Composition for inhibiting plaque formation

A composition of quaternary ammonium salts and cocoyl arginine ethyl DL-pyrrolidone carboxylate effectively targets Fusobacterium to inhibit plaque formation, achieving efficient plaque suppression through synergistic or additive bactericidal actions.

JP2025094780APending Publication Date: 2025-06-25SUNSTAR INC
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Patent Information

Application Number
JP2023210526
Authority / Receiving Office
JP · JP
Patent Type
Applications
Current Assignee / Owner
Filing Date
2023-12-13
Publication Date
2025-06-25

AI Technical Summary

Technical Problem

Existing compositions are ineffective in efficiently suppressing plaque formation, particularly by targeting Fusobacterium, which is a key bacterium involved in the initial stage of plaque development.

Method used

A composition combining quaternary ammonium salts, such as cetylpyridinium chloride, with cocoyl arginine ethyl DL-pyrrolidone carboxylate (CAE) is used, with specific ratios and concentrations to enhance bactericidal activity against Fusobacterium.

Benefits of technology

The combination effectively sterilizes Fusobacterium, thereby significantly suppressing plaque formation, demonstrating synergistic or additive bactericidal effects depending on the chain length of CAE used.

✦ Generated by Eureka AI based on patent content.

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Abstract

To provide a composition for inhibiting plaque formation.SOLUTION: A composition for inhibiting plaque formation comprises a quaternary ammonium salt, and cocoyl arginine ethyl DL-pyrrolidone carboxylate (cocoyl arginine ethyl PCA salt) represented by general formula (1). In the formula, R represents CnH2n+1, and n represents 7, 9, 11, 13, or 15.SELECTED DRAWING: None
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Description

Technical Field

[0001] The present disclosure relates to a composition for suppressing plaque formation and the like. Specifically, it relates to a composition for suppressing plaque formation containing a quaternary ammonium salt and cocoyl arginine ethyl DL-pyrrolidone carboxylate, and the like.

Background Art

[0002] Plaque (dental plaque) is considered to be a cause of dental caries and periodontal disease.

[0003] Generally speaking, plaque is formed as follows. That is, first, a thin film of protein derived from saliva and physiological gingival sulcus exudate called "pellicle" is formed on the surface of the tooth, and facultative anaerobic bacteria (initial adherent bacteria) such as Streptococcus attach to the tooth surface through the pellicle. Bacteria such as Fusobacterium that co-aggregate with various oral bacteria attach to these initial adherent bacteria, and late adherent bacteria such as Porphyromonas gingivalis and Treponema denticola, which are anaerobic bacteria, further attach and aggregate through the bacteria, and the plaque matures.

Prior Art Documents

Non-Patent Documents

[0004]

Non-Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0005] An object of the present invention is to provide a composition for suppressing plaque formation.

Means for Solving the Problems

[0006] The inventors have found that when a quaternary ammonium salt and a specific cocooyl arginine ethyl DL-pyrrolidone carboxylate (cocooyl arginine ethyl PCA salt) are used in combination, they exhibit excellent bactericidal activity against Fusobacterium, which is responsible for the initial stage of plaque formation, and have further improved it.

[0007] This disclosure includes, for example, the subject matter described in the following items. Item 1. A composition for suppressing plaque formation, containing a quaternary ammonium salt and cocooyl arginine ethyl DL-pyrrolidone carboxylate (cocooyl arginine ethyl PCA salt) represented by the following general formula (1). [Chemical formula] [In the formula, R represents C n H 2n+1 and n represents 7, 9, 11, 13, or 15.] Item 2. With respect to the total content of the cocooyl arginine ethyl PCA salt represented by the general formula (1) contained, the content of the cocooyl arginine ethyl PCA salt in which R is C9H 19 is 0 to 30% by mass, and the content of the cocooyl arginine ethyl PCA salt in which R is C 11 H 23 is 40% by mass or more, the composition according to Item 1. Item 3. With respect to 1 part by mass of the quaternary ammonium salt, the total content of the cocooyl arginine ethyl PCA salt in which R is C 13 H 27 and the cocooyl arginine ethyl PCA salt in which R is C 15 H 31 is 0.50 part by mass or less, the composition according to Item 1 or 2. Item 4. The composition according to any one of Items 1 to 3, wherein the quaternary ammonium salt is cetylpyridinium chloride. Item 5. The composition according to any one of Items 1 to 4, which is for killing Fusobacterium.

Advantages of the Invention

[0008] There is provided a method for efficiently sterilizing Fusobacterium, which is a mediating bacterium in plaque formation. As a result, it is also possible to efficiently suppress plaque formation.

Brief Description of the Drawings

[0009]

Figure 1

Figure 2

Figure 3

Figure 4

Modes for Carrying Out the Invention

[0010] Hereinafter, each embodiment included in the present disclosure will be described in more detail. The composition for suppressing plaque formation included in the present disclosure contains a quaternary ammonium salt and cocoyl arginine ethyl DL-pyrrolidone carboxylate. In this specification, the composition may be referred to as "the composition for suppressing plaque formation of the present disclosure".

[0011] Examples of the quaternary ammonium salt include alkylpyridinium salts having 10 to 16 carbon atoms. Examples of the alkylpyridinium salts having 10 to 16 carbon atoms include cetylpyridinium chloride, dodecylpyridinium chloride, and the like. These can be used alone or in combination of two. Among them, cetylpyridinium chloride is preferable.

[0012] Cocoyl arginine ethyl DL-pyrrolidone carboxylate (which may be referred to as cocoyl arginine ethyl PCA salt, or CAE, etc. in this specification) is represented by the following general formula (1). [Chemical formula] [In the formula, R represents C n H 2n+1 , and n represents 7, 9, 11, 13, or 15.]

[0013] Coconut oil arginine ethyl · DL - pyrrolidone carboxylate means that when R is C7H 15 (n = 7) CAE, C9H 19 (n = 9) CAE, C 11 H 23 (n = 11) CAE, C 13 H 27 (n = 13) CAE, and C 15 H 31 (n = 15) CAE, and can be at least one selected from the group consisting of them. Coconut oil arginine ethyl · DL - pyrrolidone carboxylate may be a single species or a combination of two or more species.

[0014] Among them, R is preferably C9H 19 (n = 9), and C 11 H 23 (n = 11), and C 11 H 23 (n = 11) is more preferable.

[0015] Coconut oil arginine ethyl · DL - pyrrolidone carboxylate is not particularly limited, such as a synthetic product, a commercially available product, etc. For example, as a commercially available coconut oil arginine ethyl · DL - pyrrolidone carboxylate, "CAE" manufactured by Ajinomoto Co., Inc. can be used. Also, coconut oil arginine ethyl · DL - pyrrolidone carboxylate may be a further purified product of a commercially available coconut oil arginine ethyl · DL - pyrrolidone carboxylate.

[0016] In the composition for suppressing plaque formation of the present disclosure, with respect to 1 part by mass of the quaternary ammonium salt, in the general formula (1), when R is C 13 H 27Cocoyl arginine ethyl PCA salt where (n = 13) and C 15 H 31 The total content of cocoyl arginine ethyl PCA salt where (n = 15) is preferably 0.50 part by mass or less. The upper or lower limit of the range may be, for example, 0, 0.0001, 0.001, 0.01, 0.1, 0.2, 0.21, 0.22, 0.23, 0.24, 0.25, 0.26, 0.27, 0.28, 0.29, 0.3, 0.31, 0.32, 0.33, 0.35, 0.38, 0.40, 0.43, 0.45 or 0.49 part by mass. For example, the range may be 0 to 0.50 part by mass, or 0 to 0.35 part by mass.

[0017] In the plaque formation inhibitory composition of the present disclosure, for 1 part by mass of the quaternary ammonium salt, in general formula (1), R is C 13 H 27 The content of cocoyl arginine ethyl PCA salt where (n = 13) can be, for example, 0.50 part by mass or less. The upper or lower limit of the range may be, for example, 0, 0.0001, 0.001, 0.01, 0.05, 0.1, 0.2, 0.21, 0.22, 0.23, 0.24, 0.25, 0.26, 0.27, 0.28, 0.29, 0.30, 0.31, 0.32, 0.33, 0.34, 0.35, 0.36, 0.37, 0.38, 0.39, 0.40, 0.41, 0.42, 0.43, 0.44, 0.45, 0.46, 0.47, 0.48 or 0.49 part by mass. For example, the range may be 0 to 0.50 part by mass, or 0 to 0.3 part by mass.

[0018] In the plaque formation inhibitory composition of the present disclosure, for 1 part by mass of the quaternary ammonium salt, in general formula (1), R is C 15 H 31The content of cocoyl arginine ethyl PCA salt where (n = 15) can be, for example, 0.50 parts by mass or less. The upper or lower limit of this range can be, for example, 0, 0.0001, 0.001, 0.01, 0.05, 0.1, 0.2, 0.21, 0.22, 0.23, 0.24, 0.25, 0.26, 0.27, 0.28, 0.29, 0.30, 0.31, 0.32, 0.33, 0.34, 0.35, 0.36, 0.37, 0.38, 0.39, 0.40, 0.41, 0.42, 0.43, 0.44, 0.45, 0.46, 0.47, 0.48 or 0.49 parts by mass. For example, this range may be 0 to 0.50 parts by mass, or may be 0 to 0.3 parts by mass.

[0019] In the plaque formation inhibitory composition of the present disclosure, for 1 part by mass of the quaternary ammonium salt, in the general formula (1), R is C9H 19 (n = 9) of cocoyl arginine ethyl PCA salt and C 11 H 23 The total content of cocoyl arginine ethyl PCA salt where (n = 11) is not particularly defined, but can be, for example, 0.01 to 10 parts by mass, more preferably 0.05 to 5.0 parts by mass, and still more preferably 0.1 to 2.0 parts by mass.

[0020] In the plaque formation inhibitory composition of the present disclosure, for 1 part by mass of the quaternary ammonium salt, in the general formula (1), R is C9H 19 The content of cocoyl arginine ethyl PCA salt where (n = 9) is not particularly defined, but can be, for example, 0.001 to 2.0 parts by mass, more preferably 0.005 to 1.0 parts by mass, and still more preferably 0.01 to 0.5 parts by mass.

[0021] In the plaque formation inhibitory composition of the present disclosure, for 1 part by mass of the quaternary ammonium salt, in the general formula (1), R is C 11 H 23(n = 11) The content of cocoyl arginine ethyl PCA salt is not particularly defined, but can be, for example, 0.005 to 10.0 parts by mass, more preferably 0.01 to 5.0 parts by mass, and still more preferably 0.05 to 2.0 parts by mass.

[0022] In the plaque formation inhibitory composition of the present disclosure, for 1 part by mass of the quaternary ammonium salt, in the general formula (1), R is C7H 15 (n = 7) The content of cocoyl arginine ethyl PCA salt can be, for example, 1.0 part by mass or less. The upper or lower limit of this range can be, for example, 0, 0.01, 0.05, 0.1, 0.2, 0.3, 0.4, 0.5, 0.55, 0.6, 0.65, 0.7, 0.75, 0.80, 0.85, 0.90 or 0.95 parts by mass. For example, this range can be 0 to 1.00 part by mass.

[0023] In the plaque formation inhibitory composition of the present disclosure, the total content of the above-mentioned cocoyl arginine ethyl PCA salt with respect to 1 part by mass of the quaternary ammonium salt is not particularly defined, but can be 0.01 to 5.0 parts by mass, more preferably 0.1 to 10 parts by mass, and still more preferably 0.3 to 5.0 parts by mass.

[0024] The content of the quaternary ammonium salt contained in the composition for suppressing plaque formation of the present disclosure can be, for example, about 0.001 to 0.5% by mass. The upper or lower limit of the range can be, for example, 0.0015, 0.003, 0.005, 0.0075, 0.01, 0.02, 0.03, 0.04, 0.05, 0.06, 0.07, 0.08, 0.09, 0.1, 0.11, 0.12, 0.13, 0.14, 0.15, 0.16, 0.17, 0.18, 0.19, 0.2, 0.21, 0.22, 0.23, 0.24, 0.25, 0.26, 0.27, 0.28, 0.29, 0.3, 0.31, 32, 0.33, 0.34, 0.35, 0.36, 0.37, 0.38, 0.39, 0.4, 0.41, 0.42, 0.43, 0.44, 0.45, 0.46, 0.47, 0.48, or 0.49% by mass. For example, the range may be about 0.005 to 0.5% by mass, or about 0.01 to 0.3% by mass.

[0025] The total content of the above-mentioned cocoyl arginine ethyl DL-pyrrolidone carboxylate contained in the plaque formation-inhibiting composition of the present disclosure can be, for example, about 0.001 to 1.0% by mass. The upper or lower limit of this range can be, for example, 0.002, 0.003, 0.004, 0.005, 0.006, 0.007, 0.008, 0.009, 0.01, 0.02, 0.03, 0.04, 0.05, 0.06, 0.07, 0.08, 0.09, 0.1, 0.11, 0.12, 0.13, 0.14, 0.15, 0.16, 0.17, 0.18, 0.19, 0.2, 0.21, 0.22, 0.23, 0.24, 0.25, 0.26, 0.27, 0.28, 0.29, 0.3, 0.31, 32, 0.33, 0.34, 0.35, 0.36, 0.37, 0.38, 0.39, 0.4, 0.41, 0.42, 0.43, 0.44, 0.45, 0.46, 0.47, 0.48, 0.49, 0.50, 0.51, 0.52, 0.53, 0.54, 0.55, 0.56, 0.57, 0.58, 0.59, 0.60, 0.61, 0.62, 0.63, 0.64, 0.65, 0.67, 0.68, 0.69, 0.70, 0.71, 0.72, 0.73, 0.74, 0.75, 0.76, 0.77, 0.78, 0.79, 0.80, 0.81, 0.82, 0.83, 0.84, 0.85, 0.86, 0.87, 0.88, 0.89, 0.90, 0.91, 0.92, 0.93, 0.94, 0.95, 0.96, 0.97, 0.98 or 0.99% by mass. For example, this range may be about 0.005 to 0.3% by mass, or about 0.01 to 0.1% by mass.

[0026] Per the total content of the above-mentioned cocoyl arginine ethyl DL-pyrrolidone carboxylate contained in the plaque formation-inhibiting composition of the present disclosure, in general formula (1), R is C9H 19 (where n = 9), the content of CAE may be, for example, about 0 to 30% by mass. The upper or lower limit of this range may be about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, or 25% by mass. For example, this range may be about 1 to 25% by mass. In other words, in the plaque formation-inhibiting composition of the present disclosure, in general formula (1), R is C9H19 (For n = 9), the content of CAE may be, for example, about 0 to 0.15% by mass. The upper or lower limit of this range may be about 0.0001, 0.001, 0.002, 0.003, 0.004, 0.005, 0.006, 0.007, 0.008, 0.009, 0.01, 0.05, or 0.1% by mass. For example, this range may be about 0.0001 to 0.1% by mass.

[0027] Per total content of the above-described cocoyl arginine ethyl DL-pyrrolidone carboxylate contained in the plaque formation-inhibiting composition of the present disclosure, in general formula (1), R is C 11 H 23 (For n = 11), the content of CAE may be, for example, about 40 to 100% by mass. The upper or lower limit of this range may be, for example, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, or 95% by mass. For example, this range may be about 50 to 95% by mass. In other words, in general formula (1) contained in the plaque formation-inhibiting composition of the present disclosure, R is C 11 H 23 (For n = 11), the content of CAE may be, for example, about 0.002 to 0.5% by mass. The upper or lower limit of this range may be, for example, 0.01, 0.015, 0.02, 0.025, 0.03, 0.035, 0.04, 0.045, 0.05, 0.1, 0.2, 0.3, or 0.4% by mass. For example, this range may be about 0.01 to 0.4% by mass.

[0028] Per total content of the above-described cocoyl arginine ethyl DL-pyrrolidone carboxylate contained in the plaque formation-inhibiting composition of the present disclosure, in general formula (1), R is C7H 15 (For n = 7), the content of CAE may be, for example, about 0 to 30% by mass. The upper or lower limit of this range may be about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, or 29% by mass. For example, this range may be about 1 to 15% by mass. In other words, in the general formula (1) included in the plaque formation inhibitory composition of the present disclosure, R is C7H 15 (n = 7) The content of CAE may be, for example, about 0 to 0.075% by mass. The upper or lower limit of the range may be about 0.0001, 0.001, 0.002, 0.003, 0.004, 0.005, 0.006, 0.007, 0.008, 0.009, 0.01, or 0.05% by mass. For example, the range may be about 0.0001 to 0.05% by mass.

[0029] Based on the total content of the above-mentioned cocoyl arginine ethyl · DL-pyrrolidone carboxylate contained in the plaque formation inhibitory composition of the present disclosure, in the general formula (1), R is C 13 H 27 (n = 13) The content of CAE may be, for example, about 0 to 30% by mass. The upper or lower limit of the range may be about 1, 5, 10, 15, 20, or 25% by mass. For example, the range may be about 1 to 25% by mass. In other words, in the general formula (1) included in the plaque formation inhibitory composition of the present disclosure, R is C 13 H 27 (n = 13) The content of CAE may be about 0 to 0.15% by mass. The upper or lower limit of the range may be about 0.0001, 0.001, 0.002, 0.003, 0.004, 0.005, 0.006, 0.007, 0.008, 0.009, 0.01, 0.05, or 0.1% by mass. For example, the range may be about 0.0001 to 0.1% by mass.

[0030] Based on the total content of the above-mentioned cocoyl arginine ethyl · DL-pyrrolidone carboxylate contained in the plaque formation inhibitory composition of the present disclosure, in the general formula (1), R is C 15 H 31 (n = 15) The content of CAE may be, for example, about 0 to 10% by mass. The upper or lower limit of the range may be about 1, 2, 3, 4, 5, 6, 7, 8, or 9% by mass. For example, the range may be about 1 to 9% by mass. In other words, in the general formula (1) included in the plaque formation inhibitory composition of the present disclosure, R is C 15 H 31 (n = 15) The content of CAE may be, for example, about 0 to 0.05% by mass. The upper or lower limit of the range may be about 0.0001, 0.001, 0.002, 0.003, 0.004, 0.005, 0.006, 0.007, 0.008, 0.009, or 0.01% by mass. For example, the range may be about 0.0001 to 0.01% by mass.

[0031] Based on the total content of the above-mentioned cocoyl arginine ethyl DL-pyrrolidone carboxylate included in the plaque formation inhibitory composition of the present disclosure, in the general formula (1), R is C 13 H 27 (n = 13) CAE and C 15 H 31 (n = 15) The total content of CAE may be, for example, about 0 to 30% by mass. The upper or lower limit of the range may be about 1, 5, 10, 15, 20, or 25% by mass. For example, the range may be about 1 to 25% by mass. In other words, in the general formula (1) included in the plaque formation inhibitory composition of the present disclosure, R is C 13 H 27 (n = 13) CAE and C 15 H 31 (n = 15) The total content of CAE may be, for example, about 0 to 0.15% by mass. The upper or lower limit of the range may be about 0.0001, 0.001, 0.002, 0.003, 0.004, 0.005, 0.006, 0.007, 0.008, 0.009, 0.01, 0.05, or 0.1% by mass. For example, the range may be about 0.0001 to 0.1% by mass.

[0032] Based on the total content of the above-mentioned cocoyl arginine ethyl DL-pyrrolidone carboxylate included in the plaque formation inhibitory composition of the present disclosure, in the general formula (1), R is C9H 19 (n = 9) CAE and C 11 H 23The total content of CAE (n=11) may be, for example, about 40 to 100 mass%. The upper or lower limit of the range may be, for example, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, or 95 mass%. For example, the range may be about 50 to 95 mass%. In other words, the plaque formation-suppressing composition of the present disclosure is a compound represented by the general formula (1), in which R is CH 19 (n=9) CAE and C 11 H 23 The total content of CAE (n=11) is not particularly limited, but may be about 0.001 to 1 mass %, more preferably 0.005 to 0.5 mass %, and further preferably about 0.01 to 0.2 mass %. The composition for inhibiting plaque formation according to the present disclosure is also a compound represented by the general formula (1), wherein R is CH 19 (n=9) CAE and C 11 H 23 (n=11) CAE, R is CH 19 (n=9) CAE C per 1 mass part 11 H 23 (n=11) The content of CAE can be, for example, about 1 to 100 parts by mass. The upper or lower limit of the range may be, for example, 2, 3, 4, 5, 6, 7, 8, 9, 10, 20, 30, 40, 50, 60, 70, 80, or 90 parts by mass. For example, the range may be about 1 to 5 parts by mass.

[0033] The total content of the above-mentioned ethyl cocoyl arginine·DL-pyrrolidone carboxylate contained in the composition for inhibiting plaque formation of the present disclosure is 15 (n=7) CAE, C9H 19 (n=9) CAE and C 11 H 23 The total content of CAE (n=11) may be, for example, about 40 to 100 mass%. The upper or lower limit of the range may be, for example, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, or 95 mass%. For example, the range may be about 50 to 95 mass%. In other words, in the general formula (1) included in the plaque formation inhibitory composition of the present disclosure, R is C7H 15 (n = 7) of CAE, C9H 19 (n = 9) of CAE and C 11 H 23 (n = 11) of the total content of CAE may be about 0.002 to 0.5% by mass. The upper or lower limit of the range may be, for example, 0.01, 0.015, 0.02, 0.025, 0.03, 0.035, 0.04, 0.045, 0.05, 0.1, 0.2, 0.3, or 0.4% by mass. For example, the range may be about 0.01 to 0.4% by mass.

[0034] In the general formula (1) included in the plaque formation inhibitory composition of the present disclosure, R is C 13 H 27 (n = 13) of CAE and C 15 H 31 (n = 15) of the total content of CAE, the content of R being C 11 H 23 (n = 11) of CAE may be, for example, 1.3 parts by mass or more. The upper or lower limit of the range may be, for example, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 25, or 30 parts by mass. For example, the range may be about 1.3 to 30 parts by mass.

[0035] In the general formula (1) included in the plaque formation inhibitory composition of the present disclosure, R is C 13 H 27 (n = 13) of CAE and C 15 H 31 (n = 15) of the total content of CAE, the content of R being C9H 19 (n = 9) of CAE and C 11 H 23 (n = 11) of CAE may be, for example, 1.5 parts by mass or more. The upper or lower limit of the range may be, for example, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, 25, or 30 parts by mass. For example, the range may be about 1.5 to 30 parts by mass.

[0036] The composition for suppressing plaque formation of the present disclosure contains the above-mentioned quaternary ammonium salt and cocoyl arginine ethyl DL-pyrrolidone carboxylate, and may further contain other components. Examples of such other components include pharmacologically or food hygienically acceptable bases, carriers, solvents, dispersants, emulsifiers, buffers, stabilizers, excipients, binders, disintegrants, lubricants, thickeners, surfactants, antioxidants, preservatives, coating agents, coloring agents, fragrances, pH adjusters, etc., and further components and materials that can be used as foods or feeds are exemplified. These components can be used alone or in combination of two or more.

[0037] The composition for suppressing plaque formation of the present disclosure can be, for example, a solid composition, a liquid composition, or the like. The composition for suppressing plaque formation of the present disclosure can be used, for example, as pharmaceuticals, quasi-drugs, etc. Further, the form of the composition for suppressing plaque formation of the present disclosure is not particularly limited, but according to a conventional method, for example, it can be made into forms (dosage forms) such as ointments, pastes, pastes, gels, liquids, sprays, mouthwashes, liquid dentifrices, dentifrices, gums, troches, etc. Among them, mouthwashes, liquid dentifrices, dentifrices, ointments, pastes, liquids, and gels are preferred.

[0038] The composition for suppressing plaque formation of the present disclosure can be prepared by a known method or a method easily conceivable from a known method. For example, it can be prepared by appropriately mixing the above-mentioned quaternary ammonium salt and cocoyl arginine ethyl DL-pyrrolidone carboxylate, and other components as necessary.

[0039] In addition, examples of the microorganisms targeted by the composition for suppressing plaque formation of the present disclosure include Fusobacterium, Aggregatibacter, etc. Here, the Fusobacterium is not particularly limited as long as it is a bacterium of the genus Fusobacterium that is a mediating bacterium between early adherent bacteria and late adherent bacteria in plaque formation, but Fusobacterium nucleatum is preferably exemplified.

[0040] Since the composition for suppressing plaque formation of the present disclosure has a bactericidal effect on Fusobacterium, it can also be preferably used for killing Fusobacterium.

[0041] The composition for suppressing plaque formation of the present disclosure can be used as an oral composition.

[0042] The subject to which the composition for suppressing plaque formation of the present disclosure is applied is not particularly limited, and humans and non-human mammals are preferably mentioned. As non-human mammals, livestock and pets are preferable, and more specifically, for example, dogs, cats, mice, rats, horses, cows, sheep, monkeys, etc. can be mentioned. In addition, since the composition for suppressing plaque formation of the present disclosure contains the above-mentioned quaternary ammonium salt and cocoyl arginine ethyl DL-pyrrolidone carboxylate and can efficiently kill Fusobacterium, which is a mediating bacterium, it can be said that it is particularly suitable for applying to the oral cavity of a subject in which plaque has not been formed or is in the process of formation (late adherent bacteria are not attached).

[0043] In addition, in this specification, “comprising” includes “consisting essentially of” and “consisting of” (The term “comprising” includes “consisting essentially of” and “consisting of.”). Further, the present disclosure includes all combinations of any of the constituent elements described in this specification.

[0044] In addition, the various characteristics (properties, structures, functions, etc.) described for each of the above-described embodiments of the present disclosure may be combined in any way in identifying the subject matter encompassed by the present disclosure. That is, the present disclosure includes all subject matters consisting of any combination of the various characteristics that can be combined described in this specification.

Examples

[0045] The content of the present disclosure will be specifically described using the following experimental examples. However, the present disclosure is not limited thereto in any way. In the following, unless otherwise specified, the experiments are carried out under atmospheric pressure and normal temperature conditions. Also, unless otherwise specified, "%" means "% by mass".

[0046] Experimental Example 1: Examination of the effect of the difference between CAE used in combination with CPC and the side chain R in CAE on the sterilization of Fusobacterium Cetylpyridinium chloride (CPC) and cocooyl arginine ethyl DL-pyrrolidone carboxylate (cocooyl arginine ethyl PCA salt; CAE, manufactured by Ajinomoto Co., Inc.) were each dissolved in water to a concentration of 0.05% by mass and 0.04% by mass, respectively, and used as a bactericidal agent solution. Similarly, CAEs with different side chains n were also prepared to a concentration of 0.04% by mass each. In the figure, n represents the number of carbon atoms of the alkyl group represented by R of CAE represented by the general formula (1). Also, in the figure, it was found that "CAE" is a CAE mixture containing 55.0% of CAE with n = 11, 24.0% of CAE with n = 13, 8.0% of CAE with n = 7, 9.0% of CAE with n = 9, and 4.0% of CAE with n = 15 by conventional analysis.

[0047] Fusobacterium nucleatum ssp. nucleatum ATCC23726 was used as the test bacterium.

[0048] The test bacterium was inoculated into 10 ml of GAM broth medium (Nissui Pharmaceutical Co., Ltd.) and anaerobically cultured at 37°C for 2 days. The culture solution was used as a test bacterium solution (adjusted to about 1×10 9 CFU / ml).

[0049] 200 μl of the test bacterium solution was mixed with 200 μl of the bactericidal agent solution. 100 μl of the mixed solution was collected 60 seconds after mixing, and 900 μl of drug-inactivated PBS added with soybean lecithin and Tween 80 to final concentrations of 0.07% and 0.5%, respectively, was added (the mixed solution was diluted 10-fold) to inactivate the bactericidal action of the bactericidal agent. Also, the mixed solution was serially diluted with drug-inactivated PBS, and the mixed solution was diluted 101 ~10 7 diluted up to 10-fold (step mixture diluent).

[0050] 100 μl each of the prepared step mixture diluent was spread on a sheep blood agar medium for CDC anaerobic bacteria (Nippon Becton Dickinson Co., Ltd.), and anaerobically cultured at 37°C for 3 days, and the viable cell count was counted.

[0051] The results are shown in Fig. 1. Fig. 1 is a graph with the number of sterilization digits on the vertical axis. The number of sterilization digits was calculated by subtracting Log[viable cell count (CFU / ml)] when using the disinfectant solution from Log[viable cell count (CFU / ml)] when using water as a control. A higher number of sterilization digits indicates a higher sterilization effect. As shown in Fig. 1, it was found that CAE showed a remarkable sterilization effect when used in combination with CPC. Furthermore, CAE with R being C9H 19 (n = 9) or C 11 H 23 (n = 11) was found to show a remarkable sterilization effect when used in combination with CPC.

[0052] When two types of antibiotics (A and B) are used in combination, the FIC index is known as an index for evaluating the way the effect appears (Yutaka Toyokawa et al., Problems in the checkerboard method using a two-fold dilution series for measuring the combined effect, CHEMOTHERAPY / Vol. 42 (1994) No. 7). Usually, the FIC index is calculated by the following formula using the MIC (minimum inhibitory concentration). FIC index = (MIC when using drug A in combination / MIC of drug A alone) + (MIC when using drug B in combination / MIC of drug B alone) Applying this concept, the synergistic and additive effects when CPC and CAE were used in combination were determined by the following formula and evaluation criteria. (Viable cell count when using CPC and CAE in combination / Viable cell count of CPC alone) + (Viable cell count when using CPC and CAE in combination / Viable cell count of CAE alone) <Evaluation criteria> 0.5 or less: Synergistic effect 0.5 < ~1 or less: Additive effect 1<~2 or less: Irrelevant 2< : Antagonistic

[0053]

Table 1

[0054] As shown in Table 1, when R is C9H 19 (n = 9), or C 11 H 23 (n = 11), the CAE shows a synergistic effect with CPC. However, when R is C 13 H 27 (n = 13), or C 15 H 31 (n = 15), the CAE was suggested to show an antagonistic effect against CPC. On the other hand, when R is C7H 15 (n = 7), an additive effect was shown.

[0055] Experimental Example 2: Examination of the effect of the n = 11 composition ratio in CAE on the bactericidal effect against Fusobacterium The bactericidal effects of various bactericidal agent solutions were evaluated in the same manner as in Experimental Example 1, except that the contact time was changed to 30 seconds and the test bacterium was changed to Fusobacterium nucleatum ssp. nucleatum ATCC25586. The bactericidal agent solutions were prepared by mixing a CAE mixture (the same as that used in Experimental Example 1) and CAE with n = 11 and dissolving them in water so that the CAE with n = 11 had each concentration. The specific preparation method is described at the bottom of Table 1.

[0056] The composition ratios of each chain length in CAE of each bactericidal agent solution are shown in Table 2. All aqueous solutions have a concentration in which the solute is approximated to 0.04% (w / w).

[0057]

Table 2

[0058] As shown in Figure 2, the bactericidal effect of CAE combined with the bactericide CPC is C 11 H 23It was found that the compositional ratio of CAE where (n = 11) increases significantly.

[0059] Experimental Example 3: Examination of the difference in bactericidal effect against Fusobacterium at the combined concentration of CAE and CPC In the same manner as in Experimental Example 1, only the test bacterium was changed to Fusobacterium nucleatum ssp. nucleatum ATCC25586, and the bactericidal effects of various bactericidal agent solutions were evaluated. The bactericidal agent solutions were prepared with water so that the CAE mixture (the same as that used in Experimental Example 1) was 0.04, 0.08, and 0.16% by mass. For CPC, it was prepared at 0.02 and 0.05% by mass. When CPC and CAE were used in combination, they were prepared to reach the final concentration. Note that A in the figure indicates the same as the bactericidal agent solution A used in Example 2.

[0060] Table 3 shows the content ratio of CAE with each chain length in each bactericidal agent solution.

[0061]

Table 3

[0062] As shown in Figure 3, compared with 0.08%_A, 0.05%CPC + 0.08%_A and 0.02%CPC + 0.08%_A have a reduced number of bactericidal digits, so it was confirmed that the actions of CPC and CAE are antagonistic. Similarly, compared with 0.16%_A, 0.05%CPC + 0.16%_A has a reduced number of bactericidal digits, so it was confirmed that the actions of CPC and CAE are antagonistic. On the other hand, compared with 0.04%_A, 0.05%CPC + 0.04%_A has an increased number of bactericidal digits, so it was confirmed that the actions of CPC and CAE are not antagonistic. From these facts, R is C 13 H 27 (n = 13) of CAE and C 15 H 31When the total amount of CAE is (n = 15), it shows no antagonistic effect when it is 0.24 parts by mass per 1 part by mass of CPC1, while it shows an antagonistic effect when it is 0.44 parts by mass.

[0063] Experimental Example 4: Examination of the influence of the composition ratios of n = 9 and n = 11 in CAE on the bactericidal effect against Fusobacterium In the same manner as in Experimental Example 1, only the test bacterium was changed to Fusobacterium nucleatum ssp. nucleatum ATCC25586, and the bactericidal effects of various bactericidal liquid preparations were evaluated. The bactericidal liquid preparations were prepared by dissolving CAE in water. In the figure, A indicates the same as the bactericidal liquid preparation A used in Example 2. Further, the bactericidal liquid preparation E was an aqueous solution prepared by mixing a 0.04% (w / w) aqueous solution of CAE with n = 9 (C9H19) and the D liquid in Table 2 at a ratio of 3:1, and a CAE mixture containing 25% of CAE with n = 9 and 75% of CAE with n = 11 was prepared.

[0064] As shown in Fig. 4, it was found that the CAE mixture containing 25% of CAE with n = 9 and 75% of CAE with n = 11 had a particularly strong bactericidal effect.

Claims

1. A quaternary ammonium salt, and a composition for suppressing plaque formation containing 【Chemical 1】 [wherein, R represents C n H 2n+1 ; and n represents 7, 9, 11, 13, or 15.] cocoyl arginine ethyl DL-pyrrolidone carboxylate (cocoyl arginine ethyl PCA salt) represented by the following general formula (1).

2. R is C 9 H 19 The content of co-coil arginine ethyl PCA salt which is is 0 to 30% by mass, and R is C 11 H 23 The composition according to claim 1, wherein the content of the coiled arginine ethyl PCA salt, which is with respect to the total content of cocoyl arginine ethyl PCA salt represented by the general formula (1) contained The total content of cocooyl arginine ethyl PCA salt where R is C 13 H 27 and cocooyl arginine ethyl PCA salt where R is C 15 H 31 is 0.50 part by mass or less per 1 part by mass of the quaternary ammonium salt, the composition according to claim 1 or 2.

3.

4. The composition according to claim 1 or 2, wherein the quaternary ammonium salt is cetylpyridinium chloride.

5. The composition according to claim 1 or 2, which is for killing Fusobacterium.