JPH0748237A - Composition for oral cavity - Google Patents

Abstract

PURPOSE:To provide a composition for oral cavity having excellent tooth surface protective effect, also highly good in feel when used. CONSTITUTION:This composition for oral cavity contains (A) 0.001-50 (esp. 0.1-5)wt.% of a phosphoric monoester of formula I(R<1> is 6-20C straight or branched alkyl or alkenyl; X<1> and X<2> are such that one of them is basic amino acid residue, the other being H, alkali metal, ammonium, alkylamine, alkanolamine or basic amino acid residue; n is 0-4) and (B) 0.001-30 (esp. 0.005-5)wt.% of a silicone, e.g. dimethylpolysiloxane, methylphenylpolysiloxane, polyethermodified silicone, pref. 200-5000 cps in viscosity. The component A may be prepared by neutralizing a mixture of (a) a compound of formula II (Y<1> and Y<2> are each H, alkali metal, ammonium, alkylamine or alkanolamine) and (b) a basic amino acid at the molar ratio b/a of 1.0-1.8.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an oral composition which contains a phosphoric acid ester and a silicone having an excellent tooth surface-protecting action and has an excellent tooth-protecting action and a feeling of use.

[0002]

2. Description of the Related Art Phosphate esters (hereinafter referred to as "AP") are less irritating and form a film on the tooth surface to improve the acid resistance of the tooth, and are excellent in suppressing plaque formation and preventing dental caries. There is. Therefore, the use of AP in oral compositions has been conventionally proposed. For example, JP-A-53-47
Japanese Patent No. 542 (USP4152421) describes a dentifrice agent which does not change the taste of foods and drinks, which contains a monoalkyl phosphate ester salt as a foaming agent;
-500061 publication (USP 4366146),
A toothpaste composition for preventing spot formation, which contains a monoalkyl phosphate as a film-forming substance, is described;
Japanese Unexamined Patent Publication No. 2-200619 (USP501937)
3) For use as toothpaste and mouthwash that do not change the taste of foods and drinks containing di-medium-chain alkyl phosphates, di-long-chain alkyl phosphates and monoalkyl phosphates with excellent anti-cariogenic activity. Suitable aqueous compositions are described; also US Pat. No. 4,036,950 describes dentifrices containing abrasives, cationic germicides and polyoxyethylene alkyl ether phosphates.

However, the taste of AP is generally bad, and there is a problem that bitterness remains especially after use. Further, when a formulation containing AP is allowed to act in the mouth, an AP-Ca salt similar to scum of Ken Ken is produced. However, there is a problem in that the tingling sensation during use is uncomfortable. However, the present inventors have found that by using a basic amino acid salt of AP, a stable oral composition with improved bad taste can be obtained, and the patent application was filed previously (Japanese Patent Application No. -24339
issue). However, even this oral composition was not sufficiently satisfactory in terms of usability.

On the other hand, as an example in which silicones are applied to an oral composition, JP-A-63-190817 (U
SP4950479), JP-A-2-200618 (USP5078988) and the like describe oral preparations in which silicone coats the surface of teeth to prevent tooth decay, plaque formation and tooth coloring.

However, even if silicone is used in these preparations, the feel is hardly improved, the coating properties are not uniform, and it is very difficult to improve the acid resistance.

[0006]

The object of the present invention is to provide an AP
Another object of the present invention is to provide a composition for oral cavity which contains a silicone and silicone and has an excellent effect of protecting the tooth surface and a feeling of use.

[0007]

Under the circumstances, as a result of intensive studies by the present inventors, when AP and silicones are used in combination, a high tooth surface protecting action is obtained due to their synergistic effect. The present invention has been completed by finding that an oral composition having the improved feeling of use can be obtained.

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

[0009]

[Chemical 3]

(In the formula, R ¹ represents a linear or branched alkyl or alkenyl group having 6 to 20 carbon atoms, and X ¹ and X
^{One of 2} represents a basic amino acid residue, the other represents a hydrogen atom, an alkali metal, ammonium, an alkylamine, an alkanolamino or a basic amino acid residue, and n represents a number of 0 to 4). The present invention provides an oral composition containing acid monoesters and silicones.

The present invention also provides the following components (A) and (B).
And (C): (A) The following general formula (2)

[0012]

[Chemical 4]

(In the formula, R ¹ represents a linear or branched alkyl or alkenyl group having 6 to 20 carbon atoms, and Y ¹ and Y
² are the same or different and represent a hydrogen atom, an alkali metal, ammonium, an alkylamine or an alkanolamine, and n is a number of 0 to 4), a phosphoric acid monoester represented by (B) a basic amino acid, (C) Silicones,
The present invention provides a composition for oral cavity containing

In the phosphoric acid monoesters (1) and (2) used in the present invention, the number of carbon atoms represented by R ¹ is 6 to 6
Examples of the linear or branched alkyl or alkenyl group of 20 include hexyl group, octyl group, decyl group, dodecyl group, tetradecyl group, hexadecyl group, octadecyl group, eicosyl group, 2-ethylhexyl group, dodecenyl group, oleyl group, Examples thereof include an elaidyl group. Of these R ¹ , an alkyl group having 8 to 20 carbon atoms, particularly 10 to 20 carbon atoms, further 12 to 16 carbon atoms, and further 14 carbon atoms is preferable. Further, these alkyl groups, alkenyl groups and the like may have a single chain length, or may be a mixture of a plurality of alkyl groups having different chain lengths.

The basic amino acid is not limited to naturally occurring arginine, lysine, and histidine, but is not limited to these, has a carboxyl group and an amino group in the molecule, is water-soluble, and has a pH of its aqueous solution. Is 7 or more. Of these, arginine is particularly preferable.

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 acid monoester (2) is subjected to alkaline conditions, desalted by electrodialysis, and neutralized with a basic amino acid (B). In the neutralization, an alkali metal salt, an amine salt, an organic amine salt or the like may be partially contained so long as it does not hinder the neutralization.
In addition, basic amino acid (B) and phosphoric acid monoester (2)
The molar ratio of (B) / (2) = 0.8 to 2.0, especially 1.
It is preferably 0 to 1.8.

In the present invention, the phosphoric acid monoesters (1) obtained as described above may be blended to form an oral composition, but the phosphoric acid monoester (2) of the above component (A) is used. And a basic amino acid of the component (B) may be blended to neutralize in the composition. In addition, component (A) and component (B)
In the case of blending both of them, the blending amount of the component (B) is a molar ratio of (B) / (A) = 0.8 to 2.0, particularly 1.0 to 1.8.
Is desirable. In this case, it is considered that the component (A) and the component (B) react with each other in the obtained composition to form the phosphoric acid monoesters (1).

In the present invention, the phosphoric acid monoesters (1) or (2) are contained in an amount of 0.001 to 50% by weight (hereinafter simply referred to as “%”), particularly 0.05 to 10% by weight in the total composition.
%, Further 0.1 to 5%, especially 0.1 to 3%,
It is preferable in terms of flavor and phase stability. If it exceeds 50%, bitterness and gelation problems tend to occur.

The silicones used in the present invention are not particularly limited as long as they are water-insoluble and have a film-forming ability, and their shapes are oil, solution, emulsion and oil. Any form such as compound can be used.

The silicones have a viscosity of 10 to 10
000cs, especially 200 to 5000cs of dimethylpolysiloxane, methylphenylpolysiloxane; silicone resin, polyether-modified silicone, etc. are preferred, and 1
It is also possible to use a high degree of polymerization dimethylpolysiloxane having a 0% solution concentration of 1,000 to 10,000 cs.

Further, it is particularly preferable to use these silicones as an emulsion type (O / W type) obtained by emulsifying with water using various emulsifiers in order to obtain the effects of the present invention. Examples of such a silicone emulsion include a silicone resin emulsion KM72F (manufactured by Shin-Etsu Chemical Co., Ltd.) and a methylpolysiloxane emulsion K.
Commercially available products such as M880 (produced by Shin-Etsu Chemical Co., Ltd.) can be used.

These silicones have a composition of 0.
001 to 30%, especially 0.001 to 10%, and further 0.0
A blending amount of 05 to 5% is preferable in terms of feel and phase stability. If it exceeds 30% by weight, the feel and the problem of silicone separation are likely to occur.

In addition to the above-mentioned essential components, the oral composition of the present invention contains an oral vehicle that is generally used within a range that does not impair the effects of the present invention, and a toothpaste, powder toothpaste, liquid toothpaste,
It can be in the form of mouthwash, mouthwash, mouthrinse, gum massage cream, oral troche, chewing gum, candy and the like. Of these forms, mouthwash, mouthrinse,
Liquid composition of mouthwash, toothpaste, powdered toothpaste, liquid toothpaste,
A solid or pasty composition such as a gum massage cream and an oral troche is preferable. Such oral vehicles include abrasives, binders, wetting agents, surfactants, fragrances, sweeteners, preservatives, pigments, water, bactericides, water-soluble fluorides, and other active ingredients. .

Here, as the abrasive, calcium hydrogen phosphate for polishing, calcium carbonate, calcium pyrophosphate, insoluble sodium metaphosphate, potassium metaphosphate, silicic acid anhydride, hydrous silicic acid, aluminum silicate, zirconium silicate, bentonite, zeolite , Aluminum oxide, aluminum hydroxide, resins and mixtures thereof. Among these, silicic acid anhydride, hydrous silicic acid, aluminum hydroxide, calcium carbonate, and zeolite are particularly preferable. Examples of the binder include sodium carboxymethyl cellulose, methyl cellulose, hydroxyethyl cellulose, alginate, carrageenan, gum arabic, polyvinyl alcohol, tragacanth gum, starch, sodium polyacrylate and the like. As a wetting agent,
Examples thereof include polyethylene glycol, propylene glycol, sorbitol, glycerin, maltitol, xylitol and the like. Of these, glycerin, sorbitol and the like are preferable.

The surfactant is used as a foaming agent or a stabilizer for an oily substance, and various surfactants other than the phosphoric acid ester are used. Examples of preferable 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 ester, alkyl glycosides, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, alkyldimethylamine oxide, carbobetaine, hydroxycarbobetaine, phosphobetaine, hydroxyphosphobetaine, sulfobetaine, hydroxysulfobetaine, etc. To be Of these, polyoxyethylene hydrogenated castor oil, polyoxyethylene polyoxypropylene block copolymer, sucrose fatty acid ester, alkyl glycosides, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester and other water-soluble nonionic surfactants and amphoteric Surfactants are especially preferred.

As the fragrance, natural fragrances such as spearmint oil, peppermint oil, wintergreen oil, sassafras oil, clove oil, sage oil, eucalyptus oil, mayonnaise oil, cinnamon oil, thyme oil, lemon oil and orange oil; and l-
Examples thereof include synthetic fragrances such as menthol, anethole, carvone, eugenol, thymol, methyl salicylate.
Examples of the sweetener include saccharin, saccharin sodium, stevioside, neohesperidyl dihydrochalcone, berlartine, p-methoxycinnamic aldehyde, glycyrrhizinate, aspartame (aspartylphenylalanine methyl ester) and the like. As bactericides, chlorhexidines, quaternary ammonium salts,
Examples include triclosan and alkyldiaminoethylglycine hydrochloride. Examples of antiseptics include benzoic acid, sodium benzoate, parahydroxybenzoic acid ester, salicylic acid, sodium salicylate, sorbic acid, and isopropylmethylphenol. 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 esters, allantoin chlorohydroxyaluminum, azulene, lysozyme chloride, hinokitiol, β-glycyrrhetinic acid, dipotassium glycyrrhizinate, proteases, crude drug extracts, etc. Is mentioned.

The blending amount of these oral vehicles differs depending on the form of the oral composition, and in the case of a liquid composition, the liquid composition contains an abrasive, among the above-mentioned oral vehicles,
All vehicles except binders can be blended, but basically phosphate monoesters (1) or (2) should be 0.05
-10%, silicones 0.05-5%, wetting agent 1
-30%, alcohol and water 50-96% are preferable. The weight ratio of water: alcohol is preferably 1: 1 to 200: 1, and more preferably 5: 1 to 100: 1. It is preferable to add 1 to 20% of alcohol in the total composition.

In the case of a paste-like composition, all of the above-mentioned oral vehicles can be blended, but basically, phosphate ester (1) or (2) is added in an amount of 0.05 to 10%, and silicones are added. It is preferable to contain 0.005 to 5%, an abrasive to 10 to 75%, a binder to 0.5 to 5%, and a wetting agent and water to 10 to 85%. Here, the abrasive is preferably 20 to 75% for toothpaste and 10 to 30% for liquid toothpaste. Further, in the case of a solid composition such as toothpaste,
Solid components of the vehicle for oral cavity can be blended, but basically 0.05% of phosphoric acid ester (1) or (2) is used.
10 to 10%, 0.005 to 10% of silicones, and 60 to 99% of an abrasive are preferably blended.

Of the vehicle for oral cavity, it is preferable to add 0.01 to 5% of the flavor and the sweetener in total. The pH of the oral composition of the present invention is 5 to 9.5, particularly 6 to 8.
It is preferably within the range.

Of the oral compositions of the present invention, a solid composition such as powdered dentifrice can be usually prepared by mechanically mixing the above solid components and silicones. The paste composition can be usually 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 is regularly added.
It is preferably applied 1 to 3 times daily. Among the oral compositions, mouth rinse is most preferable, and after brushing, the mouth rinse contains about 10 ml of the mouth rinse of the present invention, rinsed for about 30 seconds, and then spit out, whereby the tooth surface can be well protected.

[0032]

EFFECTS OF THE INVENTION The oral composition of the present invention has an excellent effect of protecting the surface of teeth and has a very good feeling in use.

[0033]

The present invention will be described in more detail below with reference to examples, but the present invention is not limited thereto.

Example 1 A mouthwash was prepared according to the formulation shown in Table 1 and the feeling of use was tested by the following method. The results are shown in Table 2. Further, the tooth surface protecting action was also evaluated by the following method. The results are shown in Table 3.

(Evaluation of the feeling of use) 20 panelists were asked to rinse the mouthwash with 10 ml of the mouthwash for 30 seconds, and the overall evaluation at that time (do you like the mouthwash), the feel of the mouth (of the mouthwash) Do you like the feel), are your teeth slippery (which is better),
If you have a squeaky feeling in your mouth (it's better not),
The evaluation was made in three grades of ◯, Δ and ×. For each item, the number of ○ is 60% or more, ○, 30% or more and less than 60% is △, 30%
Less than is shown in Table 2 as x.

(Evaluation of Tooth Surface Protecting Effect) 10 ml of mouthwash and bovine teeth were treated in the human mouth for 30 seconds and then decalcified with a lactic acid buffer solution of pH 4.0. Tooth hardness at that time (dentin)
Was measured with time using a Vickers hardness meter (Load: 10 g). When the hardness was decreased by less than 10% after 6 hours from the start of the measurement, the hardness was evaluated as ○, the deterioration of 10% or more and less than 20% was evaluated as Δ, and the deterioration of 20% or more was evaluated as ×.

[0037]

[Table 1]

[0038]

[Table 2]

[0039]

[Table 3]

Hereinafter, the oral compositions of the present invention were obtained according to the formulations of Examples 2 to 6.

Example 2 (Mouthwash)

[Table 4] Sorbit solution 15.0 (%) Ethanol 5.0 Monoalkyl phosphoric acid (C14) 0.5 Polyoxyethylene (EO = 60) Hardened castor oil 0.2 Silicone emulsion (KM72F; Shin-Etsu Chemical Co., Ltd.) 0.3 Methyl p-hydroxybenzoate 0.05 l-Arginine 0.4 Chlorhexidine hydrochloride 0.05 Perfume 0.2 Purified water Balance 100.0 (%)

Example 3 (Mouthwash)

[Table 5] Sorbit solution 10.0 (%) Ethanol 4.0 Monoalkyl phosphoric acid (C14) 0.4 Silicone emulsion (Methyl polysiloxane emulsion KM880; Silicone content about 85%; Shin-Etsu Chemical Co., Ltd.) 0 .1 l-arginine 0.4 p-hydroxybenzoic acid butyl 0.1 benzalkonium chloride 0.05 fragrance 0.15 l-menthol 0.05 purified water balance 100.0 (%)

Example 4 (Mouthwash)

[Table 6] Sorbit solution 5.0 (%) Glycerin 5.0 Ethanol 5.0 Monoalkyl phosphoric acid (C14) 0.2 Polyoxyethylene (EO = 60) Hardened castor oil 0.1 Silicone emulsion (KM72F Manufactured by Shin-Etsu Chemical Co., Ltd.) 0.1 isopropylmethylphenol 0.1 l-lysine 0.18 chlorhexidine hydrochloride 0.01 sodium fluoride 0.05 fragrance 0.1 purified water balance 100.0 (%)

Example 5 (dentifrice)

[Table 7] Aluminum hydroxide 30.0 (%) Solbit solution 35.0 Propylene glycol 5.0 PEG600 2.0 Silicone emulsion [Emulsion containing 30% of methylphenyl polysiloxane (KF50; Shin-Etsu Chemical Co., Ltd.)] 1.0 Sodium benzoate 0.2 Sodium saccharin 0.1 Sodium monofluorophosphate 0.7 Silicic anhydride 5.0 Monoalkylphosphoric acid (C12) 1.5 Hydroxyethyl cellulose 0.8 l-Arginine 1.2 Glycyrrhetinic acid 0.1 Perfume 0.9 Purified water Balance 100.0 (%)

Example 6 (dentifrice)

Table 8 Hydrous silicic acid 30.0 (%) Sorbit solution 30.0 Glycerin 5.0 PEG600 3.0 Sodium benzoate 0.2 Silicone emulsion [Polyether-modified silicone (KS506; manufactured by Shin-Etsu Chemical Co., Ltd.) 60] % Emulsion] 2.0 Saccharin sodium 0.1 Sodium fluoride 0.2 Silicic anhydride 15.0 Monoalkyl phosphoric acid (C12) arginine salt ^* 1.5 Carboxymethyl cellulose 1.0 Perfume 0.9 Purified water Balance 100.0 (%) *: Arginine / monoalkyl phosphoric acid = 1.3 (molar ratio)

Claims (4)

[Claims] 1. The following general formula (1): (In the formula, R ¹ represents a linear or branched alkyl or alkenyl group having 6 to 20 carbon atoms, ^one of X ¹ and X ² represents a basic amino acid residue, the other represents a hydrogen atom, an alkali metal, An oral composition containing a phosphoric acid monoester represented by ammonium, an alkylamine, an alkanolamine or a basic amino acid residue, and n representing a number of 0 to 4, and a silicone. 2. The oral composition according to claim 1, wherein the silicones are in an emulsion form. 3. The following components (A), (B) and (C): (A) The following general formula (2): (In the formula, R ¹ represents a linear or branched alkyl or alkenyl group having 6 to 20 carbon atoms, Y ¹ and Y ² are the same or different, and are a hydrogen atom, an alkali metal, ammonium, an alkylamine or an alkanolamine. And n is 0 to
A phosphoric acid monoester represented by 4),
An oral composition containing (B) a basic amino acid and (C) a silicone. 4. The oral composition according to claim 3, wherein the silicones are in an emulsion form.