JP2018191592A - Hardening inhibitor for palm oil - Google Patents
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Abstract
【課題】パーム系油脂を配合した油脂組成物の経時的な硬化を抑制できる硬化抑制剤を提供する。【解決手段】主構成脂肪酸がラウリン酸であるソルビタン脂肪酸エステルを有効成分とするパーム系油脂の硬化抑制剤。【選択図】 なしPROBLEM TO BE SOLVED: To provide a curing inhibitor capable of suppressing the curing over time of an oil / fat composition containing a palm-based oil / fat. SOLUTION: An agent for suppressing hardening of palm-based fats and oils containing sorbitan fatty acid ester whose main constituent fatty acid is lauric acid as an active ingredient. [Selection diagram] None
Description
本発明は、パーム系油脂の硬化抑制剤に関する。 The present invention relates to a curing inhibitor for palm-based fats and oils.
マーガリン、ファットスプレッド、ショートニング等の油脂製品は、従来製菓・製パン・調理用油脂等として広く用いられている。これら油脂製品には、求められる品質に応じて様々な油脂が配合されるが、とりわけパーム系油脂は比較的安価で手に入ることから広く使用されている。また、近年、健康に対する関心の高まりを受けて、トランス酸残基を有する油脂の使用が忌避される傾向があることから、トランス酸残基を実質的に有さないパーム系油脂の使用が好まれている。 Oil and fat products such as margarine, fat spread, and shortening have been widely used as confectionery, bread making, cooking oils and fats and the like. Various fats and oils are blended in these fats and oils depending on the quality required, and palm oils and fats are particularly widely used because they are relatively inexpensive and available. In recent years, the use of palm-based fats and oils having substantially no trans-acid residues is preferred because the use of fats and oils having trans-acid residues tends to be avoided in response to growing interest in health. It is rare.
しかし、パーム系油脂は粗大結晶を生成し易く、パーム系油脂を配合した油脂製品の保存中に粗大結晶が生成すると、その商品価値が著しく損なわれることが従来問題となっていた。 However, palm-based fats and oils easily produce coarse crystals, and when coarse crystals are produced during the storage of fats and oils blended with palm-based fats and oils, the commercial value has been significantly impaired.
このような粗大結晶の生成を抑制する方法としては、例えば、ソルビタン脂肪酸エステルを含有する油脂の結晶成長抑制剤であって、該ソルビタン脂肪酸エステルの構成脂肪酸１００％中、炭素数１０〜１４の飽和脂肪酸、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％以上であることを特徴とする油脂の結晶成長抑制剤（特許文献１）、パーム油６０〜８０質量部、パーム核油１０〜３０質量部、及び液状油１０〜２０質量部のエステル交換油であって、１０℃でのＳＦＣが２５〜４０、２０℃でのＳＦＣが１５〜２５、３０℃でのＳＦＣが５〜１５である可塑性油脂１０〜７０質量％及びパーム油３０〜９０質量％を配合した、融点が３０〜４０℃である中融点油脂を用いる方法（特許文献２）、エステル化率が２０％以上５０％未満のソルビタン飽和脂肪酸エステルを添加することを特徴とする、パーム油そのものの粒状結晶生成抑制方法（特許文献３）等が提案されている。 As a method for suppressing the formation of such coarse crystals, for example, an oil crystal growth inhibitor containing sorbitan fatty acid ester, which is saturated with 10 to 14 carbon atoms in 100% constituent fatty acid of the sorbitan fatty acid ester. Fat and oil crystal growth inhibitor (Patent Document 1), palm oil 60, wherein the content of fatty acid, saturated fatty acid having 16 to 18 carbon atoms and saturated fatty acid having 20 to 22 carbon atoms is 10% or more. ~ 80 parts by mass, 10-30 parts by mass of palm kernel oil, and 10-20 parts by mass of liquid oil, SFC at 10 ° C is 25-40, SFC at 20 ° C is 15-25, A method of using a medium melting point oil and fat having a melting point of 30 to 40 ° C., blended with 10 to 70% by weight of plastic fat and oil having an SFC of 5 to 15 at 30 ° C. and 30 to 90% by weight of palm oil (Patent Documents) ), Esterification ratio is characterized by the addition of sorbitan saturated fatty acid ester of less than 20% 50% The method of granular crystal formation inhibitory palm oil itself (Patent Document 3) have been proposed.
一方、パーム系油脂を配合した油脂製品は、保存中に次第に硬く変化し、製品のひび割れや伸展性の低下をもたらすといった問題もある。しかし、この問題の解決において、上記の技術は実用上必ずしも満足できるものではない。 On the other hand, fats and oils products containing palm-based fats and oils have a problem that they gradually change during storage, resulting in cracking of the products and deterioration of extensibility. However, in solving this problem, the above technique is not always satisfactory in practice.
本発明は、パーム系油脂を配合した油脂組成物の経時的な硬化を抑制できる硬化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 hardening inhibitor which can suppress hardening with time of the oil-fat composition which mix | blended palm oil and fat.
本発明者らは、上記課題に対して鋭意検討を行った結果、主構成脂肪酸がラウリン酸であるソルビタン脂肪酸エステルを使用することにより、上記課題が解決されることを見出し、この知見に基づいて本発明を成すに至った。 As a result of intensive studies on the above problems, the present inventors have found that the above problems can be solved by using a sorbitan fatty acid ester whose main constituent fatty acid is lauric acid, and based on this finding The present invention has been accomplished.
すなわち、本発明は、下記の（１）及び（２）からなっている。
（１）主構成脂肪酸がラウリン酸であるソルビタン脂肪酸エステルを有効成分とするパーム系油脂の硬化抑制剤。
（２）前記（１）に記載の硬化抑制剤を含有するパーム系油脂組成物。
That is, the present invention comprises the following (1) and (2).
(1) A curing inhibitor for palm-based fats and oils containing a sorbitan fatty acid ester whose main constituent fatty acid is lauric acid as an active ingredient.
(2) A palm-based oil / fat composition containing the curing inhibitor according to (1).
本発明のパーム系油脂の硬化抑制剤を添加して得られるパーム系油脂組成物は、保存中の経時的な硬化が抑制されている。 The palm-based fat composition obtained by adding the palm-based fat / oil curing inhibitor of the present invention is suppressed from being cured with time during storage.
本発明で用いられるソルビタン脂肪酸エステルは、ソルビトール及び／又はその縮合物と脂肪酸との直接エステル化反応により製造されるものであって、ラウリン酸を主構成脂肪酸とするものである。該ソルビタン脂肪酸エステルのエステル化率に特に制限はないが、通常２５〜８０％である。ここで、エステル化率（％）は下記式により算出される。尚、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。 The sorbitan fatty acid ester used in the present invention is produced by a direct esterification reaction between sorbitol and / or a condensate thereof and a fatty acid, and has lauric acid as a main constituent fatty acid. Although there is no restriction | limiting in particular in the esterification rate of this sorbitan fatty acid ester, Usually, it is 25 to 80%. Here, the esterification rate (%) is calculated by the following formula. In addition, the ester value and the hydroxyl value in the following formula are [2.2.3-1996 ester value] and [2.3.3 of “Reference Oil Analysis Test Method (I)” (edited by Japan Oil Chemists' Society). 6-1996 hydroxyl number].
本発明で用いられるソルビタン脂肪酸エステルのソルビタン型含有量に特に制限はないが、通常３０質量％以上である。ソルビタン型含有量とは、ソルビタン脂肪酸エステルを構成するアルコール（例えば、ソルビトール、ソルビタン、ソルバイド等）１００質量％中のソルビタンの含有量（質量％）を意味する。 Although there is no restriction | limiting in particular in sorbitan type content of the sorbitan fatty acid ester used by this invention, Usually, it is 30 mass% or more. The sorbitan type content means the content (mass%) of sorbitan in 100 mass% of alcohol (for example, sorbitol, sorbitan, sorbide, etc.) constituting the sorbitan fatty acid ester.
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及び／又はその縮合物としては、例えば、ソルビトールとしては、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。また、ソルビトールの縮合物としては、ソルビトールが分子内脱水により、水１分子の脱水したソルビタン、水２分子の脱水したソルバイド等が挙げられる。 As sorbitol and / or its condensate used as a raw material of the sorbitan fatty acid ester used in the present invention, for example, as sorbitol, D-sorbitol liquid containing 50.0 to 70.0% by mass of D-sorbitol or white Examples thereof include powdered or granular D-sorbitol. Examples of the condensate of sorbitol include sorbitan in which one molecule of water is dehydrated by intramolecular dehydration of sorbitol, sorbide in which two molecules of water are dehydrated, and the like.
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は、ラウリン酸又はラウリン酸とラウリン酸以外の脂肪酸とを含有する脂肪酸混合物である。 The fatty acid used as a raw material of the sorbitan fatty acid ester used in the present invention is a fatty acid mixture containing lauric acid or lauric acid and a fatty acid other than lauric acid.
ここで、本発明で用いられるソルビタン脂肪酸エステルにおいて「ラウリン酸を主構成脂肪酸とする」とは、該ソルビタン脂肪酸エステルを構成する脂肪酸（構成脂肪酸）の大部分はラウリン酸であるが、本発明の目的及び効果が達成される範囲で、ラウリン酸以外の脂肪酸が一種類又は二種類以上含まれてもよいとの意味である。より具体的には、該ソルビタン脂肪酸エステルの構成脂肪酸１００質量％中のラウリン酸の含有量は、通常５０質量％以上、好ましくは７０質量％以上、より好ましくは８０質量％以上、更に好ましくは９０質量％以上である。 Here, in the sorbitan fatty acid ester used in the present invention, “having lauric acid as the main constituent fatty acid” means that most of the fatty acids (constituent fatty acids) constituting the sorbitan fatty acid ester are lauric acid. It means that one type or two or more types of fatty acids other than lauric acid may be included as long as the purpose and effect are achieved. More specifically, the content of lauric acid in 100% by mass of the constituent fatty acid of the sorbitan fatty acid ester is usually 50% by mass or more, preferably 70% by mass or more, more preferably 80% by mass or more, and still more preferably 90%. It is at least mass%.
また、本発明で用いられるソルビタン脂肪酸エステルの構成脂肪酸は、本発明の硬化抑制剤を添加したパーム系油脂組成物の硬化抑制及びその食感に与える影響の観点から、炭素数２０以上の脂肪酸を実質的に含まないことが好ましい。「炭素数２０以上の脂肪酸を実質的に含まない」とは、該ソルビタン脂肪酸エステルの構成脂肪酸１００質量％中の炭素数２０以上の脂肪酸の含有量が１０質量％未満、好ましくは５質量％未満、より好ましくは１質量％未満であることを指す。 In addition, the constituent fatty acid of the sorbitan fatty acid ester used in the present invention is a fatty acid having 20 or more carbon atoms from the viewpoint of inhibiting the curing of the palm-based oil / fat composition to which the curing inhibitor of the present invention has been added and affecting its texture. It is preferable that it does not contain substantially. “Substantially free of fatty acids having 20 or more carbon atoms” means that the content of fatty acids having 20 or more carbon atoms in 100% by mass of constituent fatty acids of the sorbitan fatty acid ester is less than 10% by mass, preferably less than 5% by mass. More preferably, it is less than 1% by mass.
ここで、本発明で用いられるソルビタン脂肪酸エステルの構成脂肪酸１００質量％中のラウリン酸及びラウリン酸以外の脂肪酸の含有量は、該ソルビタン脂肪酸エステルの製造の原料である脂肪酸１００質量％中の含有量と同じであるが、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 lauric acid and fatty acid other than lauric acid in 100% by mass of the constituent fatty acid of the sorbitan fatty acid ester used in the present invention is the content in 100% by mass of the fatty acid that is a raw material for producing the sorbitan fatty acid ester. However, this content may be measured by carrying out the following steps (1) to (3) on the produced sorbitan fatty acid ester.
(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.
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１．２〜３．０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 1.2 to 3.0 mol with respect to 1 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等が挙げられる。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、炭酸ナトリウム等が挙げられる。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%.
本発明で用いられるソルビタン脂肪酸エステルの製造装置及び当該装置を用いた製造条件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等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等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 using the manufacturing apparatus of the sorbitan fatty acid ester used by this invention, and the said apparatus, For example, the said esterification reaction, for example, a stirrer, a jacket for heating, a baffle plate, an inert gas blowing pipe, In a normal reaction vessel equipped with a thermometer and a water separator with a cooler, etc., sorbitol, fatty acid, and catalyst are supplied and mixed with stirring, and esterification is performed under any inert gas atmosphere such as nitrogen or carbon dioxide. The reaction is carried out by heating at a predetermined temperature for a certain time while removing water generated by the reaction out of the system. The reaction temperature is usually in the range of 180 to 260 ° C, preferably in the range of 200 to 250 ° C. The reaction pressure 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.
ラウリン酸を主構成脂肪酸とするソルビタン脂肪酸エステルとしては、例えば、Ｌ−３００（製品名；脂肪酸組成：ラウリン酸５４．９質量％、ミリスチン酸質量１８．１％、パルミチン酸１１．３質量％、その他１５．７質量％；エステル化率２５％；ソルビタン型含有量４１．５質量％；理研ビタミン社製）等が商業的に製造・販売されており、本発明ではこれを用いることができる。 Examples of the sorbitan fatty acid ester having lauric acid as a main constituent fatty acid include L-300 (product name; fatty acid composition: lauric acid 54.9% by mass, myristic acid mass 18.1%, palmitic acid 11.3% by mass, Others such as 15.7% by mass; esterification rate 25%; sorbitan type content 41.5% by mass; manufactured by Riken Vitamin Co., Ltd.) are commercially available and can be used in the present invention.
本発明においてパーム系油脂とはパーム油及びこれを原料とし分別、硬化等の加工を施した油脂のことであり、パームオレインやスーパーパームオレイン、パームステアリン又はこれらを硬化したものを挙げることができる。 In the present invention, the palm-based fats and oils are palm oils and fats and oils that have been processed by separation, curing, and the like using these as raw materials, and examples include palm olein, super palm olein, palm stearin, and those obtained by curing these. .
本発明のパーム系油脂の硬化抑制剤（以下、単に「硬化抑制剤」ともいう）は、上記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。本発明の硬化抑制剤は、上記ソルビタン脂肪酸エステルをそのままパーム系油脂組成物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、これを硬化抑制剤としてパーム系油脂組成物に添加して用いても良い。 The palm oil fat curing inhibitor of the present invention (hereinafter, also simply referred to as “curing inhibitor”) comprises the above sorbitan fatty acid ester as an active ingredient. The curing inhibitor of the present invention may be used by adding the sorbitan fatty acid ester as it is to the palm oil composition, or by preparing a preparation containing the sorbitan fatty acid ester, and using this as a curing inhibitor. You may add and use to a composition.
本発明のパーム系油脂組成物は、少なくともパーム系油脂を原料として製造される油脂組成物に本発明の硬化抑制剤を添加した食用油脂組成物である。このような食用油脂組成物の形態としては、例えば油中水型乳化物であるマーガリン、ファットスプレッド及び水分をほとんど含まないショートニング等の可塑性油脂組成物が挙げられる。ここで、マーガリンは、食用油脂含有率が８０質量％以上のものをいい、ファットスプレッドは食用油脂含有率が８０質量％未満のものをいう。 The palm oil-and-fat composition of the present invention is an edible oil-and-fat composition obtained by adding the curing inhibitor of the present invention to an oil-and-fat composition manufactured using at least palm-based oil and fat as a raw material. Examples of the edible oil / fat composition include margarine which is a water-in-oil emulsion, fat spread, and a plastic oil / fat composition such as shortening containing almost no moisture. Here, margarine means that the edible fat content is 80% by mass or more, and fat spread means that the edible fat content is less than 80% by mass.
本発明のパーム系油脂組成物の原料にパーム系油脂と共にパーム系油脂以外の食用油脂を用いる場合、その種類に特に制限はないが、例えばカカオ脂、ヤシ油、パーム核油、オリーブ油、キャノーラ油、米ぬか油、サフラワー油、ハイオレイックサフラワー油、大豆油、コーン油、なたね油、ひまわり油、ハイオレイックひまわり油、綿実油及び落花生油等の植物油脂、乳脂、牛脂、ラード、魚油、鯨油等の動物油脂、これらの動植物油脂を分別処理又は水素添加処理したもの、更にこれらの動植物油脂単独又は二種類以上を任意に組み合わせてエステル交換処理したもの等が挙げられる。 When edible fats and oils other than palm fats and oils are used together with palm fats and oils as the raw material for the palm fats and oils composition of the present invention, the type is not particularly limited, but for example cacao butter, palm oil, palm kernel oil, olive oil, canola oil , Rice bran oil, safflower oil, high oleic safflower oil, soybean oil, corn oil, rapeseed oil, sunflower oil, high oleic sunflower oil, cottonseed oil and peanut oil, etc. Examples include animal oils and fats, those obtained by fractionating or hydrogenating these animal and vegetable oils and fats, and those obtained by subjecting these animal and vegetable oils and fats to a transesterification process in an arbitrary combination.
本発明のパーム系油脂組成物中の硬化抑制剤の含有量は、パーム系油脂組成物の形態、パーム系油脂組成物中のパーム系油脂の含有量、目的とする硬化抑制の程度等により異なり一様ではないが、例えばパーム系油脂組成物に含有される食用油脂１００質量部に対して、主構成脂肪酸がラウリン酸であるソルビタン脂肪酸エステルの含有量が通常０．０５〜５．０質量部、好ましくは０．１〜３．０質量部、更に好ましくは０．２〜１．０であるように調整することができる。 The content of the curing inhibitor in the palm-based oil / fat composition of the present invention varies depending on the form of the palm-based oil / fat composition, the content of the palm-based fat / oil in the palm-based oil / fat composition, the degree of intended curing inhibition, and the like. Although it is not uniform, for example, the content of sorbitan fatty acid ester whose main constituent fatty acid is lauric acid is usually 0.05 to 5.0 parts by mass with respect to 100 parts by mass of edible oils and fats contained in the palm-based oil or fat composition. , Preferably 0.1 to 3.0 parts by mass, more preferably 0.2 to 1.0.
また、本発明のパーム系油脂組成物中のパーム系油脂の含有量に特に制限はないが、例えばパーム系油脂組成物に含有される食用油脂１００質量部に対して、パーム系油脂の含有量が通常３０質量部以上、好ましくは６０質量部以上であるように調整することができる。パーム系油脂の含有量がこのように高い値であっても、本発明の硬化抑制剤の効果が発揮されることにより、パーム系油脂組成物の保存中の硬化が抑制される。 Moreover, although there is no restriction | limiting in particular in content of the palm oil fat in the palm oil fat composition of this invention, For example, with respect to 100 mass parts of edible oil fat contained in a palm oil fat composition, content of palm oil fat Is usually 30 parts by mass or more, preferably 60 parts by mass or more. Even if the content of the palm-based fat / oil is such a high value, the curing of the palm-based fat / oil composition is suppressed by exerting the effect of the curing inhibitor of the present invention.
本発明のパーム系油脂組成物の製造方法は特に限定されず、自体公知の方法を用いることができる。以下に、マーガリン及びファットスプレッドの製造方法を例示する。例えば、油脂及び本発明の硬化抑制剤を混合し、５０〜８０℃、好ましくは６０〜７０℃に加熱して溶解し、所望により酸化防止剤（例えば抽出トコフェロール等）、着色料（例えばβ−カロテン等）、香料（例えばミルクフレーバー等）、乳化剤（例えばレシチン、グリセリン脂肪酸エステル等）等を添加して油相とする。一方、精製水に、所望により乳又は乳製品（例えば全粉乳、脱脂粉乳等）、食塩、砂糖類、酸味料（例えばクエン酸等）を加え、５０〜７０℃に加熱して溶解し水相とする。次に、油相と水相を通常の攪拌・混合槽を用いて混合し、得られた混合液を送液ポンプで急冷捏和装置に送液し、油脂の結晶化と練捏を連続的に行いマーガリン又はファットスプレッドを得る。また乳化工程をとらず、油相と水相をそれぞれ定量ポンプで急冷捏和装置に送液し、以下同様に処理しマーガリン又はファットスプレッドを得ることもできる。得られたマーガリン又はファットスプレッドは、更に、２５〜３０℃で１２〜７２時間テンパリングされるのが好ましい。 The manufacturing method of the palm oil fat composition of the present invention is not particularly limited, and a method known per se can be used. Below, the manufacturing method of a margarine and a fat spread is illustrated. For example, fats and oils and the curing inhibitor of the present invention are mixed and dissolved by heating to 50 to 80 ° C., preferably 60 to 70 ° C., and optionally an antioxidant (for example, extracted tocopherol) or the like, and a colorant (for example, β- Carotene, etc.), fragrance (eg, milk flavor, etc.), emulsifier (eg, lecithin, glycerin fatty acid ester, etc.) and the like are added to obtain an oil phase. On the other hand, milk or dairy products (for example, whole milk powder, skim milk powder, etc.), salt, sugars, acidulants (for example, citric acid, etc.) are added to purified water as desired, and dissolved by heating to 50 to 70 ° C. And Next, the oil phase and the aqueous phase are mixed using a normal stirring / mixing tank, and the resulting mixture is fed to a quenching kneader with a feed pump to continuously crystallization and kneading of fats and oils. To get a margarine or fat spread. Also, without taking the emulsification step, the oil phase and the water phase can be respectively sent to a quenching and kneading device with a metering pump, and then treated in the same manner to obtain margarine or fat spread. The obtained margarine or fat spread is preferably tempered at 25-30 ° C. for 12-72 hours.
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］
［ソルビタン脂肪酸エステルの製造］
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた３Ｌの四つ口フラスコに、ソルビトール（商品名：ソルビトールＳ；物産フードサイエンス社製）を９１６．８ｇ仕込み、次に脂肪酸混合物（商品名：ラウリン酸Ｌ−９８；脂肪酸組成：ラウリン酸９８質量％、ミリスチン酸２質量％；丸善薬品産業社製）１４８３．２ｇを仕込み、触媒として水酸化ナトリウム３．４ｇ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２．５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、主構成脂肪酸がラウリン酸であるソルビタン脂肪酸エステル（試作品Ａ；エステル化率５０％；ソルビタン型含有量７２．４質量％）約１９２０ｇを得た。
[Production Example 1]
[Production of sorbitan fatty acid ester]
916.8 g of sorbitol (trade name: sorbitol S; manufactured by Food Science Co., Ltd.) was charged into a 3 L four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, and then a fatty acid mixture (product) Name: Lauric acid L-98; Fatty acid composition: Lauric acid 98% by mass, Myristic acid 2% by mass; manufactured by Maruzen Pharmaceutical Co., Ltd.) 1483.2g, 3.4g of sodium hydroxide as catalyst was added, nitrogen was added under normal pressure The esterification reaction was carried out in a gas stream for 2.5 hours at 235 ° C. until the acid value was 10 or less. The obtained reaction product was cooled to obtain about 1920 g of a sorbitan fatty acid ester whose main constituent fatty acid is lauric acid (prototype A; esterification rate 50%; sorbitan type content 72.4% by mass).
［製造例２］
［ソルビタン脂肪酸エステルの製造］
撹拌機、温度計、ガス吹込管及び水分離器を取り付けた３Ｌの四つ口フラスコに、ソルビトール（商品名：ソルビトールＳ；物産フードサイエンス社製）を７２７．２ｇ仕込み、次に脂肪酸混合物（商品名：ラウリン酸Ｌ−９８；脂肪酸組成：ラウリン酸９８質量％、ミリスチン酸２質量％；丸善薬品産業社製）１６７２．８ｇを仕込み、触媒として水酸化ナトリウム１．２ｇ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５．０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、主構成脂肪酸がラウリン酸であるソルビタン脂肪酸エステル（試作品Ｂ；エステル化率７５％；ソルビタン型含有量９３．６質量％）約１９６０ｇを得た。
[Production Example 2]
[Production of sorbitan fatty acid ester]
727.2 g of sorbitol (trade name: Sorbitol S; manufactured by Food Science Co., Ltd.) was charged into a 3 L four-necked flask equipped with a stirrer, thermometer, gas blowing tube and water separator, and then a fatty acid mixture (product) Name: Lauric acid L-98; Fatty acid composition: Lauric acid 98% by mass, Myristic acid 2% by mass; manufactured by Maruzen Pharmaceutical Industry Co., Ltd.) 1672.8g, sodium hydroxide 1.2g was added as a catalyst, nitrogen was added under normal pressure The esterification reaction was performed for 5.0 hours at 235 ° C. until the acid value was 10 or less in a gas stream. The obtained reaction product was cooled to obtain about 1960 g of sorbitan fatty acid ester (prototype B; esterification rate 75%; sorbitan type content 93.6% by mass) whose main constituent fatty acid is lauric acid.
［試験例］
［ファットスプレッドの製造及び評価］
（１）ファットスプレッドの原材料
１）精製パーム油（商品名：ＲＰＯ；植田製油社製）
２）菜種白絞油（商品名：日清菜種サラダ油（Ｓ）；日清オイリオグループ社製）
３）硬化抑制剤
３−１）ソルビタン脂肪酸エステル（試作品Ａ；主構成脂肪酸：ラウリン酸）
３−２）ソルビタン脂肪酸エステル（試作品Ｂ；主構成脂肪酸：ラウリン酸）
３−３）ソルビタン脂肪酸エステル（市販品Ａ；商品名：Ｌ−３００；主構成脂肪酸：ラウリン酸；理研ビタミン社製）
３−４）ソルビタン脂肪酸エステル（市販品Ｂ；商品名：ポエムＯ−８０Ｖ；主構成脂肪酸：オレイン酸；理研ビタミン社製）
３−５）ソルビタン脂肪酸エステル（市販品Ｃ；商品名：ポエムＳ−６５Ｖ；主構成脂肪酸：ステアリン酸；理研ビタミン社製）
３−６）ソルビタン脂肪酸エステル（市販品Ｄ；商品名：ポエムＳ−３２０ＹＮ；主構成脂肪酸：ステアリン酸；理研ビタミン社製）
３−７）ソルビタン脂肪酸エステル（市販品Ｅ；商品名：製品名：ポエムＢ−１５０；主構成脂肪酸：ベヘニン酸；理研ビタミン社製）
４）グリセリン脂肪酸エステル（商品名：エマルジーＭＳ；理研ビタミン社製）
５）レシチン（商品名：ＴＯＰＣＩＴＨＩＮ ＵＢ；カーギルジャパン社製）
６）イオン交換水
７）食塩（日本食塩製造社製）
[Test example]
[Manufacture and evaluation of fat spread]
(1) Fat spread raw materials 1) Refined palm oil (trade name: RPO; Ueda Oil Co., Ltd.)
2) White rapeseed oil (trade name: Nissin rapeseed salad oil (S); manufactured by Nisshin Oilio Group)
3) Curing inhibitor 3-1) Sorbitan fatty acid ester (prototype A; main constituent fatty acid: lauric acid)
3-2) Sorbitan fatty acid ester (prototype B; main constituent fatty acid: lauric acid)
3-3) Sorbitan fatty acid ester (commercial product A; trade name: L-300; main constituent fatty acid: lauric acid; manufactured by Riken Vitamin Co., Ltd.)
3-4) Sorbitan fatty acid ester (commercial product B; trade name: Poem O-80V; main constituent fatty acid: oleic acid; manufactured by Riken Vitamin Co., Ltd.)
3-5) Sorbitan fatty acid ester (commercial product C; trade name: Poem S-65V; main constituent fatty acid: stearic acid; manufactured by Riken Vitamin Co., Ltd.)
3-6) Sorbitan fatty acid ester (commercially available product D; trade name: Poem S-320YN; main constituent fatty acid: stearic acid; manufactured by Riken Vitamin Co., Ltd.)
3-7) Sorbitan fatty acid ester (commercial product E; trade name: product name: Poem B-150; main constituent fatty acid: behenic acid; manufactured by Riken Vitamin Co., Ltd.)
4) Glycerin fatty acid ester (trade name: Emulgie MS; manufactured by Riken Vitamin Co., Ltd.)
5) Lecithin (trade name: TOPCITHIN UB; manufactured by Cargill Japan)
6) Ion-exchanged water 7) Sodium chloride (manufactured by Nippon Salt Manufacturing Co., Ltd.)
（２）ファットスプレッドの製造方法
表１に示した２倍量の原材料を用いて、下記１）〜４）の工程に従いファットスプレッドを作製した。
１）イオン交換水に食塩を加えて溶解し、６０℃に加温して水相とした。
２）精製パーム油及び菜種白絞油からなる配合油に硬化抑制剤、グリセリン脂肪酸エステル及びレシチンを加えて溶解し、７０℃に加温して油相とした。
３）２）の油相をＴＫホモミキサー（型式：ＭＡＲＫ ＩＩ；プライミクス社製）で３０００ｒｐｍで攪拌しながら、１）の水相を徐々に加え、全て加えた後、同回転速度で２分間撹拌し、更に１００００ｒｐｍで５分間撹拌し、Ｗ／Ｏ乳化させた。
４）得られた乳化液を常法により急冷捏和後、円柱型のプラスチック製容器（直径６５ｍｍ、高さ４０ｍｍ）に充填したものを２５℃で２４時間テンパリング処理をし、ファットスプレッド１〜７を得た。
５）対照として、硬化抑制剤を使用せずに上記１）〜４）を同様に実施し、硬化抑制剤を含有しないファットスプレッド８を得た。
(2) Manufacturing method of fat spread Using the double amount of raw materials shown in Table 1, a fat spread was produced according to the following steps 1) to 4).
1) Salt was added to ion-exchanged water for dissolution, and the mixture was heated to 60 ° C. to obtain an aqueous phase.
2) A curing inhibitor, a glycerin fatty acid ester and lecithin were added to and dissolved in a blended oil consisting of refined palm oil and rapeseed white squeezed oil, and heated to 70 ° C. to obtain an oil phase.
3) While stirring the oil phase of 2) with a TK homomixer (model: MARK II; manufactured by Primix) at 3000 rpm, gradually add the water phase of 1), and after adding all, stir for 2 minutes at the same rotational speed. The mixture was further stirred at 10000 rpm for 5 minutes to emulsify W / O.
4) After quenching and kneading the obtained emulsion by a conventional method, a cylindrical plastic container (diameter 65 mm, height 40 mm) filled with tempering treatment at 25 ° C. for 24 hours, fat spreads 1 to 7 Got.
5) As a control, the above 1) to 4) were similarly carried out without using a curing inhibitor, and a fat spread 8 containing no curing inhibitor was obtained.
（３）硬度の測定
プラスチック製容器に充填された１０℃のファットスプレッド１〜８について、１０℃で８時間保存後及び１０℃で１ヶ月間保存後のそれぞれの時点において、テクスチャーアナライザー（製品名：Ｅｚ Ｔｅｓｔ；島津製作所社製）を用いて２５℃の環境下で硬度を測定した。測定では、直径５ｍｍの円柱プランジャーを使用し、該プランジャーをファットスプレッド表面より１０ｍｍ押し込んだ際の最大応力（Ｎ）を硬度とした。１ヶ月間保存後の硬度及び硬度増加率（８時間保存後の硬度を基準として１ヶ月間保存後の硬度を百分率で表したもの）について、以下の評価基準に従いそれぞれ記号化した。結果を表２に示す。
＜１ヶ月間保存後の硬度＞
○：３．０Ｎ未満
△：３．０Ｎ以上、３．５Ｎ未満
×：３．５Ｎ以上
＜硬度増加率＞
○：１５０％未満
△：１５０％以上、１７０％未満
×：１７０％以上
(3) Measurement of hardness Texture analyzer (product name) at each time point after storage at 10 ° C. for 8 hours and after storage at 10 ° C. for 1 month for 10 ° C. fat spreads 1 to 8 filled in a plastic container. : Ez Test; manufactured by Shimadzu Corporation), the hardness was measured under an environment of 25 ° C. In the measurement, a cylindrical plunger having a diameter of 5 mm was used, and the maximum stress (N) when the plunger was pushed 10 mm from the fat spread surface was defined as hardness. The hardness after storage for 1 month and the rate of increase in hardness (representing the hardness after storage for 1 month as a percentage based on the hardness after storage for 8 hours) were symbolized according to the following evaluation criteria. The results are shown in Table 2.
<Hardness after storage for 1 month>
○: Less than 3.0N Δ: 3.0N or more, less than 3.5N ×: 3.5N or more <Hardness increase rate>
○: Less than 150% Δ: 150% or more, less than 170% ×: 170% or more
表２の結果から、ラウリン酸を主構成脂肪酸とするソルビタン脂肪酸エステルを硬化抑制剤として添加して得られたファットスプレッド１〜３は、いずれの評価項目においても「○」であった。これに対し、ラウリン酸以外の脂肪酸を主構成脂肪酸とするソルビタン脂肪酸エステルを硬化抑制剤として添加して得られたファットスプレッド４〜７及び対照のファットスプレッド８では、いずれかの評価項目において「△」以下であり、本発明の実施例に比べて劣っていた。 From the results of Table 2, fat spreads 1 to 3 obtained by adding sorbitan fatty acid ester having lauric acid as a main constituent fatty acid as a curing inhibitor were “◯” in any evaluation item. On the other hand, in the fat spreads 4 to 7 and the control fat spread 8 obtained by adding a sorbitan fatty acid ester having a fatty acid other than lauric acid as a main constituent fatty acid as a curing inhibitor, “△” It was below and was inferior compared with the Example of this invention.
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