JP2627709B2 - Oral composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a stable and palatable oral composition containing a phosphate ester having an excellent tooth surface protecting effect.

[0002]

2. Description of the Related Art Phosphate esters (hereinafter referred to as "AP") are less irritating, form a film on the tooth surface, improve the acid resistance of the tooth, and are excellent in suppressing plaque formation and preventing dental caries. I have. Accordingly, the use of AP in oral compositions has been proposed in the past. For example, JP-A-53-47
No. 542 (US Pat. No. 4,152,421) describes a dentifrice containing a monoalkyl phosphate salt as a foaming agent which does not change the taste of food and drink;
No. 500061 (US Pat. No. 4,366,146) states that
A dentifrice-preventing dentifrice composition containing a monoalkyl phosphate as a film-forming substance is described;
JP-A-2-200619 (USP 501937)
3) For use as a dentifrice and mouthwash which does not change the taste of foods and drinks which have di-medium chain alkyl phosphate, di long chain alkyl phosphate and monoalkyl phosphate and have excellent anti-caries activity. Suitable aqueous compositions are described; and US Pat. No. 4,036,950 describes dentifrices containing abrasives, cationic disinfectants and polyoxyethylene alkyl ether phosphates.

[0003] However, when actually formulating an oral composition containing AP, a basic compound is used to neutralize the phosphate group. The use of amines or alkanolamines has caused the following problems.

[0004] That is, the alkali metal salt of AP has a high Krafft point, crystallizes in the preparation, becomes non-uniform, and has a problem in stability. Accordingly, it is difficult to apply the composition to a dosage form such as a transparent uniform mouthwash. In addition, although the alkylamine salt and alkanolamine salt of AP have low Krafft points, they are highly irritating and have a problem in safety. Further, in the storage test, coloring occurs and there is a problem in stability. Furthermore, A
The taste of P is generally poor, and the problem is that bitterness remains after use.

[0005] On the other hand, basic amino acid salts of AP are conventionally known compounds. For example, JP-A-58-180
No. 496 discloses an arginine salt of a phosphate ester and an emulsifier containing the same; Japanese Patent Application Laid-Open No. 1-319410 (US Pat. No. 5,085,854) discloses a monoalkyl phosphate arginine salt, a nonionic surfactant, an oil agent and water. Translucent emulsified cosmetics are described. However,
These are all compounded as emulsifiers in cosmetics, and there is no disclosure at all about the possibility of mixing a basic amino acid salt of AP into an oral composition.

[0006]

SUMMARY OF THE INVENTION An object of the present invention is to provide an oral composition containing AP, which is excellent in protecting the tooth surface, contains a stable and delicious taste.

[0007]

Means for Solving the Problems Under such circumstances, the present inventors have conducted intensive studies, and as a result, by using a basic amino acid such as arginine or lysine to neutralize AP, the Kraft point is lowered. The present inventors have found that a composition for oral cavity which is stable without being colored even when stored for a long period of time, has an excellent protective effect on the tooth surface, and has a surprisingly improved taste can be obtained.

That is, the present invention provides the following general formula (1)

[0009]

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(In the formula, R ¹ represents a linear or branched alkyl or alkenyl group having 6 to 20 carbon atoms which may be substituted by a fluorine atom, and ^one of X ¹ and X ² represents a basic amino acid residue. A hydrogen atom, an alkali metal, an ammonium, an alkylamine, an alkanolamino or a basic amino acid residue, and n represents a number from 0 to 4). To provide a composition for use.

Further, the present invention provides the following components (A) and (B): (A) The following general formula (2)

[0012]

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(Wherein R ¹ represents a linear or branched alkyl or alkenyl group having 6 to 20 carbon atoms which may be substituted by a fluorine atom, and Y ¹ and Y ² are the same or different and each represents a hydrogen atom , An alkali metal, ammonium, an alkylamine or an alkanolamine, wherein n is a number from 0 to 4), and (B) a basic amino acid. It is.

In the phosphoric acid monoesters (1) and (2) used in the present invention, a linear or branched alkyl or alkenyl having 6 to 20 carbon atoms which may be substituted by a fluorine atom represented by R ^1. Examples of the group include a hexyl group, octyl group, decyl group, dodecyl group, tetradecyl group, hexadecyl group, octadecyl group, eicosyl group, 2-ethylhexyl group, dodecenyl group, oleyl group, elaidyl group, and the like. Among these R ^{1 s} , those having 8 to 2 carbon atoms
An alkyl group having 0, especially 10 to 20, more preferably 12 to 16 and further 14 carbon atoms is preferred. These alkyl groups and alkenyl groups may have a single chain length or a mixture of a plurality of alkyl groups having different chain lengths.

The basic amino acids include naturally occurring arginine, lysine, and histidine, but are not limited to those having a carboxyl group and an amino group in the molecule, are water-soluble, and have a pH of aqueous solution. Should be 7 or more. Of these, arginine is particularly preferred.

The phosphoric acid monoesters (1) used in the present invention can be produced by a known method. Examples of the production method include a method in which a commercially available phosphoric monoester (2) is made alkaline, then desalted by electrodialysis, and neutralized with a basic amino acid (B). At the time of neutralization, an alkali metal salt, an amine salt, an organic amine salt, or the like may be partially contained to such an extent that the neutralization is not inhibited.
In addition, basic amino acid (B) and phosphoric acid monoester (2)
Is (B) / (2) = 0.8 to 2.0, especially 1.
It is preferably 0 to 1.8.

In the present invention, the composition for oral cavity may be prepared by blending the phosphoric acid monoesters (1) obtained as described above, but the components (A) and (B) may be blended. May be neutralized in the composition. When both the component (A) and the component (B) are blended, the blending amount of the component (B) is (B) / (A) = 0.8 to 2.0, particularly 1.0 to 1.0 in a molar ratio.
It is desirable that the amount be 1.8. In this case, it is considered that the component (A) and the component (B) react in the obtained composition, and phosphoric acid monoesters (1) are generated.

The content of the phosphoric acid monoesters (1) or (2) in the oral composition of the present invention is 0.001 to 50% by weight (hereinafter simply referred to as "%"), preferably 0.1% by weight. 05
-10%, more preferably 0.1-5%, particularly preferably 0.1-3%. If the content is less than 0.001%, the effect of protecting the teeth is weak, and if it exceeds 50%, the stability of the preparation deteriorates.

The oral composition of the present invention contains, in addition to the above-mentioned essential components, an oral vehicle which is generally used within a range not to impair the effects of the present invention, and includes toothpaste, powder toothpaste, liquid toothpaste,
Mouthwash (mouthwash), mouthwash, mouth rinse, gum massage cream, oral troche, chewing gum, candy and the like can be provided. Of these forms, mouthwash, mouth rinse,
Gargle liquid composition or toothpaste, powder toothpaste, liquid toothpaste,
A solid or paste-like composition such as a gum massage cream or an oral troche is preferred. Such oral vehicles include abrasives, binders, wetting agents, surfactants, flavors, sweeteners, preservatives, pigments, water, bactericides, water-soluble fluorides, silicones, and other active ingredients. No.

The abrasives used herein are calcium hydrogen phosphate, calcium carbonate, calcium pyrophosphate, insoluble sodium metaphosphate, potassium metaphosphate, silicic anhydride, hydrous silicic acid, aluminum silicate, zirconium silicate, bentonite, zeolite for polishing. , Aluminum oxide, aluminum hydroxide, resin and mixtures thereof. Of these, silicic anhydride, hydrous silicic acid, aluminum hydroxide, calcium carbonate, and zeolite are particularly preferred. Examples of the binder include sodium carboxymethylcellulose, methylcellulose, hydroxyethylcellulose, alginate, carrageenan, gum arabic, polyvinyl alcohol, tragacanth gum, starch, and sodium polyacrylate. As a humectant,
Examples include polyethylene glycol, propylene glycol, sorbitol, glycerin, maltitol, xylitol and the like. Of these, glycerin and sorbitol are preferred. The surfactant is used as a foaming agent or a stabilizer for oily substances, and various surfactants other than the phosphoric ester are used. Examples of preferred surfactants include sodium alkyl sulfate, sodium alkylbenzene sulfonate, sodium N-acyl sarcosinate, N-acyl glutamate, polyoxyethylene hydrogenated castor oil, polyoxyethylene polyoxypropylene block copolymer (pluronic type) ), Sucrose fatty acid esters, alkyl glycosides, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, alkyldimethylamine oxide, carbobetaine, hydroxycarbobetaine, phosphobetaine, hydroxyphosphobetaine, sulfobetaine, hydroxysulfobetaine and the like. Can be Among them, water-soluble nonionic surfactants such as polyoxyethylene hydrogenated castor oil, polyoxyethylene polyoxypropylene block copolymer, sucrose fatty acid ester, alkyl glycosides, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, and amphoteric Surfactants are particularly preferred.

As the flavor, natural flavors such as spearmint oil, peppermint oil, winter green oil, sassafras oil, clove oil, sage oil, eucalyptus oil, mayonnaise oil, cinnamon oil, thyme oil, lemon oil and orange oil;
Synthetic flavors such as menthol, anethole, carvone, eugenol, thymol, methyl salicylate and the like can be mentioned.
Examples of the sweetener include saccharin, saccharin sodium, stevioside, neohesperidyl dihydrochalcone, berraltin, p-methoxycinnamic aldehyde, glycyrrhizinate, aspartame (aspartylphenylalanine methyl ester) and the like. Chlorhexidines, quaternary ammonium salts,
Triclosan, alkyldiaminoethylglycine hydrochloride and the like. Preservatives include benzoic acid, sodium benzoate, parahydroxybenzoate and the like. Examples of the water-soluble fluoride include sodium fluoride and sodium monofluorophosphate. Other active ingredients include chlorophyll compounds, sodium chloride,
Vitamin C, vitamin E, nicotinic acid ester, allantoinchlorohydroxyaluminum, azulene, lysozyme chloride, hinokitiol, β-glycyrrhetinic acid,
Examples include dipotassium glycyrrhizinate, protease, and crude drug extracts.

The amount of the oral vehicle varies depending on the form of the oral composition. In the case of a liquid composition, the liquid vehicle contains an abrasive,
Although all vehicles except the binder can be blended, basically, the phosphoric acid monoesters (1) or (2) are added in 0.05%.
-10%, wetting agent 1-30%, alcohol and water 5
It is preferably contained in an amount of 0 to 96%. Here, the weight ratio of water: alcohol is 1: 1 to 200: 1, especially 5: 1 to 1: 1.
100: 1 is preferred. Alcohol is one in the total composition
It is preferable to mix it by 20%.

In the case of a paste-like composition, all of the above-mentioned oral vehicles can be blended. However, basically, 0.05 to 10% of a phosphate (1) or (2) and an abrasive are used. It preferably contains 10 to 75%, 0.5 to 5% of a binder, and 10 to 85% of a wetting agent and water. Here, the abrasive is preferably 20 to 75% for toothpaste and 10 to 30% for liquid toothpaste. In the case of a solid composition such as a toothpaste, a solid component can be blended in the oral vehicle, but the phosphate ester (1) or (2) is basically added in an amount of 0.05 to 10%. It is preferable to mix 60 to 99% of an abrasive.

[0024] Of the oral vehicles, it is preferable to add a total of 0.01 to 5% of a flavor and a sweetener. The oral composition of the present invention has a pH of 5 to 9.5, particularly 6 to 8.
Is preferably within the range.

Among the oral compositions of the present invention, a solid composition such as toothpaste can be prepared usually by mechanically mixing the solid components. In addition, the paste composition,
Usually, it can be prepared by mechanically degassing and mixing the above components.

In order to protect the tooth surface using the oral composition of the present invention, the oral composition of the present invention must be regularly
Preferably, it is applied 1-3 times daily. Of the oral compositions, mouth rinse is most preferred. The tooth rinse can be well protected by including about 10 ml of the mouth rinse of the present invention in the mouth after brushing, rinsing for about 30 seconds, and then exhaling.

[0027]

The oral composition of the present invention has an excellent tooth surface protection effect, is stable and has a good taste.

[0028]

The present invention will be described below in more detail with reference to examples, but the present invention is not limited to these examples. Examples 1 and 2 Mouthwashes were prepared according to the formulation shown in Table 1 and stored under the conditions shown in Table 2 to test the stability. Table 2 shows the results.
The flavor was also evaluated by the following method. Table 3 shows the results. Flavor evaluation method: Mouthwash 1 using 20 panelists
The mouth was rinsed with 0 ml for 30 seconds, and the feel at that time was evaluated on a three-point scale of ○ △ ×.
% Was rated as Δ, and less than 40% was rated as x. Comparative Example 3 is 3
Crystals are precipitated at 0 ° C. or lower. Therefore, the temperature of all samples was adjusted to 35 ° C. for evaluation.

[0029]

[Table 1]

[0030]

[Table 2]

[0031]

[Table 3]

The oral compositions of the present invention were obtained using the formulations of Examples 3 to 10. Example 3 (mouthwash)

[0033]

[Table 4]

Example 4 (Mouthwash)

[0035]

[Table 5]

Example 5 (Mouthwash)

[0037]

[Table 6]

Example 6 (Mouthwash-gel)

[0039]

[Table 7]

Example 7 (Dentifrice)

[0041]

[Table 8]

Embodiment 8

[0043]

[Table 9]

Embodiment 9

[0045]

[Table 10]

Embodiment 10

[0047]

[Table 11]

Example 11 An oil component and an aqueous component were separately dissolved and then mixed to obtain a transparent mouth rinse. The product is preferably used by brushing it with normal brushing, rinsing it in the mouth for about 30 seconds, and then exhaling.

[0049]

[Table 12]

 ────────────────────────────────────────────────── ─── Continued on the front page (72) Inventor Yuichi Hioki 1293-7, Rojuya, Wakayama City, Wakayama Prefecture JP-A-6-271440 (JP, A)

Claims (2)

(57) [Claims] 1. The following general formula (1): (Wherein, R ¹ represents a linear or branched alkyl or alkenyl group having 6 to 20 carbon atoms which may be substituted by a fluorine atom, and ^one of X ¹ and X ² represents a basic amino acid residue And the other is a hydrogen atom, an alkali metal, an ammonium, an alkylamine, an alkanolamine or a basic amino acid residue, and n is a number from 0 to 4). . 2. The following components (A) and (B): (A) the following general formula (2): (Wherein, R ¹ represents a linear or branched alkyl or alkenyl group having 6 to 20 carbon atoms which may be substituted by a fluorine atom, and Y ¹ and Y ² are the same or different and each represent a hydrogen atom, an alkali An oral composition comprising a phosphoric acid monoester represented by the following formula (B): a metal, ammonium, an alkylamine or an alkanolamine, and n represents a number from 0 to 4).