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JP3382192B2 - Encapsulated color pigment - Google Patents
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JP3382192B2 - Encapsulated color pigment - Google Patents

Encapsulated color pigment

Info

Publication number
JP3382192B2
JP3382192B2 JP35278199A JP35278199A JP3382192B2 JP 3382192 B2 JP3382192 B2 JP 3382192B2 JP 35278199 A JP35278199 A JP 35278199A JP 35278199 A JP35278199 A JP 35278199A JP 3382192 B2 JP3382192 B2 JP 3382192B2
Authority
JP
Japan
Prior art keywords
color pigment
encapsulated
pigment
monomer
color
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
JP35278199A
Other languages
Japanese (ja)
Other versions
JP2001072887A (en
Inventor
博美 南部
竜太 土屋
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kao Corp
Original Assignee
Kao Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kao Corp filed Critical Kao Corp
Priority to JP35278199A priority Critical patent/JP3382192B2/en
Priority to PCT/JP2000/003852 priority patent/WO2001002493A1/en
Publication of JP2001072887A publication Critical patent/JP2001072887A/en
Application granted granted Critical
Publication of JP3382192B2 publication Critical patent/JP3382192B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001Post-treatment of organic pigments or dyes
    • C09B67/0004Coated particulate pigments or dyes
    • C09B67/0008Coated particulate pigments or dyes with organic coatings
    • C09B67/0013Coated particulate pigments or dyes with organic coatings with polymeric coatings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/11Encapsulated compositions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02Preparations containing skin colorants, e.g. pigments
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0097Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09CTREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C3/00Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/10Treatment with macromolecular organic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41Particular ingredients further characterized by their size
    • A61K2800/412Microsized, i.e. having sizes between 0.1 and 100 microns
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42Colour properties
    • A61K2800/43Pigments; Dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Description

【発明の詳細な説明】Detailed Description of the Invention

【0001】[0001]

【発明の属する技術分野】本発明は、着色顔料を架橋ポ
リマーでカプセル化したカプセル化着色顔料、その製
法、及びこれを含有する化粧料に関する。
TECHNICAL FIELD The present invention relates to an encapsulated color pigment in which a color pigment is encapsulated with a crosslinked polymer, a process for producing the same, and a cosmetic containing the same.

【0002】[0002]

【従来の技術】ファンデーション等のメイクアップ化粧
料には、各種の着色顔料が配合されている。しかし、着
色顔料は、配合系に含まれる粉体、油剤、界面活性剤等
の物質との接触や、熱、光等により、結晶成長を起こし
たり、変色や分解を生ずるという問題があった。また着
色顔料は、製品の安定性を悪化させたり、配合系におけ
る分散性が悪く、目的とする着色力が出なかったり、製
品の色とこれを肌に塗布したときの色が大きく異なる等
の問題もあった。
2. Description of the Related Art Makeup cosmetics such as foundations contain various color pigments. However, the color pigment has a problem that it causes crystal growth, discoloration or decomposition due to contact with powders, oil agents, surfactants and other substances contained in the compounding system, heat, light and the like. In addition, the color pigment may deteriorate the stability of the product, may have poor dispersibility in the compounding system, may not provide the desired coloring power, or may have a large difference between the product color and the color when applied to the skin. There was also a problem.

【0003】これらの着色顔料に関する問題の防止策と
して、着色顔料の表面処理や、ポリマーによるカプセル
化がある。このカプセル化の方法としては、例えば主と
して以下に示す3法が挙げられる。
As measures for preventing the problems relating to these color pigments, there are surface treatment of color pigments and encapsulation with polymers. Examples of the encapsulation method include, for example, the following three methods.

【0004】A)in situ重合法 顔料を界面活性剤を含む水中に分散させておき、これに
ビニルモノマー(主としてスチレン、炭素数1〜4の
(メタ)アクリレート等の高極性モノマー)と重合開始
剤を加え、加温、攪拌しながら重合反応を行い、ろ過、
水洗を繰り返してポリマー被覆顔料を得る方法である。
A) In situ polymerization method A pigment is dispersed in water containing a surfactant, and a vinyl monomer (mainly styrene, a highly polar monomer such as (meth) acrylate having 1 to 4 carbon atoms) is initiated to initiate polymerization. The agent is added, the polymerization reaction is performed while heating and stirring, filtration,
It is a method of obtaining a polymer-coated pigment by repeating washing with water.

【0005】B)コアセルベーション法 ポリマーをベンゼン、トルエン等の有機溶媒に溶解させ
ておき、これに顔料を加えて撹拌、分散させ、次にメタ
ノール、エタノール等のアルコールを加えて顔料表面に
ポリマーを析出させ、ろ過、洗浄を繰り返してポリマー
被覆顔料を得る方法である。
B) Coacervation method The polymer is dissolved in an organic solvent such as benzene and toluene, and the pigment is added to this and stirred and dispersed, and then alcohol such as methanol and ethanol is added to the polymer on the surface of the pigment. Is precipitated, and filtration and washing are repeated to obtain a polymer-coated pigment.

【0006】C)液中乾燥法 ポリマーをベンゼン、トルエン等の有機溶媒に溶解させ
ておき、これに顔料を加えて撹拌、分散させ、その後、
溶媒を留去してポリマー被覆顔料を得る方法である。
C) In-Liquid Drying Polymer is dissolved in an organic solvent such as benzene or toluene, and a pigment is added to this polymer and the mixture is stirred and dispersed.
In this method, the solvent is distilled off to obtain a polymer-coated pigment.

【0007】しかしながら、これらの方法では、溶解パ
ラメーターの高いモノマー又は溶解パラメータの高い有
機溶媒(コアセルベーション法,液中乾燥法)を使用し
ているために、製造過程において有機顔料の結晶成長を
生じ、これにより顔料のポリマー被覆が不十分となった
り、顔料の粗大化による着色力の低下を起こすという問
題があった。また、被覆剤が高い極性を有するポリマー
の未架橋のものないしパーオキシド開始剤により緩く架
橋されたものであるため、たとえ十分に被覆されていて
も、化粧品配合に使用する極性油剤等により容易に可塑
化、溶解してしまい、顔料の結晶成長、変色、分解等を
起こすという問題があった。
However, in these methods, since a monomer having a high solubility parameter or an organic solvent having a high solubility parameter (coacervation method, in-liquid drying method) is used, crystal growth of the organic pigment is caused in the production process. There is a problem in that the polymer coating of the pigment becomes insufficient due to this, and the coloring power decreases due to the coarsening of the pigment. Further, since the coating agent is an uncrosslinked polymer having a high polarity or is loosely crosslinked with a peroxide initiator, even if it is sufficiently coated, it is easily plasticized by a polar oil agent or the like used for cosmetic formulation. However, there is a problem that the pigment crystal grows, discolors, decomposes, and the like.

【0008】[0008]

【発明が解決しようとする課題】本発明の課題は、着色
顔料の結晶成長を起こすことのないように架橋ポリマー
で被覆された、簡便に製造可能な、またこれを化粧料に
配合した場合には着色顔料本来の鮮やかな色彩と着色力
を発揮し、色の安定性、製品の安定性、顔料分散性、塗
布色の均一性及び使用感に優れた化粧料を与えるカプセ
ル化着色顔料、及びこれを含有する化粧料を提供するこ
とである。
SUMMARY OF THE INVENTION An object of the present invention is to provide a cross-linked polymer coated so as not to cause crystal growth of a coloring pigment, which can be easily produced and which is incorporated into a cosmetic composition. Is an encapsulated color pigment that exhibits the original vivid color and coloring power of the color pigment, and that provides a cosmetic with excellent color stability, product stability, pigment dispersibility, coating color uniformity, and usability. It is to provide a cosmetic containing this.

【0009】[0009]

【課題を解決するための手段】本発明は、着色顔料を芯
物質とし、Fedorsの方法により計算した溶解パラ
メータが8.80以下のビニルモノマーとラジカル重合
性基を2つ以上有するモノマーである架橋剤を必須と
し、該ビニルモノマーと該架橋剤の総量が50重量%以
上であるモノマーを重合して得られる架橋ポリマーを壁
材とするカプセル化着色顔料を提供するものである。
DISCLOSURE OF THE INVENTION The present invention uses a coloring pigment as a core substance and a dissolution parameter calculated by the method of Fedors.
Meter 8.80 following bi Nirumonoma over and radical polymerization
A crosslinking agent is a monomer having a sex group two or more as essential, the total amount of the vinyl monomer and the crosslinking agent is 50 wt% or less
The present invention provides an encapsulated color pigment having a wall material of a crosslinked polymer obtained by polymerizing the above monomers.

【0010】[0010]

【発明の実施の形態】本発明のカプセル化着色顔料の膜
剤である架橋ポリマーの原料として用いられるビニルモ
ノマーは、着色顔料の結晶成長防止の観点から、溶解パ
ラメーターが8.80以下であることが必要である。
BEST MODE FOR CARRYING OUT THE INVENTION The vinyl monomer used as a raw material for a cross-linked polymer which is a film agent for an encapsulated color pigment of the present invention must have a solubility parameter of 8.80 or less from the viewpoint of preventing crystal growth of the color pigment. Is.

【0011】本明細書にいう溶解パラメーターとは、Fe
dorsの方法〔R. F. Fedors. Polyme. Eng. Sic., 14, 1
47(1974)〕により計算された値であり、この溶解パラメ
ーターが8.80以下であるビニルモノマーとしては、フッ
素化されていてもよい炭素数8以上(より好ましくは炭
素数8〜40)の直鎖又は分岐アルキルの(メタ)アクリ
レート、分子鎖の片末端にラジカル重合性基を有するジ
メチルポリシロキサン化合物が挙げられる。具体例とし
ては、オクチル(メタ)アクリレート、2-エチルヘキシ
ル(メタ)アクリレート、ラウリル(メタ)アクリレー
ト、ミリスチル(メタ)アクリレート、パルミチル(メ
タ)アクリレート、ステアリル(メタ)アクリレート、
イソステアリル(メタ)アクリレート、ベヘニル(メ
タ)アクリレート、炭素鎖6以上の2-(パーフルオロア
ルキル)エチル(メタ)アクリレート、分子鎖の片末端
に(メタ)アクリル基を有する分子量500〜10,000のジ
メチルポリシロキサン化合物等が挙げられる。
The solubility parameter as used herein means Fe
dors method [RF Fedors. Polyme. Eng. Sic., 14, 1
47 (1974)], and as the vinyl monomer having a solubility parameter of 8.80 or less, a linear monomer having 8 or more carbon atoms (more preferably 8 to 40 carbon atoms) which may be fluorinated. Alternatively, a branched alkyl (meth) acrylate or a dimethylpolysiloxane compound having a radically polymerizable group at one end of the molecular chain can be used. Specific examples include octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, myristyl (meth) acrylate, palmityl (meth) acrylate, stearyl (meth) acrylate,
Isostearyl (meth) acrylate, behenyl (meth) acrylate, 2- (perfluoroalkyl) ethyl (meth) acrylate having 6 or more carbon chains, dimethyl having a (meth) acrylic group at one end of the molecular chain and a molecular weight of 500 to 10,000. Examples thereof include polysiloxane compounds.

【0012】架橋剤は、形成される壁材を物理的及び化
学的に強固なものとするために用いられる。架橋剤とし
ては、ラジカル重合性基を2つ以上有するモノマーが挙
げられ、具体例としては、エチレングリコールジ(メ
タ)アクリレート、ジエチレングリコールジ(メタ)ア
クリレート、トリエチレングリコールジ(メタ)アクリ
レート、ポリエチレングリコールジ(メタ)アクリレー
ト、1,3-ブタンジオールジ(メタ)アクリレート、1,4-
ブタンジオールジ(メタ)アクリレート、1,6-ヘキサン
ジオールジ(メタ)アクリレート、ネオペンチルグリコ
ールジ(メタ)アクリレート、1,10-デカンジオールジ
(メタ)アクリレート、プロピレングリコールジ(メ
タ)アクリレート、ポリプロピレングリコールジ(メ
タ)アクリレート、トリメチロールプロパントリ(メ
タ)アクリレート、ペンタエリスリトールトリ(メタ)
アクリレート、ペンタエリスリトールテトラ(メタ)ア
クリレート、ジペンタエリスリトールヘキサ(メタ)ア
クリレート等の(メタ)アクリレート残基を2つ以上有
するモノマーが挙げられる。
The cross-linking agent is used to make the formed wall material physically and chemically strong. Examples of the cross-linking agent include monomers having two or more radically polymerizable groups, and specific examples include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol. Di (meth) acrylate, 1,3-butanediol di (meth) acrylate, 1,4-
Butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1,10-decanediol di (meth) acrylate, propylene glycol di (meth) acrylate, polypropylene Glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate
Examples thereof include monomers having two or more (meth) acrylate residues such as acrylate, pentaerythritol tetra (meth) acrylate, and dipentaerythritol hexa (meth) acrylate.

【0013】これらのモノマーの組成比としては、溶解
パラメーターが8.80以下であるビニルモノマーと架橋剤
の総量が50重量%以上で、かつ溶解パラメーターが8.80
以下であるビニルモノマーと架橋剤の重合比率が90/10
〜10/90、特に80/20〜20/80となるようにするのが好
ましい。
The composition ratio of these monomers is such that the total amount of the vinyl monomer having a solubility parameter of 8.80 or less and the crosslinking agent is 50% by weight or more, and the solubility parameter is 8.80.
The following polymerization ratio of vinyl monomer and cross-linking agent is 90/10
It is preferable to be -10/90, especially 80 / 20-20 / 80.

【0014】本発明のカプセル化着色顔料の芯物質であ
る着色顔料としては、水に不溶性の有機系着色顔料(不
溶性アゾ顔料)及び有機系レーキ着色顔料が挙げられ、
具体例としては、黄色系顔料として、黄色205号、黄色4
01号等のハンザイエロー、ジスアゾイエロー、キノリン
イエロー等が、赤色系顔料として、赤色202号、赤色204
号、赤色226号等が、青色系顔料として、青色404号(フ
タロシアニンブルー)等が挙げられ、表面処理が施され
ているものであってもよい。これらのうち、特に黄色40
1号及び赤色202号が好ましい。またこれら着色顔料は、
2種以上の混合物、又は体質顔料等との混合物としてカ
プセル化してもよい。
Examples of the color pigment as the core substance of the encapsulated color pigment of the present invention include water-insoluble organic color pigments (insoluble azo pigments) and organic lake color pigments.
As a specific example, as a yellow pigment, yellow 205, yellow 4
No. 01 and other Hansa Yellow, Disazo Yellow, Quinoline Yellow, etc. are red pigments such as Red No. 202 and Red 204
No. 226, Red No. 226, and the like, and blue pigments such as Blue No. 404 (phthalocyanine blue) and the like, which may be surface-treated. Of these, especially yellow 40
No. 1 and Red No. 202 are preferred. In addition, these color pigments
You may encapsulate as a mixture of 2 or more types, or a mixture with an extender pigment.

【0015】重合開始剤としては、油溶性アゾ系開始
剤、パーオキシド系開始剤が挙げられ、具体例として
は、2,2′-アゾビスイソブチロニトリル(AIBN)、2,
2′-アゾビスイソバレロニトリル、2,2′-アゾビス(2-
メチルブチロニトリル)、ベンゾイルパーオキシド(BP
O)、ラウロイルパーオキシド(LPO)等が挙げられる。
Examples of the polymerization initiator include oil-soluble azo initiators and peroxide initiators, and specific examples include 2,2'-azobisisobutyronitrile (AIBN), 2,
2'-azobisisovaleronitrile, 2,2'-azobis (2-
Methyl butyronitrile), benzoyl peroxide (BP
O), lauroyl peroxide (LPO) and the like.

【0016】本発明のカプセル化着色顔料及びその芯物
質である着色顔料の粒径は、着色力とカプセル化率によ
って異なるが、カプセル化着色顔料は平均粒径0.1〜50
μm、特に0.2〜30μmが、着色顔料は平均粒径0.01〜10
μm、特に0.02〜5μmが好ましい。またカプセル中に内
包される着色顔料の内包量も着色力とカプセル化率によ
って異なるが、1〜90重量%、特に5〜50重量%が好ま
しい。
The particle size of the encapsulated color pigment of the present invention and the color pigment as the core substance thereof varies depending on the coloring power and the encapsulation rate, but the encapsulated color pigment has an average particle size of 0.1 to 50.
μm, especially 0.2 to 30 μm, the color pigment has an average particle size of 0.01 to 10
μm, particularly preferably 0.02 to 5 μm. The amount of the color pigment contained in the capsule also varies depending on the coloring power and the encapsulation rate, but is preferably 1 to 90% by weight, particularly preferably 5 to 50% by weight.

【0017】本発明のカプセル化着色顔料は、着色顔料
の存在下で、溶解パラメーターが8.80以下であるビニル
モノマーと架橋剤を主体とするモノマーを懸濁重合する
ことによって製造できる。
The encapsulated color pigment of the present invention can be produced by suspension polymerization of a vinyl monomer having a solubility parameter of 8.80 or less and a monomer mainly containing a crosslinking agent in the presence of the color pigment.

【0018】すなわち、ビニルモノマー、架橋剤、着色
顔料及び重合開始剤よりなるビニルモノマー分散液を、
分散剤、乳化剤の存在下、水中に分散あるいは懸濁させ
液滴とし、重合反応を行うことによって目的とするカプ
セル化着色顔料を製造することができる。
That is, a vinyl monomer dispersion liquid comprising a vinyl monomer, a cross-linking agent, a color pigment and a polymerization initiator,
The target encapsulated color pigment can be produced by dispersing or suspending in water in the presence of a dispersant and an emulsifier to form droplets and carrying out a polymerization reaction.

【0019】また、ほかの方法として、着色顔料を分散
剤、乳化剤の存在下、あらかじめ水中に分散させてお
き、次いでビニルモノマー、架橋剤及び重合開始剤より
なるビニルモノマー分散液をその着色顔料分散液に加え
て、再度分散することによりモノマー溶液と顔料を合一
させた液滴とし、重合反応を行うことによっても目的と
するカプセル化着色顔料を製造することができる。
As another method, a color pigment is previously dispersed in water in the presence of a dispersant and an emulsifier, and then a vinyl monomer dispersion liquid containing a vinyl monomer, a crosslinking agent and a polymerization initiator is dispersed in the color pigment. The target encapsulated colored pigment can also be produced by adding the liquid and then dispersing it again to form a droplet in which the monomer solution and the pigment are united and performing a polymerization reaction.

【0020】さらに、原料となる着色顔料が水で希釈さ
れたウエットケーク着色顔料である場合には、ウエット
ケーク着色顔料とビニルモノマーとを混合し、生じた水
相を除去した後、架橋剤存在下に懸濁重合することによ
っても目的とするカプセル化着色顔料を製造することが
できる。この場合、架橋剤はビニルモノマーとともにウ
エットケーク着色顔料と混合してもよいし、水相除去後
に添加してもよい。より具体的には、ウエットケーク着
色顔料とビニルモノマーとを混合し、生じた着色水相を
除去して着色顔料が分散したモノマー分散液を得る。必
要に応じて、このモノマー分散液を少なくとも1回水で
洗浄し、架橋剤を加え、必要により分散剤、乳化剤を添
加して水中にモノマーを分散あるいは懸濁させ液滴と
し、重合反応を行う。
Further, when the starting color pigment is a wet cake color pigment diluted with water, the wet cake color pigment and vinyl monomer are mixed, the resulting aqueous phase is removed, and then a crosslinking agent is present. The target encapsulated color pigment can also be produced by suspension polymerization below. In this case, the crosslinking agent may be mixed with the wet cake color pigment together with the vinyl monomer, or may be added after removing the aqueous phase. More specifically, a wet cake color pigment and a vinyl monomer are mixed and the resulting colored aqueous phase is removed to obtain a monomer dispersion liquid in which the color pigment is dispersed. If necessary, this monomer dispersion is washed at least once with water, a cross-linking agent is added, and if necessary, a dispersant and an emulsifier are added to disperse or suspend the monomer in water to form droplets and carry out a polymerization reaction. .

【0021】ビニルモノマー分散液には、カプセル化着
色顔料が目的とする物性を損なわない範囲内で、必要に
応じて有機溶媒を加えてもよい。このような有機溶媒と
しては、例えば、直鎖又は環状の飽和炭化水素系溶剤
(n-ペンタン、n-ヘキサン、n-ヘプタン、n-オクタン、
n-ノナン、n-デカン、シクロヘキサン等)、直鎖又は環
状の不飽和炭化水素系溶剤(トルエン、キシレン等)、
ケトン系有機溶剤(アセトン、メチルエチルケトン
等)、エステル系有機溶剤(酢酸エチル、酢酸ブチル
等)、直鎖又は環状のポリジメチルシロキサン等が挙げ
られる。
If necessary, an organic solvent may be added to the vinyl monomer dispersion liquid as long as the encapsulated color pigment does not impair the desired physical properties. As such an organic solvent, for example, a linear or cyclic saturated hydrocarbon solvent (n-pentane, n-hexane, n-heptane, n-octane,
n-nonane, n-decane, cyclohexane, etc.), linear or cyclic unsaturated hydrocarbon solvent (toluene, xylene, etc.),
Examples thereof include ketone organic solvents (acetone, methyl ethyl ketone, etc.), ester organic solvents (ethyl acetate, butyl acetate, etc.), and linear or cyclic polydimethylsiloxane.

【0022】ここで着色顔料の分散には、ホモジナイザ
ー、高圧ホモジナイザー、超音波分散機、アトライター
ミル、ボールミル、サンドミル等の分散機が用いられ
る。また分散・乳化剤としては、ラウリル硫酸ナトリウ
ム、セチル硫酸ナトリウム、ポリオキシエチレンラウリ
ルエーテル硫酸ナトリウム等のアニオン性界面活性剤、
その他の、カチオン性界面活性剤、ノニオン性界面活性
剤等の低分子の界面活性剤;ポリビニルアルコール、ポ
リビニルピロリドン、ヒドロキシエチルセルロース、ヒ
ドロキシプロピルセルロース、ゼラチン、デンプン、カ
ルボキシメチルセルロース、ポリビニルアルキルエーテ
ル等の高分子分散剤;硫酸バリウム、硫酸カリウム、炭
酸バリウム、炭酸カルシウム、炭酸マグネシウム、リン
酸カルシウム等の難水溶性無機塩が挙げられる。
Here, for the dispersion of the color pigment, a homogenizer, a high pressure homogenizer, an ultrasonic disperser, an attritor mill, a ball mill, a sand mill or the like is used. As the dispersing / emulsifying agent, anionic surfactants such as sodium lauryl sulfate, sodium cetyl sulfate and sodium polyoxyethylene lauryl ether sulfate,
Other low-molecular-weight surfactants such as cationic surfactants and nonionic surfactants; polymers such as polyvinyl alcohol, polyvinylpyrrolidone, hydroxyethyl cellulose, hydroxypropyl cellulose, gelatin, starch, carboxymethyl cellulose and polyvinyl alkyl ether Dispersants: sparingly water-soluble inorganic salts such as barium sulfate, potassium sulfate, barium carbonate, calcium carbonate, magnesium carbonate and calcium phosphate.

【0023】重合の温度及び時間は、用いるモノマー等
によって異なるが、重合温度は20〜95℃が、重合時間は
3〜20時間が好ましい。
The temperature and time of polymerization vary depending on the monomers used and the like, but the polymerization temperature is preferably 20 to 95 ° C., and the polymerization time is preferably 3 to 20 hours.

【0024】重合後、濾過、遠心分離等により固液分離
し、水相を除去し、必要に応じて水洗を行った後、減圧
乾燥、噴霧乾燥、凍結乾燥等の通常の手段によって、カ
プセル化着色顔料を粉体として単離することができる。
また必要に応じて凝集物の解砕を行う。
After the polymerization, solid-liquid separation is carried out by filtration, centrifugation, etc., the aqueous phase is removed, and if necessary, washing with water is carried out, followed by encapsulation by usual means such as vacuum drying, spray drying and freeze drying. The color pigment can be isolated as a powder.
If necessary, the aggregates are disintegrated.

【0025】以上のようにして得られた本発明のカプセ
ル化着色顔料を配合しうる化粧料としては、その製品形
態、形状等を問わないが、ファンデーション、頬紅、ア
イシャドウ、マスカラ、アイライナー、アイブロウ、口
紅、ネイルエナメルメイクアップ化粧料が好ましい。化
粧料に対するカプセル化着色顔料の配合量は、0.1〜50
重量%、特に0.2〜30重量%が好ましい。
The cosmetics to which the encapsulated color pigment of the present invention obtained as described above can be mixed are not limited in terms of product form, shape, etc., but may be foundation, blusher, eye shadow, mascara, eyeliner, Eyebrow, lipstick and nail enamel makeup cosmetics are preferred. The amount of the encapsulated coloring pigment mixed with the cosmetic is 0.1 to 50.
%, Especially 0.2 to 30% by weight is preferred.

【0026】また更に本発明の化粧料には、通常化粧品
用原料として用いられる他の成分、例えば白色顔料、体
質顔料、着色顔料、パール顔料、天然鉱物、有機粉末、
油剤、紫外線防御剤、ゲル化剤、ワックス、金属石鹸、
界面活性剤、保湿剤、防腐剤、香料、その他各種添加剤
を適宜選択して配合することができる。
Furthermore, in the cosmetic of the present invention, other components usually used as raw materials for cosmetics, such as white pigments, extender pigments, coloring pigments, pearl pigments, natural minerals, organic powders,
Oil agent, UV protection agent, gelling agent, wax, metal soap,
Surfactants, moisturizers, preservatives, perfumes, and various other additives can be appropriately selected and added.

【0027】[0027]

【実施例】実施例1 300mLのビーカーに、ラウリルメタクリレート56g、エ
チレングリコールジメタクリレート19g及びラウロイル
パーオキシド1.5gを仕込み、溶解後に黄色401号25gを
添加して分散した。その後、この分散液を1%ポリビニ
ルアルコール(日本合成化学工業製,ゴーセノールGH-1
7)水溶液750g中に加えて、超音波分散機を用いて分散
した(平均粒径2.2μm)。次いで、得られた分散液を10
00mLのセパラブルフラスコに仕込み、窒素置換後、200r
pmで攪拌しながら、75℃で8時間、窒素雰囲気下で重合
を行った。重合終了後、遠心分離にて固体を集め、水で
洗浄し、減圧乾燥後、カプセル化した黄色401号95gを
得た(平均粒径2.0μm,黄色401号の内包率25重量
%)。
Example 1 A 300-mL beaker was charged with 56 g of lauryl methacrylate, 19 g of ethylene glycol dimethacrylate and 1.5 g of lauroyl peroxide, and after dissolution, 25 g of yellow No. 401 was added and dispersed. Then, this dispersion was mixed with 1% polyvinyl alcohol (Nippon Gosei Kagaku Kogyo, Gohsenol GH-1).
7) The solution was added to 750 g of the aqueous solution and dispersed using an ultrasonic disperser (average particle size 2.2 μm). Then, the dispersion obtained is mixed with 10
Charge into a 00 mL separable flask, replace with nitrogen, and then
Polymerization was carried out at 75 ° C. for 8 hours under a nitrogen atmosphere while stirring at pm. After the completion of the polymerization, the solid was collected by centrifugation, washed with water, and dried under reduced pressure to obtain 95 g of encapsulated Yellow No. 401 (average particle size 2.0 μm, inclusion rate of Yellow No. 401 of 25% by weight).

【0028】実施例2 300mLのビーカーに、イソステアリルアクリレート68
g、ジビニルベンゼン17g及び2,2′-アゾビス(2-メチ
ルブチロニトリル)1.0gを仕込み、溶解した。その
後、黄色401号15gをアトライターミルにて1%ポリビ
ニルアルコール(日本合成化学工業製,ゼーセノールGH
-17)水溶液750g中に分散した分散液中に、先に調製し
ておいた開始剤を含む上記モノマー溶液を加え、更に超
音波分散機を用いて分散した(平均粒径2.5μm)。次い
で、得られた分散液を1000mLのセパラブルフラスコに仕
込み、窒素置換後、200rpmで攪拌しながら、80℃で8時
間、窒素雰囲気下で重合を行った。重合終了後、遠心分
離にて固体を集め、水で洗浄し、減圧乾燥後、カプセル
化した黄色401号93gを得た(平均粒径2.7μm,黄色401
号の内包率15重量%)。
EXAMPLE 2 Isostearyl acrylate 68 was added to a 300 mL beaker.
g, 17 g of divinylbenzene and 1.0 g of 2,2'-azobis (2-methylbutyronitrile) were charged and dissolved. Then, 15 g of yellow No. 401 was mixed with 1% polyvinyl alcohol (Nippon Gosei Kagaku Kogyo, Seesenol GH) with an attritor mill.
-17) To the dispersion liquid dispersed in 750 g of an aqueous solution, the above-prepared monomer solution containing the initiator was added, and further dispersed using an ultrasonic disperser (average particle diameter 2.5 μm). Then, the obtained dispersion was charged into a 1000 mL separable flask, and after nitrogen replacement, polymerization was carried out at 80 ° C. for 8 hours under a nitrogen atmosphere while stirring at 200 rpm. After the completion of the polymerization, the solid was collected by centrifugation, washed with water, and dried under reduced pressure to obtain 93 g of encapsulated yellow 401 (average particle size 2.7 μm, yellow 401
The inclusion rate of the issue is 15% by weight).

【0029】実施例3 300mLのビーカーに、ラウリルメタクリレート40g、1,6
-ヘキサンジオールジメタクリレート50g及びラウロイ
ルパーオキシド1.2gを仕込み、溶解後に黄色401号10g
を添加して分散した。その後、この分散液を1.0%ラウ
リル硫酸ナトリウム(花王製,エマールO)水溶液750
g中に加え、高圧ホモジナイザーを用いて分散した(平
均粒径2.5μm)。次いで、得られた分散液を1000mLのセ
パラブルフラスコに仕込み、窒素置換後、200rpmで攪拌
しながら、75℃で8時間、窒素雰囲気下で重合を行っ
た。重合終了後、遠心分離にて固体を集め、水で洗浄
し、減圧乾燥後、カプセル化した黄色401号94gを得た
(平均粒径2.5μm,黄色401号の内包率10重量%)。
Example 3 In a 300 mL beaker, 40 g of lauryl methacrylate, 1,6
-Hexanediol dimethacrylate (50 g) and lauroyl peroxide (1.2 g) were charged, and after dissolution, yellow No. 401 (10 g)
Was added and dispersed. Then, this dispersion is added with a 750% 1.0% aqueous solution of sodium lauryl sulfate (manufactured by Kao, Emal O).
It was added to the dispersion medium (g) and dispersed using a high-pressure homogenizer (average particle size 2.5 μm). Then, the obtained dispersion was charged into a 1000 mL separable flask, and after purging with nitrogen, polymerization was carried out at 75 ° C. for 8 hours under a nitrogen atmosphere while stirring at 200 rpm. After completion of the polymerization, solids were collected by centrifugation, washed with water, and dried under reduced pressure to obtain 94 g of encapsulated Yellow No. 401 (average particle size 2.5 μm, inclusion rate of Yellow No. 401 of 10% by weight).

【0030】実施例4 300mLのビーカーに、2-エチルヘキシルアクリレート40
g、ラウリルアクリレート20g、1,3-ブタンジオールジ
メタクリレート35g及びラウロイルパーオキシド1.3g
を仕込み、溶解後に赤色202号15gを添加して分散し
た。その後、この分散液を0.5%ポリビニルアルコール
(日本合成化学工業製,ゴーセノールGH-17)水溶液750
g中に加え、高圧ホモジナイザーを用いて分散した(平
均粒径3.5μm)。次いで、得られた分散液を1000mLのセ
パラブルフラスコに仕込み、窒素置換後、200rpmで攪拌
しながら、75℃で8時間、窒素雰囲気下で重合を行っ
た。重合終了後、遠心分離にて固体を集め、水で洗浄
し、減圧乾燥後、カプセル化した赤色20号92gを得た
(平均粒径3.2μm,赤色202号の内包率5重量%)。
Example 4 A 300 mL beaker was charged with 2-ethylhexyl acrylate 40
g, 20 g of lauryl acrylate, 35 g of 1,3-butanediol dimethacrylate and 1.3 g of lauroyl peroxide
After being dissolved, 15 g of Red No. 202 was added and dispersed. Then, this dispersion was added with a 0.5% polyvinyl alcohol (Nippon Gosei Kagaku Kogyo, Gohsenol GH-17) aqueous solution 750.
It was then dispersed in a high pressure homogenizer (average particle size 3.5 μm). Then, the obtained dispersion was charged into a 1000 mL separable flask, and after purging with nitrogen, polymerization was carried out at 75 ° C. for 8 hours under a nitrogen atmosphere while stirring at 200 rpm. After the completion of the polymerization, the solid was collected by centrifugation, washed with water, and dried under reduced pressure to obtain 92 g of encapsulated Red No. 20 (average particle size 3.2 μm, inclusion rate of Red No. 202 of 5% by weight).

【0031】実施例5 300mLのビーカーに、ポリジメチルシロキシプロピルメ
タクリレート(チッソ社製,サイラプレーンFM0711,Mw
1000)30g、イソステアリルメタクリレート20g、エチ
レングリコールジメタクリレート45g及びラウロイルパ
ーオキシド2.0gを仕込み、溶解後に黄色401号5gを添
加して分散した。その後、この分散液を0.5%ポリビニ
ルアルコール(日本合成化学工業製,ゴーセノールGH-1
7)/0.1%ラウリル硫酸ナトリウム(花王製,エマール
O)水溶液750g中に加え、超音波分散機を用いて分散
した(平均粒径3.7μm)。次いで、得られた分散液を10
00mLのセパラブルフラスコに仕込み、窒素置換後、200r
pmで攪拌しながら、75℃で8時間、窒素雰囲気下で重合
を行った。重合終了後、遠心分離にて固体を集め、水で
水洗し、減圧乾燥後、カプセル化した黄色401号97gを
得た(平均粒径3.5μm,黄色401号の内包率5重量
%)。
Example 5 In a 300 mL beaker, polydimethylsiloxypropyl methacrylate (manufactured by Chisso Corporation, Silaplane FM0711, Mw) was used.
1000) 30 g, isostearyl methacrylate 20 g, ethylene glycol dimethacrylate 45 g and lauroyl peroxide 2.0 g were charged, and after dissolution, 5 g of yellow No. 401 was added and dispersed. Then, this dispersion was mixed with 0.5% polyvinyl alcohol (Nippon Gosei Kagaku Kogyo, Gohsenol GH-1
7) /0.1% sodium lauryl sulfate (manufactured by Kao, Emal O) was added to 750 g of the aqueous solution and dispersed using an ultrasonic disperser (average particle diameter 3.7 μm). Then, the dispersion obtained is mixed with 10
Charge into a 00 mL separable flask, replace with nitrogen, and then
Polymerization was carried out at 75 ° C. for 8 hours under a nitrogen atmosphere while stirring at pm. After the completion of the polymerization, the solid was collected by centrifugation, washed with water and dried under reduced pressure to obtain 97 g of encapsulated Yellow No. 401 (average particle size 3.5 μm, inclusion rate of Yellow No. 401 of 5% by weight).

【0032】実施例6 300mLのビーカーに、ラウリルメタクリレート37.5g、エ
チレングリコールジメタクリレート37.5g、ラウロイル
パーオキシド1.5gを仕込み、溶解する。ついで黄色401
号ウエットケーク( 黄色401号25gと水75gからなる)に
上記モノマー溶液を加え混合し、ウエットケークより排
出された着色水を除去し、黄色401号が分散したモノマ
ー溶液を得る。この黄色401号分散モノマー溶液に水100
gを添加混合した後に、着色した水を除去する。この操
作を再度おこなって得られた黄色401号分散モノマー溶
液を1%ポリビニルアルコール(日本合成化学工業製、
ゴーセノールGH-17)水溶液750g中に加えて、超音波分
散機を用いて分散した(平均粒径2.2μm) 。次いで、
該分散液を1000mLのセパラブルフラスコに仕込み、窒素
置換後、200rpmで攪拌しながら、75℃で8時間、窒素雰
囲気下で重合を行った。重合終了後、遠心分離にて固体
を集め、水で洗浄し、減圧乾燥後、カプセル化した黄色
401号96gを得た(平均粒径2.1μm、黄色401号の内包率
25重量%) 。
Example 6 A 300 mL beaker was charged with 37.5 g of lauryl methacrylate, 37.5 g of ethylene glycol dimethacrylate and 1.5 g of lauroyl peroxide and dissolved. Followed by yellow 401
The above-mentioned monomer solution is added to No. Wet Cake (composed of 25 g of Yellow No. 401 and 75 g of water) and mixed to remove colored water discharged from the wet cake to obtain a monomer solution having Yellow No. 401 dispersed therein. Add 100 parts of water to this yellow 401 dispersion monomer solution.
After adding and mixing g, the colored water is removed. This operation was performed again to obtain a yellow 401 dispersion monomer solution and 1% polyvinyl alcohol (manufactured by Nippon Synthetic Chemical Industry,
Gohsenol GH-17) was added to 750 g of an aqueous solution and dispersed using an ultrasonic disperser (average particle size 2.2 μm). Then
The dispersion was charged into a 1000 mL separable flask, and after purging with nitrogen, polymerization was carried out at 75 ° C. for 8 hours under a nitrogen atmosphere while stirring at 200 rpm. After the polymerization was completed, the solid was collected by centrifugation, washed with water, dried under reduced pressure, and then encapsulated in yellow.
Obtained 96 g of No. 401 (average particle size 2.1 μm, inclusion rate of yellow No. 401)
25% by weight).

【0033】比較例1 300mLのビーカーに、スチレン75g及びラウロイルパー
オキシド2.0gを仕込み、溶解後に黄色401号25gを添加
して分散した。その後、この分散液を1.0%ポリビニル
アルコール(日本合成化学工業製,ゴーセノールGH-1
7)水溶液750g中に加え、超音波分散機を用いて分散し
た(平均粒径3.9μm)。次いで、得られた分散液を1000
mLのセパラブルフラスコに仕込み、窒素置換後、200rpm
で攪拌しながら、75℃で8時間、窒素雰囲気下で重合を
行った。重合終了後、遠心分離にて固体を集め、水で洗
浄し、減圧乾燥後、カプセル化した黄色401号95gを得
た(平均粒径3.7μm,黄色401号の内包率25重量%)。
Comparative Example 1 A 300 mL beaker was charged with 75 g of styrene and 2.0 g of lauroyl peroxide, and after dissolution, 25 g of Yellow No. 401 was added and dispersed. Then, this dispersion was mixed with 1.0% polyvinyl alcohol (Nippon Gosei Kagaku Kogyo, Gohsenol GH-1
7) The mixture was added to 750 g of an aqueous solution and dispersed using an ultrasonic disperser (average particle size 3.9 μm). Then, the dispersion obtained is 1000
Charge into a mL separable flask, replace with nitrogen, then 200 rpm
Polymerization was carried out at 75 ° C. for 8 hours under a nitrogen atmosphere while stirring at. After the completion of the polymerization, the solid was collected by centrifugation, washed with water, and dried under reduced pressure to obtain 95 g of encapsulated Yellow No. 401 (average particle diameter 3.7 μm, inclusion rate of Yellow No. 401 of 25% by weight).

【0034】比較例2 200mLのビーカーに、PMMA樹脂(旭化成製,デルペット7
20V)90g及びトルエン900gを仕込み、溶解後に赤色22
6号10gを添加して分散した。その後、この分散液を0.5
%ポリビニルアルコール(日本合成化学工業製,ゴーセ
ノールGH-17)/0.2%ラウリル硫酸ナトリウム水溶液20
00g中に加え、超音波分散機を用いて分散した(平均粒
径2.3μm)。次いで、得られた分散液を5000mLのナスフ
ラスコに仕込み、60℃、減圧下にて溶媒であるトルエン
を留去した。その後、遠心分離にて固体を集め、水で洗
浄し、減圧乾燥後、カプセル化した黄色401号91gを得
た(平均粒径2.5μm,黄色401号の内包率10重量%)。
Comparative Example 2 In a 200 mL beaker, PMMA resin (Asahi Kasei, Delpet 7
20V) 90g and toluene 900g were charged, and after dissolution, red 22
No. 6 No. 10 g was added and dispersed. Then, this dispersion is 0.5
% Polyvinyl alcohol (Nippon Gosei Kagaku Kogyo, Gohsenol GH-17) /0.2% sodium lauryl sulfate aqueous solution 20
It was added to 00 g and dispersed using an ultrasonic disperser (average particle diameter 2.3 μm). Then, the obtained dispersion was charged into a 5000 mL eggplant flask, and the solvent toluene was distilled off at 60 ° C. under reduced pressure. Then, the solid was collected by centrifugation, washed with water, and dried under reduced pressure to obtain 91 g of encapsulated Yellow No. 401 (average particle size 2.5 μm, inclusion rate of Yellow No. 401 of 10% by weight).

【0035】試験例1 実施例1〜6及び比較例1及び2で得られたカプセル化
着色顔料について、その着色力と退色度を評価した(表
2)。
Test Example 1 The encapsulating color pigments obtained in Examples 1 to 6 and Comparative Examples 1 and 2 were evaluated for their tinting strength and fading degree (Table 2).

【0036】(評価方法) (1) 着色力(Qt値): (イ)カプセル化着色顔料1gをタルクで希釈し100g
としたものを分析粉砕機(日本理化学機械社製)にて15
000rpmで2分間混合した後、30kg/cm2のプレス圧で成型
する。 (ロ)測色機〔村上色彩技術研究所社製,CMS1200(測
色径6mmφ)〕にて、成型品の分光反射率を測定し、以
下の計算式(1)及び(2)を用い、式(3)にて表される値を
着色力(Qt)とする。重価係数についてはJIS規格Z 872
2-1971に記載の2度視野における標準の光C(5nm間
隔)の値を用いる。
(Evaluation method) (1) Coloring power (Qt value): (a) 1 g of the encapsulated color pigment was diluted with talc to obtain 100 g.
With the analytical crusher (manufactured by Nihon Rikagaku Kikai) 15
After mixing at 000 rpm for 2 minutes, it is molded with a pressing pressure of 30 kg / cm 2 . (B) The spectral reflectance of the molded product is measured with a colorimeter [Murakami Color Research Laboratory Co., Ltd., CMS1200 (colorimetric diameter 6 mmφ)], and the following calculation formulas (1) and (2) are used. The value represented by equation (3) is the coloring power (Qt). Regarding the weight factor, JIS standard Z 872
The value of standard light C (5 nm interval) in the 2-degree visual field described in 2-1971 is used.

【0037】[0037]

【数1】 [Equation 1]

【0038】Qt=Qx+Qy+Qz (3)Qt = Qx + Qy + Qz (3)

【0039】〔Qt:着色力, Qx, Qy, Qz:式(2)で与
えられる値〕
[Qt: coloring power, Qx, Qy, Qz: values given by equation (2)]

【0040】(2) 退色度(ΔE):表1に示すモデル
処方の粉体部を分析粉砕器で粉砕し、これに紫外線防御
剤を加え、更に粉砕する。この粉砕物を固形ファンデー
ション用の金型にプレス成型して、測色し、この値を基
準値とする(L,a,b)。このものを80℃で7日放置した
後に再度測色して、基準値と7日放置後の測色値との色
差を退色度とした(ΔE=[(ΔL)2+(Δa)2+(Δ
b)2)]1/2;表2)。なお、退色度2.0以下で使用可能で
ある。
(2) Degree of fading (ΔE): The powder part of the model formulation shown in Table 1 is crushed by an analytical crusher, an ultraviolet protective agent is added to this, and further crushed. This crushed product is press-molded in a solid foundation mold, the color is measured, and this value is used as a reference value (L, a, b). After this was left at 80 ° C for 7 days, the color was measured again, and the color difference between the reference value and the colorimetric value after 7 days was taken as the degree of fading (ΔE = [(ΔL) 2 + (Δa) 2 + (Δ
b) 2 )] 1/2 ; Table 2). It can be used with a fading degree of 2.0 or less.

【0041】[0041]

【表1】 [Table 1]

【0042】[0042]

【表2】 [Table 2]

【0043】試験例2(実施例7〜10,比較例3) 表3に示す組成の固形ファンデーションを常法により製
造し、60℃にて7日間放置し、放冷後の化粧料につい
て、その使用感と塗布色を官能評価した。
Test Example 2 (Examples 7 to 10 and Comparative Example 3) Solid foundations having the compositions shown in Table 3 were produced by a conventional method, allowed to stand at 60 ° C. for 7 days, and allowed to cool. The feeling of use and the coating color were sensory evaluated.

【0044】(使用感)10人の専門パネラーにより、主
に塗布感と塗布後の化粧感についての官能評価を行い、
次の基準で評価した。 ◎:8人以上が良いと判断した ○:5〜7人が良いと判断した △:2〜4人が良いと判断した ×:1人未満が良いと判断した
(Feeling of use) Sensory evaluations were mainly conducted on the feeling of application and the feeling of makeup after application by 10 professional panelists.
The following criteria evaluated. ◎: 8 people or more were judged good ○: 5 to 7 people were judged to be good △: 2 to 4 people were judged to be good ×: Less than 1 person was judged to be good

【0045】(塗布色)10人の専門パネラーにより、主
に塗布色についての官能評価を行い、次の基準で評価し
た。 ◎:8人以上が良いと判断した ○:5〜7人が良いと判断した △:2〜4人が良いと判断した ×:1人未満が良いと判断した
(Coating Color) The sensory evaluation of the coating color was mainly conducted by 10 professional panelists, and the evaluation was carried out according to the following criteria. ◎: 8 people or more were judged good ○: 5 to 7 people were judged to be good △: 2 to 4 people were judged to be good ×: Less than 1 person was judged to be good

【0046】[0046]

【表3】 [Table 3]

【0047】試験例3(実施例11〜13,比較例4) 表4に示す組成の乳化ファンデーションを常法により製
造し、試験例2と同様にして官能評価を行った。
Test Example 3 (Examples 11 to 13, Comparative Example 4) Emulsion foundations having the compositions shown in Table 4 were produced by a conventional method, and sensory evaluation was performed in the same manner as in Test Example 2.

【0048】[0048]

【表4】 [Table 4]

【0049】試験例3(実施例14〜16,比較例5) 表に示す組成の油性ファンデーションを常法により製造
し、試験例2と同様にして官能評価を行った。
Test Example 3 (Examples 14 to 16 and Comparative Example 5) Oily foundations having the compositions shown in the table were produced by a conventional method, and sensory evaluation was conducted in the same manner as in Test Example 2.

【0050】[0050]

【表5】 [Table 5]

【0051】[0051]

【発明の効果】本発明のカプセル化着色顔料は、前記の
ごとく、着色顔料の結晶成長を起こさせずに架橋ポリマ
ーで被覆したカプセル化着色顔料であり、懸濁重合によ
り簡便且つ良好に製造可能である。この顔料を化粧料に
配合すると、下記実施例に示すように、着色顔料本来の
鮮やかな色彩と着色力を生かしつつ、配合系における色
の安定性、配合性、塗布色の均一性及び使用感を与え
る。
As described above, the encapsulated color pigment of the present invention is an encapsulated color pigment coated with a cross-linked polymer without causing crystal growth of the color pigment, and can be easily and favorably produced by suspension polymerization. Is. When this pigment is blended in cosmetics, as shown in the following examples, the color stability, blendability, uniformity of coating color and feeling of use in the blending system are achieved while making full use of the vivid color and coloring power inherent in the color pigment. give.

───────────────────────────────────────────────────── フロントページの続き (56)参考文献 特開 昭60−824(JP,A) 特開 平8−48899(JP,A) 特開 平7−331111(JP,A) 特開2000−53545(JP,A) 特開2000−226307(JP,A) 特開 平4−181950(JP,A) 特開 平7−248644(JP,A) 特開 平9−151342(JP,A) 特開2000−219749(JP,A) 特開2000−219841(JP,A) (58)調査した分野(Int.Cl.7,DB名) C09B 67/08 A61K 7/00 C09B 67/20 ─────────────────────────────────────────────────── ─── Continuation of the front page (56) References JP-A-60-824 (JP, A) JP-A-8-48899 (JP, A) JP-A-7-331111 (JP, A) JP-A-2000-53545 (JP, A) JP 2000-226307 (JP, A) JP 4-181950 (JP, A) JP 7-248644 (JP, A) JP 9-151342 (JP, A) JP 2000-219749 (JP, A) JP 2000-219841 (JP, A) (58) Fields investigated (Int.Cl. 7 , DB name) C09B 67/08 A61K 7/00 C09B 67/20

Claims (5)

(57)【特許請求の範囲】(57) [Claims] 【請求項1】 着色顔料を芯物質とし、Fedorsの
方法により計算した溶解パラメータが8.80以下のビ
ニルモノマーとラジカル重合性基を2つ以上有するモノ
マーである架橋剤を必須とし、該ビニルモノマーと該
架橋剤の総量が50重量%以上であるモノマーを重合し
て得られる架橋ポリマーを壁材とするカプセル化着色顔
料。
1. A color pigment as a core material, the Fedors
Mono- solubility parameter calculated by the method has two or more 8.80 or less bicycloalkyl <br/> Nirumonoma over and a radical polymerizable group
A crosslinking agent which is mers as essential, the vinyl monomer and the
An encapsulated color pigment having a wall material of a crosslinked polymer obtained by polymerizing a monomer having a total amount of the crosslinking agent of 50% by weight or more .
【請求項2】 着色顔料が、黄色401号及び/又は赤色20
2号である請求項1記載のカプセル化着色顔料。
2. The coloring pigment is Yellow No. 401 and / or Red No. 20.
The encapsulated color pigment according to claim 1, which is No. 2.
【請求項3】 着色顔料の存在下で、Fedorsの方
法により計算した溶解パラメータが8.80以下のビニ
ルモノマーとラジカル重合性基を2つ以上有するモノマ
ーである架橋剤を必須とし、該ビニルモノマーと該架
橋剤の総量が50重量%以上であるモノマーを懸濁重合
する請求項1又は2記載のカプセル化着色顔料の製法。
3. Fedors in the presence of color pigments
Monomer solubility parameters calculated by law has two or more 8.80 or less of vinyl <br/> Rumonoma over and a radical polymerizable group
A crosslinking agent which is over an essential, the vinyl monomer and the cross
The method for producing an encapsulated color pigment according to claim 1 or 2 , wherein a monomer having a total amount of the cross-linking agent of 50% by weight or more is suspension-polymerized.
【請求項4】 ウェットケークの着色顔料と、Fedo
rsの方法により計算した溶解パラメータが8.80以
下のビニルモノマーとを混合し、生じた水相を除去した
後、ラジカル重合性基を2つ以上有するモノマーである
架橋剤の存在下に懸濁重合する請求項1又は2記載のカ
プセル化着色顔料の製法。
4. A wet-cake color pigment, and Fedo
The dissolution parameter calculated by the rs method is 8.80 or more.
Mixing a vinyl monomer over the bottom, resulting the aqueous phase was removed, according to claim 1 or 2, wherein the suspension polymerization in the presence of a <br/> crosslinking agent is a monomer having a radical polymerizable group at least two Of the encapsulated colored pigment of.
【請求項5】 請求項1又は2記載のカプセル化着色顔
料を含有する化粧料。
5. A cosmetic containing the encapsulated color pigment according to claim 1 or 2.
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JP6706984B2 (en) * 2016-07-13 2020-06-10 大日精化工業株式会社 Method for producing resin beads containing organic pigment
JP6879691B2 (en) * 2016-08-10 2021-06-02 アイカ工業株式会社 Organic fine particles
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