JP7342688B2 - Oral composition - Google Patents

Description

The present invention relates to an oral composition containing allantoin and/or tranexamic acid, which is suppressed from discoloration and discoloration even after storage, has excellent appearance stability, and has good taste.

Alleviation of inflammation is effective in preventing periodontal diseases, and it is known to include active ingredients having an amino group, such as tranexamic acid and allantoin, as anti-inflammatory agents in oral compositions.
On the other hand, in oral compositions, fragrances are essential for preparing highly palatable preparations, and among these, compounds with aldehyde groups and mentofuran are extremely important ingredients both in terms of efficacy and ease of use. It is an indispensable flavor component for the preparation of oral compositions with high palatability.
However, when a fragrance is blended with an active ingredient that has an amino group in an oral composition, it may be difficult to maintain the appearance of the preparation depending on the type of flavor ingredient, and when a compound that has an aldehyde group is blended, A problem arose in that the active ingredient and the compound having an aldehyde group reacted, causing the oral composition to become colored or discolored, and ensuring stability in appearance became an issue.

In Patent Document 1 (Japanese Patent No. 5842565), sodium lauryl sulfate is added to a mouthwash composition containing tranexamic acid, which is an active ingredient having an amino group, and cinnamic aldehyde. Prevents discoloration after storage for months. Furthermore, in Patent Document 2 (Japanese Patent Publication No. 62-16926), a specific compatible aldehyde flavoring agent is added to a toothpaste containing tranexamic acid, resulting in discoloration after storage at 50°C for 2 days. , suppresses discoloration.
However, with conventional technology, it is not possible to suppress the coloring and discoloration of oral compositions due to the reaction between active ingredients having an amino group and fragrance components such as compounds having an aldehyde group, even when stored at high temperatures for long periods of time. This was difficult, and a technology that would further suppress discoloration and discoloration over time was desired.

Patent No. 5842565 Special Publication No. 62-16926 JP 2019-99483 Publication

The present invention has been made in view of the above circumstances, and is an oral composition containing allantoin and/or tranexamic acid that suppresses discoloration and discoloration of the preparation even when stored at high temperatures for a long period of time, has excellent appearance stability, and has good taste. The purpose is to provide something.

As a result of intensive studies to achieve the above object, the present inventors found that an oral composition containing allantoin or tranexamic acid having an amino group and a compound having an aldehyde group or mentofuran as a fragrance component, When low-molecular-weight polyacrylate is blended in a specific ratio, it has an excellent effect of suppressing discoloration and discoloration over time, and even when stored at high temperatures for long periods, discoloration (coloration, discoloration) of the preparation is suppressed and appearance stability is improved. Furthermore, it was found that the unpleasant taste was suppressed, good taste was maintained, high palatability was ensured, and excellent appearance stability could be provided.
That is, according to the present invention, (A) one or more selected from allantoin and tranexamic acid, (B) one or more selected from aldehyde group-containing compounds and mentofuran, and (C) a weight average molecular weight of 1, 000 to 20,000 polyacrylate, and the (C)/(A) mass ratio is 0.1 to 21. They discovered that discoloration is suppressed, the appearance is excellent in stability, and the taste is also good, leading to the present invention.

Not only when a compound having an aldehyde group is added as a fragrance component to an oral composition containing allantoin or tranexamic acid as an anti-inflammatory agent, but also when mentofuran is added, the preparation becomes discolored and discolored over time, causing a change in appearance. A problem occurred that the stability decreased. However, in the present invention, in an oral composition, especially a dentifrice composition, by combining the components (A) and (B) with the component (C), the Coloration and discoloration of the preparation over time were suppressed by the component (C), and the appearance stability was excellent. In this case, when the mass ratio of (C)/(A) is within a specific range, component (C) surprisingly acts specifically as a discoloration inhibitor for the combination system of components (A) and (B). This ensures a good taste without developing the unique unpleasant taste of component (C) itself, suppresses discoloration of the preparation (coloration, discoloration) even after long-term storage at high temperatures, and is effective in the Examples described below. As shown, the discoloration of the preparation was suppressed even after storage at 60° C. for one month, and an excellent discoloration inhibiting effect could be provided.
Polyacrylic acid or a salt thereof having a weight average molecular weight of 100,000 or more, usually about 300,000, is generally used as a binder for oral compositions. On the other hand, in the present invention, the above-mentioned particularly remarkable effect could be imparted by (C) a specific low molecular weight polyacrylate.
The effect of the present invention is that by combining components (A), (B), and (C), the mass ratio of (C)/(A) can be obtained within a specific range. As shown, if component (C) is not blended, the discoloration suppressing effect is poor even if polyacrylate with a weight average molecular weight of 300,000 is blended (Comparative Examples 1 and 2), and component (C) is blended. Even if the mass ratio of (C)/(A) was inappropriate, the effect of inhibiting discoloration or the taste (lack of unpleasant taste) was poor (Comparative Examples 3 and 4).
Furthermore, Patent Document 3 (Japanese Unexamined Patent Application Publication No. 2019-99483) discloses that by combining a specific low molecular weight polyacrylate with menthol and a specific aldehyde fragrance, the irritation can be suppressed and a refreshing feeling can be imparted. be. In contrast, the present invention uses component (C) to suppress discoloration and unpleasant taste of a combined system of components (A) and (B).

Therefore, the present invention provides the following oral composition.
[1]
(A) one or more selected from allantoin and tranexamic acid,
(B) contains one or more selected from compounds having an aldehyde group and mentofuran; and (C) a polyacrylate having a weight average molecular weight of 1,000 to 20,000, where (C)/(A) is the mass An oral cavity composition characterized in that the ratio is 0.1 to 21.
[2]
The oral composition according to [1], wherein the component (B) is selected from trans-2-hexenal, phenylacetaldehyde, citral, and mentofuran.
[3]
[1] or [2] containing 0.005 to 1% by mass of component (A), 0.0001 to 0.5% by mass of component (B), and 0.01 to 1% by mass of component (C) Oral composition as described.
[4]
The oral cavity composition according to any one of [1] to [3], which is a dentifrice composition.

According to the present invention, discoloration and discoloration of the preparation are suppressed even when stored for a long period of time at high temperatures, resulting in excellent appearance stability, and oral cavity containing allantoin or tranexamic acid, which suppresses unpleasant taste and has good taste and high palatability. A composition for use can be provided. This oral composition has an anti-inflammatory effect due to allantoin or tranexamic acid, and is suitable for preventing or suppressing periodontal diseases such as gingivitis.

The oral composition of the present invention comprises (A) one or more selected from allantoin and tranexamic acid, (B) one or more selected from aldehyde group-containing compounds and mentofuran, and (C) a weight average molecular weight of 1, 000 to 20,000 polyacrylate, and the mass ratio (C)/(A) is 0.1 to 21.

Component (A) is allantoin and tranexamic acid, and either one may be used alone or both may be used in combination. These are anti-inflammatory agents that have an amino group as a common structure.
Commercially available products can be used. For example, allantoin is a product manufactured by Merck Co., Ltd. under the trade name RonaCare Allantoin, a product manufactured by Permakem Asia Co., Ltd., etc., and tranexamic acid is a product manufactured by Kyowa Pharma Chemical Co., Ltd. products etc. can be used.
The blending amount of component (A) is preferably 0.005 to 1% (mass%, hereinafter the same), more preferably 0.01 to 0.5%, based on the entire composition. The larger the amount is, the more anti-inflammatory effect can be obtained, but the amount is preferably 1% or less from the viewpoint of discoloration suppressing effect. If it exceeds 1%, the preparation may turn yellow or brown over time.

Component (B) is a compound having an aldehyde group, mentofuran. These are fragrance ingredients, and both can be used in combination. Component (B) has the effect of suppressing the development of its own unpleasant taste caused by the combination of component (C). It also has the effect of suppressing the unpleasant taste caused by ingredients other than component (C).
Component (B) includes trans-2-hexenal, phenylacetaldehyde, propanal, citral, ethyl vanillin, cinnamic aldehyde, mentofuran, etc., especially from the viewpoint of suppressing discoloration of the preparation, and among them, trans-2-hexenal. , phenylacetaldehyde, citral, and mentofuran are preferred.
Component (B) may be a compound having an aldehyde group or mentofuran, or both may be used in combination, or one type may be used alone, or two or more types may be used in combination in terms of effect expression.
Component (B) can be isolated from essential oils or synthesized, or can be blended in a state contained in essential oils without being isolated from essential oils, such as peppermint containing mentofuran. Oil can be added.
As the component (B), commercially available products such as those manufactured by Inoue Perfume Seisakusho Co., Ltd., Toyotama Perfume Co., Ltd., and Hasegawa Perfume Co., Ltd. can also be used.

The blending amount of component (B) is preferably 0.0001 to 0.5%, more preferably 0.0005 to 0.1% of the total composition. The more blended, the better the taste and the suppression of unpleasant taste, but it is preferably 0.5% or less from the viewpoint of discoloration suppressing effect.

Component (C) is a polyacrylate having a weight average molecular weight of 1,000 or more and 20,000 or less. Component (C) is a discoloration inhibitor, and exhibits a discoloration inhibiting effect that suppresses discoloration and discoloration of the preparation caused by the combination of components (A) and (B) even over time.
The weight average molecular weight (Mw) of the polyacrylate is from 1,000 to 20,000, preferably from 1,000 to 10,000. When the weight average molecular weight is 1,000 or more, a sufficient discoloration suppressing effect can be obtained. When it is 20,000 or less, a sufficient discoloration suppressing effect can be ensured. If it exceeds 20,000, the effect of inhibiting discoloration may decrease and the preparation may turn yellow to brown over time.
The weight average molecular weight was measured by GPC (gel permeation chromatography) using the method and measurement conditions described in Japanese Patent No. 5740859 (the same applies hereinafter). Specifically, it is shown below.
Method for measuring weight average molecular weight;
The weight average molecular weight is a value measured using a gel permeation chromatograph/multi-angle laser light scattering detector (GPC-MALLS) under the following conditions.
Mobile phase: 0.3M NaClO ₄ ,
NaN ₃ aqueous solution column: TSKgelα-M 2 pre-columns: TSKguardcolumn α
Standard substance: polyethylene glycol

The polyacrylate of component (C) is preferably a linear polyacrylate from the viewpoint of discoloration inhibiting effect. As the salt, monovalent salts are preferred, alkali metal salts or ammonium salts are more preferred, alkali metal salts such as sodium salts and potassium salts are still more preferred, and sodium salts are particularly preferred.
As such a polyacrylate, a commercially available product sold by Polyscience Co., Ltd. or Toagosei Co., Ltd. may be used. Specifically, commercially available products include sodium polyacrylate (Mw: 1,000); linear, manufactured by Polyscience; sodium polyacrylate (Mw: 6,000); linear; manufactured by Toagosei Co., Ltd. manufactured by Polyscience Co., Ltd., Jurimer AC-10NP, AC-10NPD, Aron T-50, sodium polyacrylate (Mw: 9,000); linear, manufactured by Polyscience Co., Ltd., sodium polyacrylate (Mw: 20,000); Aron A-20UN, manufactured by Toagosei Co., Ltd., can be used.
In addition, the polyacrylate of component (C) has a weight average molecular weight lower than that of the crosslinked polyacrylate as a binder normally used in dentifrices, and is a polyacrylate salt known as a binder. It is different from If a polyacrylate other than component (C) is used instead of component (C), or if polyacrylic acid that is not in the form of a salt is used, discoloration of the preparation cannot be suppressed and the discoloration suppressing effect is inferior.

The blending amount of component (C) is preferably 0.01 to 1%, more preferably 0.05 to 0.5% of the total composition. When the blending amount is 0.01% or more, a sufficient discoloration suppressing effect can be obtained. When the content is 1% or less, the unique unpleasant taste caused by the component (C) itself can be sufficiently suppressed, and a good taste can be maintained.

In the oral composition of the present invention, (C)/(A), which indicates the quantitative ratio of component (A) to component (C), is 0.1 to 21 as a mass ratio, preferably 0.5 to It is 15. When the mass ratio of (C)/(A) is within the above range, unpleasant taste can be suppressed and an excellent discoloration suppressing effect can be obtained. If it is less than 0.1, the effect of suppressing discoloration will be poor, and the preparation will turn yellow to brown over time, and if it exceeds 21, the unpleasant taste of the component (C) itself cannot be suppressed, resulting in poor taste and decreased palatability. .

The oral composition of the present invention can be prepared as a dentifrice, a mouthwash, a liniment, a patch, etc., but is particularly suitable as a dentifrice, a mouthwash, especially a dentifrice, and is a dentifrice composition. is preferred. The dosage form can be liquid, liquid, paste, etc., and the dentifrice is preferably a toothpaste, a liquid dentifrice, a liquid dentifrice, a moisturized dentifrice, etc., especially a toothpaste. Further, in addition to the above-mentioned components, other optional components depending on the intended use, dosage form, etc. may be appropriately blended within a range that does not impede the effects of the present invention. Specifically, toothpastes may contain surfactants, abrasives, thickeners, binders, and if necessary, sweeteners, preservatives, pigments, fragrances, and various active ingredients.

As the surfactant, an anionic surfactant or a nonionic surfactant may be blended.
Examples of the anionic surfactant include alkyl sulfates having an alkyl group having 12 to 14 carbon atoms, particularly 12 carbon atoms, acylamino acid salts, acyl taurine salts, and the like. The acyl group of the acylamino acid salt and the acyl taurine salt each preferably has 12 to 14 carbon atoms, more preferably 12 carbon atoms. Specific examples of alkyl sulfates include lauryl sulfate and myristyl sulfate. Examples of the acyl amino acid salts include acyl glutamates such as lauroyl glutamate and myristoyl glutamate, and acyl sarcosine salts such as lauroyl sarcosine salt. Examples of the acyl taurine salt include lauroylmethyl taurine salt and the like. The salt is preferably an alkali metal salt such as sodium salt or potassium salt. These can be used alone or in combination of two or more, but alkyl sulfates, acyl sarcosine salts, and acyl taurine salts are particularly preferred. Among these, anionic surfactants having a hydrocarbon group (lauryl group) having 12 carbon atoms are preferable, and alkyl sulfates (sodium salts) are particularly preferable in terms of usability such as dispersibility of the preparation than other surfactants. It is more preferable because it has excellent properties.
Examples of nonionic surfactants include polyoxyethylene alkyl ether, polyoxyethylene-polyoxypropylene block copolymer, polyoxyethylene hydrogenated castor oil, polyoxyethylene ether of glycerin ester, sucrose fatty acid ester, and alkylol. Examples include amides and glycerin fatty acid esters. Among these, polyoxyethylene alkyl ether and polyoxyethylene hydrogenated castor oil are preferably used in terms of solubilization of perfume components and stable blending. The polyoxyethylene alkyl ether preferably has an alkyl chain having 14 to 20 carbon atoms. The polyoxyethylene alkyl ether preferably has an average number of added moles of ethylene oxide of 3 to 30. The polyoxyethylene hydrogenated castor oil preferably has an average number of added moles of ethylene oxide of 10 to 100. In particular, when incorporated into a dentifrice composition, it is preferable that the average number of added moles of ethylene oxide is 10 to 30.

Abrasives include crystalline silica, amorphous silica, silica gel, silica-based abrasives such as aluminosilicate, zeolite, calcium hydrogen phosphate anhydrate, calcium hydrogen phosphate dihydrate, calcium pyrophosphate, calcium carbonate, water. Examples include aluminum oxide, alumina, magnesium carbonate, tertiary magnesium phosphate, zirconium silicate, tertiary calcium phosphate, hydroxyapatite, quaternary calcium phosphate, and synthetic resin abrasives. The amount of abrasive is usually 5 to 70%, particularly 10 to 50% of the total composition.

Examples of thickeners include sugar alcohols such as sorbitol, xylitol, and erythritol, and polyhydric alcohols such as propylene glycol, butylene glycol, glycerin, and polyethylene glycol. The amount of the thickening agent is usually 0 to 70%, particularly 3 to 50% of the total composition.

The binder can be an organic or inorganic binder. Specifically, organic caking agents such as cellulose derivatives such as sodium carboxymethylcellulose, methylcellulose, and hydroxymethylcellulose, alginic acid derivatives, gums such as xanthan gum, carrageenan, polyvinyl alcohol, and sodium polyacrylate having a weight average molecular weight higher than that of component (C) are used. Among them, inorganic binders, particularly thickening silica, are preferred from the viewpoint of suppressing discoloration and unpleasant taste of the preparation. The amount of the binder added is usually 0.1 to 10% by weight, particularly 0.1 to 5% by weight of the entire composition.

Examples of sweeteners include sodium saccharin.
Examples of preservatives include benzoates such as sodium benzoate, and paraoxybenzoic acid esters such as methylparaben, ethylparaben, and butylparaben.
Examples of pigments include food pigments such as brilliant blue and tartrazine, and pigments such as titanium oxide.

Active ingredients (medicinal ingredients) include, for example, bactericidal or antibacterial agents such as chlorhexidine, triclosan, isopropylmethylphenol, cetylpyridinium chloride, benzethonium chloride, benzalkonium chloride, zinc gluconate, zinc citrate, and ethane hydroxy diphosphonate. tartar prevention agents such as glycyrrhizic acid and its salts, anti-inflammatory agents such as epsilon aminocaproic acid, enzyme agents such as dextranase, mutanase, lysozyme chloride, vitamins such as ascorbic acid and tocopherol acetate, astringents such as sodium chloride. , aluminum lactate, strontium chloride, and other hypersensitivity suppressants; and sodium fluoride, sodium monofluorophosphate, stannous fluoride, and other fluorides. These can be used in effective amounts within a pharmaceutically acceptable range.

EXAMPLES Hereinafter, the present invention will be specifically explained with reference to Examples and Comparative Examples, but the present invention is not limited to the Examples below. In addition, in the following examples, % indicates mass % unless otherwise specified.

[Examples, comparative examples]
Dentifrice compositions (dentifrices) having the compositions shown in Tables 1 to 9 were prepared by conventional methods, used as test dentifrice compositions, and evaluated by the following method. The results are also listed in the table.

(1) Method for evaluating the appearance stability (discoloration suppressing effect) of the formulation The dentifrice composition was placed in a 26 mm diameter laminated tube container (LDPE55/PET12/LDPE20/white LDPE60/EMAA20) whose innermost layer was made of linear low-density polyethylene. /AL10/EMAA30/LDPE20/LLDPE30 (manufactured by Dainippon Printing Co., Ltd.)) was filled with 50 g and stored in a constant temperature bath at 60° C. for one month, and then returned to room temperature. The product appearance (degree of discoloration) when the dentifrice composition was extruded from the laminated tube container was compared with a dentifrice composition of the same composition stored at -5°C for one month, and discoloration was inhibited using the following evaluation criteria. The effectiveness was evaluated. In addition, each dentifrice composition was white immediately after preparation.
Evaluation criteria for discoloration suppression effect ◎: No change in color compared to the control product ○: Almost no change in color compared to the control product △: No change in color (yellow to browning) compared to the control product Yes ×: There is a significant change in color (yellow to browning) compared to the control product.

(2) Evaluation method for taste (absence of unpleasant taste) Ten test subjects placed 1 g of the dentifrice composition on their toothbrushes and brushed for 3 minutes to clean their oral cavity.The taste (absence of unpleasant taste) was evaluated according to the following rating criteria. Sensory evaluation was performed. The average score of the 10 people was calculated, and the taste (lack of unpleasantness) was evaluated using the following evaluation criteria.
Scoring criteria for taste (lack of unpleasant taste) 4 points: No unpleasant taste in the mouth 3 points: Almost no unpleasant taste in the oral cavity 2 points: Somewhat unpleasant taste in the oral cavity 1 point: Extremely unpleasant taste in the oral cavity Evaluation criteria for perceived taste (lack of sarcasm) ◎: Average score of 3.5 points or more and 4.0 points or less ○: Average score of 3.0 points or more and less than 3.5 points △: Average score of 2.0 points or more and 3.0 points Less than a score ×: Average score of 1.0 points or more and less than 2.0 points

Details of the raw materials used are shown below.
(A) Component Allantoin Product name: RonaCare Allantoin, manufactured by Merck Co., Ltd. Tranexamic acid manufactured by Kyowa Pharma Chemical Co., Ltd. (B) Component trans-2-hexenal manufactured by Inoue Fragrance Manufacturing Co., Ltd. Phenylacetaldehyde manufactured by Toyotama Fragrance Co., Ltd. Citral Manufactured by Hasegawa Fragrance Co., Ltd. Mentofuran Manufactured by Toyotama Fragrance Co., Ltd. (C) Component Sodium polyacrylate (Mw: 1,000)
Linear, manufactured by Polyscience, sodium polyacrylate (Mw: 6,000)
Linear, product name: Jurimer AC-10NP, manufactured by Toagosei Co., Ltd. Sodium polyacrylate (Mw: 9,000)
Linear, manufactured by Polyscience, sodium polyacrylate (Mw: 20,000)
Linear, product name: Aron A-20UN, manufactured by Toagosei Co., Ltd. Sodium polyacrylate (Mw: 300,000) (comparison product)
Polyscience Company

Claims (4)

(A) one or more selected from allantoin and tranexamic acid,
(B) contains one or more selected from trans-2-hexenal, phenylacetaldehyde, citral , and mentofuran; and (C) a polyacrylate having a weight average molecular weight of 1,000 to 10,000 ; An oral composition characterized in that (A) has a mass ratio of 0.1 to 21. The oral composition according to claim 1, wherein component (B) is selected from trans-2-hexenal, phenylacetaldehyde , and menthofuran. The oral cavity according to claim 1 or 2, containing 0.005 to 1% by mass of component (A), 0.0001 to 0.5% by mass of component (B), and 0.01 to 1% by mass of component (C). Composition for use. The oral composition according to any one of claims 1 to 3, which is a dentifrice composition.