WO2001001787A2 - Water-in-oil type emulsified fat and/or oil composition - Google Patents
Water-in-oil type emulsified fat and/or oil composition Download PDFInfo
- Publication number
- WO2001001787A2 WO2001001787A2 PCT/JP2000/004359 JP0004359W WO0101787A2 WO 2001001787 A2 WO2001001787 A2 WO 2001001787A2 JP 0004359 W JP0004359 W JP 0004359W WO 0101787 A2 WO0101787 A2 WO 0101787A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil
- water
- composition
- fat
- fatty acid
- Prior art date
Links
Classifications
-
- 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
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
- A23D7/0053—Compositions other than spreads
-
- 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
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
- A23D7/0056—Spread compositions
-
- 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
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/01—Other fatty acid esters, e.g. phosphatides
- A23D7/011—Compositions other than spreads
-
- 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
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/01—Other fatty acid esters, e.g. phosphatides
- A23D7/013—Spread compositions
Definitions
- the present invention relates to a water-in-oil type emulsified fat and/or oil composition which comprises a diglyceride and which is excellent in a flavor release during the time for ingestion thereof.
- the water-in-oil type emulsified fat and/or oil composition of the present invention is preferably and suitably utilized in a margarine, a fat spread, a butter cream, a shortening, etc.
- Diglyceride has been revealed to be a fat or oil, after which is eaten, which hardly increases the concentration of a neutral fat in blood and hardly constitutes a body fat (JP-A 10-176181) . Therefore, the diglyceride is expected to be used as the substitution of a conventional fat or oil in a (water-in-oil emulsion) food having a large amount of the fat or oil such as a cooking oil, in particular, a margarine and a spread.
- the present inventors have further continued in the investigation of the water-in-oil type emulsified fat and/or oil composition. As the result, they found the problem that the foods containing diglycerides in the high concentration during the time for ingestion and the foods are not good in flavor release related directly to the degree of good taste thereof. This phenomenon is not observed in a fat and/or oil being mainly based on a triglyceride.
- the present inventors have found that in a system of the water-in-oil type emulsion containing diglycerides in the high concentration, emulsification is so stable that the rate of the phase reversal of the emulsion from W/O type to O/W type in the mouth delays, thus affecting much of the flavor release.
- the present invention provides a water-in-oil type emulsified fat and/or oil composition which is c ⁇ rposed of (1) the aqueous phase based on water and (2) the oil phase of fat and/or oil comprising 15 % by weight or more, based on the total oils and fats, of diglycerides, and the composition including a flavor component (s) , 30 % by weight or more of the said emulsified composition being able to be reversed in phase within one minute after it has been introduced into water at 36 C° .
- the fat(s) and/or oil(s) of the present invention comprise preferably 15 to 90 % by weight of diglycerides and 85 to 10 % by weight of triglycerides.
- the composition of the present invention may comprise 0.05 to 20 % by weight, preferably 0.1 to
- the fatty acid constituting the diglyceride used in the present invention includes a C 6 to C 22 saturated or unsaturated fatty acid, preferably a C 16 to C 22 unsaturated fatty acid.
- an unsaturated fatty acid is desirable in the amount of 55 % by weight or more.
- a fat or oil containing a large amount of an unsaturated fatty acid- residue for example, including a vegetable (or plant) fat or oil such as safflower oil, olive oil, cottonseed oil, rapeseed oil, corn oil, soybean oil and palm oil; further, an animal fat or oil such as lard, beef-tallow and butter; and a fractional oil thereof, a transesterified oil thereof and a hyrogenated oil (hardened oil) thereof may be used.
- a vegetable (or plant) fat or oil such as safflower oil, olive oil, cottonseed oil, rapeseed oil, corn oil, soybean oil and palm oil
- an animal fat or oil such as lard, beef-tallow and butter
- a fractional oil thereof, a transesterified oil thereof and a hyrogenated oil (hardened oil) thereof for example, including a vegetable (or plant) fat or oil such as safflower oil, olive oil, cottonseed oil, rape
- the diglyceride is obtained by ester-exchanging reaction (, ester-interchanging reaction or transesterification) of a mixture of one or more of these fats and oils and glycerol in the presence of a catalyst or by ester-exchanging reaction of a mixture of a fatty acid composition having the high levels of unsaturated fatty acids and glycerol in the presence of a catalyst.
- ester-exchanging reaction ester-interchanging reaction or transesterification
- An excess of monoglycerides formed in a mixture of the generated diglycerides can be removed by a molecular distillation method or a chromatography method.
- the remaining monoglycerides are desirably removed to make it as small as possible.
- the content thereof is 5 % by weight or less (preferably 2 % by weight or less), there is no problem.
- the content of diglycerides in the present invention is preferably 15 % by weight or more, particularly preferably 15 to 90 % by weight based on the amount of the fats and oils.
- the content is particularly preferably 45 % by weight or more from the viewpoint of controlling triglycerides in blood and inhibiting the accumulation of body fat.
- the flavor component referred to in the present invention means all additives, related to tastes and aromas, such as perfumes, tasting agents (proteinous materials, amino acids etc.), spices, salts and sugars, and these are blended in an aqueous phase and/or an oil phase.
- the degree of the phase reversal referred to in the present invention can be confirmed by means of the concentration of the flavor component blended in the aqueous phase in water, when 5 g of the emulsified fat and/or oil composition was dispersed in 50 g of water with a magnetic stirrer (with a bar of 2.5 cm in length,
- the degree of the phase reversal is represented in terms of the concentration of the salt in water after the emulsified composition have been dispersed in water at an oral
- the concentration of the sugar may be measured by the same way as those in mentioned above. It is desired that 30 % or more, preferably 50 % or more and particularly preferably 80 % or more of the emulsion is made to reverse in phase for an initial one minute. When the degree of the phase reversal is less than 30 %, the strength of the flavor release is considerably low and the start of the release delays.
- composition exhibiting such a physical property can also be prepared even by selecting an ordinarily used formulation ingredient and an amount thereof.
- the demulsifier shown below (which is not ordinarily used in a W/O type emulsion) is advantageously used in order to easily obtain such a composition.
- the demulsifier referred to in the present invention is an additive functioning as a flavor enhancer or a flavor release- enhancer, which makes the phase reverse rapidly in the mouth during the time for ingestion, without affecting the stability in the emulsification during storage, to realize the excellent flavor release.
- a polyglycerol fatty acid ester As the demulsifier, a polyglycerol fatty acid ester, a water-soluble decomposed protein, lysolecithin, a sucrose fatty acid ester, a monoglyceride organic acid ester and a sorbitan fatty acid ester described below may be used.
- the polyglycerol fatty acid ester should be a mono-, di- or poly- ester of a saturated or unsaturated fatty acid having 10 to 22 carbon atoms, wherein the fatty acid constitutes the polyglycerol fatty acid ester, and polyglycerol and it should have HLB of 7 or more (preferably 11 or more) . If the HLB is less than 7, the flavor release is worsened on the contrary.
- the decomposed protein one or more kinds obtained by decomposing a milk protein, a vegetable (or plant) protein, an egg protein or the like with an enzyme or acid may be used.
- the milk protein for use includes casein, lactalbumin, lactoglobulin, lactoferrin, whey (or milk serum) , skim milk powder (or non-fat milk powder) , whole milk powder, butter milk powder, milk serum protein, milk etc.
- the plant protein includes soybean protein, wheat protein, corn protein etc.
- the egg protein includes ovalbumin, conalbumin, ovomucoid, ovoglobulin, egg white protein, yolk protein, whole egg protein etc.
- the decomposed protein obtained bydecomposing one of these water solubility is mentioned. If they are water-insoluble, the flavor release is worsened on the contrary due to gelation of the protein. Further, the decomposing treatment is carried preferably out before blending but it may be carried out during or after emulsification.
- the lysolecithin is a water-soluble compound constituted from a fatty acid being a C 10 to C 22 saturated or unsaturated fatty acid and it has HLB of 8 or more (preferably 12 or more) . If the HLB is less than 8, the flavor release is worsened on the contrary.
- the sucrose fatty acid ester should be a mono-, di-, or polyester of a saturated or unsaturated fatty acid having 10 to 22 carbon atoms, wherein the fatty acid constitutes the sucrose fatty acid ester, and sucrose; and it should have HLB of 5 or more (preferably 8 or more) . If the HLB is less than 5, the flavor release is worsened on the contrary.
- the monoglyceride organic acid ester is one having 1 or 2 organic acids bonded to a monoglyceride constituted of a saturated or unsaturated fatty acid having 10 to 22 carbon atoms and it should have HLB of 8 or more. If the HLB is less than 8, the flavor release is worsened on the contrary.
- the sorbitan fatty acid ester should be constituted from a saturated or unsaturated fatty acid having 10 to 22 carbon atoms, and it should have HLB of 8 or more.
- polysorbates known as Tween series from Atlas Ltd.
- polyoxyethylene sorbitan monostearate Tween 60
- polyoxyethylene sorbitan tristearate Tween 65
- polyoxyethylene sorbitan monooleate Tween 80
- polyoxyethylene sorbitan monolaurate Tween 20
- polyoxyethylene sorbitan monopalmitate Tween 40
- HLB HLB of the polyglycerol fatty acid, monoglyceride organic acid ester or sorbitan fatty acid ester
- HLB HLB of lysolecithin or the sucrose fatty acid ester
- the demulsifier is added in such an amount as to exhibit the action of demulsification (effect of improving the flavor release) .
- the demulsifier is preferably added to the aqueous phase, there is no problem if it is added to the oil phase. Its approximate amount is within the range of 0.01 to 5 % by weight, preferably 0.1 to 1 % by weight, in the composition.
- the starting material of an edible fat or oil used in the present invention may be one or more selected from vegetable fats and oils including soybean oil, rapeseed oil, palm oil, corn oil, cottonseed oil, coconut oil and palm kernel oil; and animal fats and oils including lard, fish oil and milk fat; and those obtained by hydrogenation or ester-exchange of these oils, for use.
- the solid fat content (SFC) in the oil phase used in the present invention may be usually within the range of 1 to 35 at
- a dairy product, an emulsifier or the like as a sub-component in the oil phase may be blended with the composition of the present invention.
- milk protein, starch, a thickening polysaccharide, a thermoplastic protein (gelatin etc. ) or the like may be blended with the aqueous phase based on water.
- an anti-oxidant including tocopherol, an ascorbyl ester such as palmitate and stearate, a tea leaf, a herb such as rosemary, a natural anti-oxidizing component extracted from a leaf or a root of a peach may be used together in order to inhibit the deterioration of the water-in-oil type emulsified fat and/or oil composition .
- the filtrate was subjected to molecular distillation, decoloration and deodorization to obtain the diglyceride (consisting of diglyceride content of 85 % by weight, monoglyceride content of 1.3 % by weight and triglyceride content of 13.7 % by weight and having open tube melting point of
- the degree of phase reversal of the obtained water-in-oil type emulsified fat and/or oil composition was measured in the following manner.
- the evaluation criteria are as follows.
- Examples 1 to 4 was 15.3 at 20 °C or 8.8 at 30 °C; and SFC in the oil phase in Example 5 was 9.8 at 20 °C or 6.0 at 30 °C.
- C Polyglycerol fatty acid ester having HLB of 15 (ML-750, provided by Sakamoto Yakuhin Kogyo Co.; Ltd.)
- D Polyglycerol fatty acid ester having HLB of 11 (SO-750, provided by Sakamoto Yakuhin Co., Ltd.)
- E Whey protein (provided by Morinaga Milk Industry Co., Ltd.)
- F Sucrose fatty acid ester having HLB of 1 (F-10, provided by
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Edible Oils And Fats (AREA)
- Fats And Perfumes (AREA)
- Colloid Chemistry (AREA)
- Cosmetics (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE60026528T DE60026528T2 (en) | 1999-06-30 | 2000-06-30 | EMULSIFIED FAT OR OIL COMPOSITION OF WATER IN OIL TYPE |
EP00942425A EP1227733B1 (en) | 1999-06-30 | 2000-06-30 | Water-in-oil type emulsified fat and/or oil composition |
BRPI0012066-9A BR0012066B1 (en) | 1999-06-30 | 2000-06-30 | Water-in-oil emulsified composition. |
US10/019,427 US6764707B1 (en) | 1999-06-30 | 2000-06-30 | Water-in-oil type emulsified fat and/or oil composition |
CA2373832A CA2373832C (en) | 1999-06-30 | 2000-06-30 | Water-in-oil type emulsified fat and/or oil composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11/184762 | 1999-06-30 | ||
JP18476299A JP3662445B2 (en) | 1999-06-30 | 1999-06-30 | Water-in-oil emulsified fat composition |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2001001787A2 true WO2001001787A2 (en) | 2001-01-11 |
WO2001001787A3 WO2001001787A3 (en) | 2002-06-06 |
Family
ID=16158893
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2000/004359 WO2001001787A2 (en) | 1999-06-30 | 2000-06-30 | Water-in-oil type emulsified fat and/or oil composition |
Country Status (10)
Country | Link |
---|---|
US (1) | US6764707B1 (en) |
EP (1) | EP1227733B1 (en) |
JP (1) | JP3662445B2 (en) |
CN (2) | CN1195419C (en) |
AT (1) | ATE319321T1 (en) |
BR (1) | BR0012066B1 (en) |
CA (1) | CA2373832C (en) |
DE (1) | DE60026528T2 (en) |
ES (1) | ES2258463T3 (en) |
WO (1) | WO2001001787A2 (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6495536B1 (en) | 1999-08-24 | 2002-12-17 | Kao Corporation | Fat or oil composition |
US6635777B1 (en) | 1999-06-17 | 2003-10-21 | Kao Corporation | Acid oil-in-water emulsified composition |
US6743459B2 (en) | 2000-12-15 | 2004-06-01 | Kao Corporation | Acidic oil-in-water type emulsion composition |
US6762203B2 (en) | 1999-08-03 | 2004-07-13 | Kao Corporation | Oil composition |
US6858247B2 (en) | 1999-06-16 | 2005-02-22 | Kao Corporation | Fat composition |
EP1627036B2 (en) † | 2003-05-28 | 2015-06-17 | Kao Corporation | Perfume composition |
Families Citing this family (18)
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JP4693139B2 (en) * | 2000-04-21 | 2011-06-01 | 昭和産業株式会社 | Emulsifier composition and oil and fat composition containing the same |
DE60227389D1 (en) * | 2001-08-23 | 2008-08-14 | Westgate Biolog Ltd | USE OF MILK SERUM APOPROTEINS IN THE PROPHYLAXIS OR TREATMENT OF MICROBIAL OR VIRUS INFECTIONS |
TWI331017B (en) * | 2002-09-13 | 2010-10-01 | Kao Corp | Oil or fat compositions |
EP1689239B1 (en) * | 2003-12-04 | 2008-03-12 | Unilever N.V. | Shelf stable homogeneous suspension |
JP4506284B2 (en) * | 2004-05-27 | 2010-07-21 | 日本電気株式会社 | Multilevel frequency shift keying identification method and apparatus |
JP4262179B2 (en) * | 2004-09-21 | 2009-05-13 | 花王株式会社 | Acid oil-in-water emulsified composition |
TWI363600B (en) * | 2004-09-21 | 2012-05-11 | Kao Corp | Acidic oil-in-water emulsion composition |
US20060105092A1 (en) * | 2004-11-12 | 2006-05-18 | Kraft Foods Holdings, Inc. | Trans-fatty acid free shortening |
EP1693436A1 (en) * | 2005-02-21 | 2006-08-23 | Cargill Inc. | Hardened vegetable oils and derivatives thereof |
DE102005031468A1 (en) * | 2005-07-04 | 2007-01-18 | Basf Ag | Aqueous suspensions of poorly water-soluble or water-insoluble active ingredients and dry powder prepared therefrom |
JP4664176B2 (en) * | 2005-09-30 | 2011-04-06 | 理研ビタミン株式会社 | Plastic oil composition |
JP5253014B2 (en) * | 2008-06-27 | 2013-07-31 | 株式会社カネカ | Water-in-oil emulsified fat composition |
JP5925638B2 (en) | 2011-08-22 | 2016-05-25 | 花王株式会社 | Oil composition |
CN103957721B (en) * | 2011-12-01 | 2016-08-17 | 株式会社钟化 | Foaming characteristic oil-in-water type emulsified fat-and-oil composition |
WO2014005797A1 (en) * | 2012-07-06 | 2014-01-09 | Unilever N.V. | Fat powder and process for the preparation of edible water-in-oil emulsion comprising it |
PL2941131T3 (en) * | 2013-03-29 | 2020-03-31 | Intercontinental Great Brands Llc | Transparent and transluscent liquid filled candy; process of making thereof; sugar-free liquid edible composition; and use thereof |
JP7129779B2 (en) * | 2017-01-16 | 2022-09-02 | 月島食品工業株式会社 | Water-in-oil emulsified fat composition for filling |
CN111713564B (en) * | 2020-04-17 | 2023-01-24 | 天津科技大学 | Collagen-based artificial edible solid fat and preparation method thereof |
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GB1564801A (en) * | 1975-11-07 | 1980-04-16 | Unilever Ltd | Phase inverting low fat spreads |
EP0417562A1 (en) * | 1989-09-01 | 1991-03-20 | Kao Corporation | Water-in-oil emulsion composition |
WO1996032022A1 (en) * | 1995-04-13 | 1996-10-17 | Unilever N.V. | Edible plastic spread |
US5879735A (en) * | 1994-02-18 | 1999-03-09 | Loders-Croklaan B.V. | Fat blends, based on diglycerides |
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US4284655A (en) | 1980-04-22 | 1981-08-18 | Scm Corporation | Low-fat comestible spread substitutes |
GB8418154D0 (en) | 1984-07-17 | 1984-08-22 | Unilever Plc | Edible fat composition |
US4959160A (en) * | 1987-04-15 | 1990-09-25 | Iscor Limited | Process for the treatment of contaminated emulsion |
US4882187A (en) * | 1987-07-02 | 1989-11-21 | Thomas J. Lipton Inc. | Edible spread and process for the preparation thereof |
JP2689816B2 (en) * | 1991-12-18 | 1997-12-10 | 不二製油株式会社 | Oils and fats for creams and low oil creams using them |
JP3195700B2 (en) | 1993-10-23 | 2001-08-06 | 株式会社スペクトラ | Voice analyzer |
AU1705595A (en) | 1994-02-18 | 1995-09-04 | Loders Croklaan B.V. | Fat blends containing diglycerides |
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CA2272579A1 (en) * | 1997-09-24 | 1999-04-01 | Snow Brand Milk Products Co., Ltd. | Low-fat spread |
EP0968655A4 (en) * | 1997-12-03 | 2003-05-21 | Snow Brand Milk Products Co Ltd | Spread |
JP3550017B2 (en) | 1998-03-03 | 2004-08-04 | 花王株式会社 | Water-in-oil type emulsified fat composition |
JP3779505B2 (en) | 1999-08-24 | 2006-05-31 | 花王株式会社 | Oil composition |
JP3752127B2 (en) | 2000-03-21 | 2006-03-08 | 花王株式会社 | Oil composition |
-
1999
- 1999-06-30 JP JP18476299A patent/JP3662445B2/en not_active Expired - Fee Related
-
2000
- 2000-06-30 CN CNB008096899A patent/CN1195419C/en not_active Expired - Fee Related
- 2000-06-30 DE DE60026528T patent/DE60026528T2/en not_active Expired - Lifetime
- 2000-06-30 US US10/019,427 patent/US6764707B1/en not_active Expired - Lifetime
- 2000-06-30 WO PCT/JP2000/004359 patent/WO2001001787A2/en active IP Right Grant
- 2000-06-30 AT AT00942425T patent/ATE319321T1/en not_active IP Right Cessation
- 2000-06-30 ES ES00942425T patent/ES2258463T3/en not_active Expired - Lifetime
- 2000-06-30 CA CA2373832A patent/CA2373832C/en not_active Expired - Fee Related
- 2000-06-30 EP EP00942425A patent/EP1227733B1/en not_active Expired - Lifetime
- 2000-06-30 CN CN2005100091637A patent/CN1659970A/en active Pending
- 2000-06-30 BR BRPI0012066-9A patent/BR0012066B1/en not_active IP Right Cessation
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GB1564801A (en) * | 1975-11-07 | 1980-04-16 | Unilever Ltd | Phase inverting low fat spreads |
EP0417562A1 (en) * | 1989-09-01 | 1991-03-20 | Kao Corporation | Water-in-oil emulsion composition |
US5879735A (en) * | 1994-02-18 | 1999-03-09 | Loders-Croklaan B.V. | Fat blends, based on diglycerides |
WO1996032022A1 (en) * | 1995-04-13 | 1996-10-17 | Unilever N.V. | Edible plastic spread |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6858247B2 (en) | 1999-06-16 | 2005-02-22 | Kao Corporation | Fat composition |
US6635777B1 (en) | 1999-06-17 | 2003-10-21 | Kao Corporation | Acid oil-in-water emulsified composition |
US7041328B2 (en) | 1999-06-17 | 2006-05-09 | Kao Corporation | Acid oil-in-water emulsified composition |
US6762203B2 (en) | 1999-08-03 | 2004-07-13 | Kao Corporation | Oil composition |
US6852758B2 (en) | 1999-08-03 | 2005-02-08 | Kao Corporation | Oil composition |
US6495536B1 (en) | 1999-08-24 | 2002-12-17 | Kao Corporation | Fat or oil composition |
US6743459B2 (en) | 2000-12-15 | 2004-06-01 | Kao Corporation | Acidic oil-in-water type emulsion composition |
EP1627036B2 (en) † | 2003-05-28 | 2015-06-17 | Kao Corporation | Perfume composition |
Also Published As
Publication number | Publication date |
---|---|
JP3662445B2 (en) | 2005-06-22 |
CA2373832C (en) | 2012-03-06 |
WO2001001787A3 (en) | 2002-06-06 |
EP1227733A2 (en) | 2002-08-07 |
DE60026528D1 (en) | 2006-05-04 |
CA2373832A1 (en) | 2001-01-11 |
US6764707B1 (en) | 2004-07-20 |
ATE319321T1 (en) | 2006-03-15 |
CN1195419C (en) | 2005-04-06 |
JP2001008617A (en) | 2001-01-16 |
DE60026528T2 (en) | 2006-10-05 |
EP1227733B1 (en) | 2006-03-08 |
CN1659970A (en) | 2005-08-31 |
CN1420727A (en) | 2003-05-28 |
ES2258463T3 (en) | 2006-09-01 |
BR0012066B1 (en) | 2013-02-05 |
BR0012066A (en) | 2002-04-02 |
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