JPS6053598A - Plastic fat, manufacture and coating agent - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a plastic oil, a method for producing the same, and a coating containing the same.

Edible fats and oils are used for various purposes by taking advantage of their '4'/I-containing properties. One example is coating oils and spray oils for confectionery, in which case the oils not only improve the flavor of foods but also function as a protective film.

The physical properties of oils and fats used for this purpose include being physically and chemically strong, having low permeability to water vapor, and having a good texture. In general, confectionery coatings include cacao extract, 2, -
Doputter is often used.Although hard butter has a good texture, its coating lacks plasticity and is brittle.

Insufficient for some purposes. It is desirable that the oil and fat for membrane rupture have a small melting range, like hard butter, and also have plasticity and extensibility. Acetin fat, which is mainly composed of glycerol diacetomonostearate, is well known as a fat that satisfies these physical properties. However, this oil is just like its name! ! Il: Because it has an acid group, it may generate the pungent odor of acetic acid when hydrolyzed. Furthermore, the process is complicated, as excessive H[acid] is required during production, and when acetic anhydride is used as a raw material, a large amount of acetic acid is produced as a by-product.

The inventors of the present invention have conducted extensive research in order to produce a plastic fat with physical properties similar to acetin fat without such drawbacks by combining four long-chain fatty acids, and have now found that the total number of carbon atoms in the constituent fatty acids is The present invention was completed by discovering that a specific triglyceride having a triglyceride of 58 or more and having a bisaturated phase and an unsaturated phase satisfies this condition.

That is, in the present invention, the total number of carbon atoms of the constituent fatty acids is 58 or more, and each constituent fatty acid is a saturated fatty acid with a carbon number of 22 or more, a saturated fatty acid with a carbon number of 18 or more, and a saturated fatty acid with a carbon number of 16 to
The present invention provides a plastic fat and oil made from triglyceride, which is an unsaturated fatty acid of No. 22, as a living body, a method for producing the plastic fat and oil, and a coating material containing the plastic fat and oil.

Distearyl monoolein (S20) is well known as a typical disaturated-unsaturated triglyceride, and in this glyceride, the unsaturated acid bonding positions are α and β.
Regardless, also its mixture ya! (20t) It is a brittle solid in the vicinity. Furthermore, since the polymorphism detected by X-rays takes the β-form, a so-called fat bloom may occur depending on the solidification conditions. However, regardless of whether the oil or fat according to the present invention is cooled quickly or gradually, the solidified appearance is transparent (paraffin-like) and extensible.

x+1iIi again! Diffraction analysis shows that when stored at room temperature, it is in the β'-form and its plasticity is stably maintained over a long period of time.

The fatty acids constituting the plastic fats and oils of the present invention include saturated fatty acids having 22 or more carbon atoms (especially behenic acid), saturated fatty acids having 18 or more carbon atoms (preferably stearic acid, arachinic acid, behenic acid), and 16 to 22 carbon atoms. unsaturated fatty acids (preferably those with 18 carbon atoms such as oleic acid, linoleic acid, lylunic acid, etc.)
It is an unsaturated fatty acid.

Typical triglycerides that are the main component of the plastic fats and oils of the present invention are dibehenyl monolinoleate or monooleate, but one of the kA phase acids may be replaced with stearic acid or arachidic acid, or a mixture thereof may be used. good.

The bonding position of the unsaturated fatty acid may be either α or β, but a mixture thereof is preferred.

Dibehenylmonostearin and the like are already found in the literature as triglycerides with long-chain saturated fatty acids such as behenic acid.The physical properties of this fat and oil are similar to ordinary solid fats with a high melting point, and the plastic fat and oil of the present invention It's completely different.

Generally, in order to impart plasticity to fats and oils, liquid oil is mixed with a suitable solid fat, melted, and then rapidly cooled.

Manufactured by kneading. Shortening is a typical example. However, in this case, its physical properties vary depending on the conditions of quenching and kneading, and it does not have the extensibility of acetin fat or the plastic fat of the present invention.

The 5R plastic fat and oil having the specific constituent fatty acids of the present invention can be used as it is or mixed with other known ingredients to coat the surface of foods as a coating fat or a coating oil or fat as well as a mountain fat composition.

As the coating oil/fat, the plastic oil/fat having the specific constituent fatty acids of the present invention may be melted and used as it is, or may be mixed with other fat/oil to the extent that the physical properties are not affected. There are no particular restrictions on the fats and oils that can be used in combination as long as they are edible, including soybean rII].

rapeseed, palm gamma, corn, A'd oil,
Vegetable oils such as coconut oil and palm kernel oil, lard, fish oil,
Any of animal fats and oils such as whale oil and milk fat can be used, and those obtained by hydrogenation and transesterification of these can also be used.

The plastic oil and fat of the present invention can be used as a food coating agent not only for chocolate coating of cakes as mentioned in the examples, but also as a spray oil for dry fruits such as raisins, nuts, etc., and as a moisture-proofing and drying agent. C can be used as an edible coating oil for necessary chikusu products (for example, jelly).

Also, as a coating agent, in addition to cases where only oils and fats are used like spray oil, sand, milk, cocoa, chocolate licker, etc. are used like chocolate coating.
It can be mixed with peanut butter, powdered almonds, powdered cheese, etc. and used as a coating for confectionery. For example, in chocolate coating, 25 to 50% of the fat or oil according to the present invention (or a mixture of other fats and oils without detracting from the characteristics of the fat or oil according to the present invention), 1 part cocoa powder
0-15%, chocolate licker 0-15%, milk powder 0
It is preferable to use a range of 15% to 15% and 35 to 55% sugar.

In this case, if you replace part or all of the cocoa powder and chocolate licker with peanut butter or powdered almonds, you can obtain a product that takes advantage of the characteristics of each flavor.

Although the method for producing the plastic fat of the present invention is not particularly limited, the following production method is suitable.

Fatty acid diglycerides with carbon atoms of 18 or more always having fatty acid residues of carbon atoms of 22 or more (particularly behenic acid residues) such as grise real dibehene, grise stomach rustearyl behen, and oleic anhydride, inglobenyl oleate, etc. There is a method of esterifying an unsaturated fatty acid having 16 to 22 carbon atoms with a fatty conductor.-A fatty acid having 22 or more carbon atoms (especially behenic acid) such as Tribehen or extremely hardened Hierucanola r1h. Vegetable oils (e.g. soybean oil, rapeseed oil, safflower oil) made from unsaturated fatty acids with residual fatty acid triglycerides containing 18 or more carbon atoms 60 to 60M lid% and saturated fatty acid content of 20 M lids or less (for example, soybean oil, rapeseed oil, safflower oil) 70
There is also a method of transesterifying a mixed oil with heavy fluorophores and separating the transesterified oil to obtain the desired fat or oil. In this case, transesterification involves randomly arranging fatty acids, and the catalyst used is 0.1 to 0.3% by weight of commonly used tuthorium metesort, caustic soda, etc. based on the fat and oil, and the reaction temperature was Perform at 70-150C. After the reaction, the catalyst 'f: is removed by washing with water. In this case, the saturated fatty acid triglyceride having 18 or more carbon atoms may be a transesterification product of methyl or ethyl ester of a fatty acid having 18 or more carbon atoms and triacetin. Sensitizer fractionation is n-
A bath agent used to separate fats and oils such as hexane and acetone.Use 2 to 5 times the amount of the total fats and oils. This solvent is bathed in transesterified oil, cooled to 15 to 25 cK, and the precipitated trisaturated phase glyceride is separated by P. The desired product is obtained by cooling 1 liter to 15 to 5 centimeters and collecting the precipitated disaturated-unsaturated glyceride.

Hereinafter, the present invention will be explained in further detail with reference to Examples.

Example-1 Extremely hardened high quality rapeseed oil (fatty acid composition: palmitic acid 2.9%, stearic acid 40.7%, arachidic acid 7.4%, behenic acid 46.9%, i2.0%) 5
a wt% and Tefshiwa oil (palmitic acid 6.5%,
Stearic acid 2.5%, oleic acid 16.0%, linoleic acid 74.1%, linolic acid 0.9%) 50 wt% mixed oil based on fats and oils. , catalyzed by 1% sodium methylate and treated at 80C for 30 minutes to obtain transesterified oil. This transesterified oil was dissolved in acetone of 11% and 95%.
After melting at 60C, the mixture is cooled to 251 m' with stirring to remove the precipitated trisaturated triglyceride-based high melting point part (yield: 15% based on the transesterified oil).
The liquid was stirred and cooled to 3-5C, and the precipitated target fraction (medium melting point fraction) was collected.

After removing the bath additive, this section is deodorized by a conventional method to obtain the desired product.

The high melting point fraction and low melting point fraction produced as by-products in this step can be mixed with the raw material before transesterification and reused.

Example-2 Methyl behenate (stearic acid 14.2%, arachidic acid 11.4%, behenic acid 72.0%, other 2.5%)
ooy, rapeseed oil () 3.6% walmitic acid, 1.7% stearic acid, 957.7% olein, su/-fil
22.2, %, lylunic acid 12.7%, erucic acid 2
．． 5%)500Ji',)! Mix acetin 110I, oil-resistant 5. % of sodium methylate as a catalyst, the reaction was carried out at 20% Hg and 70C while removing by-product methyl acetate, to obtain a transesterified fat.

This transesterified fat is 2.51nl per gram of fat! n of
- Dissolve in hexane, cool to 17 to 19C, and separate the precipitated high melting point part. This R liquid was cooled to 0 to 2C, and the precipitated target intermediate melting point fraction was collected and treated in the same manner as in Example 1 to obtain the target product.

Example-6 Tribehene (stearic acid 10.9%, arachidic acid 8.9%)
5%, behenic acid 80.6%) 200.9. Soybean oil (10.6% palmitic acid, 41% stearic acid, 24.4% oleic acid, 53.7% linoleic acid, 7.2% linuric acid)
) 200& was subjected to transesterification and solvent fractionation in the same manner as in Example-1 to obtain the desired classification.

Example-4 High boiling point category of extremely hardened fish oil fatty acids (balmy: 1
rRL5%, stearic acid 18.2%, arachine ts5
8.8%, behenic acid 67.2%, other 1.7%) and safflower oil 50wt%.
After transesterifying the 0 wt % mixed oil in the same manner as in Example-1, the bath agent fractionation was performed to obtain the desired classification.

Comparative Example 1 For comparison, a mixed oil of ~11% hardened soybean oil (2001/) (lumitic acid 10.5%, stearic acid 89.5%) containing no behenic acid or arachidic acid and safflower oil 200I was used. Transesterification and solvent fractionation were performed according to Example 1, and the intermediate melting point fraction was collected.

The analytical values of the intermediate melting point category obtained in Examples 1 to 4 and Comparative Example 1 are shown in Table 1, and the triglyceride composition determined by gas chromatography and the appearance after storage at 20p for one month are shown in Table 2.
Shown below. In addition, FIG. 1 shows the X-ray diffraction patterns of each intermediate melting point category measured after storage for 20C11 months. In the figure, A shows the results of Examples 1 to 4, and B shows the results of Comparative Example 1.

(Note) C54: s2u, C56: ASU, O
: AAυ, BSU.

58 c6o: ABU, 06□: Mainly B2U, however, S represents stearic acid, U represents C18 unsaturated acid, B represents behenic acid, and A represents arachidic acid.

Example-5 72Ii glycerol dibehenate (glycerol dibehenate 4-) 73.1%, glycerol behenyl arachine) 15.4%, glycerol behenyl stearate)
8.1%, others 3.4%) 3211) Unsaturated fatty acid inglobil ester (fatty acid composition: valmitic acid 1
．． 5%, oleic [62.5%, linoleic acid 27.8%
, rirunic acid 8.4%) woha, r) Reacted at 220C for 5 minutes using Rue/sulfonic acid (0.5%) as a catalyst to give an iodine value of 45.1. Melting point 43.5 C, glyceride composition C6272, 1%, a6o15.5%%o588.1
%, and 2.4% of other disaturated-unsaturated triglycerides were obtained. The appearance of this oil and fat after storage for 20C for 1 month was paraffin-like and extensible.

Example 6 As an example showing one of the characteristics of the fat according to the present invention, coating chocolate using the fat of Example 1.2 (29% fat, 12% chocolate licker, 5% cocoa butter, 54% 11B) 2.2 I! A sponge cake cut into cubes (containing 35.0% moisture) was destroyed on the entire surface, and the cake and a desiccator containing a desiccant (silica gel) were stored at 25C to reduce the MW due to evaporation of water in the cake. The decrease was measured. The oil and fat used for comparison in this case was a commercially available trans-type hard putter (melting point: 36.5C, iodine value: 69.1).

The results are shown in Figure 2. In the figure, 1 is the result when the fat of Example 1 was used, 2 is the result when the fat of Example 2 was used, and 5 is the result when commercially available trans-type hard butter was used. The data are shown in terms of the decrease in mold cavities for three cakes at a time.

It can be seen that when coated with the oil and fat according to the present invention, water evaporates less.

Example 7 Moisture Absorption Test of Fried Peanuts Peanuts were fried using the oil and fat of Example 6 and commercially available palm oil, and the peanuts were stored in 251Z" humidity of 80%.
105 tl: We investigated the "υ constant" due to drying loss. Figure 5 shows the Mj value. In addition, in the figure, j rJ, -1 is the result when the balm oil was used for rinsing, and 2 is the result when the oil and fat of Example 5 was used for 7 rinsing. It can be seen that the peanuts fried with the oil and fat according to the present invention and whose surface is supported have low hygroscopicity.

[Brief explanation of the drawing]

Figure 1 shows the X-ray diffraction diagram of the medium melting point classification obtained in Examples 1 to 4 and Comparative Example 1 after storage for 1 month, and Figure 2 shows the moisture permeability test by coating a sponge cake conducted in Example 5. FIG. 3 is a graph showing the results of the moisture absorption test of fried peanuts conducted in Example 6. Applicant's agent Kaoru Furuya 1 Figure 111 → 2θ 2 Figure 5 10 15 20 Number of preservation days) Figure 3 Number of preservation days (days):'r-Senkou 7 cities 11 yen, FS ('1 from) Showa 5
November 9, 2811 Manabu Shiga, Commissioner of the Patent Office, Patent Application 1982-161667 '-La 2, Title of Invention: Plastic oils and fats, their manufacturing process, and coatings containing the same 3, Person making the amendment'lf Related Patent Applicant (081) Kao Seikyo Co., Ltd. 4, Agent Scope of Claims in Specification and Invention C, Detailed Explanation Box 16, Contents of Draw 1F (1) Scope of Patent No. 671 Claims amended as shown in the attached sheet (+) Specification-t4J:i, line 12, after "and", insert "consisting of saturated fatty acids with 20 or more carbon atoms and unsaturated fatty acids with 16 to 22 carbon atoms" (1 ) 4th page, lines 12-13 ``triglyceride'' has been changed to [mixed acid group triglyceride, revised 1F. (1) Page 4, lines 16-19 “Each constituent fatty acid...
...Triglyceride fatty acid and unsaturated fatty acid having 16 to 22 carbon atoms, mixed acid group triglyceride" (+) tii p. 14, lines 19-20, after "Mainly plasticizing fats and oils", it has been changed to ``For more details, the constituent fatty acids are 20 carbon atoms. 30 to 70,000% (preferably 40 to 65% by weight) of the following saturated fatty acids, and 20 to 60Φ, jij-% (preferably 25 to 65%) of unsaturated fatty acids having 16 to 22 carbon atoms.
Insert (1) ``Plastic fats and oils that contain 50% of heavy weight products) and are mainly composed of mixed acid groups of saturated fatty acids with 20 or more carbon atoms and unsaturated fatty acids with 16 to 22 carbon atoms, liglycerate'' (1) Same page 5 2QIr paraffin from line 11 and bottom of page 15
respectively as "Wa-nx"+Ig(1) same 5 pages 15-1
Line 7, “22 to 1- carbon atoms, 18 carbon atoms” is revised to “20 carbon atoms” II-(1), p. 5, 17-
Delete line 18 “stearic acid,” (1) Change “- stearic acid,” to page 6, line 5 [-・Tsuga stearic acid,”]
(1) From the last line on page 8 to line 1 on page 9, “crycerol stearyl behen” was corrected as “glycerol araquinyl hehen.” (1) On page 9, lines 1 to 3, “22 or more carbon atoms. "-'s...
...having a carbon number of 18 or more-J. (1) Revised page 9, line 6, "Gokuhen" to "Extreme", (1)
9th page, lines 7-9 "Contains 40% or more of saturated fatty acids with 20 to 1 carbon atoms." ” and 7r +l-(1) same page 9+. Line o − i [contains saturated fatty acids, hl
"Contains 80% or more by weight of unsaturated fatty acids" has been corrected. ”
[Major revision] To (1) same page 1 t■r Saturated fatty acids", then "to 4
Insert "Contains more than 1% in 0 weight" (1) Correct "5 times the amount" in line 6 on page 10 to "10 times the amount" (1) 1st page 10, column 7 "15 to 25°C" ” to “0-35
°C (preferably 15 to 35 °C when acetone is used as a solvent, and 0 to 30 °C when n-hexane is used as a solvent)" and revised 1-(1) same page 10 line 8 "Measure .P solution at -5~5°C
” to “F” (first stage). When using the same solvent for the first stage separation, heat the first stage liquid at -25°C or more.
20°C (preferably O to 20°C when acetone is used as the solvent, -250C to 5°C when n − -, xane is used as the solvent) j and gr +l (1) Same page 10, line 10 "Obtain the target product" should be replaced with "Obtain the target product (second stage). In addition, if the fractionated solvents in the first stage 11 and the first stage are different, after distilling off the solvent of the first stage It lI" liquid, Add 2 to 10 parts of solvent to dissolve the mixture, cool to -25 to 20°C, and collect the precipitated disaturated-unsaturated glyceride to obtain the desired product. (1) The first column of fatty acid composition (χ) in Table 1 on page 14
Column 1'' 6th from the right [CI8=' was corrected to 18=1' (1) From the top of the appearance column in Table 2 on page 14 #II
f and line 2, "paraffin-like" was corrected to "1-wax-like" (]) Page 11, line 44, A, contains a small amount of arachidic acid. '', change the line and increase the size of Comparative Example 2 by 1 cow. Comparative Example 2 For comparison, Tribehen (10.9% stearic acid, 8.5% Arachine chuan, 80.6% behenic acid)
) 200g, soybean oil (palmitenoic acid 1O96%, stearic acid 41%, oleic acid 24.4%, S/-L resistance 53
．． 7%, Rirunbutsu 7.2%) 200g of mixed oil was transesterified in the same manner as in Example-1 to obtain transesterified sleeves (
Example 3 (product without solvent separation). In the comparative example 2? 1) The analytical values of the obtained fats and oils are shown in Table 3, and the appearance after triglyceride determination by Cass chromatography is shown in Table 4. (Note) J'C52; S2U, C54; S2U, C56:
ΔsUC,; AAU, BSU, CEO; AB
U, C62: B2U・Cea; B2A・C66;
B3 is the -L form, however, S represents stearic acid, U represents 018 unsaturated acid, B represents hehenic acid, and A represents arachinbutyric acid. 2. Claims Plastic oil and fat mainly composed of cerides. A method for producing plastic fats and oils that involves chill exchange reaction and then solvent fractionation to obtain triglyceride monomers. 3. Triglyceridol 't', which is a triglyceridol containing 1111 fatty acids of 20"- or more; I, < is the transesterification product of ethyl ester and triacetin. A method for producing a plastic fat and oil according to item 2. A method for producing a plastic fat and oil mainly composed of glyceride, which is characterized by carrying out an esterification reaction with an unsaturated monomer derivative having 16 to 22 carbon atoms. 1: A coating material characterized by containing a plastic oil and fat.

Claims (1)

[Claims] 1. Saturated fatty acids with a total carbon number of 558 or more, and each constituent fatty acid has 22 or more carbon atoms, 411 JJki fatty acids with 18 or more carbon atoms, and saturated fatty acids with 16 to 16 carbon atoms. Is it bI fertility that is mainly composed of triglycerides, which are 22 unsaturated fatty acids? Sangetsuji. 2 18 carbon atoms containing fatty acid residues having 22 or more carbon atoms
The above fatty acid triglyceride (IJ)" is characterized by transesterifying 30 to 60% of heavy waves and 40 to 70% of vegetable oil having a saturated fatty acid content of 20% or less, followed by solvent fractionation. Total carbon number of constituent fatty acids: 58 or more, and each constituent fatty acid has 22 or more carbon atoms, saturated fatty acids with 18 or more carbon atoms, and 1 carbon number.
A method for producing plastic fats and oils mainly composed of triglycerides, which are 6-22 unsaturated fatty acids. & Fatty acid triglycerides with carbon number 18 or more have 1 carbon number
3. The method for producing plastic fats and oils according to claim 2, which is a transesterification product of methyl or ethyl ester of 8 or more fatty acids and triacetin. Tun Fatty acid residue with carbon number 22 or more must have carbon number 1
Characterized by subjecting a fatty acid diglyceride of 8 or more and a derivative of an unsaturated fatty acid having 16 to 22 carbon atoms to an esterification reaction, the constituent fatty acids have a condensation score of 58 or more, and each constituent fatty acid has a carbon number of Saturated fatty acids with 22 or more carbon atoms, saturated Jjh fatty acids with 18 or more carbon atoms, and 16-2 carbon atoms
A method for producing plastic fats and oils mainly composed of triglycerides, which are unsaturated fatty acids. 5. The total number of carbon atoms in the constituent fatty acids is 58 or more. And each constituent fatty acid is a saturated fatty acid with a carbon number of 22 or more, and a saturated fatty acid with a carbon number of 18 or more and a carbon number of 16 to 2.
Triglyceride, which is an unsaturated fatty acid of 2, is a living body. A coating agent characterized by the fact that it contains T-plastic oil.