JPH10330232A - Composition for oral cavity - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject composition good in smell and taste, excellent in foamability, low in irritability, not causing the change of palate and useful for tooth pastes, etc., by compounding a specific amidocarboxylic acid or its salt. SOLUTION: This composition contains an amidocarboxylic acid of formula III (R1 is a 8-22C alkyl, etc.; R2 is H, a 1-6C alkyl, etc.; R3 is a group of formula IV, etc.; M is H, an alkali metal, etc.), or its salt (mono-N-laurylmalic acid amide, etc.), in an amount of 0.05-20 wt.%, preferably 0.1-5 wt.%, based on the whole composition. The compound of formula III is obtained from inexpensive raw materials at a good yield by reacting an amine of formula I (octylamine, etc.), with a dicarboxylic acid (malic acid, etc.), in the absence of a catalyst or in the presence of a basic catalyst in a solvent-free state or in a proper solvent.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to an oral composition having a good flavor, excellent foaming properties, low irritation, and little change in taste after use.

[0002]

2. Description of the Related Art Surfactants are incorporated in oral compositions such as dentifrices to enhance detergency and to impart a pleasant feeling upon use. You. Such surfactants have the effect of dispersing the oral composition in the oral cavity, the effect of promoting the dispersion and penetration of the medicinal component in the oral composition, the effect of foaming into the oral cavity by foaming, and the like. In addition, since it is used in the mouth, it is required to have high safety such as good taste and smell, and extremely low effects on the oral mucosa.

[0003] Conventionally, oral compositions include, as anionic surfactants, alkyl sulfates, fatty acid monoglyceride sulfates, N-acyl sarcosine salts and the like.
As a nonionic surfactant, sucrose fatty acid ester,
Polyoxyethylene-polyoxypropylene glycol block polymers, polyoxyethylene hydrogenated castor oil, and the like have been used.

[0004] However, among the anionic surfactants, alkyl sulfates and fatty acid monoglyceride sulfates have good foaming, but to varying degrees, irritation to the oral mucosa is recognized, and unpleasant tastes themselves. And had a smell. In addition, N-acyl sarcosine salts have improved taste, but have a problem of detachment of oral mucosa.

On the other hand, sucrose fatty acid esters of nonionic surfactants, polyoxyethylene-polyoxypropylene glycol block polymers and polyoxyethylene hydrogenated castor oil, although showing high safety, are higher than anionic surfactants. However, there was a problem that the foamability was remarkably inferior and a sufficient function could not be provided, and none of the above-mentioned conditions was satisfied.

In addition, since a single surfactant cannot satisfy the above-mentioned conditions (dispersibility, penetration promoting effect, foaming property, flavor, safety), the combination of two or more surfactants causes problems. Some proposals have been made to try to solve it. Examples of those improved by combining two or more kinds of surfactants include a combination of a glucose fatty acid ester and an N-acyl amino acid (JP-A-3-200714), and a combination of an alkyl sulfate ester salt and a glucose fatty acid ester (JP-A-Hei 3 -200713) has been proposed.

However, since two or more surfactants must be added, the production becomes complicated and the production efficiency deteriorates.

Accordingly, there has been a demand for a surfactant for an oral composition which can satisfy the above requirements even when used alone.

[0009]

Means for Solving the Problems and Embodiments of the Invention The present invention has been made in response to the above-mentioned demands, and comprises adding an amide carboxylic acid represented by the following general formula (1) or a salt thereof to provide a flavor. Good, excellent foaming, and low irritation,
Further, the present invention provides an oral composition having little change in taste after use.

[0010]

Embedded image

In the above general formula (1), R ₁Is a hydrophobic group
And is a long chain group having 8 to 22 carbon atoms, preferably 1
0-18 linear or branched alkyl groups, alkenyl
Or a hydroxyalkyl group. R ₁Has a carbon number of
If it is less than 8, the surface activity becomes insufficient, while it exceeds 22.
If so, solubility becomes worse.

R _TwoIs a hydrogen atom or a straight chain having 1 to 6 carbon atoms
Or branched alkyl or hydroxyalkyl groups
When the number of carbon atoms exceeds 6, the solubility becomes poor.

R _ThreeIs generally the dicarboxylic acid HOOC-R _Three−
COOH, specifically derived from malic acid or tartaric acid
Come. These dicarboxylic acids have D-form or L-form optical properties.
The isomers may be used alone or racemic.

M represents a hydrogen atom or a counter ion of a neutralized salt, and is an alkali metal, an alkaline earth metal, ammonium or an organic amine.

The compound of the above formula (1) can be prepared, for example, by reacting an amine represented by the following general formula (2) with a dicarboxylic acid represented by the following general formula (3) without using a solvent or an appropriate solvent. By reacting in the presence of a catalyst or a basic catalyst and passing through an imide compound, and possibly neutralizing, the compound can be synthesized from inexpensive raw materials in a high yield by a usual method.

[0016]

Embedded image(Where R ₁, R _Two, R _ThreeIs the same as above. )

Specific examples of the amine represented by the general formula (2) include primary amines such as octylamine, decylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine and behenylamine, and octylmethylamine. Secondary amines such as decylmethylamine, dodecylmethylamine, dodecylethylamine, dodecylhydroxyethylamine, tetradecylmethylamine, hexadecylmethylamine, octadecylmethylamine and tetradecylhydroxypropylamine can be exemplified.

The dicarboxylic acid represented by the general formula (3) includes malic acid or tartaric acid.

Specific examples of the amide carboxylic acid represented by the general formula (1) or a salt thereof include mono-N-lauryl malic amide, mono-N-decyl malic amide and mono-N-decyl malic amide.
N-decyltartaramide or salts thereof such as potassium salt, sodium salt, ammonium salt, triethanolamine salt and the like can be mentioned.

In the oral composition of the present invention, the amount of the amide carboxylic acid represented by the general formula (1) or a salt thereof is not particularly limited, but is preferably 0.05 to 20% by weight in the whole composition. Is preferably incorporated in an amount of 0.1 to 5% by weight.

The oral composition of the present invention may be in the form of a dentifrice composition such as a toothpaste, a powdered toothpaste, a liquid dentifrice, a prophylaxis paste, a mouthwash, a gingival massage cream, a troche, etc. In this case, in addition to the essential components, various known components may be used depending on the type of the oral composition.

For example, in the case of a dentifrice composition, as an abrasive, for example, calcium hydrogen phosphate dihydrate and calcium hydrogen phosphate anhydrous, calcium carbonate, calcium pyrophosphate, insoluble sodium metaphosphate, amorphous Porous silica, crystalline silica, precipitated amorphous silica, aluminosilicate, aluminum oxide, aluminum hydroxide,
Microcrystalline cellulose, resin, tribasic magnesium phosphate,
One or more base materials such as magnesium carbonate and zeolite can be used in combination.

Further, binders such as carboxymethylcellulose, hydroxyethylcellulose, alginate, carrageenan, gum arabic, xanthan gum, polyvinyl alcohol and gelatin, thickeners such as sorbitol, glycerin and propylene glycol, peppermint,
Essential oils such as spearmint, fragrances such as fragrance materials such as l-menthol, carvone, eugenol, anethole, saccharin sodium, stevioside, neohesperidyl dihydrochalcone, glycyrrhizin, perillartin, p
-Sweeteners such as methoxycinnamic aldehyde and thaumatin, preservatives such as sodium benzoate and parabens, and lysozyme chloride, dextranase, lytic enzyme, mutanase, chlorohexidine or a salt thereof, sorbic acid, alexidine, hinokitiol, cetyl chloride Pyridinium, benzethonium chloride, triclosan, allantoin, ε-aminocaproic acid, tranexamic acid, azulene, vitamin E, sodium monofluorophosphate, sodium fluoride, stannous fluoride, water-soluble primary or secondary phosphate, pyrroline An active ingredient such as acid salt, tripolyphosphate, hexametaphosphate, quaternary ammonium compound, sodium chloride and the like, a dye, and a solvent such as ethanol and water can be blended. In addition, the compounding quantity of the said component can be made into a usual dose.

Further, conventionally used surfactants such as lauryl sulfate, myristyl sulfate, α-olefin sulfonate, N-acyl sarcosine, fatty acid monoglyceride sulfate, sucrose fatty acid ester, polysulfate, etc. Oxyethylene-polyoxypropylene glycol block polymer, polyoxyethylene hydrogenated castor oil, fatty acid monoalkanolamide,
Imidazolinium betaine, alkyl amide betaine,
An amine oxide or the like can be used in combination.

The oral composition of the present invention can be prepared by a conventional method according to the type.

[0026]

The oral composition of the present invention has the above formula (1)
By blending the amide carboxylic acid or a salt thereof, the flavor is good, the foaming property is excellent, the stimulation is low, and the change in taste after use is small.

[0027]

EXAMPLES Hereinafter, the present invention will be described in detail with reference to Synthesis Examples and Test Examples of the amide carboxylic acid and salts thereof used in the present invention, and Examples of the oral composition of the present invention. The present invention is not limited to the following embodiments.

Synthesis of Amidocarboxylic Acid and Its Salt [Synthesis Example 1] Synthesis of mono-N-laurylmalic acid amide sodium salt 44.25 g of DL-malic acid, 55.6 dodecylamine
g and 45 g of dioxane were charged into a 300 ml four-necked flask and heated to 100 ° C. When the reflux of dioxane started, the reaction temperature was gradually raised to 140 ° C., and the reaction was further performed at the same temperature for 4 hours. Dioxane and by-produced water were completely distilled off to obtain an imide compound. The reaction-completed solid was dissolved in 200 ml of isopropyl alcohol (IPA),
44 g of an aqueous sodium hydroxide solution was added, and the mixture was stirred at 60 ° C. for 2 hours. The reaction solution was cooled to room temperature, and the precipitated solid was collected by filtration, further washed with IPA (100 ml) three times, and dried to obtain mono-N-lauryl malic acid amide sodium salt (purity: 99%).

The properties and the results of measurement and analysis are shown below. Properties: White crystals Melting point: Decomposes at 200 ° C. or higher Nitrogen analysis: 4.2% (theoretical value: 4.3%) Infrared absorption spectrum (IR): -CONH-1640 cm ^-1 -COONa 1583 cm ^-1 NMR (D ₂ O?) 0.66 (t, 3H) 1.08 (bs, 18H) 1.21 to 1.39 (m, 2H) 2.11 to 2.56 (m, 1H) 2.34 to 2.49 (M, 1H) 2.86 to 3.05 (m, 2H) 4.06 to 4.21 (m, 1H) Acid value (mgKOH / g): 171.7 (theoretical 173.5) Mass spectrometry: FAB (ionization method) (M + H) + [indicating a positive ion]; 324 M = C ₁₆ H ₃₀ O ₄ NNa

[Synthesis Example 2] Synthesis of potassium mono-N-lauryl malate amide The intermediate N-lauryl sulfate imide obtained in Synthesis Example 1 was recrystallized with hexane, and 30 g of the dried crystals were dispersed in 100 ml of water. And 18.5 g of a 40% aqueous KOH solution was added thereto, followed by 50
After stirring at 1 ° C. for 1 hour, the concentration was adjusted with water and
-A 20% aqueous solution of potassium lauryl malate amide was obtained. Acid value (mgKOH / g): 33.5 (theoretical 33.1)

Synthesis Example 3 Synthesis of potassium mono-N-decylmalate amide An intermediate N-decylmalimide was prepared in the same manner as in Synthesis Example 1 except that 47.2 g of decylamine was used instead of dodecylamine. Thus, a 20% aqueous solution of potassium mono-N-decylmalate was obtained in the same manner as in Synthesis Example 2. The properties of the powder (purity 95%, moisture 5%) obtained by drying and purifying this aqueous solution are shown. Properties: White crystals Melting point: Decomposed at 200 ° C. or higher Nitrogen analysis: 4.3% (theoretical value: 4.5%) Infrared absorption spectrum (IR): -CONH-1640 cm ^-1 -COONa 1583 cm ^-1 NMR (D ₂ O?) 0.66 (t, 3H) 1.08 (bs, 18H) 1.21 to 1.39 (m, 2H) 2.11 to 2.56 (m, 1H) 2.34 to 2.49 (M, 1H) 2.86 to 3.05 (m, 2H) 4.06 to 4.21 (m, 1H) Acid value (mgKOH / g): 171.7 (theoretical 180.4) Mass spectrometry: FAB (ionization method) (M + H) + [indicating a positive ion]; 312 M = C ₁₄ H ₂₆ O ₄ NK

[Synthesis Example 4] Synthesis of mono-N-decyltartaramide amide triethanolamine salt 99 g of tartaric acid, 94 g of decylamine and 90 of dioxane
g, 50 g of water in a 1 liter four-necked flask,
The temperature was raised to 100 ° C. When the reflux of dioxane started, the reaction temperature was gradually raised to 140 ° C., and the mixture was further reacted at the same temperature for 4 hours. Dioxane and water were completely distilled off to obtain an imide compound. IPA (300 ml) was added to and dissolved in the imide, and a 40% aqueous sodium hydroxide solution (44 g) was added, followed by stirring at 60 ° C. for 3 hours. One liter of IPA was further added to the reaction solution, and the mixture was cooled to room temperature. The precipitated solid was collected by filtration, washed three times with 1 liter of IPA, dried, and dried with sodium mono-N-decyltartaramide 165.
g was obtained. 20 g of this sodium salt was placed in a 1-liter beaker, 400 ml of water was added, the mixture was heated to 60 ° C. to dissolve, adjusted to pH 2 with 4N HCl, and further stirred at the same temperature for 2 hours. The precipitated solid was extracted with ether,
After repeated washing with water, the solvent was distilled off to obtain mono-N-decyltartaramide [acid type compound] (purity: 98%).

The properties and the results of measurement and analysis are shown below. Sexual shape: white crystals Melting point: 200 ° C. or higher in decomposition of nitrogen analysis: 4.8% (4.8% theoretical) Infrared absorption spectrum ^{(IR): - CONH- 1640cm -1} -COOH 1740cm -1 NMR (D 2 O?) 0.87 (t, 3H) 1.25 (bs, 14H) 1.43 to 1.61 (m, 2H) 3.16 to 3.35 (dt, 2H) 4.45 (bs, 1H) 4.63 (d, 1H) acid number (mg KOH / g): 192.2 (theoretical 194.2) mass spectrometry: FAB (ionization method) (M + H) + [showing positive ion]; 290 M = C ₁₄ H ₂₇ O ₄ N

Next, 10 g of this mono-N-decyltartaramide was dispersed in 100 ml of water, 5.6 g of triethanolamine was added, and the mixture was dissolved by stirring at 50 ° C. for 1 hour. The concentration was adjusted with water to obtain a 10% aqueous solution of mono-N-decyltartaric acid amide triethanolamine salt. Acid value (mgKOH / g): 12.0 (theoretical value 12.0)

Evaluation of Oral Composition Containing Amidocarboxylate
Using the foaming agents (surfactants) shown in Table 1, a toothpaste composition having the following formulation was prepared. The following methods were used to evaluate the foamability, taste, and irritability of these toothpaste compositions, and changes in taste after use. Toothpaste composition formulation (% by weight) Amorphous silica 25.0 Sorbitol solution 40.0 Propylene glycol 3.0 Saccharin Na 0.15 Fragrance 1.0 CMC-Na 1.2 Preservative 0.5 Surfactant Table Quantity of purified water shown in 1 Total 100.0

Evaluation of foaming property Using the toothpaste prepared according to the above formulation, foaming property was evaluated by the following method. Foamability evaluation method 2 g of the above dentifrice was dispersed in 18 ml of purified water, and
The solution was permeated for 20 seconds in a colorimetric tube with a ml stopper and the height of the foam after 30 minutes was measured.

[0037]

[Table 1]

As shown in Table 1, it was confirmed that the amide carboxylic acid of the present invention had the same good foaming properties as the alkyl sulfate.

Evaluation of taste and irritation and change in taste before and after use The above toothpaste was evaluated for the presence or absence of taste and irritation and change in taste before and after use. The changes in taste, irritation, and taste were evaluated by a toothpaste test conducted by eight well-trained professional panels and evaluated according to the following criteria. Evaluation criteria of taste ○: Good (no bitterness) △: Slightly bitter ×: Evaluation criteria of irritation which is strongly bitter and unbearable for use ○: No irritation △: Slightly irritated ×: Change in taste which is irritated and unbearable for use evaluation criteria ○: None of taste change △: although the change of taste is a little recognized, × seen the characteristics of the original taste: the change in taste is large, do not know the characteristics of the original taste

[0040]

[Table 2]

As shown in Table 2, it was recognized that the amide carboxylic acid of the present invention had a good taste, was low in irritation, and had little change in taste before and after use.

Examples will be described below. [Example 1] Toothpaste Sodium mono-N-lauryl malate 1.5% by weight Propylene glycol 2.5 CMC-Na 1.0 Carrageenan 0.2 Paraben 0.2 Sorbit 25 Saccharin sodium 0.18 Monofluorophosphoric acid Sodium 0.73 Calcium hydrogen phosphate 45 Perfume 1.0 Purified water Balance 100.0% by weight

Example 2 Toothpaste Sodium mono-methyl-N-lauryl malate 1.5% by weight Propylene glycol 2.5 Xanthan gum 0.6 Sodium polyacrylate 0.6 Paraben 0.01 Glycerin 20 Saccharin sodium 0 .15 Tranexamic acid 0.05 Dipotassium glycyrrhizinate 0.05 Aluminum hydroxide 45 Sodium lauryl sulfate 0.3 Perfume 1.2 Purified water Balance 100.0% by weight

Example 3 Toothpaste Potassium mono-N-lauryl malate potassium 1.2% by weight Propylene glycol 2.5 Xanthan gum 0.6 Carrageenan 0.4 Paraben 0.05 Sorbit 30 Sodium saccharin 0.1 Hydrogen phosphate Calcium 40 Alumina 1.0 Fragrance 0.8 Purified water Balance 100.0% by weight

Example 4 Toothpaste Potassium mono-N-decylmalate 1.8% by weight Propylene glycol 3.0 CMC-Na 0.8 Sodium polyacrylate 0.6 Paraben 0.15 Sorbit 35 Saccharin sodium 0. 2 Sodium monofluorophosphate 0.73 Aluminum hydroxide 45 Fragrance 1.0 Purified water Balance 100.0% by weight

Example 5 Toothpaste Mono-N-decyltartaramide amide triethanolamine 2.2% by weight Propylene glycol 3.0 CMC-Na 0.8 Carrageenan 0.3 Glycerin 25 Saccharin sodium 0.3 NaF 0.21 Silica 25 Calcium hydrogen phosphate 50 Titanium dioxide 0.5 Lauroyl diethanolamide 0.2 Perfume 1.0 Purified water Balance 100.0% by weight

Example 6 Toothpaste Potassium mono-N-laurylmalate 1.8% by weight Propylene glycol 2.5 CMC-Na 1.2 Paraben 0.1 Sorbit 22 Saccharin sodium 0.12 Salt 10 Calcium carbonate 42 Sodium lauryl sulfate 0.5 Perfume 1.0 Purified water Balance 100.0% by weight

Example 7 Toothpaste Sodium mono-methyl-N-lauryl malate 1.5% by weight Propylene glycol 1.0 CMC-Na 0.4 Paraben 0.2 Glycerin 6.0 Saccharin sodium 0.2 Carbonate Calcium 80 Flavor 1.0 Purified water Balance 100.0% by weight

Example 8 Liquid Toothpaste Potassium Mono-N-Lauryl Malate 1.8% by Weight Propylene Glycol 2.5 Xanthan Gum 0.25 Sorbit 45 Glycerin 20 Saccharin Sodium 0.12 NaF 0.21 Silica 20 Decaglycerin Fatty Acid Ester 0.3 Perfume 0.5 Blue No. 1 Trace purified water Balance 100.0% by weight

Example 9 Water Toothpaste Sodium mono-N-lauryl malate 1.8% by weight Glycerin 18 Sodium saccharin 0.1 Tranexamic acid 0.05 Ethyl alcohol 8 Fragrance 0.4 Blue No. 1 Trace amount of purified water residue 100.0% by weight

Example 10 Mouth Wash Solution Potassium Mono-N-Lauryl Malate 0.5% by Weight Paraben 0.02 Sorbit 15 Sodium Saccharin 0.05 Dipotassium Glycyrrhizinate 0.05 Ethyl Alcohol 10 Perfume 0.8 Purification Water balance 100.0% by weight

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[Procedure amendment]

[Submission date] November 14, 1997

[Procedure amendment 1]

[Document name to be amended] Statement

[Correction target item name] 0021

[Correction method] Change

[Correction contents]

The oral composition of the present invention can be in the form of a dentifrice composition such as a toothpaste, a powdered toothpaste, a liquid dentifrice, a prophylactic paste, a water dentifrice, a mouthwash, a gingival massage cream, a troche and the like. However, in this case, in addition to the essential components, various known components may be used depending on the type of the oral composition.

[Procedure amendment 2]

[Document name to be amended] Statement

[Correction target item name] 0023

[Correction method] Change

[Correction contents]

Further, a binder such as carboxymethylcellulose (sodium salt), hydroxyethylcellulose, alginate, carrageenan, gum arabic, xanthan gum, polyvinyl alcohol and gelatin, a thickener such as sorbitol, glycerin and propylene glycol, peppermint and spearmint Essential oils such as 1-menthol,
Fragrances such as fragrance materials such as carvone, eugenol, anethole, etc., sweeteners such as saccharin sodium, stevioside, neohesperidyl dihydrochalcone, glycyrrhizin, perillartin, p-methoxycinnamic aldehyde, thaumatin, preservatives such as sodium benzoate and parabens , Lysozyme chloride, dextranase, lytic enzyme, mutanase, chlorohexidine or a salt thereof, sorbic acid, alexidine, hinokitiol, cetylpyridinium chloride, benzethonium chloride, triclosan, allantoin, ε-aminocaproic acid, tranexamic acid,
Azulene, vitamin E, sodium monofluorophosphate, sodium fluoride, stannous fluoride, water-soluble primary or secondary phosphate, pyrophosphate, tripolyphosphate,
Active ingredients such as hexametaphosphate, quaternary ammonium compounds, sodium chloride, etc., dyes, and ethanol, water and the like as solvents can be blended. In addition, the compounding quantity of the said component can be made into a usual dose.

[Procedure amendment 3]

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[Correction contents]

The properties and the results of measurement and analysis are shown below. Properties: White crystal Melting point: Decomposed at 200 ° C or higher Nitrogen analysis: 4.2% (theoretical value: 4.3%) Infrared absorption spectrum (IR): -CONH-1640 cm ^-1 -COONa 1583 cm ^-1 NMR (D ₂ O?) 0.66 (t, 3H) 1.08 (bs, 18H) 1.21 to 1.39 (m, 2H) 2.11 to 2.56 (m, 1H) 2.34 to 2.49 (M, 1H) 2.86 to 3.05 (m, 2H) 4.06 to 4.21 (m, 1H) Acid value (mgKOH / g): 171.7 (theoretical 173.5) Mass spectrometry: FAB (ionization method) (M + H) ⁺ [indicating a positive ion]; 324 M = C ₁₆ H ₃₀ O ₄ NNa

[Procedure amendment 4]

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[Synthesis Example 2] Synthesis of potassium mono-N-lauryl malate amide The intermediate N-lauryl malate imide obtained in Synthesis Example 1 was recrystallized with hexane, and 30 g of the dried crystals were added to 100 ml of water. After dispersing, 18.5 g of a 40% KOH aqueous solution was added and stirred at 50 ° C. for 1 hour, the concentration was adjusted with water to obtain a 20% aqueous solution of potassium mono-N-laurylmalate amide. Acid value (mgKOH / g): 33.5 (theoretical 33.1)

[Procedure amendment 5]

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Synthesis Example 3 Synthesis of potassium mono-N-decylmalate amide An intermediate N-decylmalimide was prepared in the same manner as in Synthesis Example 1 except that 47.2 g of decylamine was used instead of dodecylamine. Thus, a 20% aqueous solution of potassium mono-N-decylmalate was obtained in the same manner as in Synthesis Example 2. The properties of the powder (purity 95%, moisture 5%) obtained by drying and purifying this aqueous solution are shown. Properties: White crystals Melting point: Decomposes at 200 ° C or higher Nitrogen analysis: 4.3% (theoretical value: 4.5%) Infrared absorption spectrum (IR): -CONH-1640 cm ^-1 -COONa 1583 cm ^-1 NMR (D ₂ O?) 0.66 (t, 3H) 1.08 (bs, 18H) 1.21 to 1.39 (m, 2H) 2.11 to 2.56 (m, 1H) 2.34 to 2.49 (M, 1H) 2.86 to 3.05 (m, 2H) 4.06 to 4.21 (m, 1H) Acid value (mgKOH / g): 171.7 (theoretical 180.4) Mass spectrometry: FAB (ionization method) (M + H) ⁺ [indicating a positive ion]; 312 M = C ₁₄ H ₂₆ O ₄ NK

[Procedure amendment 6]

[Document name to be amended] Statement

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[Correction method] Change

[Correction contents]

The properties and the results of measurement and analysis are shown below. Sexual shape: white crystals Melting point: 200 ° C. or higher in decomposition of nitrogen analysis: 4.8% (4.8% theoretical) Infrared absorption spectrum ^{(IR): - CONH- 1640cm -1} -COOH 1740cm -1 NMR (D 2 O?) 0.87 (t, 3H) 1.25 (bs, 14H) 1.43 to 1.61 (m, 2H) 3.16 to 3.35 (dt, 2H) 4.45 (bs, 1H) 4.63 (d, 1H) acid number (mg KOH / g): 192.2 (theoretical 194.2) mass spectrometry: FAB (ionization method) (M + H) ⁺ [showing positive ion]; 290 M = C ₁₄ H ₂₇ O ₄ N

[Procedure amendment 7]

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[0037]

[Table 1]

[Procedure amendment 8]

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[Correction contents]

[0040]

[Table 2]

[Procedure amendment 9]

[Document name to be amended] Statement

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Example 2 Toothpaste

[Procedure amendment 10]

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Example 7 Toothpaste

 ────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Shigeyuki Ueda 1-3-7 Honjo, Sumida-ku, Tokyo Lion Corporation

Claims (1)

[Claims] 1. An oral composition comprising an amide carboxylic acid represented by the following general formula (1) or a salt thereof. Embedded image