WO2019039385A1 - Microcapsule, composition et film pour cosmétiques - Google Patents

Microcapsule, composition et film pour cosmétiques Download PDF

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Publication number
WO2019039385A1
WO2019039385A1 PCT/JP2018/030452 JP2018030452W WO2019039385A1 WO 2019039385 A1 WO2019039385 A1 WO 2019039385A1 JP 2018030452 W JP2018030452 W JP 2018030452W WO 2019039385 A1 WO2019039385 A1 WO 2019039385A1
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WIPO (PCT)
Prior art keywords
component
microcapsules
group
microcapsule
cooling sensation
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PCT/JP2018/030452
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English (en)
Japanese (ja)
Inventor
達也 薄
川上　浩
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富士フイルム株式会社
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Publication of WO2019039385A1 publication Critical patent/WO2019039385A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11—Encapsulated compositions
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/87—Polyurethanes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/14—Polymerisation; cross-linking
    • B01J13/18—In situ polymerisation with all reactants being present in the same phase
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/12—Processes in which the treating agent is incorporated in microcapsules
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes

Definitions

  • the present disclosure relates to microcapsules, compositions and cosmetic sheets.
  • cooling agents that are applied to the skin and the like to develop a cooling sensation
  • development for various uses of cooling agents has been attempted.
  • talls such as menthol are conventionally known as typical components, and are used in creams, lotions, cleaning agents and the like.
  • menthol etc. feels cold at the moment of application to the skin, but the effect of cold sensation gradually diminishes over time. For this reason, the function which expresses a feeling of cold lasts for a long time, and a means which can give a feeling of cold as needed at a desired time is desired.
  • Various methods have been proposed for sustaining a cold sensation for a long time.
  • microcapsules in which an active ingredient such as a perfume is encapsulated in an aldehyde-containing resin such as melamine resin, a formaldehyde scavenger, and a surfactant has been proposed. It is believed to be effective. Furthermore, the microcapsules contained in the liquid laundry composition are attached to clothes, and when the clothes are dried, the microcapsules attached to clothes, such as perfumes and antiperspirant active substances encapsulated in microcapsules under predetermined conditions And the like, which are mentioned as advantages (see Japanese Patent No. 5864700).
  • menthol which is widely used as a cooling agent, may not be able to form microcapsules even when urethane resin, melamine resin, etc., which are general-purpose microcapsule wall materials, are used. found.
  • the present disclosure has been made in view of the above. That is, The problem to be solved by one embodiment of the present invention is to provide a microcapsule in which the function to develop a cold sensation lasts for a long time and can develop a cold sensation as needed at a desired time.
  • the problem to be solved by the other embodiments of the present invention is that the function of expressing cold feeling lasts for a long time, and can be given a cold feeling as needed at a desired time, and can be applied to various applications. It is an object of the present invention to provide a cosmetic composition which is a composition and its application.
  • R 1 represents an alkyl group or an alkenyl group
  • R 2 represents a hydrocarbon group.
  • the compounds represented by the general formula (I) also include their isomers.
  • R 4 and R 5 each independently represent a hydrocarbon group.
  • the dashed line connecting R 5 and the carbon atom in the 6-membered ring linked to R 5 represents a single bond or absence.
  • R 4 , R 5 and R 6 each independently represent a hydrocarbon group, and X represents an oxygen atom.
  • Y 1 represents a single bond or an oxygen atom
  • Y 2 represents -C (R YA ) (R YB )-
  • R YA and R YB each independently represent a hydrogen atom or an alkyl Represents a group
  • Z represents an alkylene group or a carbonyl group
  • R 7 and R 8 each independently represent a hydrogen atom or a hydrocarbon group.
  • the cooling component having no hydroxy group contains at least one member selected from the group consisting of camphor, menthone, carvone, menthyl acetate, 1,8-cineole, and plegon. It is a microcapsule as described in any one.
  • ⁇ 5> The microcapsule according to any one of ⁇ 1> to ⁇ 4>, which further includes a persistent sensation component as an included component.
  • ⁇ 6> The microcapsule according to ⁇ 5>, wherein the cooling sensation persistent component is at least one of menthyl glyceryl ether and menthyl lactate.
  • thermoresponsive composition Assuming that the number average wall thickness of the ⁇ 7> microcapsules is ⁇ and the average primary particle diameter of the microcapsules is D, the wall thickness ratio ( ⁇ / D ratio) to the particle diameter is 0.002 to 0.05.
  • the thermoresponsive composition according to any one of ⁇ 1> to ⁇ 6>.
  • composition comprising the microcapsule according to any one of ⁇ 1> to ⁇ 7>.
  • composition according to ⁇ 8> further comprising a dispersion medium of microcapsules.
  • composition according to ⁇ 8> or ⁇ 9> which further contains a cationic surfactant and is a softener for clothing.
  • the cleaning agent for clothing according to ⁇ 8> or ⁇ 11> further comprising at least one surfactant selected from the group consisting of anionic surfactants, nonionic surfactants and amphoteric surfactants.
  • the composition as described in 9> The composition as described in ⁇ 9> which is ⁇ 12> cosmetics.
  • a cosmetic sheet comprising: a support; and the composition according to ⁇ 9> impregnated in the support.
  • the function to develop a cold sensation lasts for a long time, and can develop a cold sensation as needed at a desired time.
  • the function of expressing cold feeling lasts for a long time, and can provide cold feeling as needed at a desired time, and a composition applicable to various uses and The cosmetic sheet which is the application can be provided.
  • a numerical range indicated by using “to” means a range including numerical values described before and after “to” as the minimum value and the maximum value, respectively.
  • the upper limit value or the lower limit value described in a certain numerical value range may be replaced with the upper limit value or the lower limit value of the other stepwise description numerical value range in the numerical value range described stepwise in the present disclosure.
  • the upper limit value or the lower limit value described in a certain numerical range may be replaced with the value shown in the example.
  • a combination of preferred embodiments is a more preferred embodiment.
  • the amount of each component in the composition means the total amount of the plurality of substances present in the composition unless a plurality of substances corresponding to each component are present in the composition. Do.
  • the term "step" is included in the term if the intended purpose of the step is achieved, even if it can not be distinguished clearly from the other steps, not only an independent step. .
  • the microcapsule of the present disclosure includes a capsule wall containing at least one selected from the group consisting of a urethane resin, a urea resin, and a melamine resin, and a cooling sensation component having no hydroxy group which is an included component.
  • microcapsule including microcapsule wall and inclusion component is used to mean “microcapsule in a state where the inclusion component is contained inside the capsule wall”.
  • inclusion component included in the microcapsule may be simply referred to as “inclusion”.
  • the cooling sensation component can be obtained by using a cooling sensation component having no hydroxy group as the inclusion component, and setting the capsule wall to be a capsule wall containing at least one selected from the group consisting of a urethane resin, a urea resin and a melamine resin. Stable microcapsules are obtained which are stably held in the capsule wall and can develop a cooling sensation at a desired time. It is considered that the cooling sensation component having a hydroxy group such as menthol partially inhibits the film formation by the coexistent urethane resin, urea resin, melamine resin and the like wall material.
  • At least one capsule wall material selected from the group consisting of urethane resin, urea resin and melamine resin excellent in stability it is stable by using a cooling sensation component having no hydroxy group as the inclusion component. It is believed that microcapsules can be formed and microcapsules can be obtained which can develop a cooling sensation at a desired time.
  • Cool sensation component not having hydroxy group contains a cooling sensation component having no hydroxy group (hereinafter, may be referred to as a specific cooling sensation component) as an inclusion component.
  • the specific cooling sensation component may contain only one type, or may contain two or more types.
  • the cold sensation component refers to a component that can give a cold feeling, a cool feeling, etc., that is, a component having a cold sensation function.
  • the cooling sensation component in the present disclosure is not a component that imparts a cooling sensation due to a decrease in skin temperature due to a volatile component such as ethanol adhering to the skin and volatilizing, and penetrates the skin such as l-menthol, camphor, etc. It is a component that sensitarily cools by activating the cold receptor and transmitting it to the brain via nerves.
  • a cooling sensation component selected from cyclic monoterpene compounds having no hydroxy group is preferably mentioned.
  • a compound represented by the following general formula (I), a compound represented by the general formula (II), a compound represented by the general formula (III), and a general formula (IV) It is preferred to include at least one compound selected from the group consisting of
  • R 1 represents an alkyl group or an alkenyl group
  • R 2 represents a hydrocarbon group.
  • the compounds represented by the general formula (I) also include their isomers.
  • R 1 is preferably an alkyl group, and examples of the alkyl group include alkyl groups having 1 to 6 carbon atoms such as methyl and ethyl.
  • alkenyl group alkenyl groups having 2 to 6 carbon atoms can be mentioned.
  • R 3 represents an alkyl group, and examples of the alkyl group include alkyl groups having 1 to 6 carbon atoms such as methyl and ethyl.
  • R 4 and R 5 each independently represent a hydrocarbon group.
  • the dashed line connecting R 5 and the carbon atom in the 6-membered ring linked to R 5 represents a single bond or absence. That is, R 5 and the carbon atom in the 6-membered ring linked to R 5 may be linked by a single bond or linked by a double bond.
  • R 4 include an alkyl group and an alkenyl group, and an alkyl group is preferable.
  • the alkyl group include alkyl groups having 1 to 6 carbon atoms such as methyl and ethyl.
  • alkenyl group alkenyl groups having 2 to 6 carbon atoms can be mentioned.
  • R 4 , R 5 and R 6 each independently represent a hydrocarbon group, and X represents an oxygen atom.
  • R 4 and R 6 are preferably each independently an alkyl group, and examples of the alkyl group include alkyl groups having 1 to 6 carbon atoms such as methyl and ethyl.
  • R 5 is preferably a branched alkyl group, and examples thereof include an alkyl group having 3 to 6 carbon atoms, and preferred examples include —C (CH 3 ) 2 and the like.
  • Y 1 represents a single bond or an oxygen atom
  • Y 2 represents -C (R YA ) (R YB )-
  • R YA and R YB each independently represent a hydrogen atom or Represents an alkyl group.
  • Z represents an alkylene group or a carbonyl group.
  • R 7 and R 8 each independently represent a hydrogen atom or a hydrocarbon group.
  • R YA and R YB in Y 2 each independently represent a hydrogen atom or an alkyl group, preferably an alkyl group, and as the alkyl group, an alkyl group having 1 to 6 carbon atoms such as a methyl group or an ethyl group is preferred. It can be mentioned.
  • Z represents an alkylene group or a carbonyl group.
  • R 7 and R 8 are preferably each independently an alkyl group, and examples of the alkyl group include alkyl groups having 1 to 6 carbon atoms such as methyl and ethyl.
  • the specific cooling component preferably includes at least one selected from the group consisting of camphor, menthone, carvone, menthyl acetate, and 1,8-cineole, and plegon.
  • carvone includes R carvone which is an optical isomer, and S carvone. The structures of these compounds are shown below.
  • specific cooling sensation component as the inclusion component of the microcapsule only one type may be used, or two or more types may be used.
  • the specific cooling sensation component as the inclusion component can be appropriately selected and used according to the purpose of use of the microcapsule.
  • the total cooling sensation component in an inclusion component is a specific cooling sensation component.
  • the total cooling sensation component in an inclusion component is a specific cooling sensation component, you may use together a specific cooling sensation component and another cooling sensation component.
  • the upper limit of the content of the specific cooling sensation component in the total cooling sensation component is not particularly limited.
  • the content of the specific cooling sensation component in all cooling sensation components can be 95% by mass or less, and may be 90% by mass or less.
  • the total amount of the contained component is a specific cooling sensation component.
  • the total amount of the contained component is a specific cooling sensation component.
  • the specific cooling sensation component there is no restriction
  • the content of the specific cooling sensation component relative to the total amount of the inclusion component can be 95% by mass or less as a preferable range, can be 90% by mass or less according to the purpose, and can be 80% by mass or less And 70% by mass or less.
  • the microcapsules may contain an included component other than the specific cooling sensation component (hereinafter, may be referred to as another included component).
  • an included component other than the specific cooling sensation component hereinafter, may be referred to as another included component.
  • a fragrance a cooling sensation component other than the specific cooling sensation component
  • a cooling sensation maintaining component a solvent, a coloring agent, a stabilizer and the like can be mentioned.
  • the inclusion component contains a cooling sensation maintaining component.
  • the cooling sensation persistent component is selected from compounds having good compatibility with the specific cooling sensation component and having lower volatility compared to the specific cooling sensation component. Specifically, esterification products and etherification products of the cooling sensation component are representative.
  • the cooling sensation maintaining component is preferably at least one of menthyl glyceryl ether and menthyl lactate.
  • the content of the cooling sensation maintaining component when including the cooling sensation maintaining component as the inclusion component is preferably 10 parts by mass to 200 parts by mass, and 20 parts by mass to 100 parts by mass with respect to 100 parts by mass of the specific cooling sensation component. Part is more preferable, and 30 parts by mass to 60 parts by mass is more preferable.
  • the inclusion component may contain a solvent as an oil component of the so-called oil phase.
  • the solvent include fatty acid ester compounds such as tri (caprylic capric acid) glyceryl, isopropyl myristate, alkyl naphthalene compounds such as diisopropyl naphthalene, diaryl alkane compounds such as 1-phenyl-1-xylylethane, isopropylbiphenyl And aromatic hydrocarbons such as alkylbiphenyl compounds such as triarylmethane compounds, alkylbenzene compounds, benzyl naphthalene compounds, diaryl alkylene compounds, and arylindane compounds; aliphatic hydrocarbons such as dibutyl phthalate and isoparaffins; Natural animal and vegetable oils such as camellia oil, soybean oil, corn oil, cottonseed oil, rapeseed oil, olive oil, coconut oil, castor oil, fish oil, etc .; and high boiling fractions of
  • the inclusion component may optionally contain a co-solvent as an oil phase component for enhancing the solubility of the wall material in the oil phase when producing the microcapsules.
  • Cosolvents do not include the solvents mentioned above.
  • the auxiliary solvent include ketone compounds such as methyl ethyl ketone, ester compounds such as ethyl acetate, alcohol compounds such as isopropyl alcohol, and the like.
  • the co-solvent has a boiling point of 130 ° C. or less.
  • the content of the auxiliary solvent in the inclusion component is preferably less than 50% by mass, more preferably less than 30% by mass, and still more preferably less than 20% by mass, with respect to the total mass of the inclusion component.
  • the microcapsule of the present disclosure may contain at least one kind of a coloring material as an included component for the purpose of improving design.
  • a coloring material as an included component
  • the solvent resistance of the coloring material as the inclusion component can be improved, and the selection of a wide range of coloring materials including the coloring material having a relatively low solvent resistance is It will be possible.
  • the coloring material is contained in the microcapsule as the inclusion component, the coloring material is preferably a dye from the above viewpoint.
  • the coloring material may contain only one kind, or two or more kinds.
  • the content of the coloring material in the case of including the coloring material as the inclusion component, and it can be appropriately selected according to the purpose such as the designability and the ease of confirming the presence of the microcapsule.
  • the content of the coloring material increases, the content of the specific cooling sensation component as the active component relatively decreases, so the content of the coloring material is 2% by mass or less based on the total mass of the inclusion component Is preferred.
  • the inclusion component may contain a flavor.
  • a flavor As the spice, synthetic spice, natural essential oil, natural spice described in "Patent Office, well-known common technology collection (flavor) Part III, perfume spice, page 49-page 103, published on June 15, 2001" From animal and plant extracts and the like, suitable ones can be appropriately selected and used.
  • Monoterpenes such as pinene, myrcene, camphene, R limonene, Sesquiterpenes such as Cedrene, Caryophyllene, Longifolene, Synthetic perfumes such as 1,3,5-undecatriene, ⁇ -amylcinnamyl aldehyde, dihydrojasmone, methylionone, ⁇ -damascone, acetyl cedrene, methyl dihydrojasmonate, cyclopentadecanolide, etc.
  • Natural essential oils such as orange essential oil, lemon essential oil, bergamot essential oil, mandarin essential oil, Etc.
  • the content of the flavor in the inclusion component is preferably 40% by mass or less, more preferably 30% by mass or less, and most preferably 25% by mass or less.
  • the inclusion component preferably does not contain a cooling sensation component other than the specific cooling sensation component (hereinafter, may be referred to as another cooling sensation component).
  • another cooling sensation component may contain a small amount of a cooling component having a hydroxy group in the molecule such as menthol, dihydrocarbeol and methyl salicylate.
  • content of another cooling sensation component in the case of including other cooling sensation components as an inclusion component 15 mass% or less is preferable, 10 mass% or less is more preferable, and 8 mass% or less is the most preferable.
  • the lower limit of the content in the case of containing other cold sensation components is 0.01% by mass or more, and when it is 0.01% by mass or more, the effect of the addition of the other cooling sensation components Is obtained.
  • the microcapsule of the present disclosure includes a capsule wall for containing the specific cooling sensation component described above as an inclusion component. Since the capsule wall in the present disclosure contains at least one selected from the group consisting of urethane resin, urea resin and melamine resin, it is stable even when the wall thickness is thin, and the microcapsules are stressed as needed. It is excellent in the responsiveness at the time of making a capsule wall collapse and making the effect of the specific cooling sensation component which is an included component express. Furthermore, the capsule wall in the present disclosure is also good in biocompatibility.
  • polyurethane resin, Urea resin A polyurethane, a polyurea, a polyurethane polyurea and the like included in a urethane resin and a urea resin which are preferable examples of the capsule wall will be described.
  • polyurethane, polyurea, polyurethane polyurea and the like are preferably polymers obtained by using an isocyanate compound and an organic solvent, more preferably a polymer having at least one of a urethane bond and a urea bond, and polyurethane polyurea More preferable.
  • an isocyanate compound, a silane coupling agent, etc. are mentioned, An isocyanate compound is preferable, and an isocyanate compound having two or more isocyanate groups in one molecule is preferable among them.
  • isocyanate compound for example, m-phenylene diisocyanate, p-phenylene diisocyanate, 2,6-tolylene diisocyanate, 2,4-tolylene diisocyanate, naphthalene-1,4-diisocyanate, diphenylmethane-4,4'-diisocyanate, 3,3'-Dimethoxy-biphenyl diisocyanate, 3,3'-dimethyldiphenylmethane-4,4'-diisocyanate, xylylene-1,4-diisocyanate, xylylene-1,3-diisocyanate, 4-chloroxylylene-1,3 -Diisocyanate, 2-methylxylylene-1,3-diisocyanate, 4,4'-diphenylpropane diisocyanate, 4,4'-diphenylhexafluoropropane diisocyanate, trimethylene diisocyanate
  • the difunctional diisocyanate compound as a wall material which forms a capsule wall was illustrated above, the trifunctional triisocyanate compound and the tetrafunctional tetraisocyanate compound which are guessed from the compound illustrated above form a capsule wall You may use as a wall material. Moreover, as a wall material which forms a capsule wall, the adduct of the said isocyanate compound and bifunctional alcohol, such as an ethylene glycol type compound or a bisphenol type compound, or phenol is also mentioned.
  • Examples of condensates, polymers or adducts using an isocyanate compound include biuret or isocyanurate which is a trimer of the above-mentioned bifunctional isocyanate compound, a polyol such as trimethylolpropane, and a bifunctional isocyanate compound
  • Examples of the adduct include polyfunctional compounds, formalin condensates of benzene isocyanate, polymers of isocyanate compounds having a polymerizable group such as methacryloyloxyethyl isocyanate, and lysine triisocyanate.
  • the isocyanate compound is described in "Polyurethane resin handbook” (edited by Keiji Iwata, published by Nikkan Kogyo Shimbun, Ltd. (1987)). This document can be referred to when selecting the isocyanate compound as a wall material which forms a capsule wall.
  • the capsule wall of the microcapsule contains a polymer of a trifunctional or higher functional isocyanate is preferable.
  • trifunctional or more than trifunctional isocyanate the trifunctional or more than trifunctional aromatic isocyanate compound, the trifunctional or more than trifunctional aliphatic isocyanate compound etc. are mentioned, for example.
  • trifunctional or higher isocyanate compounds examples include bifunctional isocyanate compounds (compounds having two isocyanate groups in the molecule) and compounds having three or more active hydrogen groups in the molecule (eg trifunctional or higher polyols, It is also preferable to use trifunctional or higher isocyanate compounds (adduct type) as adducts (adducts) with polyamines or polythiols, etc., and trimers of bifunctional isocyanate compounds (biuret type or isocyanurate type).
  • trifunctional or higher isocyanate compounds may be an adduct of xylylene-1,4-diisocyanate or xylylene-1,3-diisocyanate with trimethylolpropane, a biuret, an isocyanurate, etc. .
  • the commercially available product include Takenate (registered trademark) D-102, D-103, D-103H, and D-103M2. , P49-75S, D-110N, D-120N (is
  • Takenate (registered trademark) D-110N, D-120N, D-140N, and D-160N of Mitsui Chemical Co., Ltd. is more preferable as the adduct type trifunctional or higher isocyanate compound.
  • isocyanurate type trifunctional or higher isocyanate compound commercially available commercial products may be used.
  • biuret-type trifunctional or higher isocyanate compound commercially available commercial products may be used.
  • Melamine resins include resins such as reactants of aldehydes and amines.
  • the aldehyde includes formaldehyde.
  • amines include melamine, urea, benzoguanamine, glycoluryl and mixtures thereof.
  • Suitable melamine resins include methylolmelamine, methylated methylolmelamine, iminomelamine and mixtures thereof.
  • Suitable ureas for the preparation of melamine resins include dimethylol urea, methylated dimethylol urea, urearesorcinol and mixtures thereof.
  • a commercially available product may be used as a material suitable for producing a capsule wall containing a melamine resin, and the commercially available product is, for example, Solutia Inc., USA. , Cytec Industries, Sigma Aldrich, etc.
  • the microcapsules preferably have an average primary particle size of 3 ⁇ m to 100 ⁇ m, more preferably 5 ⁇ m to 50 ⁇ m, and still more preferably 8 ⁇ m to 30 ⁇ m.
  • the particle size of the microcapsules is a value measured using Microtrac MT3300EXII (manufactured by Nikkiso Co., Ltd.).
  • the average primary particle size of the microcapsules is appropriately selected in the above-mentioned range according to the purpose of use of the microcapsules.
  • the average primary particle size be larger. Specifically, the range of 8 ⁇ m to 50 ⁇ m is more preferable.
  • the average primary particle size is preferably smaller from the viewpoint that the feel is better. Specifically, the range of 3 ⁇ m to 30 ⁇ m is more preferable.
  • the number average wall thickness of the microcapsules depends on various conditions such as the type of capsule wall material, the inclusion amount of the inclusion in the capsule, and the particle diameter of the capsule, but from the viewpoint of pressure response and inclusion, 30 nm
  • the range of ⁇ 1000 nm is preferable, the range of 50 nm ⁇ 500 nm is more preferable, and the range of 80 nm ⁇ 300 nm is more preferable.
  • the number average wall thickness of the microcapsules is appropriately selected according to the purpose of use of the microcapsules.
  • a mode in which the microcapsules are carried on a sheet and used for example, when used for decorative sheets or when added to softeners to be carried between fibers of clothes, non-woven fabric, woven fabric
  • the number average wall thickness is more preferably in the range of 80 nm to 500 nm from the viewpoint that when held stably in a fiber such as cloth, it does not disintegrate and it easily disintegrates quickly when stressed.
  • the number average wall thickness is preferably in the range of 30 nm to 300 nm, from the viewpoint of being easily disintegrated when touching the skin. .
  • the wall thickness ratio ( ⁇ / D ratio) to the particle diameter is preferably 0.002 to 0.05, and 0 .003 to 0.02 is more preferable, and 0.005 to 0.015 is more preferable.
  • ⁇ / D ratio is in the above range, it is excellent in both the stable retention of the specific cooling sensation component and the responsiveness in the case of collapsing the microcapsule wall as necessary.
  • the ⁇ / D ratio of the microcapsules is appropriately selected in the above range according to the purpose of use of the microcapsules.
  • the microcapsules are carried on a sheet and used, for example, when used for decorative sheets or the like, or when microcapsules are added to a softener or the like to be carried between fibers of clothes And ⁇ / D ratio of 0.002 to 0 from the viewpoint that when they are stably held in fibers such as non-woven fabrics and woven fabrics, they do not disintegrate and they easily disintegrate quickly when stress is applied.
  • the range of .015 is more preferable.
  • the ⁇ / D ratio is 0.005 to 0.03, from the viewpoint that they are easily disintegrated when the skin is touched. The range is more preferred.
  • the number average wall thickness of microcapsules refers to the thickness (nm) of the resin film (so-called capsule wall) that forms the capsule particles of microcapsules, and the number average wall thickness refers to the individual capsule walls of five microcapsules
  • the average thickness obtained by measuring the thickness (nm) of the metal by means of a scanning electron microscope (SEM) and averaging. Specifically, first, the microcapsule solution is applied on any support and dried to form a coating film. The cross section of the dry coated film containing the obtained microcapsules is formed, and the formed cross section is observed using an SEM, and the cross section of the selected individual microcapsules is selected after selecting any five microcapsules. To determine the thickness of the capsule wall and calculate the average value.
  • the wall thickness of the microcapsule is governed by the relationship between the capsule wall and the inclusion and the particle size of the microcapsule as represented by the following equation, and the particle size of the microcapsule, the density of the capsule wall, the solute in the microcapsule
  • the amount of solvent and auxiliary solvent, and the amount of wall material can be adjusted.
  • the capsule wall can be adjusted to a thin thickness by, for example, increasing the amount of inclusions such as a solute, a solvent, an auxiliary solvent, and a wall material contained in the microcapsule.
  • the ratio of the mass of the microcapsule-encapsulating component to the mass of the capsule wall is preferably 5 to 50.
  • the mass of the inclusion component indicates the total amount of the specific cooling sensation component and other inclusion components optionally contained, such as a cooling sensation maintenance component.
  • the mass ratio of the microcapsule-encapsulating component to the mass of the capsule wall is in the above range, the particle diameter is in the above-mentioned median diameter range and a thin thickness (specifically, for example, a number average wall thickness of 10 nm to 200 nm) Microcapsules can be easily obtained and have excellent stress response.
  • the mass ratio of the inclusion component to the capsule wall is more preferably 8 to 20.
  • the microcapsule is a process of preparing an emulsion by dispersing an oil phase containing a specific cooling sensation component and other inclusion components contained as necessary in an aqueous phase containing an emulsifier (hereinafter, step (I) And a wall material forming the microcapsule wall (hereinafter, capsule wall) are polymerized at the interface between the oil phase and the aqueous phase to form a capsule wall, and the microcapsule containing at least a specific cooling sensation component as an inclusion component It is preferable to include the step of forming (hereinafter, step (II)).
  • step (I) the oil phase can be dispersed in the aqueous phase to prepare an emulsion.
  • the oil phase contains at least a specific cooling sensation component, a cooling sensation maintaining component and the like optionally used in combination, and a wall material.
  • the details of the specific cooling sensation component and the cooling sensation maintenance component are as described above.
  • a coloring material is contained as an included component in the microcapsule for the purpose of improving the designability, it is preferable to include the coloring material in the oil phase.
  • the amount of wall material contained in the oil phase may be, for example, in the range of more than 0.5% by mass and 30% by mass or less, preferably 2% by mass to 20% by mass, based on the total mass of the oil phase And more preferably 5% by mass to 15% by mass.
  • the concentration of the capsule wall material in the oil phase can be appropriately adjusted in view of the size, wall thickness, etc. of the microcapsules.
  • the aqueous phase to which the above oil phase is added preferably contains at least an aqueous medium and an emulsifier.
  • the aqueous medium is preferably water, and ion exchange water or the like can be used.
  • the content of the aqueous medium is preferably 20% by mass to 80% by mass, more preferably 30% by mass to 70% by mass, and still more preferably, based on the total mass of the emulsion which is a mixture of the oil phase and the aqueous phase. It is 40% by mass to 60% by mass.
  • Emulsifiers include dispersants or surfactants, or combinations thereof.
  • the dispersant for example, polyvinyl alcohol and its modified product, polyacrylamide and its derivative, ethylene-vinyl acetate copolymer, styrene-maleic anhydride copolymer, ethylene-maleic anhydride copolymer, isobutylene- Maleic anhydride copolymer, polyvinyl pyrrolidone, ethylene-acrylic acid copolymer, vinyl acetate-acrylic acid copolymer, carboxymethyl cellulose, methyl cellulose, casein, gelatin, starch and its derivatives, gum arabic, sodium alginate and the like And polyvinyl alcohol are preferred.
  • the dispersant is preferably a compound which does not react with the wall material or is very difficult to react, and when using, for example, gelatin having a reactive amino group in the molecular chain, gelatin which has been treated to lose reactivity in advance. It is preferable to use
  • nonionic surfactant nonionic surfactant, anionic surfactant, cationic surfactant, amphoteric surfactant etc. are mentioned.
  • the surfactant is not particularly limited, and conventionally known surfactants can be used.
  • the surfactant may be used alone or in combination of two or more.
  • the concentration of the emulsifier is preferably more than 0% by mass and 20% by mass or less, more preferably 0.005% by mass to 10% by mass, with respect to the total mass of the emulsion which is a mixture of an oil phase and an aqueous phase. 01% by mass to 10% by mass is more preferable, and 1% by mass to 5% by mass is particularly preferable.
  • the water phase may optionally contain other components such as UV absorbers, antioxidants, preservatives and the like.
  • Other components may be contained in the range of more than 0% by mass and 20% by mass or less based on the total mass of the aqueous phase, and may be contained in the range of more than 0.1% by mass and 15% by mass or less. You may contain in 1 to 10 mass% or less range.
  • Dispersion refers to dispersing the oil phase as oil droplets in the water phase (emulsification). Dispersion can be carried out using means commonly used for dispersion of oil phase and water phase (for example, homogenizer, Manton goalie, ultrasonic disperser, dissolver, caddy mill, or other known dispersing device).
  • means commonly used for dispersion of oil phase and water phase for example, homogenizer, Manton goalie, ultrasonic disperser, dissolver, caddy mill, or other known dispersing device).
  • the mixing ratio of oil phase to water phase is preferably 0.1 to 1.5, more preferably 0.2 to 1.2, and still more preferably 0.4 to 1.0. preferable.
  • the mixing ratio is in the range of 0.1 to 1.5, an appropriate viscosity can be maintained, the production suitability is excellent, and the stability of the emulsion is excellent.
  • step (II) the wall material is polymerized at the interface between the oil phase and the water phase to form a capsule wall, thereby forming a microcapsule.
  • the polymerization is carried out by causing a wall material contained in the oil phase in the emulsion to polymerize at the interface with the water phase, and is preferably performed under heating.
  • the reaction temperature in polymerization varies depending on the type of wall material and the like, but is usually 40 ° C. to 100 ° C., preferably 50 ° C. to 80 ° C.
  • the reaction time also differs depending on the type of wall material and the like, but is usually about 0.5 hour to 10 hours, preferably about 1 hour to 5 hours.
  • the polymerization time can be shortened by raising the polymerization temperature, but when using inclusions or wall materials that may be decomposed at high temperature, a polymerization initiator that operates at low temperature is selected and the above-mentioned preferable reaction temperature range It may be polymerized at a relatively low temperature.
  • aqueous solvent for example, water, an aqueous solution of acetic acid, etc.
  • a dispersant for aggregation prevention may be added.
  • a charge control agent such as nigrosine or any other auxiliary agent may be added.
  • Auxiliary agents can be added at the time of formation of the capsule wall or at any time.
  • microcapsule of the present disclosure can generally be produced through the steps (I) and (II) described above.
  • compositions of the present disclosure include the microcapsules of the present disclosure as described above.
  • the composition of the present disclosure can be applied to various applications by including the microcapsules of the present disclosure that can stably hold the specific cooling sensation component and perform a cooling sensation function at any time.
  • the composition of the present disclosure is not particularly limited except containing the microcapsule of the present disclosure, and may further include various components other than the microcapsule depending on the purpose of the composition.
  • Various components other than microcapsules may be referred to as "other components”.
  • other components a dispersion medium, a viscosity modifier, etc. are mentioned.
  • the composition of the present disclosure preferably further contains a dispersion medium of microcapsules in addition to the microcapsules.
  • a dispersion medium of microcapsules By further including a dispersion medium of microcapsules, the composition of the present disclosure can be easily blended when used in various applications.
  • the dispersion medium in the composition is appropriately selected according to the purpose of use of the composition.
  • the dispersion medium is preferably a liquid component that does not affect the wall material of the microcapsules.
  • an aqueous solvent and the like can be mentioned. Examples of the aqueous solvent include water, alcohol, a mixture of water and alcohol, and the like, and as the aqueous solvent, ion exchange water can be used.
  • the content of the dispersion medium in the composition of the present disclosure may be appropriately selected according to the application.
  • compositions of the present disclosure may contain a viscosity modifier.
  • a viscosity modifier that can be used in combination with the dispersion medium to be used can be selected according to the type of dispersion medium described above.
  • an aqueous viscosity modifier such as a water-soluble polymer may be selected.
  • polyvinyl alcohol As a viscosity modifier of the water system, polyvinyl alcohol, modified polyvinyl alcohol, hydroxyethyl cellulose, hydroxypropyl cellulose, epichlorohydrin modified polyamide, ethylene-maleic anhydride copolymer, styrene-maleic anhydride copolymer, isobutylene-maleic anhydride salicylic acid copolymer
  • examples thereof include polymers, polyacrylic acids, polyacrylamides, methylol-modified polyacrylamides, starch derivatives, casein, gelatin and the like.
  • a water resistance improver or an emulsion of a hydrophobic polymer (for example, an acrylic resin emulsion, styrene-butadiene latex, etc.) may be added.
  • a hydrophobic polymer for example, an acrylic resin emulsion, styrene-butadiene latex, etc.
  • the viscosity modifier used in the composition is preferably a component having good transparency from the viewpoint of hardly affecting the appearance.
  • a viscosity modifier with favorable transparency polyvinyl alcohol (PVA) is preferable and modified PVA, such as carboxy modified polyvinyl alcohol or alkyl ether modified polyvinyl alcohol, is more preferable.
  • the content of the viscosity modifier in the composition may be selected according to the purpose. Usually, 5% by mass to 30% by mass is preferable, and 10% by mass to 20% by mass is more preferable with respect to the total solid content of the composition.
  • composition of the present disclosure can contain the dispersion medium described above and other components other than the viscosity modifier.
  • other components include stabilizers, colorants, surfactants, crosslinking agents, lubricants, ultraviolet light absorbers, antioxidants, and antistatic agents.
  • the composition of the present disclosure can further contain a colorant.
  • the coloring material can be contained outside the microcapsule separately from the coloring material as the inclusion component of the microcapsule described above.
  • the content of the colorant relative to the total solid content of the composition is preferably 0.001% by mass to 0.5% by mass, and 0.005% by mass to 0.2% by mass. More preferable.
  • a desired hue can be given to a composition in content of a color material in the said range.
  • compositions of the present disclosure can be used in a variety of applications.
  • the composition may include, for example, a softener for clothes, a detergent for clothes, a cosmetic, a cosmetic sheet, and the like that can impart a cool feeling to the skin if desired.
  • the composition of the present disclosure can be made into a fabric softener by further including a cationic surfactant.
  • the composition which is a softener for clothes according to the present disclosure is such that the cationic surfactant and the microcapsules contained in the composition are adsorbed to the fibers of the clothes by immersing the clothes in the composition, dehydrating and drying the clothes. , Into fine gaps between fibers and held in clothing. For this reason, softening, antistatic properties, and the like are imparted to the clothes, and further, by including the microcapsules containing the specific cooling sensation component, it is possible to provide the skin with the cooling sensation at a desired time.
  • the specified coolness component is stably contained in the microcapsule in addition to the soft comfort, so the clothing is rubbed even after aging, etc.
  • the specific cooling sensation component can be brought into contact with the skin to give a cooling sensation.
  • the microcapsules are gradually disintegrated and a cold sensation is gradually given to the skin.
  • the softener for clothes it is preferable that 0.3% by mass to 3% by mass of the microcapsule and 10% by mass to 30% by mass of the cationic surfactant be contained in the total amount of the composition.
  • known components contained in a fabric softener such as antifoaming agents, coloring materials, perfumes and the like can be further included.
  • water such as ion exchange water is preferable.
  • the composition of the present disclosure further includes at least one surfactant selected from the group consisting of an anionic surfactant, a nonionic surfactant and an amphoteric surfactant, thereby forming a laundry detergent. be able to.
  • the composition which is the laundry detergent of the present disclosure comprises at least one surfactant selected from the group consisting of an anionic surfactant, a nonionic surfactant and an amphoteric surfactant as a main component of the detergent.
  • the specified coolness component is stably contained in the microcapsules held between the fibers of the clothes, so the clothes are rubbed even after aging, etc.
  • the specific cooling sensation component can be brought into contact with the skin to give a cooling sensation.
  • the microcapsules are gradually disintegrated and a cold sensation is gradually given to the skin.
  • the cleaning agent for clothes it is preferable that 0.1% by mass to 10% by mass of microcapsules and 1% by mass to 30% by mass in total of surfactants are contained in the total amount of the composition.
  • known ingredients contained in the detergent for clothing such as brighteners, fatty acids, enzymes, bleaches, thickeners, pH adjusters, colorants, perfumes and the like can be further included.
  • water such as ion exchange water, is preferable.
  • the composition containing the microcapsule in the present disclosure and the dispersion medium of the microcapsule can be applied to the cosmetic as it is.
  • the cosmetic it can be optionally applied to liquid cosmetic such as lotion, creamy cosmetic, skin cosmetic such as skin cleanser, hair cosmetic such as hair restorer, hair cleanser (shampoo), etc. .
  • the composition of the present disclosure which is a cosmetic, can be stressed to cause the microcapsules in contact with the skin to disintegrate and give the skin a cooling sensation.
  • the microcapsules adhere to the hair and rub the hair, or when the hair is combed with a comb, etc., the microcapsules can be broken by stress to give a cool feeling to the scalp.
  • the microcapsules containing the specific cooling sensation component can be stably stored for a longer time by filling the spray container, which is preferable.
  • the cosmetic is applied to the skin or hair by spraying, the dispersion medium and the microcapsules adhere to the skin or hair. Then, by putting the skin with cotton or fingers, massaging the scalp, etc., the microcapsules are disintegrated by applying stress to the microcapsules, and the specific cooling sensation component adheres to the skin or scalp, resulting in a cooling sensation.
  • the composition of the present disclosure which is a cosmetic, can optionally contain known components that can be contained in the cosmetic. Examples of known components that may be contained in cosmetics include aqueous media such as alcohols, oils, surfactants as washing or dispersing components, active ingredients that penetrate the skin, coloring materials, perfumes, and the like.
  • the composition of the present disclosure can be made into a cosmetic sheet by including a support and a composition containing the dispersion medium of the present disclosure described above impregnated in the support.
  • the support is not particularly limited as long as it can hold a liquid component.
  • a fiber assembly having voids holding moisture inside, such as a non-woven fabric and a woven fabric, and a porous body such as a sponge sheet are preferable.
  • the microcapsule is disintegrated by pressing the support against the skin and rubbing it, giving the skin a cooling sensation due to the specific cooling sensation component at any time. be able to.
  • a cleansing sheet for skin cleansing can be obtained.
  • the cleansing sheet for skin cleansing is also one aspect of the cosmetic sheet in the present disclosure.
  • the cosmetic sheet is preferably packaged by a water-impermeable packaging material in order to keep the composition stable from the viewpoint of sustainability of the effect.
  • the microcapsules of the present disclosure and the composition containing the microcapsules can exhibit a cooling sensation effect at any time when necessary and can be applied to various uses.
  • the fabric softener for clothing, the cleaning agent for clothing, the cosmetics, the sheet for cosmetics, etc. which were already described are the examples, and are not limited to the said description.
  • the median diameter (D50) of the volume standard of microcapsules was measured using Microtrac MT3300EXII (manufactured by Nikkiso Co., Ltd.).
  • the number average wall thickness of the microcapsules is obtained by applying the microcapsule solution on polyethylene terephthalate (PET) having an undercoat layer and drying it to form a coated film in a plane parallel to the normal direction of the film surface.
  • PET polyethylene terephthalate
  • the wall thickness in the cross section of five microcapsules arbitrarily selected is measured by cutting the cross section to form a cross section and observing the formed cross section with a scanning electron microscope (SEM), and calculating the average value I asked for it.
  • SEM scanning electron microscope
  • Example 1 Preparation of microcapsule (A) dispersion- In 7 parts of Coconad (registered trademark) MT (Kao Co., Ltd.), 17 parts of R carbon which is a specific cooling sensation component and 4.3 parts of R limonene which is a fragrance were dissolved to obtain a solution A.
  • solution B was obtained.
  • step (I) the above solution B was added to a solution of 3.5 parts of polyvinyl alcohol (PVA-217E, Kuraray Co., Ltd.) dissolved in 57 parts of water, and the mixture was emulsified and dispersed (step (I)). 65 parts of water was added to the emulsion obtained by the emulsification and dispersion, and the mixture was heated to 70 ° C. with stirring, and stirring was continued for 1 hour while maintaining the temperature, and then cooled.
  • PVA-217E polyvinyl alcohol
  • microcapsules (A) in which R-carvone, which is a specific cooling sensation component, is encapsulated in the capsule wall of polyurethaneurea are solidified. A dispersion containing 30% concentration was obtained.
  • Example 2 In Example 1, the content of the trimethylolpropane adduct of tolylene diisocyanate used for preparation of the solution B (DIC Corporation, Burnock D-750) was changed from 1.7 parts to 3.4 parts. A dispersion containing microcapsules (B) was obtained in the same manner as in Example 1 except for the above.
  • Example 3 In Example 1, the content of the trimethylolpropane adduct of tolylene diisocyanate used for preparation of the solution B (DIC Corp., Burnock D-750) was changed from 1.7 parts to 10.2 parts. A dispersion containing microcapsules (C) was obtained in the same manner as in Example 1 except for the above.
  • Example 4 A dispersion liquid containing microcapsules (D) was prepared in the same manner as in Example 1 except that 17 parts of R-carbon, which is the specific cooling sensation component used in preparation of solution A, was changed to 17 parts of camphor. Obtained.
  • Example 5 In Example 1, 7 parts of menthyl glyceryl ether which is a component for maintaining cold feeling is used in place of 7 parts of Coconad MT (Kao Co., Ltd.) used for preparation of solution A, and 17 parts of R carbon which is a specific component A dispersion containing microcapsules (E) was obtained in the same manner as in Example 1 except that 17 parts of 1-menton was used.
  • Example 6 In Example 1, 7 parts of menthyl glyceryl ether as a cooling sensation maintenance component are used using 7 parts of menthyl lactate as a cooling sensation maintenance component instead of 7 parts of Coconade MT (Kao Co., Ltd.) used for preparation of solution A.
  • a dispersion liquid containing microcapsules (F) was obtained in the same manner as in Example 1 except that 17 parts of R-carbon, which is the specific cooling sensation component, was replaced with 17 parts of 1-mentone using.
  • Example 7 Dispersion including microcapsules (G) in the same manner as in Example 1 except that 17 parts of R-carbon, which is a specific cooling sensation component used in preparation of solution A, was replaced with 17 parts of 1-mentone. I got a liquid.
  • Example 8 Dispersion containing microcapsules (H) in the same manner as in Example 1 except that 17 parts of R-carbon, which is the specific cooling sensation component used in preparation of solution A, was replaced with 17 parts of menthyl acetate. I got
  • Example 9 A microcapsule (I) was prepared in the same manner as in Example 1 except that 17 parts of R-carbon, which is a specific cooling sensation component used in preparation of solution A, was replaced with 17 parts of 1,8-cineole. The resulting dispersion was obtained.
  • Example 10 (Melamine formaldehyde wall capsule) 200 parts of 25 parts of butyl acrylate-acrylic acid copolymer (Colloid C 351 as an emulsifier (trade name: solid content 25%, pka: 4.5 to 4.7, manufactured by Kemira Chemicals, Inc.) 25 parts) It was dissolved in water to obtain a mixed solution. The pH of the resulting mixture was adjusted to 4.0 with sodium hydroxide solution. A mixed solution A was obtained by adding 8 parts of a partially methylated methylolmelamine resin (Cymel 385: trade name, solid content 80%, manufactured by Cytec Industries) to the mixed solution whose pH was adjusted.
  • a partially methylated methylolmelamine resin (Cymel 385: trade name, solid content 80%, manufactured by Cytec Industries)
  • Liquid mixture C is 10 parts of butyl acrylate-acrylic acid copolymer (emulsifier, Colloid C 351: trade name, solid content 25%, pka: 4.5 to 4.7, manufactured by Kemira Chemicals, Inc.), distilled water It contains 120 g, a sodium hydroxide solution for adjusting pH to 4.8, and 25 parts of a partially methylated methylolmelamine resin (Cymel 385: trade name, 80% solids, manufactured by Cytec Industries).
  • emulsifier Colloid C 351: trade name, solid content 25%, pka: 4.5 to 4.7, manufactured by Kemira Chemicals, Inc.
  • distilled water It contains 120 g, a sodium hydroxide solution for adjusting pH to 4.8, and 25 parts of a partially methylated methylolmelamine resin (Cymel 385: trade name, 80% solids, manufactured by Cytec Industries).
  • the emulsion containing mixture C and sodium sulfate was heated to 70 ° C. and allowed to stand overnight with continuous stirring while maintaining the temperature to complete the encapsulation. 23 parts of acetoacetamide (Sigma Aldrich) was added to the suspension for which encapsulation was completed to obtain a dispersion containing microcapsules (J).
  • Example 1 The same operation as in Example 1 was carried out except that in Example 1, 17 parts of R-carbon, which is the specific cooling sensation component used in preparation of solution A, was replaced with 17 parts of 1-menthol, which is the comparative cooling sensation component. However, no wall material was formed, and microcapsules were not obtained.
  • the resulting white slurry was allowed to stand overnight at room temperature (25 ° C.), and this was spray-dried to obtain white powdery l-menthol inclusion ⁇ -cyclodextrin, which was used as comparative particles. It is considered that all l-menthol is included in cyclodextrin because the resulting powder does not show any specific odor of l-menthol.
  • Example 3 The same operation as in Example 10 was carried out except that in Example 10, 17 parts of R-carbon, which is the specific cooling sensation component used in preparation of solution A, was replaced with 17 parts of 1-menthol, which is the comparative cooling sensation component. However, no wall material was formed, and microcapsules were not obtained.
  • a liquid composition containing 0.5% of (6PO) 0.5%, the microcapsules of any of Examples 1-10 or Comparative Example 2 or 2% as a solid content and the balance purified water was prepared. 3 g of the obtained liquid composition was impregnated into 1 g of a 10 cm square non-woven fabric (trade name: RH, manufactured by Daiwabo Polytech) to obtain a cleaning sheet for skin wiping as a sample.
  • the cleaning sheet for skin cleansing may be referred to as a "cleaning sheet”.
  • the microcapsule of the present disclosure can stably hold a cooling sensation component as an inclusion component, and can exhibit a cooling sensation effect at a desired time, and can be applied to various uses. Furthermore, the compositions of the present disclosure, including the microcapsules of the present disclosure, can be applied to various applications as well. Specifically, it is used for applications such as cleaning agents for clothing, softeners for clothing, skin cosmetics, cosmetics such as hair cosmetics, cleaning sheets for skin cleaning, and cosmetic sheets such as cold feeling sheets. It is suitable.

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Abstract

L'invention concerne une microcapsule comprenant : une paroi de capsule contenant au moins un élément choisi dans le groupe constitué des résines d'uréthane, des résines d'urée, des résines acryliques et des résines de mélamine; et un composant à sensation de fraîcheur qui est un composant encapsulé et ne contient pas de groupe hydroxyle. L'invention concerne également une application des microcapsules.
PCT/JP2018/030452 2017-08-21 2018-08-16 Microcapsule, composition et film pour cosmétiques WO2019039385A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113329812A (zh) * 2019-05-21 2021-08-31 弗门尼舍有限公司 制备微胶囊的方法
CN115627641A (zh) * 2022-09-26 2023-01-20 黛思(常州)无纺布有限公司 一种持久性口罩凉感剂及其制备方法

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