Surfactant-containing composition

Abstract

To provide means that prevents the occurrence of precipitation (cloudiness) even when a composition containing an amino acid-based surfactant and nicotinic acid is stored at low temperature.SOLUTION: A composition contains (A) nicotinic acid or a salt thereof and (B) an amino acid-based surfactant with a linear acyl group. In the mass chromatogram of LC / MS measurements, the peak area ratio shows that at least 99% of (B) has C12 linear acyl groups.SELECTED DRAWING: None

Description

Technical Field

[0001] The present disclosure relates to surfactant-containing compositions and the like, and more specifically, to a composition comprising an amino acid-based surfactant having a linear acyl group and nicotinic acid or a salt thereof, and uses of the same.

Background Art

[0002] Surfactants are incorporated into oral compositions for various purposes. For example, they may be incorporated as a bactericidal component or as a foaming agent. In addition, nicotinic acid, which is a type of niacin, may be incorporated into oral compositions, for example, in expectation of an anti-inflammatory effect.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] The present inventors have been advancing the development of an oral composition containing an amino acid-based surfactant and nicotinic acid, and have found that when a composition containing an amino acid-based surfactant and nicotinic acid is stored at low temperature, precipitation (cloudiness) may occur in some cases.

[0005] Accordingly, the cause of this cloudiness was further investigated.

Means for Solving the Problems

[0006] The inventors have found that the carbon chain length of the acyl group in the amino acid-based surfactant used may be related to the occurrence of turbidity. More specifically, they selected amino acid-based surfactants having linear acyl groups as the amino acid-based surfactants to be used in combination with nicotinic acid, and further found that when 99% or more of the peak area ratio of the mass chromatogram of these amino acid-based surfactants has C12 linear acyl groups, turbidity does not occur.

[0007] This disclosure includes, for example, the following subjects: Section 1. (A) Nicotinic acid or its salt, and (B) Amino acid-based surfactants having linear acyl groups It contains, Of (B), 99% or more of the peak area ratios in the LC / MS measurement of the mask chromatogram are amino acid-based surfactants having a C12 linear acyl group. composition. Section 2. (A) Nicotinic acid or its salt, and (B) Amino acid-based surfactants having linear acyl groups It contains, (B) Of these, 99% or more of the peak area ratio of the mass chromatogram measured by LC / MS is lauroyl glutamic acid or its salt. composition. Section 3. A composition for oral use, as described in item 1 or 2. Section 4. The composition according to any one of claims 1 to 3, comprising (A) nicotinic acid or a salt thereof in an amount of 10 parts by mass or less per 1 part by mass of (B) an amino acid-based surfactant having a linear acyl group. Section 5. (A) A composition according to any one of items 1 to 4, containing 0.01 to 2% by mass of nicotinic acid or a salt thereof. [Effects of the Invention]

[0008] A stable composition is provided that contains an amino acid-based surfactant and nicotinic acid or a salt thereof, and does not become cloudy even when stored at low temperatures. This composition is useful, for example, as an oral composition. [Modes for carrying out the invention]

[0009] The embodiments included in this disclosure will be described in more detail below. This disclosure preferably includes, but is not limited to, compositions containing (A) nicotinic acid or a salt thereof and (B) an amino acid-based surfactant having a linear acyl group, and their uses, etc. This disclosure includes everything disclosed herein and recognizable to those skilled in the art. Nicotinic acid or a salt thereof may be referred to as component (A), and the amino acid-based surfactant having a linear acyl group as component (B). Furthermore, a composition containing such components (A) and (B) may be referred to as the composition of this disclosure.

[0010] As the salt of nicotinic acid, alkali metal salts are preferred, sodium salts or potassium salts are more preferred, and sodium salts are even more preferred. Nicotinic acid or its salts can be used alone or in combination of two or more. Nicotinic acid is preferred among them.

[0011] The compositions of this disclosure preferably contain (A) nicotinic acid or a salt thereof in an amount of 10 parts by mass or less, and more preferably 0.01 to 10 parts by mass, of (B) an amino acid-based surfactant having a linear acyl group, per 1 part by mass. The upper or lower limit of this range (0.01 to 10) may be, for example, 0.02, 0.03, 0.04, 0.06, 0.08, 0.1, 0.2, 0.4, 0.6, 0.8, 1, 1.5, 2, 3, 4, 5, 6, 7, 8, 9, or 9.5. For example, the range may be 0.01 to 8, or 0.02 to 5.

[0012] Furthermore, the compositions of this disclosure preferably contain 0.01 to 2% by mass of component (A). The upper or lower limits of this range may be, for example, 0.02, 0.03, 0.04, 0.05, 0.08, 0.1, 0.3, 0.5, 0.7, 0.9, 1, 1.2, 1.5, 1.7, or 1.9% by mass. For example, the range may be 0.03 to 1.5% by mass.

[0013] (B) Amino acid-based surfactants having a linear acyl group are compounds having a structure in which a linear fatty acid and an amino acid are bonded, and more specifically, compounds having a structure in which the COOH group of the linear fatty acid and the NH2 group of the amino acid are bonded (-CO-NH-). For example, lauroyl glutamic acid has a structure in which lauric acid and glutamic acid are bonded. Examples of such linear fatty acids include C8-C16 linear fatty acids, and more specifically, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, etc. Examples of such amino acids include glutamic acid or its salts, aspartic acid or its salts, glycine, alanine, sarcosine, etc.

[0014] (B) The amino acid-based surfactant having a linear acyl group may have a salt in the amino acid portion, and as salts, alkali metal salts, ammonium salts, or triethanolamine salts are preferred, sodium salts or potassium salts are more preferred, and sodium salts are even more preferred.

[0015] Furthermore, the compositions of this disclosure preferably contain component (B) in an amount of, for example, 0.01 to 0.5% by mass. The upper or lower limit of this range may be, for example, 0.02, 0.05, 0.1, 0.2, 0.3, or 0.4% by mass. For example, this range may be 0.02 to 0.4% by mass.

[0016] However, in the composition of the present disclosure, 99% or more (preferably 99.2% or more, more preferably 99.4% or more) of the contained amino acid-based surfactant (B) having a linear acyl group is an amino acid-based surfactant having a C12 linear acyl group. When the proportion of the amino acid-based surfactant having a C12 linear acyl group in component (B) is less than 99%, clouding tends to occur particularly during low-temperature storage.

[0017] The proportion of the amino acid-based surfactant having a C12 linear acyl group in the component (B) is a value determined by LC / MS (liquid chromatography-mass spectrometry). That is, it is determined as follows. The sum of the peak areas of all peaks in the mass chromatogram measured at the mass-to-charge ratio (m / z) values derived from the entire amino acid-based surfactant having a linear acyl group (for example, when the surfactant is a metal salt, this corresponds to the molecular weight with the metal moiety removed) is taken as the total peak sum value indicating the proportion of the amino acid-based surfactant having that specific linear acyl group. Then, all the total peak sum values of the measured amino acid-based surfactants having linear acyl groups are added together to obtain the overall total peak sum value. The proportion of the amino acid-based surfactant having a specific linear acyl group refers to the ratio of the total peak sum value of the amino acid-based surfactant having that specific linear acyl group, when the overall total peak sum value is taken as 100%.

[0018] For example, as the amino acid-based surfactant having a linear acyl group, suppose (i) lauroyl glutamic acid (having a C12 linear acyl group) is mainly detected, and in addition, (ii) palmitoyl glutamic acid (having a C16 linear acyl group) and (iii) myristoyl glutamic acid (having a C14 linear acyl group) are also detected. If the ratio of the sum of all peak areas in the mass chromatogram of (i), the sum of all peak areas in the mass chromatogram of (ii), and the sum of all peak areas in the mass chromatogram of (iii) is 99.5:0.2:0.3, the proportion of lauroyl glutamic acid (having a C12 linear acyl group) is calculated as 99.5%.

[0019] From this, the proportion of the amino acid-based surfactant having a C12 linear acyl group in the component (B) can be referred to as the peak area ratio in the mass chromatogram obtained by LC / MS measurement, and this notation may be used in the present specification for convenience.

[0020] As the amino acid-based surfactant having a C12 linear acyl group, lauroyl glutamic acid or a salt thereof is more preferred. That is, as the composition of the present disclosure, a composition comprising (A) nicotinic acid or a salt thereof, and (B) an amino acid-based surfactant having a linear acyl group, wherein 99% or more (preferably 99.2% or more, more preferably 99.4% or more) of the peak area ratio in the mass chromatogram obtained by LC / MS measurement among (B) is lauroyl glutamic acid or a salt thereof, is more preferred.

[0021] Incidentally, as the (B) amino acid-based surfactant having a linear acyl group, a commercially available product can also be purchased and used. Such commercially available products are usually sold as products containing the target amino acid-based surfactant having a linear acyl group at high purity, but components having acyl groups with different carbon numbers may be mixed therein as impurities. For example, when the target surfactant is lauroyl glutamic acid (having a C12 linear acyl group), there may also be cases where palmitoyl glutamic acid (having a C16 linear acyl group) and myristoyl glutamic acid (having a C14 linear acyl group) are also contained as impurities. In such a case, as described above, for use in the composition of the present disclosure, it is preferable to select and use a commercially available product in which 99% or more of the peak area ratio in the mass chromatogram obtained by LC / MS measurement is lauroyl glutamic acid.

[0022] Furthermore, as described above, component (B) is a compound having a structure in which a linear fatty acid and an amino acid are bonded. While not limited to this, especially when using commercially available products, it is preferable that component (B) contained in the composition of this disclosure is a compound having a structure in which linear fatty acids of different carbon chain lengths are bonded to the same amino acid. Of these, it is preferable that component (B) having an acyl group with a carbon chain length of C12 accounts for 99% or more of the peak area ratio of the mass chromatogram measured by LC / MS.

[0023] The compositions of this disclosure may contain, alone or in addition to two or more optional components that can be incorporated into, for example, oral compositions, as long as they do not impair the effects.

[0024] For example, nonionic surfactants, anionic surfactants, or amphoteric surfactants can be incorporated as surfactants. Specifically, examples of nonionic surfactants include sugar fatty acid esters such as sucrose fatty acid esters, maltose fatty acid esters, and lactose fatty acid esters; fatty acid alkanolamides; glycerin fatty acid esters; sorbitan fatty acid esters; fatty acid monoglycerides; polyoxyethylene alkyl ethers with a polyoxyethylene addition coefficient of 8 to 10 and 13 to 15 carbon atoms in the alkyl group; polyoxyethylene alkylphenyl ethers with a polyoxyethylene addition coefficient of 10 to 18 and 9 carbon atoms in the alkyl group; diethyl sebacate; polyoxyethylene hydrogenated castor oil; and fatty acid polyoxyethylene sorbitan. Examples of anionic surfactants include sulfate ester salts such as sodium lauryl sulfate and sodium polyoxyethylene lauryl ether sulfate; sulfosuccinates such as sodium lauryl sulfosuccinate and sodium polyoxyethylene lauryl ether sulfosuccinate; and sodium cocoyl methyl taurate. Examples of amphoteric surfactants include betaine-type surfactants such as lauryldimethylaminoacetic acid betaine and coconut oil fatty acid amidopropyldimethylaminoacetic acid betaine; imidazoline-type surfactants such as alkylcarboxymethylhydroxyethylimidazolinium betaine and N-cocoyl-N-carboxymethyl-N-hydroxyethylethylenediamine sodium; and amino acid-type surfactants such as N-lauryldiaminoethylglycine. These surfactants can be used individually or in combination of two or more. The amount used is usually 0.1 to 5% by mass of the total composition.

[0025] In the compositions of this disclosure, if a surfactant is further contained, it is particularly preferable to use imidazolinium betaine, and among these, alkylcarboxymethylhydroxyethylimidazolinium betaine (sodium cocoamphoacetate) is preferred. When imidazolinium betaine is used, it may be contained in the compositions of this disclosure in amounts of, for example, 0.05 to 5% by mass. The upper or lower limit of this range (0.05 to 5% by mass) may be, for example, 0.1, 0.2, 0.5, 0.8, 1, 1.5, 2, 2.5, 3, 3.5, 4, or 4.5% by mass. For example, it is also preferable that the range be 0.1 to 3% by mass.

[0026] Furthermore, as flavoring agents, for example, menthol, carboxylic acid, anethole, eugenol, methyl salicylate, limonene, ocimene, n-decyl alcohol, citronellol, α-terpineol, methyl acetate, citronenyl acetate, methyl eugenol, cineole, linalool, ethyl linalool, thymol, spearmint oil, peppermint oil, lemon oil, orange oil, sage oil, rosemary oil, cinnamon oil, perilla oil, wintergreen oil, clove oil, eucalyptus oil, pimento oil, d-camphor, d-borneol, fennel oil, cinnamon oil, cinnamaldehyde, peppermint oil, vanillin, and other fragrances can be used. These can be added individually or in combination of two or more in amounts of, for example, 0.001 to 1.5% by mass of the total composition.

[0027] Furthermore, sweeteners such as sodium saccharin, potassium acesulfamethamate, stevioside, neohesperidyl dihydrochalcone, perillartin, thaumatin, aspartylphenylalanyl methyl ester, and p-methoxycinnamic aldehyde can be used. These can be added in amounts of, for example, 0.01 to 1% by mass relative to the total amount of the composition.

[0028] Furthermore, sorbitol, ethylene glycol, propylene glycol, glycerin, 1,3-butylene glycol, polypropylene glycol, xylitol, maltitol, lactitol, polyoxyethylene glycol, etc., can be used as humectants, either individually or in combination of two or more.

[0029] As preservatives, parabens such as methylparaben, ethylparaben, propylparaben, and butylparaben, sodium benzoate, phenoxyethanol, and alkyldiaminoethylglycine hydrochloride may be included.

[0030] As coloring agents, legally approved pigments such as Blue No. 1, Yellow No. 4, Red No. 202, and Green No. 3, mineral pigments such as ultramarine, enhanced ultramarine, and navy blue, and titanium dioxide may be added.

[0031] As pH adjusters, citric acid, phosphoric acid, malic acid, pyrophosphate, lactic acid, tartaric acid, glycerophosphate, acetic acid, nitric acid, or chemically possible salts thereof, or sodium hydroxide may be included. These can be included individually or in combination of two or more so that the pH of the composition is in the range of 4 to 8, preferably 5 to 7. The amount of pH adjuster may be, for example, 0.01 to 2% by weight.

[0032] The composition disclosed herein contains not only dodecylpyridinium chloride, but also, as pharmaceutically active ingredients, vitamin E derivatives such as dl-α-tocopherol acetate, tocopherol succinate, or tocopherol nicotinate; amphoteric bactericides such as dodecyldiaminoethylglycine; nonionic bactericides such as triclosan, isopropylmethylphenol, and hinokitiol; anionic bactericides such as sodium lauroyl sarcosinate; cationic bactericides such as cetylpyridinium chloride, chlorhexidine hydrochloride, benzalkonium chloride, and benzethonium chloride; dextranase, amylase, protease, mutanase, lysozyme, and lysozyme (Lite). Enzymes such as oxenzyme, alkali metal monofluorophosphates such as sodium monofluorophosphate and potassium monofluorophosphate, fluorides such as sodium fluoride and stannous fluoride, tranexamic acid and epsilon-aminocaproic acid, aluminum chlorohydroxyl allantoin, dihydrocholesterol, glycyrrhetinic acid, glycyrrhizic acid, sodium copper chlorophyllin, glycerophosphate, chlorophyll, sodium chloride, caropeptide, allantoin, carbazochrome, hinokitiol, potassium nitrate, and palatinite can be blended individually or in combination of two or more. Although not particularly limited, the compositions of this disclosure are especially preferably further containing isopropylmethylphenol. When isopropylmethylphenol is further contained, its content is, for example, about 0.005 to 2.0% by mass. The upper or lower limits of this range may be, for example, 0.01, 0.02, 0.03, 0.04, 0.05, 0.06, 0.07, 0.08, 0.09, 0.1, 0.2, 0.3, 0.4, 0.5, 0.8, 1.0, or 1.5 mass%. For example, the range may be approximately 0.01 to 1.5 mass%.

[0033] Furthermore, it is possible to add alcohols, silicones, apatite, white petrolatum, paraffin, liquid paraffin, microcrystalline wax, squalane, Plastibase, etc., as base materials.

[0034] Furthermore, the compositions of this disclosure can be prepared by known methods or by methods readily conceivable from known methods. For example, they can be prepared by appropriately mixing dodecylpyridinium chloride and glycyrrhizic acid or a salt thereof, and other components as needed.

[0035] The compositions of this disclosure can be preferably used, for example, as oral compositions. The subjects to whom the compositions of this disclosure can be applied are not particularly limited, but humans and non-human mammals are preferred. Preferred non-human mammals include livestock and pets, and more specifically, dogs, cats, mice, rats, horses, cattle, sheep, monkeys, etc.

[0036] In this specification, the term "comprising" includes both "consisting essentially of" and "consisting of." Furthermore, this disclosure encompasses all combinations of the constituent elements described herein.

[0037] Furthermore, the various characteristics (properties, structure, function, etc.) described in each embodiment of this disclosure above may be combined in any way to identify the subject matter covered by this disclosure. In other words, this disclosure covers all subject matter consisting of any combination of the combinable characteristics described herein. [Examples]

[0038] The embodiments of this disclosure will be described in more detail below with examples, but the embodiments of this disclosure are not limited to the examples below.

[0039] The compositions were prepared by mixing each component according to the composition shown in Table 1. The component values ​​in Table 1 are shown in mass percent. Two types of lauroyl glutamate (N-lauroyl-L-glutamate sodium) were used: (B1) and (B2). Both (B1) and (B2) are commercially available products sold as N-lauroyl-L-glutamate sodium, but they are products from different distributors. Alkyl carboxymethyl hydroxyethyl imidazolinium betaine (sodium cocoamphoacetate) was used as imidazolinium betaine.

[0040] Each composition was then stored at 5°C for one month, and visual inspection was performed to check for precipitation (clouding). Those that remained transparent were marked with ○, and those that showed precipitation (clouding) were marked with ×. The results are shown in Table 1.

[0041] [Table 1]

[0042] Based on these results, it was concluded that the presence or absence of precipitation (turbidity) was due to differences in the lauroyl glutamate used.

[0043] Therefore, the lauroyl glutamates (B1) and (B2) used were analyzed by LC-MS, and from the peaks of the obtained MS spectra, it was found that while acyl glutamates with a C12 acyl group (i.e., lauroyl glutamate) were mainly present, acyl glutamates with acyl groups of other carbon chain lengths were also detected. Detailed results are shown in Table 2.

[0044] [Table 2]

Claims

1. (A) Nicotinic acid or its salts, and (B) Amino acid-based surfactant having a linear acyl group It contains, Of (B), 99% or more of the peak area ratios in the LC / MS measurement of the mask chromatogram are amino acid-based surfactants having C12 linear acyl groups. composition.

2. (A) Nicotinic acid or its salts, and (B) Amino acid-based surfactant having a linear acyl group It contains, (B) Of these, 99% or more of the peak area ratio of the mass chromatogram measured by LC / MS is lauroyl glutamic acid or its salt. composition.

3. The composition according to claim 1 or 2, which is an oral composition.

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