JPH0338517A - Composition for oral cavity - Google Patents

Abstract

PURPOSE:To obtain a composition for oral cavity useful for preventing dental caries, periodontosis, etc., having coating ability of tooth plane and effects such as inhibition of bacterial plaque formation, acid resistance and pigmentation inhibition, comprising a specific fluoroalkyl phosphate or a salt thereof as an active ingredient. CONSTITUTION:A composition for oral cavity comprising one or more of a fluoroalkyl phosphate shown by the formula (Rf is 6-16C fluoroalkyl), formula II and a salt thereof (e.g. metallic salt, amine salt or ammonium salt). The composition can be made into a dosage form such as toothpaste, tooth powder, liquid dentifrice, mouth wash or gargling tablet. The amount of the compound shown by formula I or formula II blended is 0.01-30.0wt.%, preferably 0.1-2.0wt.% in the composition.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an oral composition, and more particularly, a composition containing a specific fluoroalkyl phosphate and/or a salt thereof as an active ingredient, which has tooth surface coating ability. The present invention relates to an oral composition.

[Conventional technology]

Human dental plaque is mostly protected from oral bacteria and plays an important role in the progression of caries, tartar, and periodontal disease (gingivitis, periodontitis). Antibacterial agents such as chlorhexidine and enzymes such as dextranase have been used so far in attempts to control plaque. Additionally, fluoride compounds such as sodium fluoride have been used to prevent caries and strengthen tooth structure.

On the other hand, fluoroalkyl compounds that inhibit plaque formation by forming complexes with calcium were proposed in US Patent Application No. 4,170.636.

In addition, fluoroalkyl compounds that are used together with sodium fluoride and the like to promote fluoroapatite formation by increasing their adsorption and persistence have been proposed in U.S. Patent Application Nos. 4,243,658 and 4,353.892. Ta.

[Problem to be solved by the invention]

Many oral compositions containing drugs for preventing dental caries and periodontal disease are commercially available. However, the current situation is that it has not been sufficiently effective. This is largely due to the fact that the effect is short-lived even when brushing teeth, etc., and that there is little residual drug. In addition, when tea or tobacco pigments adhere to the tooth surface, it damages the appearance, but there are no oral compositions on the market that inhibit this pigmentation, and known fluoroalkyl compounds do not coat the tooth surface. There are no known substances that have the ability to inhibit plaque formation, acid resistance, and pigmentation inhibition.

[Means to solve the problem]

Therefore, in view of the above-mentioned current situation, the present inventors have conducted intensive research and found that a specific fluoroalkyl phosphate ester and/or its salt has a remarkable ability to inhibit dental plaque formation and acid resistance by coating the tooth surface. , has been found to have the ability to inhibit pigmentation, leading to the completion of the present invention.

That is, the present invention provides an oral cavity product containing as an active ingredient one or more selected from fluoroalkyl phosphate esters or salts thereof represented by the following general formula (1) or (If). A composition is provided.

(In the formula, R2 is a saturated or unsaturated fluoroalkyl group having 6 to 16 carbon atoms.) Hereinafter, the present invention will be explained in detail.

The fluoroalkyl phosphate ester represented by the general formula (1) or (■) used in the present invention or its salt may be produced using any method, but for example, the method disclosed in JP-A-63-126886 By using the method described in (method for producing polyfluoroalkyl phosphoric acid, Imamura et al.), a mono(fluoroalkyl) phosphate represented by general formula (1) can be selectively produced. Regarding the bis(fluoroalkyl) phosphate represented by the general formula (II), JP-A No. 59-1379
It can be produced by using the method described in Publication No. 1 (method for producing phosphoric acid diester, Kurosaki et al.).

The above production method can produce a fluoroalkyl phosphate ester having a single carbon number or a mixture of a plurality of carbon numbers. In the case of manufacturing, it can be manufactured by using a fluoroalkyl alcohol having a single carbon number as a raw material.

Regarding the various fluoroalkyl phosphate ester salts used in the present invention, after producing the acid type fluoroalkyl phosphate ester using the above-mentioned method, a counterion of a metal or an inorganic or organic base such as an amine is added. Any salt can be produced by adding and neutralizing.

Examples of the fluoroalkyl phosphate salts include metal salts of alkali metals, aluminum, etc., amon salts, ammonium salts, etc. of alkylamines, alkanolamines, etc.

The oral composition of the present invention includes toothpaste, powdered toothpaste, liquid toothpaste,
Possible embodiments include mouthwash, gargling tablets, gingival pine surge cream, chewing gum, pastilles, oral pasta, and the like.

In the oral composition of the present invention, the above-mentioned fluoroalkyl phosphate ester and/or salt thereof is present in the composition at 0.0
1 to 30.0% by weight, preferably 0°1 to 2.0% by weight
It is appropriate to mix them in the following proportions.

Here, a mono(fluoroalkyl)phosphate ester and/or a salt thereof represented by the general formula (1) and a general formula (II
It is preferable to use the bis(fluoroalkyl) phosphate ester and/or its salt represented by ) alone, but a mixture thereof can also be used. Also, general formula (1)
When using a mono(fluoroalkyl) phosphate represented by the formula (1) and/or a salt thereof, one of the two hydroxyl groups of the fluoroalkyl phosphate represented by the above general formula (1) is a sodium salt or a potassium salt. and one in which both of the two hydroxyl groups have become sodium salt or potassium salt, in a weight ratio of 100:O to 20:8.
It is preferable to use a ratio of 0.

Further, as long as the fluoroalkyl chain Rt of the fluoroalkyl phosphate ester or its salt used in the present invention has 6 to 16 carbon atoms, it can be used either with a single carbon number or a mixture of multiple carbon numbers. However, those with a single carbon number are preferred.

Further, the degree of fluorination of the fluoroalkyl group R2 of the fluoroalkyl phosphate ester or salt thereof used in the present invention is preferably 10 to 100%.

Here, the degree of fluorination refers to the rate at which hydrogen atoms in an alkyl group are substituted with fluorine atoms.

The other components of the oral composition of the present invention are intended for use,
It can be changed as appropriate depending on the mode of use. Furthermore, any of the components used in conventional oral compositions can be used. For example, in the case of toothpaste, calcium diphosphate, calcium carbonate, calcium pyrophosphate,
Insoluble sodium metaphosphate, amorphous silica, crystalline silica, aluminosilicate, aluminum oxide, aluminum hydroxide, abrasives such as resin, caking of carboxymethyl cellulose, hydroxyethyl cellulose, alginate, carrageenan, gum arabic, polyvinyl alcohol, etc. Thickening agents such as polyethylene glycol, sorbitol, glycerin, propylene glycol, sodium lauryl sulfate, sodium dodecylbenzenesulfonate, sodium N-lauroylsarcosinate, N-acylglutamate, cy=stM fatty acid ester, monoalkyl phosphorus Foaming agents such as acid esters, essential oils such as peppermint and spearmint, l-menthol, carvone,
Flavoring materials such as eugenol and anethole, sodium saccharin, stevioside, neohesberidyl dihydrochalcone, glycyrrhizin, verlartin,
It is produced by mixing ingredients such as a sweetener such as P-methoxycinnamoldehyde and a preservative with water and following a conventional method.

In addition, in mouthwashes and other mouthwashes, ingredients are appropriately blended depending on the properties of the product.

In addition, in the present invention, sodium chloride, vitamin C
1-vitamin E1 nicotinic acid ester, allantoin chlorhydroxyaluminum, azulene, water-soluble primary or diphosphate, quaternary ammonium compound, fluoride compound, lysozyme chloride, hinokitiol, zeolite, chlorhexidine, protease, crude drug extraction It is also possible to incorporate active ingredients such as substances.

〔Effect of the invention〕

The present invention makes it possible to provide an oral composition containing a drug that has the ability to coat the tooth surface, and by coating the tooth surface, it imparts water repellency to the tooth surface, which was difficult to do with antibacterial agents, enzymes, etc. By imparting sustainability, it is possible to obtain certain effects such as inhibiting plaque formation, acid resistance, and inhibiting pigmentation. Oral compositions effective in inhibiting deposition can be provided.

Next, experimental examples of the present invention will be shown to specifically explain the effects of the present invention.

Experimental example 1 (plaque formation inhibition experiment) As a tooth model, hydroxyapatite pieces (10×1
0x2 mm, manufactured by Asahi Kogaku Co., Ltd.), the sample was immersed in 1.01% by weight shown in Table 1 for 5 minutes, and then washed with deionized water for 5 minutes. 20 + sg of dental plaque collected from the human oral cavity was inoculated into 30 - of the saliva supernatant collected from the human, the hydroxyapatite piece was immersed, and anaerobically cultured at 37°C for 24 hours to form dental plaque. Then, use Prospec staining solution (
(manufactured by Mento Dental Industry Co., Ltd.). After drying, plaque formation was measured using a color difference meter 10010P (manufactured by Nippon Heavy Industries Co., Ltd.), and the relative value to the control was calculated.

The results are shown in Table 1, and the salts of fluoroalkyl phosphate represented by general formula (1) or (I[) had a remarkable ability to inhibit dental plaque formation.

Table Experimental Example 2 (Acid Resistance Experiment) 1 g of hydroxyapatite powder (manufactured by Wako Seyaku Kogyo Co., Ltd.) was suspended in 3011 deionized water. To this, add 10ml of the sample solution shown in Table 2.Final, 0% by weight
), and was allowed to act for 3 minutes. The precipitate, which had been filtered and washed twice with deionized water, was suspended in 100 ad deionized water, and 3.0 ad
50% by weight of lactic acid (adjusted to pif 4.0) was added.

After reacting for 30 minutes, the pH and the amount of Ca"" eluted were measured.

pH was measured using pH meter F-8 (manufactured by Horiba, Ltd.).
+ was measured using an ion analyzer EA940 (manufactured by Orion Research).

The results are shown in Table 2, and the salts of fluoroalkyl phosphates represented by general formula (1) or (II) had remarkable acid resistance.

Table 2 Experimental Example 3 (Pigmentation Inhibition Experiment) As a tooth model, hydroxyapatite pieces (10X1
After immersing the sample in 1.0% by weight of the sample shown in Table 3 for 5 minutes, the sample was washed with deionized water for 5 minutes. On the other hand, 0.1% by weight tannic acid aqueous solution (pf17
．． (adjusted to 0) and 0.1% by weight ferrous sulfate aqueous solution were mixed in equal amounts, and the hydroxyapatite piece was immersed for 30 minutes.
Stained. After drying, pigmentation was measured using a color difference meter 10010P (manufactured by Nihon Heavy Industries Co., Ltd.), and the relative value to the control was calculated.

The results are shown in Table 3, and the salts of fluoroalkyl phosphate represented by general formula (1) or (II) had a remarkable ability to inhibit pigmentation.

Table 3 [Examples] Next, the present invention will be explained in more detail by showing examples of the present invention, but the present invention is not limited to these examples.

Example 1 Degas and mix the following ingredients, And so.

Ct. FttCHtC)ltOPO(OH)ONaC+
oFztCHtCHzOPO(ONa)g Toothpaste Aluminum hydroxide Silicic anhydride Carboxymethyl cellulose Sodium lauryl sulfate Sodium saccharin Glycerin 70% Sorbit liquid Fragrance Purified water Paste Toothpaste 0.20% by weight 0.20 30.00 2.00 2.00 1.50 0.10 10.00 is, o.

0.80 Appropriate amount Example 2 The following components were degassed and mixed to obtain a transparent dentifrice.

C@Ft? CToCH*0PO(OH)ONa Anhydrous silicate carboxymethyl cellulose Purified water 1.00% by weight 35.00 1.20 Appropriate amount Example 3 The following components were degassed and emulsified to prepare a coating agent.

(C1Fl?CHgCHtO)tPOONa Monoethanol Fruit Liquid Paraffin Polyvinyl Alcohol Fatty Acid Monoglyceride Glycerin Flavor Powder Sig Sugar Creamy Gingiva 0.50% by weight 0.10 7.00 5.00 3.00 15.00 0.10 Appropriate Amount Example 4 The following ingredients were mixed and a small amount of water was added to make a paste, which was then molded into a disk shape and dried to obtain a troche.

(CsF l?CHICH!O)! To P.O.O.
1.00% by weight citric acid
0.10 Aspartame 0.10 Dextrin io, o.

Gum Arabic 3.00 Flavor
Microporous Sugar Appropriate Amount Example 5 The following ingredients were heated and kneaded and molded into chewing gum.

CtJttCHxCHzOPO(OH)ONa
O, 50% by weight gum base 20.
00 Corn syrup 20.00 Sucrose fatty acid ester 2.00 Sodium saccharin 0.10 Glycerin
20.0070% sorbitol liquid
35.00 Perfume 0.80 Coloring agent Small quantity Example 6 The following components were mixed to obtain a liquid preservative.

Honjima is used after being diluted with water to about 10 times.

C1Fl? CH,CHtOPO(OH)OK
2.00 wt% CsP+tCHgCHgOPO (OK
)t 2.00 ethanol
10.00 Satucharin Sodium 0.5
0 monoethanolamine 0. 10 Chlorhexidine gluconate 0.10 Pluronic F102
0.50 Perfume 0.20 Total 100.00% by weight Next, usage examples of the present invention will be shown to specifically explain the effects of the present invention.

Usage Example 1 Five men aged 25 to 40 and five women aged 20 to 35 used the toothpaste presented in Example 1. As a result, all participants felt that their tooth surfaces felt smoother immediately after use, and the next day, eight patients complained that there was less plaque on their teeth.

Use Example 2 The rutting agent presented in Example 6 was used on five men aged 25 to 40 and five women aged 20 to 35. As a result, all of them reported feeling refreshed and their tooth surfaces felt smooth immediately after use.

Claims (1)

[Claims] 1. It is characterized by containing as an active ingredient one or more selected from fluoroalkyl phosphate esters or salts thereof represented by the following general formula (I) or (II): Oral composition. ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(II) 2. The oral composition according to claim 1, wherein the salt of the fluoroalkyl phosphate is selected from metal salts, amine salts, and ammonium salts. 3. One of the two hydroxyl groups of the fluoroalkyl phosphate represented by the general formula (I) becomes a sodium salt or a potassium salt, and one in which both of the two hydroxyl groups become a sodium salt or a potassium salt. Claim 1: Contains the following in a weight ratio of 100:0 to 20:80.
Or the oral composition according to 2. 4. R_f of the fluoroalkyl phosphate ester or salt thereof represented by general formula (I) or (II) is a saturated fluoroalkyl group having a single carbon number, according to any one of claims 1 to 3. Oral composition. 5. R_f of the fluoroalkyl phosphate ester or its salt represented by general formula (I) or (II) is fluorination degree 1
Claims 1 to 4 are 0 to 100% fluoroalkyl groups.
The oral composition according to any one of the above.