JP6322531B2 - Liquid composition for soft capsule filling - Google Patents

Liquid composition for soft capsule filling Download PDF

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JP6322531B2
JP6322531B2 JP2014187556A JP2014187556A JP6322531B2 JP 6322531 B2 JP6322531 B2 JP 6322531B2 JP 2014187556 A JP2014187556 A JP 2014187556A JP 2014187556 A JP2014187556 A JP 2014187556A JP 6322531 B2 JP6322531 B2 JP 6322531B2
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monoglyceride
fatty acid
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孝紀 安部
孝紀 安部
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Riken Vitamin Co Ltd
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Description

本発明は、ソフトカプセル充填用液状組成物に関する。   The present invention relates to a liquid composition for filling soft capsules.

難油溶性や粉末状の有効成分を含有するソフトカプセル剤は、一般に、有効成分を食用油脂に分散して調製した分散液を、ゼラチンを皮膜とするカプセルに充填して製造される。その際、有効成分を食用油脂中に安定に分散させるための分散剤として、従来グリセリン脂肪酸エステルやミツロウが使用されている(特許文献1参照)。   Soft capsules containing a hardly oil-soluble or powdery active ingredient are generally produced by filling a capsule having gelatin as a coating with a dispersion prepared by dispersing an active ingredient in edible fats and oils. At that time, glycerin fatty acid esters and beeswax have been conventionally used as dispersants for stably dispersing active ingredients in edible fats and oils (see Patent Document 1).

しかし、分散剤にミツロウを使用したソフトカプセル剤は、生体内での有効成分の溶出に難があり、有効成分の効果が生体内で十分に発揮されないおそれがあることが知られている。そこで、ミツロウを使用せず、反応モノグリセライドや蒸留モノグリセライド等の複数種類の乳化剤を組合せて使用することにより、食用油脂中に難油溶性成分を分散せしめたソフトカプセル充填用液状組成物(特許文献2〜5参照)等が提案されている。   However, it is known that soft capsules using beeswax as a dispersant have difficulty in elution of active ingredients in vivo, and the effects of active ingredients may not be sufficiently exhibited in vivo. Therefore, a liquid composition for filling soft capsules in which a hardly oil-soluble component is dispersed in edible fats and oils by using a combination of a plurality of emulsifiers such as reactive monoglyceride and distilled monoglyceride without using beeswax (Patent Documents 2 and 2). 5)) has been proposed.

しかし、上記ソフトカプセル充填用液状組成物は、食用油脂中の難油溶性成分の分散性において、なお改善の余地が残されている。また、このようなソフトカプセル充填用液状組成物には、保存中に硬度が上昇するものがある。一旦硬度が上昇すると、該組成物をソフトカプセルに充填するには、撹拌等により硬度を低減させる処理が必要になるため、製造効率の点から好ましくない。   However, the liquid composition for filling soft capsules still has room for improvement in the dispersibility of the hardly oil-soluble component in edible fats and oils. Some of these soft capsule filling liquid compositions have increased hardness during storage. Once the hardness is increased, filling the soft capsule with the composition requires a treatment to reduce the hardness by stirring or the like, which is not preferable from the viewpoint of production efficiency.

特開平7−138151号公報JP 7-138151 A 特開2009−079011号公報JP 2009-079011 A 特開2009−079012号公報JP 2009-079012 A 特開2009−242334号公報JP 2009-242334 A 特開2011−057566号公報JP 2011-057566 A

本発明は、食用油脂中に有効成分として難油溶性成分を分散せしめたソフトカプセル充填用液状組成物であって、食用油脂中での難油溶性成分の分散性がさらに改善され、且つ保存中の硬度の上昇が抑制されたソフトカプセル充填用液状組成物を提供することを課題とする。   The present invention is a liquid composition for filling soft capsules in which a hardly oil-soluble component is dispersed as an active ingredient in an edible oil and fat, the dispersibility of the hardly oil-soluble component in the edible oil and fat is further improved, and the composition is being stored It is an object of the present invention to provide a soft capsule filling liquid composition in which an increase in hardness is suppressed.

本発明者は、上記課題を解決するため、鋭意検討した結果、特定の4種類の食品用乳化剤を使用することにより、上記課題が解決されることを見出し、この知見に基づいて本発明をなすに至った。   As a result of intensive studies in order to solve the above problems, the present inventor has found that the above problems can be solved by using four specific types of food emulsifiers, and the present invention is made based on this finding. It came to.

即ち、本発明は、食用油脂中に難油溶性成分を分散せしめた組成物であって、食用油脂中に難油溶性成分を分散せしめた組成物であって、(a)主構成脂肪酸の炭素数が16〜20の反応モノグリセライド、(b)主構成脂肪酸の炭素数が22の反応モノグリセライド、(c)蒸留モノグリセライド及び(d)主構成脂肪酸の炭素数が22のポリグリセリン脂肪酸エステルを含有することを特徴とするソフトカプセル充填用液状組成物、
からなっている。
That is, the present invention is a composition in which a hardly oil-soluble component is dispersed in an edible oil and fat, and is a composition in which a hardly oil-soluble component is dispersed in an edible oil and fat, and (a) carbon of a main constituent fatty acid. A reaction monoglyceride having 16 to 20 carbon atoms, (b) a reaction monoglyceride having 22 carbon atoms in the main constituent fatty acid, (c) distilled monoglyceride, and (d) a polyglycerol fatty acid ester having 22 carbon atoms in the main constituent fatty acid. A liquid composition for filling soft capsules,
It is made up of.

本発明のソフトカプセル充填用液状組成物は、食用油脂中での難油溶性成分の分散安定性が良好である。
本発明のソフトカプセル充填用液状組成物は、保存中の硬度の上昇が抑制されているため、該組成物をソフトカプセルに充填するために硬度を低減させる処理が不要である。
The liquid composition for filling soft capsules of the present invention has good dispersion stability of the hardly oil-soluble component in edible fats and oils.
The liquid composition for filling soft capsules of the present invention suppresses the increase in hardness during storage, and therefore does not require a treatment for reducing the hardness in order to fill the soft capsules with the composition.

本発明で用いられる食用油脂としては、例えばコメ油、コーン油、キャノーラ油、オリーブ油、米ぬか油、大豆油、大豆白絞油、サフラワー油、ごま油、パーム油、パーム核油、やし油、ヒマワリ油、綿実油、菜種油、菜種白絞油、落花生油、グレープシード油、しそ油等の植物性油脂、牛脂、豚脂、魚油、乳脂又はラード等の動物性油脂、中鎖脂肪酸トリグリセリド(MCT)及びこれらのエステル交換油、分別油、水素添加油又はプロピレングリコールジ脂肪酸エステル等が挙げられる。これら食用油脂は、1種又は2種以上を任意に組み合わせて用いることができる。   Examples of edible oils and fats used in the present invention include rice oil, corn oil, canola oil, olive oil, rice bran oil, soybean oil, soybean white oil, safflower oil, sesame oil, palm oil, palm kernel oil, coconut oil, Sunflower oil, cottonseed oil, rapeseed oil, rapeseed white squeezed oil, vegetable oils such as peanut oil, grape seed oil, and perilla oil, animal fats such as beef fat, pork fat, fish oil, milk fat or lard, medium chain fatty acid triglyceride (MCT) And transesterified oils, fractionated oils, hydrogenated oils, propylene glycol difatty acid esters, and the like. These edible fats and oils can be used alone or in combination of two or more.

本発明で用いられる難油溶性成分は、親油性の低い物質から構成され、本発明のソフトカプセル充填用液状組成物の有効成分を構成するものである。具体的には、本発明における難油溶性成分とは、粉末の形態であって、食用油脂100gに該粉末1gを入れ20℃で混合したとき、30分以内に溶解しない物質を指すものとする。   The hardly oil-soluble component used in the present invention is composed of a substance having low lipophilicity and constitutes an active component of the liquid composition for filling soft capsules of the present invention. Specifically, the hardly oil-soluble component in the present invention refers to a substance that is in the form of powder and does not dissolve within 30 minutes when 1 g of the powder is added to 100 g of edible oil and fat and mixed at 20 ° C. .

このような難油溶性成分としては、例えば、ビタミン類(特にアスコルビン酸、ビタミンB1、B2、B6、B12等の水溶性ビタミン)、クエン酸、ヒアルロン酸、カルシウムパウダー等の栄養補助成分;ローヤルゼリーエキス末(粉末)、プロポリスエキス末、ブルーベリーエキス末、アガリクスエキス末、サメ軟骨抽出エキス末、ウコン末、イチョウ葉エキス末、ギムネマエキス末、その他の動植物粉末、乳糖、オリゴ糖、キトサン、食物繊維等の健康食品成分;或いは生薬エキス末、漢方、医薬組成物等の薬効成分が挙げられる。これら難油溶性成分は1種又は2種以上を任意に組み合わせて用いることができる。   Examples of such hardly oil-soluble ingredients include vitamins (especially water-soluble vitamins such as ascorbic acid, vitamins B1, B2, B6, and B12), nutritional supplements such as citric acid, hyaluronic acid, and calcium powder; royal jelly extract Powder (Powder), Propolis Extract Powder, Blueberry Extract Powder, Agaricus Extract Powder, Shark Cartilage Extract Extract Powder, Turmeric Powder, Ginkgo Leaf Extract Powder, Gymnema Extract Powder, Other Animal and Plant Powders, Lactose, Oligosaccharide, Chitosan, Dietary Fiber, etc. Or other medicinal ingredients such as herbal extract powder, Chinese medicine, and pharmaceutical compositions. These hardly oil-soluble components can be used alone or in combination of two or more.

本発明で言うところの反応モノグリセライドは、グリセリンと脂肪酸とのエステル化反応生成物又はグリセリンと油脂(トリグリセライド)とのエステル交換反応生成物から未反応のグリセリンを可及的に除去したものであって、モノグリセライド(グリセリンモノ脂肪酸エステル)、ジグリセライド(グリセリンジ脂肪酸エステル)及びトリグリセライド(グリセリントリ脂肪酸エステル)を含有する混合物である。該反応モノグリセライド100%中のモノグリセライドの含有量は、通常40〜60%であり、好ましくは45〜55%である。また、反応モノグリセライド100%中のジグリセライドの含有量は、通常25〜45%であり、好ましくは35〜45%である。反応モノグリセライド100%中のトリグリセライドの含有量は、通常1〜15%であり、好ましくは1〜10%である。   The reaction monoglyceride referred to in the present invention is obtained by removing as much as possible unreacted glycerin from the esterification reaction product of glycerin and fatty acid or the transesterification reaction product of glycerin and fat (triglyceride). , Monoglyceride (glycerin monofatty acid ester), diglyceride (glycerin difatty acid ester) and triglyceride (glycerin trifatty acid ester). The content of monoglyceride in 100% of the reaction monoglyceride is usually 40 to 60%, preferably 45 to 55%. The content of diglyceride in 100% of the reaction monoglyceride is usually 25 to 45%, preferably 35 to 45%. The content of triglyceride in 100% of the reaction monoglyceride is usually 1 to 15%, preferably 1 to 10%.

上記反応モノグリセライドの組成、すなわち反応モノグリセライド中のモノグリセライド、ジグリセライド及びトリグリセライドの含有量は、反応モノグリセライドをHPLC(高速液体クロマトグラフィー)で分析することにより求められる。具体的には、以下に示す分析条件にて反応モグリセライドを分析し、分析後、データ処理装置によりクロマトグラム上に記録された被検試料の各成分に対応するピークについて、積分計を用いてピーク面積を測定する。測定されたピーク面積に基づいて、面積百分率としてモノグリセライド含有量、ジグリセライド含有量及びトリグリセライド含有量を求めることができる。
HPLC分析条件を以下に示す。
The composition of the reaction monoglyceride, that is, the contents of monoglyceride, diglyceride and triglyceride in the reaction monoglyceride can be determined by analyzing the reaction monoglyceride by HPLC (high performance liquid chromatography). Specifically, the reaction moglyceride is analyzed under the analysis conditions shown below, and after the analysis, the peak corresponding to each component of the test sample recorded on the chromatogram by the data processor is used with an integrator. Measure the peak area. Based on the measured peak area, the monoglyceride content, the diglyceride content, and the triglyceride content can be obtained as area percentages.
The HPLC analysis conditions are shown below.

(HPLC分析条件)
装置:島津高速液体クロマトグラフ
データ処理ソフトウェア(型式:LCsolution ver.1.0;島津製作所社製)
ポンプ(型式:LC−20AD;島津製作所社製)
カラムオーブン(型式:CTO−20A;島津製作所社製)
オートサンプラ(型式:SIL−20A;島津製作所社製)
検出器:RI検出器(型式:RID−10A;島津製作所社製)
カラム:GPCカラム(型式:SHODEX KF−801;昭和電工社製)及びGPCカラム(型式:SHODEX KF−802;昭和電工社製)の2本連結
移動相:THF(テトラヒドロフラン)
流量:1.0mL/min
カラム温度:40℃
サンプル濃度:0.01g/1mLTHF
サンプル注入量:20μL(in THF)
(HPLC analysis conditions)
Apparatus: Shimadzu high-performance liquid chromatograph data processing software (model: LC solution ver. 1.0; manufactured by Shimadzu Corporation)
Pump (Model: LC-20AD; manufactured by Shimadzu Corporation)
Column oven (model: CTO-20A; manufactured by Shimadzu Corporation)
Autosampler (model: SIL-20A; manufactured by Shimadzu Corporation)
Detector: RI detector (model: RID-10A; manufactured by Shimadzu Corporation)
Column: GPC column (model: SHODEX KF-801; manufactured by Showa Denko KK) and GPC column (model: SHODEX KF-802; manufactured by Showa Denko KK), two-linked mobile phase: THF (tetrahydrofuran)
Flow rate: 1.0 mL / min
Column temperature: 40 ° C
Sample concentration: 0.01 g / 1 mL THF
Sample injection volume: 20 μL (in THF)

上記反応モノグリセライドの製法としては、例えば、(1)グリセリンと油脂とのエステル交換反応による製法、(2)グリセリンと脂肪酸とのエステル化反応による製法が挙げられる。これら製法の概略を、以下の(1)及び(2)にそれぞれ示す。   As a manufacturing method of the said reaction monoglyceride, the manufacturing method by (1) esterification reaction of glycerol and fats and oils and (2) the manufacturing method by esterification reaction of glycerol and a fatty acid are mentioned, for example. The outline of these production methods is shown in the following (1) and (2), respectively.

(1)エステル交換反応による反応モノグリセライドの製法
例えば、撹拌機、加熱用のジャケット、邪魔板等を備えた通常の反応容器に、グリセリン及び油脂を2:1のモル比で仕込み、通常触媒として、例えば水酸化ナトリウムを加えて撹拌混合し、窒素ガス雰囲気下、例えば180〜260℃、好ましくは200〜250℃で、0.5〜15時間、好ましくは1〜3時間加熱してエステル交換反応を行う。反応圧力条件は、常圧下又は減圧下が好ましい。得られた反応液は、グリセリン、モノグリセライド、ジグリセライド、トリグリセライド等を含む混合物である。
反応終了後、反応液中に残存する触媒を中和し、次に反応液を、好ましくは、減圧下で蒸留して残存するグリセリンを留去し、必要であれば脱塩、脱色、ろ過等の処理を行い、最終的に、全体に対してモノグリセライドを40〜60%、ジグリセライドを25〜45%含む反応モノグリセライドを得る。
(1) Production method of reaction monoglyceride by transesterification For example, in a normal reaction vessel equipped with a stirrer, a heating jacket, a baffle plate, etc., glycerin and fats and oils are charged in a molar ratio of 2: 1. For example, sodium hydroxide is added and stirred and mixed, and the ester exchange reaction is carried out by heating at a temperature of 180 to 260 ° C., preferably 200 to 250 ° C., for 0.5 to 15 hours, preferably 1 to 3 hours in a nitrogen gas atmosphere. Do. The reaction pressure condition is preferably normal pressure or reduced pressure. The obtained reaction liquid is a mixture containing glycerin, monoglyceride, diglyceride, triglyceride and the like.
After completion of the reaction, the catalyst remaining in the reaction solution is neutralized, and then the reaction solution is preferably distilled under reduced pressure to distill off the remaining glycerin. If necessary, desalting, decolorization, filtration, etc. Finally, a reaction monoglyceride containing 40-60% monoglyceride and 25-45% diglyceride is obtained.

(2)エステル化反応による反応モノグリセライドの製法
例えば、撹拌機、加熱用のジャケット、邪魔板等を備えた通常の反応容器にグリセリン及び脂肪酸を1:1のモル比で仕込み、必要に応じ酸又はアルカリを触媒として添加し、窒素又は二酸化炭素等の任意の不活性ガス雰囲気下で、例えば180〜260℃の範囲、好ましくは200〜250℃で0.5〜5時間、好ましくは1〜3時間加熱してエステル化反応を行う。得られた反応液は、グリセリン、モノグリセライド、ジグリセライド、トリグリセライド等を含む混合物である。
反応終了後、反応液中に残存する触媒を中和し、次に反応液を、好ましくは、減圧下で蒸留して残存するグリセリンを留去し、必要であれば脱塩、脱色、ろ過等の処理を行い、最終的に、全体に対してモノグリセライドを40〜60%、ジグリセライドを25〜45%含む反応モノグリセライドを得る。
(2) Production method of reaction monoglyceride by esterification reaction For example, a normal reaction vessel equipped with a stirrer, a heating jacket, a baffle plate and the like is charged with glycerin and fatty acid at a molar ratio of 1: 1, and an acid or Alkali is added as a catalyst and under any inert gas atmosphere such as nitrogen or carbon dioxide, for example in the range of 180-260 ° C, preferably 200-250 ° C for 0.5-5 hours, preferably 1-3 hours. Esterification reaction is performed by heating. The obtained reaction liquid is a mixture containing glycerin, monoglyceride, diglyceride, triglyceride and the like.
After completion of the reaction, the catalyst remaining in the reaction solution is neutralized, and then the reaction solution is preferably distilled under reduced pressure to distill off the remaining glycerin. If necessary, desalting, decolorization, filtration, etc. Finally, a reaction monoglyceride containing 40-60% monoglyceride and 25-45% diglyceride is obtained.

本発明においては、上記反応モノグリセライドの中でも、主構成脂肪酸の炭素数が16〜20の反応モノグリセライド及び主構成脂肪酸の炭素数が22の反応モノグリセライドを組合せて用いられる。主構成脂肪酸の炭素数が16〜20の反応モノグリセライドとしては、例えば主構成脂肪酸がパルミチン酸(炭素数16)の反応モノグリセライド、主構成脂肪酸がステアリン酸(炭素数18)の反応モノグリセライド、主構成脂肪酸がアラキジン酸(炭素数20)の反応モノグリセライド等が挙げられ、中でも、主構成脂肪酸がパルミチン酸及び/又はステアリン酸の反応モノグリセライドが好ましい。また、主構成脂肪酸の炭素数が22の反応モノグリセライドとしては、主構成脂肪酸がベヘン酸の反応モノグリセライドが挙げられる。   In the present invention, among the above-mentioned reaction monoglycerides, a reaction monoglyceride having 16 to 20 carbon atoms in the main constituent fatty acid and a reaction monoglyceride having 22 carbon atoms in the main constituent fatty acid are used in combination. Examples of the reactive monoglyceride having 16 to 20 carbon atoms in the main constituent fatty acid include, for example, a reactive monoglyceride in which the main constituent fatty acid is palmitic acid (16 carbon atoms), a reactive monoglyceride in which the main constituent fatty acid is stearic acid (18 carbon atoms), and a main constituent fatty acid. Is a reaction monoglyceride of arachidic acid (carbon number 20). Among them, a reaction monoglyceride in which the main constituent fatty acid is palmitic acid and / or stearic acid is preferable. Moreover, as a reaction monoglyceride whose carbon number of a main constituent fatty acid is 22, the reaction monoglyceride whose main constituent fatty acid is behenic acid is mentioned.

本発明において、反応モノグリセライドについて「主構成脂肪酸」とは、反応モノグリセライドを構成する全脂肪酸100質量%中、60質量%以上、好ましくは75質量%以上を占める脂肪酸をいう。従って、例えば主構成脂肪酸の炭素数16〜18の反応モノグリセライドは、該反応モノグリセライドを構成する全脂肪酸100質量%中、炭素数16〜18の範囲に含まれる脂肪酸が60質量%以上を占めるものを意味する。同様に、主構成脂肪酸の炭素数18の反応モノグリセライドは、該反応モノグリセライドを構成する全脂肪酸100質量%中、炭素数18の脂肪酸(即ち、ステアリン酸等)が60質量%以上を占めるものを意味する。また、後述の蒸留モノグリセライド及びポリグリセリン脂肪酸エステルについての「主構成脂肪酸」の定義もこれと同じである。   In the present invention, the “main constituent fatty acid” in the reaction monoglyceride means a fatty acid occupying 60% by mass or more, preferably 75% by mass or more, in 100% by mass of the total fatty acids constituting the reaction monoglyceride. Therefore, for example, the reaction monoglyceride having 16 to 18 carbon atoms of the main constituent fatty acid is one in which the fatty acid contained in the range of 16 to 18 carbon atoms occupies 60 mass% or more in 100 mass% of all fatty acids constituting the reaction monoglyceride. means. Similarly, the reaction monoglyceride having 18 carbon atoms of the main constituent fatty acid means that the fatty acid having 18 carbon atoms (that is, stearic acid, etc.) accounts for 60 mass% or more in 100 mass% of the total fatty acids constituting the reaction monoglyceride. To do. The definition of “main constituent fatty acid” for the distilled monoglyceride and polyglycerin fatty acid ester described later is the same as this.

主構成脂肪酸の炭素数が16〜20の反応モノグリセライドとしては、例えば、ポエムP−200(製品名;主構成脂肪酸の炭素数16〜18;モノグリセライド含有量約52%;理研ビタミン社製)、ポエムV−200(製品名;主構成脂肪酸の炭素数18;モノグリセライド含有量約50%;理研ビタミン社製)等が商業的に製造及び販売されており、本発明ではこれらの市販品を用いることができる。また、主構成脂肪酸の炭素数が22の反応モノグリセライドとしては、ポエムB−200(製品名;モノグリセライド含有量約47%;理研ビタミン社製)等が商業的に製造及び販売されており、本発明ではこれらの市販品を用いることができる。   Examples of the reaction monoglyceride having 16 to 20 carbon atoms of the main constituent fatty acid include Poem P-200 (product name; 16 to 18 carbon atoms of the main constituent fatty acid; monoglyceride content: about 52%; manufactured by Riken Vitamin Co., Ltd.), Poem V-200 (product name; carbon number of main constituent fatty acid: 18; monoglyceride content: about 50%; manufactured by Riken Vitamin Co., Ltd.) and the like are commercially produced and sold. In the present invention, these commercially available products may be used. it can. In addition, as the reaction monoglyceride having 22 carbon atoms in the main constituent fatty acid, Poem B-200 (product name; monoglyceride content: about 47%; manufactured by Riken Vitamin Co., Ltd.) is commercially produced and sold. Then, these commercially available products can be used.

本発明で用いられる蒸留モノグリセライドは、上述した製法により得られる反応モノグリセライドを精製し、モノグリセライドの含有量を高めたものである。該蒸留モノグリセライド100%中のモノグリセライドの含有量は、通常90%以上である。本発明で用いられる蒸留モノグリセライドを構成する脂肪酸に特に制限はないが、例えば食用可能な動植物油脂を起源とする炭素数6〜24の直鎖の飽和脂肪酸(例えば、カプロン酸、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、アラキジン酸、ベヘン酸、リグノセリン酸)等が好ましく、より好ましくはパルミチン酸、ステアリン酸、ベヘン酸である。   The distilled monoglyceride used in the present invention is obtained by purifying the reaction monoglyceride obtained by the above-described production method and increasing the monoglyceride content. The content of monoglyceride in 100% of the distilled monoglyceride is usually 90% or more. Although there is no restriction | limiting in particular in the fatty acid which comprises the distilled monoglyceride used by this invention, For example, a C6-C24 linear saturated fatty acid (for example, caproic acid, caprylic acid, capric acid originated from edible animal and vegetable fats and oils) Lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid) and the like, more preferably palmitic acid, stearic acid, and behenic acid.

上記蒸留モノグリセライド100%中のモノグリセライドの含有量は、上記分析条件にてHPLCを用いて分析することにより求められる。具体的には、蒸留モノグリセライドを上記HPLC分析条件で分析後、データ処理装置によりクロマトグラム上に記録された被検試料の各成分に対応するピークについて、積分計を用いてピーク面積を測定し、測定されたピーク面積に基づいて、面積百分率としてモノグリセライドの含有量を求めることができる。   The content of monoglyceride in 100% of the distilled monoglyceride is determined by analyzing using HPLC under the above analysis conditions. Specifically, after analyzing the distilled monoglyceride under the above HPLC analysis conditions, the peak area corresponding to each component of the test sample recorded on the chromatogram by the data processor is measured using an integrator, Based on the measured peak area, the monoglyceride content can be determined as an area percentage.

本発明で用いられる蒸留モノグリセライドは、上述した反応モノグリセライドを精製することにより製造することができる。精製方法としては、例えば流下薄膜式分子蒸留装置又は遠心式分子蒸留装置等を用いて真空蒸留する方法が挙げられる。これらの方法を用いて精製することにより、モノグリセライドを全体の90%以上含む蒸留モノグリセライドを得ることができる。該蒸留モノグリセライド中のモノグリセライド含有量の上限は、通常99%程度である。   The distilled monoglyceride used in the present invention can be produced by purifying the above-described reaction monoglyceride. Examples of the purification method include a vacuum distillation method using a falling film molecular distillation apparatus or a centrifugal molecular distillation apparatus. By purifying using these methods, a distilled monoglyceride containing 90% or more of the whole monoglyceride can be obtained. The upper limit of the monoglyceride content in the distilled monoglyceride is usually about 99%.

蒸留モノグリセライドとしては、例えば、エマルジーP−100(製品名;主構成脂肪酸の炭素数16〜18;モノグリセライド含有量約98%;理研ビタミン社製)、ポエムS−100(製品名;主構成脂肪酸の炭素数18;モノグリセライド含有量約98%;理研ビタミン社製)、ポエムB−100(製品名;主構成脂肪酸の炭素数22;モノグリセライド含有量約96%;理研ビタミン社製)等が商業的に製造及び販売されており、本発明ではこれらを用いることができる。   Examples of the distilled monoglyceride include Emulsy P-100 (product name: 16 to 18 carbon atoms of main constituent fatty acid; monoglyceride content: about 98%; manufactured by Riken Vitamin Co., Ltd.), Poem S-100 (product name: main constituent fatty acid) Carbon number 18; monoglyceride content about 98%; manufactured by Riken Vitamin Co., Ltd.), Poem B-100 (product name; carbon number 22 of main constituent fatty acid; monoglyceride content about 96%; manufactured by Riken Vitamin Co., Ltd.) These are manufactured and sold and can be used in the present invention.

本発明で用いられる主構成脂肪酸の炭素数が22のポリグリセリン脂肪酸エステルは、ポリグリセリンとベヘン酸とのエステル化反応生成物であり、エステル化反応など自体公知の方法で製造され得る。   The polyglycerol fatty acid ester having 22 carbon atoms of the main constituent fatty acid used in the present invention is an esterification reaction product of polyglycerol and behenic acid and can be produced by a method known per se such as an esterification reaction.

本発明で用いられる主構成脂肪酸の炭素数が22のポリグリセリン脂肪酸エステルの原料として用いられるポリグリセリンとしては、通常グリセリンに少量の酸またはアルカリを触媒として添加し、窒素または二酸化炭素などの任意の不活性ガス雰囲気下で、例えば約180℃以上の温度で加熱し、重縮合反応させて得られる重合度の異なるポリグリセリンの混合物が挙げられる。また、ポリグリセリンは、グリシドールまたはエピクロルヒドリンなどを原料として得られるものであっても良い。反応終了後、必要であれば中和、脱塩または脱色などの処理を行って良い。該ポリグリセリンとしては、グリセリンの平均重合度が通常約2〜20、好ましくは約2〜15のポリグリセリンが挙げられる。具体的には、例えばジグリセリン(平均重合度:約2.0)、トリグリセリン(平均重合度:約3.0)、テトラグリセリン(平均重合度:約4.0)、ヘキサグリセリン(平均重合度:約6.0)、オクタグリセリン(平均重合度:約8.0)およびデカグリセリン(平均重合度:約10.0)などが挙げられ、特にトリグリセリンおよびテトラグリセリンが好ましい。   As the polyglycerol used as a raw material of the polyglycerol fatty acid ester having 22 carbon atoms of the main constituent fatty acid used in the present invention, a small amount of acid or alkali is usually added to glycerol as a catalyst, and any of nitrogen, carbon dioxide and the like For example, a mixture of polyglycerin having different degrees of polymerization obtained by heating at a temperature of about 180 ° C. or higher under an inert gas atmosphere to cause a polycondensation reaction may be mentioned. Polyglycerin may be obtained using glycidol or epichlorohydrin as a raw material. After completion of the reaction, a treatment such as neutralization, desalting or decolorization may be performed if necessary. Examples of the polyglycerin include polyglycerin having an average degree of polymerization of glycerin of usually about 2 to 20, preferably about 2 to 15. Specifically, for example, diglycerin (average polymerization degree: about 2.0), triglycerin (average polymerization degree: about 3.0), tetraglycerin (average polymerization degree: about 4.0), hexaglycerin (average polymerization) Degree: about 6.0), octaglycerin (average degree of polymerization: about 8.0), decaglycerin (average degree of polymerization: about 10.0) and the like, and triglycerin and tetraglycerin are particularly preferred.

本発明で用いられる主構成脂肪酸の炭素数が22のポリグリセリン脂肪酸エステルの原料として用いられるベヘン酸としては、特に制限はないが、純度が50%以上のものが好ましい。純度が50%以上であると、難油溶性成分の分散安定性が十分に得られる。   The behenic acid used as a raw material for the polyglycerol fatty acid ester having 22 carbon atoms of the main constituent fatty acid used in the present invention is not particularly limited, but preferably has a purity of 50% or more. When the purity is 50% or more, sufficient dispersion stability of the hardly oil-soluble component can be obtained.

本発明で用いられる主構成脂肪酸の炭素数が22のポリグリセリン脂肪酸エステルの好ましい製法の概略は以下の通りである。例えば、ポリグリセリンとしてトリグリセリンを用いる場合、攪拌機、加熱用のジャケット、邪魔板などを備えた通常の反応容器に、トリグリセリンとベヘン酸を約1:2〜1:3のモル比で仕込み、通常触媒として水酸化ナトリウムを加えて攪拌混合し、窒素ガス雰囲気下で、エステル化反応により生成する水を系外に除去しながら、所定温度で加熱する。反応温度は通常、180〜260℃の範囲、好ましくは200〜250℃の範囲である。また、反応圧力条件は常圧下または減圧下で、反応時間は0.5〜15時間、好ましくは1〜3時間である。反応の終点は、通常反応混合物の酸価を測定し、約12以下を目安に決められる。   The outline of the preferable manufacturing method of the polyglycerol fatty acid ester whose carbon number of the main constituent fatty acid used in the present invention is 22 is as follows. For example, when triglycerin is used as polyglycerin, triglycerin and behenic acid are charged in a molar ratio of about 1: 2 to 1: 3 in a normal reaction vessel equipped with a stirrer, a heating jacket, a baffle plate, and the like. Usually, sodium hydroxide is added as a catalyst and stirred and mixed, and heated at a predetermined temperature in a nitrogen gas atmosphere while removing water generated by the esterification reaction out of the system. The reaction temperature is usually in the range of 180 to 260 ° C, preferably in the range of 200 to 250 ° C. The reaction pressure condition is normal pressure or reduced pressure, and the reaction time is 0.5 to 15 hours, preferably 1 to 3 hours. The end point of the reaction is usually determined by measuring the acid value of the reaction mixture and about 12 or less.

エステル化反応終了後、必要に応じて反応混合物中に残存する触媒を中和し、必要であれば脱塩、脱色、ろ過などの処理を行い、最終的に、本発明の主構成脂肪酸の炭素数が22のポリグリセリン脂肪酸エステルを得る。   After completion of the esterification reaction, the catalyst remaining in the reaction mixture is neutralized as necessary, and if necessary, treatments such as desalting, decoloring, and filtration are performed, and finally, the carbon of the main constituent fatty acid of the present invention A polyglycerol fatty acid ester of 22 is obtained.

主構成脂肪酸の炭素数が22のポリグリセリン脂肪酸エステルとしては、例えば、ポエムHB(商品名;トリグリセリン脂肪酸エステル;理研ビタミン社製)、ポエムJ−46B(商品名;テトラグリセリン脂肪酸エステル;理研ビタミン社製)等が商業的に製造及び販売されており、本発明ではこれらを用いることができる。   Examples of the polyglycerol fatty acid ester having 22 main constituent fatty acids include Poem HB (trade name; triglycerin fatty acid ester; manufactured by Riken Vitamin Co., Ltd.), Poem J-46B (trade name; tetraglycerin fatty acid ester; RIKEN vitamin) Etc.) are commercially produced and sold, and these can be used in the present invention.

本発明のソフトカプセル充填用液状組成物は、本発明の効果を奏する限り、必要に応じて上記食用油脂、難油溶性成分、主構成脂肪酸の炭素数が16〜20の反応モノグリセライド、主構成脂肪酸の炭素数が22の反応モノグリセライド、蒸留モノグリセライド及び主構成脂肪酸の炭素数が22のポリグリセリン脂肪酸エステル以外のその他の成分を含んでもよい。   As long as the liquid composition for filling soft capsules of the present invention exhibits the effects of the present invention, the edible oil and fat, the hardly oil-soluble component, the reactive monoglyceride having 16 to 20 carbon atoms of the main constituent fatty acid, Other components other than the reaction monoglyceride having 22 carbon atoms, the distilled monoglyceride, and the polyglycerol fatty acid ester having 22 carbon atoms of the main constituent fatty acid may be included.

その他の成分としては、モノエステル体含有量が50%以上のジグリセリン脂肪酸エステル、酸化防止剤(例えば、抽出トコフェロール、アスコルビン酸パルミチン酸エステル)等が挙げられる。その他の成分は1種又は2種以上を組み合わせて用いることができる。   Examples of other components include diglycerin fatty acid esters having a monoester content of 50% or more, antioxidants (for example, extracted tocopherol, ascorbyl palmitate), and the like. Other components can be used alone or in combination of two or more.

なお、その他の成分として、上記モノエステル体含有量が50%以上のジグリセリン脂肪酸エステルを本発明のソフトカプセル充填用液状組成物に使用すると、該組成物を充填したソフトカプセル剤を摂取した際に、胃液中で難油溶性成分が容易に分散し、生体内への有効成分の吸収促進が期待できるため好ましい。   In addition, when the diglycerin fatty acid ester having a monoester content of 50% or more is used as the other component in the soft capsule filling liquid composition of the present invention, when the soft capsule filled with the composition is ingested, It is preferable because the hardly oil-soluble component is easily dispersed in the gastric juice and the absorption of the active ingredient into the living body can be expected to be accelerated.

本発明のソフトカプセル充填用液状組成物は、上記食用油脂、難油溶性成分、主構成脂肪酸の炭素数が16〜20の反応モノグリセライド、主構成脂肪酸の炭素数が22の反応モノグリセライド、蒸留モノグリセライド、主構成脂肪酸の炭素数が22のポリグリセリン脂肪酸エステル及び必要に応じてモノエステル体含有量が50%以上のジグリセリン脂肪酸エステルを混合及び撹拌しながら、これらの成分を均一に分散させることにより製造される。具体的には、例えば、食用油脂、主構成脂肪酸の炭素数が16〜20の反応モノグリセライド、主構成脂肪酸の炭素数が22の反応モノグリセライド、蒸留モノグリセライド、主構成脂肪酸の炭素数が22のポリグリセリン脂肪酸エステル及び必要に応じてモノエステル体含有量が50%以上のジグリセリン脂肪酸エステルを、例えば、60〜90℃、好ましくは70〜80℃に加熱して均一に混合及び撹拌して溶解液を調製した後、該溶解液を例えば40〜60℃に冷却し、更に難油溶性成分を加えて混合及び撹拌し、該難油溶性成分を均一に分散して製造される。なお、主構成脂肪酸の炭素数が16〜20の反応モノグリセライド、主構成脂肪酸の炭素数が22の反応モノグリセライド、蒸留モノグリセライド、主構成脂肪酸の炭素数が22のポリグリセリン脂肪酸エステル及びモノエステル体含有量が50%以上のジグリセリン脂肪酸エステルは、これらを予め混合し、加熱して溶融させたものを使用することができる。混合及び撹拌するための装置に特に制限はないが、例えば、バイオミキサー、ホモジェッター等の高速撹拌機又は高速粉砕機を用いることができる。   The liquid composition for filling soft capsules of the present invention comprises the above edible oil and fat, a hardly oil-soluble component, a reactive monoglyceride having 16 to 20 carbon atoms in the main constituent fatty acid, a reactive monoglyceride having 22 carbon atoms in the main constituent fatty acid, a distilled monoglyceride, It is produced by uniformly dispersing these components while mixing and stirring a polyglycerol fatty acid ester having 22 carbon atoms in the constituent fatty acid and, if necessary, a diester fatty acid ester having a monoester content of 50% or more. The Specifically, for example, edible fats and oils, a reaction monoglyceride having 16 to 20 carbon atoms in the main constituent fatty acid, a reaction monoglyceride having 22 carbon atoms in the main constituent fatty acid, a distilled monoglyceride, and a polyglycerol having 22 carbon atoms in the main constituent fatty acid. Fatty acid esters and diglycerin fatty acid esters having a monoester content of 50% or more as necessary are heated to, for example, 60 to 90 ° C., preferably 70 to 80 ° C., and uniformly mixed and stirred to obtain a solution. After the preparation, the solution is cooled to 40 to 60 ° C., for example, and the hardly oil-soluble component is added, mixed and stirred, and the hardly oil-soluble component is uniformly dispersed. In addition, the reaction monoglyceride having 16 to 20 carbon atoms of the main constituent fatty acid, the reaction monoglyceride having 22 carbon atoms of the main constituent fatty acid, the distilled monoglyceride, the polyglycerol fatty acid ester having the main constituent fatty acid of 22 carbon atoms, and the monoester content However, the diglycerin fatty acid ester of 50% or more may be prepared by mixing these in advance and heating and melting them. Although there is no restriction | limiting in particular in the apparatus for mixing and stirring, For example, high-speed stirrers, such as a biomixer and a homojetter, or a high-speed grinder can be used.

本発明のソフトカプセル充填用液状組成物100質量%中の食用油脂の含有量は特に限定されないが、例えば、通常20〜95質量%、好ましくは25〜90質量%、より好ましくは30〜80質量%である。本発明において食用油脂の含有量が上記範囲であれば、難油溶性成分を食用油脂中に十分に分散させることができるとともに、食用油脂中における難油溶性成分の分散安定性が良好である。   The content of the edible fat / oil in 100% by mass of the liquid composition for filling soft capsules of the present invention is not particularly limited, but is usually 20 to 95% by mass, preferably 25 to 90% by mass, and more preferably 30 to 80% by mass. It is. In the present invention, if the content of the edible oil / fat is in the above range, the hardly oil-soluble component can be sufficiently dispersed in the edible oil / fat, and the dispersion stability of the hardly oil-soluble component in the edible oil / fat is good.

本発明のソフトカプセル充填用液状組成物100質量%中の難油溶性成分の含有量は、特に限定されないが、例えば、通常1〜70質量%、好ましくは3〜60質量%、より好ましくは10〜50質量%である。本発明において難油溶性成分の含有量が上記範囲であれば、難油溶性成分を食用油脂中に十分に分散させることができる。また、食用油脂中での難油溶性成分の分散安定性が良好であるため、ソフトカプセル剤中で難油溶性成分の分離が生じない。   The content of the hardly oil-soluble component in 100% by mass of the liquid composition for filling soft capsules of the present invention is not particularly limited, but is usually 1 to 70% by mass, preferably 3 to 60% by mass, more preferably 10 to 10% by mass. 50% by mass. If content of a hardly oil-soluble component is the said range in this invention, a hardly oil-soluble component can fully be disperse | distributed in edible fats and oils. Moreover, since the dispersion stability of the hardly oil-soluble component in the edible fat is good, the hardly oil-soluble component is not separated in the soft capsule.

本発明のソフトカプセル充填用液状組成物100質量%中の主構成脂肪酸の炭素数が16〜20の反応モノグリセライドの含有量は、特に限定されないが、例えば、通常0.25〜14質量%、好ましくは0.25〜10質量%、より好ましくは0.5〜8質量%である。本発明において該反応モノグリセライドの含有量が上記範囲であれば、食用油脂中での難油溶性成分の分散安定性が良好であるため、ソフトカプセル剤中で難油溶性成分の分離が生じない。また、ソフトカプセル充填用液状組成物の保存中における硬度の上昇が抑制され、該組成物をソフトカプセルに充填する工程が容易になる。   The content of the reaction monoglyceride having 16 to 20 carbon atoms of the main constituent fatty acid in 100% by mass of the liquid composition for filling soft capsules of the present invention is not particularly limited, but is usually 0.25 to 14% by mass, preferably, for example. It is 0.25-10 mass%, More preferably, it is 0.5-8 mass%. In the present invention, if the content of the reactive monoglyceride is in the above range, the dispersion stability of the hardly oil-soluble component in the edible fat is good, so that the hardly oil-soluble component is not separated in the soft capsule. In addition, an increase in hardness during storage of the liquid composition for filling soft capsules is suppressed, and the process of filling the soft capsules with the composition becomes easy.

本発明のソフトカプセル充填用液状組成物100質量%中の主構成脂肪酸の炭素数が22の反応モノグリセライドの含有量は、特に限定されないが、例えば、通常0.25〜14質量%、好ましくは0.25〜10質量%、より好ましくは0.5〜8質量%である。本発明において該反応モノグリセライドの含有量が上記範囲であれば、食用油脂中での難油溶性成分の分散安定性が良好であるため、ソフトカプセル剤中で難油溶性成分の分離が生じない。また、ソフトカプセル充填用液状組成物の保存中における硬度の上昇が抑制され、該組成物をソフトカプセルに充填する工程が容易になる。   The content of the reaction monoglyceride having 22 carbon atoms of the main constituent fatty acid in 100% by mass of the liquid composition for filling soft capsules of the present invention is not particularly limited, but is usually 0.25 to 14% by mass, preferably 0.00. It is 25-10 mass%, More preferably, it is 0.5-8 mass%. In the present invention, if the content of the reactive monoglyceride is in the above range, the dispersion stability of the hardly oil-soluble component in the edible fat is good, so that the hardly oil-soluble component is not separated in the soft capsule. In addition, an increase in hardness during storage of the liquid composition for filling soft capsules is suppressed, and the process of filling the soft capsules with the composition becomes easy.

本発明のソフトカプセル充填用液状組成物100質量%中の蒸留モノグリセライドの含有量は、特に限定されないが、例えば、通常0.5〜15質量%、好ましくは0.5〜10質量%、より好ましくは1〜8質量%である。本発明において該蒸留モノグリセライドの含有量が上記範囲であれば、食用油脂中での難油溶性成分の分散安定性が良好であるため、ソフトカプセル剤中で難油溶性成分の分離が生じない。また、ソフトカプセル充填用液状組成物の保存中における硬度の上昇が抑制され、該組成物をソフトカプセルに充填する工程が容易になる。   The content of the distilled monoglyceride in 100% by mass of the liquid composition for filling soft capsules of the present invention is not particularly limited, but is usually 0.5 to 15% by mass, preferably 0.5 to 10% by mass, and more preferably. 1 to 8% by mass. In the present invention, when the content of the distilled monoglyceride is in the above range, the dispersion stability of the hardly oil-soluble component in the edible fat is good, and therefore the hardly oil-soluble component is not separated in the soft capsule. In addition, an increase in hardness during storage of the liquid composition for filling soft capsules is suppressed, and the process of filling the soft capsules with the composition becomes easy.

本発明のソフトカプセル充填用液状組成物100質量%中の主構成脂肪酸の炭素数が22のポリグリセリン脂肪酸エステルの含有量は、特に限定されないが、例えば、通常0.25〜14質量%、好ましくは0.25〜10質量%、より好ましくは0.5〜8質量%である。本発明において該蒸留モノグリセライドの含有量が上記範囲であれば、食用油脂中での難油溶性成分の分散安定性が良好であるため、ソフトカプセル剤中で難油溶性成分の分離が生じない。また、ソフトカプセル充填用液状組成物の保存中における硬度の上昇が抑制され、該組成物をソフトカプセルに充填する工程が容易になる。   The content of the polyglycerol fatty acid ester having 22 carbon atoms of the main constituent fatty acid in 100% by mass of the liquid composition for filling soft capsules of the present invention is not particularly limited, but is usually 0.25 to 14% by mass, preferably, for example. It is 0.25-10 mass%, More preferably, it is 0.5-8 mass%. In the present invention, when the content of the distilled monoglyceride is in the above range, the dispersion stability of the hardly oil-soluble component in the edible fat is good, and therefore the hardly oil-soluble component is not separated in the soft capsule. In addition, an increase in hardness during storage of the liquid composition for filling soft capsules is suppressed, and the process of filling the soft capsules with the composition becomes easy.

また、本発明のソフトカプセル充填用液状組成物にモノエステル体含有量50%以上のジグリセリン脂肪酸エステルを使用する場合、該組成物100質量%中のモノエステル体含有量50%以上のジグリセリン脂肪酸エステルの含有量は、特に限定されないが、例えば、通常0.05〜1.5質量%、好ましくは、0.05〜1質量%、より好ましくは0.1〜1質量%である。本発明において該ジグリセリン脂肪酸エステルの含有量が上記範囲であると、生体内(例えば、胃液中)において難油溶性成分が十分に分散するため、ソフトカプセル剤の摂取により難油溶性成分の効果が十分に発揮されることが期待できる。   When a diglycerin fatty acid ester having a monoester content of 50% or more is used in the liquid composition for filling soft capsules of the present invention, the diglycerin fatty acid having a monoester content of 50% or more in 100% by mass of the composition is used. Although content of ester is not specifically limited, For example, it is 0.05-1.5 mass% normally, Preferably, it is 0.05-1 mass%, More preferably, it is 0.1-1 mass%. In the present invention, when the content of the diglycerin fatty acid ester is within the above range, the poorly oil-soluble component is sufficiently dispersed in the living body (for example, in the gastric juice). It can be expected to be fully used.

このようにして得られるソフトカプセル充填用液状組成物を、常法に従い、ゼラチンを主成分とする皮膜で包み込むことによりソフトカプセル剤を製造することができる。具体的には、例えば、2枚のゼラチンシートの間に内容物としてソフトカプセル充填用液状組成物を一定量注入して打ち抜く方法によりソフトカプセル剤を製造することができる。   Soft capsules can be produced by wrapping the thus obtained liquid composition for filling soft capsules with a film mainly composed of gelatin according to a conventional method. Specifically, for example, a soft capsule can be produced by a method of injecting a predetermined amount of a liquid composition for filling a soft capsule between two gelatin sheets and punching it out.

以下に本発明を実施例に基づいてより具体的に説明するが、本発明はこれらに限定されるものではない。   Hereinafter, the present invention will be described more specifically based on examples, but the present invention is not limited thereto.

[ソフトカプセル充填用液状組成物の作製]
(1)ソフトカプセル充填用液状組成物作製のための原材料
1)菜種サラダ油(J−オイルミルズ社製)
2)コーンスターチ(三和澱粉工業社製)
3)リボフラビン(理研ビタミン社製)
4)主構成脂肪酸の炭素数が16〜18の反応モノグリセライド(商品名:ポエムP−200;モノグリセライド含有量約52%;理研ビタミン社製)
5)主構成脂肪酸の炭素数が18の反応モノグリセライド(商品名:ポエムV−200;モノグリセライド含有量約50%;理研ビタミン社製)
6)主構成脂肪酸の炭素数が22の反応モノグリセライド(商品名:ポエムB−200;モノグリセライド含有量約47%;理研ビタミン社製)
7)蒸留モノグリセライド(商品名:エマルジーP−100;モノグリセライド含有量約98%;理研ビタミン社製)
8)蒸留モノグリセライド(商品名:ポエムS−100;モノグリセライド含有量約98%;理研ビタミン社製)
9)主構成脂肪酸の炭素数が22のポリグリセリン脂肪酸エステル(商品名:ポエムHB;トリグリセリン脂肪酸エステル;理研ビタミン社製)
10)主構成脂肪酸の炭素数が22のポリグリセリン脂肪酸エステル(商品名:ポエムJ−46B;テトラグリセリン脂肪酸エステル;理研ビタミン社製)
[Preparation of liquid composition for soft capsule filling]
(1) Raw materials for preparation of liquid composition for soft capsule filling 1) Rapeseed salad oil (manufactured by J-Oil Mills)
2) Corn starch (manufactured by Sanwa Starch Kogyo Co., Ltd.)
3) Riboflavin (manufactured by Riken Vitamin)
4) Reaction monoglyceride having 16 to 18 carbon atoms of main constituent fatty acid (trade name: Poem P-200; monoglyceride content: about 52%; manufactured by Riken Vitamin Co., Ltd.)
5) Reaction monoglyceride whose main constituent fatty acid has 18 carbon atoms (trade name: Poem V-200; monoglyceride content: about 50%; manufactured by Riken Vitamin Co., Ltd.)
6) Reaction monoglyceride whose main constituent fatty acid has 22 carbon atoms (trade name: Poem B-200; monoglyceride content: about 47%; manufactured by Riken Vitamin Co., Ltd.)
7) Distilled monoglyceride (trade name: Emulsy P-100; monoglyceride content: about 98%; manufactured by Riken Vitamin Co., Ltd.)
8) Distilled monoglyceride (trade name: Poem S-100; monoglyceride content: about 98%; manufactured by Riken Vitamin Co., Ltd.)
9) Polyglycerin fatty acid ester having 22 carbon atoms in the main constituent fatty acid (trade name: Poem HB; triglycerin fatty acid ester; manufactured by Riken Vitamin Co., Ltd.)
10) Polyglycerin fatty acid ester having 22 main constituent fatty acids (trade name: Poem J-46B; tetraglycerin fatty acid ester; manufactured by Riken Vitamin Co., Ltd.)

(2)原材料の配合組成
ソフトカプセル充填用液状組成物(実施品1〜4及び比較品1〜5)の作製に使用した原材料の配合組成を表1に示した。この内、実施品1〜4は本発明に係る実施例であり、比較品1〜5はそれらに対する比較例である。
(2) Composition of raw materials Table 1 shows the composition of raw materials used for the preparation of liquid compositions for filling soft capsules (Examples 1 to 4 and Comparative products 1 to 5). Of these, Examples 1 to 4 are examples according to the present invention, and Comparative Examples 1 to 5 are comparative examples for them.

Figure 0006322531
Figure 0006322531

(3)ソフトカプセル充填用液状組成物の作製
表1に示した配合組成に基づいてソフトカプセル充填用液状組成物を作製した。即ち、主構成脂肪酸の炭素数が16〜20の反応モノグリセライド、主構成脂肪酸の炭素数が22の反応モノグリセライド、蒸留モノグリセライド、主構成脂肪酸の炭素数が22のポリグリセリン脂肪酸エステルを菜種サラダ油に加え、これを80℃に加熱して撹拌し、これらの食品用乳化剤を該サラダ油中に溶解させた。得られた溶解液を水浴中で50℃まで冷却し、これを室温下でミキサー(型式:ウルトラタラックスT−25ベーシック;IKAジャパン社製)を使用して8000rpmで撹拌しながらコーンスターチ及びリボフラビンを加えて、さらに8000rpmで10分間撹拌し、コーンスターチ及びリボフラビンがサラダ油中に分散した分散液を得た。このとき、溶解液ないし分散液の温度が40〜50℃になるように温水または冷水を使用して適宜温度調整した。得られた分散液を真空脱泡処理した後、水浴中で25℃まで冷却し、ソフトカプセル充填用液状組成物約150g(実施品1〜4及び比較品1〜5)を得た。
(3) Preparation of liquid composition for filling soft capsules Based on the formulation shown in Table 1, a liquid composition for filling soft capsules was prepared. That is, a reaction monoglyceride having 16 to 20 carbon atoms of the main constituent fatty acid, a reaction monoglyceride having 22 carbon atoms of the main constituent fatty acid, a distilled monoglyceride, and a polyglycerol fatty acid ester having 22 carbon atoms of the main constituent fatty acid are added to the rapeseed salad oil, This was heated to 80 ° C. and stirred to dissolve these food emulsifiers in the salad oil. The obtained lysate was cooled to 50 ° C. in a water bath, and this was stirred at 8000 rpm using a mixer (model: Ultra Turrax T-25 Basic; manufactured by IKA Japan) at room temperature. In addition, the mixture was further stirred at 8000 rpm for 10 minutes to obtain a dispersion in which corn starch and riboflavin were dispersed in salad oil. At this time, the temperature of the solution or dispersion was appropriately adjusted using hot water or cold water so that the temperature of the solution or dispersion was 40 to 50 ° C. The obtained dispersion was vacuum degassed and then cooled to 25 ° C. in a water bath to obtain about 150 g of a liquid composition for filling soft capsules (Examples 1 to 4 and Comparative products 1 to 5).

(4)ソフトカプセル充填用液状組成物の評価
上述した方法により作製したソフトカプセル充填用液状組成物(実施品1〜4及び比較品1〜5)の各々について下記の評価試験を実施した。結果を表2に示した。
(4) Evaluation of liquid composition for filling soft capsules The following evaluation tests were performed on each of the liquid compositions for filling soft capsules (Examples 1 to 4 and Comparative Examples 1 to 5) prepared by the above-described method. The results are shown in Table 2.

[難油溶性成分の分離の評価]
ソフトカプセル充填用液状組成物(実施品1〜4及び比較品1〜5)の各々を遠沈管(容量50mL;プラスチック製)に50g入れ、これを遠心機(型式:SL−IV;佐久間製作所社製)を用いて回転数3000rpmで15分間遠心した。その後、遠心分離機から遠沈管を取り出し、遠沈管の試料について、難油溶性成分(コーンスターチ及びリボフラビン)の分離の有無を目視により観察した。
[Evaluation of separation of hardly oil-soluble components]
50 g of each of the liquid compositions for filling soft capsules (implemented products 1 to 4 and comparative products 1 to 5) is put into a centrifuge tube (capacity 50 mL; made of plastic), and this is centrifuged (model: SL-IV; manufactured by Sakuma Seisakusho). ), And centrifuged at 3000 rpm for 15 minutes. Thereafter, the centrifuge tube was taken out from the centrifuge, and the presence or absence of separation of the hardly oil-soluble components (corn starch and riboflavin) was visually observed in the centrifuge tube sample.

[硬度の評価]
ソフトカプセル充填用液状組成物(実施品1〜4及び比較品1〜5)の各々をプラスチック製の円錐台形状の容器(容量90mL;内径:上部65mm、底部45mm)に40g充填し、25℃で24時間保存した後、硬度を測定した。硬度の測定では、テクスチャアナライザ(型式:EZ−Test;φ14円柱型治具装着;進入速度120mm/min;島津製作所社製)を使用し、円柱型治具を組成物の表面からその内部に10mm進入させるまでの間に測定される最大応力(N)を硬度とした。
[Evaluation of hardness]
Each of the liquid compositions for filling soft capsules (Examples 1 to 4 and Comparative products 1 to 5) was filled into a plastic truncated cone-shaped container (capacity 90 mL; inner diameter: upper part 65 mm, bottom part 45 mm) at 25 ° C. After storage for 24 hours, the hardness was measured. For the measurement of hardness, a texture analyzer (model: EZ-Test; φ14 cylindrical jig mounted; entry speed 120 mm / min; manufactured by Shimadzu Corporation) was used, and the cylindrical jig was placed 10 mm from the surface of the composition to the inside. The maximum stress (N) measured before entering was determined as the hardness.

Figure 0006322531
Figure 0006322531

表2の結果から明らかなように、実施品1〜4のいずれも、難油溶性成分の分離が生じておらず、これらの硬度は最大でも1.21Nに抑制されていた。一方、比較品1〜4では、いずれも難油溶性成分の分離が生じ、中でも、比較品4は、その硬度が2.52Nに上昇していた。また、比較品5では、難油溶性成分の分離は生じなかったが、その硬度は2.00Nに上昇していた。即ち、比較品1〜5は、いずれもソフトカプセル剤への使用に適さないものであった。   As is clear from the results in Table 2, none of the Examples 1 to 4 caused separation of the hardly oil-soluble component, and their hardness was suppressed to 1.21 N at the maximum. On the other hand, in comparative products 1 to 4, separation of the hardly oil-soluble component occurred, and in particular, the hardness of comparative product 4 increased to 2.52N. Further, in Comparative product 5, the hardly oil-soluble component was not separated, but the hardness increased to 2.00 N. That is, Comparative products 1 to 5 were all unsuitable for use in soft capsules.

Claims (1)

食用油脂中に難油溶性成分を分散せしめた組成物であって、(a)主構成脂肪酸の炭素数が16〜20の反応モノグリセライド、(b)主構成脂肪酸の炭素数が22の反応モノグリセライド、(c)蒸留モノグリセライド及び(d)主構成脂肪酸の炭素数が22のポリグリセリン脂肪酸エステルを含有することを特徴とするソフトカプセル充填用液状組成物。   A composition in which a hardly oil-soluble component is dispersed in an edible fat, and (a) a reactive monoglyceride having 16 to 20 carbon atoms in the main constituent fatty acid, (b) a reactive monoglyceride having 22 carbon atoms in the main constituent fatty acid, A liquid composition for filling soft capsules comprising (c) distilled monoglyceride and (d) a polyglycerol fatty acid ester having 22 main constituent fatty acids.
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