JP2008127399A - Solid-liquid separation inhibitor of oil and fat - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain an oil and fat composition that does not cause a solid-liquid separation such as precipitation of a solid fat, separation of a liquid fat, etc., with time. <P>SOLUTION: The oil and fat composition comprises a solid-liquid separation inhibitor composed of a polyglycerin fatty acid ester constituted of constituent fatty acids consisting of (A) one or more kinds selected from 16-22C saturated fatty acids and (B) one or more kinds selected from 8-14C saturated fatty acids and 16-22C unsaturated fatty acids in the molar ratio of the constituent fatty acids (A) of 0.3-0.9 and in the molar ratio of the constituent fatty acids (B) of 0.1-0.7 based on the total molar amount. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

  The present invention relates to a polyglycerol fatty acid ester having an effect of preventing solid-liquid separation of fats and oils. More specifically, by adding polyglycerin fatty acid ester as a solid-liquid separation inhibitor to fats and oils, solid-liquid separation such as precipitation of solid fats and separation of liquid oils does not occur over time, The present invention relates to an oil and fat composition having excellent stability.

  For the purpose of expanding the plastic range, plastic fats such as margarine, shortening, and cream are mixed with solid oils such as palm oil, lard, and hydrogenated modified hard oil, and liquid oils such as soybean oil and rapeseed oil. Oils and fats are used. However, depending on the storage state, the oil and fat composition has a problem of solid-liquid separation in which solid fat precipitates over time or liquid oil is separated on the surface. Moreover, the hardened oil utilized for the oil and fat composition contains trans-type unsaturated fatty acids except for the extremely hardened oil that is completely hydrogenated. Trans-unsaturated fatty acids have been suggested to increase LDL cholesterol and triglycerides in the blood and cause cardiovascular disease. Therefore, in recent years, trans-unsaturated fatty acids have been reduced or not included. A plastic fat composition is desired. Therefore, it is possible to increase the mixing ratio of solid oil such as palm oil and lard and liquid oil such as soybean oil and rapeseed oil, and to obtain an oil and fat composition without reducing the ratio of hardened oil or containing it at all. This will cause solid-liquid separation over time. Moreover, by this, preferable hardness in the use temperature range which is a property required as an oil-fat composition, plasticity in a wide temperature range, etc. become inadequate.

  As a method for solving this problem, a method of adding a monoglyceride of behenic acid and glycerin, which is a fatty acid having 20 or more carbon atoms (Patent Document 1), is disclosed, but a small amount that does not impair the flavor of food. The fact is that a sufficient effect is not obtained by addition.

JP 2000-119687 A

  Therefore, in the present invention, the above-mentioned problems are solved, and in a fat composition in which solid fat and liquid oil are mixed, solid fat separation such as precipitation of solid fat over time or separation of liquid oil occurs. It is providing the oil-fat composition excellent in stability.

  As a result of intensive studies by the inventor, the present inventors have found that even if the amount of polyglycerin fatty acid ester is small, solid-liquid separation of the oil and fat composition is prevented, and the present invention has been completed.

  That is, the present invention is a polyglycerin fatty acid ester for preventing solid-liquid separation of fats and oils, and in particular, the fatty acid constituting the polyglycerin fatty acid ester is selected from (A) saturated fatty acids having 16 to 22 carbon atoms. And (B) one or more selected from saturated fatty acids having 8 to 14 carbon atoms and unsaturated fatty acids having 16 to 22 carbon atoms. ) And (B), the molar ratio of the constituent fatty acid (A) is 0.3 to 0.9, and the molar ratio of the constituent fatty acid (B) is 0.1 to 0.7. The solid-liquid separation inhibitor. The esterification rate of the polyglycerin fatty acid ester is more preferably 40% or more.

  The present invention is an oil or fat composition containing the solid-liquid separation inhibitor.

  According to the present invention, it is possible to provide an oil / fat composition having excellent stability without causing solid-liquid separation such as precipitation of solid fat and separation of liquid oil over time.

  The present invention will be described below based on embodiments. The solid-liquid separation inhibitor of the present embodiment is a polyglycerin fatty acid ester obtained by esterifying polyglycerin and a fatty acid, and is used as a solid-liquid separation inhibitor that prevents solid-liquid separation of the oil and fat composition.

  The fatty acid constituting the polyglycerol fatty acid ester is one or more selected from saturated fatty acids having 16 to 22 carbon atoms, saturated fatty acids having 8 to 14 carbon atoms and unsaturated fatty acids having 16 to 22 carbon atoms. It is more preferable to have one or more selected from

  If the saturated fatty acid having 16 to 22 carbon atoms, the saturated fatty acid having 8 to 14 carbon atoms, and the unsaturated fatty acid having 16 to 22 carbon atoms are applicable to the conditions of the carbon number and saturated or unsaturated, Although not particularly limited, linear fatty acids are mainly selected. Saturated fatty acids having 16 to 22 carbon atoms include palmitic acid, stearic acid, arachidic acid, and behenic acid, and saturated fatty acids having 8 to 14 carbon atoms include caprylic acid, capric acid, lauric acid, and myristic acid. Examples of the unsaturated fatty acid having 16 to 22 carbon atoms include palmitoleic acid, oleic acid, elaidic acid, linoleic acid, linolenic acid, arachidonic acid, erucic acid, eicosapentaenoic acid, and docosahexaenoic acid.

The molar ratio of each fatty acid in the constituent fatty acids of the polyglycerol fatty acid ester is not particularly limited,
(A): one or more selected from saturated fatty acids having 16 to 22 carbon atoms,
(B): one or more selected from saturated fatty acids having 8 to 14 carbon atoms and unsaturated fatty acids having 16 to 22 carbon atoms,
In the total molar amount of (A) and (B), the molar ratio of (A) is 0.3 to 0.9, and the molar ratio of (B) is 0.1 to 0.7. Demonstrates better solid-liquid separation prevention effect.
The average degree of polymerization of the polyglycerol constituting the polyglycerol fatty acid ester is not limited, but is preferably 2 to 20. Here, the average degree of polymerization is the average degree of polymerization (n) of polyglycerin calculated from the hydroxyl value by end group analysis. Specifically, the average degree of polymerization is calculated from the following formulas (Formula 1) and (Formula 2).
(Formula 1) Molecular weight = 74n + 18
(Formula 2) Hydroxyl value = 56110 (n + 2) / Molecular weight The hydroxyl value in the above (Formula 2) is a numerical value that is an index of the number of hydroxyl groups contained in polyglycerin, and is free contained in 1 g of polyglycerin. The number of milligrams of potassium hydroxide required to neutralize the acetic acid required to acetylate the hydroxyl group. The number of milligrams of potassium hydroxide is calculated according to the Japan Oil Chemists 'Society edited by “The Japan Oil Chemists' Society, Standard Oil Analysis Test Method (I), 2003 edition”.

  Since the polyglycerin fatty acid ester of this embodiment increases the esterification rate, the solid-liquid separation preventing effect of the oil / fat composition and the dispersibility in the oil / fat composition increase, so the esterification rate is 40% or more. More preferably. Here, the esterification rate is the average degree of polymerization of polyglycerol (n) calculated from the hydroxyl value by end group analysis, the number of hydroxyl groups (n + 2) of this polyglycerol, and the fatty acid added to the polyglycerol. When the number of moles is (M), (M / (n + 2)) × 100 = value calculated by esterification rate (%). The hydroxyl value is a value calculated in the same manner as the hydroxyl value described above.

  The polyglycerol fatty acid ester of the present embodiment can be produced by a known esterification reaction. For example, a fatty acid and polyglycerin can be produced by an esterification reaction in the presence of an alkali catalyst such as sodium hydroxide. The esterification reaction is performed until almost all of the charged fatty acid is esterified. That is, the reaction is sufficiently performed until almost no free fatty acid is consumed.

  The fats and oils used in the fat and oil composition in the present embodiment are not limited. For example, as solid fats, palm oil, palm kernel oil, cacao butter, coconut oil, lard, milk fat, chicken fat, beef tallow and these The fractionated fats and oils are exemplified. Further, it may be hydrogenated hydrogenated animal or vegetable oil or extremely hydrogenated oil completely hydrogenated. As liquid oil, soybean oil, rapeseed oil, corn oil, sesame oil, perilla oil, linseed oil, peanut oil, safflower oil, safflower oil with high oleic acid, cottonseed oil, grape seed oil, macadamia nut oil, hazelnut oil, pumpkin seed oil, walnut Examples include oil, cocoon oil, tea seed oil, sesame oil, olive oil, mustard oil, rice oil, rice bran oil, wheat germ oil, safflower oil, sunflower oil, and fractionated fats and oils thereof. Further, diglyceride and / or monoglyceride may be contained or formulated. Moreover, sterol, sterol ester, etc. may contain arbitrarily in fats and oils.

  When polyglycerin fatty acid ester is added to fats and oils, polyglycerin fatty acid esters melted at a temperature of 60 ° C. or lower are usually added to fats and oils heated to 50 ° C. or higher. Dissolve polyglycerol fatty acid ester. Then, the fats and oils composition which prevented solid-liquid separation is obtained by cooling fats and oils.

  The polyglycerin fatty acid ester used as the oil / fat solid-liquid separation preventing agent of the present embodiment can enhance the effect of oil / fat solid-liquid separation with an increase in the amount of addition thereof. The addition amount of the polyglycerin fatty acid ester may be an amount of 0.01 to 10.0% by weight in the oil and fat composition, and more preferably 0.5% by weight or more.

  EXAMPLES The present invention will be specifically described below based on examples, but the present invention is not limited to the examples. In the examples, “polyglycerin # 750” manufactured by Sakamoto Yakuhin Kogyo Co., Ltd. was used for polyglycerin having an average degree of polymerization of 10, and “polyglycerin # 500” manufactured by Sakamoto Yakuhin Kogyo Co., Ltd. was used for polyglycerin having an average degree of polymerization of 6. "Polyglycerin # 310" manufactured by Sakamoto Pharmaceutical Co., Ltd. was used as polyglycerin having an average degree of polymerization of 4.

<Example 1>
Esterification rate: 100 g of polyglycerin having an average degree of polymerization of 10 and a mixed fatty acid consisting of 82.6 g of capric acid and 326.4 g of behenic acid are placed in a reaction vessel and reacted at 250 ° C. in an alkaline and nitrogen stream with sodium hydroxide. 90% polyglycerol fatty acid ester was obtained.

<Example 2>
Esterification rate: 100 g of polyglycerin having an average degree of polymerization of 4, mixed fatty acid consisting of 103.0 g of myristic acid and 307.3 g of behenic acid was placed in a reaction vessel and reacted at 250 ° C. in an alkaline and nitrogen stream with sodium hydroxide. 70% polyglycerol fatty acid ester was obtained.

<Example 3>
Esterification rate: 100 g of polyglycerin having an average degree of polymerization of 10 and a mixed fatty acid consisting of 81.2 g of oleic acid and 391.7 g of behenic acid are placed in a reaction vessel and reacted at 250 ° C. in an alkaline and nitrogen stream with sodium hydroxide. 90% polyglycerol fatty acid ester was obtained.

<Example 4>
A mixed fatty acid consisting of 100 g of polyglycerin having an average degree of polymerization of 10 and 86.3 g of stearic acid, 310.0 g of behenic acid, and 85.7 g of oleic acid is placed in a reaction vessel, and at 250 ° C. under alkaline and nitrogen flow with sodium hydroxide. The reaction was performed to obtain a polyglycerol fatty acid ester having an esterification rate of 95%.

<Example 5>
A mixed fatty acid consisting of 100 g of polyglycerin having an average degree of polymerization of 6 and 38.4 g of lauric acid, 54.5 g of stearic acid, and 195.8 g of behenic acid is placed in a reaction vessel, and at 250 ° C. under alkaline and nitrogen flow with sodium hydroxide. The reaction was performed to obtain a polyglycerol fatty acid ester having an esterification rate of 60%.

<Example 6>
A mixed fatty acid composed of 100 g of polyglycerin having an average degree of polymerization of 4 and 53.3 g of capric acid, 263.8 g of stearic acid, and 105.3 g of behenic acid was placed in a reaction vessel, and the mixture was alkalinized with sodium hydroxide and at 250 ° C. under a nitrogen stream. Reaction was performed to obtain a polyglycerol fatty acid ester having an esterification rate of 80%.

<Example 7>
100 g of polyglycerin having an average degree of polymerization of 10 and 272.0 g of behenic acid were placed in a reaction vessel and reacted at 250 ° C. in an alkaline and nitrogen stream with sodium hydroxide to obtain a polyglycerin fatty acid ester having an esterification rate of 50%. .

<Example 8>
100 g of polyglycerin having an average degree of polymerization of 10 and 407.9 g of behenic acid were put in a reaction vessel and reacted at 250 ° C. in an alkaline and nitrogen stream with sodium hydroxide to obtain a polyglycerin fatty acid ester having an esterification rate of 75%. .

<Example 9>
Esterification rate: 100 g of polyglycerin having an average degree of polymerization of 4, mixed fatty acid consisting of 237.8 g of palmitic acid and 79.0 g of behenic acid was placed in a reaction vessel and reacted at 250 ° C. in an alkaline and nitrogen stream with sodium hydroxide. 60% polyglycerol fatty acid ester was obtained.

<Example 10>
Esterification rate: 100 g of polyglycerin having an average degree of polymerization of 6, mixed fatty acid consisting of 61.4 g of palmitic acid and 272.2 g of stearic acid was placed in a reaction vessel and reacted at 250 ° C. under alkaline and nitrogen flow with sodium hydroxide. 75% polyglycerol fatty acid ester was obtained.

<Example 11>
A mixed fatty acid consisting of 100 g of polyglycerin having an average degree of polymerization of 10 and 129.7 g of palmitic acid, 143.9 g of stearic acid, and 172.3 g of behenic acid is placed in a reaction vessel, and at 250 ° C. under alkaline and nitrogen flow with sodium hydroxide. The reaction was performed to obtain a polyglycerol fatty acid ester having an esterification rate of 95%.

  The confirmation test about the solid-liquid-separation prevention effect of the oil-fat composition was conducted on the polyglycerin fatty acid ester of the above examples based on the following Test Example 1. Further, as a comparative example, a commercially available glycerin monobehenate ester was also tested for confirming the effect of preventing solid-liquid separation.

[Test Example 1]
Solid-liquid separation test of oil and fat composition 30 parts of purified palm oil of solid fat and 70 parts of soybean oil of liquid oil were heated to 80 ° C and mixed. To this mixed oil, the polyglycerol fatty acid ester of Examples 1 to 11 and the commercially available ester of the comparative example were added and dissolved uniformly to contain 1 wt% and 3 wt% of the polyglycerol fatty acid ester or the commercially available ester. An oil and fat composition was prepared. Next, the oil and fat composition was allowed to cool in an incubator at 20 ° C. for 1 day. Thereafter, the state of the oil and fat composition was visually confirmed.

Evaluation of Test Example 1 was performed as follows based on the state of the oil and fat composition.
A: Solid-liquid separation is not seen at all, and it is in a uniform state.
○: Some liquid oil on the surface is spotted.
Δ: A considerable amount of liquid oil is observed on the surface.
X: Solid fat and liquid oil are completely separated.

The results of Test Example 1 are shown in Table 1. The molar ratio is the ratio of each constituent fatty acid to the total molar amount of fatty acids constituting the polyglycerol fatty acid ester.

（注）：１は、脂肪酸が二重結合１個を持つことを表す

(Note): 1 represents that the fatty acid has one double bond.

  As shown in Table 1, solid-liquid separation occurred in the comparative examples at 1% by weight and 3% by weight. On the other hand, the oil and fat compositions to which the polyglycerin fatty acid esters of Examples 1 to 11 were added had no solid-liquid separation at an addition amount of 1% by weight, and were in a uniform state. Especially about Examples 1-6, the spot of liquid oil was not seen on the surface of the oil-fat composition, and it was in a smooth and glossy state. That is, it can be confirmed that only the polyglycerin fatty acid ester of the present invention is excellent in the solid-liquid separation preventing effect of the oil and fat composition.

  Next, the test based on the following Test Example 2 was performed about the daily change of the state of the oil-fat composition to which the polyglycerol fatty acid ester of the Example was added and the oil-fat composition to which the commercially available ester of the Comparative Example was added.

[Test Example 2]
As in Test Example 1, 1% by weight of the polyglycerin fatty acid ester of Examples 1 to 6 was added to an oil / fat composition consisting of 30 parts of refined palm oil and 70 parts of soybean oil, and uniformly dissolved to prepare an oil / fat composition. . Moreover, the polyglyceryl fatty acid ester of Examples 7-11 and the commercially available ester of a comparative example were each added 3 weight%, and were dissolved uniformly, and prepared the oil-fat composition. Next, each oil and fat composition was cooled in an incubator at 20 ° C., and the state of the oil and fat composition was visually confirmed.

Evaluation of Test Example 2 was performed as follows based on the state of the oil and fat composition.
A: Solid-liquid separation is not seen at all, and it is in a uniform state.
○: Some liquid oil on the surface is spotted.
Δ: A considerable amount of liquid oil is observed on the surface.
X: Solid fat and liquid oil are completely separated.

  As shown in Table 2, solid-liquid separation was not seen in the oil and fat compositions to which the polyglycerin fatty acid esters of Examples 1 to 11 were added, even after 2 months had elapsed, and was in a uniform state. That is, it can be confirmed that the polyglycerol fatty acid ester is excellent in long-term stability of the solid-liquid separation preventing effect.

  Next, based on the following Test Example 3, a confirmation test of the effect of preventing solid-liquid separation was performed on an oil / fat composition composed of each oil / fat.

[Test Example 3]
In accordance with Test Example 1, a test for confirming the effect of preventing solid-liquid separation of each of the oil and fat compositions of the polyglycerin fatty acid ester of Examples and Comparative Examples was performed. The representative results of this test are shown in Table 3. In Table 3, “% by weight” represents the amount of each oil and fat composition containing the esters of Examples and Comparative Examples.

Evaluation of Test Example 3 was performed as follows based on the state of the oil and fat composition.
A: Solid-liquid separation is not seen at all, and it is in a uniform state.
○: Some liquid oil on the surface is spotted.
Δ: A considerable amount of liquid oil is observed on the surface.
X: Solid fat and liquid oil are completely separated.

  As shown in Table 3, the comparative example could not prevent the solid-liquid separation of each oil and fat composition even when the content was 3% by weight. On the other hand, it was confirmed that the polyglycerin fatty acid ester of Examples 2 and 4 can prevent solid-liquid separation of each oil and fat composition with a content of 1% by weight.

Claims (4)

  A solid-liquid separation inhibitor for fats and oils comprising a polyglycerin fatty acid ester.   The fatty acid constituting the polyglycerin fatty acid ester has (A) one or more selected from saturated fatty acids having 16 to 22 carbon atoms, and (B) saturated fatty acids and carbon atoms having 8 to 14 carbon atoms. 1 or 2 or more types selected from 16 to 22 unsaturated fatty acids, and in the total molar amount of the constituent fatty acids (A) and (B), the molar ratio of the constituent fatty acids (A) is 0.3 to The solid-liquid separation inhibitor, characterized in that the molar ratio of the constituent fatty acid (B) is 0.1 to 0.7.   The solid-liquid separation inhibitor according to claim 2, wherein the esterification rate of the polyglycerin fatty acid ester is 40% or more.   The oil-fat composition containing the solid-liquid separation preventing agent of Claims 1-3.