JPH09175965A - Suppressing agent for plaque formation and composition for oral cavity - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtaiix the subject composition excellent in suppressing effect for bacterial adhesion to the surface of a tooth, capable of effectively inhibiting the formation of a plaque and effectively utilized for the prevention of a diseases in an oral cavity. SOLUTION: This suppressing agent for a plaque formation is obtained by blending a polymer selected from a homopolymer of dimethyldiallylammonium chloride and a copolymer of dimethyldiallylammonium chloride with at least one kind of polymerizable monomer having an ethylenically unsaturated hydrocarbon bond, and a betaine-type surfactant.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a plaque formation inhibitor and an oral composition containing the same.

[0002]

2. Description of the Related Art
The following are proposals relating to oral compositions using a technique of suppressing adhesion of microorganisms and inhibiting plaque formation by coating the tooth surface with a specific drug or the like. Oral composition containing a polyamino acid sulfonate polymer (JP-A-58-93725) Oral composition containing a sulfonated vinyl aromatic polymer (JP-A-59-88416) Polyvinyl sulfonic acid and vehicle Anti-plaque oral composition containing a perfluoroalkyl surfactant and a vehicle (JP-A-1-96115) Acrylic acid polymer was added Oral composition (JP-A-3-14511) Composition for oral cavity containing a specific peptide (JP-A-3-14511)
No. 261717 and No. 3-261718) Oral composition containing a fluoroalkyl phosphate ester (JP-A-3-38517) Composition for oral cavity containing a silicone derivative (JP-A-4)
No. 120014) Oral composition in which a specific alkyl betaine is blended (Japanese Patent Laid-Open No. 4-134025) However, all of the agents blended in the oral composition for the purpose of suppressing plaque formation are microbial. It cannot be said that the effect of suppressing the adhesion to the tooth surface is sufficiently satisfied, and therefore, the development of a plaque formation inhibitor having a higher effect of suppressing the adhesion is desired.

[0003] The present invention has been made in view of the above circumstances,
It is an object of the present invention to provide a plaque formation inhibitor which has an excellent effect of suppressing the adhesion of microorganisms to the tooth surface and which can effectively prevent plaque formation, and an oral composition containing the same.

[0004]

Means for Solving the Problems and Modes for Carrying Out the Invention The present inventor has conducted extensive studies to achieve the above object, and as a result, at least one of dimethyldiallylammonium chloride homopolymer and dimethyldiallylammonium chloride was obtained.
Surprisingly, when a tooth surface is coated with a polymer selected from copolymers of polymerizable monomers having ethylenically unsaturated hydrocarbon bonds and a betaine-type surfactant, the adhesion of microorganisms is surprisingly effective. It suppresses plaque formation and exerts satisfactory plaque formation prevention effect. Therefore, by using dimethyldiallylammonium-containing polymer and betaine-type surfactant, plaque formation is suppressed and oral diseases are prevented (caries prevention). It was found that a plaque formation inhibitor effective for prevention of periodontal disease) can be obtained, and the present invention has been completed.

The above dimethyldiallylammonium-containing polymer is blended as a coating material in hair cosmetics, skin care cosmetics, etc. (JP-A-63-1).
No. 22613, No. 63-132814, Japanese Patent Laid-Open No. Hei 5
It is known that when it is blended with a toothpaste composition, it has excellent shape retention (Japanese Patent Laid-Open No. Sho 60-60).
-1116), it has not been previously known that such a polymer has the above-mentioned excellent effects by using it in combination with a betaine-type surfactant, and that it is used as a plaque formation inhibitor. It is a new finding by the person.

Therefore, the present invention provides a plaque formation inhibitor comprising the above polymer and a betaine type surfactant, and an oral composition containing the plaque formation inhibitor.

The present invention will be described in more detail below. The plaque formation inhibitor of the present invention comprises a homopolymer of dimethyldiallylammonium chloride and a polymerization having dimethyldiallylammonium chloride and at least one ethylenically unsaturated hydrocarbon bond. It is characterized by comprising a polymer selected from copolymers with possible monomers and a betaine type surfactant.

Here, the dimethyldiallylammonium-containing polymer is a homopolymer obtained by polymerizing dimethyldiallylammonium chloride represented by the following structural formula (1), or has dimethyldiallylammonium chloride and an ethylenically unsaturated hydrocarbon bond. It is a copolymer obtained by copolymerizing at least one kind of a polymerizable monomer. In this case, the polymerizable monomer having an ethylenically unsaturated hydrocarbon bond is preferably one represented by the following structural formula (2).

[0009]

Embedded image (However, in the formula, R ¹ represents a COOH group or a CONH ₂ group.
R ² is a hydrogen atom or a lower alkyl group having 1 to 5 carbon atoms such as a methyl group. )

As the polymerizable monomer having an ethylenically unsaturated hydrocarbon group of the above formula (2), acrylic acid, methacrylic acid, acrylamide, etc. are preferable.

Specific examples of such a dimethyldiallylammonium chloride-containing polymer include Mercoat (trade name) manufactured by Calgon Co., Ltd., such as Mercoat 100, which is a homopolymer of dimethyldiallylammonium chloride, and dimethyldiallylammonium chloride. Mercoat 280 which is a copolymer with acrylic acid, Mercoat 550 which is a copolymer of dimethyldiallylammonium chloride and acrylamide, and Mercoat Plus 3330 which is a three-component copolymer of dimethyldiallylammonium chloride and acrylic acid and acrylamide (see the following structural formula) Etc.

[0012]

Embedded image

On the other hand, as the betaine-type surfactant, a linear one represented by the following structural formula (3) and any one of the following structural formulas (4), (5) and (6), or a combination thereof The mixture of imidazolium type betaine and salts thereof can be effectively used.

[0014]

Embedded image

However, in the formula, R ³ is an alkyl group having 8 to 20 carbon atoms, an alkenyl group, a fatty acid amide alkyl group, R ⁴ ,
R ⁵ is an alkyl group having 1 to 3 carbon atoms, A is a carboxyl group, a sulfonyl group or a phosphonyl group, and n is 1 to 4. R ⁶ is an alkyl group having 5 to 19 carbon atoms, an alkenyl group, a fatty acid amidoalkyl group, and R ⁷ is a hydroxyalkyl group having 1 to 4 carbon atoms or a carboxyalkoxyalkyl group having 3 to 6 carbon atoms.

These betaine type surfactants include:
Octyl dimethylamino acetic acid betaine, decyl dimethyl amino acetic acid betaine, lauryl dimethyl amino acetic acid betaine, myristyl dimethyl amino acetic acid betaine, palmityl dimethyl amino acetic acid betaine, stearyl dimethyl amino acetic acid betaine, oleyl dimethyl amino acetic acid betaine, octanoic amide propyl betaine, decane Acid amidopropyl betaine, lauric acid amidopropyl betaine, myristic acid amidopropyl betaine, palmitic acid amidopropyl betaine, stearic acid amidopropyl betaine, oleic acid amidopropyl betaine, hexanoic acid amidopropyl betaine, 2-nonyl-N-hydroxyethyl- N-carboxymethyl imidazolinium betaine, 2-undecyl-N-hydroxyethyl-
N-carboxymethyl imidazolinium betaine, 2-
Tridecyl-N-hydroxyethyl-N-carboxymethyl imidazolinium betaine, 2-pentadecyl-N
-Hydroxyethyl-N-carboxymethylimidazolinium betaine, 2-heptadecyl-N-hydroxyethyl-N-carboxymethylimidazolinium betaine, 2-nonyl-N-carboxyethoxyethyl-N-
Carboxymethylimidazolinium betaine, 2-undecyl-N-carboxyethoxyethyl-N-carboxymethylimidazolinium betaine, 2-tridecyl-
N-carboxyethoxyethyl-N-carboxymethylimidazolinium betaine, 2-pentadecyl-N-carboxyethoxyethyl-N-carboxymethylimidazolinium betaine, 2-heptadecyl-N-carboxyethoxyethyl-N-carboxymethylimidazoline Nium betaine, decyl dimethyl amino propane sulfonate, lauryl dimethyl amino propane sulfonate,
Myristyl dimethylamino propane sulfonate, palmityl dimethyl amino propane sulfonate, stearyl dimethyl amino propane sulfonate, decyl dimethyl amino-2-hydroxy propane sulfonate, lauryl dimethyl amino-2-hydroxy propane sulfonate, myristyl dimethyl amino-2-hydroxy propane sulfonate, pal Examples thereof include mityl dimethylamino-2-hydroxypropane sulfonate, stearyl dimethylamino-2-hydroxypropane sulfonate and salts thereof. As salts, Na, K, NH ₄ , M
g and the like. These betaine-type surfactants have 1
They may be used alone or in combination of two or more.

The mixing ratio of the dimethyldiallylammonium-containing polymer and the betaine-type surfactant is appropriately selected.
It is preferable that the amount is 5 to 99.5 parts by weight, particularly 5 to 95 parts by weight, and the betaine-type surfactant is 99.5 to 0.5 parts by weight, especially 95 to 5 parts by weight.

The oral composition of the present invention contains the above-mentioned plaque formation inhibitor. In this case, the amount of the dimethyldiallylammonium-containing polymer blended is 0.00 based on the total composition.
01 to 5% by weight, particularly 0.001 to 1% by weight is preferable, and if it is less than 0.0001% by weight, a sufficient effect may not be obtained, and if it exceeds 5% by weight, the viscosity becomes high and the usability is impaired. In some cases, the amount of the betaine surfactant added is 0.0001 to 5% by weight, more preferably 0.001 to 2% by weight, based on the total weight of the composition.

The oral composition of the present invention is prepared and applied as toothpaste such as toothpaste and liquid toothpaste, mouthwash, mouthwash, chewing gum and the like. In addition to the components, any appropriate component may be added depending on the dosage form. Specifically, toothpaste such as toothpaste, crystalline silica, amorphous silica, as an abrasive,
Other silica-based abrasives, aluminosilicate, aluminum oxide, aluminum hydroxide, insoluble sodium metaphosphate, insoluble potassium metaphosphate, titanium oxide, dibasic calcium phosphate dihydrate, heavy calcium carbonate,
Light calcium carbonate (usually 3 to 99% by weight),
Carrageenan, carboxymethyl cellulose, methyl cellulose, hydroxymethyl cellulose as a binder,
Cellulose derivatives such as sodium carboxymethyl hydroxymethyl cellulose, alkali metal alginates such as sodium alginate, propylene glycol alginate, xanthan gum, tragacanth gum, karaya gum, gums such as gum arabic, polyvinyl alcohol, sodium polyacrylate, carboxyvinyl polymer, polyvinylpyrrolidone Synthetic binders such as, gelling silica, gelling aluminum silica, inorganic binders such as veganto and laponite (usually 0.5 to 10% by weight), sorbit, glycerin, ethylene glycol as thickeners , Propylene glycol, 1,3-butylene glycol, polyethylene glycol, polypropylene glycol, xylit, maltite, lactit, etc. It can be blended by weight%).

Examples of the surfactant include sodium lauryl sulfate, sodium α-olefinsulfonate, sodium dodecylbenzenesulfonate, sodium laurylsulfoacetate, sodium N-lauroylsarcosinate, N-acylglutamate and sucrose. Fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxyethylene polyoxypropylene block copolymer, alkyl glycosides, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, alkyl dimethylamine oxide, etc., and the compounding amount is usually 0
~ 5% by weight.

Further, as optional components, for example, saccharin sodium, stevioside, neohesperidyl dihydrochalcone, glycyrrhizin, perillartine, thaumatin, asparatyl phenylalanine methyl ester, p
-Methoxycinnamic aldehyde, sucrose, fructose, sweeteners such as sodium cyclamate, spearmint oil,
Peppermint oil, wintergreen oil, sassafras oil, clove oil, eucalyptus oil, sage oil, mayard oil,
Perfume such as thyme oil, lemon oil, orange oil, 1-menthol, carvone, anethole, eugenol, thymol, methyl salicylate, benzoic acid, sodium benzoate,
Preservatives such as p-hydroxypropylbenzoic acid, p-hydroxybutylbenzoic acid, lower fatty acid monoglyceride, quaternary ammonium salts, triclosan, fungicides such as alkyldiaminoethylglycine hydrochloride, epsilon aminocaproic acid, tranexamic acid,
Enzymes such as dextranase, amylase, protease, mutanase, lysozyme, lytic enzyme, retechenzyme, sodium monofluorophosphate, potassium monofluorophosphate, sodium fluoride, ammonium fluoride, stannous fluoride and other fluorides , Chlorhexidine salts, dihydrocholesterol, glycyrrhetin salts, glycyrrhetinic acid, chlorophyll, caropeptide, vitamins, azulene, lysozyme chloride, anticalculus agent, antiplaque agent, potassium nitrate, aluminum lactate and the like can be added. In addition, the addition amount of these optional components can be a normal amount as long as the effect of the present invention is not hindered.

[0022]

The plaque formation inhibitor of the present invention has an excellent effect of inhibiting the adhesion of microorganisms to the tooth surface and can effectively prevent the formation of plaque, and it can be effectively used for the prevention of oral diseases. You can

[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 1] As an experiment for suppressing the adhesion of microorganisms to the tooth surface, the components shown in Table 1 were applied to the saliva-coated hydroxyapatite plate Streptococcus sanguis ATC.
The adhesion suppressing effect of C10558 was evaluated by the following method. The results are shown in Table 1. (1) A hydroxyapatite piece (manufactured by Asahi Optical Co., Ltd.) was used as a tooth model and immersed in human filtered saliva at 37 ° C. for 2 hours. (2) After dipping in the following sample for 30 minutes, it was washed with distilled water. (3) 0.05M · KCl, 1mM · KH ₂ PO ₄ , 1m
PH 7.0 consisting of M · CaCl ₂ , 1 mM MgCl ₂
After immersing in the above-mentioned bacterial solution (OD ₅₅₀ = 0.1) dispersed in the above buffer solution at 37 ° C. for 18 hours, it was stained with fuchsin, and the cell adhesion area was calculated by image analysis. (4) The bacterial cell attachment inhibition rate relative to the control was calculated according to the following formula.

[0025]

[Equation 1]

From the results shown in Table 1, it was confirmed that the polymer selected from the group consisting of the dimethyldiallylammonium chloride-containing polymer of the present invention and the copolymer of dimethyldiallylammonium chloride and at least one polymerizable monomer having an ethylenically unsaturated hydrocarbon bond. It was confirmed that the inclusion of the betaine-type surfactant has an excellent effect of suppressing the adhesion of microorganisms to the tooth surface.

[0027]

[Table 1]

[Example 1] Toothpaste Aluminum hydroxide 45% by weight Sorbit 30 Sodium lauryl sulfate 0.8 Sodium alginate 0.6 Xanthan gum 0.3 Sodium saccharin 0.1 Myristic acid diethanolamide 1.6 Propylene glycol 5 Perfume 1. 3 Marcoat 280 0.05 Lauryl dimethylamino acetic acid betaine 0.05 Water Residual 100.0% by weight

Example 2 Toothpaste Dicalcium Phosphate Dihydrate 50% by Weight Solbit 30 Sodium Lauryl Sulfate 0.8 Sodium Alginate 0.6 Xanthan Gum 0.3 Sodium Saccharin 0.1 Myristic Acid Diethanolamide 1.6 Propylene Glycol 5 Perfume 1.3 Marquat 280 0.05 Coconut oil fatty acid amidopropyldimethylaminoacetic acid betaine 0.05 Water Residual 100.0% by weight

[Example 3] Toothpaste Silica 20% by weight Sorbit 60 Sodium lauryl sulfate 0.9 Sodium saccharin 0.15 Polyoxyethylene hydrogenated castor oil 1.5 Propylene glycol 5 Perfume 1.5 Xanthan gum 0.5 Sodium fluoride 0 .1 Polyoxyethylene glycol # 4000 0.5 Mercoat 100 0.02 2-Undecyl-N-carboxymethyl-N-hydroxy 0.02 Ethylimidazolinium betaine water Residual total 100.0% by weight

[Example 4] Liquid dentifrice Silica 18% by weight Sorbit 55 Sodium lauryl sulfate 1 Sodium saccharin 0.1 Myristic acid diethanolamide 1.2 Propylene glycol 2 Perfume 1.4 Glycerin 18 Xanthan gum 0.1 Decaglyceryl laurate 0. 5 Sodium sulfate (anhydrous) 0.3 Mercoat 280 0.05 Palmityl dimethylamino-2-hydroxypropane 0.05 Sulfonate water Residual 100.0% by weight

[Example 5] Mouthwash Denatured ethanol 1.6 wt% Polyoxyethylene hydrogenated castor oil 2 Citric acid 0.01 Trisodium citrate 0.3 Saccharin sodium 0.1 Merquat 280 0.1 2-Undecyl- N-hydroxyethyl-N-carboxy 0.1 Methyl imidazolinium betaine Fragrance 0.5 Glycerin 10 Water Residual amount 100.0 wt%

Example 6 Mouthwash Ethanol 10% by weight Sodium saccharin 0.05 Sodium monofluorophosphate 0.05 Chlorohexidine gluconate 0.01 Dye 0.01 Sodium benzoate 0.05 Antioxidant 0.01 Perfume 0.3 Marquat 100 0.02 Lauryldimethylaminoacetic acid betaine 0.25 POE sodium myristyl sulfate 0.3 Water balance 100.0% by weight

[Example 7] Mouthwash 90% ethanol 20% by weight polyoxyethylene (80 mol) sorbitan monotaurate 0.5 Perfume 1.5 Marquat 100 0.05 Lauryl dimethylamino acetic acid betaine 0.01 Triclosan 0. 05 Lauroyl sarcosine sodium 0.05 Water residual 100.0% by weight

[Example 8] Chewing gum Gum base 20% by weight Fragrance 1 Triclosan 0.01 Lauroyl sarcosine sodium 0.01 Calcium carbonate 2 Starch candy 15 Sugar 58 Marquat 550 0.05 Lauryl dimethylamino acetic acid betaine 0.02 Water balance 100 0.0% by weight

Claims (2)

[Claims] 1. A polymer selected from a homopolymer of dimethyldiallylammonium chloride and a copolymer of dimethyldiallylammonium chloride and at least one polymerizable monomer having an ethylenically unsaturated hydrocarbon bond, and a betaine-type surfactant. A plaque formation inhibitor characterized in that 2. An oral composition comprising the plaque formation inhibitor according to claim 1.