JP2021132586A - Thickening or fixation agent of fat - Google Patents

Abstract

To provide a thickening or fixation agent of fat that is easily dissolved in fat, and can thicken or fix the fat with a small addition amount, and can suppress separation of the fat for a long time, fat containing the thickening or fixation agent of the fat, further food and drink containing these.SOLUTION: With a thickening or fixation agent of fat containing polyglycerol fatty acid ester having an esterification rate of 70% or higher obtained by esterifying: constituent polyglycerol having average polymerization degree of 11 to 20; and constituent fatty acid containing 60% or larger of behenic acid, and at least one or more kinds selected from (1) at least one or more kinds of straight chain saturated fatty acids having 16 to 22 carbons, and (2) at least one or more kinds selected from the group consisting of straight chain saturated fatty acid having 8 to 14 carbons, branched fatty acid having 18 to 22 carbons and unsaturated fatty acid having 18 to 22 carbons, in which a molar ratio of (1) and (2) is 0.91 : 0.09 to 0.99: 0.01, thickening or fixation agent of the fat is achieved with a small amount addition, and the fat can be suppressed from separating for a long time.SELECTED DRAWING: None

Description

本発明は、特定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油脂の増粘又は固化剤、及び油脂の増粘又は固化剤を含有する油脂、更にはそれらを用いた飲食品に関する。 The present invention relates to a fat and oil thickening or solidifying agent containing a specific polyglycerin fatty acid ester, a fat and oil containing a fat and oil thickening or solidifying agent, and foods and drinks using them.

食品分野において液状油脂を増粘又は固化させる技術としては、油脂を水素添加する方法が一般的に知られている。しかしながら、油脂中の不飽和脂肪酸が飽和脂肪酸となりそれに伴い融点が高くなるため使用しづらく、食品に供した場合口どけが悪くなる問題があった。また、水素添加する方法では、一部の不飽和脂肪酸のシス型結合がトランス型に変化し、このトランス脂肪酸が人体へ健康影響を及ぼすリスクについて近年問題視されている。
このような問題を改善するために液状の油脂を増粘又は固化させる技術としては、ポリグリセリン脂肪酸エステルを添加する方法が挙げられ、主構成脂肪酸をベヘン酸とし、エステル化度を５０％以上としたポリグリセリン脂肪酸エステルの使用が知られていた（例えば、特許文献１参照。）。 As a technique for thickening or solidifying liquid fats and oils in the food field, a method of hydrogenating fats and oils is generally known. However, it is difficult to use because the unsaturated fatty acid in the fat and oil becomes a saturated fatty acid and the melting point rises accordingly, and there is a problem that the melt-in-the-mouth becomes worse when it is used for food. Further, in the hydrogenation method, the cis-type bond of some unsaturated fatty acids is changed to the trans-type, and the risk that this trans-fatty acid has a health effect on the human body has been regarded as a problem in recent years.
As a technique for thickening or solidifying liquid fats and oils in order to improve such problems, there is a method of adding a polyglycerin fatty acid ester, in which the main constituent fatty acid is behenic acid and the degree of esterification is 50% or more. The use of polyglycerin fatty acid esters has been known (see, for example, Patent Document 1).

しかしながら、従来技術においてポリグリセリン脂肪酸エステルの構成ポリグリセリンの平均重合度は特定されておらず、増粘又は固化した油脂のゲル強度は十分ではなく、液状の油脂を増粘又は固化させる場合、ポリグリセリン脂肪酸エステルの添加量を増加しなければならず、食感や口どけが悪くなり満足できるものではなかった。 However, in the prior art, the average degree of polymerization of the constituent polyglycerin of the polyglycerin fatty acid ester has not been specified, the gel strength of the thickened or solidified fat or oil is not sufficient, and when the liquid fat or oil is thickened or solidified, poly The amount of glycerin fatty acid ester added had to be increased, and the texture and mouthfeel were poor, which was not satisfactory.

特許第３４９７７８０号公報Japanese Patent No. 3497780

本発明は、油脂に対し容易に溶解し、少量の添加で油脂を増粘又は固化することが可能であり、長期間油脂の分離抑制が可能な油脂の増粘又は固化剤、及び油脂の増粘又は固化剤を含有する油脂、更にはそれらを含有する飲食品を提供することを目的とするものである。 INDUSTRIAL APPLICABILITY The present invention provides a thickening or solidifying agent for fats and oils that easily dissolves in fats and oils, can thicken or solidify the fats and oils with a small amount of addition, and can suppress separation of the fats and oils for a long period of time, and an increase in fats and oils. It is an object of the present invention to provide fats and oils containing a viscous or solidifying agent, as well as foods and drinks containing them.

本発明者らは上記課題を解決するために鋭意努力した結果、次に示す特定の組成を有するポリグリセリン脂肪酸エステルを常温で液状の油脂に少量添加することで増粘又は固化可能であることを見出し、本発明の完成に至った。特定の組成のポリグリセリン脂肪酸エステルとは、平均重合度が１１〜２０の構成ポリグリセリンと、ベヘン酸の割合が６０％以上であり、（１）炭素数１６〜２２の直鎖飽和脂肪酸を少なくとも１種以上、（２）炭素数８〜１４の直鎖飽和脂肪酸、炭素数１８〜２２の分岐脂肪酸及び炭素数１８〜２２の不飽和脂肪酸からなる群より選択される少なくとも１種以上を含有し、（１）：（２）のモル比が０．９１：０．０９〜０．９９：０．０１である構成脂肪酸とをエステル化させたポリグリセリン脂肪酸エステルであって、そのエステル化率は７０％以上のものである。 As a result of diligent efforts to solve the above problems, the present inventors have found that thickening or solidification can be achieved by adding a small amount of a polyglycerin fatty acid ester having the following specific composition to a liquid fat or oil at room temperature. The heading has led to the completion of the present invention. The polyglycerin fatty acid ester having a specific composition includes a constituent polyglycerin having an average degree of polymerization of 11 to 20 and a bechenic acid having a ratio of 60% or more, and (1) at least a linear saturated fatty acid having 16 to 22 carbon atoms. Contains at least one selected from the group consisting of (2) linear saturated fatty acids having 8 to 14 carbon atoms, branched fatty acids having 18 to 22 carbon atoms, and unsaturated fatty acids having 18 to 22 carbon atoms. , (1): (2) is a polyglycerin fatty acid ester obtained by esterifying a constituent fatty acid having a molar ratio of 0.91: 0.09 to 0.99: 0.01, and the esterification rate is It is 70% or more.

本発明における油脂の増粘又は固化剤は、油脂に対し容易に溶解し、少量の添加で油脂を増粘又は固化することが可能であり、長期間油脂の分離抑制が可能となる。また、本発明の油脂の増粘又は固化剤を含有した油脂を飲食品に使用した場合は、食感がよく、保型性に優れ、油浮きが少ない。 The thickening or solidifying agent for fats and oils in the present invention easily dissolves in fats and oils, can thicken or solidify fats and oils with a small amount of addition, and can suppress separation of fats and oils for a long period of time. Further, when the fat or oil containing the thickening or solidifying agent of the fat or oil of the present invention is used for food or drink, the texture is good, the shape retention is excellent, and the oil floating is small.

以下、本発明を詳細に説明する。
本発明における油脂の増粘又は固化剤は、特定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。ポリグリセリン脂肪酸エステルの構成成分として、ポリグリセリン、脂肪酸が挙げられる。本発明におけるポリグリセリン脂肪酸エステルの構成ポリグリセリンは、平均重合度が１１〜２０であり、１３〜２０が好ましい。平均重合度が１１より低いポリグリセリンを用いた場合、十分なゲル強度は得られず、長期間油脂の分離を抑えることができない。ポリグリセリンの平均重合度は高い程、ゲル強度が高く、低添加量で固化を達成する。平均重合度が２０より高いポリグリセリンを用いた場合、強固なゲルが得られるものの、食品に添加した際の食感が望ましくない。
ここで言うポリグリセリンの平均重合度とは、末端基分析法による水酸基価から算出されるポリグリセリンの平均重合度である。詳しくは、（式１） 及び（式２） から算出した平均重合度である。 Hereinafter, the present invention will be described in detail.
The thickening or solidifying agent for fats and oils in the present invention is characterized by containing a specific polyglycerin fatty acid ester. Examples of the constituent components of the polyglycerin fatty acid ester include polyglycerin and fatty acids. The constituent polyglycerin of the polyglycerin fatty acid ester in the present invention has an average degree of polymerization of 11 to 20, preferably 13 to 20. When polyglycerin having an average degree of polymerization of less than 11 is used, sufficient gel strength cannot be obtained, and separation of fats and oils cannot be suppressed for a long period of time. The higher the average degree of polymerization of polyglycerin, the higher the gel strength, and the lower the amount of addition, the higher the solidification. When polyglycerin having an average degree of polymerization of more than 20 is used, a strong gel can be obtained, but the texture when added to food is not desirable.
The average degree of polymerization of polyglycerin referred to here is the average degree of polymerization of polyglycerin calculated from the hydroxyl value by the end group analysis method. Specifically, it is the average degree of polymerization calculated from (Equation 1) and (Equation 2).

（式１）平均重合度＝（１１２．２×１０^３−１８×水酸基価）／（７４×水酸基価−５６．１×１０^３）
（式２）水酸基価＝（ａ−ｂ）×２８．０５／試料の採取量（ｇ）
ａ：空試験による０．５Ｎ水酸化カリウム溶液の消費量（ｍｌ）
ｂ：本試験による０．５Ｎ水酸化カリウム溶液の消費量（ｍｌ）
上記（式１） 中の水酸基価は社団法人日本油化学会編「日本油化学会制定 基準油脂分析試験法（Ｉ）１９９６年度版」に準じて（式２）で算出される。 (Equation 1) Average polymerization degree = (112.2 × ¹⁰ 3 -18 × hydroxyl value) / (74 × hydroxyl value -56.1 × ¹⁰ 3)
(Equation 2) Hydroxyl value = (ab) × 28.05 / Sample collection amount (g)
a: Consumption of 0.5N potassium hydroxide solution by blank test (ml)
b: Consumption (ml) of 0.5N potassium hydroxide solution in this test
The hydroxyl value in the above (Equation 1) is calculated by (Equation 2) according to the "Standard Oil and Fat Analysis Test Method (I) 1996 Edition established by the Japan Oil Chemists'Association" edited by the Japan Oil Chemists' Society.

本発明におけるポリグリセリン脂肪酸エステルの構成ポリグリセリンの全ての水酸基のうち一級水酸基が占める割合（以降、一級水酸基含有率という）は５０％以上が好ましい。これよりも一級水酸基含有率が低いポリグリセリンを用いた場合、十分なゲル強度は得られず、長期間油脂の分離を抑えることができない場合がある。ポリグリセリンの一級水酸基含有率は高い程、ゲル強度が高く、低添加量で固化を達成する。そのため、ポリグリセリンの一級水酸基含有率は５５％以上がより好ましい。 Constituent composition of polyglycerin fatty acid ester in the present invention The ratio of primary hydroxyl groups to all hydroxyl groups of polyglycerin (hereinafter referred to as primary hydroxyl group content) is preferably 50% or more. When polyglycerin having a lower primary hydroxyl group content than this is used, sufficient gel strength cannot be obtained, and separation of fats and oils may not be suppressed for a long period of time. The higher the primary hydroxyl group content of polyglycerin, the higher the gel strength, and the lower the amount of addition, the more solidification is achieved. Therefore, the primary hydroxyl group content of polyglycerin is more preferably 55% or more.

本発明におけるポリグリセリン脂肪酸エステルの構成ポリグリセリンの一級水酸基含有率は、炭素原子に対する核磁気共鳴スペクトル（ＮＭＲ）を測定する以下の方法を用いて算出される。ポリグリセリン５００ｍｇを重水２．８ｍｌに溶解し、ろ過後ゲートつきデカップリングにより^１３Ｃ−ＮＭＲ（１２５ＭＨｚ）スペクトルを得る。ゲートデカップルド測定手法によりピーク強度は炭素数に比例する。一級水酸基と二級水酸基の存在を示す^１３Ｃ化学シフトはそれぞれメチレン炭素（ＣＨ_２ＯＨ）が６３ｐｐｍ付近、メチン炭素（ＣＨＯＨ）が７１ｐｐｍ付近であり、２種それぞれのシグナル強度の分析により、一級水酸基と二級水酸基の存在比を算出する。但し、二級水酸基を示すメチン炭素（ＣＨＯＨ）は、一級水酸基を示すメチレン炭素に結合するメチン炭素にさらに隣接するメチレン炭素ピークと重なり、それ自体の積分値を得られないため、メチン炭素（ＣＨＯＨ）と隣り合うメチレン炭素（ＣＨ_２）の７４ｐｐｍ付近のシグナル強度により積分値を算出する。 The composition of the polyglycerin fatty acid ester in the present invention The primary hydroxyl group content of polyglycerin is calculated using the following method for measuring a nuclear magnetic resonance spectrum (NMR) with respect to a carbon atom. 500 mg of polyglycerin is dissolved in 2.8 ml of heavy water, and after filtration, a ¹³ C-NMR (125 MHz) spectrum is obtained by decoupling with a gate. The peak intensity is proportional to the number of carbon atoms by the gate decoupled measurement method. ^{The 13} C chemical shifts indicating the presence of primary and secondary hydroxyl groups are methylene carbon (CH ₂ OH) around 63 ppm and methine carbon (CHOH) around 71 ppm, respectively. And the abundance ratio of secondary hydroxyl groups are calculated. However, the methine carbon (CHOH) showing a secondary hydroxyl group overlaps with the methylene carbon peak further adjacent to the methine carbon bonded to the methylene carbon showing a primary hydroxyl group, and the integrated value of itself cannot be obtained. Therefore, the methine carbon (CHOH) cannot be obtained. ) And the signal intensity of methylene carbon (CH ₂ ) adjacent to 74 ppm are used to calculate the integrated value.

本発明におけるポリグリセリン脂肪酸エステルの構成ポリグリセリンとしては、平均重合度と一級水酸基含有率が上記値を有するものであれば、合成品を用いても市販品を用いてもよい。
本発明におけるポリグリセリン脂肪酸エステルの構成ポリグリセリンの一級水酸基含有率を調整する方法としては、特に限定されるものではないが、例えば、ポリグリセリンに一級水酸基に選択的に反応する試薬、即ち、一級水酸基の保護基となる試薬を反応させて、ポリグリセリンの極性を変化させた後、一級水酸基を多く有するポリグリセリンほど極性が低くなることを利用して、一級水酸基を有するポリグリセリンを適宜選択することにより、一級水酸基含有率を調整できる。選択したポリグリセリンは、当業者に公知の方法に従って、保護基の脱離処理を行うとよい。 As the constituent polyglycerin of the polyglycerin fatty acid ester in the present invention, a synthetic product or a commercially available product may be used as long as the average degree of polymerization and the primary hydroxyl group content have the above values.
Composition of Polyglycerin Fatty Ester in the Present Invention The method for adjusting the primary hydroxyl group content of polyglycerin is not particularly limited, but for example, a reagent that selectively reacts with polyglycerin on a primary hydroxyl group, that is, primary. After reacting a reagent that serves as a protective group for hydroxyl groups to change the polarity of polyglycerin, polyglycerin having more primary hydroxyl groups has a lower polarity, and polyglycerin having primary hydroxyl groups is appropriately selected. Thereby, the primary hydroxyl group content can be adjusted. The selected polyglycerin may be subjected to elimination treatment of the protecting group according to a method known to those skilled in the art.

本発明におけるポリグリセリン脂肪酸エステルの構成脂肪酸は、十分なゲル強度を得るため、構成脂肪酸中のベヘン酸の割合が６０％以上であることが必要である。なお、この割合は、全構成脂肪酸のモル数に対するベヘン酸のモル数の割合を示す。更に高いゲル強度を得るには、構成脂肪酸中のベヘン酸の割合は７０％以上が好ましく、８０％以上がより好ましい。 The constituent fatty acids of the polyglycerin fatty acid ester in the present invention need to have a behenic acid ratio of 60% or more in the constituent fatty acids in order to obtain sufficient gel strength. This ratio indicates the ratio of the number of moles of behenic acid to the number of moles of all constituent fatty acids. In order to obtain a higher gel strength, the ratio of behenic acid in the constituent fatty acids is preferably 70% or more, more preferably 80% or more.

本発明におけるポリグリセリン脂肪酸エステルの構成脂肪酸は、ゲル強度を上昇させる点から、（１）炭素数１６〜２２の直鎖飽和脂肪酸を少なくとも１種以上、（２）炭素数８〜１４の直鎖飽和脂肪酸、炭素数１８〜２２の分岐脂肪酸及び炭素数１８〜２２の不飽和脂肪酸からなる群より選択される少なくとも１種以上を含有可能である。構成脂肪酸の比率として（１）：（２）のモル比が、０．９１：０．０９〜０．９９：０．０１のとき、低添加量で油脂を増粘又は固化できゲル強度が高く、長期間油脂の分離抑制が可能となり好ましい。構成脂肪酸（１）にはパルミチン酸、ステアリン酸、アラキジン酸、ベヘン酸が挙げられ、構成脂肪酸（２）にはカプリル酸、カプリン酸、ラウリン酸、ミリスチン酸、オレイン酸、エルカ酸、イソステアリン酸等が挙げられるが、構成脂肪酸（２）の範囲であれば、特に限定されるものではない。効果の点より、構成脂肪酸（１）はベヘン酸、ステアリン酸、パルミチン酸が好ましく、ベヘン酸がより好ましい。構成脂肪酸（２）はオレイン酸、カプリル酸が好ましい。（１）：（２）のモル比の（１）の部分が下限を外れる場合、ゲル強度は低下し、低添加量で固化を達成できない。 The constituent fatty acids of the polyglycerin fatty acid ester in the present invention are (1) at least one kind of linear saturated fatty acid having 16 to 22 carbon atoms and (2) linear fatty acid having 8 to 14 carbon atoms from the viewpoint of increasing gel strength. It can contain at least one selected from the group consisting of saturated fatty acids, branched fatty acids having 18 to 22 carbon atoms and unsaturated fatty acids having 18 to 22 carbon atoms. When the molar ratio of constituent fatty acids (1): (2) is 0.91: 0.09 to 0.99: 0.01, fats and oils can be thickened or solidified with a low addition amount, and the gel strength is high. It is preferable because the separation of fats and oils can be suppressed for a long period of time. Examples of the constituent fatty acid (1) include palmitic acid, stearic acid, arachidic acid, and behenic acid, and examples of the constituent fatty acid (2) include caprylic acid, capric acid, lauric acid, myristic acid, oleic acid, erucic acid, and isostearic acid. However, the range is not particularly limited as long as it is in the range of the constituent fatty acid (2). From the viewpoint of effect, the constituent fatty acid (1) is preferably behenic acid, stearic acid, or palmitic acid, and more preferably behenic acid. The constituent fatty acid (2) is preferably oleic acid or caprylic acid. (1): When the portion (1) of the molar ratio of (2) deviates from the lower limit, the gel strength decreases and solidification cannot be achieved with a low addition amount.

本発明のポリグリセリン脂肪酸エステルのエステル化率は７０％以上である。これよりもエステル化率が低い場合、十分なゲル強度は得られず、長期間油脂の分離抑制が不可能となる。エステル化率は、高いほどゲル強度が高く、低添加量で固化を達成する。そのため、エステル化率は７５％以上が好ましく、８０％以上がより好ましい。ポリグリセリン脂肪酸エステルのエステル化率は、次式で算出できる。
エステル化率（％）＝（ポリグリセリンに付加している構成脂肪酸のモル数／構成ポリグリセリンの総水酸基の数）×１００ The esterification rate of the polyglycerin fatty acid ester of the present invention is 70% or more. If the esterification rate is lower than this, sufficient gel strength cannot be obtained, and it becomes impossible to suppress the separation of fats and oils for a long period of time. The higher the esterification rate, the higher the gel strength, and solidification is achieved with a low addition amount. Therefore, the esterification rate is preferably 75% or more, more preferably 80% or more. The esterification rate of the polyglycerin fatty acid ester can be calculated by the following formula.
Esterification rate (%) = (number of moles of constituent fatty acids added to polyglycerin / number of total hydroxyl groups of constituent polyglycerin) × 100

本発明におけるポリグリセリン脂肪酸エステルは、上記の各成分の上記条件を満たすような組成でポリグリセリンと脂肪酸を仕込み、水酸化ナトリウム等の触媒を加え、常圧もしくは減圧下においてエステル化反応を行うことで製造することが可能である。 The polyglycerin fatty acid ester in the present invention is prepared by charging polyglycerin and fatty acid in a composition satisfying the above conditions of each of the above components, adding a catalyst such as sodium hydroxide, and performing an esterification reaction under normal pressure or reduced pressure. It is possible to manufacture with.

本発明の油脂の増粘又は固化剤により増粘又は固化される油脂は、飲食品原料として使用される油脂であれば特に限定されるものではなく、また、化粧品原料として使用される油脂や油剤も含まれる。例えば、油脂としては、アボガド油、アマニ油、アルガン油、アーモンド油、エゴマ油、オリーブ油、オレンジラフィー油、カカオ脂、キャロット油、キューカンバー油、牛脂、ココナッツ油、グレープシード油、ゴマ油、小麦胚芽油、コメヌカ油、サザンカ油、サフラワー油、シア脂、ダイズ油、タートル油、チョウジ油、茶油、月見草油、ツバキ油、トウモロコシ油、豚脂、ナタネ油、ハトムギ油、パーム油、パーム核油、ピーナッツ油、ヒマシ油、ヒマワリ油、ヘーゼルナッツ油、マカデミアナッツ油、ミンク油、メドウフォーム油、綿実油、ヤシ油、ローズヒップ油、乳脂、ハトムギ油、ホホバ油、ラベンダー油、卵黄油、米油、ラノリン、ローズマリー油等、ロウ類としては、カルナウバロウ、キャンデリラロウ、鯨ロウ、ミツロウ、モンタンロウ、ライスワックス、ラノリンワックス等、炭化水素油類としてはイソドデカン、スクワラン、セレシン、パラフィン、プリスタン、流動パラフィン、流動イソパラフィンワセリン等、脂肪酸類としてはアラキドン酸、イソステアリン酸、ウンデシレン酸、エルカ酸、オレイン酸、カプリン酸、カプリル酸、ステアリン酸、セバシン酸、パーム核脂肪酸、パルミチン酸、ヒドロキシステアリン酸、ベヘン酸、ミリスチン酸、ヤシ油脂肪酸、ラノリン脂肪酸、リノール酸、リノレン酸等、高級アルコール類としてはイソステアリルアルコール、オレイルアルコール、オクチルドデカノール、オクチルアルコール、キミルアルコール、ステアリルアルコール、セタノール、セトステアリルアルコール、デシルアルコール、バチルアルコール、ヘキシルデカノール、ヘキシルデカノール、ベヘニルアルコール、ミリスチルアルコール、ラウリルアルコール、ラノリンアルコール等、シリコーン油類としてはジメチコン、ジフェニルジメチコン、シクロペンタシロキサン、トリシロキサン、メチルフェニルポリシロキサン等、エステル油類としてはアジピン酸ジオクチル、アジピン酸ジイソプロピル、アジピン酸ジイソブチル、アジピン酸ジ２−ヘキシルデシル、アジピン酸ジヘプチルウンデシル、アボカド油脂肪酸エチル、安息香酸アルキル、イソステアリルグリセリル、イソステアリン酸ヘキシルデシル、イソステアリン酸イソプロピル、イソステアリン酸オクチルドデシル、イソステアリン酸イソセチル、イソステアリン酸イソステアリル、イソステアリン酸グリセリル、イソステアリン酸コレステリル、イソノナン酸イソトリデシル、イソノナン酸イソノニル、イソノナン酸イソデシル、イソノナン酸トリデシル、イソパルミチン酸オクチル、イソペラルゴン酸オクチル、エチルヘキサン酸セチル、エルカ酸オクチルドデシル、エチルヘキサン酸セトステアリル、エチレングリコール脂肪酸エステル、エルカ酸オクチルドデシル、オクタン酸アルキル（Ｃ１４，Ｃ１６，Ｃ１８）、オクタン酸イソセチル、オクタン酸セテアリル、オクタン酸ステアリル、オクタン酸セチル、オクタン酸イソステアリル、オレイン酸エチル、オレイン酸オレイル、オレイン酸オクチルドデシル、オレイン酸デシル、オレイン酸フィトステリル、カプリン酸セチル、カプリル酸セチル、コハク酸ジオクチル、コハク酸ポリプロピレングリコールオリゴエステル、酢酸ラノリン、ジイソステアリン酸グリセリル、ジイソステアリン酸ネオペンチルグリコール、ジカプリル酸プロピレングリコール、ジカプリン酸ネオペンチルグリコール、ジオクタン酸ネオペンチルグリコール、ジオクタン酸エチレングリコール、ジオレイン酸エチレングリコール、ジカプリン酸プロピレングリコール、ジメチルオクタン酸ヘキシルデシル、ジメチルオクタン酸オクチルドデシル、ジペラルゴン酸プロピレングリコール、ステアリン酸ヘキシルデシル、炭酸ジアルキル、デカイソステアリン酸デカグリセリル、テトラオクタン酸ペンタエリスリチル、テトライソステアリン酸ジグリセリル、トリイソステアリン酸グリセリル、トリイソステアリン酸ジグリセリル、トリイソステアリン酸ポリグリセリル、トリイソステアリン酸トリメチロールプロパン、トリオレイン酸グリセリル、トリカプリル酸グリセリル、トリオクタノイン、トリオクタン酸トリメチロールプロパン、トリ（カプリル酸／カプリン酸）グリセリル、乳酸ラウリル、乳酸オクチルドデシル、ネオデカン酸ヘキシルデシル、ノナイソステアリン酸デカグリセリル、パルミチン酸イソステアリル、パルミチン酸イソプロピル、パルミチン酸オクチル、パルミチン酸イソセチル、ヒドロキシステアリン酸オクチル、ミリスチン酸イソトリデシル、ミリスチン酸イソセチル、ミリスチン酸イソステアリル、ミリスチン酸イソプロピル、ミリスチン酸オクチルドデシル、ラウリン酸イソステアリル、ラノリン脂肪酸イソプロピル、ラウリン酸ヘキシル、リシノレイン酸オクチルドデシル、リノール酸トコフェロール、リシノール酸オクチルドデシル、リンゴ酸ジイソステアリル等、シリコーン類としてはアミノプロピルジメチコン、アルキルメチコン、アルコキシ変性ポリシロキサン、（ジメチコン／ビニルジメチコン）クロスポリマー、（ステアロキシメチコン／ジメチコン）コポリマー、（ジメチルシロキサン／メチルセチルオキシシロキサン）コポリマー、ステアリルジメチコン、セチルジメチコンシリコン、メチルハイドロジェンポリシロキサン、フェニルトリメチコン、ポリエーテル変性オルガノポリシロキサン、ポリオキシアルキレンアルキルメチルポリシロキサン・メチルポリシロキサン共重合体等、植物の茎、花、蕾、葉、根、果実皮、樹皮、樹脂由来の精油等が挙げられる。なお、効果の点より、アマニ油、オリーブ油、サフラワー油、ダイズ油、ナタネ油、パーム油、ヒマワリ油、ヤシ油が好ましい。 The fats and oils that are thickened or solidified by the thickening or solidifying agent of the fats and oils of the present invention are not particularly limited as long as they are used as raw materials for foods and drinks, and fats and oils and oils that are used as raw materials for cosmetics. Is also included. For example, as fats and oils, avocado oil, flaxseed oil, argan oil, almond oil, egoma oil, olive oil, orange raffy oil, cacao fat, carrot oil, cucumber oil, beef fat, coconut oil, grape seed oil, sesame oil, wheat germ oil , Coconut oil, Southernka oil, Saflower oil, Shea butter, Soybean oil, Turtle oil, Chouji oil, Tea oil, Evening primrose oil, Camellia oil, Corn oil, Pork fat, Rapeseed oil, Hatomugi oil, Palm oil, Palm kernel oil , Peanut oil, sunflower oil, sunflower oil, hazelnut oil, macadamia nut oil, mink oil, meadowfoam oil, cottonseed oil, palm oil, rosehip oil, milk fat, coconut oil, jojoba oil, lavender oil, egg yolk oil, rice oil, lanolin , Rosemary oil, etc., as waxes, carnauba wax, candelilla wax, whale wax, beeswax, montan wax, rice wax, lanolin wax, etc. Liquid isoparaffin vaseline and other fatty acids include arachidonic acid, isostearic acid, undecylene acid, erucic acid, oleic acid, capric acid, capric acid, stearic acid, sebacic acid, palm kernel fatty acid, palmitic acid, hydroxystearic acid, bechenic acid, Higher alcohols such as myristic acid, coconut oil fatty acid, lanolin fatty acid, linoleic acid, and linolenic acid include isostearyl alcohol, oleyl alcohol, octyldodecanol, octyl alcohol, chimyl alcohol, stearyl alcohol, cetanol, cetostearyl alcohol, and decyl. Alcohol, batyl alcohol, hexyldecanol, hexyldecanol, behenyl alcohol, myristyl alcohol, lauryl alcohol, lanolin alcohol, etc., silicone oils such as dimethicone, diphenyldimethicone, cyclopentasiloxane, trisiloxane, methylphenylpolysiloxane, etc. Dioctyl acid, diisopropyl adipate, diisobutyl adipate, di2-hexyldecyl adipate, diheptylundecyl adipate, ethyl avocado oil fatty acid, alkyl benzoate, isostearyl glyceryl, hexyldecyl isostearate, isopropyl isostearate, isostearic acid Octyldodecyl, isosetyl isostearate, isostearyl isostearate, glyceryl isostearate , Cholesteryl isostearate, Isotridecyl isononanoate, Isononyl isononanoate, Isodecyl isononanoate, Tridecyl isononanoate, Octyl isopalmitate, Octyl isoperalgonate, Cetyl ethylhexanate, Octyldodecylerkaate, Setostearyl ethylhexanate, Ethylene glycol fatty acids Estel, octyldodecyl erucate, alkyl octanoate (C14, C16, C18), isosetyl octanoate, cetearyl octatel, stearyl octanoate, cetyl octateate, isostearyl octanoate, ethyl oleate, oleyl oleate, octyl oleate Dodecyl, decyl oleate, phytosteryl oleate, cetyl capryate, cetyl caprylate, dioctyl succinate, polypropylene glycol oligoester succinate, lanolin acetate, glyceryl diisostearate, neopentyl glycol diisostearate, propylene glycol dicaprylate, neo dicaprate Pentyl glycol, neopentyl glycol dioctanoate, ethylene glycol dioctanoate, ethylene glycol dioleate, propylene glycol dicaprate, hexyldecyl dimethyloctanoate, octyldodecyldimethyloctanoate, propylene glycol diperargonate, hexyldecyl stearate, dialkyl carbonate, deca Decaglyceryl isostearate, pentaerythrityl tetraoctanoate, diglyceryl tetraisostearate, glyceryl triisostearate, diglyceryl triisostearate, polyglyceryl triisostearate, trimethylolpropane triisostearate, glyceryl trioleate, glyceryl tricaprylate, Trioctanoin, trimethylolpropane trioctanoate, glyceryl tri (caprylic acid / capric acid), lauryl lactate, octyldodecyl lactate, hexyldecyl neodecanoate, decaglyceryl nonaisostearate, isostearyl palmitate, isopropyl palmitate, octyl palmitate , Isocetyl palmitate, Octyl hydroxystearate, Isotridecyl myristate, Isocetyl myristate, Isostearyl myristate, Isopropyl myristate, Octyldodecyl myristate, Isostearyl laurate, Lanoline fatty acid isopropyl, Hexil laurate, Oc licinoleate As silicones, aminopropyl dimethicone, alkylmethicone, alkoxy-modified polysiloxane, (dimethicone / vinyldimethicone) crosspolymer, (stealoxymethicone / dimethicone), etc. Copolymer, (dimethylsiloxane / methylcetyloxysiloxane) copolymer, stearyldimethicone, cetyldimethicone silicon, methylhydrogenpolysiloxane, phenyltrimethicone, polyether-modified organopolysiloxane, polyoxyalkylenealkylmethylpolysiloxane / methylpolysiloxane co-weight Examples thereof include plant stems, flowers, buds, leaves, roots, fruit bark, bark, and resin-derived essential oils such as coalescence. From the viewpoint of effect, flaxseed oil, olive oil, safflower oil, soybean oil, rapeseed oil, palm oil, sunflower oil, and coconut oil are preferable.

本発明の油脂の増粘又は固化剤を含有する油脂を用いた飲食品は、特に限定されるものではなく、調理用素材、加工食品、調理済食品等が挙げられ、例えば、業務用家庭用の揚げ油、炒め油、離型油、天板油、マーガリン、ファットスプレッド、ショートニング、フラワーペースト、クリーム類、粉末油脂類、乳化油脂類等の油脂・加工油脂、即席麺、カップ麺、即席スープ・シチュー類等の即席食品、カレー、スープ・シチュー類、パスタソース、中華食品の素、どんぶりの素等のレトルト食品・缶詰類、高カロリー飲料、流動食、栄養バランス食、栄養補助食品、特定保健用食品等の機能食品、パン、マカロニ・スパゲティ等のパスタ類、ピザパイ、麺類、ケーキミックス、加工米飯、シリアル等の小麦粉・デンプン食品、キャラメル、キャンディ、チューインガム、チョコレート、クッキー・ビスケット、ケーキ、パイ、スナック、クラッカー、和菓子、米菓子、豆菓子、ゼリー、プリン等の菓子・デザート、しょうゆ、みそ、ソース類等の基礎調味料、カレー・シチュー用ルー、たれ、ドレッシング、マヨネーズ風調味料、麺つゆ、鍋料理用つゆ、ラー油、マスタード、からし、わさび、おろししょうが、おろしにんにく、キムチの素、デミグラスソース、ホワイトソース、トマトソース等の複合調味料、乳、加工乳、発酵乳、ヨーグルト類、乳酸菌飲料、チーズ、アイスクリーム類、調整粉乳、クリーム類等の乳製品、水産缶詰、魚肉ハム・ソーセージ、水産練り製品、油漬け魚肉缶詰等の水産加工品、ピーナツバター、ジャム・マーマレード、チョコレートクリーム、メンマ加工品、ザーサイ加工品、ねりごま・ごまペースト等の農産加工品、畜肉ハム・ソーセージ、畜産缶詰、ペースト類、ハンバーグ、ミートボール、味付け畜肉缶詰等の畜産加工品、冷凍食品、冷蔵食品、パック入りや店頭販売用惣菜等の調理済み・半調理済み食品の他、愛玩動物用ペットフード、家畜用飼料が挙げられる。効果の点より、炒め油、マーガリン、ファットスプレッド、カレー、パスタソース、中華食品の素、チョコレート、カレー・シチュー用ルー、ソース、ドレッシング、マヨネーズ風調味料、ラー油、チョコレートクリームが好ましい。 Foods and drinks using fats and oils containing a thickening or solidifying agent for fats and oils of the present invention are not particularly limited, and examples thereof include cooking materials, processed foods, cooked foods, and the like, for example, for commercial household use. Fried oil, roasting oil, mold release oil, top plate oil, margarine, fat spread, shortening, flower paste, creams, powdered fats and oils, emulsified fats and oils, etc. Instant foods such as curry, soups / stews, pasta sauces, Chinese food ingredients, retort foods / canned foods such as bowls, high-calorie beverages, liquid foods, nutritionally balanced foods, nutritional supplements, for specified health use Functional foods such as foods, pasta such as bread, macaroni spaghetti, pizza pie, noodles, cake mix, processed rice, wheat flour / starch foods such as cereals, caramel, candy, chewing gum, chocolate, cookies / biscuits, cakes, pies, Snacks, crackers, Japanese confectionery, rice confectionery, bean confectionery, jelly, pudding and other confectionery / desserts, soy sauce, miso, sauces and other basic seasonings, curry / stew roux, sauce, dressing, mayonnaise-style seasoning, noodle soup , Pot cooking soup, ra oil, mustard, mustard, wasabi, grated ginger, grated garlic, kimchi no moto, demiglas sauce, white sauce, tomato sauce and other complex seasonings, milk, processed milk, fermented milk, yogurt, lactic acid bacteria Beverages, cheese, ice cream, dairy products such as prepared milk powder, creams, canned fishery products, fish hams and sausages, fish paste products, processed marine products such as oil-pickled fish meat canned foods, peanut butter, jam marmalade, chocolate cream, menma Processed products, processed products of Zasai, processed agricultural products such as sesame and sesame paste, livestock hams and sausages, canned livestock, pastes, hamburgers, meat balls, processed livestock products such as seasoned canned livestock, frozen foods, refrigerated foods, packs In addition to cooked and semi-cooked foods such as prepared foods for sale in stores and over-the-counter foods, pet foods for pet animals and feeds for livestock can be mentioned. From the viewpoint of effect, fried oil, margarine, fat spread, curry, pasta sauce, Chinese food base, chocolate, roux for curry stew, sauce, dressing, mayonnaise-like seasoning, chili oil, chocolate cream are preferable.

本発明の油脂の増粘又は固化剤を油脂に用いることで、油不溶物の分散安定性に優れる香味油を提供することが可能である。
本発明の油脂の増粘又は固化剤により増粘又は固化される香味油は、油脂としての物性の他、食品に好ましい香味を含有する油性物質であり、特に限定されるものではないが、例えば、香味を人工的に付与することなくそのまま油脂として利用されているゴマ油、オリーブ油、ピーナツ油、アーモンド油、クルミ油、ピスタチオ油、ラード、バター、鶏油等のほか、油脂に香味を人工的に付与したものが挙げられる。後者の例としては、油脂にタマネギ、ネギ、ニンニク、ショウガ、ニラ、トウガラシ、トマト等の野菜類、ローズマリー、タイム、ローレル、バジル、オレガノ、タラゴン、ディル、フェンネル、サボリー、チャービル、ミント、レモングラス、マジョラム、アニス、オールスパイス、カホクザンショウ、カルダモン、クミン、グリーンペッパー、クローブ、コショウ、コリアンダー、サフラン、サンショウ、シソ、シナモン、スターアニス、セージ、ターメリック、タラゴン、ナツメグ、バニラ、パプリカ、フェンネル、ホースラディッシュ、ラディッシュ、ワサビ、マスタード、チンピ等のハーブ・香辛料類、しょうゆ、みそ、カレー、鰹節、鯖節、昆布等の調味料類加工食品類、カツオ、サバ、貝柱、エビ、イカ、タコ等の魚介類やその加工品、タマゴ、鶏肉、牛肉、豚肉、チーズ等のタンパク性素材類をそのままあるいは乾燥、焙煎して、油脂に浸漬して香りを付与した、あるいは固体状態で分散させた香味油が挙げられる。油脂に直接メントールや果物系等の香料、バター、チーズ、バニラ等の香料を付与したものであってもよい。 By using the thickening or solidifying agent of the fat and oil of the present invention for the fat and oil, it is possible to provide a flavor oil having excellent dispersion stability of the oil-insoluble matter.
The flavor oil that is thickened or solidified by the thickening or solidifying agent of the fat and oil of the present invention is an oily substance that contains a flavor that is preferable for foods in addition to the physical properties of the fat and oil, and is not particularly limited, but for example. In addition to sesame oil, olive oil, peanut oil, almond oil, walnut oil, pistachio oil, lard, butter, chicken oil, etc., which are used as fats and oils without artificially adding flavor, flavors are artificially added to fats and oils. The ones given can be mentioned. Examples of the latter include fats and oils, vegetables such as onions, onions, garlic, ginger, nira, capsicum, tomatoes, rosemary, thyme, laurel, basil, oregano, tarragon, dill, fennel, savory, charville, mint, lemon. Glass, Majorum, Anis, All Spice, Kahokuzansho, Cardamon, Cumin, Green Pepper, Clove, Pepper, Coriander, Saffron, Sansho, Perilla, Cinnamon, Star Anis, Sage, Turmeric, Taragon, Natsumeg, Vanilla, Paprika, Herbs and spices such as fennel, horse radish, radish, wasabi, mustard, chimpi, seasonings such as soy sauce, miso, curry, eel, mackerel, kelp, processed foods, bonito, mackerel, shellfish, shrimp, squid, Seafood such as octopus and processed products thereof, and proteinaceous materials such as egg, chicken, beef, pork, and cheese are dried or roasted as they are, or soaked in fats and oils to add aroma or dispersed in a solid state. Examples include the seasoned oil. Perfume such as menthol or fruit, butter, cheese, vanilla or the like may be directly added to the fat or oil.

本発明における油不溶物とは、上記に挙げた油脂中に常温で固体状態に分散し、油脂に不溶のものであれば特に限定されるものではないが、例えば、食塩、唐辛子やバジル等の香辛料、糖質、甘味料、旨味調味料、酸味料、酵母、蛋白加水分解物、畜肉、野菜、きのこ類、魚介類が挙げられる。 The oil-insoluble matter in the present invention is not particularly limited as long as it is dispersed in the above-mentioned fats and oils in a solid state at room temperature and is insoluble in fats and oils, but for example, salt, pepper, basil and the like. Examples include spices, sugars, sweeteners, flavor seasonings, acidulants, yeasts, protein hydrolysates, livestock meat, vegetables, mushrooms, and seafood.

油不溶物の分散安定性に優れた油脂は、特に限定されるものではないが、例えば油脂を６０℃以上に加熱し、本発明の油脂の増粘又は固化剤を十分に溶解させた後、室温又は冷蔵下で冷却することにより得られる。本発明における油脂の増粘又は固化剤の含有量の下限は、油脂に対して０．０５重量％以上であり、０．１重量％以上が好ましく、０．５重量％以上がより好ましい。上限は特に限定されるものではないが、食感の点より、油脂に対して１０重量％以下であり、５重量％以下が好ましく、２．５重量％以下がより好ましく、油脂の種類及び分散させる油不溶物の種類によって異なる。
以下、実施例及び比較例を挙げて本発明を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。 The fats and oils having excellent dispersion stability of the oil-insoluble matter are not particularly limited, but for example, after heating the fats and oils to 60 ° C. or higher and sufficiently dissolving the thickening or solidifying agent of the fats and oils of the present invention, the fats and oils are not particularly limited. Obtained by cooling at room temperature or in a refrigerator. The lower limit of the content of the thickening or solidifying agent of the fat or oil in the present invention is 0.05% by weight or more, preferably 0.1% by weight or more, and more preferably 0.5% by weight or more with respect to the fat or oil. The upper limit is not particularly limited, but from the viewpoint of texture, it is 10% by weight or less, preferably 5% by weight or less, more preferably 2.5% by weight or less, and the type and dispersion of the fat and oil. It depends on the type of oil insoluble matter to be made.
Hereinafter, the present invention will be specifically described with reference to Examples and Comparative Examples, but the present invention is not limited thereto.

実施例１
平均重合度が１３．９で、一級水酸基含有率が５７％のポリグリセリン１９．４ｇとベヘン酸（Ｃ２２）７４．１５ｇ、オレイン酸（Ｃ１８Ｆ１）６．４５ｇを反応フラスコに入れ、水酸化カリウム０．１ｇを加えた後、２６０℃でエステル化反応することにより、本発明品１の油脂の増粘又は固化剤として、エステル化率８２％のポリグリセリン脂肪酸エステルを得た。（構成脂肪酸中のベヘン酸の割合は８１％。構成脂肪酸として（１）炭素数１６〜２２の直鎖飽和脂肪酸、（２）炭素数８〜１４の直鎖飽和脂肪酸、炭素数１８〜２２の分岐脂肪酸及び炭素数１８〜２２の不飽和脂肪酸としたとき、（１）としてベヘン酸、（２）としてオレイン酸のモル比は、０．９１：０．０９。） Example 1
19.4 g of polyglycerin having an average degree of polymerization of 13.9 and a primary hydroxyl group content of 57%, 74.15 g of behenic acid (C22), and 6.45 g of oleic acid (C18F1) were placed in a reaction flask, and potassium hydroxide was 0. After adding 1 g, an esterification reaction was carried out at 260 ° C. to obtain a polyglycerin fatty acid ester having an esterification rate of 82% as a thickening or solidifying agent for the fat and oil of the product 1 of the present invention. (The ratio of behenic acid in the constituent fatty acids is 81%. As constituent fatty acids, (1) linear saturated fatty acids having 16 to 22 carbon atoms, (2) linear saturated fatty acids having 8 to 14 carbon atoms, and 18 to 22 carbon atoms. When the branched fatty acid and the unsaturated fatty acid having 18 to 22 carbon atoms are used, the molar ratio of behenic acid as (1) and oleic acid as (2) is 0.91: 0.09.)

実施例２
平均重合度が１９．７で、一級水酸基含有率が５９％のポリグリセリン１９．７ｇとベヘン酸（Ｃ２２）７３．８８ｇ、オレイン酸（Ｃ１８Ｆ１）６．４２ｇを反応フラスコに入れ、水酸化カリウム０．１ｇを加えた後、２６０℃でエステル化反応することにより、本発明品２の油脂の増粘又は固化剤として、エステル化率８３％のポリグリセリン脂肪酸エステルを得た。（実施例１と同様に算定したとき、構成脂肪酸中のベヘン酸の割合は８１％。構成脂肪酸（１）としてベヘン酸、（２）としてオレイン酸のモル比は、０．９１：０．０９。） Example 2
19.7 g of polyglycerin having an average degree of polymerization of 19.7 and a primary hydroxyl group content of 59%, 73.88 g of behenic acid (C22), and 6.42 g of oleic acid (C18F1) were placed in a reaction flask, and potassium hydroxide was 0. After adding 1 g, an esterification reaction was carried out at 260 ° C. to obtain a polyglycerin fatty acid ester having an esterification rate of 83% as a thickening or solidifying agent for the fat and oil of the product 2 of the present invention. (When calculated in the same manner as in Example 1, the proportion of behenic acid in the constituent fatty acids is 81%. The molar ratio of behenic acid as the constituent fatty acid (1) and oleic acid as the constituent fatty acid (2) is 0.91: 0.09. .)

実施例３
平均重合度が１０．７で、一級水酸基含有率が５６％のポリグリセリン１９．４ｇとベヘン酸（Ｃ２２）７４．１５ｇ、オレイン酸（Ｃ１８Ｆ１）６．４５ｇを反応フラスコに入れ、水酸化カリウム０．１ｇを加えた後、２６０℃でエステル化反応することにより、本発明品３の油脂の増粘又は固化剤として、エステル化率８０％のポリグリセリン脂肪酸エステルを得た。（実施例１と同様に算定したとき、構成脂肪酸中のベヘン酸の割合は８１％。構成脂肪酸（１）としてベヘン酸、（２）としてオレイン酸のモル比は、０．９１：０．０９。） Example 3
19.4 g of polyglycerin having an average degree of polymerization of 10.7 and a primary hydroxyl group content of 56%, 74.15 g of behenic acid (C22), and 6.45 g of oleic acid (C18F1) were placed in a reaction flask, and potassium hydroxide was 0. After adding 1 g, an esterification reaction was carried out at 260 ° C. to obtain a polyglycerin fatty acid ester having an esterification rate of 80% as a thickening or solidifying agent for the fat and oil of the product 3 of the present invention. (When calculated in the same manner as in Example 1, the proportion of behenic acid in the constituent fatty acids is 81%. The molar ratio of behenic acid as the constituent fatty acid (1) and oleic acid as the constituent fatty acid (2) is 0.91: 0.09. .)

実施例４
平均重合度が１４．６で、一級水酸基含有率が６４％のポリグリセリン１９．４ｇとベヘン酸（Ｃ２２）７４．１５ｇ、オレイン酸（Ｃ１８Ｆ１）６．４５ｇを反応フラスコに入れ、水酸化カリウム０．１ｇを加えた後、２６０℃でエステル化反応することにより、本発明品４の油脂の増粘又は固化剤として、エステル化率８３％のポリグリセリン脂肪酸エステルを得た。（実施例１と同様に算定したとき、構成脂肪酸中のベヘン酸の割合は８１％。構成脂肪酸（１）としてベヘン酸、（２）としてオレイン酸のモル比は、０．９１：０．０９。） Example 4
19.4 g of polyglycerin having an average degree of polymerization of 14.6 and a primary hydroxyl group content of 64%, 74.15 g of behenic acid (C22), and 6.45 g of oleic acid (C18F1) were placed in a reaction flask, and potassium hydroxide was 0. After adding 1 g, an esterification reaction was carried out at 260 ° C. to obtain a polyglycerin fatty acid ester having an esterification rate of 83% as a thickening or solidifying agent for the fat and oil of the product 4 of the present invention. (When calculated in the same manner as in Example 1, the proportion of behenic acid in the constituent fatty acids is 81%. The molar ratio of behenic acid as the constituent fatty acid (1) and oleic acid as the constituent fatty acid (2) is 0.91: 0.09. .)

実施例５
平均重合度が１４．３で、一級水酸基含有率が５２％のポリグリセリン１９．４ｇとベヘン酸（Ｃ２２）７４．１５ｇ、オレイン酸（Ｃ１８Ｆ１）６．４５ｇを反応フラスコに入れ、水酸化カリウム０．１ｇを加えた後、２６０℃でエステル化反応することにより、本発明品５の油脂の増粘又は固化剤として、エステル化率８３％のポリグリセリン脂肪酸エステルを得た。（実施例１と同様に算定したとき、構成脂肪酸中のベヘン酸の割合は８１％。構成脂肪酸（１）としてベヘン酸、（２）としてオレイン酸のモル比は、０．９１：０．０９。） Example 5
19.4 g of polyglycerin having an average degree of polymerization of 14.3 and a primary hydroxyl group content of 52%, 74.15 g of behenic acid (C22), and 6.45 g of oleic acid (C18F1) were placed in a reaction flask, and potassium hydroxide was 0. After adding 1 g, an esterification reaction was carried out at 260 ° C. to obtain a polyglycerin fatty acid ester having an esterification rate of 83% as a thickening or solidifying agent for the fat and oil of the product 5 of the present invention. (When calculated in the same manner as in Example 1, the proportion of behenic acid in the constituent fatty acids is 81%. The molar ratio of behenic acid as the constituent fatty acid (1) and oleic acid as the constituent fatty acid (2) is 0.91: 0.09. .)

実施例６
平均重合度が１３．５で、一級水酸基含有率が４３％のポリグリセリン１９．４ｇとベヘン酸（Ｃ２２）７４．１５ｇ、オレイン酸（Ｃ１８Ｆ１）６．４５ｇを反応フラスコに入れ、水酸化カリウム０．１ｇを加えた後、２６０℃でエステル化反応することにより、本発明品６の油脂の増粘又は固化剤として、エステル化率８２％のポリグリセリン脂肪酸エステルを得た。（実施例１と同様に算定したとき、構成脂肪酸中のベヘン酸の割合は８１％。構成脂肪酸（１）としてベヘン酸、（２）としてオレイン酸のモル比は、０．９１：０．０９。） Example 6
19.4 g of polyglycerin having an average degree of polymerization of 13.5 and a primary hydroxyl group content of 43%, 74.15 g of behenic acid (C22), and 6.45 g of oleic acid (C18F1) were placed in a reaction flask, and potassium hydroxide was 0. After adding 1 g, an esterification reaction was carried out at 260 ° C. to obtain a polyglycerin fatty acid ester having an esterification rate of 82% as a thickening or solidifying agent for the fat and oil of the product 6 of the present invention. (When calculated in the same manner as in Example 1, the proportion of behenic acid in the constituent fatty acids is 81%. The molar ratio of behenic acid as the constituent fatty acid (1) and oleic acid as the constituent fatty acid (2) is 0.91: 0.09. .)

実施例７
平均重合度が１３．９で、一級水酸基含有率が５７％のポリグリセリン１９．８ｇとベヘン酸（Ｃ２２）６０．１５ｇ、ステアリン酸（Ｃ１８）１３．６３ｇ、オレイン酸（Ｃ１８Ｆ１）６．４２ｇを反応フラスコに入れ、水酸化カリウム０．１ｇを加えた後、２６０℃でエステル化反応することにより、本発明品７の油脂の増粘又は固化剤として、エステル化率８３％のポリグリセリン脂肪酸エステルを得た。（実施例１と同様に算定したとき、構成脂肪酸中のベヘン酸の割合は６４％。構成脂肪酸（１）としてベヘン酸とステアリン酸、（２）としてオレイン酸のモル比は、０．９１：０．０９。） Example 7
19.8 g of polyglycerin having an average degree of polymerization of 13.9 and a primary fatty acid content of 57%, 60.15 g of behenic acid (C22), 13.63 g of stearic acid (C18), and 6.42 g of oleic acid (C18F1). A polyglycerin fatty acid ester having an esterification rate of 83% can be used as a thickening or solidifying agent for the fat and oil of the product 7 of the present invention by placing it in a reaction flask, adding 0.1 g of potassium hydroxide, and then performing an esterification reaction at 260 ° C. Got (When calculated in the same manner as in Example 1, the proportion of behenic acid in the constituent fatty acids was 64%. The molar ratio of behenic acid and stearic acid as the constituent fatty acids (1) and oleic acid as the constituent fatty acids (2) was 0.91: 0.91: 0.09.)

実施例８
平均重合度が１３．９で、一級水酸基含有率が５７％のポリグリセリン１９．５ｇとベヘン酸（Ｃ２２）６８．４３ｇ、パルミチン酸（Ｃ１６）５．６４ｇ、オレイン酸（Ｃ１８Ｆ１）６．４４ｇを反応フラスコに入れ、水酸化カリウム０．１ｇを加えた後、２６０℃でエステル化反応することにより、本発明品８の油脂の増粘又は固化剤として、エステル化率８３％のポリグリセリン脂肪酸エステルを得た。（実施例１と同様に算定したとき、構成脂肪酸中のベヘン酸の割合は７３％。構成脂肪酸（１）としてベヘン酸とパルミチン酸、（２）としてオレイン酸のモル比は、０．９１：０．０９。） Example 8
19.5 g of polyglycerin having an average degree of polymerization of 13.9 and a primary hydroxyl content of 57%, 68.43 g of behenic acid (C22), 5.64 g of palmitic acid (C16), and 6.44 g of oleic acid (C18F1). A polyglycerin fatty acid ester having an esterification rate of 83% can be used as a thickening or solidifying agent for the fat and oil of the product 8 of the present invention by placing it in a reaction flask, adding 0.1 g of potassium hydroxide, and then performing an esterification reaction at 260 ° C. Got (When calculated in the same manner as in Example 1, the proportion of behenic acid in the constituent fatty acids was 73%. The molar ratio of behenic acid and palmitic acid as the constituent fatty acids (1) and oleic acid as the constituent fatty acids (2) was 0.91: 0.91: 0.09.)

実施例９
平均重合度が１３．９で、一級水酸基含有率が５７％のポリグリセリン１９．４ｇとベヘン酸（Ｃ２２）７７．３８ｇ、カプリル酸（Ｃ８）３．２２ｇを反応フラスコに入れ、水酸化カリウム０．１ｇを加えた後、２６０℃でエステル化反応することにより、本発明品９の油脂の増粘又は固化剤として、エステル化率８３％のポリグリセリン脂肪酸エステルを得た。（実施例１と同様に算定したとき、構成脂肪酸中のベヘン酸の割合は８１％。構成脂肪酸（１）としてベヘン酸、（２）としてカプリル酸のモル比は、０．９１：０．０９。） Example 9
19.4 g of polyglycerin having an average degree of polymerization of 13.9 and a primary hydroxyl group content of 57%, 77.38 g of behenic acid (C22), and 3.22 g of caprylic acid (C8) were placed in a reaction flask, and potassium hydroxide was 0. After adding 1 g, an esterification reaction was carried out at 260 ° C. to obtain a polyglycerin fatty acid ester having an esterification rate of 83% as a thickening or solidifying agent for the fat and oil of the product 9 of the present invention. (When calculated in the same manner as in Example 1, the proportion of behenic acid in the constituent fatty acids was 81%. The molar ratio of behenic acid as the constituent fatty acid (1) and caprylic acid as the constituent fatty acid (2) was 0.91: 0.09. .)

実施例１０
平均重合度が１３．９で、一級水酸基含有率が５７％のポリグリセリン１９．４ｇとベヘン酸（Ｃ２２）７７．３８ｇ、オレイン酸（Ｃ１８Ｆ１）３．２２ｇを反応フラスコに入れ、水酸化カリウム０．１ｇを加えた後、２６０℃でエステル化反応することにより、本発明品１０の油脂の増粘又は固化剤として、エステル化率８２％のポリグリセリン脂肪酸エステルを得た。（実施例１と同様に算定したとき、構成脂肪酸中のベヘン酸の割合は８５％。構成脂肪酸（１）としてベヘン酸、（２）としてオレイン酸のモル比は、０．９５：０．０５。） Example 10
19.4 g of polyglycerin having an average degree of polymerization of 13.9 and a primary hydroxyl group content of 57%, 77.38 g of behenic acid (C22), and 3.22 g of oleic acid (C18F1) were placed in a reaction flask, and potassium hydroxide was 0. After adding 1 g, an esterification reaction was carried out at 260 ° C. to obtain a polyglycerin fatty acid ester having an esterification rate of 82% as a thickening or solidifying agent for the fats and oils of the product 10 of the present invention. (When calculated in the same manner as in Example 1, the ratio of behenic acid in the constituent fatty acids is 85%. The molar ratio of behenic acid as the constituent fatty acid (1) and oleic acid as the constituent fatty acid (2) is 0.95: 0.05. .)

実施例１１
平均重合度が１３．９で、一級水酸基含有率が５７％のポリグリセリン１９．４ｇとベヘン酸（Ｃ２２）７８．９９ｇ、オレイン酸（Ｃ１８Ｆ１）１．６１ｇを反応フラスコに入れ、水酸化カリウム０．１ｇを加えた後、２６０℃でエステル化反応することにより、本発明品１１の油脂の増粘又は固化剤として、エステル化率８１％のポリグリセリン脂肪酸エステルを得た。（実施例１と同様に算定したとき、構成脂肪酸中のベヘン酸の割合は８７％。構成脂肪酸（１）としてベヘン酸、（２）としてオレイン酸のモル比は、０．９８：０．０２。） Example 11
19.4 g of polyglycerin having an average degree of polymerization of 13.9 and a primary hydroxyl group content of 57%, 78.9 g of bechenic acid (C22), and 1.61 g of oleic acid (C18F1) were placed in a reaction flask, and potassium hydroxide was 0. After adding 1 g, an esterification reaction was carried out at 260 ° C. to obtain a polyglycerin fatty acid ester having an esterification rate of 81% as a thickening or solidifying agent for the fats and oils of the product 11 of the present invention. (When calculated in the same manner as in Example 1, the ratio of behenic acid in the constituent fatty acids is 87%. The molar ratio of behenic acid as the constituent fatty acid (1) and oleic acid as the constituent fatty acid (2) is 0.98: 0.02. .)

実施例１２
平均重合度が１３．９で、一級水酸基含有率が５７％のポリグリセリン２１．８ｇとベヘン酸（Ｃ２２）７１．９４ｇ、オレイン酸（Ｃ１８Ｆ１）６．２６ｇを反応フラスコに入れ、水酸化カリウム０．１ｇを加えた後、２６０℃でエステル化反応することにより、本発明品１２の油脂の増粘又は固化剤として、エステル化率７１％のポリグリセリン脂肪酸エステルを得た。（実施例１と同様に算定したとき、構成脂肪酸中のベヘン酸の割合は８１％。構成脂肪酸（１）としてベヘン酸、（２）としてオレイン酸のモル比は、０．９１：０．０９。） Example 12
21.8 g of polyglycerin having an average degree of polymerization of 13.9 and a primary hydroxyl group content of 57%, 71.94 g of behenic acid (C22), and 6.26 g of oleic acid (C18F1) were placed in a reaction flask, and potassium hydroxide was 0. After adding 1 g, an esterification reaction was carried out at 260 ° C. to obtain a polyglycerin fatty acid ester having an esterification rate of 71% as a thickening or solidifying agent for the fats and oils of the product 12 of the present invention. (When calculated in the same manner as in Example 1, the proportion of behenic acid in the constituent fatty acids is 81%. The molar ratio of behenic acid as the constituent fatty acid (1) and oleic acid as the constituent fatty acid (2) is 0.91: 0.09. .)

実施例１３
平均重合度が１３．９で、一級水酸基含有率が５７％のポリグリセリン２０．６ｇとベヘン酸（Ｃ２２）７３．０５ｇ、オレイン酸（Ｃ１８Ｆ１）６．３５ｇを反応フラスコに入れ、水酸化カリウム０．１ｇを加えた後、２６０℃でエステル化反応することにより、本発明品１３の油脂の増粘又は固化剤として、エステル化率７６％のポリグリセリン脂肪酸エステルを得た。（実施例１と同様に算定したとき、構成脂肪酸中のベヘン酸の割合は８１％。構成脂肪酸（１）としてベヘン酸、（２）としてオレイン酸のモル比は、０．９１：０．０９。） Example 13
20.6 g of polyglycerin having an average degree of polymerization of 13.9 and a primary hydroxyl group content of 57%, 73.05 g of bechenic acid (C22), and 6.35 g of oleic acid (C18F1) were placed in a reaction flask, and potassium hydroxide was 0. After adding 1 g, an esterification reaction was carried out at 260 ° C. to obtain a polyglycerin fatty acid ester having an esterification rate of 76% as a thickening or solidifying agent for the fat and oil of the product 13 of the present invention. (When calculated in the same manner as in Example 1, the proportion of behenic acid in the constituent fatty acids is 81%. The molar ratio of behenic acid as the constituent fatty acid (1) and oleic acid as the constituent fatty acid (2) is 0.91: 0.09. .)

比較例１
平均重合度が９．０で、一級水酸基含有率が５５％のポリグリセリン１９．０ｇとベヘン酸（Ｃ２２）７４．５２ｇ、オレイン酸（Ｃ１８Ｆ１）６．４８ｇを反応フラスコに入れ、水酸化カリウム０．１ｇを加えた後、２６０℃でエステル化反応することにより、比較品１の油脂の増粘又は固化剤として、エステル化率８０％のポリグリセリン脂肪酸エステルを得た。（実施例１と同様に算定したとき、構成脂肪酸中のベヘン酸の割合は８１％。構成脂肪酸（１）としてベヘン酸、（２）としてオレイン酸のモル比は、０．９１：０．０９。） Comparative Example 1
19.0 g of polyglycerin having an average degree of polymerization of 9.0 and a primary hydroxyl group content of 55%, 74.52 g of behenic acid (C22), and 6.48 g of oleic acid (C18F1) were placed in a reaction flask, and potassium hydroxide was 0. After adding 1 g, an esterification reaction was carried out at 260 ° C. to obtain a polyglycerin fatty acid ester having an esterification rate of 80% as a thickening or solidifying agent for the fats and oils of Comparative Product 1. (When calculated in the same manner as in Example 1, the proportion of behenic acid in the constituent fatty acids is 81%. The molar ratio of behenic acid as the constituent fatty acid (1) and oleic acid as the constituent fatty acid (2) is 0.91: 0.09. .)

比較例２
平均重合度が１３．９で、一級水酸基含有率が５７％のポリグリセリン２１．０ｇとベヘン酸（Ｃ２２）４９．７７ｇ、パルミチン酸（Ｃ１６）２２．９１ｇ、オレイン酸（Ｃ１８Ｆ１）６．３２ｇを反応フラスコに入れ、水酸化カリウム０．１ｇを加えた後、２６０℃でエステル化反応することにより、比較品２の油脂の増粘又は固化剤として、エステル化率８０％のポリグリセリン脂肪酸エステルを得た。（実施例１と同様に算定したとき、構成脂肪酸中のベヘン酸の割合は５１％。構成脂肪酸（１）としてベヘン酸とパルミチン酸、（２）としてオレイン酸のモル比は、０．９２：０．０８。） Comparative Example 2
21.0 g of polyglycerin having an average degree of polymerization of 13.9 and a primary hydroxyl content of 57%, 49.77 g of bechenic acid (C22), 22.91 g of palmitic acid (C16), and 6.32 g of oleic acid (C18F1). Put it in a reaction flask, add 0.1 g of potassium hydroxide, and then carry out an esterification reaction at 260 ° C. to obtain a polyglycerin fatty acid ester with an esterification rate of 80% as a thickening or solidifying agent for the fats and oils of Comparative Product 2. Obtained. (When calculated in the same manner as in Example 1, the proportion of behenic acid in the constituent fatty acids was 51%. The molar ratio of behenic acid and palmitic acid as the constituent fatty acids (1) and oleic acid as (2) was 0.92 :. 0.08.)

比較例３
平均重合度が１３．９で、一級水酸基含有率が５７％のポリグリセリン１９．４ｇとベヘン酸（Ｃ２２）８０．６ｇを反応フラスコに入れ、水酸化カリウム０．１ｇを加えた後、２６０℃でエステル化反応することにより、比較品３の油脂の増粘又は固化剤として、エステル化率８１％のポリグリセリン脂肪酸エステルを得た。（実施例１と同様に算定したとき、構成脂肪酸中のベヘン酸の割合は８９％。構成脂肪酸（１）としてベヘン酸、（２）の脂肪酸は含有せず、モル比は、１：０。） Comparative Example 3
19.4 g of polyglycerin having an average degree of polymerization of 13.9 and a primary hydroxyl group content of 57% and 80.6 g of behenic acid (C22) were placed in a reaction flask, 0.1 g of potassium hydroxide was added, and then 260 ° C. By the esterification reaction in (1), a polyglycerin fatty acid ester having an esterification rate of 81% was obtained as a thickening or solidifying agent for the fats and oils of Comparative Product 3. (When calculated in the same manner as in Example 1, the ratio of behenic acid in the constituent fatty acids was 89%. Behenic acid was not contained as the constituent fatty acid (1), and the fatty acid of (2) was not contained, and the molar ratio was 1: 0. )

比較例４
平均重合度が１３．９で、一級水酸基含有率が５７％のポリグリセリン１９．８ｇとベヘン酸（Ｃ２２）６４．９６ｇ、オレイン酸（Ｃ１８Ｆ１）１５．２４ｇを反応フラスコに入れ、水酸化カリウム０．１ｇを加えた後、２６０℃でエステル化反応することにより、比較品４の油脂の増粘又は固化剤として、エステル化率８２％のポリグリセリン脂肪酸エステルを得た。（実施例１と同様に算定したとき、構成脂肪酸中のベヘン酸の割合は６９％。構成脂肪酸（１）としてベヘン酸、（２）としてオレイン酸のモル比は、０．８：０．２。） Comparative Example 4
19.8 g of polyglycerin having an average degree of polymerization of 13.9 and a primary hydroxyl group content of 57%, 64.96 g of behenic acid (C22), and 15.24 g of oleic acid (C18F1) were placed in a reaction flask, and potassium hydroxide was 0. After adding 1 g, an esterification reaction was carried out at 260 ° C. to obtain a polyglycerin fatty acid ester having an esterification rate of 82% as a thickening or solidifying agent for the fats and oils of Comparative Product 4. (When calculated in the same manner as in Example 1, the ratio of behenic acid in the constituent fatty acids is 69%. The molar ratio of behenic acid as the constituent fatty acid (1) and oleic acid as the constituent fatty acid (2) is 0.8: 0.2. .)

比較例５
平均重合度が１３．９で、一級水酸基含有率が５７％のポリグリセリン２４．０ｇとベヘン酸（Ｃ２２）６９．９２ｇ、オレイン酸（Ｃ１８Ｆ１）６．０８ｇを反応フラスコに入れ、水酸化カリウム０．１ｇを加えた後、２６０℃でエステル化反応することにより、比較品５の油脂の増粘又は固化剤として、エステル化率６３％のポリグリセリン脂肪酸エステルを得た。（実施例１と同様に算定したとき、構成脂肪酸中のベヘン酸の割合は８１％。構成脂肪酸（１）としてベヘン酸、（２）としてオレイン酸のモル比は、０．９１：０．０９。） Comparative Example 5
24.0 g of polyglycerin having an average degree of polymerization of 13.9 and a primary hydroxyl group content of 57%, 69.92 g of behenic acid (C22), and 6.08 g of oleic acid (C18F1) were placed in a reaction flask, and potassium hydroxide was 0. After adding 1 g, an esterification reaction was carried out at 260 ° C. to obtain a polyglycerin fatty acid ester having an esterification rate of 63% as a thickening or solidifying agent for the fats and oils of Comparative Product 5. (When calculated in the same manner as in Example 1, the proportion of behenic acid in the constituent fatty acids is 81%. The molar ratio of behenic acid as the constituent fatty acid (1) and oleic acid as the constituent fatty acid (2) is 0.91: 0.09. .)

試験例１
５０ｍｌのガラス瓶（口内径φ３２×胴径φ４５×高さ７８ｍｍ）に本発明品１〜１３、及び比較品１〜５のいずれかを１．１２５ｇと油脂としてナタネ白絞油（ボーソー油脂株式会社製）を４８．８７５ｇ秤量した。それらを９０℃で加熱溶解し、２０℃で２時間静置することで、本発明品又は比較品を２．２５重量％添加した油脂を調製した。
得られた試料のゲル強度の測定を行った。ゲル強度とは、プランジャーが１ｍｍ進んだ時の反発強度（ｇ）で表される。ゲル強度の測定には、（株）レオテック製のＦＵＤＯＨ ＲＨＥＯＭＥＴＥＲ ＲＴ−２００２Ｄ−Ｄを用い、プランジャーには円柱形の直径１２．７ｍｍのものを用いた。
試験例１のゲル強度の結果を表１、２に示した。 Test Example 1
Rapeseed white squeezed oil (manufactured by Bosoh Oil & Fat Co., Ltd.) with 1.125 g of any of the products 1 to 13 of the present invention and the comparative products 1 to 5 in a 50 ml glass bottle (mouth inner diameter φ32 x body diameter φ45 x height 78 mm). ) Weighed 48.875 g. By heating and dissolving them at 90 ° C. and allowing them to stand at 20 ° C. for 2 hours, oils and fats to which the product of the present invention or the comparative product was added in an amount of 2.25% by weight were prepared.
The gel strength of the obtained sample was measured. The gel strength is represented by the repulsive strength (g) when the plunger advances by 1 mm. A FUDOH RHEOMETER RT-2002D-D manufactured by Leotech Co., Ltd. was used for measuring the gel strength, and a cylindrical plunger having a diameter of 12.7 mm was used.
The results of gel strength of Test Example 1 are shown in Tables 1 and 2.

試験例２
５０ｍｌのガラス瓶（口内径φ３２×胴径φ４５×高さ７８ｍｍ）に本発明品１〜１３、及び比較品１〜５を０．２ｇと香味油としてネギ油（ユウキ食品株式会社製）を４９．８ｇ秤量した。それらを９０℃で加熱溶解し、２０℃で２時間静置させ、本発明品又は比較品を０．４重量％添加した油脂を調製した。これに油不溶物としてバジルを０．１５ｇ混合することで試料を調製した。
この試料を２０℃で保存し、保存１日後、５日後、２０日後に油脂中でのバジルの分散状態を確認した。 Test Example 2
2. 8 g was weighed. They were heated and dissolved at 90 ° C. and allowed to stand at 20 ° C. for 2 hours to prepare a fat or oil to which the product of the present invention or a comparative product was added in an amount of 0.4% by weight. A sample was prepared by mixing 0.15 g of basil as an oil-insoluble matter.
This sample was stored at 20 ° C., and the dispersed state of basil in fats and oils was confirmed 1 day, 5 days, and 20 days after storage.

試験例２で確認した油脂中でのバジルの分散状態の評価基準は、バジルの沈降で生じる上清の体積割合とした。上清の体積割合(％)の測定は、（式２）より算出した。
（式２） (ネギ油液面の高さ５３ｍｍ−上清と沈降したバジルとの境界面の高さＸｍｍ)×１００／ネギ油液面の高さ５３ｍｍ
試験例２の結果を表３に示した。 The evaluation standard for the dispersed state of basil in the fat and oil confirmed in Test Example 2 was the volume ratio of the supernatant generated by the precipitation of basil. The measurement of the volume ratio (%) of the supernatant was calculated from (Equation 2).
(Equation 2) (Height of green onion oil level 53 mm-Height of interface between supernatant and sedimented basil X mm) x 100 / Height of green onion oil level 53 mm
The results of Test Example 2 are shown in Table 3.

試験例３
５０ｍｌのガラス瓶（口内径φ３２×胴径φ４５×高さ７８ｍｍ）に本発明品１〜１３を０．５ｇと香味油としてネギ油（ユウキ食品株式会社製）を４９．５ｇ秤量した。それらを９０℃で加熱溶解し、２０℃で２時間静置させ、本発明品を１．０重量％添加した油脂を調製した。これに油不溶物としてバジルを０．１５ｇ混合することで試料を調製した。
この試料を２０℃で保存し、保存１日後に油脂中でのバジルの分散状態を確認した。 Test Example 3
0.5 g of the products 1 to 13 of the present invention and 49.5 g of green onion oil (manufactured by Yuuki Foods Co., Ltd.) were weighed in a 50 ml glass bottle (mouth inner diameter φ32 × body diameter φ45 × height 78 mm). They were heated and dissolved at 90 ° C. and allowed to stand at 20 ° C. for 2 hours to prepare a fat and oil to which 1.0% by weight of the product of the present invention was added. A sample was prepared by mixing 0.15 g of basil as an oil-insoluble matter.
This sample was stored at 20 ° C., and one day after storage, the dispersed state of basil in fats and oils was confirmed.

試験例４
５０ｍｌのガラス瓶（口内径φ３２×胴径φ４５×高さ７８ｍｍ）に本発明品１〜１３を０．０５ｇと香味油としてネギ油（ユウキ食品株式会社製）を４９．９５ｇ秤量した。それらを９０℃で加熱溶解し、２０℃で２時間静置させ、本発明品を０．１重量％添加した油脂を調製した。これに油不溶物としてバジルを０．１５ｇ混合することで試料を調製した。
この試料を２０℃で保存し、保存１日後に油脂中でのバジルの分散状態を確認した。 Test Example 4
In a 50 ml glass bottle (mouth inner diameter φ32 × body diameter φ45 × height 78 mm), 0.05 g of the products 1 to 13 of the present invention and 49.95 g of green onion oil (manufactured by Yuuki Foods Co., Ltd.) as a flavor oil were weighed. They were heated and dissolved at 90 ° C. and allowed to stand at 20 ° C. for 2 hours to prepare oils and fats to which the product of the present invention was added in an amount of 0.1% by weight. A sample was prepared by mixing 0.15 g of basil as an oil-insoluble matter.
This sample was stored at 20 ° C., and one day after storage, the dispersed state of basil in fats and oils was confirmed.

試験例５
５０ｍｌのガラス瓶（口内径φ３２×胴径φ４５×高さ７８ｍｍ）に本発明品１〜１３を０．０２５ｇと香味油としてネギ油（ユウキ食品株式会社製）を４９．９７５ｇ秤量した。それらを９０℃で加熱溶解し、２０℃で２時間静置させ、本発明品を０．０５重量％添加した油脂を調製した。これに油不溶物としてバジルを０．１５ｇ混合することで試料を調製した。
この試料を２０℃で保存し、保存１日後に油脂中でのバジルの分散状態を確認した。 Test Example 5
0.025 g of the products 1 to 13 of the present invention and 49.975 g of green onion oil (manufactured by Yuuki Foods Co., Ltd.) were weighed in a 50 ml glass bottle (mouth inner diameter φ32 × body diameter φ45 × height 78 mm). They were heated and dissolved at 90 ° C. and allowed to stand at 20 ° C. for 2 hours to prepare oils and fats to which the product of the present invention was added in an amount of 0.05% by weight. A sample was prepared by mixing 0.15 g of basil as an oil-insoluble matter.
This sample was stored at 20 ° C., and one day after storage, the dispersed state of basil in fats and oils was confirmed.

試験例３〜５で確認した油中でのバジルの分散状態の評価基準は、バジルの沈降で生じる上清の体積割合とし、試験例２と同様に算出した。
試験例３〜５の結果を表４に示した。 The evaluation criteria for the dispersed state of basil in oil confirmed in Test Examples 3 to 5 was the volume ratio of the supernatant generated by the precipitation of basil, and was calculated in the same manner as in Test Example 2.
The results of Test Examples 3 to 5 are shown in Table 4.

試験例６
５０ｍｌのガラス瓶（口内径φ３２×胴径φ４５×高さ７８ｍｍ）に本発明品１を０．２ｇと油脂として菜種油（日清オイリオグループ株式会社製）、オリーブ油（株式会社Ｊ−オイルミルズ製）、ゴマ油（かどや製油株式会社製）のいずれかを４９．８ｇ秤量した。それらを９０℃で加熱溶解し、２０℃で２時間静置させ、本発明品１を０．４重量％添加した油脂を調製した。これに油不溶物としてバジルを０．１５ｇ混合することで試料を調製した。
この試料を２０℃で保存し、保存１日後、５日後、２０日後に油脂中でのバジルの分散状態を確認した。 Test Example 6
In a 50 ml glass bottle (mouth diameter φ32 x body diameter φ45 x height 78 mm), 0.2 g of the product 1 of the present invention and rapeseed oil (manufactured by Nisshin Oillio Group Co., Ltd.), olive oil (manufactured by J-Oil Mills Co., Ltd.), 49.8 g of any of the sesame oils (manufactured by Kadoya Sesame Co., Ltd.) was weighed. They were heated and dissolved at 90 ° C. and allowed to stand at 20 ° C. for 2 hours to prepare an oil or fat to which 0.4% by weight of the product 1 of the present invention was added. A sample was prepared by mixing 0.15 g of basil as an oil-insoluble matter.
This sample was stored at 20 ° C., and the dispersed state of basil in fats and oils was confirmed 1 day, 5 days, and 20 days after storage.

試験例６で確認した油脂中でのバジルの分散状態の評価基準は、バジルの沈降で生じる上清の体積割合とし、試験例２と同様に算出した。
試験例６の結果を表５に示した。 The evaluation standard of the dispersed state of basil in the fat and oil confirmed in Test Example 6 was the volume ratio of the supernatant generated by the sedimentation of basil, and was calculated in the same manner as in Test Example 2.
The results of Test Example 6 are shown in Table 5.

表１〜表２の結果から明らかなように、ナタネ白絞油に本発明品１〜１３を２．２５％添加し固化させた油脂は、ゲル強度６５以上の高いゲル強度を示した。これに対し、比較品１〜５を添加し増粘又は固化させた油脂は、本発明品１〜１３を添加し得られたものよりゲル強度が低く、低添加量で増粘又は固化を達成できなかった。 As is clear from the results in Tables 1 and 2, the fats and oils obtained by adding 2.25% of the products 1 to 13 of the present invention to the rapeseed white squeezed oil and solidifying the oil showed a high gel strength of 65 or more. On the other hand, the fats and oils thickened or solidified by adding Comparative Products 1 to 5 have lower gel strength than those obtained by adding Products 1 to 13 of the present invention, and achieve thickening or solidification with a low addition amount. could not.

表３の結果から明らかなように、香味油に本発明品１〜１３を添加し油不溶物としてバジルを分散させた油脂は、長期保存時も油不溶物の沈降による上清の体積割合が小さく、分散安定性にも優れた。一方、表３の結果から明らかなように、香味油に比較品１〜５を添加し油不溶物を分散させた油脂は、本発明品１〜１３を添加し得られたものより上清の体積割合が大きかった。特に、長期保存時にその割合の変動が大きく、分散安定性に劣った。 As is clear from the results in Table 3, the fats and oils obtained by adding the products 1 to 13 of the present invention to the flavor oil and dispersing basil as an oil-insoluble matter have a volume ratio of the supernatant due to the precipitation of the oil-insoluble matter even during long-term storage. It is small and has excellent dispersion stability. On the other hand, as is clear from the results in Table 3, the fats and oils obtained by adding Comparative Products 1 to 5 to the flavor oil and dispersing the oil-insoluble matter are more supernatant than those obtained by adding Products 1 to 13 of the present invention. The volume ratio was large. In particular, the ratio fluctuated greatly during long-term storage, and the dispersion stability was inferior.

表４の結果から明らかなように、香味油に本発明品１〜１３を各添加量で添加し油不溶物としてバジルを分散させた油脂は、いずれの添加量でも油不溶物の沈降による上清の体積割合が小さく、分散安定性に優れた。
表５の結果から明らかなように、各種の油脂に本発明品１を添加し油不溶物を分散させた油脂は、いずれの油脂でも油不溶物の沈降による上清の体積割合が小さく、分散安定性に優れた。 As is clear from the results in Table 4, the fats and oils in which products 1 to 13 of the present invention are added to the flavor oil in each addition amount and basil is dispersed as an oil insoluble matter are obtained by sedimentation of the oil insoluble matter in any addition amount. The volume ratio of Qing is small and the dispersion stability is excellent.
As is clear from the results in Table 5, the fats and oils obtained by adding the product 1 of the present invention to various fats and oils and dispersing the oil-insoluble matter have a small volume ratio of the supernatant due to the precipitation of the oil-insoluble matter, and are dispersed. Excellent stability.

以上本発明の油脂の増粘又は固化剤を油脂に添加することにより、少量の添加で増粘又は固化した油脂を得ることが可能であり、更には、油不溶物の分散安定性に優れた油脂を得ることも可能であり、飲食品に好適に用いることが可能となり、産業上の貢献は大である。 As described above, by adding the thickening or solidifying agent of the fat and oil of the present invention to the fat and oil, it is possible to obtain the fat and oil thickened or solidified by adding a small amount, and further, the dispersion stability of the oil insoluble matter is excellent. It is also possible to obtain oils and fats, which can be suitably used for foods and drinks, and has a great industrial contribution.

Claims (6)

下記条件（Ａ）〜（Ｄ）を満たす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油脂の増粘又は固化剤。
（Ａ）ポリグリセリン脂肪酸エステルの構成ポリグリセリンの平均重合度が１１〜２０
（Ｂ）ポリグリセリン脂肪酸エステルの構成脂肪酸中のベヘン酸の割合が６０％以上
（Ｃ）ポリグリセリン脂肪酸エステルの構成脂肪酸が、（１）炭素数１６〜２２の直鎖飽和脂肪酸を少なくとも１種以上、（２）炭素数８〜１４の直鎖飽和脂肪酸、炭素数１８〜２２の分岐脂肪酸及び炭素数１８〜２２の不飽和脂肪酸からなる群より選択される少なくとも１種以上を含有し、（１）：（２）のモル比が０．９１：０．０９〜０．９９：０．０１
（Ｄ）ポリグリセリン脂肪酸エステルのエステル化率が７０％以上 A thickening or solidifying agent for fats and oils, which contains a polyglycerin fatty acid ester that satisfies the following conditions (A) to (D).
(A) Composition of Polyglycerin Fatty Acid Ester The average degree of polymerization of polyglycerin is 11 to 20.
(B) The ratio of behenic acid in the constituent fatty acids of the polyglycerin fatty acid ester is 60% or more. (C) The constituent fatty acids of the polyglycerin fatty acid ester are (1) at least one linear saturated fatty acid having 16 to 22 carbon atoms. , (2) Containing at least one selected from the group consisting of linear saturated fatty acids having 8 to 14 carbon atoms, branched fatty acids having 18 to 22 carbon atoms and unsaturated fatty acids having 18 to 22 carbon atoms, and (1). ): The molar ratio of (2) is 0.91: 0.09 to 0.99: 0.01
(D) The esterification rate of polyglycerin fatty acid ester is 70% or more. 構成ポリグリセリンの水酸基のうち、１級水酸基含有率が５０％以上であることを特徴とする請求項１記載の油脂の増粘又は固化剤。 The thickening or solidifying agent for fats and oils according to claim 1, wherein the content of primary hydroxyl groups among the hydroxyl groups of the constituent polyglycerin is 50% or more. 請求項１又は２記載の油脂の増粘又は固化剤を含有する油脂。 A fat or oil containing a thickening or solidifying agent for the fat or oil according to claim 1 or 2. 請求項３記載の油脂が香味油である油脂の増粘又は固化剤を含有する油脂。 A fat or oil containing a thickening or solidifying agent for the fat or oil according to claim 3, wherein the fat or oil is a flavor oil. 請求項１又は２記載の油脂の増粘又は固化剤を０．０５重量％以上含有することを特徴とする請求項３又は４記載の油脂。 The fat or oil according to claim 3 or 4, wherein the fat or oil thickening or solidifying agent according to claim 1 or 2 is contained in an amount of 0.05% by weight or more. 請求項３〜５いずれか記載の油脂を含有する飲食品。 A food or drink containing the fat or oil according to any one of claims 3 to 5.