JP7124403B2 - dentifrice composition - Google Patents

Description

TECHNICAL FIELD The present invention relates to a dentifrice composition that contains salts having medicinal properties, improves unpleasant taste during use, reduces irritation in the oral cavity, and provides an excellent feeling of use.

Conventionally, salts such as potassium nitrate, potassium chloride, potassium citrate, potassium oxalate, sodium chloride, etc., have been used as active ingredients having medicinal effects in dentifrice compositions for the purpose of preventing oral diseases such as hypersensitivity and gingival and periodontitis. It can be mixed with things.

On the other hand, N-substituted-p-menthane-carboxamides are known as cooling or refreshing agents for dentifrice compositions. -125440, No. 2015-182983, No. 2016-102076;

JP 2014-125440 A JP 2015-182983 A JP 2016-102076 A Japanese translation of PCT publication No. 2014-507440 Japanese Patent Publication No. 2012-508741 Japanese Patent Publication No. 2011-520925

However, the salt-containing dentifrice composition may leave an unpleasant taste such as saltiness, pungent taste, or bitterness as an unpleasant taste during use, and may cause irritation in the oral cavity. There is room for improvement in terms of feeling.

The present invention has been devised in view of the above circumstances, and provides a dentifrice composition that contains salts having medicinal effects, improves unpleasant taste during use, reduces irritation in the oral cavity, and has an excellent feeling of use. for the purpose.

As a result of intensive studies to achieve the above object, the present inventors have found that a specific amount of a specific N-substituted-p-menthane-carboxamide is added to a dentifrice composition containing a specific salt having medicinal properties. And when combined with a specific surfactant, the unpleasant taste derived from the salt is suppressed to improve the unpleasant taste, and the oral irritation caused by the salt is suppressed to reduce the irritation. It was found that the feeling of use is improved by
That is, according to the present invention, (A) a dentifrice composition containing one or more salts selected from potassium nitrate, potassium chloride, potassium citrate, potassium oxalate and sodium chloride, (B) N-(4 -Cyanomethylphenyl)-2-isopropyl-5-methylcyclohexanecarboxamide, and (C) one or more selected from nonionic surfactants and amphoteric surfactants to reduce unpleasant taste during use. The present inventors have found that it is possible to provide a dentifrice composition that improves and reduces the feeling of irritation in the oral cavity and provides an excellent feeling of use, and has completed the present invention.

In the present invention, when the components (B) and (C) are combined with the component (A), the offensive taste caused by the component (A) is suppressed by the component (B), and further suppressed by using the component (C) in combination. The unpleasant taste is improved to give a good taste, and even if the unique oral irritation caused by the component (A) is strengthened by the combined use of the component (B), the irritation in the oral cavity is reduced. I could hardly feel it, and I was able to obtain a special effect.
As will be shown in Comparative Examples below, when component (B) is absent, even if N-ethyl-p-menthane-3-carboxamide is blended, the lack of offensive taste during use is inferior, and (C) When the ingredients were lacking, the feeling of irritation in the oral cavity during use was inferior.

Accordingly, the present invention provides the following dentifrice compositions.
[1]
(A) one or more salts selected from potassium nitrate, potassium chloride, potassium citrate, potassium oxalate and sodium chloride;
(B) N-(4-cyanomethylphenyl)-2-isopropyl-5-methylcyclohexanecarboxamide and (C) one or more selected from nonionic surfactants and amphoteric surfactants. dentifrice composition.
[2]
The dentifrice according to [1], containing 0.5 to 15% by mass of component (A), 0.00001 to 0.01% by mass of component (B), and 0.01 to 3% by mass of component (C). Composition.
[3]
Nonionic surfactants include sucrose fatty acid esters, polyglycerol fatty acid esters, sorbitan fatty acid esters having alkyl chains of 8 to 20 carbon atoms; average addition of ethylene oxide having alkyl chains of 8 to 20 carbon atoms; polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbit fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyethylene glycol fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether having a molar number of 20 to 100; Polyoxyethylene hydrogenated castor oil, polyoxyethylene castor oil, and polyoxyethylene hydrogenated castor oil having an average added mole number of 20 to 100, and a molar ratio of the average added mole number of ethylene oxide/the average added mole number of propylene oxide being 0.2 to 7. The dentifrice composition according to [1] or [2], which is at least one selected from polyoxyethylene-polyoxypropylene copolymers.
[4]
[1] to [3], wherein the amphoteric surfactant is one or more selected from alkyl betaine, betaine acetate, imidazolinium betaine, amidopropyl betaine, and amine oxide having an alkyl chain of 8 to 20 carbon atoms; A dentifrice composition according to any one of the above.

According to the present invention, it is possible to provide a dentifrice composition that contains a specific salt having medicinal effects, improves unpleasant taste during use, reduces irritation in the oral cavity, and has excellent usability.

The present invention will be described in further detail below. The dentifrice composition of the present invention comprises (A) one or more salts selected from potassium nitrate, potassium chloride, potassium citrate, potassium oxalate and sodium chloride, (B) N-(4-cyanomethylphenyl)-2 -isopropyl-5-methylcyclohexanecarboxamide, (C) one or more surfactants selected from nonionic surfactants and amphoteric surfactants.

Component (A) is one or more salts selected from potassium nitrate, potassium chloride, potassium citrate, potassium oxalate and sodium chloride, with potassium nitrate and sodium chloride being particularly preferred. These salts are active ingredients having medicinal effects, and have the following effects.
・Potassium nitrate, potassium chloride, potassium citrate, potassium oxalate: Preventive effect on hypersensitivity ・Sodium chloride: Preventive effect on gums and periodontitis, tightening effect on gums, etc.

The blending amount of component (A) is preferably 0.5 to 15% (% by mass, hereinafter the same), more preferably 1 to 10%, and still more preferably 1 to 7% of the total composition. When the compounding amount is 0.5% or more, the expected medicinal effect is sufficiently exhibited, and when it is 15% or less, the unpleasant taste due to itself is sufficiently improved, and the oral irritation is sufficiently reduced. can be suppressed to
The component (A) may be present in the composition in a dissolved state or in an undissolved state, and the total blending amount thereof is preferably within the above range.

(B) N-(4-cyanomethylphenyl)-2-isopropyl-5-methylcyclohexanecarboxamide suppresses the unpleasant taste derived from the component (A) and has the effect of improving the unpleasant taste.
When an N-substituted-p-menthane-carboxamide other than the component (B) is used instead of the component (B), the above effects are inferior.
As N-(4-cyanomethylphenyl)-2-isopropyl-5-methylcyclohexanecarboxamide, commercially available products such as Evacool 180 (trade name, manufactured by Givaudan Japan Co., Ltd.) can be used.

The blending amount of component (B) is preferably 0.00001 to 0.01%, more preferably 0.00003 to 0.002%, based on the total composition. When the amount is 0.00001% or more, the unpleasant taste is sufficiently improved. If it is 0.01% or less, it is possible to sufficiently prevent the deterioration of the sensation of irritation in the oral cavity.

Component (C) is one or more selected from nonionic surfactants (C-1) and amphoteric surfactants (C-2), and may be component (C-1) or component (C-2). However, the components (C-1) and (C-2) may be used in combination in terms of effect expression. Component (C) enhances the above action of component (B) and has an action of reducing irritation in the oral cavity.

As nonionic surfactants (C-1), polyhydric alcohol types in which polyhydric alcohols and fatty acids are linked by ester bonds, hydrophobic raw materials with hydroxyl groups such as higher alcohols and alkylphenols, mainly ethylene oxide (ethylene oxide ) added thereto, and a polyethylene glycol type in which ethylene oxide is added to a fatty acid or a polyhydric alcohol fatty acid ester. Preferred polyhydric alcohols are sucrose, sorbitan, and polyglycerin.
Examples of the polyhydric alcohol type include sucrose fatty acid esters, polyglycerin fatty acid esters, sorbitan fatty acid esters, etc. having alkyl chains of 8 to 20 carbon atoms, among which sucrose fatty acid esters and polyglycerin fatty acid esters are preferred. Polyethylene glycol type polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbit fatty acid esters, and polyoxyethylene glycerin fatty acid having an alkyl chain of 8 to 20 carbon atoms and an average number of added moles of ethylene oxide of 20 to 100. Esters, polyethylene glycol fatty acid esters, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers; polyoxyethylene hydrogenated castor oil and polyoxyethylene castor oil having an average addition mole number of ethylene oxide of 20 to 100; average ethylene oxide Examples include polyoxyethylene polyoxypropylene copolymers having a molar ratio of added moles/average added moles of propylene oxide of 0.2 to 7, among which polyoxyethylene hydrogenated castor oil and polyoxyethylene alkyl ether. , polyoxyethylene sorbitan fatty acid ester is preferred, and polyoxyethylene hydrogenated castor oil is more preferred.
These nonionic surfactants can be used singly or in combination of two or more.

The nonionic surfactant (C-1) is selected so that the HLB value of the nonionic surfactant to be blended is 6 to 20, particularly 9 to 18, suppressing unpleasant taste and reducing irritation in the oral cavity. point, it is more preferable.
The above HLB (Hydrophile-Lipophile Balance) value is the HLB according to Griffin (the same shall apply hereinafter).

Amphoteric surfactants (C-2) include betaine-type amphoteric surfactants such as alkylbetaine, betaine acetate, imidazolinium betaine, amidopropylbetaine and sulfobetaine, and amine oxides. In addition, those having an alkyl chain of 8 to 20 carbon atoms are preferred, and alkyl betaine, acetate betaine, imidazolinium betaine and amidopropyl betaine having the above alkyl chain are preferred. Among these, betaine type amphoteric surfactants are more preferred.

Betaine-based amphoteric surfactants include, for example, alkylbetaines (laurylbetaine, stearylbetaine, etc.), betaine acetates (lauryldimethylaminoacetic acid betaine, stearyldimethylaminoacetic acid betaine, etc.), imidazolinium betaine (2-alkyl-N-carboxy methyl-N-hydroxyethylimidazolinium betaine, N-lauroyl-N'-carboxymethyl-N'-hydroxyethylethylenediamine sodium, etc.), fatty acid amidopropyl betaine (lauramidopropyl betaine, coconut oil fatty acid amidopropyl betaine, etc.) , sulfobetaine (lauryl hydroxysulfobetaine, etc.). Among these, betaine acetate, imidazolinium betaine, and fatty acid amidopropyl betaine are preferable, and lauryldimethylaminoacetic acid betaine, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, N-lauroyl-N'- Carboxymethyl-N'-hydroxyethylethylenediamine sodium and coconut oil fatty acid amidopropyl betaine are more preferred. In particular, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaines, cocoamidopropylbetaines, and especially cocoamidopropylbetaines are preferred because of their good taste without bitterness.
These amphoteric surfactants can be used singly or in combination of two or more.

The blending amount of component (C) is preferably 0.01 to 3%, more preferably 0.1 to 1.5% of the total composition. When the blending amount is 0.01% or more, the unpleasant taste is sufficiently improved, and the irritation in the oral cavity is sufficiently reduced. When it is 3% or less, it is possible to prevent bitterness and oiliness due to the component (C) itself from manifesting as an unpleasant taste, and to maintain good taste.

The dentifrice composition of the present invention can be prepared as dentifrices such as toothpaste, liquid dentifrice and wet dentifrice, especially toothpaste. In addition to the above ingredients, known ingredients that are usually used in dentifrice compositions can be blended according to the dosage form, etc., as necessary, as long as the effects of the present invention are not impaired. Optional ingredients that can be blended include abrasives, binders, surfactants other than component (C), sweeteners, flavoring agents, pH adjusters, preservatives, and medicinal ingredients other than component (A).

Abrasives include calcium phosphate-based abrasives such as dicalcium phosphate dihydrate or anhydrate, monocalcium phosphate, tricalcium phosphate, and calcium pyrophosphate; precipitated silica, aluminosilicate, zirconosilicate, and titanium-bonded silica. silica-based abrasives such as calcium carbonate; calcium carbonate-based abrasives such as calcium carbonate; Two or more kinds can be blended. Among these, in particular, silica-based abrasives mainly composed of silicates such as precipitated silica, aluminosilicate, zirconosilicate, titanium-bonded silica, calcium carbonate-based abrasives, and silica-based abrasives such as precipitated silica 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. 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. , inorganic powders such as calcium sulfate, and mixtures thereof. In particular, silica and zeolite are preferred, and silica granules and zeolite granules are 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.

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. These can be used alone or in combination of two or more. The content of the binder is preferably 1.4 to 10%, particularly 1.4 to 3%, of the total composition.

Any surfactant can be used, including anionic surfactants. Specifically, alkyl sulfate, α-olefin sulfonate, hydrogenated coconut fatty acid monoglyceride monosulfate, lauryl sulfoacetate, N-acyl taurate such as N-methyl-N-acyl taurate, acyl sarcosinate , N-acyl-L-glutamate and the like. These can use 1 type(s) or 2 or more types. Among them, anionic surfactants containing a sulfonic acid group are preferable, and alkyl sulfates and α-olefin sulfonates are more preferable in terms of foamability and foam quality. Examples of the salt include sodium salt, potassium salt, ammonium salt and the like, with sodium salt being particularly preferred.
The alkyl sulfate preferably has 12 to 14 carbon atoms in the alkyl group, and specifically includes sodium lauryl sulfate and sodium myristoyl sulfate.
As the α-olefin sulfonate, an alkali metal salt such as sodium or potassium of an α-olefin sulfonate having 14 to 16 carbon atoms can be used. (common name: sodium tetradecenesulfonate) is preferred.
A preferred blending amount of the anionic surfactant is 0.6 to 2.5%, particularly 1 to 2.5%, of the total composition.

Sweetening agents include saccharin sodium, glycerin, stevioside, stevia extract, paramethoxycinnamic aldehyde, neohesperidyl dihydrochalcone, perillartine, glycyrrhizin, thaumatin, asparatylphenylalanine methyl ester and the like.

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.

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. Preservatives include paraoxybenzoic acid esters and sodium benzoate.

Medicinal ingredients include enzymes such as dextranase, amylase, protease, and mutanase; anti-inflammatory agents such as tranexamic acid, epsilon aminocaproic acid, aluminum chlorohydroxyallantoin, azulene, glycyrrhizinate, and glycyrrhizinate; cell activators such as vitamins Bactericides such as isopropylmethylphenol, cetylpyridinium chloride, benzalkonium chloride, hinokitiol, lysozyme chloride; water-soluble copper compounds such as copper chlorophyll and copper gluconate; anticalculus agents such as zeolite; agent; amino acids such as alanine, glycine, and proline; The amount of these medicinal ingredients to be blended is 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, and natural rubber can be blended as long as the effects of the present invention are not impaired.

EXAMPLES The present invention will be specifically described below by showing Examples, Comparative Examples, and Formulation 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 3 was prepared by a conventional method, and the feeling during use was evaluated by the following method. The results are also shown in Tables 1-3.

Evaluation method of feeling in use Evaluation of feeling in use was performed 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 Corporation) and brushed for 3 minutes. Disgust during use (absence of disgust) and sensation of irritation in the oral cavity during use (absence of irritation) were each judged according to the following scoring criteria, and the average score of four persons was obtained and evaluated according to the following evaluation criteria.
Here, the nasty taste is an unpleasant taste felt in the oral cavity due to the salty taste of salts or the like. The sensation of irritation in the oral cavity is a sensation of tingling stimulation to the oral mucosa.
<Sarcasm during use (no disgust)>
Rating Criteria 5: No unpleasant taste 4: Almost no unpleasant taste 3: Some unpleasant taste, but no problem level 2: Unpleasant taste 1: Strong unpleasant taste Evaluation criteria ◎: average score of 4 points or more ○: average score of 3 or more and less than 4 points ×: average score of less than 3 points

<Irritation in the oral cavity during use (no irritation)>
Scoring criteria 5: Did not feel stimulation 4: Almost did not feel stimulation 3: Slightly felt stimulation, but no problem level 2: Felt stimulation 1: Very much stimulation Evaluation criteria ◎: Average score is 4 points or more ○: average score is 3 or more and less than 4 points ×: average score is less than 3 points

Details of raw materials used are shown below.
(A) Component Potassium nitrate; Potassium nitrate (manufactured by Otsuka Chemical Co., Ltd.)
Sodium chloride; selected special grade salt (manufactured by Nihonkaisui Co., Ltd.)
(B) Component N-(4-cyanomethylphenyl)-2-isopropyl-5-methylcyclohexanecarboxamide; Evercool 180 (manufactured by Givaudan Japan Co., Ltd.)
(C) Component (C-1) Polyoxyethylene (20) hydrogenated castor oil; NIKKOL HCO-20, average added mole number of ethylene oxide 20 (manufactured by Nikko Chemicals Co., Ltd.)
(C-1) Polyoxyethylene (60) hydrogenated castor oil; NIKKOL HCO-60, average added mole number of ethylene oxide 60 (manufactured by Nikko Chemicals Co., Ltd.)
(C-1) polyoxyethylene (20) sorbitan isostearate; NIKKOL TI-10V, average added mole number of ethylene oxide 20 (manufactured by Nikko Chemicals Co., Ltd.)
(C-2) coconut oil fatty acid amidopropyl betaine; TEGO Betain CK (manufactured by EVONIK)

*；Reference example

*；Reference example

A formulation example is shown below.

[Prescription example 1]
(A) potassium chloride 5
(B) N-(4-cyanomethylphenyl)-2-isopropyl-5-methylcyclohexanecarboxamide 0.0001
(C-1) polyoxyethylene (20) hydrogenated castor oil 0.7
abrasive silica 15
Sorbit solution (70%) 30
Propylene glycol 3
Thickening silica 4
Xanthan gum 1.5
Sodium Lauryl Sulfate 1.6
Sodium fluoride 0.3
Saccharin sodium 0.18
Perfume 1
water residue
Total 100%

[Prescription Example 2]
(A) potassium citrate 5
(B) N-(4-cyanomethylphenyl)-2-isopropyl-5-methylcyclohexanecarboxamide 0.0001
(C-1) polyoxyethylene (20) hydrogenated castor oil 0.7
abrasive silica 15
Sorbit solution (70%) 30
Propylene glycol 3
Thickening silica 4
Xanthan gum 1.5
Sodium Lauryl Sulfate 1.6
Sodium fluoride 0.2
Saccharin sodium 0.18
Perfume 1
water residue
Total 100%

[Prescription Example 3]
(A) potassium oxalate 5
(B) N-(4-cyanomethylphenyl)-2-isopropyl-5-methylcyclohexanecarboxamide 0.0001
(C-1) polyoxyethylene (20) hydrogenated castor oil 0.7
abrasive silica 15
Sorbit solution (70%) 30
Propylene glycol 3
Thickening silica 4
Xanthan gum 1.5
Sodium Lauryl Sulfate 1.6
Sodium fluoride 0.2
Saccharin sodium 0.18
Perfume 1
water residue
Total 100%

[Prescription Example 4]
(A) potassium nitrate 5
(B) N-(4-cyanomethylphenyl)-2-isopropyl-5-methylcyclohexanecarboxamide 0.0001
(C-1) polyoxyethylene (20) hydrogenated castor oil 0.7
abrasive silica 15
Sorbit solution (70%) 30
Propylene glycol 3
Thickening silica 4
Xanthan gum 1.5
Sodium Lauryl Sulfate 1.6
Sodium fluoride 0.3
Saccharin sodium 0.18
Perfume 1
water residue
Total 100%

Claims (2)

(A) 0.5 to 15% by mass of one or more salts selected from potassium nitrate, potassium chloride, potassium citrate, potassium oxalate and sodium chloride;
(B) 0.00001 to 0.01% by mass of N-(4-cyanomethylphenyl)-2-isopropyl-5-methylcyclohexanecarboxamide
and (C) 0.01 to 3% by mass of fatty acid amidopropyl betaine having an alkyl chain with 8 to 20 carbon atoms
A dentifrice composition characterized by comprising 2. The dentifrice composition according to claim 1, wherein component (C) is coconut oil fatty acid amidopropylbetaine.