WO2006036059A1 - Stable creamer - Google Patents
Stable creamer Download PDFInfo
- Publication number
- WO2006036059A1 WO2006036059A1 PCT/NL2005/000697 NL2005000697W WO2006036059A1 WO 2006036059 A1 WO2006036059 A1 WO 2006036059A1 NL 2005000697 W NL2005000697 W NL 2005000697W WO 2006036059 A1 WO2006036059 A1 WO 2006036059A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- carbohydrate
- protein
- creamer
- fat
- conjugate
- 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
Links
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J3/00—Working-up of proteins for foodstuffs
- A23J3/04—Animal proteins
- A23J3/08—Dairy proteins
- A23J3/10—Casein
-
- 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 OR TREATMENT THEREOF
- A23C11/00—Milk substitutes, e.g. coffee whitener compositions
- A23C11/02—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins
- A23C11/08—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins containing caseinates but no other milk proteins nor milk fats
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L9/00—Puddings; Cream substitutes; Preparation or treatment thereof
- A23L9/20—Cream substitutes
- A23L9/22—Cream substitutes containing non-milk fats but no proteins other than milk proteins
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- This invention relates to a method for preparing a creamer, to a creamer that is well resistant to separation, and to the use of a particular constituent as anti-separation agent.
- Creamers are fat-containing compositions which form an emulsion in a suitable amount of water. Creamers are used to make a food creamier. Creamers are also used to change the color of a food, in particular for imparting a white color, or to make the color lighter.
- Creamers can be administered dry - usually in powder form - or as liquid. Creamers can be used as end product, for instance as coffee or tea creamer, or as semifinished product in the preparation of a food, for instance an instant soup or sauce.
- a creamer generally contains a surface-active substance having an emulsifying action. Suitable for this purpose is, for instance, a protein such as caseinate.
- a disadvantage of a protein as surface -active substance in a creamer is the resistance of a protein-containing creamer to separation. In particular upon exposure to high temperatures, a low pH and/or a high content of polyvalent cations, in particular calcium ions, a creamer based on (milk) protein has a tendency to separate.
- a stabilizing salt such as a sodium or potassium salt of a phosphate or a citrate.
- a stabilizing salt does not lead to the desired result in some products, in particular an acid soup such as tomato soup.
- the salt can have an adverse effect on the taste, for instance when used in coffee, in particular coffee concentrates in cans ("canned coffee").
- One object of the invention is to provide a protein-containing creamer which is well-resistant to separation, also when it is used in a food having an acidic pH, and/or in a hot food and/or in a food having a high polyvalent cation content, in particular a high calcium content (i.e. with a high hardness).
- a further object of the invention is to provide a method for preparing such a creamer.
- a particular conjugate of a protein and in particular a conjugate of a protein and a carbohydrate polymer, is eminently suitable to be used in a creamer having a good resistance to separation, also when the creamer is used in an acid food, and/or a hot food and/or a food having a high degree of hardness.
- the creamer according to this invention provides the functionality so characteristic of protein-containing creamers, whereby a good creaminess of the food is combined with both sufficient whitening power and a neutral taste, which is an advantage over creamers where use is made of an emulsifying substitute for proteins, such as, for instance, emulsifying starch.
- the invention accordingly relates to a creamer comprising a fat and a protein-carbohydrate polymer conjugate as emulsifier, the carbohydrate polymer being built up from at least three monosaccharide units.
- a “conjugate” is herein understood to mean a compound consisting of a protein and one or more reducing carbohydrates, the carbohydrates being bound to the protein via a covalent bond.
- This covalent bond will as a rule be formed between an ⁇ -amino group of a lysine side chain of the protein and the aldehyde group of the carbohydrate. The formation of such a covalent bond is known as the first step in the Maillard reaction.
- a protein-carbohydrate conjugate in which the carbohydrate polymer is built up from at least three monosaccharide units is very suitable as anti- separation agent in a creamer.
- a creamer according to the invention also has a very good resistance to separation if the creamer is administered to a liquid having a degree of hardness of at least 15 °DH.
- United States patent application US 2001/041211 discloses a powdered agglomerated creamer, which is especially soluble at low temperatures, and which can undergo freeze/thaw cycles, as well as a method for the manufacture of such a creamer and the use thereof in cooled drinks.
- the creamer preferably comprises a sweetener (carbohydrate), a water-soluble or water-dispersible protein and an edible oil having a melting point below 20 0 C.
- Examples 1 and 2 of the above-mentioned United States patent application use potassium phosphate and sodium citrate as anti-separation agent.
- European patent application EP-A-O 579 328 relates to powder-form creamers for beverages and soups, consisting of fat, carbohydrate and protein, the protein being chicken albumen. The creamer forms a foam on the surface. It is noted that the chicken protein provides a better and stabler foam than for instance casein or casemate. The chicken protein furthermore denatures already at room temperature, during foam formation. Further, especially a glycose syrup having a DE of 36 is utilized (see Examples I and IV).
- Examples 10 and 11 of US-A-5,571,334 show a creamer comprising a protein, a fat, and a starch having a DE of 1-5.
- Example 1 discloses a protein-carbohydrate mixture, present in a creamer, which contains no fat. There does not seem to be any conjugate formation involved, nor is the use of an anti-separation agent suggested.
- a creamer according to the invention is very suitable for use in an acid food such as coffee (usually having a pH of about 4.8-5.4) or an acid soup, such as tomato soup (usually having a pH of about 4-4.5).
- the invention furthermore relates to a creamer comprising a fat and a protein-carbohydrate conjugate, the carbohydrate being built up from at least three monosaccharide units, which creamer, also in the absence of a stabilizing salt, is resistant to separation if the creamer is present in a liquid having a pH in the range of about 3.5 to about 7.5 and/or having a temperature in the range of about 70-100 0 C and/or having a hardness of about 15-30 0 DH.
- the creamer is resistant to separation at a temperature, pH and hardness in the specified ranges. In an embodiment, at the above-mentioned pH and hardness, the creamer is even resistant to separation at a temperature of up to about 150 0 C or more.
- UHT ultra-high temperature treatment
- an emulsion of the creamer is stable in a beverage, i.e., for at least 15 min after addition of the creamer to the beverage, whitening power is maintained and no fat separation is to be seen.
- a creamer according to the invention is preferably in powder form.
- the creamer according to the invention can, if desired, contain a stabilizing salt, for instance in a relatively low concentration, for instance less than 1 wt. % based on the creamer dry matter.
- a stabilizing salt for instance in a relatively low concentration, for instance less than 1 wt. % based on the creamer dry matter.
- the creamer is at least substantially free of added phosphate and/or added citrate. More preferably, a creamer according to the invention is at least substantially free of any added stabilizing salt.
- substantially free is meant herein that there is at least less of the salt present than is necessary in a conventional creamer with an unconjugated mixture of carbohydrate and protein as emulsifier to provide a sufficient stability at high temperature in an acid environment of a high hardness.
- substantially free is understood to mean a content of less than about 0.2 wt.% based on the creamer dry matter, more particularly a content of 0-0.1 wt.%.
- Dry matter is herein understood to include all components except water.
- Protein-carbohydrate conjugates are known, for that matter.
- WO 00/18249 describes a process whereby a whey protein is glycosylated by storing powdered whey protein in an environment whose moistness and temperature are controlled. What is contemplated is to reduce the further occurrence of Maillard continuation reactions.
- the use of such a glycosylated protein in creamer for enhancing stability of the creamer at a high temperature, low pH and/or high degree of hardness is not mentioned.
- the present inventors have found that the process described in WO00/18249 generally leads to a difficult-to-handle, sticky or caked powdered protein- carbohydrate conjugate. Further, it has been found that a protein-carbohydrate conjugate which is disclosed in WO 00/18249 is not well-resistant to separation in a creamer at high hardness and/or low pH and/or high temperature (See present Example 3).
- a creamer having a good stability to separation also at high hardness and/or low pH and/or high temperature
- the invention furthermore relates to a method for manufacturing a creamer, comprising:
- the creamer is prepared by - mixing a protein and a carbohydrate to form a mixture divided on a molecular scale, in particular by dissolving both components in a solvent; then
- the creamer can then be used as liquid creamer.
- the creamer is dried, more preferably to a powder-form creamer.
- a powder-form creamer has been found in general not to be sticky and not to give rise to any caking during storage when it is stored under conventional conditions.
- a method according to the invention not only provides a creamer having desirable properties with a view to storage and with a view to its use, but is also simple in design and can be easily carried out on an industrial scale.
- a method according to the invention can be very suitably carried out with standard equipment for a creamer preparation line. Thermostatted and moisture-controlled storage rooms are not needed.
- the reaction conditions are chosen such that a protein-carbohydrate conjugate with a glycosylation degree (average number of carbohydrate groups per lysine residue x 100%) of at least 15% is formed, more preferably at least 20% as determined by means of the OPA method. This method is described in Broersen et al., Biotechnology and Bioengineering, vol 86, No 1, April 5, 2004, pp. 78-87.
- the glycosylation degree is up to 100%. From practical considerations (time and cost of preparation), a glycosylation degree of 50% or less is particularly preferred.
- raw materials for a creamer in the framework of the invention conventional materials can be chosen.
- the protein is preferably selected from milk proteins and vegetable proteins, as well as combinations thereof. Very good results have been achieved with caseins and casemates. Particularly suitable vegetable proteins are proteins that can be used as milk protein substitutes, such as wheat protein or soy protein.
- the method according to the invention can in principle be used for the preparation of any type of protein-carbohydrate conjugate, hence also for conjugates having mono- and/or disaccharides therein.
- any reducing carbohydrate can be deployed.
- the reducing carbohydrate can comprise one or more monosaccharides, disaccharides and/or polysaccharides.
- Polysaccharides' is herein understood to mean in particular carbohydrates having at least three saccharide units. Also counted among the polysaccharides are oligosaccharides, i.e. polysaccharides built up from 3-10 saccharide units.
- a creamer which comprises a protein-carbohydrate conjugate of which the carbohydrate is built up from at least three monosaccharide units
- a carbohydrate which is built up from at least three monosaccharide units
- a protein-carbohydrate conjugate prepared with a carbohydrate containing three or more monosaccharide units per molecule has been found to have a better resistance to separation than a conjugate prepared with a monosaccharide or disaccharide (such as lactose), in particular at a temperature of about 90-100 0 C, and/or a high hardness and/or a low pH.
- a monosaccharide or disaccharide such as lactose
- At least the greater part of the polysaccharide molecules have a chain length of at least 6. From practical considerations, such as glycosylation rate considerations, preferably at least the greater part of the polysaccharide molecules have a chain length of less than 20.
- the content of carbohydrates (used for the formation of the conjugate) built up from at least three saccharide units is at least 95 wt.% based on the total carbohydrate content (used for the formation of the conjugate). More preferably, the content of carbohydrates having a chain length of 6-20 is at least 95 wt.% based on the total carbohydrate content.
- oligosaccharides in particular tri- to decasaccharides
- polysaccharides which are at least substantially built up from galactose, fructose, glucose, lactose units or a combination thereof.
- Very good results have been achieved with a creamer containing a conjugate which has been prepared from a protein, preferably a milk protein or vegetable protein, and a maltodextrin.
- the maltodextrin has a dextrose equivalent (DE) - as determined by the Lane Eynon method (AOAC Official Method 935.62) - of about 5 to about 15. More preferably, the maltodextrin contains less than 5 wt.% of mono- and disaccharides.
- DE dextrose equivalent
- the term fat is herein understood to mean a fatty acid glyceride (understood to include a mixture of fatty acid glycerides), in particular a fatty acid triglyceride.
- 'Fats' is understood to include oils (fats which are liquid at room temperature).
- the creamer comprises a solid fat, i.e. a fat which is solid at room temperature (25 0 C).
- the fat can be of vegetable or animal origin. Good results have been obtained with a hardened fat, such as hardened palm fat.
- a reaction mixture is prepared from water, fat, protein and carbohydrate, in which the protein- carbohydrate conjugate is subsequently formed.
- the amounts used can be set within wide limits, depending inter alia on the desired degree of glycosylation.
- the weight ratio of protein to carbohydrate is from about 1:2 to about 1:6, more preferably from about 1:3 to about 1:5, in particular 1:4.
- the needed fat/oil for the manufacture of the creamer can be added wholly or partly to the reaction mixture.
- the amount of water is preferably set at a content corresponding to an a w value (water saturation degree) (for instance as determined using a Novasina a w meter) in the range of from about 0.3 to about 0.8.
- a w value water saturation degree
- the a w is preferably at most 0.75.
- a w is set at a value in the range of 0.63-0.75, in particular 0.65-0.70.
- the glycosylation rate is high and on the other hand stirrability is good and the extent of undesired continuation reactions is low.
- Very good results have been achieved by means of a method in which the a w was about 0.69.
- water is preferably added to a content of at least 8 wt.% based on the weight of the protein plus carbohydrate (in particular at a protein to carbohydrate weight ratio of from 1:2 to 1:6, for instance about 1:4). More preferably, the water content is at least 11 wt.%.
- the water content in the reaction mixture is preferably at most about 25 wt.%, more preferably at most about 20%, still more preferably at most about 14 wt.%, based on the weight of the protein plus carbohydrate.
- the formation of the conjugate preferably takes place at a temperature above the melting point of the fat, in particular at a temperature between about 30 0 C and about 90 0 C.
- the reaction temperature is preferably at least about 50 0 C, more preferably at least 55 °C.
- the reaction temperature is preferably at most about 85 0 C. At such a temperature, few to no undesired Maillard continuation reactions occur. To prevent lumping during the reaction in a simple manner, the temperature is preferably at most about 70 0 C, in particular at most about 60 0 C. However, if a tendency to lumping arises, this can also be reduced or prevented at higher temperature, for instance by stirring more intensively.
- the reaction mixture is allowed to react for at least about 1 hour, preferably for at least about 6 hours. Usually, it is sufficient to allow the reaction mixture to react for about 18 hours at a maximum (in particular at a temperature of at least 55 0 C). Very good results have been achieved with a reaction time of less than about 10 hours, in particular at a temperature of at least 55 0 C.
- the progress of the reaction can be monitored, by measuring the extent of glycosylation continuously or intermittently. Very suitable for this purpose is the OPA method.
- the mixture of water, fat and protein-carbohydrate conjugate is usually processed further. It is not necessary to store the mixture (for a longer time) at a controlled air humidity.
- extra water and/or extra fat and/or extra carbohydrate is added to the mixture to obtain the desired emulsion of fat in water.
- the ratios of water, fat and protein-carbohydrate conjugate and possibly carbohydrate in the emulsion can be as specified in the following table: Typical range for main constituents of a liquid creamer
- the creamer can contain one or more additives that are suitable for use in a creamer.
- the creamer can for instance contain a low-molecular emulsifier. Suitable low-molecular emulsifiers are generally known in the art. Examples are monoglycerides such as glycerol monostearate. Other suitable emulsifiers are for instance described in Emulsifiers, Eagan Press Handbook Series, C. E. Stauffer, 1999.
- the emulsion is pasteurized or sterilized. Because of the resistance to separation of the emulsion in the presence of the protein- carbohydrate conjugate, UHT is very suitable to inactivate or kill off microorganisms.
- the emulsion can be spray-dried, thereby yielding a powder- form creamer.
- spray-drying technique a conventional technique for creamers can be used, such as described, for instance, in "Spraydrying Handbook", fifth edition, 1991, Keith Masters, Editor: Longman Scientific and Technical, ISBN 0582062667. Typical range for main constituents of a powdered creamer
- a powdered creamer comprises in a preferred embodiment up to 25 wt. % protein-carbohydrate conjugate (based on the total weight).
- a creamer according to the invention can be used as such as an end product, for instance instead of milk in coffee or tea.
- a creamer according to the invention in a food, for instance in an acid food, such as tomato soup.
- the invention accordingly relates also to a food comprising a creamer according to the invention.
- the food has, in one embodiment, at least an aqueous phase whose degree of hardness is at least 5 0 DH, preferably 15-30 0 DH.
- the pH is preferably 3.5 - 7.5.
- the pH is herein the value as determined when the food has been brought into a liquid form intended for consumption.
- the food is usually heat-stable, which means in particular that the food is resistant to separation, at least for a few seconds (e.g. 2-10), preferably for at least 15 min, at a temperature of about 70-150 0 C, in particular of about 90 0 C.
- the food is a liquid food, for instance a soup, a sauce or a beverage, such as an alcoholic beverage.
- a conventional food such as a food with a creamer based on non-conjugated protein
- such a food has been found to be very stable, also at a high temperature, for instance of about 90 0 C, and/or a low (acidic) pH and/or hard water.
- a creamer in an acid soup such as tomato soup.
- the food is a concentrate, preferably a powdered concentrate.
- Preferred examples of such concentrates are sauce, soup, coffee (in particular for variants such as cappuccino, cafe au lait, and the like) and tea.
- the food is an instant product.
- the stability was determined in water of a pH of 3.5 (after addition of powder: pH 4.2), a hardness of 30° DH and a temperature of 90 0 C. Both were unstable. Directly after addition of the water, the protein began to separate.
- Example 2 14.7 kg of the dried caseinate/maltodextrin powder as obtained in Example 1 were mixed with 45.3 kg fat. Next, 0.7 kg water was gradually admixed with vigorous stirring, so that the total water content was about 12 wt.% based on the weight of caseinate/maltodextrin powder.
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- Dairy Products (AREA)
- Grain Derivatives (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1027141A NL1027141C2 (en) | 2004-09-29 | 2004-09-29 | Stable creamer. |
| NL1027141 | 2004-09-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2006036059A1 true WO2006036059A1 (en) | 2006-04-06 |
Family
ID=34974604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/NL2005/000697 Ceased WO2006036059A1 (en) | 2004-09-29 | 2005-09-27 | Stable creamer |
Country Status (2)
| Country | Link |
|---|---|
| NL (1) | NL1027141C2 (en) |
| WO (1) | WO2006036059A1 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2025235A1 (en) * | 2007-08-08 | 2009-02-18 | Stichting Top Institute Food and Nutrition | Use of globular protein - oligosaccharide conjugates |
| WO2013006045A1 (en) | 2011-07-01 | 2013-01-10 | Friesland Brands B.V. | Acid-stable creamer or whitener composition |
| US8399039B2 (en) | 2007-11-29 | 2013-03-19 | Nestec S.A. | Shelf stable liquid whitener and process of making thereof |
| WO2015041377A1 (en) * | 2013-09-17 | 2015-03-26 | 남양유업 주식회사 | Method for preparing coffee creamer containing raw milk or skim milk and having improved milk flavor without adding phosphate |
| WO2017022490A1 (en) * | 2015-07-31 | 2017-02-09 | 不二製油グループ本社株式会社 | Method for producing polysaccharide-protein complex |
| CN106535648A (en) * | 2014-07-18 | 2017-03-22 | 雀巢产品技术援助有限公司 | Creamer free from added emulsifier(s), buffer(s) and stabilizing salts |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2325651A1 (en) * | 1972-05-22 | 1973-12-13 | Abbott Lab | Low-calorie fat-free milk substitute - for whitening coffee, tea, soups etc |
| EP0579328A1 (en) * | 1992-07-14 | 1994-01-19 | Campina Melkunie B.V. | Powder-form, foaming creamer |
| US5571334A (en) * | 1994-03-31 | 1996-11-05 | Opta Food Ingredients, Inc. | Starch-based opacifying agent for foods and beverages |
| US20010041211A1 (en) * | 1996-08-21 | 2001-11-15 | Beeson Christine A. | Cold beverage creamer |
| DE20317533U1 (en) * | 2002-11-18 | 2004-02-12 | Unilever N.V. | Particulate cream comprising fat and food compositions comprising this cream |
-
2004
- 2004-09-29 NL NL1027141A patent/NL1027141C2/en not_active IP Right Cessation
-
2005
- 2005-09-27 WO PCT/NL2005/000697 patent/WO2006036059A1/en not_active Ceased
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2325651A1 (en) * | 1972-05-22 | 1973-12-13 | Abbott Lab | Low-calorie fat-free milk substitute - for whitening coffee, tea, soups etc |
| EP0579328A1 (en) * | 1992-07-14 | 1994-01-19 | Campina Melkunie B.V. | Powder-form, foaming creamer |
| US5571334A (en) * | 1994-03-31 | 1996-11-05 | Opta Food Ingredients, Inc. | Starch-based opacifying agent for foods and beverages |
| US20010041211A1 (en) * | 1996-08-21 | 2001-11-15 | Beeson Christine A. | Cold beverage creamer |
| DE20317533U1 (en) * | 2002-11-18 | 2004-02-12 | Unilever N.V. | Particulate cream comprising fat and food compositions comprising this cream |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2025235A1 (en) * | 2007-08-08 | 2009-02-18 | Stichting Top Institute Food and Nutrition | Use of globular protein - oligosaccharide conjugates |
| US8399039B2 (en) | 2007-11-29 | 2013-03-19 | Nestec S.A. | Shelf stable liquid whitener and process of making thereof |
| WO2013006045A1 (en) | 2011-07-01 | 2013-01-10 | Friesland Brands B.V. | Acid-stable creamer or whitener composition |
| WO2015041377A1 (en) * | 2013-09-17 | 2015-03-26 | 남양유업 주식회사 | Method for preparing coffee creamer containing raw milk or skim milk and having improved milk flavor without adding phosphate |
| CN106535648A (en) * | 2014-07-18 | 2017-03-22 | 雀巢产品技术援助有限公司 | Creamer free from added emulsifier(s), buffer(s) and stabilizing salts |
| WO2017022490A1 (en) * | 2015-07-31 | 2017-02-09 | 不二製油グループ本社株式会社 | Method for producing polysaccharide-protein complex |
| CN107846939A (en) * | 2015-07-31 | 2018-03-27 | 不二制油集团控股株式会社 | The manufacture method of polysaccharide protein complex |
| JPWO2017022490A1 (en) * | 2015-07-31 | 2018-05-24 | 不二製油株式会社 | Method for producing polysaccharide-protein complex |
| CN107846939B (en) * | 2015-07-31 | 2022-08-12 | 不二制油集团控股株式会社 | Method for producing polysaccharide-protein complex |
Also Published As
| Publication number | Publication date |
|---|---|
| NL1027141C2 (en) | 2006-03-30 |
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