent materials that can be used include inorganic materials such as extender pigments (e.g., mica, talc, silica (e.g., fumed silica)), calcium carbonate, clay, alumina, and titanium oxide, organic materials such as organopolysiloxane elastomers and polyvinylidene copolymers, and waxes.
  • Matting agents can be used alone or in combination of two or more types.
  • the matting agent material and the coloring material overlap, and the blending of such materials results in a matte surface of the film, the material is treated as a matting agent.
  • beads there are no particular limitations on the type of beads, and examples of beads that can be used include inorganic beads made of silica gel, natural stone, glass, etc.; resin beads such as polystyrene resin and polyacrylic resin; and composite beads that combine inorganic and resin materials.
  • shape of the beads There are also no particular limitations on the shape of the beads, and they are not limited to spheres, but can have a variety of shapes such as hemispheres, spindles, cubes, and rectangular parallelepipeds. Beads can be used alone or in combination of two or more types.
  • “beads” refers to components that generally exhibit decorative properties and have parts that are larger than the maximum length of the coloring material, pearl agent, and matte agent described above.
  • color materials, pearling agents, matting agents, cloth, rubber materials, and beads in the first agent. If these are compounded in the second agent, when the second agent is applied to the application surface of the first agent, the agent may harden during the process, and these materials may become easily localized, which may result in uneven coloring. From the viewpoint of suppressing defects such as uneven coloring, it is advantageous to compound these materials in the first agent. Furthermore, color materials, pearling agents, matting agents, cloth, rubber materials, and beads may be compounded in the second agent to the extent that defects such as uneven coloring do not occur, but it is advantageous for these not to be included in the second agent.
  • the present disclosure's applied film-forming agent for lips can be used as a lip cosmetic.
  • lip cosmetic include lipstick and lip gloss.
  • the method of using the applied-type film-forming agent for lips of the present disclosure is not particularly limited, and may include, for example, any of the following steps. Since such a method allows makeup to be applied to the lips, the method may also be called a makeup method.
  • the method of using the applied-type film-forming agent for lips of the present disclosure does not include methods of surgery, treatment, or diagnosis for humans: Applying the first agent to the lips to form a first agent layer, and then applying the second agent onto the first agent layer to form a film, or The second agent is applied to the lips to form a second agent layer, and then the first agent is applied onto the second agent layer to form a film; or, the first agent and the second agent are mixed to prepare a mixture, and then the mixture is applied to the lips to form a film.
  • the preferred method of use is to apply the first agent to the lips to form a first agent layer, and then apply the second agent onto this first agent layer and crosslink it to form a film.
  • the materials described above can be used for the first and second agents in the same way.
  • This method may be performed once, or the method may be performed multiple times (e.g., two or more times, or three or more times) on the formed film.
  • the method may include, for example, any of the following operations.
  • FIG. 2 shows an example in which the applied film-forming agent for lips of the present disclosure is used as a lipstick and the method is performed multiple times (two or three times): A process of applying a first agent to the formed coating to form a first agent layer, and then applying a second agent onto the first agent layer to further form a coating; or An operation of applying a second agent to the formed coating to form a second agent layer, and then applying a first agent onto the second agent layer to further form a coating; or an operation of mixing the first agent and the second agent to prepare a mixture, and then applying the mixture to the formed coating to further form a coating.
  • a forming agent containing optional ingredients such as pearling agents, matting agents, beads, cloth, etc. may be used at a certain stage.
  • a film may be formed using a forming agent that does not contain pearling agents, etc., and then a first agent containing pearling agents, etc. may be applied to the formed film to form a first agent layer, and then a second agent may be applied on the first agent layer to further form a film containing pearling agents, etc.
  • an optional ingredient such as a pearling agent may be mixed with the first agent and the second agent to prepare a mixture, and then the mixture may be applied to the formed film to further form a film containing pearling agents, etc.
  • a layer different from the forming agent or film of the present disclosure may be applied to the lips before the first agent, the second agent, or a mixture including the first agent and the second agent is applied to the lips; the first agent may be applied to the lips to form a first agent layer, a different layer may be applied on the first agent layer, and then the second agent may be applied to cover the different layer; the second agent may be applied to the lips to form a second agent layer, a different layer may be applied on the second agent layer, and then the first agent may be applied to cover the different layer; or a film may be formed, and then a different layer may be applied to the film.
  • This operation may also be performed when multiple films are stacked.
  • the materials constituting the different layers include at least one selected from the group consisting of pearling agents, matting agents, beads, cloth, rubber materials (e.g., rubber sheets made of silicone rubber, etc.), lipstick, and gloss.
  • the different layers may be applied to the entire surface of the lips, or may be applied partially as shown in FIG. 3.
  • non-adhesive materials When applying materials such as pearling agents, matting agents, cloth, rubber materials, and beads (sometimes simply referred to as "non-adhesive materials") to the film, a mixture of a material that can exhibit adhesive properties to the film and a non-adhesive material may be used to apply the film, or the non-adhesive material may be applied to the film after applying an adhesive material to the non-adhesive material or the film.
  • the non-adhesive material since the film formed by the forming agent of the present disclosure can exhibit adhesive properties before it is completely crosslinked, the non-adhesive material may be applied to the film before it is completely crosslinked, and the film may then be completely crosslinked (FIG. 3).
  • the method of using the presently disclosed applied film-forming agent for lips can also be used as a cosmetic treatment.
  • moisture can be unknowingly lost, leading to a state in which the stratum corneum on the surface of the lips is unable to maintain its moisture content.
  • the lips lack moisture, the skin on the lips is unable to effectively produce the moisturizing components it produces itself (Nature Moisturizing Factor (NMF)).
  • NMF ture Moisturizing Factor
  • the barrier function and moisturizing function of the lip surface are reduced, making the lips more susceptible to damage, which is thought to cause a loss of moisture and lead to dry lips and other problems.
  • the occlusion effect of the film (the effect of preventing moisture from escaping from the lips) can keep the lips well moisturized.
  • the function of producing moisturizing ingredients produced by the skin of the lips itself is improved, and the turnover in the stratum corneum is also improved, making problems such as chapped lips less likely to occur, and improving the cosmetic effect.
  • the term "cosmetic method" refers to applying the presently disclosed film-forming agent for lips to the lips to form a film and beautify the condition of the lips, or a method for beautifying the condition of the lips, and is different from a method of surgery, treatment, or diagnosis of a human being.
  • first or second agent there are no particular limitations on the method for applying the first or second agent to the lips, the different layers described above, or the first or second agent layer, and for example, methods such as spreading with fingers, spray application, transfer, etc. can be used.
  • the first agent and/or the second agent are separated into water and oil, it is preferable to shake these agents to forcibly form a two-phase system (oil-in-water type or water-in-oil type) from the viewpoint of crosslinking reactivity between the first agent and the second agent, etc.
  • the applied-type film-forming agent for lips of the present disclosure can be provided as a kit having the above-mentioned first and second agents constituting the forming agent.
  • the kit may also have any other optional components, such as a component for facilitating application of the first agent, etc. to the lips, or a material constituting the different layers described above.
  • Optional components include, for example, instructions for use, brushes, cotton swabs, cutters, scissors, materials constituting the different layers described above (for example, pearlescent agents, matte agents, beads, cloth, rubber materials, lipstick, and gloss), cleansers for removing film from the lips, mirrors, etc.
  • instructions for use can include not only general instructions for use attached in the form of a document within the kit, but also, for example, instructions for use printed on packaging containers such as the packaging container that contains the kit or the tube into which the first agent, etc. is injected.
  • the kit may be configured such that the first and second agents are not brought into contact with each other, for example, by packaging the agents in separate containers or in separate compartments of a container having two or more compartments.
  • the agents may also be configured to be applied one at a time or to be mixed together before or during use.
  • the thickness of the film prepared using the above-mentioned application-type film-forming agent for lips of the present disclosure is not particularly limited, and can be appropriately adjusted in consideration of, for example, breathability, invisibility, occlusion to the skin, aesthetics, etc.
  • the thickness of the film can be, for example, 0.5 ⁇ m or more, 1 ⁇ m or more, 10 ⁇ m or more, 30 ⁇ m or more, or 40 ⁇ m or more.
  • There is no particular limit to the upper limit of the thickness but it can be, for example, 150 ⁇ m or less, 100 ⁇ m or less, 90 ⁇ m or less, 80 ⁇ m or less, 70 ⁇ m or less, 60 ⁇ m or less, or 50 ⁇ m or less.
  • the thickness can be defined as the average value calculated by measuring the thickness of any part of the film five times using a high-precision digital micrometer (MDH-25MB, manufactured by Mitutoyo Corporation).
  • ⁇ Gloss retention test> A panel of 20 experts applied the first and second agents of the test sample in order to form a film on their lips, and after 2 hours, the gloss retention of the film was evaluated according to the following criteria.
  • a and B are considered to be acceptable, and C is considered to be unacceptable:
  • (Evaluation criteria) A: 15 or more of 20 expert panelists evaluated that the product had a gloss retention effect.
  • B 10 to 14 expert panelists out of 20 evaluated that the coating had a gloss retention effect.
  • C Nine or less of the 20 expert panelists rated the product as having a gloss retention effect.
  • Color retention test A panel of 20 experts applied the first and second agents of the test sample in order to form a film on their lips, and after 2 hours, the color retention of the film was evaluated according to the following criteria.
  • a and B ratings can be considered as passing, and C rating can be considered as failing:
  • C Nine or less expert panelists out of 20 evaluated the color retention effect.
  • Peel resistance test 1 A panel of 20 experts applied the first and second agents of the test sample to the lips of the skin to form a film. After 2 hours, the film was evaluated for its resistance to peeling according to the following criteria. Here, A and B are considered to be acceptable, and C is considered to be unacceptable: (Evaluation criteria) A: 15 or more out of 20 expert panelists evaluated that the coating on the lips did not peel off. B: 10 to 14 expert panelists out of 20 evaluated that the coating on the lips did not peel off. C: Nine or less out of 20 expert panelists evaluated that the coating on the lips did not peel off.
  • Test sample 1 was a lip-applied film-forming agent of the present disclosure consisting of a first agent and a second agent
  • test sample 2 was a liquid-type lipstick containing a conventional film-forming agent.
  • the first agent was applied to a white paper surface using a doctor blade to a thickness of about 100 ⁇ m, and then the second agent was spread with a finger on the surface of the first agent and left for 30 minutes to form a film.
  • lipstick was applied to a white paper surface using a doctor blade to a thickness of about 100 ⁇ m and left for 30 minutes.
  • a tissue was applied to the film and lipstick obtained on the paper surface, and the tissue was pressed against the paper surface with both hands for about 3 seconds, and then the tissue was peeled off and the color transfer to the tissue was visually observed.
  • Test Example 1 Each test sample in Test Example 1 was prepared according to the following method. In Test Example 1, the above-mentioned gloss retention test, color retention test, and peel resistance test 1 were carried out. The results are shown in Tables 1 and 2. The blending amounts in Tables 1 and 2 are in parts by mass.
  • a first agent was prepared by uniformly mixing 47.7 parts by mass of vinyl dimethicone containing an unsaturated portion (vinyl group) at a ratio of 0.11 mmol/g as the first unsaturated organopolysiloxane, 0.7 parts by mass of hydrogen dimethicone containing a hydride functionalized portion (Si—H group) at a ratio of 7.55 mmol/g as the first hydride functionalized polysiloxane, 8.0 parts by mass of synthetic wax, 20.0 parts by mass of dimethicone, 21.6 parts by mass of diphenylsiloxyphenyl trimethicone, 0.5 parts by mass of diisostearyl malate, 0.5 parts by mass of glyceryl diisostearate, and 1.0 part by mass of Red No. 202 as a coloring material.
  • a second agent was prepared by uniformly mixing 1.0 part by weight of a mixture of vinyl dimethicone, divinyl disiloxane, and platinum catalyst, 20.0 parts by weight of isododecane, and 79.0 parts by weight of dimethicone. Note that the vinyl dimethicone and divinyl disiloxane contained in the mixture containing the platinum catalyst are not taken into consideration when calculating "H” (the total molar amount of hydride-functionalized moieties in the hydride-functionalized polysiloxane) and "V” (the total molar amount of unsaturated moieties in the unsaturated organopolysiloxane) in the table.
  • H the total molar amount of hydride-functionalized moieties in the hydride-functionalized polysiloxane
  • V the total molar amount of unsaturated moieties in the unsaturated organopolysiloxane
  • Examples 1 to 3 and Comparative Example 2 The first and second agents were prepared in the same manner as in Comparative Example 1, except that the blending amounts of each component in the first agent were changed to the ratios shown in Table 1.
  • Examples 4 to 15 The first and second agents were prepared in the same manner as in Comparative Example 1, except that the components and their amounts in the first agent were changed to those shown in Table 2.
  • Test Example 2 Each test sample in Test Example 2 was prepared according to the following method. In Test Example 2, the above-mentioned peel resistance test 2 was carried out. The results are shown in FIG.
  • Example 4 The first agent was prepared by uniformly mixing 75.4 parts by mass of vinyl dimethicone containing 0.11 mmol/g of unsaturated moieties (vinyl groups) as the first unsaturated organopolysiloxane, 14.6 parts by mass of hydrogen dimethicone containing 7.55 mmol/g of hydride functionalized moieties (Si-H groups) as the first hydride functionalized polysiloxane, 2.5 parts by mass of diisostearyl malate, 2.5 parts by mass of glyceryl diisostearate, and 5.0 parts by mass of Red No. 202 as a coloring material.
  • the total molar amount (V) of the unsaturated moieties in the unsaturated organopolysiloxane was 8.3 mmol
  • the total molar amount (H) of the hydride functionalized moieties in the hydride functionalized polysiloxane was 110.2 mmol
  • the molar ratio of the total molar amount (H) of the hydride functionalized moieties to the total molar amount (V) of the unsaturated moieties was 13.3.
  • Comparative Example 3 Lipstick containing a conventional film-forming agent A lipstick was prepared by uniformly mixing 8.5 parts by weight of polyethylene, 1.5 parts by weight of microcrystalline wax, 54.0 parts by weight of cyclopentasiloxane, 2.5 parts by weight of diisostearyl malate, 12.5 parts by weight of trimethylsiloxysilicate as a film-forming agent, 3.5 parts by weight of triethylhexanoin, 10.0 parts by weight of mica, 2.5 parts by weight of glyceryl diisostearate, and 5.0 parts by weight of Red No. 202 as a coloring material.
  • Test Example 3 The test samples in Test Example 3 were prepared according to the following method. In Test Example 3, the finish when the coatings were stacked was evaluated. The results are shown in FIG.
  • Example 5 A first agent was prepared by uniformly mixing 40.5 parts by mass of vinyl dimethicone containing an unsaturated portion (vinyl group) at a ratio of 0.11 mmol/g as the first unsaturated organopolysiloxane, 7.9 parts by mass of hydrogen dimethicone containing a hydride functionalized portion (Si-H group) at a ratio of 7.55 mmol/g as the first hydride functionalized polysiloxane, 20.0 parts by mass of dimethicone, 11.6 parts by mass of diphenylsiloxyphenyl trimethicone, 10.0 parts by mass of dimethicone-treated fumed silica, and 10.0 parts by mass of Red No.
  • the total molar amount (V) of unsaturated moieties in the unsaturated organopolysiloxane was 4.5 mmol
  • the total molar amount (H) of hydride-functionalized moieties in the hydride-functionalized polysiloxane was 59.6 mmol
  • the molar ratio of the total molar amount (H) of hydride-functionalized moieties to the total molar amount (V) of unsaturated moieties was 13.2.
  • Test Example 4 The test sample in Test Example 4 was prepared according to the following method. In Test Example 4, the finish when beads were applied to the film was evaluated. The results are shown in Figure 3. The beads used were spherical acrylic resin beads with the shape and size shown in Figure 3. In addition, the first agent was applied to the lips, and then the second agent was applied, and the beads were applied directly to the film before the crosslinking reaction was completely completed.
  • Example 6 (First Agent) The first agent was prepared by uniformly mixing 50.53 parts by mass of vinyl dimethicone containing an unsaturated portion (vinyl group) at a ratio of 0.015 mmol/g as the first unsaturated organopolysiloxane, 7.87 parts by mass of hydrogen dimethicone containing a hydride functionalized portion (Si-H group) at a ratio of 4.35 mmol/g as the first hydride functionalized polysiloxane, 22.0 parts by mass of dimethicone, 10.0 parts by mass of hydrogenated polyisobutene, 1.6 parts by mass of diisostearyl malate, 7.0 parts by mass of dimethicone-treated fumed silica, and 1.0 part by mass of Blue No.
  • the total molar amount (V) of unsaturated moieties in the unsaturated organopolysiloxane was 0.758 mmol
  • the total molar amount (H) of hydride-functionalized moieties in the hydride-functionalized polysiloxane was 34.23 mmol
  • the molar ratio of the total molar amount (H) of hydride-functionalized moieties to the total molar amount (V) of unsaturated moieties was 45.2.

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Abstract

L'invention concerne un agent filmogène de type application sur les lèvres capable de former un film qui est moins susceptible de peler et présente une excellente durabilité de film comme le maquillage longue durée sur les lèvres, qui sont fréquemment en mouvement.　Un agent filmogène de type application sur les lèvres selon la présente invention comprend : un premier agent contenant un agent réactif réticulable qui constitue un film ; et un second agent contenant un catalyseur pour réticuler l'agent réactif réticulable. Le rapport molaire de la quantité molaire totale de fractions fonctionnalisées par hydrure dans un polysiloxane fonctionnalisé par hydrure contenu dans le premier agent et le second agent sur la quantité molaire totale de fractions insaturées dans un organopolysiloxane insaturé contenu dans le premier agent et le second agent est de 1,2 à 50,0.
PCT/JP2023/037212 2022-10-28 2023-10-13 Agent filmogène de type application sur les lèvres et méthode d'utilisation dudit agent filmogène WO2024090246A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070142575A1 (en) * 2005-12-21 2007-06-21 Tao Zheng Cosmetic compositions having in-situ hydrosilylation cross-linking
JP2009520002A (ja) * 2005-12-20 2009-05-21 ロレアル 少なくとも１つはシリコーン系である化合物ａおよびｂを付けることを含む、ケラチン質のメイクアップまたはケア方法
JP2019503396A (ja) * 2015-11-09 2019-02-07 シセイドー アメリカズ コーポレーション 皮膚への適用のための組成物及び方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009520002A (ja) * 2005-12-20 2009-05-21 ロレアル 少なくとも１つはシリコーン系である化合物ａおよびｂを付けることを含む、ケラチン質のメイクアップまたはケア方法
US20070142575A1 (en) * 2005-12-21 2007-06-21 Tao Zheng Cosmetic compositions having in-situ hydrosilylation cross-linking
JP2019503396A (ja) * 2015-11-09 2019-02-07 シセイドー アメリカズ コーポレーション 皮膚への適用のための組成物及び方法

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