JP2019112370A - Microbial adhesion inhibitor for dental prosthesis - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a microbial adhesion inhibitor for a dental prosthesis having excellent microbial adhesion inhibitory performance. A copolymer having a structural unit represented by the general formula (1) and a structural unit represented by the general formula (2) is contained, and the content of the copolymer is 0.003% by mass or more. A microbial adhesion inhibitor for dental prostheses in an amount of 1% by mass or less. [Selection diagram] None

Description

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

  A dental prosthesis is an artifact that is supplemented to restore the condition of the teeth when there is a tooth loss or loss. Tooth loss and loss causes include fractures, caries, and periodontal disease. Dental prostheses are essential for the treatment of tooth loss or loss, as the increase in missing or missing teeth causes functional deterioration such as chewing, swallowing and speech, which can in turn lead to deterioration of physical condition or illness. is there.

  On the other hand, when using a prosthesis, its maintenance becomes important. For example, it is known that a denture tends to form a gap under the denture base because a dent is easily formed (Non-Patent Document 1). In general, plaques are accumulated and aggregated by late-fixing bacteria here to form plaques, after which early-fixing bacteria such as Streptococcus mutans attach and grow. Plaques formed of teeth, gums and dental prostheses cause dental caries, periodontal diseases, and mucosal abnormalities. Therefore, the inhibition of adhesion of early colonizing bacteria such as Streptococcus mutans is also important in the maintenance of dental prostheses.

  In addition, it is also known that the implant user has an increased risk of causing periodontitis when plaque is formed at the implant root portion as compared with natural teeth (Non-patent Document 2). Plaques formed on the prosthesis are easily transmitted to surrounding healthy teeth, and failure to maintain the prosthesis can cause loss of healthy teeth.

In particular, a denture is composed of an artificial tooth such as ceramic and a denture base such as a resin resin, and is removable by the user. Therefore, although the user carries out daily maintenance, maintenance by using a denture cleaner alone tends to be insufficient in plaque removal effect, and maintenance by brushing with a dedicated brush is recommended.
However, some denture users may scratch the denture base by false brushing, and the wound may be a hotbed for plaque formation and cause oral diseases. Therefore, there is a need for a method for suppressing the adhesion of microorganisms by a denture user in a simpler method.

  Under the circumstances, a coating agent that suppresses plaque adhesion to a prosthesis and a denture has been actively developed. For example, a coating composition comprising a fluorine-containing polymer (patent documents 1 and 2) and a coating composition comprising a copolymer of 2-methacryloyloxyethyl phosphorylcholine and (meth) acrylic acid ester are disclosed (patent document 3) ).

JP 10-139614 A International Publication No. 2006/016649 JP 2004-194874 A

Hiroki Futagawa et al., "Adhesion of oral candida and biofilm formation", Journal of Japanese Society for Medical Mycology, 46, pp. 233-242, 2005. Yasumasa Kawashima et al., "Observation of microbiota in the pocket around the implant-comparison due to the cause of tooth loss in the implanted part", Japan Oral Implant Society Journal, Volume 16, No. 4, pp. 507-512, 2003

According to the coating agent described in patent documents 1-3, the further improvement of what can control adhesion of the microorganism to a dental prosthesis was called for.
The subject of the present invention is made in view of the above-mentioned conventional problem, and is providing the microorganism adhesion control agent for dental prostheses which is excellent in the adhesion control performance of microorganisms.

  The inventors of the present invention have conducted intensive studies to solve the above-described conventional problems, and as a result, they are a microorganism adhesion inhibitor for dental prostheses, which contains a specific amount of a copolymer having two specific structural units. It has been found that the adhesion of microorganisms to dental prostheses can be suppressed, and the present invention has been completed.

That is, the present invention provides the following.
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 The microorganism adhesion inhibitor for dental prostheses which is less than%.

(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)

  ADVANTAGE OF THE INVENTION According to this invention, the microorganism adhesion inhibitor for dental prostheses which is excellent in the adhesion suppression performance of microorganisms 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.

[Microbial adhesion inhibitor for dental prostheses]
The microorganism adhesion inhibitor for dental prostheses of the present invention comprises a copolymer having a constituent unit represented by the following general formula (1) and a constituent unit represented by the following general formula (2), The combination content is 0.003% by mass or more and 1% by mass or less, and microbe adhesion to the dental prosthesis can be effectively suppressed, so that oral malodor prevention by the dental prosthesis user can be prevented. And periodontal disease prevention becomes 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], - (C = O) -NH- [amide bond], or -O- (C = O) - represents the [oxycarbonyl bond], from the viewpoint to the availability of raw materials, _-C 6 _{H 4} - [phenylene] -(C = O) -O- [ester bond] or-(C = O) -NH- [amide bond] is preferable.

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, from the viewpoint of improving the affinity between the microorganism adhesion inhibitor for dental prosthesis and the dental prosthesis. The stearyl group of formula 18 is more preferred.
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 or less.
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 dental prostheses>
The amount of the copolymer in the microorganism adhesion inhibitor for dental prostheses 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 microorganism adhesion inhibitor for dental prostheses is preferably 0.004% by mass or more, more preferably 0.005% by mass or more, and preferably 0.5% by mass. % Or less, 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 microbe adhesion inhibitor for dental prostheses of the present invention is a drug which can be used for the composition for oral cavity if necessary, a buffer, a wetting agent, a surfactant, a sweetener, a thickener, a thickener, a solvent, a coloring material, an organic Acids, inorganic salts, antioxidants, stabilizers, preservatives, sequestrants, sequestering agents, flavors, flavors, refreshing agents, pigments and the like may be contained.

Particularly, the agent for suppressing adhesion of a microorganism to a dental prosthesis 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 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 microorganism adhesion inhibitor for dental prostheses contains a wetting agent, the content thereof is preferably 0.01 to 50% by mass, more preferably 0.01 to 30% by mass, and further 0.01 to 20% by mass Preferably, 1 to 12% by mass is 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, and when the microorganism adhesion inhibitor for dental prostheses contains a buffer, the content thereof is 0.01% by mass -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, and when the microorganism adhesion inhibitor for dental prostheses contains a preservative, its content is 0.01 to 5% by mass. preferable.
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 agent for suppressing adhesion of a microorganism to a dental prosthesis of the present invention can suppress the adhesion of microorganisms to the surface of a dental prosthesis or a dental prosthesis by using it as a raw material of a dental prosthesis or a surface coating agent of the dental prosthesis. Although it is possible, it is preferable to use the copolymer dissolved or suspended in a solvent for application or coating to a dental prosthesis.
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 microbe adhesion inhibitor for dental prostheses of this invention contains a solvent, 50 mass% or more is preferable, 80 mass% or more is more preferable, 90 mass% or more is still more preferable.

<Production method of microorganism adhesion inhibitor for dental prosthesis>
There is no restriction | limiting in particular in the manufacturing method of the microorganism adhesion inhibitor for dental prostheses 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 microorganism adhesion inhibitor for dental prostheses>
There are no particular limitations on the mode of use of the microorganism adhesion inhibitor for dental prostheses of the present invention, but denture cleansers, denture removers, oral moisturizers, mouthrinses, mouthwashes, dentifrices, mouth fresheners, It can be used as a chewable agent and the like, and can be used in the form of liquid, viscous liquid, gel, tablet and the like.

<Material of dental prosthesis>
The material of the dental prosthesis to which the microorganism adhesion inhibitor for dental prosthesis of the present invention is applied is not particularly limited, and examples thereof include polystyrene, polyethylene, polypropylene, polyurethane, polyethylene terephthalate, polymethyl methacrylate, nylon, polyimide, polycarbonate, Resins, such as polyether ketone, polyisobutylene, acrylic resin, and silicone resin, Metal materials, such as stainless steel, pure titanium, and a titanium alloy, Ceramic materials, such as zirconia, Inorganic materials, such as glass, etc. are mentioned.
Among these, it is preferable that the material of the dental prosthesis contains an acrylic resin from the viewpoint of adhesion with the microorganism adhesion inhibitor for dental prosthesis of the present invention.

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
For dental prosthesis of Example 1 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 it. A microorganism adhesion inhibitor was prepared.

Comparative Example 1
A microorganism adhesion inhibitor for dental prosthesis 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 reaction mixture was cooled to room temperature, purified water was added to the mixture to a total amount of 100 g, and the mixture was stirred to prepare a microorganism adhesion inhibitor for dental prosthesis of Example 2.

Example 3 and Comparative Example 2
A microorganism adhesion inhibitor for dental prostheses 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 microorganism adhesion inhibitor for dental prosthesis of Comparative Example 3 was prepared by stirring.

The following bacteria adhesion inhibition evaluation was performed about the microorganisms adhesion inhibitor for dental prostheses of Examples 1-3 and Comparative Examples 1-3 which were obtained by the above-mentioned method. 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 denture base resin (Akron No. 5 manufactured by GC Corporation, diameter 10 mm x length) The product was polymerized and molded to 2 mm and allowed to stand for 1 minute. In addition, the resin for denture base 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 denture base resin 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 resin for denture base, and cultured for 5 hours to adhere S. mutans to resin for denture base.

(Procedure 7) The S. mutans solution was removed, and the denture base resin 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 denture base resin, and allowed to stand for 10 minutes to stain S. mutans.
(Procedure 9) The Victoria Blue solution was removed, and the denture base resin was washed twice with 0.5 mL of the decolorizing solution.
(Procedure 10) The denture base resin 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 denture base resin, 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.
In the present evaluation, the larger the amount of attached bacteria, the higher the absorbance. Therefore, the lower the absorbance, the better the bacteria adhesion inhibitor for dental prostheses is.

Bacterial adhesion inhibition rate (%) = (A _c- A _s ) / A _c × 100
A _c: control (purified water) absorbance obtained from denture resin treated with A _s: Examples and Comparative Examples dental prosthesis for microbial attachment inhibitor treated with denture obtained absorbance from the resin of

  ADVANTAGE OF THE INVENTION According to this invention, the microorganism adhesion inhibitor for dental prostheses which is excellent in the adhesion suppression performance of microorganisms can be provided.

Claims (5)

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 The microorganism adhesion inhibitor for dental prostheses which is less than%.

(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 prosthesis microbe adhesion inhibitor according to claim 1, wherein the copolymer is (glyceryl glycerylamidoethyl / stearyl methacrylate) copolymer.   Furthermore, the microbe adhesion inhibitor for dental prostheses of Claim 1 or 2 which contains the wetting agent which consists of polyhydric alcohol.   The dental prosthesis microbe adhesion inhibitor according to claim 3, wherein the content of the wetting agent is 0.01 to 50% by mass.   The dental prosthesis microbe adhesion inhibitor according to any one of claims 1 to 4, wherein the material of the dental prosthesis contains an acrylic resin.