JP6644482B2 - Surface-treated powder, method for producing the same, and cosmetic containing the same - Google Patents
Surface-treated powder, method for producing the same, and cosmetic containing the same Download PDFInfo
- Publication number
- JP6644482B2 JP6644482B2 JP2015118784A JP2015118784A JP6644482B2 JP 6644482 B2 JP6644482 B2 JP 6644482B2 JP 2015118784 A JP2015118784 A JP 2015118784A JP 2015118784 A JP2015118784 A JP 2015118784A JP 6644482 B2 JP6644482 B2 JP 6644482B2
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- powder
- treated
- present
- product
- surface treatment
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- 239000000843 powder Substances 0.000 title claims description 135
- 239000002537 cosmetic Substances 0.000 title claims description 45
- 238000004519 manufacturing process Methods 0.000 title claims description 36
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- 239000000126 substance Substances 0.000 claims description 24
- 125000003277 amino group Chemical group 0.000 claims description 17
- 239000010702 perfluoropolyether Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
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- 239000012756 surface treatment agent Substances 0.000 description 34
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XOALFFJGWSCQEO-UHFFFAOYSA-N tridecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C=C XOALFFJGWSCQEO-UHFFFAOYSA-N 0.000 description 1
- BPCXHCSZMTWUBW-UHFFFAOYSA-N triethoxy(1,1,2,2,3,3,4,4,5,5,8,8,8-tridecafluorooctyl)silane Chemical compound CCO[Si](OCC)(OCC)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCC(F)(F)F BPCXHCSZMTWUBW-UHFFFAOYSA-N 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Landscapes
- Cosmetics (AREA)
Description
本発明は、撥水性、撥油性に優れ、且つ使用感に優れた表面処理粉体および該粉体を含有する化粧料に関する。 TECHNICAL FIELD The present invention relates to a surface-treated powder excellent in water repellency and oil repellency and excellent in usability, and a cosmetic containing the powder.
化粧料には、化粧料用粉体として様々な粉体が用いられており、その使用目的に合わせて、随時種々の化合物で表面処理が行なわれている。また、汗・涙・雨などによる化粧くずれや皮脂・化粧料の油分などによる化粧くずれの防止を目的として、撥水性、撥油性をもたせるための表面処理に関する研究が行われている。 Various powders are used for cosmetics as powders for cosmetics, and surface treatment is performed with various compounds as needed in accordance with the purpose of use. In addition, for the purpose of preventing makeup loss due to sweat, tears, rain, etc., and makeup loss due to sebum, oil of cosmetics, etc., studies on surface treatments for imparting water repellency and oil repellency have been conducted.
従来、提案されている撥水性、撥油性に優れるフッ素化合物で処理した粉体としては、例えば、パーフルオロアルキル基を有するリン酸エステルで粉体の表面処理をした撥水撥油性粉体（特許文献１）、パーフルオロアルキルシランで粉体を処理した撥水撥油性顔料（特許文献２）、パーフルオロポリエーテルアルキルリン酸及びその塩等で基材粉体の表面を処理した化粧用粉体（特許文献３）、パーフルオロアルキル・ポリオキシアルキレン共変性シリコーンにて表面処理された改質粉体（特許文献４）、トリデカフルオロオクチルトリエトキシシラン化合物を表面処理した撥水撥油性化粧料用粉体顔料（特許文献５）、パーフルオロアクリレート共重合体が表面に被覆された顔料粉体（特許文献６）、パーフルオロポリエーテル変性ポリウレタンウレタンを表面処理した撥水撥油性化粧料用粉体顔料（特許文献７）等が挙げられ、いずれも化粧料用の粉体として利用されている。 Conventionally proposed powders treated with a fluorine compound having excellent water repellency and oil repellency include, for example, water-repellent and oil-repellent powders that have been surface-treated with a phosphoric ester having a perfluoroalkyl group (Patent Literature 1), a water- and oil-repellent pigment obtained by treating a powder with a perfluoroalkylsilane (Patent Document 2), a cosmetic powder obtained by treating the surface of a base powder with a perfluoropolyetheralkylphosphoric acid, a salt thereof, and the like. (Patent Document 3), Modified powder surface-treated with perfluoroalkyl / polyoxyalkylene co-modified silicone (Patent Document 4), Water- and oil-repellent cosmetic surface-treated with tridecafluorooctyltriethoxysilane compound Powder pigment for use (Patent Document 5), pigment powder having a surface coated with a perfluoroacrylate copolymer (Patent Document 6), perfluoropolyether-modified poly Repellent cosmetic powders pigment surface-treated with urethane urethane (Patent Document 7), and the like, all of which are available as a powder for cosmetics.
しかしながら、これらのフッ素化合物を持ってしても、撥水性、撥油性と使用感触の両立について、必ずしも十分満足できるものではなかった。 However, even with these fluorine compounds, it has not always been possible to sufficiently satisfy both water repellency, oil repellency, and feel during use.
一方、本発明者らが着目した一般式（１）で表されるアミノ基を有するパーフルオロポリエーテル化合物は、パーフルオロアルキレン又はパーフルオロアルキルと結合しているエーテル酸素を２個以上有するパーフルオロアルコキシ基の繰り返し単位から誘導されるポリパーフルオロポリエーテル鎖が構造中に組み込まれ、かつ、一般式（１）の末端構造中にカチオン性のアミノ基が側鎖として存在する、その中和塩が水溶性のパーフルオロポリエーテル化合物である。一般にアミノ基を有する有機化合物は、吸着性を有するので、凝集剤、毛髪のコンディショニング剤、織物の表面改質剤、紙のサイジング剤として利用されている。 On the other hand, the perfluoropolyether compound having an amino group represented by the general formula (1) which the present inventors have noticed is a perfluoroalkylene or a perfluoroalkylene compound having two or more ether oxygens bonded to a perfluoroalkyl. A neutralized salt thereof wherein a polyperfluoropolyether chain derived from a repeating unit of an alkoxy group is incorporated in the structure, and a cationic amino group is present as a side chain in the terminal structure of the general formula (1). Is a water-soluble perfluoropolyether compound. In general, an organic compound having an amino group has an adsorptive property, and is therefore used as a flocculant, a hair conditioning agent, a fabric surface modifier, and a paper sizing agent.
本発明に係わる一般式（１）は、パーフルオロポリエーテル鎖が末端アミノ基に組み込まれた化合物であるが、これを原料とした各種誘導体（特許文献８〜１０）が界面活性剤、消火薬剤として報告されている。しかしながら、粉体の処理剤として利用するものではなく、化粧用としても応用もなされていない。 The general formula (1) according to the present invention is a compound in which a perfluoropolyether chain is incorporated in a terminal amino group. It has been reported as. However, it is not used as a powder treatment agent, nor is it applied to cosmetics.
本発明は、撥水性、撥油性に優れ、肌への塗布時の感触が滑らかで付着性も良好な表面処理粉体及びその製造方法、並びにこの表面処理粉体を配合した化粧料を提供することにある。 The present invention provides a surface-treated powder which has excellent water repellency and oil repellency, has a smooth feel when applied to the skin, and has good adhesion, a method for producing the same, and a cosmetic containing the surface-treated powder. It is in.
本発明者らは鋭意研究を進めた結果、化学式（１）で表されるアミノ基を有するパーフルオロポリエーテル化合物を表面処理剤として利用することで、この表面処理粉体は撥水性、撥油性に優れるため汗や皮脂による化粧崩れを防止できること、また、肌への塗布時の感触が滑らかで付着性も良好であることを見出し、本発明を完成するに到った。 The present inventors have conducted intensive research and have found that by using a perfluoropolyether compound having an amino group represented by the chemical formula (1) as a surface treatment agent, this surface-treated powder has water repellency and oil repellency. The present invention has been found to be able to prevent makeup collapse due to sweat or sebum because of its superiority, and to have a smooth feel and good adhesion when applied to the skin, and have completed the present invention.
本発明により、撥水性、撥油性に優れ、肌への塗布時の感触が滑らかで付着性も良好な表面処理粉体を提供することができる。本発明の表面処理粉体は従来の撥水撥油性粉体とは異なり、化粧品で用いられる種々の粉体との混和性にも優れており、容易に感触に優れた高機能な化粧料を提供することができる。具体的には、汗や水などによる化粧崩れがおこりにくいメーキャップ化粧料や紫外線防御用化粧料、容器や衣服などに色移りしにくい口紅やファンデーションなどの化粧料を提供することができ、及びその製造方法、並びにこの表面処理粉体を配合した化粧料を提供できる。 According to the present invention, it is possible to provide a surface-treated powder which is excellent in water repellency and oil repellency, has a smooth feel when applied to the skin, and has good adhesion. The surface-treated powder of the present invention is different from conventional water- and oil-repellent powders in that it has excellent miscibility with various powders used in cosmetics, and provides highly functional cosmetics that are easy to feel and feel. Can be provided. More specifically, it is possible to provide makeup cosmetics and ultraviolet protection cosmetics that are less likely to lose their makeup due to sweat, water, and the like, and cosmetics such as lipstick and foundation that do not easily transfer color to containers and clothes. It is possible to provide a production method and a cosmetic containing the surface-treated powder.
以下、本発明の表面処理粉体について詳述する。
本発明は、一般式（１）；
（但し、ｍは０〜５の整数を表し、ｎは平均値で０〜２０の整数を表し、Ｒ１は炭素数２〜６のアルキレン基を表し、Ｒ２は水素原子または炭素数の合計が１〜８のアルキル基、アラルキル基、アリール基を表し、Ｒ３は水素原子または炭素数の合計が１〜８のアルキル基、アラルキル基、アリール基を表し、Ｘはフッ素原子、または炭素数１〜３のパーフルオロアルキル基を表し、ＺはＮＨまたはＮ−ＣＨ３または酸素原子を表す。）で示される、アミノ基を有するパーフルオロポリエーテル化合物によって基材粉体の表面が処理されていることを特徴とする表面処理粉体である。
Hereinafter, the surface-treated powder of the present invention will be described in detail.
The present invention provides a compound represented by the general formula (1):
(However, m represents an integer of 0 to 5, n represents an integer of 0 to 20 on average, R1 represents an alkylene group having 2 to 6 carbon atoms, and R2 represents a hydrogen atom or a total of 1 carbon atoms. Represents an alkyl group, an aralkyl group, or an aryl group having 8 to 8 carbon atoms, R3 represents a hydrogen atom or an alkyl group, an aralkyl group, or an aryl group having a total of 1 to 8 carbon atoms, and X represents a fluorine atom or 1 to 3 carbon atoms. Wherein Z represents NH or N-CH3 or an oxygen atom.), And the surface of the base powder is treated with a perfluoropolyether compound having an amino group. Surface-treated powder.
本発明に関わるアミノ基を有するパーフルオロポリエーテル化合物中の繰り返し構造中のＸはフッ素原子、または炭素数１〜３のパーフルオロアルキル基であれば上記効果を充分に呈するものであるが、Ｘがトリフルオロメチル基であることが特に好ましい。
本発明に係わるアミノ基を有するパーフルオロポリエーテル化合物は例えば、米国特許２７６４６０３号、米国特許３２５０８０８号などを参考に合成できる。
If X in the repeating structure in the perfluoropolyether compound having an amino group according to the present invention is a fluorine atom or a perfluoroalkyl group having 1 to 3 carbon atoms, the above effect is sufficiently exhibited. Is particularly preferably a trifluoromethyl group.
The perfluoropolyether compound having an amino group according to the present invention can be synthesized with reference to, for example, US Pat. No. 2,764,603 and US Pat. No. 3,250,808.
本発明は、前記表面処理成分を処理する事により、従来では得られない撥油性と感触、付着性、更には他の表面処理粉体との混和性を両立した粉体が得られることにある。表面処理量について制限するものではないが、本発明の表面処理成分は基材粉体１００質量部に対して、１以上５０質量部であることが好ましい。 An object of the present invention is to provide a powder having both oil repellency and feel, adhesiveness, and even miscibility with other surface-treated powders, which have not been obtained conventionally, by treating the surface treatment component. . Although the amount of surface treatment is not limited, the amount of the surface treatment component of the present invention is preferably 1 to 50 parts by mass based on 100 parts by mass of the substrate powder.
本発明に係わるアミノ基を有するパーフルオロポリエーテル化合物の性状は、パーフルオロポリエーテル部のＸの種類、または分子量に依存して常温で液体〜固体を呈する。また、アミノ基を持つことから中和塩は水に溶解又は分散する。
本発明に係わるアミノ基を有するパーフルオロポリエーテル化合物は、前処理することなくそのまま用いても十分な効果を発揮するが、適当な酸性物質で中和した塩を用いることが好ましい。
The properties of the perfluoropolyether compound having an amino group according to the present invention are liquid to solid at room temperature depending on the type of X in the perfluoropolyether portion or the molecular weight. Further, since the neutralized salt has an amino group, the neutralized salt is dissolved or dispersed in water.
Although the perfluoropolyether compound having an amino group according to the present invention exerts a sufficient effect when used without any pretreatment, it is preferable to use a salt neutralized with a suitable acidic substance.
中和に用いられる酸性物質としては、特に制限されるものではないが、例えば、次のような酸性物質が挙げられる。またこれらの酸性物質は１種または２種以上を混合して用いても構わない。硫酸、硝酸、塩酸、リン酸、ケイ酸、炭酸、ギ酸、酢酸、プロピオン酸、安息香酸、ケイヒ酸、サリチル酸、シュウ酸、マロン酸、コハク酸、アジピン酸、酒石酸、リンゴ酸、クエン酸、グルタル酸、セバシン酸、フマル酸、マレイン酸、メシル酸、トシル酸、ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、オレイン酸、リノール酸、リノレン酸、ベヘン酸、ソルビン酸、グルタミン酸、アスパラギン酸、アスコルビン酸、エリソルビン酸などが挙げられる。 The acidic substance used for neutralization is not particularly limited, and examples thereof include the following acidic substances. These acidic substances may be used alone or in combination of two or more. Sulfuric acid, nitric acid, hydrochloric acid, phosphoric acid, silicic acid, carbonic acid, formic acid, acetic acid, propionic acid, benzoic acid, cinnamic acid, salicylic acid, oxalic acid, malonic acid, succinic acid, adipic acid, tartaric acid, malic acid, citric acid, glutar Acid, sebacic, fumaric, maleic, mesylic, tosylic, lauric, myristic, palmitic, stearic, oleic, linoleic, linolenic, behenic, sorbic, glutamic, aspartic, ascorbic Acid, erythorbic acid and the like.
表面処理剤を使用して基材粉体の表面を処理する方法は、一般的には湿式法、乾式法の２方法がある。湿式法は溶剤、もしくは水／溶剤溶液に基材粉体を分散し、ここに攪拌しながら、表面処理剤を添加し、均一にコート後ろ過して、乾燥し表面処理粉体を得るものである。乾式法はヘンシェルミキサー、ボールミルなどに基材粉体を加え、表面処理剤を加え、良く混合後乾燥、加熱して処理粉体を得るものである。 There are generally two methods for treating the surface of the base material powder using a surface treatment agent, a wet method and a dry method. In the wet method, a substrate powder is dispersed in a solvent or a water / solvent solution, a surface treatment agent is added thereto with stirring, the mixture is uniformly coated, filtered, and dried to obtain a surface treatment powder. is there. In the dry method, a base powder is added to a Henschel mixer, a ball mill, or the like, a surface treatment agent is added, mixed well, dried and heated to obtain a treated powder.
本発明における表面処理の方法は特に制限するものでは無いが、乾式法、湿式法のどちらを用いても優れた撥水性、撥油性に優れ、肌への塗布時の感触を付与することができる。均質な表面処理をするには湿式法がより好ましい。 The method of the surface treatment in the present invention is not particularly limited, but it is possible to provide excellent water repellency and oil repellency by using either the dry method or the wet method, and to impart a feeling when applied to the skin. . For uniform surface treatment, a wet method is more preferable.
具体的には、一般式（１）で表されるアミノ基を有するパーフルオロポリエーテル化合物は酸性下で水に溶解する。したがって、一般式（１）で表されるアミノ基を有するパーフルオロポリエーテル化合物で粉体表面を処理するためには基材粉体を水に分散し、ｐＨ３．０以下の酸性下で表面処理剤を加え、良く混合して、ろ過、乾燥して処理粉体を得ることができる。 Specifically, the perfluoropolyether compound having an amino group represented by the general formula (1) dissolves in water under acidic conditions. Therefore, in order to treat the powder surface with the perfluoropolyether compound having an amino group represented by the general formula (1), the base powder is dispersed in water, and the surface treatment is performed under acidic condition of pH 3.0 or less. The agent can be added, mixed well, filtered and dried to obtain a treated powder.
上述のようにして得られる本発明の表面処理粉体は撥水性、撥油性に優れ、且つ肌への塗布時の感触が滑らかで、肌との付着性にも優れる。 The surface-treated powder of the present invention obtained as described above is excellent in water repellency and oil repellency, has a smooth feel when applied to the skin, and has excellent adhesion to the skin.
更に、本発明に係わる基材粉体の表面処理にあたっては、本発明の効果を損なわない範囲で、一般式（１）以外の表面処理剤を同時又は連続的に基材粉体に表面処理することができる。本発明に使用できる表面処理剤としては、例えばパーフルオロポリエーテル変性アミノシラン、パーフルオロオクチルトリエトキシシラン、炭素数９〜１５のフルオロアルコールリン酸、トリフルオロプロピルシクロペンタシロキサン、ＰＥＧ８トリフルオロプロピルジメチコンコポリマー等の本発明に係わる表面処理剤以外のフッ素系化合物、ハイドロジェンシリコーン、アミノシリコーン、反応性オルガノポリシロキサン、アルキルシランなどのシリコーン化合物、有機チタネート、ポリオレフィン、レシチン及び／又はその塩、水添レシチン及び／又はその塩などのレシチン類、アシル化アミノ酸及び／又はその塩、酸性エステル油、脂肪酸及び／又はその塩類、デキストリン脂肪酸エステル、フラクトオリゴ糖脂肪酸エステル、コラーゲン、高級アルコール、エステル、ワックス、金属石鹸などが挙げられるが、これらに限定されるものではない。 Further, in the surface treatment of the substrate powder according to the present invention, a surface treatment agent other than the general formula (1) is simultaneously or continuously surface-treated on the substrate powder within a range that does not impair the effects of the present invention. be able to. Examples of the surface treatment agent that can be used in the present invention include perfluoropolyether-modified aminosilane, perfluorooctyltriethoxysilane, fluoroalcohol phosphoric acid having 9 to 15 carbon atoms, trifluoropropylcyclopentasiloxane, PEG8 trifluoropropyldimethicone copolymer And the like, fluorine compounds other than the surface treating agent according to the present invention, silicone compounds such as hydrogen silicone, amino silicone, reactive organopolysiloxane and alkylsilane, organic titanates, polyolefins, lecithin and / or salts thereof, and hydrogenated lecithin And / or salts thereof, such as lecithins, acylated amino acids and / or salts thereof, acidic ester oils, fatty acids and / or salts thereof, dextrin fatty acid esters, fructooligosaccharide fatty acid esters, cola Gen, higher alcohols, esters, waxes, and the like metal soaps, but not limited thereto.
上記パーフルオロポリエーテル変性アミノシランは、特開昭５８−１２２９７９号公報に準じた方法で合成できる。パーフルオロオクチルトリエトキシシランは、Ｇｅｌｅｓｔ，Ｉｎｃ．製のものを利用できる。炭素数９〜１５のフルオロアルコールリン酸は、特開２００４−２７７３８９号公報に準じた方法で合成できる。トリフルオロプロピルシクロペンタシロキサンは、信越化学工業社のＫＦ−５００２などが利用できる。ＰＥＧ８トリフルオロプロピルジメチコンは、信越化学工業社のＦＰＤ−６１３１などを利用できる。反応性オルガノポリシロキサンとしては、信越化学工業社のＫＦ９９（メチコン）、ＫＦ９９０１（ハイドロジェンジメチコン）等、ＫＦ−９９０８（トリエトキシシリルエチルポリジメチルシロキシエチルジメチコン）、ＫＦ−９９０９（トリエトキシシリルエチルポリジメチルシロキシエチルヘキシルジメチコン）、ＫＰ−５７４（（アクリレーツ／アクリル酸トリデシル／メタクリル酸トリエトキシシリルプロピル／メタクリル酸ジメチコン）コポリマー）、ＫＦ―７３１２（トリメチルシロキシケイ酸とシクロペンタシロキサンの混合物）、ＫＦ―９００１（トリメチルシロキシケイ酸のデカメチルシクロペンタシロキサン５０％溶液）等を使用できる。アルキルシランとしては、ダウコーニング社のＺ−６３４１（オクチルトリエトキシシラン）やデグサ社のＦ−８２６１（トリデカフルオロオクチルトリエトキシシラン）等を使用できる。有機チタネートとしては、味の素社のプレンアクトＫＲ−ＴＴＳ（イソプロピルトリイソステアロイルチタネート）等が使用できる。ポリオレフィンとしては、例えば、特開昭６３−１７９９７２号公報に記載の公知の化合物や、ポリプロピレンを酸化して得られる酸化ポリエチレン、マレイン化ポリエチレン、酸化ポリプロピレン等を使用できる。水添レシチン及び／又はその塩類としては、例えば、日光ケミカルズ社のレシノールＳ−１０（水素添加大豆リン脂質）、キユーピー社の卵黄レシチンＰＬ−１００Ｐ（水素添加卵黄リン脂質）等を使用できる。アシル化アミノ酸及び／又はその塩としては、日光ケミカル社のサルコシネートＭＮ（ミリストイルメチルアミノ酢酸ナトリウム）、アラニネートＬＮ−３０（ラウロイルメチルアラニンナトリウム）、サルコシネートＣＮ−３０（ココイルサルコシンナトリウム）、サルコシネートＯＨ（オレオイルサルコシン）等、味の素社のアミソフトＨＳ−２１（Ｎ−ステアロイル−Ｌ−グルタミン酸ニナトリウム）等、ＳＥＰＰＩＣ社のＳＥＰＩＬＩＦＴ ＤＰＨＰ（ジパルミトイルヒドロキシプロリン）等を使用できる。 The above-mentioned perfluoropolyether-modified aminosilane can be synthesized by a method according to JP-A-58-122979. Perfluorooctyltriethoxysilane is available from Gelest, Inc. Made of products can be used. Fluoroalcohol phosphoric acid having 9 to 15 carbon atoms can be synthesized by a method according to JP-A-2004-277389. As trifluoropropylcyclopentasiloxane, KF-5002 manufactured by Shin-Etsu Chemical Co., Ltd. or the like can be used. As PEG8 trifluoropropyl dimethicone, FPD-6131 of Shin-Etsu Chemical Co., Ltd. or the like can be used. Examples of the reactive organopolysiloxane include KF99 (methicone), KF9901 (hydrogen dimethicone), KF-9908 (triethoxysilylethyl polydimethylsiloxyethyl dimethicone), and KF-9909 (triethoxysilylethyl poly). Dimethylsiloxyethylhexyl dimethicone), KP-574 ((Acrylates / tridecyl acrylate / triethoxysilylpropyl methacrylate / dimethicone methacrylate) copolymer), KF-7312 (mixture of trimethylsiloxysilicic acid and cyclopentasiloxane), KF-9001 (50% solution of trimethylsiloxysilicic acid in decamethylcyclopentasiloxane) and the like can be used. As the alkylsilane, Z-6341 (octyltriethoxysilane) manufactured by Dow Corning or F-8261 (tridecafluorooctyltriethoxysilane) manufactured by Degussa can be used. As the organic titanate, Ajinomoto's Plenact KR-TTS (isopropyl triisostearoyl titanate) or the like can be used. As the polyolefin, for example, known compounds described in JP-A-63-179972, polyethylene oxide obtained by oxidizing polypropylene, maleated polyethylene, polypropylene oxide, and the like can be used. As the hydrogenated lecithin and / or salts thereof, for example, resinol S-10 (hydrogenated soybean phospholipid) of Nikko Chemicals Co., Ltd., egg yolk lecithin PL-100P (hydrogenated yolk phospholipid) of KUPY, etc. can be used. Examples of the acylated amino acids and / or salts thereof include sarcosinate MN (sodium myristoylmethylaminoacetate), alaninate LN-30 (sodium lauroylmethylalanine), sarcosinate CN-30 (cocoyl sarcosine sodium), and sarcosinate OH (oleic acid) from Nikko Chemical Co., Ltd. Oil sarcosine), Ajinomoto's Amisoft HS-21 (N-stearoyl-L-glutamate disodium), and SEPPIC's SEPILIFT DPHP (dipalmitoylhydroxyproline).
これら表面処理剤の使用量を限定するものではないが、本発明の表面処理剤の特性を損なわない程度に使用することが好ましい。好ましくは０．１から２０質量％程度である。
本発明に用いられる基材粉体としては、従来化粧料用粉体として用いられている粉体であれば特に制限されず、例えば、次のような基材粉体が挙げられる。またこれらの基材粉体は１種または２種以上を混合して用いても構わない。
The use amount of these surface treatment agents is not limited, but is preferably used to such an extent that the characteristics of the surface treatment agent of the present invention are not impaired. Preferably it is about 0.1 to 20% by mass.
The base powder used in the present invention is not particularly limited as long as it is a powder conventionally used as a cosmetic powder, and examples thereof include the following base powders. These base powders may be used alone or in combination of two or more.
酸化鉄、酸化亜鉛、酸化チタン、酸化セリウム、酸化マグネシウム、酸化ジルコニウム、硫酸バリウム、酸化クロム、群青、ベンガラ、炭酸マグネシウム、炭酸カルシュウム、マイカ、セリサイト、タルク、シリカ、カオリン、水酸化クロム、亜鉛華、カーボンブラック、アルミナ、ケイ酸アルミニウム、ケイ酸マグネシウム、窒化ホウ素、シリカ−アルミナ粉末、ベントナイト、スメクタイトなどの無機顔料、ナイロンパウダー、ポリウレタンパウダー、ポリメチルメタクリレート、スチレン−ジビニルベンゼン共重合体、ポリエチレン粉体、シリコーン樹脂、テフロン（登録商標）パウダー、シリコーンガム、シルクパウダー、カルナバワックス、ライスワックス、デンプン、微結晶セルロースなどの有機粉体、ローダミンＢ等の有機色素、赤色２０１号、黒色４０１号、黄色４号、青色1号等のジルコニウム、バリウム又はアルミニウムレーキ等の有機着色料、雲母チタン、酸化鉄コーティング雲母などの複合粉体、表面処理がなされている粉体などが挙げられ、形状としては、球状、板状、針状、繊維状など通常化粧料に用いられる形状、粒径であれば構わない。 Iron oxide, zinc oxide, titanium oxide, cerium oxide, magnesium oxide, zirconium oxide, barium sulfate, chromium oxide, ultramarine, red iron, magnesium carbonate, calcium carbonate, mica, sericite, talc, silica, kaolin, chromium hydroxide, zinc Hana, carbon black, alumina, aluminum silicate, magnesium silicate, boron nitride, silica-alumina powder, bentonite, inorganic pigments such as smectite, nylon powder, polyurethane powder, polymethyl methacrylate, styrene-divinylbenzene copolymer, polyethylene Organic powders such as powder, silicone resin, Teflon (registered trademark) powder, silicone gum, silk powder, carnauba wax, rice wax, starch, microcrystalline cellulose, and organic colors such as rhodamine B Red 201, black 401, yellow 4, blue 1, etc., organic colorants such as zirconium, barium or aluminum lake, composite powders such as titanium mica, iron oxide coated mica, powders which have been surface treated The shape may be any shape, such as a sphere, a plate, a needle, or a fibrous shape, and a particle size which are commonly used for cosmetics.
次に本発明の化粧料について詳述する。
本発明の化粧料は、上述の本発明の表面処理粉体を含有するもので、その剤型は任意であり、一般に従来の化粧料用粉体を含有する化粧料はすべて含まれる。このような化粧料としては、例えば、ファンデーション、コンシーラー、白粉、ほほ紅などのフェイシャル化粧料、アイシャドウ、マスカラ、アイライナー、眉墨、口紅、ネイルエナメルなどといったメークアップ化粧料及び日焼け止め化粧品、乳液、ローションなどの基礎化粧料等が挙げられる。また、化粧料の他、皮膚外用剤、医薬用軟膏等にも好適に使用できる。
Next, the cosmetic of the present invention will be described in detail.
The cosmetic of the present invention contains the above-mentioned surface-treated powder of the present invention, and its dosage form is arbitrary, and generally includes all cosmetics containing conventional powders for cosmetics. Such cosmetics include, for example, foundations, concealers, white powder, facial cosmetics such as blush, eye shadow, mascara, eyeliner, eyebrows, lipstick, nail enamel, etc. , Lotions and the like. In addition to cosmetics, it can also be suitably used for skin external preparations, pharmaceutical ointments, and the like.
本発明の表面処理粉体の配合量は、通常０．０１〜９９．９質量％であり、化粧料の形態や目的用途に応じて変動する。化粧料として香料等の他の成分を配合させること、十分な撥水性、撥油効果及び好ましい感触を得るためには、表面処理粉体の配合量が０．１〜９９質量％の範囲であることが好ましい。より具体的には、化粧料の種類により、例えば固形粉体化粧料には２０〜８０質量％、クリーム状化粧料には５〜５０質量％、乳液状化粧料には２〜３０質量％、ローション類には２〜２０質量％を配合するのがさらに好ましい。 The compounding amount of the surface-treated powder of the present invention is usually 0.01 to 99.9% by mass, and varies depending on the form of the cosmetic and the intended use. In order to mix other ingredients such as fragrances as a cosmetic, to obtain a sufficient water repellency, oil repellency and a favorable feel, the amount of the surface-treated powder is in the range of 0.1 to 99% by mass. Is preferred. More specifically, depending on the type of cosmetics, for example, 20 to 80% by mass for solid powder cosmetics, 5 to 50% by mass for creamy cosmetics, 2 to 30% by mass for emulsion cosmetics, It is more preferable to mix 2 to 20% by mass with lotions.
本発明の化粧料に配合できる、本発明に係わる表面処理粉体以外の成分としては、目的とする化粧料の種類に応じて、通常の化粧料に配合される成分から適宜選択して使用することができる。これらの成分としては、例えば、流動パラフィン、ワセリンなどの炭化水素、植物油脂、ロウ類、合成エステル油、シリコーン系の油相成分、フッ素系の油相成分、高級アルコール類、低級アルコール、脂肪酸類、増粘剤、紫外線吸収剤、粉体、無機・有機顔料、色材、各種界面活性剤、多価アルコール、糖、高分子化合物、生理活性成分、経皮吸収促進剤、溶媒、酸化防止剤、香料、防腐剤、各種添加剤等が挙げられるがこれらに限定されるものではない。 As the components other than the surface-treated powder according to the present invention, which can be blended with the cosmetic of the present invention, depending on the kind of the target cosmetic, it is used by appropriately selecting from the components blended with ordinary cosmetics. be able to. Examples of these components include liquid paraffin, hydrocarbons such as petrolatum, vegetable oils and fats, waxes, synthetic ester oils, silicone oil phase components, fluorine oil phase components, higher alcohols, lower alcohols, and fatty acids. , Thickeners, ultraviolet absorbers, powders, inorganic and organic pigments, coloring materials, various surfactants, polyhydric alcohols, sugars, polymer compounds, physiologically active ingredients, transdermal absorption enhancers, solvents, antioxidants , Fragrances, preservatives, various additives, and the like, but are not limited thereto.
本発明の化粧料は、通常の方法に従って製造することができる。本発明の化粧料用粉体を配合した化粧料は、耐水性・耐皮脂性に優れ、汗及び皮脂等による化粧崩れを防止し、且つ肌上への化粧料の塗布時の感触が滑らかで、付着性に優れ、しっとりした使用感を与えることができる。
以下に実施例を挙げて本発明を具体的に説明するが、本発明の技術的範囲はこれらに限定されるものではない。
The cosmetic of the present invention can be produced according to a usual method. The cosmetic containing the cosmetic powder of the present invention has excellent water resistance and sebum resistance, prevents makeup collapse due to sweat and sebum, and has a smooth feel when applying the cosmetic on the skin. It has excellent adhesion and can give a moist feeling.
Hereinafter, the present invention will be described specifically with reference to Examples, but the technical scope of the present invention is not limited thereto.
１．製造方法
（表面処理剤の製造法１）
ヘキサフルオロプロピレン１．５ｇとヘキサフルオロプロピレンオキシド１３．２８ｇを混合し、ｍ−キシレンヘキサフルオライド６０ｇに溶解した。フッ化セシウム０．１ｇと塩化リチウム０．１ｇ触媒存在下、８０℃で加熱重合したポリマーに対し、Ｎ，Ｎ−ジメチル−１，３−プロパンジアミン１．５ｇを水酸化ナトリウム０．１ｇ存在下１２０℃で反応、蒸留精製して平均重合度ｎ＝８である下記化学式（２）に示す目的の表面処理剤を１５．２ｇ得た。
1.5 g of hexafluoropropylene and 13.28 g of hexafluoropropylene oxide were mixed and dissolved in 60 g of m-xylene hexafluoride. In the presence of 0.1 g of cesium fluoride and 0.1 g of lithium chloride, 1.5 g of N, N-dimethyl-1,3-propanediamine and 0.1 g of sodium hydroxide were added to the polymer heated and polymerized at 80 ° C. The mixture was reacted at 120 ° C. and purified by distillation to obtain 15.2 g of a target surface treatment agent represented by the following chemical formula (2) having an average degree of polymerization n = 8.
（表面処理剤の製造法２）
任意の鎖長を有するパーフルオロアルキレン化合物に対し、パーフルオロフアルキルオキシド化合物をｍ−キシレンヘキサフルオライド溶媒中、０．１質量％のフッ化セシウムと０．１質量％の塩化リチウム存在下加熱重合したポリマーに対し、Ｎ，Ｎ−ジメチル−１，３−プロパンジアミンを水酸化ナトリウム触媒中反応させて、蒸留精製することで下記化学式（３）に示す目的とする表面処理剤を得た。得られた表面処理剤のｍ、ｎ、Ｘは下記表１に示す通りである。
For a perfluoroalkylene compound having an arbitrary chain length, a perfluoroalkyl oxide compound is heated in an m-xylene hexafluoride solvent in the presence of 0.1% by mass of cesium fluoride and 0.1% by mass of lithium chloride. The polymerized polymer was reacted with N, N-dimethyl-1,3-propanediamine in a sodium hydroxide catalyst and purified by distillation to obtain a target surface treatment agent represented by the following chemical formula (3). M, n, and X of the obtained surface treating agent are as shown in Table 1 below.
（表面処理剤の製造方法３）
任意の鎖長を有するパーフルオロアルキレン化合物に対し、パーフルオロフアルキルオキシド化合物をｍ−キシレンヘキサフルオライド溶媒中、０．１質量％のフッ化セシウムと０．１質量％の塩化リチウム存在下加熱重合したポリマーに対し、Ｎ，Ｎ−ジメチル−３−アミノ−１−エタノールを水酸化ナトリウム触媒中反応させて、蒸留精製することで下記化学式（４）に示す目的とする各種表面処理剤を得た。得られた表面処理剤のｍ、ｎ、Ｘは下記表１に示す通りである。
For a perfluoroalkylene compound having an arbitrary chain length, a perfluoroalkyl oxide compound is heated in an m-xylene hexafluoride solvent in the presence of 0.1% by mass of cesium fluoride and 0.1% by mass of lithium chloride. The polymerized polymer is reacted with N, N-dimethyl-3-amino-1-ethanol in a sodium hydroxide catalyst, and purified by distillation to obtain various surface treatment agents of interest represented by the following chemical formula (4). Was. M, n, and X of the obtained surface treating agent are as shown in Table 1 below.
（表面処理粉体の製造方法１）
ヘンシェルミキサーに顔料酸化チタン９５０ｇを入れ、表面処理剤の製造法１で合成した前記化学式（２）に示す表面処理剤５０ｇを３重量％リン酸水溶液中４５０ｇに溶解したものを加えて攪拌した。攪拌後、１１０℃で４時間乾燥し、アトマイザー粉砕した表面処理粉体を本発明品１とした。
(Production method 1 of surface-treated powder)
950 g of pigment titanium oxide was placed in a Henschel mixer, and a solution prepared by dissolving 50 g of the surface treating agent represented by the chemical formula (2) synthesized in Production Method 1 of a surface treating agent in 450 g of a 3% by weight phosphoric acid aqueous solution was added and stirred. After stirring, the powder was dried at 110 ° C. for 4 hours and atomized and pulverized to obtain a surface-treated powder, which was designated as product 1 of the present invention.
（表面処理粉体の製造方法２）
ビーカーに顔料酸化チタン９５．０ｇを秤り取り、精製水１００ｇを加えてよく攪拌した。ここにリン酸を加えてｐＨ３として、表面処理剤の製造法１で合成した前記化学式（２）に示す表面処理剤５．０ｇ加え、３０分間混合後ろ過した。これを取り出し乾燥機にて１１０℃で４時間乾燥し、アトマイザー粉砕した表面処理粉体を本発明品２とした。
(Production method 2 of surface-treated powder)
95.0 g of pigment titanium oxide was weighed and placed in a beaker, and 100 g of purified water was added thereto, followed by sufficient stirring. Phosphoric acid was added thereto to adjust the pH to 3, and 5.0 g of the surface treating agent represented by the chemical formula (2) synthesized by the method 1 for producing a surface treating agent was added, followed by mixing for 30 minutes and filtration. This was taken out and dried at 110 ° C. for 4 hours with a dryer, and the surface-treated powder pulverized with an atomizer was designated as product 2 of the present invention.
（表面処理粉体の製造方法３）
ヘンシェルミキサーに顔料酸化チタン９５０ｇを入れ、表面処理剤の製造法２で合成した前記化学式（３）に示す表面処理剤５０ｇを３重量％リン酸水溶液中４５０ｇに溶解したものを加えて攪拌した。攪拌後、１１０℃で４時間乾燥し、アトマイザー粉砕した表面処理粉体を本発明品３〜１０および比較品１〜４とした。用いた表面処理剤の種類は下記表１に示すｍ、ｎ、Ｘの通りである。
(Production method 3 of surface treated powder)
950 g of pigment titanium oxide was placed in a Henschel mixer, and a solution prepared by dissolving 50 g of the surface treatment agent represented by the chemical formula (3) synthesized in Production Method 2 of the surface treatment agent in 450 g of a 3% by weight phosphoric acid aqueous solution was added and stirred. After stirring, the powder was dried at 110 ° C. for 4 hours and atomized and pulverized. The types of surface treatment agents used are as shown in Table 1, below, m, n, and X.
（表面処理粉体の製造方法４）
ビーカーに顔料酸化チタン９５．０ｇを秤り取り、精製水１００ｇを加えてよく攪拌した。ここにリン酸を加えてｐＨ３として、表面処理剤の製造法２で合成した前記化学式（３）に示す表面処理剤または表面処理剤の製造法３で合成した前記化学式（４）に示す表面処理剤を５．０ｇ加え、３０分間混合後ろ過した。これを取り出し乾燥機にて１１０℃で４時間乾燥し、アトマイザー粉砕した表面処理粉体を本発明品１１〜１６および比較品５〜８とした。用いた表面処理剤の種類は下記表１に示すｍ、ｎ、Ｘの通りである。
(Production method 4 of surface-treated powder)
95.0 g of pigment titanium oxide was weighed and placed in a beaker, and 100 g of purified water was added thereto, followed by sufficient stirring. Here, phosphoric acid is added to adjust the pH to 3, and the surface treatment agent represented by the chemical formula (3) synthesized by the surface treatment agent production method 2 or the surface treatment represented by the chemical formula (4) synthesized by the surface treatment agent production method 3 5.0 g of the agent was added, mixed for 30 minutes and filtered. This was taken out and dried at 110 ° C. for 4 hours with a dryer, and atomized and pulverized surface-treated powders were designated as inventive products 11 to 16 and comparative products 5 to 8. The types of surface treatment agents used are as shown in Table 1, below, m, n, and X.
２．評価方法
（撥水性、撥油性）
試料を平板な容器に入れ、１００ｋｇ／ｃｍ２の力で平坦な表面を作り、ここに水滴、スクワラン滴を静かに落として、接触角を測定した。
2. Evaluation method (water repellency, oil repellency)
The sample was placed in a flat container, a flat surface was formed with a force of 100 kg / cm 2 , and water drops and squalane drops were gently dropped on the flat surface, and the contact angle was measured.
（付着性）
上腕内側部に試料を均質に擦り付け、これを刷毛ではき取った時に付着して
いる様子を肉眼観察し、以下の５点のスコアで評価し、その平均を求めた。
５： 未処理粉体よりも付着性に優れる
４： 未処理粉体よりも比較的付着性に優れる
３： 未処理粉体と同程度
２： 未処理粉体よりも比較的崩れやすい
１： 未処理粉体よりもかなり崩れやすい
(Adhesiveness)
The sample was uniformly rubbed against the inner part of the upper arm, and when the sample was scraped off with a brush, the state of adhesion was visually observed, evaluated by the following five scores, and the average was obtained.
5: better adhesion than untreated powder 4: relatively better adhesion than untreated powder 3: comparable to untreated powder 2: relatively more fragile than untreated powder 1: not Much easier to crumble than treated powder
（感触）モニター５名で、塗布時の滑らかさを以下の５点のスコアで評価し、その平均
を求めた。
５： 未処理粉体よりもかなり良い
４： 未処理粉体より良い
３： 未処理粉体と同程度
２： 未処理粉体よりも比較的劣る
１： 未処理粉体よりもかなり劣る
(Feeling) Five monitors evaluated the smoothness at the time of application with the following five scores, and the average was obtained.
5: significantly better than untreated powder 4: better than untreated powder 3: comparable to untreated powder 2: relatively poorer than untreated powder 1: significantly less than untreated powder
３．評価結果
評価結果を表１に示す。乾式表面処理、湿式表面処理のどちらの表面処理方法を用いても撥水、撥油性、感触に優れた良好な粉体が得られた。感触に関しては乾式処理を用いた方が良く、撥水性、撥油性に関しては湿式処理を用いた方が良好という結果が得られた。
比較品１〜７に示すように、重合度ｎが大きい場合や、パーフルオロアルキル基ｍ、Ｘが長すぎると付着性、感触が極端に劣り、また、側鎖にパーフルオロアルキル基がなく、水素原子の場合には撥水、撥油性が著しく劣るという結果が得られた。
3. Evaluation results Table 1 shows the evaluation results. A good powder having excellent water repellency, oil repellency and feel was obtained by using either of the surface treatment methods of the dry surface treatment and the wet surface treatment. It was found that the dry treatment was better for the feel and the wet treatment was better for the water repellency and oil repellency.
As shown in Comparative Products 1 to 7 , when the degree of polymerization n is large, or when the perfluoroalkyl groups m and X are too long, the adhesion and feel are extremely poor, and there is no perfluoroalkyl group in the side chain. In the case of a hydrogen atom, the result that water repellency and oil repellency were remarkably inferior was obtained.
１．製造方法
（表面処理剤の製造法４）
ヘキサフルオロプロピレン１．５ｇとヘキサフルオロプロピレンオキシド１３．２８ｇを混合し、ｍ−キシレンヘキサフルオライド６０ｇに溶解した。フッ化セシウム０．１ｇと塩化リチウム０．１ｇ触媒存在下、８０℃で加熱重合して得られた平均重合度が８であるポリマー酸フッ化物に対し、各種アミン化合物１．５モル等量を水酸化ナトリウム０．１ｇ存在下１２０℃で反応させ、蒸留精製することで下記化学式（５）に示す目的とする各種表面処理剤を得た。得られた表面処理剤のＺ、Ｒ１、Ｒ２、Ｒ３は下記表２に示す通りである。
1.5 g of hexafluoropropylene and 13.28 g of hexafluoropropylene oxide were mixed and dissolved in 60 g of m-xylene hexafluoride. In the presence of 0.1 g of cesium fluoride and 0.1 g of lithium chloride, 1.5 mol equivalents of various amine compounds were added to the polymer oxyfluoride having an average degree of polymerization of 8 obtained by heating at 80 ° C. in the presence of a catalyst. The mixture was reacted at 120 ° C. in the presence of 0.1 g of sodium hydroxide, and purified by distillation to obtain various target surface treatment agents represented by the following chemical formula (5). Z, R 1 , R 2 , and R 3 of the obtained surface treating agent are as shown in Table 2 below.
（表面処理粉体の製造方法５）
ビーカーに顔料酸化チタン９５．０ｇを秤り取り、精製水１００ｇを加えてよく攪拌した。ここにリン酸を加えてｐＨ３として、表面処理剤の製造法３で合成した前記化学式（５）に示す表面処理剤５．０ｇ加え、３０分間混合後ろ過した。これを取り出し乾燥機にて１１０℃で４時間乾燥し、アトマイザー粉砕した表面処理粉体を本発明品１７〜３２および比較品９〜１２とした。
(Production method 5 of surface-treated powder)
95.0 g of pigment titanium oxide was weighed and placed in a beaker, and 100 g of purified water was added thereto, followed by sufficient stirring. Phosphoric acid was added thereto to adjust the pH to 3, and 5.0 g of the surface treatment agent represented by the chemical formula (5) synthesized in Production Method 3 of the surface treatment agent was added, followed by mixing for 30 minutes and filtration. This was taken out and dried at 110 ° C. for 4 hours with a drier, and atomized and pulverized surface-treated powders were designated as inventive products 17 to 32 and comparative products 9 to 12.
２．評価方法
（撥水性、撥油性）
試料を平板な容器に入れ、１００ｋｇ／ｃｍ２の力で平坦な表面を作り、ここに水滴、スクワラン滴を静かに落として、接触角を測定した。
2. Evaluation method (water repellency, oil repellency)
The sample was placed in a flat container, a flat surface was formed with a force of 100 kg / cm 2 , and water drops and squalane drops were gently dropped on the flat surface, and the contact angle was measured.
（感触）
モニター５名で、塗布時の滑らかさを以下の５点のスコアで評価し、その平均
を求めた。
５： 未処理粉体よりもかなり良い
４： 未処理粉体より良い
３： 未処理粉体と同程度
２： 未処理粉体よりも比較的劣る
１： 未処理粉体よりもかなり劣る
(Feel)
Five monitors evaluated the smoothness at the time of application with the following five scores, and the average was calculated.
5: significantly better than untreated powder 4: better than untreated powder 3: comparable to untreated powder 2: relatively poorer than untreated powder 1: significantly less than untreated powder
３．評価結果
評価結果を表２に示す。アミド体、エステル体のどちらの表面処理剤を用いても良好な撥水、撥油性、感触の粉体が得られた。表面処理剤としてＮ−エチルアミド化合物では感触が優れず、Ｒ１、Ｒ２、Ｒ３が長鎖脂肪酸である場合は撥油性に著しい低下が見られた。
3. Evaluation results Table 2 shows the evaluation results. Powders with good water repellency, oil repellency and feel were obtained using either the amide or ester surface treatment agent. The N-ethylamide compound as a surface treatment agent did not have a good feel, and when R1, R2, and R3 were long-chain fatty acids, a remarkable decrease in oil repellency was observed.
１．製造方法
（表面処理粉体の製造方法６）
ビーカーに顔料酸化チタン１００．０ｇを秤り取り、精製水１００ｇを加えてよく攪拌した。ここに下記表３に示す酸を加えてＰＨ３として、表面処理剤の製造法１で合成した前記化学式（２）に示す表面処理剤を加え、３０分間混合後ろ過した。これを取り出し乾燥機にて１１０℃で４時間乾燥し、アトマイザー粉砕した表面処理粉体を本発明品３３〜４３とした。
1. Production method (Production method 6 for surface-treated powder)
100.0 g of pigment titanium oxide was weighed into a beaker, 100 g of purified water was added, and the mixture was stirred well. To this, an acid shown in Table 3 below was added to obtain PH3, the surface treatment agent represented by the chemical formula (2) synthesized by the method 1 for producing a surface treatment agent was added, and the mixture was mixed for 30 minutes and filtered. This was taken out and dried at 110 ° C. for 4 hours with a drier, and atomized and pulverized surface-treated powders were designated as products 33 to 43 of the present invention.
２．評価方法
（撥水性、撥油性）
試料を平板な容器に入れ、１００ｋｇ／ｃｍ２の力で平坦な表面を作り、ここに水滴、スクワラン滴を静かに落として、接触角を測定した。
2. Evaluation method (water repellency, oil repellency)
The sample was placed in a flat container, a flat surface was formed with a force of 100 kg / cm 2 , and water drops and squalane drops were gently dropped on the flat surface, and the contact angle was measured.
（感触）
モニター５名で、塗布時の滑らかさを以下の５点のスコアで評価し、その平均を求めた。
５： 未処理粉体よりもかなり良い
４： 未処理粉体より良い
３： 未処理粉体と同程度
２： 未処理粉体よりも比較的劣る
１： 未処理粉体よりもかなり劣る
(Feel)
Five monitors evaluated the smoothness at the time of application with the following five scores, and the average was calculated.
5: significantly better than untreated powder 4: better than untreated powder 3: comparable to untreated powder 2: relatively poorer than untreated powder 1: significantly less than untreated powder
３．評価結果
評価結果を表３に示す。酸性物質の種類を問わず、良好な撥水性、撥油性、感触の粉体が得られた。中和を行う際の酸の種類による撥水性、撥油性、感触の違いに大きな影響は見られなかったが、未中和よりも中和した表面処理剤を用いた方が高い効果が得られた。
１．製造方法
（表面処理粉体の製造方法６）
ヘンシェルミキサーに顔料酸化チタン９４ｇを入れ、表面処理剤の製造法１で合成した前記化学式（２）に示す表面処理剤５ｇを３重量％リン酸水溶液中４５ｇに溶解したものを加えて攪拌した。次いでさらに本発明でいう一般式（１）以外の表面処理剤１ｇを別途添加し、再度攪拌した。攪拌後、１１０℃で４時間乾燥し、アトマイザー粉砕した表面処理粉体を本発明品４４〜４９とした。
1. Production method (Production method 6 for surface-treated powder)
94 g of pigment titanium oxide was placed in a Henschel mixer, and a solution prepared by dissolving 5 g of the surface treating agent represented by the chemical formula (2) synthesized in Production Method 1 of the surface treating agent in 45 g of a 3% by weight phosphoric acid aqueous solution was added and stirred. Next, 1 g of a surface treating agent other than the general formula (1) referred to in the present invention was separately added, followed by stirring again. After stirring, the powder was dried at 110 ° C. for 4 hours and atomized and pulverized to obtain surface-treated powders of the present invention.
２．評価方法
（撥水性、撥油性）
試料を平板な容器に入れ、１００ｋｇ／ｃｍ２の力で平坦な表面を作り、ここに水滴、スクワラン滴を静かに落として、接触角を測定した。
2. Evaluation method (water repellency, oil repellency)
The sample was placed in a flat container, a flat surface was formed with a force of 100 kg / cm 2 , and water drops and squalane drops were gently dropped on the flat surface, and the contact angle was measured.
（感触）
モニター５名で、塗布時の滑らかさを以下の５点のスコアで評価し、その平均を求めた。
５： 未処理粉体よりもかなり良い
４： 未処理粉体より良い
３： 未処理粉体と同程度
２： 未処理粉体よりも比較的劣る
１： 未処理粉体よりもかなり劣る
(Feel)
Five monitors evaluated the smoothness at the time of application with the following five scores, and the average was calculated.
5: significantly better than untreated powder 4: better than untreated powder 3: comparable to untreated powder 2: relatively poorer than untreated powder 1: significantly less than untreated powder
３．評価結果
評価結果を表４に示す。多くの組み合わせで、パーフルオロポリエーテル化合物単独と同程度の撥水性、撥油性と感触が得られた。本実験においてもアミノ基を有するパーフルオロポリエーテル化合物との併用により、相乗的に機能の改善が認められた。
１．製造方法
（表面処理粉体の製造方法６）
ヘンシェルミキサーに化粧用顔料９５ｇを入れ、表面処理剤の製造法１で合成した前記化学式（２）に示す表面処理剤５ｇを３重量％リン酸水溶液中４５ｇに溶解したものを加えて攪拌した。攪拌後、１１０℃で４時間乾燥し、アトマイザー粉砕した表面処理粉体を本発明品５０〜６３とした。
1. Production method (Production method 6 for surface-treated powder)
95 g of a cosmetic pigment was put into a Henschel mixer, and a solution prepared by dissolving 5 g of the surface treating agent represented by the chemical formula (2) synthesized in Production Method 1 of a surface treating agent in 45 g of a 3% by weight phosphoric acid aqueous solution was added and stirred. After stirring, the powder was dried at 110 ° C. for 4 hours and atomized and pulverized to obtain surface-treated powders of the present invention.
２．評価方法
（撥水性、撥油性）
試料を平板な容器に入れ、１００ｋｇ／ｃｍ２の力で平坦な表面を作り、ここに水滴、スクワラン滴を静かに落として、接触角を測定した。
2. Evaluation method (water repellency, oil repellency)
The sample was placed in a flat container, a flat surface was formed with a force of 100 kg / cm 2 , and water drops and squalane drops were gently dropped on the flat surface, and the contact angle was measured.
（感触）
モニター５名で、塗布時の滑らかさを以下の５点のスコアで評価し、その平均
を求めた。
５： 未処理粉体よりもかなり良い
４： 未処理粉体より良い
３： 未処理粉体と同程度
２： 未処理粉体よりも比較的劣る
１： 未処理粉体よりもかなり劣る
(Feel)
Five monitors evaluated the smoothness at the time of application with the following five scores, and the average was calculated.
5: significantly better than untreated powder 4: better than untreated powder 3: comparable to untreated powder 2: relatively poorer than untreated powder 1: significantly less than untreated powder
３．評価結果
評価結果を表５に示す。多くの無機顔料、有機顔料において、良好な撥水性、撥油性と感触が得られた。
化粧下地
（処方） （質量％）
Ａ 水 残部
グリセリン ５．０
ステアロキシＰＧヒドロキシＰＧヒドロキシエチル
スルフォン酸ナトリウム ２．０
Ｂ パーフルオロアルキル（Ｃ４−１４）エトキシジメチコン １３．０
シクロメチコン １０．０
ジメチコン ６．０
メトキシケイヒ酸オクチル ４．０
エタノール ３．０
イソステアリルグリセリン ３．０
１、３−ブチレングリコール ２．０
カーボマー（４％水溶液） ２．０
ナイロン１２ ２．０
表面処理１２−ナイロンパウダー（本発明品６２） ２．０
表面処理酸化チタン（本発明品２） ２．０
表面処理ベンガラ（本発明品５５） ０．５
表面処理酸化鉄（本発明品５６） ０．５
表面処理酸化鉄（本発明品５７） ０．１
（調製方法）Ａ相を常温にてホモミキサーにて攪拌しなら、Ｂ相を加えて乳化した。
（結果）ＳＰＦ３０／ＰＡ＋＋で、撥水性、撥油性に優れ、感触の良い化粧下地を得た。
Makeup base (prescription) (% by mass)
A water balance glycerin 5.0
Stearyloxy PG hydroxy PG hydroxyethyl
Sodium sulfonate 2.0
B perfluoroalkyl (C4-14) ethoxydimethicone 13.0
Cyclomethicone 10.0
Dimethicone 6.0
Octyl methoxycinnamate 4.0
Ethanol 3.0
Isostearyl glycerin 3.0
1,3-butylene glycol 2.0
Carbomer (4% aqueous solution) 2.0
Nylon 12 2.0
Surface treatment 12-Nylon powder (Product 62 of the present invention) 2.0
Surface-treated titanium oxide (Product 2 of the present invention) 2.0
Surface treatment bengara (product 55 of the present invention) 0.5
Surface treated iron oxide (Product 56 of the present invention) 0.5
Surface-treated iron oxide (Product 57 of the present invention) 0.1
(Preparation method) If phase A was stirred at room temperature with a homomixer, phase B was added and emulsified.
(Results) With SPF30 / PA ++, a cosmetic base with excellent water repellency and oil repellency and a good touch was obtained.
パウダーファンデーション
（処方） （質量％）
Ａ 表面処理マイカ（本発明品５２） 残部
表面処理タルク（本発明品５１） １５．０
表面処理セリサイト（本発明品５３） １０．０
ナイロン１２ １０．０
Ｂ ジメチコン ７．０
ミリスチン酸イソセチル ５．０
メトキシケイヒ酸オクチル ５．０
（ジフェニルジメチコン／ビニルフェニルジメチコン／
シルセスキオキサン）クロスポリマー ３．０
トリ（カプリル／カプリン酸）グリセリル ３．０
水添ポリイソブテン ３．０
（調製方法）Ｂ成分をよく混和し、Ａ成分を加えて均一になるまでさらに混和し、容器に充填して製品とした。
（結果）ＳＰＦ２５／ＰＡ＋＋で、撥水撥油性に優れ、感触の良いファンデーションを得た。
Powder foundation (prescription) (% by mass)
A Surface-treated mica (Invention product 52) Remaining Surface-treated talc (Invention product 51) 15.0
Surface treatment sericite (Product 53 of the present invention) 10.0
Nylon 12 10.0
B Dimethicone 7.0
Isocetyl myristate 5.0
Octyl methoxycinnamate 5.0
(Diphenyldimethicone / vinylphenyldimethicone /
Silsesquioxane) crosspolymer 3.0
Tri (caprylic / capric acid) glyceryl 3.0
Hydrogenated polyisobutene 3.0
(Preparation method) The B component was mixed well, the A component was added, and further mixed until uniform, and the mixture was filled in a container to obtain a product.
(Results) With SPF25 / PA ++, a foundation with excellent water and oil repellency and good touch was obtained.
リキッドファンデーション
（処方） （質量％）
Ａ 精製水 残部
ブチレングリコール ５．０
グリセリン ２．０
カルボマー ０．１
フェノキシエタノール ３．０
Ｂ シクロペンタシロキサン ２０．０
表面処理酸化チタン（本発明品１） ５．０
表面処理酸化亜鉛（本発明品５０） ６．０
ＰＥＧ−９ポリジメチルシロキシエチルジメチコン ２．０
（アクリルサンアルキル／ジメチコン）コポリマー ２．０
（ジメチコン／ビニルジメチコン）クロスポリマー ２．０
フィトステロールイソステアレート １．０
色材 適量
（調製方法）Ｂ相をディスパーで良く混合後、均一溶液としたＡ相にホモミキサー攪拌しながら、加えて乳化した。
（結果）撥水性、撥油性に優れた乳液状ファンデーションを得た。紫外線防御能もＳＰＦ２０、ＰＡ＋＋と高い値を示した。
Liquid foundation (prescription) (% by mass)
A Purified water Remainder Butylene glycol 5.0
Glycerin 2.0
Carbomer 0.1
Phenoxyethanol 3.0
B cyclopentasiloxane 20.0
Surface-treated titanium oxide (Product 1 of the present invention) 5.0
Surface-treated zinc oxide (50 of the present invention) 6.0
PEG-9 polydimethylsiloxyethyl dimethicone 2.0
(Acrylic Sanalkyl / Dimethicone) Copolymer 2.0
(Dimethicone / vinyl dimethicone) crosspolymer 2.0
Phytosterol isostearate 1.0
Coloring material An appropriate amount (preparation method) The phase B was mixed well with a disper, and the mixture was added to the homogeneous solution A while stirring with a homomixer and emulsified.
(Result) An emulsion foundation having excellent water repellency and oil repellency was obtained. The UV protection ability also showed a high value of SPF20 and PA ++.
Ｗ／Ｏ紫外線防御化粧品
（表面処理粉体の製造方法７）
ヘンシェルミキサーに微粒子酸化亜鉛９５ｇを入れ、表面処理剤の製造法１で合成した前記化学式（２）に示す表面処理剤５ｇを３重量％リン酸メタノール溶液１５ｇに分散したものを加えて攪拌した。攪拌後、１１０℃で４時間乾燥したものを本発明品６４とした。
W / O UV protection cosmetic (Production method 7 of surface treated powder)
95 g of fine zinc oxide particles were placed in a Henschel mixer, and 5 g of the surface treating agent represented by the chemical formula (2) synthesized by the method 1 for producing a surface treating agent dispersed in 15 g of a 3% by weight methanolic phosphoric acid solution was added thereto, followed by stirring. After stirring and drying at 110 ° C. for 4 hours, the product 64 of the present invention was obtained.
（表面処理粉体の製造方法８）
ヘンシェルミキサーに微粒子酸化チタン９５ｇを入れ、表面処理剤の製造法１で合成した前記化学式（２）に示す表面処理剤５ｇを３重量％リン酸メタノール溶液１５ｇに分散したものを加えて攪拌した。攪拌後、１１０℃で４時間乾燥したものを本発明品６５とした。
(Production method 8 of surface-treated powder)
95 g of fine particle titanium oxide was placed in a Henschel mixer, and 5 g of the surface treatment agent represented by the chemical formula (2) synthesized in Production Method 1 of the surface treatment agent dispersed in 15 g of a 3% by weight methanolic phosphate solution was added thereto, followed by stirring. After stirring and drying at 110 ° C. for 4 hours, the product 65 of the present invention was obtained.
（処方） （質量％）
Ａ ジメチコン １０．０
ジフェニルシロキシフェニルトリメチコン ５．０
（ジメチコン／メチコン）・コポリマー ６．０
セレシン ５．０
トリオクタン酸トリメチロールプロパン ５．０
セスキイソステアリン酸ソルビタン ４．０
カルナウバロウ １．０
表面処理微粒子酸化亜鉛（本発明品６４） １０．０
表面処理微粒子酸化チタン（本発明品６５） ２．０
表面処理タルク（本発明品５１） ２．０
表面処理セリサイト（本発明品５３） ２．０
シクロメチコン ３．０
メトキシケイヒ酸オクチル ５．０
ミネラルオイル １．０
ワセリン １．０
Ｂ ジプロピレングリコール ２．０
ヒアルロン酸ナトリウム ０．２
水 残部
（調製方法）Ａ成分を７０℃に加熱し、本発明粉体以外を均一に溶解させた後、ホモミキサーまたはディスパーミキサーでゆっくりと攪拌しながらＡにＢを徐々に加えた後、強く攪拌して乳化を行う。
（結果）撥水性、撥油性に優れ、使用感の良いＷ／Ｏ型の紫外線防御化粧品が得られた。また本発明処理粉体の分散性は高く、高い紫外線防御能を示した。ＳＰＦ３５、ＰＡ＋＋＋
(Prescription) (% by mass)
A dimethicone 10.0
Diphenylsiloxyphenyltrimethicone 5.0
(Dimethicone / methicone) copolymer 6.0
Ceresin 5.0
Trimethylolpropane trioctanoate 5.0
Sorbitan sesquiisostearate 4.0
Carnauba wax 1.0
Surface treated fine particle zinc oxide (Product 64 of the present invention) 10.0
Surface-treated fine particle titanium oxide (Product 65 of the present invention) 2.0
Surface treated talc (Invention product 51) 2.0
Surface treated sericite (Product 53 of the present invention) 2.0
Cyclomethicone 3.0
Octyl methoxycinnamate 5.0
Mineral oil 1.0
Vaseline 1.0
B dipropylene glycol 2.0
Sodium hyaluronate 0.2
Water Remaining part (Preparation method) After heating the component A to 70 ° C. and uniformly dissolving the components other than the powder of the present invention, slowly adding B to A while slowly stirring with a homomixer or disper mixer, Stir to emulsify.
(Results) A W / O-type UV protective cosmetic having excellent water repellency and oil repellency and good feeling in use was obtained. Further, the dispersibility of the treated powder of the present invention was high, and a high ultraviolet protection ability was exhibited. SPF35, PA ++++
紫外線防御機能を有するファンデーション
（表面処理粉体の製造方法９）
ヘンシェルミキサーに合成金雲母９４ｇを入れ、表面処理剤の製造法１で合成した前記化学式（２）に示す表面処理剤５ｇを３重量％リン酸メタノール溶液４５ｇに分散したものを加えて攪拌した。攪拌後、アミノ変性シリコーンを１ｇ加えてさらに攪拌した。攪拌後、１１０℃で４時間乾燥したものを本発明品６６とした。
Foundation having UV protection function (Production method of surface-treated powder 9)
94 g of synthetic phlogopite was placed in a Henschel mixer, and a dispersion of 5 g of the surface treatment agent represented by the chemical formula (2) synthesized in Production Method 1 of the surface treatment agent in 45 g of a 3% by weight methanolic phosphate solution was added and stirred. After stirring, 1 g of amino-modified silicone was added and further stirred. After stirring and drying at 110 ° C. for 4 hours, the product 66 of the present invention was obtained.
（処方） （質量％）
表面処理タルク（本発明品５１） 残部
表面処理合成金雲母（本発明品６６） １０．０
表面処理微粒子酸化亜鉛（本発明品６４） ５．０
メトキシケイヒ酸オクチル ６．０
ミネラルオイル ５．０
微粒子シリカ ３．０
フィトステリルイソステレート ３．０
ジメチコン ３．０
ナイロン粉末 ３．０
トリエチルヘキサノイン ３．０
水 ３．０
トリイソステアリン酸ポリグリセリル−２ １．０
色材 １．０
（調製方法）全ての成分をヘンシェルミキサーにて均一になるまで混合し、容器に充填して製品とした。
（結果）肌に対する伸び、滑らかさ、付着性に優れ、オイルへの分散性に優れ、色むらの無いファンデーションが得られた。ＳＰＦ２５、ＰＡ＋＋
(Prescription) (% by mass)
Surface-treated talc (product 51 of the present invention) Remaining surface-treated synthetic phlogopite (product 66 of the present invention) 10.0
Surface treated fine particle zinc oxide (Product 64 of the present invention) 5.0
Octyl methoxycinnamate 6.0
Mineral oil 5.0
Fine particle silica 3.0
Phytosteryl isosterate 3.0
Dimethicone 3.0
Nylon powder 3.0
Triethylhexanoin 3.0
Water 3.0
Polyglyceryl-2 triisostearate 1.0
Color material 1.0
(Preparation method) All components were mixed until uniform using a Henschel mixer and filled into a container to obtain a product.
(Results) A foundation was obtained which was excellent in elongation, smoothness, and adhesion to the skin, excellent in dispersibility in oil, and without color unevenness. SPF25, PA ++
口紅
（表面処理粉体の製造方法１０）
ビーカーにベンガラ９５．０ｇを秤り取り、精製水１００ｇを加えてよく攪拌した。ここに下記表３に示す酸を加えてｐＨ３として、表面処理剤の製造法１で合成した前記化学式（２）に示す表面処理剤を５．０ｇ加え、３０分間混合後ろ過した。これを取り出し乾燥機にて１１０℃で４時間乾燥し、アトマイザー粉砕した表面処理粉体を本発明品６７とした。
Lipstick (Production method 10 of surface-treated powder)
95.0 g of Bengala was weighed and placed in a beaker, 100 g of purified water was added, and the mixture was stirred well. An acid shown in Table 3 below was added to adjust the pH to 3, and 5.0 g of the surface treating agent represented by the chemical formula (2) synthesized by the method 1 for producing a surface treating agent was added. After mixing for 30 minutes, the mixture was filtered. This was taken out and dried at 110 ° C. for 4 hours with a drier, and the surface-treated powder pulverized by the atomizer was designated as product 67 of the present invention.
（処方） （質量％）
ポリブテン ６０．０
リンゴ酸イソステアリル １０．０
トリオクタノイン １０．０
パルミチン酸デキストリン ３．０
トリイソステアリン酸ジグリセリン ３．０
テトライソステアリン酸ペンタエリスリチル ３．０
（ジメチコン／メチコン）コポリマー ２．０
ジメチコン ２．０
炭酸カルシウム １．０
ミリスチン酸デキストリン １．０
表面処理酸化チタン（本発明品４８） １．０
表面処理ベンガラ（本発明品６７） １．０
表面処理マイカ（本発明品５２） １．０
その他色材、香料 残部
（調製方法）全ての成分をはかりとり、ロールミルを使用して均一に混和して作成した。
（結果）顔料の分散性に優れ鮮やかな色調の口紅が得られた。付着性に優れ、容器などへの色移りし難いものが得られた。
(Prescription) (% by mass)
Polybutene 60.0
Isostearyl malate 10.0
Trioctanoin 10.0
Dextrin palmitate 3.0
Diglycerin triisostearate 3.0
Pentaerythrityl tetraisostearate 3.0
(Dimethicone / methicone) copolymer 2.0
Dimethicone 2.0
Calcium carbonate 1.0
Dextrin myristate 1.0
Surface-treated titanium oxide (Invention product 48) 1.0
Surface treatment bengara (product 67 of the present invention) 1.0
Surface treated mica (Invention product 52) 1.0
Other Coloring Materials, Perfume Remaining (Preparation Method) All the components were weighed and uniformly mixed using a roll mill to prepare a mixture.
(Result) A lipstick having excellent pigment dispersibility and a vivid color tone was obtained. A product having excellent adhesion and hardly causing color transfer to a container or the like was obtained.
皮膜形アイライナー
（処方） （質量％）
Ａ 表面処理酸化鉄（黒）（本発明品５７） １４．０
グリセリン ５．０
ポリオキシエチレンソルビタンモノオレイン酸エステル １．０
防腐剤 適量
水 １９．０
Ｂ 酢酸ビニル樹脂エマルション ４５．０
カルボキシメチルセルロース（１０％水溶液） １５．０
クエン酸アセチルトリブチル ５．０
香料 適量
（調製方法）精製水にグリセリン、ポリオキシエチレンソルビタンモノオレイン酸エステルを加え、加熱融解した後、表面処理酸化鉄(黒)を加えてコロイドミルでＡを調製する。７０℃に加温したＢをＡに混合し、ホモミキサーで均一に分散し、容器に充填して製品とした。
（結果）化粧持ちの良い、撥水・撥油性を示す付着性に優れたアイライナーが得られた。
Film type eyeliner (prescription) (% by mass)
A Surface-treated iron oxide (black) (Product 57 of the present invention) 14.0
Glycerin 5.0
Polyoxyethylene sorbitan monooleate 1.0
Preservatives qs water 19.0
B Vinyl acetate resin emulsion 45.0
Carboxymethylcellulose (10% aqueous solution) 15.0
Acetyltributyl citrate 5.0
Fragrance Appropriate amount (preparation method) Glycerin and polyoxyethylene sorbitan monooleate are added to purified water, heated and melted, and surface-treated iron oxide (black) is added to prepare A in a colloid mill. B heated to 70 ° C. was mixed with A, uniformly dispersed with a homomixer, and filled in a container to obtain a product.
(Results) An eyeliner having good makeup and exhibiting excellent water and oil repellency and excellent adhesion was obtained.
フェルトペンタイプアイライナー
（処方） （質量％）
Ａ 表面処理カーボンブラック（本発明品６３） ５．０
ポリオキシエチレン（１０）ドデシルエーテル ２．０
精製水 ８０．０
Ｂ グリセリン １０．０
防腐剤 適量
香料 適量
水 残部
（調製方法）水にポリオキシエチレン（１０）ドデシルエーテルを溶解した後、表面処理カーボンブラックを加えボールミルで均一に粉砕し、Ａを調製した。ＡにＢを加え、均一に分散した後、容器に充填して製品とした。
（結果）化粧くすみがなく、撥水・撥油性を示す発色に優れたペンタイプのアイライナーが得られた。
Felt pen type eyeliner (prescription) (% by mass)
A Surface-treated carbon black (Product 63 of the present invention) 5.0
Polyoxyethylene (10) dodecyl ether 2.0
Purified water 80.0
B Glycerin 10.0
Preservative Appropriate amount Fragrance Appropriate amount Water Remainder (Preparation method) After dissolving polyoxyethylene (10) dodecyl ether in water, surface-treated carbon black was added and uniformly ground with a ball mill to prepare A. B was added to A, dispersed uniformly, and then filled into a container to obtain a product.
(Results) A pen-type eyeliner having no cosmetic dullness and exhibiting excellent water repellency and oil repellency was obtained.
ウォータープルーフマスカラ
（処方） （質量％）
Ａ 表面処理酸化鉄（黒）（本発明品５７） ５．０
アクリル酸アルキルコポリマーアンモニウム ３０．０
防腐剤 適量
水 １０．０
Ｂ 軽質イソパラフィン ３０．０
固形パラフィン ８．０
ラノリンワックス ８．０
セスキオレイン酸ソルビタン ４．０
香料 適量
（調製方法）水に表面処理酸化鉄(黒)を加えてホモミキサーで分散したのち、アクリル酸アルキルコポリマーアンモニウムを加えて加熱して、Ａを調製した。Ｂを加え、ホモミキサーで均一に乳化分散した後、容器に充填して製品とした。
（結果）優れた撥水・撥油性を示し、化粧持ちの良いマスカラが得られた。
Waterproof mascara (prescription) (% by mass)
A Surface-treated iron oxide (black) (Product 57 of the present invention) 5.0
Alkyl acrylate copolymer ammonium 30.0
Preservatives qs water 10.0
B Light isoparaffin 30.0
Solid paraffin 8.0
Lanolin wax 8.0
Sorbitan sesquioleate 4.0
Flavor A suitable amount (preparation method) was added to surface-treated iron oxide (black) in water, dispersed by a homomixer, and then added with an alkyl acrylate ammonium copolymer and heated to prepare A. B was added, and the mixture was uniformly emulsified and dispersed with a homomixer, and then filled into a container to obtain a product.
(Results) Mascara showing excellent water repellency and oil repellency and having a long lasting makeup was obtained.
ルースタイプアイシャドー
（処方） （質量％）
表面処理マイカ（本発明品５２） ２８．０
オキシ塩化ビスマス ４０．０
シリカ １０．０
表面処理酸化チタン（本発明品１） ５．０
表面処理ベンガラ（本発明品５５） ６．０
表面処理酸化鉄（黄）（本発明品５６） ５．０
表面処理カーボンブラック（本発明品６３） １．０
表面処理微粒子酸化チタン（本発明品６５） ５．０
（調製方法）すべての原料を量り入れ、ミキサーで均一に分散し、容器に充填して製品とした。
（結果）肌触りが良好で、密着感に優れた、化粧くすみしない、撥水・撥油性を有する優れたアイシャドーが得られた。
Loose type eye shadow (prescription) (% by mass)
Surface treated mica (Invention product 52) 28.0
Bismuth oxychloride 40.0
Silica 10.0
Surface-treated titanium oxide (Product 1 of the present invention) 5.0
Surface treatment bengara (Product 55 of the present invention) 6.0
Surface treated iron oxide (yellow) (Product 56 of the present invention) 5.0
Surface-treated carbon black (Product 63 of the present invention) 1.0
Surface-treated fine particle titanium oxide (Product 65 of the present invention) 5.0
(Preparation method) All raw materials were weighed, uniformly dispersed by a mixer, and filled in a container to obtain a product.
(Results) An excellent eye shadow having good texture, excellent adhesion, non-dulling makeup, and water and oil repellency was obtained.
乳化タイプアイシャドー
（処方） （質量％）
Ａ 表面処理タルク（本発明品５１） １０．０
表面処理カオリン（本発明品５４） ２．０
表面処理ウルトラマリン（本発明品５８） ４．０
表面処理クロムグリーン（本発明品５９） １．０
Ｂ ミリスチン酸イソプロピル ８．０
流動パラフィン ５．０
ステアリン酸 ３．０
モノラウリン酸プロピレングリコール ３．０
Ｃ ブチレングリコール ５．０
グリセリン １．０
トリエタノールアミン １．２
防腐剤 適量
水 残部
（調製方法）Ａをブレンダーで均一に混合した。Ｃを加熱溶解した後、Ａを加え、攪拌混合した。Ｂを加熱融解し、混合したＡとＣに攪拌しながら加え、ホモミキサーにより乳化分散した。室温まで攪拌冷却し、容器に充填して製品とした。
（結果）表面処理により金属イオンの溶出が抑えられた、発色の優れた、耐水性、耐油性の良いリキッドアイシャドーが得られた。
Emulsifying type eye shadow (prescription) (% by mass)
A Surface-treated talc (Product 51 of the present invention) 10.0
Surface treated kaolin (Product 54 of the present invention) 2.0
Surface treated ultramarine (Invention product 58) 4.0
Surface-treated chrome green (Product 59 of the present invention) 1.0
B Isopropyl myristate 8.0
Liquid paraffin 5.0
Stearic acid 3.0
Propylene glycol monolaurate 3.0
C butylene glycol 5.0
Glycerin 1.0
Triethanolamine 1.2
Preservative Appropriate amount Water The remainder (preparation method) A was uniformly mixed with a blender. After heating and dissolving C, A was added and mixed with stirring. B was melted by heating, added to the mixed A and C while stirring, and emulsified and dispersed by a homomixer. The mixture was stirred and cooled to room temperature and filled in a container to obtain a product.
(Results) A liquid eye shadow having excellent coloring and excellent water resistance and oil resistance, in which elution of metal ions was suppressed by the surface treatment, was obtained.
鉛筆タイプ眉墨
（処方） （質量％）
Ａ 表面処理酸化鉄（黒）（本発明品５７） ２０．０
表面処理酸化カオリン（本発明品５４） １５．０
表面処理タルク（本発明品５１） １０．０
表面処理酸化チタン（本発明品１） ５．０
Ｂ （ミリスチン酸／パルミチン酸／ステアリン酸／
リシノレイン酸／エイコサン二酸）グリセリズ ２０．０
ステアリン酸 １０．０
ミツロウ ５．０
硬化ヒマシ油 ５．０
ワセリン ４．０
ラノリン ３．０
流動パラフィン ３．０
（調製方法）Ａをブレンダーで均一に混合した。Ｂを加熱融解し、Ａを加え、混練した。芯に成型し、木にはさんで鉛筆形状とした。
（結果）肌への感触が滑らかで良好な、撥水・撥油性を有した優れた眉墨が得られた。
Pencil type eyebrow ink (prescription) (% by mass)
A Surface treated iron oxide (black) (Product 57 of the present invention) 20.0
Surface-treated oxidized kaolin (Product 54 of the present invention) 15.0
Surface-treated talc (Invention product 51) 10.0
Surface-treated titanium oxide (Product 1 of the present invention) 5.0
B (myristic acid / palmitic acid / stearic acid /
Ricinoleic acid / eicosane diacid) glycerides 20.0
Stearic acid 10.0
Beeswax 5.0
Hardened castor oil 5.0
Vaseline 4.0
Lanolin 3.0
Liquid paraffin 3.0
(Preparation method) A was uniformly mixed with a blender. B was heated and melted, A was added and kneaded. It was molded into a core and sandwiched between trees to form a pencil.
(Results) An excellent eyebrow ink having a water-repellent and oil-repellent property with a smooth and good feel to the skin was obtained.
本発明の表面処理粉体は、従来兼ね備えることが困難だった撥水性、撥油性、感触、付着性を有しているため、これを用いて化粧の乗りや感触が良く、化粧持ちの良い化粧料を提供する。 Since the surface-treated powder of the present invention has water repellency, oil repellency, feel, and adhesiveness, which have been difficult to provide in the past, it is used to make makeup and feel good, and to have a long lasting makeup. Offer a fee.
Claims (5)
（但し、ｍは２を表し、ｎは平均値で１〜２０の整数を表し、Ｒ１は炭素数２〜６のアルキレン基を表し、Ｒ２は水素原子または炭素数の合計が１〜８のアルキル基、アラルキル基、アリール基を表し、Ｒ３は水素原子または炭素数の合計が１〜８のアルキル基、アラルキル基、アリール基を表し、Ｘはフッ素原子、または炭素数１〜３のパーフルオロアルキル基を表し、ＺはＮＨまたはＮ−ＣＨ３または酸素原子を表す。） A surface-treated powder, wherein the surface of a base powder is treated with a perfluoropolyether compound having an amino group, represented by the general formula (1).
(However, m represents 2, n represents an integer of 1 to 20 on average, R 1 represents an alkylene group having 2 to 6 carbon atoms, and R 2 represents a hydrogen atom or a total of 1 to 8 carbon atoms. Represents an alkyl group, an aralkyl group, or an aryl group, R 3 represents a hydrogen atom or an alkyl group, an aralkyl group, or an aryl group having a total of 1 to 8 carbon atoms, and X represents a fluorine atom or 1 to 3 carbon atoms. It represents a perfluoroalkyl group, Z is represents NH or N-CH 3 or an oxygen atom.)
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