JPH05287296A - Edible hardened oil - Google Patents
Edible hardened oilInfo
- Publication number
- JPH05287296A JPH05287296A JP4088585A JP8858592A JPH05287296A JP H05287296 A JPH05287296 A JP H05287296A JP 4088585 A JP4088585 A JP 4088585A JP 8858592 A JP8858592 A JP 8858592A JP H05287296 A JPH05287296 A JP H05287296A
- Authority
- JP
- Japan
- Prior art keywords
- milk fat
- trans
- oil
- fat
- hydrogenated
- 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.)
- Granted
Links
Landscapes
- Confectionery (AREA)
- Edible Oils And Fats (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、食用硬化油、詳しく
は、製菓用に適する食用硬化油に関する。FIELD OF THE INVENTION The present invention relates to a hardened edible oil, and more particularly to a hardened edible oil suitable for confectionery.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】従来、
乳脂は、風味の面から油脂加工技術の応用がほとんどさ
れていなかった。しかし、近年、コレステロールの除
去、あるいはソフトタイプのバターやマーガリンの製造
のため、乳脂を分別、ウインタリングしてソフト化ある
いはハード化したり、新しい技術である超臨界抽出の技
術開発が進められている。また、乳脂を水添（硬化）し
て、保型性を高めたり、チョコレートの抗ブルーム添加
剤（アンチブルーム剤）としての応用検討が既になされ
ている。2. Description of the Related Art Conventionally, the problems to be solved by the invention
As for milk fat, almost no application of the oil and fat processing technology has been made from the aspect of flavor. However, in recent years, in order to remove cholesterol or to produce soft type butter and margarine, milk fat is separated and winterized to be softened or hardened, and a new technology, supercritical extraction, is being developed. .. In addition, hydrogenation (curing) of milk fat to enhance shape retention and application of chocolate as an anti-bloom additive (anti-bloom agent) have already been studied.
【０００３】しかし、乳脂の脂肪酸組成は飽和酸が多
く、水添されるとさらに飽和酸が増加し、硬化油の融点
のわりには、口溶けが悪くかつ食感がザラつく欠点があ
る。一般に、乳脂のように沃素価が低い（即ち構成脂肪
酸の不飽和度が低い）油脂を水添する場合、通常の水添
で得られる油脂とトランス異性化水添のような特殊な水
添で得られる油脂との物性の差は小さいか、又はほとん
ど無いと考えられていた。そこで、従来知られている異
性化水添もほとんどが沃素価４０以上の油脂に適用され
ており（特公昭５７−７４８９３号公報参照）、乳脂の
ように沃素価の低い油脂に適用する試みはなされておら
ず、わずかにラウリン脂肪（パーム核脂肪）という特殊
な油脂に適用されているだけである（特開昭６４−６０
３２６号公報参照）。However, the fatty acid composition of milk fat has a large amount of saturated acid, and when hydrogenated, the saturated acid further increases, and the melting point of hydrogenated oil has the drawbacks of poor melting in the mouth and rough texture. Generally, in the case of hydrogenating fats and oils having a low iodine value (that is, low unsaturation degree of constituent fatty acids) such as milk fat and fats, it is possible to use oils and fats obtained by ordinary hydrogenation and special hydrogenation such as trans isomerization hydrogenation. It was thought that the difference in physical properties from the obtained fats or oils was small or almost nonexistent. Therefore, most of the conventionally known isomerized hydrogenation has been applied to fats and oils having an iodine value of 40 or more (see Japanese Patent Publication No. 57-74893), and attempts to apply it to fats and oils having a low iodine value such as milk fat have been made. No, it is only applied to a special oil called lauric fat (palm kernel fat) (JP-A-64-60).
326).
【０００４】従って、本発明の目的は、口溶けが良好で
かつ酸化安定性、保型性及び耐ブルーム性に優れた食用
硬化油を提供することにある。Therefore, an object of the present invention is to provide a hardened edible oil which is well melted in the mouth and is excellent in oxidation stability, shape retention and bloom resistance.
【０００５】[0005]
【課題を解決するための手段】本発明者らは、近年、利
用が増える傾向のある乳脂を硬化して高度に利用する方
法を鋭意検討した結果、乳脂を、異性化水添することに
より上記目的が達成されることを知見した。本発明は、
上記知見に基づいてなされたもので、異性化水添された
乳脂及び／又は加工乳脂であって、異性化水添により実
質的に生成したトランス酸についての〔トランス／（シ
ス＋トランス）〕値の、トランス平衡値に対する割合
が、６５〜９８％であり、且つ融点が３２〜３８℃であ
る食用硬化油を提供するものである。Means for Solving the Problems In recent years, the present inventors have earnestly studied a method of curing and highly utilizing milk fat, which tends to be used more frequently, and as a result, the milk fat is subjected to isomerization and hydrogenation as described above. It was found that the purpose was achieved. The present invention is
[Trans / (cis + trans)] value for trans acid substantially produced by isomerization and hydrogenation, which was made on the basis of the above findings and is isomerized and hydrogenated milk fat and / or processed milk fat. Of edible hydrogenated oil having a melting point of 32 to 38 ° C. and a ratio of trans to equilibrium value of 65 to 98%.
【０００６】以下、本発明の食用硬化油について詳細に
説明する。本発明の食用硬化油は、異性化水添によりト
ランス酸を多量に含む硬化乳脂である。The edible hardened oil of the present invention will be described in detail below. The hardened edible oil of the present invention is hardened milk fat containing a large amount of trans acid by isomerization and hydrogenation.
【０００７】本発明の食用硬化油の原料油脂としては、
乳脂及び分別もしくはエステル交換等の処理を施された
加工乳脂を挙げることができる。上記乳脂としては、沃
素価が２５〜４７のものを使用することが好ましく、２
８〜４０のものがさらに好ましい。As the raw material fat of the hardened edible oil of the present invention,
Mention may be made of milk fat and processed milk fat subjected to a treatment such as fractionation or transesterification. As the milk fat, it is preferable to use one having an iodine value of 25 to 47.
It is more preferably 8 to 40.
【０００８】本発明の食用硬化油の製造に使用される異
性化水添の反応触媒としては、一般に使用されているニ
ッケル触媒、イオウ被毒触媒等広範囲のものが使用で
き、例えば、ニッケル触媒、銅・ニッケル触媒、銅・ク
ロム・マンガン触媒等公知の水添触媒が挙げられる。上
記水添触媒の使用量は、原料油脂に対して、好ましくは
０．０５〜３．０ｗｔ％、更に好ましくは０．１〜２．
０ｗｔ％である。一方、被毒物質として、含硫アミノ
酸、例えば、メチオニンを用いることが好ましい。上記
被毒物質の使用量は、原料油脂に対して、好ましくは４
０〜５００ｐｐｍ、更に好ましくは５０〜２５０ｐｐｍ
である。尚、上記反応触媒としては、上記ニッケル触媒
に上記含硫アミノ酸（被毒物質）を少量添加したもの
が、効率的であり、好ましい。As the isomerization hydrogenation reaction catalyst used in the production of the hardened edible oil of the present invention, a wide range of catalysts such as commonly used nickel catalysts and sulfur poisoning catalysts can be used. Known hydrogenation catalysts such as copper / nickel catalysts and copper / chromium / manganese catalysts can be used. The amount of the hydrogenation catalyst used is preferably 0.05 to 3.0 wt%, and more preferably 0.1 to 2% with respect to the raw material oil and fat.
It is 0 wt%. On the other hand, it is preferable to use a sulfur-containing amino acid such as methionine as the poisoning substance. The amount of the poisoning substance used is preferably 4 with respect to the raw material oil and fat.
0 to 500 ppm, more preferably 50 to 250 ppm
Is. As the reaction catalyst, a catalyst obtained by adding a small amount of the sulfur-containing amino acid (poisoning substance) to the nickel catalyst is efficient and preferable.
【０００９】本発明の食用硬化油の製造における上記原
料油脂の異性化水添は、上記反応触媒の存在下に、通
常、好ましくは１８０〜２４０℃程度の温度で、水素を
常圧下または加圧下に、原料油脂と接触せしめて実施す
ることができる。The isomerization and hydrogenation of the above-mentioned raw material fats and oils in the production of the hardened edible oil of the present invention is carried out in the presence of the above-mentioned reaction catalyst, usually at a temperature of preferably 180 to 240 ° C. under a normal pressure or a pressure of hydrogen. In addition, it can be carried out by contacting with the raw material oil and fat.
【００１０】原料油脂（乳脂）を、異性化水添すること
により実質的に生成したトランス酸は、異性化水添乳脂
中のトランス酸から原料油脂（乳脂）中のトランス酸を
除いたものである。ここで、Ｔ＝トランス／（シス＋ト
ランス）は、全二重結合中に含まれるトランス二重結合
の割合を表すものとして、トランス酸量１００％である
トリエライジンの沃素価（８６．０）から、次の〔数
１〕によって計算することができる〔鈴木ら、油化学、
３１、１０、（１９８２）等参照〕。The trans acid substantially produced by isomerizing and hydrogenating a raw material fat (milk fat) is a trans acid in the isomerized hydrogenated milk fat from which the trans acid in the raw fat or oil (milk fat) is removed. is there. Here, T = trans / (cis + trans) represents the ratio of trans double bonds contained in all double bonds, and the iodine value (86.0) of trielaidin having a trans acid amount of 100%. Can be calculated by the following [Equation 1] [Suzuki et al.
31, 10, (1982), etc.].
【００１１】[0011]
【数１】Ｔ＝乳脂中のトランス酸量（％）×（トリエラ
イジンの沃素価／乳脂の沃素価）＝乳脂中のトランス酸
量（％）×（８６．０／乳脂の沃素価）## EQU1 ## T = trans acid amount in milk fat (%) × (trieridine iodine value / milk fat iodine value) = trans acid amount in milk fat (%) × (86.0 / fat iodine value)
【００１２】上記〔数１〕から、乳脂の沃素価及びトラ
ンス酸量を測定すれば、その乳脂のＴ値を求めることが
でき、この沃素価及びトランス酸量は、例えば、ＧＬＣ
法〔鈴木ら、油化学，３０，２９，（１９８１）等参
照〕等により測定することができる。From the above [Formula 1], the T value of the milk fat can be determined by measuring the iodine value and the trans acid amount of the milk fat. The iodine value and the trans acid amount can be determined by, for example, GLC.
Method (see Suzuki et al., Oil Chemistry, 30, 29, (1981) etc.) and the like.
【００１３】また、上記Ｔの平衡値（トランス平衡値，
Ｔmax ）は、経験的に約７０％であることから、異性化
水添乳脂のＴ値のＴmax に対する割合（ｒ）は、次の
〔数２〕で表せる〔鈴木ら、油化学，３０，２９，（１
９８１）等参照〕。In addition, the equilibrium value of T (transformer equilibrium value,
Since T max ) is empirically about 70%, the ratio (r) of T value of isomerized hydrogenated milk fat to T max can be expressed by the following [Equation 2] [Suzuki et al. , 29, (1
981) etc.].
【００１４】[0014]
【数２】ｒ（％）＝（Ｔ／Ｔmax ）×１００## EQU2 ## r (%) = (T / T max ) × 100
【００１５】本発明の食用硬化油においては、含硫アミ
ノ酸（被毒物質）の添加量を調節することにより、水素
添加された乳脂のトランス体含量をコントロールするこ
とができるが、異性化水添により実質的に生成するトラ
ンス酸量についての〔トランス／（シス＋トランス）〕
値が、上記トランス平衡値に対して６５〜９８％、好ま
しくは７５〜９５％となるように異性化水添が行われ
る。In the edible hydrogenated oil of the present invention, the trans-form content of hydrogenated milk fat can be controlled by adjusting the addition amount of sulfur-containing amino acid (poisoning substance). [Trans / (cis + trans)] for the amount of trans acid substantially generated by
The isomerization hydrogenation is carried out so that the value becomes 65 to 98%, preferably 75 to 95%, with respect to the trans equilibrium value.
【００１６】また、本発明の食用硬化油においては、異
性化水添操作の調節により、融点をある程度任意に調整
することができるが、該融点は、３２〜３８℃、好まし
くは３３〜３６℃に調整される。本発明の食用硬化油
は、異性化水添後、通常の操作により脱臭油等としても
よく、例えば、製菓用等の用途に用いられる。In the edible hydrogenated oil of the present invention, the melting point can be adjusted to some extent by adjusting the isomerization hydrogenation operation, but the melting point is 32 to 38 ° C, preferably 33 to 36 ° C. Adjusted to. The hydrogenated edible oil of the present invention may be deodorized oil or the like by a usual operation after isomerization and hydrogenation, and is used for confectionery, for example.
【００１７】また、本発明の食用硬化油には、他の油脂
を添加して用いても良く、これらの油脂としては、例え
ば、乳脂、分別乳脂等が挙げられる。上記油脂は、該油
脂の種類及び用途等により異なるが、通常、該油脂と本
発明の食用硬化油との比が、（前者）／（後者）＝９５
〜０／５〜１００（重量基準）となるように添加するこ
とが好ましい。Other fats and oils may be added to the hardened edible oil of the present invention, and examples of these fats and oils include milk fat and fractionated milk fat. The above-mentioned fats and oils differ depending on the type and use of the fats and oils, but usually the ratio of the fats and oils and the hardened edible oil of the present invention is (the former) / (the latter) = 95.
It is preferable to add it so that it will be ˜0 / 5 to 100 (weight basis).
【００１８】[0018]
【実施例】以下に、実施例を比較例とともに挙げ、本発
明の食用硬化油を具体的に説明する。EXAMPLES Hereinafter, the edible hardened oil of the present invention will be specifically described with reference to Examples and Comparative Examples.
【００１９】実施例−１ 沃素価３３．３の精製乳脂８００ｇを、３リットルのス
テンレス製オートクレーブにとり、水添触媒（日産ガー
ドラー（株）製Ｇ−９５Ｅ）を油脂（精製乳脂）に対し
０．１５ｗｔ％添加し、同時にメチオニンを１３０ｐｐ
ｍ添加し、水素を２Ｋｇ／ｃｍ2 Ｇの圧力で０．０５リ
ットル／ｍｉｎで流して反応させた。この際の反応温度
は２１０℃、攪拌は５００ｒｐｍであった。反応時間３
００分で沃素価が２９．１の異性化水添乳脂（Ａ）が得
られた。触媒をろ過した後、白土を０．５％添加し、１
１０℃で３０分間脱色し、ろ過して得られた脱色油を２
５０℃で１時間水蒸気蒸留を行い脱臭油を得た。なお、
得られた脱臭油には酸化防止のためトコフェロールを１
００ｐｐｍ添加した。融点は、３２．７℃、トランス体
の割合は、２７．４％、また、実質的に生成したトラン
ス酸についてのＴ値の割合ｒは、平衡値（Ｔmax ）に対
して８９％であった。更に、水添触媒の添加量を０．２
ｗｔ％、メチオニンの添加量を２００ｐｐｍに変えた他
は、上記（Ａ）の製造と同様にして水添反応を行い、反
応時間３００分で、沃素価２８．３、融点３５．０℃の
異性化水添乳脂（Ｂ）を得た。得られた異性化水添乳脂
（Ｂ）についても、上記（Ａ）と同様にして脱臭油を得
た。Example 1 800 g of purified milk fat having an iodine value of 33.3 was placed in a 3 liter stainless steel autoclave, and a hydrogenation catalyst (G-95E manufactured by Nissan Gardler Co., Ltd.) was added to oil (purified milk fat) in an amount of 0. Add 15 wt% and at the same time add 130 pp of methionine
Then, hydrogen was flown at a pressure of 2 Kg / cm 2 G at a rate of 0.05 liter / min to cause a reaction. The reaction temperature at this time was 210 ° C., and the stirring was 500 rpm. Reaction time 3
At 00 minutes, an isomerized hydrogenated milk fat (A) having an iodine value of 29.1 was obtained. After filtering the catalyst, add 0.5% clay.
Decolorize for 30 minutes at 10 ° C and filter to 2
Steam distillation was carried out at 50 ° C. for 1 hour to obtain a deodorized oil. In addition,
Tocopherol was added to the obtained deodorized oil to prevent oxidation.
00 ppm was added. The melting point is 32.7 ° C., the ratio of the trans isomer is 27.4%, and the T value ratio r of the substantially produced trans acid is 89% with respect to the equilibrium value (T max ). It was Furthermore, the amount of hydrogenation catalyst added is 0.2
wt%, except that the amount of methionine added was changed to 200 ppm, the hydrogenation reaction was carried out in the same manner as in the production of (A) above, and the reaction time was 300 minutes and the isomerism was 28.3 with a melting point of 35.0 ° C. A hydrogenated milk fat (B) was obtained. With respect to the obtained isomerized hydrogenated milk fat (B), a deodorized oil was obtained in the same manner as in the above (A).
【００２０】比較例−１ 沃素価３３．３の精製乳脂８００ｇを、３リットルのオ
ートクレーブにとり、水添触媒（日産ガードラー（株）
製、Ｇ−９５Ｅ）を油脂に対して０．１ｗｔ％添加し、
０．１４リットル／ｍｉｎ，２Ｋｇ／ｃｍ2 Ｇの条件で
水素を供給した。反応温度は１８０℃、攪拌は５００ｐ
ｐｍで実施した。反応時間２２分で、沃素価が２７．５
の通常水添乳脂（Ｃ）が得られた。トランス体の割合は
１０．５％であった。さらに反応時間３５分で沃素価が
２６．１の通常水添乳脂（Ｄ）が得られた。トランス体
の割合は、１１．７％であった。（Ｃ）、（Ｄ）共に、
触媒ろ過後の脱色、脱臭は実施例−１に準じた。また、
酸化防止のためトコフェロールを１００ｐｐｍ添加し
た。下記〔表１〕に、精製乳脂および実施例−１で得ら
れた異性化水添乳脂（Ａ，Ｂ）及び比較例−１で得られ
た通常水添乳脂（Ｃ，Ｄ）の物性を示した。通常水添乳
脂はＳＦＣの値は特に３５℃以上で高く、口溶けの点で
問題があった。これに対し、異性化水添乳脂は３５℃以
上でのＳＦＣは小さく、口溶けが優れていた。Comparative Example-1 800 g of purified milk fat having an iodine value of 33.3 was placed in a 3 liter autoclave and hydrogenated catalyst (Nissan Gardler Co., Ltd.) was used.
Manufactured by G-95E) is added to the fats and oils in an amount of 0.1 wt%,
Hydrogen was supplied under the conditions of 0.14 liter / min and 2 Kg / cm 2 G. Reaction temperature is 180 ° C, stirring is 500p
pm. The reaction time was 22 minutes and the iodine value was 27.5.
The normally hydrogenated milk fat (C) was obtained. The ratio of trans form was 10.5%. Further, a normally hydrogenated milk fat (D) having an iodine value of 26.1 was obtained after a reaction time of 35 minutes. The ratio of trans form was 11.7%. Both (C) and (D)
Decolorization and deodorization after catalyst filtration were in accordance with Example-1. Also,
Tocopherol was added at 100 ppm to prevent oxidation. The following [Table 1] shows the physical properties of the purified milk fat, the isomerized hydrogenated milk fat (A, B) obtained in Example-1 and the normal hydrogenated milk fat (C, D) obtained in Comparative Example-1. It was Usually, hydrogenated milk fat has a high SFC value especially at 35 ° C. or higher, and has a problem in melting in the mouth. On the other hand, the isomerized hydrogenated milk fat had a small SFC at 35 ° C or higher and was excellent in melting in the mouth.
【００２１】[0021]
【表１】 [Table 1]
【００２２】実施例−２ 実施例−１及び比較例−１で調製した異性化水添乳脂及
び通常水添乳脂（Ａ）（Ｂ）（Ｃ）（Ｄ）をそれぞれ下
記〔表２〕に示した配合でチョコレートを試作し、２０
℃／３０℃それぞれ３．２時間のサイクルによりブルー
ム耐性試験を行った。下記〔表３〕及び〔表４〕に、ブ
ルーム耐性試験の結果を示した。この結果から、乳脂を
添加したチョコレートは、試験期間中でもブルームの発
生が認められ、また、通常水添乳脂を添加したチョコレ
ートも僅かにブルームの発生が認められた。これに対し
て、異性化水添乳脂（本発明の食用硬化油）を添加した
チョコレートは、ブルームの発生が認められず、耐ブル
ーム効果が認められた。Example-2 The isomerized hydrogenated milk fats (A) (B) (C) (D) prepared in Example-1 and Comparative Example-1 are shown in the following [Table 2]. Prototype chocolate with a different formulation, 20
A bloom resistance test was performed by a cycle of 3.2 ° C./30° C. each. The results of the bloom resistance test are shown in the following [Table 3] and [Table 4]. From these results, it was confirmed that the chocolate to which the milk fat was added had bloom even during the test period, and the chocolate to which the hydrogenated milk fat was added usually had slight bloom. On the other hand, in the chocolate to which the isomerized hydrogenated milk fat (hardened oil for cooking of the present invention) was added, blooming was not observed and the bloom resistance effect was recognized.
【００２３】[0023]
【表２】 [Table 2]
【００２４】[0024]
【表３】 [Table 3]
【００２５】[0025]
【表４】 [Table 4]
【００２６】[0026]
【発明の効果】本発明の食用硬化油は、口溶けが良好で
かつ酸化安定性、保型性、耐ブルーム性に優れた油脂で
あるため、現在まで使用が制限されていた製菓用油脂に
配合することにより物性的に優れた組成物等の用途に利
用することができる。EFFECTS OF THE INVENTION The hardened edible oil of the present invention is a fat and oil which is well melted in the mouth and is excellent in oxidation stability, shape retention and bloom resistance. By doing so, it can be used for applications such as compositions having excellent physical properties.
Claims (3)
脂であって、異性化水添により実質的に生成したトラン
ス酸についての〔トランス／（シス＋トランス）〕値
の、トランス平衡値に対する割合が、６５〜９８％であ
り、且つ融点が３２〜３８℃である食用硬化油。1. A trans equilibrium value of a [trans / (cis + trans)] value of a trans acid substantially produced by isomerization and hydrogenation, which is isomerized and hydrogenated milk fat and / or processed milk fat. Edible hydrogenated oil having a ratio of 65 to 98% and a melting point of 32 to 38 ° C.
量％、その他の油脂９５〜０重量％からなる製菓用脂
肪。2. A fat for confectionery comprising 5 to 100% by weight of the hardened edible oil according to claim 1 and 95 to 0% by weight of other fats and oils.
である請求項２記載の製菓用脂肪。3. The fat for confectionery according to claim 2, wherein the other fat and oil is milk fat and / or fractionated milk fat.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP08858592A JP3329483B2 (en) | 1992-04-09 | 1992-04-09 | Edible hardened oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP08858592A JP3329483B2 (en) | 1992-04-09 | 1992-04-09 | Edible hardened oil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05287296A true JPH05287296A (en) | 1993-11-02 |
| JP3329483B2 JP3329483B2 (en) | 2002-09-30 |
Family
ID=13946923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP08858592A Expired - Lifetime JP3329483B2 (en) | 1992-04-09 | 1992-04-09 | Edible hardened oil |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3329483B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009089684A (en) * | 2007-10-11 | 2009-04-30 | Nisshin Oillio Group Ltd | Low trans-fatty acid oil and fat composition |
| WO2013161808A1 (en) * | 2012-04-24 | 2013-10-31 | 株式会社明治 | Baked composite confection having suppressed oil/fat migration |
| WO2013161807A1 (en) * | 2012-04-25 | 2013-10-31 | 株式会社明治 | Baked composite confection and method for producing same |
| JP2017042157A (en) * | 2015-08-28 | 2017-03-02 | ミヨシ油脂株式会社 | Oil and fat composition and method for producing the same and emulsified oil and fat composition |
-
1992
- 1992-04-09 JP JP08858592A patent/JP3329483B2/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009089684A (en) * | 2007-10-11 | 2009-04-30 | Nisshin Oillio Group Ltd | Low trans-fatty acid oil and fat composition |
| WO2013161808A1 (en) * | 2012-04-24 | 2013-10-31 | 株式会社明治 | Baked composite confection having suppressed oil/fat migration |
| JPWO2013161808A1 (en) * | 2012-04-24 | 2015-12-24 | 株式会社明治 | Baked composite confectionery with reduced fat transfer |
| WO2013161807A1 (en) * | 2012-04-25 | 2013-10-31 | 株式会社明治 | Baked composite confection and method for producing same |
| JPWO2013161807A1 (en) * | 2012-04-25 | 2015-12-24 | 株式会社明治 | Baked composite confectionery and method for producing the same |
| JP2017042157A (en) * | 2015-08-28 | 2017-03-02 | ミヨシ油脂株式会社 | Oil and fat composition and method for producing the same and emulsified oil and fat composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3329483B2 (en) | 2002-09-30 |
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