US20100008869A1 - Method for preventing coloration of catechins and dentifrice composition - Google Patents

Method for preventing coloration of catechins and dentifrice composition Download PDF

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US20100008869A1
US20100008869A1 US12/374,099 US37409907A US2010008869A1 US 20100008869 A1 US20100008869 A1 US 20100008869A1 US 37409907 A US37409907 A US 37409907A US 2010008869 A1 US2010008869 A1 US 2010008869A1
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Prior art keywords
catechin
water
catechins
polymer
gum
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Inventor
Michiya Takagi
Satoshi Ueno
Koji Mine
Hideaki Kubo
Ikuhisa Ichimura
Gen Nakauchi
Kazushi Oshino
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Kao Corp
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Kao Corp
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Priority claimed from JP2006199515A external-priority patent/JP4308230B2/ja
Priority claimed from JP2006199516A external-priority patent/JP5351379B2/ja
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Assigned to KAO CORPORATION reassignment KAO CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: NAKAUCHI, GEN, ICHIMURA, IKUHISA, KUBO, HIDEAKI, MINE, KOJI, OSHINO, KAZUSHI, TAKAGI, MICHIYA, UENO, SATOSHI
Publication of US20100008869A1 publication Critical patent/US20100008869A1/en
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    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8176—Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/042—Gels
    • 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
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/18—Antioxidants, e.g. antiradicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
    • C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1545—Six-membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95

Definitions

  • the present invention relates to a method of suppressing coloration of catechins and hydrogel particles containing a water-insoluble complex of catechins.
  • the present invention also relates to a dentifrice composition containing catechins.
  • Catechin, tannin, etc. are known as polyphenols contained in tea leaves. Particularly, catechins are known to have various physiological functions such as antioxidative action, antibacterial action, blood cholesterol-level-rise suppressive action, blood-pressure-rise suppressive action and blood-sugar-level-rise inhibitory action. However, catechins themselves are potent antioxidants and thus have a problem of undergoing oxidization and polymerization during storage. Further, catechins have a problem of discoloration upon oxidation and/or polymerization, thus restricting the degree of freedom of their application to pharmaceutical preparations. Accordingly, there is demand for a method of suppressing oxidation and polymerization of catechins.
  • JP-A 9-47654 relates to removal of polyphenols since the presence of excessive polyphenols in products deteriorates the commodity value, and is thus different in purpose from a method of suppressing oxidation and polymerization of catechins.
  • JP-A 8-333380 discloses a process for producing tea saponin, wherein an extract extracted with a water-containing lower alcohol from hot-water extraction residues of tea leaves is treated with water-insoluble polyvinyl pyrrolidone, thereby removing catechins from the extract.
  • JP-A 1-218550 discloses a process for producing tannin-free tea, which contains adding insoluble polyvinyl pyrrolidone to a filtered extract extracted with hot water, etc. from anaerobically treated tea leaves, and then filtering the extract.
  • dental caries and periodontitis are caused by dental bacteria. Accordingly, dental caries and periodontitis are prevented generally by killing dental bacteria or suppressing their activity with a dental composition compounded with a bacteriocide. Particularly with increasing natural-product orientation in recent years, a naturally derived component is used as the bacteriocide to avoid use of a chemically synthesized substance.
  • a green tea extract and its components that are tea polyphenol compounds (catechins etc.) are known to be effective in suppressing proliferation of dental bacteria (for example, JP-A 1-90124, JP-A 2-25413, JP-A 3-86814, etc.).
  • the present invention provides a method of suppressing coloration of catechins, which includes adding, to catechins, a water-soluble polymer (referred to hereinafter as polymer A) capable of forming a water-insoluble complex with catechins.
  • a water-soluble polymer referred to hereinafter as polymer A
  • the present invention also provides hydrogel particles containing a water-insoluble complex of catechins and polymer A.
  • the present invention provides a dentifrice composition containing hydrogel particles containing catechin and a water-soluble polymer forming a water-insoluble complex with catechin, a binder and water.
  • the present invention provides use of a water-soluble polymer forming a water-insoluble complex with catechin in suppressing coloration of catechin. Further, the present invention provides dentifrice use of a composition containing hydrogel particles containing catechin and a water-soluble polymer forming a water-insoluble complex with catechin, a binder and water.
  • JP-A 9-47654 discloses a polyphenol adsorbent containing a composite material containing an insoluble polyvinyl pyrrolidone contained in a base material of regenerated cellulose substance.
  • JP-A 8-333380 relates to removal of catechins, etc. that are unnecessary substances other than the objective substance saponin and is different in purpose from a method of suppressing oxidation and polymerization of catechins.
  • JP-A 1-218550 relates to removal of tannin components in an extract and is different in purpose from a method of suppressing oxidation and polymerization of catechins.
  • the present invention provides a method of preventing discoloration of catechins by suppressing coloration thereof, as well as hydrogel particles of catechins whose coloration is suppressed.
  • the present invention provides a dentifrice composition excellent in sense of use wherein catechins are stably maintained, and when used, the catechins act effectively on teeth and gum.
  • catechins can be stabilized by forming a water-insoluble complex with polymer A, thereby suppressing coloration of the catechins.
  • the dentifrice composition of the present invention maintains catechins stably, permits catechins to act effectively in the vicinity of the surfaces of teeth and gum, to improve the state of teeth and gum, and is excellent in sense of use.
  • catechins are non-polymer catechins and include, for example, non-epicatechins such as catechin, gallocatechin, catechingallate and gallocatechingallate, and epicatechins such as epicatechin, epigallocatechin, epicatechingallate and epigallocatechingallate.
  • Catechins can be obtained by concentration, purification, etc. of a green tea extract extracted from tea leaves with hot water or a water-soluble organic solvent.
  • commercially available green tea extract concentrates such as “Polyphenon” available from Mitsui Norin Co., Ltd, “Thea-furan” from Ito En, Ltd., and “Sunphenon” from Taiyo Kagaku Co., Ltd. can be used and subjected to regulation of components, thereby yielding green tea extracts serving the purpose of the present invention.
  • the polymer A used in the present invention is not particularly limited as long as it is a water-soluble polymer forming a water-insoluble complex with catechins.
  • the water-insoluble complex refers to a substance precipitated from water as insoluble matter when an aqueous solution of catechins is mixed with an aqueous solution of polymer A. Precipitation of the water-insoluble complex can be confirmed by turbidity of the mixture or by the presence of a peak originating from the water-insoluble complex when the mixture is measured with a laser diffraction/scattering particle size distribution analyzer.
  • the polymer A includes polyvinyl pyrrolidone, polyvinyl alcohol, and hydroxyethyl cellulose, among which polyvinyl pyrrolidone (hereinafter abbreviated sometimes as PVP) is preferable.
  • PVP polyvinyl pyrrolidone
  • the weight-average molecular weight of polymer A is preferably 6000 or more, more preferably 60000 or more, even more preferably 400000 or more, even more preferably 1300000 or more.
  • the molecular weight is preferably 3000000 or less, more preferably 2000000 or less, from the viewpoint of obtaining a fine water-insoluble complex by preventing the water-insoluble complex from forming clumpy aggregates.
  • the weight-average molecular weight of polymer A is a value determined for example by a laser diffraction scattering method that is a general weight-average molecular weight measuring method.
  • the amount of polymer A added is preferably 1 to 4 times, more preferably 1 to 3 times, even more preferably 1.2 to 2.2 times, the weight of the catechins, from the viewpoint of effectively suppressing coloration of catechins.
  • an aqueous solution of polymer A, etc. are added to an aqueous solution of catechins, etc. and mixed by means of a stirrer or the like, thereby forming a water-insoluble complex to suppress coloration of the catechins.
  • the hydrogel particles of the present invention contain a water-insoluble complex of catechins and polymer A.
  • the “hydrogel” referred to in the present invention refers to a water-containing swollen body of a water-insoluble polymer (gel former) formed with water as a solvent.
  • the gel former is preferably a naturally occurring polymer compound and includes, for example, seaweed extracts such as agar, ⁇ -carrageenan, ⁇ -carrageenan, ⁇ -carrageenan, furcelleran, alginate, and propylene glycol alginate; plant seed viscous substances such as guar gum, locust bean gum, tamarind seed polysaccharides, tara gum, and quassia gum; plant fruit viscous substances such as pectin and arabinogalactan; viscous substances produced by microorganisms, such as xanthan gum, scleroglucan, pullulan, dextran, gellan gum and curdlan; animal proteins such as gelatin, albumin and casein; vegetable proteins such as soy protein and wheat protein; cellulose and derivatives thereof, such
  • the dissolution temperature of agar in water is generally 75° C. or more, mainly 75 to 90° C., and when agar is dissolved in water and then cooled, the gelling temperature is 30 to 45° C.
  • the water-insoluble complex of catechins and polymer A is dispersed in a continuous phase containing a gel former and water and included in the hydrogel particles of the present invention.
  • the amount of polymer A is preferably 1 to 4 times, more preferably 1 to 3 times, even more preferably 1.2 to 2.2 times, the weight of the catechins, from the viewpoint of effectively suppressing the coloration of catechins.
  • the content of the water-insoluble complex of catechins and polymer A in the hydrogel particles of the present invention is preferably 12% by weight or less, more preferably 8% by weight or less, even more preferably 6% by weight or less, from the viewpoint of obtaining a fine water-insoluble complex by preventing the water-insoluble complex from forming clumpy aggregates.
  • the content of the gel former in the hydrogel particles of the present invention is preferably 0.25 to 5.0% by weight, more preferably 0.5 to 4.0% by weight, even more preferably 1.0 to 3.0% by weight, from the viewpoint of preventing the hydrogel particles from collapsing upon incorporation into another preparation.
  • the hydrogel particles of the present invention may contain water-soluble organic compounds such as sugars and polyhydric alcohols and components such as a colorant, a preservative and a water-soluble perfume in addition to the water-insoluble complex of the present invention, the gel former, and water.
  • water-soluble organic compounds such as sugars and polyhydric alcohols
  • components such as a colorant, a preservative and a water-soluble perfume in addition to the water-insoluble complex of the present invention, the gel former, and water.
  • the sugars include glucose, galactose, fructose, mannose, mannitol, saccharose, maltose, and lactose.
  • the polyhydric alcohols include glycerin, sorbitol, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, and oligosaccharide.
  • the average particle size of the hydrogel particles of the present invention is preferably 5 to 10000 ⁇ m, more preferably 100 to 10000 ⁇ m, even more preferably 200 to 5000 ⁇ m.
  • the average particle size of the hydrogel particles is expressed in weight average particle size that is determined by subjecting 100 g of the particles to wet classification in water by using sieves with various mesh screens and then removing excess water therefrom with filter paper (sieve method).
  • the shape of the hydrogel particle of the present invention is not particularly limited, but is preferably the shape of a body of revolution which is composed of a curved surface.
  • the “body of revolution which is composed of a curved surface” refers to a three-dimensional body defined by rotating a closed plane formed by a continuous curve and a virtual axis, but does not include a three-dimensional body having a flat surface, such as a triangular pyramid, circular cylinder, etc.
  • the shape of the hydrogel particle is more preferably spherical or elliptical.
  • the process for producing the hydrogel particles of the present invention is not particularly limited.
  • a gel former such as agar and polymer A are mixed with deionized water and then dissolved sufficiently by heating at a temperature higher than the dissolution temperature.
  • An aqueous solution of catechins is added to, and mixed with, the mixture and then subjected to a general dropping, spraying or stirring method to yield hydrogel particles.
  • the dropping method utilizes such a property of the mixture as to form droplets by its surface or interfacial tension upon ejection through an orifice.
  • the droplets are cooled in a gaseous phase (e.g., air) or liquid phase to solidify into hydrogel particles.
  • a gaseous phase e.g., air
  • the mixture ejected through an orifice is preferably vibrated.
  • the spraying method uses a spray nozzle through which the mixture is sprayed into a gaseous phase such that droplets of the mixture are formed by the surface tension.
  • the droplets are cooled in the gaseous phase to solidify into hydrogel particles.
  • the mixture is poured into a solution which has a property of being substantially unmixable with the mixture and which is regulated to a temperature equal to or higher than the gelation temperature.
  • the solution is stirred such that the mixture is atomized by the shearing force of stirring, whereby droplets are formed by the surface tension.
  • the droplets are cooled in a liquid which is substantially unmixable with the mixture to solidify into hydrogel particles.
  • the temperature of the mixture when ejected, sprayed, or poured is preferably between the gelation temperature and 100° C.
  • the temperature of the oil-in-water dispersion is preferably higher than the gelation temperature by 10° C. or more, more preferably higher than the gelation temperature by 20° C. or more. It should be noted that the upper limit of this temperature is the boiling point of water, i.e., 100° C.
  • the hydrogel of the present invention can be incorporated into cosmetics, detergents, bath agents, etc.
  • the hydrogel can also be incorporated into an oral composition, particularly a dentifrice composition.
  • the hydrogel particles contained in the dentifrice composition of the present invention contain the catechins and a water-soluble polymer (hereinafter referred to polymer A) forming a water-insoluble complex with the catechins.
  • polymer A a water-soluble polymer
  • the “hydrogel” refers to a water-containing swollen body of a water-insoluble polymer (gel former) with water as solvent, and the gel former is preferably a naturally occurring polymer compound.
  • the content of catechins in the hydrogel particles of the present invention is preferably 0.001 to 10% by mass, more preferably 0.001 to 6% by mass, even more preferably 0.01 to 2% by mass, from the viewpoint of the efficient action of catechins on gums and of the stability of hydrogel particles.
  • the content of polymer A is preferably 1 to 4 times, more preferably 1 to 3 times, even more preferably 1.2 to 2.2 times, the mass of the catechins.
  • the content of the water-insoluble complex in the hydrogel particles is preferably 12% by mass or less, more preferably 8% by mass or less, even more preferably 6% by mass or less, from the viewpoint of obtaining a fine water-insoluble complex by suppressing the water-insoluble complex from forming clumpy aggregates.
  • the gel former used in the hydrogel particles is as described above.
  • the content of the gel former in the hydrogel particles of the present invention is as described above, from the viewpoint of preventing the hydrogel particles from collapsing upon incorporation into a dentifrice composition.
  • the hydrogel particles of the present invention may contain water-soluble organic compounds such as sugars and polyhydric alcohols and components such as a colorant, a preservative and a water-soluble perfume as described above, in addition to catechins, polymer A, the gel former and water.
  • water-soluble organic compounds such as sugars and polyhydric alcohols
  • components such as a colorant, a preservative and a water-soluble perfume as described above, in addition to catechins, polymer A, the gel former and water.
  • the dentifrice composition of the present invention contains the hydrogel particles described above, a binder and water.
  • the binder used in the present invention includes, for example, sodium alginate, carboxymethylcellulose sodium, carrageenan, xanthan gum, sodium polyacrylate, hydroxyethyl cellulose, hydroxypropyl cellulose, pectin, tragacanth gum, gum arabic, guar gum, karaya gum, locust bean gum, gellan gum, tamarind gum, psyllium seed gum, polyvinyl alcohol, sodium chondroitin sulfate, and a methoxy ethylene-maleic anhydride copolymer, among which sodium alginate, carboxymethylcellulose sodium, carrageenan, and xanthan gum are preferable.
  • sodium alginate is preferably one having an intramolecular mannuronic acid/guluronic acid ratio (M/G ratio) of 0.5 to 2.5, which is easily available commercially from Kimica corporation and Dainippon Pharmaceutical Co., Ltd.
  • Carboxymethylcellulose sodium is preferably one having an etherification degree of 0.6 to 2.5, which is easily available commercially from Daicel Chemical Industries, Ltd. and Dai-ichi Kogyo Seiyaku Co., Ltd., more preferably one having an etherification degree of 0.8 to 1.5.
  • Carrageenan that can be used may be any of 3 isomers ( ⁇ -, ⁇ - and ⁇ -carrageenans) and is easily and commercially available from Kelco Co., Ltd., MRC Polysaccharide co., Ltd., Taiyo Kagaku Co., Ltd., etc., more preferably ⁇ - or ⁇ -carrageenan.
  • Xanthan gum that can be used is commercially available from Taiyo Kagaku Co., Ltd., Kelco Co., Ltd., Dainippon Pharmaceutical Co., Ltd. etc., and when used in combination with carboxymethyl cellulose, is preferably xanthan gum with low cellulase activity from which a small amount of contaminating cellulase was removed.
  • the binders may be used singly or as a mixture of two or more thereof, and the content of the binder in the composition is preferably 0.1 to 3% by mass, more preferably 0.1 to 2% by mass, even more preferably 0.2 to 1.2% by mass, from the viewpoint of attaining storage stability, the viscosity of the composition, and higher pleasant cooling sensation.
  • the content of the hydrogel particles in the dentifrice composition of the present invention is preferably 0.01 to 15% by mass, more preferably 0.1 to 10% by mass, even more preferably 1 to 5% by mass, from the stability of the dentifrice composition.
  • the amount of water in the dentifrice composition of the present invention is preferably 1 to 50% by mass, more preferably 5 to 40% by mass, even more preferably 10 to 30% by mass, from the viewpoint of attaining storage stability and higher pleasant cooling sensation.
  • the dentifrice composition of the present invention can further be compounded with powdery or granular erythritol having a particle size of less than 355 ⁇ m, from the viewpoint of pleasant cooling sensation and taste.
  • erythritol there occurs 3 types of isomers that are L-erythritol, D-erythritol and meso-erythritol, and any of these structures can be used in the present invention.
  • Erythritol that can be used may be an ordinarily available one and includes, for example, crystalline erythritol obtained by fermenting glucose and re-crystallizing the product.
  • the crystalline erythritol is available as commercial products from Nikken Chemicals Co., Ltd., Mitsubishi-Kagaku Foods Corporation, Celestare, etc. Erythritol having a large particle size may be used after regulation of particle size by pulverization.
  • a roller mill, a hammer mill, a high-speed grinder or a pulverizer is generally used, among which a high-speed grinder or a hammer mill excellent in production efficiency with easy regulation of particle size is preferably used in pulverization.
  • the particle size of erythritol is preferably 45 ⁇ m or more to less than 355 ⁇ m, more preferably 53 ⁇ m or more to less than 300 ⁇ m, even more preferably 75 ⁇ m or more to less than 250 ⁇ m, from the viewpoint of long-lasting pleasant cooling sensation in the mouth.
  • Erythritol having a particle size of 45 ⁇ m or more is preferable because the pleasant cooling sensation is long-lasting without instantaneous dissolution in the mouth.
  • Erythritol having a particle size of less than 355 ⁇ m is readily dissolved in the mouth and can demonstrate a pleasant cooling sensation.
  • the particle size of erythritol is measured in the following manner.
  • the amount of erythritol incorporated into the dentifrice composition of the present invention is preferably 15 to 60% by mass, more preferably 20 to 55% by mass, even more preferably 25 to 50% by mass, even more preferably 30 to 50% by mass, from the viewpoint of a pleasant cooling sensation.
  • Erythritol is desirably dispersed in a powdery state in the dentifrice composition.
  • erythritol is introduced preferably in the form of powder in the final stage of production.
  • erythritol is hardly dissolved in water and can be present in a powdery state in the dentifrice composition.
  • the dentifrice composition of the present invention may further contain an abrasive.
  • the abrasive includes not only silica such as precipitated silica, silica gel, aluminosilicate, silconosilicate, and gluconosilicate but also calcium carbonate, calcium hydrogen phosphate, calcium pyrophosphate, aluminum hydroxide, alumina, magnesium carbonate, and magnesium phosphate.
  • the content of the abrasive in the dentifrice composition of the present invention is preferably 0 to 15% by mass, more preferably 0 to 12% by mass.
  • compositions for example antioxidants, wetting agents, medicinal components, foaming agents, preservatives, flavorings, sweetening agents, pH adjusters and the like may be incorporated into the dentifrice composition of the present invention in such a range that the purpose of the present invention is not hindered.
  • the antioxidants include components having antioxidative potency or reducing power and usable in oral compositions, for example, L-ascorbic acid and salts thereof, erythorbic acid and salts thereof, ⁇ -tocopherol acetic acid, dl- ⁇ -tocopherol, rosemary extract, stevia extract, sunflower seed extract, propyl gallate, dibutyl hydroxy toluene, butyl hydroxy anisole, L-cysteine hydrochloride, phytic acid, hydroquinone and glycosides thereof, nordihydroguaiuretic acid, ascorbic higher fatty acid esters (laurate, stearate, isostearate, palmitate etc.) and guaiac gum.
  • L-ascorbic acid and salts thereof erythorbic acid and salts thereof
  • ⁇ -tocopherol acetic acid dl- ⁇ -tocopherol
  • rosemary extract stevia extract
  • sunflower seed extract propyl gallate
  • Salts of L-ascorbic acid, erythorbic acid or ⁇ -tocopherol acetic acid include sodium salts, calcium salts, ferrous salts and palmitate salt. These antioxidants may be used singly or as a mixture of two or more selected antioxidants.
  • the content of the antioxidant in the dentifrice composition of the present invention is preferably 0.0005 to 50% by mass, more preferably 0.001 to 20% by mass, even more preferably 0.01 to 5% by mass, from the viewpoint of suppressing a change in color of outside.
  • the wetting agents include, for example, glycerin, sorbitol, polyethylene glycol, propylene glycol, ethylene glycol, 1,3-butylene glycol, polypropylene glycol, xylitol, erythritol, maltitol and lactitol, and a combination of one or two or more thereof may be incorporated into the composition.
  • the content of these wetting agents in the dentifrice composition of the present invention is preferably 40 to 95% by mass, more preferably 60 to 80% by mass, from the viewpoint of securing transparency.
  • the dentifrice composition of the present invention can be formed in a usual manner into a paste dentifrice composition, a liquid dentifrice composition, a gel-like dentifrice composition, etc. depending on its intended use.
  • FIG. 1 is a graph showing the relationship between brightness difference obtained in Test Example 1 and the degree of elution of catechins in Test Example 2.
  • FIG. 2 is a graph showing the effect of dentifrice composition A on the gum.
  • FIG. 3 is a graph showing the effect of dentifrice composition B on the gum.
  • the average particle size of hydrogel particles was measured by the sieve method described above.
  • aqueous solution prepared by dissolving 20 g of polyvinyl pyrrolidone (K-15, weight-average molecular weight 8000, manufactured by ISP) in 330 g of deionized water was mixed by a homomixer (8000 r/min, 1 minute) with an aqueous solution (20° C.) prepared by dissolving 10 g of catechin powder (Sunphenon 100S manufactured by Taiyo Kagaku Co., Ltd.) in 140 g of deionized water, to yield an aqueous catechin/PVP complex dispersion with the composition in Table 1.
  • the average particle size of the hydrogel particles was 195 ⁇ m.
  • Example 3 The aqueous catechin/PVP complex dispersion obtained in Example 1, the catechin/PVP complex-included hydrogel particles in Example 2 and the aqueous catechin solution in Comparative Example 1 were used to prepare preparations with the compositions shown in Table 3.
  • the resulting preparations were stored at 50° C. for 1 month and measured for brightness difference before and after storage, and by this brightness difference, the degree of discoloration was evaluated. The results are shown in Table 3.
  • a transparent case with an internal size of 3 cm ⁇ 3 cm ⁇ 1 cm was filled up with the preparation after storage.
  • nine points in KODAK GRAY SCALE that is, A, 2, 4, 6, 8, 10, 12, 14 and B (assumed to be color densities 1 to 9, respectively) as color density standards, and CASMATCH (manufactured by Dai Nippon Printing Co., Ltd.), were photographed on a white paper in the same visual field. The photographing was conducted at a constant shutter speed, stop and focal distance under uniform lighting with a ring light.
  • the photographed image was color-corrected with CASMATCH in an ADOBE PHOTOSHOP, then the brightness (brightness in HSB color model) in a site to be measured was quantified with WINROOF (Mitani Corporation), and the difference between the brightness of the sample stored at 50° C. for 1 month and the initial brightness was determined as the degree of discoloration by using the following equation:
  • aqueous catechin/PVP complex dispersion obtained in Example 1, the catechin/PVP complex-included hydrogel particles in Example 2, and the aqueous catechin solution in Comparative Example 1 were used to prepare aqueous sodium lauryl sulfate solutions with the compositions shown in Table 4.
  • the amount of catechin eluted into the aqueous sodium lauryl sulfate solution after 1 month of storage at room temperature was quantified by the following method to determine the degree of elution. The results are shown in Table 4.
  • aqueous sodium lauryl sulfate solution aqueous sodium lauryl sulfate solution
  • phosphate buffer aqueous sodium lauryl sulfate solution
  • iron tartrate reagent aqueous catechin solutions of known concentration are prepared from catechin powder (Sunphenon 100S) and used to prepare a calibration curve. The concentration of catechin in the sample is determined from the calibration curve to determine the degree of elution.
  • the iron tartrate reagent is prepared by dissolving 100 mg ferrous sulfate (7H 2 O) and 500 mg sodium potassium tartrate in water to prepare a 100 ml solution.
  • the phosphate buffer is prepared by mixing M/15 disodium hydrogenphosphate and M/15 dipotassium hydrogenphosphate at a ratio of 84:16.
  • the measurement results of brightness difference in Test Example 1 are plotted against the degree of elution of catechin obtained in Test Example 2, to show the relationship between the degree of elution and the brightness difference in FIG. 1 . From FIG. 1 , it was found that as the degree of elution into the aqueous sodium lauryl sulfate solution decreases, the brightness difference decreases. That is, it was found that the effect of suppressing discoloration increases with a decreasing degree of catechin into the aqueous sodium lauryl sulfate solution when the PVP/catechin complex is mixed with the aqueous sodium lauryl sulfate solution, and the oxidation and/or polymerization of catechin can be suppressed and the stability of catechin is high.
  • aqueous solution prepared by dissolving 12.5 g of agar (UP-37) and 10.0 g of PVP (K-30, weight-average molecular weight of 60000) in 327.5 g of deionized water was mixed by a homomixer (8000 r/min, 1 minute) with an aqueous solution (20° C.) prepared by dissolving 5 g of catechin powder (Sunphenon 100S) in 145 g of deionized water, and then sprayed into a gaseous phase to yield catechin/PVP complex-included hydrogel particles having the composition and average particle size shown in Table 5.
  • Catechin/PVP complex-included hydrogel particles having the composition and average particle size shown in Table 5 were obtained in the same manner as in Example 3 except that 10.0 g of PVP (K-60, weight-average molecular weight of 400000, manufactured by ISP) was used.
  • Catechin/PVP complex-included hydrogel particles having the composition and average particle size shown in Table 5 were obtained in the same manner as in Example 3 except that 10.0 g of PVP (K-90, weight-average molecular weight of 1300000) was used.
  • the catechin/PVP complex-included hydrogel particles prepared in Examples 3 to 5 were used to prepare aqueous sodium lauryl sulfate solutions with the compositions shown in Table 6.
  • the amount of catechin eluted into the sodium lauryl sulfate solution after 10 days of storage at room temperature was quantified in the same manner as in Test Example 2 to determine the degree of elution. The results are shown in Table 6.
  • aqueous solution prepared by dissolving 12.5 g of agar (UP-37), 3.0 g of PVP (K-30) and 9.0 g of PVP (K-90) in 325.5 g of deionized water was mixed by a homomixer (8000 r/min, 1 minute) with an aqueous solution (20° C.) prepared by dissolving 10 g catechin powder (Sunphenon 100S) in 140 g of deionized water, and then sprayed into a gaseous phase to yield catechin/PVP complex-included hydrogel particles having the composition and average particle size shown in Table 7.
  • aqueous solution prepared by dissolving 12.5 g of agar (UP-37), 3.5 g of PVP (K-30) and 10.5 g of PVP (K-90) in 323.5 g of deionized water was mixed by a homomixer (8000 r/min, 1 minute) with an aqueous solution (20° C.) prepared by dissolving 10 g of catechin powder (Sunphenon 100S) in 140 g of deionized water, and then sprayed into a gaseous phase to yield catechin/PVP complex-included hydrogel particles having the composition and average particle size shown in Table 7.
  • aqueous solution prepared by dissolving 12.5 g of agar (UP-37), 5.0 g of PVP (K-30) and 15.0 g of PVP (K-90) in 323.5 g of deionized water was mixed by a homomixer (8000 r/min, 1 minute) with an aqueous solution (20° C.) prepared by dissolving 10 g of catechin powder (Sunphenon 100S) in 140 g of deionized water, and then sprayed into a gaseous phase to yield catechin/PVP complex-included hydrogel particles having the composition and average particle size shown in Table 7.
  • aqueous solution prepared by dissolving 12.5 g of agar (UP-37), 5.5 g of PVP (K-30) and 16.5 g of PVP (K-90) in 323.5 g of deionized water was mixed by a homomixer (8000 r/min, 1 minute) with an aqueous solution (20° C.) prepared by dissolving 10 g of catechin powder (Sunphenon 100S) in 140 g of deionized water, and then sprayed into a gaseous phase to yield catechin/PVP complex-included hydrogel particles having the composition and average particle size shown in Table 7.
  • Example 9 Hydrogel particles Agar(UP-37) 2.5 2.5 2.5 2.5 2.5 (% by weight) Polyvinyl pyrrolidone (K-30) 0.6 0.7 1.0 1.1 Polyvinyl pyrrolidone (K-90) 1.8 2.1 3.0 3.3 Catechin (Sunphenon 100S) 2.0 2.0 2.0 2.0 Deionized water 93.1 92.7 91.5 91.1 Weight ratio of catehin/PVP 1/1.2 1/1.4 1/2.0 1/2.2 Average particle diameter ( ⁇ m) 215 230 210 220
  • the catechin/PVP complex-included hydrogel particles prepared in Example 2 and Examples 6 to 9 were used to prepare aqueous sodium lauryl sulfate solutions with the compositions shown in Table 8.
  • the amount of catechin eluted into the aqueous sodium lauryl sulfate solution after 20 days of storage at room temperature was quantified in the same manner as in Test Example 2 to determine the degree of elution. The results are shown in Table 8.
  • the dentifrice composition of the present invention will be described by reference to the following examples.
  • aqueous solution prepared by dissolving 15 g of agar (UP-37 manufactured by Ina Food Industry Co., Ltd.) and 16 g of PVP (K-90, weight-average molecular weight of 1300000, manufactured by ISP) in 319 g of deionized water was mixed by a homomixer (8000 r/min, 1 minute) with an aqueous solution (20° C.) prepared by dissolving 10 g of tea extract (Sunphenon 100S, catechin content 60 to 70%, manufactured by Taiyo Kagaku Co., Ltd.) in 140 g of deionized water, and then sprayed into a gaseous phase to yield hydrogel particles with the composition shown in Table 9.
  • the average particle size of the hydrogel particles was 200 ⁇ m.
  • the hydrogel particles obtained in Production Example 1 or the tea extract (Sunphenon 100S, catechin content 60 to 70%, manufactured by Taiyo Kagaku Co., Ltd.) was used to prepare dentifrice composition A (Comparative Product) and dentifrice composition B (Invented Product) having the compositions shown in Table 10.
  • the resulting dentifrice compositions A and B were evaluated for their discoloration and taste by the following methods. The results are shown in Table 10. The effect on the gum was also examined by the following method. The results are shown in FIGS. 2 and 3 .
  • the resulting dentifrice composition was filled in a container, stored at 50° C. for 1 month, and measured for brightness difference after storage by the following method, and by this brightness difference, the degree of discoloration was evaluated.
  • a transparent case with an internal size of 3 cm ⁇ 3 cm ⁇ 1 cm PS CASE No. 1, manufactured by AS ONE
  • nine points in KODAK GRAY SCALE that is, A, 2, 4, 6, 8, 10, 12, 14 and B (assumed to be color densities 1 to 9, respectively) as color density standards
  • CASMATCH manufactured by Dai Nippon Printing Co., Ltd.
  • the photographing was conducted at a constant shutter speed, stop and focal distance under uniform lighting with a ring light.
  • the photographed image was color-corrected with CASMATCH in an ADOBE PHOTOSHOP, then the brightness (brightness in HSB color model) in a site to be measured was quantified with WINROOF (Mitani Corporation), and the difference between the brightness of the sample stored at 50° C. for 1 month and the (initial) brightness just after production was determined as the degree of discoloration by using the following equation (I):
  • Flavors of the dentifrice compositions A and B were evaluated by a panel of 9 experts under the following 3 criteria, and the results are shown in mean value.
  • the dentifrice compositions A and B were used respectively for 1 week by 9 male and female persons in their twenties to fifties and examined for change in BOP (Bleeding On Probing) before and after use.
  • BOP Bleeding On Probing refers to a state of bleeding occurring when a WHO probe is removed after insertion into the bottom of the gum in a periodontal pocket (gap between tooth and gum). Bleeding does not occur when the gum is healthy, while bleeding easily occurs when there is inflammation in the pocket and the bottom of the gum. That is, the gum is in a worse state as the number of BOP sites increases.
  • composition B Composition Polyethylene glycol 600 * 1 4 4 (%) Sodium fluorate 0.2 0.2 Sorbit liquid(70% aqueous solution) 40 40 Abrasive silica * 2 10 10 Thickening silica * 3 5 5 5 Sodium lauryl sulfate 1 1 Carboxymethylcellulose sodium * 4 0.5 0.5 DL-malic acid 0.1 0.1 Ascorbic acid 0.1 0.1 Anhydrous sodium pyrophosphate 0.2 0.2 Saccharine sodium 0.1 0.1 Perfume 1 1 Colorant Trace amount Trace amount Tea extrat * 5 0.06 — Hydrogel particles in Production example 1 — 3 Purified water Balance Balance Total 100 100 Results of Degree of discoloration 63.4 1.2 evaluation Taste 2.5 1.67 * 1 Polyethylene glycol with an average molecular weight of 600 * 2 Solbocyl AC43 (Ineos Silicas Limited) * 3 Solbocyl TC15 (Ineos Silicas Limited) * 4 CMC ⁇ 1150> manufactured by Da
  • the dentifrice composition B containing the catechin-included hydrogel particles of the present invention as compared with the dentifrice composition A containing catechins as they are without being included, was significantly prevented from discoloring and was superior in taste.
  • the hydrogel particles obtained in Production Example 1 or the tea extract (Sunphenon 100S, catechin content 60 to 70%, manufactured by Taiyo Kagaku Co., Ltd.) was used to prepare dentifrice composition C (Comparative Product) and dentifrice composition D (Invented Product) having the compositions shown in Table 11.
  • the resulting dentifrice compositions C and D were evaluated for their discoloration and taste by the same methods as in Example 10. The results are shown in Table 11.
  • the dentifrice composition D containing the catechin-included hydrogel particles of the present invention as compared with the dentifrice composition C containing catechins as they are without being included, was significantly prevented from discoloring and was superior in taste.

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WO2008010403A1 (fr) 2008-01-24
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EP2045248A1 (fr) 2009-04-08
TW200821290A (en) 2008-05-16

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