JP6196168B2 - Inhibitor of crystal growth of lauric oil - Google Patents

Inhibitor of crystal growth of lauric oil Download PDF

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JP6196168B2
JP6196168B2 JP2014019092A JP2014019092A JP6196168B2 JP 6196168 B2 JP6196168 B2 JP 6196168B2 JP 2014019092 A JP2014019092 A JP 2014019092A JP 2014019092 A JP2014019092 A JP 2014019092A JP 6196168 B2 JP6196168 B2 JP 6196168B2
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晋哉 山根
晋哉 山根
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本発明は、ラウリン系油脂の結晶成長抑制剤に関する。   The present invention relates to a crystal growth inhibitor for lauric fats and oils.

ヤシ油やパーム核油等、炭素数12のラウリン酸を主要構成脂肪酸とするラウリン系油脂は、冷感を伴った良好な口融け及び淡白な風味を有しており、例えばチョコレート、アイスクリーム等の冷菓、マーガリン・ショートニング等の可塑性油脂組成物、起泡性クリーム、コーヒーホワイトナー・調整乳等の液状又は粉末状の乳製品又は油脂組成物等、種々の油脂含有食品に使用されている。   Laurin-based fats and oils containing lauric acid having 12 carbon atoms as a main constituent fatty acid, such as coconut oil and palm kernel oil, have a good melt with a cold feeling and a light white flavor, such as chocolate and ice cream. It is used in various fat-containing foods such as frozen confectionery, margarine / shortening plastic oil and fat compositions, foaming creams, liquid white or powdered dairy products such as coffee whitener and adjusted milk, and oil and fat compositions.

しかし、ラウリン系油脂は特に低温下で結晶が成長し易く、ラウリン系油脂を使用した油脂含有食品は、その結晶成長に起因する品質悪化が生じることがある。例えば、ラウリン系油脂を使用したコーヒーホワイトナーは、冷蔵保存時に乳化状態が不安定になることが知られている。   However, lauric fats and oils are particularly prone to grow crystals at low temperatures, and fat-containing foods using lauric fats and oils may deteriorate in quality due to the crystal growth. For example, it is known that a coffee whitener using lauric fats and oils becomes unstable in emulsified state during refrigerated storage.

このような問題に対し、ラウリン系油脂を使用したコーヒーホワイトナーの技術分野では、乳化安定性向上のためにラウリン系油脂の分別液体部を使用する方法(特許文献1)、ラウリン系油脂と液体油脂を併用する方法(特許文献2及び3)等が提案されている。   In order to solve such problems, in the technical field of coffee whiteners using lauric fats and oils, a method using a fractionated liquid part of lauric fats and oils for improving emulsification stability (Patent Document 1), lauric fats and liquids Methods for using oils and fats together (Patent Documents 2 and 3) have been proposed.

しかし、上記方法によるコーヒーホワイトナーは十分な粘性が得られず、クリーム感が劣り、コーヒーに添加した場合の分散性も悪い。しかも、上記方法は、コーヒーホワイトナー等の特定の技術分野での使用を想定しており、ラウリン系油脂を使用した油脂含有食品全般に応用可能なものではない。   However, the coffee whitener according to the above method cannot obtain a sufficient viscosity, has a poor cream feeling, and has poor dispersibility when added to coffee. Moreover, the above method is assumed to be used in a specific technical field such as a coffee whitener, and is not applicable to all fat-containing foods using lauric fats and oils.

そこで、ラウリン系油脂の結晶成長を直接抑制すれば、ラウリン系油脂を原料とする様々な形態の油脂含有食品について、ラウリン系油脂の結晶成長に起因する好ましくない現象を抑制できると考えられる。従って、ラウリン系油脂に添加することにより、その結晶成長を抑制できる結晶成長抑制剤が強く望まれている。   Therefore, if the crystal growth of lauric fats and oils is directly suppressed, it is considered that undesired phenomena due to the crystal growth of lauric fats and oils can be suppressed in various forms of fat and oil-containing foods made from lauric fats and oils. Therefore, there is a strong demand for a crystal growth inhibitor that can suppress the crystal growth when added to lauric oils.

特開2005−204653号公報JP 2005-204653 A 特開平07−079698号公報Japanese Patent Laid-Open No. 07-079698 特許第4003804号公報Japanese Patent No. 4003804

本発明は、ラウリン系油脂に添加することにより、その結晶成長を抑制できる結晶成長抑制剤を提供することを目的とする。   An object of this invention is to provide the crystal growth inhibitor which can suppress the crystal growth by adding to a lauric oil and fat.

本発明者は、上記課題に対して鋭意検討を行った結果、脂肪酸組成及びエステル化率に特徴があるソルビタン脂肪酸エステルにより上記課題が解決されることを見出し、この知見に基づいて本発明を成すに至った。   As a result of intensive studies on the above problems, the present inventor has found that the above problems can be solved by sorbitan fatty acid esters characterized by fatty acid composition and esterification rate, and the present invention is made based on this finding. It came to.

すなわち、本発明は、下記の(1)及び(2)からなっている。
(1)下記条件(A)及び(B)を満たすソルビタン脂肪酸エステルを有効成分とすることを特徴とするラウリン系油脂の結晶成長抑制剤。
(A):構成脂肪酸中の炭素数10〜14の脂肪酸含有量が45%以上;
(B):エステル化率が35〜85%。
(2)前記(1)に記載の結晶成長抑制剤を含有することを特徴とするラウリン系油脂組成物。
That is, the present invention comprises the following (1) and (2).
(1) A crystal growth inhibitor for lauric fats and oils characterized in that a sorbitan fatty acid ester satisfying the following conditions (A) and (B) is an active ingredient.
(A): The fatty acid content of 10 to 14 carbon atoms in the constituent fatty acid is 45% or more;
(B): The esterification rate is 35 to 85%.
(2) A lauric oil / fat composition comprising the crystal growth inhibitor according to (1).

本発明の結晶成長抑制剤を添加したラウリン系油脂組成物は、結晶成長が抑制されている。   In the lauric oil / fat composition to which the crystal growth inhibitor of the present invention is added, crystal growth is suppressed.

図1は、実施例の結晶成長抑制剤(試作品F)を添加したラウリン系油脂組成物に生成した結晶の状態を示す光学顕微鏡写真(倍率500倍)である。FIG. 1 is an optical micrograph (magnification 500 times) showing the state of crystals produced in the lauric oil composition to which the crystal growth inhibitor (prototype F) of the example was added. 図2は、比較例の結晶成長抑制剤(試作品H)を添加したラウリン系油脂組成物に生成した結晶の状態を示す光学顕微鏡写真(倍率500倍)である。FIG. 2 is an optical micrograph (magnification 500 times) showing the state of crystals produced in a lauric oil composition to which a crystal growth inhibitor (prototype H) of a comparative example was added. 図3は、比較例の結晶成長抑制剤(試作品L)を添加したラウリン系油脂組成物に生成した結晶の状態を示す光学顕微鏡写真(倍率500倍)である。FIG. 3 is an optical micrograph (magnification 500 times) showing the state of crystals produced in the lauric oil composition to which the crystal growth inhibitor (prototype L) of the comparative example was added.

本発明で用いられるソルビタン脂肪酸エステルは、下記条件(A)及び(B)を満たすものである。   The sorbitan fatty acid ester used in the present invention satisfies the following conditions (A) and (B).

[条件(A)について]
本発明で用いられるソルビタン脂肪酸エステルは、構成脂肪酸100%中、炭素数10〜14の脂肪酸(好ましくは飽和脂肪酸)の含有量が45%以上、好ましくは50%以上、より好ましくは60%以上である。炭素数10〜14の脂肪酸の含有量が45%未満であると、ラウリン系油脂の結晶成長抑制効果が十分に得られず、好ましくない。炭素数が10〜14の脂肪酸としては、カプリン酸(炭素数10)、ラウリン酸(炭素数12)及びミリスチン酸(炭素数14)が挙げられ、好ましくはラウリン酸である。
[Condition (A)]
The sorbitan fatty acid ester used in the present invention has a fatty acid content of 10 to 14 carbon atoms (preferably a saturated fatty acid) in 100% constituent fatty acids of 45% or more, preferably 50% or more, more preferably 60% or more. is there. If the content of the fatty acid having 10 to 14 carbon atoms is less than 45%, the effect of suppressing the crystal growth of lauric fats and oils cannot be sufficiently obtained, which is not preferable. Examples of the fatty acid having 10 to 14 carbon atoms include capric acid (10 carbon atoms), lauric acid (12 carbon atoms), and myristic acid (14 carbon atoms), and lauric acid is preferable.

ここで、条件(A)の構成脂肪酸の含有量とは、ソルビタン脂肪酸エステルの製造の原料となる脂肪酸100%中の含有量を指すが、この含有量は、製造されたソルビタン脂肪酸エステルについて下記工程(1)〜(3)を実施して測定しても良い。
(1)試料の調製
「基準油脂分析試験法(I)」(社団法人 日本油化学会編)の[2.4.1.2−1996 メチルエステル化法(三フッ化ホウ素メタノール法)]に準じて試料を調製する。
(2)測定方法
「基準油脂分析試験法(I)」(社団法人 日本油化学会編)の[2.4.2.2−1996 脂肪酸組成(FID昇温ガスクロマトグラフ法)]に準じて測定する。
(3)定量
データ処理装置により記録されたピーク面積の総和に対する各ピーク面積の百分率をもって構成脂肪酸の含有量とする。
Here, the content of the constituent fatty acid in the condition (A) refers to the content in 100% of the fatty acid used as a raw material for producing the sorbitan fatty acid ester, and this content is the following process for the produced sorbitan fatty acid ester: You may measure by implementing (1)-(3).
(1) Preparation of sample In “2.4.1.2-1996 methyl esterification method (boron trifluoride methanol method)” of “Standard oil analysis test method (I)” (edited by the Japan Oil Chemists' Society). Prepare a sample according to the procedure.
(2) Measuring method Measured according to [2.4.2.2-1996 Fatty acid composition (FID temperature rising gas chromatograph method)] of "Standard oil analysis test method (I)" (edited by the Japan Oil Chemists' Society). To do.
(3) Quantification The percentage of each peak area with respect to the total peak area recorded by the data processing apparatus is taken as the content of constituent fatty acids.

[条件(B)について]
本発明で用いられるソルビタン脂肪酸エステルのエステル化率は35〜85%であり、より好ましくは50〜80%である。エステル化率が35%未満であると、ラウリン系油脂の収縮抑制効果が十分に得られず、好ましくない。またエステル化率が85%を超えるソルビタン脂肪酸エステルは、反応時間が著しく延長することや、得られるソルビタン脂肪酸エステルが着色するなどの問題があるため、工業的な生産又は商業的に販売されている市販品の入手が困難であるため好ましくない。
[Condition (B)]
The esterification rate of the sorbitan fatty acid ester used in the present invention is 35 to 85%, more preferably 50 to 80%. If the esterification rate is less than 35%, the effect of suppressing the shrinkage of lauric fats and oils cannot be sufficiently obtained, which is not preferable. In addition, sorbitan fatty acid esters having an esterification rate exceeding 85% have problems such as a significant increase in reaction time and coloring of the obtained sorbitan fatty acid esters, so that they are industrially produced or sold commercially. Since it is difficult to obtain a commercial product, it is not preferable.

ここで、エステル化率(%)は下記式により算出される。なお、下記式中のエステル価及び水酸基価は、「基準油脂分析試験法(I)」(社団法人 日本油化学会編)の[2.3.3−1996 エステル価]及び[2.3.6−1996 ヒドロキシル価]に準じて測定される。   Here, the esterification rate (%) is calculated by the following formula. In addition, the ester value and the hydroxyl value in the following formula are shown in [2.3.3-1996 Ester Value] and [2.3. 6-1996 hydroxyl number].

Figure 0006196168
Figure 0006196168

本発明で用いられるソルビタン脂肪酸エステルの原料として用いられるソルビトールとしては、例えば、D−ソルビトールを50.0〜70.0質量%含有するD−ソルビトール液或いは白色粉末又は粒状のD−ソルビトールが挙げられる。   Examples of sorbitol used as a raw material for the sorbitan fatty acid ester used in the present invention include D-sorbitol liquid containing 50.0 to 70.0% by mass of D-sorbitol, white powder, or granular D-sorbitol. .

本発明で用いられるソルビタン脂肪酸エステルの原料として用いられる脂肪酸としては、上記条件(A)を満たすものが好ましく用いられる。   As the fatty acid used as a raw material for the sorbitan fatty acid ester used in the present invention, those satisfying the above condition (A) are preferably used.

本発明で用いられるソルビタン脂肪酸エステルの製造(エステル化反応)において、ソルビトールに対する脂肪酸の仕込み量は、ソルビトール1モルに対して1.4〜3.5モル程度であるのが好ましい。   In the production (esterification reaction) of the sorbitan fatty acid ester used in the present invention, the amount of fatty acid charged relative to sorbitol is preferably about 1.4 to 3.5 mol per mol of sorbitol.

本発明で用いられるソルビタン脂肪酸エステルの製造方法は特に限定されないが、例えばソルビトールと脂肪酸とのエステル化反応は無触媒で行って良く、又は酸触媒あるいはアルカリ触媒を用いて行っても良いが、アルカリ触媒の存在下で行われるのが好ましい。酸触媒としては、例えば、濃硫酸、p−トルエンスルホン酸などが挙げられる。アルカリ触媒としては、例えば水酸化カリウム、水酸化ナトリウム、炭酸カリウム、炭酸ナトリウムなどが挙げられる。アルカリ触媒の使用量は、全仕込み量(乾燥物換算)の0.01〜1.0質量%、好ましくは0.05〜0.5質量%である。   The production method of the sorbitan fatty acid ester used in the present invention is not particularly limited. For example, the esterification reaction between sorbitol and a fatty acid may be performed without a catalyst, or may be performed using an acid catalyst or an alkali catalyst. It is preferably carried out in the presence of a catalyst. Examples of the acid catalyst include concentrated sulfuric acid and p-toluenesulfonic acid. Examples of the alkali catalyst include potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate and the like. The usage-amount of an alkali catalyst is 0.01-1.0 mass% of the total preparation amount (dry matter conversion), Preferably it is 0.05-0.5 mass%.

上記製造に用いる製造装置としては特に限定されないが、例えば上記エステル化反応は、例えば攪拌機、加熱用のジャケット、邪魔板、不活性ガス吹き込み管、温度計及び冷却器付き水分分離器などを備えた通常の反応容器に、ソルビトール、脂肪酸、及び触媒を供給して攪拌混合し、窒素又は二酸化炭素などの任意の不活性ガス雰囲気下で、エステル化反応により生成する水を系外に除去しながら、所定温度で一定時間加熱して行われる。反応温度は通常、180〜260℃の範囲、好ましくは200〜250℃の範囲である。また、反応圧力条件は減圧下又は常圧下で、反応時間は0.5〜15時間、好ましくは1〜4時間である。反応の終点は、通常反応混合物の酸価を測定し、10以下を目安に決められる。   Although it does not specifically limit as a manufacturing apparatus used for the said manufacture, For example, the said esterification reaction was equipped with the water separator with a stirrer, the jacket for a heating, a baffle plate, an inert gas blowing tube, a thermometer, a cooler, etc., for example. While supplying sorbitol, a fatty acid, and a catalyst to a normal reaction vessel and stirring and mixing, under any inert gas atmosphere such as nitrogen or carbon dioxide, water generated by the esterification reaction is removed from the system, It is performed by heating at a predetermined temperature for a certain time. The reaction temperature is usually in the range of 180 to 260 ° C, preferably in the range of 200 to 250 ° C. The reaction pressure conditions are reduced pressure or normal pressure, and the reaction time is 0.5 to 15 hours, preferably 1 to 4 hours. The end point of the reaction is usually determined by measuring the acid value of the reaction mixture and taking 10 or less as a guide.

エステル化反応終了後、触媒を用いた場合は、反応混合物中に残存する触媒を中和しても良い。その際、エステル化反応の温度が200℃以上の場合は液温を180〜200℃に冷却してから中和処理を行うのが好ましい。また反応温度が200℃以下の場合は、そのままの温度で中和処理を行って良い。中和後、その温度で好ましくは0.5時間以上、更に好ましくは1〜10時間放置する。未反応のソルビトール又はソルビトール分子内縮合物が下層に分離した場合はそれを除去するのが好ましい。   When a catalyst is used after completion of the esterification reaction, the catalyst remaining in the reaction mixture may be neutralized. In that case, when the temperature of esterification reaction is 200 degreeC or more, it is preferable to neutralize after cooling liquid temperature to 180-200 degreeC. Moreover, when reaction temperature is 200 degrees C or less, you may neutralize at the same temperature. After neutralization, it is allowed to stand at that temperature for preferably 0.5 hours or more, more preferably 1 to 10 hours. When unreacted sorbitol or sorbitol intramolecular condensate is separated into the lower layer, it is preferably removed.

本発明においてラウリン系油脂とは、油脂の構成脂肪酸組成において炭素数12の飽和脂肪酸含量が50質量%以上である油脂をいい、具体的にはヤシ油、パーム核油、さらには、これらの油脂に水素添加、分別、エステル交換等の物理的又は化学的処理の1種又は2種以上の処理を施した油脂を挙げることができる。本発明においては、これらの油脂を単独で用いても良く、又は2種以上を組み合わせて用いても良い。   In the present invention, the lauric fats and oils refer to fats and oils having a saturated fatty acid content of 12 or more carbon atoms in the constituent fatty acid composition of the fats and oils, specifically coconut oil, palm kernel oil, and these fats and oils. And fats and oils subjected to one or more physical or chemical treatments such as hydrogenation, fractionation, and transesterification. In the present invention, these fats and oils may be used alone or in combination of two or more.

本発明のラウリン系油脂の結晶成長抑制剤(以下、単に「結晶成長抑制剤」ともいう)は、上記条件(A)及び(B)を満たすソルビタン脂肪酸エステルを有効成分とするものである。本発明の結晶成長抑制剤は、上記条件(A)及び(B)を満たすソルビタン脂肪酸エステルをそのままラウリン系油脂に添加して用いても良く、又は該ソルビタン脂肪酸エステルを含有する製剤を調製し、これを結晶成長抑制剤としてラウリン系油脂に添加して用いても良い。その添加方法に特に制限はないが、例えば本発明の結晶成長抑制剤をラウリン系油脂に加え、これを約60〜120℃に加熱して混合溶解することにより容易に実施することができる。   The crystal growth inhibitor (hereinafter also simply referred to as “crystal growth inhibitor”) of the lauric fat according to the present invention comprises a sorbitan fatty acid ester satisfying the above conditions (A) and (B) as an active ingredient. The crystal growth inhibitor of the present invention may be used by adding a sorbitan fatty acid ester that satisfies the above conditions (A) and (B) as it is to a lauric oil or fat, or a preparation containing the sorbitan fatty acid ester is prepared, You may add this to a lauric oil and fat as a crystal growth inhibitor. Although there is no restriction | limiting in particular in the addition method, For example, it can carry out easily by adding the crystal growth inhibitor of this invention to a lauric oil and fat, heating this to about 60-120 degreeC, and carrying out mixing dissolution.

本発明のラウリン系油脂組成物は、本発明の結晶成長抑制剤を添加したラウリン系油脂及び該ラウリン系油脂を原料として製造される油脂組成物である。具体的には、本発明の結晶成長抑制剤をラウリン系油脂に直接添加してなる油脂組成物の他、該油脂組成物を原料として製造される食用油脂組成物が挙げられ、そのような食用油脂組成物としては、例えばチョコレート類、ホイップクリーム用油脂組成物(起泡性水中油型乳化組成物)、サンドクリーム用油脂組成物、冷菓の被覆用油脂組成物、菓子又はパンの被覆用油脂組成物、マーガリン、ファットスプレッド又はショートニング等の可塑性油脂組成物、コーヒーホワイトナー・調整乳等の液状又は粉末状の乳製品又は油脂組成物等が挙げられる。これら食用油脂組成物の製造方法に特に制限はなく、これらは、慣用の装置を用いて、常法により製造することができる。   The lauric oil / fat composition of the present invention is a lauric oil / fat to which the crystal growth inhibitor of the present invention is added and an oil / fat composition produced from the lauric oil / fat as a raw material. Specifically, in addition to an oil composition obtained by directly adding the crystal growth inhibitor of the present invention to a lauric oil, an edible oil composition produced using the oil composition as a raw material is exemplified. Examples of the fat composition include chocolates, whipped cream fat composition (foamable oil-in-water emulsified composition), sand cream fat composition, frozen confectionery fat composition, confectionery or bread coating fat. Examples thereof include a plastic oil composition such as a composition, margarine, fat spread or shortening, and a liquid or powdered dairy product or oil composition such as coffee whitener or adjusted milk. There is no restriction | limiting in particular in the manufacturing method of these edible oil-fat compositions, These can be manufactured by a conventional method using a conventional apparatus.

本発明のラウリン系油脂組成物中の上記ソルビタン脂肪酸エステルの含有量は、該油脂組成物の形態、該油脂組成物中のラウリン系油脂の含有量、目的とする結晶成長抑制効果の程度等により異なり一様ではないが、例えば該油脂組成物に含有されるラウリン系油脂100質量部に対して、通常0.1〜2.0質量部、好ましくは0.2〜1.2質量部となるように調整することができる。   The content of the sorbitan fatty acid ester in the lauric oil / fat composition of the present invention depends on the form of the oil / fat composition, the content of the lauric oil / fat in the oil / fat composition, the degree of the intended crystal growth inhibiting effect, and the like. Although it is different and not uniform, for example, it is usually 0.1 to 2.0 parts by weight, preferably 0.2 to 1.2 parts by weight with respect to 100 parts by weight of lauric fats and oils contained in the fat composition Can be adjusted as follows.

以下、実施例をもっ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。   Hereinafter, the present invention will be specifically described with reference to examples, but the present invention is not limited thereto.

[製造例1]
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた2Lの四つ口フラスコに、ソルビトールを428g仕込み、次にラウリン酸L−98(商品名;脂肪酸組成:ラウリン酸98%、ミリスチン酸2%;丸善薬品産業社製)330.5g、ステアリン酸65(商品名;ステアリン酸含有量65%;パルミチン酸含有量35%;ミヨシ油脂社製)264.4g及びベヘニン酸85(商品名;ベヘニン酸含有量90%;アラキジン酸含有量8%;ステアリン酸含有量2%;ミヨシ油脂社製)66.1gを仕込み、触媒として水酸化ナトリウム1.38gを加え、常圧下、窒素ガス気流中、235℃で酸価10以下となるまで約1.5時間エステル化反応を行った。得られた反応生成物を冷却し、ソルビタン脂肪酸エステル(試作品A;エステル化率35%)約850gを得た。
[Production Example 1]
428 g of sorbitol was charged into a 2 L four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, and then lauric acid L-98 (trade name; fatty acid composition: 98% lauric acid, myristic acid 20.5; 330.5 g, manufactured by Maruzen Pharmaceutical Industry Co., Ltd., stearic acid 65 (trade name; stearic acid content 65%; palmitic acid content 35%; manufactured by Miyoshi Oil & Fats Co., Ltd.) 264.4 g and behenic acid 85 (trade name; Behenic acid content 90%; arachidic acid content 8%; stearic acid content 2%; made by Miyoshi Oil & Fats Co., Ltd.) 66.1 g, sodium hydroxide 1.38 g was added as a catalyst, and under normal pressure in a nitrogen gas stream The esterification reaction was carried out at 235 ° C. until the acid value became 10 or less for about 1.5 hours. The obtained reaction product was cooled to obtain about 850 g of sorbitan fatty acid ester (prototype A; esterification rate: 35%).

[製造例2]
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた2Lの四つ口フラスコに、ソルビトールを367g仕込み、次にラウリン酸L−98(商品名;脂肪酸組成:ラウリン酸98%、ミリスチン酸2%;丸善薬品産業社製)446.0g、ステアリン酸65(商品名;ステアリン酸含有量65%;パルミチン酸含有量35%;ミヨシ油脂社製)356.8g及びベヘニン酸85(商品名;ベヘニン酸含有量90%;アラキジン酸含有量8%;ステアリン酸含有量2%;ミヨシ油脂社製)89.2gを仕込み、触媒として水酸化ナトリウム0.58gを加え、常圧下、窒素ガス気流中、235℃で酸価10以下となるまで約3.0時間エステル化反応を行った。得られた反応生成物を冷却し、ソルビタン脂肪酸エステル(試作品B;エステル化率60%)約1070gを得た。
[Production Example 2]
A 2 L four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator was charged with 367 g of sorbitol, then lauric acid L-98 (trade name; fatty acid composition: lauric acid 98%, myristic acid 26.0; Maruzen Pharmaceutical Industry Co., Ltd.) 446.0 g, stearic acid 65 (trade name; stearic acid content 65%; palmitic acid content 35%; Miyoshi Oil & Fats Co., Ltd.) 356.8 g and behenic acid 85 (trade name; Behenic acid content 90%; arachidic acid content 8%; stearic acid content 2%; manufactured by Miyoshi Oil & Fats Co., Ltd.) 89.2 g, sodium hydroxide 0.58 g was added as a catalyst, and under normal pressure in a nitrogen gas stream The esterification reaction was carried out at 235 ° C. for about 3.0 hours until the acid value became 10 or less. The obtained reaction product was cooled to obtain about 1070 g of sorbitan fatty acid ester (prototype B; esterification rate 60%).

[製造例3]
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた2Lの四つ口フラスコに、ソルビトールを342g仕込み、次にラウリン酸L−98(商品名;脂肪酸組成:ラウリン酸98%、ミリスチン酸2%;丸善薬品産業社製)543.3g、ステアリン酸65(商品名;ステアリン酸含有量65%;パルミチン酸含有量35%;ミヨシ油脂社製)434.6g及びベヘニン酸85(商品名;ベヘニン酸含有量90%;アラキジン酸含有量8%;ステアリン酸含有量2%;ミヨシ油脂社製)108.7gを仕込み、触媒として水酸化ナトリウム0.54gを加え、常圧下、窒素ガス気流中、235℃で酸価10以下となるまで約4時間エステル化反応を行った。得られた反応生成物を冷却し、ソルビタン脂肪酸エステル(試作品C;エステル化率80%)約1210gを得た。
[Production Example 3]
A 2 L four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator was charged with 342 g of sorbitol, then lauric acid L-98 (trade name; fatty acid composition: lauric acid 98%, myristic acid 23.3% (made by Maruzen Pharmaceutical Industry Co., Ltd.) 543.3 g, stearic acid 65 (trade name; stearic acid content 65%; palmitic acid content 35%; manufactured by Miyoshi Oil & Fats Co., Ltd.) 434.6 g and behenic acid 85 (trade name; 108.7 g of behenic acid content 90%; arachidic acid content 8%; stearic acid content 2%; manufactured by Miyoshi Oil & Fats Co., Ltd.), 0.54 g of sodium hydroxide as a catalyst, and nitrogen gas stream under normal pressure The esterification reaction was carried out at 235 ° C. for about 4 hours until the acid value became 10 or less. The obtained reaction product was cooled to obtain about 1210 g of sorbitan fatty acid ester (prototype C; esterification rate 80%).

[製造例4]
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた2Lの四つ口フラスコに、ソルビトールを361g仕込み、次にラウリン酸L−98(商品名;脂肪酸組成:ラウリン酸98%、ミリスチン酸2%;丸善薬品産業社製)740.7g及びステアリン酸65(商品名;ステアリン酸含有量65%;パルミチン酸含有量35%;ミヨシ油脂社製)185.2gを仕込み、触媒として水酸化ナトリウム0.59gを加え、常圧下、窒素ガス気流中、235℃で酸価10以下となるまで約4.0時間エステル化反応を行った。得られた反応生成物を冷却し、ソルビタン脂肪酸エステル(試作品D;エステル化率75%)約1090gを得た。
[Production Example 4]
A 2 L four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator was charged with 361 g of sorbitol, then lauric acid L-98 (trade name; fatty acid composition: lauric acid 98%, myristic acid 2%; made by Maruzen Pharmaceutical Industry Co., Ltd.) 740.7g and stearic acid 65 (trade name; stearic acid content 65%; palmitic acid content 35%; made by Miyoshi Yushi Co., Ltd.) 185.2g, sodium hydroxide as catalyst 0.59 g was added, and the esterification reaction was performed for about 4.0 hours under normal pressure in a nitrogen gas stream at 235 ° C. until the acid value became 10 or less. The obtained reaction product was cooled to obtain about 1090 g of sorbitan fatty acid ester (prototype D; esterification rate 75%).

[製造例5]
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた2Lの四つ口フラスコに、ソルビトールを458g仕込み、次にラウリン酸L−98(商品名;脂肪酸組成:ラウリン酸98%、ミリスチン酸2%;丸善薬品産業社製)571.1g、ベヘニン酸85(商品名;ベヘニン酸含有量90%;アラキジン酸含有量8%;ステアリン酸含有量2%;ミヨシ油脂社製)30.0gを仕込み、触媒として水酸化ナトリウム1.29gを加え、常圧下、窒素ガス気流中、235℃で酸価10以下となるまで約1.5時間エステル化反応を行った。得られた反応生成物を冷却し、ソルビタン脂肪酸エステル(試作品E;エステル化率35%)約825gを得た。
[Production Example 5]
458 g of sorbitol was charged into a 2 L four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, and then lauric acid L-98 (trade name; fatty acid composition: 98% lauric acid, myristic acid 21.1; manufactured by Maruzen Pharmaceutical Industry Co., Ltd.) 571.1 g, behenic acid 85 (trade name; behenic acid content 90%; arachidic acid content 8%; stearic acid content 2%; manufactured by Miyoshi Oil & Fats Co., Ltd.) 30.0 g First, 1.29 g of sodium hydroxide was added as a catalyst, and an esterification reaction was carried out under normal pressure in a nitrogen gas stream at 235 ° C. until the acid value became 10 or less for about 1.5 hours. The obtained reaction product was cooled to obtain about 825 g of sorbitan fatty acid ester (prototype E; esterification rate: 35%).

[製造例6]
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた2Lの四つ口フラスコに、ソルビトールを409g仕込み、次にラウリン酸L−98(商品名;脂肪酸組成:ラウリン酸98%、ミリスチン酸2%;丸善薬品産業社製)679.1g、ベヘニン酸85(商品名;ベヘニン酸含有量90%;アラキジン酸含有量8%;ステアリン酸含有量2%;ミヨシ油脂社製)35.7gを仕込み、触媒として水酸化ナトリウム1.45gを加え、常圧下、窒素ガス気流中、235℃で酸価10以下となるまで約1.5時間エステル化反応を行った。得られた反応生成物を冷却し、ソルビタン脂肪酸エステル(試作品F;エステル化率45%)約890gを得た。
[Production Example 6]
409 g of sorbitol was charged into a 2 L four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, and then lauric acid L-98 (trade name; fatty acid composition: 98% lauric acid, myristic acid 29.1%, manufactured by Maruzen Pharmaceutical Industry Co., Ltd.) 679.1 g, behenic acid 85 (trade name; behenic acid content 90%; arachidic acid content 8%; stearic acid content 2%; manufactured by Miyoshi Oil & Fats Co., Ltd.) 35.7 g First, 1.45 g of sodium hydroxide was added as a catalyst, and an esterification reaction was performed for about 1.5 hours at 235 ° C. under an atmospheric pressure under a nitrogen gas stream until the acid value became 10 or less. The obtained reaction product was cooled to obtain about 890 g of sorbitan fatty acid ester (prototype F; esterification rate: 45%).

[製造例7]
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた2Lの四つ口フラスコに、ソルビトールを356g仕込み、次にラウリン酸L−98(商品名;脂肪酸組成:ラウリン酸98%、ミリスチン酸2%;丸善薬品産業社製)914.8g及びベヘニン酸85(商品名;ベヘニン酸含有量90%;アラキジン酸含有量8%;ステアリン酸含有量2%;ミヨシ油脂社製)48.1gを仕込み、触媒として水酸化ナトリウム0.61gを加え、常圧下、窒素ガス気流中、235℃で酸価10以下となるまで約4.0時間エステル化反応を行った。得られた反応生成物を冷却し、ソルビタン脂肪酸エステル(試作品G;エステル化率80%)約1120gを得た。
[Production Example 7]
A 2 L four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator was charged with 356 g of sorbitol, then lauric acid L-98 (trade name; fatty acid composition: 98% lauric acid, myristic acid 91% of 2%; manufactured by Maruzen Pharmaceutical Industry Co., Ltd.) and 48.1 g of behenic acid 85 (trade name; 90% behenic acid content; 8% arachidic acid content; 2% stearic acid content; manufactured by Miyoshi Oil & Fats Co., Ltd.) Then, 0.61 g of sodium hydroxide was added as a catalyst, and an esterification reaction was carried out in a nitrogen gas stream under normal pressure at 235 ° C. until the acid value became 10 or less for about 4.0 hours. The obtained reaction product was cooled to obtain about 1120 g of sorbitan fatty acid ester (prototype G; esterification rate 80%).

[製造例8]
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた2Lの四つ口フラスコに、ソルビトール347gを仕込み、次にステアリン酸65(商品名;ステアリン酸含有量65%;パルミチン酸含有量35%;ミヨシ油脂社製)1035.4gを仕込み、触媒として水酸化ナトリウム0.65gを加え、常圧下、窒素ガス気流中、235℃で酸価10以下となるまで約3.0時間エステル化反応を行った。得られた反応生成物を冷却し、ソルビタン脂肪酸エステル(試作品H;エステル化率65%)約1140gを得た。
[Production Example 8]
A 2 L four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator was charged with 347 g of sorbitol, and then stearic acid 65 (trade name; stearic acid content 65%; palmitic acid content 35 %; Made by Miyoshi Oil & Fats Co., Ltd.) 1035.4g, 0.65g of sodium hydroxide was added as a catalyst, and the esterification reaction took about 3.0 hours under normal pressure in a nitrogen gas stream at 235 ° C until the acid value was 10 or less. Went. The obtained reaction product was cooled to obtain about 1140 g of sorbitan fatty acid ester (prototype H; esterification rate 65%).

[製造例9]
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた2Lの四つ口フラスコに、ソルビトールを355g仕込み、次にラウリン酸L−98(商品名;脂肪酸組成:ラウリン酸98%、ミリスチン酸2%;丸善薬品産業社製)126.6g、ステアリン酸65(商品名;ステアリン酸含有量65%;パルミチン酸含有量35%;ミヨシ油脂社製)682.0g及びベヘニン酸85(商品名;ベヘニン酸含有量90%;アラキジン酸含有量8%;ステアリン酸含有量2%;ミヨシ油脂社製)165.6gを仕込み、触媒として水酸化ナトリウム0.62gを加え、常圧下、窒素ガス気流中、235℃で酸価10以下となるまで約3.0時間エステル化反応を行った。得られた反応生成物を冷却し、ソルビタン脂肪酸エステル(試作品I;エステル化率60%)約1130gを得た。
[Production Example 9]
A 2 L four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator was charged with 355 g of sorbitol, then lauric acid L-98 (trade name; fatty acid composition: 98% lauric acid, myristic acid 2%; manufactured by Maruzen Pharmaceutical Industry Co., Ltd.) 126.6 g, stearic acid 65 (trade name; stearic acid content 65%; palmitic acid content 35%; manufactured by Miyoshi Oil & Fats Co., Ltd.) 682.0 g and behenic acid 85 (trade name; Behenic acid content 90%; arachidic acid content 8%; stearic acid content 2%; manufactured by Miyoshi Oil & Fats Co., Ltd.) 165.6 g, 0.62 g sodium hydroxide as a catalyst, and nitrogen gas stream under normal pressure The esterification reaction was carried out at 235 ° C. for about 3.0 hours until the acid value became 10 or less. The obtained reaction product was cooled to obtain about 1130 g of sorbitan fatty acid ester (prototype I; esterification rate 60%).

[製造例10]
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた2Lの四つ口フラスコに、ソルビトールを443g仕込み、次にラウリン酸L−98(商品名;脂肪酸組成:ラウリン酸98%、ミリスチン酸2%;丸善薬品産業社製)188.6g、ステアリン酸65(商品名;ステアリン酸含有量65%;パルミチン酸含有量35%;ミヨシ油脂社製)377.3g及びベヘニン酸85(商品名;ベヘニン酸含有量90%;アラキジン酸含有量8%;ステアリン酸含有量2%;ミヨシ油脂社製)62.9gを仕込み、触媒として水酸化ナトリウム1.33gを加え、常圧下、窒素ガス気流中、235℃で酸価10以下となるまで約1.5時間エステル化反応を行った。得られた反応生成物を冷却し、ソルビタン脂肪酸エステル(試作品J;エステル化率30%)約830gを得た。
[Production Example 10]
A 2 L four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator was charged with 443 g of sorbitol, then lauric acid L-98 (trade name; fatty acid composition: lauric acid 98%, myristic acid 28.6; Maruzen Pharmaceutical Co., Ltd.) 188.6 g, stearic acid 65 (trade name; stearic acid content 65%; palmitic acid content 35%; manufactured by Miyoshi Oil & Fats Co., Ltd.) 377.3 g and behenic acid 85 (trade name; Behenic acid content 90%; arachidic acid content 8%; stearic acid content 2%; manufactured by Miyoshi Oil & Fats Co., Ltd.) 62.9g, sodium hydroxide 1.33g was added as a catalyst, and under normal pressure in a nitrogen gas stream The esterification reaction was carried out at 235 ° C. until the acid value became 10 or less for about 1.5 hours. The obtained reaction product was cooled to obtain about 830 g of sorbitan fatty acid ester (prototype J; esterification rate 30%).

[製造例11]
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた2Lの四つ口フラスコに、ソルビトールを337g仕込み、次にラウリン酸L−98(商品名;脂肪酸組成:ラウリン酸98%、ミリスチン酸2%;丸善薬品産業社製)341.1g及びステアリン酸65(商品名;ステアリン酸含有量65%;パルミチン酸含有量35%;ミヨシ油脂社製)682.1g及びベヘニン酸85(商品名;ベヘニン酸含有量90%;アラキジン酸含有量8%;ステアリン酸含有量2%;ミヨシ油脂社製)113.7gを仕込み、触媒として水酸化ナトリウム0.70gを加え、常圧下、窒素ガス気流中、235℃で酸価10以下となるまで約4.0時間エステル化反応を行った。得られた反応生成物を冷却し、ソルビタン脂肪酸エステル(試作品K;エステル化率80%)約1250gを得た。
[Production Example 11]
A 2 L four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator was charged with 337 g of sorbitol, and then lauric acid L-98 (trade name; fatty acid composition: lauric acid 98%, myristic acid. 34% by Maruzen Pharmaceutical Industries Co., Ltd.) and stearic acid 65 (trade name; stearic acid content 65%; palmitic acid content 35%; manufactured by Miyoshi Oil & Fats Co., Ltd.) 682.1 g and behenic acid 85 (trade name; Behenic acid content 90%; arachidic acid content 8%; stearic acid content 2%; manufactured by Miyoshi Oil & Fats Co., Ltd.) 113.7 g, 0.70 g of sodium hydroxide as a catalyst, and nitrogen gas stream under normal pressure The esterification reaction was performed for about 4.0 hours at 235 ° C. until the acid value was 10 or less. The obtained reaction product was cooled to obtain about 1250 g of sorbitan fatty acid ester (prototype K; esterification rate 80%).

[製造例12]
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた2Lの四つ口フラスコに、ソルビトール550gを仕込み、次にラウリン酸L−98(商品名;脂肪酸組成:ラウリン酸98%、ミリスチン酸2%;丸善薬品産業社製)295.6g、ステアリン酸65(商品名;ステアリン酸含有量65%;パルミチン酸含有量35%;ミヨシ油脂社製)172.4g及びベヘニン酸85(商品名;ベヘニン酸含有量90%;アラキジン酸含有量8%;ステアリン酸含有量2%;ミヨシ油脂社製)24.6gを仕込み、触媒として水酸化ナトリウム1.13gを加え、常圧下、窒素ガス気流中、235℃で酸価10以下となるまで約1.5時間エステル化反応を行った。得られた反応生成物を冷却し、ソルビタン脂肪酸エステル(試作品L;エステル化率23%)約800gを得た。
[Production Example 12]
A 2 L four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator was charged with 550 g of sorbitol, and then lauric acid L-98 (trade name; fatty acid composition: 98% lauric acid, myristic acid 25.6% (made by Maruzen Pharmaceutical Industry Co., Ltd.) 295.6 g, stearic acid 65 (trade name; stearic acid content 65%; palmitic acid content 35%; made by Miyoshi Oil & Fats) 172.4 g and behenic acid 85 (trade name; Behenic acid content 90%; arachidic acid content 8%; stearic acid content 2%; manufactured by Miyoshi Oil & Fats Co., Ltd.) 24.6g, sodium hydroxide 1.13g was added as a catalyst, and nitrogen gas stream under normal pressure The esterification reaction was carried out at 235 ° C. until the acid value became 10 or less for about 1.5 hours. The obtained reaction product was cooled to obtain about 800 g of sorbitan fatty acid ester (prototype L; esterification rate: 23%).

[製造例13]
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた2Lの四つ口フラスコに、ソルビトールを492g仕込み、次にラウリン酸L−98(商品名;脂肪酸組成:ラウリン酸98%、ミリスチン酸2%;丸善薬品産業社製)523.7g及びステアリン酸65(商品名;ステアリン酸含有量65%;パルミチン酸含有量35%;ミヨシ油脂社製)27.6gを仕込み、触媒として水酸化ナトリウム1.22gを加え、常圧下、窒素ガス気流中、235℃で酸価10以下となるまで約1.5時間エステル化反応を行った。得られた反応生成物を冷却し、ソルビタン脂肪酸エステル(試作品M;エステル化率30%)約810gを得た。
[Production Example 13]
492 g of sorbitol was charged into a 2 L four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, and then lauric acid L-98 (trade name; fatty acid composition: lauric acid 98%, myristic acid 23.7% (made by Maruzen Pharmaceutical Industry Co., Ltd.) 523.7 g and stearic acid 65 (trade name; stearic acid content 65%; palmitic acid content 35%; manufactured by Miyoshi Oil & Fats Co., Ltd.) 27.6 g, sodium hydroxide as a catalyst 1.22 g was added, and the esterification reaction was carried out under normal pressure in a nitrogen gas stream at 235 ° C. until the acid value became 10 or less for about 1.5 hours. The obtained reaction product was cooled to obtain about 810 g of sorbitan fatty acid ester (prototype M; esterification rate 30%).

ここで、製造例1〜13で製造したソルビタン脂肪酸エステル(試作品A〜M)の構成脂肪酸100%中、炭素数10〜14、炭素数16〜18及び炭素数20〜22の脂肪酸含有量(%)並びにこれらのエステル化率を表1に示す。   Here, in 100% of the constituent fatty acids of the sorbitan fatty acid esters (prototypes A to M) produced in Production Examples 1 to 13, the content of fatty acids having 10 to 14 carbon atoms, 16 to 18 carbon atoms, and 20 to 22 carbon atoms ( %) And their esterification rates are shown in Table 1.

Figure 0006196168
Figure 0006196168

なお、表1に示したソルビタン脂肪酸エステルのうち、試作品A〜G(製造例1〜7)は、本発明に係る実施例であり、試作品H〜M(製造例8〜13)は、これらに対する比較例である。   In addition, among sorbitan fatty acid esters shown in Table 1, prototypes A to G (Production Examples 1 to 7) are examples according to the present invention, and prototypes H to M (Production Examples 8 to 13) are It is a comparative example for these.

[試験例]
[ラウリン系油脂の結晶成長抑制試験]
ヤシ硬化油(商品名:硬化ヤシ油;不二製油社製)50g及びキャノーラ油(日清オイリオグループ社製)50gからなる配合油に、製造例1〜13で得たソルビタン脂肪酸エステル(試作品A〜M)各0.5gを結晶成長抑制剤として添加し、これを80℃に加熱して混合・溶解し、ラウリン系油脂組成物を調製した。得られた油脂組成物の適量をカバーガラス上にサンプリングし、その上に別のカバーガラスをかぶせて油脂組成物を挟み込んだ。次に、顕微鏡用加熱冷却ステージ(LINKAM社製)を用いて該油脂組成物を10℃/分の速度で60℃まで昇温し、3分間保持した後、10℃/分の速度で20℃まで冷却した。続いて、20℃に設定した恒温器内に該油脂組成物を2週間保存し、その結晶状態を偏光顕微鏡(NIKON社製)で観察し、下記評価基準により記号化した。また、対照として、結晶成長抑制剤無添加のものも同様に試験した。結果を表2に示す。
○:ほとんどが10μm以下の大きさの結晶
△:半数以上が10〜20μmの大きさの結晶
×:ほとんどが20μm以上の大きさの結晶
[Test example]
[Crystal growth inhibition test of lauric fats and oils]
Sorbitan fatty acid esters (prototypes) obtained in Production Examples 1 to 13 to a blended oil consisting of 50 g of hydrogenated palm oil (trade name: hydrogenated palm oil; manufactured by Fuji Oil Co., Ltd.) and 50 g of canola oil (Nisshin Oilio Group) A to M) 0.5 g of each was added as a crystal growth inhibitor, and this was heated to 80 ° C. and mixed and dissolved to prepare a lauric oil composition. An appropriate amount of the obtained oil / fat composition was sampled on a cover glass, and another cover glass was placed thereon to sandwich the oil / fat composition. Next, the oil and fat composition was heated to 60 ° C. at a rate of 10 ° C./min using a microscope heating / cooling stage (manufactured by LINKAM), held for 3 minutes, and then 20 ° C. at a rate of 10 ° C./min. Until cooled. Subsequently, the oil and fat composition was stored in a thermostat set to 20 ° C. for 2 weeks, and its crystal state was observed with a polarizing microscope (manufactured by NIKON) and symbolized according to the following evaluation criteria. In addition, as a control, a test without addition of a crystal growth inhibitor was similarly tested. The results are shown in Table 2.
○: Most crystals having a size of 10 μm or less Δ: Crystals having a size of more than half of 10 to 20 μm ×: Most crystals having a size of 20 μm or more

Figure 0006196168
Figure 0006196168

表2の結果から明らかなように、本発明の結晶成長抑制剤(試作品A〜G)を添加したラウリン系油脂組成物は、結晶の成長が十分に抑制されていた。これに対し、比較例の結晶成長抑制剤(試作品H〜M)を添加したラウリン系油脂組成物及び対照のラウリン系油脂組成物では、比較的大きな結晶が見られ、本発明のものに比べて劣っていた。   As is clear from the results in Table 2, the lauric oil / fat composition to which the crystal growth inhibitor of the present invention (prototypes A to G) was added had crystal growth sufficiently suppressed. On the other hand, comparatively large crystals are seen in the lauric fat composition and the control lauric fat composition to which the crystal growth inhibitor of the comparative example (prototypes H to M) is added, and compared with that of the present invention. It was inferior.

Claims (2)

下記条件(A)及び(B)を満たすソルビタン脂肪酸エステル(但し、構成脂肪酸中の炭素数16〜18の飽和脂肪酸及び炭素数20〜22の飽和脂肪酸の含有量がいずれも10%であるものを除く)を有効成分とすることを特徴とするラウリン系油脂の結晶成長抑制剤。
(A):構成脂肪酸中の炭素数10〜14の脂肪酸含有量が80%以上;
(B):エステル化率が35〜85%。
Sorbitan fatty acid ester satisfying the following conditions (A) and (B) (however, the content of the saturated fatty acid having 16 to 18 carbon atoms and the saturated fatty acid having 20 to 22 carbon atoms in the constituent fatty acid is 10%) ) , A crystal growth inhibitor for lauric oils and fats.
(A): The fatty acid content of 10 to 14 carbon atoms in the constituent fatty acid is 80 % or more;
(B): The esterification rate is 35 to 85%.
請求項1に記載の結晶成長抑制剤を含有することを特徴とするラウリン系油脂組成物。   A lauric oil composition comprising the crystal growth inhibitor according to claim 1.
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