CN105358128B - Oral biological film remover and composition for oral cavity - Google Patents
Oral biological film remover and composition for oral cavity Download PDFInfo
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- CN105358128B CN105358128B CN201480038713.5A CN201480038713A CN105358128B CN 105358128 B CN105358128 B CN 105358128B CN 201480038713 A CN201480038713 A CN 201480038713A CN 105358128 B CN105358128 B CN 105358128B
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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
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/24—Phosphorous; Compounds thereof
-
- 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
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
-
- 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
- A61K8/345—Alcohols containing more than one hydroxy group
-
- 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
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
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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
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
- A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
-
- 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
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- 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
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
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- 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
Abstract
Oral biological film remover containing (A) alpha-alkene sulfonate and (B) condensed phosphate (B-1) and/or amphoteric surfactant (B-2) is provided, and removes the high composition for oral cavity of effect containing oral biological film obtained by above-mentioned (A) ingredient and (B) ingredient.
Description
Technical field
The present invention relates to the removings of the oral biological film of biomembrane the reason of chemically efficiently removing as saprodontia
Agent and composition for oral cavity.
Background technique
In the past, technology was removed as the plaque (tartar) in dentifrice, object caused by the detergent with grinding agent etc.
Rationality removes, and biochemical caused by enzyme etc. removes etc..
When being removed using detergent, in order to play the amount that its effect needs to increase grinding agent, hardness is improved, but adjoint
Abrasive power rise, have the harmfulness for being easy to generate tooth and gingival lesions etc., irritating possibility.On the other hand, in order to steady
Determine mixed enzyme, need and with various stabilizers, the case where the use feelings such as blistering and taste that have an impact.
In addition, in recent years, if can be captured tartar as biomembrane, removing biomembrane, then can more effectively remove tartar.It is right
In removing intraoral biomembrane, the physical method that toothbrush is not used only is useful, and toothbrush can not be touched
The chemical method that biomembrane removes is also useful.Biomembrane is the coaggregant and exocellular polysaccharide class structure by various oral cavity bacteriums
At.Therefore, as chemical removing method, it is known to inhibit the antierythrite of aggregation effect using having and use and decompose born of the same parents
The protease or dextranase of the enzyme of exo polysaccharides, the method for becoming dextranase etc., but there are also improved spaces for its effect.
Furthermore it is known that surfactant has cleaning function, detergent use can be used as in composition for oral cavity.This feelings
Under condition, it is known that lauryl sulfoacetate sodium is activating agent (the patent text without the distinctive stimulation of anionic surfactant
Offer 1: Japanese Patent Laid-Open 6-72836 bulletin).
But status all the time is surfactant, from its osmosis, the viewpoint of clean surfaceization effect is examined
Consider, although only having the effect of slight it is believed that it removes effect with tartar, but is not regarded as that surface is used alone
There is sufficient tartar or even biomembrane to remove effect when activating agent.
In addition, being disclosed in patent document 2 (Japanese patent special table 2008-519043 bulletin) and using sulfoacetic acid alkyl
Alkali metal salts or ammonium salt and water-soluble zinc salt method, but sulfoacetic acid alkyl salt is for reducing the constringent of zinc salt
Compound, there is no the removing effects for showing biomembrane.Further, patent document 3 (Japanese Patent Laid-Open 9-508120
Bulletin) composition for oral cavity of the toothpaste for containing lauryl sulfoacetate sodium as mitigation to the stimulation of mucous membrane of mouth is disclosed,
But it does not relate to improve biomembrane removing effect.
On the other hand, it is known that condensed phosphate has the effect of removing tooth spot (patent document 4: Japan chemically
The flat 9-175966 bulletin of open patent), but it is not regarded as that there is sufficient tartar and life when exclusive use condensed phosphate
Object film removes effect.
Existing technical literature
Patent document
Patent document 1: Japanese Patent Laid-Open 6-72836 bulletin
Patent document 2: Japanese patent special table 2008-519043 bulletin
Patent document 3: Japanese Patent Laid-Open 9-508120 bulletin
Patent document 4: Japanese Patent Laid-Open 9-175966 bulletin
Summary of the invention
Subject to be solved by the invention
Project of the invention is to provide a kind of the reason of chemically efficiently removing as saprodontia in view of the foregoing
Biomembrane oral biological film remover and composition for oral cavity.
The means to solve the problem
The present invention passes through further investigation to reach the project of aforementioned present invention, as a result, it has been found that passing through and using (A) alpha-olefin
Sulfonate and (B) condensed phosphate (B-1) and/or amphoteric surfactant (B-2) are able to solve the above subject.
Specifically, the present inventors has found, by combination (A) alpha-alkene sulfonate and (B) condensed phosphate (B-1),
The removing effect of oral biological film can be significantly improved, and is able to suppress the distinctive bitter taste of (A) ingredient, is furthermore possible to assign suitable
When blistering (I invention).
In I invention, (A) ingredient and (B-1) ingredient, especially (A)/(B-1) mass ratio are in the range of 0.1~10
When, it specifically and synergistically works, enhancing dispersion removes the effect of oral biological film.Furthermore it is possible to inhibit from (A) ingredient
Bitter taste assigns the blistering appropriate as caused by (A) ingredient.
That is, shown in embodiment as be described hereinafter and comparative example, when the alpha-alkene sulfonate of (A) ingredient is used alone, production
The removal rate of biomembrane is stuck in less than 70%.It moreover has been found that even if the biomembrane removal rate in condensed phosphate (B-1) is insufficient
50%, do not have sufficient biomembrane yet and remove effect, but and with (A) ingredient and when (B-1) ingredient, unexpectedly two kinds of ingredients are assisted
With working, sufficient biomembrane can be obtained and remove effect.It moreover has been found that in this case, even if by other than (A) ingredient
Anionic surfactant, such as NaLS, are used in combination with condensed phosphate, are also unable to get sufficient biomembrane and remove
Special function and effect in the case where going effect, above-mentioned biomembrane removing effect to be (A) ingredient and (B-1) ingredient and use.Into
One step, alpha-alkene sulfonate has bitter taste, in the past, practical in oral preparation although disclosing its use in the literature
In be belong to the material of avoidance, and the present inventors find will (A) ingredient and (B-1) ingredient and used time, be able to suppress from (A)
The bitter taste of ingredient assigns good use feeling, maintains blistering appropriate caused by (A) ingredient, and the system for being suitble to actual use is made
Agent, thereby completing the present invention.
In addition, the present inventors passes through further investigation to reach the project of aforementioned present invention, as a result, it has been found that passing through combination
(A) alpha-alkene sulfonate and (B) amphoteric surfactant (B-2), can significantly improve the removing effect of oral biological film, and
It is able to suppress the distinctive bitter taste of (A) ingredient, is furthermore possible to assign blistering (Section II invention) appropriate.
In (II) invention, (A) ingredient and range of (B-2) ingredient, especially (A)/(B-2) mass ratio 0.2~8
It when interior, specifically and synergistically works, enhancing dispersion removes the effect of oral biological film.Furthermore it is possible to inhibit to be originated from (A) ingredient
Bitter taste, assign the blistering appropriate as caused by (A) ingredient.
That is, shown in embodiment as be described hereinafter and comparative example, when the alpha-alkene sulfonate of (A) ingredient is used alone, production
The removal rate of biomembrane is stuck in less than 70%.Although it moreover has been found that the biomembrane removal rate in amphoteric surfactant (B-2)
Less than 50%, does not have sufficient biomembrane removing effect even if being used in combination with by it with other surfaces activating agent and be not considered as energy yet
Make biomembrane remove effect to improve, but by (A) ingredient and (B-2) ingredient and used time, unexpectedly two kinds of ingredients synergistically work,
Sufficient biomembrane, which can be obtained, by surfactant system removes effect.It moreover has been found that in this case, even if by (A)
Anionic surfactant other than ingredient, such as NaLS, are used in combination with amphoteric surfactant, are also unable to get
Sufficient biomembrane removes effect, and above-mentioned biomembrane, which removes effect, to be and use (A) ingredient and special effect when (B-2) ingredient
Effect.It further finds, alpha-alkene sulfonate has bitter taste, practical although disclosing its use in the literature in the past
Above its use is to be avoided, but when (A) ingredient is with (B-2) ingredient, be able to suppress the hardship from (A) ingredient
Taste assigns good use feeling, is furthermore possible to blistering appropriate caused by maintaining (A) ingredient, the system for being suitble to actual use is made
Agent completes the present invention.
It, can be specifically when further mixing (C) quaternary ammonium salt, (D) xylitol and/or antierythrite in Section II invention
It assigns superior oral biological film and removes effect.
In this case, further preferably (A) ingredient, (B-2) ingredient, the further preferably dentifrice of (C) ingredient
Composition, or further preferably (A) ingredient, (B-2) ingredient, the further preferably mouthrinse composition of (D) ingredient.
Therefore, (I invention) of the invention provides following oral biological film removers and composition for oral cavity.
A kind of (I-1) oral biological film remover contains (A) alpha-alkene sulfonate and (B-1) condensed phosphate.
The oral biological film remover that (I-2) such as (I-1) is recorded, wherein the mass ratio of (A)/(B-1) is 0.1~10.
The oral biological film remover that (I-3) such as (I-1) or (I-2) is recorded, wherein the alpha-alkene sulfonate of (A) ingredient
It is the alpha-alkene sulfonate that carbon atom number is 14~16.
(I-4) a kind of composition for oral cavity, which is characterized in that contain (A) alpha-alkene sulfonate and (B-1) polycondensation phosphoric acid
Salt.
The composition for oral cavity that (I-5) such as (I-4) is recorded, wherein the mass ratio of (A)/(B-1) is 0.1~10.
The composition for oral cavity that (I-6) such as (I-4) or (I-5) is recorded, wherein contain (A) ingredient alpha-alkene sulfonate 0.3
~5 mass %.
The composition for oral cavity that (I-7) such as (1-4), (I-5) or (I-6) is recorded, wherein contain (B-1) ingredient polycondensation phosphorus
0.1~5 mass % of hydrochlorate.
The composition for oral cavity that any one of (I-8) such as (I-4)~(I-7) is recorded, is Dentrifice composition or mouthwash
Composition.
The composition for oral cavity that any one of (I-9) such as (I-4)~(I-8) is recorded, is oral biological film removing oral cavity
Use composition.
Therefore, (Section II invention) of the invention provides following oral biological film remover and composition for oral cavity.
A kind of (II-1) oral biological film remover contains (A) alpha-alkene sulfonate and (B-2) amphoteric surfactant.
The oral biological film remover that (II-2) such as (II-1) is recorded, wherein the mass ratio of (A)/(B-2) is 0.2~8.
The oral biological film remover that (II-3) such as (II-1) or (II-2) is recorded, wherein the amphoteric surface of (B-2) ingredient
Activating agent be selected from fatty acid amide alkyl betaine, imidazolinium betaine and oxyneurine a kind with
On glycine betaine system amphoteric surfactant.
The oral biological film remover that (II-4) such as (II-1), (II-2) or (II-3) is recorded, wherein the α-of (A) ingredient
Alkene sulfonate is the alpha-alkene sulfonate that carbon atom number is 14~16.
The oral biological film remover that (II-5) any one of such as (II-1)~(II-4) is recorded, wherein further contain
(C) quaternary ammonium salt.
The oral biological film remover that (II-6) such as (II-5) is recorded, wherein the quaternary ammonium salt of (C) ingredient is selected from western pyrrole chlorine
1 kind or more of ammonium, benzalkonium chloride and benzethonium chloride.
The oral biological film remover that (II-7) any one of such as (II-1)~(II-6) is recorded, wherein further contain
(D) xylitol and/or antierythrite.
(II-8) a kind of composition for oral cavity, which is characterized in that contain (A) alpha-alkene sulfonate and (B-2) amphoteric surface
Activating agent.
The composition for oral cavity that (II-9) such as (II-8) is recorded, wherein the mass ratio of (A)/(B-2) is 0.2~8.
The composition for oral cavity that (II-10) such as (II-8) or (II-9) is recorded, wherein contain (A) ingredient alpha-olefin sulfonic acid
0.1~3 mass % of salt, 0.05~5 mass % of (B-2) ingredient amphoteric surfactant.
The composition for oral cavity that (II-11) such as (II-8), (II-9) or (II-10) is recorded, wherein further contain (C)
0.003~0.05 mass % of quaternary ammonium salt.
The composition for oral cavity that (II-12) any one of such as (II-8)~(II-11) is recorded, wherein further contain (D)
0.1~2 mass % of xylitol and/or antierythrite.
The composition for oral cavity that (II-13) such as any one of (II-8)~(II-12) is recorded, be Dentrifice composition or
Mouthrinse composition.
The composition for oral cavity that (II-14) any one of such as (II-8)~(II-13) is recorded is that oral biological film removes
Use composition for oral cavity.
The effect of invention
Oral biological film remover of the invention and composition for oral cavity are chemically removing the original as saprodontia
Excellent effect in terms of the oral biological film of cause.Furthermore it is possible to which bitter taste is inhibited to assign good use feeling, blistering appropriate is assigned.
Specific embodiment
Hereinafter, the present invention will be described in further detail.
The present invention is containing (A) alpha-alkene sulfonate and (B) condensed phosphate (B-1) and/or amphoteric surfactant
(B-2) oral biological film remover.In addition, the present invention is the composition for oral cavity containing above-mentioned (A) and (B) ingredient.
In the present invention, I invention is characterized in that, and uses (A) alpha-alkene sulfonate and the polycondensation phosphoric acid as (B) ingredient
Salt (B-1).
By and with (A) alpha-alkene sulfonate and (B-1) ingredient, the dispersion that can significantly improve biomembrane, which removes, is imitated
Fruit can suitably assign foaming characteristic furthermore it is possible to inhibit the bitter taste of (A) ingredient.
As (A) alpha-alkene sulfonate, the alkali gold such as sodium, potassium of alpha-olefin sulfonic acid that carbon atom number is 14~16 can be used
Belong to salt, the preferably alpha-alkene sulfonate of carbon atom number 14.These can be can obtain can be used for the commercially available of oral preparations
Product.
The condensed phosphate (B-1) and (A) ingredient and used time, biomembrane of (B) ingredient used in I invention remove effect
It improves, in addition, inhibiting bitter taste, assigns foaming characteristic appropriate.
As the condensed phosphate of (B) ingredient, the water-soluble poly phosphoric acid of straight-chain shown in the following general formula (1) can be used
Salt.For example, sodium pyrophosphate or potassium pyrophosphate, the sodium tripolyphosphate of n=3 or potassium tripolyphosphate, n=of polymerization degree n=2 can be enumerated
4 sodium tetrapolyphosphate or four PA 800Ks, five polyphosphate sodiums of n=5, further high polymerization degree sodium metaphosphate or metaphosphoric acid
Potassium etc..These can be used alone or combine two or more use, wherein be suitably coke from the aspect of effect embodiment
Sodium phosphate, potassium pyrophosphate, sodium tripolyphosphate, particularly preferred sodium tripolyphosphate.
Mn+2PnO3n+1 (1)
(in formula, M indicates Na or K, n≤2.)
Sodium pyrophosphate (peaceful Chemical Industries Co. Ltd. system, northeast Chemical Co., Ltd. system), coke specifically can be used
Potassium phosphate (peaceful Chemical Industries Co. Ltd. system, East Asia synthesize Chemical Co., Ltd. system), sodium tripolyphosphate (peaceful Chemical Industries
Co. Ltd. system, Central Xiao Zi Co., Ltd. (セ Application ト ラ Le nitre (strain)) system, (Japan, builder Co., Ltd., Japan
ビ ル ダ ー (strain)) system), potassium tripolyphosphate (peaceful Chemical Industries Co. Ltd. system), sodium tetrapolyphosphate (peaceful Chemical Industries strain
Formula commercial firm system), five polyphosphate sodiums (peaceful Chemical Industries Co. Ltd. system) etc..
In I invention, for the mixed proportion of (A) ingredient and (B-1) ingredient in particular range, oral biological film removes effect
It is more excellent.(A)/(B-1) ratio is not particularly limited, but as mass ratio preferably 0.1~10, more preferably 0.2~5, into
It is preferably one step 0.6~3, particularly preferably 1.2~3.
When within the scope of aforementioned proportion, it is more excellent that biomembrane removes effect.In addition, assigning good from bitter taste is inhibited
From the aspect of bubble, preferred proportion value is 10 or less.
In addition, in the present invention, Section II invention is characterized in that, and use (A) alpha-alkene sulfonate and as the two of (B) ingredient
Property surfactant (B-2).
By and with (A) alpha-alkene sulfonate and (B-2) ingredient, the dispersion that can significantly improve biomembrane, which removes, is imitated
Fruit can suitably assign foaming characteristic furthermore it is possible to inhibit the bitter taste of (A) ingredient.
In this case, (A) ingredient is identical as above-mentioned I invention.
(B) ingredient amphoteric surfactant (B-2) used in Section II invention, by being used in combination with (A) ingredient, oral cavity biology
The dispersion of film removes significant effect and improves, in addition, inhibiting bitter taste, assigns foaming characteristic appropriate.
As amphoteric surfactant, glycine betaine system, such as fatty acid amide alkyl betaine, imidazoline can be used
Glycine betaine, oxyneurine.Wherein, the carbon atom number of fatty acid is 8~18, and the carbon atom number of optimizing alkyl is 1~5
Fatty acid amide alkyl betaine, more preferable fatty acid amide propyl glycine betaine.As such fatty acid amide propyl beet
The fatty acid distribution of coconut oil amido propyl betaine that exogenesis rule (medicine part outer article raw material standard) are recorded can be used in alkali.
Amphoteric surfactant can be the commercially available product that can be used for oral preparations that can be obtained.Specifically, as coconut palm
Fatty acid oil amido propyl betaine can enumerate commercially available product name TEGO Betain CK OK (EVONIK corporation).
In Section II invention, for the mixed proportion of (A) ingredient and (B-2) ingredient in particular range, oral biological film removes effect
Fruit is more excellent.In this case, preferably (A)/(B-2) is further excellent than being by quality ratio 0.2~8, more preferably 0.4~5
It is selected as 0.4~4, particularly preferably 0.5~3.1.When within the scope of aforementioned proportion, it is more excellent that biomembrane removes effect.In addition, from
Assign more good blistering, from the aspect of further suppressing bitter taste, preferably 8 or less.
The present invention, especially Section II invention, preferably further mix (C) quaternary ammonium salt, and when mixing (C) quaternary ammonium salt, oral cavity is raw
The dispersion of object film removes effect and further increases.In addition, blistering further increases.
As the quaternary ammonium salt of (C) ingredient, Cetylpyridinium Chloride, benzalkonium chloride, benzethonium chloride etc. can be enumerated, these can be used 1
Kind uses two or more, especially from the aspect of biomembrane removing effect, more preferable Cetylpyridinium Chloride.
When mixing (C) ingredient, from the viewpoint of improving biomembrane removing effect, preferably (A)/(C) exists by quality ratio
It is mixed in the range of 10~500.
The present invention, especially Section II invention preferably further mix (D) xylitol and/or antierythrite, mixing (D) wood
When sugar alcohol and/or antierythrite, the dispersion of oral biological film removes effect and further increases.It, can be in addition, as (D) ingredient
Individually mixing xylitol or antierythrite, can also mix xylitol and antierythrite.
When mixing (D) ingredient, from the viewpoint of improving biomembrane removing effect, preferably (A)/(D) exists by quality ratio
It is mixed in the range of 0.01~5.
The oral biological film remover of I invention can be suitably mixed into composition for oral cavity.In this case,
In the composition for oral cavity of I invention, the combined amount of (A) ingredient be preferably composition it is whole 0.3~5% (quality %, under
Together.), more preferable 0.5~5.0%.Combined amount is more, and biomembrane removing effect is higher, at 0.3% or more, can assign sufficiently
Biomembrane remove effect.Furthermore it is possible to assign good foaming characteristic.When below 5%, bitter taste will not become by force, in use
It is preferred that.
In addition, in the composition for oral cavity of I invention, the combined amount of (B-1) ingredient be preferably composition it is whole 0.1~
5%, more preferable 0.2~5%, further preferred 0.3~5%.(B-1) combined amount of ingredient is more, and biomembrane removes effect and gets over
Height, but from the bitter taste that is inhibited, assigns good blistering, obtains using from the aspect of upper preferred material, preferably 5% or less.
The oral biological film remover of Section II invention is suitable for being mixed in composition for oral cavity, contains (A) alpha-olefin sulphur
Hydrochlorate and amphoteric surfactant (B-2) as (B) ingredient, further preferably (C) quaternary ammonium salt, furthermore further preferably
Contain (D) xylitol and/or antierythrite.Particularly if contain (A) ingredient, (B-2) ingredient, further preferably (C)
The Dentrifice composition of ingredient, or contain (A) ingredient, (B-2) ingredient, further preferably the mouthwash group of (D) ingredient
When closing object, oral biological film removes effect and further increases.
In the composition for oral cavity of Section II invention, the combined amount of (A) ingredient is preferably whole 0.1~3% of composition.This
In the case of kind, especially in Dentrifice composition, (A) ingredient 0.3~3% is preferably mixed, particularly preferably mixes 0.5~2.5%.
In addition, preferably mixing (A) ingredient 0.1~3% in mouthrinse composition, 0.1~2.5% is particularly preferably mixed, is particularly preferably mixed
Close 0.1~1%.Combined amount is more, and biomembrane removing effect is higher, at 0.1% or more, can assign sufficient biomembrane and remove
Effect.Furthermore it is possible to assign good foaming characteristic.When below 3%, bitter taste will not become by force, in use preferably.
In addition, the combined amount of (B-2) ingredient is preferably whole 0.05 of composition in the composition for oral cavity of Section II invention
~5%, particularly preferably 0.1~5%, more preferably 0.3~5%, further preferred 0.5~3%.(B-2) mixing of ingredient
Amount is more, and biomembrane removing effect is higher, good blistering is assigned, but furthermore in order not to generate bitter taste, preferably below 5%.
When mixing (C) quaternary ammonium salt, especially in the Dentrifice composition involved in Section II invention, preferred group of combined amount
Close 0.003~0.05%, more preferable the 0.005~0.01% of object entirety.Combined amount is more, and it is higher that biomembrane removes effect.For
Do not generate the mucosal irritation of quaternary ammonium salt, preferably 0.05% or less.
It is excellent especially in the mouthrinse composition that Section II invention is related to when mixing (D) xylitol and/or antierythrite
Selecting its combined amount is whole 0.1~2%, more preferably 0.3~1% of composition.The more biomembranes of combined amount remove effect more
It is high.In order not to generate bitter taste, preferably below 2%.
Composition for oral cavity of the invention can be prepared into the form of liquid, liquid, paste etc., can pass through common side
Method is prepared into the dentifrices such as toothpaste, liquid dentifrice, liquid dentifrice, profit tooth powder (profit Dentistry mill) processed, mouthwash etc..
It in this case, can also as needed within the scope of the effect of the invention in addition to mentioned component
Other any ingredients are mixed according to dosage form.It specifically, can be with mixed-abrasive, adhesive, thickener, table in the case where dentifrice
Solvent, the pH adjusting agent etc. of face activating agent, sweetener, preservative, fragrance, pigment, various effective components, water etc..In addition, gargling
Can be mixed in the case where water wetting agent, surfactant, solvent, pH adjusting agent, preservative, fungicide, fragrance, sweetener,
Pigment, various effective components etc..
The specific example of any ingredient is shown below, but the ingredient that can be mixed in composition of the invention is not limited to this
A little ingredients.
As grinding agent, it is silica-based that crystalline silicon dioxide, amorphous silicon di-oxide, silica gel, alumina silicate etc. can be enumerated
Grinding agent, zeolite, calcium phosphate dibasic anhydrous, calcium phosphate dibasic dihydrate, calcium pyrophosphate, calcium carbonate, aluminium hydroxide, aluminium oxide, carbonic acid
Magnesium, tricresyl phosphate magnesium, zirconium silicate, tricalcium phosphate, hydroxyapatite, tetracalcium phosphate, synthetic resin system grinding agent etc..The feelings of dentifrice
Under condition, these grinding agents usually can with blend compositions it is whole 5~70%, especially can with blend compositions it is whole 10~
50%.
As adhesive, pulullan polysaccharide, gelatin, methylcellulose, hydroxyethyl cellulose, hydroxy propyl cellulose can be enumerated
Element, sodium carboxymethylcellulose, carragheen, sodium alginate, xanthan gum, Sodium Polyacrylate, Arabic gum, guar gum, locust bean gum,
Polyvinyl alcohol, polyvinylpyrrolidone etc. can be used alone or combine two or more use.These adhesives usually can be with
0~10%, especially the 0.1~5% of blend compositions entirety.
As thickener (wetting agent), it is polynary that D-sorbite or propylene glycol, butanediol, glycerol, polyethylene glycol etc. can be enumerated
Alcohol.The combined amount of these thickeners is usually whole 0~70%, especially 3~50% of composition.
As surfactant, anionic surfactant, the non-ionic surface that can be mixed other than (A) ingredient are living
Property agent, it is, for example, possible to use the anionic surfactants such as sulfate of alkyl sulfate, fatty acid glyceride, polyoxy second
Allylic alkylation ether, polyox-yethylene-polyoxypropylene block copolymer, Crodaret, polyglyceryl fatty acid ester,
The nonionic surfactants such as sucrose fatty ester, fatty acid alkyl alcohol amide.These surfactants can be used a kind or
Two or more, usually can be with 0~10%, especially the 0.1~5% of blend compositions entirety.In addition, other than (A) ingredient yin from
The combined amount of sub- property surfactant can be 0%, in the case where mixing, preferably 0.1~1.5%, particularly preferred 0.1~
1.0%.
As sweetener, saccharin sodium, stevioside, neohesperidin dihydrochalcone etc. can be enumerated.As preservative, can mix
Close p-hydroxybenzoates such as sodium benzoate, methyl p-hydroxybenzoate, ethyl-para-hydroxybenzoate etc..
As fragrance, mentha piperita oil (ペ パ ー ミ Application ト oil can be applied in combination), oleum menthae viridis, fennel oil, eucalyptus oil,
Wintergreen, cinnamon oil, caryophyllus oil, thyme linaloe oil, sage oil, lemon oil, orange oil, peppermint oil (Ha ッ カ oil), cardamom oil,
Coriander oil, mandarin oil, lime oil, lavender oil, rosemary oil, oreodaphene, oil of chamomile, caraway oil, marjoram oil, laurel
Oil, lemongrass oil, origanum oil, pinke needle oil, neroli oil, attar of rose, jasmine oil, oil of grapefruit, platinum shaddock oil (ス ウ ィ ー テ ィ ー
Oil), shaddock oil, concrete of iris, American mint essential oil, Rosa Damascana, the natural perfume materials such as flores aurantii, and to the progress of these natural perfume materials
The fragrance and l- that working process (except front-end volatiles, removing tails, fractionation, liquid-liquid extraction, refining, fragrance powder-processed) obtains
Menthol, carvol, anethole, cineole, gaultherolin, cinnamic acid, eugenol, menthoxypropane -1 3-l-,
2- glycol, thymol, linalool, bergamio, limonene, menthones, menthyl acetate, N- substitution-are to terpane -3- first
Amide, firpene, octanal, citral, pulegone, carvacryl acetate, anisaldehyde, ethyl acetate, ethyl butyrate, cyclohexylpropionic acid
It is allyl ester, methyl anthranilate, ethyl methylphenylglycidate, vanillic aldehyde, undecalactone, hexanal, butanol, different
Amylalcohol, hexenol, dimethyl sulfide, methyl cyclopentenyl ketone, furfural, trimethylpyrazine, ethyl lactate, ethyl thioacetate etc.
Single fragrance, in addition, strawberry flavor, apple aroma, banana flavor, pineapple taste, grape flavor, mango taste, butter taste, milk taste, fruit mix
Compounding fragrances such as taste, tropical fruit (tree) taste etc. can be used for the well known spices material of composition for oral cavity.
As pigment, the pigment that can be used in composition for oral cavity can be used according to panel tone.As edible pigment,
Such as gorgeous indigo plant, tartrazines can be enumerated etc., titanium oxide etc. can be enumerated as pigment.
As effective component (medicinal ingredient), can in the range of pharmacy is allowed effective quantity using such as Chlorhexidine,
Triclosan, isopropyl methyl phenol, zinc gluconate, the sterilizations such as zinc citrate or bacteriostatic agent, the teeth such as ethanehydroxy bisphosphate
Prevention of stones agent, the anti-inflammatory agents such as tranexamic acid, glycyrrhizic acid and its salt, allantoin aluminium chloride, sodium fluoride, sodium monofluorophosphate etc.
Fluoride, the coating agents such as hydroxyethyl cellulose dimethyl diallyl ammonium chloride, dextranase, mutase, chlorinated lysozyme etc.
Enzyme agent, the vitamins such as ascorbic acid, D-α-tocopherol acetate, the astringents such as sodium chloride, aluctyl, strontium chloride, potassium nitrate etc. are felt
Allergy inhibitor, fluorides such as sodium fluoride, sodium monofluorophosphate, stannous fluoride etc..
In addition, can be with mixed ethanol, water etc. as solvent.
When composition for oral cavity is Dentrifice composition, preferred solvent is water, and preferably the content of water is that composition is whole
60% or less.In addition, the case where composition for oral cavity is mouthrinse composition, preferred solvent is the mixing of water or water and ethyl alcohol
Solvent, preferred alcohol are 10% or less whole of composition.
The pH of composition can be the range of common composition for oral cavity, but pH at preferably 25 DEG C is 5.5~8.5,
More preferable 6~8.Furthermore it is possible to adjust pH using pH adjusting agent as needed, sodium hydroxide, salt can be enumerated as pH adjusting agent
Acid, sodium carbonate, sodium bicarbonate, boric acid or its salt etc., wherein be suitably sodium hydroxide, potassium hydroxide, hydrochloric acid.These pH are adjusted
As long as pH value can be adjusted in above range by the combined amount of agent.
[embodiment]
Hereinafter, display embodiment and comparative example, prescription example, the present invention is specifically described, but the invention is not limited to
Following embodiments.In addition, % indicates quality % when being not particularly limited in following examples.
[embodiment I, Comparative Example I]
The Dentrifice composition that component shown in table 1,2 is prepared according to method shown in following, is evaluated with following methods.As a result
It is recorded in table 1,2 together.
The preparation method of Dentrifice composition:
Firstly, (B-1) ingredient condensed phosphate, water soluble ingredient used are mixed in containing D-sorbite at normal temperature
After in the purified water of the thickeners such as liquid, further mixed adhesive, stabilizer are dispersed with dispersion machine.Add in kneader
After entering dispersion liquid, grinding agent mixing, fragrance, (A) ingredient alpha-alkene sulfonate is added.About 5kPa will be decompressed in kneader and
Deaeration is carried out, continues to be mixed to get Dentrifice composition.In addition, the composition of comparative example is made according to the method described above
It is standby.
The evaluation method > of < oral biological film removing effect
(1) production method of model organism film
By diameter 7mm × thickness 3.5mm hydroxyapatite (HA) plate (Asahi Lite Optical Co., Ltd's system), filtered with through 0.45 μm
The non-stimulated saliva of people of device filtering is handled 4 hours, and the carrier as model organism film production, culture solution uses minimal buffering methanol
(ベ イ サ Le メ デ ィ ウ system system チ Application) culture solution (BMM)*1.Bacterial strain use for making model organism film is typical from the U.S.
Actinomyces viscosus (the Actinomyces that culture collection (American Type Culture Collection) is bought
Viscosus) ATCC43146, small veillonellasp (Veillonella parvula) ATCC17745, core Fusobacterium
(Fusobacterium nucleatum) ATCC10953, Streptococcus oralis (Streptococcusoralis) ATCC10557,
Streptococcus mutans (Streptococcusmutans) ATCC25175.By this 5 kinds of bacterial strains respectively with 1 × 107Cfu/mL (cfu: bacterium
Fall to form unit) mode be inoculated into the rotating circular disk reactor (culture tank) for being previously added BMM3000mL, and through saliva
Processed HA carrier together cultivate 24 hours under 37 DEG C, anaerobic condition by (5vol% carbon dioxide, 95vol% nitrogen).Then,
BMM culture medium culture 10 days is supplied continuously with replacement rate 5vol%/hour ratio at identical conditions, is formed on the surface HA
The model organism film of 5 kinds of strains mixing.
(2) the removing effect of model organism film
By the model organism film transfer of formation to 24 hole porous plates (Sumitomo Bakelite company (Sumitomo ベ ー Network ラ イ ト society)
System), Dentrifice composition (3 times of saliva dilution of the centrifuged supernatant using acquisition from Healthy People of 2mL preparation is added
(10000rpm, 10 minutes)), impregnate 3 minutes (group of Dentrifice composition will not be added as control sample).Then PBS is used
(and Wako Pure Chemical Industries corporation) 1mL is washed 6 times, is led in the test tube (diameter 13mm × 10mm) added with identical PBS2mL
Ultrasonication (200 μ A, 10 seconds) is crossed to be dispersed.The dispersion liquid is measured in the turbidity (OD) of wavelength 550nm, to measure
Biomembrane remaining quantity.
The biomembrane of subject composition removes effect, the removal rate relative to control group is found out by following formula, according to following
Benchmark determines that oral biological film removes effect from the removal rate.
Biomembrane removal rate (%)=(turbidity-subject composition turbidity of control group)/control group turbidity
×100
The determinating reference of oral biological film removing effect
◎ ◎: biomembrane removal rate is 95% or more
◎: biomembrane removal rate is 90% less than 95%
Zero: biomembrane removal rate is 80% less than 90%
△: biomembrane removal rate is 70% less than 80%
×: biomembrane removal rate is 50% less than 70%
××: biomembrane removal rate is less than 50%
*1The component of BMM: with the quality representation in 1 liter.
Peptone (Becton and Dickinson corporation): 4g/L
Tryptone (BectonandDickinson corporation): 2g/L
Yeast extract (BectonandDickinson corporation): 2g/L
Mucoprotein (Sigma corporation): 5g/L
Hemin (Sigma corporation): 2.5mg/L
Vitamin K (and Wako Pure Chemical Industries corporation): 0.5mg/L
KCl (and Wako Pure Chemical Industries corporation): 1g/L
Cysteine (and Wako Pure Chemical Industries corporation): 0.2g/L
Distilled water: surplus (carries out constant volume in such a way that total amount reaches 1L, autoclave handles 20 points at 121 DEG C
Clock.)
< hardship the presence or absence of is hidden and the evaluation method > of the superiority and inferiority of blistering
The presence or absence of bitter taste of Dentrifice composition shown in table and the superiority and inferiority of blistering carry out sense organ by following methods
Evaluation.
It takes on Dentrifice composition 1g to toothbrush, brushes teeth 3 minutes and evaluated according to following scoring benchmark.It is evaluated by 6
Person evaluates the superiority and inferiority of the presence or absence of bitter taste and blistering based on the following evaluation criteria.
The presence or absence of bitter taste
Evaluation criteria
5: not feeling bitter taste
4: hardly feeling bitter taste
3: slightly feeling that hardship is hidden
2: feeling that hardship is hidden
1: feeling that powerful hardship is hidden
Evaluation criteria
◎: average value is at 4 points or more 5 points or less
Zero: average value is at 3 points less than 4 points
△: average value is at 2 points less than 3 points
×: average value is at 1 point less than 2 points
The superiority and inferiority of blistering
Evaluation criteria
5: blistering is very good
4: blistering is slightly good
3: blistering is general
2: blistering is slightly worse
1: blistering is very poor
Evaluation criteria
◎: average value is at 4 points or more 5 points or less
Zero: average value is at 3 points less than 4 points
△: average value is at 2 points less than 3 points
×: average value is at 1 point less than 2 points
Using raw material shown in detailed description are as follows.
(A) ingredient
Tetradecene sodium sulfonate (alpha-olefin (C 14) sodium sulfonate): Lion Corporation's system
(B) ingredient
(B-1) sodium tripolyphosphate: peaceful Chemical Industries Co. Ltd. system
(B-1) sodium pyrophosphate: peaceful Chemical Industries Co. Ltd. system
(B-1) potassium pyrophosphate: peaceful Chemical Industries Co. Ltd. system
[table 1]
[table 2]
[embodiment II, Comparative Example I I]
Preparing the composition for oral cavity of component shown in table 3~6 according to method shown in following, (table 3,4 is dentifrice composition
Object, table 5,6 are mouthrinse composition), it is evaluated with method same as described above.As a result it is recorded in table 3~6 together.
In addition, carrying out sensory evaluation with superiority and inferiority of the following methods to the presence or absence of bitter taste of mouthrinse composition and blistering.
By mouthwash 10mL containing washing one's face and rinsing one's mouth 20 seconds in entrance, the presence or absence of bitter taste when gargling is determined based on above-mentioned scoring benchmark.
It is evaluated based on above-mentioned evaluation criteria according to 6 being averaged for estimator.
The preparation method of Dentrifice composition:
Firstly, water soluble ingredient used in sodium fluoride etc. is mixed in the thickener containing D-sorbitol solution etc. at normal temperature
Purified water in, then further mixed adhesive and (B-2) ingredient simultaneously, further mix (C) ingredient, with dispersion machine into
Row dispersion.After the powder mixing of above-mentioned dispersion liquid, grinding agent etc. is added in kneader, fragrance, (A) ingredient is added.It will mediate
It is decompressed to about 5kPa in machine and carries out deaeration, continues to be mixed to get Dentrifice composition.
The preparation method of mouthwash agent composition:
(A) ingredient, (B-2) ingredient, (D) ingredient and other raw materials are successively added to by the preparation of mouthrinse composition
Stirring makes its uniform dissolution in purified water.In addition, using three-in-one motor (ス リ ー ワ ン モ ー タ ー in manufacture) (BL1200,
HEIDON corporation).
Dentrifice composition, the mouthrinse composition of comparative example are prepared according to the method described above.
Using raw material shown in detailed description are as follows.
(A) ingredient
Tetradecene sodium sulfonate (alpha-olefin (C14) sodium sulfonate): Lion Corporation's system
(B) ingredient
(B-2) fatty acid distribution of coconut oil amido propyl betaine: 30% product (combined amount in each example is pure content), TEGO
Betain CK OK, EVONIK Co. Ltd. system
(B-2) imidazolinium betaine: Nikko Chemicals Co., Ltd (daylight ケ ミ カ Le ズ (strain)) system
(B-2) oxyneurine: Nikko Chemicals Co., Ltd's system
(C) Cetylpyridinium Chloride: Wako Pure Chemical Industries, Ltd.'s system
(C) benzalkonium chloride: Wako Pure Chemical Industries, Ltd.'s system
(C) benzethonium chloride: Japan Oil Co's system
(D) xylitol: ROCKET Amada Co., Ltd. (ロ ケ ッ ト ジ ャ パ Application (strain)) system
(D) antierythrite: Wako Pure Chemical Industries, Ltd.'s system
[table 3]
Dentrifice composition
[table 4]
Dentrifice composition
[table 5]
Mouthrinse composition
[table 6]
Mouthrinse composition
By the result in table it is found that and with (A) ingredient and when (B) ingredient, oral biological film removes significant effect and improves.This
Outside, bitter taste is inhibited.Further, composition for oral cavity, especially Dentrifice composition have blistering appropriate.
Prescription example is shown below.In addition, same as described above using raw material.
[prescription example I-1] mouthwash
(A)/(B-1) compare: 1.6
The oral biological film of the mouthwash removes excellent effect, and furthermore bitter taste is inhibited, and blistering is good.
[prescription example II-1] mouthwash
(A)/(B-2) compare: 3.0
The biomembrane of the mouthwash removes excellent effect, and furthermore bitter taste is inhibited.
Claims (14)
1. a kind of oral biological film remover, the polycondensation phosphorus indicated containing (A) alpha-alkene sulfonate and (B) the following general formula (1)
Hydrochlorate (B-1),
Mn+2PnO3n+1 (1)
In formula, M expression Na or K, n≤2,
(A)/(B-1) mass ratio is 0.1~10, and the alpha-alkene sulfonate of (A) ingredient is the α-that carbon atom number is 14~16
Alkene sulfonate.
2. oral biological film remover as described in claim 1, wherein (B) ingredient also includes amphoteric surfactant (B-
2), the mass ratio of (A)/(B-2) is 0.2~8.
3. oral biological film remover as claimed in claim 2, wherein amphoteric surfactant (B-2) is from fatty acid acyl
The glycine betaine system both sexes table of a kind or more selected in amine alkyl betaine, imidazolinium betaine and oxyneurine
Face activating agent.
4. oral biological film remover as claimed in claim 1 or 2, wherein further contain (C) quaternary ammonium salt.
5. oral biological film remover as claimed in claim 4, wherein the quaternary ammonium salt of (C) ingredient is selected from Cetylpyridinium Chloride, benzene
1 kind or more for pricking oronain and benzethonium chloride.
6. oral biological film remover as claimed in claim 1 or 2, wherein further contain (D) xylitol and/or red moss
Sugar alcohol.
7. a kind of composition for oral cavity, which is characterized in that indicated containing (A) alpha-alkene sulfonate and (B) the following general formula (1)
Condensed phosphate (B-1),
Mn+2PnO3n+1 (1)
In formula, M expression Na or K, n≤2,
(A)/(B-1) mass ratio is 0.1~10, and the alpha-alkene sulfonate of (A) ingredient is the α-that carbon atom number is 14~16
Alkene sulfonate.
8. composition for oral cavity as claimed in claim 7, wherein the composition for oral cavity contains (A) ingredient alpha-olefin sulphur
0.3~5 mass % of hydrochlorate, 0.1~5 mass % of (B-1) ingredient.
9. composition for oral cavity as claimed in claim 7 or 8, wherein (B) ingredient also includes amphoteric surfactant (B-
2), the mass ratio of (A)/(B-2) is 0.2~8.
10. composition for oral cavity as claimed in claim 9, wherein the composition for oral cavity contains (A) ingredient alpha-olefin
0.1~3 mass % of sulfonate, 0.05~5 mass % of (B-2) ingredient.
11. composition for oral cavity as claimed in claim 7 or 8, wherein further contain 0.003~0.05 matter of (C) quaternary ammonium salt
Measure %.
12. composition for oral cavity as claimed in claim 7 or 8, wherein further contain (D) xylitol and/or antierythrite
0.1~2 mass %.
13. composition for oral cavity as claimed in claim 7 or 8 is Dentrifice composition or mouthrinse composition.
14. composition for oral cavity as claimed in claim 7 or 8 is oral biological film removing composition for oral cavity.
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| PCT/JP2014/069020 WO2015008823A1 (en) | 2013-07-18 | 2014-07-17 | Elimination agent for oral cavity biofilm and oral cavity composition |
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| JP2016138047A (en) * | 2015-01-26 | 2016-08-04 | ライオン株式会社 | Dentifrice composition |
| JP6874688B2 (en) * | 2015-11-30 | 2021-05-19 | ライオン株式会社 | Toothpaste composition and oral biofilm remover |
| JP6617535B2 (en) * | 2015-11-30 | 2019-12-11 | ライオン株式会社 | Dentifrice composition |
| WO2017094582A1 (en) | 2015-11-30 | 2017-06-08 | ライオン株式会社 | Oral composition |
| WO2017094583A1 (en) * | 2015-11-30 | 2017-06-08 | ライオン株式会社 | Oral composition |
| WO2017094579A1 (en) * | 2015-11-30 | 2017-06-08 | ライオン株式会社 | Dentifrice composition and oral biofilm removing agent |
| JP7031253B2 (en) * | 2017-11-29 | 2022-03-08 | ライオン株式会社 | Toothpaste composition |
| JP7173043B2 (en) * | 2017-11-30 | 2022-11-16 | ライオン株式会社 | Oral stain remover, oral stain formation inhibitor, and oral composition |
| JP7264619B2 (en) * | 2017-12-27 | 2023-04-25 | 花王株式会社 | oral composition |
| JP7281423B2 (en) * | 2019-02-28 | 2023-05-25 | 花王株式会社 | oral composition |
| CN114502131A (en) | 2019-09-30 | 2022-05-13 | 宝洁公司 | Oral care compositions comprising stannous ion source, neutral amino acid and polyphosphate |
| WO2022064598A1 (en) * | 2020-09-24 | 2022-03-31 | ライオン株式会社 | Polyhydric alcohol-based dentifrice composition |
| KR102633791B1 (en) * | 2020-12-22 | 2024-02-02 | 주식회사 엘지생활건강 | Composition comprising phosphate for removal biofilm |
| KR20220107992A (en) | 2021-01-26 | 2022-08-02 | 주식회사 마루치 | Oral composition for preventing and improving sensitive teeth |
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- 2014-07-17 WO PCT/JP2014/069022 patent/WO2015008824A1/en active Application Filing
- 2014-07-17 CN CN201711248901.2A patent/CN107875031B/en active Active
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- 2014-07-17 MY MYPI2015704543A patent/MY177921A/en unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2015008823A1 (en) | 2017-03-02 |
| WO2015008824A1 (en) | 2015-01-22 |
| JPWO2015008824A1 (en) | 2017-03-02 |
| MY177921A (en) | 2020-09-26 |
| CN105358128A (en) | 2016-02-24 |
| CN107875031B (en) | 2021-08-20 |
| KR102146681B1 (en) | 2020-08-21 |
| JP6269672B2 (en) | 2018-01-31 |
| KR20160031997A (en) | 2016-03-23 |
| JP6299761B2 (en) | 2018-03-28 |
| WO2015008823A1 (en) | 2015-01-22 |
| CN107875031A (en) | 2018-04-06 |
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