JP2019112371A - Microbial adhesion inhibitor for tooth surface - Google Patents

Abstract

To provide a microbial adhesion inhibitor for a tooth surface which can adhere to the tooth surface without using any binder component and has excellent microbial adhesion-inhibiting performance.SOLUTION: The microbial adhesion inhibitor for a tooth surface comprises a copolymer which has a constitutional unit represented by general formula (1) and a constitutional unit represented by general formula (2). The content of the copolymer is from 0.003 mass% to 1 mass% inclusive.SELECTED DRAWING: None

Description

  The present invention relates to a microorganism adhesion inhibitor for tooth surfaces which is excellent in the microorganism adhesion suppression performance.

  Dental plaque is an aggregate composed of microbes adhering to the tooth surface and a matrix between bacterial cells, and causes oral diseases such as caries and periodontal disease. Therefore, not forming dental plaque on the tooth surface is a measure to prevent caries. The enamel that constitutes the tooth surface is mostly composed of a calcium phosphate structure called hydroxyapatite. Therefore, the tooth surface is different from the material used in dental prostheses, and it is known that the adsorption of proteins, amino acids, sugars, etc. is high due to electrostatic interaction and hydrogen bonding interaction with hydroxyl group. It is considered to be a place where dental plaque is easily formed (Non-Patent Documents 1 and 2).

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

JP, 2011-153101, A

Atsushi Yamamoto et al., "Application and Future Challenges of Hydroxyapatite Surface in the Bioindustry", Journal of the Crystal Growth Society of Japan, Vol. 33, No. 5, pp. 388-394, 2006 Hideki Aoki et al., “Amazon of Biomaterial Apatite and Surface Technology”, Surface Technology, Vol. 58, No. 12, pp. 744-750, 2007

In the oral microbe adhesion preventing agent described in Patent Document 1, in order to keep the phosphorylcholine group-containing polymer in the oral cavity, a water-soluble polysaccharide as a binder component and a poly (meth) acrylic acid derivative as a compatibilizing component are blended. It was not always easy for the user to use.
The subject of the present invention is made in view of the above-mentioned conventional problem, and while being able to make a microorganism adhesion control agent adhere to a tooth surface without using a binder component, excellent microorganism adhesion suppression performance It is to provide a microorganism adhesion inhibitor for tooth surfaces having the

  As a result of intensive studies to solve the above-mentioned conventional problems, the present inventors have found that a dental surface microbe adhesion inhibitor containing a specific amount of a copolymer having two specific structural units, The inventors have found that adhesion of microorganisms to tooth surfaces can be suppressed without using a binder or the like, and the present invention has been completed.

That is, the present invention is summarized in 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), wherein the content of the copolymer is 0.003% by mass The microorganism adhesion inhibitor for tooth surfaces which is 1 mass% or less.

(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 ₆ H ₄ —, —C ₆ H ₁₀ —, — (C = O) —O—, — (C) R ² represents a divalent group selected from = O) —NH— or —O— (C = O) —, and L ² represents an alkyl group having 10 to 22 carbon atoms)

[2] The dental deposit microbe adhesion inhibitor as described in [2] above, wherein the copolymer is (glyceryl glycerylamidoethyl stearyl methacrylate) copolymer.
[3] The dental surface microbe adhesion inhibitor as described in the above [1] or [2], further comprising a wetting agent comprising a polyhydric alcohol.
[4] The dental surface microorganism adhesion inhibitor according to the above [3], wherein the content of the wetting agent is 0.01 to 50% by mass.

  According to the dental surface microbe adhesion inhibitor of the present invention, it is possible to adhere the microbial adhesion inhibitor to the tooth surface without using a binder component, and for dental surfaces having excellent microbe adhesion suppression performance. A microorganism adhesion inhibitor can be provided.

Hereinafter, the present invention will be described in more detail.
In the present specification, "(meth) acrylate" means "acrylate or methacrylate", and the same applies to other similar terms.
Further, in the present specification, when preferable numerical ranges (for example, ranges of content and weight average molecular weight) are described stepwise, the lower limit value and the upper limit value can be combined independently. For example, in the description “preferably 10 or more, more preferably 20 or more, and preferably 100 or less, more preferably 90 or less”, “preferred lower limit: 10” and “preferred upper limit: 90” are combined Can be "10 or more and 90 or less". Also, for example, in the description of “preferably 10 to 100, more preferably 20 to 90”, “10 to 90” can be similarly obtained.

[Microbe adhesion inhibitor for tooth surface]
The dental deposit microbe adhesion inhibitor of the present invention comprises a copolymer having a constitutional unit represented by the following general formula (1) and a constitutional unit represented by the following general formula (2), and the copolymer Content of 0.003% by mass or more and 1% by mass or less, and because adhesion of microbes to the tooth surface can be effectively suppressed, prevention of dental caries and periodontal disease of the user It will be possible.

Hereinafter, the configuration of the copolymer will be described in detail.
<Constituent Unit Represented by General Formula (1) [Constituent Unit (1)]>

(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.
Moreover, in the said General formula (1), n represents the integer of 1-4, From a viewpoint of the availability of a raw material, 1-3 are preferable, and 1-2 are more preferable.

  The compound used as the raw material of the structural unit represented by said General formula (1) can be manufactured by a well-known method. For example, in the presence of a catalyst for hydrolysis, a compound obtained by subjecting an acetalized form of glycerol and a (meth) acrylate having an isocyanate group to urethanation reaction in the presence of a catalyst for urethanization reaction is It can be produced by a method such as hydrolysis in a contained solvent.

Formula (1) becomes a constituent unit of the raw material represented by the compound can be represented by the following general formula (1a), among others, methacrylic acid glyceryl amidoethyl R ¹ is 2 is n methyl (Also referred to herein as "glycerol-1-methacryloyloxyethyl urethane" or "GMU") is preferred.

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

<Constituent Unit Represented by General Formula (2) [Constituent Unit (2)]>

(In the general formula (2), R ² represents a hydrogen atom or a methyl group, L ¹ represents —C ₆ H ₄ —, —C ₆ H ₁₀ —, — (C = O) —O—, — (C) R ² represents a divalent group selected from = O) —NH— or —O— (C = O) —, 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 from the viewpoint of the availability of the raw material, —C ₆ 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 a carbon number of 10 to 22, and specifically, n-decyl group, lauryl group, myristyl group, palmityl group, stearyl group, arachidyl group, behenyl group And oleyl group, linole group, linoleyl group, and isostearyl group. Among these, an alkyl group having 10 to 20 carbon atoms is preferable, and an alkyl group having 12 to 18 carbon atoms is more preferable, with 18 carbon atoms, from the viewpoint of improving the affinity between the dental surface microorganism adhesion inhibitor and the tooth surface. More preferred is a stearyl group which is an alkyl group of
Specific examples of the compound serving as the raw material of the structural unit represented by the general formula (2) include lauryl (meth) acrylate and stearyl (meth) acrylate, among which lauryl (meth) acrylate is preferred. And stearyl (meth) acrylate are preferable, and more specifically, it is preferable that the copolymer is (glycerylamidoethyl methacrylate / stearyl methacrylate) copolymer.

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

<Percentage of Constituent Units (1) and (2)>
20 mol% or more is preferable, as for content of structural unit (1) with respect to the sum total of structural unit (1) and structural unit (2) in the said copolymer, 30 mol% or more is more preferable, and 40 mol% or more Still more preferable, 50 mol% or more is still more preferable, and 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 still more preferable.

<Other configuration unit>
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, but the structural unit (1) And consisting only of the structural unit (2).
Examples of the other structural units include linear or branched alkyl (meth) acrylates and cyclic alkyl (meth) acrylates other than the compounds serving as the raw materials of the structural units represented by the general formulas (1) and (2). Aromatic group-containing (meth) acrylate, styrene-based monomer, vinyl ether monomer, vinyl ester monomer, hydrophilic hydroxyl-containing (meth) acrylate, acid group-containing monomer, nitrogen-containing group-containing unit amount Structural units derived from polymerizable monomers selected from the group, amino group-containing monomers, and cationic group-containing monomers.

  When a copolymer contains other structural units, 30 mol% or less is preferable, as for the ratio of the other structural unit in all the structural units, 20 mol% or less is more preferable, and 10 mol% or less is still more preferable. That is, 70 mol% or more is preferable, as for the ratio of the said structural unit (1) and structural unit (2) in all the structural units, 80 mol% or more is more preferable, and 90 mol% or more is still more preferable.

<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 equal to or more than the lower limit, the microorganism adhesion suppressing performance is improved, and when the weight average molecular weight is equal to or less than the upper limit, 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 GFC analysis is performed using, for example, high performance liquid chromatography system CCP & 8020 series (made by Tosoh Corp.) It can be measured.

<Amount of copolymer in microbe adhesion inhibitor for tooth surface>
The amount of the copolymer in the tooth surface microbe adhesion inhibitor 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 adhesion of microorganisms can not be obtained, and even if the amount of the copolymer exceeds the upper limit, an effect corresponding to the added amount is obtained. It becomes difficult to obtain. From the above viewpoint, the amount of the copolymer in the dental surface microbe adhesion inhibitor is preferably 0.004% by mass or more, more preferably 0.005% by mass or more, and preferably 0.5% by mass. The following content is more preferably 0.1% by mass or less, still more preferably 0.05% by mass or less.

<Method of producing copolymer>
The copolymer used in the present invention can be produced by a general method for producing a copolymer. For example, it may be produced by dissolving a compound serving as a raw material of the 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. it can.
Examples of the solvent include lower alcohols such as methanol, ethanol and propanol.
Moreover, as a polymerization initiator, for example, 2,2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethyl-valeronitrile), benzoyl peroxide, and n-propylperoxy carbonate And the like, and known initiators such as peroxide initiators can be used.
The polymerization temperature is not particularly limited, but is preferably 0 ° C to 80 ° C.

<Optional component>
The dental surface microbe adhesion inhibitor of the present invention comprises a drug which can be optionally used in an oral composition, a buffer, a wetting agent, a surfactant, a sweetening agent, a thickening agent, a solvent, a coloring material, an organic acid Inorganic salts, antioxidants, stabilizers, preservatives, sequestering agents, sequestering agents, flavors, flavoring agents, refreshing agents, pigments and the like may be contained.

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

Examples of the drug include isopropylmethylphenol, depotassium chloride, benzalkonium chloride, benzethonium chloride, alkyldiaminoethylglycine hydrochloride, chlorhexidine hydrochloride, chlorhexidine gluconate, triclosan, and a bactericidal agent such as 1,8-cineole;
Anti-inflammatory agents such as sodium azulene sulfonate, allantoin, glycyrrhizic acid and salts thereof, and β-glycyrrhetinic acid;
Vitamin agents such as ascorbic acid and salts thereof, pyridoxine hydrochloride, dl-α-tocopherol acetate, and dl-α-tocopherol nicotinate;
Hemostatic agents such as epsilon-aminocaproic acid and tranexamic acid;
Hypersensitive stimulants such as potassium nitrate and aluminum lactate;
Expectorants such as 1,8-cineole; adsorbents such as zeolite;
Anticalculus agents such as disodium dihydrogen pyrophosphate, sodium pyrophosphate and zinc chloride;
Caries preventive agents such as sodium fluoride and sodium monofluorophosphate;
A breath freshener such as sodium copper chlorophyllin;
Detergents such as polyoxyethylene lauryl ether (8 to 10 E.O.) and sodium lauroyl sarcosine;
Sodium chloride and astringent agents such as l-menthol;
Plaque removing agents such as sodium monohydrogen phosphate, trisodium phosphate, polyethylene glycol, and polyvinyl pyrrolidone; and the like.

  Examples of the buffer include citric acid, phosphoric acid, malic acid, gluconic acid, and salts thereof. When the dental surface microbe adhesion inhibitor contains a buffer, the content thereof is 0.01% by mass to 3 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 amidopropyl betaine, and fatty acid amido betaine.

Examples of preservatives include polyhexanide hydrochloride, benzoic acid, benzoate, and parabens. When the dental surface microbe adhesion inhibitor contains a preservative, its content is preferably 0.01 to 5% by mass. .
Sweetening agents include saccharin, stevioside, sucralose, aspartame, acesulfame potassium, and licorice extract.

  Examples of thickening agents include, but are not limited to, cellulose thickening agents such as methyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose and carboxymethyl cellulose, hyaluronic acid and salts thereof, chondroitin sulfate and salts thereof, and alginic acid. And salts thereof, gellan gum, polysaccharides such as xanthan gum, and the like.

The microbe adhesion inhibitor for tooth surface of the present invention can suppress microbe adhesion to the tooth surface by using it as a coating agent for the tooth surface, but when coating on 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 applications such as water and ethanol, but water is preferable.
The solvent may also contain salts, surfactants, preservatives and the like for the purpose of pH adjustment and preservative.
When the dental attachment prevention agent for dental surfaces of the present invention contains a solvent, the content thereof is preferably 50% by mass or more, more preferably 80% by mass or more, and still more preferably 90% by mass or more.

<Method of producing microbe adhesion inhibitor for tooth surface>
There is no restriction | limiting in particular in the manufacturing method of the microbe adhesion inhibitor for tooth surfaces of this invention, It can manufacture by mixing and stirring the said copolymer in solvent, such as water. Specifically, it can be manufactured by a method of stirring the copolymer with respect to purified water heated to about 60 to 90 ° C., and a solution of an optional component such as glycerin or 1,3-butylene glycol Alternatively, the copolymer may be charged, stirred at about 60 to 90 ° C., cooled to room temperature, and then purified water may be added to the solution and stirred.

<Aspects of using a microbe adhesion inhibitor for tooth surface>
There is no particular limitation on the mode of use of the microorganism adhesion inhibitor for tooth surface of the present invention, but it is used as an oral moisturizer, mouthwash, mouthwash, dentifrice, mouth freshener, chewable agent, denture cleaner, etc. It can be used in the form of liquid, viscous liquid, gel, tablet and the like.

Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited thereto.
Synthesis Example: Synthesis of (glyceryl amidoethyl methacrylate / stearyl methacrylate) copolymer
In a four-necked flask, 330 g of (R, S) -1,2-isopropylidene glycerol and 50 ml of pyridine were added, and a dropping funnel and a calcium tube were attached. To this solution, 368 g (manufactured by Showa Denko KK) of 2-methacryloyloxyethyl isocyanate was slowly dropped at room temperature under light shielding. Then, it was made to react in the oil bath set to 50 degreeC for 7 hours.
After completion of the reaction, pyridine and excess (R, S) -1,2-isopropylidene glycerol were distilled off under reduced pressure to give 621 g (91% yield) of (R, S) -1,2-white solid in a yield of 91%. The isopropylidene glycerol 3- methacryloyl oxyethyl urethane was obtained.

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

8.9 g (about 0.036 mol) of 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 Placed in a flask. Next, nitrogen was blown into the obtained solution for 30 minutes, and then 0.12 g of 2,2'-azobisisobutyro nitrile was added at 60 ° C and polymerization reaction was performed for 8 hours. The polymerization solution was added dropwise to 3 L of diethyl ether while stirring, and the deposited precipitate was filtered and vacuum dried at room temperature for 48 hours to obtain (glyceryl amidoethyl methacrylate / stearyl methacrylate) copolymer.
In addition, 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, that is, the GMU with respect to the total of the structural unit derived from GMU and the structural unit derived from SMA The amount of structural units derived from was 60 mol%, and the weight average molecular weight in terms of polyethylene glycol as determined by gel filtration chromatography (GFC) analysis was 50,000.

Example 1
The microorganism for tooth surface of Example 1 is added by adding 0.005 g of (glyceryl amidoethyl methacrylate / stearyl methacrylate) copolymer prepared in the above synthesis example to 99.995 g of purified water heated to 80 ° C. and stirring. An adhesion inhibitor was prepared.

Comparative Example 1
A dental attachment microorganism adhesion inhibitor of Comparative Example 1 was prepared according to the method described in Example 1 except that the composition of the blended components was changed to that shown in Table 1.

Example 2
Into a mixed solution of 4.75 g of glycerin and 4.75 g of 1,3-butylene glycol, 0.025 g of (glycerylamidoethyl methacrylate / stearyl methacrylate) copolymer was added and dissolved by stirring at 80 ° C. . After dissolution, the mixture was cooled to room temperature, purified water was added so as to make the total amount 100 g with respect to the mixture, and the mixture was stirred to prepare a tooth adhesion microorganism adhesion inhibitor of Example 2.

Example 3 and Comparative Example 2
The dental surface microbe 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 blended components 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 is stirred at 80 ° C. and cooled to room temperature, and then purified water is added so that the total amount is 100 g with respect to the mixture. The tooth surface microorganism adhesion inhibitor of Comparative Example 3 was prepared by stirring.

  The following bacteria adhesion inhibitory evaluation was performed about the microbe adhesion inhibitor for tooth surfaces of Example 1-3 obtained by the above-mentioned method, and Comparative Examples 1-3. The results are shown in Table 1.

<Antibacterial adhesion evaluation>
(Procedure 1) Streptococcus mutans NBRC 13 955 (hereinafter also referred to as "S. mutans") was inoculated into Brain Heart Infusion Medium (manufactured by Becton Dickinson) and cultured overnight.
(Procedure 2) The cultured S. mutans solution was centrifuged and washed with phosphate buffer.
(Procedure 3) The phosphate buffer solution was prepared so that the optical density (660 nm) of the S. mutans solution would be 1.0.
(Procedure 4) 1 mL each of the compositions of Examples 1 to 3 and Comparative Examples 1 to 3 were added to a 24-well microplate, and hydroxyapatite pellets (CELLYARD pellt D5-T2, HOYA (strain (Hereinafter referred to as "HAp board") and allowed to stand for 30 seconds.
In addition, the HAp plate was separately added to 1 mL of purified water and allowed to stand for 1 minute. This is the 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 Procedure 3 was added to a 24-well microplate containing an HAp plate and cultured for 5 hours to allow S. mutans to adhere to the HAp plate.
(Procedure 7) The S. mutans solution was removed, and the HAp plate was washed three times with 1 mL of phosphate buffer.
(Procedure 8) 0.5 mL each of Victoria Blue solution was added to a 24-well microplate containing an HAp plate, and 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 the 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 an HAp plate, and Victoria Blue solution incorporated into S. mutans was extracted.
(Procedure 12) 0.1 mL of the extracted Victoria Blue solution was weighed out, and the absorbance at 595 nm was measured using a microplate reader (Model: SpectraMax M3, manufactured by Molecular Devices Japan).

The bacterial adhesion inhibition rate was calculated by the following equation.
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, the better. Therefore, the lower the absorbance is, the better the tooth adhesion prevention agent against microbe adhesion is.
The evaluation results are shown in Table 1.

  According to the present invention, it is possible to provide a microorganism adhesion inhibitor for tooth surfaces having an excellent ability to suppress the adhesion of microorganisms, while being capable of adhering the microorganism adhesion inhibitor to tooth surfaces without using a binder component. Can.

Claims (4)

It contains a copolymer having a constitutional unit represented by the following general formula (1) and a constitutional unit represented by the following general formula (2), and the content of the copolymer is 0.003 mass% or more and 1 mass % Or less tooth surface microbe 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 ₆ H ₄ —, —C ₆ H ₁₀ —, — (C = O) —O—, — (C) R ² represents a divalent group selected from = O) —NH— or —O— (C = O) —, and L ² represents an alkyl group having 10 to 22 carbon atoms)   The dental attachment microorganism adhesion inhibitor according to claim 1, wherein the copolymer is (glyceryl glycerylamidoethyl / stearyl methacrylate) copolymer.   The dental surface microbe adhesion inhibitor according to claim 1 or 2, further comprising a wetting agent comprising a polyhydric alcohol.   The dental attachment microorganism adhesion inhibitor according to claim 3, wherein the content of the wetting agent is 0.01 to 50% by mass.