JP2009215262A - Sucrose fatty acid ester and emulsifier for oil-in-water type emulsion compositions - Google Patents
Sucrose fatty acid ester and emulsifier for oil-in-water type emulsion compositions Download PDFInfo
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Images
Abstract
Description
本発明は、特定のエステル組成を持つショ糖脂肪酸エステル、及び、該ショ糖脂肪酸エステルを含有する水中油型乳化組成物用乳化剤に関するものである。 The present invention relates to a sucrose fatty acid ester having a specific ester composition, and an emulsifier for an oil-in-water emulsion composition containing the sucrose fatty acid ester.
ショ糖脂肪酸エステルは、ショ糖(スクロース)の水酸基に脂肪酸がエステル結合してなる非イオン界面活性剤であり、安全性が高いことから、様々な分野に用いられている。上記ショ糖には1分子中に8つの水酸基があるため、一般に、ショ糖脂肪酸エステルは、エステル化度の異なるエステルの混合物として製造され、市販されている。 Sucrose fatty acid esters are nonionic surfactants in which fatty acids are ester-bonded to the hydroxyl groups of sucrose (sucrose) and are used in various fields because of their high safety. Since the above sucrose has eight hydroxyl groups in one molecule, sucrose fatty acid esters are generally produced as a mixture of esters having different degrees of esterification and are commercially available.
かかるショ糖脂肪酸エステルに関し、下記特許文献1〜5には、エステル化度が2のジエステル成分を50重量%以上含有するものを、化粧品、医薬品、食品等の分野に用いることが提案されている。
Regarding such sucrose fatty acid esters, the following
すなわち、特許文献1には、ショ糖脂肪酸ジエステル及びイオン性界面活性剤を乳化剤として用いることで、皮膚上での撥水性や保持性に優れた水中油型乳化組成物が開示され、特許文献2には、有効成分のマイクロカプセルとしてのベシクルを形成する成分として、ショ糖脂肪酸ジエステルを用いることで、長期にわたって安定で有効成分の洩れを少なくすることが開示されている。
That is,
また、特許文献3,4には、ショ糖脂肪酸ジエステル及びイオン性界面活性剤を併用することで、安定性、使用性に優れ、良好な増粘ゲル化を行うことができる増粘ゲル化剤が開示され、また、特許文献5には、ショ糖脂肪酸ジエステルを、イオン性界面活性剤と高級脂肪酸アルコール及び/又は高級脂肪酸とともに増粘ゲル化剤として用いて、皮膚上の撥水性や保持性に優れる水中油型乳化組成物を得る点が開示されている。
上記文献に開示の技術では、全ショ糖脂肪酸エステルに対してジエステル成分を50重量%以上にすることを要件としているが、実際に、水に溶解させたときの溶解性や、化粧品用途における保湿性の観点から見ると、必ずしも最良の範囲ではないことが判明した。例えば、ジエステル成分が50重量%以上であったとしても、トリエステル以上のエステル成分が多いと、ショ糖脂肪酸エステル自体の水溶性が劣り、また、モノエステル成分が多いと、形成されたラメラ相に十分な水分を保持することができないという問題がある。 The technique disclosed in the above document requires that the diester component is 50% by weight or more based on the total sucrose fatty acid ester, but the solubility when actually dissolved in water and the moisturizing in cosmetic applications. From the viewpoint of sex, it turned out to be not necessarily the best range. For example, even if the diester component is 50% by weight or more, if the ester component is more than the triester, the water solubility of the sucrose fatty acid ester itself is poor, and if the monoester component is much, the formed lamellar phase There is a problem that sufficient water cannot be retained.
そして、更に、かかるエステル組成について鋭意検討したところ、特定のエステル組成を持つショ糖脂肪酸エステルが、水中油型乳化組成物の乳化剤として用いたときに該乳化組成物の経時安定性を特異的に改善できることを見い出した。 Further, when the sucrose fatty acid ester having a specific ester composition was used as an emulsifier of the oil-in-water emulsion composition, the aging stability of the emulsion composition was specifically determined. I found that it can be improved.
本発明は、上記の知見に基づいてなされたものであり、水に溶解させたときの溶解性に優れる、つまり水に溶解させたときに容易にラメラ相を形成するとともに、保湿性(水分保持能力)に優れ、更に水中油型乳化組成物の経時安定性を特異的に改善することができるショ糖脂肪酸エステルを提供することを目的とする。 The present invention has been made on the basis of the above knowledge, and has excellent solubility when dissolved in water, that is, it easily forms a lamellar phase when dissolved in water, and has moisture retention (moisture retention). It is an object of the present invention to provide a sucrose fatty acid ester that is excellent in ability) and that can specifically improve the temporal stability of an oil-in-water emulsion composition.
本発明に係るショ糖脂肪酸エステルは、エステル化度が1のモノエステル成分26〜35重量%、エステル化度が2のジエステル成分55〜65重量%、及びエステル化度が3以上のエステル成分5〜14重量%よりなるものである。また、本発明に係る水中油型乳化組成物のための乳化剤は、該ショ糖脂肪酸エステルを含有するものである。 The sucrose fatty acid ester according to the present invention comprises a monoester component having a degree of esterification of 26 to 35% by weight, a diester component having a degree of esterification of 55 to 65% by weight, and an ester component 5 having a degree of esterification of 3 or more. It consists of ˜14% by weight. Moreover, the emulsifier for the oil-in-water type emulsion composition which concerns on this invention contains this sucrose fatty acid ester.
本発明によれば、ショ糖脂肪酸エステルのエステル組成を上記の通り規定したことにより、ショ糖脂肪酸エステルを水に溶解させたときの溶解性に優れるとともに、保湿性(水分保持能力)にも優れ、更には、水中油型乳化組成物の経時安定性を特異的に改善することができる。 According to the present invention, by defining the ester composition of the sucrose fatty acid ester as described above, the sucrose fatty acid ester is excellent in solubility when dissolved in water, and also excellent in moisture retention (moisture retention ability). Furthermore, the stability over time of the oil-in-water emulsion composition can be specifically improved.
以下、本発明の実施に関連する事項について詳細に説明する。 Hereinafter, matters related to the implementation of the present invention will be described in detail.
本発明に係るショ糖脂肪酸エステルは、エステル化度が1のモノエステル成分(ショ糖脂肪酸モノエステル。以下、単に「モノエステル」ということがある。)の含有量が26〜35重量%であり、エステル化度が2のジエステル成分(ショ糖脂肪酸ジエステル、以下、単に「ジエステル」ということがある。)の含有量が55〜65重量%であり、エステル化度が3以上のエステル成分(ショ糖脂肪酸ポリエステル。以下、単に「ポリエステル」ということがある。)の含有量が5〜14重量%である、ショ糖脂肪酸エステルの混合物である。かかるエステル組成を図示すると、図1において斜線で示した範囲であり、ショ糖脂肪酸エステルの中でも極限られた範囲を規定するものである。 The sucrose fatty acid ester according to the present invention has a content of a monoester component having a degree of esterification of 1 (sucrose fatty acid monoester; hereinafter, simply referred to as “monoester”) of 26 to 35% by weight. The content of a diester component having a degree of esterification of 2 (sucrose fatty acid diester, hereinafter simply referred to as “diester”) is 55 to 65% by weight, and an ester component having a degree of esterification of 3 or more A mixture of sucrose fatty acid esters in which the content of sugar fatty acid polyester (hereinafter sometimes referred to simply as “polyester”) is 5 to 14% by weight. Such an ester composition is shown in a hatched range in FIG. 1 and defines a limited range among sucrose fatty acid esters.
このようにエステル組成を規定したのは次の理由による。すなわち、モノエステルの含有量を35重量%以下とすることで、水溶液としたときの水分保持能力を高くすることができ、例えば化粧品に用いた場合における保湿効果を高めることができる。逆に言えば、モノエステルの含有量が35重量%を超えると、熱重量分析(TG)で観察した水分蒸散が段階的でなくなることから、水溶液中で形成されたラメラ相に十分な水分を取り込み保持しているとは言えず、早期に蒸散してしまう。 The reason why the ester composition is defined in this way is as follows. That is, by setting the monoester content to 35% by weight or less, it is possible to increase the water retention ability when it is used as an aqueous solution, and to enhance the moisturizing effect when used in cosmetics, for example. Conversely, if the monoester content exceeds 35% by weight, the water evaporation observed by thermogravimetric analysis (TG) is not stepwise, so that sufficient water is added to the lamellar phase formed in the aqueous solution. It cannot be said that it is taken up and held, and evaporates early.
また、ポリエステルの含有量が14重量%以下であることにより、水に対する溶解性に優れる。また、ジエステルの含有量を55重量%以上とすることにより、上記した水溶液の水分保持能力をより顕著に高めることができる。そして、これらの規定とともに、モノエステルの含有量を26重量%以上、ジエステルの含有量を65重量%以下、ポリエステルの含有量を5重量部以上と規定することで、水中油型乳化組成物の経時安定性を特異的に改善することができる。 Moreover, when the content of the polyester is 14% by weight or less, the solubility in water is excellent. Moreover, the water | moisture retention capability of above-mentioned aqueous solution can be improved more notably by making content of a diester 55 weight% or more. And with these regulations, the monoester content is defined as 26% by weight or more, the diester content is defined as 65% by weight or less, and the polyester content is defined as 5 parts by weight or more. Stability over time can be specifically improved.
上記ポリエステルとしては、エステル化度が3のトリエステルを主成分とすることが好ましく、詳細には、全ショ糖脂肪酸エステル中で、トリエステル成分が5〜14重量%であり、エステル化度が4以上の成分が0〜5重量%であることが好ましく、エステル化度4以上の成分は含まれていなくてもよい。
The polyester preferably contains a triester having a degree of esterification of 3 as a main component. Specifically, in all sucrose fatty acid esters, the triester component is 5 to 14% by weight, and the degree of esterification is It is preferable that 4 or more components are 0-5 weight%, and the component of
上記ショ糖脂肪酸エステルを構成する脂肪酸としては、炭素数12〜22の飽和または不飽和の、直鎖または分岐を持つものが挙げられ、1種または2種以上組み合わせて用いられる。好ましくは炭素数14〜20の飽和脂肪酸であり、更に好ましくはステアリン酸とパルミチン酸の混合物であり、特に好ましくはステアリン酸/パルミチン酸=60/40〜90/10(重量比)である。 As fatty acid which comprises the said sucrose fatty acid ester, C12-C22 saturated or unsaturated, linear or branched thing is mentioned, It uses 1 type or in combination of 2 or more types. Preferred is a saturated fatty acid having 14 to 20 carbon atoms, more preferred is a mixture of stearic acid and palmitic acid, and particularly preferred is stearic acid / palmitic acid = 60/40 to 90/10 (weight ratio).
上記エステル組成を持つショ糖脂肪酸エステルは、既知の合成方法を利用して調製することができる。一般に、ショ糖脂肪酸エステルの合成方法としては、ジメチルホルムアミドやジメチルスルホキシド等の反応溶媒中で、アルカリ触媒の存在下、ショ糖と脂肪酸アルキルエステル(例えば脂肪酸メチル)とを反応させる方法(溶媒法:特公昭35−13102号公報)や、溶媒を用いずに水を使ってショ糖を脂肪酸石鹸と共に溶融混合物とした後、触媒の存在下に脂肪酸アルキルエステルと反応させる方法(水媒法:特公昭51−14485号公報)などが挙げられる。これらの合成方法で得られた反応生成物から、未反応の糖や脂肪酸アルキルエステル、溶媒などの夾雑物を除去した後、カラム等を用いて分画し、分画物を適宜組み合わせて配合することにより、上記エステル組成を持つショ糖脂肪酸エステルを調製することができる。また、市販のショ糖脂肪酸エステルを複数組み合わせて混合したり、あるいはまた、市販のショ糖脂肪酸エステルを、カラム等を用いて分画し、分画物を適宜に組み合わせて配合したり、また、これらの分画物を上記で合成したショ糖脂肪酸エステルまたはその分画物と適宜に組み合わせて配合することにより、上記エステル組成を持つショ糖脂肪酸エステルを調製することもできる。 The sucrose fatty acid ester having the above ester composition can be prepared by using a known synthesis method. In general, as a method for synthesizing a sucrose fatty acid ester, a method of reacting sucrose with a fatty acid alkyl ester (for example, fatty acid methyl) in a reaction solvent such as dimethylformamide or dimethyl sulfoxide in the presence of an alkali catalyst (solvent method: Japanese Patent Publication No. 35-13102) or a method in which water is used without using a solvent to make sucrose into a molten mixture together with a fatty acid soap and then reacted with a fatty acid alkyl ester in the presence of a catalyst (aqueous medium method: Japanese Patent Publication) 51-14485). After removing impurities such as unreacted sugar, fatty acid alkyl ester, and solvent from the reaction products obtained by these synthesis methods, fractionation is performed using a column or the like, and the fractions are appropriately combined and blended. Thus, a sucrose fatty acid ester having the above ester composition can be prepared. Further, a plurality of commercially available sucrose fatty acid esters are mixed and mixed, or alternatively, a commercially available sucrose fatty acid ester is fractionated using a column or the like, and the fractions are appropriately combined and blended, A sucrose fatty acid ester having the above ester composition can also be prepared by blending these fractions in combination with the sucrose fatty acid ester synthesized above or an appropriate fraction thereof.
本発明に係るショ糖脂肪酸エステルは、医薬品、化粧品、食品分野等における界面活性剤として用いることができる。特には、水中油型(O/W)乳化組成物を調製するための乳化剤として、あるいは、有効成分のマイクロカプセルとしてのベシクルを形成するためのベシクル形成剤として用いることが好適であり、具体的な用途としては、ローション、保湿クリーム、表皮からの水分蒸発を抑制できる水分閉塞性クリームなどの各種の皮膚外用剤への利用が好ましい例として挙げられる。 The sucrose fatty acid ester according to the present invention can be used as a surfactant in pharmaceuticals, cosmetics, foods and the like. In particular, it is preferably used as an emulsifier for preparing an oil-in-water (O / W) emulsion composition, or as a vesicle forming agent for forming vesicles as microcapsules of active ingredients. Preferable applications include application to various skin external preparations such as a lotion, a moisturizing cream, and a moisture-occlusive cream capable of suppressing moisture evaporation from the epidermis.
水中油型乳化組成物用乳化剤として用いる場合、該乳化剤は、上記ショ糖脂肪酸エステルのみで構成してもよく、また、該ショ糖脂肪酸エステルとともに、イオン性界面活性剤や、グリセリン脂肪酸エステル、プロピレングリコール脂肪酸エステル、ソルビタン脂肪酸エステル、レシチン、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンソルビタン脂肪酸エステル、ポリオキシエチレン脂肪酸エステル、ポリオキシエチレンヒマシ油、ポリオキシエチレングリセリルエーテル脂肪酸エステル、アルキルポリグルコシドなどに代表される非イオン界面活性剤などの他の界面活性剤を併用してもよい。前記イオン性界面活性剤としては、特に限定されないが、例えば、アシルグルタミン酸塩やステアロイル乳酸塩、スルホコハク酸塩、エーテルカルボン酸塩などのアニオン活性剤や、アルキルアンモニウム塩、ステアリン酸ジメチルアミノプロピルの有機酸塩などのカチオン活性剤、アルキル(アミド)ベタインやアルキルジメチルアミンオキシドなどの両性活性剤が挙げられ、炭素数12〜22の脂肪酸石鹸を用いることが好ましい。 When used as an emulsifier for an oil-in-water emulsion composition, the emulsifier may be composed only of the sucrose fatty acid ester, and together with the sucrose fatty acid ester, an ionic surfactant, glycerin fatty acid ester, propylene Represented by glycol fatty acid ester, sorbitan fatty acid ester, lecithin, polyoxyethylene alkyl ether, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene castor oil, polyoxyethylene glyceryl ether fatty acid ester, alkyl polyglucoside, etc. Other surfactants such as nonionic surfactants may be used in combination. Examples of the ionic surfactant include, but are not limited to, anionic surfactants such as acyl glutamate, stearoyl lactate, sulfosuccinate, and ether carboxylate, alkyl ammonium salts, and organic compounds such as dimethylaminopropyl stearate. Cationic activators such as acid salts and amphoteric activators such as alkyl (amido) betaines and alkyldimethylamine oxides can be mentioned, and it is preferable to use fatty acid soaps having 12 to 22 carbon atoms.
該乳化剤には、また、ステアリルアルコールやセチルアルコールなどの高級アルコール、フィトステロールなどのステロール誘導体、キサンタンガムやカルボマーなどに挙げられるような天然系多糖類・合成系の増粘剤・水溶性高分子、粘土鉱物や無水ケイ酸などの無機増粘剤、タルク・カオリン・雲母などの無機粉末、ポリアミド樹脂粉末・ポリスチレン粉末などの有機粉末・有機顔料・色素などの粉末、その他、保湿剤、皮膜剤、紫外線吸収剤、金属イオン封鎖剤、アミノ酸類、pH調整剤、皮膚栄養剤、ビタミン類、酸化防止剤、香料などの食品、化粧品、医薬分野において一般的に使用される素材を適宜使用することができる。 Examples of the emulsifier include higher alcohols such as stearyl alcohol and cetyl alcohol, sterol derivatives such as phytosterol, natural polysaccharides such as xanthan gum and carbomer, synthetic thickeners, water-soluble polymers, clays Inorganic thickeners such as minerals and silicic anhydride, inorganic powders such as talc, kaolin and mica, organic powders such as polyamide resin powder and polystyrene powder, powders such as organic pigments and pigments, etc., moisturizers, coating agents, ultraviolet rays Absorbers, sequestering agents, amino acids, pH adjusters, skin nutrients, vitamins, antioxidants, perfumes and other foods, cosmetics, and materials commonly used in the pharmaceutical field can be used as appropriate. .
水中油型乳化組成物中への上記ショ糖脂肪酸エステルの配合量は、特に限定されないが、0.5〜30重量%であることが好ましく、より好ましくは1〜10重量%である。 Although the compounding quantity of the said sucrose fatty acid ester in an oil-in-water type emulsion composition is not specifically limited, It is preferable that it is 0.5-30 weight%, More preferably, it is 1-10 weight%.
水中油型乳化組成物において、連続相である水相としては、水及び各種水溶液が挙げられ、化粧品、医薬品等の各種皮膚外用剤に配合される水溶性成分としてのエタノールや、プロピレングリコール、ブチレングリコールなどの多価アルコール、単糖やオリゴ糖などの糖類を配合してもよい。また、分散相である油相としても、特に限定されず、メチルシリコーンやジメチルシリコーンなどのシリコン油に代表される合成系油剤、ステアリン酸やイソステアリン酸などの高級脂肪酸、パラフィンやミネラル油などの鉱物油や炭化水素、パルミチン酸イソプロピルやミリスチン酸イソプロピルなどのエステル油、動植物油などの天然油脂やミツロウ・カルナバワックスなどのワックス類が挙げられる。水中油型乳化組成物には、また、これら水相及び油相に溶解しない粉体や顔料等を分散させて配合してもよい。 In the oil-in-water emulsion composition, the aqueous phase that is a continuous phase includes water and various aqueous solutions. Ethanol, propylene glycol, butylene as water-soluble ingredients to be blended in various skin external preparations such as cosmetics and pharmaceuticals. You may mix | blend polyhydric alcohols, such as glycol, and saccharides, such as a monosaccharide and an oligosaccharide. Also, the oil phase which is a dispersed phase is not particularly limited, and synthetic oils represented by silicone oil such as methyl silicone and dimethyl silicone, higher fatty acids such as stearic acid and isostearic acid, and minerals such as paraffin and mineral oil Examples thereof include oils and hydrocarbons, ester oils such as isopropyl palmitate and isopropyl myristate, natural fats and oils such as animal and vegetable oils, and waxes such as beeswax and carnauba wax. The oil-in-water emulsified composition may also be blended by dispersing powders or pigments that do not dissolve in the water phase and oil phase.
以下、本発明を実施例により具体的に説明するが、本発明の範囲はこれに限定されるものではない。 Hereinafter, the present invention will be specifically described by way of examples, but the scope of the present invention is not limited thereto.
1.ショ糖脂肪酸エステルの調製
下記表1及び図1に示すエステル組成を持つショ糖脂肪酸エステル(ステアリン酸/パルミチン酸=75/25(重量比))を調製した。調製は、「Determination of Sucrose Fatty Acid Esters by High-performance Liquid Chromatography」(J. Oleo Sci., Vol. 50, No. 4, 2001, p249-254)に記載の方法に従って、各エステルの純物質をHPLCにより分取し、必要に応じて各エステルを混合することにより行った。
1. Preparation of Sucrose Fatty Acid Esters Sucrose fatty acid esters (stearic acid / palmitic acid = 75/25 (weight ratio)) having the ester composition shown in Table 1 and FIG. 1 were prepared. The preparation was carried out according to the method described in “Determination of Sucrose Fatty Acid Esters by High-performance Liquid Chromatography” (J. Oleo Sci., Vol. 50, No. 4, 2001, p249-254). It fractionated by HPLC and performed by mixing each ester as needed.
エステル組成の分析は、ゲル濾過クロマトグラフィー(GPC)による。具体的には、条件を、カラム:Megapak GEL 201(日本分光株式会社製)、20mmφ×500mm×2本、溶離液:テトラヒドロフラン、流速:3ml/分、検出器:RI、カラム温度:常温とし、試料500mg及びラウリン酸(内部標準物質)200mgをテトラヒドロフラン10mlに溶解し、この溶液60μlを注入し分析した。そして、得られたクロマトグラムにおける各々のエステル部のピーク面積と内部標準物質との面積比を相対感度で補正することにより、各エステルの含有量を算出した。 Analysis of the ester composition is by gel filtration chromatography (GPC). Specifically, the conditions are as follows: column: Megapak GEL 201 (manufactured by JASCO Corporation), 20 mmφ × 500 mm × 2, eluent: tetrahydrofuran, flow rate: 3 ml / min, detector: RI, column temperature: room temperature, 500 mg of a sample and 200 mg of lauric acid (internal standard substance) were dissolved in 10 ml of tetrahydrofuran, and 60 μl of this solution was injected and analyzed. And the content of each ester was computed by correct | amending the area ratio of the peak area of each ester part and internal standard substance in the obtained chromatogram with relative sensitivity.
2.水溶液の透明性評価
上記で得られた各ショ糖脂肪酸エステルについて、4重量%水溶液を調製した。詳細には、各ショ糖脂肪酸エステルの粉末4重量部をイオン交換水96重量部に添加し、攪拌して80℃で溶解させた(T.K.ホモミキサー(特殊機化工業株式会社製)/ディスパー翼/1500rpm/15分)。その後、60℃まで冷却させて、下記評価基準に沿って目視で5段階にて透明性評価を行った。
2. Evaluation of Transparency of
評価基準は、透明な場合を「◎」、半透明な場合を「○」、微濁の場合を「△」、白濁の場合を「×」、不溶の場合を「××」とした。 The evaluation criteria were “」 ”for transparent,“ ◯ ”for translucent,“ Δ ”for slightly turbid,“ × ”for white turbid,“ xxx ”for insoluble.
結果は、下記表1及び図2に示す通りであり、トリエステル以上のポリエステル成分が35重量%を超えると、完全に透明溶解しなかった。また、ポリエステル成分が35重量%より多い場合、水に均一に分散、膨潤したとしても、時間とともに水相とショ糖脂肪酸エステルの膨潤した相に分離してしまった。 The results are as shown in Table 1 and FIG. 2 below. When the polyester component above the triester exceeded 35% by weight, it was not completely transparently dissolved. Further, when the amount of the polyester component was more than 35% by weight, even if the polyester component was uniformly dispersed and swollen in water, it separated into an aqueous phase and a sucrose fatty acid ester swollen phase with time.
3.水溶液の水分保持能評価
上記透明性評価で調製した4重量%水溶液を用いて、セイコーインスツル株式会社製熱分析システム「SSC/5200 TG/DTA220」にて、熱重量分析(TG)を実施した。熱履歴(昇温条件)を第1条件と第2条件の2つにした。
3. Evaluation of Water Retention Capacity of Aqueous Solution Using the 4 wt% aqueous solution prepared in the above-described transparency evaluation, thermogravimetric analysis (TG) was performed with a thermal analysis system “SSC / 5200 TG / DTA220” manufactured by Seiko Instruments Inc. . Two thermal histories (temperature raising conditions) were used, the first condition and the second condition.
第1条件は、30℃から80℃まで1℃/分で昇温するものである。サンプル量は約8mgに統一した。そして、得られた微分曲線から段階的な水分消失の有無を観察し、これを水分減量特性として、結果を表1及び図3に示した。表及び図中、「1」は重量の減少変化が1段階であること、「2」は2段階であること、「3」は3段階であることを示し、「2〜3」は2段階と3段階の中間的な減量挙動であることを示す。 The first condition is to raise the temperature from 30 ° C. to 80 ° C. at 1 ° C./min. The sample amount was unified to about 8 mg. And the presence or absence of the water | moisture content loss in steps was observed from the obtained differential curve, this was made into the moisture loss characteristic, and the result was shown in Table 1 and FIG. In the tables and figures, “1” indicates that the weight change is one step, “2” indicates two steps, “3” indicates three steps, and “2-3” indicates two steps. And 3 stages of intermediate weight loss behavior.
また、上記第1条件において、微分ピークから判断し、1段階目の水分蒸発から2段階目の水分蒸発に移行する点において残存している水分量(サンプルに使用した水を100とした時に、それに対して残存している水分の重量%)を算出した。結果を、表1(一段階後水分残量)及び図4に示す。 Further, in the first condition, the amount of water remaining at the point of transition from the first-stage moisture evaporation to the second-stage moisture evaporation as determined from the differential peak (when water used for the sample is 100, On the other hand, the remaining water (% by weight) was calculated. The results are shown in Table 1 (remaining moisture after one stage) and FIG.
第2条件は、40℃一定で1時間保持するものであり、保持した後に残存しているサンプル中の水分量(重量%)を測定した。サンプル量は約10mgに統一した。結果を、表1(定温試験水分残量)及び図5に示す。 The second condition is to hold at a constant temperature of 40 ° C. for 1 hour, and the moisture content (% by weight) in the sample remaining after holding was measured. The sample amount was unified to about 10 mg. The results are shown in Table 1 (constant temperature test moisture remaining amount) and FIG.
表1及び図3に示されるように、モノエステル成分が35重量%よりも多い範囲では、水分蒸散が段階的ではなかった。一般に、ラメラ相に取り込まれた水分は蒸発しにくく、それ以外の自由水は蒸発しやすいことから、1段階で水分が消失しているものは、ラメラ相への水分の取り込みがなく、自由水のみが存在していると考えられる。そのため、モノエステル成分が35重量%よりも多い範囲では、得られたラメラ相に十分な水分を取り込んでいるとは言えず、図4,5に示されるように、早期に水分が蒸散してしまうものであった。 As shown in Table 1 and FIG. 3, moisture transpiration was not stepwise in the range where the monoester component was more than 35% by weight. In general, the water taken in the lamellar phase is difficult to evaporate, and the other free water is easy to evaporate. Only is considered to exist. Therefore, in the range where the monoester component is more than 35% by weight, it cannot be said that sufficient moisture has been taken into the obtained lamellar phase, and as shown in FIGS. It was an end.
また、図5に示す定温試験での水分残量から明らかなように、ジエステル成分を55重量%以上とすることで、水分保持能がより顕著に向上していた。 Further, as apparent from the remaining amount of water in the constant temperature test shown in FIG. 5, the water retention ability was significantly improved by setting the diester component to 55% by weight or more.
4.乳化液の経時安定性評価
上記1で得られた各ショ糖脂肪酸エステルを乳化剤として用いて水中油型乳化液を調製した。乳化液の調製は、各ショ糖脂肪酸エステルの粉末4重量部をイオン交換水80重量部に添加し、攪拌して80℃で溶解させた(T.K.ホモミキサー(特殊機化工業株式会社製)/ディスパー翼/1500rpm/15分)。その後、大豆白絞油16重量部を添加し、乳化を行った(T.K.ホモミキサー(特殊機化工業株式会社製)/ホモミキサー翼/8000rpm/5分)。得られた乳化液を室温まで冷却した後、40℃に保存して、翌日(1日後)と5日後と7日後に乳化安定性を評価した。
4). Evaluation of stability of emulsion over time An oil-in-water emulsion was prepared using each sucrose fatty acid ester obtained in 1 above as an emulsifier. For the preparation of the emulsion, 4 parts by weight of each sucrose fatty acid ester powder was added to 80 parts by weight of ion-exchanged water, and the mixture was stirred and dissolved at 80 ° C. (TK homomixer (Special Machine Industries, Ltd. Manufactured) / disper blade / 1500 rpm / 15 minutes). Thereafter, 16 parts by weight of soybean white squeezed oil was added and emulsified (TK homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) / Homomixer blade / 8000 rpm / 5 minutes). The obtained emulsion was cooled to room temperature and then stored at 40 ° C., and the emulsion stability was evaluated the next day (after 1 day), 5 days, and 7 days.
評価基準は、安定性良好で均一な場合を「○」、わずかながら油脂分離が確認できた場合を「△」、油脂分離がはっきりと確認できた場合を「×」とした。 The evaluation criteria were “◯” when the stability was good and uniform, “Δ” when the oil separation was confirmed slightly, and “X” when the oil separation was clearly confirmed.
結果は、表1及び図6に示す通りであり、モノエステル:ジエステル:ポリエステル(トリエステル以上)=26〜35重量%:55〜65重量%:5〜14重量%の範囲内にある実施例のショ糖脂肪酸エステルでは、経時安定性が特異的に優れていた。
以上の結果から、ショ糖脂肪酸エステルのエステル組成を、モノエステル:ジエステル:ポリエステル=26〜35重量%:55〜65重量%:5〜14重量%とすることにより、水に溶解させたときの溶解性に優れるとともに、水分保持能力に優れ(従って、化粧品等の皮膚外用剤に用いたときの保湿性に優れ)、更には、水中油型乳化組成物の経時安定性を特異的に改善することができた。 From the above results, when the ester composition of sucrose fatty acid ester is monoester: diester: polyester = 26 to 35 wt%: 55 to 65 wt%: 5 to 14 wt%, when dissolved in water Excellent solubility and moisture retention ability (and therefore excellent moisturizing properties when used in skin preparations such as cosmetics), and specifically improves the temporal stability of oil-in-water emulsion compositions. I was able to.
本発明に係るショ糖脂肪酸エステルは、医薬品、化粧品、食品分野等における界面活性剤として利用することができ、特に、水中油型(O/W)乳化組成物を調製するための乳化剤として好適に用いられる。 The sucrose fatty acid ester according to the present invention can be used as a surfactant in the fields of pharmaceuticals, cosmetics, foods, etc., and is particularly suitable as an emulsifier for preparing an oil-in-water (O / W) emulsion composition. Used.
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