CN113853194A - Oral composition and gingiva massaging feeling imparting agent - Google Patents
Oral composition and gingiva massaging feeling imparting agent Download PDFInfo
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- CN113853194A CN113853194A CN202080034777.3A CN202080034777A CN113853194A CN 113853194 A CN113853194 A CN 113853194A CN 202080034777 A CN202080034777 A CN 202080034777A CN 113853194 A CN113853194 A CN 113853194A
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- Prior art keywords
- oral composition
- massaging
- feeling
- gum
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- 210000004195 gingiva Anatomy 0.000 title claims abstract description 10
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- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 claims abstract description 23
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- 229940035436 maltitol Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
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- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 229940102398 methyl anthranilate Drugs 0.000 description 1
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- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
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- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
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- 229940077082 red pepper extract Drugs 0.000 description 1
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- 239000010666 rose oil Substances 0.000 description 1
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- 239000010670 sage oil Substances 0.000 description 1
- 208000026451 salivation Diseases 0.000 description 1
- 108700004121 sarkosyl Proteins 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
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- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229940079841 sodium copper chlorophyllin Drugs 0.000 description 1
- 235000013758 sodium copper chlorophyllin Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 229940045944 sodium lauroyl glutamate Drugs 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 229940045885 sodium lauroyl sarcosinate Drugs 0.000 description 1
- 229940075560 sodium lauryl sulfoacetate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229960004711 sodium monofluorophosphate Drugs 0.000 description 1
- 229950005425 sodium myristyl sulfate Drugs 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- IWIUXJGIDSGWDN-UQKRIMTDSA-M sodium;(2s)-2-(dodecanoylamino)pentanedioate;hydron Chemical compound [Na+].CCCCCCCCCCCC(=O)N[C@H](C([O-])=O)CCC(O)=O IWIUXJGIDSGWDN-UQKRIMTDSA-M 0.000 description 1
- UAJTZZNRJCKXJN-UHFFFAOYSA-M sodium;2-dodecoxy-2-oxoethanesulfonate Chemical compound [Na+].CCCCCCCCCCCCOC(=O)CS([O-])(=O)=O UAJTZZNRJCKXJN-UHFFFAOYSA-M 0.000 description 1
- UPUIQOIQVMNQAP-UHFFFAOYSA-M sodium;tetradecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCOS([O-])(=O)=O UPUIQOIQVMNQAP-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- ANOBYBYXJXCGBS-UHFFFAOYSA-L stannous fluoride Chemical compound F[Sn]F ANOBYBYXJXCGBS-UHFFFAOYSA-L 0.000 description 1
- 229960002799 stannous fluoride Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 description 1
- 229940013618 stevioside Drugs 0.000 description 1
- OHHNJQXIOPOJSC-UHFFFAOYSA-N stevioside Natural products CC1(CCCC2(C)C3(C)CCC4(CC3(CCC12C)CC4=C)OC5OC(CO)C(O)C(O)C5OC6OC(CO)C(O)C(O)C6O)C(=O)OC7OC(CO)C(O)C(O)C7O OHHNJQXIOPOJSC-UHFFFAOYSA-N 0.000 description 1
- 235000019202 steviosides Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 1
- 229910001637 strontium fluoride Inorganic materials 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YIGWVOWKHUSYER-UHFFFAOYSA-F tetracalcium;hydrogen phosphate;diphosphate Chemical compound [Ca+2].[Ca+2].[Ca+2].[Ca+2].OP([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O YIGWVOWKHUSYER-UHFFFAOYSA-F 0.000 description 1
- GBNXLQPMFAUCOI-UHFFFAOYSA-H tetracalcium;oxygen(2-);diphosphate Chemical compound [O-2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GBNXLQPMFAUCOI-UHFFFAOYSA-H 0.000 description 1
- 239000010678 thyme oil Substances 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- GYDJEQRTZSCIOI-LJGSYFOKSA-N tranexamic acid Chemical compound NC[C@H]1CC[C@H](C(O)=O)CC1 GYDJEQRTZSCIOI-LJGSYFOKSA-N 0.000 description 1
- 229960000401 tranexamic acid Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- ICUTUKXCWQYESQ-UHFFFAOYSA-N triclocarban Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 ICUTUKXCWQYESQ-UHFFFAOYSA-N 0.000 description 1
- 229960001325 triclocarban Drugs 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- WGIWBXUNRXCYRA-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WGIWBXUNRXCYRA-UHFFFAOYSA-H 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011746 zinc citrate Substances 0.000 description 1
- 235000006076 zinc citrate Nutrition 0.000 description 1
- 229940068475 zinc citrate Drugs 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
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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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
-
- 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
- A61K8/31—Hydrocarbons
-
- 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
-
- 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
- A61K8/96—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
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth 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)
- Microbiology (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Mycology (AREA)
- Emergency Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Cosmetics (AREA)
Abstract
The invention provides a gingiva massaging feeling imparting agent which has an excellent effect of imparting a massaging feeling to gingiva and imparts a unique and high massaging feeling from the time of use in the oral cavity to the time after use, and an oral composition containing the same. An oral composition comprising: (a) more than 1 selected from sanshool and derivatives thereof, and (b) alpha-phellandrene. An oral composition comprises (A) Sichuan pepper extract and (B) Pink pepper extract. The oral composition further comprises (C) citral. The oral composition further comprises 1 or more selected from (D) citral diethyl acetal and citral dimethyl acetal. A gingiva massaging feeling imparting agent comprising components (A) and (B). A massaging feeling-imparting agent for gums further comprises component (C). A massaging feeling-imparting agent for gums further comprises component (D).
Description
Technical Field
The present invention relates to a gingival massaging feeling-imparting agent which has an excellent effect of imparting a massaging feeling to the gingiva and imparts a unique massaging feeling even after use in the oral cavity, and an oral composition containing the same.
Background
In oral compositions such as dentifrice, the feeling of effect is felt at the site of use, particularly at the gum, during and after use in the oral cavity, and the effect is expected to be improved in terms of prevention or suppression of periodontal diseases such as daily gingival inflammation, halitosis, and the like. From such a viewpoint, an oral composition which imparts a more satisfactory feeling of effect to the gum has been desired.
However, when stimulus components such as spilanthol and red pepper are mixed as flavors used in conventional oral compositions, the astringent, pungent, and bitter taste stimulus sensations are imparted, so that the gum can be given a firm feeling and a moderate stimulus feeling, and the effect feeling of various active ingredients mixed in the oral composition can be produced.
Patent document 1 (japanese patent No. 5251350) discloses: a dentifrice composition comprising a refreshing feeling-imparting agent such as sodium chloride or menthol, monomenthyl succinate and a specific surfactant in combination has a medicinal effect (tightening feeling of gum and moderate irritation), and further comprises an essential oil or extract such as spilanthol, black pepper and red pepper. As a technique for producing an effect feeling by applying a flavor such as Japanese pepper, patent document 2 (Japanese patent No. 5748626) proposes an oral composition in which a combined system of Japanese pepper extract and guaiacol or ethylguaiacol at a specific ratio is used as a bactericide, which has a good medicinal effect feeling and effect feeling, and a supercritical extract of Japanese pepper (Zanthoxylum piperitum) belonging to the genus Zanthoxylum is used as the Japanese pepper extract. Patent document 3 (patent No. 5897843) discloses: patent document 4 (japanese patent laid-open publication No. 2015-43769) discloses that a specific flavor extract such as capsicum, zanthoxylum piperitum, and black pepper is mixed in an oral composition to enhance and maintain the taste and pleasant feeling of mints: the oral composition containing hydroxy-alpha-sanshool and/or 2-phenylbutenal has strong salivation effect and moistening effect. Patent document 5 (japanese patent laid-open No. 2012 and 246278) discloses that an extract of a plant of the genus zanthoxylum of the family rutaceae or the like as a pungent ingredient having astringency can be applied as a refreshing agent to an oral composition, and patent document 6 (patent No. 5171104) discloses that when α -phellandrene and menthol are mixed in a specific ratio in an oral composition, the refreshing feeling of menthol is enhanced.
Documents of the prior art
Patent document
Patent documents: japanese patent No. 5251350
Patent document 2: japanese patent No. 5748626
Patent document 3: japanese patent No. 5897843
Patent document 4: japanese laid-open patent publication No. 2015-43769
Patent document 5: japanese laid-open patent publication No. 2012 and 246278
Patent document 6: japanese patent No. 5171104
Disclosure of Invention
Technical problem to be solved by the invention
The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a gingival massaging sensation imparting agent which has an excellent effect of imparting a massaging sensation to the gingiva without using a stimulating component such as spilanthol and which imparts a unique massaging sensation in the oral cavity from the time of use to the time after use, and an oral composition containing the same.
Means for solving the problems
The present inventors have made intensive studies to achieve the above object, and as a result, have recognized that: when the above-mentioned components (a) selected from 1 or more of sanshool and its derivatives, particularly component (a) derived from Sichuan pepper, and (b) alpha-phellandrene, particularly component (b) derived from Pink pepper, are used in combination, the gum is given a unique massaging feeling. Further, the present inventors have found that a system combining components (a) and (B), particularly a system combining component (a) a sichuan pepper extract and a pink pepper extract, is mixed into an oral composition as an effective component for imparting a massaging sensation to gums, whereby the oral composition is excellent in the effect of imparting a massaging sensation to gums, can impart a pleasant and moderately high unique massaging sensation to gums even after use in the oral cavity, and can ensure a good feeling of use with suppressed unpleasant taste, and have completed the present invention.
That is, in the present invention, when the components (a) and (B), particularly the components (a) and (B), are used in combination, the two components act synergistically with each other to provide a massage feeling, and a unique massage feeling can be satisfactorily provided to the gum from the time of use to the time of use in the oral cavity (the gum is massaged by a moderate stimulation such as breaking of fine bubbles to the gum, and the gum feels a tight state).
More specifically, when the component (a) (component (a)) is mixed alone and the component (B) (component (B)) is mixed alone, the effect of imparting a massaging sensation to the gums is low, and the massaging sensation of the gums during use or after use is poor. However, surprisingly, in the present invention, by using the components (a) and (B) together (components (a) and (B)), it is possible to provide a superior massaging feeling to the gum while maintaining a good taste without feeling unpleasant irritation or the like caused by these components as an unpleasant taste (see examples described later).
The action and effect of the present invention are specific and specific action and effect to the specific combination system, and the effect of imparting a massage feeling is poor when the component (a) (component (a)) is absent or the component (B) (component (B)) is absent (see comparative examples 1 and 2 described later).
Patent document 1 discloses an improvement in the medicinal effect due to sodium chloride or the like, and an improvement in the taste due to addition of red pepper, black pepper extract (main component is piperine) or the like, and patent document 2 discloses an improvement in the medicinal effect due to the use of a mountain pepper extract or the like in combination with a bactericide. Further, patent document 6 is to enhance the cooling sensation of menthol by α -phellandrene. On the other hand, in the present invention, the components (a) and (B) (the components (a) and (B)) are used in combination to give a unique massaging feeling to the gum, and the specific and special actions and effects of the combination system in the present invention cannot be expected from patent documents 1 to 6 which do not mention the combination use of these components.
Accordingly, the present invention provides the following oral composition and gum massaging feeling imparting agent.
〔1〕
An oral composition comprising:
(a) selected from sanshool and its derivatives, and
(b) alpha-phellandrene.
〔2〕
The oral composition according to [ 1] which comprises 0.00004 to 0.05 mass% of the component (a), 0.0002 to 0.04 mass% of the component (b), and a mass ratio of (a)/(b) of 0.001 to 250.
〔3〕
An oral composition comprises (A) Sichuan pepper extract and (B) Pink pepper extract.
〔4〕
The oral composition according to [ 3], wherein the Sichuan pepper extract (A) contains 40% by mass or more of (a) 1 or more selected from sanshool and derivatives thereof.
〔5〕
The oral composition according to [ 3] or [ 4], wherein the pink pepper extract (B) contains not less than 20% by mass of (B) α -phellandrene.
〔6〕
The oral composition according to any one of [ 3] to [ 5], wherein the mass ratio of (A)/(B) is 0.001 to 100.
〔7〕
The oral composition according to any one of [ 3] to [ 6 ], which comprises 0.0001 to 0.1 mass% of the component (A).
〔8〕
The oral composition according to any one of [ 3] to [ 7 ], which comprises 0.001 to 0.1 mass% of the component (B).
〔9〕
The oral composition according to any one of [ 1] to [ 8 ], further comprising (C) citral in an amount of 0.001 to 0.2 mass%.
〔10〕
The oral composition according to any one of [ 1] to [ 9 ], further comprising 0.001 to 0.1 mass% of (D) at least one selected from citral diacetal and citral diacetal.
〔11〕
The oral composition according to any one of [ 1] to [ 10 ], which is a dentifrice composition.
〔12〕
A gingiva massage feeling imparting agent comprising (A) Sichuan pepper extract and
(B) pink pepper extract.
〔13〕
The agent for imparting a massaging sensation to a gum according to [ 12 ], wherein the mass ratio of (A)/(B) is 0.001 to 100.
〔14〕
The gingival massaging sensation imparting agent according to [ 12 ] or [ 13 ], wherein the composition further comprises (C) citral.
〔15〕
The agent for imparting a massaging sensation to the gum according to any one of [ 12 ] to [ 14 ], further comprising (D) 1 or more selected from citral diacetal and citral diacetal.
ADVANTAGEOUS EFFECTS OF INVENTION
The present invention can provide a gingival massaging feeling-imparting agent which has an excellent effect of imparting a massaging feeling to the gingiva and imparts a unique and high massaging feeling even after use in the oral cavity, and an oral composition containing the same. According to the present invention, it is possible to provide a gum having a unique massaging feeling with a good taste with low irritation without adding any irritant component such as spilanthol or red pepper which is relatively strong in irritation, and to provide a gum with a unique massaging feeling without adding any such irritant component, and to be effective for preventing or suppressing periodontal diseases such as gingivitis.
Detailed Description
The present invention will be described in further detail below. The oral composition of the present invention comprises (a) at least one selected from sanshool and derivatives thereof and (B) α -phellandrene, and preferably comprises (a) Sichuan pepper extract and (B) Pink pepper extract. (A) The Sichuan pepper extract preferably contains (a) at least 1 selected from sanshool and derivatives thereof and (B) the Pink pepper extract preferably contains (B) alpha-phellandrene in a specific amount. In the present invention, these components are effective components for imparting a massaging sensation to the gums, and a system in which the components (a) and (B) are used in combination, particularly a system in which the components (a) and (B) are used in combination, functions as a massaging sensation imparting agent for the gums.
(a) The component (A) is 1 or 2 or more selected from sanshool and its derivatives, and the preferred sanshool derivative is hydroxy sanshool (hereinafter, sanshool and hydroxy sanshool are simply referred to as sanshools). (a) The component (A) is preferably derived from Sichuan pepper and may be mixed in the form of (A) Sichuan pepper extract, although the component (A) is specifically sanshool, and is also included in Zanthoxylum piperitum (chemical name: Zanthoxylum piperitum) and the like, from the viewpoint of giving a massaging feeling to gums.
Sichuan pepper as a raw material of Sichuan pepper extract (A) is generally known as Zanthoxylum bungeanum, and can be obtained by drying pericarp of Zanthoxylum bungeanum (scientific name: zanuun bungeanum, English name: Sichuan pepper), a deciduous shrub of Zanthoxylum genus of Rutaceae, China.
The Sichuan pepper extract can be obtained by using the above-mentioned raw materials and by using known methods, such as essential oils and extracts obtained by steam distillation and commercially available extracts obtained by solvents; supercritical extraction with carbon dioxide is used. Among them, the supercritical carbon dioxide extract is preferably used in order to impart a massaging feeling to the gum.
By performing the supercritical extraction using carbon dioxide as described above, an extract containing sanshools in a specific amount or more can be obtained.
The Sichuan pepper extract preferably contains 40% by mass or more, particularly preferably 50% or more, of the component (a), particularly sanshools, in order to impart a massaging feeling to the gums.
As described above, the extract of Sichuan pepper can be any commercially available product, for example, Sichuan pepper net CO manufactured by CHARABOT corporation2Extract (SICHUAN PEPER ABSOLUTE CO)2EXTRACT, EXTRACT obtained by supercritical extraction with carbon dioxide, and sanshool content 50%), etc.
(a) The amount of the component (c), particularly sanshool, is preferably 0.00004% or more, more preferably 0.00004 to 0.05%, and still more preferably 0.0002 to 0.005% of the total composition. When the amount of the compound is within the above range, unpleasant taste accompanying stimulation is suppressed, good taste is maintained, and a massage feeling that the gum is tensed is sufficiently obtained.
When the Sichuan pepper extract (A) is mixed, the amount to be mixed is preferably 0.0001 to 0.1%, more preferably 0.0005 to 0.01% of the total composition. When the amount is 0.0001% or more, a sufficient massaging feeling of the gum can be obtained. When the content is 0.1% or less, the massage feeling in use can be sufficiently ensured, and unpleasant taste accompanying its own stimulation can be sufficiently suppressed to ensure good taste.
The amount of component (a) in the oral composition is preferably within the above range, and (a) the sichuan pepper extract may be mixed within the above range.
(b) α -phellandrene is also included in nutmeg, fennel, mint, and the like, but is preferably derived from pink pepper from the viewpoint of imparting a massaging feeling to the gums, and may be mixed in the form of (B) a pink pepper extract.
(B) As the Pink pepper extract, there can be used an essential oil obtained from the fruit of Pink pepper (academic name; Schinus molle, Piper Brazilian, Anacardiaceae; Frankia velutina, or academic name; Schinus terebinthifolius, Piper Brazilian, Anacardiaceae; Piper muscat (アカツユ)) as a raw material thereof.
The essential oil can be obtained by extracting the plant of the above raw material by a known method. For example, commercially available essential oils obtained by steam distillation, extracts obtained by solvents and the like, and supercritical extracts using carbon dioxide can be used. The extraction solvent can be water, lower monohydric alcohol such as ethanol, etc., and the extraction conditions and post-treatment can be conventional method.
By performing the extraction as described above, an extract containing a specific amount or more of α -phellandrene can be obtained.
The pink pepper extract preferably contains not less than 20% of α -phellandrene, particularly preferably 20 to 40%, and particularly preferably 30 to 40%, from the viewpoint of imparting a massaging feeling to gums.
As the above-mentioned pink pepper extract, commercially available products such as those manufactured by v.mane Fils perfumery (pink pepper extract, supercritical extract of pink pepper fruit, α -phellandrene content 35%) can be used.
(b) The amount of α -phellandrene is 0.0002% or more, particularly preferably 0.0002 to 0.04%, more preferably 0.001 to 0.02% of the total composition. When the amount of the additive is within the above range, unpleasant taste accompanying stimulation is suppressed and good taste is maintained, and a satisfactory massaging feeling that makes the gum tight can be sufficiently obtained.
When the pink pepper extract (B) is mixed, the mixing amount thereof is preferably 0.001 to 0.1%, more preferably 0.005 to 0.05% of the total composition. When the amount is 0.001% or more, a sufficient massaging feeling of the gum can be obtained. When the content is 0.1% or less, the massage feeling after use is sufficiently secured, and the unpleasant taste accompanying the stimulation itself can be suppressed, thereby securing a good taste.
The pink pepper extract (B) is preferably used in an amount within the above range, and may be mixed within the range, in the oral composition.
In the present invention, (a)/(b), which represents the amount ratio of the component (a) to the component (b), is preferably 0.001 to 250, more preferably 0.001 to 150, and particularly preferably 0.01 to 5 in terms of mass ratio. When the amount is within the above range, the massaging feeling of the gum is particularly excellent, and the unpleasant taste accompanying the stimulation can be sufficiently suppressed.
The mass ratio of (A)/(B) representing the amount ratio of the component (A) to the component (B) is preferably 0.001 to 100, and particularly preferably 0.01 to 2. When the amount is within the above range, the massaging feeling of the gum is particularly excellent, and the unpleasant taste accompanying the stimulation is sufficiently suppressed.
In the oral composition of the present invention, (C) citral is preferably further mixed. When the citral (C) is blended, the massaging feeling of the gum during use can be particularly enhanced.
As the citral, a single product of citral may be used, and in addition, essential oils containing citral, such as lemon oil, orange oil, grapefruit oil, and the like, may also be used.
(C) As citral, commercially available products can be used, and for example, a product manufactured by Changchuan flavor Kabushiki Kaisha (Ltd.) can be used.
(C) The amount of citral to be mixed is preferably 0.001 to 0.2%, more preferably 0.005 to 0.1%, of the total composition. When the amount is within this range, the massaging effect on the gum during use can be more sufficiently enhanced, and the unpleasant taste accompanying the oily feeling itself can be sufficiently suppressed, so that a good feeling of use can be ensured.
In the oral composition of the present invention, it is preferable that 1 or more selected from citral diethyl acetal and citral dimethyl acetal (D) is further mixed. When the component (D) is blended, the massaging feeling of the gum after use can be particularly enhanced. When the component (D) and the component (C) are mixed together, the massaging feeling of the gum is further enhanced during and after use, and a more excellent massaging feeling can be imparted.
As the citral diethyl acetal and citral dimethyl acetal, respective single products can be used.
The citral diacetal and citral diacetal may be commercially available products, and for example, products manufactured by Koshika Kogyo K.K. may be used.
(D) The amount of the component (B) is preferably 0.001 to 0.1%, more preferably 0.005 to 0.05% of the total composition. When the amount of the surfactant is within this range, the massaging feeling of the gum after use can be more sufficiently enhanced, and the unpleasant taste accompanying the oily feeling thereof can be sufficiently suppressed, so that the use feeling with good taste can be maintained.
The oral composition of the present invention is preferably a dentifrice composition which can be formulated into a dentifrice such as a toothpaste, a liquid dentifrice, a wet powder dentifrice, a mouthwash or a deodorant spray in the form of a paste or a liquid, and is particularly preferably a dentifrice or a mouthwash, and is particularly preferably a dentifrice, and is particularly preferably a toothpaste, and is preferably a dentifrice composition.
If necessary, other known additives may be added to the composition according to the dosage form within a range not to impair the effects of the present invention. For example, a surfactant, a polishing agent, a thickener, a binder, a sweetener, an antiseptic, various active ingredients, a coloring agent, a pH adjuster, a perfume, and the like may be mixed, and these ingredients and water may be mixed to produce the composition.
Examples of the surfactant include anionic surfactants, nonionic surfactants, cationic surfactants, and amphoteric surfactants. Specifically, 1 kind of the following substances may be used alone or 2 or more kinds may be used in combination.
Anionic surfactant:
alkyl sulfates such as sodium lauryl sulfate and sodium myristyl sulfate; acyl taurines such as lauroyl methyl taurin or salts thereof; sodium lauryl sulfoacetate; an alpha-olefin sulfonate; acyl sarcosinates such as sodium lauroyl sarcosinate; acyl amino acid salts such as sodium lauroyl glutamate;
nonionic surfactant:
polyoxyethylene fatty acid esters such as polyoxyethylene hydrogenated castor oil; polyoxyethylene higher alcohol ethers such as polyoxyethylene lauryl ether and polyoxyethylene cetyl ether; sugar fatty acid esters such as sucrose fatty acid ester, sugar alcohol fatty acid ester, sorbitan fatty acid ester, glycerin fatty acid ester, and polyglycerin fatty acid ester;
cationic surfactant:
distearyl methyl ammonium chloride, stearyl dimethyl benzyl ammonium chloride
Amphoteric surfactant:
betaine systems such as 2-alkyl-N-carboxymethyl-N-hydroxyethyl imidazolinebetaine and fatty acid amidopropylbetaine.
The amount of the surfactant to be mixed is preferably 0.1 to 10%, particularly 0.5 to 8%, of the whole composition.
Examples of the polishing agent include silica-based polishing agents such as silicic anhydride, silica gel, aluminosilicate, zirconium silicate, and crystalline zirconium silicate, calcium phosphate-based polishing agents such as calcium hydrogen phosphate monohydrate, calcium dihydrate, tricalcium phosphate, tetracalcium phosphate, octacalcium phosphate, and calcium pyrophosphate, alumina, titania, polymethyl methacrylate, insoluble calcium metaphosphate, calcium carbonate, magnesium phosphate, zeolite, hydroxyapatite, fluorapatite, and synthetic resin-based polishing agents. The abrasive may not be mixed (0% in the mixing amount), but when the abrasive is mixed, the mixing amount is preferably 2 to 50%, particularly 10 to 40%, of the whole composition.
Examples of the thickener include sugar alcohols such as sorbitol, xylitol, erythritol, maltitol, mannitol, and reduced starch saccharide, and polyols such as glycerol, propylene glycol, polyethylene glycol having an average molecular weight (average molecular weight described in pharmaceutical department external product material specification 2006) of 200 to 6,000, and ethylene glycol.
The amount of the thickener is usually 5 to 50% of the total composition.
Examples of the binder include organic binders such as sodium polyacrylate, xanthan gum, carrageenan, sodium alginate, propylene glycol alginate, sodium carboxymethylcellulose, hydroxyethylcellulose, Carbopol (Carbopol), guar gum, gelatin, crystalline cellulose, polyvinyl alcohol, and polyvinylpyrrolidone, and inorganic binders such as gelled silica, gelled alumina silica, montmorillonite, kaolin, and bentonite. The amount of the organic binder is preferably 0.01 to 5% by weight of the entire composition, and the amount of the inorganic binder is preferably 0.1 to 10% by weight of the entire composition.
Examples of the sweetener include saccharin sodium, aspartame, stevioside, stevia extract, neohesperidin dihydrochalcone, perillartine (perillatin), and the like.
Examples of the preservative include parabens such as methyl paraben and ethyl paraben, benzoic acid such as sodium benzoate, and salts thereof.
As any active ingredient, known active ingredients usually mixed in oral compositions, such as fluoride, bactericide, anti-inflammatory agent, enzyme, plant extract, tartar inhibitor, plaque inhibitor and the like, may be mixed in an effective amount in a range not to impair the effects of the present invention. Specifically, fluoride such as sodium fluoride, stannous fluoride, strontium fluoride, sodium monofluorophosphate, etc., sodium orthophosphate, tranexamic acid, epsilon-aminocaproic acid, tocopherol acetate, alpha-bisabolol, dihydrocholesterol, chlorhexidine salts, azurin, glycyrrhizin, glycyrrhetinic acid, glycyrrhizic acid or its salts, sodium copper chlorophyllin, copper compounds such as chlorophyll and copper gluconate, chelating phosphate compounds such as glycerophosphate, hydroxamic acid or its derivatives, sodium tripolyphosphate, methoxyethylene, epidihydrocholesterol, isopropylmethylphenol, benzethonium chloride, cetylpyridinium chloride, chloroaluminum allantoate, ascorbic acid or its salts, ascorbyl phosphate or its salts, lysozyme chloride, triclocarban, zinc citrate, and phellodendron extract.
As the colorant, blue No. 1, yellow No. 4, green No. 3, and the like may be mixed in a usual amount.
The pH regulator may be organic acid such as citric acid, lactic acid, malic acid, etc. or its salt, phosphoric acid or its salt, or inorganic compound such as hydrochloric acid, sodium hydroxide, potassium hydroxide, etc.
Examples of the perfume include natural perfumes such as anise oil, wintergreen oil, thyme oil, sage oil, cardamom oil, coriander oil, lavender oil, chamomile oil, caraway oil, marjoram oil, oregano oil, pine needle oil, orange flower oil, rose oil, jasmine oil, iris extract, rose essential oil, and orange flower; and those obtained after processing (pre-cut removal, post-cut removal, fractionation, liquid-liquid extraction, rectification, flavor pulverization, etc.) of these natural flavors; a single perfume such as menthol, carvone, anethole, methyl salicylate, thymol, linalool, linalyl acetate, menthone, menthyl acetate, pinene, octanal, pulegone, carvone acetate, anisaldehyde, ethyl acetate, ethyl butyrate, allyl cyclohexane propionate, methyl anthranilate, ethyl methylphenyl epoxypropionate, vanillin, undecalactone, hexanal, propanol, butanol, isoamyl alcohol, hexenol, dimethyl sulfide, methyl cyclopentenolone, furfural, trimethylpyrazine, ethyl lactate, methyl lactate, ethyl thioacetate, etc., known flavor raw materials used in oral compositions such as a flavoring agent such as strawberry flavor, apple flavor, banana flavor, pineapple flavor, grape flavor, mango flavor, butter flavor, milk flavor, fruit mix flavor, tropical fruit flavor, and the like may also be used. The amount of these perfume materials is not particularly limited, but is preferably 0.000001 to 1% of the composition. In addition, the perfume for perfuming using the perfume raw material is preferably used in the composition in an amount of 0.1-2%.
The oral composition of the present invention may or may not be mixed with ethanol, and the content of ethanol is preferably 0 to 50% or 3 to 40% of the total composition. In the oral composition, the flavor or the like to be mixed in the composition may contain a trace amount of ethanol, and in addition to these, the ethanol may not be mixed, and in this case, the content of ethanol may be 1% or less, particularly 0.5% or less, and further 0.3% or less.
In addition, the present invention provides a gum massaging feeling-imparting agent comprising (a) a Sichuan pepper extract and (B) a pink pepper extract. In this case, as described above, the components (a) and (B) are used in combination as an effective component for imparting a massaging feeling to the gum, and these combined systems are contained. In this case, the details of the extraction methods, the types of substances contained, the quantitative ratios of the components, the amounts to be mixed, and the like for the component (a) and the component (B) are the same as those described above.
[ examples ]
The present invention will be specifically explained below by way of examples, comparative examples and formulation examples, but the present invention is not limited to the following examples. In the following examples,% represents mass% unless otherwise specified.
[ examples and comparative examples ]
Dentifrice compositions (paste dentifrice) shown in tables 2 to 5 were prepared by a usual method according to the compositions shown in table 1. The obtained dentifrice compositions were evaluated by the methods described later, and the results are also shown in the table.
[ Table 1]
The composition of the (onium) perfume is shown below.
The use of the starting materials is shown below.
(A) Sichuan PEPPER extract (trade name; Sichuan PEPPER ABSOLUTE CO)2EXTRACT, manufactured by CHARABOT, having a sanshool content of 50%)
(B) Pink pepper extract (made by v. man Fils spice (ltd.) and containing 35% of alpha-phellandrene)
Spilanthol (comparative) (spilanthol, containing approximately 70% spilanthol), manufactured by gaozhou perfumery industry Co., Ltd.)
Capsicum extract (comparative) (product of Yongqi Tang local shop, red pepper extract)
(C) Citral (made by Changluchuan spice)
(D) Citral diethyl acetal (manufactured by Jingshang perfumery Co., Ltd.)
(D) Citral dimethyl acetal (manufactured by Jingshang spice)
Evaluation method
Evaluated by 10 experimenters. 1g of the dentifrice composition was set in a toothbrush (DENTOR SYSTEMA toothbrush, Standard, manufactured by Shiwang corporation), and after use, the dentifrice composition was brushed for 3 minutes and rinsed with water. The experimenter performs a sensory test under absolute evaluation on the presence or absence of a massaging feeling of the gum during use, a massaging feeling of the gum after use, and an unpleasant taste, based on the following scale criteria. The average scores of 10 were obtained and evaluated according to the following evaluation criteria.
Here, the massaging feeling of the gum during use means that the gum is massaged by a moderate stimulation to the gum such as breakage of fine bubbles during use of the dentifrice composition in the oral cavity, and the gum feels tense. The massaging feeling of the gum after use means that the gum feels massaged and tensed as described above even after 3 minutes has elapsed after rinsing with water.
(i) Massaging feeling of gum in use
Scoring benchmark
And 5, dividing: the massaging feeling of the gum is very strongly felt
And 4, dividing: the massaging feeling of the gum is sensed very strongly
And 3, dividing: feel the massage feeling of the gum
And 2, dividing: slightly feel the massaging feeling of the gum
1 minute: no feeling of massaging the gum
Evaluation criteria
Average score of massaging feeling of gum in use
:: 4.0 min to 5.0 min
Very good: 3.5 min or more and less than 4.0 min
O: 3.0 min or more and less than 3.5 min
And (delta): 2.0 min or more and less than 3.0 min
X: 1.0 minute or more and less than 2.0 minutes
(ii) Massaging feeling of gum after use
Scoring benchmark
And 5, dividing: the massaging feeling of the gum is very strongly felt
And 4, dividing: the massaging feeling of the gum is sensed very strongly
And 3, dividing: feel the massage feeling of the gum
And 2, dividing: slightly feel the massaging feeling of the gum
1 minute: no feeling of massaging the gum
Evaluation criteria
Average score of massaging feeling of gum after use
:: 4.0 min to 5.0 min
Very good: 3.5 min or more and less than 4.0 min
O: 3.0 min or more and less than 3.5 min
And (delta): 2.0 min or more and less than 3.0 min
X: 1.0 minute or more and less than 2.0 minutes
(iii) Presence or absence of unpleasant taste
Scoring benchmark
And 4, dividing: hardly gives an unpleasant taste
And 3, dividing: slightly unpleasant taste but without problems
And 2, dividing: unpleasant taste
1 minute: the unpleasant taste is very strongly felt
Evaluation criteria
Average score of the presence or absence of unpleasant taste
Very good: 3.5 min or more and 4.0 min or less
O: 3.0 min or more and less than 3.5 min
And (delta): 2.0 min or more and less than 3.0 min
X: 1.0 minute or more and less than 2.0 minutes
[ Table 2]
[ Table 3]
[ Table 4]
Note: in example 23, α -Phellandrene (α -Phellandrene natural, manufactured by Sigma-Aldrich) having an α -Phellandrene content of 85% was used as the component (b), and the component was mixed with 0.008%.
[ Table 5]
The results in tables 2 to 4 show that the dentifrice composition (examples) containing the components (a) and (B) (components (a) and (B)) of the present invention is excellent in both the massaging feeling of the gum during use and the massaging feeling of the gum after use, and further, the unpleasant taste is suppressed and the taste is good. On the other hand, as is clear from the results in table 5, the dentifrice composition (comparative example) containing no component (a) or (B) (component (a) or (B)) had poor massaging feeling of gums during use and massaging feeling of gums after use.
[ prescription example 1] toothpaste
(a) V (b) mass ratio; 0.07
(A) V (B) mass ratio; 0.05
[ prescription example 2] toothpaste
(a) V (b) mass ratio; 0.07
(A) V (B) mass ratio; 0.05
[ prescription example 3] toothpaste
(a) V (b) mass ratio; 0.07
(A) V (B) mass ratio; 0.05
[ prescription example 4] toothpaste
(a) V (b) mass ratio; 0.07
(A) V (B) mass ratio; 0.05.
Claims (15)
1. an oral composition comprising:
(a) selected from sanshool and its derivatives, and
(b) alpha-phellandrene.
2. The oral composition according to claim 1, comprising 0.00004 to 0.05 mass% of the component (a), 0.0002 to 0.04 mass% of the component (b), and the mass ratio of (a)/(b) is 0.001 to 250.
3. An oral composition comprises (A) Sichuan pepper extract and (B) Pink pepper extract.
4. The oral composition according to claim 3, wherein the Sichuan pepper extract (A) contains 40% by mass or more of (a) 1 or more selected from sanshool and derivatives thereof.
5. The oral composition according to claim 3 or 4, wherein (B) the Pink pepper extract contains 20% by mass or more of (B) α -phellandrene.
6. The oral composition according to any one of claims 3 to 5, wherein the mass ratio of (A)/(B) is 0.001 to 100.
7. The oral composition according to any one of claims 3 to 6, comprising 0.0001 to 0.1 mass% of the component (A).
8. The oral composition according to any one of claims 3 to 7, comprising 0.001 to 0.1 mass% of the component (B).
9. The oral composition according to any one of claims 1 to 8, further comprising (C) citral in an amount of 0.001 to 0.2% by mass.
10. The oral composition according to any one of claims 1 to 9, further comprising 0.001 to 0.1 mass% of (D) 1 or more selected from citral diacetal and citral diacetal.
11. The oral composition according to any one of claims 1 to 10, which is a dentifrice composition.
12. A gingiva massaging feeling imparting agent comprises (A) Sichuan pepper extract and (B) Pink pepper extract.
13. The agent for imparting a massaging sensation to the gum according to claim 12, wherein the mass ratio of (A)/(B) is 0.001 to 100.
14. The gingival massaging sensation imparting agent according to claim 12 or 13, further comprising (C) citral.
15. The agent for imparting a massaging sensation to the gums according to any one of claims 12 to 14, further comprising (D) 1 or more selected from citral diacetal and citral diacetal.
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JP5748626B2 (en) | 2011-09-21 | 2015-07-15 | サンスター株式会社 | Oral composition |
CN102727407B (en) * | 2012-03-31 | 2013-11-20 | 重庆和信农业发展有限公司 | Health-care toothpaste containing Chinese prickly ash extracts |
EP2842428B1 (en) * | 2013-08-27 | 2018-08-08 | Symrise AG | Oral composition |
KR20150043769A (en) | 2013-10-15 | 2015-04-23 | 주식회사 엘지화학 | Anode for lithium secondary battery, preparation method thereof and lithium secondary battery comprising the same |
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2020
- 2020-07-16 CN CN202080034777.3A patent/CN113853194A/en active Pending
- 2020-07-16 JP JP2021533984A patent/JP7567791B2/en active Active
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JP2002234887A (en) * | 2000-10-13 | 2002-08-23 | Kao Corp | Citral acetal |
WO2013021635A1 (en) * | 2011-08-11 | 2013-02-14 | 株式会社ロッテ | Spice extract-containing composition for oral cavity |
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WO2021015091A1 (en) | 2021-01-28 |
JPWO2021015091A1 (en) | 2021-01-28 |
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