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WO1998035567A1 - Agents gelifiants et gels contenant ces agents gelifiants - Google Patents

Agents gelifiants et gels contenant ces agents gelifiants Download PDF

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Publication number
WO1998035567A1
WO1998035567A1 PCT/NZ1998/000019 NZ9800019W WO9835567A1 WO 1998035567 A1 WO1998035567 A1 WO 1998035567A1 NZ 9800019 W NZ9800019 W NZ 9800019W WO 9835567 A1 WO9835567 A1 WO 9835567A1
Authority
WO
WIPO (PCT)
Prior art keywords
casein
matrix
dispersion
product
water
Prior art date
Application number
PCT/NZ1998/000019
Other languages
English (en)
Inventor
Richard Beyer
Patrick Joseph Silcock
Original Assignee
University Of Otago
Kiwitech Limited
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by University Of Otago, Kiwitech Limited filed Critical University Of Otago
Priority to AU60078/98A priority Critical patent/AU747859B2/en
Publication of WO1998035567A1 publication Critical patent/WO1998035567A1/fr

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
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/80—Feeding-stuffs specially adapted for particular animals for aquatic animals, e.g. fish, crustaceans or molluscs
    • 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
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
    • A23L29/275—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of animal origin, e.g. chitin
    • A23L29/281—Proteins, e.g. gelatin or collagen
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/30—Encapsulation of particles, e.g. foodstuff additives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/42—Proteins; Polypeptides; Degradation products thereof; Derivatives thereof, e.g. albumin, gelatin or zein

Definitions

  • This invention relates to gelling agents, gels and to processes for preparing them. It also relates to products comprising the gels, in particular matrices for delivering active agent and food products.
  • Gels are formed from macromolecular hydrocolloids and have the ability to form non- deformable structures with low impact resistance.
  • the classical gelling agent which has been most widely studied, is gelatine.
  • This is also the only known food grade hydrocolloid which is a protein.
  • Gelatine is, nutritionally, a low quality protein and gels incorporating it have the disadvantages that they tend to harden on storage and may develop undesirable textural properties.
  • Gelatine may also have negative religious and/or health connotations for some consumers, as it is produced in a manner destructive of animals and there may also be concerns arising from a perceived link with Transmissible Spongiform Encephalopathies such as Bovine Spongiforms Encephalopathy or Creutzfeld-Jacob Disease
  • the present invention may broadly be said to consist in a gelling agent which comprises modified casein, the native structure of the casein having been disrupted sufficiently to cause a composition to which the casein is added in use to gel.
  • the gelling agent comprises a dispersion of modified casein in water and a suitable plasticiser, preferably glycerol.
  • the present invention provides a method of preparing a gelling agent which comprises the steps of:
  • the present invention may broadly be said to consist in a process of preparing a gelled product which comprises adding a gelling agent as defined above to a gellable composition.
  • the invention may broadly be said to consist in a process of preparing a gelled product which involves the use of casein as a gelling agent.
  • the present invention may broadly be said to consist in a gelled product which includes a gelling agent as defined above.
  • the gelled product is a food product.
  • the gelled product is a delivery matrix which comprises (a) a matrix which includes the modified casein; and (b) an active agent incorporated in the matrix,
  • the present invention may broadly be said to consist in a method of preparing a gelled product which comprises the foH ⁇ wing steps:
  • the dispersion also comprises a plasticiser (preferably glycerol) and a suitable buffer to maintain the pH in the range of about 6.1 to about 10. 10.
  • a plasticiser preferably glycerol
  • a suitable buffer to maintain the pH in the range of about 6.1 to about 10.
  • the invention relates generally to gelled products and to macromolecular gelling agents used in their preparation.
  • the ability of a macromolecule to gel depends on interaction between molecules at restricted points along the macromolecule. Portions of the molecule that do not interact disperse in the continuous phase (usually water). Energy is usually required to disrupt the native structures of hydrocolloids. For instance, gelatine is manufactured by applying heat to collagen.
  • the applicants have discovered that the native structure of casein can be disrupted sufficiently for gel formation. This can be achieved, for example, by heating, generally to a temperature of about 95- 110°C or above. It is this finding by the applicants which forms the basis for the present invention.
  • the invention provides a gelling agent which comprises modified casein, in which the native structure of the casein has been disrupted sufficiently to cause a composition to which the casein is added to gel.
  • the gelling agent preferably comprises a dispersion of the modified casein in a suitable plasticiser (preferably glycerol or glycerol combined with propylene glycol (1,2-propanediol) and water, although other forms of the modified casein are by no means excluded.
  • the gelling agents of the present invention have a number of potential applications.
  • the gelling agents may be used in food products.
  • the gelling agents may be used in preparing non-edible gels.
  • they may form part of a delivery matrix in which a matrix containing the modified casein encapsulates an active agent.
  • the preferred formulation of a particular gelling agent of the present invention will depend on the desired end use of the gel.
  • alteration of the amount of plasticiser if any present will change the characteristics of the resultant gel. Similar changes can be effected by changing the identity of the plasticiser.
  • 1,2-propanediol as a plasticiser instead of, or partially instead of glycerol, results in a softer gel with a lower melting point. This may be desirable for some applications, for example where volatiles are to be entrapped or encapsulated by the gel matrix.
  • the gelling agents of the invention are used in preparing food products.
  • the gelling agents, and gelled products containing them may be prepared by first forming a dispersion comprising water and preferably an edible plasticiser, most preferably glycerol, with the dispersion having a pH in the range of about 6.1 to about 8.0. It is preferred that the pH is about 7.5. It is generally desirable that the pH be within the above range when the gelling agent is to be incorporated into a food product, as the resulting gel may be waxy and brittle if the pH is lower than this, or may be unpalatable if the pH is above the upper limit of the range.
  • a preferred buffer is a combination of sodium citrate, calcium carbonate and sodium carbonate. It is preferred that the sodium citrate is present in an amount of about 1.0% to 2.0%, more preferably about 2.0%, by weight of the resulting gel, that the sodium carbonate is present in an amount of about 0.2% to 0.8%, more preferably about 0.4%, by weight of the gel, and that the calcium carbonate is present in an amount of about 0.4% to 1.0%, more preferably about 0.8% by weight of the gel.
  • the calcium carbonate acts as a texture modifier, resulting in a gel with a firmer texture, which is desirable when the gel is to be used as a confectionery product such as a wine gum.
  • the firmer texture is believed to result from interaction between the calcium ion and the casein.
  • glycerol is present in an amount of about 40% to about 55% by weight of the gelled product.
  • Glycerol is a humectant and acts as a plasticiser in the gel.
  • the above range of glycerol concentrations has been found to be desirable for preparing gelled food products having a texture suitable for confectionery products such as wine gums. Of course, for other applications, a harder or softer gel may be desirable and the glycerol concentration should be adjusted accordingly.
  • the water acts to disperse the buffer.
  • the gelled product in which the gelled product is suitable for use as a winegum type product, sufficient water is added so that water is present in an amount of about 26.7% to 34.6% by weight of the gel, more preferably about 30.2% by weight.
  • casein is washed before use in order to remove low molecular weight material.
  • the presence of such low molecular weight material may result in the product having a bitter aftertaste.
  • a suitable method of washing the casein is to use distilled water, preferably at a ratio of about 20: 1 water: casein. The water and the casein are mixed together, and the mixture stirred for approximately one hour, the temperature then increased slowly to 30 C and held for approximately 30 minutes. The mixture is then put on ice, stirred for a further two hours and the small molecular weight casein is removed by filtration, that is, it remains in the filtrate.
  • Other suitable methods of washing the casein will be apparent to those skilled in the art.
  • casein is added to the mixture.
  • the casein should be added sufficiently slowly to avoid the formation of lumps.
  • the proportion of casein in the gel is about 18% by weight. Concentrations of casein significantly lower than this may produce gels which are too soft and fail to hold their shape after gelling, whereas significantly higher concentrations may produce gels which are too hard and do not have the 'gummy' texture required when the product is to be a confectionery product such as a wine gum. It will of course be appreciated that gels which are either soft or hard will be appropriate for applications other than as a confectionery such as a wine gum. Gels which contain more or less than 18% by weight of modified casein are therefore in no way excluded from the present invention.
  • the washed casein will retain a significant amount of water. This means that the water content of the casein will need to be determined and the amounts of water and casein adjusted accordingly, to give the desired proportions of water and casein in the composition.
  • the mixture should continue to be stirred.
  • the mixture is heated to a sufficient temperature and for a sufficient time to disrupt the native structure of the casein sufficiently to allow gel formation to occur. It is preferred that the mixture be heated until the temperature reaches about HO C, more preferably about 112 C, or when foaming lessens.
  • the heating time required will depend on the rate of heating, but in practice, a heating time of between about 6 and 13 minutes will usually be sufficient.
  • the resulting solution which is the gelling agent, is then removed from the heat.
  • additional components are then added to the solution. These preferred additional components are:
  • a sweetening agent is a combination of fructose and aspartame.
  • alternative sweetening agents both nutritive and non- nutritive will be known to persons skilled in the art, and may also be used.
  • a concentration of fructose of about 6.0% to about 10.0% by weight of the gel, most preferably about 8.0% by weight, and aspartame, in an amount of about 0.1% by weight of the gel have been found to produce an acceptable level of sweetness.
  • the amounts of the sweetening agents may of course be adjusted depending on the desired level of sweetness in the gel.
  • the resultant gel may have a bitter aftertaste.
  • a suitable flavor modifier will eliminate this.
  • the flavor modifier is maltol (3-hydroxy-2-methyl-4-pyrone), present in an amount of about 0.1% by weight of the gel. Maltol minimizes bitterness and enhances sweetness.
  • a texture modifier is a particularly preferred texture modifier which has been found to improve the texture of the gel.
  • carrageenan which is preferably added in an amount of about 0.15% to about 0.25% by weight of the gel.
  • alternative texture modifiers for example gums such as carboxy methyl cellulose, may also be used.
  • Components (1) to (3) are stirred into the solution after it has been removed from the heat, until all components have been dispersed. If desired, food grade colorings and/ or flavorings may then also be added.
  • the resulting mixture is then allowed to cool and set. It is preferred that the mixture be poured into a mould so that the gel sets in a desired shape.
  • the gelled product can be coated with an agent which hardens the outside of the gel. If such a coating is desired, then approximately one hour after pouring, the gelled product can be removed from the mould and coated with the hardening agent.
  • a preferred hardening agent is a citric acid/ calcium citrate dip, consisting of an aqueous solution comprising about 15% by weight citric acid and 1% by weight calcium citrate.
  • the pH of the dip is preferably about 2.0, which is lower than the isoelectric point of casein (pH 4.5).
  • Casein and distilled water were stirred for one hour at a 20: 1 ratio waterxasein. The temperature was increased slowly to 30 C and held for 30 minutes. The sample was then put on ice and stirred for a further 2 hours and filtered. A moisture determination of the casein indicated an average moisture content of 63.4% and the above formulation was calculated to provide a final moisture content of 30.2% and a casein content of 18.0%.
  • the resulting gelled product had a texture and flavour suitable for use as a winegum type confectionery product.
  • the gelling agents of the present invention may also be used in products other than food products, for example as part of a delivery matrix.
  • a matrix comprising the modified casein encapsulates an active agent for which a slow or controlled release from the composition is desired.
  • the delivery matrices comprising the gelling agents of the present invention may conveniently be prepared by first preparing a modified casein matrix, melting the matrix, adding the active agent and any other desired ingredients (such as an emulsifier if required), and then allowing the mixture to cool and set into a desired shape.
  • the modified casein matrix may generally be prepared by heating casein in the presence of water and preferably a plasticiser, and at a pH of about 6.1 to about 10.10. It is preferred that the heating be carried out under basic conditions, and preferably at a pH of about 9.7.
  • One preferred buffer which may be used to achieve the desired pH is sodium carbonate, but other buffers, such as potassium carbonate, trisodium phosphate and calcium hydroxide may also be used.
  • plasticiser used is glycerol, but other plasticisers, such as sorbitol, may also be used and are by no means excluded from the invention.
  • casein be heated in the presence of a cross- linking agent such as dimethyl adipate.
  • a cross-linking agent increases the molecular weight of the modified casein and also decreases its solubility, resulting in a firmer gel.
  • the preferred method of preparation is to dissolve the buffer in water, add the plasticiser and the cross-linking agent, and heat the mixture to 50 C before adding the casein. Once the casein is added, the mixture is heated further, preferably to around 130 C, and continued until the casein is cross-linked sufficiently to reduce solubility. Following the heating, the mixture is allowed to cool and set into a desired shape.
  • An active agent can then be incorporated into the matrix, with the aid of an emulsif ⁇ er if required, by melting the matrix together with the emulsifier (preferably at a temperature of around 70 C-80 C) and mixing in the active agent until homogeneity is achieved.
  • a suitable emulsifier is a mixture of 80% Datem (mono- and diglyceride monoacetyl and diacetyl tartaric acid) /20% Calcium phosphate, although other suitable emulsifiers will be apparent to those skilled in the art. The mixture may then be moulded into the desired shape.
  • the active agent can be any substance which it is desired to incorporate in a delivery matrix.
  • the active agent could be a pharmaceutical.
  • it could be an insect or animal attractant or repellant, as in the examples which follow.
  • the relative amounts of the components used in preparing the modified casein matrix will again depend on the end use to which the gelled product is to be put.
  • an example of a suitable matrix formulation is as follows: about 34% glycerol, about 32.6% lactic acid casein, about 21.7% water, about
  • the relative proportions of the modified casein matrix, active agent and emulsifier in the final gelled product will also depend on the nature of the active agent and the end use to which the product is to be put. Generally, it has been found that active agent can be incorporated satisfactorily into the modified casein matrix at a weight ratio of up to about 1: 10 active agent:modified casein matrix.
  • a suitable composition may comprise around 5% by weight active agent, 1% emulsifier and 94% modified casein matrix. Emulsification difficulties may be experienced if the concentration of active agent is much higher, for example around 20% by weight.
  • Glucono-d-lactone is the preferred acid for achieving the decrease in pH because of its low solubility and because it brings about a slow decrease in pH.
  • other weak organic acids such as citric acid may also be used; these would have the advantage of being less expensive than glucono-d-lactone.
  • the sodium carbonate was dissolved in the water; glycerol and dimethyl adipate were added and stirred. The mixture was heated to 50 C, the casein added and heating continued to 130 C. The mixture was poured onto a board, flattened and left to cool. The cray attractant was incorporated into the matrix with the aid of an emulsifier in the proportions outlined below:
  • the attractant was occluded using the following method:
  • the matrix was cut into small pieces and heated with the emulsifier in a crucible in a water bath. The mass was heated until the matrix had melted (temperature between 70°C and 80°C). The mass was mixed until homogeneous. The mass was removed from the heat and the attractant was weighed directly into the mass and mixed until homogeneous, with extra heating to facilitate mixing. The mass was removed from the crucible and moulded into the desired shape.
  • compositions were prepared, varying the proportion of cray attractant (20%, 10% and 1% attractant). These formulations were prepared using the same method as described above but with the following modification: the cray attractant was weighed onto a small piece of paraffin film ( ⁇ 0.01g) then added to the matrix without requiring removal of the matrix from the heat,. These formulations were as follows:
  • the resulting composition can be used to attract crayfish by placing the composition in craypots. It is believed the attractant will release slowly from the composition and will therefore have the advantage of lasting for a considerable time, generally around two days.
  • composition containing entrapped torn cat pheromone was prepared, having the following formulation:
  • the casein matrix was prepared using the same method as described above in Example 2.
  • the torn cat pheromone was dispersed in the acetone and then blended with the vegetable oil.
  • the casein matrix was melted and the torn cat pheromone, acetone and vegetable oil were added and mixed until homogeneous.
  • the base was then moulded into the desired shape.
  • the resulting composition is believed to release torn cat pheromone at a slow rate. Without wishing to be bound by any theory, it is believed the active ingredient will diffuse through the casein matrix and volatilise. As herbivores are believed to be repelled by the scent of carnivore pheromones, it is envisaged that the composition has potential utility in repelling herbivores. For example, discs of the composition can be attached to trees (eg pine seedlings) which require protection from herbivores such as possums.
  • a composition in the form of discs incorporating mink anal gland pheromone (3,3- dimethyl- l,2-dithiolane (DMDT)) was prepared, using the method described above in Example 2 (entrapped cray attractant).
  • the formulation for the composition was as follows:
  • DMDT is a carnivore odor which appears to induce a fear response in possums.
  • the compositions containing entrapped DMDT are therefore believed to be potentially useful as a repellent for herbivores.
  • they may be attached to pine seedlings in order to repel possums from the seedlings.
  • the modified casein matrix formulation is as follows:
  • composition of the finished products were as follows:
  • Component % (weight /weight) casein matrix 97.0 emulsifier (80% Datem/ 20% Ca3P ⁇ 4) 2.0 male stoat anal gland extract 1.0
  • Component % (weight /weight) casein matrix 97.0 emulsifier (80% Datem/ 20% Ca3P ⁇ 4) 2.0 female stoat anal gland extract 1.0
  • the casein matrix used for the rat repellents was the same as that used for the stoat anal glands.
  • composition of the finished products were as follows:
  • Component % (weight /weight) casein matrix 93.0 emulsifier (80% Datem/ 20% Ca3PO-i) 2.0
  • a fly attractant was incorporated into two matrices: a solid gel matrix (as above), and a thick paste-like matrix.
  • the product was prepared as per the stoat product with the exception the attractant was added at 2% and 10%.
  • the composition of the products were as follows:
  • the product was prepared as per the stoat product with one exception.
  • Sodium sulfide was dispersed in the extra water (added to aid melting) at a rate of 1.5% (w/w) of the fly attractant.
  • casein matrix was reformulated to produce a paste-type product at room temperature (it gels at low temperatures).
  • the modified formulation is as follows: Component % (weight /weight)
  • the water and propylene glycol are mixed;
  • thin boiling starch (TB840), sodium carbonate, calcium carbonate and xanthan gum are dry blended (powdered mix);
  • the powdered mix is dispersed in the water and propylene glycol and mixed until free of lumps;
  • the mixture is heated to between 95°C and 100°C for 10 minutes;
  • the maltodextrin (DE 10) is added and mixed until dispersed; The hot mass is cooled to room temperature.
  • a fly attractant can be prepared from the above product by the following method: The casein paste matrix is warmed to between 25°C and 30°C; the emulsifier and sodium sulphide dispersed in the matrix; the attractant added and mixed until dispersed.
  • the mass can either packed off directly into a suitable tube or heated to 35°C (to facilitate filling) then packed off into a suitable tube.
  • the texture/ viscosity of the product can be easily altered, for example by:
  • novel gelling agents and gels according to the present invention will find widespread acceptance.
  • they are suitable for use in food products such as confectionery, as described above.
  • the geUed products according to the invention wiU possess enhanced textural properties on storage as compared with currently available gels formed from gelatine.
  • the gelling agents may be employed in the preparation of non- edible gels.
  • Such gels may for example form part of a deUvery matrix, as described above.
  • Pharmaceutical/ medical appUcations are also possible.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Zoology (AREA)
  • Nutrition Science (AREA)
  • Health & Medical Sciences (AREA)
  • Birds (AREA)
  • Animal Husbandry (AREA)
  • Marine Sciences & Fisheries (AREA)
  • Insects & Arthropods (AREA)
  • Biochemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Jellies, Jams, And Syrups (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Colloid Chemistry (AREA)
  • Medicinal Preparation (AREA)

Abstract

L'invention concerne des agents gélifiants à base de caséine modifiée, des gels, et leurs procédés de préparation. L'agent gélifiant à base de caséine modifiée est de la caséine dans laquelle la structure endogène a été rompue.
PCT/NZ1998/000019 1997-02-17 1998-02-16 Agents gelifiants et gels contenant ces agents gelifiants WO1998035567A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU60078/98A AU747859B2 (en) 1997-02-17 1998-02-16 Gelling agents and gels containing them

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NZ314255 1997-02-17
NZ31425597 1997-02-17

Related Child Applications (3)

Application Number Title Priority Date Filing Date
US09367501 A-371-Of-International 1999-11-29
US09/987,320 Continuation-In-Part US6610348B2 (en) 1997-02-17 2001-11-14 Gelling agents and gels containing them
US09/987,320 Continuation US6610348B2 (en) 1997-02-17 2001-11-14 Gelling agents and gels containing them

Publications (1)

Publication Number Publication Date
WO1998035567A1 true WO1998035567A1 (fr) 1998-08-20

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PCT/NZ1998/000019 WO1998035567A1 (fr) 1997-02-17 1998-02-16 Agents gelifiants et gels contenant ces agents gelifiants

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WO (1) WO1998035567A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3119315A1 (fr) * 2021-02-02 2022-08-05 Virbac « gel diffuseur de pheromones »

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5358730A (en) * 1991-02-08 1994-10-25 Bongrain S.A. Process for coagulating or gelling a nondenatured protein and product thereof

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Publication number Priority date Publication date Assignee Title
JPS6037941A (ja) * 1983-08-10 1985-02-27 Meiji Milk Prod Co Ltd ゼリ−状食品ベ−スの製造方法
JP2782458B2 (ja) * 1989-07-13 1998-07-30 雪印乳業株式会社 透明なカゼインゲル化物の調製方法

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5358730A (en) * 1991-02-08 1994-10-25 Bongrain S.A. Process for coagulating or gelling a nondenatured protein and product thereof

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
COLLOIDS AND SURFACES, Vol. 50, 1990, ROEFS S.P.F.M. et al., "Structure of Acid Casein Gels 1. Formation and Model of Gel Network", pages 141-159. *
DERWENT ABSTRACT, Accession No. 85-089475, Class D13; & JP,A,60 037 941 (MEIJI MILK PROD CO LTD) 27 February 1985. *
DERWENT ABSTRACT, Accession No. 91-105641, Class D13; & JP,A,03 047 042 (SNOW BRAND MILK PRODUCTS) 28 February 1991. *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3119315A1 (fr) * 2021-02-02 2022-08-05 Virbac « gel diffuseur de pheromones »
WO2022167389A1 (fr) * 2021-02-02 2022-08-11 Virbac Gel diffuseur de pheromones

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Publication number Publication date
AU747859B2 (en) 2002-05-23
AU6007898A (en) 1998-09-08

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