WO2006007662A1 - Procedes d'augmentation de la stabilite de la mousse - Google Patents

Procedes d'augmentation de la stabilite de la mousse Download PDF

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Publication number
WO2006007662A1
WO2006007662A1 PCT/AU2005/001081 AU2005001081W WO2006007662A1 WO 2006007662 A1 WO2006007662 A1 WO 2006007662A1 AU 2005001081 W AU2005001081 W AU 2005001081W WO 2006007662 A1 WO2006007662 A1 WO 2006007662A1
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WO
WIPO (PCT)
Prior art keywords
calcium
casein
water
phenol
composition
Prior art date
Application number
PCT/AU2005/001081
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English (en)
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WO2006007662A8 (fr
Inventor
Richard Pelham Garland
Original Assignee
Phoscal Holdings Pty 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
Priority claimed from AU2004904081A external-priority patent/AU2004904081A0/en
Application filed by Phoscal Holdings Pty Limited filed Critical Phoscal Holdings Pty Limited
Publication of WO2006007662A1 publication Critical patent/WO2006007662A1/fr
Publication of WO2006007662A8 publication Critical patent/WO2006007662A8/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/12—Aerosols; Foams
    • A61K9/122—Foams; Dry foams
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents

Definitions

  • This invention relates to methods for increasing the foam stability of compositions using casein phosphoproteins.
  • Foam formation is a property that has many applications.
  • the degree of usefulness of a foam often depends on the stability of the foam, which in turn is dependent on a number of physical and chemical properties of the composition, such as the surfactant properties and the film strength.
  • a composition that forms a stable foam possesses a high film strength and surfactant properties.
  • There are a large number of applications where it is desirable to maximise the foam stability of various compositions for both aesthetic reasons (for example, food and beverage applications) and also for reasons of function, such as enhancement of the efficacy of certain products (for example, oral care products).
  • certain complexes of casein phosphoproteins have increased foam stability and therefore have a potentially wide variety of applications.
  • the present invention provides a method for increasing the foam stability of a composition, said method comprising the addition to said composition of a formulation comprising a water-soluble or water-dispersible form of at least one isolated and purified casein phosphoprotein, or salt thereof, complexed with calcium phosphate.
  • the present invention provides a method for increasing the foam stability of a composition, said method comprising the addition to said composition of a formulation comprising a water-soluble or water-dispersible form of at least one isolated and purified casein phosphoprotein, or salt thereof, complexed with at least one bioactive constituent, wherein the bioactive constituent is selected from the group consisting of calcium phosphate, and calcium phosphate admixed with at least one other bioactive constituent.
  • the present invention provides a method for increasing the foam stability of a composition, said method comprising the addition to said composition of a formulation comprising a water-soluble or water-dispersible form of at least one isolated- and purified casein phosphoprotein, or salt thereof, complexed with calcium phosphate, and wherein said purified casein phosphoprotein, or salt thereof, is complexed with calcium phosphate at a pH of between about 6.5 to about 10.
  • the method of the first, second or third embodiments may be used to increase the foam stability of any suitable composition.
  • the method may be used in compositions where casemate can be used for its foaming ability both for increasing foam stability, and also where it is advantageous to use less protein relative to other components in order to achieve the same foaming effect.
  • the compositions may include: foodstuffs such as milk (for example milk used in drinks such as cappuccinos and the like), cakes and cheeses etc, pharmaceutical products, and possibly even keg beer.
  • the method of the third embodiment may also comprise the addition to said composition of a formulation comprising a water-soluble or water-dispersible form of at least one isolated and purified casein phosphoprotein, or salt thereof, complexed with at least one bioactive constituent, wherein the bioactive constituent is calcium phosphate admixed with at least one other bioactive constituent.
  • the present invention provides a method for increasing the contact time of a bioactive constituent to a biological surface, said method comprising administration of a formulation comprising a water-soluble or water- dispersible form of at least one isolated and purified casein phosphoprotein, or salt thereof, complexed with at least one bioactive constituent, wherein the bioactive constituent is calcium phosphate.
  • the method of the fourth embodiment may also comprise administration of a formulation comprising a water-soluble or water-dispersible form of at least one isolated and purified casein phosphoprotein, or salt thereof, complexed with at least one bioactive constituent, wherein the bioactive constituent is calcium phosphate admixed with at least one other bioactive constituent.
  • the present invention provides a method for increasing the contact time of a bioactive constituent to a biological surface, said method comprising administering a composition prepared in accordance with the method of any one of the first, second or third embodiments.
  • the biological surface may include all tissues of the oral cavity, and may also include skin, and the alimentary tract, including the lining of the stomach and the intestinal walls.
  • the formulations used in the methods of the invention may comprise at least one of the phosphoproteins disclosed herein.
  • the biological surface may be a dental surface such as teeth and gums.
  • casein is used in a manner which includes orthophosphate and fluorophosphate such that the words may herein be used interchangeably.
  • isolated and purified should be understood to mean a form of casein that has been extracted, removed and purified to a more pure form than that actually present in the natural form.
  • casein as it is present in milk is present in a water insoluble, micellar form and requires the presence of sufficient quantities of ions such as magnesium and citrate to maintain its micellar structure.
  • casein protein in s accordance with the present invention has been isolated and purified from milk, and in doing so, contains essentially no magnesium and citrate etc.
  • increasing foam stability in the first, second or third embodiments should be understood to mean that the foam stability of the composition to which the formulation is added is greater following addition of the formulation, than the o foam stability of the initial composition prior to addition of the formulation.
  • Figure 1 Plot of the percentage foam heights of the formulations of the methods of the present invention together with data obtained for some other casein o phosphoprotein/phosphopeptide formulations.
  • Figure 2 Visual representation of the foam heights of the formulations used in the methods of the present invention (tube 1), and that of comparative formulations (casein peptone complexed with 3% calcium phosphate (tube 3) and sodium caseinate (tube 2)). Best Mode of Performing the Invention
  • the present invention is based on the discovery that formulations comprising phosphoproteins complexed with bioactive constituents such as calcium phosphate display remarkably, and unexpectedly high foam stability. As such, the methods of the
  • compositions are useful where it is desired to increase the foam stability of a composition, whether the composition be a solution, suspension or mixture.
  • the formulations may be used to increase the bioavailability of mineral or vitamin supplements.
  • the formulations used in the methods of the invention may be used to coat small particles of a mineral, for example calcium carbonate or calcium o citrate.
  • the combination of increased foam stability of the formulation and small particle size results in a high ratio of casein phosphoprotein calcium phosphate complex to mineral supplement and thus helps assist in maintaining solubility of the mineral until it is transported to the intestine thereby increasing the overall bioavailability of the calcium supplement.
  • the isolated and purified casein phosphoprotein may comprise at least one casein phosphoprotein as disclosed in Whitney, R. Proteins of Milk. In: Fundamentals of Dairy Chemistry 3 rd Edn. (1988) (ed. N.P.
  • the casein phosphoprotein may be selected from the group consisting of: ⁇ -casein, ⁇ -casein, K- 0 casein, and mixtures thereof.
  • the casein phosphoprotein may be selected from the group consisting of:
  • ⁇ -Casein X a -5P (genetic variants-A 1 , A 2 , A 3 , B, C-4P, D-4P, and E)
  • ⁇ -Casein X a -lP (f 29-209) (genetic variants-A 1 , A 2 , A 3 , and B) 3.
  • ⁇ -Casein X a -(f 106-209) (genetic variants-A 1 , A 3 , and B)
  • the phosphoproteins may alternatively be obtained from suitable plant sources.
  • the phosphoprotein may be present in the form of a salt.
  • the salt may be selected from the group consisting of: a metal salt, an alkaline metal salt, a transition metal salt or an alkaline earth metal salt.
  • the alkaline metal salt may be selected from the group consisting of: a sodium salt and a potassium salt.
  • the alkaline earth metal salt may be selected from the group consisting of: a calcium salt, a strontium salt and a magnesium salt.
  • the transition metal salt may be selected from the group consisting of: a zinc salt, a copper salt and a nickel salt.
  • the metal salt may be an aluminium salt.
  • the formulations of the present invention may include one or more phosphatase inhibitors.
  • the phosphatase inhibitors may be selected from the group consisting of: fluoride ions, vinyl ether maleic acid polymers, and divalent and trivalent metal ions.
  • the casein phosphoprotein may be isolated and purified from bovine, ovine or caprine milk.
  • the casein phosphoprotein for use in the methods of the invention may be any commercially available casein phosphoprotein. Note that unless otherwise stated, all percentages of components of the formulations used in the methods of the invention are by weight, based on the total weight of the formulations.
  • the amount of phosphoprotein present in the formulations may be between about
  • the amount of phosphoprotein present in the formulations may be between about 0.01 and 25%.
  • the amount of phosphoprotein present in the formulations may be between about 0.5 and 20%.
  • the amount of phosphoprotein present in the formulations may be between about 1% and 10%.
  • the amount of phosphoprotein present in the formulations may be between about 2% and 7%.
  • the amount of phosphoprotein present in the formulations may be approximately 3.5%.
  • the formulations contain calcium phosphate in the form of a complex with the at least one casein phosphoprotein, or salt thereof.
  • the casein calcium phosphate complex present in the formulations is a discrete chemical entity and not merely a mixture of phosphoprotein and calcium phosphate as separate species in solution.
  • the complex is understood to exist in the form of a reconstituted, or artificial casein micelle in which amorphous calcium phosphate is stabilised.
  • the amorphous calcium phosphate is in the form of nanometre-sized particles, hence the aggregate may also be described as nanoclusters.
  • the casein calcium phosphate complex is prepared by addition of a source of soluble calcium ions and a source of soluble phosphate ions to a solution of a water-soluble salt of casein that has been adjusted to a pH of about 6.5 to about 10.
  • a water-soluble salt of casein that has been adjusted to a pH of about 6.5 to about 10.
  • the water-soluble salt of casein is sodium caseinate, and the pH is adjusted to between 8 and 10.
  • the casein calcium phosphate complex is prepared by dissolving sodium caseinate and disodium phosphate in water, and adjusting the pH of the mixture to between about 6.5 to about 10. A solution of calcium chloride may then added. In order to maximise the foam stability of a solution comprising the casein calcium phosphate complex, it is desirable to prepare the complex under conditions such that a stoichiometric excess of phosphate ions are added to the solution comprising the water- soluble salt of casein present relative to the amount of calcium ions that are added.
  • the Applicant believes that the formulations comprising a complex of casein and calcium phosphate are able to increase the contact time of a bioactive constituent with a biological surface as a result of the superior film strength and surfactant properties of the complex as compared to, for example caseinate per se. In this way, the complex is able to "cling" to the biological surface for an extended period, thereby facilitating delivery of bioactive constituents to the surface.
  • the amount of complex present in the formulations may be between about 0.0001 and about 60%.
  • the amount of complex present in the formulations may be between about 0.01 and 25%.
  • the amount of complex present in the formulations may be between about 0.5 and 20%.
  • the amount of complex present in the formulations may be between about 1% and 10%.
  • the amount of complex present in the formulations may be between about 2% and 7%.
  • the amount of complex present in the formulations may be approximately 3.5%.
  • the amount of calcium present in the formulations may be between about 0.0001% and about 5%.
  • the amount of calcium present in the formulations may be between about 0.001% and 0.5%.
  • the amount of calcium present in the formulations may be between about 0.002% and 0.1%.
  • the amount of calcium present in the formulations may be between about 0.01% and 0.06%.
  • the amount of calcium present in the formulations may be about 0.04%.
  • the amount of phosphate present in the formulations may be between about 0.0001% and about 10%.
  • the amount of phosphate present in the formulations may be between about 0.001% and 1.0%.
  • the amount of phosphate present in the formulations may be between about 0.002% and 0.5%.
  • the amount of phosphate present in the formulations may be between about 0.02% and 0.5%.
  • the amount of phosphate present in the formulations may be between about 0.05% to 0.2%.
  • the formulations may have a pH of about 4.7 and 10.
  • the formulations may have a pH of between about 8 and 10.
  • the formulations may have a pH of between about 6 and 8.5.
  • the formulations may have a pH of between about 6.5 and 7.5.
  • the formulations for use in the methods of the invention may be sterile formulations.
  • the formulations may be pasteurised.
  • pasteurisation substantially eliminates or reduces bacterial contamination that could cause odorous bacterial breakdown of the formulation, or cause illness in the recipient of the end product comprising the formulation.
  • the bioactive constituent may be an inorganic bioactive constituent or an organic bioactive constituent.
  • Inorganic bioactive constituents may be selected from the group consisting of: calcium, phosphate, fluorophosphate, fluoride, zirconia, magnesium, barium, zinc, iron, copper, aluminium, tin, silver and salts of said bioactive constituents selected from the group consisting of: titanium dioxide, zinc oxide, calcium fluoride, sodium fluoride, stannous fluoride, calcium phosphate, calcium fluorophosphate and calcium oxide.
  • the casein phosphoprotein acts to sequester the bioactive constituent such as calcium phosphate to form an amorphous complex as described herein which may be used as a soluble source of calcium and phosphate ions.
  • Fluoride sources used in the formulations may include: sodium fluoride, stannous fluoride, sodium monofluorophosphate, zinc ammonium fluoride, tin ammonium fluoride, calcium fluoride or cobalt ammonium fluoride.
  • Fluoride ions may be provided at a level of from about Oppm to ⁇ OOOppm, Oppm to 3000 ppm, 5 ppm to 1500 ppm, or 50 ppm to 1500 ppm.
  • Surfactants such as soap, anionic, nonionic, cationic, amphoteric and/or zwitterionic surfactants may also be present in the formulations as a bioactive constituent, or as an additional agent within the formulations.
  • the surfactants may be present in a range of 0% to 15%, 0.1% to 15% or 0.25 to 10% by weight.
  • the surfactants may be sodium decyl sulfate, sodium lauryl sarcosinate and sodium dodecylbenzene sulfonate.
  • the amount of inorganic bioactive constituents present in the formulations may be between about 0.005% and 50%, 0.2 and 35%, 0.5% and 15% or 0.5% and 10%.
  • the bioactive constituents may comprise organic bioactive constituents which bind to the casein protein, yet do not affect its biological activity.
  • the organic bioactive constituents include the antimicrobial agents outlined below.
  • the organic bioactive constituent may also include corticosteroid hormones, such as Cortisol, adrenocorticotropin, corticotropin; pain killing agents such as aspirin and/or paracetamol; vitamins and/or optical brighteners for improvement in the appearance of teeth, such as stilbene disulfonic acid.
  • corticosteroid hormones such as Cortisol, adrenocorticotropin, corticotropin
  • pain killing agents such as aspirin and/or paracetamol
  • vitamins and/or optical brighteners for improvement in the appearance of teeth such as stilbene disulfonic acid.
  • Many of the organic bioactive constituents safeguard the formulation against ultra-violet or visual light radiolytic degradation.
  • the amount of organic bioactive constituents present in the formulations may be between about 0.005% and about 30%, about 1% and about 20%, about 1% and about 15% or about 1 and about 5%.
  • the isolated and purified casein protein present in the formulations used in the invention may also be subject to bacterial contamination and odorous breakdown. Therefore, the bioactive constituent present in the formulation may itself be at least one antimicrobial agent, or may further comprise at least one antimicrobial agent as a further bioactive constituent, together with other bioactive constituents. Any antimicrobial agent used in commerce is also suitable for use in the formulations of the present invention.
  • the antimicrobial agent may include an organic antimicrobial agent, wherein the organic antimicrobial agent is typically water-soluble.
  • the anti-microbial agent may be selected from the group consisting of: halogenated diphenyl ethers, such as: 2,4,4-trichloro-2-hydroxy-diphenyl ether (triclosan); phenolic compounds, including phenol and its homologues, such as: 2-methyi- phenol, 3 -methyl-phenol, 4-methyl phenol, 4-ethyl phenol, 2,4-dimethyl-phenol, 3,4- dimethyl-phenol, 2,6-dimethyl-phenol, 2,2-methylene bis (4-chloro-6-bromo-phenol); mono- and poly-alkyl and aromatic halophenols, including p-chlorophenols such as: methyl-p-chlorophenol, ethyl-p-chlorophenol, n-propyl-p-chlorophenol, n-butyl- chlorophenol; -o-chlorophenols; p-bromophenols; -o-bromophenols; resorcino
  • the antimicrobial agent may be selected from the group consisting of: glycerol, ethanol, sorbitol, mannitol, sodium benzoate, methyl-p-hydroxybenzoate, ethyl-p- hydroxybenzoate, N-propyl p-hydroxybenzoate, butyl-p-hydroxybenzoate, phenoxy ethanol and quaternary ammonium salts, such as benzethonium chloride, and diisobutyl- phenoxyethoxyethyl dimethyl benzyl ammonium chloride.
  • antimicrobial agents may include amidines, such as substituted guanidine, including, chlorhexidine, and other known bis-biguanidines; and cationic tertiary amines.
  • amidines such as substituted guanidine, including, chlorhexidine, and other known bis-biguanidines
  • cationic tertiary amines Any suitable flavouring or sweetening material may also be employed.
  • suitable flavouring constituents are flavouring oils. For example, oil of spearmint, peppermint, wintergreen, sassafras, clove, sage, eucalyptus, marjoram, cinnamon, lemon, and orange, and methyl salicylate.
  • Suitable sweetening agents include sucrose, lactose, maltose, dextrose, levulose, sorbitol, xylitol, d-tryptophan, dihydrochalcones, sodium cyclamate, perillartme, APM (aspartyl phenyl alanine, methyl ester), and saccharine.
  • flavouring and sweetening agents may together comprise from about 0.1% to about 10% by weight or more of the formulation, and more typically, from about 0.1% to about 5% by weight or more of the formulation.
  • formulations that may be used in the methods of the invention are as follows, wherein all proportions are expressed by weight:
  • a formulation for use in the methods of the invention may contain a viscosity modifier as follows:
  • a formulation for use in the methods of the invention may contain a Vitamin as follows:
  • a formulation for use in the methods of the invention may contain an extra mineral as follows:
  • a formulation for use in the methods of the invention may contain an enzyme as follows:
  • a formulation for use in the invention may be spray-dried to form a powder, including the following components:
  • the formulations for use in the invention may be spray dried or freeze dried.
  • the formulations of the invention may be spray dried or freeze dried and later resuspended or dissolved for use.
  • the formulations may be used in spray dried form depending on the intended application.
  • Spray-dried and freeze dried formulations can be prepared using standard techniques known to those skilled in the art.
  • a spray-dried powder of the above formulation may be obtained from a Niro Production Minor Spray Drier (Niro Australia Pty. Ltd, Blackburn VIC, Australia), with an inlet temperature of about 200 0 C, and a flow rate that controlled the outlet temperature to about 85°C.
  • the resultant spray-dried powder may be added to any composition in which it is desired to increase the foam stability of said composition.
  • casein calcium phosphate complex is prepared by first dissolving in water a mixture of sodium casemate (Tatua Co-operative Dairy Co Ltd ) and disodium phosphate (Ajax Chemicals) (food grade), before adjusting the pH of the mixture to a pH of between about 6.5 to about 10. The pH may alternatively be adjusted to between about 8 and about 10.
  • This homogeneous mixture provides a stock solution of the casein calcium phosphate complex comprising approximately 35g /L sodium caseinate, 0.7g/L calcium and 1.2 g/L phosphate. In this instance, the complex reflects a molar excess of approximately 8% phosphate.
  • the bioactive constituents with the exception of calcium chloride and ethanol, are provided as solids, to be dissolved or maintained in aqueous solution or suspension.
  • Solution 2 Formulation of the present invention (labelled as "Phoscal” on the graph)
  • Solution 4 A calcium phosphocaseinate derivative at pH 7.4.
  • Solution 5 Casein pliosphopeptide-calcium phosphate complex
  • Solution 6 A calcium phosphocaseinate derivative at pH 9.
  • Solution 7 The formulation of the present invention at pH 7.4 (in this instance, a molar excess of approximately 64% phosphate is reflected).
  • Solutions 3, 4 and 6 were found to attain comparably higher initial foam heights s than solutions 1 and 5, with these initial foam heights decreasing more gradually with increasing time, thereby indicating some minor degree of foam stability. In stark contrast
  • Solutions 2 and 7 demonstrate an excellent foam height which remains essentially constant over a time period of 10 to 30 minutes after agitation has ceased. This result indicates a markedly superior foam stability of the formulations used in the methods of Q the present invention.
  • a formulation for use in accordance with the invention may be prepared according to the following: 1) Part A: To 920 ml of water add 1.75 g of disodium phosphate and ImI of 19 molar sodium hydroxide and warm to 6O 0 C. Add 35 g of sodium caseinate to the solution with stirring and stir until all the caseinate had dispersed.
  • Part B Slowly add a solution of 1.75 g of calcium chloride dihydrate in 65ml of water. Continue stirring with an overhead mixer for 2 - 3 hours. In this instance, the complex would reflect a molar excess of approximately 64% phosphate.
  • a formulation for use in accordance with the invention, producing a complex reflecting a molar excess of approximately 63% phosphate may be prepared according to the following:

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Nutrition Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Communicable Diseases (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Zoology (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Detergent Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

L'invention se rapporte à un procédé d'augmentation de la stabilité de la mousse d'une composition. Ce procédé consiste à ajouter dans la composition une formulation contenant une forme hydrosoluble ou hydrodispersible d'au moins une phosphoprotéine de caséine purifiée, ou un sel de celle-ci, complexé avec du phosphate de calcium.
PCT/AU2005/001081 2004-07-22 2005-07-22 Procedes d'augmentation de la stabilite de la mousse WO2006007662A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
AU2004904081 2004-07-22
AU2004904081A AU2004904081A0 (en) 2004-07-22 Methods for Increasing Foam Stability
AU2004904938A AU2004904938A0 (en) 2004-08-30 Methods for increasing foam stability
AU2004904938 2004-08-30

Publications (2)

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WO2006007662A1 true WO2006007662A1 (fr) 2006-01-26
WO2006007662A8 WO2006007662A8 (fr) 2006-06-15

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010068093A1 (fr) 2008-12-08 2010-06-17 Campina Nederland Holding B.V. Poudre contenant une graisse en particules, sa préparation et son utilisation

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000006108A1 (fr) * 1998-07-29 2000-02-10 Pacific Biolink Pty. Limited Formulations de caseine destinees a la delivrance de constituants bioactifs
WO2002094204A1 (fr) * 2001-05-21 2002-11-28 The University Of Melbourne Matieres dentaires restauratrices
WO2004035077A1 (fr) * 2002-10-18 2004-04-29 Patrick Joseph Silcock Preparations a base de phosphoproteines pour l'apport d'ions metaux bioactifs et remineralisation des dents

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000006108A1 (fr) * 1998-07-29 2000-02-10 Pacific Biolink Pty. Limited Formulations de caseine destinees a la delivrance de constituants bioactifs
WO2002094204A1 (fr) * 2001-05-21 2002-11-28 The University Of Melbourne Matieres dentaires restauratrices
WO2004035077A1 (fr) * 2002-10-18 2004-04-29 Patrick Joseph Silcock Preparations a base de phosphoproteines pour l'apport d'ions metaux bioactifs et remineralisation des dents

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010068093A1 (fr) 2008-12-08 2010-06-17 Campina Nederland Holding B.V. Poudre contenant une graisse en particules, sa préparation et son utilisation

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