WO1994009098A1 - Triglyceride fractionation - Google Patents

Triglyceride fractionation Download PDF

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Publication number
WO1994009098A1
WO1994009098A1 PCT/EP1993/002776 EP9302776W WO9409098A1 WO 1994009098 A1 WO1994009098 A1 WO 1994009098A1 EP 9302776 W EP9302776 W EP 9302776W WO 9409098 A1 WO9409098 A1 WO 9409098A1
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Prior art keywords
fraction
ssu
stearin
fractionation
palm oil
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Ceased
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PCT/EP1993/002776
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French (fr)
Inventor
John Bernard Harris
Stephen Raymond Moore
Christopher Rawlins
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Loders Croklaan BV
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Loders Croklaan BV
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Priority to AU51764/93A priority Critical patent/AU670336B2/en
Priority to JP06509598A priority patent/JP2000516268A/en
Priority to EP93922927A priority patent/EP0664828B2/en
Priority to CA002146141A priority patent/CA2146141C/en
Priority to DE69303826T priority patent/DE69303826T3/en
Application filed by Loders Croklaan BV filed Critical Loders Croklaan BV
Priority to US08/926,994 priority patent/US5849940A/en
Priority to DK93922927T priority patent/DK0664828T4/en
Publication of WO1994009098A1 publication Critical patent/WO1994009098A1/en
Priority to KR1019950701456A priority patent/KR0182273B1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D9/00Other edible oils or fats, e.g. shortenings or cooking oils
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, 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
    • C11B7/00Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
    • C11B7/0008Separation 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
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, 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
    • C11B7/00Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
    • C11B7/0008Separation 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
    • C11B7/0025Separation 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

Definitions

  • our invention concerns with a process that results in the production of the desired fat mixtures. Therefore, our invention concerns a process for preparing a fat fraction, suitable as fat component in non-lauric, non- hydrogenated, cool melting, non-temper, non-trans filling or coating fats.
  • the SUS content of the products isolated should be at least 65 wt%, preferably at least 70 wt .
  • the starting triglyceride preferably contains at least 6 wt% of the SSU triglycerides.
  • the starting fats are also rich in SUS-triglycerides.
  • Suitable fats, meeting above criteria are: palm oil, palm oil fractions, mixtures thereof, in particular palm oil stearin, and more particularly a palm oil stearin, obtained after dry fractionation. Very useful results can be obtained by using mixtures of palm oil and dry fractionated palm oil stearin, in particular mixtures with more than 20 wt% of the stearin.
  • the fractionation is performed by mixing 1-6 1 of solvent per gram of fat at 50°C; cooling the solution obtained to 12-14°C, collecting the precipitate formed; extracting said precipitate under specific conditions with solvent of 10°C; filtering the slurry from the extraction step, resulting in the high melting product and a filtrate; the filtrate is cooled to 1-3°C and the new precipitate is collected; this new precipitate is extracted again under very specific conditions; after filtering of the slurry of this second extraction the intermediate melting product is separated, the filtrate also obtained is subjected to a removal of the solvent giving the liquid oil.
  • the extraction steps are incomparable with washing steps and have main advantages over a washing.
  • the fractionation can be carried out as dry fractionation, or as wet fractionation, while also combinations of these two can be applied.
  • dry fractionation we prefer to perform a multi-step dry fractionation as disclosed in our European Patent application 399 597.
  • the fractionation can be a two-step of a multi-step fractionation process.
  • the stearin fraction of 1) is subjected to a second wet fractionation with an organic solvent (again hexane, petr. ether or acetone) at 15-25°C. This time the olein (or bottom) fraction is collected as the product enriched in SSU (at least 12 wt%) . This olein fraction is separated in a yield of 25-80 wt%, preferably 35-80 wt%, based on the stearin fraction of step 1) .
  • An alternative route is to perform the first wet fractionation at 15-25°C, collecting the olein fraction, consisting predominantly of UUU; SUU; SSU and SUS triglycerides. Subjecting this olein fraction to a second wet fractionation at -5 to 5°C and collecting the stearin fraction as product fraction.
  • the olein fraction is separated in the first step in a yield of 45-90 wt%, preferably 55-85 wt%, while the stearin fraction in the second stage is separated in a yield of 25-80 wt%, preferably 40-50 wt%.
  • wet fractionation amounts of 1-8, preferably 3-7 1 solvent per kg triglyceride material are used. The exact amount will vary with the type of solvent and with the fractionation temperature applied.
  • dry fractionation steps in particular as a multi- step process, can also be applied.
  • the products resulting from the process are very suitable for application in the fat part of fillings or coatings of confectionery products, such as chocolate bars or bonbons.
  • the use of these compounds will impart cool melting and non-temper properties to the filling or coating compositions of the confectionery product.
  • Example 1 of EP 81 881 was carried out, starting from a palm oil stearin with the following triglyceride composition:

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Analytical Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Fats And Perfumes (AREA)
  • Edible Oils And Fats (AREA)
  • Confectionery (AREA)

Abstract

The invention concerns a fractionation process for the production of triglycerides with at least 12 wt% SSU (S = saturated fatty acids; U = unsaturated fatty acids) by subjecting a fat with at least 5 wt% SSU to a fractionation, achieving an enrichment factor for the SSU enrichment of at least 1.5.

Description

Triαlvceride fractionation
In British patent application 9121578.0 we have disclosed non-temper confectionery fats, containing minimal working amounts of fat of the SSO-type. These fat compositions are obtained by adding externally the working amount of SSO.
Above method has, however, the disadvantage that we must have free access to SSO-type triglycerides. Although several methods are known by which these fats can be synthesized, it would offer a main advantage when triglyceride mixtures could be obtained along non-synthetic routes, e.g. by applying fractionation techniques only, that contain enough of the SSO component to make them suitable as additive for polymorphic fats that otherwise needed tempering. Even more advantages could be achieved when fat mixtures could be obtained that do not need to be tempered anymore, because of the presence of enough of the SSO triglycerides.
In fact, our invention concerns with a process that results in the production of the desired fat mixtures. Therefore, our invention concerns a process for preparing a fat fraction, suitable as fat component in non-lauric, non- hydrogenated, cool melting, non-temper, non-trans filling or coating fats. This process is characterized by: performing a fractionation on a triglyceride composition, containing at least 5 wt% SSU triglycerides (S= C16-C22 saturated fatty acid, preferably C16-C18; U= mono- or poly- unsaturated C18-C22 fatty acid; preferably oleic acid) , removing at least part of the trisaturated triglycerides and/or at least part of the di- and tri-unsaturated triglycerides and isolating a triglyceride composition with an SSU content of at least 12 wt%, preferably 12-20 wt%, which content is at least 1.5 times, preferably at least 1.7 times, most preferably at least 2.0 times the SSU content of the starting triglycerides composition. Simultaneously, the SUS content of the products isolated should be at least 65 wt%, preferably at least 70 wt .
The starting triglyceride, preferably contains at least 6 wt% of the SSU triglycerides. As the endproducts are meant to be used as confectionery fats, the starting fats are also rich in SUS-triglycerides. Suitable fats, meeting above criteria are: palm oil, palm oil fractions, mixtures thereof, in particular palm oil stearin, and more particularly a palm oil stearin, obtained after dry fractionation. Very useful results can be obtained by using mixtures of palm oil and dry fractionated palm oil stearin, in particular mixtures with more than 20 wt% of the stearin.
From EP 81 881 a process is known, wherein a palm oil stearin is subjected to a solvent fractionation. Three fractions are obtained, i.e. a first fraction with a melting point above 45°C, a second fraction with a melting point between 33 and 44°C and a third, liquid fraction. The fractionation is performed by mixing 1-6 1 of solvent per gram of fat at 50°C; cooling the solution obtained to 12-14°C, collecting the precipitate formed; extracting said precipitate under specific conditions with solvent of 10°C; filtering the slurry from the extraction step, resulting in the high melting product and a filtrate; the filtrate is cooled to 1-3°C and the new precipitate is collected; this new precipitate is extracted again under very specific conditions; after filtering of the slurry of this second extraction the intermediate melting product is separated, the filtrate also obtained is subjected to a removal of the solvent giving the liquid oil. According to page 9, lines 22-42 the extraction steps are incomparable with washing steps and have main advantages over a washing. Nothing is disclosed about the SSU-content of the starting palm oil stearin, the SSU content of the end products, enrichment in the SSU content or the production of non-temper confectionery fats. In our process we do not apply the very specific extraction (= non-cashing) steps, as prescribed by the above EP 81 881.
Wet fractionations of palm oil-based materials are known from a.o. DE 2,921,499; DE 1,792,606; US 3,686,240; US 4,055,679; EP 347,006 or EP 78,568. However, in none of these references it is mentioned that the product obtained has an SSU-content of at least 12 wt%, while an enrichment with a factor 1.5 for the SSU-content is achieved.
The fractionation can be carried out as dry fractionation, or as wet fractionation, while also combinations of these two can be applied. In case a dry fractionation is performed, we prefer to perform a multi-step dry fractionation as disclosed in our European Patent application 399 597.
Depending on the type of starting material the fractionation can be a two-step of a multi-step fractionation process.
The best results are obtained, when we apply a two-step wet fractionation process.
In a two-step process, starting from palm oil stearin the following steps can be applied:
1. wet fractionation with an organic solvent, such as hexane, petr. ether and in particular acetone, at -5 to 5°C, yielding a stearin fraction, preferably in yields of 45-85 wt%, more preferably 45-75 wt% based on the palm oil stearin. This fraction predominantly consists of SSS, SUS and SSU triglycerides.
2. The stearin fraction of 1) is subjected to a second wet fractionation with an organic solvent (again hexane, petr. ether or acetone) at 15-25°C. This time the olein (or bottom) fraction is collected as the product enriched in SSU (at least 12 wt%) . This olein fraction is separated in a yield of 25-80 wt%, preferably 35-80 wt%, based on the stearin fraction of step 1) .
An alternative route, however, is to perform the first wet fractionation at 15-25°C, collecting the olein fraction, consisting predominantly of UUU; SUU; SSU and SUS triglycerides. Subjecting this olein fraction to a second wet fractionation at -5 to 5°C and collecting the stearin fraction as product fraction.
In this case the olein fraction is separated in the first step in a yield of 45-90 wt%, preferably 55-85 wt%, while the stearin fraction in the second stage is separated in a yield of 25-80 wt%, preferably 40-50 wt%.
In the wet fractionation amounts of 1-8, preferably 3-7 1 solvent per kg triglyceride material are used. The exact amount will vary with the type of solvent and with the fractionation temperature applied.
Working within the process parameter set out above will in general result in a product with at least 12 wt% SSU, whereas the ratio between the weight content SSU in the product and the weight content of SSU in starting material is at least 1.5. Simultaneously, its SUS content will be more than 65 wt%.
Although wet fractionation steps are disclosed in detail above, dry fractionation steps, in particular as a multi- step process, can also be applied.
The products resulting from the process are very suitable for application in the fat part of fillings or coatings of confectionery products, such as chocolate bars or bonbons. The use of these compounds will impart cool melting and non-temper properties to the filling or coating compositions of the confectionery product.
Therefore, also fillings or coating compositions for confectionery products, wherein at least part of the fat components is a fat, obtainable according to our process, are also part of the invention.
Example
Four different triglyceride compositions A, B, C and D with the composition mentined in table I were subjected to a double wet fractionation.
The conditions for the wet fractionations are given in table II. The olein fractions of step 2 were collected. Their SSU content is given in table III.
Table I
Figure imgf000007_0001
S= saturated C16/C18 0= oleic Ln= linoleic DB= double bonds Table II
Figure imgf000008_0001
* based on starting material
Figure imgf000008_0002
It will be evident from the above results that although starting material D meets the requirement of SSU content, the product obtained from this material D is too low in SSU. This means that other yields or temperatures must be applied for this fat, when one wants to cope with the SSU content of the end product.
Comparative example
Example 1 of EP 81 881 was carried out, starting from a palm oil stearin with the following triglyceride composition:
SLnS 6.6 wt% SSLn 1.8 soo 13.9
Figure imgf000008_0003
The conditions, mentioned in EP 81 881 were used. A product enriched in SSU was obtained. This product had the following composition:
SLnS 7.9 wt% SSLn 1.4 SOO 10.4
Figure imgf000009_0001
So, in this process we could not achieve an enrichment in the SSU-component of more than 1.5 (found: 1.41) . Moreover, the SUS content of this fraction was rather low (66.8 wt%) .

Claims

1. A process for preparing a fat fraction, suitable as fat component in non-lauric, non-hydrogenated, cool- melting, non-temper, non-trans filling or coating fats characterised by: performing a fractionation on a triglyceride composition, containing at leat 5 wt% SSU triglycerides (S= saturated fatty acid C16-C22; U- mono- or poly-unsaturated fatty acids C18-C22) removing at least part of the trisaturated triglycerides and/or at least part of the di- and tri-unsaturated triglycerides and isolating a triglyceride composition with an SSU content of at least 12 wt%, preferably 12-20 wt%, which content is at least 1.5 times, preferably at least 1.7 times, most preferably at least 2 times the SSU content of the starting triglyceride composition.
2. Process according to claim 1, wherein the SSU content of the starting triglyceride composition is at least 6 wt%.
3. Process according to claim 1, wherein the SUS content (S and U identical with S and U of claim 1) of the product isolated is at least 65 wt%, preferably at least 70 wt%.
4. Process according to claims 1 or 2, wherein the starting triglyceride composition is palm oil, fractions of palm oil or mixtures thereof, in particular a stearin fraction of palm oil, especially a stearin fraction obtained after dry fractionation of palm oil.
5. Process according to claim 1, wherein a palm oil stearin is fractionated in two steps.
6. Process according to claim 5, wherein the two steps both comprise wet fractionation.
7. Process according to claims 5 or 6, wherein the fractionation comprises the following steps:
1) a wet fractionation of the palm oil stearin with an organic solvent at -5 to 5°C, yielding a stearin fraction, consisting predominantly of SSS, SUS and SSU triglycerides.
2) a wet fractionation of the stearin fraction of 1) with an organic solvent at 15-25°C and collecting the olein fraction as the product, enriched in SSU.
8. Process according to claim 7, wherein the stearin fraction of step l) is separated in a yield of 45-85 wt%, preferably 45-75 wt%, based on the palm oil stearin, while the olein fraction of step 2) is separated in a yield of 25-80 wt%, preferably 35-80 wt%, based on the stearin fraction of step 1) .
9. Process according to claims 5 or 6, wherein the fractionation comprises the following steps:
1) a wet fractionation of the palm oil stearin with an organic solvent at 15-25°C separating an olein fraction, consisting predominantly of U3; SUU; SSU and SUS-triglycerides
2) a wet fractionation of the olein fraction of 1) with an organic solvent at -5 to 5°C and collecting the stearin fraction as the product, enriched in SSU.
10. Process according to claim 9, wherein the olein fraction of step 1) is separated in a yield of 45-90 wt%, preferably 55-85 wt%, based on the palm oil stearin, while the stearin fraction of step 2) is separated in a yield of 25-80 wt%, preferably 40-50 wt%, based on the olein fraction step 1) .
11. Process according to claims 6-10, wherein the wet fractionations are carried out, using hexane, petroleum ether or preferably acetone as solvent in amounts of 1-8 1 per kg triglyceride.
12. Filling- or coating compositions for confectionery products, wherein part of the fat component is a fat, obtainable according to the process of claims 1-11.
13. Use of a triglyceride composition, containing SSU- type triglycerides in confectionery fats, characterised in that the triglyceride compositions, obtainable according to the process of claims 1-11 are used to impart cool melting, non-temper properties to the filling or coating composition of a confectionery product.
PCT/EP1993/002776 1992-10-16 1993-10-08 Triglyceride fractionation Ceased WO1994009098A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
DK93922927T DK0664828T4 (en) 1992-10-16 1993-10-08 Triglyceride Fractionation
JP06509598A JP2000516268A (en) 1992-10-16 1993-10-08 Triglyceride fractionation
EP93922927A EP0664828B2 (en) 1992-10-16 1993-10-08 Triglyceride fractionation
CA002146141A CA2146141C (en) 1992-10-16 1993-10-08 Triglyceride fractionation
DE69303826T DE69303826T3 (en) 1992-10-16 1993-10-08 TRIGLYCERIDE FACTIONATION
AU51764/93A AU670336B2 (en) 1992-10-16 1993-10-08 Triglyceride fractionation
US08/926,994 US5849940A (en) 1992-10-16 1993-10-08 Triglyceride fractionation
KR1019950701456A KR0182273B1 (en) 1992-10-16 1995-04-15 Triglyceride fractionation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP92309489.0 1992-10-16
EP92309489 1992-10-16

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WO1994009098A1 true WO1994009098A1 (en) 1994-04-28

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PCT/EP1993/002776 Ceased WO1994009098A1 (en) 1992-10-16 1993-10-08 Triglyceride fractionation

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US (1) US5849940A (en)
EP (1) EP0664828B2 (en)
JP (1) JP2000516268A (en)
KR (1) KR0182273B1 (en)
AT (1) ATE140722T1 (en)
AU (1) AU670336B2 (en)
CA (1) CA2146141C (en)
DE (1) DE69303826T3 (en)
MY (1) MY109839A (en)
WO (1) WO1994009098A1 (en)
ZA (1) ZA937603B (en)

Cited By (1)

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WO2009013473A1 (en) * 2007-07-23 2009-01-29 Loders Croklaan B.V. Confectionery compositions

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MY122480A (en) * 2000-05-29 2006-04-29 Premium Vegetable Oils Sdn Bhd Trans free hard structural fat for margarine blend and spreads
US20030003195A1 (en) * 2001-06-20 2003-01-02 Unilever Bestfoods North America, Division Of Conopco, Inc. Oily paste which contains herbs
US20030235642A1 (en) * 2002-03-13 2003-12-25 Huxel Edward T. Method of dry fractionation to reduce trans double bonds in vegetable oils
MXPA05001630A (en) * 2002-08-12 2005-04-25 Unilever Nv Triglyceride fat.
JP4651270B2 (en) * 2003-03-20 2011-03-16 株式会社Adeka Oil composition
US7618670B2 (en) * 2004-06-14 2009-11-17 Premium Vegetable Oils Sdn. Bhd. Trans free non-hydrogenated hard structural fat and non-hydrogenated hard palm oil fraction component
CA2641706C (en) * 2006-02-08 2014-12-23 Fuji Oil Company, Limited Edible products with low content of saturated and trans unsaturated fats
US7645473B2 (en) * 2006-06-13 2010-01-12 Loders Croklaan Usa Llc Fat composition
ATE526826T1 (en) * 2007-07-11 2011-10-15 Loders Croklaan Bv GLYCERIDE COMPOSITION FOR USE AS A COATING GREASE
CA2693608C (en) 2007-07-11 2014-04-22 Loders Croklaan B.V. Composition comprising triglycerides
JP2012055268A (en) * 2010-09-10 2012-03-22 Kaneka Corp Method of manufacturing oil and fat composition
MY169820A (en) 2011-09-09 2019-05-16 Sime Darby Plantation Berhad A method for producing triacylglycerol oil
KR102862613B1 (en) * 2019-10-22 2025-09-23 주식회사 삼양사 Method for preparing triglyceride with high yield through wet fractionation using solvent mixture
US20230115992A1 (en) * 2020-03-11 2023-04-13 Fuji Oil Holdings Inc. Oil and fat for chocolate products which is suitable for complex confection

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WO1983000418A1 (en) * 1981-07-31 1983-02-17 Scm Corp Hard butter and process for making same
EP0081881A2 (en) * 1981-12-15 1983-06-22 Societe Des Produits Nestle S.A. A process for the solvent fractionation of palm oil stearines and products obtained with said process

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US3492130A (en) * 1966-11-21 1970-01-27 Scm Corp Hard butter compositions and method of production
FR2303072A1 (en) * 1975-03-04 1976-10-01 Unilever Nv FAT PLASTIC PRODUCT
WO1983000418A1 (en) * 1981-07-31 1983-02-17 Scm Corp Hard butter and process for making same
EP0081881A2 (en) * 1981-12-15 1983-06-22 Societe Des Produits Nestle S.A. A process for the solvent fractionation of palm oil stearines and products obtained with said process

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Publication number Priority date Publication date Assignee Title
WO2009013473A1 (en) * 2007-07-23 2009-01-29 Loders Croklaan B.V. Confectionery compositions
US8986772B2 (en) 2007-07-23 2015-03-24 Loders Croklaan B.V. Confectionery compositions

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JP2000516268A (en) 2000-12-05
KR0182273B1 (en) 1999-04-01
US5849940A (en) 1998-12-15
DE69303826T3 (en) 2000-12-28
DE69303826D1 (en) 1996-08-29
EP0664828B1 (en) 1996-07-24
EP0664828A1 (en) 1995-08-02
AU5176493A (en) 1994-05-09
EP0664828B2 (en) 2000-09-13
DE69303826T2 (en) 1996-12-19
CA2146141A1 (en) 1994-04-28
MY109839A (en) 1997-08-30
CA2146141C (en) 2001-03-13
ATE140722T1 (en) 1996-08-15
ZA937603B (en) 1995-04-13
AU670336B2 (en) 1996-07-11

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