WO2013092117A2 - Composition d'hygiène orale - Google Patents

Composition d'hygiène orale Download PDF

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Publication number
WO2013092117A2
WO2013092117A2 PCT/EP2012/073591 EP2012073591W WO2013092117A2 WO 2013092117 A2 WO2013092117 A2 WO 2013092117A2 EP 2012073591 W EP2012073591 W EP 2012073591W WO 2013092117 A2 WO2013092117 A2 WO 2013092117A2
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WO
WIPO (PCT)
Prior art keywords
tea extract
oral care
green tea
care composition
catechins
Prior art date
Application number
PCT/EP2012/073591
Other languages
English (en)
Other versions
WO2013092117A3 (fr
Inventor
Nandini BALARAM SINGH
Gautam Banerjee
Suresh Murigeppa NADAKATTI
Smitha Ashok Upadhyaya
Original Assignee
Unilever N.V.
Unilever Plc
Hindustan Unilever Limited
Conopco, Inc., D/B/A Unilever
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Unilever N.V., Unilever Plc, Hindustan Unilever Limited, Conopco, Inc., D/B/A Unilever filed Critical Unilever N.V.
Publication of WO2013092117A2 publication Critical patent/WO2013092117A2/fr
Publication of WO2013092117A3 publication Critical patent/WO2013092117A3/fr

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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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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 present invention relates to an oral care composition more particularly to an oral care composition for anti-inflammatory benefit.
  • Oral care and oral hygiene is one of the most important requirements for a healthy life. Everyday most of the people brush their teeth to keep themselves orally hygienic. Many people brush their teeth at least twice each day and sometimes even more than twice. On the other hand due to lack of proper dental care a number of people suffer from inflammation in their gums which causes irritation and diseases in their mouth.
  • the most commonly known oral care compositions are toothpaste, tooth powder and mouthwash. People throughout the world use these compositions for their oral health and hygiene.
  • US2006/0140881 discloses an oral care composition containing: a free-B-ring flavonoids and a flavan; as well as at least one bioavailability-enhancing agent. Methods of using the oral compositions are also provided.
  • US2008/069783 discloses an oral cavity cleaning composition, comprising 35-50 parts by weight of tea leaves extract, 10-25 parts by weight of Stevia leaf extract, 10-25 parts by weight of lemon extract, 10-15 parts by weight of mint leaf extract, 10-20 parts by weight of Lonicerae Flos extract, 20-30 parts by weight of kuding tea leaf extract, 5-10 parts by weight of xylitol and 25-35 parts by weight of ethanol. All ingredients in the composition are obtained from edible plants that are very effective in oral cavity care.
  • Catechins in general are known for their health benefit.
  • green tea is also well known for its health benefits.
  • catechins in general and those present in the green tea tend to be oxidized at the pH of the oral care composition and therefore no longer available to provide for the desired benefit. Therefore there is a need for developing an oral care composition containing catechins (such as green tea catechins) which is able to provide desired antiinflammatory benefit.
  • one of the objects of the present invention is to overcome or ameliorate at least one of the disadvantages of the prior art, or to provide a suitable alternative. It is yet another object of the present invention to provide an anti-inflammatory oral care composition.
  • the present inventors while working with oral care compositions comprising green tea surprisingly found that low amount of green tea when combined with black tea extract in a particular ratio is able to provide the desired antiinflammatory benefits thereby satisfying one or more of the aforesaid objects.
  • an oral care composition comprising:
  • the amount of polyphenols in the black tea extract is from 25 to 40% by dry weight and the ratio of green tea extract to polyphenols in the black tea extract is from 1 :1 to 1 :50.
  • the present invention provides a process of making an oral care composition comprising the steps of mixing 0.01 to 5% by weight of green tea extract of Camellia sinensis and 0.01 to 5% by weight of a black tea extract of Camellia sinensis with an orally acceptable base, wherein the amount of polyphenols in the black tea extract is from 25 to 40% by dry weight and the ratio of green tea extract to polyphenols in the black tea extract is from 1 :1 to 1 :50.
  • the present invention provides the use of an oral care composition of the first aspect for anti-inflammatory benefit.
  • the present invention provides an oral care composition of the first aspect wherein the source of catechins is a green tea extract of Camellia sinensis.
  • the present invention provides an oral care composition comprising:
  • the amount of polyphenols in the black tea extract is from 25 to 40% by dry weight and the ratio of green tea extract to polyphenols in the black tea extract is from 1 :1 to 1 :50.
  • the oral care composition of the invention comprises 0.01 to 5%, preferably 0.1 to 5% and more preferably 1 to 4% by weight of green tea extract.
  • the source of green tea extract is Camellia sinensis.
  • Green tea is well known in the world of teas. Generally green tea is produced by steaming or pan-firing the tea leaves immediately after plucking so that enzyme action is inhibited and endogenous components in the leaves are retained in the product mainly unchanged. Therefore, the taste is primarily determined by the choice of clone, time of the plucking, shoot maturity and the cultivation method.
  • Major constituents of green tea polyphenols are (-) epicatechin, (-)
  • epigallocatechin (-) epicatechingallate and epigallocatechingallate (EGCG).
  • the preferable source of catechins for the composition of the present invention is green tea extract.
  • the green tea extract is preferably fine granulated and comprises Gallic acid, catechins and their derivatives viz. Gallic acid,
  • the green tea extract preferably used for making the oral care formulation of the invention comprises 50 to 75 %, preferably 55 to 75% and more preferably 60 to 75% of polyphenols by dry weight of green tea extract.
  • the green tea extract preferably used for making the oral care formulation of the invention comprises 8 - 14 % of Epigallocatechin by dry weight of green tea extract, preferably 9 -14 % and more preferably 10 - 14%.
  • the green tea extract preferably used for making the oral care formulation of the present invention comprises 25 - 40%, preferably 28 - 40% and more preferably 32 - 40% of Epigallocatechin gallate by dry weight of green tea extract.
  • the green tea extract preferably used for making the oral care formulation of the present invention comprises 2 - 8%, preferably 3 - 8% , more preferably 4 - 8% and most preferably 5 -8% of Epicatechin gallate by dry weight of green tea extract.
  • the Epicatechins content of the green tea extract is between 2 - 8 %, preferably 3 - 8 % and more preferably 4 - 8 % by dry weight of the green tea extract.
  • the caffeine content of the green tea extract is in between 6 - 14%, preferably 8 - 14% and more preferably 10 - 14%.
  • the green tea extract is from Camellia sinensis var. sinensis and/or Camellia sinensis var. assamica.
  • Commercially available green tea powder with the particular specification as stated above (in terms of polyphenols, EGC, EGCG, ECG content) may be used for making the oral care composition.
  • purified green tea catechins may be used instead of green tea extract.
  • the oral care composition of the present invention also comprises 0.01 to 5%, preferably 1 to 5% and more preferably 1 to 4% of black tea extract of Camellia sinensis.
  • the black tea extract comprises 25 - 40%, preferably 28 - 40% and more preferably 30 - 40% of polyphenols by dry weight of black tea extract.
  • the aqueous extract of black tea is preferably made by extracting black tea leaf with water in a ratio of 1 :5 to 1 :30 at a temperature of 80 - 98°C for 10 minutes to 2 hours. After the extraction process preferably the extract is subjected to centrifugation to separate out the residual leaf and the aqueous extract. Then the aqueous extract is dried preferably in a spray dryer to get black tea extract powder.
  • black tea extract in liquid form may be used for making the compositions of the invention.
  • the preferred ratio of one or more catechins to polyphenols in the black tea extract is from 1 : 10 to 1 :50 and more preferably from 1 : 15 to 1 :50.
  • the oral care composition of the invention comprises an orally acceptable base.
  • the orally acceptable base is a base formulation which is suitable for application in the human mouth.
  • the oral compositions can be formulated in any suitable form, such as gels, mouthwashes, toothpowders and toothpastes.
  • the oral care compositions of the present invention may comprise optional, conventional ingredients such as pharmaceutically acceptable carriers like starch, sucrose, water or water/alcohol systems etc.. Small amounts of surfactants may also be included, such as anionic, nonionic and amphoteric surfactants.
  • the oral care composition may contain all the usual oral care composition ingredients. They may also comprise particulate abrasive materials such as silicas, aluminas, calcium carbonates, dicalcium phosphates, calcium pyrophosphates
  • the oral care composition may comprise humectants such as glycerol, sorbitol, propylene glycol, xylitol, lactitol and so on.
  • Binders and thickeners such as sodium carboxymethyl-cellulose, xanthan gum, gum arabic etc. may also be included, as well as synthetic polymers such as polyacrylates and carboxyvinyl polymers such as Carbopol.
  • Flavours such as peppermint and spearmint oils may also be included, as well as preservatives, opacifying agents, colouring agents, pH-adjusting agents, sweetening agents and so on.
  • Anti-bacterial agents may also be included such as Triclosan, chlorhexidine, copper-, zinc- and stannous salts such as zinc citrate, sodium zinc citrate and stannous pyrophosphate, sanguinarine extract, metronidazole.
  • Further examples of anti-bacterial agents are quaternary ammonium compounds such as cetylpyridinium chloride; bis-guanides such as chlorhexidine digluconate, hexetidine, octenidine, alexidine; halogenated bisphenolic compounds such as 2,2' methylenebis-(4-chloro-6-bromophenol).
  • Polymeric compounds which can enhance the delivery of active ingredients such as anti-bacterial agents can also be included.
  • examples of such polymers are copolymers of polyvinylmethylether with maleic anhydride and other similar delivery enhancing polymers.
  • Anti-caries agents such as sodium- and stannous fluoride, aminefluorides, monosodium fluorophosphate, casein, plaque buffers such as urea, calcium lactate, calcium glycerophosphate, strontium polyacrylates may also be included.
  • Other optional ingredients include vitamins such as Vitamin C, and plant extracts.
  • Desensitising agents such as potassium citrate, potassium chloride, potassium tartrate, potassium bicarbonate, potassium oxalate, potassium nitrate as well as strontium salts may also be included.
  • Buffers and salts to buffer the pH and ionic strength of the compositions may also be included.
  • the pH of the compositions usually ranges from 5-10, preferably 6-9 and especially preferably 7-8.5.
  • Liposomes and other encapsulates may also be used to improve delivery or stability of active ingredients.
  • the oral compositions may comprise anti-calculus agents such as alkalimetal pyrophosphates, hypophosphite-containing polymers, organic phosphonates, phosphocitrates etc..
  • anti-calculus agents such as alkalimetal pyrophosphates, hypophosphite-containing polymers, organic phosphonates, phosphocitrates etc.
  • compositions may comprise functional biomolecules such as bacteriocins, antibodies, enzymes and so on.
  • effervescing systems such as sodium bicarbonate/citric acid systems, colour change systems, and so on.
  • the oral care composition When formulated as a mouthwash, the oral care composition usually comprises a water/alcohol solution, flavour, humectant, sweetener and colorant.
  • the present invention also provides for a process of making an oral care composition comprising the steps of mixing 0.01 to 5% by weight of green tea extract of Camellia sinensis and 0.01 to 5% by weight of a black tea extract of Camellia sinensis with an orally acceptable base, wherein the amount of polyphenols in the black tea extract is from 25 to 40% by dry weight and the ratio of green tea extract to polyphenols in the black tea extract is from 1 :1 to 1 :50.
  • the process comprises the steps of mixing 0.1 to 5%, more preferably 1 to 4 % of green tea extract and 0.1 to 5%, preferably 1 to 4 % of black tea extract of the Camellia sinensis species with an orally acceptable base.
  • the amount of polyphenols in the black tea extract is from 25 to 40%, preferably 28 to 40% and more preferably 30 to 40% by dry weight, and the ratio of one or more catechins to polyphenols in the black tea extract is from 1 :1 to 1 :50 preferably 1 : 10 to 1 :50 and more preferably from 1 : 15 to 1 :50.
  • the mixing may be preferably carried out in a conventional mixer used for making such formulation.
  • Sileverson® mixer is the preferred one.
  • the present invention also provides the use of an oral care composition as for anti-inflammatory benefit.
  • Example 1 Preparation of an oral care composition of the invention
  • Toothpaste compositions were made according to the formulations in Table 1. Table 1
  • Green tea extract 1.5 0.5 0.1
  • SCMC Sodium carboxymethyl cellulose
  • SLS sodium lauryl sulfate
  • FGNC Fine ground natural chalk
  • silica trade name- Mfil®, supplier - Madhu silica pvt. Ltd., India
  • SMFP sodium monofluorophosphate
  • Green tea extract powder (Trade name - Sunphenone® having a polyphenol content of ⁇ 60%, EGCG content -32%, ECG content ⁇ 6.7%, EGC content ⁇ 12.8% and EC content of ⁇ 5% by dry weight, Supplier- Taiyo Green Power Co Ltd., Japan) and black tea extract powder (having a polyphenol content of ⁇ 30 %). Then mixing was continued for 5 minutes.
  • the black tea extract powder was made by taking Lipton® Yellow label leaf tea product available in the market.
  • the leaf tea was extracted with water in a ratio of 1 :20 at a temperature of 92 ⁇ 2°C for 45 minutes.
  • the extract was subjected to ultra filtration to obtain concentrated extract and then it was dried in a spray dryer to obtain the black tea extract powder.
  • Example 2 Conversion of green tea catechins at high pH of the toothpaste
  • a toothpaste was made using the formulation of Table 1 , except instead of both black tea extract and green tea extract, only green tea catechins were added at a level of 5% by dry weight of the toothpaste.
  • This toothpaste was stored in a tube at ⁇ 25°C and the catechin content was measured after 4 months and 1 1 months using the ISO method for the determination of catechins, using high performance liquid chromatography (ISO 14502-2:2005). The results are summarized in Table 2.
  • the pH of the toothpaste was 9.
  • Fresh blood was withdrawn by vein puncture from healthy volunteers (free of infection) and collected into a vacutainer containing heparin (to prevent coagulation of the samples).
  • RPMI medium was prepared by mixing 10.4 g of RPMI-1640 (from Sigma having Cat. No. 6504), 1 .5 g of sodium bicarbonate (from SRL), 2.5 g of glucose and 2.38 g of Hepes (from Sigma) in 900 mL of autoclaved Mili-Q water. After adjusting the pH to ⁇ 7.2, the solution was filtered using a membrane filter (from Pall Corporation, Specification - vacucap 90pf filter unit, pore size 0.2 micron), followed by adding 10 mL of antibiotic-antimycotic solution (from Sigma, Cat No. A5955). Finally the volume was made up to 1 L with autoclaved Mili-Q water.
  • each test sample (as shown in Table 3) which has 100 ⁇ of Escherichia coli lipopolysaccharide (E. coli LPS from Sigma, Cat. No. L-4130) was added to the wells in the culture plate.
  • the concentration of LPS was 100 ng/mL, diluted in RPMI medium.
  • a control well (C-1 ) was maintained in which there was no LPS (i.e. only 0.5 mL of blood and 0.5 mL of RPMI medium) and another control (C-2) with only LPS (0.5 mL of blood with 0.5 mL of RPMI medium containing 100 ⁇ of LPS) was maintained separately.
  • the culture plate was then incubated in an incubator (Forma series II water jacket CO 2 incubator: Thermo Scientific) at a temperature of ⁇ 37°C with 5% CO 2 for 24 hours. After incubation the culture plate was centrifuged at 1900 g for ⁇ 10 minutes. The supernatant was then collected and aliquoted (in tubes) and stored in a freezer maintained at -70°C for 12 hours.
  • a 96-well microtiter plate (Nunc-lmmuno Plates MaxiSorp F96, Cat. No. 468667) was taken and coated with a solution of 100 ⁇ _ / well (concentration: 2 ⁇ 9/ ⁇ _) of primary antibody (antihuman IL-6, R& D Systems, cat no AF-206-NA). After that the plate was kept for 12 hours at a temperature of ⁇ 4°C without any
  • the 96 well plate was taken out from the refrigerator and washed with 300 ⁇ _ / well of wash buffer.
  • the wash buffer was prepared by adding 0.05% (v/v) of Tween 20 in 500 ml_ of phosphate buffered saline (4 g NaCI + 0.1 g KCI + 0.58 g Na 2 HP0 4 + 0.1 g KH 2 P0 4 in 500 ml_ of autoclaved Mili-Q water). The washing step was done three times. The plate was then drained completely till all the liquid was removed. Then the plate was blocked with 300 ⁇ _ / well of 5% (w/v) skimmed milk in phosphate buffered saline (PBS) for 2 hours at ⁇ 25°C.
  • PBS phosphate buffered saline
  • the washing step was repeated three times.
  • 100 ⁇ _ / well of human IL-6 standard (R&D Systems; Cat. No. 206-IL-050) ranging from 0.075ng/ml_ to 4.8ng/ml_ (prepared in PBS) was added to the first two strips and diluted culture supernatant (prepared above) was added in the remaining strips (all in duplicates).
  • the plate was then incubated for 2 hours at ⁇ 25°C.
  • the washing step mentioned above was repeated again thrice.
  • the plate was then drained out completely.
  • 100 ⁇ _ / well (concentration O ⁇ g/mL) of human biotinylated antibody IL-6 (R&D Systems; Cat. No. BAF-206) was added to the plate.
  • the plate was again incubated for 2 hours at ⁇ 25°C. The washing step mentioned above was repeated again thrice. The plate was then drained out completely. After that 100 L/well of 1 :200 diluted (in PBS) streptavidin-HRP conjugate (R & D Systems cat no DY 998) was added to the plate. The plate was then incubated for 30 minutes at 25°C. The washing and draining out step were repeated. This was followed by adding 100 ⁇ _ / well of 20 times water diluted TMB/H 2 0 2 substrate (Bangalore Genei, Cat No. 106035). This plate was incubated in a dark room for 10 - 20 minutes for colour development. The reaction was then stopped by adding 50 ⁇ _ / well of H 2 S0 4 having a normality of 2N.
  • OD optical density
  • the slope (A) of the standard curve (first two stripes of the plate using IL-6 standard) was calculated from the measured OD.
  • the amount of IL-6 released (ng/mL) from the sample can be calculated with the use of the following formula:
  • Amount of IL-6 released Absorbance (O.D) of the sample X- ⁇
  • Example 4 ln-vivo experiments to show that a combination of green tea catechins and black tea extract provides plaque reduction benefits
  • the volunteers for this study were selected on the basis of their oral health (i.e. without any oral inflammation) and medical history.
  • the study was conducted for 14 days (7+7) in two phases. During this period they were asked not to use any oral care product other than what was supplied to them for the study.
  • citrate buffer sodium citrate and citric acid at a ratio of 1 :10

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Botany (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

La présente invention concerne une composition d'hygiène orale, plus particulièrement une composition d'hygiène orale à effet anti-inflammatoire. Les catéchines sont, en général, connues pour leur bienfait pour la santé. Dans le monde du thé, le thé vert est également bien connu pour ses bienfaits pour la santé. Nous avons trouvé que les catéchines en général et celles présentes dans le thé vert ont tendance à être oxydées au pH de la composition d'hygiène orale et ne peuvent donc plus fournir les effets désirés. L'objectif de la présente invention est de fournir une composition d'hygiène orale avec une quantité minimale de catéchines, mais procurant les effets anti-inflammatoires désirés. Les présents inventeurs, en travaillant sur la composition d'hygiène orale comprenant des catéchines, de préférence des catéchines provenant de thé vert pour procurer des effets anti-inflammatoires, ont trouvé de manière surprenante qu'une très faible quantité de catéchines combinées à un extrait de thé noir dans un rapport particulier est apte à procurer les effets anti-inflammatoires désirés.
PCT/EP2012/073591 2011-12-20 2012-11-26 Composition d'hygiène orale WO2013092117A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN3569MU2011 2011-12-20
IN3569/MUM/2011 2011-12-20
EP12153552.0 2012-02-02
EP12153552 2012-02-02

Publications (2)

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WO2013092117A2 true WO2013092117A2 (fr) 2013-06-27
WO2013092117A3 WO2013092117A3 (fr) 2014-05-15

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016062449A1 (fr) * 2014-10-24 2016-04-28 Henkel Ag & Co. Kgaa Utilisation d'un extrait de camellia sinensis contenant du phénol dans des agents de lavage buccal et dentaire pour améliorer l'apparence de la gencive
WO2023001812A1 (fr) * 2021-07-22 2023-01-26 Isp Investments Llc Extrait de feuilles de the noir, compositions le comprenant et ses utilisations cosmetiques

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060140881A1 (en) 2004-12-22 2006-06-29 Guofeng Xu Oral care compositions containing flavonoids and flavans
US20080069783A1 (en) 2006-09-15 2008-03-20 Chun-Erh Wang Oral cavity cleaning composition

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JP2975380B2 (ja) * 1989-08-30 1999-11-10 三井農林株式会社 プラーク形成阻害剤
JPH03218320A (ja) * 1989-11-10 1991-09-25 Itouen:Kk 抗菌周病及び口臭の予防剤
JP3333584B2 (ja) * 1993-04-19 2002-10-15 三井農林株式会社 歯質の耐酸性強化組成物
JP2988928B1 (ja) * 1998-12-18 1999-12-13 三井物産株式会社 口中スプレー用組成物
US20060141039A1 (en) * 2004-12-23 2006-06-29 Colgate-Palmolive Company Oral compositions containing oxidized camellia
US8895084B2 (en) * 2004-12-23 2014-11-25 Colgate-Palmolive Company Oral care composition containing extract of unoxidized Camellia
JP2008148587A (ja) * 2006-12-14 2008-07-03 Taiyo Kagaku Co Ltd ポリフェノール組成物
JP2009219484A (ja) * 2008-02-19 2009-10-01 Kracie Seiyaku Kk 抗歯周病性口腔用組成物及び飲食品

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060140881A1 (en) 2004-12-22 2006-06-29 Guofeng Xu Oral care compositions containing flavonoids and flavans
US20080069783A1 (en) 2006-09-15 2008-03-20 Chun-Erh Wang Oral cavity cleaning composition

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016062449A1 (fr) * 2014-10-24 2016-04-28 Henkel Ag & Co. Kgaa Utilisation d'un extrait de camellia sinensis contenant du phénol dans des agents de lavage buccal et dentaire pour améliorer l'apparence de la gencive
WO2023001812A1 (fr) * 2021-07-22 2023-01-26 Isp Investments Llc Extrait de feuilles de the noir, compositions le comprenant et ses utilisations cosmetiques
FR3125425A1 (fr) * 2021-07-22 2023-01-27 Isp Investments Llc Extrait de feuilles de the noir, compositions le comprenant et ses utilisations cosmetiques

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