WO2016152545A1 - Préparation cosmétique pour ongles et kit de décoration d'ongles - Google Patents

Préparation cosmétique pour ongles et kit de décoration d'ongles Download PDF

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Publication number
WO2016152545A1
WO2016152545A1 PCT/JP2016/057498 JP2016057498W WO2016152545A1 WO 2016152545 A1 WO2016152545 A1 WO 2016152545A1 JP 2016057498 W JP2016057498 W JP 2016057498W WO 2016152545 A1 WO2016152545 A1 WO 2016152545A1
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group
compound
nail
particles
polymerizable
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PCT/JP2016/057498
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English (en)
Japanese (ja)
Inventor
大橋　秀和
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富士フイルム株式会社
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/87—Polyurethanes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • A61Q3/02—Nail coatings

Definitions

  • the present invention relates to a nail cosmetic and a nail art kit.
  • Patent Literature a nail decoration called gel nail that has been cured by irradiation with ultraviolet rays after applying a gel-like decorative curable composition containing a urethane-based resin and a photopolymerizable monomer to the nail has a clear finish. It has attracted attention for some reasons, such as high adhesion with nails and long-lasting, no odor like acrylic resin (see Patent Document 2).
  • a nail or artificial nail containing an aqueous emulsion of a polymer containing a functional group capable of undergoing a polymerization reaction upon irradiation with active energy rays, polyethylene glycol, and a photo radical initiator (except for those containing a nitrogen atom in the molecule)
  • An aqueous composition such as a curable resin composition for coating is also known (see Patent Document 3).
  • An object of the present invention is to provide a nail cosmetic and a nail art kit including the nail cosmetic, which have improved durability and reduce the burden on fingertips and nails.
  • ⁇ 1> having a polymerizable group including a three-dimensional crosslinked structure having at least one bond selected from the group consisting of a urethane bond, a thiourethane bond, a dithiourethane bond, a urea bond, and a thiourea bond
  • a nail cosmetic characterized by containing particles containing a photopolymerization initiator in ⁇ 2>
  • the nail cosmetic according to ⁇ 1>, wherein the particle has a structure represented by the following formula 1 as the three-dimensional crosslinked structure:
  • one of X 1 and X 2 represents NH, the other represents O, NH, or S, Y represents O or S, n represents an integer of 3 or more, and R represents An n-valent organic group is represented, and * represents a bonding position with another structure.
  • R 1 represents an n-valent organic group
  • R 2 represents a divalent organic group
  • n represents an integer of 3 or more
  • * represents a bonding position with another structure.
  • ⁇ 4> The nail cosmetic according to any one of ⁇ 1> to ⁇ 3>, wherein the particles have a dispersion-stable group
  • ⁇ 5> The nail cosmetic according to ⁇ 4>, wherein the dispersion-stable group is at least one of a group having a polyether structure and an ionic group.
  • ⁇ 6> The nail cosmetic according to any one of ⁇ 1> to ⁇ 5>, wherein the particle further contains a polymerizable compound inside the particle, ⁇ 7>
  • the nail cosmetic according to ⁇ 6>, wherein the polymerizable compound is a (meth) acrylate compound
  • ⁇ 8> The nail cosmetic according to ⁇ 7>, wherein the (meth) acrylate compound is an acrylate compound having three or more functions.
  • ⁇ 9> The nail cosmetic according to any one of ⁇ 1> to ⁇ 8>, further comprising a polymerizable compound, ⁇ 10>.
  • the nail cosmetic according to any one of ⁇ 1> to ⁇ 10>, further comprising a solvent, ⁇ 12> A nail art kit comprising the nail cosmetic according to any one of ⁇ 1> to ⁇ 11>.
  • a nail cosmetic with improved durability and a reduced burden on fingertips and nails and a nail art kit including the nail cosmetic are provided.
  • a numerical range indicated by using “to” indicates a range including the numerical values described before and after “to” as the minimum value and the maximum value, respectively.
  • (meth) acrylate means at least one of acrylate and methacrylate.
  • “mass%” and “part by mass” have the same meanings as “% by weight” and “part by weight”, respectively.
  • part of the chemical formula is described with H and C omitted.
  • the group means not only an unsubstituted substituent but also a case having a substituent.
  • the description of an alkyl group means not only an unsubstituted alkyl group but also an alkyl group having a substituent.
  • a combination of preferred embodiments is a more preferred embodiment.
  • the nail cosmetic of the present invention has a polymerizable group and has at least one bond selected from the group consisting of a urethane bond, a thiourethane bond, a dithiourethane bond, a urea bond, and a thiourea bond. It contains particles containing a three-dimensional crosslinked structure and containing a photopolymerization initiator inside. Details of the mechanism of action in the present invention are unknown, but are presumed as follows.
  • the nail cosmetic of the present invention has a polymerizable group in the particle containing the photopolymerization initiator inside, so that the active species generated from the photopolymerization initiator act on the surface or inside of the particle by irradiation with active energy rays.
  • An existing polymerizable group is bonded to a polymerizable group of an adjacent particle to form a crosslinked structure.
  • both the photopolymerization initiator and the polymerizable group are present in the particles, it is considered that a cured film having high sensitivity and excellent strength can be obtained.
  • membrane strengths such as water resistance and solvent resistance, is formed because particle
  • the particles have a three-dimensional cross-linking structure, voids are formed in the particles or between the particles, and the removal liquid can quickly permeate through the voids, so that it is considered that the removal of the cured film is accelerated.
  • the nail cosmetic of the present invention has a polymerizable group and has a three-dimensional crosslink having at least one bond selected from the group consisting of a urethane bond, a thiourethane bond, a dithiourethane bond, a urea bond, and a thiourea bond. It contains particles (hereinafter also referred to as “specific particles”) containing a structure and containing a photopolymerization initiator inside. That is, the specific particles contained in the nail cosmetic of the present invention have a polymerizable group.
  • the specific particle has a three-dimensional crosslinked structure, and is selected from the group consisting of a urethane bond, a thiourethane bond, a dithiourethane bond, a urea bond, and a thiourea bond in the three-dimensional crosslinked structure. It has a species bond. That is, it is preferable that a three-dimensional crosslinked structure is formed by a urethane bond, a thiourethane bond, a dithiourethane bond, a urea bond, and a thiourea bond. Furthermore, the specific particles contain a photopolymerization initiator inside.
  • the inside of the particle means a void of a three-dimensional cross-linked structure
  • the specific particle contains a photopolymerization initiator inside, the photopolymerization initiator is in a three-dimensional cross-linked structure It is said that it exists without being combined.
  • the term “particle” includes a photopolymerization initiator and the like present in the voids of the three-dimensional crosslinked structure.
  • the specific particles contain a photopolymerization initiator therein, so that a film with high sensitivity and a high crosslinkability is formed.
  • the specific particle in the present invention having a polymerizable group means that the polymerizable group in the particle is present at a position where it can react with the polymerizable group of the adjacent particle.
  • the particle exists in a position where it can react with the polymerizable group of the adjacent particle.
  • grain surface and surface vicinity at least is preferable.
  • the polymerizable group in the specific particle is preferably an ethylenically unsaturated group, more preferably an acryloyl group, a methacryloyl group, an acrylamide group, a methacrylamide group, a vinylphenyl group, a vinyl group, and / or an allyl group, and an acryloyl group.
  • a methacryloyl group, an acrylamide group, a methacrylamide group, a vinylphenyl group, and / or an allyl group are more preferable, and an acryloyl group, a methacryloyl group, an acrylamide group, and / or a methacrylamide group are particularly preferable.
  • the particles having a three-dimensional cross-linking structure having at least one type of bond selected from the group consisting of a urethane bond, a thiourethane bond, a dithiourethane bond, a urea bond, and a thiourea bond are structures represented by the following formula 1. It means that the particles have.
  • one of X 1 and X 2 represents NH, the other represents O, NH, or S, Y represents O or S, n represents an integer of 3 or more, and R represents An n-valent organic group is represented, and * represents a bonding position with another structure.
  • any one of X 1 and X 2 represents NH and the other represents O or NH.
  • Y is preferably O.
  • it means a urethane bond.
  • a thiourethane bond means a case where one of two Os of a urethane bond is S.
  • X 1 and X 2 when one of X 1 and X 2 is NH, the other is S and Y is S, it means a dithiourethane bond.
  • X 1 and X 2 when both X 1 and X 2 are NH and Y is O, it means a urea bond, and when both X 1 and X 2 are NH and Y is S, it means a thiourea bond. . n X 1 , X 2 , and Y may be the same or different.
  • n represents an integer of 3 or more, preferably an integer of 3 or more, 10 or less, more preferably an integer of 3 or more and 8 or less, and still more preferably an integer of 3 or more and 6 or less. * Represents a site that binds to another structural part.
  • R represents an n-valent organic group.
  • the organic group represented by R is an organic group composed of an element selected from the group consisting of oxygen, nitrogen, halogen, phosphorus, sulfur, silicon and boron as essential elements, with carbon and hydrogen as essential elements.
  • carbon and hydrogen are essential elements
  • an organic group composed of an element selected from the group consisting of oxygen, nitrogen, halogen, phosphorus, and sulfur is more preferable, and carbon and hydrogen are essential.
  • the element is an organic group composed of an element selected from the group consisting of oxygen, nitrogen, and sulfur.
  • Organic groups composed only of carbon atoms and hydrogen atoms are also preferred.
  • Particles having a three-dimensional cross-linking structure having at least one bond selected from the group consisting of a urethane bond, a thiourethane bond, a dithiourethane bond, a urea bond, and a thiourea bond have a structure represented by the following formula 2. More preferably, the particles have.
  • R 1 represents an n-valent organic group
  • R 2 represents a divalent organic group
  • n represents an integer of 3 or more
  • * represents a bonding position with another structure.
  • n represents an integer of 3 or more, preferably an integer of 3 or more and 10 or less, more preferably an integer of 3 or more and 8 or less, and still more preferably an integer of 3 or more and 6 or less.
  • n R 2 s may be the same or different.
  • * Represents a site that binds to another structural part.
  • bond with another structure part through S, NH, or O it is more preferable to couple
  • bonding through NH the site forms a urea bond
  • the site forms a urethane bond.
  • R 1 represents an n-valent organic group, and is preferably an n-valent organic group bonded to the carbonyl carbon via NH, O, or S, and is an n-valent organic group bonded via NH or O. It is more preferable that it is an n-valent organic group bonded through O.
  • the organic group represented by R 1 is an organic group composed of an element selected from the group consisting of oxygen, nitrogen, halogen, phosphorus, sulfur, silicon, and boron, with carbon and hydrogen as essential elements and optional elements.
  • carbon and hydrogen are essential elements, and as an optional element, an organic group composed of an element selected from the group consisting of oxygen, nitrogen, halogen, phosphorus, and sulfur is more preferable.
  • the essential element is an organic group composed of an element selected from the group consisting of oxygen, nitrogen and sulfur.
  • Organic groups composed only of carbon atoms and hydrogen atoms are also preferred.
  • n-valent organic group represented by R 1 a compound having three or more functional groups selected from an OH group, an NHR group (where R represents a hydrogen atom, an alkyl group, and an aryl group) and an SH group Therefore, a residue obtained by removing H present in the OH group, NHR group, and SH group is preferable.
  • Specific examples of the n-valent organic group represented by R 1 are preferably (R1-1) to (R1-83) shown below, more preferably (R1-1) to (R1-77), R1-1) to (R1-37) are particularly preferred.
  • a to d each independently represents an integer of 1 to 20.
  • R 2 represents a divalent organic group.
  • the divalent organic group represented by R 2 includes carbon and hydrogen as essential elements, and is composed of an element selected from the group consisting of oxygen, nitrogen, halogen, phosphorus, sulfur, silicon, and boron as an optional element. It is preferably a divalent organic group, and is a divalent organic group composed of elements selected from the group consisting of oxygen, nitrogen, halogen, phosphorus, and sulfur as essential elements, with carbon and hydrogen as essential elements. More preferably, it is more preferably a divalent organic group composed of an element selected from the group consisting of oxygen, nitrogen and sulfur with carbon and hydrogen as essential elements. A divalent organic group composed only of carbon atoms and hydrogen atoms is also preferred.
  • the divalent organic group represented by R 2 is preferably a residue obtained by removing an NCO group from a compound having two NCO groups.
  • Specific examples of the divalent organic group represented by R 2 are preferably (R2-1) to (R2-34) shown below, more preferably (R2-1) to (R2-25), R2-1) to (R2-8) are more preferable.
  • R 3 and R 4 are hydrogen atom, and the other is a methyl group.
  • Me represents a methyl group.
  • a method for introducing a polymerizable group into particles for example, (1) when a three-dimensional crosslinked structure is formed, a trifunctional or higher functional isocyanate compound or a thioisocyanate compound and water or two or more active hydrogen groups are included.
  • a method of reacting a compound with a polymerizable compound having an active hydrogen group (2) when producing a trifunctional or higher functional isocyanate compound or thioisocyanate compound, a trifunctional isocyanate compound or thioisocyanate, and an active hydrogen group After forming an isocyanate compound or thioisocyanate to which a polymerizable group has been added in advance to form a three-dimensional cross-linked structure by reacting with water or a compound having two or more active hydrogen groups.
  • Method (3) When producing particles, a polymerizable compound is used as an oil phase component together with the components constituting the particles. It is a solution, adding the aqueous phase component in the oil phase component, mixing, and a method of emulsification.
  • the above (1) or (2) is preferable, and (2) is more preferable. These three methods can be used in combination as a method for introducing a polymerizable group.
  • the specific particles have a polymerizable group, adjacent particles can be crosslinked and a film can be formed.
  • the crosslinking reaction is three-dimensional. It proceeds to form a three-dimensional network structure.
  • the particles are excellent in mechanical strength by including a three-dimensional crosslinked structure having at least one bond selected from the group consisting of urethane bond, thiourethane bond, dithiourethane bond, urea bond, and thiourea bond. A film is obtained.
  • a a trifunctional or higher functional isocyanate compound
  • b water or a compound having two or more active hydrogen groups (which forms a trifunctional or higher functional isocyanate compound), which is a component for forming particles used in the present invention.
  • c a polymerizable compound having an active hydrogen group
  • d a bifunctional or higher functional isocyanate compound and a polymerizable compound having an active hydrogen group.
  • a polymerizable isocyanate compound to which a polymerizable group has been added in advance
  • e a polymerizable compound
  • f a photopolymerization initiator
  • g a compound having a dispersion stability group
  • a compound for introducing a polymerizable group (a polymerizable compound having an active hydrogen group, a polymerizable isocyanate compound, or a polymerizable compound) and a photopolymerization initiator are preferably used as raw materials.
  • a method for forming particles (i) a, b, c, and f (optionally, at least one selected from the group consisting of d, e, and g may be added thereto) And (ii) adding at least one selected from the group consisting of a, b, d, and f (optionally consisting of c, e, and g).
  • the method of forming particles by reacting may be preferably exemplified, but the present invention is not limited thereto.
  • the three-dimensional crosslinked structure in the particles is preferably a product formed by the reaction of a trifunctional or higher functional isocyanate compound and water.
  • an isocyanate compound will be described, but the present invention can be similarly applied to a thioisocyanate compound in which an isocyanate group is replaced with a thioisocyanate group.
  • Trifunctional or higher functional isocyanate compound is a compound having three or more isocyanate groups in the molecule, preferably a compound having 3 to 10 isocyanate groups in the molecule. A compound having an isocyanate group is more preferable, and a compound having 3 to 6 isocyanate groups is still more preferable.
  • the trifunctional or higher functional isocyanate compound used in the present invention a known compound and a compound synthesized by the method described later can be used. Known compounds include, for example, compounds described in “Polyurethane Resin Handbook” (edited by Keiji Iwata, published by Nikkan Kogyo Shimbun (1987)).
  • trifunctional or higher functional isocyanate compounds (1) bifunctional or higher functional isocyanate compounds (compounds having two or more isocyanate groups in the molecule) and trifunctional or higher functional polyols, polyamines, polythiols, etc. Triad or higher isocyanate compound (adduct type) as an adduct (adduct) with the compound having the above active hydrogen group, (2) Trimer of bifunctional or higher isocyanate compound (biuret type or isocyanurate type) And (3) compounds having three or more isocyanate groups in the molecule such as formalin condensate of benzene isocyanate are preferably exemplified.
  • These trifunctional or higher functional isocyanate compounds may be a mixture containing a plurality of compounds, and the compound of the preferred embodiment shown below is preferably the main component of the mixture, and may contain other components. .
  • Adduct Type The adduct type trifunctional or higher functional isocyanate compound is preferably a compound represented by the following formula 3.
  • R 31 represents an n3 valent organic group
  • n3 represents an integer of 3 or more
  • R 32 represents a divalent organic group.
  • R 31 is preferably an n3 valent organic group bonded to the carbonyl carbon via NH, O or S, more preferably an n3 valent organic group bonded via NH or O, It is further more preferable that it is an n3 valent organic group couple
  • the organic group represented by R 31 is an organic group composed of an element selected from the group consisting of oxygen, nitrogen, halogen, phosphorus, sulfur, silicon, and boron, with carbon and hydrogen as essential elements and optional elements.
  • carbon and hydrogen are essential elements, and as an optional element, an organic group composed of an element selected from the group consisting of oxygen, nitrogen, halogen, phosphorus, and sulfur is more preferable. More preferably, the essential element is an organic group composed of an element selected from the group consisting of oxygen, nitrogen and sulfur. Organic groups composed only of carbon atoms and hydrogen atoms are also preferred.
  • an n3-valent organic group represented by R 31 a compound having three or more functional groups selected from an OH group, an NHR group (where R represents a hydrogen atom, an alkyl group, and an aryl group) and an SH group Therefore, a residue obtained by removing H present in the OH group, NHR group, and SH group is preferable.
  • n3-valent organic group represented by R 31 are preferably the above-described (R1-1) to (R1-83), more preferably (R1-1) to (R1-77), and (R1 -1) to (R1-37) are particularly preferable.
  • strength of a film is high and an external appearance becomes favorable.
  • n3 is preferably an integer of 3 to 10, more preferably an integer of 3 to 8, and still more preferably an integer of 3 to 6.
  • the divalent organic group represented by R 32 includes carbon and hydrogen as essential elements, and is composed of an element selected from the group consisting of oxygen, nitrogen, halogen, phosphorus, sulfur, silicon and boron as an optional element. It is preferably a divalent organic group, and is a divalent organic group composed of elements selected from the group consisting of oxygen, nitrogen, halogen, phosphorus, and sulfur as essential elements, with carbon and hydrogen as essential elements. More preferably, it is more preferably a divalent organic group composed of an element selected from the group consisting of oxygen, nitrogen and sulfur with carbon and hydrogen as essential elements. A divalent organic group composed only of carbon atoms and hydrogen atoms is also preferred.
  • the divalent organic group represented by R 32 is preferably a residue obtained by removing an NCO group from a compound having two NCO groups.
  • Specific examples of the divalent organic group represented by R 32 are preferably the aforementioned (R2-1) to (R2-34), more preferably (R2-1) to (R2-25), and (R2 -1) to (R2-8) are more preferable.
  • An adduct-type trifunctional or higher functional isocyanate compound can be synthesized by reacting a compound having three or more active hydrogen groups in a molecule described later with a bifunctional or higher functional isocyanate compound described later.
  • the active hydrogen group means a hydroxyl group, a primary amino group, a secondary amino group, and a mercapto group.
  • the adduct-type trifunctional or higher functional isocyanate compound is, for example, heated (50 ° C. to 100 ° C.) while stirring a compound having three or more active hydrogen groups in the molecule and a bifunctional or higher functional isocyanate compound in an organic solvent. Or by stirring at a low temperature (0 ° C.
  • the trifunctional or higher functional isocyanate compound is prepared by synthesizing an adduct (prepolymer) of a compound having two active hydrogen groups in the molecule and a bifunctional or higher functional isocyanate compound. It can also be obtained by reacting a compound having an active hydrogen group.
  • the number of moles (number of molecules) of a bifunctional or higher functional isocyanate compound to be reacted with a compound having three or more active hydrogen groups in the molecule is the active hydrogen group in the compound having three or more active hydrogen groups in the molecule.
  • a bifunctional or higher functional isocyanate compound having a mole number (number of molecules) of 0.6 times or more is used with respect to the number of moles (equivalent number of active hydrogen groups).
  • the number of moles of the bifunctional or higher functional isocyanate compound is preferably 0.6 to 5 times, more preferably 0.6 to 3 times, more preferably 0.8 to 2 times the number of moles of the active hydrogen group. preferable.
  • adduct-type trifunctional or higher functional isocyanate compounds in the present invention are shown in Table 1 below.
  • the present invention is not limited to these.
  • Table 1 compounds having trifunctional or higher functional active hydrogen groups and diisocyanate compounds are described, and further, molar equivalents at the time of addition reaction of these compounds are described.
  • the adduct-type trifunctional or higher functional isocyanate compound in the present invention is more preferably NCO102 to NCO105, NCO107, NCO108, NCO111, and NCO113 among the compounds shown in Table 1 above.
  • adduct type trifunctional or higher functional isocyanate compound in the present invention commercially available products may be used.
  • D-102, D-103, D-103H, D-103M2, P49-75S, D -110, D-120N, D-140N, D-160N Mitsubishi Chemicals Co., Ltd.
  • Death Module registered trademark
  • L75 UL57SP
  • Coronate registered trademark
  • HX HX
  • L manufactured by Nippon Polyurethane Co., Ltd.
  • P301-75E manufactured by Asahi Kasei Co., Ltd.
  • D-110, D-120N, D-140N, and D-160N are more preferable.
  • biuret type or isocyanurate type trifunctional or higher functional isocyanate compound is preferably a compound represented by the following formula 5 or formula 6.
  • R 51 to R 53 and R 61 to R 63 each independently represent a divalent organic group.
  • the divalent organic groups represented by R 51 to R 53 and R 61 to R 63 have carbon and hydrogen as essential elements, and as optional elements, oxygen, nitrogen, halogen, phosphorus, sulfur, silicon and boron
  • it is a divalent organic group composed of an element selected from the group consisting of carbon and hydrogen as essential elements, and as an optional element selected from an element selected from the group consisting of oxygen, nitrogen, halogen, phosphorus and sulfur More preferably, it is a divalent organic group, more preferably a divalent organic group composed of an element selected from the group consisting of oxygen, nitrogen and sulfur with carbon and hydrogen as essential elements. .
  • a divalent organic group composed only of carbon atoms and hydrogen atoms is also preferred.
  • the divalent organic group represented by R 51 to R 53 and R 61 to R 63 is preferably a residue obtained by removing an NCO group from a compound having two NCO groups.
  • Specific examples of the divalent organic group represented by R 51 to R 53 and R 61 to R 63 are preferably the aforementioned (R2-1) to (R2-34), and (R2-1) to (R2-25) is more preferable, and (R2-1) to (R2-8) are particularly preferable.
  • biuret-type trifunctional or higher functional isocyanate compound in the present invention commercially available products may be used.
  • isocyanurate type trifunctional or higher functional isocyanate compound in the present invention commercially available products may be used as the isocyanurate type trifunctional or higher functional isocyanate compound in the present invention.
  • D-127, D-170N, D-170HN, D-172N, D- 177N (manufactured by Mitsui Chemicals), Sumidur N3300, Death Module (registered trademark) N3600, N3900, Z4470BA (manufactured by Sumika Bayer Urethane Co., Ltd.), Coronate (registered trademark) HX, HK (Nippon Polyurethane Co., Ltd.) Manufactured), Duranate (registered trademark) TPA-100, TKA-100, TSA-100, TSS-100, TLA-100, TSE-100 (manufactured by Asahi Kasei Corporation).
  • Duranate registered trademark
  • 24A-100 manufactured by Asahi Kasei Co., Ltd.
  • D-127 manufactured by Mitsui Chemicals, Inc.
  • TKA-100 manufactured by Asahi Kasei Co., Ltd.
  • TSE-100 manufactured by Asahi Kasei Co., Ltd.
  • the particles (specific particles) in the present invention have the above-described trifunctional or higher functional isocyanate compound or thioisocyanate compound and water or two or more active hydrogen groups. It is preferably produced by reacting a compound. As a compound to be reacted with a trifunctional or higher functional isocyanate compound, water is generally used. By reacting the trifunctional or higher functional isocyanate compound with water, a three-dimensional crosslinked structure having a urea bond is formed. In addition to water, a compound having two or more active hydrogen groups is exemplified as a compound to be reacted with a trifunctional or higher functional isocyanate compound.
  • Examples of the compound having two or more active hydrogen groups include 3 in the molecule described above. Examples thereof include compounds having one or more active hydrogen groups and compounds having two active hydrogen groups in the molecule. Examples of the compound having two active hydrogen groups in the molecule include compounds having two groups selected from the group consisting of a hydroxyl group, a primary amino group, a secondary amino group, and a mercapto group in the molecule.
  • Specific examples of the compound having two active hydrogen groups in the molecule include propylene glycol, 1,4-butanediol, 1,3-butanediol, pinacol, triethylene glycol, dipropylene glycol, and 1,3-cyclohexanediol.
  • Polymerizable compound having an active hydrogen group is used to introduce a polymerizable group into the three-dimensional crosslinked structure of the particles.
  • a polymerizable group for example, (1) when forming a three-dimensional crosslinked structure having at least one type of bond selected from the group consisting of a urethane bond, a thiourethane bond, a dithiourethane bond, a urea bond, and a thiourea bond.
  • a trifunctional or higher functional isocyanate compound or thioisocyanate a method of reacting an isocyanate compound or a thioisocyanate compound, water, a compound having two or more active hydrogen groups, and a polymerizable compound having an active hydrogen group Is produced by reacting a bifunctional or higher functional isocyanate compound or thioisocyanate compound with a polymerizable compound having an active hydrogen group to form an isocyanate compound or thioisocyanate compound to which a polymerizable group has been added in advance. Reaction with a compound having two or more active hydrogen groups Used in.
  • Examples of the polymerizable compound having an active hydrogen group include compounds having at least one active hydrogen group and at least one ethylenically unsaturated bond.
  • the compound having at least one active hydrogen group and at least one ethylenically unsaturated bond can be represented by the following formula a.
  • L 1 represents an m + n-valent linking group
  • m and n are each independently 1 to 100
  • Lc represents a monovalent ethylenically unsaturated group
  • Z represents an active hydrogen group.
  • L 1 is a divalent or higher aliphatic group, a divalent or higher aromatic group, a divalent or higher heterocyclic group, —O—, —S—, —NH—, —N ⁇ , —CO—, —SO. It is preferably —, —SO 2 — or a combination thereof.
  • m and n are each independently preferably from 1 to 50, more preferably from 2 to 20, still more preferably from 3 to 10, and particularly preferably from 3 to 5.
  • an allyl group, a vinyl group, an acryloyl group, a methacryloyl group, or a vinylphenyl group is preferable, and an acryloyl group or a methacryloyl group is particularly preferable.
  • Z is preferably OH, SH, NHR (R represents a monovalent organic group) or NH 2 , more preferably OH or NH 2 , and still more preferably OH.
  • Examples of compounds having at least one active hydrogen group and at least one ethylenically unsaturated bond are shown below, but are not limited to this structure.
  • a commercially available product may be used.
  • hydroxyethyl acrylate (Osaka Organic Chemical Co., Ltd.)
  • the polymerizable isocyanate compound includes, for example, an isocyanate group of the above-described trifunctional or higher isocyanate compound, at least one active hydrogen group, and at least one ethylenic group as shown in Synthesis Scheme 3 below. It can be prepared by reacting an active hydrogen group of a compound having an unsaturated bond.
  • X 71 represents a n7 monovalent organic group
  • Z 71 represents O or NH
  • R 71 represents a hydrogen atom or a methyl group
  • X 72 represents a divalent organic group.
  • n7 represents an integer of 3 or more.
  • any of the above compounds can be suitably used, but at least one active hydrogen group and at least one ethylenically unsaturated bond are combined in the combinations shown in Table 2 below. It is preferable to use a compound obtained by reacting a compound having a compound (indicated as a polymerizable group-introducing monomer in Table 2) with a trifunctional or higher functional isocyanate compound (indicated in Table 2 as polyisocyanate).
  • active hydrogen group / NCO group represents the molar ratio of the active hydrogen group in the polymerizable group-introduced monomer to the NCO group in the polyisocyanate.
  • DA-212 and DA-920 are the following compounds.
  • trifunctional or higher functional isocyanate compounds may be used singly or in combination of two or more. These compounds having at least one active hydrogen group and at least one ethylenically unsaturated bond may be one kind or a combination of two or more kinds.
  • a compound having an isocyanate group, at least one active hydrogen group and at least one ethylenically unsaturated bond of a tri- or higher functional isocyanate compound (indicated as polyisocyanate in Table 2) (indicated as a polymerizable group-introducing monomer in Table 2)
  • the reaction is carried out in an amount of 0.03 to 0.2.
  • the compound obtained by the reaction of the trifunctional or higher functional isocyanate compound and the compound having at least one active hydrogen group and at least one ethylenically unsaturated bond has an average functional group number of isocyanate groups in the compound of 3 or less. Although a trifunctional or higher functional isocyanate group is contained in the compound, a three-dimensional crosslinked structure can be formed when the particles are produced.
  • the polymerizable compound is a compound used in (3) of the method for introducing a polymerizable group into particles, and the polymerizable compound is present inside the particles (voids of a three-dimensional cross-linked structure). It is a compound used when manufacturing this particle
  • the polymerizable compound present inside the particles is also referred to as “encapsulated polymerizable compound”.
  • polymeric compounds other than the polymeric compound which has the above-mentioned active hydrogen group are mentioned.
  • these polymerizable compounds known polymerizable compounds can be used.
  • a compound having an acryloyl group, a methacryloyl group, a vinylphenyl group, a vinyl group, and / or an allyl group as a polymerizable group is preferable, and an acryloyl group, a methacryloyl group, a vinylphenyl group, and / or a vinyl group.
  • a compound having an acryloyl group and / or a compound having a methacryloyl group ((meth) acrylate compound) is particularly preferable.
  • the polymerizable compound used in the present invention any compound having at least one polymerizable group in the molecule can be suitably used.
  • the polymerizable compound used in the present invention may be any one having a chemical form such as a monomer, an oligomer, or a polymer.
  • the CLogP value of the polymerizable compound used in the present invention is preferably 0 or more.
  • the CLogP value is an estimated value of a water / octanol partition coefficient, and is a value calculated by Chem Bio Draw Ultra Version 12.0.2.1076 (manufactured by Cambridge Soft).
  • the boiling point of the polymerizable compound used in the present invention is preferably 130 ° C or higher, more preferably 140 ° C or higher, and further preferably 150 ° C or higher. By using the compound having the above boiling point, it is possible to suppress volatilization at the time of particle production and storage of particles and cosmetics.
  • the upper limit of the boiling point of the polymerizable compound is not particularly limited.
  • polymerizable compound used in the present invention examples include butoxyethyl acrylate, ethyl carbitol acrylate, cyclohexyl acrylate, tetrahydrofurfuryl acrylate, benzyl acrylate, tridecyl acrylate, 2-phenoxyethyl acrylate, bis (4-acryloxy) Polyethoxyphenyl) propane, polyethylene glycol diacrylate, polypropylene glycol diacrylate, pentaerythritol tetraacrylate, trimethylolpropane triacrylate (for example, A-TMPT manufactured by Shin-Nakamura Chemical Co., Ltd.), ditrimethylolpropane tetraacrylate (for example, Shin-Nakamura Chemical Co., Ltd.
  • AD-TMP dipentaerythritol hexaacrylate, diacetone acrylic And acrylate compounds such as isobornyl acrylate, dicyclopentenyl acrylate, dicyclopentenyloxyethyl acrylate, dicyclopentanyl acrylate, neopentyl glycol propylene oxide adduct diacrylate (NPGPODA); n-butyl methacrylate, allyl methacrylate, Examples thereof include benzyl methacrylate, dimethylaminomethyl methacrylate, polyethylene glycol dimethacrylate, polypropylene glycol dimethacrylate, and methacrylate compounds such as 2,2-bis (4-methacryloxypolyethoxyphenyl) propane.
  • NPGPODA neopentyl glycol propylene oxide adduct diacrylate
  • NPGPODA neopentyl glycol propylene oxide adduct diacrylate
  • NPGPODA
  • the inclusion polymerizable compound is preferably a polyfunctional polymerizable compound, more preferably a trifunctional or higher functional polymerizable compound, and even more preferably a tetrafunctional or higher functional polymerizable compound from the viewpoint of crosslinkability and film strength.
  • the inclusion polymerizable compound is preferably a methacrylate compound or an acrylate compound.
  • the encapsulated polymerizable compound used in the present invention is preferably a (meth) acrylate compound, more preferably a trifunctional or higher functional (meth) acrylate compound, and even more preferably a trifunctional or higher functional acrylate compound.
  • Examples of the encapsulating polymerizable compound include, for example, JP-A-7-159983, JP-B-7-31399, JP-A-8-224982, JP-A-10-863, JP-A-9-134011, and JP-T-2004.
  • Photocurable polymerizable compounds used in the photopolymerizable composition described in each publication such as 5114014 are known, and these can also be applied to the particles in the present invention.
  • encapsulated polymerizable compound commercially available products may be used.
  • commercially available products may be used.
  • the encapsulated polymerizable compound in the present invention is prepared by dissolving the encapsulated polymerizable compound as an oil phase component together with the components constituting the particle, and adding, mixing, and emulsifying the water phase component to the oil phase component. And can be contained inside the particles.
  • the molecular weight of the encapsulated polymerizable compound in the present invention is preferably 100 to 100,000, more preferably 200 to 30,000, and still more preferably 250 to 10,000 as a weight average molecular weight. .
  • the content of the encapsulating polymerizable compound is preferably 0.1% by mass to 75% by mass, more preferably 0.5% by mass to 60% by mass. More preferably, it is 1% by mass to 50% by mass.
  • the particles (specific particles) in the present invention contain at least one photopolymerization initiator inside the particles (voids having a three-dimensional crosslinked structure).
  • the photopolymerization initiator included in the particles of the specific particles is also referred to as “encapsulated photopolymerization initiator”.
  • the particles contain a photopolymerization initiator inside, the sensitivity to active energy rays is increased, and a film having excellent strength can be obtained.
  • the particle contains a photopolymerization initiator inside, it is possible to use a photopolymerization initiator that has been conventionally difficult to use because of its high sensitivity but low dispersibility or low solubility in water.
  • the photopolymerization initiator contained in the particles (hereinafter also referred to as an encapsulated photopolymerization initiator), a known photopolymerization initiator may be appropriately selected and used according to the purpose of use of the nail cosmetic. Can do.
  • the encapsulated photopolymerization initiator is a compound that absorbs active energy rays and generates radicals that are polymerization initiation species. Examples of active energy rays include ⁇ rays, ⁇ rays, electron beams, ultraviolet rays, visible rays, and infrared rays. Among these, ultraviolet rays and / or visible rays are preferably used as active energy rays.
  • encapsulated photopolymerization initiator known compounds can be used, but preferred encapsulated photopolymerization initiators usable in the present invention include the following compounds.
  • Acetophenone derivatives eg, 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy-2-phenylacetophenone, 2-hydroxy-2-methylpropiophenone, 4'-isopropyl-2-hydroxy-2-methylpropiophenone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-1-propane, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 1- [ 4- (2-hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propan-1-one, benzoin, benzoin methyl ether, etc.); Benzophenone derivatives (for example, 4,4′-bis (dimethylamino) benzophenone, 3,3-d
  • the photopolymerization initiator can be appropriately selected according to the wavelength of light emitted from the light source used for exposure. Derivatives are preferred, and acetophenone derivatives, benzophenone derivatives, thioxanthone derivatives, and / or phosphine oxide derivatives are more preferred. These photopolymerization initiators may use the above compounds alone or in combination of two or more.
  • the encapsulated photopolymerization initiator in the present invention when producing particles, dissolves the encapsulated photopolymerization initiator as an oil phase component together with the components constituting the particles, and adds, mixes, and emulsifies the water phase component to the oil phase component. By doing so, it can be included inside the particles. Accordingly, the ClogP value of the photopolymerization initiator is preferably 0 or more.
  • the content of the encapsulated photopolymerization initiator in the present invention is preferably 0.1% by mass to 25% by mass, more preferably 0.5% by mass to 20% by mass with respect to the total mass of the specific particles.
  • the content is preferably 1% by mass to 15% by mass.
  • the particles (specific particles) in the present invention preferably have a dispersion-stable group on the surface.
  • the particles have a dispersion-stable group on the surface thereof, so that the dispersibility in the medium is further improved. Therefore, the dispersibility of the particles in the nail cosmetic can be further improved.
  • Examples of the dispersion-stable group added to the surface of the particle include a group having a polyether structure and an ionic group, and examples of the ionic group include a carboxylic acid (salt) group, a phosphonic acid (salt) group, Examples thereof include a phosphoric acid (salt) group, a sulfonic acid (salt) group, a sulfuric monoester (salt) group, and a group having a betaine structure.
  • a dispersion stability group may be used individually by 1 type, and may use 2 or more types together.
  • the dispersion stability group added to the surface of the particle is more preferably at least one of a group having a polyether structure and a carboxylic acid group.
  • the addition of the dispersion stability group to the surface of the particle is performed by reacting the above-described trifunctional or higher functional isocyanate compound and the above-described compound having two or more active hydrogen groups with the compound having the dispersion stability group. Can be done. Further, when the above-described trifunctional or higher functional isocyanate compound is produced, the bifunctional or higher functional isocyanate compound is reacted with a compound having a dispersion stability group, and the above-described isocyanate compound having a dispersion stability group added in advance is described. It can also be performed by reacting with a compound having two or more active hydrogen groups. Examples of the compound having a dispersion stability group used for addition of the dispersion stability group to the surface of the particle include compounds having the above dispersion stability group.
  • a compound having a group having a polyether structure and a compound having a carboxylic acid group are preferable.
  • the compound having a group having a polyether structure include a compound having a polyoxyalkylene chain. Specific examples include polyethylene oxide, polypropylene oxide, polytetramethylene oxide, polystyrene oxide, polycyclohexylene oxide, polyethylene oxide-polypropylene oxide-block copolymer, polyethylene oxide-polypropylene oxide random copolymer, and the like.
  • polyethylene oxide, polypropylene oxide, and polyethylene oxide-polypropylene oxide block copolymers are preferable, and polyethylene oxide is more preferable.
  • the compound having a group having a polyether structure include polyethylene oxide monoethers (monoethers include monomethyl ether, monoethyl ether, etc.), polyethylene oxide monoesters (monoesters include monoesters). Acetic acid ester, mono (meth) acrylic acid ester, etc. are mentioned).
  • the compound having a carboxylic acid group or other ionic dispersion stability group include the following.
  • the compound having a carboxylic acid group or other ionic dispersion-stable group may be partially neutralized with an inorganic salt machine such as sodium hydroxide and an organic base such as triethylamine.
  • TMP trimethylolpropane
  • XDI xylene diisocyanate
  • EO polyethylene glycol monomethyl ether
  • Adduct Mitsubishi Chemicals, Takenate (registered trademark) D-116N) and / or reaction product of 2,2-bis (hydroxymethyl) propionic acid (DMPA) and isophorone diisocyanate (IPDI) (carvone It is preferable to use an isocyanate compound containing an acid group.
  • the amount of the compound having a dispersion-stable group used for addition of the dispersion-stable group to the surface of the particle is preferably 0.1% by mass to 40% by mass with respect to the mass of the particle, and 1% by mass to 35% by mass. Is more preferable, and 3% by mass to 30% by mass is even more preferable.
  • the method for producing the specific particles in the present invention is not particularly limited, but the trifunctional or higher functional isocyanate compound and / or the thioisocyanate compound (or the trifunctional or higher functional isocyanate compound to which a polymerizable group is added and / or the oil phase component).
  • a method for introducing a polymerizable group into particles (1) a method using a polymerizable compound having an active hydrogen group when forming a three-dimensional cross-linked structure, and (2) preliminarily polymerizable. Examples thereof include a method using an isocyanate compound or a thioisocyanate compound to which a group is added, and (3) a method using a polymerizable compound together with components constituting the particles, and any of these may be selected.
  • the trifunctional or higher functional isocyanate compound and / or thioisocyanate compound (or trifunctional or higher functional isocyanate compound and / or thioisocyanate compound to which a polymerizable group is added) as described above as an oil phase component, photopolymerization.
  • an oil phase component and an aqueous phase component using an initiator and, if necessary, a polymerizable compound, water as an aqueous phase component, mix both, and prepare an emulsified dispersion using an emulsifier such as a homogenizer.
  • an aqueous dispersion containing particles can be obtained.
  • the isocyanate groups (and / or thioisocyanate groups) are cross-linked by the reaction of the isocyanate groups (and / or thioisocyanate groups) of the trifunctional or higher functional isocyanate compound (and / or thioisocyanate compound) with water.
  • Particles containing a polymerization initiator are formed.
  • preferred embodiments of particle formation include (1) an oil phase component containing a trifunctional or higher functional isocyanate compound to which a polymerizable group is added and a photopolymerization initiator, and water as an aqueous phase component.
  • Preferred examples include a trifunctional or higher functional isocyanate compound, a polymerizable compound, and an oil phase component containing a photopolymerization initiator and water as the aqueous phase component.
  • the oil phase component further contains an isocyanate compound to which a dispersion stability group has been added.
  • the isocyanate group reacts with water to produce an amine, and the produced amine reacts with the isocyanate group to form a urea bond.
  • a urethane bond a urethane bond
  • a thiourethane bond a dithiourethane bond
  • a urea bond a thiourea bond by reaction with an isocyanate group and / or a thioisocyanate group
  • the above-mentioned polyfunctional alcohols, polyfunctional phenols, polyfunctional amines having a hydrogen atom on the nitrogen atom, polyfunctional thiols, and the like are used as the compound that forms. These compounds may be used individually by 1 type, and may use 2 or more types together.
  • polyfunctional alcohols such as water, propylene glycol, glycerin and trimethylolpropane
  • polyfunctional amines such as bis (hexamethylene) triamine, ethylenediamine and diethylenetriamine, and pentaerythritol tetra (3-mercaptopropionate)
  • polyfunctional thiol it is preferable to use water and / or a polyfunctional alcohol from the viewpoint of production stability, and it is more preferable to use water.
  • the above trifunctional or higher functional isocyanate compound and / or the trifunctional or higher functional thioisocyanate compound water, polyfunctional alcohol, polyfunctional phenol, polyfunctional amine having a hydrogen atom on the nitrogen atom,
  • a compound having the dispersion stability group described above By including a compound having a dispersion-stable group as a raw material during the production of the particles, the dispersion-stable group can be added to the surface of the particles.
  • a dispersant, a surfactant and the like may be added.
  • the dispersant and the surfactant are added to the oil phase component and / or the aqueous phase component depending on the solubility thereof.
  • a surfactant it is preferable to add a surfactant in order to improve the stability of the emulsified dispersion.
  • the surfactant may be added to either the oil phase or the aqueous phase, but it is usually preferable to add it to the aqueous phase because of its low solubility in organic solvents.
  • the addition amount is preferably 0.1% by mass to 5% by mass and more preferably 0.5% by mass to 3% by mass with respect to the total solid content of the oil phase.
  • surfactants used for emulsification and dispersion are considered to be excellent surfactants having a relatively long-chain hydrophobic group.
  • “Surfactant Handbook” (Nishiichiro et al., Published in industrial books (1980)).
  • alkali metal salts such as alkyl sulfates, alkyl sulfonic acids, and alkyl benzene sulfonic acids can be used.
  • alkyl sulfate salts are preferred.
  • the average particle diameter of the specific particles is preferably 0.01 ⁇ m to 10.0 ⁇ m from the viewpoint of dispersibility, more preferably 0.01 ⁇ m to 5 ⁇ m, and still more preferably 0.05 ⁇ m to 1 ⁇ m.
  • the average particle diameter of the particles can be measured by a light scattering method.
  • the average particle diameter in this specification is a value measured by LA-910 (manufactured by Horiba, Ltd.).
  • the specific particles are preferably contained in the nail cosmetic from 1% by mass to 90% by mass, more preferably from 3% by mass to 85% by mass from the viewpoint of dispersibility and crosslinkability, and more preferably 5% by mass. More preferably, the content is from 80% to 80% by mass.
  • the content of the particles is a value including a compound such as a photopolymerization initiator existing inside the particles (voids having a three-dimensional crosslinked structure).
  • the particles (specific particles) used in the nail cosmetic of the present invention may be added to the nail cosmetic in the form of an aqueous solution after production. After the production, water is removed by evaporation to obtain a particle aqueous solution having a desired concentration. It may be added to the material. In addition, after the production, water may be completely removed by evaporation or centrifugation, and then added to the nail cosmetic and redispersed.
  • Photopolymerization initiator In the nail cosmetic of the present invention, a photopolymerization initiator may be added to the outside of the specific particles in addition to the photopolymerization initiator contained in the specific particles. As said photoinitiator, the thing similar to the above-mentioned photoinitiator (encapsulated photoinitiator) is mentioned.
  • a polymer and / or oligomer may be added outside the specific particles.
  • the weight average molecular weight of the polymer and / or oligomer used in the nail cosmetic of the present invention is preferably 2,000 or more and 300,000 or less, more preferably 3,000 or more and 200,000 or less. Is more preferably from 5,000 to 150,000, and particularly preferably from 5,000 to 100,000. It is excellent in the adhesiveness and temporal stability of the hardened
  • the weight average molecular weight (Mw) of the polymer and oligomer in the present invention is a weight average molecular weight in terms of polystyrene measured by gel permeation chromatography (GPC) using tetrahydrofuran (THF) as a solvent.
  • GPC gel permeation chromatography
  • THF tetrahydrofuran
  • the type of the polymer and / or oligomer is not particularly limited, and known polymer species (poly (meth) acrylic acid ester, poly (meth) acrylic acid amide, polyurethane, polyester, polyether, polyurea, polycarbonate, polyamide, Polystyrene, polyolefin, polyvinyl alcohol, polyvinyl butyral, vinyl resin, etc.) can be used.
  • the polymer and / or oligomer preferably has an ethylenically unsaturated group capable of radical polymerization.
  • polymers and / or oligomers having a structure represented by the following formula A are preferable, and polymers and / or oligomers having a structure represented by formula A in the polymer main chain. It is particularly preferred. By having this structure, adhesion is particularly excellent.
  • P-16 to P-22 Specific examples (P-16 to P-22) of polymers and / or oligomers used in the present invention are shown below. The present invention is not limited to these.
  • Unit-1 to Unit-5 indicate the isocyanate compound used in the synthesis of the polymer, the compound having an active hydrogen group, and the like, and the polymerization reaction is performed so that the respective molar ratios are obtained. Went.
  • the abbreviations in the table are as follows.
  • TDI Tolylene diisocyanate
  • Diol-9 2,2-bis (4-hydroxycyclohexyl) propane
  • Diol-5 Polytetrabutylene glycol (Mw: 2,000)
  • HEMA 2-hydroxyethyl methacrylate
  • HPMA 2-hydroxypropyl methacrylate
  • MDI bis (4-isocyanatophenyl) methane
  • HDI hexamethylene diisocyanate
  • Diol-6 polypropylene glycol (Mw: 1,000)
  • Diol-10 Glycerin monomethacrylate MMA: Methyl methacrylate
  • BMA n-Butyl methacrylate
  • ADPA Adipic acid dichloride Nitrocellulose: DHX40-70 (manufactured by Inabata Sangyo Co., Ltd.)
  • Diamin-2 Polypropylene glycol diamine (Mw: 2,000)
  • the polymer and / or oligomer used in the present invention is preferably a polymer and / or oligomer having an amino group.
  • the amino group any of primary, secondary, and tertiary amino groups can be used. From the viewpoint of ease of production of the polymer and / or oligomer, adhesion and removability, and stability over time. A tertiary amino group is preferred.
  • the amino group in the polymer and / or oligomer may be introduced at any of the side chain, inside the main chain, and at the end of the main chain, and may be introduced at two or more positions.
  • the amino group is preferably a group represented by the following formulas B and C.
  • R b1 and R b2 each independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
  • L b1 represents a single bond or a divalent linking group
  • R b1 , R b2 At least two members selected from the group consisting of L b1 may be connected to each other to form a ring, and the wavy line portion represents a bonding position with another structure.
  • R c1 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
  • L c1 and L c2 each independently represents a single bond or a divalent linking group
  • R c1 , L c1 and at least two members selected from the group consisting of L c2 may be linked to each other to form a ring, and the wavy line portion represents a bonding position with another structure.
  • R b1 and R b2 in Formula B are preferably an alkyl group having 1 to 10 carbon atoms, and an alkyl group having 1 to 6 carbon atoms from the viewpoint of the balance between solubility in an aqueous acid solution and water resistance.
  • the alkyl group having 1 to 4 carbon atoms is more preferable, and the alkyl group having 1 to 2 carbon atoms is particularly preferable.
  • L b1 in Formula B include a single bond, an alkylene group having 1 to 20 carbon atoms (which may have a substituent, and part of the carbon atoms may be replaced by a hetero atom), carbon number And an arylene group having 6 to 20 (which may have a substituent and a part of carbon atoms may be replaced by a heteroatom), a single bond, an alkylene group having 1 to 20 carbon atoms, a carbon number of 2 It is preferably an oxyalkylene group having 20 to 20 carbon atoms or a polyoxyalkylene group having 2 to 20 carbon atoms, more preferably an alkylene group having 1 to 20 carbon atoms or a polyoxyalkylene group having 2 to 20 carbon atoms.
  • alkylene group having 1 to 20 carbon atoms is particularly preferable, and an alkylene group having 1 to 10 carbon atoms is most preferable.
  • at least two selected from the group consisting of R b1 , R b2 and L b1 may be connected to each other to form a ring.
  • R c1 is preferably an alkyl group having 1 to 10 carbon atoms, and preferably an alkyl group having 1 to 6 carbon atoms, from the viewpoint of the balance between solubility in an aqueous acid solution and water resistance. More preferred is an alkyl group having 1 to 4 carbon atoms.
  • specific examples of L c1 and L c2 include a single bond and an alkylene group having 1 to 20 carbon atoms (which may have a substituent, and some of the carbon atoms may be replaced with a hetero atom.
  • An arylene group having 1 to 20 carbon atoms (which may have a substituent, and part of the carbon atoms may be replaced by a hetero atom), a single bond, an alkylene group having 1 to 20 carbon atoms And preferably an oxyalkylene group having 2 to 20 carbon atoms or a polyoxyalkylene group having 2 to 20 carbon atoms, preferably an alkylene group having 1 to 20 carbon atoms or a polyoxyalkylene group having 2 to 20 carbon atoms. More preferred is an alkylene group having 1 to 20 carbon atoms, and most preferred is an alkylene group having 1 to 10 carbon atoms.
  • at least two selected from the group consisting of R c1 , L c1 and L c2 may be linked to each other to form a ring.
  • the amine value of the polymer and / or oligomer used in the present invention is preferably 0.1 to 10 mmol / g, more preferably 0.25 to 9 mmol / g, and 0.5 to 8 mmol / g. More preferably it is. It is excellent in adhesiveness and removability as it is the said range.
  • a method for measuring the amine value for example, a sample is placed in a beaker, acetic acid is added, and the mixture is stirred and dissolved. And can be obtained by titrating with a titration apparatus.
  • the amine value is the amount of perchloric acid consumed when titrated, expressed as the number of moles per gram of sample (solid content).
  • polymers and / or oligomers having an amino group used in the present invention are shown below.
  • the present invention is not limited to these.
  • the polymers and / or oligomers in the table are obtained by polymerizing the compounds shown in the units in the table at the molar ratio in the table.
  • IPDI isophorone diisocyanate
  • TDI tolylene diisocyanate
  • HDI hexamethylene diisocyanate
  • MDI bis (4-isocyanatophenyl) methane
  • Diol-1 3-dimethylamino-1,2-propanediol
  • Diol-2 as diol monomer
  • Diol-3 N-butyldiethanolamine
  • Diol-4 1,5-pentanediol
  • Diol-5 Polytetrabutylene glycol (Mw: 2,000)
  • Diol-6 Polypropylene glycol (Mw: 1,000)
  • Diol-7 3-diethylamino-1,2-propanediol
  • Diol-8 1,4-butanediol Diamin-1: 3,3-diamino-N
  • a water-soluble polymer and / or oligomer can also be suitably used.
  • the water-soluble polymer and / or oligomer is preferably a polymer and / or oligomer that dissolves by 0.1 g or more with respect to 100 g of distilled water, more preferably a polymer and / or oligomer that dissolves by 0.2 g or more, and 0.5 g or more. Soluble polymers and / or oligomers are particularly preferred. By having water solubility in the above range, it becomes easy to produce nail cosmetics using water.
  • Examples of the water-soluble polymer and / or oligomer used in the present invention include a carboxylic acid (salt) group, a sulfonic acid (salt) group, a phosphoric acid (salt) group, a phosphonic acid (salt) group, a quaternary ammonium base, and a hydroxyl group.
  • the counter cation of the carboxylic acid (salt) group, sulfonic acid (salt) group, phosphoric acid (salt) group, phosphonic acid (salt) group is an alkali metal cation such as sodium or potassium, or an alkaline earth such as calcium or magnesium. Metal cations, ammonium cations, or phosphonium cations are preferred, and alkali metal cations such as sodium and potassium are particularly preferred.
  • the alkyl group of the ammonium group of the quaternary ammonium base is preferably a methyl group or an ethyl group.
  • the counter anion is preferably a halide ion such as chloride ion or bromide ion, sulfate anion, nitrate anion, phosphate anion, sulfonate anion, carboxylate anion, carbonate anion, halide ion, sulfonate anion, Carboxylic acid anions are particularly preferred.
  • the substituent on the nitrogen atom of the carboxylic acid amide group is preferably an alkyl group having 8 or less carbon atoms, and particularly preferably an alkyl group having 6 or less carbon atoms.
  • the connecting chain length (the number of repeating ethyleneoxy units) of the polyethylene glycol chain is preferably 2 or more, and particularly preferably 4 or more.
  • water-soluble polymer and / or oligomer used in the present invention are shown below.
  • the present invention is not limited to these.
  • the polymers and / or oligomers in the table are obtained by polymerizing the compounds shown in the units in the table at the molar ratio in the table.
  • the polymer and / or oligomer used in the present invention can be produced by a known method (eg, radical polymerization, polycondensation, etc.). These polymers and / or oligomers may be used alone or in combination of two or more.
  • the content of the polymer and / or oligomer in the nail cosmetic used in the present invention is preferably 0 to 90% by mass, more preferably 5 to 80% by mass, and particularly preferably 10 to 70% by mass. In this range, the adhesion and removability of the cured product are improved.
  • a polymerizable compound may be added to the outside of the particle in addition to the polymerizable compound contained in the particle.
  • the polymerizable compound include compounds having an ethylenically unsaturated group, acrylonitrile, styrene, and various radically polymerizable compounds such as various unsaturated polyesters, unsaturated polyethers, unsaturated polyamides, and unsaturated urethanes.
  • a compound having an ethylenically unsaturated group is preferable, and a compound having a (meth) acryl group is particularly preferable.
  • One of the ethylenically unsaturated compounds used in the present invention is a radically polymerizable monomer having an amino group.
  • the amino group any of primary, secondary, and tertiary amino groups can be used, but it is a tertiary amino group from the viewpoint of temporal stability, adhesion and removability of the radical polymerizable monomer. It is preferable.
  • the amino group is preferably a group represented by the following formula B or C.
  • R b1 and R b2 each independently represent a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
  • L b1 represents a single bond or a divalent linking group
  • R b1 , R b2 At least two members selected from the group consisting of L b1 may be connected to each other to form a ring, and the wavy line portion represents a bonding position with another structure.
  • R c1 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
  • L c1 and L c2 each independently represents a single bond or a divalent linking group
  • R c1 , L c1 and at least two members selected from the group consisting of L c2 may be linked to each other to form a ring, and the wavy line portion represents a bonding position with another structure.
  • R b1 and R b2 in Formula B are preferably an alkyl group having 1 to 10 carbon atoms, and an alkyl group having 1 to 6 carbon atoms from the viewpoint of the balance between solubility in an aqueous acid solution and water resistance.
  • the alkyl group having 1 to 4 carbon atoms is more preferable, and the alkyl group having 1 to 2 carbon atoms is particularly preferable.
  • L b1 in Formula B include a single bond, an alkylene group having 1 to 20 carbon atoms (which may have a substituent, and part of the carbon atoms may be replaced by a hetero atom), carbon number And an arylene group having 6 to 20 (which may have a substituent and a part of carbon atoms may be replaced by a heteroatom), a single bond, an alkylene group having 1 to 20 carbon atoms, a carbon number of 2 It is preferably an oxyalkylene group having 20 to 20 carbon atoms or a polyoxyalkylene group having 2 to 20 carbon atoms, more preferably an alkylene group having 1 to 20 carbon atoms or a polyoxyalkylene group having 2 to 20 carbon atoms.
  • alkylene group having 1 to 20 carbon atoms is particularly preferable, and an alkylene group having 1 to 10 carbon atoms is most preferable.
  • at least two selected from the group consisting of R b1 , R b2 and L b1 may be connected to each other to form a ring.
  • R c1 is preferably an alkyl group having 1 to 10 carbon atoms, and preferably an alkyl group having 1 to 6 carbon atoms, from the viewpoint of the balance between solubility in an aqueous acid solution and water resistance. More preferred is an alkyl group having 1 to 4 carbon atoms.
  • specific examples of L c1 and L c2 include a single bond and an alkylene group having 1 to 20 carbon atoms (which may have a substituent, and some of the carbon atoms may be replaced with a hetero atom.
  • An arylene group having 1 to 20 carbon atoms (which may have a substituent, and part of the carbon atoms may be replaced by a hetero atom), a single bond, an alkylene group having 1 to 20 carbon atoms And preferably an oxyalkylene group having 2 to 20 carbon atoms or a polyoxyalkylene group having 2 to 20 carbon atoms, preferably an alkylene group having 1 to 20 carbon atoms or a polyoxyalkylene group having 2 to 20 carbon atoms. More preferred is an alkylene group having 1 to 20 carbon atoms, and most preferred is an alkylene group having 1 to 10 carbon atoms.
  • at least two selected from the group consisting of R c1 , L c1 and L c2 may be linked to each other to form a ring.
  • radical polymerizable monomers having an amino group a radical polymerizable monomer having a structure represented by the following formula A is more preferable. By having this structure, adhesion and removability with an aqueous solution are particularly excellent.
  • radical polymerizable monomer having an amino group used in the present invention examples include 2-dimethylaminoethyl methacrylate, 3-dimethylaminopropyl acrylamide, 2-diethylaminoethyl methacrylate, 4-dimethylaminomethylstyrene, N-butylbis ( 2-methacryloyloxyethyl) amine, 1,2,2,6,6-pentamethyl-4-piperidine methacrylate and the like.
  • the present invention is not limited to these.
  • ethylenically unsaturated compound used in the present invention is a radical polymerizable monomer having no amino group.
  • radical polymerizable monomer having no amino group include (meth) acrylic acid; methyl (meth) acrylate, ethyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, Monofunctional (meth) acrylic acid esters such as 2-hydroxypropyl (meth) acrylate, glycerin mono (meth) acrylate, isobornyl (meth) acrylate; 2-hydroxyethyl (meth) acrylamide, N, N-dimethylacrylamide, N , N-diethylacrylamide, isopropylacrylamide, morpholineacrylamide, and other monofunctional (meth) acrylamides; N-vinylpyrrolidone, N-vinylcaprolactam, and other N-viny
  • radical polymerizable monomers having no amino group are (meth) acrylic acid, N, N-dimethylacrylamide, N, N-diethylacrylamide, morpholine acrylamide, N-2-hydroxyethyl (meth) acrylamide, N -Vinylpyrrolidone, N-vinylcaprolactam, 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, glycerin monomethacrylate, N- [tris (3-acryloylaminopropyl) Oxymethylene) methyl] acrylamide, diethylene glycol bis (3-acryloylaminoproyl) ether, polyethylene glycol di (meth) acrylate, or polypropylene glycol di (meth) a Relate is preferably contained, and (meth) acrylic acid, N, N-dimethylacrylamide, N-2-hydroxyethyl (meth)
  • radical polymerizable monomers may be used alone or in combination of two or more.
  • the content of the polymerizable compound in the nail cosmetic of the present invention is preferably 0 to 90% by mass, more preferably 5 to 80% by mass, and particularly preferably 10 to 70% by mass. In this range, the adhesion and removability of the cured product are improved.
  • a solvent may be used for dissolving each component or adjusting the ease of application of the nail cosmetic.
  • a solvent having a boiling point of 50 to 150 ° C. at 1 atm is preferable, and a solvent having a boiling point of 60 to 140 ° C. is particularly preferable.
  • solvent examples include water; alcohols such as methanol, ethanol, isopropyl alcohol, 1-propanol, 1-butanol, 2-butanol, t-butyl alcohol, 2-methyl-1-propanol, and 1-methoxy-2-propyl alcohol.
  • alcohols such as methanol, ethanol, isopropyl alcohol, 1-propanol, 1-butanol, 2-butanol, t-butyl alcohol, 2-methyl-1-propanol, and 1-methoxy-2-propyl alcohol.
  • Hydrocarbons such as hexane, heptane, toluene and xylene; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dimethoxyethane and diphenyl ether; esters such as methyl acetate, ethyl acetate, butyl acetate and ⁇ -butyrolactone; acetone , Ketones such as methyl ethyl ketone and cyclohexanone; amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and N-ethylpyrrolidone; dimethyl carbonate, die Carbonates such as carbonate and propylene carbonate; ureas such as tetramethylurea and 1,3-dimethyl-2-imidazolidinone; halogenated hydrocarbons such as chloroform, dichloromethane and chlorobenz
  • solvents water, methanol, ethanol, isopropyl alcohol, 1-propanol, 1-butanol, 2-butanol, t-butyl alcohol, 2-methyl-1-propanol, 1-methoxy-2-propyl alcohol, acetic acid, And / or acetonitrile is preferable, and water, ethanol, isopropyl alcohol, and / or acetic acid are more preferable.
  • the content of the solvent in the nail cosmetic of the present invention is preferably 0 to 80% by mass, more preferably 5 to 70% by mass, and particularly preferably 10 to 60% by mass. In this range, the applicability and drying properties of the nail cosmetic are improved.
  • known compounds can be added to the nail cosmetic of the present invention as necessary. Specifically, other polymer particles (emulsions, etc.), sensitizing dyes, polymerization inhibitors, pigments, dyes, fragrances, ultraviolet (UV) absorbers, antioxidants, fillers, various elastomers, plasticizers, thickeners , Additives such as thixotropy imparting agent, silane coupling agent, titanate coupling agent, chelating agent, flame retardant, and surfactant.
  • the nail cosmetic of the present invention can be produced by mixing the above ingredients by a known method.
  • [Particle] represents a specific particle
  • (A) represents a photopolymerization initiator
  • (B) represents a polymer and / or oligomer
  • (C) represents a polymerizable compound
  • (D) Represents a solvent.
  • a method for producing nail makeup using the nail cosmetic of the present invention is to apply a nail cosmetic on an object such as a nail, nail cosmetic, or artificial nail by a known method, and then irradiate with light to form a cured product.
  • the method of forming is mentioned.
  • the method for applying the nail cosmetic of the present invention onto an object is not particularly limited and may be carried out by a known method, but a method using a brush or brush, spray coating, ink jet coating, bar Examples include coater coating, spin coating, curtain coating, dip coating, air knife coating, blade coating, and roll coating.
  • the coating thickness on the object of the nail cosmetic of the present invention varies depending on the application, but is preferably 1 nm to 1 mm, more preferably 10 nm to 0.5 mm, and particularly preferably 100 nm to 0.4 mm. Within this range, good adhesion and removability are realized.
  • the method of applying light after applying the nail cosmetic of the present invention to an object is not particularly limited, and is a known light source (for example, sunlight, high-pressure mercury lamp, fluorescent lamp, UV lamp, light-emitting diode (LED) lamp, A known light irradiation method using an LED laser or the like (for example, full surface exposure, scanning exposure, etc.) can be used.
  • the light irradiation time is not particularly limited as long as the photocurable composition is cured. As a method of forming a cured product of the nail cosmetic on the object, the above method can be repeated.
  • the nail makeup using the nail cosmetic of the present invention can be removed by a known method. Specifically, a method of polishing with a file, a method of cutting with a sword or knife, a method of covering with nail makeup with cotton dampened with acetone, leaving it embrittled for a few minutes, embrittled with a stick, etc. Examples thereof include a method of immersing in an aqueous solution having a pH for several minutes, embrittlement and then peeling with a tweezers or the like or peeling with a stick, and a method of combining them.
  • the nail art kit of the present invention includes the nail cosmetic of the present invention and tools necessary for applying them to the nails.
  • the preferred embodiments of the nail cosmetic of the present invention in the nail art kit of the present invention are the same as those described above.
  • Specific examples of tools necessary for performing nail surgery include nail cosmetics other than the nail cosmetic of the present invention for color or top use, nail files such as files, and flats for applying nail cosmetics.
  • Brushes and brushes such as brushes, exposure devices such as UV light, wiping or cleaning liquids, wiping wipes, nail brushes, dust brushes, nail foam used for lengthening nails, acrylic resin, glass, metal Or decorative stones made of natural stone, nail seals, decorative powders such as glitter and holograms, cutters, spatulas, sticks, tweezers, separators that increase finger spacing to prevent contact between nails, etc. Not limited.
  • TMP Trimethylolpropane
  • HXDI 1,3-bis (isocyanatomethyl) cyclohexane
  • AcOEt ethyl acetate
  • TMP Trimethylolpropane
  • HXDI 1,3-bis (isocyanatemethyl) cyclohexane
  • AcOEt ethyl acetate
  • NCO101 to NCO103, NCO105 to NCO119, NCO201, NCO203 to NCO222 NCO101 to NCO103 and NCO105 to NCO119 in Table 6 below were produced in the same manner as NCO104. Further, NCO 201 and NCO 203 to NCO 222 shown in Table 7 below were produced in the same manner as NCO 202.
  • NCO202 solid content 35% by mass
  • Irgacure registered trademark
  • BASF encapsulated photopolymerization initiator
  • aqueous phase component As an aqueous phase component, 0.4 g of sodium dodecyl sulfate was dissolved in 50 g of distilled water. The aqueous phase component was added to the oil phase component, mixed, and emulsified at 12,000 rpm for 10 minutes using a homogenizer. The obtained emulsion was added to 25 g of distilled water, stirred for 30 minutes at room temperature (23 ° C., the same applies hereinafter), and then stirred for 3 hours at 50 ° C. to distill off ethyl acetate.
  • aqueous phase component As an aqueous phase component, 0.4 g of sodium dodecyl sulfate was dissolved in 50 g of distilled water. The aqueous phase component was added to the oil phase component, mixed, and emulsified at 12,000 rpm for 10 minutes using a homogenizer. The obtained emulsion was added to 25 g of distilled water, stirred at room temperature for 30 minutes, and then stirred at 50 ° C. for 3 hours to distill off ethyl acetate. Subsequently, stirring was continued while distilling off water at 50 ° C., and stirring was stopped when the solid content concentration of the dispersion liquid of particles 4 reached about 40% by mass, whereby a dispersion liquid of particles 1 was obtained. The average particle diameter of the particles measured by the light scattering method was 0.21 ⁇ m.
  • Particles 5 to 7 are the same as Particle 4 except that the trifunctional isocyanate compound (NCO202) and dipentaerythritol hexaacrylate used in Particle 4 are changed to the isocyanate compounds and inclusion polymerizable compounds shown in Table 8 below.
  • NCO202 trifunctional isocyanate compound
  • Table 8 dipentaerythritol hexaacrylate
  • the aqueous phase component was added to the oil phase component, mixed, and emulsified at 12,000 rpm for 10 minutes using a homogenizer.
  • the obtained emulsion was added to 25 g of distilled water, stirred at room temperature for 30 minutes, and then stirred at 50 ° C. for 3 hours to distill off ethyl acetate. Subsequently, stirring was continued while distilling off water at 50 ° C., and stirring was stopped when the solid content concentration of the dispersion liquid of particles 8 reached about 40% by mass to obtain a dispersion liquid of particles 8.
  • the average particle diameter of the particles measured by the light scattering method was 0.19 ⁇ m.
  • aqueous phase component As an aqueous phase component, 0.4 g of sodium dodecyl sulfate and 0.033 g of sodium hydroxide were dissolved in 50 g of distilled water. The aqueous phase component was added to the oil phase component, mixed, and emulsified at 12,000 rpm for 10 minutes using a homogenizer. The obtained emulsion was added to 25 g of distilled water, stirred at room temperature for 30 minutes, and then stirred at 50 ° C. for 3 hours to distill off ethyl acetate. Thereafter, stirring was continued while distilling off water at 50 ° C., and when the solid content concentration of the dispersion liquid of particles 11 reached about 40% by mass, the stirring was stopped to obtain a dispersion liquid of particles 11. The average particle diameter of the particles measured by the light scattering method was 0.15 ⁇ m.
  • NCO202 solid content 35% by mass
  • a trifunctional or higher functional isocyanate compound having a polymerizable group added trimethylolpropane
  • xylene diisocyanate trimethylolpropane
  • polyethylene glycol monomethyl ether adduct Mitsubishi Chemicals ( Co., Ltd., Takenate D-116N 50% ethyl acetate solution, 3.5 g isocyanate compound added with a dispersion-stable group
  • isocyanate compound 2 added with a dispersion-stable group (ethyl acetate solution, solid content 35% by mass) 2.51 g
  • Irgacure (registered trademark) 819 manufactured by BASF) 1 g (encapsulated photopolymerization initiator) was dissolved in 5 g of ethyl acetate.
  • aqueous phase component As an aqueous phase component, 0.4 g of sodium dodecyl sulfate and 0.033 g of sodium hydroxide were dissolved in 50 g of distilled water. The aqueous phase component was added to the oil phase component, mixed, and emulsified at 12,000 rpm for 10 minutes using a homogenizer. The obtained emulsion was added to 25 g of distilled water, stirred at room temperature for 30 minutes, and then stirred at 50 ° C. for 3 hours to distill off ethyl acetate. Thereafter, stirring was continued while distilling off water at 50 ° C., and stirring was stopped when the solid content concentration of the dispersion liquid of particles 14 was about 40% by mass to obtain a dispersion liquid of particles 14. The average particle size of the particles measured by the light scattering method was 0.16 ⁇ m.
  • aqueous phase component As an aqueous phase component, 0.4 g of sodium dodecyl sulfate and 0.033 g of sodium hydroxide were dissolved in 50 g of distilled water. The aqueous phase component was added to the oil phase component, mixed, and emulsified at 12,000 rpm for 10 minutes using a homogenizer. The obtained emulsion was added to 25 g of distilled water, stirred at room temperature for 30 minutes, and then stirred at 50 ° C. for 3 hours to distill off ethyl acetate.
  • NCO101 solid content 35% by mass
  • NPGPODA neopentylglycol propylene oxide adduct diacrylate
  • Irgacure 1 g (registered photopolymerization initiator) of registered trademark 819 (manufactured by BASF) was dissolved in 18 g of ethyl acetate.
  • aqueous phase component As an aqueous phase component, 0.4 g of sodium dodecyl sulfate was dissolved in 50 g of distilled water. The aqueous phase component was added to the oil phase component, mixed, and emulsified at 12,000 rpm for 10 minutes using a homogenizer. The obtained emulsion was added to 25 g of distilled water, stirred at room temperature for 30 minutes, and then stirred at 50 ° C. for 3 hours to distill off ethyl acetate. Then, stirring was further continued while distilling off water at 50 ° C., and the stirring was stopped when the solid content concentration of the dispersion liquid of particles 18 reached about 40% by mass to obtain a dispersion liquid of particles 18. The average particle diameter of the particles measured by the light scattering method was 0.19 ⁇ m.
  • TPO represents Lucirin (registered trademark) TPO (2,4,6-trimethylbenzoyldiphenylphosphine oxide, manufactured by BASF).
  • Irgacure® 184 is 1-hydroxycyclohexyl phenyl ketone manufactured by BASF.
  • Irgacure (registered trademark) 819 is bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide manufactured by BASF.
  • UA-306T is manufactured by Kyoeisha Chemical Co., Ltd. (pentaerythritol triacrylate, toluene diisocyanate, urethane prepolymer).
  • Examples 1 to 3 Comparative Examples 1 and 2
  • Table 9 shows the evaluation results.
  • the description of “-” in the table means that the above component is not contained.
  • top gel manufactured by Mogabrook Co., Ltd.
  • a brush was similarly irradiated with an ultraviolet lamp (36 W) for 2 minutes.
  • an ultraviolet lamp 36 W
  • nail makeup was made on the nails of 10 people.
  • the total film thickness of the color layer and the top layer was about 250 ⁇ m.
  • Ten people who applied nail makeup were allowed to live their daily lives as they were, and the number of days until the appearance of the nail makeup was poor (floating from the nail, lacking nail makeup, scratching, etc.) was measured. Table 9 shows the number of days until appearance failure occurs in the nail makeup of five people.
  • the nail cosmetic produced in the same manner was covered with a cotton soaked with acetone after 1 day from the production, and further covered with aluminum foil over the cotton and left for 15 minutes. Thereafter, after removing the aluminum foil and cotton, the removal was carried out by gradually removing the nail cosmetic using an orange stick. Table 9 shows the time required for removal with an orange stick and the result of visual observation of the nail surface after removal.
  • C Nail surface whitened
  • Aqueous emulsion (1) acrylic self-crosslinkable photocurable emulsion, functional group: acryloyl group, solid content: about 40% by mass, number average molecular weight of polymer: about 100,000, manufactured by Cray Valley, CRAYMUL -2717 (trademark)
  • Aqueous emulsion (2) urethane-based non-self-crosslinking photocurable emulsion, functional group: acryloyl group, solid content: about 40% by mass, number average molecular weight of polymer: about 100,000, manufactured by Albertingk, LUX -2411 (trademark) Polyethylene glycol: manufactured by Sasol, LIPOXOL 1500 (trademark), weight average molecular weight: about 1,500 Carnauba wax: Carnaubawax (trademark) manufactured by Toa Kasei Co., Ltd. Leveling agent: foam-breaking polysiloxane, BYK Chemie, BYK028
  • the nail cosmetic of the present invention has high water resistance and scratch resistance and high durability.
  • Example 10 Each component of the amount (part by mass) shown in Table 10 was weighed into a brown glass bottle, and then sufficiently stirred and mixed at room temperature to obtain a composition. With respect to the obtained composition, the above tests were performed and evaluated. Table 10 shows the evaluation results.
  • Example 9 Each component in an amount (parts by mass) shown in Table 11 was weighed into a brown glass bottle, and then sufficiently stirred and mixed at room temperature to obtain a composition. With respect to the obtained composition, the above tests were performed and evaluated. The evaluation results are shown in Table 11.
  • Example 12 Each component of the amount (part by mass) shown in Table 12 was weighed into a brown glass bottle, and then sufficiently stirred and mixed at room temperature to obtain a composition. With respect to the obtained composition, the above tests were performed and evaluated. The evaluation results are shown in Table 12.
  • Example 16 to 18 Each component of the amount (part by mass) shown in Table 13 was weighed into a brown glass bottle, and then sufficiently stirred and mixed at room temperature to obtain a composition. With respect to the obtained composition, the above tests were performed and evaluated. The evaluation results are shown in Table 13.
  • Monomer (1) in Table 13 has the following structure.
  • Examples 19 to 21, Comparative Example 3 The dispersion liquid of particles 1 obtained as described above was subjected to centrifugal separation at 14,500 rpm for 30 minutes to precipitate the solid particles. The separated supernatant was removed by decantation, and the remaining solid was spread thinly on an unbaked plate and dried at room temperature at 23 ° C. for 3 days. In this way, a solid of particles 1 (particle 1D) was obtained. Similarly, solid particles 8D and particles 14D were obtained from the dispersion of particles 8 and the dispersion of particles 14, respectively. In accordance with the formulation shown in Table 14, each component was weighed into a glass container, added with glass beads, and mixed for 1 hour in a paint shaker. Thus, a nail cosmetic was prepared.
  • the obtained nail cosmetic was applied onto the nails of 10 humans and cured by irradiation with an ultraviolet lamp (36 W) for 2 minutes.
  • the thickness of the cured coating was about 150 ⁇ m ( ⁇ 10 ⁇ m).
  • a commercially available calgel # CG-03 fresh pink (manufactured by Mogabrook Co., Ltd.) was applied as a color layer on the formed film with a brush and irradiated with an ultraviolet lamp (36 W) for 1 minute.
  • a commercially available top gel manufactured by Mogabrook Co., Ltd.
  • each component was weighed into a brown polyethylene bottle and mixed at 40 ° C. for 24 hours.
  • a nail cosmetic was prepared.
  • the obtained nail cosmetic was applied onto the nails of 10 humans and cured by irradiation with an ultraviolet lamp (36 W) for 2 minutes.
  • the thickness of the cured coating was about 150 ⁇ m ( ⁇ 10 ⁇ m).
  • a commercially available calgel # CG-03 fresh pink (manufactured by Mogabrook Co., Ltd.) was applied as a color layer on the formed film with a brush and irradiated with an ultraviolet lamp (36 W) for 1 minute.
  • top gel manufactured by Mogabrook Co., Ltd.
  • a brush was similarly irradiated with an ultraviolet lamp (36 W) for 2 minutes.
  • an ultraviolet lamp 36 W
  • nail makeup was made on the nails of 10 people.
  • the total film thickness of the color layer and the top layer was about 250 ⁇ m.

Abstract

La présente invention concerne une préparation cosmétique pour ongles qui dure plus longtemps et qui permet de réduire la charge au bout des doigts et sur les ongles et un kit de décoration d'ongles comprenant la préparation cosmétique pour ongles. La préparation cosmétique pour ongles selon la présente invention se caractérise en ce qu'elle contient des particules qui comprennent chacune des groupes polymérisables, notamment une structure réticulée en trois dimensions ayant au moins un type de liaison choisi dans le groupe constitué de liaisons uréthane, de liaisons thio-uréthane, de liaisons dithio-uréthane, de liaisons urée et de liaisons thio-urée, et en ce qu'elle contient un initiateur de photopolymérisation à l'intérieur. Le kit de décoration d'ongles selon la présente invention se caractérise en ce qu'il comprend la préparation cosmétique pour ongles.
PCT/JP2016/057498 2015-03-24 2016-03-10 Préparation cosmétique pour ongles et kit de décoration d'ongles WO2016152545A1 (fr)

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JP6483316B1 (ja) * 2018-08-03 2019-03-13 株式会社マックスオーガニック ジェルネイル用ジェル
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WO2018092745A1 (fr) * 2016-11-17 2018-05-24 三井化学株式会社 Procédé de production d'une résine de polyuréthanne, résine de polyuréthanne et article moulé
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WO2019069802A1 (fr) * 2017-10-05 2019-04-11 三井化学株式会社 Résine de polyuréthanne, article moulé, et procédé de production d'une résine de polyuréthanne
JP6483316B1 (ja) * 2018-08-03 2019-03-13 株式会社マックスオーガニック ジェルネイル用ジェル
JP2020019753A (ja) * 2018-08-03 2020-02-06 株式会社マックスオーガニック ジェルネイル用ジェル

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