US20010043908A1 - Liquid oral compositions comprising a calcium compound and an acidulant - Google Patents

Liquid oral compositions comprising a calcium compound and an acidulant Download PDF

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Publication number
US20010043908A1
US20010043908A1 US09/125,471 US12547198D US2001043908A1 US 20010043908 A1 US20010043908 A1 US 20010043908A1 US 12547198 D US12547198 D US 12547198D US 2001043908 A1 US2001043908 A1 US 2001043908A1
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composition
calcium
acid
drink
beverage
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Granted
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US09/125,471
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US6319490B1 (en
Inventor
David Myatt Parker
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SmithKline Beecham Ltd
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SmithKline Beecham Ltd
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Assigned to SMITHKLINE BEECHAM P.L.C. reassignment SMITHKLINE BEECHAM P.L.C. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: PARKER, DAVID MYATT
Publication of US20010043908A1 publication Critical patent/US20010043908A1/en
Assigned to SMITHKLINE BEECHAM PLC reassignment SMITHKLINE BEECHAM PLC CHANGE OF ADDRESS Assignors: SMITHKLINE BEECHAM PLC
Assigned to SMITHKLINE BEECHAM PLC reassignment SMITHKLINE BEECHAM PLC CHANGE ADDRESS OF ASSIGNEE Assignors: SMITHKLINE BEECHAM PLC
Granted legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/02—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation containing fruit or vegetable juices
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/385—Concentrates of non-alcoholic beverages
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/68—Acidifying substances
    • 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
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/16—Inorganic salts, minerals or trace elements
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/191—Carboxylic acids, e.g. valproic acid having two or more hydroxy groups, e.g. gluconic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/06—Aluminium, calcium or magnesium; Compounds thereof, e.g. clay
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/06—Aluminium, calcium or magnesium; Compounds thereof, e.g. clay
    • A61K33/10—Carbonates; Bicarbonates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • 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

  • the present invention relates to compositions for oral use, such as acidic beverages and oral healthcare compositions, and to the use of calcium in such compositions to alleviate or prevent the tooth damage associated with the consumption of acid.
  • the present invention alleviates palatability problems associated with calcium addition to beverages.
  • Calcium is the most abundant mineral in the body. The vast majority of calcium is deposited in the bones and teeth but the mineral is also essential for other bodily functions such as the regulation of nerve function, the contraction of muscles and clotting of blood. Calcium is a common constituent of beverages being derived from fruit ingredients and from hard water when this is used in beverage production without prior softening. Values for the concentration of calcium occurring in this way are typically in the range 0.005-0.02% w/w. Interest in the general nutritional benefits of diet fortification by calcium ion has led to a search for practical ways to incorporate this ion in beverages at higher levels from 0.02% w/w to 2% w/w. The use of calcium as a supplement for beverages has been described in W088/03762.
  • the present invention is based on the discovery that effective reduction of tooth erosion in acidic oral compositions can be achieved with lower amounts of calcium relative to the acidulant when the pH of the composition is also controlled.
  • the present invention provides a liquid composition for oral use containing a calcium compound and an acidulant characterised in that calcium is present in the range of 0.3 to 0.8 mol per mol of acid and that the amount of calcium and acidulant in the composition is selected so that the pH of the composition is from 3.5 to 4.5.
  • the present invention provides the use of calcium as a tooth erosion inhibitor in an acidic liquid composition for oral use by adding a calcium compound to the composition so that calcium is present in the range of 0.3 to 0.8 mol per mol of acid, the amount of calcium and acidulant in the composition being selected so that the pH of the composition is from 3.5 to 4.5.
  • the present invention provides a method of reducing the tooth erosion properties of an acidic oral composition which comprises adding a calcium compound to the acidic liquid oral composition so that calcium is present in the range of 0.3 to 0.8 mol per mol of acid, and if necessary or desired adjusting the pH by addition of an alkali so that the pH of the composition is from 3.5 to 4.5.
  • the present invention provides a process for preparing a composition of this invention which comprises adding a calcium compound to an acidic liquid oral composition so that calcium is present in the range of 0.3 to 0.8 mol per mol of acid, and if necessary or desired adjusting the pH by addition of an alkali so that the pH of the composition is from 3.5 to 4.5.
  • the present invention is applicable to aqueous acidic substances for oral consumption such as acidic beverages, fruit juices, ciders, wines, vinegars and pickles and diverse acidic dairy products and also to other liquid substances to be taken orally such as acidic mouth washes and medicines.
  • the buffering capacity of the formulation is reduced by partial neutalization of the acid, which allows saliva to neutralise residues in the mouth more rapidly.
  • the absolute concentration of calcium used in the present invention is not critical as this will vary according to the nature and concentration of the acids present.
  • the acid solution may contain organic and/or inorganic acids and may be supplemented with vitamins such as ascorbic acid.
  • the calcium concentration may vary from 0.001 mol. per liter to more than 0.05 mol. per liter.
  • the calcium ion concentration may vary from 0.0002 mol. per liter to more than 0.01 mol. per liter.
  • the calcium may be added as any convenient salt such as calcium carbonate, calcium hydroxide, calcium citrate, calcium malate, calcium lactate, calcium chloride, calcium glycerophosphate or calcium formate or any other salt to minimize any adverse flavour contribution to the composition.
  • any convenient salt such as calcium carbonate, calcium hydroxide, calcium citrate, calcium malate, calcium lactate, calcium chloride, calcium glycerophosphate or calcium formate or any other salt to minimize any adverse flavour contribution to the composition.
  • the invention may be carried out by mixing the acid (e.g. citric acid) with its corresponding calcium salt (e.g. calcium citrate) or another calcium salt. It may be advantageous to mix the acid with an alkaline calcium salt such as calcium carbonate or calcium hydroxide thereby minimizing the concentration of acid applied to the formulation.
  • the acid can also be mixed with inorganic calcium salts such as calcium chloride.
  • the molar ratio of calcium to acid may be 0.3-0.75, more typically 0.3-0.65. preferably 0.3-0.55. Most preferably the molar ratio is at least 0.4, and a value of about 0.5 has been found to be especially effective.
  • the pH of the formulation may be adjusted to the desired range by the addition of the calcium compound to the appropriate proportion relative to the acid. If necessary, depending on the acid present, the pH may be further adjusted by the application of an alkali e.g. sodium hydroxide or a suitable salt for example sodium citrate, sodium malate or sodium lactate.
  • an alkali e.g. sodium hydroxide or a suitable salt for example sodium citrate, sodium malate or sodium lactate.
  • the pH of the composition is preferably not more than 4, most preferably from 3.7 to 3.9. Compositions with a pH of about 3.8 have been found to be especially effective.
  • Typical citric or malic acid concentration in a concentrated fruit beverage would be in the range 0.1% w/w to 4% w/w.
  • acid concentrations are typically in the range 0.01 % w/w to 1% w/w.
  • Other potable acids conventional for beverages may also be used, such as lactic acid. Mixtures of potable acids may be used.
  • the acid composition is a drink concentrate prepared from a natural fruit juice, such as blackcurrant juice, for example a flavoured syrup concentrate.
  • the calcium may be added in a suitable form either to the concentrate, especially when the beverage is sold to the consumer as a concentrate for dilution before drinking, or when diluting the syrup concentrate for preparation of a “ready to drink” diluted concentrate.
  • the product contains reduced levels of sugar or carbohydrate or is of low calorie type containing intense sweeteners.
  • the oral composition may contain magnesium or other ions as adjuncts for remineralisation. It may also contain an effective amount of malic acid or potable salts thereof to maintain the solubility of the calcium so as to prevent or minimize the precipitation of insoluble calcium salts. Added malic acid may provide as little as 10% of the total acidity of the beverage, the remainder of the acidity being provided by other, preferably naturally present, acids such as citric acid, or by ascorbic acid.
  • the invention may be applied in a variety of beverages such as concentrates, still fruit drinks, or carbonated soft drinks and in particular to health drinks such as blackcurrant juice drinks or vitamin added beverages.
  • the invention is advantageously applied to drinks containing natural or added citric acid.
  • the beverages may be unsweetened or sweetened with sugar or intense sweeteners such as saccharine, aspartyl phenyl alanyl methyl ester, or other sweeteners known in the art.
  • the beverages may also contain other conventional additives such as sodium benzoate, sorbic acid, sodium metabisulfite, ascorbic acid, flavourings, colorings and carbon dioxide.
  • the beverages may be prepared by mixing the ingredients according to conventional methods.
  • the solid ingredients may be dissolved in water or in hot water if required prior to addition to the other components.
  • drinks are pasteurised prior to filling in bottles or cans or other packs or are “in-pack pasteurised” after filling.
  • a concentrated beverage product, for dilution with five parts of water prior to consumption was prepared by mixing the ingredients as follows.
  • the calcium carbonate was added to the other ingredients as a final addition.
  • Blackcurrant juice concentrate SG 1.27 84 liter Aspartyl phenyl alanyl methyl ester* 1.15 Kg Acesulfame K 1.8 Kg Ascorbic acid 0.8 Kg Sodium benzoate 0.325 Kg Sodium metabisulfite 0.145 Kg Blackcurrant flavouring 0.3 liter Water up to final volume 1000 liter Calcium carbonate 4.2 Kg
  • the concentrate is adjusted to pH 3.7 with sodium hydroxide solution. On dilution of the concentrate with five parts water (to drinking strength), the pH of the composition is typically found to be 3.85.
  • a ready to drink beverage was prepared by mixing ingredients as follows: Ingredients % w/w Sugar 10 Sodium benzoate 0.01 Orange juice 5.04 Ascorbic acid 0.03 Citric acid monohydrate 0.15 Flavouring 0.005 Colouring 0.004 Water by difference 86 Calcium carbonate 0.048 Sodium hydroxide sufficient to adjust to pH 3.9 Carbon dioxide 0.48
  • the mol ratio of calcium : acid is 0.46 (orange juice is typically 1 % w/w citric acid)
  • a ready to drink beverage was prepared by mixing ingredients as follows: Ingredients % w/w Sugar 8 Sodium benzoate 0.01 Apple juice 10 Ascorbic acid 0.03 Malic acid 0.15 Flavouring 0.005 Colouring 0.004 Water by difference 82 Calcium carbonate 0.093 Sodium hydroxide sufficient to adjust to pH 3.9.
  • the mol ratio of calcium: acid is 0.74 (apple juice is typically 0.6 % w/w malic acid)
  • a beverage was produced by mixing ingredients as follows: Blackcurrant concentrate 16.78 liters Aspartyl phenyl alanyl methyl ester 0.54 kg Acesulfame K 0.11 kg Ascorbic acid 0.45 kg Flavouring 0.55 liters Calcium hydroxide 0.52 kg Water to 1000.00 liters
  • the calcium hydroxide was added as a slurry with a portion of the water as a final addition and was sufficient to produce a beverage containing calcium in a molar ratio of 0.5:1 calcium to citric acid.
  • the resultant beverage had a pH of 3.8.
  • the batch was flash pasteurised and packed into 250 ml “Tetra-Brik” containers.
  • each subject After a washout period, each subject then commenced the next treatment period with a fresh enamel specimen.
  • the results are given in the following table and represent microns of enamel lost by the given treatment after the given exposure time and are the means found for the twelve subjects. 5 days 10 days 15 days water 0.098 0.153 0.166 blackcurrant 0.341 0.376 0.407 orange juice 0.911 1.459 2.543
  • a flavoured concentrate was prepared by mixing the following ingredients together with stirring.
  • the calcium hydroxide was added last as a slurry in cold water and the volume adjusted to 1000L with water.
  • Ingredient Unit Quantity Blackcurrant Concentrate L 67.1 Sweetener Kg 3.33 Ascorbic Acid Kg 2.28 Preservatives Kg .0.45 Flavouring L 1.2 Calcium Hydroxide kg 2.96 Water to 1000 liters
  • the beverage concentrate was flash pasteurised at 93° C. for 42 seconds and filled into 600 ml bottles.
  • the molar ratio of calcium to citric acid was 0.4 and the final pH was 3.7.
  • the beverage concentrate was tested for storage stability both at ambient and at 30° C. After a period of 9 months no precipitation of insoluble calcium was observed.
  • a beverage was produced by mixing ingredients as follows: Blackcurrant concentrate 10.07 liters Aspartyl phenyl alanyl methyl ester 0.21 kg Acesulfame K 0.07 kg Ascorbic acid 0.27 kg Lactic acid 80% w/w 0.66 liters Potassium sorbate 0.1 kg Sodium metabisulfite 0.02 kg Flavouring 0.56 liters Calcium hydroxide 0.52 kg Water to 600.00 liters
  • the calcium hydroxide was added as a slurry with a portion of the water as a final addition and was sufficient to produce a beverage containing calcium in a molar ratio of 0.45:1 calcium to citric acid/lactic acid.
  • the resultant beverage had a pH of 3.85.
  • the batch was packed in 250 ml containers and “in-pack” pasteurised.
  • a cola concentrate was prepared by mixing the following ingredients together orthophosphoric acid SG 1.585 41 l citric acid 120 Kg caffeine BP 5.3 Kg cola emulsion 29.25 l caramel double strength 125 l water to 400 l
  • a cola syrup with a throw of 1+5 was then prepared by mixing the following ingredients together Aspartyl phenyl alanyl methyl ester 1.8 Kg soluble saccharin 500 g cola concentrate 25 l cola booster 600 mls calcium hydroxide 3.108 Kg water to 1000 l
  • the calcium hydroxide was added as a slurry with a portion of the water as a final addition and the cola syrup was then diluted with carbonated water, canned and in-pack pasteurised to produce a finished product with a pH of 3.5 and a calcium to acid molar ratio of 0.6.
  • a mouthwash was prepared by mixing the following ingredients: % W/W ethanol 96% BP 8 soluble Saccharin 0.06 cetylpyridinium chloride 0.05 Tego Betain CK-KB5 0.2 flavouring 0.12 sodium acetate trihydrate 0.05 acetic acid 80% 0.1575 calcium chloride dihydrate 0.123 deionised water 91.24
  • a ready to drink beverage was prepared by mixing ingredients as follows: Ingredients % w/v Sodium benzoate 0.01 Malic acid 0.30 Flavouring 0.1 Artificial sweetener 0.05 Water by difference 99.5 Calcium hydroxide 0.083
  • the resultant pH of the composition is typically found to be 3.85 and has a calcium to acid molar ratio of 0.5.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Inorganic Chemistry (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Mycology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Non-Alcoholic Beverages (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
US09/125,471 1996-02-20 1997-02-12 Liquid oral compositions comprising a calcium compound and an acidulant Granted US20010043908A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9603518.3A GB9603518D0 (en) 1996-02-20 1996-02-20 Novel process
GB9603518.3 1996-02-20

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US20010043908A1 true US20010043908A1 (en) 2001-11-22

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US09/125,471 Expired - Fee Related US6319490B1 (en) 1996-02-20 1997-02-12 Liquid oral compositions comprising a calcium compound and an acidulant
US09/125,471 Granted US20010043908A1 (en) 1996-02-20 1997-02-12 Liquid oral compositions comprising a calcium compound and an acidulant
US09/978,993 Expired - Fee Related US6719963B2 (en) 1996-02-20 2001-10-16 Liquid oral compositions comprising a calcium compound and an acidulant
US10/733,992 Expired - Fee Related US6908909B2 (en) 1996-02-20 2003-12-10 Liquid oral compositions comprising a calcium compound and an acidulant

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US09/125,471 Expired - Fee Related US6319490B1 (en) 1996-02-20 1997-02-12 Liquid oral compositions comprising a calcium compound and an acidulant

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US09/978,993 Expired - Fee Related US6719963B2 (en) 1996-02-20 2001-10-16 Liquid oral compositions comprising a calcium compound and an acidulant
US10/733,992 Expired - Fee Related US6908909B2 (en) 1996-02-20 2003-12-10 Liquid oral compositions comprising a calcium compound and an acidulant

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US (4) US6319490B1 (ro)
EP (2) EP1382263B1 (ro)
JP (2) JPH11507842A (ro)
KR (1) KR100301344B1 (ro)
CN (1) CN1149021C (ro)
AP (1) AP1184A (ro)
AR (1) AR005910A1 (ro)
AT (2) ATE339115T1 (ro)
AU (1) AU719631B2 (ro)
BG (1) BG64364B1 (ro)
BR (1) BR9707618A (ro)
CA (1) CA2247114C (ro)
CH (1) CH690815A5 (ro)
CY (2) CY2511B1 (ro)
CZ (1) CZ297770B6 (ro)
DE (3) DE69736683T2 (ro)
DK (2) DK0874558T3 (ro)
EA (2) EA002852B1 (ro)
ES (2) ES2208873T3 (ro)
FI (1) FI981781A0 (ro)
GB (2) GB9603518D0 (ro)
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SA (1) SA97180011B1 (ro)
SE (2) SE521489C2 (ro)
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TR (1) TR199801623T2 (ro)
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UA (1) UA61903C2 (ro)
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050100637A1 (en) * 2003-11-12 2005-05-12 Robert Murray Carbohydrate and electrolyte replacement composition
US20060251573A1 (en) * 2004-03-19 2006-11-09 Musick Charles D Titanium dioxide nanopowder manufacturing process
US20070160958A1 (en) * 2004-09-29 2007-07-12 Belikov Andrei V Method and apparatus for tooth rejuvenation and hard tissue modification
US20080280260A1 (en) * 2004-09-29 2008-11-13 Belikov Andrei V Method and Apparatus for Tooth Rejuvenation and Hard Tissue Modification
US20100129497A1 (en) * 2008-11-24 2010-05-27 Stokely-Van Camp, Inc. Use of novel carbohydrates and carbohydrate blends to provide a sports beverage with increased absorption
US20110064859A1 (en) * 2009-09-17 2011-03-17 Conopco, Inc., D/B/A Unilever Frozen confection

Families Citing this family (49)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9603518D0 (en) * 1996-02-20 1996-04-17 Smithkline Beecham Plc Novel process
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