JPS62250074A - Water-repellent, oil-repellent pigment and production thereof - Google Patents
Water-repellent, oil-repellent pigment and production thereofInfo
- Publication number
- JPS62250074A JPS62250074A JP9305486A JP9305486A JPS62250074A JP S62250074 A JPS62250074 A JP S62250074A JP 9305486 A JP9305486 A JP 9305486A JP 9305486 A JP9305486 A JP 9305486A JP S62250074 A JPS62250074 A JP S62250074A
- Authority
- JP
- Japan
- Prior art keywords
- pigment
- repellent
- water
- oil
- compound
- 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.)
- Granted
Links
- 239000000049 pigment Substances 0.000 title claims abstract description 31
- 239000005871 repellent Substances 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 4
- 239000007864 aqueous solution Substances 0.000 claims abstract description 3
- 239000010452 phosphate Substances 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 abstract description 5
- -1 amine phosphate Chemical class 0.000 abstract description 3
- 239000011248 coating agent Substances 0.000 abstract description 3
- 238000000576 coating method Methods 0.000 abstract description 3
- 235000021317 phosphate Nutrition 0.000 abstract 2
- 230000000052 comparative effect Effects 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000010445 mica Substances 0.000 description 12
- 229910052618 mica group Inorganic materials 0.000 description 12
- 239000003921 oil Substances 0.000 description 11
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 6
- 238000011282 treatment Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 239000004408 titanium dioxide Substances 0.000 description 3
- LVOJOIBIVGEQBP-UHFFFAOYSA-N 4-[[2-chloro-4-[3-chloro-4-[(5-hydroxy-3-methyl-1-phenylpyrazol-4-yl)diazenyl]phenyl]phenyl]diazenyl]-5-methyl-2-phenylpyrazol-3-ol Chemical compound CC1=NN(C(O)=C1N=NC1=CC=C(C=C1Cl)C1=CC(Cl)=C(C=C1)N=NC1=C(O)N(N=C1C)C1=CC=CC=C1)C1=CC=CC=C1 LVOJOIBIVGEQBP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 210000004243 sweat Anatomy 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241001251094 Formica Species 0.000 description 1
- LTGPFZWZZNUIIK-LURJTMIESA-N Lysol Chemical compound NCCCC[C@H](N)CO LTGPFZWZZNUIIK-LURJTMIESA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 101150029512 SCG2 gene Proteins 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 description 1
- 101150061397 cnfn gene Proteins 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000005660 hydrophilic surface Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- WTFXARWRTYJXII-UHFFFAOYSA-N iron(2+);iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+2].[Fe+3].[Fe+3] WTFXARWRTYJXII-UHFFFAOYSA-N 0.000 description 1
- LDHBWEYLDHLIBQ-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide;hydrate Chemical compound O.[OH-].[O-2].[Fe+3] LDHBWEYLDHLIBQ-UHFFFAOYSA-M 0.000 description 1
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/55—Phosphorus compounds
- A61K8/556—Derivatives containing from 2 to 10 oxyalkylene groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/11—Encapsulated compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
- A61K2800/43—Pigments; Dyes
Abstract
Description
【発明の詳細な説明】
産業上の利用分野；
本発明は下記化学式で示すフルオロアルキルジ（オキシ
エチル）アミンリン酸塩エステル（１）および／または
ω）（ＦＡＥＰで総称する。）で被覆さルた撥水性撥油
性顔料とその製造方法に関するものでめる。DETAILED DESCRIPTION OF THE INVENTION Industrial field of application: The present invention is directed to a method for treating a fluoroalkyl di(oxyethyl)amine phosphate ester (1) and/or ω) (collectively referred to as FAEP) represented by the following chemical formula. Contains information on water- and oil-repellent pigments and their production methods.
（ＣｎＦｎ、ｉＣＨ，ＣＨｔＯ）、 Ｐ−ＯＮ（ｆ（
、）（ＣＨ，ＣＨ，ＯＨ）＊ （１）Ｃｎｆ’ｎ◆５
ｃｄｎｃＨｓＯＰ （ＯＮ（Ｈｚ）（ＣＨｇＣ馬ＯＨ
） ｘ Ｊ ｘ （ＩＱただしｎは６〜１８の整数
を示す。(CnFn, iCH, CHtO), P-ON(f(
,)(CH,CH,OH)* (1)Cnf'n◆5
cdncHsOP (ON (Hz) (CHgC horse OH)
) x J x (IQ where n indicates an integer from 6 to 18.
な２上記化合物（Ｉ）、ω）は撥水性・撥油性を与える
成分で６って、これに他の性質を付与する成分を加える
ことにより他の属性を生じたとしても、不発明の権利に
関係しない。2 The above compound (I), ω) is a component that imparts water repellency and oil repellency.6 Even if other attributes are created by adding a component that imparts other properties to it, there is no right to non-invention. Not related to.
背景技術：
化粧用顔料は、界面化学的に、親水性（疎油性）と親油
性（疎水性）とに大別することができる。Background Art: Cosmetic pigments can be roughly classified into hydrophilic (oleophobic) and lipophilic (hydrophobic) based on surface chemistry.
固体表面の親水性・親油性を評価する方法として、Ｎ２
ガス吸着によシ全表面積を測定し、さらに、水蒸気を吸
着させて親水性表面積のみを測定し表面親油度（９６）
＝ １００−表面親水度 （２）の関係式から表
面親水度と表面親油度を定義する。一般に無機質の顔料
は親水性が強く、有機質の顔料は親油性であることが多
い。As a method for evaluating the hydrophilicity and lipophilicity of solid surfaces, N2
The total surface area is measured by gas adsorption, and then only the hydrophilic surface area is measured by adsorbing water vapor to determine the surface lipophilicity (96).
= 100-surface hydrophilicity Surface hydrophilicity and surface lipophilicity are defined from the relational expression (2). In general, inorganic pigments are strongly hydrophilic, and organic pigments are often lipophilic.
撥水性・撥油性で示される性質は、分子の極性に基因す
る上記の親水性・、親油性と異なり、実用的・巨視的な
性質で、一般的には、背反的な傾向はあるものの両性質
を併せ持つ場合もあり得るのである。撥水性・撥油性に
は耐水性・耐油性に通ずる意味もｂシ、特に顔料などの
属性を論するのに適している。Unlike the above-mentioned hydrophilic and lipophilic properties, which are based on the polarity of molecules, the properties indicated by water repellency and oil repellency are practical and macroscopic properties, and in general, they are both properties, although there are contradictory tendencies. It is possible that they have both properties. Water repellency and oil repellency have similar meanings to water resistance and oil resistance, and are particularly suitable for discussing attributes of pigments.
例えば化粧用顔料の場合、撥水性がないと、汗・涙・雨
などにより化粧くずれし易く、撥油性がないと皮脂・化
粧料の油分などにより化粧くずれする。For example, in the case of cosmetic pigments, if they are not water repellent, the makeup will easily come off due to sweat, tears, rain, etc., and if they are not oil repellent, the makeup will come off due to sebum, oil from cosmetics, etc.
顔料に撥水性を与える手段として、脂肪酸処理、ロジン
処理、シリコン油処理などが行われてきたが、撥油性を
付与する方法は現在までに提案されていない。Fatty acid treatment, rosin treatment, silicone oil treatment, etc. have been used as means for imparting water repellency to pigments, but no method for imparting oil repellency has been proposed to date.
解決しようとする問題点：
上記事情にかんがみ、本発明は撥水性と撥油性を併せ待
つ顔料およびその製造法を提供する。Problems to be Solved: In view of the above circumstances, the present invention provides a pigment that exhibits both water repellency and oil repellency, and a method for producing the same.
問題点を解決する丸めの手段：
本発明では、顔料類を前記したＦＡＥＰ（化合物（１）
およＪまたはω））で処理する。Rounding means for solving the problem: In the present invention, the pigments are FAEP (compound (1)) as described above.
and J or ω)).
顔料類を例示すると、無機顔料としては、酸化チタン、
ベンガラ、黄酸化鉄、黒酸化鉄、群青、亜鉛華、酸化マ
グネシウム、酸化ジルコニウム、マイカ、セリサイト、
タルク、シリカ、カオリン、水酸化クロム、カーボンブ
ラック、
有機顔料としては、リソールルピｙＢ、Ｌ−キレツドＣ
，リソールレッド、ローダミンＢ１ヘリンドンピンクＣ
Ｎ、パーマ−トンレッド、ベンジジンオレンジＧ、フタ
ロシアニンブル一覧などがおる。Examples of pigments include titanium oxide, inorganic pigments,
Red iron oxide, yellow iron oxide, black iron oxide, ultramarine, zinc white, magnesium oxide, zirconium oxide, mica, sericite,
Talc, silica, kaolin, chromium hydroxide, carbon black, organic pigments include Lysol Lupi YB, L-Kiretsudo C
, Lysole Red, Rhodamine B1 Herringdon Pink C
N, Palmerton Red, Benzidine Orange G, Phthalocyanine Blue, etc.
前記したＦＡＥＰの化学式（１）、■でｎを６〜１３と
制限した理由は、ｎが６以下の場合充分な泉水・撥油性
が得られないためで、またｎが１４以上の場合、理由は
明確でないが、充分な効果がないためである。しかしな
がら、ｎが８〜１１の場合、特に効果が大である。ジ（
オキシエチル）アミソリン酸塩の部分は大きな極性を持
ってお〕、そのため顔料の表面に強固に吸着することが
可能で、これに連なるフルオロアルキル基が顔料の表面
から外方に突出し、フッ化炭素の撥水・撥油性により、
所望の性質が生じていると思われる。The reason why n is limited to 6 to 13 in chemical formula (1) of FAEP mentioned above is that if n is 6 or less, sufficient spring water and oil repellency cannot be obtained, and if n is 14 or more, the reason is that n is limited to 6 to 13. Although it is not clear, this is because it does not have sufficient effect. However, when n is 8 to 11, the effect is particularly great. Ji(
The oxyethyl)amisophosphate moiety has high polarity and can therefore be strongly adsorbed onto the surface of the pigment, and the fluoroalkyl group connected to it protrudes outward from the surface of the pigment, resulting in the formation of fluorocarbons. Due to water and oil repellency,
It appears that the desired properties are occurring.
本発明の撥水・撥油性顔料を製造する丸めには、前記し
た顔料の１または２以上の混合物に水を加えてスラリー
状態とし、一方前記ＦＡＥＰに水を加え攪拌して０．１
１〜５重量％のエマルジョン状態にしたものを除徐に江
刺・混合した後、常温または高温静置などによってエマ
ルジョンを破壊し、顔料粒子の表面をＦＡＥＰの連続層
で被覆させる。その後、洗浄、濾過、乾燥工程を経て、
本発明の撥水・撥油性の顔料が生成する。In order to produce the water- and oil-repellent pigments of the present invention, water is added to a mixture of one or more of the pigments described above to form a slurry, and water is added to the FAEP and stirred to give a 0.1
After the emulsion of 1 to 5% by weight is slowly mixed, the emulsion is broken by standing at room temperature or high temperature, and the surface of the pigment particles is coated with a continuous layer of FAEP. After that, after washing, filtration and drying process,
The water- and oil-repellent pigment of the present invention is produced.
ＦＡＥＰ被覆熟理時の顔料の濃度について特に制限する
理由はないが、例えば５〜２０重量％の比較的高濃度で
、充分な攪拌混合が可能であるから、小型装置で大量処
理が可能である。一方被覆処理温度は１０〜８５゛Ｃす
なわち、大気温度の下で行えば良く、特に加熱冷却の必
要はない。There is no particular reason to limit the pigment concentration during FAEP coating, but at a relatively high concentration of, for example, 5 to 20% by weight, sufficient stirring and mixing is possible, so large-scale processing is possible with a small device. . On the other hand, the coating treatment temperature may be 10 to 85°C, that is, atmospheric temperature, and there is no particular need for heating or cooling.
実施例１
内容積２０００ ｍのビーカーに水ｔｏｏｏ ＊金入れ
、攪拌しながら市販のマイカ粉（脇田鉱業株式会社製マ
イカＮａ５５００ ） １００ ｆを投入し、充分攪拌
し、スラリ−とした。これに攪拌しながらＦＡＥＰ（ｎ
＝９、化合物（１） ： （ＩＦ）モル比１：１）の１
５重量％、水ａｍ １８．６ ｆ ｔ−徐徐に添７１１
１ Ｌ、終了後１００分間攪拌を行い、その後、ヌツチ
ェで吸引濾過し、乾燥器内で、６０℃で８時間乾燥し、
乳鉢で粉砕して、試料１を得た。Example 1 Into a beaker with an internal volume of 2000 m, 100 f of commercially available mica powder (mica Na5500 manufactured by Wakita Mining Co., Ltd.) was poured into a beaker with too much water and stirred, and thoroughly stirred to form a slurry. Add FAEP (n) to this while stirring.
=9, compound (1): (IF) molar ratio 1:1)
5% by weight, water am 18.6 ft-slowly added 711
1 L, stirred for 100 minutes after completion, then suction filtered with Nutsche, dried in a dryer at 60°C for 8 hours,
Sample 1 was obtained by grinding in a mortar.
実施例２
実施例１において、マイカ粉のかわシに、市販タルク粉
（日本タルク株式会社製タルクＭＳＡ）を用い、ＦＡＥ
Ｐ（ｎ＝９、化合物（■）：■モル比＝１：１）２’ｌ
を用いた以外、実施例１と実質的に同一条件で処理して
、試料２を得た。Example 2 In Example 1, commercially available talc powder (talc MSA manufactured by Nippon Talc Co., Ltd.) was used for mica powder, and FAE
P (n = 9, compound (■): ■ molar ratio = 1:1) 2'l
Sample 2 was obtained by processing under substantially the same conditions as in Example 1, except that .
実施例８
実施例１において、マイカ粉の代わりに、セリサイト粉
（堀江加工株式会社製セリサイ）ＨＣ）を用い、ＦＡＥ
Ｐ（化合物（Ｉ） ： Ｑｌ）モル比＝１＝１）５４ｇ
を用いた以外、実施例１と実質的に同一条件で処理して
試料８を得た。Example 8 In Example 1, sericite powder (Sericite HC manufactured by Horie Kako Co., Ltd.) was used instead of mica powder, and
P (compound (I): Ql) molar ratio = 1 = 1) 54 g
Sample 8 was obtained by processing under substantially the same conditions as in Example 1, except that .
実施例４
＊施例１において、マイカ粉の代わりに、二酸化チタン
粉（石原産業株式会社製二酸化チタンＣＢ−５０）を用
い、上記ＦＡＥＰ１８．５１を用いた以外実施例１と実
質的に同一条件で処理して、試料４を得た。Example 4 *Substantially the same conditions as Example 1 except that in Example 1, titanium dioxide powder (Titanium Dioxide CB-50 manufactured by Ishihara Sangyo Co., Ltd.) was used instead of mica powder, and the above FAEP 18.51 was used. Sample 4 was obtained.
実施例５
内容積２０００ ｍｌのビーカーにエチルアルコール５
重量％水溶液１００ ｍをとり、これにヘリンドンピン
クＣＮ １００ ｇを投入し、充分かき混ぜスラリー状
にした。これに水９００ Ｊ１／を江刺し充分攪拌し、
これに乳濁状の１５ｆｆｉｉ１％ＦＡＫＰ溶液１８．５
Ｎを徐徐に江刺し、以下実施例１と実質的に同じ処理を
行い、試料５ｔ−得た。Example 5 5 ethyl alcohol in a beaker with an internal volume of 2000 ml
100 ml of the wt% aqueous solution was taken, 100 g of Herringdon Pink CN was added thereto, and the mixture was sufficiently stirred to form a slurry. Add 900 J1 of water to this and stir thoroughly.
Add to this 18.5 ml of emulsified 15ffii 1% FAKP solution.
N was gradually added to the sample, and substantially the same treatment as in Example 1 was performed to obtain 5 tons of samples.
実施例６
実施例５において、顔料へリントンピンクＣＮの代わシ
に、ベンジジンオレンジＧを用いた以外、実施例５と実
質的に同じ沈埋を行い試料６を得た０
比較例１
内容積２０００ｍのビーカーで、２Ｎのメチルハイドロ
ポリシロキサン（信越化学株式会社製、商品名ＫＦ−９
９）を１２０１の１．１．１− ）リクロロエタン（ｆ
亜合成株式会社製、商品名スリーワン）に溶解し、これ
に市販のマイカ（脇田鉱業株式会社製、商品名マイカＮ
ａ５５０Ｇ ）を加え、よく混練し均一状態とした。こ
れｔ−２５ｍ ｘ ２ｏ ｃｌｌの琺瑯製／（ットに拡
げて一夜放置し、溶剤を蒸発させた。さらに溶剤臭がな
くなるまで、６０℃の電気乾燥器で乾燥し、市販のジュ
ースミキサーで粉砕した。その後、１５０°Ｃに保った
電気乾燥器で６時間処理し、メチルポリシロキサンの重
合を行わせ、比較試料１を得九〇
比較例２
顔料として、マイカの代わりに、メルク（日本タルク株
式会社製商品名タルクＭＳＡ）を使用し、１．ｌ、１−
ドルクロロエタン１２０ｆの代わシに１０ｏｆを使用
した以外は、比較例１と実質的に同じ操作金柑い、比較
試料２を得た。Example 6 Sample 6 was obtained by substantially the same embedding as in Example 5, except that Benzidine Orange G was used instead of the pigment Herrington Pink CN.Comparative Example 1 Sample 6 was obtained with an internal volume of 2000 m. In a beaker, add 2N methylhydropolysiloxane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KF-9).
9) to 1201 of 1.1.1-)lichloroethane (f
Commercially available mica (manufactured by Wakita Mining Co., Ltd., trade name Mica
a550G) was added and kneaded well to obtain a uniform state. This was spread on a 25m x 2o CLL enamel plate and left overnight to evaporate the solvent. It was further dried in an electric dryer at 60°C until the solvent odor disappeared, and then ground in a commercially available juice mixer. Thereafter, it was treated in an electric dryer kept at 150°C for 6 hours to polymerize methylpolysiloxane, yielding Comparative Sample 1. 1.l, 1-
Comparative Sample 2 was obtained using substantially the same procedure as in Comparative Example 1, except that 10of was used instead of 120f of dolchloroethane.
比較例８
顔料として、マイカの代わ９に、セリサイトを用いた以
外は、実質的に比較例１と同じ操作を行い、比較試料８
’ｔ−得た。Comparative Example 8 Comparative Sample 8 was obtained by performing substantially the same operation as Comparative Example 1, except that sericite was used as the pigment instead of mica.
't-got it.
比較例４
顔料として、マイカの代θシに、酸化チタンを用い、１
，１．１−）リクロロエタン１２０ ｆの代わシに、８
０ＩＩｔ−使用した以外は実質的に比較例１と同じ操作
を行−１比較試料４を得た。Comparative Example 4 Titanium oxide was used as a pigment in place of mica, and 1
, 1.1-) instead of 120 f of dichloroethane, 8
Comparative Sample 4 was obtained in substantially the same manner as in Comparative Example 1 except that 0IIt- was used.
比較例５
比較例１において、顔料マイカの代わシにヘリンドンピ
ンクＣＮを用い、２００ｆの１．１．１−）リクロロエ
チレンと、電気乾燥器の温度を１００℃とした以外、比
較例１と実質的に同じ操作を行い、比較試料６を得た。Comparative Example 5 Comparative Example 1 except that Herringdon Pink CN was used instead of the pigment mica, 200f of 1.1.1-)lichloroethylene was used, and the temperature of the electric dryer was 100°C. Comparative sample 6 was obtained by performing substantially the same operation as above.
比較例６
比較例１に２いて、顔料マイカの代わりにヘリンドンビ
ンクＣＮと、２００ｆの１．１．１−）リクロロエタン
を用い、電気乾燥器の温度を１００℃とした以外は、比
較例１と実質的に同じ操作を行い、比較例６を得た。Comparative Example 6 Comparative Example 1 and 2 except that Herringdon Vink CN and 200f 1.1.1-)lichloroethane were used instead of the pigment mica, and the temperature of the electric dryer was 100°C. Comparative Example 6 was obtained by performing substantially the same operation as in Example 1.
本発明試料１〜６、比較試料１〜６および、沈埋を行わ
ない未処理試料１（マイカ使用）、２（タルク使用）、
８（セリサイト使用）、４（二酸化チタン使用）につい
て、撥水性および、オレイン酸およびヒマシ油に対する
撥油性を試験した結果を第１表に示す。ただし、評価基
準として Ｏ：（完全に浮上している。）、Δ：（一部
浮上している。）、Ｘ：（完全に沈降している。）を示
す。Invention samples 1 to 6, comparative samples 1 to 6, and untreated samples 1 (using mica), 2 (using talc),
Table 1 shows the results of tests for water repellency and oil repellency against oleic acid and castor oil for Samples No. 8 (using sericite) and No. 4 (using titanium dioxide). However, the evaluation criteria are O: (completely floating), Δ: (partially floating), and X: (completely sinking).
発明の効果：
第１表に示した実施例から明らかなように、不発明の撥
水撥油性顔料は、未処理顔料および、シリコン系処理に
比べて、卓抜した撥水撥油性を持っている。Effects of the invention: As is clear from the examples shown in Table 1, the uninvented water- and oil-repellent pigment has outstanding water- and oil-repellency compared to untreated pigments and silicone-based treatments. .
それゆえ、例えば、化粧用顔料として使用した場合、汗
・涙・雨などによる化粧くずれを防止することができる
など、種種の産業に利用することができる。Therefore, for example, when used as a cosmetic pigment, it can be used in various industries, such as preventing makeup from fading due to sweat, tears, rain, etc.
Claims (1)
数を示す。） からなるフルオロアルキルジ（オキシエチル）アミンリ
ン酸塩エステル群の少なくとも１化合物で表面を被覆さ
れた撥水撥油性顔料。 ２ 一般式 ▲数式、化学式、表等があります▼ なる化合物（ I ）と、 一般式 ▲数式、化学式、表等があります▼ なる化合物（II） （化合物（ I ）、（II）の一般式中ｎは６〜１３の整
数を示す。） からなるフルオロアルキルジ（オキシエチル）アミンリ
ン酸塩エステル群の少なくとも１化合物の水溶液中に顔
料を浸漬し、乾燥粉砕する工程を含む撥水撥油性顔料の
製造法。[Claims] 1. A compound (I) with the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. A compound (II) with the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. , in the general formula (II), n represents an integer of 6 to 13. 2 Compound (I) with the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ Compound (II) with the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. (n is an integer of 6 to 13.) Production of a water- and oil-repellent pigment, comprising the step of immersing the pigment in an aqueous solution of at least one compound of the fluoroalkyl di(oxyethyl)amine phosphate ester group consisting of Law.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9305486A JPS62250074A (en) | 1986-04-21 | 1986-04-21 | Water-repellent, oil-repellent pigment and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9305486A JPS62250074A (en) | 1986-04-21 | 1986-04-21 | Water-repellent, oil-repellent pigment and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62250074A true JPS62250074A (en) | 1987-10-30 |
| JPH0586984B2 JPH0586984B2 (en) | 1993-12-15 |
Family
ID=14071792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9305486A Granted JPS62250074A (en) | 1986-04-21 | 1986-04-21 | Water-repellent, oil-repellent pigment and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62250074A (en) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03246210A (en) * | 1990-02-23 | 1991-11-01 | Daito Kasei Kogyo Kk | Cosmetic |
| JPH04330007A (en) * | 1991-02-01 | 1992-11-18 | Daito Kasei Kogyo Kk | Cosmetic |
| JPH0525019A (en) * | 1991-07-19 | 1993-02-02 | Kao Corp | Powder for cosmetic and cosmetic containing the same |
| JPH0967232A (en) * | 1995-08-31 | 1997-03-11 | Kao Corp | Cosmetic |
| WO2000061697A1 (en) * | 1999-04-12 | 2000-10-19 | Daikin Industries, Ltd. | Powdery water-and-oil repellent, process for producing the same, and use thereof |
| EP1672036A1 (en) | 2004-12-16 | 2006-06-21 | Kao Corporation | Pearlescent pigment |
| EP1672037A1 (en) | 2004-12-16 | 2006-06-21 | Kao Corporation | Pearlescent pigment |
| DE102007061701A1 (en) | 2007-12-19 | 2009-06-25 | Eckart Gmbh | Metallic effect pigments, process for their preparation and use thereof and powder coating |
| WO2009142047A1 (en) | 2008-05-21 | 2009-11-26 | 三好化成株式会社 | Surface-treated powder and cosmetic comprising the same |
| WO2010114111A1 (en) | 2009-03-30 | 2010-10-07 | Daikin Industries, Ltd. | Fluorine-modified silicone polymer, surface treated powder and cosmetics comprising powder |
| WO2010114112A1 (en) | 2009-03-30 | 2010-10-07 | Daikin Industries, Ltd. | Powder surface-treated with fluorine-modified aminosilane and cosmetics comprising the same |
| WO2010114110A1 (en) | 2009-03-30 | 2010-10-07 | Daikin Industries, Ltd. | Alkoxylated fluorine-modified siloxane polymer, surface treated powder and cosmetics comprising the same |
| WO2011024364A1 (en) | 2009-08-31 | 2011-03-03 | 三好化成株式会社 | Composition for cosmetic preparation having ultraviolet shielding effect and sebum solidifying ability, and cosmetic preparation |
| WO2013031594A1 (en) | 2011-08-29 | 2013-03-07 | Ａｇｃセイミケミカル株式会社 | Copolymer for cosmetics, surface treatment agent for cosmetic powder, powder for cosmetics, and cosmetic preparation |
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-
1986
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|---|---|---|---|---|
| JPH03246210A (en) * | 1990-02-23 | 1991-11-01 | Daito Kasei Kogyo Kk | Cosmetic |
| JPH04330007A (en) * | 1991-02-01 | 1992-11-18 | Daito Kasei Kogyo Kk | Cosmetic |
| JP2509392B2 (en) * | 1991-02-01 | 1996-06-19 | 大東化成工業株式会社 | Cosmetics |
| JPH0525019A (en) * | 1991-07-19 | 1993-02-02 | Kao Corp | Powder for cosmetic and cosmetic containing the same |
| JPH0967232A (en) * | 1995-08-31 | 1997-03-11 | Kao Corp | Cosmetic |
| WO2000061697A1 (en) * | 1999-04-12 | 2000-10-19 | Daikin Industries, Ltd. | Powdery water-and-oil repellent, process for producing the same, and use thereof |
| EP1672036A1 (en) | 2004-12-16 | 2006-06-21 | Kao Corporation | Pearlescent pigment |
| EP1672037A1 (en) | 2004-12-16 | 2006-06-21 | Kao Corporation | Pearlescent pigment |
| US8603504B2 (en) | 2005-03-30 | 2013-12-10 | Ajinomoto Co., Inc. | Cosmetic powder |
| DE102007061701A1 (en) | 2007-12-19 | 2009-06-25 | Eckart Gmbh | Metallic effect pigments, process for their preparation and use thereof and powder coating |
| WO2009077191A1 (en) * | 2007-12-19 | 2009-06-25 | Eckart Gmbh | Metallic pigments, method for the production thereof and use thereof and coating powder |
| WO2009142047A1 (en) | 2008-05-21 | 2009-11-26 | 三好化成株式会社 | Surface-treated powder and cosmetic comprising the same |
| WO2010114112A1 (en) | 2009-03-30 | 2010-10-07 | Daikin Industries, Ltd. | Powder surface-treated with fluorine-modified aminosilane and cosmetics comprising the same |
| WO2010114110A1 (en) | 2009-03-30 | 2010-10-07 | Daikin Industries, Ltd. | Alkoxylated fluorine-modified siloxane polymer, surface treated powder and cosmetics comprising the same |
| WO2010114111A1 (en) | 2009-03-30 | 2010-10-07 | Daikin Industries, Ltd. | Fluorine-modified silicone polymer, surface treated powder and cosmetics comprising powder |
| WO2011024364A1 (en) | 2009-08-31 | 2011-03-03 | 三好化成株式会社 | Composition for cosmetic preparation having ultraviolet shielding effect and sebum solidifying ability, and cosmetic preparation |
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| WO2013031594A1 (en) | 2011-08-29 | 2013-03-07 | Ａｇｃセイミケミカル株式会社 | Copolymer for cosmetics, surface treatment agent for cosmetic powder, powder for cosmetics, and cosmetic preparation |
| US10064803B2 (en) | 2011-08-29 | 2018-09-04 | Agc Seimi Chemical Co., Ltd. | Copolymer for cosmetics, surface treatment agent for cosmetic powder, powder for cosmetics, and cosmetic preparation |
| WO2013057945A1 (en) | 2011-10-18 | 2013-04-25 | 日本曹達株式会社 | Surface-covered inorganic powder |
| KR20140068168A (en) | 2011-10-18 | 2014-06-05 | 닛뽕소다 가부시키가이샤 | Surface-covered inorganic powder |
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| Publication number | Publication date |
|---|---|
| JPH0586984B2 (en) | 1993-12-15 |
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