JP2013040146A - Coumaric acid amide derivative - Google Patents
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Description
本発明はクマル酸アミド誘導体に関し、特に化粧料、家庭用洗剤等の広範囲の分野において利用可能な光分解性界面活性剤として有用なクマル酸アミド誘導体に関する。 The present invention relates to a coumaric acid amide derivative, and particularly to a coumaric acid amide derivative useful as a photodegradable surfactant that can be used in a wide range of fields such as cosmetics and household detergents.
液体−液体、液体−固体界面に吸着してそれらの界面の性質を著しく変える性質を界面活性といい、界面活性剤とはその界面活性を有する成分のことを言う。界面活性剤の持つ界面活性作用には乳化、可溶化、分散、浸透、洗浄、潤滑等が含まれるため、各産業にとって必須成分の一つである。 The property of adsorbing at the liquid-liquid or liquid-solid interface to remarkably change the properties of those interfaces is called surface activity, and the surfactant is a component having the surface activity. Since the surface active action of the surfactant includes emulsification, solubilization, dispersion, penetration, washing, lubrication, etc., it is one of the essential components for each industry.
例えば化粧料産業では、皮膚外用剤の一つである乳液の基剤安定化という目的で主に活用されている。しかし従来の界面活性剤では種類の選定、または相当量の配合により基剤安定性は向上するものの、塗布した後、まれに肌荒れの原因の一つとなり、この観点から界面活性剤の存在が問題とされることもあった。すなわち、界面活性剤は、基剤の安定性向上の観点から数多くの皮膚外用剤には欠かせない成分である一方で、ごくまれに起こる肌荒れを引き起こすというイメージから製剤の商品価値を損なうこともあるという課題があった。 For example, in the cosmetic industry, it is mainly used for the purpose of stabilizing the base of an emulsion, which is one of external preparations for skin. However, with conventional surfactants, the stability of the base is improved by selecting the type or blending a considerable amount, but after application it is rarely one of the causes of rough skin. From this viewpoint, the presence of the surfactant is a problem. Sometimes it was said. In other words, surfactants are indispensable ingredients for many topical skin preparations from the standpoint of improving the stability of the base, but they also impair the commercial value of the formulation from the image that it causes rare skin roughness. There was a problem that there was.
近年、ジェミニ型（双子型）と言われる界面活性剤が提案されている（例えば特許文献１参照）。これは従来の界面活性剤に比べて界面活性能に優れるため、配合が少量でも基剤安定性に優れ且つ肌荒れを起こしにくい。そのことから化粧料用途を中心に開発が進められているものの、製法が難しく且つ高価な原料を使用する必要があるため、なかなか実用化が進んでいない。 In recent years, a surfactant called gemini type (twin type) has been proposed (see, for example, Patent Document 1). This is superior in surface active ability as compared with conventional surfactants, so even in a small amount, it is excellent in base stability and hardly causes rough skin. For this reason, development has been progressing mainly for cosmetics use, but since the production method is difficult and it is necessary to use an expensive raw material, it has not been practically used.
そこで基剤中では界面活性剤として機能するものの、光照射により界面活性剤が分解したり、その機能が低下するものが望まれていた。そういった界面活性剤を配合すれば、基剤中での安定性は保たれるけれども、皮膚に塗布した後は、上記のごくまれに起こる肌荒れをなくすことが期待される。 Therefore, it is desired that the base material functions as a surfactant, but the surfactant is decomposed by light irradiation or its function is lowered. If such a surfactant is blended, stability in the base is maintained, but it is expected to eliminate the above-mentioned rare rough skin after application to the skin.
光で分解する界面活性剤は種々提案されている（例えば非特許文献１〜３参照）。しかしこれらは分解後、特に有効な成分にはならない。
また、光に応答する成分としても種々提案されている（例えば特許文献２参照）。しかしこれらは接着剤やコーティング剤に用いた場合、製品に残存する界面活性剤に起因した塗布層の泡立ち、接着性、耐水性の問題を解決したものであり、基剤安定性や肌荒れ防止を目的としたものではなく、またその効果も満足できるものではない。
さらに、ポリアルコキシカルビノール桂皮酸エステルを含有する光保護剤も提案されている（例えば特許文献３参照）。しかしこの成分は界面活性剤ではないため、上記の期待されている効果は認められない。
Various surfactants that decompose by light have been proposed (see, for example, Non-Patent Documents 1 to 3). However, they do not become particularly effective ingredients after decomposition.
Various components that respond to light have been proposed (see, for example, Patent Document 2). However, when these are used in adhesives and coating agents, they solve the problems of foaming, adhesion, and water resistance of the coating layer caused by the surfactant remaining in the product, and they improve the stability of the base and the prevention of rough skin. It is not intended and its effect is not satisfactory.
Furthermore, a photoprotective agent containing polyalkoxycarbinol cinnamate has also been proposed (see, for example, Patent Document 3). However, since this component is not a surfactant, the above expected effect is not recognized.
本発明は前記従来技術に鑑みなされたものであり、その解決すべき課題は、光照射前は優れた界面活性能を有するものの、光照射後はクマリン誘導体（香料）とアミン（保湿剤）に効率よく分解するクマル酸アミド誘導体を提供することにある。 The present invention has been made in view of the above prior art, and the problem to be solved is that it has an excellent surface activity before light irradiation, but is coumarin derivative (fragrance) and amine (humectant) after light irradiation. The object is to provide a coumaric acid amide derivative that decomposes efficiently.
本発明者等が前記課題に鑑み鋭意研究した結果、特定のクマル酸アミド誘導体が、光照射前は優れた界面活性能を有するものの、光照射後はクマリン誘導体（香料）とアミン（保湿剤）に効率よく分解することを見出し、本発明を完成するに至った。 As a result of intensive studies conducted by the present inventors in view of the above problems, a specific coumaric acid amide derivative has excellent surface activity before light irradiation, but after light irradiation, a coumarin derivative (fragrance) and an amine (humectant) Thus, the present invention was completed.
すなわち、本発明にかかるクマル酸アミド誘導体は、下記一般式（１）で示されることを特徴とする。
本発明にかかる光分解性界面活性剤は、前記クマル酸アミド誘導体からなることを特徴とする。
本発明にかかる化粧料は、前記光分解性界面活性剤を含むことを特徴とする。
前記化粧料において、光分解性界面活性剤を０．０１〜１０質量％含むことが好適である。
The photodegradable surfactant according to the present invention is characterized by comprising the coumaric acid amide derivative.
The cosmetic according to the present invention includes the photodegradable surfactant.
The cosmetic preferably contains 0.01-10% by mass of a photodegradable surfactant.
本発明にかかるクマル酸アミド誘導体は、光照射前は優れた界面活性能を有するものの、光照射後はクマリン誘導体（香料）とアミン（保湿剤）に効率よく分解することができる。 The coumaric acid amide derivative according to the present invention has excellent surface activity before light irradiation, but can be efficiently decomposed into a coumarin derivative (fragrance) and an amine (humectant) after light irradiation.
以下、本発明の実施の形態について詳しく説明するが、本発明はこれに限定されるものではない。
本発明にかかるクマル酸アミド誘導体は、下記一般式（１）で示される化合物である。
Hereinafter, embodiments of the present invention will be described in detail, but the present invention is not limited thereto.
The coumaric acid amide derivative according to the present invention is a compound represented by the following general formula (1).
式（１）中、Ｒ１は、炭素数４〜８の炭化水素基である。Ｒ１の炭素数が４未満では、界面活性能が低くなる。また、８を超えると、水への溶解性が低くなる。
Ｒ１としては、ｎ−ブチル、ｉ−ブチル、ｓ−ブチル、ｔ−ブチル、ペンチル、イソペンチル、ネオペンチル、ヘキシル、イソヘキシル、ネオヘキシル、ヘプチル、イソペンチル、ネオペンチル、オクチル、イソオクチル、ネオオクチル基等が挙げられる。
本発明において、Ｒ１は炭素数４のアルキル基であることが好適である。
In formula (1), R 1 is a hydrocarbon group having 4 to 8 carbon atoms. When R 1 has less than 4 carbon atoms, the surface activity is low. Moreover, when it exceeds 8, the solubility to water becomes low.
Examples of R 1 include n-butyl, i-butyl, s-butyl, t-butyl, pentyl, isopentyl, neopentyl, hexyl, isohexyl, neohexyl, heptyl, isopentyl, neopentyl, octyl, isooctyl, neooctyl group and the like.
In the present invention, R 1 is preferably an alkyl group having 4 carbon atoms.
Ｒ２及びＲ３は同一もしくは異なってもよい水素又は置換基であって、該置換基は、オキシエチレン基を有していてもよい。
Ｒ２及び／又はＲ３は、下記式（２）で示される置換基であってもよい。
R 2 and R 3 may be the same or different hydrogen or a substituent, and the substituent may have an oxyethylene group.
R 2 and / or R 3 may be a substituent represented by the following formula (2).
式（２）中、Ｒ４は、CmH2mで表されるアルキレン基であり、１≦ｍ≦５である。
ｎは、オキシエチレン基の平均付加モル数を表し、０≦ｎ≦２０である。
Ｒ５は、水素原子、または、ClH2l+1で表されるアルキル基であり、１≦ｌ≦５である。
In formula (2), R 4 is an alkylene group represented by C m H 2m , and 1 ≦ m ≦ 5.
n represents the average addition mole number of an oxyethylene group, and 0 ≦ n ≦ 20.
R 5 is a hydrogen atom or an alkyl group represented by C l H 2l + 1 , and 1 ≦ l ≦ 5.
本発明のクマル酸アミド誘導体において、Ｒ２及びＲ３の少なくとも一つが式（２）で示される置換基であることが好ましい。
また、クマル酸アミド誘導体を光分解性界面活性剤として用いる場合、親水性を上げるために、Ｒ２及び／又はＲ３に、式（２）で示され、ｎが１以上、さらにはｎが６以上、特にｎが９以上の置換基を含むことが好ましい。
In the coumaric acid amide derivative of the present invention, at least one of R 2 and R 3 is preferably a substituent represented by the formula (2).
When a coumaric acid amide derivative is used as a photodegradable surfactant, in order to increase hydrophilicity, R 2 and / or R 3 is represented by the formula (2), n is 1 or more, and n is It is preferable that the substituent contains 6 or more, particularly n is 9 or more.
本発明にかかるクマル酸アミド誘導体は光照射により、（化４）に示されるように、クマリン誘導体とアミンに分解する。 The coumaric acid amide derivative according to the present invention is decomposed by irradiation with light into a coumarin derivative and an amine as shown in (Chemical Formula 4).
このような本発明のクマル酸アミド誘導体は、光照射前は優れた界面活性能を有し、安定性の向上や洗浄力の付与に寄与するが、光照射後は分解することから、光分解性界面活性剤として用いることができる。 Such a coumaric acid amide derivative of the present invention has excellent surface activity before light irradiation and contributes to improvement of stability and imparting detergency, but it decomposes after light irradiation. It can be used as a surfactant.
なお、光照射・分解後に生成されるクマリン誘導体は、桜餅様の香りを有する香料であり、同じく生成されるアミンは、保湿剤として機能し得る。
このため、本発明の光分解性界面活性剤は、化粧料に配合することが好ましい。
近年、化粧料に汎用されている界面活性剤は、漠然と悪いイメージを持たれる場合があり、肌に及ぼす影響を懸念している消費者も多い。しかし、本発明の光分解性界面活性剤は、容器から肌へと塗布した後、日常生活中の太陽光照射により界面活性能が低下し、香料および保湿剤になるため、そのようなイメージを持つ消費者にとっても、安心して使用することができる。
In addition, the coumarin derivative produced | generated after light irradiation and decomposition | disassembly is a fragrance | flavor which has a cherry-blossom-like fragrance, and the amine produced | generated similarly can function as a moisturizer.
For this reason, it is preferable to mix | blend the photodegradable surfactant of this invention with cosmetics.
In recent years, surfactants widely used in cosmetics may have a vaguely bad image, and many consumers are concerned about the effect on the skin. However, since the photodegradable surfactant of the present invention is applied to the skin from the container, and the surface active ability is reduced by sunlight irradiation in daily life, it becomes a fragrance and a humectant. It can be used with peace of mind even for consumers.
本発明のクマル酸アミド誘導体を光分解性界面活性剤として化粧料に配合する場合、その配合量は、特に限定されるものではないが、化粧料全量中０．０１〜１０質量％であることが好適である。また、０．１〜５質量％であることが特に好適である。光分解性界面活性剤の配合量が０．０１質量％未満では、安定性が悪くなる場合があり、また、１０質量％を超えると、使用感触に悪影響を及ぼす場合がある。 When the coumaric acid amide derivative of the present invention is blended in a cosmetic as a photodegradable surfactant, the blending amount is not particularly limited, but is 0.01 to 10% by mass in the total amount of the cosmetic. Is preferred. Moreover, it is especially suitable that it is 0.1-5 mass%. When the blending amount of the photodegradable surfactant is less than 0.01% by mass, the stability may be deteriorated, and when it exceeds 10% by mass, the use feeling may be adversely affected.
化粧料に配合する場合、上記必須成分であるクマル酸アミド誘導体に加えて、通常の化粧料に用いられるその他の任意成分を、本発明の効果を損なわない質的・量的な範囲内で、配合することもできる。
そのような任意成分としては、例えば、油分、ワックス、増粘剤、ゲル化剤、金属石鹸、水溶性高分子、油溶性高分子、薬剤、酸化防止剤、顔料、染料、パール剤、ラメ剤、有機・無機粉末等が挙げられる。
When blended in cosmetics, in addition to the coumaric acid amide derivative, which is an essential component, other optional components used in ordinary cosmetics, within a qualitative and quantitative range that does not impair the effects of the present invention, It can also be blended.
Examples of such optional components include oil, wax, thickener, gelling agent, metal soap, water-soluble polymer, oil-soluble polymer, drug, antioxidant, pigment, dye, pearl agent, lame agent. And organic / inorganic powders.
また、化粧料の使用用途は、特に限定されるものではなく、例えば、クリーム、乳液、ローション、エッセンス等のスキンケア化粧料、へアクリーム、ヘアローション、整髪料等のヘアケア化粧料、サンスクリーン、ボディクリーム、ボディローション等のボディケア化粧料、口紅、マスカラ、アイライナー、ネールエナメル、ファンデーション等のメーキャップ化粧料等の化粧料に利用することができる。 In addition, the usage of the cosmetic is not particularly limited, for example, skin care cosmetics such as creams, emulsions, lotions, essences, hair care cosmetics such as hair creams, hair lotions, hair stylings, sunscreens, It can be used for body care cosmetics such as body cream and body lotion, and cosmetics such as makeup cosmetics such as lipstick, mascara, eyeliner, nail enamel and foundation.
本発明のクマル酸アミド誘導体は、以上に説明した光分解性界面活性剤として化粧料に配合する以外にも、あらゆる光分解性物質（例えば、分散剤、表面処理剤、乳化重合用界面活性剤、洗浄料、農薬等）として好適に用いることもできる。 The coumaric acid amide derivative of the present invention is not limited to the above-described photodegradable surfactants, and other photodegradable substances (for example, dispersants, surface treatment agents, surfactants for emulsion polymerization). , Cleaning agents, agricultural chemicals, etc.).
本発明について、以下に実施例を挙げてさらに詳述するが、本発明はこれにより何ら限定されるものではない。
はじめに、以下の実施例で用いたクマル酸アミド誘導体（化合物１）の合成方法について以下に示す。
The present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto.
First, a method for synthesizing a coumaric acid amide derivative (Compound 1) used in the following Examples is shown below.
・化合物１の合成方法
（化合物Ａの合成）
ウンベリフェロン１０ｇ（１．５４×１０-2ｍｏｌ）にアセトン３００ｍＬ、炭酸カリウム（１．５４×１０-2ｍｏｌ）、１−ブロモブタン１６．９ｇ（１．５４×１０-2ｍｏｌ）を加え、６０℃で１７時間還流を行った。その後、吸引ろ過で炭酸カリウムを取り除き、ろ液をエバポレーターにより濃縮し、未反応の１−ブロモブタンを除去した。得られた固体を、酢酸エチルと水で分液を行った（炭酸水素ナトリウムによる洗浄を２回、水洗を１回）。エバポレーターにより酢酸エチルを除去し、下記（化５）で示される化合物Ａ（黄色固体）を１２．９１ｇ（収率９６％）得た。
Synthesis method of compound 1 (synthesis of compound A)
To 10 g (1.54 × 10 −2 mol) of umbelliferone, 300 mL of acetone, potassium carbonate (1.54 × 10 −2 mol) and 16.9 g (1.54 × 10 −2 mol) of 1-bromobutane were added, Refluxing was performed at 60 ° C. for 17 hours. Thereafter, potassium carbonate was removed by suction filtration, and the filtrate was concentrated by an evaporator to remove unreacted 1-bromobutane. The obtained solid was subjected to liquid separation with ethyl acetate and water (washing with sodium hydrogen carbonate twice and washing with water once). Ethyl acetate was removed by an evaporator to obtain 12.91 g (yield 96%) of compound A (yellow solid) represented by the following (Chemical Formula 5).
（化合物Ｂの合成）
化合物Ａ（ブチル基導入ウンベリフェロン）０．５ｇ（２．２９×１０-3ｍｏｌ）、脱水メタノール２０ｍＬ、ナトリウムメトキシド０．７６８ｇ（１．４２×１０-3ｍｏｌ）を加え、室温で６時間撹拌した。水を加えることで、未反応のナトリウムメトキシドが水酸化ナトリウムとなることを利用して、加水分解を行った。なお、加水分解は６０℃で２時間還流を行った。その後、エバポレーターによりメタノールを除去し、ｐＨが７となるまで塩酸水溶液をゆっくり滴下した。白色固体を吸引ろ過により取り出し、乾燥して下記（化６）で示される化合物Ｂを０．７６８ｇ（収率５５．５％）得た。
(Synthesis of Compound B)
Compound A (butyl group-introduced umbelliferone) 0.5 g (2.29 × 10 −3 mol), dehydrated methanol 20 mL, sodium methoxide 0.768 g (1.42 × 10 −3 mol) was added, and 6 at room temperature was added. Stir for hours. Hydrolysis was performed utilizing the fact that unreacted sodium methoxide became sodium hydroxide by adding water. The hydrolysis was refluxed at 60 ° C. for 2 hours. Thereafter, methanol was removed by an evaporator, and an aqueous hydrochloric acid solution was slowly added dropwise until the pH reached 7. The white solid was taken out by suction filtration and dried to obtain 0.768 g (yield 55.5%) of Compound B represented by the following (Chemical Formula 6).
化合物Ｂ（ブチル基導入ｏ−クマル酸）０．２３ｇ(１．０２×１０-3ｍｏｌ)
、脱水テトラヒドロフラン２０ｍＬ、NH2CH2CH2CH2O(CH2CH2O)9CH3 ０．８７ｇ(２．０３×１０-3ｍｏｌ) 、１−エチル−３−(３−ジメチルアミノプロピル)カルボジイミド塩酸塩０．３９ｇ(６．０９×１０-3ｍｏｌ)
、脱水ジクロロメタン１０ｍＬを加え、ＤＭＡＰを触媒量、トリエチルアミンを０．３１ｇ(３．０６×１０-3ｍｏｌ)加え室温で２４時間撹拌した。エバポレーターによりテトラヒドロフラン及びジクロロメタンを除去し、酢酸エチルと水で分液を行った（塩酸水溶液による洗浄を２回、水洗を１回）。有機層をエバポレーターにより除去し、得られた粘性液体に対してカラムクロマトグラフィーを行った。充填剤には、ワコールＣ−２００(和光純薬工業株式会社)を、展開溶媒にはクロロホルム：メタノール＝１９:１の混合溶媒(重量比)を用いた。カラム精製後、エバポレーターで展開溶媒を除去し、目的物である下記（化７）で示される化合物１（黄色粘体）を０．５１ｇ（収率７７．８％）得た。
Compound B (butyl group-introduced o-coumaric acid) 0.23 g (1.02 × 10 −3 mol)
, 20 mL of dehydrated tetrahydrofuran, NH 2 CH 2 CH 2 CH 2 O (CH 2 CH 2 O) 9 CH 3 0.87 g (2.03 × 10 −3 mol), 1-ethyl-3- (3-dimethylaminopropyl) ) Carbodiimide hydrochloride 0.39 g (6.09 × 10 −3 mol)
Then, 10 mL of dehydrated dichloromethane was added, a catalytic amount of DMAP and 0.31 g (3.06 × 10 −3 mol) of triethylamine were added, and the mixture was stirred at room temperature for 24 hours. Tetrahydrofuran and dichloromethane were removed by an evaporator, and liquid separation was performed with ethyl acetate and water (washing with aqueous hydrochloric acid twice and washing with water once). The organic layer was removed by an evaporator, and the obtained viscous liquid was subjected to column chromatography. Wacoal C-200 (Wako Pure Chemical Industries, Ltd.) was used as the filler, and a mixed solvent (weight ratio) of chloroform: methanol = 19: 1 was used as the developing solvent. After column purification, the developing solvent was removed with an evaporator to obtain 0.51 g (yield 77.8%) of Compound 1 (yellow viscous body) represented by the following (Chemical Formula 7), which is the target product.
次に、クマル酸アミド誘導体の光分解について検討を行った。
以下の測定条件で、化合物１に３６５ｎｍの光を照射し、各照射エネルギーのＵＶスペクトルを測定した。結果を図１に示す。
Next, photodecomposition of coumaric acid amide derivatives was examined.
Under the following measurement conditions, Compound 1 was irradiated with 365 nm light, and the UV spectrum of each irradiation energy was measured. The results are shown in FIG.
（測定条件）
照射波長：３６５ｎｍ
光源：水銀−キセノンランプ ＳＡＮ−ＥＩＳＵＰＥＲＣＵＲＥ−２０３Ｓ
バンドパスフィルター（３６５ｎｍ） ＵＶＤ−３６Ａ
セル:石英セル（光路長１ｍｍ）
溶媒 :水
濃度:４．２６×１０-4ｍｏｌ／Ｌ
紫外可視分光光度計：Ａｇｉｌｅｎｔ ８４５３
(Measurement condition)
Irradiation wavelength: 365 nm
Light source: mercury-xenon lamp SAN-EISUPERCURE-203S
Band pass filter (365nm) UVD-36A
Cell: Quartz cell (optical path length 1mm)
Solvent: Water concentration: 4.26 × 10 −4 mol / L
UV-Vis spectrophotometer: Agilent 8453
図１によると、照射エネルギーが増加するにつれて、２００ｎｍ付近のクマリン由来のピークが増加し、３２０ｎｍ付近の化合物１由来のピークが減少していることがわかった。
このようなピークが確認できたこと、および、ＵＶ照射に伴いクマリン由来の香りがあったことから、化合物１の下記（化８）に示されるような光分解の達成が示唆された。
According to FIG. 1, it was found that as the irradiation energy increased, the peak derived from coumarin around 200 nm increased and the peak derived from compound 1 near 320 nm decreased.
The fact that such a peak could be confirmed and that there was a scent derived from coumarin accompanying UV irradiation suggested that the photolysis of Compound 1 as shown in the following (Chemical Formula 8) was achieved.
次に、（光分解前の）化合物１のスクアラン／水の界面張力を測定し、ＵＶ光照射（光分解）後と比較を行った。測定は２５℃で行い、協和界面科学社製 Ｄｒｏｐ Ｍａｓｔｅｒ ７００を用いた。スクアランはＷａｋｏ社製のものを用いた。なお、スクアラン／水の界面張力は４４．３ｍＮ／ｍであった。結果を図２に示す。 Next, the interfacial tension of squalane / water of compound 1 (before photolysis) was measured and compared with that after UV light irradiation (photolysis). The measurement was performed at 25 ° C., and a Drop Master 700 manufactured by Kyowa Interface Science Co., Ltd. was used. A squalane manufactured by Wako was used. The interfacial tension of squalane / water was 44.3 mN / m. The results are shown in FIG.
図２によると、光分解前の化合物１は濃度が増加するに従って界面張力が低下し、ある一点から界面張力が一定となった。この屈曲点をｃｍｃ（＝０．２１ｍｍｏｌ／Ｌ）とした。この結果から化合物１が界面活性能を有していることが分かる。
一方、光照射後は、光分解により界面張力が劇的に増加している。なお、ｃｍｃの２倍の濃度での分解率は８２％と算出できている。高濃度では分解に伴う界面張力の増加は小さい。これは分解後に残存した界面活性剤が界面張力を低下させているためと考えられる。
According to FIG. 2, the interfacial tension of Compound 1 before photolysis decreased as the concentration increased, and the interfacial tension became constant from a certain point. The bending point was cmc (= 0.21 mmol / L). From this result, it can be seen that Compound 1 has surface activity.
On the other hand, after light irradiation, the interfacial tension is dramatically increased by photolysis. The decomposition rate at a concentration twice that of cmc can be calculated as 82%. At high concentrations, the increase in interfacial tension accompanying decomposition is small. This is presumably because the surfactant remaining after the decomposition reduces the interfacial tension.
以下に、本発明のクマル酸アミド誘導体を光分解性界面活性剤として配合した化粧料の配合処方例を挙げるが、本発明の技術範囲はこれらにより限定されるものではない。 Hereinafter, examples of blending formulations of cosmetics in which the coumaric acid amide derivative of the present invention is blended as a photodegradable surfactant will be described, but the technical scope of the present invention is not limited thereto.
配合処方例１：乳液
（配合成分） （質量％）
（１）流動パラフィン ６．０
（２）スクワラン ２．０
（３）化合物１ ２．０
（４）１，３−ブチレングリコール ２．５
（５）ジプロピレングリコール １．５
（６）エタノール ３．０
（７）カルボキシビニルポリマー ０．２
（８）水酸化カリウム ０．１
（９）エデト酸三ナトリウム ０．０５
（１０）フェノキシエタノール ０．５
（１１）香料 ０．１
（１２）精製水 残 余
Formulation Example 1: Emulsion (Compounding ingredients) (mass%)
(1) Liquid paraffin 6.0
(2) Squalane 2.0
(3) Compound 1 2.0
(4) 1,3-butylene glycol 2.5
(5) Dipropylene glycol 1.5
(6) Ethanol 3.0
(7) Carboxyvinyl polymer 0.2
(8) Potassium hydroxide 0.1
(9) edetate trisodium 0.05
(10) Phenoxyethanol 0.5
(11) Fragrance 0.1
(12) Residue of purified water
配合処方例２：クリーム
（配合成分） （質量％）
（１）流動パラフィン ８．０
（２）水添ポリイソブテン ３．０
（３）化合物１ ２．５
（４）モノステアリン酸ソルビタン １．５
（５）セテアリルアルコール ６．０
（６）ステアリン酸ＰＥＧ−１００ １．５
（７）グリセリン ５．０
（８）１，３−ブチレングリコール ３．０
（９）ヒアルロン酸ナトリウム ０．５
（１０）Ｌ−アルギニン塩酸塩 ０．０２
（１１）エデト酸三ナトリウム ０．０５
（１２）フェノキシエタノール ０．４
（１３）香料 ０．１
（１４）精製水 残 余
Formulation Example 2: Cream (Compounding ingredients) (mass%)
(1) Liquid paraffin 8.0
(2) Hydrogenated polyisobutene 3.0
(3) Compound 1 2.5
(4) Sorbitan monostearate 1.5
(5) Cetearyl alcohol 6.0
(6) PEG-100 stearate 1.5
(7) Glycerin 5.0
(8) 1,3-butylene glycol 3.0
(9) Sodium hyaluronate 0.5
(10) L-arginine hydrochloride 0.02
(11) Trisodium edetate 0.05
(12) Phenoxyethanol 0.4
(13) Fragrance 0.1
(14) Purified water residue
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2002069485A (en) * | 2000-08-25 | 2002-03-08 | Kawaken Fine Chem Co Ltd | Thickner composition containing fatty acid alkanolamide and liquid detergent formation containing the same |
| JP2004513217A (en) * | 2000-11-08 | 2004-04-30 | ザ、プロクター、エンド、ギャンブル、カンパニー | Photolabile pro-fragrance conjugate |
| JP2010254946A (en) * | 2008-09-30 | 2010-11-11 | Dainippon Printing Co Ltd | Photosensitive resin composition, pattern-forming material comprising the photosensitive resin composition, method for forming pattern, article using the photosensitive resin composition, and photo-latent resin curing accelerator |
| JP2012211276A (en) * | 2011-03-31 | 2012-11-01 | Dainippon Printing Co Ltd | Base generator, photosensitive resin composition, pattern-forming material comprising the photosensitive resin composition, method of producing relief pattern by using the photosensitive resin composition, and molded article |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002069485A (en) * | 2000-08-25 | 2002-03-08 | Kawaken Fine Chem Co Ltd | Thickner composition containing fatty acid alkanolamide and liquid detergent formation containing the same |
| JP2004513217A (en) * | 2000-11-08 | 2004-04-30 | ザ、プロクター、エンド、ギャンブル、カンパニー | Photolabile pro-fragrance conjugate |
| JP2010254946A (en) * | 2008-09-30 | 2010-11-11 | Dainippon Printing Co Ltd | Photosensitive resin composition, pattern-forming material comprising the photosensitive resin composition, method for forming pattern, article using the photosensitive resin composition, and photo-latent resin curing accelerator |
| JP2012211276A (en) * | 2011-03-31 | 2012-11-01 | Dainippon Printing Co Ltd | Base generator, photosensitive resin composition, pattern-forming material comprising the photosensitive resin composition, method of producing relief pattern by using the photosensitive resin composition, and molded article |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105838388A (en) * | 2015-02-03 | 2016-08-10 | Jsr株式会社 | Liquid crystal aligning agent, liquid crystal alignment film and manufacturing method therefor, liquid crystal element, polymer, diamine and acid dianhydride |
| CN105838388B (en) * | 2015-02-03 | 2020-12-29 | Jsr株式会社 | Liquid crystal aligning agent, liquid crystal alignment film, method for producing liquid crystal alignment film, liquid crystal element, polymer, diamine, and acid dianhydride |
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