JP2001335448A - Dentifrice composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a dentifrice composition for remarkably preventing decrease in residual ratio of a hydroxy-2-pyridone derivative or its salt with time. SOLUTION: This dentifrice composition is characterized by using both the hydroxy-2-pyridone derivative or its salt and inorganic powder having >=0.05 mmol/g acidity as an abrasive.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

FIELD OF THE INVENTION The present invention relates to a hydroxy-2-
The present invention relates to a dentifrice composition containing a pyridone derivative or a salt thereof.

[0002]

BACKGROUND OF THE INVENTION Conventionally, it has been known that hydroxy-2-pyridone derivatives and salts thereof have an effect of inhibiting plaque formation (JP-A-7-8).
No. 2126). However, the hydroxy-2-pyridone derivative and its salt have a problem that the residual ratio decreases with time, particularly when the compound is incorporated into a dentifrice composition, and it is desired to solve this problem. In addition, it has been proposed to increase the plaque formation inhibitory effect by using a hydroxy-2-pyridone derivative or a salt thereof in combination with a polyoxyethylene / polyoxypropylene block copolymer (Japanese Patent Laid-Open No. Hei 10 (1999)).
However, there is a need for a method for more effectively preventing a decrease in the residual ratio when a hydroxy-2-pyridone derivative or a salt thereof is incorporated into a dentifrice composition.

[0003]

Means for Solving the Problems and Embodiments of the Invention The present inventors have conducted intensive studies in order to respond to the above-mentioned demands. As a result, in a dentifrice composition containing a hydroxy-2-pyridone derivative or a salt thereof, Acidity of 0.0 as abrasive
It has been found that when an inorganic powder of 5 mmol / g or more is used, a decrease in the residual ratio of the hydroxy-2-pyridone derivative or a salt thereof that is sparingly soluble in water in a dentifrice composition is remarkably prevented. The present invention has been accomplished.

Hereinafter, the present invention will be described in more detail.
The dentifrice composition of the present invention is obtained by using a hydroxy-2-pyridone derivative or a salt thereof in combination with an inorganic powder having an acidity of 0.05 mmol / g or more as an abrasive.

In the present invention, a hydroxy-2-pyridone derivative or a salt thereof is represented by the following general formula (1).

[0006]

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In the above formula (1), R ¹ and R ² are each a hydrogen atom or a hydroxyl group, and at least one of R ¹ and R ² is a hydroxyl group. R ³ , R ⁴ , and R ⁵ are each a hydrogen atom or a monovalent organic group, and examples of the monovalent organic group include an alkyl group, an alkenyl group, a cycloalkyl group, a bicycloalkyl group, a cycloalkyl-alkyl group, Aryl group, aralkyl group, arylalkenyl group, aryloxyalkyl group, arylmercaptoalkyl group,
Examples thereof include a benzhydryl group, a phenylsulfonylalkyl group, a furyl group, and a furylalkenyl group. Examples thereof include an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, and a cycloalkyl group having 3 to 18 carbon atoms. A cycloalkyl-alkyl group and a benzyl group are preferred.

The hydroxy-2-pyridone derivative of the above formula (1) has a 1-hydroxy-2-pyridone or 3-hydroxy-2-pyridone skeleton, and each has a tautomer. In the case of a 1-hydroxy-2-pyridone skeleton, a 2-hydroxypyridine-N-oxide skeleton or the like exists as an isomer, and in the case of a 3-hydroxy-2-pyridone skeleton, a 2,3-dihydroxypyridine skeleton or the like exists. Exists. The present invention includes these isomers.

Further, the above hydroxy-2-pyridone derivative can be used as a salt using a suitable base. Examples of the salt form include sodium, potassium, magnesium, calcium, strontium, zinc, copper, aluminum, lanthanum, iron, tin and other monovalent or polyvalent metal salts, ammonium salts, monoethanolamine, diethanolamine, triethanolamine, Salts with ethylenediaminehydroxylamines, salts with basic amino acids such as arginine and lysine, or salts with basic peptides and basic proteins containing basic amino acids are widely available and pharmaceutically acceptable Can be selected as appropriate.

The compounding amount of the hydroxy-2-pyridone derivative of the formula (1) or a salt thereof is preferably 0.01 to 10% (mass percentage, the same applies hereinafter), particularly preferably 0.1 to 5%.
If it is less than 01%, plaque formation may not be suppressed. Further, if the content is more than 10%, there may be a problem in use feeling and formulation.

In the present invention, the inorganic powder used as an abrasive has an acidity of at least 0.05 mmol / g, preferably from 0.05 to 1 mmol / g, more preferably from 0.1 to 0.7 mmol / g. / G. If the acidity of the solid acid is less than 0.05 mmol / g, hydroxy-2
-The pyridone derivative or a salt thereof cannot be sufficiently stabilized.

As the inorganic powder, Na ₂ O.ZrO ₂
・ SiO ₂ , K ₂ O ・ Al ₂ O ₃・ SiO ₂ , TiO ₂・ Si
O ₂ , ZrO ₂ · SiO ₂ , Na ₂ O · MgO · SiO _{2 and the} like can be mentioned, and one of these can be used alone or in combination of two or more.

The amount of the inorganic powder (abrasive) can be 5 to 60%, especially 10 to 50% of the whole composition.

In the present invention, an abrasive other than the above-mentioned inorganic powder may be blended as long as the effects of the present invention are not impaired.

The dentifrice composition of the present invention is prepared in the form of toothpaste, liquid dentifrice and the like. Depending on the form and the like, in addition to the above-mentioned components, the usual compounding ingredients such as thickeners and binders , A surfactant, a sweetener, a preservative, an active ingredient, and the like, and can be produced by mixing these ingredients with water.

The thickener includes glycerin, sorbitol, xylitol, propylene glycol, polyethylene glycol and the like.

Examples of the binder include carrageenan, sodium alginate, propylene glycol alginate, xanthan gum, polyacrylic acid, sodium polyacrylate, carboxyvinyl polymer, tragacanth gum, guar gum, locust bean gum, sodium carboxymethylcellulose, hydroxyethylcellulose, hydroxypropyl Examples include cellulose, methylcellulose, gellan gum, gelatin, curdlan, gum arabic, agar, pectin, polyvinyl alcohol, polyvinylpyrrolidone, pullulan and the like.

Examples of the surfactant include anionic surfactants, cationic surfactants, and nonionic surfactants. Specific examples thereof include sodium lauryl sulfate, sodium N-lauroyl sarcosine, and α-olefin sulfone. Sodium acid, N-acylglutamate, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, N-acyltaurate, sucrose fatty acid ester, alkylol amide, HLB is 13
And polyoxyethylene hydrogenated castor oil, polyglycerin fatty acid ester, pluronic, polyoxyethylene sorbitan monostearate and the like.

As sweeteners, sodium saccharin,
Examples include stevioside, stevia extract, paramethoxycinnamic aldehyde, neohesperidyl dihydrochalcone, and perillartin.

Examples of the flavor include terpenes such as 1-menthol, carvone, anethole, limonene and the like, and derivatives thereof. Examples of the coloring agent include Blue No. 1, Yellow No. 4, and titanium dioxide.

Examples of the active ingredient include cationic fungicides such as chlorohexidine, benzethonium chloride, benzalkonium chloride, cetylpyridinium chloride, and decalinium chloride, phenolic compounds such as triclosan, hinokitiol, and biosol, dextranase, and mutanase. Enzymes such as lysozyme, amylase, protease, lytic enzyme and superoxide dismutase; vitamins such as vitamin E and vitamin C; alkali metal monofluorophosphates such as sodium monofluorophosphate and potassium monofluorophosphate; Sodium, fluorides such as stannous fluoride, tranexamic acid, epsilon aminocaproic acid, aluminum chlorohydroxyallantoin, dihydrocholesterol, glycyrrhizic acid, glycyrrhetic Phosphate, bisabolol, glycerophosphate, chlorophyll, sodium chloride, polyvinyl pyrrolidone, polyethylene glycol, water-soluble inorganic phosphoric acid compounds and the like, can be blended these known active ingredients one or more.

[0022]

The dentifrice composition of the present invention comprises hydroxy-2
-The pyridone derivative or the salt thereof has a remarkably prevented decrease in the residual ratio over time.

[0023]

EXAMPLES Hereinafter, the present invention will be described in detail with reference to experimental examples and examples, but the present invention is not limited to the following examples.

[Experimental Example] A toothpaste composition having the following composition using the abrasives shown in Table 1 was prepared, filled in a laminate tube, stored at 40 ° C. for one month, and the remaining amount of pyroctone olamine was measured. Was measured by liquid chromatography.
Table 2 shows the results. In addition, the measuring method of the acidity of the abrasive of Table 1, the measuring method of pyrocton olamine, and the conditions of a liquid chromatography are as follows. Toothpaste composition abrasive 25% pyrocton olamine 0.2 propylene glycol 3 carrageenan 0.5 sodium carboxymethylcellulose 0.6 sorbitol 50 saccharin 0.2 sodium fluoride 0.21 sodium lauryl sulfate 2 fragrance 1 purified water balance 100. 0%

Acidity measurement method 10 to 10 mL Erlenmeyer flask with stopper
Add 20 mL of benzene and add 0.2-1 g of sample. An indicator (methyl red: pKa = + 4.8)
A few mL of a benzene solution (0.1%) in which is dissolved is added and shaken. Next, titration is performed with a benzene solution of 0.1 N n-butylamine. Indicator color (red) is basic color (yellow)
The point changed to is the end point. Acidity (mmol / g) = A / B A: Titration (mL) × 0.1 B: Sampling amount Pirrocton olamine measurement method 1 g of toothpaste is precisely weighed, and a methanol / water mixture (80:
20) After extraction and filtration with 25 mL, the value is determined from the peak area of liquid chromatography. Residual amount (%) = (amount determined from peak area / blended amount) x
100 liquid chromatography conditions Column: L-column ODS Mobile phase: methanol / water = 80/20 Detector: UV absorption spectrophotometer

[0026]

[Table 1]

[0027]

[Table 2]

From the above results, it was confirmed that the abrasive was 0.05 m
It is recognized that the use of an inorganic powder having an acidity of at least mol / g can significantly prevent a decrease in the amount of hydroxy-2-pyridone derivatives remaining over time.

Hereinafter, embodiments will be described. [Example 1] Toothpaste Abrasive A 25% Piroctoneolamine 0.1 Propylene glycol 3 Sodium carboxymethylcellulose 1 Glycerin 35 Sodium fluoride 0.21 Dextranase 0.2 Saccharin 0.15 Sodium lauryl sulfate 1.5 Perfume 1 Purified water Remaining total 100.0%

Example 2 Toothpaste Abrasive B 15% pyroctone olamine 0.3 propylene glycol 3 carrageenan 0.5 sodium alginate 0.6 sorbite 20 glycerin 20 polyethylene glycol # 400 2 sodium monofluorophosphate 0. 76 Dextranase 0.2 Saccharin 0.2 Sodium lauryl sulfate 1.5 Fragrance 1 Purified water Remaining 100.0%

[Example 3] Toothpaste Abrasive C 25% Pyrocton olamine 0.5 Propylene glycol 3 Xanthan gum 0.5 Sodium polyacrylate 0.6 Glycerin 35 Saccharin 0.15 Sodium lauryl sulfate 1.5 Fragrance 1 Purified water remaining 100.0%

Example 4 Toothpaste Piloctone olamine 0.2% Abrasive D 10 Propylene glycol 3 Sodium carboxymethyl cellulose 0.7 Carrageenan 0.5 Sorbit 40 Polyethylene glycol # 4000 0.3 Saccharin 0.2 Lauryl sulfate Sodium 1.5 Flavor 1 Purified water Remaining total 100.0%

Example 5 Toothpaste Piloctone olamine 0.4% Abrasive A 18 Propylene glycol 3 Xanthan gum 0.6 Sodium alginate 0.5 Sorbit 45 Saccharin 0.15 Sodium lauryl sulfate 2.0 Sodium bicarbonate 0 .5 Perfume 1 Purified water Remaining 100.0%

Example 6 Liquid Toothpaste Piroctoneolamine 0.1% Abrasive C 17 Propylene glycol 3 Xanthan gum 0.3 Glycerin 25 Sorbitol 30 Sodium fluoride 0.21 Saccharin 0.15 Sodium lauryl sulfate 1.5 Fragrance 1 purified water remaining 100.0%

Example 7 Liquid Dentifrice Pirocton Olamine 0.3% Abrasive D 15 Propylene Glycol 3 Xanthan Gum 0.2 Carrageenan 0.1 Glycerin 20 Sorbit 35 Sodium Monofluorophosphate 0.76 Saccharin 0.15 Lauryl Sodium sulfate 1.5 Perfume 1 Purified water Remaining total 100.0%

 ──────────────────────────────────────────────────続 き Continued on the front page F term (reference) 4C083 AB372 AB382 AB472 AC122 AC132 AC782 AC851 AC852 AC862 AC902 AD042 AD092 AD272 AD302 AD352 AD472 CC41 EE01 EE37

Claims (1)

[Claims] 1. A dentifrice composition comprising a hydroxy-2-pyridone derivative or a salt thereof in combination with an inorganic powder having an acidity of 0.05 mmol / g or more as an abrasive.