JP6988463B2 - Microbial adhesion inhibitor for tooth surface - Google Patents

Description

The present invention relates to a microbial adhesion inhibitor for tooth surfaces, which has excellent microbial adhesion inhibitory performance.

Dental plaque is an aggregate composed of microorganisms adhering to the tooth surface and an intercellular substrate, and causes oral diseases such as dental caries and periodontal disease. Therefore, preventing dental plaque from forming on the tooth surface is a measure to prevent dental caries. Most of the enamel that constitutes the tooth surface has a calcium phosphate-based structure called hydroxyapatite. Therefore, it is known that the tooth surface has different properties from the material used in dental prostheses, and has high adsorptivity for proteins, amino acids, sugars, etc. due to electrostatic interaction and hydrogen bond interaction with hydroxyl groups. It is considered to be a place where dental plaque is likely to form (Non-Patent Documents 1 and 2).

Patent Document 1 is characterized in that a phosphorylcholine group-containing polymer is used as a microorganism adhesion-preventing component, a water-soluble polysaccharide is used as a binder component, and a poly (meth) acrylic acid derivative is used as a compatibilizing component. Inhibitors are disclosed.

Japanese Unexamined Patent Publication No. 2011-153101

Akira Yamamoto et al., "Application of Hydroxyapatite Surfaces in Bio-Industry and Future Challenges", Journal of Japan Crystal Growth Society, Vol. 33, No. 5, pp.388-394, 2006 Hideki Aoki et al., "Amazing Biomaterials Apatite and Surface Technology", Surface Technology, Vol. 58, No. 12, pp.744-750, 2007

In the oral microbial adhesion inhibitor described in Patent Document 1, a water-soluble polysaccharide is blended as a binder component and a poly (meth) acrylic acid derivative is blended as a compatibilizing component in order to retain the phosphorylcholine group-containing polymer in the oral cavity. It was necessary to do so, and it was not always easy for the user to use.
The subject of the present invention has been made in view of the above-mentioned conventional problems, and it is possible to attach a microbial adhesion inhibitor to the tooth surface without using a binder component, and it has excellent microbial adhesion inhibitory performance. It is to provide the microbial adhesion inhibitor for the tooth surface which has.

As a result of diligent studies to solve the above-mentioned conventional problems, the present inventors have provided a tooth surface microbial adhesion inhibitor containing a specific amount of a copolymer having two specific structural units. We have found that it is possible to suppress the adhesion of microorganisms to the tooth surface without using a binder or the like, and have completed the present invention.

That is, the gist of the present invention is the following [1] to [4].
[1] A copolymer having a structural unit represented by the following general formula (1) and a structural unit represented by the following general formula (2) is contained, and the content of the copolymer is 0.003% by mass. A microbial adhesion inhibitor for tooth surfaces having a mass of 1% by mass or more.

（一般式（１）において、Ｒ¹は水素原子又はメチル基を表し、ｎは１〜４の整数を表す。）

(In the general formula (1), R ¹ represents a hydrogen atom or a methyl group, and n represents an integer of 1 to 4).

（一般式（２）において、Ｒ^２は水素原子又はメチル基を表し、Ｌ^１は、−Ｃ_６Ｈ_４−、−Ｃ_６Ｈ_１０−、−（Ｃ＝Ｏ）−Ｏ−、−（Ｃ＝Ｏ）−ＮＨ−、又は−Ｏ−（Ｃ＝Ｏ）−から選ばれる２価の基を表し、Ｌ^２は炭素数１０〜２２のアルキル基を表す。）

(In the general formula (2), ^{R 2} represents a hydrogen atom or a methyl group, ^{L 1} _{is, -C 6 H 4 -, -} C 6 H 10 -, - (C = O) -O -, - (C = O) -NH- or -O- (C = O) ^{-represents a divalent group, and L 2} represents an alkyl group having 10 to 22 carbon atoms.)

[2] The microbial adhesion inhibitor for tooth surface according to the above [2], wherein the copolymer is a (glycerylamide ethyl methacrylate / stearyl methacrylate) copolymer.
[3] The microbial adhesion inhibitor for tooth surface according to the above [1] or [2], which further contains a wetting agent composed of a polyhydric alcohol.
[4] The microbial adhesion inhibitor for tooth surface according to the above [3], wherein the content of the wetting agent is 0.01 to 50% by mass.

According to the microbial adhesion inhibitor for tooth surface of the present invention, the microbial adhesion inhibitor can be adhered to the tooth surface without using a binder component, and the tooth surface has excellent microbial adhesion inhibitory performance. A microbial adhesion inhibitor can be provided.

Hereinafter, the present invention will be described in more detail.
In addition, in this specification, "(meth) acrylate" means "acrylate or methacrylate", and the same applies to other similar terms.
Further, in the present specification, when a preferable numerical range (for example, a range of content or weight average molecular weight) is described stepwise, each lower limit value and upper limit value can be independently combined. For example, in the description "preferably 10 or more, more preferably 20 or more, and preferably 100 or less, more preferably 90 or less", "preferable lower limit value: 10" and "more preferable upper limit value: 90" are combined. Therefore, it can be set to "10 or more and 90 or less". Further, for example, even in the description of "preferably 10 to 100, more preferably 20 to 90", it can be similarly set to "10 to 90".

[Microbial adhesion inhibitor for tooth surface]
The microbial adhesion inhibitor for tooth surface of the present invention contains a copolymer having a structural unit represented by the following general formula (1) and a structural unit represented by the following general formula (2), and the copolymer. The content of is 0.003% by mass or more and 1% by mass or less, and the adhesion of microorganisms to the tooth surface can be effectively suppressed. Therefore, it is possible to prevent caries and periodontal disease of the user. It will be possible.

Hereinafter, the constitution of the copolymer will be described in detail.
<Structural unit represented by the general formula (1) [Structural unit (1)]>

（一般式（１）において、Ｒ¹は水素原子又はメチル基を表し、ｎは１〜４の整数を表す。）

(In the general formula (1), R ¹ represents a hydrogen atom or a methyl group, and n represents an integer of 1 to 4).

In the general formula (1), R ¹ represents a hydrogen atom or a methyl group, and a methyl group is preferable from the viewpoint of improving the storage stability of the copolymer.
Further, in the general formula (1), n represents an integer of 1 to 4, and from the viewpoint of availability of raw materials, n is preferably 1 to 3 and more preferably 1 to 2.

The compound as a raw material of the structural unit represented by the general formula (1) can be produced by a known method. For example, a compound obtained by subjecting an acetalized form of glycerin and a (meth) acrylate having an isocyanate group to a urethanization reaction in the presence of a urethanization reaction catalyst is prepared by water in the presence of a hydrolysis catalyst. It can be produced by a method of hydrolysis in a contained solvent or the like.

The compound used as a raw material for the structural unit represented by the general formula (1) can be represented by the following general formula (1a). Among them, ^{glycerylamide ethyl methacrylate in which R 1} is a methyl group and n is 2. (Also referred to herein as "glycerol-1-methacryloyloxyethyl urethane" or "GMU") are preferred.

（一般式（１ａ）において、Ｒ¹は水素原子又はメチル基を表し、ｎは１〜４の整数を表す。）

(In the general formula (1a), R ¹ represents a hydrogen atom or a methyl group, and n represents an integer of 1 to 4).

<Structural unit represented by the general formula (2) [Structural unit (2)]>

(In the general formula (2), ^{R 2} represents a hydrogen atom or a methyl group, ^{L 1} _{is, -C 6 H 4 -, -} C 6 H 10 -, - (C = O) -O -, - (C = O) -NH- or -O- (C = O) ^{-represents a divalent group, and L 2} represents an alkyl group having 10 to 22 carbon atoms.)

In the general formula (2), R ² represents a hydrogen atom or a methyl group, and a methyl group is preferable from the viewpoint of improving the storage stability of the copolymer.
In the general formula (2), ^{L 1} is, _-C 6 _{H 4} - _[phenylene], -C _{6 H 10} - [cyclohexylene group], - (C = O) -O- [ester bond], - Represents a divalent group selected from (C = O) -NH- [amide bond] or -O- (C = O)-[oxycarbonyl bond], and represents -C _{6 from the viewpoint of availability of raw materials.} H ₄ - [phenylene], - (C = O) -O- [ester bond], or - (C = O) -NH- [amide bond] is preferred.

In the general formula (2), L ² represents an alkyl group having 10 to 22 carbon atoms, and specifically, an n-decyl group, a lauryl group, a myristyl group, a palmityl group, a stearyl group, an arachidyl group, and a behenyl group. , Oleyl group, linole group, linoleyl group, isostearyl group and the like. Among these, an alkyl group having 10 to 20 carbon atoms is preferable, an alkyl group having 12 to 18 carbon atoms is more preferable, and an alkyl group having 18 carbon atoms is more preferable, from the viewpoint of improving the affinity between the tooth surface microbial adhesion inhibitor and the tooth surface. The stearyl group, which is an alkyl group of the above, is more preferable.
Specific examples of the compound as a raw material of the constituent unit represented by the general formula (2) include lauryl (meth) acrylate and stearyl (meth) acrylate, and among them, lauryl (meth) acrylate. , And stearyl (meth) acrylate, and more specifically, the copolymer is preferably a (glycerylamide ethyl methacrylate / stearyl methacrylate) copolymer.

In the present invention, the copolymer may contain two or more kinds of structural units (1), or may contain two or more kinds of structural units (2). Further, the copolymer may have any structure such as a random copolymer or a block copolymer, or may be a mixture thereof.

<Ratio of constituent units (1) and (2)>
The content of the structural unit (1) with respect to the total of the structural unit (1) and the structural unit (2) in the copolymer is preferably 20 mol% or more, more preferably 30 mol% or more, and 40 mol% or more. Even more preferably, 50 mol% or more is further preferable, 90 mol% or less is preferable, 80 mol% or less is more preferable, 75 mol% or less is more preferable, and 70 mol% or less is further preferable.

<Other building blocks>
The copolymer used in the present invention may contain other structural units other than the structural unit (1) and the structural unit (2) as long as the effects of the present invention are not impaired. And, it is preferable that it consists only of the structural unit (2).
The other structural unit is, for example, a linear or branched alkyl (meth) acrylate or cyclic alkyl (meth) acrylate other than the compound that is the raw material of the structural unit represented by the general formulas (1) and (2). , Aromatic group-containing (meth) acrylate, styrene-based monomer, vinyl ether monomer, vinyl ester monomer, hydrophilic hydroxyl group-containing (meth) acrylate, acid group-containing monomer, nitrogen-containing group-containing single amount Examples thereof include a structural unit derived from a polymerizable monomer selected from a body, an amino group-containing monomer, and a cationic group-containing monomer.

When the copolymer contains other structural units, the ratio of the other structural units to the total structural units is preferably 30 mol% or less, more preferably 20 mol% or less, still more preferably 10 mol% or less. That is, the ratio of the structural unit (1) and the structural unit (2) to all the structural units is preferably 70 mol% or more, more preferably 80 mol% or more, still more preferably 90 mol% or more.

<Weight average molecular weight of copolymer>
The weight average molecular weight (Mw) of the copolymer is preferably 20,000 to 90,000. When the weight average molecular weight of the copolymer is at least the lower limit value, the microbial adhesion suppressing performance is improved, and when it is at least the upper limit value, the handleability of the copolymer is improved. The weight average molecular weight is more preferably 40,000 to 60,000.
The weight average molecular weight of the copolymer refers to the weight average molecular weight in terms of polyethylene glycol by gel filtration chromatography (GFC) analysis, and the GFC analysis is performed using, for example, a high performance liquid chromatography system CCP & 8020 series (manufactured by Tosoh Corporation). Can be measured.

<Amount of copolymer in microbial adhesion inhibitor for tooth surface>
The amount of the copolymer in the microbial adhesion inhibitor for tooth surface of the present invention is 0.003% by mass or more and 1% by mass or less. If the amount of the copolymer is less than the lower limit, the effect of suppressing the adhesion of microorganisms cannot be obtained, and even if the amount of the copolymer exceeds the upper limit, the effect commensurate with the addition amount can be obtained. It becomes difficult to obtain. From the above viewpoint, the amount of the copolymer in the tooth surface microbial adhesion inhibitor is preferably 0.004% by mass or more, more preferably 0.005% by mass or more, and preferably 0.5% by mass. Hereinafter, it is more preferably 0.1% by mass or less, still more preferably 0.05% by mass or less.

<Method for producing copolymer>
The copolymer used in the present invention can be produced by a general method for producing a copolymer. For example, it can be produced by dissolving a compound as a raw material of a structural unit represented by the general formula (1) and the general formula (2) in a solvent and polymerizing by radical polymerization in the presence of a radical polymerization initiator. can.
Examples of the solvent include lower alcohols such as methanol, ethanol, and propanol.
Examples of the polymerization initiator include 2,2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethyl-valeronitrile), benzoyl peroxide, and n-propylperoxycarbonate. An azo-based initiator such as, or a known initiator such as a peroxide-based initiator can be used.
The polymerization temperature is not particularly limited, but is preferably 0 ° C to 80 ° C.

<Arbitrary ingredient>
The microbial adhesion inhibitor for tooth surface of the present invention is an agent, a buffer, a wetting agent, a surfactant, a sweetener, a thickening agent, a solvent, a coloring material, and an organic acid that can be used in an oral composition as needed. , Inorganic salts, antioxidants, stabilizers, preservatives, metal ion sequestering agents, fragrances, flavoring agents, cooling agents, pigments and the like.

The microbial adhesion inhibitor for tooth surface of the present invention preferably contains a wetting agent. By using the copolymer in combination with a wetting agent, the microbial adhesion suppressing performance is improved.
The wetting agent is preferably a polyhydric alcohol, and examples of the polyhydric alcohol include glycerin, propylene glycol, 1,3-butylene glycol, pentylene glycol, dipropylene glycol, polyethylene glycol, xylitol, mannitol, and erythritol.
When the microbial adhesion inhibitor for tooth surface contains a wetting agent, the content thereof is preferably 0.01 to 50% by mass, more preferably 0.01 to 30% by mass, still more preferably 0.01 to 20% by mass. , 1-12% by mass is even more preferable. When the content of the wetting agent is within the above range, the microbial adhesion suppressing performance is further improved.

Examples of the drug include bactericides such as isopropylmethylphenol, depotassium chloride, benzalkonium chloride, benzethonium chloride, alkyldiaminoethylglycine hydrochloride, chlorhexidine hydrochloride, chlorhexidine gluconate, triclosan, and 1,8-cineole;
Anti-inflammatory agents such as sodium azulene sulfonate, allantoin, glycyrrhizic acid and its salts, and β-glycyrrhetinic acid;
Vitamin preparations such as ascorbic acid and its salts, pyridoxine hydrochloride, dl-α-tocopherol acetate, and dl-α-tocopherol nicotinate;
Hemostatic agents such as epsilon-aminocaproic acid and tranexamic acid;
Hypersensitivity relievers such as potassium nitrate and aluminum lactate;
Spouts such as 1,8-cineole; adsorbents such as zeolite;
Anti-tartar agents such as disodium dihydrogen pyrophosphate, sodium pyrophosphate, and zinc chloride;
Caries preventive agents such as sodium fluoride and sodium monofluorophosphate;
Halitosis remover such as sodium copper chlorophyllin;
Detergents such as polyoxyethylene lauryl ether (8-10EO) and sodium lauroyl sarcosine;
Astringents such as sodium chloride and l-menthol;
Dental plaque removers such as sodium monohydrogen phosphate, trisodium phosphate, polyethylene glycol, and polyvinylpyrrolidone; and the like.

Examples of the buffering agent include citric acid, phosphoric acid, malic acid, gluconic acid, and salts thereof. When the tooth surface microbial adhesion inhibitor contains a buffering agent, the content thereof is 0.01% by mass or more. 3% by mass is preferable.

Examples of the surfactant include polyoxyethylene hydrogenated castor oil, polyoxyethylene sorbitan fatty acid ester, polyglycerin fatty acid ester, acyl amino acid salt, fatty acid amide propyl betaine, fatty acid amide betaine and the like.

Examples of the preservative include polyhexanide hydrochloride, benzoic acid, benzoate, parabens and the like, and when the tooth surface microbial adhesion inhibitor contains a preservative, the content thereof is preferably 0.01 to 5% by mass. ..
Sweeteners include saccharin, stevioside, sucralose, aspartame, acesulfame potassium, and licorice extract.

The thickening agent is not particularly limited, but is a cellulosic thickening agent such as methyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose, and carboxymethyl cellulose, hypromellose and its salt, chondroitin sulfate and its salt, and alginic acid. And its salts, polysaccharides such as gellan gum, xanthan gum and the like.

The microbial adhesion inhibitor for tooth surface of the present invention can suppress the adhesion of microorganisms to the tooth surface by using it as a coating agent for the tooth surface. However, when coating the tooth surface, the copolymer is used as a solvent. It is preferable to use it by dissolving or suspending it in.
The solvent is not particularly limited as long as it is used for dental purposes such as water and ethanol, but water is preferable.
Further, the solvent may contain a salt, a surfactant, an antiseptic and the like for the purpose of adjusting the pH and preservatives.
When the microbial adhesion inhibitor for tooth surface of the present invention contains a solvent, the content thereof is preferably 50% by mass or more, more preferably 80% by mass or more, still more preferably 90% by mass or more.

<Manufacturing method of microbial adhesion inhibitor for tooth surface>
The method for producing the microbial adhesion inhibitor for tooth surface of the present invention is not particularly limited, and the copolymer can be produced by mixing the copolymer with a solvent such as water and stirring the mixture. Specifically, it can be produced by a method of stirring the copolymer with purified water heated to about 60 to 90 ° C., and a solution of an arbitrary component such as glycerin or 1,3-butylene glycol. It can also be produced by adding the above-mentioned copolymer to the solution, stirring at about 60 to 90 ° C., cooling to room temperature, and then adding purified water to this solution and stirring.

<Aspects when using a microbial adhesion inhibitor for tooth surface>
The mode of use of the microbial adhesion inhibitor for tooth surface of the present invention is not particularly limited, but it is used as an oral moisturizing agent, a mouthwash, a mouthwash, a dentifrice, a mouth refreshing agent, a chewable agent, a denture cleaning agent and the like. It can be used in the form of liquids, viscous liquids, gels, tablets and the like.

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto.
<Synthesis example: Synthesis of (glycerylamide ethyl methacrylate / stearyl methacrylate) copolymer>
330 g of (R, S) -1,2-isopropyrideneglycerol and 50 ml of pyridine were added to the 4-necked flask, and a dropping funnel and a calcium tube were attached. To this solution, 368 g of 2-methacryloyloxyethyl isocyanate (manufactured by Showa Denko KK) was slowly added dropwise at room temperature and in the dark. Then, the reaction was carried out in an oil bath set at 50 ° C. for 7 hours.
After completion of the reaction, pyridine and excess (R, S) -1,2-isopropyrideneglycerol were distilled off under reduced pressure to obtain a yield of 621 g and a yield of 91% as a white solid (R, S) -1,2-. Isopropyrideneglycerol-3-methacryloyloxyethyl urethane was obtained.

To 500 g of the obtained (R, S) -1,2-isopropyrideneglycerol-3-methacryloyloxyethyl urethane, 1.95 L of methanol and 50 ml of 4N hydrochloric acid were added, and the mixture was reacted by stirring at room temperature for 30 minutes. , The suspension became a clear solution. After further reacting by stirring for 60 minutes, the solvent was distilled off by drying under reduced pressure to obtain a colorless viscous liquid glycerol-1-methacryloyloxyethyl urethane (hereinafter, also referred to as “GMU”). The yield was 412 g and the yield was 96%.

8.9 g (about 0.036 mol) of the GMU and 8.0 g (about 0.024 mol) of stearyl methacrylate (hereinafter, also referred to as “SMA”) as a monomer to be copolymerized are dissolved in 140 g of ethanol, and four flasks are used. Placed in a flask. Then, after blowing nitrogen into the obtained solution for 30 minutes, 0.12 g of 2,2'-azobisisobutyronitrile was added at 60 ° C. and the polymerization reaction was carried out for 8 hours. The polymerization solution was added dropwise to 3 L of diethyl ether with stirring, the precipitated precipitate was filtered, and vacuum dried at room temperature for 48 hours to obtain a (glycerylamide ethyl methacrylate / stearyl methacrylate) copolymer.
The content of the structural unit (1) with respect to the total of the structural units (1) and the structural units (2) in the copolymer, that is, the GMU with respect to the total of the structural units derived from GMU and the structural units derived from SMA. The amount of the structural unit derived from was 60 mol%, and the weight average molecular weight in terms of polyethylene glycol by gel filtration chromatography (GFC) analysis was 50,000.

<Example 1>
To 99.995 g of purified water heated to 80 ° C., 0.005 g of the (glycerylamide ethyl methacrylate / stearyl methacrylate) copolymer produced in the above synthesis example was added, and the mixture was stirred to prepare the microorganism for the tooth surface of Example 1. An adhesion inhibitor was prepared.

<Comparative Example 1>
A microbial adhesion inhibitor for the tooth surface of Comparative Example 1 was prepared according to the method described in Example 1 except that the composition of the compounding ingredients was changed to that shown in Table 1.

<Example 2>
0.025 g of the (glycerylamide ethyl methacrylate / stearyl methacrylate) copolymer was added to a mixed solution of 4.75 g of glycerin and 4.75 g of 1,3-butylene glycol, and the mixture was dissolved by stirring at 80 ° C. .. After dissolution, after cooling to room temperature, purified water was added to the admixture so that the total amount was 100 g, and the mixture was stirred to prepare the microbial adhesion inhibitor for tooth surface of Example 2.

<Example 3 and Comparative Example 2>
The tooth surface microbial adhesion inhibitor of Example 3 and Comparative Example 2 was prepared according to the method described in Example 2, except that the composition of the compounding component was changed to that shown in Table 1.

<Comparative Example 3>
A mixed solution of 4.75 g of glycerin and 4.75 g of 1,3-butylene glycol was stirred at 80 ° C., cooled to room temperature, and then purified water was added to the mixed solution so that the total amount became 100 g. By stirring, the microbial adhesion inhibitor for the tooth surface of Comparative Example 3 was prepared.

The following bacterial adhesion suppression evaluations were performed on the tooth surface microbial adhesion inhibitores of Examples 1 to 3 and Comparative Examples 1 to 3 obtained by the above-mentioned method. The results are shown in Table 1.

<Evaluation of bacterial adhesion suppression>
(Procedure 1) Streptococcus mutans NBRC13955 (hereinafter, also referred to as “S. mutans”) was inoculated into Brainheart infusion medium (manufactured by Becton Dickinson) and cultured overnight.
(Procedure 2) The cultured S. mutans solution was centrifuged and washed with a phosphate buffer solution.
(Procedure 3) The S. mutans solution was prepared with a phosphate buffer solution so that the optical concentration (660 nm) was 1.0.
(Procedure 4) 1 mL each of the compositions of Examples 1 to 3 and Comparative Examples 1 to 3 was added to a 24-well microplate, and hydroxyapatite pellets (CELLYARD pellt D5-T2, HOYA Corporation) were added to each as a tooth model compound. ), Hereinafter also referred to as "HAp plate"), and allowed to stand for 30 seconds.
Further, the HAp plate was separately placed in 1 mL of purified water and allowed to stand for 1 minute. This was used as a control.

(Procedure 5) Each composition was removed, and the HAp plate was washed 3 times with 1 mL of phosphate buffer.
(Procedure 6) 0.5 mL each of the S. mutans solution prepared in step 3 was added to a 24-well microplate containing a HAp plate, and the cells were cultured for 5 hours to attach S. mutans to the HAp plate.
(Procedure 7) The S. mutans solution was removed, and the HAp plate was washed 3 times with 1 mL of phosphate buffer.
(Procedure 8) 0.5 mL of Victoria Blue solution was added to a 24-well microplate containing a HAp plate, and the mixture was allowed to stand for 10 minutes to stain S. mutans.
(Procedure 9) The Victoria blue solution was removed, and the HAp plate was washed twice with 0.5 mL of decolorizing solution.

(Procedure 10) The HAp plate was washed 3 times with 1 mL of phosphate buffer.
(Procedure 11) 0.5 mL of ethanol was added to a 24-well microplate containing a HAp plate, and the Victoria blue solution incorporated in S. mutans was extracted.
(Procedure 12) 0.1 mL of the extracted Victoria Blue solution was weighed, and the absorbance at 595 nm was measured using a microplate reader (model: SpectraMax M3, manufactured by Molecular Device Japan Co., Ltd.).

The bacterial adhesion suppression rate was calculated from the following formula.
Bacterial adhesion inhibition rate _{(%) = (A c -A} s) / A c × 100
A _c: control (purified water) absorbance obtained from the treated HAp plate in A _s: Examples and the absorption measured from HAp plate treated with Comparative Example In the present evaluation, the large amount of attached bacteria The higher the absorbance. Therefore, the lower the absorbance, the better the microbial adhesion inhibitor for the tooth surface is in the bacterial adhesion inhibitory performance.
The evaluation results are shown in Table 1.

According to the present invention, it is possible to provide a microbial adhesion inhibitor for a tooth surface, which can adhere a microbial adhesion inhibitor to the tooth surface without using a binder component and has excellent microbial adhesion inhibitory performance. Can be done.

Claims (4)

It contains a copolymer having a structural unit represented by the following general formula (1) and a structural unit represented by the following general formula (2), and the content of the copolymer is 0.003% by mass or more and 1 mass. % Or less for tooth surface S. Mutant adhesion inhibitor.

(In the general formula (1), R ¹ represents a hydrogen atom or a methyl group, and n represents an integer of 1 to 4).

(In the general formula (2), R ² represents a hydrogen atom or a methyl group, L ¹ represents − (C = O) −O−, and L ² represents an alkyl group having 12 to 18 carbon atoms. The S. for tooth surface according to claim 1, wherein the copolymer is a (glycerylamide ethyl methacrylate / stearyl methacrylate) copolymer. Mutant adhesion inhibitor. The tooth surface S. cerevisiae according to claim 1 or 2, further containing a wetting agent consisting of a polyhydric alcohol. Mutant adhesion inhibitor. The tooth surface S. cerevisiae according to claim 3, wherein the content of the wetting agent is 0.01 to 50% by mass. Mutant adhesion inhibitor.