JP3358225B2 - Water-soluble compound oil-solubilized preparation and production method thereof - Google Patents
Water-soluble compound oil-solubilized preparation and production method thereofInfo
- Publication number
- JP3358225B2 JP3358225B2 JP04141793A JP4141793A JP3358225B2 JP 3358225 B2 JP3358225 B2 JP 3358225B2 JP 04141793 A JP04141793 A JP 04141793A JP 4141793 A JP4141793 A JP 4141793A JP 3358225 B2 JP3358225 B2 JP 3358225B2
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- JP
- Japan
- Prior art keywords
- water
- oil
- weight
- soluble compound
- solubilized
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Colloid Chemistry (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Edible Oils And Fats (AREA)
- General Preparation And Processing Of Foods (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、油脂に不溶であるため
使用が制限される水溶性化合物を、油脂中に均一に可溶
化することができる水溶性化合物油溶化製剤およびその
製造方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an oil-soluble preparation of a water-soluble compound capable of uniformly solubilizing a water-soluble compound which is insoluble in fats and oils and whose use is restricted, in fats and oils, and a process for producing the same.
【０００２】[0002]
【従来の技術】特開昭６３−１３５４８３号には、水溶
性抗酸化活性物質を親油性乳化剤を用いて乳化した油中
水型の親油性抗酸化剤が開示されている。この抗酸化剤
は活性物質の有する抗酸化力を低下させることなく油脂
に対する親和性が高められたものであり、油脂中に均一
に分散させることができる。しかし、この親油性抗酸化
剤は油中水型の乳化液であるので油脂中で乳化状態を示
し、このため油脂が白濁し、その結果油脂を水溶性の色
素などで着色する際色がくすむなどの問題点がある。ま
た比重の違いなどにより、抗酸化剤が油脂中に沈殿する
などの問題点がある。2. Description of the Related Art JP-A-63-135483 discloses a water-in-oil type lipophilic antioxidant obtained by emulsifying a water-soluble antioxidant active substance with a lipophilic emulsifier. This antioxidant has an increased affinity for fats and oils without lowering the antioxidant power of the active substance, and can be uniformly dispersed in fats and oils. However, since this lipophilic antioxidant is a water-in-oil type emulsion, it shows an emulsified state in fats and oils, so that the fats and oils become cloudy, and as a result, the color becomes dull when coloring the fats and oils with a water-soluble pigment. There are problems such as. Further, there is a problem that an antioxidant is precipitated in fats and oils due to a difference in specific gravity and the like.
【０００３】また特開平２−１１１４２６号には、ポリ
グリセリン縮合リシノレイン酸エステルを用いて、油脂
中に水溶性組成物を可溶化する方法が開示されている。
しかしこの方法においても水溶性化合物を油脂中に透明
な状態で溶解させることは難しく、油相に曇りが生じた
り、水溶性組成物の溶解量が多い場合は白濁するなどの
問題点がある。Japanese Patent Application Laid-Open No. 2-111426 discloses a method of solubilizing a water-soluble composition in fats and oils using polyglycerin condensed ricinoleate.
However, even in this method, it is difficult to dissolve the water-soluble compound in a fat or oil in a transparent state, and there are problems such as clouding of the oil phase and clouding when the amount of the water-soluble composition is large.
【０００４】[0004]
【発明が解決しようとする課題】本発明の目的は、上記
問題点を解決するため、油脂に不溶の水溶性化合物を白
濁させることなく透明な状態で、しかも容易に油脂に可
溶化できる水溶性化合物油溶化製剤を提供することであ
る。本発明の別の目的は、上記水溶性化合物油溶化製剤
を簡単に効率よく製造することができる水溶性化合物油
溶化製剤の製造方法を提案することである。SUMMARY OF THE INVENTION An object of the present invention is to solve the above-mentioned problems by dissolving a water-soluble compound insoluble in fats and oils in a transparent state without clouding and easily solubilizing the fats and oils. It is to provide a compound oil solubilized formulation. Another object of the present invention is to propose a method for producing a water-soluble compound oil-solubilized preparation which can easily and efficiently produce the water-soluble compound oil-solubilized preparation.
【０００５】[0005]
【課題を解決するための手段】本発明は次の水溶性化合
物油溶化製剤およびその製造方法である。 （１）（Ａ）カテキン類を除く水溶性化合物１〜４０重
量部、（Ｂ）水または／およびアルコール１〜４０重量
部、（Ｃ）ＨＬＢが６〜１４の乳化剤１〜３５重量部、
（Ｄ）ポリグリセリン縮合リシノレイン酸エステル５〜
７０重量部、ならびに（Ｅ）酵素分解レシチン０．５〜
３０重量部を含む製剤であって、前記（Ａ）、（Ｂ）お
よび（Ｃ）成分を含む水相部が、前記（Ｄ）成分中に可
溶化状態で分散している水溶性化合物油溶化製剤。 （２）（Ａ）カテキン類を除く水溶性化合物１〜４０重
量部、（Ｂ）水または／およびアルコール１〜４０重量
部、ならびに（Ｃ）ＨＬＢが６〜１４の乳化剤１〜３５
重量部を混合して得られた水相部と、（Ｄ）ポリグリセ
リン縮合リシノレイン酸エステル５〜７０重量部と、
（Ｅ）酵素分解レシチン０．５〜３０重量部とを混合
し、前記水相部を前記（Ｄ）成分中に可溶化状態で分散
させる水溶性化合物油溶化製剤の製造方法。SUMMARY OF THE INVENTION The present invention relates to the following oil-soluble preparation of a water-soluble compound and a method for producing the same. (1) (A) 1 to 40 parts by weight of a water-soluble compound excluding catechins, (B) 1 to 40 parts by weight of water or / and alcohol, (C) 1 to 35 parts by weight of an emulsifier having an HLB of 6 to 14,
(D) Polyglycerin condensed ricinoleate 5
70 parts by weight, and (E) enzymatically degraded lecithin 0.5 to
A formulation containing 30 parts by weight, wherein an aqueous phase containing the components (A), (B) and (C) is dispersed in the component (D) in a solubilized state. Formulation. (2) (A) 1 to 40 parts by weight of a water-soluble compound excluding catechins, (B) 1 to 40 parts by weight of water and / or alcohol, and (C) emulsifiers 1 to 35 having an HLB of 6 to 14.
An aqueous phase obtained by mixing parts by weight, (D) 5 to 70 parts by weight of a polyglycerin condensed ricinoleate,
(E) A method for producing a water-soluble compound oil-solubilized preparation, which comprises mixing 0.5 to 30 parts by weight of enzymatically decomposed lecithin and dispersing the aqueous phase in a solubilized state in the component (D).
【０００６】本発明で用いられる水溶性化合物（Ａ）と
しては、カテキン類を除く水溶性の化合物であって、そ
の種類に制限はなく、水溶性であって油脂中に溶解しな
いすべての化合物が使用できる。水溶性の化合物には不
純物が含まれていてもよく、また組成物や混合物であっ
てもよく、全体として水溶性のものであればよい。例え
ばカテキン類を除く抗酸化成分、水溶性色素、水溶性ビ
タミン、アミノ酸、調味料、ミネラル、有機酸、保存
料、タンパク質、甘味料、糖質、医薬品用生理活性物質
等があげられる。[0006] The water-soluble compound (A) used in the present invention is a water-soluble compound other than catechins, and there is no particular limitation on the type thereof. All compounds that are water-soluble and do not dissolve in fats and oils are included. Can be used. The water-soluble compound may contain impurities, may be a composition or a mixture, and may be a water-soluble compound as a whole. Examples thereof include antioxidants other than catechins, water-soluble pigments, water-soluble vitamins, amino acids, seasonings, minerals, organic acids, preservatives, proteins, sweeteners, carbohydrates, and physiologically active substances for pharmaceuticals.
【０００７】具体的なものとしては、アスコルビン酸、
没食子酸、クエン酸等に代表される有機酸、ブドウ種子
抽出物、ゴマ種子抽出物、ギシギシ種子抽出物、ローズ
マリー抽出物、セージ抽出物、クローブ抽出物、タイム
種子抽出物、ナツメグ抽出物、ターメリック抽出物等に
代表される天然物抽出物、甘草、桂皮等の生薬成分、メ
チオニン、トリプトファン、システィン等のアミノ酸、
メラノイジン等のアミノ酸変換物、大豆タンパク、乳タ
ンパクやその分解物等、抗酸化性を有する成分、ステビ
ア、紅花色素、乳酸カルシウム、カゼインナトリウム、
砂糖、しょう油などがあげられる。Specifically, ascorbic acid,
Gallic acid, organic acids represented by citric acid, etc., grape seed extract, sesame seed extract, crows seed extract, rosemary extract, sage extract, clove extract, thyme seed extract, nutmeg extract, Natural product extracts such as turmeric extracts, licorice, herbal ingredients such as cinnamon, methionine, tryptophan, amino acids such as cysteine,
Amino acid conversion products such as melanoidin, soy protein, milk protein and its decomposed products, etc., components having antioxidant properties, stevia, safflower pigment, calcium lactate, sodium caseinate,
Sugar, soy sauce and the like.
【０００８】水溶性化合物（Ａ）の水溶性化合物油溶化
製剤中の含有量は１〜４０重量部、好ましくは５〜３５
重量部である。水溶性化合物（Ａ）の含有量が１重量部
未満の場合、所定量の水溶性化合物（Ａ）を溶解するた
めに油脂に添加する水溶性化合物油溶化製剤の量が多く
なり、また４０重量部を超えると製剤を油脂中に完全に
可溶化することが難しくなる。The content of the water-soluble compound (A) in the oil-soluble preparation of the water-soluble compound is from 1 to 40 parts by weight, preferably from 5 to 35 parts by weight.
Parts by weight. When the content of the water-soluble compound (A) is less than 1 part by weight, the amount of the water-soluble compound oil-solubilized preparation to be added to the fat or oil to dissolve a predetermined amount of the water-soluble compound (A) increases, and the weight of the water-soluble compound (A) increases to 40%. If the amount exceeds the above range, it is difficult to completely solubilize the preparation in fats and oils.
【０００９】（Ｂ）の成分としては水またはアルコー
ル、あるいは両者の混合物が用いられる。アルコールと
しては、食品に用いることができるアルコールが使用で
き、エタノールが好適である。水または／およびアルコ
ール（Ｂ）の水溶性化合物油溶化製剤中の含有量は１〜
４０重量部、好ましくは５〜３５重量部であって、水溶
性化合物（Ａ）を完全に溶解できる量である。水または
／およびアルコール（Ｂ）の含有量が１重量部未満の場
合、水溶性化合物（Ａ）を完全に溶解するのが難しく、
また４０重量部を超えると水溶性化合物油溶化製剤を油
脂中に十分に可溶化するのが難しくなる。As the component (B), water or alcohol or a mixture of both is used. As the alcohol, alcohol that can be used for food can be used, and ethanol is preferable. The content of water or / and alcohol (B) in the water-soluble compound oil-solubilized preparation is from 1 to
The amount is 40 parts by weight, preferably 5 to 35 parts by weight, which is an amount capable of completely dissolving the water-soluble compound (A). When the content of water or / and alcohol (B) is less than 1 part by weight, it is difficult to completely dissolve water-soluble compound (A),
If the amount exceeds 40 parts by weight, it becomes difficult to sufficiently solubilize the water-soluble compound oil-solubilized preparation in fats and oils.
【００１０】本発明で使用するＨＬＢが６〜１４の乳化
剤（Ｃ）としては、市販の各種のアニオン系、非イオン
系、カチオン系、両性系の種々の乳化剤を使用すること
ができるが、食品に用いる場合には特にテトラグリセリ
ンモノオレエート、テトラグリセリンモノラウレート、
ヘキサグリセリンモノオレエート、ヘキサグリセリンモ
ノラウレート等のポリグリセリン脂肪酸エステル、およ
びショ糖脂肪酸エステル、ソルビタン脂肪酸エステルな
どが好適である。ＨＬＢは８〜１４のものが好ましい。As the emulsifier (C) having an HLB of 6 to 14 used in the present invention, various commercially available anionic, nonionic, cationic and amphoteric emulsifiers can be used. In particular, when used for tetraglycerin monooleate, tetraglycerin monolaurate,
Polyglycerin fatty acid esters such as hexaglycerin monooleate and hexaglycerin monolaurate, and sucrose fatty acid esters and sorbitan fatty acid esters are preferred. The HLB is preferably from 8 to 14.
【００１１】乳化剤（Ｃ）の水溶性化合物油溶化製剤中
の含有量は１〜３５重量部、好ましくは５〜３０重量部
である。乳化剤（Ｃ）の含有量が１重量部未満の場合、
水溶性化合物油溶化製剤を油脂に溶解した際、可溶化せ
ずに白濁し、また３５重量部を超えると可溶化したとき
に乳化剤のくもりが生じる。The content of the emulsifier (C) in the oil-soluble preparation of a water-soluble compound is 1 to 35 parts by weight, preferably 5 to 30 parts by weight. When the content of the emulsifier (C) is less than 1 part by weight,
When the water-soluble compound oil-solubilized preparation is dissolved in fats and oils, it becomes cloudy without being solubilized, and when it exceeds 35 parts by weight, cloudiness of an emulsifier occurs when solubilized.
【００１２】本発明に使用するポリグリセリン縮合リシ
ノレイン酸エステル（Ｄ）は、主としてひまし油を原料
とする縮合リシノレイン酸とポリグリセリンとのエステ
ル化反応により得られるものであり、ポリグリセリンの
重合度は２〜１６、好ましくは４〜１０、リシノレイン
酸の縮合度は２〜１６、好ましくは２〜１０のものがよ
い。The polyglycerin condensed ricinoleate (D) used in the present invention is obtained mainly by an esterification reaction of condensed ricinoleic acid with polyglycerin using castor oil as a raw material. -16, preferably 4-10, and the degree of condensation of ricinoleic acid is 2-16, preferably 2-10.
【００１３】具体的なものとしては、テトラグリセリン
縮合リシノレイン酸エステル、ヘキサグリセリン縮合リ
シノレイン酸エステル、これらの混合物などがあげられ
る。これらは単独で、または組み合わせて使用できる。Specific examples thereof include tetraglycerin condensed ricinoleate, hexaglycerin condensed ricinoleate, and mixtures thereof. These can be used alone or in combination.
【００１４】ポリグリセリン縮合リシノレイン酸エステ
ル（Ｄ）の水溶性化合物油溶化製剤中の含有量は５〜７
０重量部、好ましくは１０〜５０重量部である。ポリグ
リセリン縮合リシノレイン酸エステル（Ｄ）の含有量が
５重量部未満の場合、水溶性化合物油溶化製剤が二相に
分離し、また７０重量部を超えると水溶性化合物油溶化
製剤を油脂に溶解したとき白濁し、可溶化が難しい。The content of the polyglycerin condensed ricinoleate (D) in the oil-soluble preparation of a water-soluble compound is 5 to 7
0 parts by weight, preferably 10 to 50 parts by weight. When the content of polyglycerin condensed ricinoleate (D) is less than 5 parts by weight, the water-soluble compound oil-solubilized preparation separates into two phases, and when the content exceeds 70 parts by weight, the water-soluble compound oil-solubilized preparation is dissolved in fats and oils. Turbid and difficult to solubilize.
【００１５】本発明で使用する酵素分解レシチン（Ｅ）
はレシチンを加水分解酵素で加水分解したものであり、
例えば天然レシチンを加水分解酵素で分解したもの、あ
るいはこれを分画したものなど、種々使用することがで
きる。なお酵素分解しないレシチンを用いても、本発明
の目的とする水溶性化合物油溶化製剤は得られない。Enzymatically degraded lecithin (E) used in the present invention
Is hydrolyzed lecithin with a hydrolase,
For example, various types can be used, such as those obtained by degrading natural lecithin with a hydrolase, or those obtained by fractionating the same. Even if lecithin that does not undergo enzymatic degradation is used, the oil-soluble preparation of a water-soluble compound intended for the present invention cannot be obtained.
【００１６】酵素分解レシチン（Ｅ）の水溶性化合物油
溶化製剤中の含有量は０．５〜３０重量部、好ましくは
５〜３０重量部である。酵素分解レシチン（Ｅ）の含有
量が０．５重量部未満の場合、水溶性化合物油溶化製剤
は油脂に可溶化せず、乳化剤中水型乳化のままとなり、
これを溶解した油脂は白濁する。また３０重量部を超え
ると水溶性化合物油溶化製剤が経時的に二相に分離する
など水溶性化合物油溶化製剤の安定性が低下するととも
に、水溶性化合物油溶化製剤を添加した油脂中で、水溶
性化合物油溶化製剤が経時的に沈澱する恐れがある。The content of the enzymatically decomposed lecithin (E) in the oil-soluble preparation of a water-soluble compound is 0.5 to 30 parts by weight, preferably 5 to 30 parts by weight. When the content of the enzyme-decomposed lecithin (E) is less than 0.5 part by weight, the water-soluble compound oil-solubilized preparation does not become solubilized in fats and oils, and remains as a water-in-emulsifier emulsifier,
The oil or fat in which this is dissolved becomes cloudy. In addition, when the amount exceeds 30 parts by weight, the stability of the water-soluble compound oil-solubilized preparation decreases, such as separation of the water-soluble compound oil-solubilized preparation into two phases over time. The water-soluble compound oil-solubilized preparation may precipitate over time.
【００１７】本発明の水溶性化合物油溶化製剤において
は、（Ｃ）成分の乳化剤は水溶性化合物（Ａ）とポリグ
リセリン縮合リシノレイン酸エステル（Ｄ）との相溶性
を高める役割を果たしていると推定される。またポリグ
リセリン縮合リシノレイン酸エステル（Ｄ）は水溶性化
合物（Ａ）を油脂中に均一に分散させる役割を果たして
いると推定される。さらに酵素分解レシチン（Ｅ）はポ
リグリセリン縮合リシノレイン酸エステル（Ｄ）と水溶
性化合物（Ａ）との乳化剤中水型乳化物の界面活性を低
下させ、均一な可溶化物とする役割を果たしていると推
定される。In the water-soluble compound oil-solubilized preparation of the present invention, it is presumed that the emulsifier of the component (C) plays a role in enhancing the compatibility between the water-soluble compound (A) and the polyglycerin condensed ricinoleate (D). Is done. It is presumed that the polyglycerin-condensed ricinoleate (D) plays a role of uniformly dispersing the water-soluble compound (A) in fats and oils. Further, the enzymatically decomposed lecithin (E) reduces the surface activity of the water-in-emulsifier of the polyglycerin-condensed ricinoleate (D) and the water-soluble compound (A), and plays a role as a uniform solubilized product. It is estimated to be.
【００１８】次に、本発明の水溶性化合物油溶化製剤の
製造方法について説明する。本発明の水溶性化合物油溶
化製剤は、水溶性化合物（Ａ）、水または／およびアル
コール（Ｂ）ならびにＨＬＢが６〜１４の乳化剤（Ｃ）
を混合して得られた水相部と、ポリグリセリン縮合リシ
ノレイン酸エステル（Ｄ）と、酵素分解レシチン（Ｅ）
とを、前記含有量となるように混合し、水相部となる前
記溶液を（Ｄ）成分中に可溶化状態で分散させることに
より製造できる。Next, a method for producing the oil-soluble preparation of a water-soluble compound of the present invention will be described. The water-soluble compound oil-solubilized preparation of the present invention comprises a water-soluble compound (A), water or / and an alcohol (B), and an emulsifier (C) having an HLB of 6 to 14.
, A polyglycerin condensed ricinoleate (D), and an enzymatically degraded lecithin (E)
Are mixed so as to have the above content, and the solution to be the aqueous phase is dispersed in the component (D) in a solubilized state.
【００１９】本発明の製造方法では、（Ａ）、（Ｂ）お
よび（Ｃ）成分を混合して溶解させることが重要であ
り、これらの３成分と同時に（Ｄ）や（Ｅ）成分を加え
て溶液を調製したり、３成分の内いずれかの成分を
（Ｄ）や（Ｅ）成分に混合したりして製剤を製造して
も、本発明の目的とする製剤は得られない。In the production method of the present invention, it is important that the components (A), (B) and (C) are mixed and dissolved, and the components (D) and (E) are added simultaneously with these three components. Preparation of a solution by preparing a solution by mixing or mixing any one of the three components with the component (D) or (E) does not provide the target formulation of the present invention.
【００２０】水相部は（Ｄ）成分と混合して乳化剤中水
型乳化液を形成した後、（Ｅ）成分を加えて可溶化する
のが好ましいが、水相部と（Ｅ）成分とを混合した後、
（Ｄ）成分を混合してもよい。また水相部、（Ｄ）成分
および（Ｅ）成分を同時に混合することもできる。The aqueous phase is preferably mixed with the component (D) to form a water-in-emulsifier emulsion and then solubilized by adding the component (E). After mixing
The component (D) may be mixed. Further, the aqueous phase, the component (D) and the component (E) can be mixed simultaneously.
【００２１】好ましい製造方法としては、次のような方
法がある。まず水または／およびエタノール（Ｂ）で完
全に溶解した水溶性化合物（Ａ）に、ＨＬＢが６〜１４
の乳化剤（Ｃ）を混合して溶解する。次にこの混合溶解
物を水相部とし、これにポリグリセリン縮合リシノレイ
ン酸エステル（Ｄ）を添加して乳化し、乳化剤中水型乳
化液を形成する。この乳化剤中水型乳化液に酵素分解レ
シチン（Ｅ）を添加して十分に混和し、乳化液を可溶化
して本発明の水溶性化合物油溶化製剤を得る。調製に際
しては、必要に応じて加熱したり、また粘度を低下させ
るために油脂等で希釈してもよい。Preferred manufacturing methods include the following. First, the HLB is added to the water-soluble compound (A) completely dissolved in water or / and ethanol (B) in an amount of 6 to 14%.
And emulsifier (C) is mixed and dissolved. Next, this mixed solution is used as an aqueous phase portion, and polyglycerin condensed ricinoleate (D) is added to this and emulsified to form a water-in-emulsifier emulsion. The enzymatically degraded lecithin (E) is added to the water-in-emulsifier emulsifier and mixed well to solubilize the emulsified liquid to obtain the oil-soluble preparation of the present invention. At the time of preparation, it may be heated if necessary, or may be diluted with oil or the like to reduce the viscosity.
【００２２】上記のような製造方法の場合、水相部に
（Ｄ）成分を加えて乳化した際、水溶性化合物（Ａ）、
水または／およびアルコール（Ｂ）ならびにＨＬＢが６
〜１４の乳化剤（Ｃ）を含む水相部が、ポリグリセリン
縮合リシノレイン酸エステル（Ｄ）により内相に含み込
まれ、外相がポリグリセリン縮合リシノレイン酸エステ
ル（Ｄ）となった乳化剤中水型乳化液、すなわちポリグ
リセリン縮合リシノレイン酸エステル中水型乳化液が形
成される。この乳化液に酵素分解レシチン（Ｅ）を加え
ることにより、乳化液の界面活性が低下して可溶化状態
となり、一相の均一な製剤が得られる。In the case of the above production method, when the component (D) is added to the aqueous phase and emulsified, the water-soluble compound (A)
Water or / and alcohol (B) and HLB of 6
Aqueous phase emulsifier in which an aqueous phase portion containing emulsifiers (C) to (C) is contained in an internal phase by polyglycerin condensed ricinoleate (D) and an external phase is polyglycerin condensed ricinoleate (D) A liquid, ie, a water-in-polyglycerin condensed ricinoleate-in-water emulsion, is formed. By adding enzymatically decomposed lecithin (E) to this emulsion, the surface activity of the emulsion is reduced to a solubilized state, and a one-phase uniform preparation is obtained.
【００２３】このようにして得られた水溶性化合物油溶
化製剤は、そのまま、または油脂で希釈したものを油脂
に添加して使用できる。油脂への添加濃度は限定され
ず、使用目的、効果に応じて適宜選択すればよく、例え
ば０．０００１〜９９重量％の濃度で添加できる。本発
明の水溶性化合物油溶化製剤は油脂に添加した場合、透
明に溶解し、白濁しない。また長期間保存しても分離が
生じない。さらに、水溶性化合物の優れた特性が油脂中
で発揮される。The water-soluble compound oil-solubilized preparation thus obtained can be used as it is or after being diluted with a fat or oil and added to the fat or oil. The concentration to be added to fats and oils is not limited, and may be appropriately selected depending on the purpose of use and effect. For example, the concentration can be 0.0001 to 99% by weight. When the water-soluble compound oil-solubilized preparation of the present invention is added to fats and oils, it dissolves transparently and does not become cloudy. Also, no separation occurs even after long-term storage. Furthermore, the excellent properties of the water-soluble compound are exhibited in fats and oils.
【００２４】[0024]
【発明の効果】以上の通り、本発明の水溶性化合物油溶
化製剤は、特定量の水溶性化合物、水または／およびア
ルコール、ならびに乳化剤を含む溶液が、特定量の酵素
分解レシチンの存在下に、特定量のポリグリセリン縮合
リシノレイン酸エステル中に可溶化状態で分散している
ので、油脂に不溶の水溶性化合物を白濁させることなく
容易に油脂に可溶化できる。As described above, the water-soluble compound oil-solubilized preparation of the present invention can be used to prepare a solution containing a specific amount of a water-soluble compound, water or / and an alcohol, and an emulsifier in the presence of a specific amount of an enzymatically degraded lecithin. Since it is dispersed in a specific amount in a polyglycerin condensed ricinoleate in a solubilized state, a water-soluble compound insoluble in fats and oils can be easily solubilized in fats and oils without clouding.
【００２５】また本発明の製造方法によれば、上記水溶
性化合物油溶化製剤を簡単に効率よく製造できる。Further, according to the production method of the present invention, the water-soluble compound oil-soluble preparation can be produced simply and efficiently.
【００２６】[0026]
【実施例】次に、実施例により本発明を詳細に説明する
が、本発明はこれらによってなんら限定されるものでは
ない。Next, the present invention will be described in detail with reference to examples, but the present invention is not limited to these examples.
【００２７】実施例１ ２００ｍｌ容ガラスビーカーにステビア製剤（ＳＫスィ
ートＺ３、商品名、山陽国策パルプ株式会社製）１０
ｇ、蒸留水１５ｇ、テトラグリセリンモノラウレート
（ＳＹグリスターＭＬ３１０、商品名、阪本薬品工業株
式会社製、ＨＬＢ＝１０．３）１０ｇを添加し、プロペ
ラミキサーで十分に攪拌、混合しながら加熱し、５０℃
まで昇温して完全に溶解した。この溶液にポリグリセリ
ン縮合リシノレート（ＳＹグリスターＣＲ−ＥＤ、商品
名、阪本薬品工業株式会社製）３５ｇを添加して十分に
攪拌、混和し、乳化剤中水型乳化液とした。この乳化剤
中水型乳化液に対して酵素分解レシチン（エルマイザー
Ａ、商品名、協和発酵工業株式会社製）１０ｇを添加
し、再び５０℃まで加熱しながら混合し、ステビア油溶
化製剤８０ｇを得た。Example 1 Stevia preparation (SK Suite Z3, trade name, manufactured by Sanyo Kokusaku Pulp Co., Ltd.) 10 in a 200 ml glass beaker
g, distilled water 15 g, tetraglycerin monolaurate (SY Glister ML310, trade name, manufactured by Sakamoto Yakuhin Kogyo Co., Ltd., HLB = 10.3) was added, and the mixture was sufficiently stirred with a propeller mixer and heated while mixing. 50 ℃
The temperature was raised to complete dissolution. To this solution was added 35 g of polyglycerin-condensed ricinoleate (SY Glister CR-ED, trade name, manufactured by Sakamoto Yakuhin Kogyo Co., Ltd.), and the mixture was sufficiently stirred and mixed to obtain a water-in-emulsifier emulsion. 10 g of enzymatically decomposed lecithin (Elmizer A, trade name, manufactured by Kyowa Hakko Kogyo Co., Ltd.) was added to the water-in-emulsifier emulsifier, and mixed while heating to 50 ° C. again to obtain 80 g of a stevia oil-solubilized preparation. .
【００２８】この製剤８ｇにコーン油９２ｇを添加し、
混合した。この製剤溶解油脂はステビアの甘味が付与さ
せており、完全に透明に溶解していた。また、この製剤
溶解油脂を４０℃で１０日間保存したが、分離、浮遊物
の生成もなく、安定であった。To 8 g of this preparation, 92 g of corn oil was added,
Mixed. This formulation-dissolved fat had the sweet taste of stevia and was completely transparent and dissolved. In addition, this formulation-dissolved fat was stored at 40 ° C. for 10 days, but was stable without separation or formation of suspended matter.
【００２９】比較例１ 実施例１において酵素分解レシチンを使用しない他は実
施例１と同様にしてステビア製剤の油溶化製剤を作成し
た。この製剤７ｇをコーン油９３ｇに添加し、混合し
た。この製剤を添加した油脂は、白濁しており、すなわ
ちこの製剤は油脂に完全に透明な状態で溶解することが
できず、油溶化製剤として不適であった。Comparative Example 1 An oil solubilized preparation of a stevia preparation was prepared in the same manner as in Example 1 except that the enzyme-degraded lecithin was not used. 7 g of this preparation was added to 93 g of corn oil and mixed. The fat or oil to which this formulation was added was cloudy, that is, this formulation could not be completely dissolved in the fat or oil and was not suitable as an oil-solubilized formulation.
【００３０】実施例２ ２００ｍｌ容ガラスビーカーに没食子酸１０ｇを、蒸留
水１０ｇおよびエタノール１０ｇに溶解し、テトラグリ
セリンモノラウレート（前記ＳＹグリスターＭＬ３１
０、ＨＬＢ＝１０．３）２０ｇを添加し、５０℃に加熱
しながらプロペラミキサーで十分に攪拌し、混合溶解し
た。この溶液にポリグリセリン縮合リシノレイン酸エス
テル（前記ＳＹグリスターＣＲ−ＥＤ）２０ｇを添加し
て、再び加熱攪拌、混和して乳化剤中水型乳化液とし
た。この乳化液に、１０ｇの酵素分解レシチン（前記エ
ルマイザーＡ）および中鎖脂肪酸トリグリセライド１５
ｇを添加し、再び加熱しながら攪拌混合して、没食子酸
油溶化製剤９５ｇを得た。得られた没食子酸油溶化製剤
をコーン油に溶解したところ、０．００１重量％から１
０重量％の範囲内で透明に可溶化した。Example 2 In a 200 ml glass beaker, 10 g of gallic acid was dissolved in 10 g of distilled water and 10 g of ethanol, and tetraglycerin monolaurate (the aforementioned SY Glister ML31) was dissolved.
(0, HLB = 10.3), and the mixture was sufficiently stirred with a propeller mixer while heating to 50 ° C., and mixed and dissolved. To this solution was added 20 g of polyglycerin-condensed ricinoleate (the SY Glister CR-ED), and the mixture was again heated, stirred and mixed to obtain a water-in-emulsifier emulsion. To this emulsion, 10 g of enzymatically degraded lecithin (the above Elmizer A) and medium-chain fatty acid triglyceride 15
g, and the mixture was stirred and mixed while heating again to obtain 95 g of a gallic acid oil-solubilized preparation. When the obtained gallic acid oil-solubilized formulation was dissolved in corn oil, the content was 0.001% by weight to 1%.
It was transparently solubilized within the range of 0% by weight.
【００３１】実施例３ １００ｍｌ容ガラスビーカーに紅花色素１ｇを蒸留水１
０ｇに溶解し、テトラグリセリンモノオレート（ＳＹグ
リスターＭＯ３１０、商品名、阪本薬品工業株式会社
製、ＨＬＢ＝８．８）５ｇを添加し、加熱しながらプロ
ペラミキサーで十分に攪拌し、混合溶解した。この溶液
にポリグリセリン縮合リシノレイン酸エステル（前記Ｓ
ＹグリスターＣＲ−ＥＤ）１０ｇを添加して、再び加熱
攪拌、混和して乳化剤中水型乳化液とした。この乳化液
に、１０ｇの酵素分解レシチン（前記エルマイザーＡ）
およびコーン油１４ｇを添加し、加熱しながら攪拌混合
して紅花色素油溶化製剤５０ｇを得た。Example 3 1 g of safflower pigment was placed in a 100 ml glass beaker and distilled water 1
Then, 5 g of tetraglycerin monooleate (SY Glister MO310, trade name, manufactured by Sakamoto Yakuhin Kogyo Co., Ltd., HLB = 8.8) was added, and the mixture was sufficiently stirred with a propeller mixer while heating to mix and dissolve. This solution was mixed with polyglycerin condensed ricinoleate (S
Y-glister (CR-ED) (10 g) was added, and the mixture was again heated, stirred and mixed to obtain a water-in-emulsifier emulsion. Add 10 g of enzymatically degraded lecithin (the above Elmizer A) to this emulsion.
Then, 14 g of corn oil was added, and the mixture was stirred and mixed while heating to obtain 50 g of a safflower pigment oil-solubilized preparation.
【００３２】得られた紅花色素油溶化製剤をコーン油に
溶解したところ、０．００１重量％から１重量％の範囲
内で濁り無く溶解した。この製剤を０．１重量％溶解し
た油脂の色は赤色を呈しており、３０℃で１か月間の保
存中、色調変化もなく、着色剤として安定であった。When the obtained safflower pigment oil solubilized preparation was dissolved in corn oil, it was dissolved without turbidity in the range of 0.001% by weight to 1% by weight. The color of the oil or fat in which 0.1% by weight of this preparation was dissolved was red, and there was no change in color tone during storage at 30 ° C. for one month, and the colorant was stable.
【００３３】実施例４ ２００ｍｌ容ガラスビーカー中で乳酸カルシウム１０ｇ
を水２５ｇに溶解し、テトラグリセリンモノラウレート
（前記ＳＹグリスターＭＬ３１０、ＨＬＢ＝１０．３）
１５ｇを添加し、加熱しながら十分に攪拌し、混合溶解
した。この溶液にポリグリセリン縮合リシノレイン酸エ
ステル（前記ＳＹグリスターＣＲ−ＥＤ）２５ｇを添加
して、再び加熱攪拌、混和して乳化剤中水型乳化液とし
た。この乳化液に、１５ｇの酵素分解レシチン（前記エ
ルマイザーＡ）を添加し、加熱しながら攪拌混合し、さ
らにコーン油１０ｇを滴下して攪拌、混合し、乳酸カル
シウム油溶化製剤１００ｇを得た。得られた乳酸カルシ
ウム油溶化製剤をコーン油に添加し、溶解したところ、
０．００１重量％から１０重量％の範囲で可溶化し、室
温で１０日間放置しても沈澱せず、均一に分散してい
た。Example 4 10 g of calcium lactate in a 200 ml glass beaker
Is dissolved in 25 g of water, and tetraglycerin monolaurate (the SY Glister ML310, HLB = 10.3)
15 g was added, and the mixture was sufficiently stirred while heating, and mixed and dissolved. To this solution was added 25 g of polyglycerin condensed ricinoleate (the SY Glister CR-ED), and the mixture was again heated, stirred and mixed to obtain a water-in-emulsifier emulsion. To this emulsion, 15 g of enzymatically decomposed lecithin (the above-mentioned Elmizer A) was added and mixed while stirring, and 10 g of corn oil was added dropwise, followed by stirring and mixing to obtain 100 g of a calcium lactate oil-solubilized preparation. The resulting calcium lactate oil solubilized formulation was added to corn oil and dissolved,
It was solubilized in the range of 0.001% by weight to 10% by weight, did not precipitate even after standing at room temperature for 10 days, and was uniformly dispersed.
【００３４】実施例５ ２００ｍｌ容ガラスビーカーに市販の濃い口醤油１０ｇ
にテトラグリセリンモノラウレート（前記ＳＹグリスタ
ーＭＬ３１０、ＨＬＢ＝１０．３）１０ｇを添加し、加
熱しながら十分に攪拌し、混合溶解した。この溶液にポ
リグリセリン縮合リシノレイン酸エステル（前記ＳＹグ
リスターＣＲ−ＥＤ）１５ｇを添加して再び加熱攪拌、
混和して乳化剤中水型乳化液とした。この乳化液に、１
５ｇの酵素分解レシチン（前記エルマイザーＡ）を添加
し、加熱しながら攪拌混合して醤油油溶化製剤１０ｇを
得た。Example 5 10 g of commercially available dark soy sauce in a 200 ml glass beaker
10 g of tetraglycerin monolaurate (the SY Glister ML310, HLB = 10.3) was added thereto, sufficiently stirred while heating, and mixed and dissolved. To this solution was added 15 g of polyglycerin condensed ricinoleate (the SY Glister CR-ED), and heated and stirred again.
It was mixed to obtain a water-in-emulsifier emulsion. In this emulsion, 1
5 g of enzymatically decomposed lecithin (the above-mentioned Elmizer A) was added, and the mixture was stirred and mixed while heating to obtain 10 g of a soy sauce oil-solubilized preparation.
【００３５】得られた醤油油溶化製剤を菜種油に添加
し、溶解したところ、０．００１重量％から５０重量％
の範囲で可溶化し、室温で１４日間放置しても分離、沈
澱の無い良好な可溶化状態を示した。またこの醤油油溶
化製剤溶解油脂は、良好な醤油風味を示し、５℃で３０
日間保存しても、変化は示さなかった。When the soy sauce oil solubilized preparation was added to rapeseed oil and dissolved, 0.001% by weight to 50% by weight was obtained.
And showed a good solubilized state without separation and precipitation even after standing at room temperature for 14 days. This soy sauce oil-solubilized preparation-dissolved fat and oil shows a good soy sauce flavor and has a 30
No changes were noted after storage for days.
【００３６】実施例６ カゼインナトリウム５ｇを水２０ｇに溶解し、テトラグ
リセリンモノラウレート（前記ＳＹグリスターＭＬ３１
０、ＨＬＢ＝１０．３）１５ｇを添加して、加熱しなが
ら十分に攪拌し、混合溶解した。この溶液にポリグリセ
リン縮合リシノレイン酸エステル（前記ＳＹグリスター
ＣＲ−ＥＤ）４０ｇを添加して、再び加熱攪拌、混和し
て乳化剤中水型乳化液とした。この乳化液に、１５ｇの
酵素分解レシチン（前記エルマイザーＡ）を添加し、加
熱しながら攪拌混合してカゼインナトリウム油溶化製剤
１００ｇを得た。得られたカゼインナトリウム油溶化製
剤は、油脂に自由な濃度で混合でき、沈澱の発生なども
認められなかった。Example 6 5 g of sodium caseinate was dissolved in 20 g of water, and tetraglycerin monolaurate (the above-mentioned SY Glister ML31) was dissolved.
(0, HLB = 10.3) was added, and the mixture was sufficiently stirred while heating to mix and dissolve. To this solution was added 40 g of polyglycerin-condensed ricinoleate (the SY Glister CR-ED), and the mixture was again heated, stirred and mixed to obtain a water-in-emulsifier emulsion. To this emulsion, 15 g of enzymatically-decomposed lecithin (the above-mentioned Elmizer A) was added and stirred and mixed while heating to obtain 100 g of sodium caseinate oil-solubilized preparation. The obtained sodium caseinate oil-solubilized preparation could be mixed with fats and oils at a free concentration, and no precipitation was observed.
【００３７】実施例７〜１０、比較例２〜６ 砂糖を表１に示す配合で油溶化製剤化した。得られた各
製剤についてその状態、油脂に添加した際の状態などを
観察した。結果を表２に示す。Examples 7 to 10 and Comparative Examples 2 to 6 Sugars were formulated into oil-solubilized formulations according to the formulation shown in Table 1. The state of each of the obtained preparations, the state when added to fats and oils, and the like were observed. Table 2 shows the results.
【００３８】[0038]
【表１】 [Table 1]
【００３９】[0039]
【表２】 [Table 2]
【００４０】表２から、実施例の製剤は、透明に可溶化
するが、本発明で示した範囲を逸脱した比較例のものは
白濁、あるいは製剤が分離して、水溶性化合物油溶化製
剤として適さないことがわかる。From Table 2, it can be seen that the preparations of the examples are transparently solubilized, whereas those of the comparative examples which deviate from the range described in the present invention are cloudy or the preparations are separated to form a water-soluble compound oil-solubilized preparation. It turns out that it is not suitable.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 ＦＩ // Ａ２３Ｄ 9/007 Ａ２３Ｄ 9/00 ５０４ (58)調査した分野(Int.Cl.7，ＤＢ名) A23L 1/035,3/3472 B01J 13/00 B01F 17/44 ────────────────────────────────────────────────── ─── Continued on the front page (51) Int.Cl. 7 identification symbol FI // A23D 9/007 A23D 9/00 504 (58) Investigated field (Int.Cl. 7 , DB name) A23L 1/035, 3/3472 B01J 13/00 B01F 17/44
Claims (2)
〜４０重量部、 （Ｂ）水または／およびアルコール１〜４０重量部、 （Ｃ）ＨＬＢが６〜１４の乳化剤１〜３５重量部、 （Ｄ）ポリグリセリン縮合リシノレイン酸エステル５〜
７０重量部、ならびに （Ｅ）酵素分解レシチン０．５〜３０重量部 を含む製剤であって、前記（Ａ）、（Ｂ）および（Ｃ）
成分を含む水相部が、前記（Ｄ）成分中に可溶化状態で
分散していることを特徴とする水溶性化合物油溶化製
剤。1. (A) Water-soluble compound 1 excluding catechins
(B) 1 to 40 parts by weight of water or / and alcohol, (C) 1 to 35 parts by weight of an emulsifier having an HLB of 6 to 14, (D) polyglycerin condensed ricinoleate 5 to
A formulation comprising 70 parts by weight, and (E) 0.5 to 30 parts by weight of enzymatically degraded lecithin, wherein (A), (B) and (C)
An aqueous solution of a water-soluble compound, wherein the aqueous phase containing the component is dispersed in the component (D) in a solubilized state.
〜４０重量部、 （Ｂ）水または／およびアルコール１〜４０重量部、な
らびに （Ｃ）ＨＬＢが６〜１４の乳化剤１〜３５重量部を混合
して得られた水相部と、 （Ｄ）ポリグリセリン縮合リシノレイン酸エステル５〜
７０重量部と、 （Ｅ）酵素分解レシチン０．５〜３０重量部と を混合し、前記水相部を前記（Ｄ）成分中に可溶化状態
で分散させることを特徴とする水溶性化合物油溶化製剤
の製造方法。2. (A) Water-soluble compound 1 excluding catechins
(B) 1 to 40 parts by weight of water or / and an alcohol, and (C) an aqueous phase obtained by mixing 1 to 35 parts by weight of an emulsifier having an HLB of 6 to 14; Polyglycerin condensed ricinoleate 5
70 parts by weight of (E) enzymatically decomposed lecithin 0.5 to 30 parts by weight, and the aqueous phase is dispersed in the component (D) in a solubilized state. Manufacturing method of solubilized preparation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04141793A JP3358225B2 (en) | 1993-03-02 | 1993-03-02 | Water-soluble compound oil-solubilized preparation and production method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP04141793A JP3358225B2 (en) | 1993-03-02 | 1993-03-02 | Water-soluble compound oil-solubilized preparation and production method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06254378A JPH06254378A (en) | 1994-09-13 |
| JP3358225B2 true JP3358225B2 (en) | 2002-12-16 |
Family
ID=12607785
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP04141793A Expired - Lifetime JP3358225B2 (en) | 1993-03-02 | 1993-03-02 | Water-soluble compound oil-solubilized preparation and production method thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3358225B2 (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1298825C (en) * | 2000-06-12 | 2007-02-07 | 不二制油株式会社 | Process for producing fat |
| ATE369831T1 (en) | 2000-06-14 | 2007-09-15 | Pure Green Co Ltd | OILY COSMETICS |
| JP5659060B2 (en) * | 2010-11-19 | 2015-01-28 | 理想科学工業株式会社 | Water-in-oil (W / O) emulsion ink for inkjet |
| JP5652557B2 (en) | 2012-05-16 | 2015-01-14 | 不二製油株式会社 | Edible oil and fat, food containing the same, and method for producing the same |
| JP6098046B2 (en) * | 2012-06-15 | 2017-03-22 | 不二製油株式会社 | Edible oil and fat, food containing the same and method for producing the same |
| KR102262708B1 (en) | 2013-07-09 | 2021-06-08 | 후지세유 그룹 혼샤 가부시키가이샤 | Frozen confectionery, and oil and fat for producing confectionery |
| AU2014347912B2 (en) | 2013-11-13 | 2018-01-04 | Fuji Oil Holdings Inc. | Fat containing polyunsaturated fatty acid |
| KR20160050826A (en) * | 2014-10-31 | 2016-05-11 | 씨제이제일제당 (주) | Emulsified oil comprising antioxidants, cooking oil comprising the emulsified oil and manufacturing methods of thereof |
| JP5786215B1 (en) * | 2015-02-09 | 2015-09-30 | フードテック・トレーディング株式会社 | Antioxidant composition and fats and oils to which it is added |
-
1993
- 1993-03-02 JP JP04141793A patent/JP3358225B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06254378A (en) | 1994-09-13 |
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