JP7167660B2 - dentifrice composition - Google Patents

Description

TECHNICAL FIELD The present invention relates to a dentifrice composition that provides a refreshing sensation in the oral cavity immediately after use and that maintains a refreshing sensation even after use.

Conventionally, cooling agents such as menthol have been used in dentifrice compositions as a component that imparts a refreshing feeling that leads to a feeling of cleaning. Cooling agents such as menthanecarboxamides are also known as components that further enhance the cooling sensation.
However, by blending these ingredients together, although it has a certain effect on the refreshing feeling during toothbrushing, the rising of the refreshing feeling at the beginning of brushing teeth is not sufficient, and the refreshing feeling is not maintained. It was not fully satisfactory, and there was still room for improvement.

Patent Document 1 (Japanese Patent Application Laid-Open No. 2014-125440) enhances flavor (taste, aroma, and cooling sensation) by adding a non-menthol cooling agent and L-menthol to an oral composition containing colored granules. And proposed that the storage stability can be improved, Patent Document 2 (JP 2016-102076), a nonionic surfactant, L-menthol and menthyl 3-hydroxybutanoate blended, further N-ethyl It is proposed that the addition of p-menthanecarboxamide or the like improves the rinsability of the oral composition and improves the lasting cool feeling remaining on the tooth surface. Patent Document 3 (Japanese National Publication of International Patent Application No. 2012-508741) discloses that a flavor composition containing a non-menthol cooling sensation agent and a composition that can be used on the oral mucous membrane surface, including a calcium ion source, etc., has a cooling effect that lasts longer than 15 minutes. Patent Document 4 (Japanese Patent Application Laid-Open No. 2013-181011) discloses that a feeling is immediately expressed, and a combination of myristoyl glutamate and a nonionic surfactant such as polyoxyethylene hydrogenated castor oil, and menthol and the like. It discloses that a liquid composition for oral cavity containing an oil-soluble flavor and water is excellent in flavor and refreshing sensation derived from the flavor.

JP 2014-125440 A JP 2016-102076 A Japanese Patent Publication No. 2012-508741 JP 2013-181011 A

It is an object of the present invention to provide a dentifrice composition that gives a refreshing sensation in the oral cavity immediately after use and maintains a refreshing sensation even after use.

The present inventors have made intensive studies to achieve the above objects, and as a result, (A) at least one salt selected from lauroyl methyl taurate, lauroyl glutamate and polyoxyethylene alkyl sulfosuccinate, and (B ) A sweetener having a relative sweetness of 200 or more and (C) N-(4-cyanomethylphenyl)-2-isopropyl-5-methylcyclohexanecarboxamide are combined in specific amounts and incorporated into a dentifrice composition. As a result, the rise of the refreshing feeling in the oral cavity immediately after the start of use is improved, and as a result, the refreshing feeling can be felt immediately after use, and the refreshing feeling can be felt continuously even after use. We found that it is possible, and came to make the present invention.

Anionic surfactants and sweeteners were not found to have a refreshing effect, and the addition of sweeteners with a high degree of sweetness sometimes caused an unpleasant taste (sweetness), but in the present invention, (A ) and (B) in combination with the component (C) of the cooling sensation agent, unexpectedly, the refreshing feeling immediately after the start of use in the oral cavity when the blending amount of each of these ingredients is within a specific range It was possible to improve the persistence of the rise of the skin and the cooling sensation over time.
Such effects of the present invention are inferior if any one of the components (A), (B) and (C) is missing, and even if these three components are included, the blending amount of any one is inappropriate. It was also inferior in the case of , and was due to the unique action of the combination of the above three components, and it was a particularly remarkable action and effect that could not be obtained by simply blending the cooling agent menthol and the cooling sensation agent.
As shown in the Comparative Examples and Examples below, when the component (A), (B) or (C) is not blended, the cooling sensation rises immediately after the start of use or the cooling sensation lasts immediately after the start of use. was bad (Comparative Examples 1, 2, 5 to 7, 10, 11). In Comparative Examples 5, 6, and 7, in which the component (A) was not blended, even if the surfactant coconut oil fatty acid amidopropyl betaine or polyoxyethylene hydrogenated castor oil was blended, the cooling sensation did not start well, and ( In Comparative Examples 10 and 11, in which component B is not blended, even when erythritol (relative sweetness of 0.8) is blended as a sweetener, the cooling sensation rises and lasts poorly, and component (C) is blended. In Comparative Examples 1 and 2, in which carboxamides were not added, the cooling sensation persisted poorly. In addition, even if the components (A), (B) and (C) were blended, if the blending amount of any one of the components was inappropriate, the cooling sensation did not rise quickly and the cooling sensation did not last long. (Comparative Examples 3, 4, 8, 9, 12, 13). On the other hand, the dentifrice compositions containing specific amounts of the components (A), (B) and (C) of the present invention shown in the examples give a cool sensation immediately after the start of use, and immediately after the start of use. 30 seconds after the start of tooth brushing, the refreshing feeling was felt, and after rinsing the oral cavity with water after brushing the teeth, the refreshing feeling was felt and lasted for 10 minutes. .

Accordingly, the present invention provides the following dentifrice composition.
[1]
(A) at least one salt selected from lauroyl methyl taurate, lauroyl glutamate and polyoxyethylene alkyl sulfosuccinate 0.5 to 5% by mass,
(B) Sweetener with a relative sweetness of 200 or more 0.05 to 0.5% by mass
and (C) N-(4-cyanomethylphenyl)-2-isopropyl-5-methylcyclohexanecarboxamide 0.00001 to 0.01% by mass
A dentifrice composition comprising:
[2]
The dentifrice composition according to [1], wherein the sweetener having a relative sweetness of 200 or more is at least one sweetener selected from sucralose, stevia, acesulfame and aspartame.
[3]
The dentifrice composition according to [2], wherein the sweetener having a relative sweetness of 200 or more is selected from sucralose and stevia.
[4]
The dentifrice composition according to any one of [1] to [3], which is a toothpaste.

According to the present invention, it is possible to provide a dentifrice composition that provides a refreshing sensation in the oral cavity immediately after use and that maintains a refreshing sensation even after use. In the present invention, the cooling sensation is sufficiently and satisfactorily felt, and it can be expected that the feeling of effectiveness such as the feeling of cleaning and the feeling of suppressing bad breath can be enhanced.

The present invention will be described in further detail below. The dentifrice composition of the present invention comprises (A) at least one salt selected from lauroyl methyl taurate, lauroyl glutamate and polyoxyethylene alkyl sulfosuccinate, and (B) a sweetener having a relative sweetness of 200 or more. , and (C) N-(4-cyanomethylphenyl)-2-isopropyl-5-methylcyclohexanecarboxamide in specific amounts.

Component (A) is a salt selected from lauroylmethyltaurate, lauroylglutamate and polyoxyethylene alkylsulfosuccinate, and these salts are preferably alkali metal salts such as sodium salts. A polyoxyethylene alkyl sulfosuccinate having an average mole number of ethylene oxide added of 1 to 9 moles can be preferably used. These may be used singly or in combination of two or more types, and may be dissolved or present in the dentifrice composition in an undissolved state. The salt is known as an anionic surfactant, and in the present invention, it has the effect of improving the cooling sensation (the cooling sensation immediately after the start of use in the oral cavity; the same shall apply hereinafter).
The blending amount of component (A) is 0.5 to 5% (% by mass, the same shall apply hereinafter) of the entire composition, preferably 0.8 to 3%. If the blending amount is less than 0.5%, the refreshing feeling is inferior. If it exceeds 5%, the cooling sensation does not rise quickly, and rather than the cooling sensation, the characteristic bitterness and sourness derived from the component (A) may become conspicuous.

Component (B) is a sweetener having a relative sweetness of 200 or more, preferably 200-700. In the present invention, (B) a sweetener having a specific relative sweetness, in combination with components (A) and (C), has the effect of improving the rise and duration of the refreshing sensation.

(B) Sweeteners having a relative sweetness of 200 or more include sucralose (relative sweetness: 600), stevia (relative sweetness: 300), acesulfame (relative sweetness: : 200), and aspartame (relative sweetness: 200) can be used. In particular, when the relative sweetness is 300 to 600, the refreshing sensation is more excellent in rising and lasting, and it is more preferable to use sucralose and stevia. In addition, these can use a commercial item.
Sweeteners with a relative sweetness of less than 200 are inferior in refreshing sensation onset and duration.

Here, the relative sweetness is the relative sweetness when the sweetness of sucrose (sugar) is 1.0. Information site, https://www.e-healthnet.mhlw.go.jp) describes the usage of substitute sweeteners as relative sweetness of substitute sweeteners to sucrose (same below).

The blending amount of component (B) is 0.05 to 0.5%, preferably 0.10 to 0.3%, of the total composition. If the blending amount is less than 0.05%, the cooling sensation will be inferior in its rise and durability. If it exceeds 0.5%, the cooling sensation will deteriorate and its durability will deteriorate.

(C) N-(4-cyanomethylphenyl)-2-isopropyl-5-methylcyclohexanecarboxamide is a cooling agent and has the effect of improving the refreshing feeling in the oral cavity. And there is an effect of improving the sustainability.
As N-(4-cyanomethylphenyl)-p-menthane-3-carboxamide, commercially available products such as trade name: Evercool G-180 manufactured by Givaudan Japan Co., Ltd. can be used.

The amount of component (C) is 0.00001 to 0.01%, preferably 0.0005 to 0.005%, of the total composition. If the blending amount is less than 0.00001%, the cooling sensation is inferior in its rising and lasting performance. If the content exceeds 0.01%, the cooling sensation will not start and last long, and the sensation of irritation such as tingling in the oral cavity will become strong, which may lead to deterioration of the feeling of use.

The dentifrice composition of the present invention can be prepared into formulations such as toothpaste, liquid dentifrice, and wet toothpaste, particularly toothpaste. In this case, in addition to the above components, other known components that are usually used in dentifrice compositions can be added as necessary as long as the effects of the present invention are not impaired. , can be prepared by a usual method by mixing these components with water. Specifically, for toothpaste, optional ingredients include abrasives, surfactants, wetting agents, binders, fragrances, preservatives, pH adjusters, and medicinal ingredients.

Abrasives include calcium phosphate-based compounds such as dicalcium phosphate dihydrate or anhydrate, monocalcium phosphate, tricalcium phosphate, and calcium pyrophosphate; silica-based abrasives; calcium carbonate-based abrasives such as calcium carbonate; You can mix the above. Among these, silica-based abrasives and calcium carbonate-based abrasives mainly composed of silicates such as precipitated silica, aluminosilicate, zirconosilicate, titanium-bonded silica, and especially silica-based abrasives such as precipitated silica, etc. Abrasives are preferred.
The precipitated silica preferably has a particle size of 1 to 40 μm and a BET specific surface area of 80 to 250 square meters per gram.
The blending amount of these abrasives is preferably 8 to 70% of the total composition.

Further, the abrasive may be granules, and granules can be blended as a component having abrasive properties. The granules are granulated particles obtained by forming water-insoluble powder into granules, and a binder may be used for granulation.
Water-insoluble powders include dicalcium phosphate, tricalcium phosphate, water-insoluble calcium metaphosphate, silica, aluminum hydroxide, magnesium phosphate, red iron oxide, calcium carbonate, calcium pyrophosphate, zeolite, aluminosilicate, magnesium carbonate, and zirconosilicate. , calcium sulfate and the like, and mixtures thereof, with silica granules and zeolite granules being particularly preferred.
The volume average particle diameter (median diameter d50) of the granules is preferably 50-500 μm. The volume average particle diameter is a value measured by a particle size distribution analyzer (Microtrac particle size distribution meter manufactured by Nikkiso Co., Ltd., dispersion medium: water).
The average disintegration strength of granules is preferably 10-200 g/piece. The average collapse strength is an automatic breaking strength measurement value of 30 granules using a rheometer (Sun Rheometer CR-200D, manufactured by Sun Scientific Co., Ltd.) (when one granule is compressed at a speed of 10 mm / min, the granule collapses It is the average value of the load measured when

As silica granules, wet-process gel process silica and precipitation process silica are preferably used, and the primary particle size is about 3 to 15 nm, preferably 4 to 10 nm. For example, a silica gel mass grown to a primary particle size of about 4 to 10 nm by a gel method is washed, dried, and pulverized to classify silica granules having an average particle size of 50 to 500 μm. A method of preparing granules by spraying and gelling in the air, and a method of preparing by growing the primary particle size to about 4 to 10 nm after agglomerating while suppressing the growth of primary particles by a sedimentation method. are known and silica granules can be prepared by these methods. Colored granules can also be used.
The blending amount of these granules is preferably 0.1 to 20% of the total composition. The total amount of abrasive compounded is preferably 8 to 70% of the total composition.

Surfactants can include anionic surfactants, nonionic surfactants, amphoteric surfactants, etc. other than component (A).
Specific examples of anionic surfactants include alkyl sulfates such as sodium lauryl sulfate, α-olefin sulfonates, hydrogenated coconut fatty acid monoglyceride monosulfates, and lauryl sulfoacetates.
Nonionic surfactants include sugar fatty acid esters, sugar alcohol fatty acid esters, polyglycerin fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene fatty acid esters such as polyoxyethylene hydrogenated castor oil, and polyoxyethylene fatty acid esters such as polyoxyethylene lauryl ether. Fatty acid alkanolamides such as oxyethylene higher alcohol ethers and lauric acid diethanolamides can be mentioned.
Amphoteric surfactants include betaines such as alkyl betaine, fatty acid amidopropyl betaine, fatty acid amidopropyl dimethylaminoacetate betaine, and alkylimidazolinium betaine.
The amount of these optional surfactants to be blended can be 0 to 5% of the total composition.

Wetting agents can be sugar alcohols and polyhydric alcohols, such as sorbitol, xylitol, erythritol, mannitol, maltitol, reduced palatinose, propylene glycol, butylene glycol, polyethylene glycol, and glycerin. The blending amount is usually 5-50%, especially 20-45% of the total composition.

Binders include xanthan gum, sodium carboxymethylcellulose, sodium polyacrylate, sodium alginate, polyvinylpyrrolidone, carrageenan, methylcellulose, sodium hydroxyethylcellulose, tragacanth gum, karaya gum, arabic gum, locust bean gum, polyvinyl alcohol, carboxyvinyl polymer, carbopol, Examples include organic binders such as Veegum and propylene glycol alginate, and inorganic binders such as thickening silica and aluminum silicate. Organic and/or inorganic binders can be included. These may be used singly or in combination of two or more. The blending amount of these binders is usually 1.4 to 10%, particularly 1.4 to 3%, of the total composition.

Fragrances include known fragrances such as menthol, anethole, carvone, eugenol, limonene, n-decyl alcohol, citronellol, α-terpineol, citronellyl acetate, cineol, linalool, ethyllinalool, vanillin, thymol, spearmint oil, peppermint oil, Lemon oil, orange oil, sage oil, rosemary oil, cinnamon oil, pimento oil, cinnamon leaf oil, perilla oil, wintergreen oil, clove oil, eucalyptus oil and the like.
In the present invention, menthol may not be blended in terms of the persistence of refreshing feeling, and the blending amount may be 0%, but menthol may be blended within a range that does not hinder the effects of the present invention. good too. When menthol is blended, its blending amount may be 1% or less, particularly 0.5% or less, and may be 0.2% or more based on the total composition.
The dentifrice composition of the present invention may contain a relatively small amount of menthol.

Preservatives include paraoxybenzoic acid esters, sodium benzoate and the like.
Examples of pH adjusters include organic acids such as citric acid and lactic acid and salts thereof; and inorganic compounds such as hydrochloric acid, sodium hydroxide, potassium hydroxide, disodium hydrogen phosphate and sodium dihydrogen phosphate.

Medicinal ingredients include fluorine-containing compounds such as sodium fluoride and sodium monofluorophosphate; enzymes such as dextranase, amylase, protease and mutanase; Anti-inflammatory agents such as glycyrrhetinate; cell activators such as sodium chloride and vitamins; bactericidal agents such as isopropylmethylphenol, cetylpyridinium chloride, benzalkonium chloride, hinokitiol and lysozyme chloride; water-soluble copper compounds; anticalculus agents such as zeolite; blood circulation promoters such as vitamin E; amino acids such as alanine, glycine, proline, and the like. In addition, the compounding amount of the medicinal component can be an effective amount within a range that does not impair the effects of the present invention.

Furthermore, as optional ingredients, inorganic compounds such as mica titanium, titanium oxide, and bentonite; cellulose-based organic powders such as crystalline cellulose; natural polymer compounds such as agar, gelatin, starch, and glucomannan; polyvinyl acetate, acrylic, Synthetic polymer compounds such as polyurethane, polyester, polyvinyl chloride, nylon powder, polyethylene powder, or copolymers thereof; waxes such as carnauba wax, rosin, rice wax, microcrystalline wax, beeswax, paraffin wax; cetanol, stearyl Higher alcohols such as alcohol; polyisobutylene, polybutadiene, polyurethane, silicone, natural rubber, etc. can be blended as long as the effects of the present invention are not impaired.

EXAMPLES Hereinafter, the present invention will be specifically described by showing examples and comparative examples, but the present invention is not limited to the following examples. In the following examples, % indicates % by mass unless otherwise specified.

[Examples, Comparative Examples]
A dentifrice composition (toothpaste) having the composition shown in Tables 1 to 5 was prepared by a conventional method, and the feel during use was evaluated by the following method. The results are also shown in the table.

Evaluation method of feeling in use The feeling in use was evaluated by four subjects. 1 g of the dentifrice composition was placed on a toothbrush (clinica advantage toothbrush, 4-row compact regular type, manufactured by Lion Co., Ltd.), and the teeth were brushed for 3 minutes in the usual manner. Rise of refreshing feeling immediately after the start of use (refreshing feeling 30 seconds after starting toothbrushing) and persistence of refreshing feeling immediately after starting use (from immediately after starting toothbrushing to 10 minutes after rinsing with water after brushing The duration of refreshing sensation) was evaluated according to the following rating criteria. The average score of each of the four people was calculated and evaluated using the following evaluation criteria.

<Rise of refreshing feeling immediately after the start of use>
Rating criteria 5: Very good 4: Good 3: Fairly good 2: Fairly bad 1: Poor Evaluation criteria ◎: Average score of 4 people is 4 points or more ○: Average score of 4 people is 3 points or more and less than 4 points △: The average score of 4 people is 2 or more and less than 3 points ×: The average score of 4 people is less than 2 points

<Sustainability of refreshing feeling immediately after the start of use>
Rating criteria 5: Very good 4: Good 3: Fairly good 2: Fairly bad 1: Poor Evaluation criteria ◎: Average score of 4 people is 4 points or more ○: Average score of 4 people is 3 points or more and less than 4 points △: The average score of 4 people is 2 or more and less than 3 points ×: The average score of 4 people is less than 2 points

Details of raw materials used are shown below.
(A) Sodium lauroyl methyl taurate Trade name: NIKKOL LMT, manufactured by Nikko Chemicals Co., Ltd. (A) Polyoxyethylene (2) alkyl (12-14) disodium sulfosuccinate Trade name: Beaulite ESS, carbon number of alkyl group 12 to 14, Sanyo Chemical Co., Ltd. (A) Sodium lauroyl glutamate Product name; Amino Surfact, Asahi Kasei Chemicals Co., Ltd. coconut oil fatty acid amidopropyl betaine (comparative product)
Product name: TEGO Betain CK, polyoxyethylene (20) hydrogenated castor oil manufactured by EVONIK (comparative product)
Trade name: NIKKOL HCO-20, manufactured by Nikko Chemicals Co., Ltd. (B) Sucralose (600 ^* )
Product name: Sucralose, San-Ei Gen SSI Co., Ltd. (B) Stevia (300 ^* )
Product name: Rebaudio AD, manufactured by Morita Chemical Co., Ltd. (B) Acesulfame (200 ^* )
Product name: Acesulfame potassium, Nutrinova Japan Co., Ltd. (B) Aspartame (200 ^* )
Product name; Aspartame, Erythritol (0.8 ^* ) manufactured by Ajinomoto Co., Inc. (comparative product)
Trade name: Erythritol, (C)N-(4-cyanomethylphenyl)-2-isopropyl-5-methylcyclohexane carboxamide manufactured by Mitsubishi Kagaku Foods Co., Ltd. Trade name: Evercool G-180,
Givaudan Japan Co., Ltd. N-ethyl-p-menthane-3-carboxamide (comparative product)
Product name: WS-3, manufactured by Givaudan Japan Co., Ltd. *: Relative sweetness (relative sweetness when the sweetness of sucrose (sugar) is taken as 1.0) See the description on the information site "e-Healthnet".
)

Claims (4)

(A) at least one salt selected from lauroyl methyl taurate, lauroyl glutamate and polyoxyethylene alkyl sulfosuccinate 0.5 to 5% by mass,
(B) Sweetener with a relative sweetness of 200 or more 0.05 to 0.5% by mass
and (C) N-(4-cyanomethylphenyl)-2-isopropyl-5-methylcyclohexanecarboxamide 0.00001 to 0.01% by mass
and wherein the sweetener is at least one selected from sucralose, stevia, acesulfame and aspartame . 2. The dentifrice composition according to claim 1, wherein the polyoxyethylene alkyl sulfosuccinate has an average number of added moles of ethylene oxide of 1 to 9 moles. The dentifrice composition according to claim 1 or 2, wherein the sweetener having a relative sweetness of 200 or more is selected from sucralose and stevia. The dentifrice composition according to any one of claims 1 to 3, which is a toothpaste.