WO2024048702A1 - ランダムエステル交換油 - Google Patents
ランダムエステル交換油 Download PDFInfo
- Publication number
- WO2024048702A1 WO2024048702A1 PCT/JP2023/031705 JP2023031705W WO2024048702A1 WO 2024048702 A1 WO2024048702 A1 WO 2024048702A1 JP 2023031705 W JP2023031705 W JP 2023031705W WO 2024048702 A1 WO2024048702 A1 WO 2024048702A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- mass
- oil
- content
- fat
- fatty acids
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings or cooking oils characterised by the production or working-up
-
- 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 random transesterified oil.
- chocolates are often used in combination with sweets and breads, and are used in a wide variety of food products. Depending on the type of use, the functions required of chocolates vary.
- Patent Document 1 In a situation where oils and fats with low trans fatty acids are desired, a method of blending seeding agents and emulsifiers into existing low melting point oils and fats has been disclosed (Patent Document 1, Patent Document 2). However, none of these methods improves fats and oils, but rather improves the crystallinity when added to chocolate when added to chocolate.
- JP 2021-153438 Publication International Publication No. 2019/194081 Japanese Patent Application Publication No. 2018-171001 Japanese Patent Application Publication No. 2018-171002
- Patent Document 3 and Patent Document 4 disclose low trans fatty acid fats and oils whose crystalline properties have been improved by transesterification. Although it has sharp melting properties in the mouth similar to cocoa butter, the disclosed fat alone is a little hard for use in soft chocolates.
- the present inventors have considered the problems that occur in soft chocolates that use oils and fats with low trans fatty acids. If an oil or fat with a lower melting point than cocoa butter is blended, the oil or fat with a relatively high melting point, such as cacao butter, will crystallize, creating grainy granular oil crystals or a coarse texture with a crumbly texture. A phenomenon called graining may occur. Recognizing such prior art, it is an object of the present invention to provide a low trans fatty acid fat or oil that reduces graining in chocolates.
- the present inventors have made extensive studies and found that the content of saturated fatty acids having 12 to 18 carbon atoms is 20% by mass or more in the constituent fatty acid composition, and Random transesterified oil in which Y/X is 0.2 or more and 1.0 or less, where X is the content of saturated fatty acids with 12 to 18 carbon atoms and Y is the content of saturated fatty acids with 12 to 14 carbon atoms.
- Y/X is 0.2 or more and 1.0 or less
- the present invention includes the following contents.
- A) The content of saturated fatty acids with 12 to 18 carbon atoms in the constituent fatty acid composition is 20% by mass or more.
- B) The content of saturated fatty acids with 12 to 18 carbon atoms in the constituent fatty acid composition is X, and the content of saturated fatty acids with 12 to 18 carbon atoms is When the content of saturated fatty acids in No. 14 is Y, Y/X is 0.2 or more and 1.0 or less
- Chocolates containing 5% to 97% by mass of oil (8)
- the fat content in the chocolate is 10% by mass to 70% by mass, the fat content in the chocolate is 3% by mass to 40% by mass, and the random transesterification of (3) or (4) Chocolates containing 5% to 97% by mass of oil.
- a method for suppressing graining of chocolate characterized by using the random transesterified oil according to (1) or (2).
- (10) A method for suppressing graining of chocolate, characterized by using the random transesterified oil of (3) or (4).
- (11) A method for producing a random transesterified oil, which comprises blending raw material oils and fats to obtain a random transesterified oil that satisfies (A) and (B) below.
- the content of saturated fatty acids having 12 to 18 carbon atoms in the constituent fatty acid composition is 20% by mass or more.
- the content of saturated fatty acids having 12 to 18 carbon atoms in the constituent fatty acid composition is X, and the content of saturated fatty acids having 12 to 18 carbon atoms is When the content of saturated fatty acids in No. 14 is Y, Y/X is 0.2 or more and 1.0 or less (12)
- the raw material fat for random transesterification contains the following fat material a and fat material b, (11 ) method for producing random transesterified oil.
- Oil and fat raw material a Vegetable oil and fat with an iodine value of 50 to 150
- Oil and fat raw material b Lauric oil and fat
- the present invention it is possible to provide fats and oils that suppress the occurrence of graining in chocolates.
- oils and fats that can be used in the random transesterified oil of the present invention include soybean oil, high erucine rapeseed oil, rapeseed oil, corn oil, cottonseed oil, peanut oil, sunflower oil, high oleic sunflower oil, rice bran oil, safflower oil, high oleic safflower oil, Vegetable oils and fats such as olive oil, sesame oil, palm oil, coconut oil, palm kernel oil, medium-chain fatty acid-bound fats and oils (MCT), shea butter, monkey fat, and cacao butter; animal fats and oils such as milk fat, beef tallow, and pork tallow; , their hardened oils, fractionated oils, hardened fractionated oils, fractionated hardened oils, processed oils and fats subjected to transesterification, and mixed oils thereof.
- soybean oil high erucine rapeseed oil, rapeseed oil, corn oil, cottonseed oil, peanut oil, sunflower oil, high oleic sunflower oil, rice bran
- chocolate can be produced without using partially hydrogenated oil containing a relatively large amount of trans fatty acids.
- the erucic acid content contained in the high erucic acid rapeseed oil is 30 mass % or more in the constituent fatty acid composition.
- the random transesterified oil of the present invention satisfies the following (A) and (B).
- (A) The content of saturated fatty acids with 12 to 18 carbon atoms in the constituent fatty acid composition is 20% by mass or more.
- (B) The content of saturated fatty acids with 12 to 18 carbon atoms in the constituent fatty acid composition is X, and the content of saturated fatty acids with 12 to 18 carbon atoms is When the content of 14 saturated fatty acids is Y, Y/X is 0.2 or more and 1.0 or less
- the content of saturated fatty acids having 12 to 18 carbon atoms is 20% by mass or more, preferably 20% by mass or more and 50% by mass or less, more preferably 20% by mass or more and 45% by mass or less, More preferably, it is 20% by mass or more and 40% by mass or less.
- Y/X is 0.2 or more and 1 .0 or less, preferably 0.2 or more and 0.8 or less, more preferably 0.2 or more and 0.7 or less.
- the random transesterified oil of the present invention has an unsaturated fatty acid content of 50% by mass or more and 80% by mass or less, preferably 52% by mass or more and 80% by mass or less, more preferably 52% by mass or more and 80% by mass or less in the (C) constituent fatty acid composition. is 55% by mass or more and 80% by mass or less.
- the random transesterified oil of the present invention has a content of saturated fatty acids having 12 to 14 carbon atoms in the constituent fatty acid composition (D) of 5% by mass or more and 30% by mass or less, preferably 5% by mass or more and 27% by mass. % or less, more preferably 5% by mass or more and 25% by mass or less, even more preferably 6% by mass or more and 23% by mass or less.
- the trans fatty acid content in the constituent fatty acid composition is preferably 5% by mass or less, more preferably 3% by mass or less, even more preferably 2% by mass or less, and most preferably 1% by mass or less. It is.
- random transesterification methods include methods using enzymes or metal catalysts (eg, sodium methylate).
- Oil and fat raw material a Vegetable oil and fat with an iodine value of 50 to 150
- Oil and fat raw material b Lauric oil and fat
- vegetable oils and fats with an iodine value of 50 to 150 used as oil and fat raw material a include soybean oil, rapeseed oil, corn oil, cottonseed oil, peanut oil, sunflower oil, rice bran oil, safflower oil, olive oil, palm olein, Examples include shea olein, and preferred are soybean oil, rapeseed oil, corn oil, cottonseed oil, sunflower oil, rice bran oil, and safflower oil with an iodine value of 70 to 145.
- the lauric oil used as the oil raw material b is an oil containing a large amount of lauric acid, which is a saturated fatty acid having 12 carbon atoms, and specifically includes coconut oil, palm kernel oil, and Examples include those hardened oils, fractionated oils, hardened fractionated oils, fractionated hardened oils, and mixed oils thereof.
- the random transesterified oil of the present invention can be suitably used for chocolates.
- chocolates are not limited to chocolate, quasi-chocolate, and chocolate-based foods defined by the National Chocolate Industry Fair Trade Council and the Chocolate-based Food Fair Trade Council, and include oils and fats as an essential ingredient. It also includes processed oil and fat foods that use cacao mass, cocoa, cacao butter, cacao butter substitutes, hard butter, etc. as ingredients, and is manufactured through general chocolate manufacturing processes.
- oils and fats derived from cacao components and milk components, non-tempering hard butter, and other oils and fats can be combined and the blending amount can be adjusted appropriately to create products suitable for various uses. Chocolates can be made.
- the fat content in the chocolate using the random transesterified oil of the present invention is 10% by mass to 70% by mass, and the fat content in the chocolate contains 3% by mass to 40% by mass of cocoa butter. and random transesterified oil in an amount of 5% to 97% by mass.
- fats and oils include fats derived from cacao raw materials such as cacao mass and cocoa powder (cocoa butter), as well as fats derived from raw materials blended into chocolates.
- the fat and oil content in chocolate is more preferably 20% by mass to 60% by mass.
- the amount of the random transesterified oil of the present invention used is preferably 8% by mass to 90% by mass, and even more preferably 10% by mass to 70% by mass, in the fat and oil content of chocolates.
- the random transesterified oil of the present invention is less than 5% by mass, the effects of the present invention may not be obtained or the texture required for chocolates may not be obtained.
- the content of cocoa butter in the chocolates is more preferably 5% by mass to 40% by mass in the fats and oils in the chocolates.
- the content of cocoa butter includes fat (cocoa butter) derived from cocoa raw materials such as cocoa mass and cocoa powder.
- chocolates using the random transesterified oil of the present invention are preferably soft chocolates.
- Soft chocolates refer to chocolates that do not have the good snap properties required of common chocolates and have plasticity at room temperature.
- graining refers to grainy granular oil crystals or a coarse texture and crumbly texture that occurs in stored chocolates. Graining is assumed to occur when fats and oils with a relatively high melting point, such as cocoa butter, crystallize when blended with fats and oils that have a lower melting point than cocoa butter, and are caused by the influence of the fats and oils contained in chocolate. is large, and the quality of graining in chocolate can be evaluated by evaluating graining with fats and oils.
- the method for producing chocolates using the random transesterified oil of the present invention can be carried out in the same manner as for producing general chocolates.
- the random transesterified oil of the present invention is essential, and other raw materials such as oils and fats, sugars, cacao mass, cacao butter, cocoa powder, various powdered foods such as powdered milk, emulsifiers, fragrances, and pigments are selected as appropriate. It can be mixed, rolled and conched.
- other general chocolate manufacturing methods such as mixing and atomization using a ball mill, bead mill, etc. can be used.
- emulsifiers that are normally used in the production of chocolates can be used.
- examples include polyglycerin fatty acid ester, sucrose fatty acid ester, organic acid monoglycerin fatty acid ester, polysorbate, and polyglycerin condensed ricinoleic acid ester. These may be used in combination of two or more types.
- Chocolate was produced according to the formulation shown in Table 1. (Unit/parts by mass) Note that the chocolate preparation conditions were in accordance with a known method. That is, appropriate amounts of oil and lecithin were added to cocoa powder, cacao mass, lactose, and sugar, and mixed with a mixer while heating to prepare a dough. This dough is processed using a roll refiner (Three-rollmill SDY300 manufactured by BUHLER). The mixture was atomized to a particle size of approximately 20 ⁇ m, the remaining oil and fat and lecithin were added thereto, and the mixture was uniformly kneaded using a conching machine (Conche) to obtain chocolate. Note that a micrometer was used to measure the particle size.
- the fat (cocoa butter) content in the cocoa powder used was calculated as 11% by mass, and the fat (cocoa butter) content in the cocoa mass was calculated as 55%.
- the fat and oil content in the chocolate was 40.2% by mass. Rapeseed oil was used as the studied oil.
- the fractionated middle melting point part obtained was decolorized/deodorized according to a conventional method to obtain fats and oils H (iodine value: 33.0 ),
- the obtained fractionated low melting point portion was decolorized/deodorized according to a conventional method to obtain fats and oils I (iodine value: 65.0).
- Table 3 shows the results of analyzing the fatty acid composition of random transesterified oils 1 to 14 according to the fatty acid composition analysis method described above.
- the fatty acid compositions of fats and oils A and B are also described.
- the content (%) of saturated fatty acids having 12 to 18 carbon atoms is X
- the content (%) of saturated fatty acids having 12 to 14 carbon atoms is Y
- the calculated values are described.
- the total amount of unsaturated fatty acids was indicated as Z.
- the following oils and fats A and B were used.
- Fat A Rapeseed oil
- Fat B Palm super olein (iodine value 67)
- the fatty acid composition of the random transesterified oil was evaluated using the following numerical values.
- X Content of saturated fatty acids having 12 to 18 carbon atoms in the constituent fatty acid composition is 20% by mass or more
- Y Content of saturated fatty acids having 12 to 14 carbon atoms in the constituent fatty acid composition is 5% by mass or more and 30% by mass or less
- Y/X 0.2 or more and 1.0 or less
- Z In the constituent fatty acid composition, the content of unsaturated fatty acids is 50% by mass or more and 80% by mass or less
- Random transesterified oils 4 to 6 and 9 to 14 which obtained good evaluation results, contain the following fat and oil raw material a and fat raw material b in the raw material fat, in addition to the above-mentioned composition.
- Oil and fat raw material a Vegetable oil and fat with an iodine value of 50 to 150
- Oil and fat raw material b Lauric oil and fat
- chocolate using the random transesterified oil of the present invention was evaluated.
- chocolate was produced according to the formulations listed in Table 1 in the same manner as above, and evaluated in the same manner as described above (method for evaluating chocolate graining). Graining was evaluated according to the evaluation criteria. The evaluation results are shown in Table 6.
- chocolate was similarly prepared and evaluated using the fat and oil A. The chocolates were formulated to contain 8% by mass of cocoa butter and 92% by mass of the studied fats and oils.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Confectionery (AREA)
- Edible Oils And Fats (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020257009160A KR20250057821A (ko) | 2022-09-02 | 2023-08-31 | 랜덤 에스테르 교환유 |
| JP2024513533A JP7491487B1 (ja) | 2022-09-02 | 2023-08-31 | ランダムエステル交換油 |
| EP23860464.9A EP4581935A4 (en) | 2022-09-02 | 2023-08-31 | RANDOM TRANSESTERIZED OIL |
| JP2024071754A JP2024094418A (ja) | 2022-09-02 | 2024-04-25 | ランダムエステル交換油 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022140176 | 2022-09-02 | ||
| JP2022-140176 | 2022-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2024048702A1 true WO2024048702A1 (ja) | 2024-03-07 |
Family
ID=90099795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2023/031705 Ceased WO2024048702A1 (ja) | 2022-09-02 | 2023-08-31 | ランダムエステル交換油 |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP4581935A4 (https=) |
| JP (2) | JP7491487B1 (https=) |
| KR (1) | KR20250057821A (https=) |
| WO (1) | WO2024048702A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2025182962A1 (ja) * | 2024-02-29 | 2025-09-04 | 不二製油株式会社 | チョコレート類 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015192651A (ja) * | 2014-03-28 | 2015-11-05 | 不二製油株式会社 | ベーカリー製品用チョコレート類及びベーカリー製品の製造法 |
| JP2016002015A (ja) * | 2014-06-16 | 2016-01-12 | 日清オイリオグループ株式会社 | チョコレート |
| JP2018171001A (ja) | 2017-03-31 | 2018-11-08 | 不二製油株式会社 | エステル交換油脂 |
| JP2018171002A (ja) | 2017-03-31 | 2018-11-08 | 不二製油株式会社 | エステル交換油脂 |
| JP2019068771A (ja) * | 2017-10-10 | 2019-05-09 | 不二製油株式会社 | チョコレート用油脂 |
| WO2019194081A1 (ja) | 2018-04-02 | 2019-10-10 | 日清オイリオグループ株式会社 | ソフトチョコレート |
| JP2021153438A (ja) | 2020-03-26 | 2021-10-07 | 日清オイリオグループ株式会社 | ソフトチョコレート |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013132284A1 (en) * | 2012-03-09 | 2013-09-12 | Cruz Adriana Fernanda | Cocoa butter substitute |
| US20180352827A1 (en) * | 2016-03-31 | 2018-12-13 | Fuji Oil Holdings Inc. | Fat composition for low-trans fat, non-tempered chocolate and chocolate |
| JP2021040501A (ja) * | 2019-09-09 | 2021-03-18 | 株式会社カネカ | ノーテンパリング型ハードバター用保存安定性向上剤 |
-
2023
- 2023-08-31 KR KR1020257009160A patent/KR20250057821A/ko active Pending
- 2023-08-31 EP EP23860464.9A patent/EP4581935A4/en active Pending
- 2023-08-31 WO PCT/JP2023/031705 patent/WO2024048702A1/ja not_active Ceased
- 2023-08-31 JP JP2024513533A patent/JP7491487B1/ja active Active
-
2024
- 2024-04-25 JP JP2024071754A patent/JP2024094418A/ja active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015192651A (ja) * | 2014-03-28 | 2015-11-05 | 不二製油株式会社 | ベーカリー製品用チョコレート類及びベーカリー製品の製造法 |
| JP2016002015A (ja) * | 2014-06-16 | 2016-01-12 | 日清オイリオグループ株式会社 | チョコレート |
| JP2018171001A (ja) | 2017-03-31 | 2018-11-08 | 不二製油株式会社 | エステル交換油脂 |
| JP2018171002A (ja) | 2017-03-31 | 2018-11-08 | 不二製油株式会社 | エステル交換油脂 |
| JP2019068771A (ja) * | 2017-10-10 | 2019-05-09 | 不二製油株式会社 | チョコレート用油脂 |
| WO2019194081A1 (ja) | 2018-04-02 | 2019-10-10 | 日清オイリオグループ株式会社 | ソフトチョコレート |
| JP2021153438A (ja) | 2020-03-26 | 2021-10-07 | 日清オイリオグループ株式会社 | ソフトチョコレート |
Non-Patent Citations (2)
| Title |
|---|
| "JOCS Standard Methods for the Analysis of Fats, Oils and Related Materials", 1996, JAPAN OIL CHEMISTS' SOCIETY, article "2.4.1.2 Methyl Esterification Method (Boron Trifluoride-Methanol Method" |
| See also references of EP4581935A4 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2025182962A1 (ja) * | 2024-02-29 | 2025-09-04 | 不二製油株式会社 | チョコレート類 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP4581935A1 (en) | 2025-07-09 |
| JP7491487B1 (ja) | 2024-05-28 |
| JP2024094418A (ja) | 2024-07-09 |
| JPWO2024048702A1 (https=) | 2024-03-07 |
| KR20250057821A (ko) | 2025-04-29 |
| EP4581935A4 (en) | 2025-12-24 |
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