WO2016136719A1 - Toothpaste composition - Google Patents
Toothpaste composition Download PDFInfo
- Publication number
- WO2016136719A1 WO2016136719A1 PCT/JP2016/055201 JP2016055201W WO2016136719A1 WO 2016136719 A1 WO2016136719 A1 WO 2016136719A1 JP 2016055201 W JP2016055201 W JP 2016055201W WO 2016136719 A1 WO2016136719 A1 WO 2016136719A1
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- WIPO (PCT)
- Prior art keywords
- viscosity
- mpa
- aqueous solution
- component
- copper
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
-
- 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
- A61K8/27—Zinc; 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
Definitions
- the present invention relates to a dentifrice composition containing a water-soluble metal salt, which has an excellent halitosis suppression effect, is rough on the surface of a preparation over time, liquid separation is suppressed, has an excellent appearance stability, and is suitable for prevention or suppression of halitosis.
- Patent Document 1 Japanese Patent Laid-Open No. 01-153622
- Patent Document 2 Japanese Patent Laid-Open No. 02-311413 proposes a technique that improves the deodorization rate of methyl mercaptan by using modified aluminum hydroxide and improves the bad breath prevention effect.
- polyethylene glycol is used as a humectant or thickener.
- Patent Document 3 JP-T 2006-506359
- Example used for dentifrice with excellent remineralization accelerating effect Patent Document 4: Japanese Patent Laid-Open No.
- the dentifrice composition containing the metal salt has a sufficient bad breath prevention effect, and it has been desired to develop a preparation that can improve the bad breath suppression effect and can be used more effectively for bad breath prevention.
- the present invention has been made in view of the above circumstances, and provides a dentifrice composition containing a water-soluble metal salt that has an excellent halitosis suppression effect and is excellent in appearance stability due to suppression of rough skin and liquid separation over time. For the purpose.
- a water-soluble metal salt selected from a copper salt and a zinc salt is 0.01 to 1% by mass
- B a Brookfield viscosity. Highly-polymerized polyethylene glycol having a 5 W / V% aqueous solution viscosity at 25 ° C. measured by a meter of 10 mPa ⁇ s or more and a 2 W / V% aqueous solution viscosity at 25 ° C. measured by the viscometer of 800 mPa ⁇ s or less.
- the bad breath suppression effect When combined with 0.01 to 0.5% by mass, the bad breath suppression effect is improved, and the surface of the dentifrice preparation over time and liquid separation are suppressed, and good appearance stability can be provided. I found it. That is, according to the present invention, by appropriately blending the component (B) into the dentifrice composition containing the component (A), the bad breath suppression effect is high and the appearance stability is excellent, or the prevention of bad breath or The inventors have found that a dentifrice composition suitable for suppression can be obtained, and have made the present invention.
- the bad breath suppression effect of water-soluble metal salts such as copper salts and zinc salts is not sufficient, and even though highly polymerized polyethylene glycol does not have a bad breath suppression effect.
- the bad breath suppression effect derived from (A) component improves, and the external appearance of a formulation is stabilized.
- the component (A) is used in an inappropriate amount in combination with the component (A)
- the surface of the preparation becomes rough over time, the texture of the dentifrice becomes poor, liquid separation occurs, and the appearance is stable.
- the components (A) and (B) are appropriately combined, the problem described above is unexpectedly solved and the effect of suppressing bad breath is enhanced without deteriorating the appearance of the preparation.
- the effect of suppressing bad breath that has been sufficiently suppressed is not recognized, and the appearance of the preparation is stabilized over time, and the surface of the preparation is roughened by wrinkles and granular aggregates after storage at 50 ° C. for 1 month. Therefore, it is possible to provide a smooth and glossy surface, improve the texture of the dentifrice, and further suppress liquid separation.
- the effect of suppressing bad breath and appearance stability of the dentifrice composition containing component (A) is improved by the highly polymerized polyethylene glycol of component (B).
- the use of polyethylene glycol as an agent cannot be predicted.
- the present invention provides the following dentifrice composition.
- a dentifrice composition comprising 0.01 to 0.5% by mass of the following highly polymerized polyethylene glycol.
- the water-soluble metal salt of component (A) is one or more selected from copper gluconate, copper citrate, copper sulfate, copper chloride, zinc gluconate, zinc sulfate and zinc citrate
- the highly polymerized polyethylene glycol of component (B) is the following (1) or (2) (1) The viscosity of a 5 W / V% aqueous solution at 25 ° C.
- a composition can be provided.
- the dentifrice composition of the present invention has (A) a water-soluble metal salt selected from a copper salt and a zinc salt, and (B) a viscosity of 10 mPa ⁇ s of a 5 W / V% aqueous solution at 25 ° C. measured with a Brookfield viscometer. It is blended with highly polymerized polyethylene glycol which is not less than s and the viscosity of the 2 W / V% aqueous solution at 25 ° C. measured with the viscometer is not more than 800 mPa ⁇ s.
- the water-soluble metal salt of component (A) is one or more selected from water-soluble copper salts and zinc salts, such as copper gluconate, copper citrate, copper sulfate, copper chloride, zinc gluconate, Zinc sulfate, zinc citrate and the like can be mentioned, and not only anhydrides but also hydrates containing crystal water such as copper sulfate pentahydrate can be used, among which copper gluconate, copper citrate, zinc citrate In particular, copper gluconate and zinc citrate are preferred.
- water-soluble copper salts and zinc salts such as copper gluconate, copper citrate, copper sulfate, copper chloride, zinc gluconate, Zinc sulfate, zinc citrate and the like can be mentioned, and not only anhydrides but also hydrates containing crystal water such as copper sulfate pentahydrate can be used, among which copper gluconate, copper citrate, zinc citrate In particular, copper gluconate and zinc citrate are
- the blending amount of the water-soluble metal salt is 0.01 to 1% (mass%, hereinafter the same) of the whole composition from the viewpoint of suppressing bad breath, preferably 0.01 to 0.5%, more preferably. Is 0.05 to 0.3%. When 0.01% or more is blended, a sufficient halitosis suppression effect is obtained. 1% or less is suitable for preventing the dentifrice from becoming worse over time.
- the blending amount of the water-soluble copper salt of the component (A) is preferably 0.0014 to 0.5%, particularly preferably 0.007 to 0.15% of the whole composition as copper.
- the blending amount of the water-soluble zinc salt is preferably 0.0014 to 0.5%, particularly 0.007 to 0.15% of the whole composition as zinc.
- the highly polymerized polyethylene glycol (B) is a polymer compound having a structure in which ethylene glycol is polymerized, and is a 5 W / V (mass / volume (capacity))% aqueous solution at 25 ° C. measured with a Brookfield viscometer.
- the viscosity is 10 mPa ⁇ s or more, and the viscosity of a 2 W / V% aqueous solution at 25 ° C. measured with the viscometer is 800 mPa ⁇ s or less.
- highly polymerized polyethylene glycol has the following viscosity physical properties (1) or (2).
- Viscosity of 5 W / V% aqueous solution at 25 ° C. is 10 to 20,000 mPa ⁇ s
- the viscosity of the 2 W / V% aqueous solution at 25 ° C. is 800 mPa ⁇ s or less.
- more preferable highly polymerized polyethylene glycol is 5 W at 25 ° C.
- the viscosity of the / V% aqueous solution is 10 to 18,000 mPa ⁇ s, particularly 30 to 10,000 mPa ⁇ s, especially 55 to 2,000 mPa ⁇ s, more particularly 55 to 250 mPa ⁇ s.
- component (B) by using highly polymerized polyethylene glycol having a viscosity within the above specific range as component (B), the effect of suppressing bad breath derived from component (A) is improved, and the roughness of the preparation surface over time is improved. Liquid separation is suppressed, and good appearance stability is given.
- the viscosity of the 5 W / V% aqueous solution is less than 10 mPa ⁇ s, the effect of improving the texture of the dentifrice cannot be sufficiently obtained, and if the viscosity of the 2 W / V% aqueous solution exceeds 800 mPa ⁇ s, The texture decreases with time.
- component (B) As the highly polymerized polyethylene glycol of component (B), the following commercially available products can be used.
- ⁇ POLYOX WSR N-10 Manufactured by Dow Chemical Co., Ltd., viscosity of 5 W / V% aqueous solution: 12 to 50 mPa ⁇ s, measuring device: Brookfield RVT, rotor No. 1, rotation speed 50 rpm, measuring temperature 25 ° C., measuring time 0.5 minutes
- ⁇ POLYOX WSR N-80 Manufactured by Dow Chemical Co., Ltd., viscosity of 5 W / V% aqueous solution: 55 to 115 mPa ⁇ s, measuring equipment: Brookfield RVT, rotor No.
- the blending amount of the highly polymerized polyethylene glycol as the component (B) is 0.01 to 0.5% of the entire composition, preferably 0.03 to 0.2%, more preferably 0.05 to 0.1%. %. If the blending amount is less than 0.01%, a sufficient bad breath suppressing effect and a dentifrice improving effect cannot be obtained. If the amount is too large, further improvement in the effect cannot be expected, and the appearance stability of the preparation decreases, and if it exceeds 0.5%, the texture of the dentifrice cannot be maintained well and liquid separation can be suppressed. Can not.
- (A) / (B) indicating the ratio of the blending amount of the component (A) and the component (B) is preferably 0.02 to 100, more preferably 0.1 to 10, particularly preferably the mass ratio. Is 0.5 to 6, more preferably 0.5 to 2. If the (A) / (B) ratio is too small, the bad breath suppression effect may not be obtained sufficiently. If it is too large, the texture of the dentifrice will not be improved sufficiently, or liquid separation will not be sufficiently suppressed. There is a case.
- the ratio of the amount of the water-soluble copper salt of component (A) as copper and the amount of component (B) is shown (A-1 ) / (B) is preferably 0.003 to 50, and more preferably 0.07 to 3 in terms of mass ratio.
- (A-2) / (B) showing the ratio of the amount of the water-soluble zinc salt of the component (A) as zinc and the amount of the component (B) is 0.003 to 50, particularly 0.07 to 3 is preferred.
- the sustainability of the halitosis suppression effect is improved, and the metallic taste derived from the component (A) is preferably suppressed.
- the propylene glycol alginate used is not particularly limited, but the viscosity of a 1% aqueous solution (20 ° C.) measured by a Brookfield viscometer is in the range of 10 to 1,300 mPa ⁇ s, particularly 10 to 200 mPa ⁇ s. preferable.
- the blending amount of propylene glycol alginate is preferably 0.01 to 3%, more preferably 0.05 to 3% of the total composition.
- the blending ratio of the component (A) to the propylene glycol alginate (C) is preferably 0.01 to 5 by mass ratio.
- the dentifrice composition of the present invention is suitably prepared as a toothpaste, a liquid dentifrice or the like, particularly as a toothpaste.
- the well-known component normally used besides the said component can be mix
- abrasives, thickeners, binders, surfactants, sweeteners, preservatives, colorants, fragrances, active ingredients other than the above, and the like are used in normal amounts within a range that does not interfere with the effects of the present invention. Can do.
- abrasive examples include silica-based abrasives such as silica gel, precipitated silica, aluminosilicate, zirconosilicate, calcium phosphate-based abrasives such as dicalcium phosphate, aluminum hydroxide, alumina, calcium carbonate, synthetic resin-based abrasives, etc. It is done.
- the blending amount of the abrasive is usually 5 to 50%.
- thickener examples include sugar alcohols such as sorbit, xylit and erythritol, and polyhydric alcohols such as glycerin and propylene glycol.
- sugar alcohols such as sorbit, xylit and erythritol
- polyhydric alcohols such as glycerin and propylene glycol.
- the amount of these thickeners is usually 5 to 50%.
- binder examples include cellulose derivatives such as sodium carboxymethyl cellulose and gums such as xanthan gum.
- the amount of the binder is usually 0 to 5%, particularly 0.1 to 5%.
- an anionic surfactant As the surfactant, an anionic surfactant, a cationic surfactant, a nonionic surfactant, and an amphoteric surfactant can be blended.
- the anionic surfactant include alkyl sulfates such as sodium lauryl sulfate.
- nonionic surfactants include polyhydric acids such as sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sugar alcohol fatty acid esters such as sucrose fatty acid esters, glycerin fatty acid esters, polyglycerin fatty acid esters, and polyoxyethylene glycerin fatty acid esters.
- Examples include alcohol fatty acid esters, polyoxyethylene alkyl ethers, polyoxyethylene fatty acid esters such as polyoxyethylene hydrogenated castor oil, and fatty acid alkanolamides.
- Examples of the cationic surfactant include alkylammonium type, and examples of the amphoteric surfactant include betaine type and imidazoline type.
- the blending amount of the surfactant is preferably 0.5 to 5% of the entire composition.
- Sweeteners include saccharin sodium and the like.
- the preservative include paraoxybenzoic acid esters such as methylparaben, benzoic acid or a salt thereof.
- the colorant include blue No. 1, yellow No. 4, and the like.
- Perfumes include peppermint oil, spearmint oil, anise oil, eucalyptus oil, winter green oil, cassia oil, clove oil, thyme oil, sage oil, lemon oil, orange oil, peppermint oil, cardamom oil, coriander oil, mandarin oil, Lime oil, lavender oil, rosemary oil, laurel oil, camomil oil, caraway oil, marjoram oil, bay oil, lemongrass oil, origanum oil, pine needle oil, neroli oil, rose oil, jasmine oil, grapefruit oil, sweetie Natural fragrances such as oil, coconut oil, Iris concrete, absolute peppermint, absolute rose, orange flower, and processing of these natural fragrances (front reservoir cut, rear reservoir cut, fractional distillation, liquid-liquid extraction, essence, powder Perfume and menthol) Carvone, Anethole, Cineol, Methyl salicylate, Synamic aldehyde, Eugenol, 3-l-Mentoxypropane-1
- the active ingredient known ingredients that are usually blended in dentifrice compositions can be used.
- fluorides, bactericides, anti-inflammatory agents, enzymes, plant extracts, anticalculus agents, antiplaque agents, etc. can be blended. .
- fluorides such as sodium fluoride and sodium monofluorophosphate
- nonionic fungicides such as isopropylmethylphenol
- cationic fungicides enzyme tranexamic acids such as dextranase, epsilon aminocaproic acid, allantoin, etc.
- the said active ingredient can be mix
- Dentifrice compositions (toothpastes) having the compositions shown in Tables 1 to 3 were prepared by a conventional method and evaluated by the following methods. The results are shown in Tables 1 to 3.
- the viscosity of the highly polymerized polyethylene glycol is the viscosity at 25 ° C. measured with a Brookfield viscometer (Brookfield RVT or RVF), as described above. Moreover, the viscosity of polyethylene glycol # 400 measured by the same method was less than the viscosity of (B) highly polymerized polyethylene glycol.
- A Copper gluconate; manufactured by Kanto Chemical Co., Ltd., copper gluconate
- A zinc citrate; manufactured by Kanto Chemical Co., Inc., zinc citrate
- B highly polymerized polyethylene glycol
- POLYOX WSR N-80 Viscosity of 5 W / V% aqueous solution manufactured by Dow Chemical Company: 85 mPa ⁇ s (rotor No. 1, rotation speed 50 rpm, measurement time 0.5 minutes)
- POLYOX WSR N-10 Manufactured by Dow Chemical Co., Ltd., viscosity of 5 W / V% aqueous solution: 35 mPa ⁇ s (rotor No.
- POLYOX WSR N-750 (Dow Chemical Co., Viscosity of 5 W / V% aqueous solution: 1,100 mPa ⁇ s (Rotor No. 2, rotation speed 10 rpm, measurement time 1 minute)) POLYOX WSR N-12K (Manufactured by Dow Chemical Co., Ltd., viscosity of 2 W / V% aqueous solution: 420 mPa ⁇ s (rotor No. 1, rotation speed 10 rpm, measurement time 1 minute)) Polyethylene glycol # 400 (Average molecular weight 380 described in Sanyo Chemical Industries, Ltd., Quasi-drug raw material standard 2006) ⁇ 420)
- a dentifrice composition having the composition shown in Table 4 was prepared by a conventional method using the same raw materials as described above, and evaluated by the same method. Moreover, the sustainability of the bad breath suppression effect (bad breath suppression continuous effect) and the metallic taste suppression effect were evaluated by the following methods. The results are also shown in Table 4.
- Table 5 shows formulation examples.
- the dentifrice compositions of the formulation examples were prepared in the same manner as described above and evaluated in the same manner. As a result, the bad breath suppressing effect, the texture of the dentifrice, and the absence of liquid separation were all excellent.
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Abstract
Description
なお、本発明において、(B)成分の高重合ポリエチレングリコールによって、(A)成分含有歯磨剤組成物の口臭抑制効果及び外観安定性が改善することは、歯磨剤組成物の粘稠剤、保湿剤としてのポリエチレングリコールの使用からは予測できない。 That is, the bad breath suppression effect of water-soluble metal salts such as copper salts and zinc salts is not sufficient, and even though highly polymerized polyethylene glycol does not have a bad breath suppression effect, By using (B) component together, the bad breath suppression effect derived from (A) component improves, and the external appearance of a formulation is stabilized. In this case, in the dentifrice composition, if the component (A) is used in an inappropriate amount in combination with the component (A), the surface of the preparation becomes rough over time, the texture of the dentifrice becomes poor, liquid separation occurs, and the appearance is stable. However, when the components (A) and (B) are appropriately combined, the problem described above is unexpectedly solved and the effect of suppressing bad breath is enhanced without deteriorating the appearance of the preparation. The effect of suppressing bad breath that has been sufficiently suppressed is not recognized, and the appearance of the preparation is stabilized over time, and the surface of the preparation is roughened by wrinkles and granular aggregates after storage at 50 ° C. for 1 month. Therefore, it is possible to provide a smooth and glossy surface, improve the texture of the dentifrice, and further suppress liquid separation.
In the present invention, the effect of suppressing bad breath and appearance stability of the dentifrice composition containing component (A) is improved by the highly polymerized polyethylene glycol of component (B). The use of polyethylene glycol as an agent cannot be predicted.
〔1〕
(A)銅塩及び亜鉛塩から選ばれる1種又は2種以上の水溶性金属塩を0.01~1質量%と、
(B)ブルックフィールド型粘度計で測定した25℃における5W/V%水溶液の粘度が10mPa・s以上であり、かつ前記粘度計で測定した25℃における2W/V%水溶液の粘度が800mPa・s以下である高重合ポリエチレングリコールを0.01~0.5質量%と
を含有してなることを特徴とする歯磨剤組成物。
〔2〕
(A)成分の水溶性金属塩が、グルコン酸銅、クエン酸銅、硫酸銅、塩化銅、グルコン酸亜鉛、硫酸亜鉛及びクエン酸亜鉛から選ばれる1種又は2種以上である〔1〕に記載の歯磨剤組成物。
〔3〕
(A)成分の水溶性金属塩が、グルコン酸銅及び/又はクエン酸亜鉛である〔1〕又は〔2〕に記載の歯磨剤組成物。
〔4〕
(B)成分の高重合ポリエチレングリコールが、下記(1)又は(2)
(1)ブルックフィールド型粘度計で測定した25℃における5W/V%水溶液の粘度が10~20,000mPa・s、
(2)(1)で粘度が20,000mPa・sを超える場合は、前記粘度計で測定した25℃における2W/V%水溶液の粘度が800mPa・s以下
のものである〔1〕、〔2〕又は〔3〕に記載の歯磨剤組成物。
〔5〕
(A)成分と(B)成分との配合量の割合を示す(A)/(B)が、質量比として0.02~100である〔1〕~〔4〕のいずれかに記載の歯磨剤組成物。
〔6〕
練歯磨剤である〔1〕~〔5〕のいずれかに記載の歯磨剤組成物。 Accordingly, the present invention provides the following dentifrice composition.
[1]
(A) 0.01 to 1% by mass of one or more water-soluble metal salts selected from copper salts and zinc salts;
(B) The viscosity of a 5 W / V% aqueous solution at 25 ° C. measured with a Brookfield viscometer is 10 mPa · s or more, and the viscosity of a 2 W / V% aqueous solution at 25 ° C. measured with the viscometer is 800 mPa · s. A dentifrice composition comprising 0.01 to 0.5% by mass of the following highly polymerized polyethylene glycol.
[2]
The water-soluble metal salt of component (A) is one or more selected from copper gluconate, copper citrate, copper sulfate, copper chloride, zinc gluconate, zinc sulfate and zinc citrate [1] The dentifrice composition described.
[3]
The dentifrice composition according to [1] or [2], wherein the water-soluble metal salt of component (A) is copper gluconate and / or zinc citrate.
[4]
The highly polymerized polyethylene glycol of component (B) is the following (1) or (2)
(1) The viscosity of a 5 W / V% aqueous solution at 25 ° C. measured with a Brookfield viscometer is 10 to 20,000 mPa · s,
(2) When the viscosity exceeds 20,000 mPa · s in (1), the viscosity of the 2 W / V% aqueous solution at 25 ° C. measured with the viscometer is 800 mPa · s or less [1], [2 ] Or the dentifrice composition according to [3].
[5]
The toothpaste according to any one of [1] to [4], wherein (A) / (B), which indicates the ratio of the blended amount of component (A) and component (B), is 0.02 to 100 as a mass ratio. Agent composition.
[6]
The dentifrice composition according to any one of [1] to [5], which is a toothpaste.
なお、上記配合量の範囲内において、(A)成分の水溶性銅塩の配合量は、銅として組成物全体の0.0014~0.5%、特に0.007~0.15%が好ましい。また、水溶性亜鉛塩の配合量は、亜鉛として組成物全体の0.0014~0.5%、特に0.007~0.15%が好ましい。 The blending amount of the water-soluble metal salt is 0.01 to 1% (mass%, hereinafter the same) of the whole composition from the viewpoint of suppressing bad breath, preferably 0.01 to 0.5%, more preferably. Is 0.05 to 0.3%. When 0.01% or more is blended, a sufficient halitosis suppression effect is obtained. 1% or less is suitable for preventing the dentifrice from becoming worse over time.
Within the above range of the blending amount, the blending amount of the water-soluble copper salt of the component (A) is preferably 0.0014 to 0.5%, particularly preferably 0.007 to 0.15% of the whole composition as copper. . The blending amount of the water-soluble zinc salt is preferably 0.0014 to 0.5%, particularly 0.007 to 0.15% of the whole composition as zinc.
5W/V%水溶液の粘度が20,000mPa・sを超える場合は、粘度測定が不能となるため、2W/V%水溶液における粘度を採用する。即ち、本発明において、高重合ポリエチレングリコールは、下記(1)又は(2)の粘度物性を有する。
(1)25℃における5W/V%水溶液の粘度が10~20,000mPa・s
(2)(1)で粘度が20,000mPa・sを超える場合は、25℃における2W/V%水溶液の粘度が800mPa・s以下
本発明において、より好ましい高重合ポリエチレングリコールは、25℃における5W/V%水溶液の粘度が10~18,000mPa・s、特に30~10,000mPa・s、とりわけ55~2,000mPa・s、更にとりわけ55~250mPa・sのものである。
本発明では、(B)成分として粘度が上記特定範囲内である高重合ポリエチレングリコールを用いることで、(A)成分由来の口臭抑制効果が向上し、また、経時における製剤表面の肌荒れが改善し、液分離が抑制され、良好な外観安定性を与える。
上記5W/V%水溶液の粘度が10mPa・sに満たないと、歯磨剤のきめの改善効果が十分に得られず、上記2W/V%水溶液の粘度が800mPa・sを超えると、歯磨剤のきめが経時で低下する。 The highly polymerized polyethylene glycol (B) is a polymer compound having a structure in which ethylene glycol is polymerized, and is a 5 W / V (mass / volume (capacity))% aqueous solution at 25 ° C. measured with a Brookfield viscometer. The viscosity is 10 mPa · s or more, and the viscosity of a 2 W / V% aqueous solution at 25 ° C. measured with the viscometer is 800 mPa · s or less.
When the viscosity of the 5 W / V% aqueous solution exceeds 20,000 mPa · s, the viscosity cannot be measured, so the viscosity in the 2 W / V% aqueous solution is adopted. That is, in the present invention, highly polymerized polyethylene glycol has the following viscosity physical properties (1) or (2).
(1) Viscosity of 5 W / V% aqueous solution at 25 ° C. is 10 to 20,000 mPa · s
(2) In (1), when the viscosity exceeds 20,000 mPa · s, the viscosity of the 2 W / V% aqueous solution at 25 ° C. is 800 mPa · s or less. In the present invention, more preferable highly polymerized polyethylene glycol is 5 W at 25 ° C. The viscosity of the / V% aqueous solution is 10 to 18,000 mPa · s, particularly 30 to 10,000 mPa · s, especially 55 to 2,000 mPa · s, more particularly 55 to 250 mPa · s.
In the present invention, by using highly polymerized polyethylene glycol having a viscosity within the above specific range as component (B), the effect of suppressing bad breath derived from component (A) is improved, and the roughness of the preparation surface over time is improved. Liquid separation is suppressed, and good appearance stability is given.
If the viscosity of the 5 W / V% aqueous solution is less than 10 mPa · s, the effect of improving the texture of the dentifrice cannot be sufficiently obtained, and if the viscosity of the 2 W / V% aqueous solution exceeds 800 mPa · s, The texture decreases with time.
・POLYOX WSR N-10
(ダウ・ケミカル社製、5W/V%水溶液の粘度:12~50mPa・s、測定機器:ブルックフィールド RVT、ローターNo.1、回転数50rpm、測定温度25℃、測定時間0.5分)
・POLYOX WSR N-80
(ダウ・ケミカル社製、5W/V%水溶液の粘度:55~115mPa・s、測定機器:ブルックフィールド RVT、ローターNo.1、回転数50rpm、測定温度25℃、測定時間0.5分)
・POLYOX WSR N-750
(ダウ・ケミカル社製、5W/V%水溶液の粘度:1,000~1,200mPa・s、測定機器:ブルックフィールド RVF、ローターNo.2、回転数10rpm、測定温度25℃、測定時間1分)
・POLYOX WSR-205
(ダウ・ケミカル社製、5W/V%水溶液の粘度:4,500~8,800mPa・s、測定機器:ブルックフィールド RVF、ローターNo.2、回転数2rpm、測定温度25℃、測定時間5分)
・POLYOX WSR-1105
(ダウ・ケミカル社製、5W/V%水溶液の粘度:8,800~17,600mPa・s、測定機器:ブルックフィールド RVF、ローターNo.2、回転数2rpm、測定温度25℃、測定時間5分)
・POLYOX WSR N-12K
(ダウ・ケミカル社製、2W/V%水溶液の粘度:400~800mPa・s、測定機器:ブルックフィールド RVF、ローターNo.1、回転数10rpm、測定温度25℃、測定時間1分) As the highly polymerized polyethylene glycol of component (B), the following commercially available products can be used.
・ POLYOX WSR N-10
(Manufactured by Dow Chemical Co., Ltd., viscosity of 5 W / V% aqueous solution: 12 to 50 mPa · s, measuring device: Brookfield RVT, rotor No. 1, rotation speed 50 rpm, measuring temperature 25 ° C., measuring time 0.5 minutes)
・ POLYOX WSR N-80
(Manufactured by Dow Chemical Co., Ltd., viscosity of 5 W / V% aqueous solution: 55 to 115 mPa · s, measuring equipment: Brookfield RVT, rotor No. 1, rotation speed 50 rpm, measuring temperature 25 ° C., measuring time 0.5 minutes)
・ POLYOX WSR N-750
(Viscosity of 5 W / V% aqueous solution manufactured by Dow Chemical Company: 1,000 to 1,200 mPa · s, measuring equipment: Brookfield RVF, rotor No. 2, rotation speed 10 rpm, measuring temperature 25 ° C., measuring time 1 minute )
・ POLYOX WSR-205
(Viscosity of 5 W / V% aqueous solution manufactured by Dow Chemical Company: 4,500-8,800 mPa · s, measuring equipment: Brookfield RVF, rotor No. 2, rotation speed 2 rpm, measuring temperature 25 ° C., measuring time 5 minutes )
・ POLYOX WSR-1105
(Viscosity of 5 W / V% aqueous solution manufactured by Dow Chemical Company: 8,800-17,600 mPa · s, measuring equipment: Brookfield RVF, rotor No. 2, rotation speed 2 rpm, measuring temperature 25 ° C., measuring time 5 minutes )
・ POLYOX WSR N-12K
(Dow Chemical Co., Ltd., viscosity of 2 W / V% aqueous solution: 400 to 800 mPa · s, measuring equipment: Brookfield RVF, rotor No. 1, rotation speed 10 rpm, measuring temperature 25 ° C., measuring time 1 minute)
なお、(A)/(B)の質量比が上記範囲内において、(A)成分の水溶性銅塩の銅としての配合量と(B)成分の配合量との割合を示す(A-1)/(B)は質量比として0.003~50、特に0.07~3が好ましい。また、(A)成分の水溶性亜鉛塩の亜鉛としての配合量と(B)成分の配合量との割合を示す(A-2)/(B)は質量比として0.003~50、特に0.07~3が好ましい。 In this invention, when (A) component and (B) component are mix | blended in an appropriate ratio, the bad breath suppression effect will be more excellent and external appearance stability will also improve more. In this case, (A) / (B) indicating the ratio of the blending amount of the component (A) and the component (B) is preferably 0.02 to 100, more preferably 0.1 to 10, particularly preferably the mass ratio. Is 0.5 to 6, more preferably 0.5 to 2. If the (A) / (B) ratio is too small, the bad breath suppression effect may not be obtained sufficiently. If it is too large, the texture of the dentifrice will not be improved sufficiently, or liquid separation will not be sufficiently suppressed. There is a case.
When the mass ratio of (A) / (B) is within the above range, the ratio of the amount of the water-soluble copper salt of component (A) as copper and the amount of component (B) is shown (A-1 ) / (B) is preferably 0.003 to 50, and more preferably 0.07 to 3 in terms of mass ratio. In addition, (A-2) / (B) showing the ratio of the amount of the water-soluble zinc salt of the component (A) as zinc and the amount of the component (B) is 0.003 to 50, particularly 0.07 to 3 is preferred.
(C)アルギン酸プロピレングリコールエステルの配合量は、組成物全体の0.01~3%が好ましく、より好ましくは0.05~3%である。前記範囲内で、口臭抑制持続効果が特に優れ、また、金属味が抑制され使用感も良好である。
また、(C)アルギン酸プロピレングリコールエステルに対する(A)成分の配合比率は質量比で0.01~5であることが好ましい。 When the (C) alginate propylene glycol ester is further blended with the dentifrice composition of the present invention, the sustainability of the halitosis suppression effect is improved, and the metallic taste derived from the component (A) is preferably suppressed. The propylene glycol alginate used is not particularly limited, but the viscosity of a 1% aqueous solution (20 ° C.) measured by a Brookfield viscometer is in the range of 10 to 1,300 mPa · s, particularly 10 to 200 mPa · s. preferable.
(C) The blending amount of propylene glycol alginate is preferably 0.01 to 3%, more preferably 0.05 to 3% of the total composition. Within the said range, a bad breath suppression sustained effect is especially excellent, and a metallic taste is suppressed and a usability | use_condition is also favorable.
The blending ratio of the component (A) to the propylene glycol alginate (C) is preferably 0.01 to 5 by mass ratio.
アニオン性界面活性剤としては、ラウリル硫酸ナトリウム等のアルキル硫酸塩などが挙げられる。非イオン性界面活性剤としては、ソルビタン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、ショ糖脂肪酸エステル等の糖アルコール脂肪酸エステル、グリセリン脂肪酸エステル、ポリグリセリン脂肪酸エステル、ポリオキシエチレングリセリン脂肪酸エステル等の多価アルコール脂肪酸エステル、ポリオキシエチレンアルキルエーテル、ポリオキシエチレン硬化ヒマシ油等のポリオキシエチレン脂肪酸エステル、脂肪酸アルカノールアミドなどが挙げられる。
カチオン性界面活性剤としては、アルキルアンモニウム型等が挙げられ、両性界面活性剤としては、ベタイン型、イミダゾリン型等が挙げられる。
界面活性剤の配合量は、組成全体の0.5~5%が好ましい。 As the surfactant, an anionic surfactant, a cationic surfactant, a nonionic surfactant, and an amphoteric surfactant can be blended.
Examples of the anionic surfactant include alkyl sulfates such as sodium lauryl sulfate. Examples of nonionic surfactants include polyhydric acids such as sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sugar alcohol fatty acid esters such as sucrose fatty acid esters, glycerin fatty acid esters, polyglycerin fatty acid esters, and polyoxyethylene glycerin fatty acid esters. Examples include alcohol fatty acid esters, polyoxyethylene alkyl ethers, polyoxyethylene fatty acid esters such as polyoxyethylene hydrogenated castor oil, and fatty acid alkanolamides.
Examples of the cationic surfactant include alkylammonium type, and examples of the amphoteric surfactant include betaine type and imidazoline type.
The blending amount of the surfactant is preferably 0.5 to 5% of the entire composition.
表1~3に示す組成の歯磨剤組成物(練歯磨)を常法によって調製し、下記方法で評価した。結果を表1~3に併記した。 [Examples and Comparative Examples]
Dentifrice compositions (toothpastes) having the compositions shown in Tables 1 to 3 were prepared by a conventional method and evaluated by the following methods. The results are shown in Tables 1 to 3.
健常人で口臭を有し、かつ1ヶ月以内に抗生物質を服用していないボランティア5名を被験者とした。被験者には前日夜から試験当日まで口腔清掃と飲食を禁止した。口臭試験は、試験開始前と歯磨きして1時間経過後(試験後)の口臭をそれぞれテドラバッグに採取し、テドラバッグに採取した呼気1リットルの口臭強度を、専門評価者3名が下記の評点基準に従い判定した。
<口臭強度の評点基準>
0点:口臭は認められない
1点:わずかな口臭が認められる
2点:口臭が認められる
3点:著しい口臭が認められる
更に、下記式により、口臭改善度を求め、試験組成物の口臭抑制効果を下記基準で評価した。
<口臭改善度の算出式>
(口臭改善度)=(試験開始前の口臭強度平均値)-(試験後の口臭強度平均値)
なお、口臭強度平均値は、各群被験者の口臭強度を平均した値である。
<口臭抑制効果の評価基準>
◎:顕著な効果あり。口臭改善度が1.5点以上
○:効果あり。口臭改善度が1.0点以上1.5点未満
△:若干の効果あり。口臭改善度が0.5点以上1.0点未満
×:効果なし。口臭改善度が0.5点未満 (1) Evaluation method of halitosis suppression effect Five volunteers who had halitosis and were not taking antibiotics within one month were subjects. Subjects were prohibited from oral cleaning and eating and drinking from the night before the test day. The breath odor test involves collecting the bad breath before the start of the test and 1 hour after brushing the tooth (after the test) in a tedra bag, and the odor intensity of 1 liter of exhaled breath collected in the tedra bag. Judgment according to
<Scoring criteria for bad breath intensity>
0 points: No bad breath is observed 1 point: A slight bad breath is observed 2 points: Bad breath is observed 3 points: Remarkable bad breath is observed Further, the degree of improvement of bad breath is obtained by the following formula, and the bad breath of the test composition is suppressed The effect was evaluated according to the following criteria.
<Calculation formula of bad breath improvement>
(Degree of bad breath improvement) = (Average bad breath intensity before the start of the test)-(Average bad breath intensity after the test)
In addition, a bad breath intensity average value is the value which averaged the bad breath intensity of the test subject of each group.
<Evaluation criteria for bad breath suppression effect>
A: There is a remarkable effect. Improvement in halitosis is 1.5 points or more. Bad breath improvement degree is 1.0 point or more and less than 1.5 point Δ: Some effect. Bad breath improvement degree of 0.5 point or more and less than 1.0 point ×: No effect. Bad breath improvement is less than 0.5 points
50℃で1ヶ月保存後、歯磨剤組成物をチューブから歯ブラシに出した時の練の外観(製剤表面の肌荒れのなさ(歯磨剤のきめ))について、評価者3名が、下記の評点基準で判定した。
評点基準
5:しわが認められなく、更に滑らかでツヤがある
4:しわが認められない
3:しわがわずかに認められるが、品質的には問題ないレベルである
2:しわが認められるが、粒状の凝集体は認められない
1:しわや粒状の凝集がかなり認められる
3名の平均点を求め、歯磨剤のきめについて下記基準で評価した。
評価基準
◎:平均点が4.5点以上
○:平均点が3.0点以上4.5点未満
△:平均点が2.0点以上3.0点未満
×:平均点が2.0点未満 (2) Method for evaluating the roughness of the preparation surface (texture of the dentifrice) After 1 month storage at 50 ° C., the appearance of the kneaded product when the dentifrice composition is taken out from the tube to the toothbrush (the roughness of the preparation surface ( About the dentifrice texture)), the three evaluators determined the following scoring criteria.
Grade criteria 5: Wrinkles are not recognized, smooth and glossy 4: Wrinkles are not recognized 3: Wrinkles are slightly recognized, but there is no problem in quality 2: Wrinkles are recognized, No granular aggregates are observed 1: Wrinkles and granular aggregates are considerably observed. The average score of three persons was determined, and the texture of the dentifrice was evaluated according to the following criteria.
Evaluation criteria ◎: Average score is 4.5 or higher ○: Average score is 3.0 or higher and lower than 4.5 △: Average score is 2.0 or higher and lower than 3.0 ×: Average score is 2.0 Less than
50℃で1ヶ月保存後、歯磨剤組成物をチューブから歯ブラシに出した時の液分離について、評価者3名が、下記の評点基準で判定した。
評点基準
5:全く液の分離が認められない
4:口元にわずかな滲みが認められるが、全体的には問題ない
3:全体的にわずかな滲みが認められるが、品質的には問題ないレベル
である
2:全体に液の分離が認められる
1:歯ブラシから落ちるほどの激しい液分離が認められる
3名の平均点を求め、液分離のなさについて下記基準で評価した。
評価基準
◎:平均点が4.5点以上
○:平均点が3.0点以上4.5点未満
△:平均点が2.0点以上3.0点未満
×:平均点が2.0点未満 (3) Evaluation Method of No Liquid Separation After storage for 1 month at 50 ° C., three evaluators determined the liquid separation when the dentifrice composition was taken out from the tube to the toothbrush according to the following criteria.
Rating criteria 5: No separation of liquid is observed 4: Slight bleeding is observed at the mouth, but overall there is no problem 3: Overall, slight bleeding is observed, but there is no problem with quality 2: Separation of liquid is observed in the whole 1: Vigorous liquid separation enough to fall from the toothbrush is observed. The average score of three persons was determined, and the absence of liquid separation was evaluated according to the following criteria.
Evaluation criteria ◎: Average score is 4.5 or higher ○: Average score is 3.0 or higher and lower than 4.5 △: Average score is 2.0 or higher and lower than 3.0 ×: Average score is 2.0 Less than
(A)グルコン酸銅;関東化学(株)製、グルコン酸銅
(A)クエン酸亜鉛;関東化学(株)製、クエン酸亜鉛
(B)高重合ポリエチレングリコール;
POLYOX WSR N-80
(ダウ・ケミカル社製、5W/V%水溶液の粘度:85mPa・s(ロー
ターNo.1、回転数50rpm、測定時間0.5分))
POLYOX WSR N-10
(ダウ・ケミカル社製、5W/V%水溶液の粘度:35mPa・s(ロー
ターNo.1、回転数50rpm、測定時間0.5分))
POLYOX WSR N-750
(ダウ・ケミカル社製、5W/V%水溶液の粘度:1,100mPa・s
(ローターNo.2、回転数10rpm、測定時間1分))
POLYOX WSR N-12K
(ダウ・ケミカル社製、2W/V%水溶液の粘度:420mPa・s(ロ
ーターNo.1、回転数10rpm、測定時間1分))
ポリエチレングリコール#400
(三洋化成工業社製、医薬部外品原料規格2006記載の平均分子量380
~420) Details of the raw materials used are shown below. The viscosity of the highly polymerized polyethylene glycol is the viscosity at 25 ° C. measured with a Brookfield viscometer (Brookfield RVT or RVF), as described above. Moreover, the viscosity of polyethylene glycol # 400 measured by the same method was less than the viscosity of (B) highly polymerized polyethylene glycol.
(A) Copper gluconate; manufactured by Kanto Chemical Co., Ltd., copper gluconate (A) zinc citrate; manufactured by Kanto Chemical Co., Inc., zinc citrate (B) highly polymerized polyethylene glycol;
POLYOX WSR N-80
(Viscosity of 5 W / V% aqueous solution manufactured by Dow Chemical Company: 85 mPa · s (rotor No. 1, rotation speed 50 rpm, measurement time 0.5 minutes))
POLYOX WSR N-10
(Manufactured by Dow Chemical Co., Ltd., viscosity of 5 W / V% aqueous solution: 35 mPa · s (rotor No. 1, rotation speed 50 rpm, measurement time 0.5 minutes))
POLYOX WSR N-750
(Dow Chemical Co., Viscosity of 5 W / V% aqueous solution: 1,100 mPa · s
(Rotor No. 2, rotation speed 10 rpm, measurement time 1 minute))
POLYOX WSR N-12K
(Manufactured by Dow Chemical Co., Ltd., viscosity of 2 W / V% aqueous solution: 420 mPa · s (rotor No. 1, rotation speed 10 rpm, measurement time 1 minute))
Polyethylene glycol # 400
(Average molecular weight 380 described in Sanyo Chemical Industries, Ltd., Quasi-drug raw material standard 2006)
~ 420)
前記口臭抑制効果の評価方法に準じ、試験後として歯磨きして4時間経過後の口臭を採取して口臭強度を判定し、更に、同様にして口臭改善度を求め、口臭抑制効果を評価した。 (4) Method of evaluating bad breath suppression effect According to the method of evaluation of bad breath suppression, brushing teeth after the test, collecting bad breath after 4 hours, determining bad breath strength, and further improving bad breath The bad breath suppression effect was evaluated.
被験者10名を用い、歯磨剤組成物約1gを歯ブラシにとり、3分間歯磨きを行った際の金属味について、金属味を全く感じないを4点、やや金属味を感じるを3点、金属味を感じるを2点、金属味を非常に感じるを1点として、判定した。
10名の平均点から以下の基準で、金属味の抑制効果を評価した。
金属味の抑制効果の評価基準:
◎:平均点が3.5点以上4.0点未満
○:平均点が3.0点以上3.5点未満
△:平均点が2.0点以上3.0点未満
×:平均点が1.0点以上2.0点未満 (5) Evaluation Method of Metallic Taste Suppressing Effect Using 10 subjects, about 1 g of the dentifrice composition was put on a toothbrush and the toothpaste was brushed for 3 minutes. Evaluation was made with 3 points for feeling taste, 2 points for feeling metallic taste, and 1 point for feeling very metallic taste.
The metal taste suppression effect was evaluated from the average score of 10 people according to the following criteria.
Evaluation criteria for metallic taste suppression effect:
◎: Average point is 3.5 or more and less than 4.0 point ○: Average point is 3.0 or more and less than 3.5 point △: Average point is 2.0 or more and less than 3.0 point ×: Average point is 1.0 to less than 2.0
1%水溶液(20℃)の粘度:20mPa・s(BL型粘度計、ロー
ターNo.1、回転数60rpm)
Viscosity of 1% aqueous solution (20 ° C.): 20 mPa · s (BL viscometer, rotor No. 1, rotation speed 60 rpm)
以下、処方例を表5に示す。処方例の歯磨剤組成物を上記と同様に調製し、同様に評価したところ、口臭抑制効果、歯磨剤のきめ、液分離のなさがいずれも◎であった。 [Prescription example]
Hereinafter, Table 5 shows formulation examples. The dentifrice compositions of the formulation examples were prepared in the same manner as described above and evaluated in the same manner. As a result, the bad breath suppressing effect, the texture of the dentifrice, and the absence of liquid separation were all excellent.
Claims (6)
- (A)銅塩及び亜鉛塩から選ばれる1種又は2種以上の水溶性金属塩を0.01~1質量%と、
(B)ブルックフィールド型粘度計で測定した25℃における5W/V%水溶液の粘度が10mPa・s以上であり、かつ前記粘度計で測定した25℃における2W/V%水溶液の粘度が800mPa・s以下である高重合ポリエチレングリコールを0.01~0.5質量%と
を含有してなることを特徴とする歯磨剤組成物。 (A) 0.01 to 1% by mass of one or more water-soluble metal salts selected from copper salts and zinc salts;
(B) The viscosity of a 5 W / V% aqueous solution at 25 ° C. measured with a Brookfield viscometer is 10 mPa · s or more, and the viscosity of a 2 W / V% aqueous solution at 25 ° C. measured with the viscometer is 800 mPa · s. A dentifrice composition comprising 0.01 to 0.5% by mass of the following highly polymerized polyethylene glycol. - (A)成分の水溶性金属塩が、グルコン酸銅、クエン酸銅、硫酸銅、塩化銅、グルコン酸亜鉛、硫酸亜鉛及びクエン酸亜鉛から選ばれる1種又は2種以上である請求項1記載の歯磨剤組成物。 The water-soluble metal salt of component (A) is one or more selected from copper gluconate, copper citrate, copper sulfate, copper chloride, zinc gluconate, zinc sulfate and zinc citrate. Dentifrice composition.
- (A)成分の水溶性金属塩が、グルコン酸銅及び/又はクエン酸亜鉛である請求項1又は2記載の歯磨剤組成物。 The dentifrice composition according to claim 1 or 2, wherein the water-soluble metal salt of the component (A) is copper gluconate and / or zinc citrate.
- (B)成分の高重合ポリエチレングリコールが、下記(1)又は(2)
(1)ブルックフィールド型粘度計で測定した25℃における5W/V%水溶液の粘度が10~20,000mPa・s、
(2)(1)で粘度が20,000mPa・sを超える場合は、前記粘度計で測定した25℃における2W/V%水溶液の粘度が800mPa・s以下
のものである請求項1、2又は3記載の歯磨剤組成物。 The highly polymerized polyethylene glycol of component (B) is the following (1) or (2)
(1) The viscosity of a 5 W / V% aqueous solution at 25 ° C. measured with a Brookfield viscometer is 10 to 20,000 mPa · s,
(2) When the viscosity exceeds 20,000 mPa · s in (1), the viscosity of the 2 W / V% aqueous solution at 25 ° C. measured with the viscometer is 800 mPa · s or less. 3. The dentifrice composition according to 3. - (A)成分と(B)成分との配合量の割合を示す(A)/(B)が、質量比として0.02~100である請求項1~4のいずれか1項記載の歯磨剤組成物。 The dentifrice according to any one of claims 1 to 4, wherein (A) / (B), which indicates the proportion of the amount of component (A) and component (B), is 0.02 to 100 as a mass ratio. Composition.
- 練歯磨剤である請求項1~5のいずれか1項記載の歯磨剤組成物。 The dentifrice composition according to any one of claims 1 to 5, which is a toothpaste.
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JP2017502374A JP6693504B2 (en) | 2015-02-26 | 2016-02-23 | Dentifrice composition |
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KR1020177023233A KR102518103B1 (en) | 2015-02-26 | 2016-02-23 | Toothpaste composition |
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JP2009001292A (en) * | 2007-06-20 | 2009-01-08 | Hitachi Zosen Corp | Method and apparatus for feeding spherical body to container |
TWI435733B (en) * | 2010-01-29 | 2014-05-01 | Colgate Palmolive Co | Oral care formulations for malodor control |
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- 2016-02-23 WO PCT/JP2016/055201 patent/WO2016136719A1/en active Application Filing
- 2016-02-23 KR KR1020177023233A patent/KR102518103B1/en active IP Right Grant
- 2016-02-23 JP JP2017502374A patent/JP6693504B2/en active Active
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JPH02311413A (en) * | 1989-05-26 | 1990-12-27 | Lion Corp | Composition for tooth paste |
US5820854A (en) * | 1997-03-27 | 1998-10-13 | The Procter & Gamble Company | Oral compositions containing polyoxyethylene |
JP2006506359A (en) * | 2002-10-04 | 2006-02-23 | ザ プロクター アンド ギャンブル カンパニー | Liquid dentifrice composition |
JP2009007292A (en) * | 2007-06-28 | 2009-01-15 | Lion Corp | Oral composition |
WO2010073975A1 (en) * | 2008-12-22 | 2010-07-01 | ライオン株式会社 | Toothpaste composition |
JP2013538199A (en) * | 2010-08-07 | 2013-10-10 | ザ・リサーチ・フアウンデーシヨン・フオー・ザ・ステート・ユニバーシテイ・オブ・ニユー・ヨーク | Oral composition comprising a zinc compound and an antimicrobial agent |
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KR20170122743A (en) | 2017-11-06 |
JPWO2016136719A1 (en) | 2017-12-07 |
CN107249547B (en) | 2020-09-01 |
JP6693504B2 (en) | 2020-05-13 |
CN107249547A (en) | 2017-10-13 |
KR102518103B1 (en) | 2023-04-06 |
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