JP4836227B2 - Composition for preventing oral dryness and alleviating oral irritation - Google Patents

Description

  This product relates to a composition for oral cavity used for rinsing the oral cavity or brushing with a toothbrush or the like.

  Conventionally, oral compositions such as toothpaste, mouthwash, and mouth fresheners containing antibacterial agents, surfactants and fragrances for the purpose of preventing bad breath, preventing oral diseases such as gingivitis, and refreshing the mouth Things are used.

  In recent years, the dry state of the oral cavity called dry mice due to reduced saliva secretion due to stress and side effects of pharmaceuticals and mouth breathing during sleep has become widely known. Drying in the oral cavity is thought to cause various problems such as an increase in the number of bacteria in the oral cavity, an increase in tongue coating, a decrease in the barrier function in the oral cavity, the occurrence of bad breath and inflammation associated therewith.

Patent Document 1 discloses a liquid throat protecting composition containing glycerin and erythritol, and describes a moisturizing feeling due to glycerin. As described above, sugar alcohols such as glycerin, sorbitol, and xylitol have been conventionally blended as components for preventing dryness in the oral cavity, but the effect of preventing drying has not been sufficient. Further, in the dry mouse state, the mucous membrane in the oral cavity is often damaged, and when a fragrance is added for the purpose of obtaining a refreshing sensation, it is accompanied by irritation to the oral cavity. Regarding the alleviation of irritation in the oral cavity, Patent Document 2 discloses a composition for oral cavity in which flavor components such as peppermint oil and baking soda are mixed to alleviate bitterness and pain in the oral cavity. Patent Document 3 discloses menthol and ethanol. An oral composition is disclosed in which the irritation and hotness of the skin are alleviated with xylitol. However, the use of baking soda or xylitol for alleviating the feeling of irritation cannot ignore the change in flavor due to the taste of these ingredients.
JP 2004-359595 A JP 2002-212041 A JP 2000-178152 A

An object of the present invention is to prevent oral dryness and to reduce oral irritation without losing the refreshing feeling of the fragrance during use, and to prevent oral dryness and oral irritation alleviation Is to provide things.

As a result of intensive studies to solve the above-mentioned problems, the inventors alleviated the dry feeling in the oral cavity by blending a polymer of 2-methacryloyloxyethyl phosphorylcholine, and the refreshing feeling of the fragrance during use. The composition for preventing dryness in the oral cavity and alleviating oral irritation was completed.

That is, the present invention
The following general formula [I]

[Wherein, R ¹ represents a hydrogen atom or a methyl group, and R ² represents a — (CHR ⁵ ) m— group or a — (CH ₂ CHR ⁵ O) m—CH ₂ CHR ⁵ — group (provided that R ⁵ Represents a hydrogen atom or a methyl group, m represents an integer of 1 to 18), R ³ represents a — (CH ₂ ) n — group (where n represents an integer of 2 to 4), and R ⁴ Represents an alkyl group having 1 to 8 carbon atoms or a hydroxyalkyl group. A homopolymer of a phosphorylcholine-like group-containing (meth) acrylate represented by formula (I) or a copolymer of another vinyl monomer copolymerizable with the monomer represented by the general formula [I]. And the weight average molecular weight of the said polymer is 2,000-5,000,000, The composition for oral dry prevention and oral irritation relaxation characterized by the above-mentioned is provided.

The compound represented by the general formula [I] is represented by the following general formula [II]:

[Wherein, R ¹ represents a hydrogen atom or a methyl group, and n is an integer of 2 to 4. It is preferable that it is a phosphorylcholine similar group containing (meth) acrylate represented by this.

A particularly preferred form of the composition for preventing oral dryness and alleviating oral irritation according to the present invention is a phosphorylcholine-like group-containing (meth) acrylate represented by the general formula [II], wherein R ¹ is a methyl group and n is 2 A compound containing 0.001 to 5% by weight of a polymer of 2-methacryloyloxyethyl phosphorylcholine, ie, 2-methacryloyloxyethyl-2 ′-(trimethylammonio) ethyl phosphate, and 0 to 1% by weight of a fragrance. It is.

According to the present invention, there is provided a composition for preventing oral dryness and reducing oral irritation, which can prevent dryness in the oral cavity and can reduce irritation to the oral cavity without damaging the refreshing feeling due to the fragrance during use. Provided.

  The compound represented by the general formula [I] can be prepared by a conventional method, and its homopolymer or copolymer can also be synthesized by a conventional method. Among them, the polymer of 2-methacryloyloxyethyl phosphorylcholine may be a homopolymer of 2-methacryloyloxyethyl phosphorylcholine, or a copolymer of this monomer and a hydrophobic and / or ionic monomer. Good. Examples of the hydrophobic monomer include alkyl methacrylate. Examples of the ionic monomer include methacrylic acid and hydroxypropyltrimethylammonium methacrylate. The homopolymer or copolymer may be a commercially available product (“Lipidure Series” manufactured by NOF Corporation).

  The amount of the homopolymer or copolymer in the composition according to the present invention is 0.001 wt% to 5 wt%. If the blending amount is less than 0.001% by weight, drying prevention and irritation mitigating effect in the oral cavity cannot be expected, and if it exceeds 5% by weight, the feeling of use is deteriorated.

  The perfume ingredients used in the present invention are not particularly limited as long as they are usually blended into oral products for the purpose of obtaining a refreshing feeling. However, the following ingredients are used as a single product or a mixture as an example. .

  Natural fragrances such as peppermint oil, spearmint oil, anise oil, eucalyptus oil, thyme oil, sage oil, mint oil, and menthol, carvone, anethole, cineol, methyl salicylate, cinnamic aldehyde, eugenol, thymol, menthone, menthyl acetate, pinene Perfumes such as. Although these compounding quantities change with fragrance | flavors, 0.001-1 weight% is desirable.

  In the product of the present invention, components that are blended in a normal oral composition, for example, a wetting agent, a solvent, a surfactant, a buffering agent, a preservative, a bactericide, Anti-inflammatory agents, pigments, sweeteners, etc. can be blended.

  Although it does not specifically limit as a wetting agent, Polyhydric alcohols, such as propylene glycol, butylene glycol, pentylene glycol, dipropylene glycol, glycerin, polyethylene glycol, maltitol, xylitol, sorbitol, erythritol, hyaluronic acid, alginic acid, carrageenan, gellan gum And polysaccharides such as betaine.

  Although it does not specifically limit as a solvent, Purified water and ethanol are mentioned.

  The surfactant is not particularly limited, but polyoxyethylene hydrogenated castor oil, polyoxyethylene alkyl ether, sorbitan fatty acid ester and its ethylene oxide adduct, glycerin fatty acid ester and its ethylene oxide adduct, polyglycerin fatty acid ester and its ethylene oxide addition , Polyoxyethylene alkyl ether phosphate, polyoxyethylene polyoxypropylene copolymer, sucrose fatty acid ester, alkyl sulfate, polyoxyethylene alkyl ether sulfate, acyl amino acid salt, fatty acid amide propyl betaine, fatty acid amide betaine, etc. Is mentioned. In particular, polyoxyethylene hydrogenated castor oil is desirable in terms of stability in the preparation and influence on taste.

  Although it does not specifically limit as a buffering agent, Citric acid, phosphoric acid, malic acid, gluconic acid, those salts, etc. are mentioned, It is desirable to adjust pH to 5-8.

  Although not particularly limited as an antiseptic and fungicide, cetylpyridinium chloride, benzalkonium chloride, benzethonium chloride, chlorhexidine gluconate, chlorhexidine hydrochloride, isopropylmethylphenol, triclosan, hinokitiol, salicylic acid and its salt, benzoic acid and its salt, Parabens, lysozyme chloride, zinc chloride, alkyldiaminoethylglycine chloride and the like can be mentioned, and the amount is usually 0.01 to 1% by weight.

  Although it does not specifically limit as an anti-inflammatory agent, Glycyrrhizic acid and its salt, Glycyrrhetin, Azulene, (epsilon) -aminocaproic acid, Pyridoxine hydrochloride, allantoin, etc. are mentioned, Usually 0.01 to 1weight% can be mix | blended.

  Although it does not specifically limit as a sweetening agent, A saccharin, stevioside, sucralose, aspartame, a licorice extract etc. are mentioned, Usually 0.001-0.1weight% can be mix | blended.

The composition for preventing oral dryness and alleviating oral irritation in the present invention can be applied to oral products such as toothpaste, mouthwash, mouth freshener, mouthwash, and mouthwash.

  EXAMPLES The present invention will be described in detail below with reference to examples, but the present invention is not limited to these examples.

[Synthesis Example 1]
2-Methacryloyloxyethyl-2 ′-(trimethylammonio) ethyl phosphate 50 g as a monomer and 0.025 g azobisisobutyronitrile as a polymerization catalyst are dissolved in 100 g of an ethanol solvent, and this solution is placed in a reactor and purged with nitrogen. Thereafter, a polymerization reaction was carried out at 50 ° C. for 10 hours in a thermostatic bath. After completion of the polymerization, reprecipitation purification was performed using a mixed solvent of ethanol and diisopropyl ether, and the purified product was vacuum dried to obtain a polymer. The yield of the polymer was 92% by weight, and the weight average molecular weight determined by GPC analysis using polyethylene glycol as a standard substance was 550,000.

[Synthesis Example 2]
A copolymer was obtained in the same manner as in Synthesis Example 1, except that a mixture of 45 g of 2-methacryloyloxyethyl-2 ′-(trimethylammonio) ethyl phosphate and 5 g of n-butyl methacrylate was used as the monomer. The copolymer yield was 95% by weight, and the weight average molecular weight determined by GPC analysis was 610,000. Furthermore, the content of n-butyl methacrylate was confirmed to be 10.5% by weight by elemental analysis of the obtained polymer.

Examples 1 to 11
Various mouthwashes were prepared by blending the polymers of Synthesis Examples 1 and 2, Fragrances 1 and 2, and other components in the proportions shown in Tables 1 to 3. As the fragrance 1, a blended fragrance mainly composed of menthol, peppermint oil, and anethole was used. As the fragrance 2, a blended fragrance mainly composed of menthol, 1,8 cineole, thymol and methyl salicylate was used.

Comparative Examples 1 to 7
Without using the polymers of Synthesis Examples 1 and 2, Fragrances 1 and 2 and other components were blended in the proportions shown in Tables 1 to 3 to prepare various mouthwashes.

Evaluation test For the mouthwashes obtained in Examples and Comparative Examples, sensory evaluation was conducted by 8 panelists using the following supplementary methods on the relaxation effect and wet feeling. That is, the mouth was rinsed with 5 mL of mouthwash for 30 seconds and then discharged. The irritation during rinsing in the mouth and the moist feeling 5 minutes after vomiting were evaluated in three stages according to the following criteria, and the average points are shown in the table.

Irritation mitigating effect 3; less irritation in the oral cavity compared to the mouthwash liquid of Comparative Example 1; 1 intraoral irritation compared to the mouthwash liquid of Comparative Example 1 1; There are many irritation in the oral cavity.

Evaluation of wet feeling 3; high wet feeling compared to the mouthwash liquid of Comparative Example 1 2; wet feeling equivalent to the mouthwash liquid of Comparative Example 1 1; compared with the mouthwash liquid of Comparative Example 1 Low wet feeling.

The results of sensory evaluation are shown in the lower part of each table.

Evaluation Results The scores of Comparative Examples 2 to 7 were 2.0 or less, and compared with Comparative Example 1, the irritation feeling and the wet feeling were equal or less. On the other hand, the scores of Examples 1 to 11 were 2.2 or more, and it was found that the stimulation relaxation effect and the wet feeling were excellent as compared with Comparative Example 1.

  From the above results, it was found that by blending a polymer of 2-methacryloyloxyethyl phosphorylcholine, an effect of alleviating irritation without impairing the refreshing feeling of the fragrance and an effect of preventing dryness in the oral cavity can be obtained.

Claims (5)

The following general formula [I]

[Wherein, R ¹ represents a hydrogen atom or a methyl group, and R ² represents a — (CHR ⁵ ) m— group or a — (CH ₂ CHR ⁵ O) m—CH ₂ CHR ⁵ — group (provided that R ⁵ Represents a hydrogen atom or a methyl group, m represents an integer of 1 to 18), R ³ represents a — (CH ₂ ) n — group (where n represents an integer of 2 to 4), and R ⁴ Represents an alkyl group having 1 to 8 carbon atoms or a hydroxyalkyl group. A homopolymer of a phosphorylcholine-like group-containing (meth) acrylate represented by formula (I) or a copolymer of another vinyl monomer copolymerizable with the monomer represented by the general formula [I]. And the weight average molecular weight of the said polymer is 2,000-5,000,000, The composition for oral cavity dry prevention and oral cavity irritation relaxation characterized by the above-mentioned. The compound represented by the general formula [I] is represented by the following general formula [II]:

[Wherein, R ¹ represents a hydrogen atom or a methyl group, and n is an integer of 2 to 4. The oral cavity dry prevention and oral irritation according to claim 1, wherein the polymer has a phosphorylcholine-like group-containing (meth) acrylate and the polymer has a weight average molecular weight of 2,000 to 5,000,000. Relaxing composition. The composition for preventing dry mouth and reducing oral irritation according to claim 1, wherein the compound represented by the general formula [II] is 2-methacryloyloxyethyl phosphorylcholine. The composition for preventing oral dryness and reducing oral irritation according to any one of claims 1 to 3, comprising 0.001 to 5% by weight of the homopolymer or copolymer and 0 to 1% by weight of a fragrance. A composition for preventing dry mouth and reducing irritation in the oral cavity, comprising 0.001 to 5% by weight of a polymer of 2-methacryloyloxyethyl phosphorylcholine and 0 to 1% by weight of a fragrance.