WO2011037296A1 - 하드버터의 제조방법 - Google Patents
하드버터의 제조방법 Download PDFInfo
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- WO2011037296A1 WO2011037296A1 PCT/KR2009/006249 KR2009006249W WO2011037296A1 WO 2011037296 A1 WO2011037296 A1 WO 2011037296A1 KR 2009006249 W KR2009006249 W KR 2009006249W WO 2011037296 A1 WO2011037296 A1 WO 2011037296A1
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- WIPO (PCT)
- Prior art keywords
- sos
- fat
- oil
- hard butter
- solvent
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Classifications
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C15/00—Butter; Butter preparations; Making thereof
- A23C15/02—Making thereof
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
- A23G1/30—Cocoa products, e.g. chocolate; Substitutes therefor
- A23G1/32—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds
- A23G1/36—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds characterised by the fats used
- A23G1/38—Cocoa butter substitutes
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
- A23G1/30—Cocoa products, e.g. chocolate; Substitutes therefor
- A23G1/32—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds
- A23G1/46—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds containing dairy products
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0008—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents
- C11B7/0025—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents in solvents containing oxygen in their molecule
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0083—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils with addition of auxiliary substances, e.g. cristallisation promotors, filter aids, melting point depressors
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- 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
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- 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
- C11C3/10—Ester interchange
Definitions
- the present invention relates to a hard butter manufacturing method, more specifically, hard containing at least 85% by weight of 1,3- distearoyl-2-oleoylglycerin (SOS) from fats and oils obtained through enzyme transesterification It relates to a method for producing butter.
- SOS 1,3- distearoyl-2-oleoylglycerin
- Hard butter developed to replace cacao butter is widely used in foods, pharmaceuticals, and cosmetics such as chocolate-based confectionery, bakery.
- Such hard butters include 1,3-dipalmitoyl-2-oleoylglycerin (POP), 1-palmitoyl-2-oleoyl-3-stearoylglycerin (POS), and 1,3-distearoyl
- POP 1,3-dipalmitoyl-2-oleoylglycerin
- POS 1-palmitoyl-2-oleoyl-3-stearoylglycerin
- SUS symmetric triglycerides having one unsaturated bond in a molecule such as 2-oleoylglycerine (SOS).
- Hard butter can be prepared by fractionating vegetable or animal fats and oils.
- fractionation consists of the following steps: First, the fat or oil is made into a liquid or molten state, and then cooled to a desired separation temperature to induce nucleation. The crystals are then grown to size and shape where separation can be effectively performed. Finally, the solid phase and the liquid phase are separated, and methods such as filtration, filter press, or centrifugation are used. Fractionation of fats and oils does not give an irreversible change in chemical composition compared to other fats and oils, and can only reversibly change the chemical composition by physical properties.
- Dry fractionation without solvents has been widely used due to the development of crystal tubes and high pressure filter presses because of the crystallization depending only on the melting point of the fat or oil itself. It is a classification technology that has been in the spotlight recently because it does not need post-treatment of the final product and there is little loss of the product. Moreover, it is considered to be a preferable method also in the safety and cost problem which are a problem in solvent classification.
- the separation precision is lower than that of the solvent fractionation, so that the liquid phase is mixed when the crystal is separated, thereby lowering the purity, and it is difficult to operate the fractionation process.
- the solvent fractionation method can improve the efficiency of separation and the like by increasing the melting point difference of triglycerides and fatty acids using organic solvents such as alcohol, hexane and acetone.
- organic solvents such as alcohol, hexane and acetone.
- the solvent is used, the viscosity of the raw material is reduced, so that the fraction can be fractionated in a short time, and the effective crystallization can be performed effectively.
- the separation degree is good, the yield is high. It is possible to increase the purity of the decision.
- the solvent fractionation method has an advantage of overcoming the disadvantages of the dry fractionation method, but because of the bulkiness in the process, there is a burden on facility investment cost and explosion risk in the case of hexane.
- solvent fractionation is widely used in the manufacture of hard butter having a precise composition because it has a high degree of separation.
- the palatability of the confectionery manufactured by the hard butter may vary according to the composition of the hard butter.
- the hard butter affects the palatability of the chocolate, it is necessary to develop a hard butter for manufacturing a confectionery including chocolate having a higher palatability.
- Chocolate made from SOS-rich hard butter tends to be preferred by many people because of its high hardness and good meltability.
- a method of fractionating at cryogenic temperatures below 0 ° C. has been used to manufacture hard butter rich in SOS, which has a disadvantage in that a long working time and a high process cost are required.
- the present inventors have completed the present invention as a result of research to develop a more economical method of manufacturing SOS hard butter having a high SOS content, which can shorten working time and reduce process cost.
- Another object of the present invention is to provide a method for manufacturing a high purity SOS hard butter that can reduce the working time and manufacturing cost.
- Another object of the present invention to provide a chocolate containing a high-purity SOS hard butter prepared by the above method.
- SOS 1,3-distaroyl-2-oleoylglycerin
- Another object of the present invention to provide a chocolate containing a high-purity SOS hard butter prepared by the above method.
- the oil-fat fraction of the high melting point is removed by crystallization, and then further lowered the temperature
- Obtaining a crystallized solid makes it possible to produce high purity SOS hard butter with an SOS content of at least 85 w / w%.
- SOS 1,3-distaroyl-2-oleoylglycerin
- the raw material fats and oils can be used to carry out the enzyme transesterification of vegetable fats and oils.
- the vegetable oil is preferably an oleic acid content of 80% or more, typically high oleic sunflower oil.
- the enzyme transesterification can be carried out by reacting vegetable oil with stearic ethyl ester in the presence of an enzyme having specificity at the sn-1,3 position.
- Enzymes having specificity at the sn-1,3 position include enzymes isolated from Rhizopus delemar, Mucor miehei, Aspergilillus miger, Rhizopus arrhizus, Rhizopus niveus, Mucor javanicus, Rhizopus javenicus, Rhizopus oxyzae , but are not limited thereto.
- the product obtained through the enzymatic transesterification reaction may be distilled at 0.1 ⁇ 0.2 mmHg, 200 ⁇ 250 °C to remove the ethyl ester to the triglyceride (Triacylglyceride, TAG) content of 98% or more.
- Triglycerides from which the ethyl ester is removed by the enzymatic transesterification and distillation have a smaller variation in quality in the SOS content than the oils naturally containing SOS, thereby providing a consistent product.
- the fats and oils carrying out the enzymatic transesterification reaction are economically advantageous since the by-product can be reused as a substrate of the enzymatic transesterification reaction.
- vegetable oils and fats can be used as raw material oils having a higher SOS content by a transesterification reaction, so that the yield of SOS hard butter can be increased.
- the solvent is capable of dissolving the raw material fat and oil is not particularly limited, for example, acetone, n-hexane, methyl ethyl ketone, ethanol, or a mixture thereof may be used.
- the fat or oil solution may be prepared to contain at least 25 w / w% of raw fat or oil, and it is desirable to increase the amount of the raw fat or oil dissolved in the solvent as much as possible.
- the solvent fractionation method may be performed using a device commonly used in the art, for example, a double jacket reactor.
- the step of crystallizing and removing the high melting point fraction may leave the oil solution at 10-25 ° C. until crystallization of the oil is achieved, and may be performed for about 2-5 hours. If crystallization is sufficient, the solid phase can be separated from the liquid phase to remove the high melting point fraction with a reduced pressure filter. The liquid phase from which the solid phase has been separated is then put back into the reactor for dissolution and then left to stand at 0-15 ° C. until crystallization of the fat or oil is achieved, for example for about 10-15 hours.
- the solid phase is separated from the liquid phase to give a solid phase.
- the solid phase thus obtained contains 85% or more of SOS as the fat or oil at the melting point.
- the solvent fractionation method can produce a high purity SOS hard butter by a fractionation method at room temperature, which is not extremely low temperature, thereby reducing the work time and cost for manufacturing the hard butter. It can be said that it is very economical way.
- the SOS hard butter prepared by the solvent fractionation method is used to prepare chocolates having good meltability as a maintenance of the melting point, and can be used to prepare chocolates having excellent palatability, and can be manufactured at low cost. It can be used for the production of phosphorus chocolate.
- the SOS hard butter prepared by the solvent fractionation method may exhibit a physical property similar to that of cocoa butter by using a mixture of natural fats or oils and fractions thereof, for example, Hard Palm Middle Fraction (HPMF).
- HPMF Hard Palm Middle Fraction
- the SOS hard butter prepared by the solvent fractionation method can be used as a fat or oil for the manufacture of chocolates with natural fats or oils and fats thereof.
- the present invention provides a chocolate comprising a hard butter prepared by the method according to the present invention.
- the chocolate refers to processed by adding other foods or food additives to the cocoa raw material obtained from the seed of Theobroma cacao tree.
- the chocolates include chocolate, milk chocolate, semi-chocolate and chocolate processed products.
- Chocolate is processed by adding sugars, fats and oils, dairy products, foods or food additives to cocoa raw materials, and refers to a cocoa raw material content of 20% or more (cocoa butter 10% or more).
- Milk chocolate is processed by adding sugars, fats and oils, dairy products, foods or food additives to cocoa raw materials, and refers to cocoa raw material content of 12% or more and milk solids of 8% or more.
- Processed chocolate refers to processed chocolate, milk chocolate or semi-chocolate with processed foods such as nuts, candies and biscuits by mixing, coating, filling and bonding.
- the preparation of such chocolates may be prepared according to conventional methods known in the art, and the hard butter prepared by the method according to the present invention may be used as a fat or oil component for preparing chocolates, If necessary, the mixture may be used in combination with a natural fat or oil.
- the hard butter prepared by the method according to the present invention can be produced chocolates with high added value, such as reducing the chocolate manufacturing cost and increasing the hard properties.
- a high-purity SOS hard butter of SOS 85% or more can be manufactured by a solvent fractionation method at room temperature, thereby reducing the operating time and reducing the process cost compared to the conventional method. It can be said.
- the hard butter prepared according to the method of the present invention can be used to exhibit properties similar to cocoa butter by mixing with natural fats or fractions thereof, for example, Hard Palm Middle Fraction (HPMF). have.
- the hard butter prepared according to the method of the present invention may be suitably mixed with natural fats or oils and fats thereof as necessary to be used as fats and oils in the manufacture of chocolate.
- FIG. 1 is a graph showing the results of confirming the triglyceride composition in the holding by HPLC for the holding after the enzyme transesterification reaction according to an embodiment of the present invention.
- Figure 2 is a graph showing the result of checking the triglyceride composition in the holding by HPLC for the final melting point obtained after fractionation with acetone according to an embodiment of the present invention.
- Figure 3 is a graph showing the results of the triglyceride composition in the holding by HPLC for the final melting point obtained after fractionation with hexane according to an embodiment of the present invention.
- Figure 4 is a graph showing the results of analyzing the solid paper content using nuclear magnetic resonance for the final melting point obtained after fractionation using acetone according to an embodiment of the SOS hard butter manufacturing method of the present invention.
- the retention yield of the filtered liquid phase was more than 98% and the liquid phase was completely dissolved at 60 ° C. in a double jacketed reactor to obtain a medium melting point retention.
- About 15 ° C. refrigerant was flowed into the reactor for about 10 hours and stirred at 30 rpm for separation of the low melting point and the middle melting point. Thereafter, the liquid phase and the solid phase were separated by filtration under reduced pressure, and acetone was distilled off under reduced pressure to obtain a middle melting point of the solid phase (weight: 255 g, total yield 25.5%, SOS yield 82%).
- Example 1 the high molecular weight sunflower oil and stearic ethyl ester (Stearic ethyl ester), Lipozyme RMIM (immobilized sn-1,3-specific lipase from Rhizomucor) miehei) to make the SOS content more than 25 w / w%.
- Synthetic fats and oils were distilled at 0.001 mbar, 230 °C to remove the ethyl ester and triglycerides (Triacylglyceride, TAG) is more than 98%.
- the retention yield of the filtered liquid phase was more than 98% and the liquid phase was completely dissolved at 60 ° C. in a double jacketed reactor to obtain a medium melting point retention.
- a 5 ° C. refrigerant was flowed into the reactor for about 10 hours and stirred at 30 rpm for separation of the low melting point and the middle melting point. Thereafter, the liquid phase and the solid phase were separated by filtration under reduced pressure, and n-hexane was distilled off under reduced pressure to obtain a solid melting point retention (weight: 250 g, total yield 25%, SOS yield 79%).
- Enzymatic transesterification changes the structure of triglycerides, which determine the physical and chemical properties of fats and oils. Therefore, in Example 1, the type and content of triglycerides in the fats and oils were confirmed using HPLC for the fats and oils before and after the enzyme transesterification reaction.
- Triglyceride analysis conditions using HPLC were carried out under the conditions shown in Table 1.
- Triglyceride structures of the fats before and after fractionation were analyzed using a reversed phase high resolution liquid chromatography-vaporized light scattering detector system.
- 30 ⁇ l of sample and 10 ml of hexane were added, filtered using a PEFE syringe filter (25 mm, 0.2 ⁇ m), and then 20 ⁇ l of the sample was injected into a 2 mm vial using an autosampler.
- Acetonitrile (solvent A) and hexane / isopropanol (solvent B) were used as a solvent, and the flow rate was 1 ml / min.
- the gradient elution (A: B, v: v) of the solvent was maintained at 80:20 for 45 minutes, changed to 54:46 until 60 minutes, and then maintained at 80:20 from 60 minutes to 70 minutes. It was 70 minutes.
- Figures 1 to 3 show triglycerides in fats and oils using HPLC for the fats before and after the enzyme transesterification (FIG. 1) and after the acetone fractionation of Example 1 (FIG. 2) and after the hexane fractionation of Example 2 (FIG. 3). It is the graph which showed the result of having confirmed a composition. According to the graph of Figure 1, the SOS content before fractionation as 13.5%, SOO 40.4%, SOS 26.7% was confirmed to be 26.7%. According to the graph of Figure 2 SOO 2.5%, POS 6.5%, SOS 86.5% SOS content after fractionation can be seen that about 60% increase.
- Solid fat content was analyzed using nuclear magnetic resonance for maintaining the melting point of the solid phase obtained in Example 1. Nuclear magnetic resonance analysis conditions for solid fat content analysis are shown in Table 2 below.
- the solid fat content analysis test using nuclear magnetic resonance was carried out in a parallel method. After acetone fractionation, 5 samples of 3 mL each were prepared. After pre-treatment of the experiment, the solution was sufficiently dissolved at 80 ° C., and then cooled at 60 ° C. for 10 minutes and 0 ° C. for 90 minutes. Thereafter, the crystals were stabilized at 26 ° C. for 40 hours, and then cooled at 0 ° C. for 90 minutes. Samples were measured after standing for 30 minutes in a Celsius bath-metal block thermostat preset at 10.0 ° C, 20.0 ° C, 25.0 ° C, 30.0 ° C, and 35.0 ° C. The measurement time of the sample was about 6 seconds.
- FIG. 4 shows the results of analyzing the solid support content using nuclear magnetic resonance for maintaining the melting point of the solid phase obtained in Example 1.
- Such high solid paper content may serve to solidify the properties of the fats and oils by mixing with lower fat papers or natural fats or oils and fractions thereof.
- Differential calorimetry can measure the melting profile (melting profile) before and after solvent fractionation, it can be seen whether the fraction of the high melting point, low melting point has been removed. DSC profiles were measured for retention of the melting point of the solid phase finally obtained by acetone fractionation in Example 1.
- the SOS hard butter has a low temperature melting portion that melts from 15 ° C to 26 ° C and a high temperature melting portion that melts from 26 ° C to 40 ° C.
- the crystal to form it can be seen that it shows the characteristics that the crystal is formed from 19 °C to 7 °C. From these results, it is possible to develop fats and oils showing desired physical properties by adjusting the mixing ratio of SOS hard butter in consideration of the characteristics of melting and crystallization of natural fats or fractions.
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Abstract
Description
기기명 | 애질런트(Agilent), 1200 HPLC Chemstation |
칼럼 | NOVA-pack C18 60Å 4㎛ (3.9 x 150mm, Waters) |
검출기 | 알텍(Alltech), ELSD(Evaporative Light Sacttering Detector) |
샘플 양 | 20 ㎕ |
용매 | 아세토나이트릴 : 헥산/ 이소프로필알콜 기울기 용매 시스템 사용 |
검출기 gain | 1 |
검출기 오븐온도 | 80℃ |
운반기체 | N2 (1.5L/min) |
NMR 기기명 | 브루커 (BRUKER), the minispec |
Frequenzy (진동수) | 60㎒ |
샘플 양 | 3 ㎖ |
전처리 온도 | 100 metal block thermostat, 0℃ |
실험 온도 | 10.0℃, 20.0℃, 25.0℃, 30.0℃, 35.0℃ |
DSC 기기명 | TA Q20 |
실험 온도 | -60 내지 80℃ |
냉각 속도 | 10℃/min (-80℃ 까지) |
승온 속도 | 5℃/min (100℃까지) |
샘플 양 | 15±5mg |
Claims (7)
- 원료 유지를 용제에 용해시켜 유지 용액을 제조하는 단계;상기 유지 용액을 10 내지 25℃로 유지하여 고융점 분획을 결정화하여 제거하는 단계; 및상기 고융점 분획이 제거된 유지 용액을 0 내지 15 ℃로 유지하여 중융점 분획을 결정화하여 수득하는 단계를 포함하는,용제분별법에 의해 트리글리세라이드 중 1,3-디스테아로일-2-올레오일글리세린(SOS)를 85 w/w% 이상 함유하는 SOS 하드버터를 제조하는 방법.
- 제 1 항에 있어서, 상기 원료 유지는 올레인산을 80% 이상 함유한 식물성 유지와 스테아릭 에틸 에스테르를 sn-1,3 위치에 특이성을 지닌 효소를 이용하여 에스테르 교환 반응을 한 후 에스테르를 제거하여 트리글리세라이드로 한 것임을 특징으로 하는 방법.
- 제 2 항에 있어서, 상기 원료 유지는 하이올레익 해바라기유인 것을 특징으로 하는 방법.
- 제 2 항에 있어서, 상기 에틸 에스테르의 제거는 0.001~0.1 mbar, 200~250℃에서 수행하는 것을 특징으로 하는 방법.
- 제 1 항에 있어서, 상기 용제는 헥산, 아세톤, 메틸 에틸 케톤, 에탄올, 또는 이들의 혼합물인 것을 특징으로 하는 방법.
- 제 1 항에 있어서, 상기 유지 용액을 제조하는 단계에서 유지 용액은 원료 유지를 25 w/w% 이상 함유하도록 제조되는 것을 특징으로 하는 방법.
- 제 1 항 내지 제 6 항 중 어느 한 항에 따른 방법에 의해 제조된 SOS 하드버터를 포함하는 초콜릿류.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP09849870A EP2484216A1 (en) | 2009-09-28 | 2009-10-28 | Production method for hard butter |
SG2012004941A SG178826A1 (en) | 2009-09-28 | 2009-10-28 | Production method for hard butter |
CN2009801616643A CN102548420A (zh) | 2009-09-28 | 2009-10-28 | 硬脂的制造方法 |
JP2012515958A JP5589071B2 (ja) | 2009-09-28 | 2009-10-28 | ハードバターの製造方法 |
RU2012102253/13A RU2511238C2 (ru) | 2009-09-28 | 2009-10-28 | Способ получения твердого масла |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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KR10-2009-0091779 | 2009-09-28 | ||
KR1020090091779A KR101075559B1 (ko) | 2009-09-28 | 2009-09-28 | 하드버터의 제조방법 |
Publications (1)
Publication Number | Publication Date |
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WO2011037296A1 true WO2011037296A1 (ko) | 2011-03-31 |
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PCT/KR2009/006249 WO2011037296A1 (ko) | 2009-09-28 | 2009-10-28 | 하드버터의 제조방법 |
Country Status (7)
Country | Link |
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EP (1) | EP2484216A1 (ko) |
JP (1) | JP5589071B2 (ko) |
KR (1) | KR101075559B1 (ko) |
CN (1) | CN102548420A (ko) |
RU (1) | RU2511238C2 (ko) |
SG (1) | SG178826A1 (ko) |
WO (1) | WO2011037296A1 (ko) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014016250A1 (en) * | 2012-07-24 | 2014-01-30 | Advanta International Bv | 1,3-specific intraesterification |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101344491B1 (ko) | 2011-11-04 | 2014-01-16 | 롯데푸드 주식회사 | 카카오 버터 대용지 또는 카카오 버터 특성 향상제용 유지조성물의 제조방법 |
MY160097A (en) * | 2013-02-13 | 2017-02-28 | Malaysian Palm Oil Board | A process to produce high oleic liquid palm oil fraction |
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MY142954A (en) * | 2005-05-13 | 2011-01-31 | Nisshin Oillio Group Ltd | Intermolecular compounds of fatty acid triglycerides |
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- 2009-09-28 KR KR1020090091779A patent/KR101075559B1/ko active IP Right Grant
- 2009-10-28 EP EP09849870A patent/EP2484216A1/en not_active Withdrawn
- 2009-10-28 CN CN2009801616643A patent/CN102548420A/zh active Pending
- 2009-10-28 RU RU2012102253/13A patent/RU2511238C2/ru active
- 2009-10-28 WO PCT/KR2009/006249 patent/WO2011037296A1/ko active Application Filing
- 2009-10-28 SG SG2012004941A patent/SG178826A1/en unknown
- 2009-10-28 JP JP2012515958A patent/JP5589071B2/ja active Active
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US4104288A (en) * | 1975-11-19 | 1978-08-01 | Fuji Oil Company, Limited | Method for producing hard butter fraction from shea fat |
US4108879A (en) * | 1977-01-20 | 1978-08-22 | Asahi Denka Kogyo K.K. | Hard butter |
KR950015109B1 (ko) * | 1992-03-11 | 1995-12-22 | 유니레버 엔 브이 | 하드스톡 지방 첨가물을 기본으로 한 개량된 초콜렛 조성물 |
KR20070117538A (ko) * | 2005-03-08 | 2007-12-12 | 후지 세유 가부시키가이샤 | 내열성 필링류 및 그 제조법 |
WO2009031679A1 (ja) * | 2007-09-07 | 2009-03-12 | The Nisshin Oillio Group, Ltd. | ハードバターの製造方法 |
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WO2014016250A1 (en) * | 2012-07-24 | 2014-01-30 | Advanta International Bv | 1,3-specific intraesterification |
US9795152B2 (en) | 2012-07-24 | 2017-10-24 | Advanta Holdings Bv | 1,3-specific intraesterification |
RU2635696C2 (ru) * | 2012-07-24 | 2017-11-15 | Эдванта Интернэшнл Бв | 1,3-селективная переэтерификация |
Also Published As
Publication number | Publication date |
---|---|
SG178826A1 (en) | 2012-04-27 |
JP5589071B2 (ja) | 2014-09-10 |
RU2511238C2 (ru) | 2014-04-10 |
KR20110034295A (ko) | 2011-04-05 |
EP2484216A1 (en) | 2012-08-08 |
KR101075559B1 (ko) | 2011-10-20 |
RU2012102253A (ru) | 2013-11-10 |
CN102548420A (zh) | 2012-07-04 |
JP2012529907A (ja) | 2012-11-29 |
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