JP6803776B2 - Nail cosmetics - Google Patents
Nail cosmetics Download PDFInfo
- Publication number
- JP6803776B2 JP6803776B2 JP2017042450A JP2017042450A JP6803776B2 JP 6803776 B2 JP6803776 B2 JP 6803776B2 JP 2017042450 A JP2017042450 A JP 2017042450A JP 2017042450 A JP2017042450 A JP 2017042450A JP 6803776 B2 JP6803776 B2 JP 6803776B2
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- JP
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- Prior art keywords
- acid
- dextrin
- fatty acid
- mol
- ester
- 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.)
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- 239000002537 cosmetic Substances 0.000 title claims description 35
- 239000004375 Dextrin Substances 0.000 claims description 112
- 229920001353 Dextrin Polymers 0.000 claims description 112
- 235000019425 dextrin Nutrition 0.000 claims description 112
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 81
- 239000000194 fatty acid Substances 0.000 claims description 81
- 229930195729 fatty acid Natural products 0.000 claims description 81
- -1 cyclic saturated Chemical class 0.000 claims description 60
- 150000004665 fatty acids Chemical class 0.000 claims description 47
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 35
- 150000002148 esters Chemical class 0.000 claims description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- 238000006467 substitution reaction Methods 0.000 claims description 21
- 238000006116 polymerization reaction Methods 0.000 claims description 20
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 19
- 239000008103 glucose Substances 0.000 claims description 19
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 15
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 14
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 12
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
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- 238000000691 measurement method Methods 0.000 claims description 5
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 4
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- 238000006243 chemical reaction Methods 0.000 description 36
- 238000004519 manufacturing process Methods 0.000 description 36
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 29
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- 239000000843 powder Substances 0.000 description 22
- 239000003921 oil Substances 0.000 description 17
- 229910001651 emery Inorganic materials 0.000 description 16
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- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 8
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 7
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 7
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- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 6
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 210000003298 dental enamel Anatomy 0.000 description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 6
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 5
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 5
- 235000021357 Behenic acid Nutrition 0.000 description 5
- 229940116226 behenic acid Drugs 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 4
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
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Landscapes
- Cosmetics (AREA)
Description
本発明は、爪用化粧料に関する。 The present invention relates to nail cosmetics.
従来より、爪用化粧料には、皮膜形成剤としてニトロセルロースが多く用いられているが、ニトロセルロースを含有する爪用化粧料を除去する際には、アセトンを主体とするエナメルリムーバーを使用する必要がある。しかしながら、アセトンを主体とするエナメルリムーバーは、使用時に引火の危険性があったり、連続使用することにより、爪が欠けたり、二枚爪になる等、爪そのものに悪影響を与える場合があるなどの問題があった。
そこで、アセトンを主体とするエナメルリムーバー以外でも除去が可能な爪用化粧料が提案されてきている。例えば、酢酸ビニル・ビニルピロリドン共重合体を用いることで、水で除去することを可能にしたマニキュア（特許文献１参照）や、特定のトリグリセライドを用いることでリムーバーを使用しなくとも塗布膜をはがすことができる水系美爪料（特許文献２参照）等が提案されている。
Conventionally, nitrocellulose is often used as a film-forming agent in nail cosmetics, but when removing nitrocellulose-containing nail cosmetics, an enamel remover mainly composed of acetone is used. There is a need. However, acetone-based enamel remover may cause a risk of ignition during use, and continuous use may adversely affect the nail itself, such as chipped nails or double nails. There was a problem.
Therefore, nail cosmetics that can be removed by other than the acetone-based enamel remover have been proposed. For example, by using a vinyl acetate / vinylpyrrolidone copolymer, a nail polish that can be removed with water (see Patent Document 1), or by using a specific triglyceride, the coating film can be peeled off without using a remover. A water-based nail polish (see Patent Document 2) that can be used has been proposed.
しかしながら、酢酸ビニル・ビニルピロリドン共重合体を用いる特許文献１の技術では、水で除去することが可能であることから、手洗い等の日常生活で落ちてしまう可能性が高く、満足のいく化粧持ちが得られていなかった。また、水及びエタノールを溶媒として用いているため満足のいく乾燥速度も得られていなかった。一方、特定のトリグリセライドを用いる特許文献２の技術では、爪を硬いものにぶつけたり引っかけたりした際に化粧膜が剥離してしまう可能性が高く、満足のいく化粧持ちが得られていなかった。 However, in the technique of Patent Document 1 using a vinyl acetate / vinylpyrrolidone copolymer, since it can be removed with water, there is a high possibility that it will fall off in daily life such as hand washing, and the makeup lasts satisfactorily. Was not obtained. Moreover, since water and ethanol are used as solvents, a satisfactory drying rate has not been obtained. On the other hand, in the technique of Patent Document 2 using a specific triglyceride, there is a high possibility that the cosmetic film is peeled off when the nail is hit or caught on a hard object, and a satisfactory makeup lasting has not been obtained.
したがって、従来の技術では、アセトンを主体とするエナメルリムーバー以外のもので除去が可能であり、且つ、日常生活の中でも化粧膜を維持でき、乾燥速度にも優れる爪用化粧料を具現化することは困難であった。 Therefore, in the conventional technique, it is possible to realize a nail cosmetic that can be removed by something other than an enamel remover mainly composed of acetone, can maintain a cosmetic film even in daily life, and has an excellent drying speed. Was difficult.
本発明者は、上記実情に鑑み、鋭意研究を行った結果、特定の構造を有するデキストリン脂肪酸エステルを５〜８０質量％含有することで、乾燥速度に優れ、アセトンを主体とするエナメルリムーバー以外のものでも除去することが可能で、化粧持ちに優れた爪用化粧料が得られることを見出し、本発明を完成させるに至った。 As a result of diligent research in view of the above circumstances, the present inventor has an excellent drying rate by containing 5 to 80% by mass of a dextrin fatty acid ester having a specific structure, other than an enamel remover mainly composed of acetone. We have found that it is possible to remove even a fatty acid and obtain a cosmetic for nails having excellent makeup retention, and have completed the present invention.
すなわち、本発明は成分（Ａ）デキストリンと脂肪酸とのエステル化物であって、デキストリンのグルコースの平均重合度が３〜１５０であり、脂肪酸が炭素数４〜２６の分岐飽和脂肪酸の１種又は２種以上を全脂肪酸に対して５０ｍｏｌ％より多く１００ｍｏｌ％以下、及び、炭素数２〜２２の直鎖飽和脂肪酸、炭素数６〜３０の直鎖又は分岐の不飽和脂肪酸及び炭素数６〜３０の環状の飽和又は不飽和脂肪酸よりなる群から選ばれる１種又は２種以上を全脂肪酸に対して０ｍｏｌ％以上５０ｍｏｌ％未満を含有し、グルコース単位当たりの脂肪酸の置換度が１．０〜３．０であるデキストリン脂肪酸エステルを５〜８０質量％含有する爪用化粧料を提供するものである。 That is, the present invention is an esterified product of the component (A) dextrin and a fatty acid, and the average degree of polymerization of glucose in the dextrin is 3 to 150, and the fatty acid is one or 2 branched saturated fatty acids having 4 to 26 carbon atoms. More than 50 mol% and 100 mol% or less of seeds or more with respect to total fatty acids, and linear saturated fatty acids having 2 to 22 carbon atoms, linear or branched unsaturated fatty acids having 6 to 30 carbon atoms, and 6 to 30 carbon atoms. One or more selected from the group consisting of cyclic saturated or unsaturated fatty acids is contained in an amount of 0 mol% or more and less than 50 mol% with respect to all fatty acids, and the degree of fatty acid substitution per glucose unit is 1.0 to 3. The present invention provides a cosmetic for nails containing 5 to 80% by mass of a dextrin fatty acid ester which is 0.
前記成分（Ａ）のデキストリン脂肪酸エステルを構成する分岐飽和脂肪酸が、炭素数１２〜２２の分岐飽和脂肪酸から選ばれる１種又は２種以上である、前記記載の爪用化粧料を提供するものである。 The present invention provides the above-mentioned nail cosmetics, wherein the branched saturated fatty acid constituting the dextrin fatty acid ester of the component (A) is one or more selected from the branched saturated fatty acids having 12 to 22 carbon atoms. is there.
前記成分（Ａ）のデキストリン脂肪酸エステルが、ＡＳＴＭ Ｄ４４５測定方法による４０℃における動粘度が８ｍｍ２／ｓである流動パラフィンをゲル化しない、前記記載の爪用化粧料を提供するものである。 The dextrin fatty acid ester of the component (A) does not gel liquid paraffin having a kinematic viscosity of 8 mm2 / s at 40 ° C. according to the ASTM D445 measurement method, and provides the above-mentioned nail cosmetics.
さらに、成分（Ｂ）として、揮発性炭化水素油を含有する前記記載の爪用化粧料を提供するものである。 Further, the above-mentioned nail cosmetic containing volatile hydrocarbon oil as a component (B) is provided.
前記成分（Ｂ）が炭素数７〜１２の揮発性炭化水素油である前記記載の爪用化粧料を提供するものである。 The present invention provides the above-mentioned nail cosmetics in which the component (B) is a volatile hydrocarbon oil having 7 to 12 carbon atoms.
前記爪用化粧料が溶剤系である前記記載の爪用化粧料を提供するものである。 The present invention provides the above-mentioned nail cosmetics in which the nail cosmetics are solvent-based.
前記爪用化粧料がエタノールで除去することができることを特徴とする前記記載の爪用化粧料を提供するものである。 The present invention provides the above-mentioned nail cosmetics, which is characterized in that the nail cosmetics can be removed with ethanol.
本発明の爪用化粧料は、乾燥速度に優れ、アセトンを主体とするエナメルリムーバー以外のものでも除去が可能であり、化粧持ちに優れるものである。 The nail cosmetics of the present invention have an excellent drying speed, can be removed by other than an enamel remover mainly composed of acetone, and have excellent makeup retention.
本発明の詳細について以下に説明する。なお、本明細書において、「〜」はその前後の数値を含む範囲を意味するものとする。 Details of the present invention will be described below. In this specification, "~" means a range including numerical values before and after it.
本発明に使用される成分（Ａ）デキストリン脂肪酸エステルは、デキストリンと脂肪酸とのエステル化物であって、デキストリンのグルコースの平均重合度が３〜１５０であり、脂肪酸が全脂肪酸に対して炭素数４〜２６の分岐飽和脂肪酸を５０ｍｏｌ％より多く含有するグルコース単位当たりの脂肪酸の置換度が１．０〜３．０である新規な物質で、塗布した際に皮膜を形成することができるものである。（以下、単に「デキストリン脂肪酸エステル」ということもある。） The component (A) dextrin fatty acid ester used in the present invention is an esterified product of dextrin and fatty acid, and the average degree of glucose polymerization of dextrin is 3 to 150, and the fatty acid has 4 carbon atoms with respect to the total fatty acid. It is a novel substance containing more than 50 mol% of branched saturated fatty acids of ~ 26 and having a fatty acid substitution degree of 1.0 to 3.0 per glucose unit, and can form a film when applied. .. (Hereinafter, it may be simply referred to as "dextrin fatty acid ester".)
本発明に使用される成分（Ａ）デキストリン脂肪酸エステルは、次の特性を有する。
（１）デキストリン脂肪酸エステルを不揮発性液状油に混合したとき液状油がゲル化しない。
「液状油がゲル化しない」とは、ＡＳＴＭ Ｄ４４５測定方法による４０℃における動粘度が８ｍｍ２／ｓである流動パラフィンを液状油とする場合、デキストリン脂肪酸エステルを５質量％（以下単に「％」で示す。）含有する該流動パラフィンを１００℃で溶解し、２４時間後２５℃で粘度を測定したとき、粘度が、Ｙａｍｃｏ ＤＩＧＩＴＡＬ ＶＩＳＣＯＭＡＴＥ粘度計ＶＭ−１００Ａ（振動式）（山一電機社製）の検出限界以下であることを意味する。なお、ゲル化する場合には、粘度が検出されることで確認できる。
The component (A) dextrin fatty acid ester used in the present invention has the following properties.
(1) When the dextrin fatty acid ester is mixed with the non-volatile liquid oil, the liquid oil does not gel.
"Liquid oil does not gel" means that when liquid paraffin having a kinematic viscosity at 40 ° C. of 8 mm2 / s according to the ASTM D445 measurement method is used as the liquid oil, the dextrin fatty acid ester is 5% by mass (hereinafter, simply "%"). (Shown.) When the liquid paraffin contained therein was dissolved at 100 ° C. and the viscosity was measured at 25 ° C. after 24 hours, the viscosity of the Yamaco DIGITAL VISCOMATE fatty acid meter VM-100A (vibration type) (manufactured by Yamaichi Denki Co., Ltd.) It means that it is below the detection limit. In the case of gelation, it can be confirmed by detecting the viscosity.
（２）デキストリン脂肪酸エステルが形成する皮膜が特定範囲の付着力（タック性）を有する。
「タック性」を、支持体に該デキストリン脂肪酸エステルを塗布し、もうひとつの支持体を相互に離れた状態から面接触させた後に、後退させて別離させ、後退を開始してから完全に別離するまでの接触点にかかる荷重変化（最大応力値）で表す場合、該デキストリン脂肪酸エステルを４０％含有する軽質流動イソパラフィン溶液をガラス板に４００μｍ厚のアプリケーターで成膜し、乾燥させた皮膜に、テクスチャーアナライザー、たとえば、テクスチャーアナライザーＴＡ．ＸＴｐｌｕｓ（Ｓｔａｂｌｅ Ｍｉｃｒｏ Ｓｙｓｔｅｍｓ社製）を用いて、プローブとして直径１２．５ｍｍ円柱状のポリアセタール樹脂（Ｄｅｌｒｉｎ（登録商標）デュポン社製）製プローブを使用し、１００ｇの荷重をかけ１０秒保持後に０．５ｍｍ／秒で離したときの荷重変化、すなわちタック性が３０〜１，０００ｇである。
(2) The film formed by the dextrin fatty acid ester has a specific range of adhesive force (tackiness).
For "tackiness", the dextrin fatty acid ester is applied to the support, and the other supports are brought into surface contact with each other from a state of being separated from each other, and then retracted and separated, and then completely separated after the regression is started. When expressed by the load change (maximum stress value) applied to the contact point, a light liquid isoparaffin solution containing 40% of the dextrin fatty acid ester was formed on a glass plate with a 400 μm-thick applicator, and dried. A texture analyzer, for example, a texture analyzer TA. Using XTplus (manufactured by Table Micro Systems), a probe made of a 12.5 mm diameter columnar polyacetal resin (manufactured by Delrin (registered trademark) DuPont) was used as a probe, and a load of 100 g was applied and held for 10 seconds. The load change when separated at 5 mm / sec, that is, the tackiness is 30 to 1,000 g.
本発明において、デキストリン脂肪酸エステルに用いられるデキストリンは、グルコース平均重合度３〜１５０、特に１０〜１００のデキストリンが好ましい。グルコース平均重合度が２以下では、得られたデキストリン脂肪酸エステルがワックス様となって油剤への溶解性が低下する。また、グルコース平均重合度が１５０を超えると、デキストリン脂肪酸エステルの油剤への溶解温度が高くなる、又は溶解性が悪くなる等の問題を生ずることがある。デキストリンの糖鎖は直鎖状、分岐鎖状、環状のいずれでもよい。 In the present invention, the dextrin used for the dextrin fatty acid ester is preferably a dextrin having a glucose average degree of polymerization of 3 to 150, particularly 10 to 100. When the average degree of polymerization of glucose is 2 or less, the obtained dextrin fatty acid ester becomes wax-like and the solubility in an oil agent is lowered. On the other hand, if the average degree of polymerization of glucose exceeds 150, problems such as a high dissolution temperature of the dextrin fatty acid ester in an oil agent or a poor solubility may occur. The sugar chain of dextrin may be linear, branched or cyclic.
本発明において、デキストリン脂肪酸エステルに用いられる脂肪酸は、炭素数４〜２６の分岐飽和脂肪酸の１種又は２種以上を必須とし、さらに炭素数２〜２２の直鎖飽和脂肪酸、炭素数６〜３０の直鎖又は分岐の不飽和脂肪酸、及び炭素数６〜３０の環状の飽和又は不飽和脂肪酸よりなる群から選ばれる１種又は２種以上（以下、これら炭素数４〜２６の分岐飽和脂肪酸以外の脂肪酸をまとめて表すときは「その他の脂肪酸」という）を含有してもよいものである。 In the present invention, the fatty acid used for the dextrin fatty acid ester requires one or more branched saturated fatty acids having 4 to 26 carbon atoms, and further, a linear saturated fatty acid having 2 to 22 carbon atoms and 6 to 30 carbon atoms. One or more selected from the group consisting of linear or branched unsaturated fatty acids and cyclic saturated or unsaturated fatty acids having 6 to 30 carbon atoms (hereinafter, other than these branched saturated fatty acids having 4 to 26 carbon atoms). When the fatty acids of the above are collectively expressed, they may contain (referred to as "other fatty acids").
本発明において、デキストリン脂肪酸エステルにおける脂肪酸の組成割合は、全脂肪酸に対して、炭素数４〜２６の分岐飽和脂肪酸の１種又は２種以上が５０ｍｏｌ％より多く１００ｍｏｌ％以下、好ましくは５５ｍｏｌ％以上１００ｍｏｌ％以下であり、その他の脂肪酸は、０ｍｏｌ％以上５０ｍｏｌ％未満、好ましくは、０ｍｏｌ％以上４５ｍｏｌ％以下である。
該炭素数４〜２６の分岐飽和脂肪酸としては、例えば、イソ酪酸、イソ吉草酸、２−エチル酪酸、エチルメチル酢酸、イソヘプタン酸、２−エチルヘキサン酸、イソノナン酸、イソデカン酸、イソトリデカン酸、イソミリスチン酸、イソパルミチン酸、イソステアリン酸、イソアラキン酸、イソヘキサコサン酸等が挙げられ、これらの１種又は２種以上を適宜選択又は組み合わせて使用することができる。これらのうち、炭素数１２〜２２のものが好ましく、特にイソステアリン酸が好ましく、構造の違い等の限定は特にない。
本発明において、イソステアリン酸とは、分岐したステアリン酸の１種、又は２種以上の混合物を意味する。例えば５，７，７−トリメチル−２−（１，３，３−トリメチルブチル）−オクタン酸は、イソブチレン２量体のオキソ反応により炭素数９の分岐アルデヒドとし、次いでこのアルデヒドのアルドール縮合により炭素数１８の分岐不飽和アルデヒドとし、次いで水素添加、酸化することにより製造することができ（以下、「アルドール縮合型」と略す）、これは例えば日産化学工業社より市販されている。２−ヘプチルウンデカン酸はノニルアルコールをガーベット反応（Ｇｕｅｒｂｅｔ反応、ゲルベ反応ともいう）により二量化し、酸化することにより製造することができ、これは例えば三菱化学社より市販されており、分岐位置の若干異なる類似混合物として、日産化学工業社より市販され、さらに出発アルコールが直鎖飽和ではない２箇所メチル分岐したタイプも同様に日産化学工業社より市販されている（以下総じて「ガーベット反応型」と略す）。また、メチル分岐イソステアリン酸は、例えばオレイン酸のダイマー製造時の副産物として得られるもので〔例えばＪ．Ａｍｅｒ．Ｏｉｌ Ｃｈｅｍ．Ｓｏｃ．５１，５２２（１９７４）に記載〕、例えば米国エメリー社などから市販されていたものがあげられる（以下「エメリー型」と略す）。エメリー型イソステアリン酸の出発物質であるダイマー酸のさらに出発物質は、オレイン酸だけでなく、リノール酸、リノレン酸等も含まれる場合がある。本発明においては特にアルドール型がより好ましい。
In the present invention, the composition ratio of fatty acid in the dextrin fatty acid ester is 100 mol% or less, preferably 55 mol% or more, in which one or more of the branched saturated fatty acids having 4 to 26 carbon atoms are more than 50 mol% and 100 mol% or less, based on the total fatty acids. It is 100 mol% or less, and other fatty acids are 0 mol% or more and less than 50 mol%, preferably 0 mol% or more and 45 mol% or less.
Examples of the branched saturated fatty acids having 4 to 26 carbon atoms include isobutyric acid, isovaleric acid, 2-ethylbutyric acid, ethylmethylacetic acid, isoheptanic acid, 2-ethylhexanoic acid, isononanoic acid, isodecanoic acid, isotridecanoic acid and iso. Examples thereof include myristic acid, isopalmitic acid, isostearic acid, isoaraquinic acid, isohexacosanoic acid and the like, and one or more of these can be appropriately selected or used in combination. Of these, those having 12 to 22 carbon atoms are preferable, isostearic acid is particularly preferable, and there are no particular restrictions such as differences in structure.
In the present invention, isostearic acid means one kind or a mixture of two or more kinds of branched stearic acid. For example, 5,7,7-trimethyl-2- (1,3,3-trimethylbutyl) -octanoic acid is converted into a branched aldehyde having 9 carbon atoms by the oxo reaction of the isobutylene dimer, and then carbon by aldol condensation of this aldehyde. It can be produced by preparing a branched unsaturated aldehyde of number 18 and then hydrogenating and oxidizing it (hereinafter, abbreviated as "aldol condensation type"), which is commercially available from, for example, Nissan Chemical Industry Co., Ltd. 2-Heptylundecanoic acid can be produced by dimerizing nonyl alcohol by a gerbet reaction (also called Guerbet reaction or Gerve reaction) and oxidizing it. This is commercially available from, for example, Mitsubishi Chemical Corporation, and has a branching position. As a slightly different similar mixture, it is commercially available from Nissan Chemical Industries, Ltd., and a type in which the starting alcohol is not linearly saturated and has two methyl branches is also commercially available from Nissan Chemical Industries, Ltd. (hereinafter generally referred to as "gerbet reaction type"). Abbreviated). Further, the methyl branched isostearic acid is obtained, for example, as a by-product of the dimer production of oleic acid [for example, J. Amer. Oil Chem. Soc. 51,522 (1974)], for example, those commercially available from Emery, USA (hereinafter abbreviated as "emery type"). Further starting material of dimer acid which is a starting material of emery type isostearic acid may include not only oleic acid but also linoleic acid, linolenic acid and the like. In the present invention, the aldol type is particularly preferable.
本発明において、デキストリン脂肪酸エステルに用いられる脂肪酸のうち炭素数２〜２２の直鎖飽和脂肪酸としては、例えば、酢酸、カプリル酸、カプリン酸、ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、アラキン酸、ベヘン酸等が挙げられ、これらの１種又は２種以上を適宜、選択又は組み合わせて使用することができる。これらの中でも、炭素数８〜２２のものが好ましく、特に炭素数１２〜２２のものが好ましい。 In the present invention, among the fatty acids used in the dextrin fatty acid ester, the linear saturated fatty acids having 2 to 22 carbon atoms include, for example, acetic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, and araquinic acid. , Behenic acid and the like, and one or more of these can be appropriately selected or used in combination. Among these, those having 8 to 22 carbon atoms are preferable, and those having 12 to 22 carbon atoms are particularly preferable.
本発明において、デキストリン脂肪酸エステルに用いられる脂肪酸のうち炭素数６〜３０の直鎖又は分岐の不飽和脂肪酸としては、例えば、モノエン不飽和脂肪酸としては、シス−４−デセン（オブツシル）酸、９−デセン（カプロレイン）酸、シス−４−ドデセン（リンデル）酸、シス−４−テトラデセン（ツズ）酸、シス−５−テトラデセン（フィセテリン）酸、シス−９−テトラデセン（ミリストレイン）酸、シス−６−ヘキサデセン酸、シス−９−ヘキサデセン（パルミトレイン）酸、シス−９−オクタデセン（オレイン）酸、トランス−９−オクタデセン酸（エライジン酸）、シス−１１−オクタデセン（アスクレピン）酸、シス−１１−エイコセン（ゴンドレイン）酸、シス−１７−ヘキサコセン（キシメン）酸、シス−２１−トリアコンテン（ルメクエン）酸等が挙げられ、ポリエン不飽和脂肪酸としては、ソルビン酸、リノール酸、ヒラゴ酸、プニカ酸、α−リノレン酸、γ−リノレン酸、モロクチ酸、ステアリドン酸、アラキドン酸、エイコサペンタエン酸、イワシ酸、ドコサヘキサエン酸、ニシン酸、ステアロール酸、クレペニン酸、キシメニン酸等が挙げられる。 In the present invention, among the fatty acids used for the dextrin fatty acid ester, the linear or branched unsaturated fatty acid having 6 to 30 carbon atoms is, for example, the monoene unsaturated fatty acid is cis-4-decene (obtusyl) acid, 9 -Decenoic (caproleine) acid, cis-4-dodecene (lindel) acid, cis-4-tetradecene (tsuzu) acid, cis-5-tetradecene (fiseterin) acid, cis-9-tetradecene (myristolein) acid, cis -6-Hexadecenoic acid, cis-9-hexadecenoic acid (palmitrein) acid, cis-9-octadecenoic acid (olein) acid, trans-9-octadecenoic acid (ellaidic acid), cis-11-octadecenoic acid (asklepin) acid, cis-11 Examples of polyene unsaturated fatty acids include eicosene (gondrain) acid, cis-17-hexacosene (ximen) acid, cis-21-triacone (lumecene) acid, and polyene unsaturated fatty acids include sorbic acid, linoleic acid, hirago acid, and punica. Examples thereof include acids, α-linolenic acid, γ-linolenic acid, moroctic acid, stearidonic acid, arachidonic acid, eikosapentaenoic acid, sardine acid, docosahexaenoic acid, heric acid, stearolic acid, crepenic acid and ximenic acid.
本発明において、デキストリン脂肪酸エステルに用いられる脂肪酸のうち炭素数６〜３０の環状の飽和又は不飽和脂肪酸は、環状構造を基本骨格の少なくとも一部に有する炭素数６〜３０の飽和又は不飽和脂肪酸を意味し、例えば９，１０−メチレン−９−オクタデセン酸；アレプリル酸、アレプリン酸、ゴルリン酸、α−シクロペンチル酸、α−シクロヘキシル酸、α−シクロペンチルエチル酸、α−シクロヘキシルメチル酸、ω−シクロヘキシル酸、５（６）−カルボキシ−４−ヘキシル−２−シクロヘキセン−１−オクタン酸、マルバリン酸、ステルクリン酸、ヒドノカルピン酸、ショールムーグリン酸などが挙げられる。 In the present invention, among the fatty acids used in the dextrin fatty acid ester, the cyclic saturated or unsaturated fatty acid having 6 to 30 carbon atoms is a saturated or unsaturated fatty acid having 6 to 30 carbon atoms having a cyclic structure in at least a part of the basic skeleton. Means, for example, 9,10-methylene-9-octadecenoic acid; arepric acid, arepric acid, gorphosphoric acid, α-cyclopentyl acid, α-cyclohexyl acid, α-cyclopentylethyl acid, α-cyclohexylmethyl acid, ω-cyclohexyl Acids include acids, 5 (6) -carboxy-4-hexyl-2-cyclohexene-1-octanoic acid, malvalic acid, sterclinic acid, hydnocarpine acid, shoal muglic acid and the like.
本発明において、新規なデキストリン脂肪酸エステルに用いられる脂肪酸として分岐飽和脂肪酸単独の場合のデキストリン脂肪酸エステルとしては、例えば以下のもの等が挙げられる。
デキストリンイソ酪酸エステル
デキストリンエチルメチル酢酸エステル
デキストリンイソヘプタン酸エステル
デキストリン２−エチルヘキサン酸エステル
デキストリンイソノナン酸エステル
デキストリンイソデカン酸エステル
デキストリンイソパルミチン酸エステル
デキストリンイソステアリン酸エステル
デキストリンイソアラキン酸エステル
デキストリンイソヘキサコサン酸エステル
デキストリン（イソ吉草酸／イソステアリン酸）エステル
In the present invention, as the fatty acid used in the novel dextrin fatty acid ester, the dextrin fatty acid ester in the case of the branched saturated fatty acid alone includes, for example, the following.
Dextrin Isobutyric Acid Ester Dextrin Ethylmethyl Acetate Ester Dextrin Isoheptanic Acid Ester Dextrin 2-Ethylhexanoic Acid Ester Dextrin Isononanoic Acid Ester Dextrin Isodecanoic Acid Ester Dextrin Isopalmitic Acid Ester Dextrin Isostearic Acid Ester Dextrin Isoaraquinic Acid Ester Dextrin (isovaleric acid / isostearic acid) ester
本発明において、デキストリン脂肪酸エステルに用いられる脂肪酸として分岐飽和脂肪酸とその他の脂肪酸との混合脂肪酸を用いた場合のデキストリン脂肪酸エステルとしては、例えば以下のもの等が挙げられる。
デキストリン（イソ酪酸／カプリル酸）エステル
デキストリン（２−エチルヘキサン酸／カプリル酸）エステル
デキストリン（イソアラキン酸／カプリル酸）エステル
デキストリン（イソパルミチン酸／カプリル酸）エステル
デキストリン（エチルメチル酢酸／ラウリン酸）エステル
デキストリン（２−エチルヘキサン酸／ラウリン酸）エステル
デキストリン（イソヘプタン酸／ラウリン酸／ベヘン酸）エステル
デキストリン（イソステアリン酸／ミリスチン酸）エステル
デキストリン（イソヘキサコサン酸／ミリスチン酸）エステル
デキストリン（２−エチルヘキサン酸／パルミチン酸）エステル
デキストリン（イソステアリン酸／パルミチン酸）エステル
デキストリン（イソステアリン酸／イソ吉草酸／パルミチン酸）エステル
デキストリン（イソノナン酸／パルミチン酸／カプロン酸）エステル
デキストリン（２−エチルヘキサン酸／パルミチン酸／ステアリン酸）エステル
デキストリン（イソデカン酸／パルミチン酸）エステル
デキストリン（イソパルミチン酸／ステアリン酸）エステル
デキストリン（イソステアリン酸／アラキン酸）エステル
デキストリン（２−エチルヘキサン酸／アラキン酸）エステル
デキストリン（２−エチル酪酸／ベヘン酸）エステル
デキストリン（イソノナン酸／リノール酸）エステル
デキストリン（イソパルミチン酸／アラキドン酸）エステル
デキストリン（イソパルミチン酸／カプリル酸／リノール酸）エステル
デキストリン（イソステアリン酸／ステアリン酸／オレイン酸）エステル
デキストリン（イソアラキン酸／パルミチン酸／ショールムーグリン酸）エステル
In the present invention, examples of the dextrin fatty acid ester when a mixed fatty acid of branched saturated fatty acid and other fatty acids are used as the fatty acid used for the dextrin fatty acid ester include the following.
Dextrin (isobutyric acid / capric acid) ester Dextrin (2-ethylhexanoic acid / capric acid) ester Dextrin (isoarakinic acid / capric acid) ester Dextrin (isopalmitic acid / capric acid) ester Dextrin (ethylmethylacetic acid / lauric acid) ester Dextrin (2-ethylhexanoic acid / lauric acid) ester dextrin (isoheptanoic acid / lauric acid / behenic acid) ester dextrin (isostearic acid / myristic acid) ester dextrin (isohexacosanoic acid / myristic acid) ester dextrin (2-ethylhexanoic acid /) Palmitic acid) Ester dextrin (isostearic acid / palmitic acid) Ester dextrin (isostearic acid / isovaleric acid / palmitic acid) Ester dextrin (isononanoic acid / palmitic acid / caproic acid) Ester dextrin (2-ethylhexanoic acid / palmitic acid / stearer) Acid) Ester dextrin (isodecanoic acid / palmitic acid) Ester dextrin (isopalmitic acid / stearic acid) Ester dextrin (isostearic acid / araquinic acid) Ester dextrin (2-ethylhexanoic acid / araquinic acid) Ester dextrin (2-ethylbutyric acid / Behenic acid) Ester dextrin (isononanoic acid / linoleic acid) Ester dextrin (isopalmitic acid / arachidonic acid) Ester dextrin (isopalmitic acid / capric acid / linoleic acid) Ester dextrin (isostearic acid / stearic acid / oleic acid) Ester dextrin (isostearic acid / stearic acid / oleic acid) Isoaraquinic acid / palmitic acid / shoal muglic acid) ester
デキストリン脂肪酸エステルのデキストリンへの脂肪酸の置換度は、グルコース単位当たり１．０〜３．０であり、好ましくは１．２〜２．８である。この置換度が１．０未満であると液状油等への溶解温度が１００℃以上と高くなり、着色や特異な臭いが生じ、好ましくない。 The degree of fatty acid substitution of the dextrin fatty acid ester with dextrin is 1.0 to 3.0, preferably 1.2 to 2.8, per glucose unit. If the degree of substitution is less than 1.0, the dissolution temperature in liquid oil or the like becomes as high as 100 ° C. or higher, and coloring or a peculiar odor is generated, which is not preferable.
（デキストリン脂肪酸エステルの製造方法）
次に、本発明に使用される成分（Ａ）のデキストリン脂肪酸エステルの製造方法について説明する。
製造方法としては、特に限定されず、公知の製法を採用することができるが、たとえば以下のようにして製造することができる。
(Manufacturing method of dextrin fatty acid ester)
Next, a method for producing the dextrin fatty acid ester of the component (A) used in the present invention will be described.
The production method is not particularly limited, and a known production method can be adopted, and for example, it can be produced as follows.
（１）グルコースの平均重合度が３〜１５０であるデキストリンと、炭素数４〜２６の分岐飽和脂肪酸誘導体の１種又は２種以上を全脂肪酸誘導体に対して５０ｍｏｌ％より多く１００ｍｏｌ％以下、及び、炭素数２〜２２の直鎖飽和脂肪酸誘導体、炭素数６〜３０の直鎖又は分岐の不飽和脂肪酸誘導体及び炭素数６〜３０の環状の飽和又は不飽和脂肪酸誘導体よりなる群から選ばれる１種又は２種以上（以下、これらの脂肪酸誘導体をまとめて表すときは「その他の脂肪酸誘導体」という）を全脂肪酸誘導体に対して０ｍｏｌ％以上５０ｍｏｌ％未満を含有する脂肪酸誘導体とを反応させる。 (1) Dextrin having an average degree of polymerization of glucose of 3 to 150 and one or more branched saturated fatty acid derivatives having 4 to 26 carbon atoms are contained in an amount of more than 50 mol% and 100 mol% or less based on all fatty acid derivatives. 1 selected from the group consisting of a linear saturated fatty acid derivative having 2 to 22 carbon atoms, a linear or branched unsaturated fatty acid derivative having 6 to 30 carbon atoms, and a cyclic saturated or unsaturated fatty acid derivative having 6 to 30 carbon atoms. A seed or two or more kinds (hereinafter, referred to as "other fatty acid derivatives" when these fatty acid derivatives are collectively represented) are reacted with a fatty acid derivative containing 0 mol% or more and less than 50 mol% with respect to all fatty acid derivatives.
（２）グルコースの平均重合度が３〜１５０であるデキストリンと、炭素数４〜２６の分岐飽和脂肪酸誘導体の１種又は２種以上とを反応させ、次いで、その生成物とその他の脂肪酸誘導体とを反応させる。
その場合、全脂肪酸誘導体に対して炭素数４〜２６の分岐飽和脂肪酸誘導体の１種又は２種以上を５０ｍｏｌ％より多く１００ｍｏｌ％以下、及び、その他の脂肪酸誘導体を全脂肪酸誘導体に対して０ｍｏｌ％以上５０ｍｏｌ％未満使用する。
(2) Dextrin having an average degree of polymerization of glucose of 3 to 150 is reacted with one or more branched saturated fatty acid derivatives having 4 to 26 carbon atoms, and then the product and other fatty acid derivatives are reacted. To react.
In that case, one or more of the branched saturated fatty acid derivatives having 4 to 26 carbon atoms are more than 50 mol% and 100 mol% or less with respect to all fatty acid derivatives, and 0 mol% of other fatty acid derivatives with respect to all fatty acid derivatives. Use more than 50 mol%.
本発明において、上記デキストリンとのエステル化反応に使用される脂肪酸誘導体としては、例えば、上記脂肪酸のハロゲン化物、酸無水物等が用いられる。
（１）及び（２）のいずれの場合も、まず、デキストリンを反応溶媒に分散し、必要に応じて触媒を添加する。これに、上記脂肪酸のハロゲン化物、酸無水物等を添加して反応させる。（１）の製造法の場合は、これらの酸を混合して同時に添加反応させ、（２）の製造法の場合は、まず反応性の低い分岐飽和脂肪酸誘導体を反応させた後、次いでその他の脂肪酸誘導体を添加反応させる。
In the present invention, as the fatty acid derivative used in the esterification reaction with the dextrin, for example, a halide of the fatty acid, an acid anhydride and the like are used.
In both cases (1) and (2), first, dextrin is dispersed in a reaction solvent, and a catalyst is added if necessary. To this, a halide of the above fatty acid, an acid anhydride or the like is added and reacted. In the case of the production method (1), these acids are mixed and reacted at the same time, and in the case of the production method (2), a branched saturated fatty acid derivative having low reactivity is first reacted, and then other A fatty acid derivative is added and reacted.
製造にあたり、これらのうちの好ましい方法を採用することができる。反応溶媒にはジメチルホルムアミド、ホルムアミド等のホルムアミド系；アセトアミド系；ケトン系；ベンゼン、トルエン、キシレン等の芳香族化合物系；ジオキサン等の溶剤を適宜使用することができる。反応触媒としてはピリジン、ピコリン等の３級アミノ化合物などを用いることができる。反応温度は原料脂肪酸等により適宜選択されるが、０℃〜１００℃の温度が好ましい。成分（Ａ）の市販品としては、例えば、ユニフィルマＨＶＹ（千葉製粉社製）等が挙げられる。 Of these, the preferred method can be adopted in the production. As the reaction solvent, a formamide type such as dimethylformamide and formamide; an acetamide type; a ketone type; an aromatic compound type such as benzene, toluene and xylene; and a solvent such as dioxane can be appropriately used. As the reaction catalyst, a tertiary amino compound such as pyridine or picoline can be used. The reaction temperature is appropriately selected depending on the raw material fatty acid and the like, but a temperature of 0 ° C to 100 ° C is preferable. Examples of commercially available products of the component (A) include Unifilma HVY (manufactured by Chiba Flour Milling Co., Ltd.) and the like.
本発明における成分（Ａ）の含有量は、５〜８０％が好ましく、さらに好ましくは、２０〜５０％である。成分（Ａ）の含有量が５％未満の場合は、十分な化粧もちが得られず、８０％を超えると満足のいく落としやすさが得られない場合がある。 The content of the component (A) in the present invention is preferably 5 to 80%, more preferably 20 to 50%. If the content of the component (A) is less than 5%, sufficient makeup retention may not be obtained, and if it exceeds 80%, satisfactory ease of removal may not be obtained.
本発明には、さらに、成分（Ｂ）として、揮発性炭化水素油を含有することが、より乾燥速度に優れる爪用化粧料を得られる点等から、より好ましい。本発明における成分（Ｂ）としては、化粧料に一般に用いられるものであれば特に制限はなく、例えば、常圧における沸点が２６０℃以下の炭化水素、ノルマルヘプタン等の直鎖の炭化水素、イソオクタン（２，２，４−トリメチルペンタン、２，３−ジメチルヘキサン等）、イソドデカン（２，２，４，６，６−ペンタメチルヘプタン等）、イソヘキサデカン、イソエイコサエン等の側鎖を有する炭化水素、或いはこれらの混合物、イソブテン、ｎ−ブテン等を重合或いは共重合（重合度は４〜６が好ましい）した後、水素添加したもの等を挙げることができ、必要に応じて１種又は２種以上を組み合わせて使用することができる。中でも炭素数７〜１２の揮発性炭化水素を用いることが、より乾燥速度に優れる爪用化粧料を得られる点等から、より好ましい。 Further, in the present invention, it is more preferable to contain a volatile hydrocarbon oil as the component (B) from the viewpoint of obtaining a nail cosmetic having a higher drying rate. The component (B) in the present invention is not particularly limited as long as it is generally used in cosmetics. For example, a hydrocarbon having a boiling point of 260 ° C. or lower at normal pressure, a linear hydrocarbon such as normal heptan, or isooctane. Hydrocarbons having side chains such as (2,2,4-trimethylpentane, 2,3-dimethylhexane, etc.), isododecane (2,2,4,6,6-pentamethylheptane, etc.), isohexadecane, isoeicosaene, etc. Alternatively, a mixture thereof, isobutene, n-butene, etc. may be polymerized or copolymerized (preferably having a degree of polymerization of 4 to 6) and then hydrogenated, etc., and one or more of them may be used as required. Can be used in combination. Above all, it is more preferable to use a volatile hydrocarbon having 7 to 12 carbon atoms from the viewpoint of obtaining a nail cosmetic having a higher drying rate.
市販品としては、ノルマルヘプタン（株式会社フジセキユ社製）、ＩＳＯＤＯＤＥＣＡＮＥ（ＩＭＣＤ（ＩＮＥＯＳ ＯＬＩＧＯＭＥＲＳ）社製）、ＩＰソルベント１６２０ＭＵ（出光興産者社製）等が挙げられ、これら１種又は２種以上用いることができる。 Examples of commercially available products include normal heptane (manufactured by Fujisekiyu Co., Ltd.), ISODODECANE (manufactured by IMCD (INEOS OLIGOMERS)), IP solvent 1620MU (manufactured by Idemitsu Kosan Co., Ltd.), and the like, and one or more of these may be used. Can be done.
本発明における成分（Ｂ）の含有量は、特に限定されないが、より乾燥速度に優れた爪用化粧料が得られる等の観点から、１〜９５％が好ましく、さらに好ましくは、５〜８０％である。 The content of the component (B) in the present invention is not particularly limited, but is preferably 1 to 95%, more preferably 5 to 80%, from the viewpoint of obtaining a nail cosmetic having a more excellent drying rate. Is.
本発明の爪用化粧料には、上記必須成分の他に、通常爪用化粧料に用いられる成分として、例えば、有機溶剤、粉体、ニトロセルロースやアルキッド樹脂等の皮膜形成剤、可塑剤、界面活性剤、酸化防止剤、紫外線吸収剤、増粘剤、香料、防腐剤、多価アルコール、低級アルコール、美容成分等を本発明の効果を損なわない範囲で、含有することができる。 In addition to the above-mentioned essential components, the nail cosmetics of the present invention include, for example, organic solvents, powders, film-forming agents such as nitrocellulose and alkyd resins, plasticizers, as components usually used in nail cosmetics. Surfactants, antioxidants, ultraviolet absorbers, thickeners, fragrances, preservatives, polyhydric alcohols, lower alcohols, beauty ingredients and the like can be contained within a range that does not impair the effects of the present invention.
有機溶剤としては、爪用化粧料に一般的に用いられるものであれば、非極性溶剤、極性溶剤のいずれでも良く、例えば、酢酸エチル、酢酸ブチル、イソプロパノール、エタノール、ジメチコン、シクロメチコン等が挙げられ、これらを１種又は２種以上用いることができる。 The organic solvent may be either a non-polar solvent or a polar solvent as long as it is generally used for nail cosmetics, and examples thereof include ethyl acetate, butyl acetate, isopropanol, ethanol, dimethicone, and cyclomethicone. These can be used alone or in combination of two or more.
粉体としては、球状、板状、針状等の形状、、微粒子、顔料級等の粒子径、多孔質、無孔質等の粒子構造、等により特に限定されず、無機粉体類、光輝性粉体類、有機粉体類、色素粉体類、複合粉体類、等が挙げられる。具体的には、酸化チタン、黒酸化チタン、コンジョウ、群青、ベンガラ、黄酸化鉄、黒酸化鉄、酸化亜鉛、酸化アルミニウム、酸化マグネシウム、酸化ジルコニウム、炭酸マグネシウム、炭酸カルシウム、酸化クロム、水酸化クロム、カーボンブラック、ケイ酸アルミニウム、ケイ酸マグネシウム、ケイ酸アルミニウムマグネシウム、マイカ、合成マイカ、合成セリサイト、セリサイト、タルク、カオリン、炭化珪素、硫酸バリウム、ベントナイト、スメクタイト、窒化硼素等の無機粉体類、オキシ塩化ビスマス、雲母チタン、酸化鉄コーティング雲母、酸化鉄雲母チタン、有機顔料処理雲母チタン、酸化チタン被覆ガラス末、アルミニウムパウダー等の光輝性粉体類、ナイロンパウダー、ポリメチルメタクリレート、アクリロニトリル−メタクリル酸共重合体パウダー、塩化ビニリデン−メタクリル酸共重合体パウダー、ポリスチレンパウダー、ポリメチルシルセスキオキサンパウダー、オルガノポリシロキサンエラストマーパウダー、ウレタンパウダー、ウールパウダー、シルクパウダー、結晶セルロース、Ｎ−アシルリジン等の有機粉体類、有機タール系顔料、有機色素のレーキ顔料等の色素粉体類、微粒子酸化チタン被覆雲母チタン、微粒子酸化亜鉛被覆雲母チタン、硫酸バリウム被覆雲母チタン、酸化チタン含有二酸化珪素、酸化亜鉛含有二酸化珪素等の複合粉体、等が挙げられ、これらを一種又は二種以上用いることができる。しかも、目的に応じて、例えば金属酸化物、金属水酸化物、フッ素化合物、シリコーン系油剤、金属石鹸、ロウ、油脂、炭化水素等で表面処理して用いることも可能である。 The powder is not particularly limited by the shape such as spherical, plate-like, needle-like, particle size such as fine particles and pigment grade, particle structure such as porous and non-porous, and the like, and inorganic powders and brilliance. Examples thereof include sex powders, organic powders, pigment powders, composite powders, and the like. Specifically, titanium oxide, black titanium oxide, mica, ultramarine, red iron oxide, yellow iron oxide, black iron oxide, zinc oxide, aluminum oxide, magnesium oxide, zirconium oxide, magnesium carbonate, calcium carbonate, chromium oxide, chromium hydroxide. , Carbon black, aluminum silicate, magnesium silicate, magnesium aluminum silicate, mica, synthetic mica, synthetic sericite, sericite, talc, kaolin, silicon carbide, barium sulfate, bentonite, smectite, boron nitride and other inorganic powders. Kind, bismuth oxychloride, titanium mica, iron oxide coated mica, titanium oxide mica, organic pigment treated mica titanium, titanium oxide coated glass powder, bright powders such as aluminum powder, nylon powder, polymethylmethacrylate, acrylonitrile- Methacrylic acid copolymer powder, vinylidene chloride-methacrylic acid copolymer powder, polystyrene powder, polymethylsilsesquioxane powder, organopolysiloxane elastomer powder, urethane powder, wool powder, silk powder, crystalline cellulose, N-acyllysine, etc. Organic powders, organic tar pigments, pigment powders such as rake pigments of organic pigments, fine particle titanium oxide coated mica titanium, fine particle zinc oxide coated mica titanium, barium sulfate coated mica titanium, titanium oxide containing silicon dioxide, oxidation Examples thereof include composite powders such as zinc-containing silicon dioxide, and one or more of these can be used. Moreover, depending on the purpose, it is also possible to use it by surface-treating it with, for example, a metal oxide, a metal hydroxide, a fluorine compound, a silicone-based oil agent, a metal soap, wax, an oil or fat, a hydrocarbon, or the like.
本発明品の製造方法は、特に限定されず、常法により調製される。例えば、上記成分（Ａ）、（Ｂ）、さらに必要に応じて任意成分を加え、これを混合することにより調製する方法が挙げられる。 The method for producing the product of the present invention is not particularly limited, and is prepared by a conventional method. For example, a method of preparing by adding the above-mentioned components (A) and (B) and, if necessary, an arbitrary component and mixing them can be mentioned.
本発明品の形態は、特に限定されず、液状、半固形状等のいずれでもよいが、塗布のしやすさの点で液状が好ましい。また、本発明の剤型は、水系、可溶化系、水中油型系、油中水型系、溶剤系等のいずれでも良く、特に限定されないが、成分（Ａ）の溶解性の点から、有機溶剤や成分（Ｂ）を溶媒に用いる溶剤系が好ましい。 The form of the product of the present invention is not particularly limited and may be liquid, semi-solid or the like, but liquid is preferable from the viewpoint of ease of application. The dosage form of the present invention may be any of water-based, solubilizing-based, oil-in-water-based, water-in-oil-based, solvent-based, etc., and is not particularly limited, but from the viewpoint of solubility of the component (A). A solvent system using an organic solvent or the component (B) as a solvent is preferable.
本発明の爪用化粧料としては、マニキュア、トップコート、ベースコート、ネイルトリートメント、ネイルクリーム等が例示できる。 Examples of the nail polish of the present invention include manicure, top coat, base coat, nail treatment, nail cream and the like.
以下に製造例と実施例をあげて本発明を詳細に説明する。尚、これらは本発明を何ら限定するものではない。 The present invention will be described in detail below with reference to production examples and examples. It should be noted that these do not limit the present invention in any way.
《デキストリン脂肪酸エステルの参考製造例》
以下に本発明に用いるデキストリン脂肪酸エステルの参考製造例を示す。また、下記方法で置換度、構成脂肪酸のｍｏｌ％、粘度、タック性を測定した。
<< Reference production example of dextrin fatty acid ester >>
A reference production example of the dextrin fatty acid ester used in the present invention is shown below. In addition, the degree of substitution, mol% of constituent fatty acids, viscosity, and tackiness were measured by the following methods.
（置換度、構成脂肪酸のｍｏｌ％の測定方法）
各試料（下記参考製造例のデキストリン脂肪酸エステル）のＩＲスペクトルを測定し、アルカリ分解後の脂肪酸量とガスクロマトグラフィーから、置換度と、構成脂肪酸のｍｏｌ％を求めた。
(Measurement method of degree of substitution and mol% of constituent fatty acids)
The IR spectrum of each sample (dextrin fatty acid ester of the following reference production example) was measured, and the degree of substitution and mol% of the constituent fatty acids were determined from the amount of fatty acid after alkali decomposition and gas chromatography.
（粘度の測定方法）
各試料（参考下記製造例のデキストリン脂肪酸エステル）を５質量％含有する流動パラフィンを１００℃で溶解し、室温（２５℃）まで冷却する。２５℃の恒温槽で２４時間保温し、以下の測定機器を用いて粘度を測定した。
尚、流動パラフィンはＡＳＴＭ Ｄ４４５測定方法による４０℃の動粘度が８ｍｍ２／ｓのものを使用した。
［測定機器］Ｙａｍｃｏ ＤＩＧＩＴＡＬ ＶＩＳＣＯＭＡＴＥ ＭＯＤＥＬ ＶＭ−１００Ａ（山一電機社製）
(Viscosity measurement method)
Liquid paraffin containing 5% by mass of each sample (reference dextrin fatty acid ester of the following production example) is dissolved at 100 ° C. and cooled to room temperature (25 ° C.). It was kept warm for 24 hours in a constant temperature bath at 25 ° C., and the viscosity was measured using the following measuring equipment.
The liquid paraffin used had a kinematic viscosity of 8 mm2 / s at 40 ° C. according to the ASTM D445 measuring method.
[Measuring equipment] Yamaco DIGITAL VISCOMATE MODEL VM-100A (manufactured by Yamaichi Electric Co., Ltd.)
（タック性の測定方法）
各試料（製造例のデキストリン脂肪酸エステル）をＩＰクリーンＬＸ（軽質流動イソパラフィン）に４０％溶解した溶液を、ガラス板に４００μｍ厚のアプリケーターで塗布し、その皮膜を室温２４時間乾燥後、７０℃で１２時間保存した後、室温２５℃におけるタック性を、以下に示す機器および条件で評価した。
［測定機器］テクスチャーアナライザーＴＡ．ＸＴｐｌｕｓ（Ｓｔａｂｌｅ Ｍｉｃｒｏ Ｓｙｓｔｅｍｓ社製）
［プローブ］１／２ Ｃｙｌ．Ｄｅｌｒｉｎ（ポリアセタール樹脂（ＰＯＭ））Ｐ／０．５）、直径１２．５ｍｍ円柱状
［測定条件］Ｔｅｓｔ Ｓｐｅｅｄ：０．５ｍｍ／ｓｅｃ， Ａｐｐｌｉｅｄ Ｆｏｒｃｅ：１００ｇ， Ｃｏｎｔａｃｔ Ｔｉｍｅ：１０ｓｅｃ
(Measuring method of tackiness)
A solution prepared by dissolving 40% of each sample (dextrin fatty acid ester of the production example) in IP Clean LX (light liquid isoparaffin) was applied to a glass plate with a 400 μm thick applicator, and the film was dried at room temperature for 24 hours and then at 70 ° C. After storage for 12 hours, the tackiness at room temperature of 25 ° C. was evaluated with the following equipment and conditions.
[Measuring equipment] Texture analyzer TA. XTplus (manufactured by Table Micro Systems)
[Probe] 1/2 Cyl. Delrin (polyacetal resin (POM)) P / 0.5), diameter 12.5 mm columnar [Measurement conditions] Test Speed: 0.5 mm / sec, Applied Force: 100 g, Contact Time: 10 sec
［参考製造例１：デキストリンイソステアリン酸（エメリー型）エステル］
平均グルコース重合度３０のデキストリン２１．４１ｇ（０．１３２ｍｏｌ）をジメチルホルムアミド７１ｇ、３−メチルピリジン６２ｇ（０．６６６ｍｏｌ）とからなる混合溶媒に７０℃で分散させ、イソステアリン酸クロライド（エメリー型）１２０ｇ（０．３９６ｍｏｌ）を３０分かけて滴下した。滴下終了後、反応温度を８０℃として５時間反応させた。反応終了後、反応液をメタノールに分散させ、上層を除去した。半固形分をメタノールで数回洗浄後、乾燥して淡黄色の樹脂状物質１０７ｇを得た。（仕込み時分岐飽和脂肪酸６０ｍｏｌ％）
尚、エメリー型の出発原料はコグニス社製のＥＭＡＲＳＯＬ８７３を用いた。本原料の脂肪酸組成は分岐飽和脂肪酸が６０ｍｏｌ％、その他の脂肪酸が４０ｍｏｌ％（パルミチン酸１０ｍｏｌ％を含む）のものを用いた。（以下同様）
置換度は２．２、分岐飽和脂肪酸６０ｍｏｌ％、その他の脂肪酸４０ｍｏｌ％（内パルミチン酸１０ｍｏｌ％）、粘度は０ｍＰａ・ｓ、タック性は１６１ｇであった。
[Reference Production Example 1: Dextrin Isostearic Acid (Emery Type) Ester]
21.41 g (0.132 mol) of dextrin having an average glucose polymerization degree of 30 was dispersed at 70 ° C. in a mixed solvent consisting of 71 g of dimethylformamide and 62 g (0.666 mol) of 3-methylpyridine, and 120 g of isostearic acid chloride (emery type). (0.396 mol) was added dropwise over 30 minutes. After completion of the dropping, the reaction was carried out for 5 hours at a reaction temperature of 80 ° C. After completion of the reaction, the reaction solution was dispersed in methanol and the upper layer was removed. The semi-solid content was washed with methanol several times and then dried to obtain 107 g of a pale yellow resinous substance. (60 mol% of branched saturated fatty acid at the time of preparation)
As the starting material for the emery type, EMARSOL873 manufactured by Cognis was used. The fatty acid composition of this raw material used was 60 mol% of branched saturated fatty acids and 40 mol% of other fatty acids (including 10 mol% of palmitic acid). (Same below)
The degree of substitution was 2.2, the branched saturated fatty acid was 60 mol%, the other fatty acids were 40 mol% (within palmitic acid 10 mol%), the viscosity was 0 mPa · s, and the tack property was 161 g.
［参考製造例２〜４：デキストリンイソステアリン酸（エメリー型）エステル］
参考製造例２記載の原料・方法に準じ、 参考製造例３は、平均グルコース重合度３０のデキストリン０．１３２ｍｏｌに対し、イソステアリン酸クロライド（エメリー型）を０．１７２ｍｏｌ用い、デキストリンイソステアリン酸（エメリー型）エステルを得た。（仕込み時分岐飽和脂肪酸６０ｍｏｌ％）
置換度１．０、分岐飽和脂肪酸６０ｍｏｌ％、その他の脂肪酸４０ｍｏｌ％（内パルミチン酸１０ｍｏｌ％）、粘度は０ｍＰａ・ｓ、タック性は３５ｇであった。
参考製造例４は、平均グルコース重合度３０のデキストリン０．１３２ｍｏｌに対し、イソステアリン酸クロライド（エメリー型）を０．２２４ｍｏｌ用い、デキストリンイソステアリン酸（エメリー型）エステルを得た。（仕込み時分岐飽和脂肪酸６０ｍｏｌ％）
置換度１．４、分岐飽和脂肪酸６０ｍｏｌ％、その他の脂肪酸４０ｍｏｌ％（内パルミチン酸１０ｍｏｌ％）、粘度は０ｍＰａ・ｓ、タック性は４５ｇであった。
参考製造例５は平均グルコース重合度３０のデキストリン０．１３２ｍｏｌに対し、イソステアリン酸クロライド（エメリー型）を０．５０２ｍｏｌ用い、デキストリンイソステアリン酸（エメリー型）エステルを得た。（仕込み時分岐飽和脂肪酸６０ｍｏｌ％）
置換度２．６、分岐飽和脂肪酸６０ｍｏｌ％、その他の脂肪酸４０ｍｏｌ％（内パルミチン酸１０ｍｏｌ％）、粘度は０ｍＰａ・ｓ、タック性は７５０ｇであった。
[Reference Production Examples 2 to 4: Dextrin Isostearic Acid (Emery Type) Ester]
According to the raw materials and methods described in Reference Production Example 2, in Reference Production Example 3, 0.172 mol of dextrin isostearic acid (emery type) is used for 0.132 mol of dextrin having an average glucose polymerization degree of 30, and dextrin isostearic acid (emery type) is used. ) Esters were obtained. (60 mol% of branched saturated fatty acid at the time of preparation)
The degree of substitution was 1.0, the branched saturated fatty acid was 60 mol%, the other fatty acids were 40 mol% (within palmitic acid 10 mol%), the viscosity was 0 mPa · s, and the tack property was 35 g.
In Reference Production Example 4, 0.224 mol of isostearic acid chloride (emery type) was used with respect to 0.132 mol of dextrin having an average glucose polymerization degree of 30, to obtain a dextrin isostearic acid (emery type) ester. (60 mol% of branched saturated fatty acid at the time of preparation)
The degree of substitution was 1.4, the branched saturated fatty acid was 60 mol%, the other fatty acids were 40 mol% (within palmitic acid 10 mol%), the viscosity was 0 mPa · s, and the tack property was 45 g.
In Reference Production Example 5, 0.502 mol of isostearic acid chloride (emery type) was used with respect to 0.132 mol of dextrin having an average glucose polymerization degree of 30, to obtain a dextrin isostearic acid (emery type) ester. (60 mol% of branched saturated fatty acid at the time of preparation)
The degree of substitution was 2.6, the branched saturated fatty acid was 60 mol%, the other fatty acids were 40 mol% (within palmitic acid 10 mol%), the viscosity was 0 mPa · s, and the tack property was 750 g.
［参考製造例５：デキストリンイソステアリン酸エステル］
イソステアリン酸クロライド（エメリー型）の代わりにイソステアリン酸クロライド（ガーベット反応型）を用いた以外は参考製造例２と同様に作成し、淡黄色の樹脂状物質８０ｇを得た。（仕込み時分岐飽和脂肪酸１００ｍｏｌ％）
尚、ガーベット反応型の出発原料は日産化学工業社製のファインオキソコール イソステアリン酸−Ｎを用いた。
置換度は１．８、イソステアリン酸１００ｍｏｌ％、粘度は０ｍＰａ・ｓ、タック性は１７３ｇであった。
[Reference Production Example 5: Dextrin Isostearate]
It was prepared in the same manner as in Reference Production Example 2 except that isostearic acid chloride (gerbet reaction type) was used instead of isostearic acid chloride (emery type), and 80 g of a pale yellow resinous substance was obtained. (100 mol% branched saturated fatty acid at the time of preparation)
As a starting material for the gerbet reaction type, fine oxochol isostearic acid-N manufactured by Nissan Chemical Industries, Ltd. was used.
The degree of substitution was 1.8, the isostearic acid was 100 mol%, the viscosity was 0 mPa · s, and the tackiness was 173 g.
［参考製造例６：デキストリンイソステアリン酸エステル］
イソステアリン酸クロライド（エメリー型）の代わりにイソステアリン酸クロライド（アルドール縮合型）を用いた以外は参考製造例２と同様に作成し、淡黄色の樹脂状物質６０ｇを得た。（仕込み時分岐飽和脂肪酸１００ｍｏｌ％）
尚、アルドール縮合型の出発原料は日産化学工業社製のファインオキソコール イソステアリン酸を用いた。
置換度は１．２、イソステアリン酸１００ｍｏｌ％、粘度は０ｍＰａ・ｓ、タック性は６１ｇであった。
[Reference Production Example 6: Dextrin Isostearate]
It was prepared in the same manner as in Reference Production Example 2 except that isostearic acid chloride (aldol condensed type) was used instead of isostearic acid chloride (emery type), and 60 g of a pale yellow resinous substance was obtained. (100 mol% branched saturated fatty acid at the time of preparation)
As the starting material for the aldol condensation type, fine oxochol isostearic acid manufactured by Nissan Chemical Industries, Ltd. was used.
The degree of substitution was 1.2, the isostearic acid was 100 mol%, the viscosity was 0 mPa · s, and the tack property was 61 g.
［参考製造例７：デキストリンイソアラキン酸／パルミチン酸エステル］
平均グルコース重合度１５０のデキストリン５１．２８ｇをジメチルホルムアミド１５０ｇ、ピリジン６０ｇとからなる混合溶媒に７０℃で分散させ、イソアラキン酸クロライド１３２ｇとパルミチン酸クロライド１２ｇの混合物を３０分間かけて滴下した。滴下終了後、反応温度を８０℃として５時間反応させた。反応終了後、反応液をメタノールに分散させ、上層を除去した。半固形分をメタノールで数回洗浄後、乾燥して淡黄色の樹脂状物質１４５ｇを得た。（仕込み時分岐飽和脂肪酸９０ｍｏｌ％）
置換度は１．１、イソアラキン酸８５ｍｏｌ％、パルミチン酸１５ｍｏｌ％、粘度は０ｍＰａ・ｓ、タック性は４５ｇであった。
[Reference Production Example 7: Dextrin Isoaraquinic Acid / Palmitic Acid Ester]
51.28 g of dextrin having an average glucose polymerization degree of 150 was dispersed in a mixed solvent consisting of 150 g of dimethylformamide and 60 g of pyridine at 70 ° C., and a mixture of 132 g of isoaraquinate chloride and 12 g of palmitic acid chloride was added dropwise over 30 minutes. After completion of the dropping, the reaction was carried out for 5 hours at a reaction temperature of 80 ° C. After completion of the reaction, the reaction solution was dispersed in methanol and the upper layer was removed. The semi-solid content was washed with methanol several times and then dried to obtain 145 g of a pale yellow resinous substance. (90 mol% of branched saturated fatty acid at the time of preparation)
The degree of substitution was 1.1, isoaraquinic acid was 85 mol%, palmitic acid was 15 mol%, the viscosity was 0 mPa · s, and the tack property was 45 g.
［参考製造例８：デキストリンイソ酪酸／カプリン酸エステル］
平均グルコース重合度５のデキストリン３４．１９ｇを３−メチルピリジン２１５ｇに７０℃で分散させ、イソ酪酸クロライド５０ｇ及びカプリン酸クロライド６０ｇの混合物を３０分間かけて滴下した。滴下終了後、反応温度を８０℃として５時間反応させた。反応終了後、反応液をメタノールに分散させ、上層を除去した。半固形分をエタノールで数回洗浄後、乾燥して淡黄色の樹脂状物質９８ｇを得た。（仕込み時分岐飽和脂肪酸６０ｍｏｌ％）
置換度は２．９、イソ酪酸６３ｍｏｌ％、カプリン酸３７ｍｏｌ％、粘度は０ｍＰａ・ｓ、タック性は２５５ｇであった。
[Reference Production Example 8: Dextrin Isobutyric Acid / Capric Acid Ester]
34.19 g of dextrin having an average glucose polymerization degree of 5 was dispersed in 215 g of 3-methylpyridine at 70 ° C., and a mixture of 50 g of isobutyric acid chloride and 60 g of capric acid chloride was added dropwise over 30 minutes. After completion of the dropping, the reaction was carried out for 5 hours at a reaction temperature of 80 ° C. After completion of the reaction, the reaction solution was dispersed in methanol and the upper layer was removed. The semi-solid content was washed with ethanol several times and then dried to obtain 98 g of a pale yellow resinous substance. (60 mol% of branched saturated fatty acid at the time of preparation)
The degree of substitution was 2.9, isobutyric acid was 63 mol%, capric acid was 37 mol%, the viscosity was 0 mPa · s, and the tack property was 255 g.
［参考製造例９：デキストリンイソパルミチン酸エステル］
平均グルコース重合度１００のデキストリン２３．６２ｇをジメチルホルムアミド７１ｇ、３−メチルピリジン６２ｇとからなる混合溶媒に７０℃で分散させ、イソパルミチン酸クロライド１００ｇを３０分間滴下した。滴下終了後、反応温度を８０℃として５時間反応させた。反応終了後、反応液をメタノールに分散させ、上層を除去した。半固形分をメタノールで数回洗浄後、乾燥して淡黄色の樹脂状物質９０ｇを得た。（仕込み時分岐飽和脂肪酸１００ｍｏｌ％）
置換度は２．０、イソパルミチン酸１００ｍｏｌ％、粘度は０ｍＰａ・ｓ、タック性は２０４ｇであった。
[Reference Production Example 9: Dextrin Isopalmitate]
23.62 g of dextrin having an average glucose polymerization degree of 100 was dispersed in a mixed solvent consisting of 71 g of dimethylformamide and 62 g of 3-methylpyridine at 70 ° C., and 100 g of isopalmitate chloride was added dropwise for 30 minutes. After completion of the dropping, the reaction was carried out for 5 hours at a reaction temperature of 80 ° C. After completion of the reaction, the reaction solution was dispersed in methanol and the upper layer was removed. The semi-solid content was washed with methanol several times and then dried to obtain 90 g of a pale yellow resinous substance. (100 mol% branched saturated fatty acid at the time of preparation)
The degree of substitution was 2.0, the isopalmitic acid was 100 mol%, the viscosity was 0 mPa · s, and the tack property was 204 g.
［参考製造例１０：デキストリンイソノナン酸／ステアリン酸エステル］
平均グルコース重合度２０のデキストリン３６．３４ｇをジメチルホルムアミド１２０ｇ、３−メチルピリジン６２ｇとからなる混合溶媒に７０℃で分散させ、イソノナン酸クロライド４１ｇ及びステアリン酸クロライド５８ｇの混合物を３０分間かけて滴下した。滴下終了後、反応温度を８０℃として５時間反応させた。反応終了後、反応液をメタノールに分散させ、上層を除去した。半固形分をメタノールで数回洗浄後、乾燥して淡黄色の樹脂状物質９５ｇを得た。（仕込み時分岐飽和脂肪酸５５ｍｏｌ％）
置換度は１．６、イソノナン酸５１ｍｏｌ％、ステアリン酸４９ｍｏｌ％、粘度は０ｍＰａ・ｓ、タック性は６４ｇであった。
[Reference Production Example 10: Dextrin Isononanoic Acid / Stearic Acid Ester]
36.34 g of dextrin having an average glucose polymerization degree of 20 was dispersed at 70 ° C. in a mixed solvent consisting of 120 g of dimethylformamide and 62 g of 3-methylpyridine, and a mixture of 41 g of isononanoic acid chloride and 58 g of stearic acid chloride was added dropwise over 30 minutes. .. After completion of the dropping, the reaction was carried out for 5 hours at a reaction temperature of 80 ° C. After completion of the reaction, the reaction solution was dispersed in methanol and the upper layer was removed. The semi-solid content was washed with methanol several times and then dried to obtain 95 g of a pale yellow resinous substance. (55 mol% of branched saturated fatty acid at the time of preparation)
The degree of substitution was 1.6, isononanoic acid was 51 mol%, stearic acid was 49 mol%, the viscosity was 0 mPa · s, and the tack property was 64 g.
［参考製造例１１：デキストリン２−エチルヘキサン酸／ベヘン酸エステル］
平均グルコース重合度２０のデキストリン５４．５６ｇをジメチルホルムアミド１５０ｇ、３−メチルピリジン１３０ｇとからなる混合溶媒に７０℃で分散させ、２−エチルヘキサン酸クロライド１４７ｇ、次いでベヘン酸クロライド３６ｇを計３０分間かけて滴下した。滴下終了後、反応温度を８０℃として５時間反応させた。反応終了後、反応液をメタノールに分散させ、上層を除去した。半固形分をメタノールで数回洗浄後、乾燥して淡黄色の樹脂状物質９５ｇを得た。（仕込み時分岐飽和脂肪酸９０ｍｏｌ％）
置換度は２．３、２−エチルヘキサン酸９５ｍｏｌ％、ベヘン酸５ｍｏｌ％、粘度は０ｍＰａ・ｓ、タック性は１３８ｇであった。
[Reference Production Example 11: Dextrin 2-Ethylhexanoic Acid / Behenic Acid Ester]
54.56 g of dextrin having an average glucose polymerization degree of 20 was dispersed at 70 ° C. in a mixed solvent consisting of 150 g of dimethylformamide and 130 g of 3-methylpyridine, and 147 g of 2-ethylhexanoic acid chloride and then 36 g of behenic acid chloride were applied for a total of 30 minutes. And dropped. After completion of the dropping, the reaction was carried out for 5 hours at a reaction temperature of 80 ° C. After completion of the reaction, the reaction solution was dispersed in methanol and the upper layer was removed. The semi-solid content was washed with methanol several times and then dried to obtain 95 g of a pale yellow resinous substance. (90 mol% of branched saturated fatty acid at the time of preparation)
The degree of substitution was 2.3, 2-ethylhexanoic acid was 95 mol%, behenic acid was 5 mol%, the viscosity was 0 mPa · s, and the tack property was 138 g.
［参考製造例１２：デキストリンイソパルミチン酸／酢酸エステル］
平均グルコース重合度２０のデキストリン２２．５６ｇをジメチルホルムアミド７１ｇ、３−メチルピリジン７０ｇとからなる混合溶媒に７０℃で分散させ、イソパルミチン酸クロライド１１０ｇ及び無水酢酸１０ｇの混合物を３０分間かけて滴下した。滴下終了後、反応温度を８０℃として５時間反応させた。反応終了後、反応液をメタノールに分散させ、上層を除去した。半固形分をメタノールで数回洗浄後、乾燥して淡黄色の樹脂状物質９６ｇを得た。（仕込み時分岐飽和脂肪酸８０ｍｏｌ％）
置換度は２．８、イソパルミチン酸７９ｍｏｌ％、酢酸２１ｍｏｌ％、粘度は０ｍＰａ・ｓ、タック性は４３０ｇであった。
[Reference Production Example 12: Dextrin Isopalmitic Acid / Acetic Acid Ester]
22.56 g of dextrin having an average glucose polymerization degree of 20 was dispersed in a mixed solvent consisting of 71 g of dimethylformamide and 70 g of 3-methylpyridine at 70 ° C., and a mixture of 110 g of isopalmitate chloride and 10 g of anhydrous acetic acid was added dropwise over 30 minutes. .. After completion of the dropping, the reaction was carried out for 5 hours at a reaction temperature of 80 ° C. After completion of the reaction, the reaction solution was dispersed in methanol and the upper layer was removed. The semi-solid content was washed with methanol several times and then dried to obtain 96 g of a pale yellow resinous substance. (80 mol% of branched saturated fatty acid at the time of preparation)
The degree of substitution was 2.8, isopalmitic acid was 79 mol%, acetic acid was 21 mol%, the viscosity was 0 mPa · s, and the tack property was 430 g.
［参考製造例１３：デキストリンイソステアリン酸（エメリー型）／オレイン酸エステル］
平均グルコース重合度４０のデキストリン１９．９９ｇをジメチルホルムアミド７１ｇ、３−メチルピリジン６２ｇとからなる混合溶媒に７０℃で分散させ、イソステアリン酸クロライド（エメリー型）１０８ｇとオレイン酸クロライド１２ｇの混合物を３０分間かけて滴下した。滴下終了後、反応温度を８０℃として５時間反応させた。反応終了後、反応液をメタノールに分散させ、上層を除去した。半固形分をメタノールで数回洗浄後、乾燥して淡黄色の樹脂状物質８８ｇを得た。（仕込み時分岐飽和脂肪酸５４ｍｏｌ％）
置換度は２．２、分岐飽和脂肪酸５４ｍｏｌ％、その他の脂肪酸４６ｍｏｌ％（内オレイン酸１０ｍｏｌ％）、粘度は０ｍＰａ・ｓ、タック性は３５０ｇであった。
[Reference Production Example 13: Dextrin Isostearic Acid (Emery Type) / Oleic Acid Ester]
19.99 g of dextrin having an average glucose polymerization degree of 40 is dispersed at 70 ° C. in a mixed solvent consisting of 71 g of dimethylformamide and 62 g of 3-methylpyridine, and a mixture of 108 g of isostearic acid chloride (emery type) and 12 g of oleate chloride is mixed for 30 minutes. Dropped over. After completion of the dropping, the reaction was carried out for 5 hours at a reaction temperature of 80 ° C. After completion of the reaction, the reaction solution was dispersed in methanol and the upper layer was removed. The semi-solid content was washed with methanol several times and then dried to obtain 88 g of a pale yellow resinous substance. (54 mol% of branched saturated fatty acid at the time of preparation)
The degree of substitution was 2.2, the branched saturated fatty acid was 54 mol%, the other fatty acid was 46 mol% (within 10 mol% of oleic acid), the viscosity was 0 mPa · s, and the tack property was 350 g.
実施例１〜１０、比較例１〜３：溶剤系マニキュア
下記表１に示す処方のマニキュアを調製し、イ．落としやすさ、ロ．化粧持ち、ハ．乾燥速度について下記の評価方法により判定した。その結果も併せて表１に示す。
Examples 1-10, Comparative Examples 1-3: Solvent-based manicure Prepare the manicures of the formulations shown in Table 1 below, and b. Easy to drop, b. Have makeup, c. The drying rate was determined by the following evaluation method. The results are also shown in Table 1.
（製造方法）
Ａ．成分（１）〜（３）を成分（４）〜（８）に加え、室温にて均一溶解する。
Ｂ．Ａに成分（９）〜（１３）を加え分散混合する。
Ｃ．Ｂを室温にて容器に充填し、溶剤系マニキュアを得た。
(Production method)
A. Ingredients (1) to (3) are added to ingredients (4) to (8) and uniformly dissolved at room temperature.
B. Ingredients (9) to (13) are added to A and dispersed and mixed.
C. B was filled in a container at room temperature to obtain a solvent-based nail polish.
〔評価方法１〕
イ．落としやすさ
ガラス板の上にドクターブレードを用いて各試料を２００μｍの厚さで塗布し、温度：２５℃，湿度：６５％ＲＨの環境下で１０分間乾燥させた後、オイルクレンジング、エタノール、アセトンの各除去剤をそれぞれ染み込ませたコットンを塗布膜に押し当てながら３０往復させ、各除去剤で各塗布膜の除去が可能かを評価した。使用したオイルクレンジングは、トリエチルヘキサンノイン（４５％）、エチルヘキサン酸セチル（２８％）、ミネラルオイル（２７％）を混合したものであり、エタノールは一般アルコール９５度合成 無変性（日本アルコール社製）、アセトンはアセトン（三井石油化学社製）を用いた。
[Evaluation method 1]
I. Easy to remove Each sample is applied to a thickness of 200 μm on a glass plate using a doctor blade, dried in an environment of temperature: 25 ° C. and humidity: 65% RH for 10 minutes, and then oil cleansing, ethanol, etc. Cotton impregnated with each of the acetone removers was pressed against the coating film and reciprocated 30 times, and it was evaluated whether each of the coating films could be removed with each of the removing agents. The oil cleansing used was a mixture of triethylhexanenoine (45%), cetyl ethylhexanate (28%), and mineral oil (27%), and ethanol was a general alcohol 95 degree synthetic non-denatured (manufactured by Nippon Alcohol Co., Ltd.). ), Acetone (manufactured by Mitsui Petrochemical Co., Ltd.) was used.
＜絶対評価基準＞
（判定）：（評価）
◎ ：オイルクレンジング、エタノール、アセトンの全てで除去が可能
○ ：エタノール、及びアセトンで除去が可能
× ：アセトンでのみ除去が可能
<Absolute evaluation criteria>
(Judgment): (Evaluation)
◎: Can be removed with all of oil cleansing, ethanol, and acetone ○: Can be removed with ethanol and acetone ×: Can be removed only with acetone
〔評価方法２〕
ロ．化粧持ち
各試料を専門パネル５名の手の爪（１０か所）全面（素の爪が見えなくなるよう）に塗布し、日常生活をおくってもらい、２４時間経過後に、各パネルの手の爪（１０か所）をデジタルカメラで撮影し、画像解析ソフト用いて塗布膜の残存率を算出し、下記絶対評価基準を用いて評点を付けた。そして、各試料ごとの評点の合計から平均値を算出し、下記判定基準を用いて判定した。ここで塗布膜の残存率とは、塗布部（爪）面積を１００％としたときの、２４時間経過後の各試料の塗布膜の面積の比率である。
[Evaluation method 2]
B. Makeup holder Apply each sample to the entire surface of the hand nails (10 places) of 5 specialized panels (so that the bare nails cannot be seen), and have them spend their daily lives. After 24 hours, the hand nails of each panel (10 places) were photographed with a digital camera, the residual rate of the coating film was calculated using image analysis software, and a score was given using the following absolute evaluation criteria. Then, the average value was calculated from the total of the scores for each sample, and the judgment was made using the following judgment criteria. Here, the residual ratio of the coating film is the ratio of the area of the coating film of each sample after 24 hours, when the area of the coated portion (nail) is 100%.
＜絶対評価基準＞
（評点）：（１０か所の爪の塗布膜の残存率の平均値）
５点：９０％以上１００％以下
４点：８０％以上９０％未満
３点：７０％以上８０％未満
２点：６０％以上７０％未満
１点：６０％未満
＜判定基準＞
（判定）：（評点（Ｎ＝５）の平均点）
◎：４．０点を超える
○：３．０点を超えて４．０点以下
△：２．０点を超えて３．０点以下
×：２．０点以下
<Absolute evaluation criteria>
(Score): (Average value of residual rate of coating film on 10 nails)
5 points: 90% or more and 100% or less 4 points: 80% or more and less than 90% 3 points: 70% or more and less than 80% 2 points: 60% or more and less than 70% 1 point: less than 60% <Criteria>
(Judgment): (Average score of score (N = 5))
⊚: More than 4.0 points ○: More than 3.0 points and less than 4.0 points △: More than 2.0 points and less than 3.0 points ×: More than 2.0 points
〔評価方法３〕
ロ．乾燥速度
温度：２５℃，湿度：６５％ＲＨの環境下で、ガラス板の上にドクターブレードを用いて各試料を２００μｍの厚さで塗布し、各試料の塗布直後から、指先で塗布膜に触れた時に塗布膜に指の跡がつかなくなるまでの時間を測定した。本測定を各試料３回行い、その平均値から下記判定基準を用いて判定した。
（判定）：（Ｎ＝３の平均時間）
◎：３分未満
○：３分以上４分未満
△：４分以上５分未満
×：５分以上
[Evaluation method 3]
B. Drying speed In an environment of temperature: 25 ° C. and humidity: 65% RH, each sample is applied to a thickness of 200 μm on a glass plate using a doctor blade, and immediately after application of each sample, it is applied to the coating film with the fingertips. The time until no finger marks were left on the coating film when touched was measured. This measurement was carried out three times for each sample, and the average value was judged using the following criteria.
(Judgment): (Average time of N = 3)
⊚: less than 3 minutes ○: 3 minutes or more and less than 4 minutes Δ: 4 minutes or more and less than 5 minutes ×: 5 minutes or more
表１の結果より明らかなように、実施例１〜１０は比較例に比べ、全ての評価項目において良好な結果が得られた。
一方、成分（Ａ）の代わりに、ニトロセルロースを用いた比較例１は、アセトン以外では落とすことが困難であった。また、成分（Ａ）の含有量が４％である比較例２は、落としやすさについては良好であったものの、化粧持ちについては満足のいくものではなかった。成分（Ａ）の含有量が８１％である比較例３は、化粧持ちについては良好であったものの、落としやすさについては満足のいくものではなかった。
As is clear from the results in Table 1, in Examples 1 to 10, better results were obtained in all the evaluation items as compared with Comparative Examples.
On the other hand, in Comparative Example 1 in which nitrocellulose was used instead of the component (A), it was difficult to remove it except for acetone. Further, Comparative Example 2 in which the content of the component (A) was 4% was good in terms of ease of removal, but was not satisfactory in terms of makeup retention. Comparative Example 3 in which the content of the component (A) was 81% was good in terms of makeup retention, but was not satisfactory in terms of ease of removal.
実施例１１：マニキュア
成分 （％）
１．イソステアリン酸デキストリン ※２ ３０
２．クエン酸アセチルトリブチル ５
３．酢酸エチル １５
４．酢酸ブチル 残量
５．ｎ−ヘプタン ２０
６．ｄｌ−カンフル ３
７．赤色２２０号 ０．１
８．酸化チタン ０．５
９．雲母チタン ※１ ５
１０．オキシベンゾン ０．５
１１．有機変性ベントナイト ※３ ２
１２．無水ケイ酸 ※４ ０．５
※２：ユニフィルマ ＨＶＹ（千葉製粉株式会社製）
※３：ＢＥＮＴＯＮＥ ３８Ｖ ＢＣ（Ｅｌｅｍｅｎｔｉｓ社製）
※４：アエロジル３００（日本アエロジル社製）
Example 11: Manicure component (%)
1. 1. Dextrin isostearate * 2 30
2. 2. Acetyl tributyl citrate 5
3. 3. Ethyl acetate 15
4. Butyl acetate Remaining amount 5. n-heptane 20
6. dl-camphor 3
7. Red No. 220 0.1
8. Titanium oxide 0.5
9. Mica Titanium * 1 5
10. Oxybenzone 0.5
11. Organic modified bentonite * 3 2
12. Silicate anhydride * 4 0.5
* 2: Unifilma HVY (manufactured by Chiba Flour Milling Co., Ltd.)
* 3: BENTONE 38V BC (manufactured by Elementis)
* 4: Aerosil 300 (manufactured by Nippon Aerosil)
［製造方法］
Ａ．成分（１）〜（１２）を分散混合する。
Ｂ．Ａを室温にて充填し、マニキュアを得た。
[Production method]
A. The components (1) to (12) are dispersed and mixed.
B. A was filled at room temperature to obtain a manicure.
得られたマニキュアは、落としやすさ、化粧持ち、乾燥速度のすべて点で満足のいくものであった。 The resulting nail polish was satisfactory in terms of ease of removal, long-lasting makeup, and drying speed.
実施例１２：ベースコート
成分 （％）
１．イソステアリン酸デキストリン※２ ３０
２．クエン酸アセチルトリブチル ５
３．酢酸エチル １５
４．酢酸ブチル 残量
５．アセトン ５
６．ｎ−ヘプタン ２０
７．有機変性ベントナイト ※３ ４
８．オキシベンゾン ０．２
９．ｄｌ−カンフル １
１０．無水ケイ酸 ※４ ２
１１．酸化チタン ２
１２．酸化鉄 ２
１３．レーヨン ０．１
Example 12: Base coat component (%)
1. 1. Dextrin isostearate * 2 30
2. 2. Acetyl tributyl citrate 5
3. 3. Ethyl acetate 15
4. Butyl acetate Remaining amount 5. Acetone 5
6. n-heptane 20
7. Organically modified bentonite * 3 4
8. Oxybenzone 0.2
9. dl-camphor 1
10. Silicate anhydride * 4 2
11. Titanium oxide 2
12. Iron oxide 2
13. Rayon 0.1
［製造方法］
Ａ．成分（１）〜（１３）を分散混合する。
Ｂ．Ａを室温にて充填し、ベースコートを得た。
[Production method]
A. The components (1) to (13) are dispersed and mixed.
B. A was filled at room temperature to obtain a base coat.
得られたベースコートは、落としやすさ、化粧持ち、乾燥速度のすべて点で満足のいくものであった。 The obtained base coat was satisfactory in terms of ease of removal, long-lasting makeup, and drying speed.
実施例１３：トップコート
成分 （％）
１．イソステアリン酸デキストリン ※２ １５
２．安息香酸ショ糖エステル ５
３．クエン酸アセチルトリブチル ５
４．酢酸エチル ２５
５．酢酸ブチル 残量
６．ｎ−ヘプタン ２５
７．イソプロパノール ５
８．無水ケイ酸 ※４ １
９．オキシベンゾン ０．２
Example 13: Topcoat component (%)
1. 1. Dextrin isostearate * 2 15
2. 2. Benzoic acid sucrose ester 5
3. 3. Acetyl tributyl citrate 5
4. Ethyl acetate 25
5. Butyl acetate Remaining amount 6. n-heptane 25
7. Isopropanol 5
8. Silicate anhydride * 4 1
9. Oxybenzone 0.2
［製造方法］
Ａ．成分（１）〜（９）を分散混合する。
Ｂ．Ａを室温にて充填し、トップコートを得た。
[Production method]
A. The components (1) to (9) are dispersed and mixed.
B. A was filled at room temperature to obtain a top coat.
得られたトップコートは、落としやすさ、化粧持ち、乾燥速度のすべて点で満足のいくものであった。 The obtained top coat was satisfactory in terms of ease of removal, long-lasting makeup, and drying speed.
Claims (7)
を５〜８０質量％含有する爪用化粧料。 Component (A) An esterified product of dextrin and fatty acid, the average degree of polymerization of glucose in dextrin is 3 to 150, and one or more of branched saturated fatty acids having 4 to 26 carbon atoms are total fatty acids. More than 50 mol% and 100 mol% or less, and linear saturated fatty acid having 2 to 22 carbon atoms, linear or branched unsaturated fatty acid having 6 to 30 carbon atoms, and cyclic saturated or unsaturated fatty acid having 6 to 30 carbon atoms. Dextrin fatty acid containing 1 or 2 or more selected from the group consisting of saturated fatty acids at 0 mol% or more and less than 50 mol% with respect to total fatty acids, and the degree of fatty acid substitution per glucose unit is 1.0 to 3.0. Cosmetics for nails containing 5 to 80% by mass of ester.
The nail cosmetic according to any one of claims 1 to 6, wherein the nail cosmetic can be removed with ethanol.
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| JP2016065807 | 2016-03-29 | ||
| JP2016065807 | 2016-03-29 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4902246B2 (en) * | 2006-03-31 | 2012-03-21 | 株式会社コーセー | Nail treatment cosmetics |
| US9193805B2 (en) * | 2010-02-19 | 2015-11-24 | Chiba Flour Milling Co., Ltd. | Dextrin fatty acid ester that does not cause gelation of liquid oil, and uses thereof |
| WO2016017624A1 (en) * | 2014-07-28 | 2016-02-04 | 株式会社 資生堂 | Oily cosmetic |
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