CN116963713A

CN116963713A - Composition containing ceramide

Info

Publication number: CN116963713A
Application number: CN202280012429.5A
Authority: CN
Inventors: 江川淳一郎; 山下美年雄
Original assignee: Kose Corp
Current assignee: Kose Corp
Priority date: 2021-01-29
Filing date: 2022-01-11
Publication date: 2023-10-27
Also published as: TW202245734A; JPWO2022163336A1; WO2022163336A1; KR20230133305A

Abstract

The present invention addresses the problem of providing a composition which suppresses the crystallization of ceramide and thereby achieves an excellent effect of improving the barrier function of the stratum corneum. The composition for solving the problem is characterized by comprising a ceramide and a uronic acid-containing polysaccharide in an aqueous solvent containing propylene glycol and/or polypropylene glycol.

Description

Composition containing ceramide

Technical Field

The present invention relates to a composition stably containing a ceramide, and more particularly, to a composition containing a ceramide and a uronic acid-containing polysaccharide in a specific aqueous solvent.

Background

Since it was clarified that lipids among plasma cells such as ceramide are closely related to the barrier function of the horny layer, attempts have been made to develop moisturizing preparations incorporating ceramides. However, the ceramide has a strong crystallinity, and from the viewpoints of improving stability and exhibiting moisturizing effect on skin, it is desired to develop a cosmetic or skin external preparation which does not cause crystallization.

As a composition for the purpose of stabilizing the blending of ceramide, a technique of stabilizing a particulate ceramide by forming a protective colloid with a water-soluble polymer has been disclosed (see patent document 1). However, in this technique, since the crystals of the ceramide are micronized, it cannot be said that the moisturizing effect is sufficiently exhibited from the viewpoint of the fusion property to the stratum corneum.

Further, a novel compound obtained by introducing a ceramide into hyaluronic acid through a covalent bond is disclosed (see patent document 2). However, this compound is not sufficient for improving the barrier function of the horny layer possessed by the ceramide type because hyaluronic acid is strongly bonded to the ceramide type.

In order to stably blend ceramide, a technique of blending a specific fatty acid and a surfactant in combination is disclosed (see patent document 3). However, in order to stabilize the ceramide, the blending amount of the surfactant needs to be increased, and thus safety and feeling of use may be impaired. On the other hand, in the case where the blending amount of the surfactant is reduced in order to obtain an excellent feel in use, the surfactant is often cloudy or translucent and opaque, and in this case, separation or milk separation occurs with time, and it is difficult to secure sufficient stability with time.

Thus, in the prior art, it is not possible to obtain a cosmetic or a skin external preparation which can inhibit crystallization of ceramide in the composition, and which does not impair the safety, feeling of use and stability as a preparation, and improve the barrier function of the horny layer.

Prior art literature

Patent literature

Patent document 1: japanese patent laid-open publication No. 2009-269882,

patent document 2: japanese patent application laid-open No. 2013-526620,

patent document 3: japanese patent application laid-open No. 2001-316217.

Disclosure of Invention

Problems to be solved by the invention

The present invention has been made in view of the above-described circumstances, and an object thereof is to provide a composition which suppresses crystallization of ceramide and thereby provides an excellent effect of improving the barrier function of the horny layer.

Means for solving the problems

The present inventors have made intensive studies to solve the above problems, and as a result, have found that by containing a ceramide and a uronic acid-containing polysaccharide in a specific aqueous solvent, crystallization of the ceramide can be suppressed, and that by applying the composition to the skin, the composition can rapidly penetrate into the stratum corneum, and an excellent effect of improving the barrier function of the stratum corneum can be obtained, thereby completing the present invention.

That is, the present invention is a composition comprising a ceramide and a uronic acid-containing polysaccharide in an aqueous solvent containing propylene glycol and/or polypropylene glycol.

ADVANTAGEOUS EFFECTS OF INVENTION

The composition of the present invention can inhibit crystallization of ceramide, thereby obtaining an excellent effect of improving the barrier function of the horny layer of ceramide.

Drawings

FIG. 1 is an optical micrograph of the composition of example 1-1.

FIG. 2 is an optical micrograph of the composition of examples 1-2.

FIG. 3 is an optical micrograph of the composition of comparative example 1-1.

Detailed Description

The ceramide used in the present invention is a nonionic amphiphilic substance having 1 or more long-chain linear and/or branched alkyl or alkenyl groups, at least 2 or more hydroxyl groups, and 1 or more amide groups (and/or amino groups) in the molecule, or a derivative obtained by binding a phosphatidylcholine residue or a sugar residue to the hydroxyl group of the nonionic amphiphilic substance, and may be a natural extract or a synthetic product. For example, natural ceramides such as sphingosine, phytosphingosine, and ceramides 1, 2, 3, 4, 5, and 6, which are long-chain fatty acid amides of these, sphingomyelin, phytosphingomyelin, and the like, sphingoglycolipid, such as cerebrosides and gangliosides, and phytoglycosphingolipids, which are phospholipid derivatives of sphingosine and phytosphingosine, can be exemplified, and 1 or 2 or more of these can be used. Among them, natural ceramide is preferable, and ceramide 2 and ceramide3 are particularly preferable from the viewpoint of suppressing crystallization and the like. Examples of commercial products of natural CERAMIDEs include Ceramide I, ceramide III, ceramide VI (manufactured by EVONIC Co., ltd.), ceramide TIC-001 (manufactured by high sand flavor Co., ltd.), ceramide 2 (manufactured by Croda Japan KK), and Ceramide AC45 (manufactured by NFCC corporation).

The content of the ceramide in the composition of the present invention is not particularly limited, but is preferably in the range of 0.001 to 3 mass% (hereinafter abbreviated as "%") from the viewpoint of touch feeling or the like, more preferably in the range of 0.001 to 1%, and still more preferably in the range of 0.01 to 0.5%.

The uronic acid-containing polysaccharide used in the present invention is a polysaccharide containing uronic acid in at least 10% or more in structure. Examples of uronic acid constituting the uronic acid-containing polysaccharide include glucuronic acid, galacturonic acid, iduronic acid, and the like, and among them, glucuronic acid is preferably contained from the viewpoint of preventing crystallization of ceramide. Examples of the polysaccharide containing glucuronic acid include mucopolysaccharides (glycosaminoglycans) such as chondroitin sulfate and hyaluronic acid, tremella polysaccharide, and the like. Tremella polysaccharide is a polysaccharide extracted from Tremella and containing mannose, xylose, and glucuronic acid as constituent sugar, and is commercially available as Tremolst TP, SL, and SLB (Japanese refinement Co., ltd.). Among them, hyaluronic acid is preferable. In the present specification, hyaluronic acid includes hyaluronic acid and derivatives thereof, and salts thereof, and the source thereof may be any of natural products (extracts), fermented products, and the like. The hyaluronic acid is not particularly limited, but hyaluronic acid dissolved or dispersed in water is preferable, and examples thereof include sodium hyaluronate, potassium hyaluronate, sodium oleoyl hyaluronate, sodium caproyl hyaluronate, sodium carboxymethyl hyaluronate, polyethylene glycol hyaluronate, crosslinked sodium hyaluronate, sodium hydroxypropyl trimethylammonium modified hyaluronate, and the like, and 1 or 2 or more of them may be used. The molecular weight of the hyaluronic acid is not particularly limited, but from the viewpoint of preventing crystallization of the ceramide, the weight average molecular weight is preferably 30 ten thousand or less, more preferably in the range of 1000 to 20 ten thousand. In the present specification, the weight average molecular weight of hyaluronic acid means a value measured by the following method.

The weight average molecular weight of the hyaluronic acid used in the present invention can be obtained by using hyaluronic acid having a known weight average molecular weight as a standard, applying high performance liquid chromatography to a sample and the standard, obtaining a standard curve from the weight average molecular weight and retention time of the standard, and obtaining a weight average molecular weight corresponding to the retention time of a sample solution. The weight average molecular weight of the standard may be determined according to japanese pharmacopoeia of thirteenth edition: intrinsic viscosity was measured by the general test method, item 36 viscometry, and was calculated according to the formula of Laurent et al (Biochim. Biophys. Acta,42, 476 (1960)).

The content of uronic acid-containing polysaccharide in the composition of the present invention is not particularly limited, but is preferably in the range of 0.001 to 5%, more preferably in the range of 0.01 to 3%, even more preferably in the range of 0.01 to 1%, from the viewpoint of preventing crystallization of ceramide.

The mass ratio of the ceramide to the uronic acid-containing polysaccharide (ceramide/uronic acid-containing polysaccharide) in the composition of the present invention is not particularly limited, but is preferably 0.001 to 1, more preferably 0.005 to 0.5, from the viewpoint of preventing crystallization of the ceramide or the like.

An aqueous solvent is used in the composition of the present invention. In the present specification, the aqueous solvent means a solvent composed of water and an aqueous component other than water. As the aqueous component, there may be used lower alcohols such as ethanol and 2-propanol, polyhydric alcohols such as ethylene glycol, glycerin, 1, 3-butanediol and propylene glycol, polyethers such as polyethylene glycol and polypropylene glycol, and the like, and 1 or 2 or more of them may be used in combination. In the composition of the present invention, propylene glycol and/or polypropylene glycol are contained in the aqueous solvent. The polypropylene glycol is a polymer of propylene glycol, and in the present invention, the polymerization degree is not particularly limited as long as it is 2 or more, and is preferably 2 to 9, more preferably 2 to 7. In addition, from the viewpoint of preventing crystallization of ceramide, the molecular weight of polypropylene glycol is preferably 400 or less, more preferably 200 or less. Examples of such polypropylene glycol having a molecular weight of 200 or less include dipropylene glycol and tripropylene glycol. The total content of propylene glycol and polypropylene glycol in the entire aqueous solvent is preferably 30% or more, more preferably 50% or more, and still more preferably 60% or more, from the viewpoint of preventing crystallization of ceramide. The content of the total aqueous solvent in the composition of the present invention is not particularly limited, but is preferably 40 to 99.9%, more preferably 60 to 99%.

The content of propylene glycol and/or polypropylene glycol in the composition is not particularly limited, but is preferably 30 to 90%, more preferably 50 to 80%, from the viewpoint of preventing crystallization of ceramide. The water content of the composition is preferably 10 to 70%, more preferably 20 to 50%, and the water content of the aqueous solvent is preferably 5 to 70%, more preferably 10 to 50%, and even more preferably 10 to 40%. Further, from the viewpoint of preventing crystallization of ceramide, etc., the content ratio of propylene glycol and/or polypropylene glycol to water ((propylene glycol and/or polypropylene glycol)/water) in the composition is preferably 0.1 to 5, more preferably 0.4 to 4, and even more preferably 1 to 4.

The composition of the present invention is not particularly limited as long as it contains a ceramide and a uronic acid-containing polysaccharide in an aqueous solvent, and preferably contains a complex composed of a ceramide and a uronic acid-containing polysaccharide, a ceramide and a uronic acid-containing polysaccharide (hereinafter referred to as "ceramide-uronic acid-containing polysaccharide complex"). The ceramide-uronic acid-containing polysaccharide complex is thought to be formed by electrostatic interaction in an aqueous solvent, and to maintain a moderate binding state. Therefore, as with the dissolved ceramide, the ceramide is applied to the skin to quickly penetrate into the stratum corneum, thereby obtaining an excellent effect of improving the barrier function of the stratum corneum. If the ceramide-uronic acid-containing polysaccharide complex is formed, the composition floats as a mist or fibrous amorphous aggregate, and becomes cloudy, so that the presence or absence of the ceramide-uronic acid-containing polysaccharide complex can be confirmed by visually observing the appearance of such a composition (see fig. 1 and 2). Further, since the complex was observed as an amorphous aggregate by observation with an optical microscope (bright field image) under the conditions described in examples, the presence or absence of such an amorphous aggregate was confirmed. In addition, the composition of the present invention is a composition in which the ceramide forms a complex with the uronic acid-containing polysaccharide, and crystals of the ceramide are not precipitated, and thus are stably present in the composition, for example, by the method of the time-lapse stability test described in examples, the composition is placed in a glass container and sealed, and after being stored at constant temperatures of 50 ℃ and 5 ℃ for 2 weeks, the presence of crystals derived from the ceramide is not observed by observation with an optical microscope (polarization field image) at any of the storage temperatures (see fig. 1 and 2). The bright field images shown in fig. 1 to 3 were obtained by observing light transmitted through or reflected from the sample by a bright field observation method, and the polarized field images were obtained by observing the light by a polarized light observation method under an orthogonal polarizer. In the polarization field image, the presence or absence of deposition of the ceramide-like crystals can be confirmed by contrast (see fig. 3).

The compositions of the present invention can also be made transparent by using nonionic surfactants having an isostearic acid backbone. The composition was visually observed for no amorphous aggregates, but the presence or absence of the amorphous aggregates was confirmed by observation with an optical microscope.

The nonionic surfactant having an isostearic acid skeleton is not particularly limited as long as it is dissolved or dispersed in water, and examples thereof include polyoxyethylene hydrogenated castor oil, polyoxyethylene glyceryl isostearate, polyglyceryl diisostearate, polyoxyethylene glyceryl isostearate, polyoxyethylene hydrogenated castor oil isostearate, polyoxyethylene sorbitan isostearate, polyoxyethylene glycol isostearate, and isostearyl polyethylene glycol. In the present invention, the nonionic surfactant having an isostearic acid skeleton is preferably polyoxyethylene glyceryl isostearate, polyglyceryl diisostearate, polyoxyethylene hydrogenated castor oil isostearate, more preferably polyoxyethylene (8) glyceryl isostearate, polyglyceryl diisostearate (10) ester, polyoxyethylene hydrogenated castor oil isostearate, and commercially available products include EMASEX GWIS-108, EMALEC RWIS-150 (manufactured by Nihon efficiency Co., ltd., above), NIKKOL Decaglyn 2-ISV (NIPPON SURFACTANT INDUSTRIES CO., LTD), and the like, from the viewpoint of preventing crystallization of ceramide. 1 or 2 or more of them may be used.

The content of the nonionic surfactant having an isostearic acid skeleton in the composition of the present invention is not particularly limited, but is preferably 0.01 to 10%, more preferably 0.05 to 5%, and even more preferably 0.1 to 2% from the viewpoint of dispersibility of the ceramide-uronic acid-containing polysaccharide complex. The mass ratio of the ceramide to the nonionic surfactant having an isostearic acid skeleton in the composition (ceramide/nonionic surfactant having an isostearic acid skeleton) is not particularly limited, but is preferably 0.001 to 1, more preferably 0.001 to 0.1, and even more preferably 0.001 to 0.05, from the viewpoint of dispersibility of the ceramide-uronic acid-containing polysaccharide complex.

In the present invention, from the viewpoint of dispersibility of the ceramide-uronic acid-containing polysaccharide complex and the like, it is further preferable to use a nonionic surfactant having an isostearic acid skeleton and/or other nonionic surfactant and/or anionic surfactant.

The nonionic surfactant (excluding nonionic surfactants having an isostearic acid skeleton) is not particularly limited, and the HLB of the nonionic surfactant is preferably 10 to 18, more preferably 10 to 16. Examples of the nonionic surfactant include sorbitan fatty acid esters, polyglycerin fatty acid esters, sucrose fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbitol fatty acid esters, polyoxyethylene glycol fatty acid esters, polyoxyethylene glycerin fatty acid esters, polyoxyethylene alkyl ethers, polyoxyethylene cholesterol ethers, polyoxyethylene phytosterol ethers, polyoxyethylene polyoxypropylene alkyl ethers, polyoxyethylene hydrogenated castor oil, polyoxyethylene fatty acid ethanolamides, polyoxyalkylene modified silicones, and polyoxyalkylene alkyl co-modified silicones. In the present invention, sucrose fatty acid ESTER, polyoxyethylene hydrogenated castor oil, polyoxyethylene cholesterol ether are more preferable, and examples of commercial products include NIKKOOL HCO-60 (NIPPON SURFACTANT INDUSTRIES CO., LTD.), EMALEX CS-10 (Nihon Emulsion Co., ltd.), DK ESTER S-160 (manufactured by first Industrial pharmaceutical Co., ltd.). From these, 1 or 2 or more kinds of use can be appropriately selected.

Herein, HLB (hydrophilic-hydrophobic balance (Hydphile-Lipophile Balance)) in the present invention is an index indicating the balance between hydrophilicity and lipophilicity, and is calculated by the following formula (1) in the fields, temple, etc.

Hlb= "Inorganism Value (IV)/organic sex value (OV)". Times.10. Cndot. Of formula 1

(refer to Jia Tian Shansheng, "organic concept graph-basis and application-"With the transmission concept-base material) "pages 11-17, published in 1984).

Examples of the anionic surfactant include fatty acid salts such as stearic acid, lauric acid and isostearic acid, alkyl sulfonate, α -olefin sulfonate, N-long chain acyl amino acid salt, N-acyl taurate, N-alkyl-N-acyl taurate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkylphenyl ether sulfate, N-acyl amino acid salt, N-acyl-N-alkyl amino acid salt, etc., particularly preferably fatty acid salt, N-alkyl-N-acyl taurate, and further preferably isostearate and/or stearyl methyl taurate. Examples of the salts include Na, K, ca, al, mg, zn and triethanolamine salts, and Na, K and triethanolamine salts are more preferable. Examples of the commercial products include ISOSTEARIC ACID EX (Kokyu Alcohol Kogyo co., ltd.) and NIKKOL SMT (NIPPON SURFACTANT INDUSTRIES co., ltd.) and 1 or 2 or more kinds of them may be appropriately selected for use.

The content of the nonionic surfactant (excluding the nonionic surfactant having an isostearic acid skeleton) and/or the anionic surfactant is not particularly limited, but is preferably 0.05 to 10%, more preferably 0.1 to 5%, still more preferably 0.15 to 4.5% from the viewpoint of dispersibility of the ceramide-uronic acid-containing polysaccharide complex.

The mass ratio of the nonionic surfactant having an isostearic acid skeleton to the nonionic surfactant (excluding the nonionic surfactant having an isostearic acid skeleton) and/or the anionic surfactant [ nonionic surfactant having an isostearic acid skeleton/{ nonionic surfactant (excluding the nonionic surfactant having an isostearic acid skeleton) and/or the anionic surfactant } ] is not particularly limited, but is preferably 0.05 to 3, more preferably 0.1 to 2, and even more preferably 0.2 to 1 from the viewpoint of dispersibility of the ceramide-uronic acid-containing polysaccharide complex.

The method for producing the composition of the present invention is not particularly limited, and the composition can be produced, for example, by mixing a ceramide-based solution in which ceramide is dissolved and a uronic acid-containing polysaccharide-based solution in which uronic acid-containing polysaccharide is dissolved by heating. Among the aqueous components constituting the aqueous solvent, propylene glycol and/or polypropylene glycol are preferably used in the ceramide-based solution from the viewpoint of suppressing crystallization of ceramide and the like. The content of propylene glycol and/or polypropylene glycol in the solvent used in the ceramide-based solution is not particularly limited, but is preferably 60% or more, more preferably 80% or more. The ceramide-based solution can be prepared by dissolving the ceramide-based solution in such a solvent by heating. The heating temperature is preferably 70 to 100 ℃, more preferably 80 to 100 ℃.

Among the aqueous components constituting the aqueous solvent, water is preferably used in the uronic acid-containing polysaccharide solution. The content of water in the solvent used for the uronic acid-containing polysaccharide solution is not particularly limited, but is preferably 50 to 99%, more preferably 70 to 99%. By dissolving uronic acid-containing polysaccharides in such a solvent, uronic acid-containing polysaccharide solutions can be prepared. The uronic acid-containing polysaccharide can be dissolved even at room temperature (25 ℃) without a special heating operation, but from the viewpoint of suppressing crystallization of the ceramide, the dissolution by heating is preferable. The heating temperature is preferably 70 to 100 ℃, more preferably 80 to 100 ℃.

The composition of the present invention can be obtained by mixing the ceramide-containing solution and the uronic acid-containing polysaccharide solution, and the composition containing a ceramide-uronic acid-containing polysaccharide complex can be preferably obtained by the above-described production method. From the viewpoint of suppressing crystallization of ceramide, etc., it is preferable to mix the ceramide-based solution and the uronic acid-containing polysaccharide-based solution at a temperature of 70 to 100 ℃.

The composition of the present invention obtained as described above can be used as it is as a cosmetic or a skin external preparation, or can be further combined with other components to prepare a cosmetic or a skin external preparation. Examples of the cosmetic composition include skin care cosmetics such as lotions, vanishing creams, eye creams, beauty lotions, massage agents, facial masks, hand creams, body lotions, body creams, and the like, cosmetics such as make-up cosmetics, and external preparations such as topical liquids, topical gels, creams, ointments, liniments, lotions, cataplasms, plasters, sprays, and aerosols. The content of the composition in the cosmetic or skin external preparation is not particularly limited, and for example, it is preferably 1 to 50%, more preferably 5 to 20% in the cosmetic or skin external preparation. The formulation is not particularly limited, and various formulations such as an aqueous cosmetic, a water-in-oil cosmetic, an oil-in-water cosmetic, and an oily cosmetic can be used. In the present specification, the external skin preparation includes quasi drugs (quasi-drugs) and medicines.

In the cosmetic or skin external preparation of the present invention, components blended in a usual cosmetic or skin external preparation can be used within a range that does not interfere with the effects of the present invention and the formation of the complex. Specific examples of such optional components include oils, alcohols, powders, water-soluble polymers, film-forming agents, surfactants, oil-soluble gelling agents, organically modified clay minerals, resins, ultraviolet absorbers, preservatives, antibacterial agents, perfumes, antioxidants, pH adjusters, chelating agents, skin-active ingredients, and the like.

Preferred formulations of the cosmetic composition of the present invention include aqueous cosmetic compositions. In the present specification, the aqueous cosmetic is a formulation in which an aqueous phase composed of an aqueous solvent is used as a continuous phase and substantially no oily component is contained. In the present specification, substantially not containing an oily component means that the content of the oily component in the cosmetic is preferably less than 0.5%, more preferably less than 0.1%, and even more preferably less than 0.05%. In the aqueous cosmetic, the effect of suppressing crystallization of the ceramide is further improved due to the improvement of transparency, and therefore, it is preferable to contain a nonionic surfactant having an isostearic acid skeleton. The nonionic surfactant having an isostearic acid skeleton may be contained in the composition or may be added separately from the composition to prepare it as a cosmetic or skin external preparation. The content of the nonionic surfactant having an isostearic acid skeleton in the aqueous cosmetic is not particularly limited, but is preferably 0.01 to 10%, more preferably 0.05 to 5%, and even more preferably 0.1 to 2% from the viewpoint of dispersibility of the ceramide-uronic acid-containing polysaccharide complex. The mass ratio of the ceramide to the nonionic surfactant having an isostearic acid skeleton (ceramide/nonionic surfactant having an isostearic acid skeleton) in the aqueous cosmetic is not particularly limited, but is preferably 0.001 to 1, more preferably 0.001 to 0.1, and even more preferably 0.001 to 0.05, from the viewpoint of dispersibility of the ceramide-uronic acid-containing polysaccharide complex.

The cosmetic or skin external preparation of the present invention was subjected to the time stability test described in examples, placed in a glass container, sealed, and stored at constant temperatures of 50 ℃ and 5 ℃ for 2 weeks, and then at any storage temperature, the presence of crystals derived from ceramide was not observed by observation with an optical microscope (see fig. 3). In this way, whether or not the ceramide forms a complex with the uronic acid-containing polysaccharide can be determined based on the presence or absence of crystallization in the stability test with time.

Examples

The present invention will be described more specifically with reference to examples, but the present invention is not limited to the examples.

Preparation of the composition (1): examples 1-1 to 1-3, comparative 1-1

The composition was prepared according to the following formulation, recipe. For each of the obtained compositions, "formation of complex", "stability immediately after production", "stability with time (5 ℃ and 50 ℃/2 weeks)" were evaluated according to the following methods and criteria. The results are shown in table 1.

< examples 1 to 1>

The composition was prepared by the following formulation, method of manufacture.

*1CERAMIDE3 (manufactured by EVONIC Co., ltd.)

*2DPG-RF (manufactured by ADEKA Co., ltd.)

*3 hyaluronic acid FCH-SU (weight average molecular weight 10 ten thousand made by Food Chemifa Co., ltd.)

(preparation method)

And (3) and (2) and (3) are heated, mixed and dissolved at 80 ℃. The two were mixed, stirred at 80℃for 10 minutes using a heating stirrer (manufactured by Ind. Tian Lihua Co.) SMH-18, and then cooled to room temperature to prepare a composition.

< examples 1 to 2>

*4Ceramide TIC-001 (manufactured by Gaoshan flavor Co., ltd.)

(preparation method)

And (3) and (2) and (3) are heated, mixed and dissolved at 80 ℃. The two were mixed, stirred at 80℃for 10 minutes using a heating stirrer SMH-18 (manufactured by Ind. Chemie Tian Lihua), and then cooled to room temperature to prepare a composition.

< examples 1 to 3>

*5TPG-H (manufactured by ADEKA Co., ltd.)

*6 sodium hyaluronate (manufactured by the senior hall company)

(preparation method)

Comparative examples 1 to 1]

(preparation method)

After the components (2) to (3) were heated, mixed and dissolved, component (1) was added, and the mixture was stirred at 80℃for 10 minutes using a heating stirrer SMH-18 (manufactured by Ind. Chemie Tian Lihua), and then cooled to room temperature to prepare the aqueous dispersion.

< evaluation >

The formation of the produced ceramide-hyaluronic acid complex and the presence or absence of crystals derived from ceramide were observed by an optical microscope (BX-51, 400 x, manufactured by olympus corporation), and confirmed according to the following criteria. The results are shown in table 1. The photomicrographs of examples 1-1, 1-2 and comparative example 1-1 are shown in FIGS. 1 to 3.

1. Formation of complexes

In the composition immediately after production, the following criteria were used for confirmation.

O: with amorphous agglomerates

X: amorphous agglomerates free

2. Stability immediately after production (presence or absence of crystals derived from ceramide)

O: no crystals derived from ceramide

X: with crystals derived from ceramides

3. Stability with time (whether crystals derived from ceramide exist or not)

The presence or absence of crystals derived from ceramide after storage at constant temperatures of 50℃and 5℃for 2 weeks was evaluated according to the following criteria.

O: no crystals derived from ceramide

X: with crystals derived from ceramides

TABLE 1

As is clear from the above Table 1 and FIGS. 1 to 2, the compositions of examples 1-1 to 1-3 each formed a complex of a ceramide and a hyaluronic acid, and the crystallization of the ceramide was suppressed even when the composition was stored at a high temperature and a low temperature. On the other hand, no complex was observed in the composition of comparative example 1-1. In addition, crystals derived from ceramide were observed immediately after production (fig. 3).

Preparation of the composition (2): examples 1-4 to 1-15, comparative 1-2

Compositions were prepared according to the following formulations and methods of preparation of tables 2-3. For each of the obtained compositions, "formation of complex", "stability immediately after production", "stability with time (5 ℃ and 50 ℃/2 weeks)" were evaluated according to the above-mentioned methods and standards. The results are shown in tables 2 to 3.

(preparation method)

Mixing (1) - (2) and (7) - (9) at 80deg.C, and mixing (3) - (6) and (10) at 80deg.C. The two were mixed, stirred at 80℃for 10 minutes using a heating stirrer SMH-18 (manufactured by Ind. Chemie Tian Lihua), and then cooled to room temperature to prepare a composition.

TABLE 2

* Sodium chondroitin sulfate 7 (Maruha Co., ltd.)

*8TREMOIST-TP (manufactured by Japanese refinement Co., ltd.)

TABLE 3

The compositions of examples 1-4 to 1-15 each showed formation of a ceramide-hyaluronic acid complex, and even when stored at high and low temperatures, crystals of ceramide were not precipitated, and were confirmed to be stable. On the other hand, the compositions of comparative examples 1-2 were not observed to have complex, and crystals of ceramide were confirmed immediately after production.

Cosmetic preparation (1): examples 2-1 to 2-3

Using the compositions prepared in examples 1-1 to 1-3, aqueous cosmetics were prepared according to the following formulations and methods, and "formation of complex", "stability immediately after production", and "stability with time" were evaluated according to the same methods and standards as described above. The dispersibility of the formed ceramide-hyaluronic acid complex was evaluated for "stability immediately after production", "production stability (5 ℃/2 weeks)", and "production stability (50 ℃/2 weeks)", according to the following methods and criteria. The results are shown in tables 4 and 5.

< example 2-1>

*9NIKKOL Decaglyn 2-ISV (NIPPON SURFACTANT INDUSTRIES CO., LTD.)

*10EMALEX RWIS-150 (manufactured by Nihon Emulsion Co., ltd.)

*11 1, 3-butanediol (Daicel Corporation)

(preparation method)

The components (1) and (2) to (6) were heated and mixed at 80℃respectively, and then the mixture was stirred at 80℃for 10 minutes using a heating stirrer SMH-18 (manufactured by Ind. Chemie Tian Lihua), followed by cooling to room temperature.

< example 2-2>

*12 EMASLEX CS-10 (manufactured by Nihon Emulsion Co., ltd.)

*13EMALEX GWIS-108 (manufactured by Nihon Emulsion Co., ltd.)

(preparation method)

< examples 2 to 3>

*14ISOSTEARIC ACID EX (Kokyu Alcohol Kogyo Co., ltd.)

*15TRIETHANOLAMINE CARE (BASF corporation)

(preparation method)

< evaluation of Dispersion stability of ceramide-hyaluronic acid Complex >

The presence or absence of sedimentation of the ceramide-hyaluronic acid complex was visually confirmed and evaluated. Specifically, the dispersion state of the compound immediately after production and the dispersion state after 2 weeks of storage at constant temperatures of 50 ℃ and 5 ℃ were evaluated according to the following criteria. The results are shown in the following table.

O: no sedimentation was observed

Delta: slight sedimentation was observed

X: sedimentation is observed

TABLE 4

TABLE 5

As shown in tables 4 and 5, the aqueous cosmetics using the compositions of examples 1-1 to 1-3 formed a complex of ceramide and hyaluronic acid, and no precipitation of crystals was observed even when stored at high and low temperatures. In addition, the complex maintains a good dispersion state, no cloudiness or precipitation occurs during storage, and high transparency is maintained.

Preparation of cosmetic (2): examples 2-4 to 2-11 and comparative example 2-1

An aqueous cosmetic was prepared according to the following formulation of table 6 and the following preparation method. The resulting aqueous cosmetics were evaluated for "formation of complex", "stability immediately after production", "stability with time", "stability immediately after production", "production stability (5 ℃/2 weeks)", and "production stability" 50 ℃/2 weeks ", as in the above method and standard. The results are shown together in table 6.

(preparation method)

Examples 2-4 to 2-11:

a: the components (1) and (3), (2) and 30 parts of (4) and the balance (4) and (5) to (12) were mixed and dissolved at 80 ℃.

B: using T.K.HOMO DIPER (manufactured by Special organic chemicals Co., ltd.), to (1) and (3) prepared in A were added (2) and (30) parts of (4) and mixed for 10 minutes.

C: the components (5) to (12) prepared in the above-mentioned method (A) were added to the component (B) and mixed for 10 minutes, and then cooled to room temperature to prepare the product.

Comparative example 2-1:

d: mixing and dissolving (1) and (3) and (4) to (12) at 80 ℃.

E: using t.k.homo DISPER (manufactured by special organic chemical company), the preparation was performed by adding (4) to (12) to (1) and (3) prepared in D, mixing for 10 minutes, and cooling to room temperature.

TABLE 6

*16 NIKKKOL SMT (NIPPON SURFACTANT INDUSTRIES CO., LTD.)

*17DK ESTER S-160 (manufactured by first Industrial pharmaceutical Co., ltd.)

As shown in Table 6, the aqueous cosmetics of examples 2-4 to 2-11 each formed a ceramide-hyaluronic acid complex, and the crystallization of ceramide was suppressed. In addition, the compound has good dispersibility, no cloudiness or precipitation is generated even during the storage at high temperature and low temperature, and good appearance with high transparency is maintained. In contrast, the aqueous cosmetic of comparative example 2-1 did not form a complex, and crystallization of ceramide was not observed immediately after production, but crystallization occurred at both high and low temperatures.

< formulation example 1 transparent toning lotion >

(preparation method)

The components (1) to (2), (3) to (4) and (5) to (9) were mixed and dissolved at 80 ℃.

Using T.K.HOMO DIPER (manufactured by Special organic chemical Co., ltd.), the components (3) to (4) were added to the components (1) to (2) and mixed for 10 minutes. After adding (5) to (9) thereto and mixing for 10 minutes, the mixture was cooled to room temperature to prepare the product.

The obtained transparent astringent was stored at high and low temperatures, and no crystallization was observed. Further, no cloudiness or precipitation was generated immediately after production and during storage, and stability was excellent.

< formulation example 2 turbid white toner >

(preparation method)

The resulting cloudy lotion was stored at high and low temperatures, and no crystal deposition was observed. In addition, no precipitate was generated immediately after production and during storage, and stability was excellent.

(preparation method)

The components (1) to (2) and (3) to (4) were heated at 80℃and then mixed, and the mixture was stirred at 80℃for 10 minutes using T.K.HOMO DIPER (manufactured by Special chemical industry Co., ltd.), followed by cooling to room temperature.

The obtained anti-wrinkle transparent cosmetic liquid was stored at high temperature and low temperature, and no precipitation of crystals was observed. Further, no cloudiness or precipitation was generated immediately after production and during storage, and stability was excellent.

Industrial applicability

The composition of the present invention contains a ceramide which is easily precipitated as crystals, and by containing a ceramide and a uronic acid-containing polysaccharide in a specific aqueous solvent, the precipitation of crystals is suppressed, and an excellent stratum corneum barrier effect due to the ceramide can be obtained. Therefore, it is preferably used as a raw material for cosmetics or external preparations for skin.

Claims

1. A composition comprising a ceramide and a uronic acid-containing polysaccharide in an aqueous solvent containing propylene glycol and/or polypropylene glycol.

2. The composition according to claim 1, wherein the mass ratio of the ceramide to the uronic acid-containing polysaccharide (ceramide/uronic acid-containing polysaccharide) is 0.001 to 1.

3. The composition of claim 1 or 2, wherein the ceramide is ceramide 2 and/or ceramide 3.

4. A composition according to any one of claims 1 to 3, wherein the uronic acid-containing polysaccharide is a glucuronic acid-containing polysaccharide.

5. The composition according to claim 4, wherein the glucuronic acid-containing polysaccharide is a mucopolysaccharide and/or a tremella polysaccharide.

6. The composition according to claim 5, wherein the mucopolysaccharide is hyaluronic acid and/or sodium chondroitin sulfate.

7. The composition of claim 6, wherein the hyaluronic acid is acetylated hyaluronic acid and/or sodium hyaluronate.

8. The composition according to claim 6 or 7, wherein the hyaluronic acid has a weight-average molecular weight of 30 ten thousand or less.

9. The composition of any one of claims 1 to 8, wherein the ceramide forms a complex with uronic acid-containing polysaccharides.

10. The composition of any of claims 1-9, wherein the polypropylene glycol is dipropylene glycol and/or tripropylene glycol.

11. A cosmetic or skin external preparation comprising the composition according to any one of claims 1 to 10.

12. The cosmetic or skin external preparation according to claim 11, further comprising a nonionic surfactant having an isostearic acid skeleton.

13. The cosmetic or dermatological external preparation according to claim 12, wherein the mass ratio of the ceramide in the composition to the nonionic surfactant having an isostearic acid skeleton (ceramide/nonionic surfactant having an isostearic acid skeleton) is 0.001 to 1.

14. A process for producing a complex composed of a ceramide and a uronic acid-containing polysaccharide, which comprises the following steps (1) to (3):

(1) A step of dissolving ceramide in an aqueous solvent by heating to obtain a ceramide solution,

(2) A step of dissolving uronic acid-containing polysaccharides in an aqueous solvent to obtain uronic acid-containing polysaccharide solution,

(3) And (2) mixing the ceramide-based solution obtained in (1) with the uronic acid-containing polysaccharide-based solution obtained in (2).

15. A method for inhibiting crystallization of ceramide, characterized in that a complex composed of ceramide and uronic acid-containing polysaccharide is formed by mixing a ceramide solution obtained by dissolving ceramide in an aqueous solvent under heating with uronic acid-containing polysaccharide solution obtained by dissolving uronic acid-containing polysaccharide in an aqueous solvent.