EP1663126A1 - Agent topique a action par voie orale sensiblement anhydre contenant une ou plusieurs matieres sensibles a l'oxydation - Google Patents

Agent topique a action par voie orale sensiblement anhydre contenant une ou plusieurs matieres sensibles a l'oxydation

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Publication number
EP1663126A1
EP1663126A1 EP04764666A EP04764666A EP1663126A1 EP 1663126 A1 EP1663126 A1 EP 1663126A1 EP 04764666 A EP04764666 A EP 04764666A EP 04764666 A EP04764666 A EP 04764666A EP 1663126 A1 EP1663126 A1 EP 1663126A1
Authority
EP
European Patent Office
Prior art keywords
green tea
oxidation
mouthwash
agent
toothpaste
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.)
Withdrawn
Application number
EP04764666A
Other languages
German (de)
English (en)
Inventor
Jürgen Herbert VOLLHARDT
Cornelia RÜTTI
Philippe Emmanuel Maillan
Christine Saecker
Horst Westenfelder
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DSM IP Assets BV
Original Assignee
DSM IP Assets BV
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Filing date
Publication date
Application filed by DSM IP Assets BV filed Critical DSM IP Assets BV
Priority to EP04764666A priority Critical patent/EP1663126A1/fr
Publication of EP1663126A1 publication Critical patent/EP1663126A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • A61K8/34—Alcohols
    • 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
    • A61K8/34—Alcohols
    • A61K8/347—Phenols
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • 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
    • A61K8/67—Vitamins
    • 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
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • 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

Definitions

  • the invention relates to an orally active topical agent selected from a toothpaste, a mouthwash and a mouthwash concentrate which contains one or more substances sensitive to oxidation, in particular one or more polyphenols from green tea. Surprisingly, it has been found that the stability of such an agent can be significantly improved if the agent has a water content of not more than 7.5% by weight, based on the total weight of the agent.
  • a number of diseases and disorders occur in the area of the oral cavity, e.g. Dental caries, gingivitis, inflammatory processes such as, in particular, periodontitis and bad breath, which is mostly caused by volatile sulfur compounds in the oral cavity, which are caused by the constipation of sulfur-containing amino acids and proteins by oral microorganisms. Furthermore, diseases of oxidative stress can occur in the biological tissue of the oral cavity. This is also often inflammation.
  • agents designed specifically for topical administration in the oral cavity and on the teeth such as, in particular, dentifrices such as toothpaste or tooth gel, sprays, mouthwashes and mouthwashes are used.
  • WO 99/17735 discloses the use of certain chelates for the treatment of bad breath, to name just one example from the large number of publications which deal with active ingredients for oral treatment of the oral cavity.
  • Fluorine compounds are known as active substances against tooth decay.
  • the use of plant extracts in dental care products or products for treating the oral cavity is also widespread, and reference can be made here, for example, to WO 02/092028 or FR 2 791 893.
  • Products with extracts from green tea are also known.
  • Green tea has a long tradition as a remedy, particularly in East Asian folk medicine. Chen Zang, a Chinese pharmacist (Tang Dynasty, 618-907), has already handed down the saying that every medicine is only a medicine for a certain disease, but tea is a medicine for all diseases.
  • the main ingredients of the green tea extract are polyphenols, so-called catechins.
  • catechins The most widely represented catechin is (-) - epigallocatechin gallate.
  • the green tea catechins are characterized by a very strong antioxidant effect. They also have an antimicrobial effect and are also deodorising against various bad smells. This combination of efficacies makes them principally for use in dental and oral care, e.g. interesting for the prevention or treatment of caries, gingivitis, periodontitis and bad breath.
  • the bacterial effectiveness protects against tooth decay and gingivitis (build-up of pauque), while the antioxidant effect prevents inflammatory processes or alleviates their course.
  • the deodorant properties reduce bad breath, on the one hand by binding bad-smelling components, but also by combating the sulfur-producing bacteria in the oral cavity due to their antimicrobial activity and thereby preventing the development of bad breath.
  • epigallocatechin gallate a green tea polyphenol
  • oral care products for example, in EP 67 476.
  • WO 02/02096 discloses that whole body wellbeing can be improved when certain topical oral compositions are administered.
  • Epigallocatechin gallate is mentioned as a possible active ingredient among many.
  • the oral formulations of the publication are also not further restricted, including caramel, chewing gum, tooth powder, etc.
  • Water is stated as a possible carrier of the oral formulations, which is generally about 5% to about 70%, preferably about 20% to about 50 % of the remedy. This value refers to all water including the water bound to auxiliary substances and to all oral formulations.
  • the total water content is not specified for a toothpaste.
  • About 2% to about 45% are given for the value of the water added as a carrier.
  • the agents disclosed by way of example all contain more than 6.5% of water added as a carrier.
  • the object of the invention is to provide new orally active topical agents which can treat the entire spectrum of diseases and disorders occurring in teeth and in the oral cavity, and which are particularly effective in caries and gingivitis, but which also reliably combat bad breath or prevent its occurrence, which are effective in the case of inflammation in the area of the oral cavity and in particular in the case of periodontosis and with which oxidative stress conditions in biological tissues of the oral cavity can also be treated.
  • the funds are supposed to have an attractive appearance, so that they can be marketed as toothpaste and mouthwash concentrate or mouthwash and this appearance should be maintained even after prolonged storage at room temperature or at least changed less than is the case with products of the prior art.
  • the solution to this problem is based on the surprising finding that the stability of substances sensitive to oxidation and in particular of polyphenols from green tea can be considerably improved if these substances, in particular the polyphenols, are formulated in agents which have a water content of not more than 7. 5% by weight, based on the total weight of the agent. If the agents have other components that promote the decomposition of oxidation-sensitive substances, especially green tea polyphenols, in particular basic components such as e.g. Cleaning agents based on silicon dioxide or lime, which are often contained in toothpastes, can further improve the stability of the oxidation-sensitive substances, in particular the green tea polyphenols, if these constituents are conditioned with an acid.
  • the invention thus provides an orally active topical agent, selected from toothpastes, mouthwashes and mouthwash concentrates, containing one or more oxidation-sensitive substances and in particular green tea polyphenols, which has a water content of 7.5% by weight or less.
  • the invention also relates to the use of oxidation-sensitive substances and in particular green tea polyphenols for the production of such an agent with a water content of 7.5% by weight or less for topical treatment of the oral cavity and / or teeth.
  • the invention also relates to a process for reducing the decomposition of oxidation-sensitive substances and in particular the discoloration of green tea polyphenols in such an orally active topical agent, which is characterized in that the water content of the agent is 7.5% by weight or less is set.
  • water which is used in the preparation of the orally active topical compositions that is to say added to the mixture as a carrier (“free water”)
  • free water has a considerably greater effect on the stability of the substances sensitive to oxidation and in particular of the green tea polyphenols, as water, which is bound to auxiliaries and additives, such as water, which is introduced into the agent via silica gel or titanium dioxide.
  • the invention thus also relates to a method for producing an orally active topical agent which contains oxidation-sensitive substances and in particular green tea polyphenols, selected from toothpastes, mouthwashes and mouthwash concentrates, in which less than 2% by weight of water is used as free, non-auxiliary or additives bound water is added, and the oral agents obtainable thereby.
  • an orally active topical agent which contains oxidation-sensitive substances and in particular green tea polyphenols, selected from toothpastes, mouthwashes and mouthwash concentrates, in which less than 2% by weight of water is used as free, non-auxiliary or additives bound water is added, and the oral agents obtainable thereby.
  • an “orally active topical agent” is understood to mean an agent which is introduced into the oral cavity and there exerts a medical, hygienic or cosmetic activity on the teeth and / or other areas of the oral cavity.
  • the agents are toothpaste, mouthwashes and mouthwash concentrates.
  • oral cavity is understood to mean the entire area of the mouth and throat area which is accessible for topical treatment.
  • a mouthwash can also be referred to as a mouthwash, but in the present case the more precise expression mouthwash is preferred since the mouthwashes according to the invention are essentially free of water.
  • the mouthwash concentrates according to the invention are generally formulated into finished mouthwashes before use by the end user by adding a diluent, usually water.
  • the substances sensitive to oxidation are not particularly restricted.
  • these are retinoids, ascorbyl compounds, ascorbic acid, Resveratrol, ubiquinones, flavonoids and / or green tea polyphenols.
  • the flavonoids and particularly preferably the green tea polyphenols are preferred.
  • Ascorbyl compounds in particular include ascorbyl phosphates, such as the ascorbyl phosphates sold under the Stay-C brand, for example sodium ascorbyl phosphate (Stay-C50).
  • the group of retinoids conceptually includes all retinoids that are safe for use in oral agents, including retinol and its esters, retinais and retinoic acid and its esters.
  • Retinol also: axerophthol; [3,7-dimethyl-9- (2,6,6-trimethyl-1-cyclohexenyl) -2,4,6,8-nonatetraen-1-ol
  • vitamin A is synonymous with vitamin A.
  • retin-1-carboxylic acid vitamin A acid, retinoic acid, tretinoin
  • esters or retin-1 al vitamin A aldehyde
  • the retinol esters according to the invention preferably have the structure
  • X preferably represents a branched or unbranched alkanoyl or alkenoyl radical of 1 to 25 carbon atoms.
  • Retinal vitamin A1 aldehyde, 3,7-dimethyl-9- (2,6,6-trimethyl-1-cyclohexenyl) -2,4,6,8-nonatetraenal
  • Retinal arises from the oxidative cleavage of carotene.
  • Retinoic acid [vitamin A acid, all-trans-3,7-dimethyl-9- (2,6,6-trimethyl-1-cyclohexenyl) -2,4,6,8-nonatetraenoic acid] is by structure
  • the ester group which is optionally present instead of the hydrogen atom of the acid is preferably an alkyl group having 1 to 25 carbon atoms.
  • the ascorbic acid is in particular L-ascorbic acid ⁇ (R) -5 - [(S) -1, 2-dihydroxyethyl] -3,4-dihydroxy-5-H-furan-2-one, vitamin C ⁇ the structural formula
  • Ascorbyl compounds are preferably understood to mean ascorbyl esters of fatty acids, particularly preferably ascorbyl palmitate. Ascorbyl compounds in the narrower sense are in particular the ascorbyl esters of the general structure
  • R can represent a branched or unbranched alkyl radical having up to 25 carbon atoms.
  • the present invention also includes ascorbylglycosides, in particular the ascorbylglucosides, in particular the ascorbyl-2-glucoside of the structure
  • Ascorbyl compounds in the narrower sense are also the ascorbyl phosphates, particularly advantageously the ascorbyl 2-phosphates of ascorbic acid or its alkali metal, alkaline earth metal, zinc salts or mixed salts of such cations.
  • a triple deprotonated ascorbyl phosphate ion is shown above, although other deprotonation stages are also advantageous in the sense of the present invention.
  • the sodium, magnesium and zinc salts for example sodium ascorbyl phosphate, are preferred.
  • Flavones or flavonoids are known and are often used in cosmetics or dermatology. Here, reference can be made in particular to WO 00/74641, to which reference can be made in this regard.
  • Flavon and its derivatives are characterized by the following basic structure (substitution positions specified):
  • flavones usually occur in glycosidated form.
  • flavonoids that can be used according to the invention are flavanones
  • Oxidation-sensitive substances in the sense of the invention are also flavonoids of the generic structural formula
  • Zi to Z 7 are independently selected from the group H, OH, alkoxy and hydroxyalkoxy, where the alkoxy or hydroxyalkoxy groups can be branched and unbranched and can have 1 to 18 carbon atoms, and wherein Gly is selected from the Group of mono- and oligoglycoside residues,
  • Zi to Z 6 are independently selected from the group H, OH, alkoxy and hydroxyalkoxy, where the alkoxy or hydroxyalkoxy groups can be branched and unbranched and can have 1 to 18 carbon atoms, and wherein Gly is selected from the Group of mono- and oligoglycoside residues, Flavonoids of the generic structural formula
  • Gly 2 or Gly 3 can also individually or together represent saturations by hydrogen atoms.
  • Gly, Gly 1 f Gly 2 and Gly 3 are preferably selected independently of one another from the group of the hexosyl radicals, in particular the rhamnosyl radicals and glucosyl radicals.
  • hexosyl radicals for example allosyl, altrosyl, galactosyl, gulosyl, idosyl, mannosyl and talosyl or pentosyl radicals, can also be used.
  • Z 1 to Z 7 can preferably be selected independently of one another from the group H, OH, methoxy, ethoxy and 2-hydroxyethoxy.
  • ⁇ -Glucosylrutin, ⁇ -Glucosylmyrictrin, ⁇ -Glucosylisoquercitrin and ⁇ -Glucosylquercitrin can be particularly mentioned.
  • flavonoids are ⁇ -glucosylrutin, naringin (aurantiin, naringenin-7-rhamnoglucoside), hesperidin (3 ', 5,7-trihydroxy-4'-methoxyflavanon-7-rutinoside,
  • Tetrahydroxyflavanone-7-glucoside Tetrahydroxyflavanone-7-glucoside
  • isoquercitrin 3,3 ', 4', 5,7-pentahydroxyflavanone-3- ( ⁇ -D-glucopyranoside).
  • oxidation-sensitive substance within the meaning of the invention is resveratrol, a style derivative found in plants.
  • the oxidation-sensitive substances are one or more green tea polyphenols which, in particular in toothpastes, mouthwashes and mouthwash concentrates of the prior art, show strong discoloration due to oxidation and therefore make the agents commercially unattractive.
  • green tea polyphenols are used in the context of this invention, these are understood to mean polyphenol compounds which are present in green tea and which can be obtained from green tea in a conventional manner by extraction and, if appropriate, further separation processes, in particular by chromatographic separation processes , Of the polyphenols found in green tea, the compound (-) - epigallocatechin-3-gallate (EGCG)
  • green tea polyphenols are optically active substances
  • a reference to such a substance means a reference to each individual stereoisomer, in particular each of the optically active enantiomers (preferably to the naturally occurring optically active enantiomer) and to any mixtures thereof, especially on racemates.
  • green tea polyphenols encompasses all polyphenols present in green tea, but in particular the compounds mentioned above, and very particularly the compound (-) - epigallocatechin-3-gallate.
  • the green tea polyphenols can be obtained in the usual way from green tea, for example by extracting the leaves of the green tea with hot water, which gives an extract which is obtained from approx. 40% polyphenols and its typical ingredients in Table 1
  • Flavanols (contains eg EGCG) 25.0 flavonols and flavonol glycosides 3.0 phenolic acids and epsides 5.0 other polyphenols 3.0 caffeine 3.0 theobrom in 0.2 Remaining ingredients
  • the green tea polyphenols or flavones in the extract e.g. as follows: mg / 100 mg of dried tea leaves (%)
  • an aqueous extract of green tea as described above, can be used, if appropriate after further concentration, to reduce the water content in the preparation of the agents according to the invention.
  • the remaining ingredients are preferably separated off as far as possible, so that only the green tea polyphenols are used.
  • the extract used preferably contains at least 30%, if appropriate after chromatic purification, more preferably at least 50%, more preferably at least 70%, in particular at least 80%, for example at least 90%, most preferably at least 95% of green tea polyphenols, in particular the green tea polyphenols specified above, in each case stated as% of the dry matter.
  • a chromatographically purified product is particularly preferably used, and even more preferably a purified product in which the content of epigallocatechin gallate is increased as much as possible, for example to 80% or more, preferably to 90% or more, based on the total amount of green tea -Polyphenols, each stated in% of the dry weight.
  • epigallocatechin gallate is particularly preferably used as green tea polyphenol, which is purified as far as possible and contains only minor traces (5% or less, preferably 3% or less, more preferably 2% or less) of the other green tea polyphenols, each indicated in % of dry matter.
  • the aqueous green tea extract can be purified chromatographically in a manner known per se, such as, for example, in Separation of individual catechins from green tea using silica gel column chromatography and HPLC. Journal of Food Lipids (2003), 10 (2), 165-177. CODEN: JFFLES ISSN: 1065-7258. Reference can also be made to EP-A 1 077 211, EP-A 1 103 550, US-A 6,210,679, WO-A 97/30597 and WO-A 95/18540, which disclose corresponding work-ups of the green tea extract and to which reference is made.
  • the aqueous green tea extract of the green tea polyphenols often already contains brown-colored degradation products of the green tea polyphenols, which gives the agent according to the invention a slightly brown discoloration. In individual cases, this may still be acceptable, provided that this discoloration is not too strong, since the discoloration does not increase significantly when the agent according to the invention is stored, when using purified green tea extract and in particular when using a chromatographically separated polyphenol fraction as described above, this problem can be avoided, however, and the topical agents obtained orally show a particularly attractive color.
  • the content of green tea polyphenols in the agent according to the invention is not particularly restricted.
  • the content of oxidation-sensitive substances, in particular green tea polyphenols is usually 0.01% by weight to 10% by weight, preferably 0.05 to 8% by weight, for example 0.1 to 5% by weight. amount, each based on the total weight of the agent according to the invention.
  • oxidation-sensitive substances in particular green tea polyphenols, but also in ascorbic acid and derivatives thereof, retinoids, in particular retinol, but also retinyl derivatives such as retinyl palmitate, resveratrol and ubiquinone, from 0.01 to 5% by weight, in particular from 0 , 01 to 3 wt .-%, for example from 0.01 to 2 wt .-%.
  • compositions While usually a considerable proportion of water is used in orally active topical compositions, since water is an excellent physiologically compatible carrier material, it is essential according to the invention that the compositions contain no more than 7.5% by weight of water, based on the total weight of the By means of otherwise oxidative decomposition of the oxidation-sensitive substances or discoloration of the green tea polyphenols occurs when the agents are stored, which gives the agents an unacceptable brown discoloration, especially if the agents are toothpaste, mouthwash or mouthwash concentrates.
  • the water content in toothpaste and mouthwashes or mouthwash concentrates is usually much higher, for example DE-A 42 37 500 describes toothpastes with a water content of well over 30% by weight and WO 02/02096 also goes from 5% to 70% % Water content in oral formulations and adds more than 6.5% free water to the preparation of the agents disclosed by way of example, so that the water bound to auxiliaries and additives results in a total water content of in any case more than 8%.
  • the water content is preferably not more than 6.5% by weight, more preferably not more than 4.8% by weight and most preferably not more than 1.9% by weight, in each case based on the Total weight of the product.
  • Karl Fischer's water determination is described, for example, in "Karl Fischer Titration: Determination of Water (Chemical Laboratory Practice / Instructions for Chemical Laboratory Practice, Vol. 20, Eugene Scholz, Springer Verlag, 1984").
  • the water (free water) used as carrier during the preparation of the composition according to the invention adversely affects the stability of the oxidation-sensitive substances and in particular the green tea polyphenols, while water bound to auxiliaries and additives has less adverse effect on the stability.
  • the agents according to the invention therefore, preferably less than 2% by weight of free water is used, more preferably 1.5% by weight or less, more preferably 1.0% by weight or less, more preferably 0.5% by weight. % or less, most preferably no free water is used at all.
  • free water is understood to mean water which is present as a liquid and is not adsorptively or bound as crystalline water to solid substances such as silica gel, sorbitol or titanium dioxide.
  • the amount of free water in the agent according to the invention results from the amount of water used as a carrier in the preparation.
  • oxidation-sensitive substances in particular green tea polyphenols
  • topical agents which act orally
  • constituents of these agents which can impair the stability of the oxidation-sensitive substances, in particular green tea polyphenols , acidifying conditioning, ie treatment with an acidic agent.
  • additives of the agent favor the decomposition and these additives can then undergo acidifying conditioning are subjected, whereby the compatibility of the additives is improved and the stability of the agent according to the invention, in particular the discoloration due to degradation products of the green tea polyphenols, is further restricted.
  • Such additives which are particularly incompatible with green tea polyphenols but also with other oxidation-sensitive substances, are compounds which react in a basic manner, i.e. Compounds that produce a pH of more than 7 in aqueous suspension or solution.
  • Such basic additives are often used in particular in toothpastes, and in particular the cleaning bodies based on silicon dioxide which are frequently present in toothpastes can be used to decompose the substances sensitive to oxidation, in particular the Green tea polyphenols, contribute to brown-colored and brown-colored decomposition products.
  • the decomposition of the oxidation-sensitive substances, in particular the discoloration of the green tea polyphenols, is therefore reduced even more according to the invention if additives which are incompatible with the oxidation-sensitive substances, in particular the green tea polyphenols, e.g. a basic cleaning body, in particular a cleaning body based on silicon dioxide, e.g. Silicic acid gel or based on lime, as is often used in toothpastes, are subjected to an acidifying conditioning step, that is to say a treatment with an acid-reacting compound (addition of the acid-reacting compound to the incompatible additive).
  • additives which are incompatible with the oxidation-sensitive substances, in particular the green tea polyphenols e.g. a basic cleaning body, in particular a cleaning body based on silicon dioxide, e.g. Silicic acid gel or based on lime, as is often used in toothpastes, are subjected to an acidifying conditioning step, that is to say a treatment with an acid-reacting compound (ad
  • the toothpastes according to the invention preferably contain a basic cleaning body, in particular a cleaning body based on silicon dioxide or aluminum dioxide, such as silica gel or aluminum hydroxide, preferably in an amount from 10% by weight to 30% by weight, more preferably from 10% by weight to 20% by weight.
  • a basic cleaning body in particular a cleaning body based on silicon dioxide or aluminum dioxide, such as silica gel or aluminum hydroxide, preferably in an amount from 10% by weight to 30% by weight, more preferably from 10% by weight to 20% by weight.
  • acid-reacting compounds are all compounds which, in a 1% solution or dispersion, have a pH of less than 7.0, more preferably a pH of 6.0 or less, even more preferably a pH - Deliver a value of 5.0 or below, especially 4.0 or below.
  • Suitable acidifying conditioning can be carried out, for example, with citric acid, e.g. with 50% citric acid. The conditioning can either be done in a separate step, the basic compound, e.g.
  • the cleaning body based on silicon dioxide is treated in a first step with the acid-reacting compound and then added to the agent according to the invention, or it can be carried out in the formulation of the agent according to the invention, as is preferred and is explained in more detail in the examples.
  • the agents according to the invention therefore preferably contain an acid-reacting compound e.g. Citric acid.
  • the acid-reacting compound is preferably present in an amount of 0.05 to 5%, in particular 0.1 to 3%, in the agent according to the invention, in particular in the toothpaste according to the invention.
  • the oral topical agents according to the invention are, for example, toothpastes which represent the center and the basis of every dental care and are therefore frequent contain oxidation-sensitive substances or form the most suitable platform for the application of the multi-active effects of green tea phenols.
  • Another important product form in dental care is mouthwash. In addition to an antimicrobial effect, they are particularly valued for their deodorization. Green tea polyphenols also offer a double effect here.
  • the oral topical agents according to the invention are therefore toothpastes, mouthwashes or mouthwash concentrates.
  • the orally active topical agents according to the invention can be pharmaceuticals, cosmetic products or hygiene products.
  • Common ingredients and additives of the toothpastes, mouthwashes and mouthwash concentrates according to the invention are known to the person skilled in the art and are described in relevant standard works such as formulation technology, H. Mollet, A. Grubenmann, Wiley VCH 2000.
  • the agents according to the invention can in particular also contain further active substances, such as antibacterial active substances, for example further extracts of natural products, which have an antibacterial effect.
  • Further possible additives of the agents according to the invention are, for example, conventional anti-caries agents such as phosphates, pyrophosphates, polyphosphates, phosphonates, polyphosphonates and mixtures thereof.
  • the toothpastes according to the invention can furthermore be customary polishing materials (or a cleaning body) such as silicon dioxide, aluminum dioxide, phosphates and mixtures thereof, such as, for example, dicalcium orthophosphate dihydrate, calcium pyrophosphate,
  • Lime can also be included as a cleaning body; in practice, ground or precipitated lime is used in particular.
  • Polyethylene fine powder can also be used as a cleaning body, e.g. Fine powder with ⁇ 10 ⁇ m particle size, e.g. is distributed by the company BASF, Ludwigshafen, Germany.
  • the toothpastes can also contain other conventional additives, e.g.
  • agents for changing the tooth color such as in particular agents for whitening the teeth, minerals, vitamins and nutrients, sweeteners, humectants, fillers, thickeners, alkali metal bicarbonates, buffers, colorants, flavorings , etc.
  • the agents according to the invention will also contain at least one carrier material.
  • a preferred carrier for the toothpastes which is particularly preferred according to the invention is glycerol, but other non-aqueous carriers known in the art, such as propylene glycol and polyglycerol, can also be used.
  • the mouthwash concentrates or mouthwashes can be produced on the basis of alcohol (ethanol) or alcohol-free. Non-alcoholic mouthwash concentrates have the advantage that they can also be used safely by children. Alcohol-containing mouthwash concentrates can be produced, for example, on the basis of a glycerol-ethanol mixture.
  • a suitable carrier material for alcohol-free mouthwash concentrates is e.g. Glycerin, propylene glycol and polyglycerin.
  • Glycerin anhydrous ad 100 epigallocatechin gallate (EGCG) 0.10 Texapon N70 (sodium lauryl sulfate) 1, 42 sodium fluoride 0.22 sodium saccharin 0.10 Carbopoi 981 (carbomer) 0.70 Syloblanc ⁇ l (silica gel) 10.00 Syloblanc 82 ( Silica gel) 10.00
  • Toothpaste was prepared by first mixing all the substances listed under A) individually in the order given at room temperature with slow stirring. Stirring was continued until a homogeneous paste was formed. In a separate vessel, the substances specified under B) were mixed at room temperature with slow stirring and added to the homogeneous paste at room temperature. It was mixed again until a homogeneous paste was formed.
  • the homogeneous paste is suitable as toothpaste and contains 0.1% by weight epigallocatechin gallate. The total water content according to Karl Fischer was 4.7%.
  • Example 1 The two toothpastes from Example 1 and Comparative Example 1 were stored for eight weeks at room temperature (25.degree. C.) and independently of this for eight weeks at 5.degree. C., and then the color was assessed colorimetrically.
  • the colorimetric assessment was based on a CIE 1976 L xaxb "Colorspace” assessment as described in "Color Physics for Industry” by Roderick McDonald, Society of Dyers & Colorists, March 1997.
  • ⁇ E [(L - L 0 ) 2 + (a - a 0 ) 2 + (b - b 0 ) 2 ] 1/2 from a so-called color space, where L stands for brightness, positive values a red colors mean negative values for a green colors mean positive values for b yellow colors and negative values for b blue colors.
  • L stands for brightness
  • positive values a red colors mean negative values for a green colors mean positive values for b yellow colors and negative values for b blue colors.
  • CM-3600d Minolta Spectrophotometer
  • the toothpaste according to the invention is more stable than the comparison product when stored at only 5 ° C.
  • the toothpaste of the comparative example on an aqueous basis was so discolored after eight weeks of storage at room temperature that the toothpaste is no longer suitable for commercial purposes.
  • the toothpaste according to the invention showed only a slight discoloration, which does not interfere with commercial use.
  • VB means the toothpaste of the comparative example and EM means the toothpaste according to the invention.
  • ⁇ E indicates the "colorspace" rating.
  • a mouthwash concentrate with the ingredients (in% w / w)
  • a comparative mouthwash concentrate which, as is customary in the prior art, contains water and the ingredients (data in% w / w)
  • Example 2 and Comparative Example 2 were stored for three months at room temperature and independently of this for three months at 5 ° C. A colorimetric determination was then carried out as in test example 1 and the result is shown in FIG. While the discoloration of the mouthwash concentrate is still acceptable at 5 ° C for the comparative product, the discoloration of the comparative product at room temperature after three months of storage is so high that the product is no longer commercially usable. There is also a certain discoloration in the mouthwash according to the invention, but this is considerably less than the discoloration of the comparative product.
  • VB means the mouthwash concentrate from the comparative example and EM means the mouthwash concentrate according to the invention from example 2.
  • ⁇ E indicates the "colorspace" rating.
  • a mouthwash concentrate with the ingredients (in% w / w)
  • Toothpastes were prepared in a conventional manner from the constituents given in the following tables.
  • the toothpastes were stored at different temperatures and after two weeks and after three weeks the content of the reaction-sensitive substance was determined in the usual way. The results are also shown in the following tables. In all toothpastes, the total water content according to Karl Fischer was less than 0.5%. 4. Toothpaste with ascorbic acid

Abstract

La présente invention concerne un agent à action par voie orale qui se présente sous forme d'un dentifrice, d'un bain de bouche ou d'un concentré pour bain de bouche et qui contient une ou plusieurs matières sensibles à l'oxydation. Cette invention est caractérisée en ce que cet agent présente une teneur en eau inférieure ou égale à 7,5 % en poids, selon Karl Fischer.
EP04764666A 2003-09-09 2004-08-31 Agent topique a action par voie orale sensiblement anhydre contenant une ou plusieurs matieres sensibles a l'oxydation Withdrawn EP1663126A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP04764666A EP1663126A1 (fr) 2003-09-09 2004-08-31 Agent topique a action par voie orale sensiblement anhydre contenant une ou plusieurs matieres sensibles a l'oxydation

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP03019674 2003-09-09
EP04764666A EP1663126A1 (fr) 2003-09-09 2004-08-31 Agent topique a action par voie orale sensiblement anhydre contenant une ou plusieurs matieres sensibles a l'oxydation
PCT/EP2004/009701 WO2005025527A1 (fr) 2003-09-09 2004-08-31 Agent topique a action par voie orale sensiblement anhydre contenant une ou plusieurs matieres sensibles a l'oxydation

Publications (1)

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EP1663126A1 true EP1663126A1 (fr) 2006-06-07

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US (1) US20070053851A1 (fr)
EP (1) EP1663126A1 (fr)
JP (1) JP2007505064A (fr)
KR (1) KR20060121866A (fr)
CN (1) CN100579504C (fr)
BR (1) BRPI0413535A (fr)
CA (1) CA2535219A1 (fr)
WO (1) WO2005025527A1 (fr)

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GB0614353D0 (en) * 2006-07-20 2006-08-30 Oraldent Ltd Oral compositions, their preparation and use
JP2008031115A (ja) * 2006-07-31 2008-02-14 Sunstar Inc 液体組成物の製造方法及び装置
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JP5707017B2 (ja) * 2008-03-07 2015-04-22 太陽化学株式会社 茶抽出物含有口腔洗浄剤
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WO2014104064A1 (fr) * 2012-12-26 2014-07-03 株式会社エーゼット Accélérateur de cicatrisation de plaie
WO2014145602A1 (fr) * 2013-03-15 2014-09-18 Api Genesis Llc Compositions de polyphénol/flavonoïde et procédés de formulation de produits d'hygiène buccale
JP2013224318A (ja) * 2013-06-20 2013-10-31 Nippon Zettoc Co Ltd 活性酸素消去剤、皮膚外用剤、口腔用組成物及び食品
JP7335040B2 (ja) * 2017-10-30 2023-08-29 エルジー ハウスホールド アンド ヘルスケア リミテッド ポンプ型歯磨剤組成物
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WO2005025527A1 (fr) 2005-03-24
BRPI0413535A (pt) 2006-10-10
CN100579504C (zh) 2010-01-13
CA2535219A1 (fr) 2005-03-24
KR20060121866A (ko) 2006-11-29
US20070053851A1 (en) 2007-03-08
JP2007505064A (ja) 2007-03-08
CN1849107A (zh) 2006-10-18

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