WO2010119781A1 - 可塑性油脂用改質剤 - Google Patents
可塑性油脂用改質剤 Download PDFInfo
- Publication number
- WO2010119781A1 WO2010119781A1 PCT/JP2010/056086 JP2010056086W WO2010119781A1 WO 2010119781 A1 WO2010119781 A1 WO 2010119781A1 JP 2010056086 W JP2010056086 W JP 2010056086W WO 2010119781 A1 WO2010119781 A1 WO 2010119781A1
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- WIPO (PCT)
- Prior art keywords
- oil
- fat
- acid
- content
- fatty acid
- Prior art date
Links
- 239000003795 chemical substances by application Substances 0.000 title abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 102
- 150000004671 saturated fatty acids Chemical class 0.000 claims abstract description 59
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 31
- 239000000194 fatty acid Substances 0.000 claims abstract description 31
- 229930195729 fatty acid Natural products 0.000 claims abstract description 31
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 29
- 238000002844 melting Methods 0.000 claims abstract description 25
- 230000008018 melting Effects 0.000 claims abstract description 25
- 235000019482 Palm oil Nutrition 0.000 claims abstract description 21
- 239000002540 palm oil Substances 0.000 claims abstract description 21
- 150000003626 triacylglycerols Chemical class 0.000 claims abstract description 18
- 239000003925 fat Substances 0.000 claims description 157
- 239000003921 oil Substances 0.000 claims description 156
- 235000019198 oils Nutrition 0.000 claims description 156
- 235000019197 fats Nutrition 0.000 claims description 155
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 57
- 239000003607 modifier Substances 0.000 claims description 54
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 27
- 239000005639 Lauric acid Substances 0.000 claims description 13
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 12
- 239000000470 constituent Substances 0.000 claims description 11
- -1 C22 saturated fatty acid Chemical class 0.000 claims description 3
- 239000013078 crystal Substances 0.000 abstract description 9
- 230000000704 physical effect Effects 0.000 abstract description 9
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 72
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 67
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 60
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 57
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 49
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 36
- 229960002446 octanoic acid Drugs 0.000 description 36
- 238000004904 shortening Methods 0.000 description 35
- 235000021314 Palmitic acid Nutrition 0.000 description 30
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 30
- 235000021355 Stearic acid Nutrition 0.000 description 29
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 29
- 239000008117 stearic acid Substances 0.000 description 29
- 235000021357 Behenic acid Nutrition 0.000 description 24
- 229940116226 behenic acid Drugs 0.000 description 24
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 17
- 238000004519 manufacturing process Methods 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 238000004821 distillation Methods 0.000 description 13
- 238000005809 transesterification reaction Methods 0.000 description 12
- 239000010409 thin film Substances 0.000 description 11
- 238000005259 measurement Methods 0.000 description 10
- 150000004667 medium chain fatty acids Chemical class 0.000 description 9
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 230000005484 gravity Effects 0.000 description 7
- 239000006188 syrup Substances 0.000 description 7
- 235000020357 syrup Nutrition 0.000 description 7
- 240000002791 Brassica napus Species 0.000 description 6
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 6
- 241000412626 Penetes Species 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 229940088594 vitamin Drugs 0.000 description 6
- 229930003231 vitamin Natural products 0.000 description 6
- 108090001060 Lipase Proteins 0.000 description 5
- 102000004882 Lipase Human genes 0.000 description 5
- 239000004367 Lipase Substances 0.000 description 5
- 108010048733 Lipozyme Proteins 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
- 235000019421 lipase Nutrition 0.000 description 5
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 5
- 230000035515 penetration Effects 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 244000299461 Theobroma cacao Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 235000019219 chocolate Nutrition 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- 150000004668 long chain fatty acids Chemical class 0.000 description 4
- 235000013310 margarine Nutrition 0.000 description 4
- 239000003264 margarine Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 235000014593 oils and fats Nutrition 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005273 aeration Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- MVLVMROFTAUDAG-UHFFFAOYSA-N ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC MVLVMROFTAUDAG-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 235000010692 trans-unsaturated fatty acids Nutrition 0.000 description 2
- VMPHSYLJUKZBJJ-UHFFFAOYSA-N trilaurin Chemical compound CCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC VMPHSYLJUKZBJJ-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical group CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical group [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003863 physical function Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000005457 triglyceride group Chemical group 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6454—Glycerides by esterification
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6458—Glycerides by transesterification, e.g. interesterification, ester interchange, alcoholysis or acidolysis
Definitions
- This invention relates to the modifier used for plastic fats and oils, such as margarine and shortening which use palm oil as the main raw material.
- palm oil When palm oil is blended as the main raw material for plastic oils and fats such as margarine and shortening, plastic oils and fats with high aeration ability are prone to change, such as coarse crystals and hardness, during storage and distribution. It is known that cannot be obtained. Therefore, the triglyceride structure of palm oil is modified by transesterification.
- Patent Document 1 discloses an oil / fat composition that can suppress a change in quality over time by mixing palm oil or palm stearin and an oil / fat containing lauric acid in a specific amount of fatty acid ratio and transesterifying. ing.
- Patent Document 2 a plant liquid oil containing a large amount of palm oil and unsaturated fatty acid is transesterified, and the constituent ratio of dipalmitoyl monooleoyl glyceride is PPO / POP ⁇ 0.5 (P: palmitic acid, O : Oleic acid) has disclosed an oil and fat composition in which coarsening of crystals is eliminated and a plastic oil and fat with little change over time can be obtained.
- an oil and fat composition in which fatty acid species constituting triglycerides and binding positions are specified.
- XXM type triglyceride saturated chain of X: C> 15, saturated chain of M: C ⁇ 15
- An oil and fat composition that significantly increases the rate of crystallization by incorporating a small amount of is disclosed.
- Patent Document 4 a saturated fatty acid (C) of C12 or lower is bonded to the 2-position, and a saturated fatty acid (S) of C16 or higher is bonded to the 1,3-position, 1,3-di (S) -2- It has been disclosed that mono (X) type triglycerides (SXS) suppress chocolate bloom. These methods are effective with respect to suppression of plastic oil fat and chocolate bloom, but are less effective in suppressing changes over time.
- Patent Document 7 discloses an intermolecular compound of (a) a disaturated medium chain fatty acid monolong chain fatty acid triglyceride and (b) a 1,3-disaturated long chain fatty acid 2-monounsaturated long chain fatty acid triglyceride.
- an intermolecular compound having a long surface distance of 65 mm or more by X-ray diffraction is disclosed. It is described that this intermolecular compound can maintain the smooth texture of chocolate containing a large amount of cocoa butter and suppress the occurrence of bloom. Moreover, it is described that this intermolecular compound is effective also in suppressing the daily hardness change of plastic fats and oils. This document does not disclose a specific method of using the plastic fat.
- compositions containing a high concentration of di-saturated medium-chain fatty acid mono-long-chain fatty acid triglycerides in which an intermolecular compound having a long-surface distance of 65 mm or more by X-ray diffraction is obtained.
- the inclusion of an equimolar amount of disaturated medium chain fatty acid mono long chain fatty acid triglyceride relative to 1,3-disaturated long chain fatty acid 2-monounsaturated long chain fatty acid triglyceride will soften the plastic fat and oil more than necessary. Or lower the melting point. Therefore, it is not preferable to use this intermolecular compound as the main raw material for margarine or shortening.
- JP 2000-212590 A Japanese Patent Laid-Open No. 10-183165 WO 98/19554 pamphlet JP-A-4-75593 Japanese Patent No. 2964230 JP 2002-38191 A International Publication No. 2006/121182 Pamphlet
- the object of the present invention is to suppress the change in physical properties such as the change in hardness and coarse crystals of a plastic oil and fat using palm oil, and to obtain a plastic oil and fat having aerobic properties, that is, a creaming property. It is to provide a modifier.
- the inventors of the present invention are composed of a triglyceride containing a saturated fatty acid (A) having a melting point of 60 ° C. or higher and a saturated fatty acid (B) having a melting point of 40 ° C. or lower as a constituent fatty acid.
- a fat and oil composition comprising a specific amount of an ABB type triglyceride in which one saturated fatty acid (A) and two saturated fatty acids (B) are combined in the whole oil and fat composition, the ABB type triglyceride, and a saturated fatty acid
- Addition of a specific amount of a modifier consisting of an oil / fat composition having a weight ratio (ABB / AAB) of not less than a certain value to an AAB type triglyceride in which two (A) and one saturated fatty acid (B) are combined As a result, it was found that the plastic fats and oils were prevented from changing physical properties, hardly changed in hardness, and had good creaming properties, and the present invention was completed.
- the first of the present invention is An oil and fat composition
- the content of C16 to C22 saturated fatty acid (A) is 50 to 70% by weight and the content of C6 to C10 saturated fatty acid (B) is 30% among all fatty acids constituting the triglyceride.
- the modifier is ⁇ 50% by weight.
- the content of the C18 saturated fatty acid (A) is 50 to 70% by weight and the content of the C8 to C10 saturated fatty acid (B) is 30 to 30% among all fatty acids constituting the triglyceride. It is the said modifier which is 50 weight%.
- the second of the present invention relates to a plastic fat containing 2 to 10% by weight of the ABB type triglyceride and substantially free of lauric acid. More specifically, in the plastic fat of the present invention, the modifier is blended so that the content of the ABB type triglyceride is 2 to 10% by weight in the whole fat and oil, and palm oil is blended in an amount of 50 to 98. It is a plastic fat that is blended in weight percent and has a lauric acid content of less than 5 weight percent.
- the plasticity when used in plastic oils and fats such as margarine and shortening using palm oil, the plasticity has an effect of suppressing changes in physical properties such as change in hardness and formation of coarse crystals and aeration (ie, creaming properties). It is possible to provide a modifying agent that can obtain fats and oils. Furthermore, according to the present invention, it is possible to provide a plastic oil and fat having a gas content with little change in physical properties such as change in hardness and generation of coarse crystals using the modifier.
- the modifier for plastic fat according to the present invention is a fat composition
- a fat composition comprising a triglyceride having a saturated fatty acid (A) having a melting point of 60 ° C. or higher and a saturated fatty acid (B) having a melting point of 40 ° C. or lower as a constituent fatty acid.
- the oil composition contains a specific amount of ABB type triglyceride in which one saturated fatty acid (A) and two saturated fatty acids (B) are combined, and the ABB type triglyceride and two saturated fatty acids (A) and saturated fatty acid.
- (B) It consists of an oil-and-fat composition whose weight ratio (ABB / AAB) with the AAB type
- bonded is in a specific range.
- the plastic fat modifier of the present invention may be simply referred to as “modifier”.
- the saturated fatty acid (A) in the present invention is a constituent fatty acid of triglyceride and is not particularly limited as long as the melting point is 60 ° C. or higher.
- Examples of the saturated fatty acid (A) include stearic acid (C18), palmitic acid (C16), arachidic acid (C20), behenic acid (C22), and the like. Since the raw material containing behenic acid (C22) is expensive, the saturated fatty acid (A) is preferably a C18 to C20 fatty acid in consideration of cost and availability.
- the saturated fatty acid (B) in the present invention is a constituent fatty acid of triglyceride and is not particularly limited as long as the melting point is 40 ° C. or lower.
- Examples of the saturated fatty acid (B) include caproic acid (C6), caprylic acid (C8), capric acid (C10), and the like. Since raw materials containing caproic acid (C6) are expensive, considering the cost and availability, the saturated fatty acid (B) is preferably a C8 to C10 fatty acid.
- the fatty acid composition in the oil and fat composition was measured as follows.
- the FID constant temperature gas chromatograph method was used.
- the FID constant temperature gas chromatograph method is a method described in “2.4.2.1 Fatty acid composition” of “Standard oil analysis test method” (issue year: 1996) edited by Japan Oil Chemistry Association.
- the ABB type triglyceride in the present invention is a triglyceride in which one saturated fatty acid (A) and two saturated fatty acids (B) are bonded, and the binding position of each fatty acid is arbitrary.
- the AAB type triglyceride in the present invention is a triglyceride in which two saturated fatty acids (A) and one saturated fatty acid (B) are combined, and the binding position of each fatty acid is arbitrary.
- the ABB type triglyceride may be simply referred to as “ABB”.
- AAB type triglyceride may be simply referred to as “AAB”.
- a C18 B C8 B C8 means a triglyceride in which one C18 saturated fatty acid (stearic acid) and two C8 saturated fatty acids (caprylic acid) are combined.
- the content of ABB in the oil composition is preferably 40 to 85% by weight in the entire oil composition.
- the content is less than 40% by weight, when the modifier is added to the plastic fat, the effect of suppressing changes in physical properties such as changes in the hardness of the plastic fat and the formation of coarse crystals may not be sufficient.
- the purification cost of the oil / fat composition that is a modifier may increase, and the ratio of ABB / AAB may increase.
- what is necessary is just to perform the measurement of the ABB content in a modifier as follows.
- the ABB content and the AAB content in the prepared plastic oil / fat modifier are analyzed by gas chromatography equipped with a capillary column and equipped with a flame ion detector, and the retention time and peak of the obtained chart are analyzed. Obtained from area ratio.
- the measurement conditions are as follows. Column: TAP-CB (manufactured by GL Sciences Inc.) Inner diameter 0.2mm, length 25m Temperature condition: Hold at starting temperature of 280 ° C. for 3 minutes, increase to 360 ° C. at a heating rate of 4 ° C./min, and hold at 360 ° C. for 5 minutes.
- the weight ratio (ABB / AAB) of ABB to AAB in the oil composition is preferably 2 to 15, and more preferably 3 to 15.
- the ratio of ABB / AAB is less than 2, the effect of suppressing the change in hardness of the plastic fat may not be sufficient.
- the ratio of ABB / AAB exceeds 15, there may be a problem in production such that the hardness of the plastic oil becomes too hard to work.
- the use amount of the modifier of the present invention is preferably adjusted so that the content of ABB is 2 to 10% by weight in the whole plastic fat. If the content of ABB in the entire plastic fat is less than 2% by weight, the effect of suppressing changes in physical properties such as hardness change and coarse crystals of the plastic fat may be insufficient. If the content of ABB in the entire plastic fat exceeds 10% by weight, the plastic fat may be softened more than necessary, and the cost is high.
- Component (I) consisting of at least one selected from fatty acids corresponding to saturated fatty acids (A), derivatives thereof and triglycerides containing saturated fatty acids (A) as main constituent fatty acids;
- a component (II) consisting of at least one selected from triglycerides containing a fatty acid corresponding to the saturated fatty acid (B), a derivative thereof and a saturated fatty acid (B) as a main constituent fatty acid;
- at least one of the components (I) and (II) needs to be a triglyceride.
- the transesterification may be performed according to a conventional method, and the catalyst may be a chemical catalyst or an enzyme catalyst.
- chemical catalysts include sodium methylate and caustic soda.
- An enzyme catalyst is a lipase that is an enzyme derived from a microorganism.
- the lipase used in the present invention may have positional specificity or may not have positional specificity.
- Examples of the lipase used in the present invention include lipases obtained from Alkaligenes, Aspergillus, Mucor, Penicillium, Canrida and the like.
- the transesterification reaction using lipase may be either a column type continuous reaction or a batch reaction.
- the use ratio of the raw oil / fat at the time of transesterification is adjusted. It is preferable to do.
- AAA, BBB, excess ABB or excess by a method such as distillation and / or selection of temperature conditions during fractionation, etc.
- the distillation method includes short process thin film distillation and molecular distillation. Moreover, it does not specifically limit as said classification method, Either the method of fractionating using organic solvents, such as acetone and hexane, and the method of fractionating without using a solvent can be used.
- the plastic oil / fat modifier of the present invention is used for the production of plastic oil / fat.
- the agent is preferably blended so that the ABB content is 2 to 10% by weight in the entire plastic fat.
- the plastic fat of the present invention preferably contains 50 to 98% by weight of palm oil.
- the plastic fat is more preferable as the amount of lauric acid contained as a constituent fatty acid is smaller.
- the content of lauric acid in the plastic fat is preferably less than 5% by weight, more preferably less than 1% by weight, and particularly preferably 0% by weight, that is, no lauric acid.
- penetration value is the consistency at the measurement temperature expressed as the penetration. After preparing the shortenings obtained in the examples and comparative examples, immediately store them at 20 ° C., and the penet values on the first day and the 45th day after storage in accordance with the consistency test method of JIS K2220-1993. The measurement was performed using a penetrometer cone (made by Mitamura Riken Kogyo Co., Ltd.) and a JIS standard product (mass 102.5 g).
- the specific gravity is determined by stopping the stirring every hour, placing the aerated fats and oils in a 27.3 ml container, removing excess oil and fat rising from the container with a spatula, measuring the weight, and measuring the results from the container. The specific gravity was calculated from the weight of fats and oils in the container minus the weight of. The evaluation standard of creaming property evaluated time until specific gravity reached the minimum value. ⁇ : Specific gravity reached 0.6 within 10 minutes. ⁇ : The specific gravity reached 0.6 within 30 minutes.
- Example 1 Production of plastic oil and fat modifier ABB type triglyceride, wherein A is stearic acid (C18), palmitic acid (C16), arachidic acid (C20) or behenic acid (C22), B is caprylic acid A C16 to C22 B C8 B C8 which is (C8), AAB type triglyceride, wherein A is stearic acid (C18), palmitic acid (C16), arachidic acid (C20) or behenic acid (C22), and B is A modifier for plastic oil and fat, which is an oil and fat composition composed of a mixture of A C16 to C22 and A C16 to C22 B C8 , which are caprylic acid (C8), was prepared as follows.
- rapeseed extremely hardened oil 92% stearic acid, 5% palmitic acid, 2% arachidic acid, 1% behenic acid or less
- MCT medium chain fatty acid triglyceride, “ACTOR M2” manufactured by Riken Vitamin Co., caprylic acid (Melting point: 16.5 ° C.): 99.8% (actual value)
- ACTOR M2 medium chain fatty acid triglyceride
- caprylic acid (Melting point: 16.5 ° C.): 99.8% (actual value)
- a random transesterification reaction was performed at 90 ° C. under vacuum for 30 minutes, water was added to stop the reaction, and the mixture was washed with water.
- 3 parts of activated clay was added, stirred under reduced pressure, and filtered in 20 minutes.
- plastic fat modifier ABB type triglyceride, A is stearic acid (C18), B is caprylic acid (C8) A C18 B C8 B C8 , AAB type triglyceride, A is A plastic fat and oil modifier, which is an oil and fat composition composed of a mixture of stearic acid (C18) and A C18 A C18 B C8 in which B is caprylic acid (C8), was prepared as follows.
- ethyl stearate manufactured by Tokyo Kasei
- MCT medium chain fatty acid triglyceride, “ACTOR M2” manufactured by Riken Vitamin Co., Ltd., caprylic acid (melting point 16.5 ° C.): 99.8% (actual measurement value)
- lipozyme RMIM Novozymes
- plastic fat modifier ABB type triglyceride wherein A is stearic acid (C18), palmitic acid (C16), arachidic acid (C20) or behenic acid (C22), B is caprylic acid A C16 to C22 B C8 B C8 which is (C8), AAB type triglyceride, wherein A is stearic acid (C18), palmitic acid (C16), arachidic acid (C20) or behenic acid (C22), and B is A modifier for plastic oil and fat, which is an oil and fat composition composed of a mixture of A C16 to C22 and A C16 to C22 B C8 , which is caprylic acid (C8), was prepared as follows.
- caprylic acid manufactured by Tokyo Chemical Industry
- lipozyme RMIM lipozyme RMIM
- the content of A C16 to C22 B C8 B C8 is 20.5%, and one of the first or third position is caprylic acid.
- the content of A C16 to C22 A C16 to C22 B C8 is 40.8%, A C16 -C22 A C16 -C22
- An oil and fat composition (87 parts) having a content of A C16 -C22 of 21.7% was obtained. After mixing 87 parts of this oil and fat composition with 58 parts of caprylic acid and 100 parts of hexane, adding 8.7 parts of Lipozyme RMIM, and conducting a 1,3-position specific transesterification reaction at 50 ° C. for 8 hours. The hexane was distilled off.
- the unreacted caprylic acid and the fatty acid of the reaction product are distilled off by thin film distillation (180 ° C., 1 Pa), and the second position is stearic acid, palmitic acid, arachidic acid, or behenic acid
- a C16 to C22 B C8 The content of B C8 is 43.4%, and the first or third position is caprylic acid.
- a C16 to C22 A C16 to C22 B C8 content is 37.9%
- An oil and fat composition (55 parts) having a C22 content of 8.1% was obtained. 110 parts of hexane is added to 55 parts of the obtained oil and fat composition, and fractionation is performed at 10 ° C.
- a C16 to C22 B C8 B C8 in which the second position was stearic acid, palmitic acid, arachidic acid or behenic acid in the entire oil and fat composition was 61.0%, and A C16 to An oil or fat composition (32 parts) having a C22 A C16 to C22 B C8 content of 25.4% was obtained.
- a C18 B C8 B C8 in which the 2nd position is stearic acid is 58.9% in the whole obtained oil and fat composition
- the content of A C18 A C18 B C8 in which the 1st or 3rd position is caprylic acid. was 19.3%.
- Example 4 Production of plastic oil and fat modifier ABB type triglyceride, wherein A is stearic acid (C18), palmitic acid (C16), arachidic acid (C20) or behenic acid (C22), B is caprylic acid (C8) A C16 to C22 B C8 B C8 and AAB type triglycerides, A is stearic acid (C18), palmitic acid (C16), arachidic acid (C20) or behenic acid (C22), B is caprylic acid A modifier for plastic oil and fat, which is an oil and fat composition composed of a mixture of A C16 to C22 and A C16 to C22 B C8 , which are (C8), was prepared as follows.
- rapeseed extremely hardened oil is mixed with 30 parts of MCT (“ACTOR M2” manufactured by Riken Vitamin Co., Ltd., caprylic acid (melting point: 16.5 ° C.): 99.8% (actual value)) and 100 parts of hexane, After adding 10 parts of lipozyme TLIM (Novozymes) and carrying out 1,3-specific transesterification reaction at 50 ° C. for 8 hours, hexane was distilled off. The obtained transesterified oil / fat was subjected to thin-film distillation (230 ° C., 1 Pa) to remove an oil / fat composition (9 parts) mainly composed of B C8 B C8 B C8 .
- the obtained oil / fat composition (91 parts) was subjected to thin-film distillation (270 ° C., 1 Pa), and the oil / fat composition (27 parts) mainly comprising A C16 to C22 B C8 B C8 and A C16 to C22 A C16 to C22
- An oil and fat composition (64 parts) mainly containing B C8 was obtained.
- 54 parts of hexane is added to the obtained oil / fat composition containing 27 parts of A C16 to C22 B C8 B C8 and fractionated at 5 ° C. to obtain A C16 to C22 A C16 to C22 B C8 .
- a part (7 parts) is removed, and hexane is distilled off.
- the content of A C16 to C22 B C8 B C8 is 81.1% in the entire oil and fat composition, and A C16 to C22 A C16 to C22 B C8.
- the oil-and-fat composition (20 parts) whose content of 9.6% was obtained.
- the content of A C18 B C8 B C8 was 75.8%, and the content of A C18 A C18 B C8 was 6.2%.
- Example 5 Production of plastic fat modifier ABB type triglyceride, wherein A is stearic acid (C18), palmitic acid (C16), arachidic acid (C20) or behenic acid (C22), B is caprylic acid A C16 to C22 B C8 to C10 B C8 to C10 which are (C8) or capric acid (C10) and AAB type triglycerides, wherein A is stearic acid (C18), palmitic acid (C16), arachidic acid (C20) Or behenic acid (C22), and B is caprylic acid (C8) or capric acid (C10) A C16 to C22 A C16 to C22 B C8 to C10
- the agent was prepared as follows.
- B C8 to C10 are prepared in the same manner as in Example 1.
- B C8 to C10 B C8 to C10 content is 45.0%
- a C16 to C22 B C8 to C10 B C8 to C10 content is 41.3%
- a C16 to C22 A C16 to C22 B C8 to C10 A transesterified oil and fat having a content of 10.7% and A C16 to C22 A C16 to C22 of 0.7% was obtained.
- the obtained transesterified oil and fat was subjected to thin-film distillation (210 ° C., 0.3 Pa), and the content of B C8 to C10 B C8 to C10 B C8 to C10 was 84.6%, and A C16 to C22 B C8 to C10 Remove the oil and fat composition (50 parts) containing B C8 to C10 of 12.7% and A C16 to C22 and A C16 to C22 of B C8 to C10 of 0.1%.
- a C16 to C22 B C8 to C10 B C8 to C10 B C8 to C10 content 5.1%, A C16 to C22 B C8 to C10 B C8 to C10 content 70.4%, A C16 to C22 A C16 to An oil and fat composition (50 parts) having a C22 B C8 to C10 content of 22.4% and an A C16 to C22 A C16 to C22 of A C16 to C22 of 1.5% was obtained.
- the content of A C18 B C8 to 10 B C8 to 10 was 68.1%, and the content of A C18 A C18 B C8 to 10 was 20.3%.
- Example 6 Production of plastic fat and oil modifier ABB type triglyceride, wherein A is stearic acid (C18), palmitic acid (C16), arachidic acid (C20) or behenic acid (C22), B is caprylic acid A C16 to C22 B C8 to C10 B C8 to C10 which are (C8) or capric acid (C10) and AAB type triglycerides, wherein A is stearic acid (C18), palmitic acid (C16), arachidic acid (C20) Or behenic acid (C22), and B is caprylic acid (C8) or capric acid (C10) A C16 to C22 A C16 to C22 B C8 to C10
- the agent was prepared as follows.
- MCT medium chain fatty acid triglyceride, “Actor M1” manufactured by Riken Vitamin Co., caprylic acid 60%, capric acid 40%
- rapeseed extremely hardened oil in the whole transesterified oil and fat, the content of B C8 to C10 B C8 to C10 is 44.0%, the content of A C16 to C22 B C8 to C10 B C8 to C10 is 40.2%, A C16-C22 A C16-C22 B C8-C10 content was 11.1%, and A C16-C22 A C16-C22 A C16-C22 content was 1.1%.
- the obtained transesterified oil and fat was subjected to thin-film distillation (220 ° C., 0.3 Pa), and the content of B C8 to C10 B C8 to C10 B C8 to C10 was 80.5%, and A C16 to C22 B C8 to C10 Remove the fat composition (52 parts) with a B C8-C10 content of 15.0% and A C16-C22 A C16-C22 and a B C8-C10 content of 0.5% in the entire fat composition.
- B C8 to C10 B C8 to C10 B C8 to C10 content is 5.6%
- a C16 to C22 B C8 to C10 B C8 to C10 content is 67.4%
- a C16 to C22 A C16 to An oil and fat composition (48 parts) having a C22 B C8 to C10 content of 22.9% and an A C16 to C22 A C16 to C22 of A C16 to C22 of 2.1% was obtained.
- the content of A C18 B C8 to 10 B C8 to 10 was 66.5%, and the content of A C18 A C18 B C8 to 10 was 21.3%.
- plastic fat modifier ABB type triglyceride wherein A is stearic acid (C18), palmitic acid (C16), arachidic acid (C20) or behenic acid (C22), B is caprylic acid A C16 to C22 B C8 B C8 which is (C8), AAB type triglyceride, wherein A is stearic acid (C18), palmitic acid (C16), arachidic acid (C20) or behenic acid (C22), and B is A modifier for plastic oil and fat, which is an oil and fat composition comprising a mixture of A C16 to C22 and A C16 to C22 B C8 which are caprylic acid (C8), was prepared as follows.
- a C16 to C22 B C8 B C8 content is 40.1%, A C16 to C22 A C16 to C22 B C8 content is 11.0%, A C16 to C22 A C16 to C22 A C16 to C22 A transesterified oil and fat having a content of 1.1% was obtained.
- the obtained transesterified oil / fat was subjected to thin-film distillation (200 ° C., 0.3 Pa), the content of BC8BC8BC8 was 82.2%, the content of A C16 to C22 B C8 B C8 was 10.2%, and A C16 ⁇ C22 A C16 ⁇ C22 B C8 content of 0.3% oil and fat composition (48 parts) is removed, and B C8 B C8 B C8 content is 5.5% in the whole oil and fat composition, A C16-C22 B C8 B C8 content 65.5%, A C16-C22 A C16-C22 B C8 content 20.7%, A C16-C22 A C16-C22 A C16-C22 content Obtained 2.3% of an oil and fat composition (52 parts). In the entire obtained fat and oil composition, the content of A C18 B C8 B C8 was 26.1%, and the content of A C18 A C18 B C8 was 3.0%.
- Example 8 Production of plastic fat and oil modifier ABB type triglyceride, wherein A is stearic acid (C18), palmitic acid (C16), arachidic acid (C20) or behenic acid (C22), B is caprylic acid and a C16 ⁇ C22 B C8 B C8 is (C8), an AAB type triglyceride, a is stearic acid (C18), palmitic acid (C16), arachidic acid (C20), or behenic acid (C22), and B A modifier for plastic oil and fat, which is an oil and fat composition comprising a mixture of A C16 to C22 and A C16 to C22 B C8 , which are caprylic acid (C8), was prepared as follows.
- MCT medium chain fatty acid triglyceride, “ACTOR M2” manufactured by Riken Vitamin Co., Ltd.
- caprylic acid against 30 parts of Hyelsin rapeseed extremely hardened oil (behenic acid 49%, stearic acid 39%, arachidic acid 8%, palmitic acid 4%) (Melting point 16.5 ° C.): 99.8% (actual measured value) 70 parts were mixed, and in the same manner as in Example 1, the content of B C8 B C8 B C8 was 45.1%, and A C16- C22 B C8 B C8 content is 40.0%, A C16 to C22 A C16 to C22 B C8 content is 10.8%, A C16 to C22 A C16 to C22 A C16 to C22 content is 0 7% transesterified oil was obtained.
- the obtained transesterified oil / fat was subjected to thin-film distillation (200 ° C., 0.3 Pa), the content of B C8 B C8 B C8 was 89.9%, and the content of A C16 to C22 B C8 B C8 was 4.
- ABB type triglycerides wherein A is stearic acid (C18), palmitic acid (C16), arachidic acid (C20) or behenic acid (C22), B is caprylic acid and a C16 ⁇ C22 B C8 B C8 is (C8), an AAB type triglyceride, a is stearic acid (C18), palmitic acid (C16), arachidic acid (C20), or behenic acid (C22), and B A modifier for plastic oil and fat, which is an oil and fat composition comprising a mixture of A C16 to C22 and A C16 to C22 B C8 , which are caprylic acid (C8), was prepared as follows.
- hexane 200 parts is added to 100 parts of the oil and fat which is the filtrate obtained in the same manner as in Example 1, and fractionation is performed at 20 ° C., which is rich in A C16 to C22 A C16 to C22 A C16 to C22 (25 parts) was removed and hexane was distilled off.
- 150 parts of hexane is added to 75 parts of this oil and fat composition and fractionated at 5 ° C. to remove low melting point components (32 parts) rich in A C16 to C20 B C8 B C8 , and hexane is distilled off.
- an oil and fat composition having a content of A C16 to C22 A C16 to C22 B C8 of 68.7% and an content of A C16 to C22 B C8 B C8 of 20.1% (43 parts) )
- the content of A C18 A C18 B C8 was 60.3%
- the content of A C18 B C8 B C8 was 18.8%.
- Example 9 to 16 Production of shortening (plastic oil and fat) 5 parts of the plastic oil and fat modifier obtained in Examples 1 to 8 and 95 parts of palm oil were melt-mixed and rapidly kneaded using a quenching kneader. To make a shortening.
- Example 9 As shown in Table 1, an oil and fat composition having a weight ratio of ABB to AAB (ABB / AAB) of 2 or more was added as a modifier so that the ABB content was 2% or more.
- Example 9 With ⁇ 16 shortenings, the daily change in hardness was small. However, the hardness was hard compared with the case where the value of ABB / AAB was large.
- the shortening of Comparative Example 3 produced only with palm oil without adding a modifier had a high hardness and a large change with time.
- the shortening of Comparative Example 4 in which the amount of the modifier added was small and the content of ABB was small the hardness was hard and the change with time was large.
- Comparative Example 1 since the oil and fat composition of Comparative Example 1 having a small value of ABB / AAB was added as a modifier, the shortening of Comparative Example 5 having a low ABB content is hard, and its aging changes It was big. Further, among the constituent fatty acids of ABB, the fatty acid composition of Comparative Example 6 in which the saturated fatty acid (A) is palmitic acid (C16) and the saturated fatty acid (B) is lauric acid (C12) is added. For shortening, even if an oil composition having a weight ratio of ABB to AAB (ABB / AAB) of 2 or more is blended so that the ABB content is 2% or more, the hardness is hard and changes with time. Was also big.
- the saturated fatty acid (A) is C16 to C22
- the saturated fatty acid (B) is C8 and C10 ABB
- the saturated fatty acid (A) is C16
- saturated fatty acid (B ) Is a C12 ABB
- a shortening in which a modifier comprising an oil and fat composition having a weight ratio of ABB to AAB (ABB / AAB) of 2 or more is added so that the ABB content is 2% or more Creaming increased compared to shortening made from palm oil alone.
- the fat and oil composition is a saturated fatty acid (A) of C16 to C22, a saturated fatty acid (B) of C8 and C10, and a weight ratio of ABB to AAB (ABB / AAB) of 2 or more. No syrup separation occurred in the shortening in which the modifier consisting of was blended so that the ABB content was 2% or more.
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Abstract
Description
融点が60℃以上の飽和脂肪酸(A)及び融点が40℃以下の飽和脂肪酸(B)を構成脂肪酸とするトリグリセリドからなる油脂組成物であって、前記油脂組成物全体中、飽和脂肪酸(A)が1つ及び飽和脂肪酸(B)が2つ結合したABB型トリグリセリドを40~85重量%含有し、前記ABB型トリグリセリドと飽和脂肪酸(A)が2つ及び飽和脂肪酸(B)が1つ結合したAAB型トリグリセリドとの重量比(ABB/AAB)が2~15である油脂組成物、
からなる可塑性油脂用改質剤に関する。
FID恒温ガスクロマトグラフ法により行った。FID恒温ガスクロマトグラフ法とは、社団法人日本油化学協会編「基準油脂分析試験法」(発行年:1996年)の「2.4.2.1 脂肪酸組成」に記載された方法である。
本発明において、作製した可塑性油脂用改質剤中のABB含量及びAAB含量は、キャピラリーカラムを装備した、水素炎イオン検出器付きのガスクロマトグラフィーにて分析し、得られたチャートのリテンションタイム及びピークエリア比より、求めた。測定条件は以下の通りである。
カラム:TAP-CB(ジーエルサイエンス株式会社製)
内径0.2mm、長さ25m
温度条件:開始温度280℃で3分間保持し、昇温速度4℃/分で360℃まで上昇させ、360℃で5分間保持する。
飽和脂肪酸(A)に対応する脂肪酸、その誘導体及び飽和脂肪酸(A)を主たる構成脂肪酸とするトリグリセリドの中から選ばれる少なくとも1種からなる成分(I)と、
飽和脂肪酸(B)に対応する脂肪酸、その誘導体及び飽和脂肪酸(B)を主たる構成脂肪酸とするトリグリセリドの中から選ばれる少なくとも1種からなる成分(II)と、
をエステル交換によって油脂組成物を得る方法がある。但し、前記成分(I)及び(II)の少なくとも一方はトリグリセリドであることが必要である。
ペネ値とは、測定温度における稠度を針入度で表したものである。実施例・比較例で得られたショートニングを作製後、直ちに20℃に保管し、保管後1日目と45日目のペネ値を、JIS K2220-1993の稠度試験法に準拠し、デジタル式オートペネトロメーター(三田村理研工業製)及びJIS標準品(質量102.5g)のペネトロメーター・コーンを用いて測定した。
ショートニングの硬さ変化は、保管後1日目と45日目のペネ値の差を用いて、以下の基準で評価した。
○:保管中のペネ値変化が10未満。
△:保管中のペネ値変化が10~30。
×:保管中のペネ値変化が30超える。
比重の経時変化を以下のように測定し、その変化の仕方を基に以下の基準で評価した。実施例・比較例で得られたショートニングを、ペネ値が150程度になるよう23℃で温調した。そのショートニング300gをホバートミキサー(ホバートコーポレーション製)の低速1で1分間砕いた。さらにシロップ314gを加え、低速1で1分間ショートニングと混合させた。その後、中速2で攪拌し始めた時点を測定開始点とし、以降5分までは1分ごと、10分までは2.5分ごと、それ以降は30分まで5分ごとに水に対する比重を測定した。比重は、各時間ごとに撹拌を止め、含気した油脂を27.3mlの容器に入れ、容器から盛り上がった余分な油脂をスパチュラですり切りして取り除いた後、重量を測定し、測定結果から容器の重量を差し引いた容器内の油脂の重量から、その比重を算出した。クリーミング性の評価基準は、比重が最低値に達するまでの時間を評価した。
○:10分以内に比重が0.6に達したもの。
△:30分以内に比重が0.6に達したもの。
実施例・比較例で得られたショートニングを、ペネ値が150程度になるよう23℃で温調した。そのショートニング300gをホバートミキサー(ホバートコーポレーション製)の低速1で1分間砕いた。さらにシロップ314gを加え、低速1で1分間ショートニングと混合させた。その後、中速2で攪拌し始めた時点を測定開始点とし、30分後に撹拌を止め、シロップの分離度合いを目視で判断した。その際の評価基準は、以下の通りとした。
○:シロップの分離がない。
△:シロップの分離が見られた。
×:シロップが著しく分離した。
ABB型トリグリセリドであって、Aがステアリン酸(C18)、パルミチン酸(C16)、アラキジン酸(C20)又はベヘン酸(C22)、Bがカプリル酸(C8)であるAC16~C22BC8BC8と、AAB型トリグリセリドであって、Aがステアリン酸(C18)、パルミチン酸(C16)、アラキジン酸(C20)又はベヘン酸(C22)、Bがカプリル酸(C8)であるAC16~C22AC16~C22BC8との混合物からなる油脂組成物である可塑性油脂用改質剤を、以下のように作製した。
菜種極度硬化油70部(ステアリン酸92%、パルミチン酸5%、アラキジン酸2%、ベヘン酸1%以下)に対して、MCT(中鎖脂肪酸トリグリセリド、理研ビタミン社製「アクターM2」、カプリル酸(融点16.5℃):99.8%(実測値))30部を混合し、90℃、真空下で脱水を行った。次に、ナトリウムメチラート0.3部を加え、90℃、真空下で30分間ランダムエステル交換反応を行い、水を加えて反応停止した後、水洗した。次に、活性白土3部を加え、減圧下で攪拌して20分後に全量濾過した。その後、濾液である油脂組成物100部に対してヘキサン200部を加えて、5℃で分別を行ってAC16~C22AC16~C22AC16~C22に富む高融点成分(63部)を除去した。その後、ヘキサンを蒸留除去して、油脂組成物全体中、AC16~C22BC8BC8の含有量が54.6%、AC16~C22AC16~C22BC8の含有量が21.8%の油脂組成物(37部)を得た。得られた油脂組成物全体中、AC18BC8BC8の含有量は49.9%、AC18AC18BC8の含有量は13.0%であった。
ABB型トリグリセリドで、Aがステアリン酸(C18)、Bがカプリル酸(C8)であるAC18BC8BC8と、AAB型トリグリセリドで、Aがステアリン酸(C18)、Bがカプリル酸(C8)であるAC18AC18BC8との混合物からなる油脂組成物である可塑性油脂用改質剤を以下のように作製した。
MCT(中鎖脂肪酸トリグリセリド、理研ビタミン社製「アクターM2」、カプリル酸(融点16.5℃):99.8%(実測値))100部にステアリン酸エチル(東京化成製)50部を混合し、1,3位特異的酵素であるリポザイムRMIM(ノボザイムズ社)を10部加え、50℃で8時間、1,3位特異的エステル交換反応を行った。反応後、未反応のステアリン酸とMCT、及び反応生成物のカプリル酸を薄膜蒸留装置(210℃、1Pa)にて留去し、油脂組成物全体中、1位又は3位の1つがステアリン酸であるAC18BC8BC8の含有量が67.0%、2位がカプリル酸であるAC18AC18BC8の含有量が17.4%の油脂組成物(44部)を得た。
ABB型トリグリセリドであって、Aがステアリン酸(C18)、パルミチン酸(C16)、アラキジン酸(C20)又はベヘン酸(C22)、Bがカプリル酸(C8)であるAC16~C22BC8BC8と、AAB型トリグリセリドであって、Aがステアリン酸(C18)、パルミチン酸(C16)、アラキジン酸(C20)又はベヘン酸(C22)、Bがカプリル酸(C8)である、AC16~C22AC16~C22BC8との混合物からなる油脂組成物である可塑性油脂用改質剤を以下のように作製した。
菜種極度硬化油100部にカプリル酸(東京化成製)65部、ヘキサン100部を混合し、リポザイムRMIM 10部を加え、50℃で8時間、1,3位特異的エステル交換反応を行った後、ヘキサンを蒸留除去した。その後、未反応のカプリル酸及び反応生成物の脂肪酸を薄膜蒸留(180℃、1Pa)にて留去し、油脂組成物全体中、2位がステアリン酸、パルミチン酸、アラキジン酸又はベヘン酸であるAC16~C22BC8BC8の含有量が20.5%、1位又は3位の1つがカプリル酸であるAC16~C22AC16~C22BC8の含有量が40.8%、AC16~C22AC16~C22AC16~C22の含有量が21.7%の油脂組成物(87部)を得た。この油脂組成物87部に対して、カプリル酸58部及びヘキサン100部を混合し、リポザイムRMIM 8.7部を加え、50℃、8時間、1,3位特異的エステル交換反応を行った後、ヘキサンを蒸留除去した。その後、未反応のカプリル酸及び反応生成物の脂肪酸を薄膜蒸留(180℃、1Pa)にて留去し、2位がステアリン酸、パルミチン酸、アラキジン酸又はベヘン酸であるAC16~C22BC8BC8の含有量が43.4%、1位又は3位がカプリル酸であるAC16~C22AC16~C22BC8の含有量が37.9%、AC16~C22AC16~C22AC16~C22の含有量が8.1%の油脂組成物(55部)を得た。得られた油脂組成物55部に対し、ヘキサン110部を加えて、10℃で分別を行い、AC16~C22AC16~C22AC16~C22に富む高融点成分(23部)を除去し、さらにヘキサンを蒸留除去して、油脂組成物全体中、2位がステアリン酸、パルミチン酸、アラキジン酸又はベヘン酸であるAC16~C22BC8BC8の含有量が61.0%、AC16~C22AC16~C22BC8の含有量が25.4%の油脂組成物(32部)を得た。得られた油脂組成物全体中、2位がステアリン酸であるAC18BC8BC8の含有量は58.9%、1位又は3位がカプリル酸であるAC18AC18BC8の含有量は19.3%であった。
ABB型トリグリセリドであって、Aがステアリン酸(C18)、パルミチン酸(C16)、アラキジン酸(C20)又はベヘン酸(C22)、Bがカプリル酸(C8)であるAC16~C22BC8BC8と、AAB型トリグリセリドで、Aがステアリン酸(C18)、パルミチン酸(C16)、アラキジン酸(C20)又はベヘン酸(C22)、Bがカプリル酸(C8)であるAC16~C22AC16~C22BC8との混合物からなる油脂組成物である可塑性油脂用改質剤を以下のように作製した。
菜種極度硬化油70部に対して、MCT(理研ビタミン社製「アクターM2」、カプリル酸(融点16.5℃):99.8%(実測値))30部、ヘキサン100部を混合し、リポザイムTLIM(ノボザイムズ社)10部を加え、50℃で8時間、1,3位特異的エステル交換反応を行った後、ヘキサンを蒸留除去した。得られたエステル交換油脂を、薄膜蒸留(230℃、1Pa)して、BC8BC8BC8を主とする油脂組成物(9部)を除去した。さらに得られた油脂組成物(91部)を薄膜蒸留(270℃、1Pa)し、AC16~C22BC8BC8を主とする油脂組成物(27部)とAC16~C22AC16~C22BC8を主とする油脂組成物(64部)を得た。得られた27部のAC16~C22BC8BC8を主とする油脂組成物に対して、ヘキサン54部を加えて、5℃で分別を行い、AC16~C22AC16~C22BC8を一部(7部)除去し、さらにヘキサンを蒸留除去して、油脂組成物全体中、AC16~C22BC8BC8の含有量が81.1%、AC16~C22AC16~C22BC8の含有量が9.6%の油脂組成物(20部)を得た。得られた油脂組成物全体中、AC18BC8BC8の含有量は75.8%、AC18AC18BC8の含有量は6.2%であった。
ABB型トリグリセリドであって、Aがステアリン酸(C18)、パルミチン酸(C16)、アラキジン酸(C20)又はベヘン酸(C22)、Bがカプリル酸(C8)又はカプリン酸(C10)であるAC16~C22BC8~C10BC8~C10と、AAB型トリグリセリドであって、Aがステアリン酸(C18)、パルミチン酸(C16)、アラキジン酸(C20)又はベヘン酸(C22)、Bがカプリル酸(C8)又はカプリン酸(C10)であるAC16~C22AC16~C22BC8~C10との混合物からなる油脂組成物である可塑性油脂用改質剤を以下のように作製した。
菜種極度硬化油30部に対して、MCT(中鎖脂肪酸トリグリセリド、ダニスコ社製、カプリル酸85%、カプリン酸15%)70部を混合し、実施例1と同様の方法で、BC8~C10BC8~C10BC8~C10の含有量が45.0%、AC16~C22BC8~C10BC8~C10の含有量が41.3%、AC16~C22AC16~C22BC8~C10の含有量が10.7%、AC16~C22AC16~C22AC16~C22の含有量が0.7%のエステル交換油脂を得た。得られたエステル交換油脂を、薄膜蒸留(210℃、0.3Pa)して、BC8~C10BC8~C10BC8~C10の含有量が84.6%、AC16~C22BC8~C10BC8~C10の含有量が12.7%、AC16~C22AC16~C22BC8~C10の含有量が0.1%の油脂組成物(50部)を除去し、油脂組成物全体中、BC8~C10BC8~C10BC8~C10の含有量が5.1%、AC16~C22BC8~C10BC8~C10の含有量が70.4%、AC16~C22AC16~C22BC8~C10の含有量が22.4%、AC16~C22AC16~C22AC16~C22の含有量が1.5%の油脂組成物(50部)を得た。得られた油脂組成物全体中、AC18BC8~10BC8~10の含有量は68.1%、AC18AC18BC8~10の含有量は20.3%であった。
ABB型トリグリセリドであって、Aがステアリン酸(C18)、パルミチン酸(C16)、アラキジン酸(C20)又はベヘン酸(C22)、Bがカプリル酸(C8)又はカプリン酸(C10)であるAC16~C22BC8~C10BC8~C10と、AAB型トリグリセリドであって、Aがステアリン酸(C18)、パルミチン酸(C16)、アラキジン酸(C20)又はベヘン酸(C22)、Bがカプリル酸(C8)又はカプリン酸(C10)であるAC16~C22AC16~C22BC8~C10との混合物からなる油脂組成物である可塑性油脂用改質剤を以下のように作製した。
菜種極度硬化油30部に対して、MCT(中鎖脂肪酸トリグリセリド、理研ビタミン社製「アクターM1」、カプリル酸60%、カプリン酸40%)70部を混合し、実施例1と同様の方法で、エステル交換油脂全体中、BC8~C10BC8~C10BC8~C10の含有量が44.0%、AC16~C22BC8~C10BC8~C10の含有量が40.2%、AC16~C22AC16~C22BC8~C10の含有量が11.1%、AC16~C22AC16~C22AC16~C22の含有量が1.1%のエステル交換油脂を得た。得られたエステル交換油脂を、薄膜蒸留(220℃、0.3Pa)して、BC8~C10BC8~C10BC8~C10の含有量が80.5%、AC16~C22BC8~C10BC8~C10の含有量が15.0%、AC16~C22AC16~C22BC8~C10の含有量が0.5%の油脂組成物(52部)を除去し、油脂組成物全体中、BC8~C10BC8~C10BC8~C10の含有量が5.6%、AC16~C22BC8~C10BC8~C10の含有量が67.4%、AC16~C22AC16~C22BC8~C10の含有量が22.9%、AC16~C22AC16~C22AC16~C22の含有量が2.1%の油脂組成物(48部)を得た。得られた油脂組成物全体中、AC18BC8~10BC8~10の含有量は66.5%、AC18AC18BC8~10の含有量は21.3%であった。
ABB型トリグリセリドであって、Aがステアリン酸(C18)、パルミチン酸(C16)、アラキジン酸(C20)又はベヘン酸(C22)、Bがカプリル酸(C8)であるAC16~C22BC8BC8と、AAB型トリグリセリドであって、Aがステアリン酸(C18)、パルミチン酸(C16)、アラキジン酸(C20)又はベヘン酸(C22)、Bがカプリル酸(C8)であるAC16~C22AC16~C22BC8との混合物からなる油脂組成物である可塑性油脂用改質剤を以下のように作製した。
パームステアリン極度硬化油30部(パルミチン酸60%、ステアリン酸38%、アラキジン酸1%以下、ベヘン酸0.1%未満)に対して、MCT(中鎖脂肪酸トリグリセリド、理研ビタミン社製「アクターM2」、カプリル酸(融点16.5℃):99.8%(実測値))70部を混合し、実施例1と同様の方法で、BC8BC8BC8の含有量が42.4%、AC16~C22BC8BC8の含有量が40.1%、AC16~C22AC16~C22BC8の含有量が11.0%、AC16~C22AC16~C22AC16~C22の含有量が1.1%のエステル交換油脂を得た。得られたエステル交換油脂を、薄膜蒸留(200℃、0.3Pa)して、BC8BC8BC8の含有量が82.2%、AC16~C22BC8BC8の含有量が10.2%、AC16~C22AC16~C22BC8の含有量が0.3%の油脂組成物(48部)を除去し、油脂組成物全体中、BC8BC8BC8の含有量が5.5%、AC16~C22BC8BC8の含有量が65.5%、AC16~C22AC16~C22BC8の含有量が20.7%、AC16~C22AC16~C22AC16~C22の含有量が2.3%の油脂組成物(52部)を得た。得られた油脂組成物全体中、AC18BC8BC8の含有量は26.1%、AC18AC18BC8の含有量は3.0%であった。
ABB型トリグリセリドであって、Aがステアリン酸(C18)、パルミチン酸(C16)、アラキジン酸(C20)又はベヘン酸(C22)、Bがカプリル酸(C8)であるAC16~C22BC8BC8と、AAB型トリグリセリドであって、Aがステアリン酸(C18)、パルミチン酸(C16)、アラキジン酸(C20)又はベヘン酸(C22)、Bがカプリル酸(C8)であるAC16~C22AC16~C22BC8の混合物からなる油脂組成物である可塑性油脂用改質剤を以下のように作製した。
ハイエルシン菜種極度硬化油30部(ベヘン酸49%、ステアリン酸39%、アラキジン酸8%、パルミチン酸4%)に対して、MCT(中鎖脂肪酸トリグリセリド、理研ビタミン社製「アクターM2」、カプリル酸(融点16.5℃):99.8%(実測値))70部を混合し、実施例1と同様の方法で、BC8BC8BC8の含有量が45.1%、AC16~C22BC8BC8の含有量が40.0%、AC16~C22AC16~C22BC8の含有量が10.8%、AC16~C22AC16~C22AC16~C22の含有量が0.7%のエステル交換油脂を得た。得られたエステル交換油脂を、薄膜蒸留(200℃、0.3Pa)して、BC8BC8BC8の含有量が89.9%、AC16~C22BC8BC8の含有量が4.2%、AC16~C22AC16~C22BC8の含有量が0.3%の油脂組成物(48部)を除去し、油脂組成物全体中、BC8BC8BC8の含有量が4.0%、AC16~C22BC8BC8の含有量が72.9%、AC16~C22AC16~C22BC8の含有量が20.3%、AC16~C22AC16~C22AC16~C22の含有量が1.5%の油脂組成物(52部)を得た。得られた油脂組成物全体中、AC18BC8BC8の含有量は30.0%、AC18AC18BC8の含有量は3.5%であった。
ABB型トリグリセリドであって、Aがステアリン酸(C18)、パルミチン酸(C16)、アラキジン酸(C20)又はベヘン酸(C22)、Bがカプリル酸(C8)であるAC16~C22BC8BC8と、AAB型トリグリセリドであって、Aがステアリン酸(C18)、パルミチン酸(C16)、アラキジン酸(C20)又はベヘン酸(C22)、Bがカプリル酸(C8)であるAC16~C22AC16~C22BC8の混合物からなる油脂組成物である可塑性油脂用改質剤を以下のように作製した。
実施例1と同様にして得た濾液である油脂100部に対して、ヘキサン200部を加えて、20℃で分別を行い、AC16~C22AC16~C22AC16~C22に富む高融点成分(25部)を除去して、ヘキサンを蒸留除去した。この油脂組成物75部に対して、ヘキサン150部を加えて、5℃で分別を行い、AC16~C20BC8BC8に富む低融点成分(32部)を除去し、さらにヘキサンを蒸留除去して、組成物全体中、AC16~C22AC16~C22BC8の含有量が68.7%、AC16~C22BC8BC8の含有量が20.1%の油脂組成物(43部)を得た。得られた油脂組成物全体中、AC18AC18BC8の含有量は60.3%、AC18BC8BC8の含有量は18.8%であった。
ABB型トリグリセリドであって、Aがパルミチン酸(C16)、Bがラウリン酸(C12)であるAC16BC12BC12と、AAB型トリグリセリドであって、Aがパルミチン酸(C16)、Bがラウリン酸(C12)であるAC16AC12BC12との混合物からなる油脂組成物である可塑性油脂用改質剤を以下のように作製した。
トリラウリン100部(東京化成製)(ラウリン酸の融点:43.5℃)にパルミチン酸(融点:63.1℃)(大和薬品製)100部、ヘキサン100部を混合し、リポザイムRMIM 10部を加え、50℃で8時間、1,3位特異的エステル交換反応を行った後、ヘキサンを蒸留除去した。その後、未反応のパルミチン酸及び反応生成物のラウリン酸を薄膜蒸留にて留去し、Bがラウリン酸であるBC12BC12BC12の含有量が25.5%、Aがパルミチン酸且つBがラウリン酸であるAC16BC12BC12の含有量が46.6%、AC16BC12AC16の含有量が17.8%の油脂組成物(92部)を得た。この油脂組成物92部に対し、ヘキサン184部を加えて、10℃で分別を行い、さらにヘキサンを蒸留除去し、油脂組成物全体中、AC16BC12BC12の含有量が51.7%、AC16BC12AC16の含有量が13.6%の油脂組成物(45部)を得た。
実施例1~8で得た可塑性油脂用改質剤5部とパーム油95部とを融解混合し、急冷捏和機を用いて急冷練り合わせを行い、ショートニングを作製した。
改質剤を添加せず、パーム油100%のショートニングを実施例9~16と同様の方法で作製した。
実施例4で作製した可塑性油脂用改質剤2部とパーム油98部を融解混合し、実施例9~16と同様にショートニングを作製した。
比較例1で得た可塑性油脂用改質剤5部とパーム油95部とを融解混合し、実施例9~16と同様にショートニングを作製した。
比較例2で得た可塑性油脂用改質剤5部とパーム油95部とを融解混合し、実施例9~16と同様にショートニングを作製した。
Claims (4)
- 融点が60℃以上の飽和脂肪酸(A)及び融点が40℃以下の飽和脂肪酸(B)を構成脂肪酸とするトリグリセリドからなる油脂組成物であって、前記油脂組成物全体中、飽和脂肪酸(A)が1つ及び飽和脂肪酸(B)が2つ結合したABB型トリグリセリドを40~85重量%含有し、前記ABB型トリグリセリドと飽和脂肪酸(A)が2つ及び飽和脂肪酸(B)が1つ結合したAAB型トリグリセリドとの重量比(ABB/AAB)が2~15である油脂組成物、
からなる可塑性油脂用改質剤。 - 前記トリグリセリドを構成する全脂肪酸の内、C16~C22の飽和脂肪酸(A)の含有量が50~70重量%であり、C6~C10の飽和脂肪酸(B)の含有量が30~50重量%である請求項1に記載の可塑性油脂用改質剤。
- 前記トリグリセリドを構成する全脂肪酸の内、C18の飽和脂肪酸(A)の含有量が50~70重量%であり、C8~C10の飽和脂肪酸(B)の含有量が30~50重量%である請求項1に記載の可塑性油脂用改質剤。
- 請求項1~3の何れか1項に記載の可塑性油脂用改質剤を可塑性油脂全体中で前記ABB型トリグリセリドの含有量が2~10重量%となるように配合するとともに、パーム油を50~98重量%配合してなり、且つラウリン酸の含有量が5重量%未満である可塑性油脂。
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JP2011509260A JP4894975B2 (ja) | 2009-04-16 | 2010-04-02 | 可塑性油脂用改質剤 |
CN201080016807.4A CN102395665B (zh) | 2009-04-16 | 2010-04-02 | 塑性油脂用改性剂 |
US13/264,714 US8354133B2 (en) | 2009-04-16 | 2010-04-02 | Modifying agent for plastic fat |
EP10764366A EP2420555A4 (en) | 2009-04-16 | 2010-04-02 | MODIFICATION AGENT FOR A PLASTIC GREASE |
CA2758891A CA2758891A1 (en) | 2009-04-16 | 2010-04-02 | Modifying agent for plastic fat |
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US (1) | US8354133B2 (ja) |
EP (1) | EP2420555A4 (ja) |
JP (1) | JP4894975B2 (ja) |
CN (1) | CN102395665B (ja) |
CA (1) | CA2758891A1 (ja) |
WO (1) | WO2010119781A1 (ja) |
Cited By (6)
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CN103181417A (zh) * | 2011-12-28 | 2013-07-03 | 丰益(上海)生物技术研发中心有限公司 | 一种油脂组合物、复合油脂组合物、制品及其制备方法 |
JP2016189724A (ja) * | 2015-03-31 | 2016-11-10 | 株式会社カネカ | パン生地および可塑性油脂組成物 |
JPWO2016204089A1 (ja) * | 2015-06-15 | 2017-06-29 | 日清オイリオグループ株式会社 | 可塑性油脂組成物 |
WO2018021199A1 (ja) * | 2016-07-27 | 2018-02-01 | 日清オイリオグループ株式会社 | 油脂組成物 |
EP3797599A1 (en) | 2019-09-26 | 2021-03-31 | Showa Sangyo Co., Ltd. | Plastic fat composition and method for producing thereof |
JP7446763B2 (ja) | 2018-10-24 | 2024-03-11 | 日清オイリオグループ株式会社 | 可塑性油脂組成物用添加剤 |
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WO2013132284A1 (en) | 2012-03-09 | 2013-09-12 | Cruz Adriana Fernanda | Cocoa butter substitute |
EP3421579B1 (en) * | 2016-02-22 | 2021-03-17 | Fuji Oil Holdings Inc. | Transesterified oil and plastic oil/fat composition using same as hardstock |
JP7261792B2 (ja) * | 2018-04-27 | 2023-04-20 | 株式会社カネカ | 新規ロールインマーガリン |
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CN103181417A (zh) * | 2011-12-28 | 2013-07-03 | 丰益(上海)生物技术研发中心有限公司 | 一种油脂组合物、复合油脂组合物、制品及其制备方法 |
JP2016189724A (ja) * | 2015-03-31 | 2016-11-10 | 株式会社カネカ | パン生地および可塑性油脂組成物 |
JPWO2016204089A1 (ja) * | 2015-06-15 | 2017-06-29 | 日清オイリオグループ株式会社 | 可塑性油脂組成物 |
WO2018021199A1 (ja) * | 2016-07-27 | 2018-02-01 | 日清オイリオグループ株式会社 | 油脂組成物 |
JP7446763B2 (ja) | 2018-10-24 | 2024-03-11 | 日清オイリオグループ株式会社 | 可塑性油脂組成物用添加剤 |
EP3797599A1 (en) | 2019-09-26 | 2021-03-31 | Showa Sangyo Co., Ltd. | Plastic fat composition and method for producing thereof |
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CN102395665B (zh) | 2013-08-07 |
JP4894975B2 (ja) | 2012-03-14 |
US8354133B2 (en) | 2013-01-15 |
CN102395665A (zh) | 2012-03-28 |
CA2758891A1 (en) | 2010-10-21 |
EP2420555A1 (en) | 2012-02-22 |
EP2420555A4 (en) | 2012-11-21 |
US20120040077A1 (en) | 2012-02-16 |
JPWO2010119781A1 (ja) | 2012-10-22 |
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