JP3088156B2 - Oral composition for preventing caries and periodontal disease - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an oral composition effective for preventing dental caries and periodontal disease.

[0002]

BACKGROUND OF THE INVENTION It has been shown that dental caries and periodontal disease are caused by dental plaque. Plaque is derived from glucosyl by using certain bacteria such as Streptococcus mutans using sucrose as a substrate. Transferase (hereinafter G
Glucan, which is a water-insoluble polysaccharide, is produced by the action of TF (abbreviated as TF), and other pathogenic bacteria (causal bacteria of periodontal disease) including Streptococcus mutans are formed around this polysaccharide. In addition, Streptococcus mutans and the like produce acids from various sugars, thereby demineralizing the enamel surface. In addition, toxins produced by bacteria can adversely affect gingiva and act as a cause of periodontal disease.

[0003] Therefore, suppressing and preventing the formation of plaque is effective for preventing dental caries and periodontal disease. As one of the means for suppressing plaque formation, there is a method for suppressing the production of glucan by GTF. Japanese Patent Application Laid-Open No. 61-216648 discloses that chitosan and the like have an effect of suppressing the production of glucan by GTF. But the effect is not enough.

[0004]

Means for Solving the Problems The inventors of the present invention have conducted intensive studies in view of the above circumstances, and as a result, it has been found that a complex in which the surface of a water-insoluble substrate coated with a water-insoluble polymer having a quaternary nitrogen inhibits GTF. The present inventors have found that the formation of plaque is extremely effectively suppressed by suppressing the formation of glucan, and the present invention has been completed.

[0005] That is, the present invention is characterized in that a complex in which the surface of a water-insoluble substrate is coated with a water-insoluble polymer having a quaternary nitrogen is blended as an active ingredient.
It is intended to provide an oral composition for preventing periodontal disease.

In the present invention, the quaternary nitrogen-containing water-insoluble polymer used for coating the surface of the water-insoluble substrate includes a molecular weight of about 1,000 to 1,000,000, preferably
About 5000 to 800,000. Examples of the water-insoluble polymer having a quaternary nitrogen include, for example, a compound represented by the general formula:

[0007]

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[Wherein A is

[0009]

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Wherein l is from 20 to 2000 and n is 100
X and Y are the same or different anions, R is an alkyl group having 6 to 18 carbon atoms, m is an integer of 2 to 10], quaternary ammonium type, betaine type, pyridyl Water-insoluble polymers having a quaternary nitrogen of the pyridinium type, diamine type or ether type are mentioned.

Specific examples of such polymers include poly
[Vinylbenzyldimethyllaurylammonium chloride], poly [vinylbenzylstearylbetaine], poly [vinylbenzyllaurylpyridylpyridinium chloride], poly [vinylbenzyllauryldiammonium chloride] and poly [vinylbenzylcetylammonylhexyl ether] are exemplified. .

The water-insoluble substrate coated with the water-insoluble polymer having a quaternary nitrogen is not particularly limited, but inorganic powders such as calcium hydrogen phosphate, calcium carbonate, alumina, silicic acid anhydride, zeolite, and polystyrene, Granular forms such as organic powders such as polyethylene and polymethyl methacrylate, and fibrous forms such as nylon floss can be used.

In order to coat the surface of these water-insoluble substrates with the water-insoluble polymer having quaternary nitrogen, for example, the following method is adopted.

[0014]

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First, a product (B) is obtained by the reaction represented by the reaction formula (1). Compound (H) is usually about 1.0 to 2.5 times mol, preferably about 1.1 to 2.1 times mol of compound (P).
It is good to make it react twice. The reaction is preferably performed in an organic solvent, and a reaction temperature of about 60 to 110 ° C is generally suitable. The product (B) can be purified by a method such as concentration, distillation, and recrystallization.

Next, by the reaction represented by the reaction formula (2),
The product (PCS) and the product (PCSDB) are obtained.
The polymerization of the reaction formula (2) can be performed by a usual method such as suspension polymerization, solution polymerization, or bulk polymerization, and the obtained polymer can be purified by a method such as reprecipitation or washing.

Next, the reaction represented by the reaction formula (3) is carried out on the surface of the water-insoluble substrate to obtain a desired complex.
In the reaction formula (3), the compound (PCS) or (P
The compound (B) is generally used in an amount of about 0.02 to 0.15 equivalent, preferably about 0.05 to 0.10, relative to 1 equivalent of CSDB) chlorine.
The reaction is preferably performed in an equivalent amount. The reaction is preferably performed in an organic solvent, and a reaction temperature of about 60 to 100 ° C is generally suitable.

In the case where a water-insoluble polymer in which the substituent represented by A in Chemical formula 1 is other than the substituent represented by Chemical formula 3 is used, it can be coated in the same manner.

The composition for oral cavity of the present invention comprises the composite obtained by coating the surface of a water-insoluble substrate thus obtained with a water-insoluble polymer having a quaternary nitrogen in an amount of about 0.1 to the total amount of the composition. 01 to 50% by weight, preferably 0.1 to 10% by weight
Mix.

The oral composition of the present invention can be prepared by a conventional method using toothpaste (eg, toothpaste, powdered toothpaste, water dentifrice, mouthwash, etc.), paste composition (eg, ointment, gingival massage cream, etc.), chewing gum The composition may be in the form of a coating such as a floss or a toothbrush, etc. In addition to the above-mentioned components, the following components may be appropriately compounded according to the form of the composition and the like.

For example, the nonionic surfactant is a fatty acid ester of a sugar or a sugar alcohol, wherein the fatty acid residue has 12 to 18 carbon atoms and an average degree of esterification of 1.1 to 2.5, preferably. 1.2 to 1.9 can be used. Examples of the fatty acid ester of the sugar or sugar alcohol include sucrose fatty acid ester, maltose fatty acid ester, maltitol fatty acid ester, maltotriitol fatty acid ester, maltotetriitol fatty acid ester, maltotetriitol fatty acid ester, maltopentai Tall fatty acid esters, maltohexaitol fatty acid esters, maltoheptitol fatty acid esters, sorbitan fatty acid esters, lactose fatty acid esters, and lactitol fatty acid esters.

In addition, as the nonionic surfactant, polyoxyethylene sorbitan monolaurate,
Polyoxyethylene sorbitan fatty acid ester such as polyoxyethylene sorbitan monostearate, polyoxyethylene hydrogenated castor oil, polyoxyethylene fatty acid ester, fatty acid ethanolamide such as lauric acid mono- or diethanolamide, fatty acid monoglyceride, polyoxyethylene higher alcohol ether , Polyoxyethylene polyoxypropylene fatty acid esters and the like can also be used.

Examples of anionic surfactants include water-soluble salts of higher alkyl sulfates having 8 to 18 carbon atoms in the alkyl group, such as sodium lauryl sulfate and sodium myristyl sulfate, α-olefin sulfonates, higher fatty acid salts. For example, sodium monoglyceride monosulfate, sodium-N-methyl-N-palmitoyl tauride, sodium-N-lauroyl-β-alanine, lauroyl sarcosinate, sodium-N-long-chain acyl basic amino acid and the like are used.

Further, as the amphoteric surfactant, for example, 2-alkyl-N-carboxymethyl-N-hydroxylethylimidazolinium betaine, alkyldiaminoethylglycine hydrochloride, betaine lauryldimethylaminoacetate and the like are used.

It should be noted that these surfactants can be used alone or in combination of two or more. Also,
The amount of the surfactant is usually 0.5% based on the whole composition.
It is from 0.01 to 5% by weight, preferably from 0.05 to 3% by weight.

The oral composition of the present invention further comprises menthol carboxylic acid, anethole, eugenol, methyl salicylate, limonene, ocimene, n-decyl alcohol, citronellol, α-terbineol, methyl acetate, citronellyl acetate, methyl Eugenol, cineol, linalool, ethyl linalool, crocodile, thymol, spearmint oil, peppermint oil, lemon oil, orange oil, sage oil, rosemary oil, cinnamon oil, pimento oil, diatom oil, perilla oil, winter green oil, cloves Oil, fragrance such as eucalyptus oil alone or in combination is 0.1 to 10% by weight, preferably 0.5 to 5% by weight based on the whole composition.
Can be blended to some degree. In addition, sweeteners such as saccharin sodium, stevioside, neoheshelidyl dihydrochalcone, glycyrrhizin, perillartin, thaumatin, asparatylphenylalanine methyl ester, p-methoxycinnamic aldehyde and the like are used in an amount of 0.01 to 1% by weight, preferably 0.05 to 1% by weight. 0.5% by weight can be blended.

For example, in the case of a paste composition such as an ointment, a cellulose derivative such as carrageenan, sodium carboxymethylcellulose, methylcellulose, hydroxyethylcellulose or sodium carboxymethylhydroxylethylcellulose, or an alkali metal alginate such as sodium alginate is used as a binder. Gums such as propylene glycol alginate, xanthan gum, xanthan gum, tragacanth gum, karaya gum, and gum arabic; synthetic binders such as polyvinyl alcohol, sodium polyacrylate, carboxyvinyl polymer, and polyvinylpyrrolidone; and inorganics such as silica gel, aluminum silica gel, veegum, and laponite. One or more kinds of binders and the like may be blended. The amount of these compounds is usually 0.3 to 5% by weight.

Further, in the production of paste or liquid oral compositions, sorbit, glycerin,
Ethylene glycol, propylene glycol, 1,3-
One or more of butylene glycol, polyethylene glycol, polypropylene glycol, xylit, maltitol, lactit and the like may be blended. The amount of these compounds is usually 10 to 70% by weight.

In the case of dentifrices, dibasic calcium phosphate dihydrate and anhydride, monobasic calcium phosphate, tribasic calcium phosphate, calcium carbonate, calcium pyrophosphate, aluminum hydroxide, alumina, silicic anhydride, silica gel, One or more of aluminum silicate, insoluble sodium metaphosphate, tribasic magnesium phosphate, magnesium carbonate, calcium sulfate, polymethyl methacrylate, bentonite, zirconium silicate, synthetic resin, and the like can be blended. The quantity is usually 5.
It is 0 to 90% by weight, and in the case of toothpaste it is 5 to 60% by weight.

In the present invention, fungicides such as cetylpyridinium chloride, chlorhexidine salts and triclosan, dextranase,
Amylase, protease, mutanase, lysozyme,
Enzymes such as lytic enzymes (Litec enzyme), alkali metal monofluorophosphates such as sodium monofluorophosphate and potassium monofluorophosphate, fluorides such as sodium fluoride and stannous fluoride, tranexamic acid and epsilon aminocaproic acid, aluminum Chlorhydroxyallantoin, dihydrocholesterol, glycyrrhizin salts, glycyrrhetinic acid, glycerophosphate, chlorophyll, sodium chloride, caropeptide,
One or more active ingredients such as a water-soluble inorganic phosphoric acid compound may be blended.

[0031]

Next, the present invention will be described more specifically with reference to experimental examples and examples, but the present invention is not limited to these examples. In addition, all "%" are weight%. Experimental Example 1 Brain Heart Infusion
The Streptococcus mutans IFO 13955 strain is cultured for 18 hours in Infusion broth, and the culture is centrifuged (6000 × g, 20 minutes, 4 ° C.) to obtain a supernatant.
Ammonium sulfate was added to the supernatant to 50% saturation, and the mixture was stirred overnight at 4 ° C. with a stirrer, and centrifuged (12,500 × g, 60 minutes, 4 minutes).
° C). The obtained sediment was used for 1/40 volume of the culture supernatant in 5 m.
A glucosyltransferase crude enzyme solution was suspended in M sodium phosphate buffer and dialyzed overnight at 4 ° C. Next, 0.4 ml of the sample dispersion shown in Table 1, 2.6 ml of a 1.5% sucrose aqueous solution and 1 ml of the above crude enzyme solution were placed in a test tube, reacted at 37 ° C. for 20 hours, and then reacted at 550 nm. Was measured for absorbance.
The index is the effect of suppressing the production of glucan, and the OD ₅₅₀ of the control was set to 100. Therefore, the smaller the value, the more effective. The compositions of the composites used in the experiments are shown in Tables 1 and 2, and the results are shown in Table 3.

[0032]

[Table 1]

[Table 2]

[0033]

[Table 3]

Example 1 In the composite 1 of Table 1, the polystyrene powder was changed to a nylon thread, and the compound (B) and the compound (PCS) were polymerized on the surface of the nylon thread to obtain a coated nylon floss. .

Example 2 Toothpaste was produced according to the following formulation according to a conventional method. Dibasic calcium phosphate dihydrate 50% glycerin 20 Sodium carboxymethyl cellulose 1.0 Fragrance 1.0 Sodium lauryl sulfate 1.0 Complex 9 (Table 2) 1.0 Saccharin sodium 1.0 Sodium fluoride 1.0 Allantoin 1.0 Water adjusted to 100%

Example 3 A water dentifrice was produced according to the following formulation according to a conventional method. Methylcellulose 3.0% Glycerin 30.0 Saccharin sodium 0.1 Fragrance 1.0 Chlorhexidine gluconate 0.01 Ethanol 3.0 Complex 5 (Table 1) 0.5 Methyl parahydroxybenzoate 0.06 Prepared in water 100%

Example 4 A gingival massage cream was produced according to the following formulation according to a conventional method. White petrolatum 8.0% propylene glycol 4.0 dextranase 1.0 stearyl alcohol 8.0 polyethylene glycol 4,000 25.0 polyethylene glycol 400 37.0 sucrose stearic acid ester 0.5 complex 3 (Table 1) 2.0) Methyl parahydroxybenzoate 0.1 water 100%

Example 5 A mouthwash was produced according to the following formulation according to a conventional method. Ethanol 10% Saccharin sodium 0.05 Fragrance 1.0 Sodium monofluorophosphate 0.1 Chlorhexidine hydrochloride 0.01 Complex 8 (Table 2) 0.5 Sucrose palmitate ester 0.5 Methyl paraoxybenzoate 0.06 Adjusted to 100% water

Example 6 A chewing gum was produced according to the following formulation according to a conventional method. Gum base Natural chicle 20 g Vinyl acetate resin 30 Ester gum 10 Wax 15 Emulsifier 5 Complex 7 (Table 2) 20 100 g

[0040]

According to the present invention, there is provided an oral composition for preventing dental caries and periodontal disease, which inhibits GTF, suppresses glucan formation, and extremely effectively suppresses plaque formation.

Continuation of the front page (56) References JP-A-5-194168 (JP, A) JP-A-5-139943 (JP, A) JP-A-5-139942 (JP, A) JP-A-60-146817 (JP) , A) JP-A-51-32743 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) A61K 7/16 A61K 7/22 A61K 31/785

Claims (1)

(57) [Claims] An oral composition for preventing dental caries and periodontal disease, comprising a complex in which the surface of a water-insoluble substrate is coated with a water-insoluble polymer having a quaternary nitrogen.