WO2019181668A1 - Composition contenant des microcapsules, composition de lessive, composition de soins de jour et composition de soins capillaires - Google Patents

Composition contenant des microcapsules, composition de lessive, composition de soins de jour et composition de soins capillaires Download PDF

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Publication number
WO2019181668A1
WO2019181668A1 PCT/JP2019/010130 JP2019010130W WO2019181668A1 WO 2019181668 A1 WO2019181668 A1 WO 2019181668A1 JP 2019010130 W JP2019010130 W JP 2019010130W WO 2019181668 A1 WO2019181668 A1 WO 2019181668A1
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Prior art keywords
microcapsule
mass
shell
structure derived
isocyanate compound
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PCT/JP2019/010130
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English (en)
Japanese (ja)
Inventor
田中　智史
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富士フイルム株式会社
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Publication of WO2019181668A1 publication Critical patent/WO2019181668A1/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
    • 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
    • A61K8/72—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
    • A61Q13/00—Formulations or additives for perfume preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • 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
    • 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
    • C11D3/50—Perfumes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers

Definitions

  • the present disclosure relates to a microcapsule-containing composition, a laundry composition, a day care composition, and a hair care composition.
  • microcapsules have added new value to customers by including and protecting functional materials such as fragrances, dyes, heat storage materials, and pharmaceutical ingredients, and releasing functional materials in response to stimuli. It is attracting attention because there is a possibility that it can be provided.
  • the shell material used in perfume microcapsules is mainly a reaction product of aldehyde and amine (for example, melamine formaldehyde resin).
  • Patent Document 1 uses a resin containing a fragrance as a core material and a wall material (shell material) containing a reaction product of an aldehyde (for example, formaldehyde) and an amine (for example, melamine). Microcapsules that have been described are described.
  • Patent Document 2 describes a polyurea microcapsule including a polyurea wall (polyurea wall) containing a reaction product of polymerization of polyisocyanate and polyamine, and a fragrance encapsulated in the polyurea wall.
  • the microcapsules as described above use pressure responsiveness to release the encapsulated component to the outside, for example, when used as a perfume microcapsule, the capsule breaks due to pressure being applied to the clothing.
  • the fragrance by the fragrance is diffused. Therefore, in the state where no pressure is applied to the capsule, the fragrance is held in the capsule and cannot be continuously obtained.
  • the problem to be solved by one embodiment of the present invention is to provide a microcapsule-containing composition by forming microcapsules having sustained release properties and high breaking strength.
  • a microcapsule-containing composition comprising a microcapsule having a shell and a core containing a fragrance, i) from a structure derived from a bifunctional aliphatic isocyanate compound and a structure derived from a bifunctional aromatic isocyanate compound Microcapsule-containing composition having at least one selected structure of 10% by mass to 70% by mass with respect to the total mass of the shell material forming the shell, and ii) the thickness of the shell is 0.3 to 2.0 ⁇ m object.
  • microcapsule-containing composition according to ⁇ 1> or ⁇ 2>, wherein the shell material contains at least one of polyurethane and polyurea or melamine formaldehyde resin.
  • the shell material includes at least one of polyurethane and polyurea having a structure derived from a polyisocyanate compound.
  • ⁇ 5> At least one structure selected from a structure derived from a trifunctional or higher functional aliphatic isocyanate compound, a structure derived from a bifunctional aliphatic isocyanate compound, and a structure derived from a bifunctional aromatic isocyanate compound;
  • ⁇ 4> The microcapsule-containing composition according to ⁇ 4>, comprising polyurethane or polyurea.
  • the shell material has a structure derived from a melamine formaldehyde prepolymer compound, a structure derived from a bifunctional aliphatic isocyanate compound, and at least one structure selected from a structure derived from a bifunctional aromatic isocyanate compound.
  • a laundry composition, day care composition or hair care composition comprising the microcapsule-containing composition according to any one of ⁇ 1> to ⁇ 7>.
  • a microcapsule-containing composition having sustained release properties is provided by forming microcapsules having sustained release properties and high breaking strength.
  • microcapsule-containing composition of the present disclosure will be described in detail.
  • a numerical range indicated using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value, respectively.
  • an upper limit value or a lower limit value described in a numerical range may be replaced with an upper limit value or a lower limit value in another numerical range.
  • the upper limit value or the lower limit value described in a certain numerical range may be replaced with the values shown in the examples.
  • shell refers to a wall of a microcapsule
  • core refers to a portion enclosed in the shell.
  • a material for forming the shell is referred to as “shell material”.
  • the components contained in the core are collectively referred to as “core material”.
  • the “encapsulation” refers to a state in which an object is covered and confined by the shell of the microcapsule.
  • the microcapsule-containing composition of the present disclosure includes a microcapsule having sustained release properties and high breaking strength.
  • the microcapsule has a shell and a core containing a fragrance.
  • the inventor of the present invention pays particular attention to the characteristics of the shell material of the microcapsule, and includes a fragrance as a core material, and i) a structure derived from a bifunctional aliphatic isocyanate compound and a bifunctional aromatic isocyanate compound
  • a microcapsule having at least one structure selected from the structures derived from (ii) having a mass of 10 to 70% by mass with respect to the total mass of the shell material and having a shell thickness of 0.3 to 2.0 ⁇ m.
  • the microcapsule in the present disclosure has a core and a shell enclosing the core, and i) at least selected from a structure derived from a bifunctional aliphatic isocyanate compound and a structure derived from a bifunctional aromatic isocyanate compound.
  • One structure has 10% by mass to 70% by mass with respect to the total mass of the shell material, and ii) the thickness of the shell is 0.3 to 2.0 ⁇ m.
  • the microcapsules in the present disclosure preferably have a breaking strength of 16 MPa or more. Accordingly, the microcapsules can be uniformly adhered to the fibers without being broken even in various processes during washing, particularly in the dehydration process. From the same viewpoint as described above, the breaking strength of the microcapsule is more preferably 18 to 35 MPa, and particularly preferably 20 to 30 MPa.
  • the breaking strength of the microcapsule can be measured by the following method.
  • the aqueous microcapsule dispersion was diluted 1000 times with water, dropped by 0.1 cc onto the slide glass, dried, and the breaking strength of the microcapsule having a diameter of about 20 ⁇ m on the slide glass was measured.
  • a microhardness meter DUH-W201 manufactured by Shimadzu Corporation was used, and the size of the microcapsule was confirmed and measured using an attached microscope.
  • a 50 ⁇ m planar indenter was used as the indenter. The destructive force of microcapsules is described in Zhang, Z. et al.
  • the microcapsules in the present disclosure have sustained release properties. Sustained release is a property in which a slight fragrance is obtained even when the core fragrance does not break the microcapsules and the fragrance is maintained for a long time. In the present disclosure, it is determined that the microcapsule has a sustained release property if the amount of the fragrance decreased after 48 hours at 25 ° C. of the cotton towel obtained by the following process is 5 to 30% by mass.
  • the fragrance reduction amount is 5% by mass or more, the released fragrance can be sufficiently felt, and when it is 30% by mass or less, the fragrance can be maintained for a long time.
  • the fragrance reduction amount is more preferably 8 to 25% by mass, and particularly preferably 10 to 20% by mass.
  • decrease amount can be measured by the method as described in sustained release evaluation by the fragrance
  • the microcapsule in the present disclosure has a shell that encloses a core.
  • the shell material forming the shell in the present disclosure preferably has at least one of polyurethane and polyurea having a structure derived from a polyisocyanate compound, or a melamine formaldehyde resin having a structure derived from a melamine formaldehyde prepolymer compound.
  • the microcapsule of the present disclosure includes a shell for enclosing the core material, and preferably includes polyurethane or polyurea as the shell material forming the shell.
  • the polyurethane and polyurea contained in the shell will be described in detail.
  • the polyurethane and polyurea in the present disclosure preferably have a structure derived from polyisocyanate from the viewpoint of storage stability. That is, the polyurethane and polyurea in the present disclosure are preferably polymers obtained using polyisocyanate from the viewpoint of storage stability. That is, the polyurethane and the polyurea preferably have a structure derived from an isocyanate compound.
  • the structure derived from the isocyanate compound includes a structure derived from a tri- or higher functional aliphatic isocyanate compound and a bifunctional aliphatic isocyanate compound. It is preferably at least one structure selected from a structure derived from a structure derived from a bifunctional aromatic isocyanate compound.
  • the polyurethane or polyurea in the present disclosure includes polyurethane polyurea.
  • polyurethane polyurea is more preferable.
  • the polyurethane, polyurea and polyurethane polyurea preferably have at least one structure selected from a structure derived from a bifunctional aliphatic isocyanate compound and a structure derived from a bifunctional aromatic isocyanate compound.
  • the shell in the present disclosure has a sustained release property by using a bifunctional isocyanate compound in the formation of polyurethane or polyurea.
  • bifunctional aliphatic isocyanate compound and the bifunctional aromatic isocyanate compound may be collectively referred to as “specific diisocyanate”.
  • the polyurethane or polyurea that is a shell material forming the shell is at least one selected from a structure derived from a specific diisocyanate, that is, a structure derived from a bifunctional aliphatic isocyanate compound and a structure derived from a bifunctional aromatic isocyanate compound. It is preferable to have the following structure.
  • the structure derived from a bifunctional aliphatic isocyanate compound refers to a structure formed by a urethane reaction or a urea reaction of a bifunctional aliphatic isocyanate.
  • the structure derived from a bifunctional aromatic isocyanate compound refers to a structure formed by the reaction of urethane or urea with a bifunctional aromatic isocyanate.
  • bifunctional aliphatic isocyanate compound examples include trimethylene diisocyanate, hexamethylene diisocyanate, propylene-1,2-diisocyanate, butylene-1,2-diisocyanate, cyclohexylene-1,2-diisocyanate, cyclohexylene-1, 3-diisocyanate, cyclohexylene-1,4-diisocyanate, dicyclohexylmethane-4,4′-diisocyanate, 1,4-bis (isocyanatemethyl) cyclohexane and 1,3-bis (isocyanatemethyl) cyclohexane, isophorone diisocyanate, lysine diisocyanate And hydrogenated xylylene diisocyanate.
  • bifunctional aromatic isocyanate compound examples include 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-chloroxyl Len-1,3-diisocyanate, 2-methylxylylene-1,3-diisocyanate, 4,4'-diphenylpropane diisocyanate, 4,4'-diphenylhexafluoropropane diisocyanate, etc. It is.
  • Isocyanate compounds are described in “Polyurethane Resin Handbook” (edited by Keiji Iwata, published by Nikkan Kogyo Shimbun (1987)).
  • the total mass ratio is preferably 10% by mass to 70% by mass, more preferably 10% by mass to 65% by mass, and still more preferably 12% by mass to 60% by mass.
  • the proportion of the structure derived from the specific diisocyanate is 10% by mass or more, the crosslinking density of the shell is lowered, and the sustained release property of the core material to be included can be enhanced.
  • the proportion of the structure derived from the specific diisocyanate is 70% by mass or less, and further 60% by mass or less, the flexibility of the shell can be easily maintained, and, for example, adhesion to fibers or hairs can be favorably maintained.
  • the polyurethane or polyurea which is a shell material forming the shell preferably has a structure derived from a tri- or higher functional aliphatic isocyanate compound.
  • a structure derived from a trifunctional or higher functional aliphatic isocyanate compound By having a structure derived from a trifunctional or higher functional aliphatic isocyanate compound, the flexibility and breaking strength of the shell can be increased, and adhesion to an object to be adhered such as fiber or hair can be obtained.
  • the structure derived from a trifunctional or higher functional aliphatic isocyanate compound refers to a structure formed by a urethane reaction or a urea reaction of a trifunctional or higher functional aliphatic isocyanate compound.
  • Examples of the trifunctional or higher functional aliphatic isocyanate compound include a bifunctional aliphatic isocyanate compound (a compound having two isocyanate groups in the molecule) and a compound having three or more active hydrogen groups in the molecule (for example, a trifunctional or higher functional group).
  • adduct adduct with a polyol, polyamine, polythiol, etc.
  • a trifunctional or higher functional isocyanate compound adduct type
  • a bifunctional aliphatic isocyanate compound trimer (biuret type or isocyanurate type) Can do.
  • a commercially available product may be used as the adduct type trifunctional or higher functional isocyanate compound.
  • HT manufactured by Bayer Corporation
  • Coronate registered trademark
  • HX manufactured by Tosoh Corporation
  • Duranate P301-75E manufactured by Asahi Kasei Co., Ltd.
  • Barnock registered trademark
  • Takenate (registered trademark) series for example, Takenate D-110N, D-120N, D-140N, D-160N, etc.
  • DIC stock More preferable is at least one selected from Vernock (registered trademark) D-750 manufactured by the company.
  • isocyanurate-type trifunctional or higher functional isocyanate compound a commercially available product may be used.
  • examples of commercially available products include Takenate (registered trademark) D-127N, D-170N, D-170HN, D-172N, D-177N (manufactured by Mitsui Chemicals), Sumidur N3300, Death Module (registered trademark) N3600.
  • biuret type trifunctional or higher functional isocyanate compound commercially available products may be used.
  • D-165N Takenate (registered trademark) D-165N, NP1200 (manufactured by Mitsui Chemicals), Desmodur (registered trademark) N3200A (Manufactured by Bayer Corporation), Duranate (registered trademark) 24A-100, 22A-75P (manufactured by Asahi Kasei Corporation) and the like.
  • the ratio of the structure derived from the trifunctional or higher aliphatic isocyanate compound to the total mass of the shell material is preferably 20% by mass to 95% by mass, and more preferably 20% by mass to 90% by mass.
  • the content is preferably 35% by mass to 80% by mass.
  • the proportion of the structure derived from the tri- or higher functional aliphatic isocyanate compound is 20% by mass or more, the shell can be provided with good flexibility and breaking strength.
  • the ratio of the structure derived from the trifunctional or higher aliphatic isocyanate compound is 95% by mass or less, it is suitable for maintaining the sustained release property to the outside of the core material.
  • the ratio of the trifunctional aliphatic isocyanate compound to the specific diisocyanate is preferably from 95/5 to 20/80, more preferably from 90/10 to 30/70, and more preferably from 90/10 to 90/10. More preferably, it is 40/60. When the ratio of the trifunctional aliphatic isocyanate compound to the specific diisocyanate is within the above range, the sustained release property of the core material is excellent.
  • Polyurethane or polyurea which is a shell material that forms a shell, may have a structure derived from other isocyanate compounds in addition to the trifunctional aliphatic isocyanate compound and the specific diisocyanate.
  • the structure derived from another isocyanate compound refers to a structure formed by the urethane reaction or urea reaction of another isocyanate compound.
  • Examples of other isocyanate compounds include trifunctional or higher functional aromatic isocyanate compounds.
  • trifunctional or higher functional aromatic isocyanate compound examples include 2,6-tolylene diisocyanate, 2,4-tolylene diisocyanate, or an adduct (adduct) of hexamethylene diisocyanate and trimethylolpropane, biuret or isocyanate. A nurate body etc. are mentioned. Commercially available products marketed as trifunctional or higher functional aromatic isocyanate compounds may be used.
  • Examples of commercially available products include Barnock (registered trademark) D-750 (manufactured by DIC Corporation), Takenate (registered trademark) D- 102, D-103, D-103H, D-103M2, D-110N, Olester (registered trademark) P49-75S (above, manufactured by Mitsui Chemicals, Inc.), Death Module (registered trademark) L75, IL-135-BA , HL-BA, Sumijoule (registered trademark) E-21-1 (manufactured by Bayer Co., Ltd.), Coronate (registered trademark) L, L-55, L-55E (manufactured by Tosoh Corporation), Bernock (registered trademark) D -750, D-800 (manufactured by DIC Corporation) and the like.
  • Barnock registered trademark
  • D-750 manufactured by DIC Corporation
  • Takenate D- 102, D-103, D-103H, D-103M2, D-110N
  • the microcapsule of the present disclosure preferably includes a shell for enclosing the core material, and preferably includes a melamine formaldehyde resin as the shell material forming the shell.
  • the melamine formaldehyde resin contained in the shell will be described in detail.
  • the melamine formaldehyde resin in the present disclosure preferably has a structure derived from a melamine formaldehyde prepolymer compound from the viewpoint of storage stability. That is, the melamine formaldehyde resin in the present disclosure is preferably a polymer obtained using a melamine formaldehyde prepolymer compound from the viewpoint of storage stability.
  • the melamine formaldehyde resin in the present disclosure also includes an aminoplast resin in which a melamine formaldehyde prepolymer compound and a polyisocyanate are crosslinked.
  • the melamine formaldehyde resin is at least one structure selected from a structure derived from a melamine formaldehyde prepolymer, a structure derived from a bifunctional aliphatic isocyanate compound, and a structure derived from a bifunctional aromatic isocyanate compound; It is preferable to have.
  • the shell in the present disclosure has a sustained release property by using a melamine formaldehyde prepolymer compound and a bifunctional isocyanate compound.
  • the difunctional isocyanate compound those described in the above-mentioned “specific diisocyanate” can be used as appropriate.
  • the melamine formaldehyde resin which is a shell material that forms a shell, preferably has a structure derived from a melamine formaldehyde prepolymer compound.
  • the melamine formaldehyde prepolymer compound is an initial polymer obtained by reacting melamine and formaldehyde, and it is preferable to use the melamine formaldehyde prepolymer compound from the viewpoint of handling when forming the shell of the microcapsule.
  • the melamine formaldehyde prepolymer compound can be produced from melamine and formaldehyde according to a conventional method. Moreover, what is marketed can be used suitably as a melamine formaldehyde prepolymer compound.
  • a melamine formaldehyde prepolymer compound for example, becamine APM, becamine M-3, becamine M-3 (60), becamine MA-S, becamine J-101, becamine J-101LF (manufactured by DIC Corporation), nicalesin S-176, nicalesin S-260 ( As mentioned above, Nippon Carbide Co., Ltd.) etc. are mentioned.
  • the ratio of the melamine formaldehyde prepolymer compound to the specific diisocyanate is preferably 95/5 to 20/80, more preferably 90/10 to 30/70, more preferably 90/10 to 40 / More preferably, it is 60.
  • the core material has excellent sustained release properties.
  • the thickness (wall thickness) of the shell (wall) of the microcapsule of the present disclosure is in the range of 0.3 ⁇ m to 2.0 ⁇ m.
  • the wall thickness of the microcapsule is 0.3 ⁇ m or more, the microcapsule can be prevented from cracking in the washing process, particularly the dehydration process, and the core material can be protected in the core.
  • the wall thickness of the microcapsule is 2.0 ⁇ m or less, the microcapsule can be provided with sustained release, and the scent can be released from the microcapsule attached to the fiber.
  • the wall thickness of the microcapsule is more preferably 0.4 ⁇ m to 1.7 ⁇ m, and still more preferably 0.4 ⁇ m to 1.5 ⁇ m.
  • the wall thickness refers to an average value obtained by averaging the individual wall thicknesses ( ⁇ m) of five microcapsules with a scanning electron microscope (SEM). Specifically, a microcapsule solution is applied on an arbitrary support and dried to form a coating film. A cross section of the obtained coating film is prepared, the cross section is observed using an SEM, arbitrary five microcapsules are selected, the cross section of each of the microcapsules is observed, and the wall thickness is measured. And calculating the average value.
  • SEM scanning electron microscope
  • the median diameter (D50) of the volume standard of the microcapsules is preferably 0.1 ⁇ m to 100 ⁇ m.
  • the volume standard median diameter (D50) of the microcapsules is more preferably 1 ⁇ m to 70 ⁇ m, and still more preferably 5 ⁇ m to 50 ⁇ m.
  • the volume standard median diameter of the microcapsules can be preferably controlled by changing dispersion conditions.
  • the median diameter of the volume standard of the microcapsule is the volume of the particle on the large diameter side and the small diameter side when the entire microcapsule is divided into two with the particle diameter at which the cumulative volume is 50% as a threshold value.
  • the diameter is the same as the total.
  • the median diameter of the volume standard of the microcapsule is measured using Microtrac MT3300EXII (manufactured by Nikkiso Co., Ltd.).
  • the level of monodispersity of the microcapsules can be expressed using a CV value (coefficient of variation).
  • the CV value is a value obtained by the following formula.
  • CV value (%) (standard deviation / volume average particle diameter) ⁇ 100 The lower the CV value, the higher the monodispersity of the microcapsules, and the higher the CV value, the lower the monodispersibility of the microcapsules.
  • the volume average particle diameter and the standard deviation are calculated using Microtrac MT3300EXII (manufactured by Nikkiso Co., Ltd.).
  • “highly monodispersed” of the microcapsule means that the CV value of the particle size distribution of the microcapsule is preferably 40% or less, more preferably 35% or less, still more preferably 30% or less, particularly preferably. It means 25% or less.
  • the lower limit of the CV value of the particle size distribution of the microcapsules is not limited, but is preferably 0% or more, and more preferably 5% or more.
  • the form of the microcapsule may be, for example, a microcapsule dispersion, preferably a microcapsule aqueous dispersion.
  • the microcapsule in the present disclosure preferably has a core encapsulated in a shell and includes a fragrance as a core material in the core.
  • the microcapsule according to the present disclosure adheres to clothes fibers or hair (hair etc.) without being destroyed even after a washing process, particularly a dehydration process, and includes a fragrance as a core material, thereby providing sustained release. It can be scented for a long time.
  • fragrance As the fragrance, synthetic fragrances, natural essential oils, and natural fragrances described in “Japan Patent Office, Well-known and commonly used technology (fragrance) Part III, cosmetic fragrances, pages 49-103, issued on June 15, 2001” Appropriate ones can be selected and used from animal and plant extracts.
  • fragrances include monoterpenes such as D-limonene, pinene, myrcene, camphene and R-limonene, sesquiterpenes such as cedrene, caryophyllene and longifolene, 1,3,5-undecatriene, ⁇ -amylcinnamyl aldehyde Synthetic fragrances such as dihydrojasmon, methylionone, ⁇ -damascone, acetyl cedrene, methyl dihydrojasmonate, cyclopentadecanolide, and natural essential oils such as orange essential oil, lemon essential oil, bergamot essential oil, and mandarin essential oil.
  • the content of the fragrance with respect to the total mass of the core material is preferably 20 to 100% by mass, more preferably 30 to 95% by mass, and particularly preferably 40 to 85% by mass.
  • the core may contain a solvent as an oil component.
  • the solvent include fatty acid ester compounds such as tri (capryl / capric acid) glyceryl and isopropyl myristate, alkylnaphthalene compounds such as diisopropylnaphthalene, diarylalkane compounds such as 1-phenyl-1-xylylethane, isopropylbiphenyl, and the like.
  • Aromatic hydrocarbons such as alkylbiphenyl compounds such as triarylmethane compounds, alkylbenzene compounds, benzylnaphthalene compounds, diarylalkylene compounds, arylindane compounds; aliphatic hydrocarbons such as dibutyl phthalate and isoparaffins; Examples include camellia oil, soybean oil, corn oil, cottonseed oil, rapeseed oil, natural animal and vegetable oils such as olive oil, coconut oil, castor oil, and fish oil; high-boiling fractions of natural products such as mineral oil.
  • the content of the solvent in the encapsulated component is preferably less than 50% by mass, more preferably 40% by mass or less, and particularly preferably 30% by mass or less with respect to the total mass of the encapsulated component.
  • the encapsulated component may contain an auxiliary solvent as an oil phase component for enhancing the solubility of each material in the oil phase when producing the microcapsules, if necessary.
  • the auxiliary solvent does not include the above solvent.
  • 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 auxiliary solvent has a boiling point of 130 ° C or lower.
  • the content of the auxiliary solvent in the encapsulated component is preferably less than 50% by mass, more preferably less than 40% by mass, and even more preferably less than 30% by mass with respect to the total mass of the encapsulated component.
  • additives such as ultraviolet absorbers, light stabilizers, antioxidants, waxes, odor inhibitors and the like can be included in the microcapsules as necessary.
  • the additive can be contained, for example, in an amount of 0% by mass to 20% by mass, preferably 1% by mass to 15% by mass, and more preferably 5% by mass to 10% by mass with respect to the total mass of the core.
  • the microcapsule-containing composition of the present disclosure preferably further contains a microcapsule dispersion medium.
  • a microcapsule dispersion medium By further containing a microcapsule dispersion medium, the microcapsule-containing composition can be easily blended when used in various applications.
  • the dispersion medium in the microcapsule-containing 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 microcapsule.
  • Preferred dispersion media include aqueous solvents, viscosity modifiers, stabilizers, and the like. Examples of the aqueous solvent include water, water, alcohol and the like, and ion-exchanged water or the like can be used.
  • what is necessary is just to select suitably content of the dispersion medium in the microcapsule containing composition of this indication according to a use.
  • the microcapsule-containing composition of the present disclosure can further contain other components in addition to the microcapsule and the dispersion medium that is a combination component.
  • other components include a surfactant, a crosslinking agent, a lubricant, an ultraviolet absorber, an antioxidant, and an antistatic agent.
  • the microcapsule-containing composition of the present disclosure preferably has an embodiment in which the microcapsule has an anionic charge on the surface and further contains a cationic surfactant. Thereby, an interaction is obtained between the microcapsule and the cationic surfactant, and a positive charge of the cationic surfactant can be imparted around the microcapsule. As a result, it becomes possible to improve the adhesion property of the microcapsule to an attachment object (for example, hair or fiber) having an anionic charge.
  • an attachment object for example, hair or fiber
  • the microcapsule has an anionic charge on the surface by measuring the zeta potential when the microcapsule is dispersed in water. When the zeta potential is negative, it indicates that the surface of the microcapsule is covered with an anionic charge.
  • the zeta potential of the microcapsule when dispersed in water, is preferably ⁇ 80 meV to ⁇ 5 meV, more preferably ⁇ 80 meV to ⁇ 11 meV, and further preferably ⁇ 50 meV to ⁇ 10 meV. preferable.
  • Zero potential (z) means the apparent electrostatic potential generated by a charged object in solution, measured by a special measurement technique.
  • a detailed discussion of the logical basis and actual relevance of the zeta potential is, for example, “Colloid Science: Zeta Potential in Colloid Sciences: Principles and Applications” (Hunter Robert J. 1981; p 1988).
  • the zeta potential of an object is measured at some distance from the surface of the object and generally does not exceed the electrostatic potential at the surface itself. However, the value can be a good measure of the ability of an object to establish an electrostatic interaction with other objects in solution, particularly molecules having multiple binding sites.
  • the zeta potential is a relative measurement value, and the value tends to depend on the measurement method.
  • the zeta potential is a value measured by the following method.
  • the apparatus uses ELSZ-2000ZS (manufactured by Otsuka Electronics Co., Ltd.).
  • the device settings are as follows.
  • the sample preparation procedure is as follows.
  • the slurry containing the target capsule is added to water so that the capsule concentration is 0.5% by mass, and the slurry is diluted.
  • the measurement concentration is adjusted as necessary so that the measurement rate falls within a preferable range by automatic detection.
  • the zeta potential of the diluted sample is measured without filtering the sample.
  • the filtered slurry is poured into a standard cell unit (manufactured by Otsuka Electronics Co., Ltd.), and the cell is inserted into the apparatus. Set the test temperature to 25 ° C. (Iv) Start the measurement after the temperature has stabilized (usually after 3 to 5 minutes). Each sample is set to measure 5 times and measured. d.
  • the zeta potential in the present disclosure is a value measured in units of “mV” as an average of three measured values for each slurry. Based on the above, the zeta potential of the microcapsule can be measured using ELSZ-2000ZS (manufactured by Otsuka Electronics Co., Ltd.).
  • the method for imparting an anionic charge to the microcapsule surface is not particularly limited, for example, a method for binding an anionic group-imparting agent to the shell, a method for imparting an anionic charge to the microcapsule surface using a surface anionizing agent, etc. Is mentioned. Among these, from the viewpoint of work efficiency, a method of imparting an anionic charge to the microcapsule surface using a surface anionizing agent is preferable.
  • an oil phase is prepared by stirring and mixing the fragrance and the shell material.
  • an aqueous solution containing an anionic group-imparting agent for example, lysine
  • the oil phase is added to the prepared aqueous phase to disperse and emulsify, and the resulting emulsion is heated and stirred and then cooled.
  • an aqueous solution of a base for example, sodium hydroxide
  • the aqueous solution containing the anionic group-imparting agent may be added after the emulsion is formed, or an aqueous base solution may be added to the aqueous phase in advance.
  • content of said each component can be changed suitably.
  • -Anionic group imparting agent- There is no restriction
  • the protective colloid means a colloid that can impart an anionic charge to the microcapsule surface by being present on the microcapsule surface.
  • the surface anionizing agent is not particularly limited as long as it can give an anionic charge to the microcapsule surface (anionic water-soluble polymers (anionic polysaccharides such as anion-modified polyvinyl alcohol, carboxymethyl cellulose, carrageenan, polyacrylic acid)). And copolymers with sodium and other monomers, copolymers with sodium polymaleate and other monomers) and anionic surfactants (sodium dodecyl sulfate, sodium lauryl sulfate, etc.).
  • anionic water-soluble polymers anionic polysaccharides such as anion-modified polyvinyl alcohol, carboxymethyl cellulose, carrageenan, polyacrylic acid
  • anionic surfactants sodium dodecyl sulfate, sodium lauryl sulfate, etc.
  • the microcapsule in the microcapsule-containing composition of the present disclosure preferably has an anion-modified polyvinyl alcohol on at least a part of the surface from the viewpoint of imparting an anionic charge to the microcapsule surface.
  • Examples of the method for forming a protective colloid on the surface of the microcapsule using the surface anionizing agent include the following methods. However, the present disclosure is not limited to the following method. First, an oil phase is prepared by stirring and mixing a solvent, a trifunctional aliphatic isocyanate and a specific diisocyanate which are shell materials. Subsequently, an aqueous solution containing a surface anionizing agent (for example, anion-modified polyvinyl alcohol) is prepared as an aqueous phase. The oil phase is added to the prepared aqueous phase and dispersed to emulsify, and the resulting emulsion is heated, stirred and cooled.
  • a surface anionizing agent for example, anion-modified polyvinyl alcohol
  • a base for example, sodium hydroxide aqueous solution
  • a base for example, sodium hydroxide aqueous solution
  • content of each above-mentioned component can be changed suitably.
  • the anion-modified polyvinyl alcohol commercially available products can be used.
  • commercially available products are Kuraray Poval KM-618 (manufactured by Kuraray Co., Ltd.), Kuraray Poval KL-318 (manufactured by Kuraray Co., Ltd.), Gohsenol L-3266 (manufactured by Nippon Synthetic Chemical Co., Ltd.), Gohsenol T-330 (Japan) Synthetic Chemical Co., Ltd.).
  • the anion-modified polyvinyl alcohol is preferably Kuraray Poval KM-618 or Gohsenol L-3266, and more preferably Kuraray Poval KM-618.
  • the microcapsule-containing composition of the present disclosure preferably contains a cationic surfactant when an anionic charge is imparted to the microcapsule surface.
  • a cationic surfactant when an anionic charge is imparted to the microcapsule surface.
  • the anion charge (minus charge) of the microcapsule and the plus charge of the cationic surfactant attract each other due to the interaction, so that the plus charge of the cationic surfactant covers the microcapsule.
  • a positive charge can be generated as a whole capsule, and the positive charge of the microcapsule attracts the negative charge of the attached object (for example, fiber or hair) to which the microcapsule adheres. Adhesion can be further improved.
  • the cationic surfactant is not particularly limited, and conventionally known cationic surfactants can be used.
  • alkylamine salts for example, quaternary ammonium salts (for example, hexadecyltrimethylammonium chloride), polyoxyethylene alkylamine salts, polyethylene Examples include polyamine derivatives.
  • a commercially available product may be used as the cationic surfactant.
  • examples of commercially available products include cation EQ-01D (NOF Corporation), cation SF-10 (manufactured by Sanyo Kasei Kogyo Co., Ltd.), cation SF-75PA (manufactured by Sanyo Kasei Kogyo Co., Ltd.), and Adecamin SF-108 (stock) The company ADEKA).
  • the microcapsule of this indication can be manufactured with the following method, for example, it is not limited to the following method.
  • the microcapsule manufacturing method of the present disclosure disperses an oil phase containing a fragrance and a polyisocyanate as a shell material in an aqueous phase containing an emulsifier.
  • the step of preparing an emulsified liquid emulsification step
  • the step of polymerizing the shell material at the interface between the oil phase and the aqueous phase to form a shell and forming microcapsules enclosing a fragrance emulsification step
  • emulsification step emulsification step
  • encapsulation step emulsification step
  • Including interfacial polymerization methods can be used as appropriate.
  • an oil phase containing a fragrance is dispersed in an aqueous phase containing an emulsifier to prepare an emulsion (emulsification step), and a shell material is added to the aqueous phase to emulsify
  • a coacervation method including a step (encapsulation step) of forming a microcapsule encapsulating a fragrance by forming a polymer layer formed of a shell material on the surface of the droplet can be used as appropriate.
  • the microcapsule manufacturing method of the present disclosure disperses an oil phase containing a fragrance and a polyisocyanate as a shell material in an aqueous phase containing an emulsifier. And a step of preparing an emulsion (emulsification step).
  • the shell is formed from a melamine formaldehyde resin, it includes a step (emulsification step) of preparing an emulsion by dispersing an oil phase containing a fragrance in an aqueous phase containing an emulsifier.
  • Emulsified liquid of the present disclosure is formed by dispersing an oil phase containing a fragrance and, if necessary, a polyisocyanate which is a shell material in an aqueous phase containing an emulsifier.
  • the oil phase of the present disclosure includes at least a fragrance.
  • the shell material may further include components such as polyisocyanate, a solvent, a co-solvent, and / or an additive.
  • solvents, cosolvents, and additives are as described in the section ⁇ Microcapsules>.
  • the shell material in the present disclosure can include a polyisocyanate or a melamine formaldehyde prepolymer. Furthermore, it is preferable that specific diisocyanate is included.
  • the shell material is, for example, more than 0.1% by mass and 20% by mass or less, preferably 0.5% by mass to 10% by mass, more preferably 1% by mass to 5% by mass with respect to the total mass of the oil phase. Contained in The concentration of the shell material can be appropriately adjusted in view of the size of the microcapsules, the wall thickness, and the like.
  • the aqueous phase of the present disclosure includes at least an aqueous medium and an emulsifier.
  • aqueous medium of the present disclosure examples include water and a mixed solvent of water and a water-soluble organic solvent, preferably water.
  • Water-soluble means that the amount of the target substance dissolved in 100% by mass of water at 25 ° C. is 5% by mass or more.
  • 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 40% by mass with respect to the total mass of the emulsion that is a mixture of an oil phase and an aqueous phase. ⁇ 60% by mass.
  • the emulsifier includes a dispersant, a surfactant, or a combination thereof.
  • dispersant examples include polyvinyl alcohol and modified products thereof, polyacrylic acid amide and derivatives thereof, ethylene-vinyl acetate copolymer, styrene-maleic anhydride copolymer, ethylene-maleic anhydride copolymer, isobutylene- Mention may be made of maleic anhydride copolymer, polyvinylpyrrolidone, ethylene-acrylic acid copolymer, vinyl acetate-acrylic acid copolymer, carboxymethylcellulose, methylcellulose, casein, gelatin, starch derivatives, gum arabic and sodium alginate. Polyvinyl alcohol is preferred. These dispersants preferably do not react with the shell material or are extremely difficult to react. For example, those having a reactive amino group in a molecular chain such as gelatin are preliminarily treated to lose the reactivity. It is necessary.
  • surfactant examples include nonionic surfactants, anionic surfactants, cationic surfactants, and amphoteric surfactants.
  • Surfactant may be used independently and may be used in combination of 2 or more type.
  • the nonionic surfactant is not particularly limited, and a conventionally known nonionic surfactant can be used.
  • a conventionally known nonionic surfactant can be used.
  • polyoxyethylene alkyl ether compounds polyoxyethylene alkyl phenyl ether compounds, polyoxyethylene polystyryl phenyl ether compounds, polyoxyethylene polyoxypropylene alkyl ether compounds, glycerin fatty acid partial ester compounds, sorbitan fatty acid moieties Ester compounds, pentaerythritol fatty acid partial ester compounds, propylene glycol mono fatty acid ester compounds, sucrose fatty acid partial ester compounds, polyoxyethylene sorbitan fatty acid partial ester compounds, polyoxyethylene sorbitol fatty acid partial ester compounds, polyethylene glycol Fatty acid ester compounds, polyglycerin fatty acid partial ester compounds, polyoxyethylenated castor oil compounds Polyoxyethylene glycerin fatty acid partial ester compound, fatty acid
  • the anionic surfactant is not particularly limited, and conventionally known anionic surfactants can be used.
  • fatty acid salt, abietic acid salt, hydroxyalkane sulfonate, alkane sulfonate, dialkyl sulfosuccinate ester salt linear alkyl benzene sulfonate, branched alkyl benzene sulfonate, alkyl naphthalene sulfonate, alkyl phenoxy poly Oxyethylenepropyl sulfonate, polyoxyethylene alkylsulfophenyl ether salt, N-methyl-N-oleyl taurine sodium salt, N-alkylsulfosuccinic acid monoamide disodium salt, petroleum sulfonate, sulfated beef oil, fatty acid alkyl ester Sulfate ester salt, alkyl sulfate ester salt, polyoxyethylene alkyl ether sulfate ester,
  • the cationic surfactant is not particularly limited, and conventionally known cationic surfactants can be used. Examples thereof include alkylamine salts, quaternary ammonium salts (for example, hexadecyltrimethylammonium chloride), polyoxyethylene alkylamine salts, polyethylene polyamine derivatives, and the like.
  • amphoteric surfactant is not particularly limited, and a conventionally known amphoteric surfactant can be used. Examples thereof include carboxybetaine, aminocarboxylic acid, sulfobetaine, aminosulfuric acid ester, imidazoline and the like.
  • the concentration of the emulsifier is preferably more than 0% by mass and 20% by mass or less, more preferably from 0.005% by mass to 10% by mass, with respect to the total mass of the emulsion that is a mixture of the oil phase and the aqueous phase.
  • the content is more preferably from 01% by mass to 10% by mass, and particularly preferably from 1% by mass to 5% by mass.
  • the aqueous phase may contain other components such as an ultraviolet absorber, an antioxidant, and a preservative as necessary.
  • Such other components are, for example, more than 0% by mass and 20% by mass or less, preferably more than 0.1% by mass and 15% by mass or less, more preferably more than 1% by mass and 10% by mass with respect to the total mass of the aqueous phase. The following may be contained.
  • Dispersion refers to dispersing (emulsifying) the oil phase of the present disclosure as oil droplets in the water phase of the present disclosure.
  • the dispersion can be carried out by means usually used for dispersion of an oil phase and an aqueous phase, for example, a homogenizer, a Manton Gory, an ultrasonic disperser, a dissolver, a teddy mill, or other known dispersion devices.
  • the mixing ratio of the oil phase to the 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. .
  • 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.
  • the method for producing a microcapsule of the present disclosure includes an interfacial polymerization method in which a shell material is polymerized at an interface between an oil phase and an aqueous phase to form a shell, and an oil phase and an aqueous phase are emulsified and then a shell material is added and polymerized.
  • a step of forming a microcapsule enclosing a fragrance is included by using a selvage method. Thereby, the microcapsule in which the fragrance
  • Polymerization is a step of polymerizing the shell material contained in the emulsion, whereby a shell is formed.
  • the polymerization is preferably performed under heating.
  • the reaction temperature in the polymerization is usually preferably 40 ° C to 100 ° C, more preferably 50 ° C to 80 ° C.
  • the polymerization reaction time is usually preferably about 0.5 to 10 hours, more preferably about 1 to 5 hours. The higher the polymerization temperature, the shorter the polymerization time, but when using inclusions or shell materials that may decompose at high temperatures, select a polymerization initiator that works at low temperatures and polymerize at relatively low temperatures. Is desirable.
  • an aqueous solution for example, water, an aqueous acetic acid solution, etc.
  • a dispersing agent for preventing aggregation may be added again during the polymerization process.
  • a charge control agent such as nigrosine, or any other auxiliary agent can be added as necessary.
  • microcapsule-containing composition of the present disclosure can be used for various applications.
  • examples of the microcapsule-containing composition may include uses such as washing, hair care, and day care.
  • the microcapsule-containing composition of the present disclosure can be made into a softener for clothing by including, for example, a core material (for example, a fragrance). Thereby, the microcapsule-containing composition of the present disclosure can be applied to a laundry composition.
  • the microcapsule-containing composition which is a softener for clothing of the present disclosure, is obtained by immersing the clothing in the microcapsule-containing composition, dehydrating and drying, so that the microcapsules contained in the microcapsule-containing composition are adsorbed on the fibers of the clothing Or enter into the fine gaps between the fibers and held by the clothing. For this reason, softening, an antistatic property, etc. are provided with respect to clothing, Furthermore, a core material can be discharge
  • the core material When wearing clothing treated with the softener for clothing of the present disclosure, the core material is stably contained in the microcapsule in addition to the soft comfort, so even after lapse of time, stress is applied by rubbing the clothing, etc.
  • the core material can be released by disintegrating the microcapsules. Moreover, even if it does not give stress in particular, by wearing clothes and acting, the microcapsules are gradually collapsed, and the core material can be gradually released.
  • the softening agent for clothing preferably contains 0.3 to 3% by mass of the core encapsulated in the microcapsule with respect to the microcapsule-containing composition in the total amount of the microcapsule-containing composition.
  • it can further contain a known component contained in the softener for clothing, such as an antifoaming agent, a coloring material, and a fragrance.
  • the dispersion medium used for the softener for clothing is preferably water such as ion exchange water.
  • the microcapsule-containing composition containing the microcapsules and the microcapsule dispersion medium in the present disclosure can be applied to the hair care composition as it is.
  • the use of the hair care composition can be arbitrarily applied to hair cosmetics such as rinses, conditioners, hair styling agents, and the like.
  • the microcapsule-containing composition of the present disclosure which is a hair cosmetic, adheres to the hair, and when the hair is rubbed or combed, the microcapsule disintegrates due to stress, and the core material Can be released.
  • the microcapsules can be stably stored for a longer time by filling the spray container.
  • the hair cosmetic is applied to the hair by spraying, the dispersion medium and the microcapsules adhere to the hair. Thereafter, by performing massage or the like on the scalp, the microcapsules are collapsed by applying stress to the microcapsules, and the core material can be attached to the hair.
  • the microcapsule-containing composition of the present disclosure that is a hair cosmetic can optionally contain known components that can be included in the hair cosmetic.
  • Known components that can be included in hair cosmetics include aqueous media such as alcohol, oil agents, surfactants as cleaning or dispersing components, active ingredients that penetrate the skin, colorants, and fragrances.
  • the microcapsule-containing composition of the present disclosure is applied to, for example, a day care composition such as a cosmetic sheet or a diaper including a support and the microcapsule-containing composition of the present disclosure described above impregnated in the support. Can do.
  • the support is not particularly limited as long as the liquid component can be retained.
  • the support is preferably a non-woven fabric, a woven fabric or the like, a fiber assembly having a void for retaining moisture therein, a porous material such as a sponge sheet, and the like.
  • the support By impregnating the support with the microcapsule-containing composition of the present disclosure, the support is pressed against the skin and rubbed, so that the microcapsules are disintegrated and the core material can be released at an arbitrary time. Moreover, it can be set as the sheet
  • Cosmetic sheets, diapers and the like are preferably packaged with a water-impermeable packaging material in order to stably hold the microcapsule-containing composition, from the viewpoint of sustaining effects.
  • the microcapsule-containing composition of the present disclosure can release the core material at an arbitrary timing at a necessary timing, it can be applied to various uses.
  • the use described above is an example thereof, and the use of the microcapsule-containing composition of the present disclosure is not limited to the above description.
  • volume-based median diameter, standard deviation, and volume average particle diameter were measured by Microtrac MT3300EXII (manufactured by Nikkiso Co., Ltd.).
  • the wall thickness was measured by observing the cross section of the microcapsule with a scanning electron microscope JSM-7800F (manufactured by JEOL Ltd.).
  • the breaking strength of the microcapsules was obtained by diluting the microcapsule aqueous dispersion 1000 times with water, and dropping and drying on a slide glass.
  • the breaking strength of microcapsules having a diameter of about 20 ⁇ m on the slad glass was measured using a microhardness meter DUH-W201 (manufactured by Shimadzu Corporation). Measurement was performed on 6 microcapsules per sample, and the average value was taken as the measured value.
  • Example 1 18.2 parts by mass of Saracos (registered trademark) HG-8 (manufactured by Nisshin Oillio Group Co., Ltd.) as a solvent, 54.7 parts by mass of D-limonene (manufactured by Yashara Chemical Co., Ltd., fragrance), and trifunctional as a shell material 13.5 parts by mass of Takenate (registered trademark) D-160N (made by Mitsui Chemicals, Inc., hexamethylene diisocyanate trimethylolpropane adduct), 4,4′-diphenylmethane diisocyanate (MDI, Wako Pure Chemical) Kogyo Co., Ltd .; specific diisocyanate compound) 4.5 parts by mass was stirred and mixed to obtain an oil phase solution.
  • Saracos registered trademark
  • HG-8 manufactured by Nisshin Oillio Group Co., Ltd.
  • D-limonene manufactured by Yashara Chemical Co., Ltd., fragrance
  • the content ratio of the structure derived from the bifunctional aromatic isocyanate compound to the total mass of the shell material is 25% by mass.
  • an oil phase solution was added to and dispersed in 157 parts of a 5.8% aqueous solution of Kuraray Poval (registered trademark) PVA-217E (manufactured by Kuraray Co., Ltd., PVA), which is polyvinyl alcohol, and the resulting emulsion was heated to 70 ° C. Warmed up. After stirring for 6 hours, 3.8 parts by mass of a 10% by mass aqueous sodium hydroxide solution was added to obtain an aqueous microcapsule dispersion.
  • the volume-based median diameter (D50) of the obtained microcapsules was 18 ⁇ m.
  • the breaking strength of the microcapsule was 20.5 MPa.
  • a microcapsule-containing composition was prepared by mixing with a fragrance-free softener (ULTRA Downy, manufactured by Procter & Gamble Japan Co., Ltd.) so that the fragrance conversion of the microcapsule produced above was 1.0 mass%. Put about 1.5 kg of cotton towel (36 cm x 36 cm) into automatic washing machine AW-422S (H) (manufactured by Toshiba Corporation), add 30 L of water, and add 10 parts by weight of the microcapsule-containing composition as a washing base softener. It was put into the injection port and a washing process (washing 10 minutes, rinsing 25 minutes, dehydration 10 minutes) was performed. Thereafter, the sample was dried for 24 hours to obtain a sample for sustained release evaluation.
  • a fragrance-free softener ULTRA Downy, manufactured by Procter & Gamble Japan Co., Ltd.
  • Example 2 A microcapsule aqueous dispersion was obtained in the same manner as in Example 1 except that the polyvinyl alcohol used in Example 1 was used as described in Table 1. The volume-based median diameter, standard deviation, volume average particle diameter, wall thickness, and microcapsule breaking strength of the obtained microcapsules were measured in the same manner as in Example 1.
  • Example 3 to Example 17 A microcapsule aqueous dispersion was obtained in the same manner as in Example 1 except that the polyvinyl alcohol used in Example 1 was changed and the type and mixing ratio of the isocyanate compound were changed as shown in Table 1. It was. The volume-based median diameter, standard deviation, volume average particle diameter, wall thickness, and microcapsule breaking strength of the obtained microcapsules were measured in the same manner as in Example 1.
  • Example 5 A microcapsule aqueous dispersion was obtained in the same manner as in Example 1 except that the type and mixing ratio of the isocyanate compound used were changed as shown in Table 1 in Example 1. The volume-based median diameter, standard deviation, volume average particle diameter, wall thickness, and microcapsule breaking strength of the obtained microcapsules were measured in the same manner as in Example 1.
  • Example 18 75 parts by mass of Isoban (registered trademark) 10 (manufactured by Kuraray Co., Ltd., 10% isobutylene-maleic anhydride copolymer aqueous solution) and 80 parts by mass of water were mixed, and the pH of this mixture was adjusted with a 10% aqueous sodium hydroxide solution. The aqueous phase solution was adjusted to 4.5.
  • Example 19 to Example 33 A microcapsule aqueous dispersion was obtained in the same manner as in Example 18 except that the type and mixing ratio of the melamine formaldehyde prepolymer and isocyanate compound used were changed as shown in Table 2. The volume-based median diameter, standard deviation, volume average particle diameter, wall thickness, and microcapsule breaking strength of the obtained microcapsules were measured in the same manner as in Example 18.
  • Example 18 a microcapsule aqueous dispersion was obtained in the same manner as in Example 18, except that the type and mixing ratio of the isocyanate compound used were changed as shown in Table 2. The volume-based median diameter, standard deviation, volume average particle diameter, wall thickness, and microcapsule breaking strength of the obtained microcapsules were measured in the same manner as in Example 18.
  • the evaluation sample (cotton towel) obtained above was cut into a square of 1/6 area, and the cut towel was immersed in 100 g of dimethyl sulfoxide and allowed to stand for 24 hours to extract the fragrance inside the microcapsule.
  • the extracted amount (mg) of the fragrance was quantified in the obtained dimethyl sulfoxide solution with a gas chromatograph analyzer (QP2010Ultra, manufactured by Shimadzu Corporation).
  • QP2010Ultra gas chromatograph analyzer
  • PVA in Table 1 represents an emulsifier.
  • Tables 1 and 2 Details of the components in Tables 1 and 2 are as follows.
  • 217E Kuraray Poval PVA-217E (partially saponified polyvinyl alcohol), manufactured by Kuraray Co., Ltd.
  • KM-618 Kuraray Poval KM-618 (anion modified polyvinyl alcohol), manufactured by Kuraray Co., Ltd.
  • D-160N Takenate D-160N (Hexamethylene diisocyanate trimethylolpropane adduct), manufactured by Mitsui Chemicals, Inc.
  • MDI 4,4′-diphenylmethane diisocyanate (manufactured by Wako Pure Chemical Industries, Ltd.)
  • HDI Hexamethylene diisocyanate (Wako Pure Chemical Industries, Ltd.)
  • DMDI 4,4′-dicyclohexylmethane diisocyanate (Wako Pure Chemical Industries, Ltd.)
  • THDI Trimethylhexamethylene diisocyanate (Wako Pure Chemical Industries, Ltd.)
  • Isoban 10 Concentrated 10% isobutylene-maleic anhydride copolymer aqueous solution, manufactured by Kuraray Co., Ltd.
  • Nikaresin S-260 Melamine-formaldehyde prepolymer, manufactured by Nippon Carbide Industries, Ltd.
  • the shell material is a microcapsule containing polyurethane or polyurea, and i) at least one selected from a structure derived from a bifunctional aliphatic isocyanate compound and a structure derived from a bifunctional aromatic isocyanate compound
  • Examples 1 to 17 which are microcapsule compositions having a structure of 10% by mass to 70% by mass with respect to the total mass of the shell material and having a shell thickness of 0.3 to 2.0 ⁇ m are as follows: It was found that the sustained release properties were superior to those of Comparative Examples 1 to 5 that did not satisfy this requirement.
  • microcapsule of the present disclosure can be suitably used as a core material, particularly in a mode in which a fragrance is included, and can exhibit various preferable functions such as fragrance protection and sustained release.

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Abstract

L'invention concerne une composition contenant des microcapsules, produite par fabrication de microcapsules à libération prolongée présentant une résistance à la rupture élevée. Cette composition contenant des microcapsules comprend des microcapsules comportant une écorce et un cœur contenant un parfum. i) Une structure dérivée d'un composé isocyanate aliphatique bifonctionnel et/ou une structure dérivée d'un composé isocyanate aromatique bifonctionnel sont contenues à hauteur de 10 à 70 % en masse par rapport à la masse totale de la matière d'écorce constituant l'écorce, et ii) l'épaisseur de l'écorce est comprise entre 0,3 et 2,0 µm.
PCT/JP2019/010130 2018-03-23 2019-03-13 Composition contenant des microcapsules, composition de lessive, composition de soins de jour et composition de soins capillaires WO2019181668A1 (fr)

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CN111117462A (zh) * 2020-01-06 2020-05-08 深圳市美施美克新材料有限公司 富含d-柠檬烯的双组份环保涂料及其制备方法

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