Composition containing ceramide-type compounds and glucose-derived O-acyl products

Abstract

The present invention provides a stable composition comprising at least one ceramide-type compound and at least one O-acyl product derived from glucose. [Solution] A composition is provided comprising (a) at least one ceramide-type compound, (b) at least one O-acyl product derived from glucose which can be obtained by partial or complete esterification of vitamin F and the hydroxyl group of glucose, (c) at least one first compound selected from the group consisting of (c1) fatty acids, (c2) aliphatic alcohols, and (c3) mixtures thereof, and (d) at least one second compound selected from the group consisting of (d1) polysaccharides, (d2) amino acids, their derivatives and salts thereof, (d3) polyamino acids and their salts, (d4) proteins, and (d5) mixtures thereof.

Description

Technical Field

[0001] The present invention relates to a composition comprising at least one ceramide-type compound and at least one O-acyl product derived from glucose, as well as a cosmetic method using this composition.

Background Art

[0002] The formulation of environmentally compatible cosmetics designed and developed in consideration of environmental issues has become a major goal in aiming to meet global-scale challenges.

[0003] Therefore, it is essential to propose more sustainable compositions, preparation methods and ingredients to address these environmental issues.

[0004] In this context, it is important to develop novel cosmetic compositions that have a better carbon footprint, in particular by promoting the use of renewable raw materials and / or materials with a good naturalness index and / or materials of natural origin.

[0005] Ceramides present in the stratum corneum of the skin form the lipid barrier necessary to retain moisture, and play an important role in maintaining moisture within the skin. Ceramides in the stratum corneum are produced by the breakdown of cerebrosides by an enzyme known as cerebrosidase. Ceramides are partially converted to phytosphingosine and sphingosine by an enzyme known as ceramidase. Phytosphingosine and sphingosine play important roles in the regulation of cell proliferation and differentiation. Six different ceramides with different functions exist in human skin.

[0006] On the other hand, substances for preventing or reducing the effects of alopecia, for example substances for reducing or slowing hair loss, or substances for inducing or stimulating the growth of head hair and / or other body hair, have been sought for many years in, for example, the cosmetics industry.

[0007] WO 93 / 02657 teaches that alkyl polyglycoside compounds and / or O-acyl derivatives of glucose, particularly glucose esters, may effectively induce and stimulate hair growth and reduce hair loss. [Prior art documents] [Patent Documents]

[0008] [Patent Document 1] WO 93 / 02657 [Patent Document 2] DE 4424530 [Patent Document 3] DE 4424533 [Patent Document 4] DE 4402929 [Patent Document 5] DE 4420736 [Patent Document 6] WO 95 / 23807 [Patent Document 7] WO 94 / 07844 [Patent Document 8] EP-A-0 646 572 [Patent Document 9] WO 95 / 16665 [Patent Document 10] FR-2 673 179 [Patent Document 11] EP-A-0 227 994 [Patent Document 12] WO 94 / 24097 [Patent Document 13] WO 94 / 10131 [Patent Document 14] EP-A-0500437 [Patent Document 15] EP-A-0647617 [Patent Document 16] EP-A-1371658 [Patent Document 17] WO03 / 068824 [Non-patent literature]

[0009] [Non-Patent Document 1] “The skin barrier: An extraordinary interface with an exceptional lipid organization”, Progress in Lipid Research 92 (2023) 101252, J Bouwstra et al., Figure 2, p. 4 [Non-Patent Document 2] D. Campoccia et al., "Semisynthetic resorbable materials from hyaluronan esterification", Biomaterials 19 (1998) pp. 2101-2127 [Non-Patent Document 3] Milton J. Rosen, Gemini Surfactants, Properties of surfactant molecules with two hydrophilic groups and two hydrophobic groups, Cosmetics & Toiletries magazine, Volume 113, December 1998, pp. 49-55. [Non-Patent Document 4] Milton J. Rosen, Recent Developments in Gemini Surfactants, Allured's Cosmetics & Toiletries magazine, July 2001, Volume 116, Issue 7, pp. 67-70 [Overview of the project] [Problems that the invention aims to solve]

[0010] Because ceramides have low solubility in water, ceramide dispersions have been found to be unstable in some cases.

[0011] Furthermore, because O-acyl products have low solubility in water, dispersions of glucose-derived O-acyl products, such as those disclosed in WO 93 / 02657, have been found to be unstable in some cases.

[0012] Therefore, the object of the present invention is to provide a stable composition comprising at least one ceramide-type compound and at least one O-acyl product derived from glucose. [Means for solving the problem]

[0013] The above objective of the present invention is, (a) at least one ceramide-type compound, (b) At least one O-acyl product derived from glucose, which can be obtained by partial or complete esterification of vitamin F with the hydroxyl group of glucose, (c) At least one first compound selected from the group consisting of (c1) fatty acids, (c2) aliphatic alcohols, and (c3) mixtures thereof, (d) At least one second compound selected from the group consisting of (d1) polysaccharides, (d2) amino acids, their derivatives and salts, (d3) polyamino acids and their salts, (d4) proteins, and (d5) mixtures thereof. This can be achieved by a composition containing [the specified element].

[0014] (a) Ceramide-type compounds are given by the following formula (I):

[0015] [ka]

[0016] [In the formula, - R1 is a linear or branched saturated or unsaturated hydrocarbon group C1~C 50 Preferably C5~C 50This group may be substituted with one or more hydroxyl groups and / or optionally interrupted with one or more oxycarbonyl (-O-CO-) groups or carbonyloxy (-CO-O-) groups. - R2 is a linear or branched saturated or unsaturated hydrocarbon group C1~C 50 Preferably C5~C 50 This group may be substituted with one or more hydroxyl groups, and / or optionally interrupted with one or more oxycarbonyl (-O-CO-) or carbonyloxy (-CO-O-) groups. It can be represented by [this].

[0017] The amount of (a) ceramide-type compound in the composition according to the present invention may be 0.001% to 10% by mass, preferably 0.005% to 5% by mass, and more preferably 0.01% to 1% by mass, based on the total mass of the composition.

[0018] (b) The O-acyl product is given by the following formula (1):

[0019] [ka]

[0020] [In the formula, R1, R2, R3, R4, and R5 may be the same or different, and are selected from hydrogen and a -CO-R group (wherein R is selected from saturated and unsaturated linear hydrocarbon chains containing 11 to 21 carbon atoms), provided that at least one of the R1 to R5 groups is not hydrogen. It may also be a mixture of compounds represented by [the given formula / method].

[0021] (b) The O-acyl product includes at least one ester of glucose and linoleic acid, particularly a monoester; at least one ester of glucose and oleic acid, particularly a monoester; at least one ester of glucose and palmitic acid, particularly a monoester; and at least one ester of glucose and stearic acid, particularly a monoester.

[0022] The amount of (b)O-acyl product in the composition according to the present invention may be 0.01% to 15% by mass, preferably 0.05% to 10% by mass, and more preferably 0.1% to 5% by mass, based on the total mass of the composition.

[0023] (c1) Fatty acids are C4~C 24 Preferably C6~C 22 , more preferably C8~C 20 They can be selected from saturated or unsaturated linear or branched fatty acids.

[0024] (c2) The aliphatic alcohol can be selected from the group consisting of cetyl alcohol, cetearyl alcohol, stearyl alcohol, behenyl alcohol, oleyl alcohol, and mixtures thereof.

[0025] The amount of (c) the first compound in the composition according to the present invention may be 0.01% to 15% by mass, preferably 0.05% to 10% by mass, and more preferably 0.1% to 5% by mass, based on the total mass of the composition.

[0026] (d1) The polysaccharide may be selected from the group consisting of chitosan, hyaluronic acid and its derivatives, polysaccharides derived from microorganisms, and mixtures thereof, preferably from the group consisting of chitosan, hyaluronic acid and its salts, xanthan gum, and mixtures thereof.

[0027] (d2) The amino acid derivative can be selected from amino acid surfactants.

[0028] (d3) The polyamino acid can be selected from polyglutamic acid.

[0029] (d4) The protein may be of plant origin.

[0030] The amount of (d) the second compound in the composition according to the present invention may be 0.001% to 15% by mass, preferably 0.005% to 10% by mass, and more preferably 0.01% to 5% by mass, based on the total mass of the composition.

[0031] The present invention also relates to a cosmetic method for keratin substances, The present invention also relates to a cosmetic method, which includes the step of applying the composition according to the present invention to a keratin substance. [Brief explanation of the drawing]

[0032] [Figure 1] This is a micrograph obtained by microscopic observation of the composition according to Example 1. [Modes for carrying out the invention]

[0033] As a result of diligent research, the inventors have discovered that it is possible to provide a stable composition comprising at least one ceramide-type compound and at least one O-acyl product derived from glucose.

[0034] Therefore, the composition according to the present invention, (a) at least one ceramide-type compound, (b) At least one O-acyl product derived from glucose, which can be obtained by partial or complete esterification of vitamin F with the hydroxyl group of glucose, (c) At least one first compound selected from the group consisting of (c1) fatty acids, (c2) aliphatic alcohols, and (c3) mixtures thereof, (d) At least one second compound selected from the group consisting of (d1) polysaccharides, (d2) amino acids, their derivatives and salts, (d3) polyamino acids and their salts, (d4) proteins, and (d5) mixtures thereof. Includes.

[0035] (a) a ceramide-type compound, (b) an O-acyl product derived from glucose, (c) the first compound, and (d) the second compound may form a complex in the form of a sheet or particles. The size of the sheet or particles may be several micrometers or several hundred micrometers, for example, 10 μm to 200 μm. The size of the complex can be measured by an optical microscope. This size may be based on the number-average diameter.

[0036] The complex may have a sheet structure in which two films sandwich a core containing (a) a ceramide-type compound, (b) an O-acyl product derived from glucose, and (c) the first compound, and these films may contain (d) the second compound.

[0037] Although not bound by theory, (c) the first compound is thought to act as a crystallization inhibitor for (a) the ceramide-type compound and (b) the glucose-derived O-acyl product, and (d) the second compound is thought to bond to the hydroxyl group of (a) the ceramide-type compound and / or the sugar moiety of (b) the glucose-derived O-acyl product or to the carboxylic acid moiety or hydroxyl group of (c) the first compound, forming a sheet-type complex via hydrogen bonds or ionic bonds.

[0038] (a) Ceramide-type compounds and (b) O-acyl products derived from glucose are, for example, difficult to dissolve or disperse in water. Therefore, (a) ceramide-type compounds and (b) O-acyl products derived from glucose tend to crystallize and form aggregates or precipitates.

[0039] However, the above-mentioned complex, comprising (a) a ceramide-type compound and (b) an O-acyl product derived from glucose in the form of a sheet or particles, can be stably dispersed in water, for example. Therefore, the composition according to the present invention is so stable that it does not form any aggregates or precipitates based on (a) a ceramide-type compound and (b) an O-acyl product derived from glucose, or forms only very small amounts of aggregates or precipitates based on (a) a ceramide-type compound and (b) an O-acyl product derived from glucose.

[0040] (a) Ceramide-type compounds are known to function as moisturizers that can impart a moist or wet feeling, and / or as whitening agents that can whiten or lighten keratinous substances such as skin. In addition, (a) ceramide-type compounds are also known to improve the barrier effect of keratinous substances such as skin.

[0041] (b) O-acyl products derived from glucose are known to have various effects as cosmetic ingredients. For example, (b) O-acyl products derived from glucose can enhance the skin's moisturizing ability and maintain skin softness and elasticity. In addition, (b) O-acyl products derived from glucose are expected to have antioxidant properties that protect the skin from free radicals. Furthermore, (b) O-acyl products derived from glucose are expected to improve the condition of hair, particularly by reducing or preventing hair loss on the scalp and other hairs, and even promoting hair growth.

[0042] Therefore, the composition according to the present invention can provide various cosmetic effects such as skin moisturizing effect, skin whitening effect, effect of protecting the skin when the stratum corneum is damaged by dry skin, improvement of skin softness and elasticity, anti-aging effect due to antioxidant properties, prevention of hair loss, and promotion of hair growth.

[0043] Furthermore, by applying the composition according to the present invention onto a keratinous substance and drying the composition, the composition according to the present invention can impart a smooth feel and ease of combing to keratinous substances such as skin and hair.

[0044] In addition, when (a) a ceramide-type compound, (b) an O-acyl product derived from glucose, (c) the first compound, and (d) the second compound in the composition according to the present invention form a composite in the form of a sheet, the sheet can impart a unique optical effect, such as a pearly color, to the composition.

[0045] (b) The O-acyl product derived from glucose may be of natural origin, renewable, and biodegradable. Therefore, the composition according to the present invention may contain environmentally friendly components.

[0046] The present invention will be described in more detail below.

[0047] (Ceramide-type compounds) The composition according to the present invention comprises (a) at least one ceramide-type compound. A single type of ceramide-type compound or a combination of different types of ceramide-type compounds can be used.

[0048] According to the present invention, the term "ceramide-type compound" is understood to mean natural or synthetic ceramides and / or glycoceramides and / or pseudoceramides and / or neoceramides.

[0049] Ceramide-type compounds are disclosed, for example, in patent applications DE 4424530, DE 4424533, DE 4402929, DE 4420736, WO 95 / 23807, WO 94 / 07844, EP-A-0 646 572, WO 95 / 16665, FR-2 673 179, EP-A-0 227 994, WO 94 / 24097 and WO 94 / 10131, as well as in the publication "The skin barrier: An extraordinary interface with an exceptional lipid organization," Progress in Lipid Research 92 (2023) 101252, J Bouwstra et al., in Figures 2 and 4, and these teachings are incorporated herein by reference.

[0050] (a) The ceramide-type compound is represented by the following general formula (I):

[0051] [Chemical Formula]

[0052] [In the formula, - R1 is a linear or branched, saturated or unsaturated hydrocarbon group C1~C 50 , preferably C5~C 50 , this group may be substituted with one or more hydroxyl groups, and / or may optionally be interrupted by one or more oxycarbonyl (-O-CO-) groups or carbonyloxy (-CO-O-) groups, - R2 is a linear or branched, saturated or unsaturated hydrocarbon group C1~C 50 , preferably C5~C 50 , this group may be substituted with one or more hydroxyl groups, and / or may optionally be interrupted by one or more oxycarbonyl (-O-CO-) groups or carbonyloxy (-CO-O-) groups] can be represented by.

[0053] In a preferred embodiment, (a) the ceramide-type compound is represented by formula (I) [wherein R1 is a linear or branched, saturated or unsaturated hydrocarbon group C 14 ~C 22 , preferably C 14 ~C 20 , for example C 15 or C 16 or C 17 , this group may be substituted with one or more hydroxyl groups, and / or may optionally be interrupted by one or more oxycarbonyl (-O-CO-) groups or carbonyloxy (-CO-O-) groups, R2 is a linear or branched, saturated or unsaturated hydrocarbon group C 14 ~C 22 , preferably C14 ~C 20 For example, C 15 This represents a compound that may be substituted with one or more hydroxyl groups and / or optionally interrupted by an oxycarbonyl (-O-CO-) group or a carbonyloxy (-CO-O-) group.

[0054] In preferred embodiments, (a) the ceramide-type compound is of formula (I) [wherein R1 is a linear or branched saturated or unsaturated hydrocarbon group C]. 15 or C 16 or C 17 This represents a group which may be substituted with one or more hydroxyl groups and / or optionally interrupted with one or more oxycarbonyl (-O-CO-) or carbonyloxy (-CO-O-) groups, and R2 is a linear or branched saturated or unsaturated hydrocarbon group C 15 This represents a compound that may be substituted with one or more hydroxyl groups and / or optionally interrupted by an oxycarbonyl (-O-CO-) group or a carbonyloxy (-CO-O-) group.

[0055] Such compounds include, for example, - 2-N-Linoleoylamino-octadecane-1,3-diol, - N-oleoyldihydrosphingosine (INCI), - 2-N-palmitoylamino-octadecane-1,3-diol, - 2-N-stearoylamino-octadecane-1,3-diol, - 2-N-[2-hydroxy-palmitoyl]-amino-octadecane-1,3-diol, - 2-N-stearoylamino-octadecane-1,3,4triol, especially N-stearoylphytosphingosine, - 2-N-palmitoylamino-hexadecane-1,3-diol, Or a mixture of these compounds.

[0056] According to a preferred embodiment, the composition according to the present invention preferably comprises (a) at least one ceramide-type compound selected from ceramides NdS, AdS, OdS, EOdS, NS, AS, OS, EOS, NG, AG, NP, AP, OP, EOP, NH, AH, OH, EOH, NSD, ASD, OSD, EOSD, NT, BS, EO-18:2, EO-18:1, hydroxypalmitoyl sphinganine, 2-oleamide-1,3-octadecanediol, and mixtures thereof.

[0057] According to a preferred embodiment, the composition according to the present invention comprises (a) at least one ceramide-type compound selected from ceramides NS, AS, OS, EOS, NP, AP, OP, EOP, hydroxypalmitoyl sphinganine, 2-oleamide-1,3-octadecanediol, and mixtures thereof.

[0058] According to a preferred embodiment, the composition according to the present invention comprises (a) at least one ceramide-type compound selected from ceramide NS, AS, EOS, NP, AP, EOP, hydroxypalmitoyl sphinganine, 2-oleamide-1,3-octadecanediol, and mixtures thereof, and more preferably selected from ceramide NS, AS, EOS, NP, AP, EOP, and mixtures thereof.

[0059] According to a preferred embodiment, the composition according to the present invention preferably comprises at least two ceramide-type compounds selected from ceramides NS, AS, EOS, NP, AP, and EOP.

[0060] According to a preferred embodiment, the composition according to the present invention preferably comprises two ceramide-type compounds selected from a mixture of ceramides (NS and AS) or (NS and EOS), or (NS and NP), or (NS and AP), or (NS and EOP), or (AS and EOS), or (AS and NP), or (AS and EOP), or (EOS and NP), or (EOS and AP), or (EOS and EOP), or (NP and AP), or (NP and EOP), or (AP and EOP).

[0061] According to a preferred embodiment, the composition according to the present invention comprises at least three ceramide-type compounds selected from ceramides NS, AS, EOS, NP, AP, and EOP.

[0062] According to a preferred embodiment, the composition according to the present invention preferably comprises three ceramide-type compounds selected from ceramides (NS, AS, and EOS), or (NS, AS, and NP), or (NS, AS, and AP), or (NS, AS, and EOP), or (AS, EOS, and NP), or (AS, EOS, and AP), or (AS, EOS, and EOP), or (EOS, NP, and AP), or (NP, AP, and EOP).

[0063] According to a preferred embodiment, the composition according to the present invention comprises at least four ceramide-type compounds selected from ceramides NS, AS, EOS, NP, AP, and EOP.

[0064] According to a preferred embodiment, the composition according to the present invention preferably comprises four ceramide-type compounds selected from ceramides (NS and AS and EOS and NP), or (NS and AS and EOS and AP), or (NS and AS and EOS and EOP), or (NS and EOS and NP and AP), or (NS and EOS and NP and EOP), or a mixture of (NS and NP and AP and EOP).

[0065] According to a preferred embodiment, the composition according to the present invention comprises at least five ceramide-type compounds selected from ceramides NS, AS, EOS, NP, AP, and EOP.

[0066] According to a preferred embodiment, the composition according to the present invention preferably comprises five ceramide-type compounds selected from ceramides (NS and AS and EOS and NP and AP) or (NS and AS and EOS and NP and EOP) or a mixture of (AS and EOS and NP and AP and EOP).

[0067] According to a preferred embodiment, the composition according to the present invention preferably comprises one, two, three, or four ceramide-type compounds selected from ceramides NS, AS, EOS, NP, AP, and EOP.

[0068] The synthesis of ceramides is described, for example, in EP-A-0500437 and EP-A-0647617.

[0069] Hydroxypalmitoyl sphinganine is a well-known and commercially available product.

[0070] 2-Oleamido-1,3-Octadecanediol is a known product and is commercially available.

[0071] Ceramide NP, also known as N-stearoyl-phytosphingosine, is a well-known and commercially available product.

[0072] Ceramide AP, also known as N-(2-hydroxystearoyl)phytosphingosine, is a well-known and commercially available product.

[0073] Ceramide EOP, also known as stearoyloxyheptacosanoyl-C27-phytosphingosine or 30-[[(1S,2S,3R)-2,3-dihydroxy-1-(hydroxymethyl)heptadecyl]amino]-30-oxotriacontyl(9Z,12Z)-9,12-octadecadienoate, is a well-known and commercially available product.

[0074] Ceramide NdS, also known as N-tetracosanoyl sphinganine, is a well-known and commercially available product.

[0075] Ceramide AdS, also known as 2-hydroxy-N-[(1S,2R)-2-hydroxy(hydroxymethyl)heptadecyl]tetracosaneamide, is a well-known and commercially available product.

[0076] Ceramide EOdS is a well-known product also known as 9,12-octadecadienoic acid (9Z,12Z)-,30-[[(1S,2R)-2-hydroxy-1-(hydroxymethyl)heptadecyl]amino]-30-oxotriacontyl ester.

[0077] Ceramide NS is also known as N-stearoyl sphinganin.

[0078] Ceramide AS, also known as 2-hydroxy-N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecene-1-yl]tetracosaneamide, is a well-known product that is commercially available.

[0079] Ceramide EOS is a well-known product also known as 9,12-octadecadienoic acid (9Z,12Z)-,30-[[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecene-1-yl]amino]-30-oxotriacontyl ester.

[0080] Ceramide NG, also known as N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecene-1-yl]octadecanamide or N-octadecanoylsphingosine, is a well-known and commercially available product.

[0081] Ceramide NH is a well-known product also known as N-[(1S,2R,3E)-2,5-dihydroxy-1-(hydroxymethyl)-3-heptadecene-1-yl]tetracosaneamide.

[0082] Ceramide AH is a well-known product also known as N-[(1S,2R,3E)-2,5-dihydroxy-1-(hydroxymethyl)-3-heptadecene-1-yl]-2-hydroxytetracosamide.

[0083] Ceramide EOH is a well-known product also known as 30-[[(1S,2R,3E)-2,5-dihydroxy-1-(hydroxymethyl)-3-heptadecene-1-yl]amino]-30-oxotriacontyl(9Z,12Z)-9,12-octadecadienoate.

[0084] (a) The ceramide-type compound may preferably be selected from the group consisting of ceramide AP, ceramide NP, ceramide EOP, and mixtures thereof.

[0085] (a) The ceramide-type compound may more preferably be ceramide NP, ceramide AP, or a mixture thereof.

[0086] The amount of (a) ceramide-type compound in the composition according to the present invention may be 0.001% by mass or more, preferably 0.005% by mass or more, and more preferably 0.01% by mass or more, based on the total mass of the composition.

[0087] On the other hand, the amount of (a) ceramide-type compound in the composition according to the present invention may be 10% by mass or less, preferably 5% by mass or less, and more preferably 1% by mass or less, based on the total mass of the composition.

[0088] Therefore, the amount of (a) ceramide-type compound in the composition according to the present invention may be 0.001% to 10% by mass, preferably 0.005% to 5% by mass, and more preferably 0.01% to 1% by mass, based on the total mass of the composition.

[0089] In one embodiment of the present invention, the composition is - A first ceramide selected from ceramide AP, NP, EOP, AS, NS, and EOS in an amount of at least 0.0001% to 5% by mass, preferably 0.001% to 1% by mass, and more preferably 0.005% to 0.1% by mass, relative to the total mass of the composition. - A second ceramide selected from ceramide AP, NP, EOP, AS, NS, and EOS in an amount of at least 0.0001% to 5% by mass, preferably 0.001% to 1% by mass, and more preferably 0.005% to 0.1% by mass, relative to the total mass of the composition. - A third ceramide selected from AP, NP, EOP, AS, NS, and EOS in an amount of at least 0.000001% to 1% by mass, preferably 0.000005% to 0.01% by mass, and more preferably 0.000007% to 0.001% by mass, relative to the total mass of the composition. Includes, The first, second, and third ceramides mentioned above are different from each other.

[0090] (O-acyl products derived from glucose) The compositions according to the present invention include (b) at least one O-acyl product derived from glucose, which can be obtained by the partial or complete esterification of vitamin F with the hydroxyl group of glucose. A single type of such O-acyl product or a combination of different types of such O-acyl products can be used.

[0091] (b) O-acyl products, which can be obtained by the partial or complete esterification of vitamin F with the hydroxyl group of glucose, have the advantage of being mainly composed of essential fatty acid derivatives that are naturally present in the human body.

[0092] (b) The O-acyl product is also more stable over time than the free acid it contains.

[0093] In addition, (b) O-acyl products can be synthesized relatively inexpensively and easily on an industrial scale.

[0094] (b) O-acyl (i.e., O-acylation) products are described in EP-A-1371658.

[0095] Those skilled in the art will know that vitamin F, a compound naturally present in fatty substances such as linseed oil, sunflower oil, or safflower oil, is, for example, C 12 ~C 20 It is known that it contains a mixture of fatty acids selected from fatty acids containing hydrocarbon chains.

[0096] Therefore, vitamin F is, for example, (in mass %) - 75% to 80% by mass of linoleic acid, - 10% to 15% by mass of oleic acid, - 4% to 8% by mass of palmitic acid, - 0.5% to 3% by mass of stearic acid, - 0% to 10% by mass of at least one other acid selected from lauric acid, myristic acid, arachidic acid, behenic acid, lauroleic acid, myristoleic acid, palmitoleic acid, and linolenic acid. It can be considered to include this.

[0097] As a result, the products disclosed herein, which can be obtained by the esterification of vitamin F, may consist of a mixture of various esters derived from the presence of various acids formed during this reaction.

[0098] Furthermore, since glucose contains five sites that can react during the esterification reaction, the products disclosed herein may include a mixture of esters formed at various positions of glucose.

[0099] In addition, the products disclosed herein may also include mixtures of monoesters and diesters that may be formed.

[0100] Therefore, the term “product” may, in this specification, mean a mixture consisting of all monoesters or diesters formed during the esterification reaction of vitamin F and glucose.

[0101] (b) The O-acyl product is given by the following formula (1):

[0102] [ka]

[0103] [In the formula, R1, R2, R3, R4, and R5 may be the same or different, and are selected from hydrogen and a -CO-R group (wherein R is selected from saturated and unsaturated linear hydrocarbon chains containing 11 to 21 carbon atoms), provided that at least one of the R1 to R5 groups is not hydrogen. It may also be a mixture of compounds represented by [the given formula / method].

[0104] (b) The ratio of the number of ester functional groups in the O-acyl product to the number of initial hydroxyl functional groups, or the degree of esterification per glucose molecule, may be in the range of, for example, 0.2 to 1, more precisely, for example, 0.2 to 0.6, or even further, for example, 0.21 to 0.4.

[0105] Furthermore, glucose may be esterified at, for example, at least one position selected from positions 1, 2, 3, and 6. In one embodiment, glucose can be esterified at at least one position selected from positions 1 and 6.

[0106] The ratio of the number of ester functional groups at position 6 to the total number of ester functional groups per glucose molecule may be, for example, in the range of 0.55:1 to 1:1, or even further, in the range of 0.70:1 to 0.98:1, or even further, in the range of 0.90:1 to 0.97:1.

[0107] The (b)O-acyl products disclosed herein may include at least one ester of glucose and linoleic acid, e.g., at least one monoester; at least one ester of glucose and oleic acid, e.g., at least one monoester; at least one ester of glucose and palmitic acid, e.g., at least one monoester; and at least one ester of glucose and stearic acid, e.g., at least one monoester.

[0108] The material may also contain glucose and at least one ester of at least one acid selected from lauric acid, myristic acid, arachidic acid, behenic acid, lauroleic acid, myristoleic acid, palmitoleic acid, and linolenic acid, such as at least one monoester.

[0109] The material may also contain glucose and at least one diester of at least one acid selected from lauric acid, myristic acid, arachidic acid, behenic acid, lauroleic acid, myristoleic acid, palmitoleic acid, linoleic acid, oleic acid, palmitic acid, stearic acid, and linolenic acid.

[0110] Therefore, in one embodiment, the products disclosed herein may, for example, collectively include the following at all positions: - 40% to 80% by mass, for example, 60% to 75% by mass, and even more, for example, 68% to 72% by mass, at least one monoester of glucose and linoleic acid, - 10% to 20% by mass, for example, 12% to 17% by mass, and even more, for example, 14% to 15% by mass, at least one monoester of glucose and oleic acid, - 5% to 20% by mass, for example, 7% to 15% by mass, and furthermore, for example, 9% to 12% by mass, at least one monoester of glucose and palmitic acid, - 0.5% to 7% by mass, for example, 1% to 5% by mass, and furthermore, for example, 2% to 4% by mass, at least one monoester of glucose and stearic acid, - 0 to 10% by mass, for example, 0.10 to 4% by mass, and more preferably, for example, 0.15 to 2% by mass, glucose and at least one monoester of at least one acid selected from lauric acid, myristic acid, arachidic acid, behenic acid, lauroleic acid, myristoleic acid, palmitoleic acid, and linolenic acid. - A diester of glucose and at least one acid selected from lauric acid, myristic acid, arachidic acid, behenic acid, lauroleic acid, myristoleic acid, palmitoleic acid, linoleic acid, oleic acid, palmitic acid, stearic acid, and linolenic acid, in an amount of 0 to 10% by mass, for example, 0.10 to 4% by mass, and more preferably, for example, 0.15 to 2% by mass.

[0111] In another embodiment, the products disclosed herein may include: - 40% to 80% by mass, for example, 60% to 75% by mass, and even more, for example, 68% to 72% by mass, of glucose and at least one ester of linoleic acid selected from, for example, 6-O-octadeca-9,12-dienoyl-D-glucopyranose, 1-O-octadeca-9,12-dienoyl-D-glucopyranose, 2-O-octadeca-9,12-dienoyl-D-glucopyranose, and 3-O-octadeca-9,12-dienoyl-D-glucopyranose. - 10% to 20% by mass, for example, 12% to 17% by mass, and even more, for example, 14% to 15% by mass, of glucose and at least one ester of oleic acid selected from, for example, 6-O-octadeca-9-enoyl-D-glucopyranose, 3-O-octadeca-9-enoyl-D-glucopyranose, 1-O-octadeca-9-enoyl-D-glucopyranose, and 2-O-octadeca-9-enoyl-D-glucopyranose. - 5% to 20% by mass, for example, 7% to 15% by mass, and more specifically, for example, 9% to 12% by mass, of glucose and at least one ester of palmitic acid selected from, for example, 6-O-hexadecanoyl-D-glucopyranose, 3-O-hexadecanoyl-D-glucopyranose, 1-O-hexadecanoyl-D-glucopyranose, and 2-O-hexadecanoyl-D-glucopyranose. - 0.5% to 7% by mass, for example, 1% to 5% by mass, and further, for example, 2% to 4% by mass, of glucose and at least one ester of stearic acid selected from, for example, 6-O-octadecanoyl-D-glucopyranose, 3-O-octadecanoyl-D-glucopyranose, 1-O-octadecanoyl-D-glucopyranose, and 2-O-octadecanoyl-D-glucopyranose. - 0 to 10% by mass, for example, 0.10 to 4% by mass, and even further, for example, 0.15 to 2% by mass, glucose and at least one ester of at least one acid selected from lauric acid, myristic acid, arachidic acid, behenic acid, lauroleic acid, myristoleic acid, palmitoleic acid, and linolenic acid. - A diester of glucose and at least one acid selected from lauric acid, myristic acid, arachidic acid, behenic acid, lauroleic acid, myristoleic acid, palmitoleic acid, linoleic acid, oleic acid, palmitic acid, stearic acid, and linolenic acid, in an amount of 0 to 10% by mass, for example, 0.10 to 4% by mass, or even further, for example, 0.15 to 2% by mass.

[0112] A method for preparing the products used in the present invention is also described in EP-A-1371658.

[0113] In particular, equation (Ia):

[0114] [ka]

[0115] (In the formula, R is a saturated or unsaturated linear or branched hydrocarbon chain containing 7 to 21 carbon atoms.) (b)O-acyl products of, as well as their optical and geometric isomers, their alpha and beta anomers, their salts, and their solvates, such as their hydrates, Formula (II):

[0116] [ka]

[0117] The first step is to prepare a mixed anhydride by reacting a carboxylic acid of formula R-COOH with a trimethylacetic acid halide of formula XC(O)-C(CH3)3 (wherein X preferably represents chlorine or bromine), The process (as a second step) involves reacting the formed mixed anhydride with glucose and its optical isomers, its alpha and beta anomers, its salts, and its solvates, such as its hydrates. It can be prepared by a method including [a specific method].

[0118] The above method makes it possible to prepare O-acyl derivatives of glucose, which can be represented by formula (Ia), esterified mainly at the 6-position only or as a mixture. In particular, the above method makes it possible to prepare glucose-derived O-acyl products that can be obtained by partial or complete esterification of glucose with vitamin F.

[0119] Preferably, the R group is a saturated or unsaturated linear or branched hydrocarbon chain containing 11 to 17 carbon atoms.

[0120] The acyl residue-COR may, in particular, be an octanoyl, decanoyl, dodecanoyl, myristoyl, hexadecanoyl, stearoyl, palmitreyl, oleyl, linoleyl, or linolenoyl residue.

[0121] Therefore, the above method prepares a mixed anhydride of formula (II) by reacting a carboxylic acid of formula R-COOH with a trimethylacetic acid halide of formula XC(O)-C(CH3)3 (wherein X preferably represents chlorine or bromine) in the first step.

[0122] Among the carboxylic acids that can be used, examples include octanoic acid, decanoic acid, dodecanoic acid, myristic acid, hexadecanoic acid, stearic acid, oleic acid, linoleic acid or linolenic acid, and mixtures thereof.

[0123] Therefore, the reaction scheme is as follows:

[0124] [ka]

[0125] The reaction may be carried out in an organic reaction solvent such as tetrahydrofuran, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, or toluene, or mixtures thereof.

[0126] This may preferably be carried out under an inert atmosphere, for example, under nitrogen.

[0127] The carboxylic acid may be activated using a base, or the corresponding carboxylate may be used directly. The base is preferably an organic base selected from, in particular, triethylamine, pyridine, 4-dimethylaminopyridine, tributylamine, and N-methylmorpholine, and mixtures thereof. The reaction may be carried out at a temperature of -25°C to +40°C, preferably -10°C to +10°C, for a duration of 5 minutes to 5 hours, particularly 30 minutes to 3 hours.

[0128] Preferably, 0.3 to 3 equivalents, and more preferably 0.5 to 1.5 equivalents, of carboxylic acid are reacted with 1 equivalent of trimethylacetate halide.

[0129] In the esterification step, the second step of the above method, the aforementioned mixed anhydride is reacted with glucose. This second step may optionally be carried out after the salt, which may have been formed during the first step, has been filtered by suction.

[0130] This second step is preferably carried out in an organic solvent, which may be the same organic solvent as in the first step. Therefore, this solvent may be tetrahydrofuran, N,N-dimethylformamide, N-methylpyrrolidone, pyridine, or toluene, or a mixture thereof.

[0131] The mixed anhydrous material is preferably dissolved in the aforementioned organic solvent before the reaction.

[0132] Preferably, glucose is dissolved beforehand in a solvent such as pyridine, dimethylformamide, N-methylpyrrolidone, and / or dimethylacetamide.

[0133] Preferably, 0.5 to 1.5, particularly 0.9 to 1.1, and even better, 1 equivalent of the mixed anhydrous material is reacted with 3 equivalents of glucose.

[0134] At least three equivalents of glucose are preferably used for the acid or mixture of acids that reacted in the first step.

[0135] The reaction may be carried out at a temperature of -25°C to +100°C, preferably 0°C to +60°C, and more preferably 20 to 25°C, for a duration of 1 to 30 hours, and especially 2 to 15 hours.

[0136] After the reaction, the solvent may be separated from the desired compound by, for example, evaporation, centrifugation, or filtration.

[0137] The obtained product may be purified by any known means, such as distillation, chromatography on a silica gel column, precipitation and / or extraction with a water / organic solvent mixture, for example.

[0138] Therefore, the above method makes it possible to prepare O-acyl derivatives of glucose, either individually or as a mixture, primarily at the 6-position, in an industrially achievable manner. In particular, the following compounds can be prepared according to this method: 6-O-octadeca-9,12-dienoyl-D-glucopyranose; 6-O-octadeca-9-enoyl-D-glucopyranose; 6-O-octadecanoyl-D-glucopyranose; 6-O-hexadecanoyl-D-glucopyranose; and mixtures thereof.

[0139] Generally, it is known that glucose is esterified primarily at position 6, and sometimes at positions 1 and / or 2 and / or 3, using the method described above.

[0140] The ratio of the number of ester functional groups at position 6 to the total number of ester functional groups per glucose molecule is generally 55% to 95%, particularly 60% to 80%, and preferably 68% to 75%.

[0141] The amount of (b) glucose-derived O-acyl product in the composition according to the present invention may be 0.01% by mass or more, preferably 0.05% by mass or more, and more preferably 0.1% by mass or more, based on the total mass of the composition.

[0142] On the other hand, the amount of (b) glucose-derived O-acyl product in the composition according to the present invention may be 15% by mass or less, preferably 10% by mass or less, and more preferably 5% by mass or less, based on the total mass of the composition.

[0143] Therefore, the amount of (b) glucose-derived O-acyl product in the composition according to the present invention may be 0.01% to 15% by mass, preferably 0.05% to 10% by mass, and more preferably 0.1% to 5% by mass, relative to the total mass of the composition.

[0144] (First compound) The composition according to the present invention comprises at least one first compound selected from the group consisting of (c)(c1) fatty acids, (c2) aliphatic alcohols, and (c3) mixtures thereof.

[0145] The amount of (c) the first compound in the composition according to the present invention may be 0.01% by weight or more, preferably 0.05% by weight or more, and more preferably 0.1% by weight or more, based on the total weight of the composition.

[0146] On the other hand, the amount of (c) the first compound in the composition according to the present invention may be 15% by mass or less, preferably 10% by mass or less, and more preferably 5% by mass or less, based on the total mass of the composition.

[0147] Therefore, the amount of (c) the first compound in the composition according to the present invention may be in the range of 0.01% to 15% by mass, preferably 0.05% to 10% by mass, and more preferably 0.1% to 5% by mass, relative to the total mass of the composition.

[0148] (c1) Fatty acid The composition according to the present invention may contain (c1) at least one fatty acid. A single type of fatty acid or a combination of different types of fatty acids can be used.

[0149] In this specification, the term "fatty acid" refers to a carboxylic acid having a long aliphatic carbon chain.

[0150] (c1) fatty acids have at least 4 carbon atoms, preferably at least 6 carbon atoms, more preferably at least 8 carbon atoms. (c1) fatty acids may contain up to 24 carbon atoms, preferably up to 22 carbon atoms, more preferably up to 20 carbon atoms. (c1) fatty acids are C4~C 24 Fatty acids, more like C6~C 22 Fatty acids, more preferably C8-C 20 It is preferable to select from fatty acids.

[0151] (c1) fatty acids can be selected from saturated or unsaturated, linear or branched fatty acids. Therefore, (c1) fatty acids are C 10 ~C 20 Preferably C 12 ~C20 , more C 14 ~C 20 They can be selected from saturated or unsaturated linear or branched fatty acids.

[0152] As unsaturated linear or branched fatty acids, monounsaturated linear or branched fatty acids or polyunsaturated linear or branched fatty acids may be used. Examples of the unsaturated portion of unsaturated linear or branched fatty acids include carbon-carbon double bonds or carbon-carbon triple bonds.

[0153] Examples of saturated fatty acids include caprylic acid (C8), pelargonic acid (C9), and capric acid (C8). 10 ), lauric acid (C 12 ), myristic acid (C 14 ), pentadecanoic acid (C 15 ), palmitic acid (C 16 ), heptadecanoic acid (C 17 ), stearic acid (C 18 ), isostearic acid (C 18 ), nonadecanoic acid (C 19 ), arachidic acid (C 20 ), behenic acid (C 22 ), and lignoceric acid (C 24 ) can be cited.

[0154] Examples of unsaturated fatty acids include myristoleic acid (C) 14 ), palmitoleic acid (C 16 ), oleic acid (C 18 ), linoleic acid (C 18 ), linolenic acid (C 18 ), elaidic acid (C 18 ), arachidonic acid (C 20 ), eicosenoic acid (C 20 ), erucic acid (C 22 ), and nervonic acid (C 24 ) can be cited.

[0155] (c1) Fatty acids are C 16 ~C 18From saturated or unsaturated linear or branched fatty acids, it is preferable to select from the group consisting of oleic acid, linoleic acid, linolenic acid, palmitic acid, stearic acid, isostearic acid, and mixtures thereof.

[0156] (c1) Fatty acids may be in the form of their free acid or their salt. Examples of fatty acid salts include inorganic salts, such as alkali metal salts (sodium salts, potassium salts, etc.) and alkaline earth metal salts (magnesium salts, calcium salts, etc.), and organic salts, such as ammonium salts (quaternary ammonium salts, etc.) and amine salts (triethanolamine salts, triethylamine salts, etc.). A single type of fatty acid salt or a combination of different types of fatty acid salts may be used. Furthermore, a combination of one or more fatty acids in the form of free acids and one or more fatty acids in the form of salts may be used, and one or more types of salts may also be used.

[0157] The amount of (c1) fatty acid in the composition according to the present invention may be 0.01% by mass or more, preferably 0.05% by mass or more, and more preferably 0.1% by mass or more, based on the total mass of the composition.

[0158] On the other hand, the amount of (c1) fatty acid in the composition according to the present invention may be 15% by mass or less, preferably 10% by mass or less, and more preferably 5% by mass or less, based on the total mass of the composition.

[0159] Therefore, the amount of (c1) fatty acid in the composition according to the present invention may be in the range of 0.01% to 15% by mass, preferably 0.05% to 10% by mass, and more preferably 0.1% to 5% by mass, relative to the total mass of the composition.

[0160] (c2) Aliphatic alcohol The composition according to the present invention may contain (c2) at least one aliphatic alcohol. A single type of aliphatic alcohol or a combination of different types of aliphatic alcohols can be used.

[0161] In this specification, the term "aliphatic" refers to the inclusion of a relatively large number of carbon atoms. Therefore, alcohols having four or more, preferably six or more, and more preferably eight or more carbon atoms are included within the range of aliphatic alcohols. Aliphatic alcohols may contain up to 24 carbon atoms, preferably up to 22, and more preferably up to 20 carbon atoms. Aliphatic alcohols may be saturated or unsaturated. Aliphatic alcohols may be linear or branched.

[0162] (c2) The aliphatic alcohol may have the structure R-OH (wherein R is selected from saturated and unsaturated, linear and branched groups containing 4 to 24 carbon atoms, e.g., 8 to 22 carbon atoms). In at least one embodiment, R is C 12 ~C 24 Alkyl and C 12 ~C 24 It is selected from alkenyl groups. R may or may not be substituted with at least one hydroxyl group.

[0163] (c2) Non-limiting examples of aliphatic alcohols that can be listed include lauryl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, behenyl alcohol, linoleyl alcohol, undecylenyl alcohol, palmitrail alcohol, arachidonyl alcohol, erucyl alcohol, cetearyl alcohol, and mixtures thereof.

[0164] Suitable examples of (c2) aliphatic alcohols include, but are not limited to, cetyl alcohol, cetearyl alcohol, stearyl alcohol, behenyl alcohol, oleyl alcohol, and mixtures thereof.

[0165] (c2) Aliphatic alcohol may also represent a mixture of aliphatic alcohols, meaning that several species of aliphatic alcohols can coexist in the form of a mixture in commercially available products. According to at least one embodiment, the aliphatic alcohol used in the composition according to the present invention is selected from a mixture of cetyl alcohol and stearyl alcohol (cetearyl alcohol).

[0166] The amount of (c2) aliphatic alcohol in the composition according to the present invention may be 0.01% by mass or more, preferably 0.05% by mass or more, and more preferably 0.1% by mass or more, based on the total mass of the composition.

[0167] On the other hand, the amount of (c2) aliphatic alcohol in the composition according to the present invention may be 15% by mass or less, preferably 10% by mass or less, and more preferably 5% by mass or less, based on the total mass of the composition.

[0168] Therefore, the amount of (c2) aliphatic alcohol in the composition according to the present invention may be in the range of 0.01% to 15% by mass, preferably 0.05% to 10% by mass, and more preferably 0.1% to 5% by mass, relative to the total mass of the composition.

[0169] (Second compound) The composition according to the present invention comprises at least one second compound selected from the group consisting of (d) (d1) polysaccharides, (d2) amino acids, their derivatives, and salts thereof, (d3) polyamino acids and their salts, (d4) proteins, and (d5) mixtures thereof.

[0170] (d) The second compound is different from (c) the first compound.

[0171] (d1) Polysaccharides, (d2) Amino acids, their derivatives, and their salts, (d3) Polyamino acids and their salts, and (d4) Proteins are distinct from one another.

[0172] The amount of (d) the second compound in the composition according to the present invention may be 0.001% by mass or more, preferably 0.005% by mass or more, and more preferably 0.01% by mass or more, based on the total mass of the composition.

[0173] On the other hand, the amount of the second compound (d) in the composition according to the present invention may be 15% by mass or less, preferably 10% by mass or less, and more preferably 5% by mass or less, based on the total mass of the composition.

[0174] Therefore, the amount of the second compound (d) in the composition according to the present invention may be in the range of 0.001% to 15% by mass, preferably 0.005% to 10% by mass, and more preferably 0.01% to 5% by mass, relative to the total mass of the composition.

[0175] (d1) Polysaccharide The composition according to the present invention may contain (d1) at least one polysaccharide. A single type of polysaccharide or a combination of different types of polysaccharides can be used.

[0176] (d1) The polysaccharide is preferably derived from natural resources such as plants and microorganisms.

[0177] (d1) Polysaccharides may preferably not be derived from cellulose.

[0178] (d1) polysaccharides are more preferably biodegradable. The term "biodegradable" means that (d1) polysaccharides can be broken down or divided in the environment or in living organisms, for example, by metabolism by microorganisms that may be present in the environment or in living organisms. Biodegradable (d1) polysaccharides can also be broken down by hydrolysis.

[0179] (d1) The polysaccharide may be nonionic or ionic, preferably ionic, more preferably cationic or anionic.

[0180] Cationic (d1) polysaccharides may have a positive charge density. The charge density of cationic (d1) polysaccharides may be 0.01 meq / g to 20 meq / g, preferably 0.05 meq / g to 15 meq / g, and more preferably 0.1 meq / g to 10 meq / g.

[0181] Anionic (d1) polysaccharides may have a negative charge density. The charge density of anionic (d1) polysaccharides may be 0.1 meq / g to 5.0 meq / g, preferably 0.2 meq / g to 4.0 meq / g, and more preferably 0.3 meq / g to 3.0 meq / g.

[0182] (d1) Examples of polysaccharides include chitosan, hyaluronic acid and its derivatives, and biopolysaccharides, which are described below. Chitosan: (d1) The polysaccharide can be selected from chitosan.

[0183] In one embodiment, chitosan may have a low molecular weight.

[0184] The molecular weight (Da) of chitosan may be 1,000 or more, preferably 2,000 or more, and more preferably 3,000 or more. On the other hand, the molecular weight (Da) of chitosan may be less than 20,000, preferably less than 15,000, and more preferably less than 10,000.

[0185] Therefore, the molecular weight (Da) of the low molecular weight chitosan may be greater than 1,000 and less than 20,000, preferably greater than 2,000 and less than 15,000, and more preferably greater than 3,000 and less than 10,000.

[0186] In another embodiment, chitosan may have a high molecular weight.

[0187] The molecular weight (Da) of chitosan may be greater than 20,000, preferably greater than 50,000, and more preferably greater than 80,000. On the other hand, the molecular weight (Da) of chitosan may be less than 1,000,000, preferably less than 500,000, and more preferably less than 300,000.

[0188] Therefore, the molecular weight (Da) of the high molecular weight chitosan may be greater than 20,000 and less than 1,000,000, preferably greater than 50,000 and less than 500,000, and more preferably greater than 80,000 and less than 300,000.

[0189] Unless otherwise defined in the description, "molecular weight" refers to the mass-average molecular weight. Molecular weight can be measured or determined by gel permeation chromatography, for example, in accordance with ASTM D5296-19.

[0190] Chitosan is extremely rare in nature. It has only been reported in the exoskeleton of certain insects, such as termite queens, and in the cell walls of certain types of fungi, specifically the Zygomycetes.

[0191] Chitosan can be obtained by the deacetylation of chitin. Chitin is a polysaccharide composed of several N-acetyl-D-glucosamine units linked together by β-linkages (1,4).

[0192] The ideal chemical structure of chitosan is a sequence of β-D-glucosamine monomers linked by glycosidic bonds (1→4).

[0193] The "chitosan" according to the present invention refers to any copolymer formed from the constituent units N-acetyl-D-glucosamine and D-glucosamine, wherein the degree of acetylation is less than 90%, preferably less than 80%, preferably less than 70%, preferably less than 60%, and preferably less than 50%. Chitosan consists of glucosamine sugar units (deacetylated units) and N-acetyl-D-glucosamine units (acetylated units) linked together by β-type bonds (1,4), and is a poly(N-acetyl-D-glucosamine)-poly(D-glucosamine) type polymer.

[0194] More preferably, the degree of acetylation of chitosan is 40% or less, preferably 35% or less, preferably 25% or less, preferably 15% or less, and preferably 10% or less.

[0195] The degree of acetylation is the percentage of acetylated units relative to the total number of units, and can be determined by Fourier transform infrared spectroscopy (FT-IR) or titration with a strong base.

[0196] The chitosan of the present invention is preferably a polysaccharide prepared from fungal sources. In particular, it is extracted and purified from safe and abundant food or biotechnologically derived fungi, such as mushrooms (Agaricus bisporus) or black mold (Aspergillus niger).

[0197] The chitosan of the present invention is preferably derived from Ascomycetes, particularly Aspergillus and / or Basidiomycetes, specifically from the mycelium of Lentinula edodes and / or button mushrooms. Preferably, the fungus is Aspergillus.

[0198] Chitosan may be of genetically modified organism (GMO) origin, but is preferably of non-GMO origin.

[0199] The chitosan according to the present invention is natural, that is, unmodified. In particular, it contains no chemical modifications whatsoever.

[0200] One method for preparing chitosan is described in WO03 / 068824.

[0201] Preferably, the chitosan used in the present invention is in powder form. It is commercially available from Kitozyme under the names Kiosmetine or Kionutrime, for example, Kiosmetine-CSH and Kiosmetine P.

[0202] Hyaluronic acid and its derivatives: (d1) The polysaccharide can be selected from hyaluronic acid and its derivatives.

[0203] Hyaluronic acid can be represented by the following chemical formula:

[0204] [ka]

[0205] In the context of this invention, the term "hyaluronic acid" specifically refers to the following formula:

[0206] [ka]

[0207] It contains the basic unit of hyaluronic acid. This is the smallest part of hyaluronic acid, which includes disaccharide dimers, namely D-glucuronic acid and N-acetylglucosamine.

[0208] In the context of this invention, the term "hyaluronic acid" refers to a linear polymer comprising the polymer units described above, linked together in the chain via alternating β(1,4) and β(1,3) glucosidic bonds, having a molecular weight (Mw) that can range between 380 and 13,000,000 daltons. This molecular weight depends primarily on the source and / or preparation method from which the hyaluronic acid is obtained.

[0209] In the context of this invention, the term "hyaluronic acid" also includes hydrolyzed hyaluronic acid.

[0210] In the context of this invention, the term "hyaluronic acid and its derivatives" also includes hyaluronic acid salts. Examples of salts include alkali metal salts such as sodium salts and potassium salts, alkaline earth metal salts such as magnesium salts, ammonium salts, and mixtures thereof. Sodium hyaluronate is preferred.

[0211] The term "hyaluronic acid and its derivatives" also, in the context of the present invention, includes hyaluronic acid esters, in particular those in which all or part of the carboxylic acid groups of the acidic functional group are esterified with an oxyethylene alkyl or alcohol, and which contain 1 to 20 carbon atoms, and in particular those in which the degree of substitution at the level of D-glucuronic acid of hyaluronic acid is in the range of 0.5% to 50%.

[0212] In particular, methyl, ethyl, n-propyl, n-pentyl, benzyl, and dodecyl esters of hyaluronic acid can be mentioned. Such esters are described in detail in D. Campoccia et al., "Semisynthetic resorbable materials from hyaluronan esterification," Biomaterials 19 (1998), pp. 2101-2127.

[0213] In one embodiment, the hyaluronic acid derivative may be, for example, acetylated hyaluronic acid or a salt thereof.

[0214] The term "hyaluronic acid and derivatives thereof" also includes cationic hyaluronic acid in the context of the present invention.

[0215] Cationic hyaluronic acid comprises at least one cationic moiety. The cationic moiety is -N + a trialkylammonium group such as (CH3)3. The cationic moiety may comprise at least one hydroxyl group. Examples of the cationic group include -CH2-CH(OH)-CH2-N + (CH3)3.

[0216] Examples of cationic hyaluronic acid include hydroxypropyltrimonium hyaluronate.

[0217] The molecular weight of hyaluronic acid and derivatives thereof is not limited. The molecular weight of hyaluronic acid and derivatives thereof may be 5 kDa or more, preferably 20 kDa or more, more preferably 100 kDa or more. The molecular weight of hyaluronic acid and derivatives thereof may be 20 MDa or less, preferably 10 MDa or less, more preferably 2,000 kDa or less. Therefore, the molecular weight of hyaluronic acid and derivatives thereof may be 5 kDa to 20 MDa, preferably 20 kDa to 10 MDa, more preferably 100 kDa to 2,000 kDa.

[0218] Unless otherwise defined in the description, "molecular weight" may mean a weight average molecular weight.

[0219] Hyaluronic acid or a derivative thereof may in particular be that supplied under the trade name HyActive™ (Mw: 10 to 150 kDa) by the company Centipro, that supplied under the trade name Cristalhyal® (Mw: 1 to 1.4 MDa) by the company Givaudan, that supplied under the trade name Nutra™ HA (Mw: 907,600 Da) by the company Bioland, that supplied under the trade name Nutra™ HAF (Mw: 74,600 Da) by the company Bioland, that supplied under the trade name Oligo™ HA (Mw: 0.5 to 10.1 kDa) by the company Bioland, that supplied under the trade name D-Factor® (Mw: 380 Da) by the company Res Pharma, or that supplied under the trade name Hybloom™ Sodium Hyaluronate (HA-T) (MW: 1,000 kDa to 1,800 kDa) by the company Bloomage Freda Biopharm.

[0220] A single hyaluronic acid or derivative thereof having a single molecular weight, or a combination of two or more types of hyaluronic acid or derivatives thereof having different molecular weights, can be used.

[0221] The hyaluronic acid or derivative thereof is preferably selected from hyaluronate, more preferably an alkali metal hyaluronate, and even more preferably sodium hyaluronate.

[0222] Biopolysaccharide: In one embodiment, (d1) the polysaccharide may be selected from microorganism-derived polysaccharides, which are referred to as biopolysaccharides.

[0223] A microorganism-derived polysaccharide or biopolysaccharide means a polysaccharide produced by a microorganism such as a pathogenic bacterium or bacterium. The microorganism-derived polysaccharide may be produced by fermentation of a sugar via a microorganism.

[0224] Microbial polysaccharides may contain units selected from mannose units, glucose units, and glucuronic acid units or galacturonic acid units within their chains, and these units may be acylated.

[0225] In particular, xanthan gum produced by the bacterium Xanthomonas campestris, as well as its variants and variants, can be mentioned.

[0226] Furthermore, scleroglucan gum produced by Sclerotium rolfsii, gellan gum produced by Pseudomonas elodea or Sphingomonias, pulllan gum produced by Aureobacidium pullulens, curdlar gum produced by Alcaligenes of the Faecalis myxogenes type, dextran gum produced by numerous organisms including Leuconostoc mesenteroides and Leuconostoc dextrantum, grifolan gum produced by Maitake mushroom (Grifola frondara), and shiitake mushroom (Lentinus) Other examples include lentinan gum produced by *Edodes*, schizophyllan gum produced by *Schizophyllum commine*, spirulinan gum produced by *Spirulina sybsyla*, and cresting gum produced by *Coriates versicolor*.

[0227] Microbial polysaccharides may be chemically modified at will.

[0228] According to certain embodiments of the present invention, the microbial polysaccharide is modified. In particular, a nonionic guar gum modified with C1-C6 (poly)hydroxyalkyl groups can be cited.

[0229] Examples of hydroxyalkyl groups include hydroxymethyl, hydroxyethyl, hydroxypropyl, and hydroxybutyl groups.

[0230] These guar gums are well known in the prior art and can be prepared, for example, by reacting the guar gum with the corresponding alkene oxide, such as propylene oxide, to obtain guar gum modified with a hydroxypropyl group.

[0231] The degree of (poly)hydroxyalkylation corresponds to the number of alkylene oxide molecules consumed by the number of free hydroxyl functional groups present on the guar gum, and is preferably in the range of 0.4 to 1.2.

[0232] Nonionic guar gums optionally modified with such hydroxyalkyl groups are sold by Rhodia Chimie under trade names such as Jaguar HP8, Jaguar HP60 and Jaguar HP120, Jaguar DC 293 and Jaguar HP 105, or by Aqualon under the name Galactasol 4H4FD2.

[0233] Examples of polysaccharides derived from microorganisms include cardran, xanthan gum, gellan gum, dextran, pullulan, sclerotium gum, and mixtures thereof.

[0234] It may be preferable that the microbial polysaccharide be selected from the group consisting of sclerotium gum, xanthan gum, and mixtures thereof.

[0235] It is preferable that the polysaccharide (d1) is selected from chitosan, hyaluronic acid and derivatives thereof, microorganism-derived polysaccharides, and mixtures thereof.

[0236] It is more preferable that the polysaccharide (d1) is selected from chitosan, hyaluronic acid and salts thereof, xanthan gum, and mixtures thereof.

[0237] It is even more preferable that the polysaccharide (d1) is selected from high-molecular-weight chitosan, hyaluronic acid and sodium hyaluronate, xanthan gum, and mixtures thereof.

[0238] The amount of the polysaccharide (d1) in the composition according to the present invention may be 0.001 mass% or more, preferably 0.005 mass% or more, more preferably 0.01 mass% or more, relative to the total mass of the composition.

[0239] On the other hand, the amount of the polysaccharide (d1) in the composition according to the present invention may be 15 mass% or less, preferably 10 mass% or less, more preferably 5 mass% or less, relative to the total mass of the composition.

[0240] Therefore, the amount of the polysaccharide (d1) in the composition according to the present invention may be 0.001 mass% to 15 mass%, preferably 0.005 mass% to 10 mass%, more preferably 0.01 mass% to 5 mass%, relative to the total mass of the composition.

[0241] (d2) Amino acids, derivatives thereof, and salts thereof The composition according to the present invention may comprise at least one compound selected from the group consisting of (d2) amino acids, derivatives thereof, and salts thereof (hereinafter, may be referred to as the (d2) compound). When two or more of the (d2) compounds are used, they may be the same or different.

[0242] In one embodiment, the (d2) compound is selected from amino acids.

[0243] An amino acid has at least one amino group and at least one carboxyl group.

[0244] The amino group may be a primary amino group, a secondary amino group, or a tertiary amino group, preferably a primary amino group or a secondary amino group, and more preferably a secondary amino group.

[0245] It is preferable that the molecular weight of the amino acid is less than 1000, more preferably less than 500, and even more preferably less than 200. Therefore, it is preferable that the amino acid is not a polymer. In other words, it is preferable that the amino acid is a nonpolymeric amino acid.

[0246] Amino acids can be selected from the group consisting of acidic amino acids, basic amino acids, and neutral amino acids. Acidic amino acids typically have one amino group and two carboxyl groups. Basic amino acids typically have two amino groups and one carboxyl group. The number of amino groups and carboxyl groups in a neutral amino acid are the same.

[0247] The amino acid may be in either the D or L form.

[0248] Amino acids may be hydrophilic or hydrophobic. Hydrophilic amino acids are preferred.

[0249] The amino acids can be selected from the group consisting of α-amino acids, β-amino acids, γ-amino acids, and δ-amino acids.

[0250] It is preferable that the amino acid be selected from α-amino acids, in which the amino group is bonded to a carbon atom to which a carboxyl group is also bonded.

[0251] α-amino acids can be selected from the group consisting of acyclic α-amino acids and cyclic α-amino acids.

[0252] Acyclic α-amino acids can be selected from the group consisting of alanine, arginine, asparagine, aspartic acid, cysteine, glutamine, glutamic acid, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan, tyrosine, and valine.

[0253] The cyclic α-amino acid can be selected from non-aromatic cyclic α-amino acids, such as pyrrolidone carboxylic acids (pyroglutamic acid or pyruduric acid). Pyrrolidone carboxylic acids can be formed by intermolecular condensation between the amino group and the carboxyl group of glutamic acid.

[0254] In another embodiment, the (d2) compound is selected from amino acid derivatives.

[0255] Derivatives of amino acids (amino acid derivatives) can be selected from amino acids in which at least one hydrogen atom on the nitrogen atom of the amino group in the amino acid is substituted with a substituent.

[0256] Examples of substituents include alkyl groups, acyl groups, alkenyl groups, alkoxyl groups, and alkoxycarbonyl groups.

[0257] The alkyl group may be linear, branched, or cyclic alkyl group. The alkyl group may be a linear or branched C1-C6 alkyl group, preferably a C1-C4 alkyl group, such as a methyl group, ethyl group, propyl group, i-propyl group, and butyl group. On the other hand, the alkyl group may be a cyclic C3-C6 alkyl group, such as a cyclopentyl group and a cyclohexyl group.

[0258] The acyl group may be a C1-C6 acyl group, such as a formyl group or an acetyl group.

[0259] The alkenyl group may be a C2-C6 alkenyl group, such as a vinyl group, an allyl group, a butylene group, a pentenyl group, or a hexenyl group.

[0260] The alkoxy group may be a C1-C6 alkoxy group, such as a methoxy group, an ethoxy group, or a propoxy group.

[0261] The alkoxycarbonyl group may be a C1-C6 alkoxycarbonyl group, such as a methoxycarbonyl group, an ethoxycarbonyl group, or a propoxycarbonyl group.

[0262] The above substituents may be further substituted with at least one group such as a halogen atom, an amino group, a nitro group, a cyano group, or a hydroxyl group, as well as an aromatic group such as a phenyl group.

[0263] It is preferable that the amino acid derivative (amino acid derivative) is selected from amino acid surfactants.

[0264] Typically, amino acid surfactants are anionic surfactants comprising at least one amino moiety and at least one carboxylic acid moiety in the form of a carboxylate. Amino acid surfactants may have two or more amino moieties and / or two or more carboxylic acid moieties in the form of a carboxylate.

[0265] The amino acid surfactant can preferably be selected from salts of N-acylated amino acids, such as alkali metal salts and alkaline earth metal salts of N-acylated amino acids, such as sodium salts, potassium salts, magnesium salts and calcium salts of N-acylated amino acids.

[0266] The acyl groups that form the N-acyl moiety of amino acid surfactants are C1-C 30 Acyl group, preferably C6-C 28 Acyl group, more preferably C 12 ~C 24 It can be an acyl group.

[0267] The amino acid surfactant may more preferably be selected from the group consisting of N-acyl sarcosinate, N-acyl alaninate, N-acyl glutamate, N-acyl aspartate, N-acyl glycinate, and mixtures thereof.

[0268] Examples of amino acid surfactants include, but are not limited to, the following: - N-acyl sarcosinates (salts), for example, sodium lauroyl sarcosinate sold by Nikkol Chemicals Co., Ltd. under the name Nikkol Sarcosinate® LN, or sold by Innospec Performance Chemicals Europe Limited under the name Pureact® LSR; sodium myristoyl sarcosinate sold by Nikkol Chemicals Co., Ltd. under the name Nikkol Sarcosinate® MN; and sodium palmitoyl sarcosinate sold by Nikkol Chemicals Co., Ltd. under the name Nikkol Sarcosinate® PN. - N-acylalaninates (salts), for example, sodium N-lauroyl-N-methylamidopropionate sold by Nikko Chemicals Co., Ltd. under the name Sodium Nikkol Alaninate (trademark) LN 30, or sold by Kawaken Fine Chemicals Co., Ltd. under the name Alanone (registered trademark) ALE; sodium cocoyl alanine sold by Ajinomoto Co., Inc. under the name Amilite (registered trademark) ACS-12; and N-lauroyl-N-methylalaninetriethanolamine sold by Kawaken Fine Chemicals Co., Ltd. under the name Alanone (registered trademark) ALTA. - N-acyl glutamate (salt), for example, sodium stearoyl glutamate sold by Ajinomoto Co., Inc. under the name Amisoft® HS-11P and by BASF Japan under the name Eumulgin® SR; sodium lauroyl glutamate sold by BASF Japan under the name Plantapon® Amino SLG-P; monococoyl glutamate triethanolamine sold by Ajinomoto Co., Inc. under the name Amisoft® CT-12; lauroyl glutamate triethanolamine sold by Ajinomoto Co., Inc. under the name Amisoft® LT-12; and disodium stearoyl glutamate sold by Ajinomoto Co., Inc. under the name Amisoft® HS-21P. - N-acyl aspartate (salt), for example, disodium N-lauroyl aspartate sold by Asahi Kasei Corporation under the name AminoFoamer® FLMS-P1; and a mixture of N-lauroyl aspartate triethanolamine and N-myristoyl aspartate triethanolamine sold by Asahi Kasei Corporation under the name AminoFoamer® FCMT-L, and - N-acylglycinates (salts), for example, sodium N-cocoylglycinate sold by Ajinomoto Co., Inc. under the name Amilite® GCS-12K; and potassium N-cocoylglycinate sold under the name Amilite® GCK-12K.

[0269] Furthermore, it may be preferable that the amino acid surfactant be selected from among amino acid-based gemini surfactants.

[0270] Gemini surfactants or dimeric surfactants are well known. For detailed descriptions of their various chemical structures and physicochemical properties, please refer to the following publications: Milton J. Rosen, Gemini Surfactants, Properties of surfactant molecules with two hydrophilic groups and two hydrophobic groups, Cosmetics & Toiletries journal, Vol. 113, December 1998, pp. 49-55, and Milton J. Rosen, Recent Developments in Gemini Surfactants, Allured's Cosmetics & Toiletries magazine, July 2001, Volume 116, Issue 7, pp. 67-70.

[0271] Amino acid gemin surfactants are anionic and contain multiple hydrophobic and hydrophilic parts.

[0272] Amino acid gemin surfactants can be selected from compounds having two or more aliphatic amide groups (hereinafter sometimes referred to as "amide compounds"). Amide compounds are defined by the following formula (A):

[0273] [ka]

[0274] [In the formula, Y' independently represents a carboxylic acid group, or an alkali salt of a carboxylic acid group, such as a sodium salt of a carboxylic acid group. j1, k1, j2, and k2 are integers such that (j1, k1, j2, k2) = (2,0,2,0), (2,0,0,2), (0,2,2,0), and (0,2,0,2). l represents an integer between 6 and 16, preferably between 8 and 14, and more preferably between 10 and 12. It can be represented by [this].

[0275] Preferably, in equation (A), l represents an integer between 8 and 12, where j1=j2=0 and k1=k2=2.

[0276] Most preferably, in equation (A), Y' is -COONa, j1=j2=0, k1=k2=2, and l=10.

[0277] Examples of the amide compounds represented by formula (A) include dilauramidoglutamidridine sodium (dilauroyl glutamate lysine Na), dimyristoyl glutamidridine sodium, and distearoyl glutamidridine sodium. Dilauramidoglutamidridine sodium (dilauroyl glutamate lysine Na) is particularly preferred. Dilauramidoglutamidridine sodium (dilauroyl glutamate lysine Na) is commercially available from Asahi Chemicals Co., Ltd. as PELLICER L-30 in an aqueous solution with a concentration of 29% by mass relative to the total mass of the aqueous solution, or as PELLICER LB-30G in an aqueous solution with a concentration of 27.3% by mass relative to the total mass of the aqueous solution.

[0278] The above amide compounds represented by formula (A) can be prepared, for example, by reacting a long-chain N-acyl acidic amino acid anhydride with a basic amino acid, such as lysine, in water and / or a mixed solvent of water and an organic solvent, or in an inert organic solvent, such as tetrahydrofuran, benzene, toluene, xylene, tetrachloromethane, chloroform, acetone, etc., or without any solvent, at a temperature of -5°C to 200°C, preferably 5°C to 100°C, more preferably 0°C to 60°C.

[0279] Therefore, the amino acid gemin surfactant may be an N-acyl glutamate / amino acid derivative, preferably a dipeptide of two N-acyl glutamates, and a basic amino acid, such as lysine.

[0280] In another embodiment, the (d2) compound is selected from a salt of an amino acid or a salt of an amino acid derivative.

[0281] The type of salt of an amino acid or amino acid derivative is not limited. The salt may be an acid salt or a base salt. Examples of acid salts include inorganic acid salts, such as hydrochloride, sulfate, nitrate, and phosphate, and organic acid salts, such as citrate, oxalate, acetate, formate, maleate, and tartrate. Examples of base salts include inorganic base salts, such as sodium salt, potassium salt, calcium salt, magnesium salt, copper salt, zinc salt, aluminum salt, and ammonium salt, and organic base salts, such as triethylammonium salt, triethanolammonium salt, pyridinium salt, and diisopropylammonium salt. Sodium salts are preferred.

[0282] (d2) The compound is preferably selected from cyclic α-amino acids and their salts, more preferably from non-aromatic cyclic α-amino acids and their salts, even more preferably from pyrrolidone carboxylic acids and their salts, and particularly from sodium pyrrolidone carboxylate (PCA-Na or PCA sodium).

[0283] The amount of compound (d2) in the composition according to the present invention may be 0.001% by mass or more, preferably 0.005% by mass or more, and more preferably 0.01% by mass or more, based on the total mass of the composition.

[0284] On the other hand, the amount of compound (d2) in the composition according to the present invention may be 15% by mass or less, preferably 10% by mass or less, and more preferably 5% by mass or less, based on the total mass of the composition.

[0285] Therefore, the amount of compound (d2) in the composition according to the present invention may be 0.001% to 15% by mass, preferably 0.005% to 10% by mass, and more preferably 0.01% to 5% by mass, relative to the total mass of the composition.

[0286] (d3) Polyglutamates and their salts The composition according to the present invention may contain (d3) at least one polyamino acid or a salt thereof. A single type of polyamino acid or a salt thereof may be used, or two or more different types of polyamino acids or salts thereof may be used in combination.

[0287] (d3) The polyamino acid is preferably selected from polyglutamic acid. Therefore, component (d3) in the composition according to the present invention is preferably at least one polyglutamic acid or a salt thereof.

[0288] Polyglutamic acid or its salts have the following chemical formula (1): ROOC-CH2CH2-CH(-COOR)-NH-[CO-CH2CH2-CH(-COOR)-NH-] n -CO-CH2CH2-CH(-COOR)-NH2(1) [In the formula, R independently represents an alkali metal atom such as a hydrogen atom, a sodium atom, and a potassium atom, or an ammonium group such as a tetramethylammonium group and a tetraethylammonium group.] n is an integer of 2 or greater, preferably 4 or greater, and more preferably 6 or greater. It may have a chemical structure represented by [this].

[0289] The polyglutamic acid or its salt represented by the above chemical formula (1) may be called γ-polyglutamic acid or its salt because the carboxylic acid group at the γ position and the amino group at the α position form a peptide bond.

[0290] It is preferable that the polyglutamic acid or its salt has a molecular weight of 1000 or more and a degree of polymerization of 8 or more (where "n" in the above chemical formula (1) is 6 or more).

[0291] It may be more preferable that the polyglutamic acid or its salt has a molecular weight of 100,000 or more and a degree of polymerization of 770 or more (where "n" in the above chemical formula (1) is 768 or more).

[0292] It may be even more preferable that the molecular weight of the polyglutamic acid or its salt is 500,000 or more, and the degree of polymerization is 3840 or more (where "n" in the above chemical formula (1) is 3838 or more).

[0293] There is no upper limit to the molecular weight of polyglutamic acid or its salts.

[0294] However, the molecular weight of polyglutamic acid or its salt may be 5,000,000 or less, and the degree of polymerization may be 38,500 or less (where "n" in the above chemical formula (1) is 38,498 or less). Preferably, the molecular weight of polyglutamic acid or its salt may be 3,000,000 or less, and the degree of polymerization may be 23,080 or less (where "n" in the above chemical formula (1) is 23,078 or less).

[0295] The glutamic acid that constitutes polyglutamic acid or its salts may be D-form, L-form, or racemic. However, considering market availability, biocompatibility, and biodegradability, it may be preferable to use polyglutamic acid composed solely of L-form glutamic acid or a mixture of L-form and D-form glutamic acid. However, polyglutamic acid composed of D-form glutamic acid, which has the same effect but is less degradable, can also be used.

[0296] The method for producing polyglutamic acid or its salts is not particularly limited. Examples include organic synthesis using a peptide synthesizer, organic synthesis by polymerization of glutamic acid N-carboxy anhydride, and organic synthesis by polymerization of N-benzyloxycarbonylglutamic acid anhydride. On the other hand, microorganisms belonging to the genus Bacillus that have the ability to produce γ-polyglutamic acid (in particular, Bacillus subtilis, Bacillus anthracis, Bacillus licheniformis, and Bacillus megaterium, which have the ability to produce γ-polyglutamic acid) can also be used in fermentation methods for producing polyglutamic acid or its salts.

[0297] In addition to natural culture media composed of natural products such as shochu distillation wastewater culture media and soybean extract culture media, the following components are used as culture media in the fermentation method: Carbon sources such as glucose, fructose, galactose, sucrose, maltose, mannose, lactose, glycerol, and starch. Inorganic nitrogen sources such as ammonium sulfate, ammonium phosphate, and ammonium hydrochloride, Organic nitrogen sources such as glutamic acid or its salts, aspartic acid or its salts, Major inorganic salts such as sodium chloride, magnesium sulfate, monopotassium phosphate, phosphorus, and disodium phosphate, Trace amounts of inorganic salts containing atoms such as iron, copper, zinc, cobalt, nickel, boron, manganese, molybdenum, tin, selenium, silicon, arsenic, vanadium, chromium, and fluorine. Vitamins such as biotin, nicotinamide, calcium pantothenate, thiamine, riboflavin, and pyridoxine hydrochloride. Organic acids such as citric acid, tartaric acid, malic acid, and glycolic acid, and Yeast extract, meat extract, potato extract, tomato extract, and natural product extracts such as soy peptides. Any synthetic medium or semi-synthetic medium consisting of any one of the following may be used at any concentration.

[0298] The microbial culture conditions may be set to a temperature range of 20°C to 37°C, and can be further controlled during the microbial growth process and the polyglutamic acid production process. The pH may be set to a range of 5.0 to 8.0, and can be further controlled during the microbial growth process and the polyglutamic acid production process.

[0299] After the completion of the culture, known methods such as acid precipitation, solvent precipitation, and membrane purification can be arbitrarily selected as methods for extracting and purifying polyglutamic acid or its salt from the culture medium.

[0300] It is preferable to use polyglutamic acid or its alkali metal salt, such as sodium polyglutamate, as the polyglutamic acid or its salt.

[0301] Commercially available products may be used as polyglutamic acid or its salts. Examples of polyglutamic acid or its salts include Hyafactor® PGA-HM, sold by Bloomage Biotechnology Co., Ltd. in China, and Bio-PGA Solution HE, HB, LB, and LE, as well as Bio PGA Na powder, sold by Ichimaru Falcos Co., Ltd. in Japan.

[0302] The amount of (d3) polyamino acids and / or salts thereof in the composition according to the present invention may be 0.001% by mass or more, preferably 0.005% by mass or more, and more preferably 0.01% by mass or more, based on the total mass of the composition.

[0303] On the other hand, the amount of (d3) polyamino acids and / or salts thereof in the composition according to the present invention may be 15% by mass or less, preferably 10% by mass or less, and more preferably 5% by mass or less, based on the total mass of the composition.

[0304] Therefore, the amount of (d3) polyamino acid and / or its salt in the composition according to the present invention may be 0.001% to 15% by mass, preferably 0.005% to 10% by mass, and more preferably 0.01% to 5% by mass, based on the total mass of the composition.

[0305] (d4) Protein The composition according to the present invention may contain (d4) at least one protein. A single type of protein may be used, or two or more different types of proteins may be used in combination.

[0306] The (d4) protein is preferably selected from plant-derived proteins. Therefore, component (d4) in the composition according to the present invention is preferably at least one plant-derived protein.

[0307] Plant-derived proteins may be polypeptides obtained from plants such as soybeans, peas, wheat, rice, corn, and sesame. The proteins may be hydrolyzed. Hydrolysis may be carried out, for example, by conventionally known methods using acids or enzymes. Plant-derived proteins may also be polypeptides obtained through industrial biotechnology methods such as genetic modification and fermentation of natural, powerful carbon sources such as cornstarch.

[0308] The plant-derived protein may be selected from the group consisting of hydrolyzed pea protein, hydrolyzed soy protein, hydrolyzed wheat protein, hydrolyzed rice protein, hydrolyzed corn protein, plant-derived recombinant silk protein, and mixtures thereof.

[0309] The plant-derived protein is preferably hydrolyzed pea protein.

[0310] The protein may contain acidic amino acids such as aspartic acid and glutamic acid, as well as basic amino acids such as arginine, histidine, and lysine.

[0311] Hydrolyzed pea protein can be prepared by hydrolysis of peas (Pisum sativum L). Commercial products such as Promois® WJ or Promois® WJ-SP manufactured by Seiwa Kasei Co., Ltd., which are aqueous solutions or powdered pea proteins with an average molecular weight of approximately 500, may be used as hydrolyzed pea protein. Hydrolyzed soy protein can be prepared by hydrolysis of soybeans (Glycine max). Commercial products such as Promois® WS or Promois® WS-HSP manufactured by Seiwa Kasei Co., Ltd., which are aqueous solutions or powdered soy proteins with an average molecular weight of approximately 700, may be used as hydrolyzed soy protein. Hydrolyzed wheat protein can be prepared by hydrolysis of wheat (Triticum). As hydrolyzed wheat protein, commercially available products such as Promois® WG or Promois® WG-SP manufactured by Seiwa Kasei Co., Ltd., which are aqueous solutions or powdered wheat protein with an average molecular weight of approximately 700, may be used. Hydrolyzed rice protein can be prepared by hydrolysis of rice (Oryza sativa). As hydrolyzed rice protein, commercially available products such as Promois® WR or Promois® WR-SP manufactured by Seiwa Kasei Co., Ltd., which are aqueous solutions or powdered rice protein with an average molecular weight of approximately 400, may be used. As a mixture of hydrolyzed wheat protein, hydrolyzed corn protein, and hydrolyzed soy protein, commercially available products such as Keraplant manufactured by TRI-K, which are aqueous solutions of wheat protein, corn protein, and soy protein, may be used. As plant-derived silk, commercially available products such as Silkgel Neo® manufactured by Givaudan, which is an aqueous gel silk produced by industrial biotechnology using fermentation, may be used.

[0312] Since the protein can be obtained from plants, the present invention can be environmentally friendly.

[0313] The amount of (d4) protein in the composition according to the present invention may be 0.001% by mass or more, preferably 0.005% by mass or more, and more preferably 0.01% by mass or more, based on the total mass of the composition.

[0314] On the other hand, the amount of (d4) protein in the composition according to the present invention may be 15% by mass or less, preferably 10% by mass or less, and more preferably 5% by mass or less, based on the total mass of the composition.

[0315] Therefore, the amount of (d4) protein in the composition according to the present invention may be 0.001% to 15% by mass, preferably 0.005% to 10% by mass, and more preferably 0.01% to 5% by mass, relative to the total mass of the composition.

[0316] (Diol) The compositions according to the present invention may include (e) at least one diol having at least one carbon chain having three or more carbon atoms, a total number of five or six carbon atoms. A single type of such diol or a combination of different types of such diols can be used.

[0317] In this specification, the term "diol" refers to a compound having two alcohol functional groups. In other words, a diol is an alcohol having two hydroxyl groups.

[0318] The number of carbon atoms in the carbon chain may be five or six.

[0319] (e) The carbon chain containing three or more carbon atoms in the diol may be linear or branched. The carbon chain must not be interrupted by heteroatoms, such as oxygen, sulfur, and nitrogen atoms. Therefore, the carbon chain may contain continuous carbon atoms.

[0320] (e) Preferably, the number of carbon chains containing three or more carbon atoms in the diol is one or two.

[0321] (e) The total number of carbon atoms in the diol is 5 or 6.

[0322] (e)diols having at least one carbon chain with a total of five or six carbon atoms, including three or more carbon atoms, may have divalent linear or branched hydrocarbon groups. The divalent linear or branched hydrocarbon groups that may be present in (e)diols may be saturated or unsaturated. (e)diols having at least one carbon chain with a total of five or six carbon atoms, including three or more carbon atoms, preferably contain divalent linear or branched saturated hydrocarbon groups, more preferably linear or branched alkylene groups, such as propylene, pentylene, and hexylene groups.

[0323] A (e)diol having at least one carbon chain containing three or more carbon atoms and having a total of five or six carbon atoms can have a linear, branched, or cyclic molecular structure, as long as it has a carbon chain containing three or more carbon atoms and having a total of five or six carbon atoms.

[0324] (e)diols having at least one carbon chain with a total number of carbon atoms of 5 or 6, including 3 or more carbon atoms, include two hydroxyl groups. 5~6 It could be a diol.

[0325] It is preferable that the (e)diol having at least one carbon chain, containing three or more carbon atoms, and having a total number of five or six carbon atoms, is selected from the group consisting of dipropylene glycol, pentylene glycol, hexylene glycol, and mixtures thereof.

[0326] It is more preferable that the (e)diol having at least one carbon chain, containing three or more carbon atoms, and having a total number of five or six carbon atoms, is selected from the group consisting of pentylene glycol, hexylene glycol, and mixtures thereof.

[0327] The amount of (e) diol described above may be 0.1% by mass or more, preferably 0.5% by mass or more, and more preferably 1% by mass or more, based on the total mass of the composition.

[0328] On the other hand, the amount of (e) diol may be 35% by mass or less, preferably 30% by mass or less, and more preferably 25% by mass or less, based on the total mass of the composition.

[0329] Therefore, the amount of (e) diol mentioned above may be 0.1% to 35% by mass, preferably 0.5% to 30% by mass, and more preferably 1% to 25% by mass, based on the total mass of the composition.

[0330] (water) The composition according to the present invention may contain (f) water.

[0331] (f) The amount of water may be 50% by mass or more, preferably 55% by mass or more, and more preferably 60% by mass or more, based on the total mass of the composition.

[0332] On the other hand, (f) the amount of water may be 99% by mass or less, preferably 98% by mass or less, and more preferably 97% by mass or less, relative to the total mass of the composition.

[0333] Therefore, (f) the amount of water may be 50% to 99% by mass, preferably 55% to 98% by mass, and more preferably 60% to 97% by mass, relative to the total mass of the composition.

[0334] (Monovalent nonpolymeric acid or its salt) The composition according to the present invention may contain (g) at least one monovalent nonpolymeric acid or a salt thereof. A single type of monovalent nonpolymeric acid or a salt thereof, or a combination of different types of monovalent nonpolymeric acids or salts thereof, can be used.

[0335] In this specification, the term "non-polymer" means that the acid is not obtained by polymerizing two or more monomers. Therefore, non-polymer acids do not correspond to acids obtained by polymerizing two or more monomers, such as polyacrylic acid.

[0336] In this specification, the term "salt" means a salt formed by adding a suitable base to a monovalent nonpolymeric acid, which can be obtained from the reaction of a monovalent nonpolymeric acid with a base according to methods known to those skilled in the art. Examples of salts include metal salts, such as salts with alkali metals like Na and K, and salts with alkaline earth metals like Mg and Ca, as well as ammonium salts.

[0337] (g) The molecular weight of the monovalent nonpolymeric acid or its salt is preferably less than 1,000, preferably 500 or less, and more preferably 200 or less.

[0338] (g) A monovalent nonpolymeric acid or a salt thereof may be included in the aqueous phase formed by (e) water. (g) A monovalent nonpolymeric acid or a salt thereof can promote the dissolution of (d1) a polysaccharide, preferably chitosan, more preferably high molecular weight chitosan, for example, in water.

[0339] (g) A monovalent nonpolymeric acid has a single acid group which can be selected from the group consisting of a carboxylic acid group, a sulfate group, a sulfonic acid group, a phosphoric acid group, a phosphonic acid group, and mixtures thereof.

[0340] (g) A monovalent nonpolymeric acid or a salt thereof may be selected from monovalent organic or inorganic acids and their salts.

[0341] (g) The monovalent nonpolymeric acid is preferably a monovalent organic acid, more preferably a monovalent nonpolymeric carboxylic acid.

[0342] The monovalent nonpolymeric carboxylic acid can be selected from hydroxy acids, preferably alpha-hydroxy acids and beta-hydroxy acids. Examples of alpha-hydroxy acids include lactic acid and glycolic acid. Examples of beta-hydroxy acids include salicylic acid.

[0343] Therefore, the monovalent nonpolymeric acid may be a monovalent nonpolymeric organic acid, preferably a monovalent nonpolymeric carboxylic acid, and more preferably a monovalent hydroxy acid, such as lactic acid and salicylic acid.

[0344] The amount of (g) monovalent nonpolymeric acid or its salt in the composition according to the present invention may be 0.01% by mass or more, preferably 0.05% by mass or more, and more preferably 0.1% by mass or more, based on the total mass of the composition.

[0345] On the other hand, the amount of (g) monovalent nonpolymeric acid or its salt in the composition according to the present invention may be 15% by mass or less, preferably 10% by mass or less, and more preferably 5% by mass or less, based on the total mass of the composition.

[0346] Therefore, the amount of (g) monovalent nonpolymeric acid or its salt in the composition according to the present invention may be 0.01% to 15% by mass, preferably 0.05% to 10% by mass, and more preferably 0.1% to 5% by mass, based on the total mass of the composition.

[0347] (pH) The pH of the composition according to the present invention may be 3 to 9, preferably 3.3 to 8.5, and more preferably 3.5 to 8.

[0348] The pH of the composition according to the present invention can be adjusted by adding at least one alkaline agent and / or at least one acid. The pH of the composition according to the present invention can also be adjusted by adding at least one buffering agent.

[0349] (Optional additives) In addition to the components described above, the compositions according to the present invention may also contain components typically used in cosmetics, specifically cationic, amphoteric, or nonionic surfactants or emulsifiers; divalent alpha-hydroxy acids such as citric acid; hydrophilic thickeners (other than (d1) polysaccharides); lipophilic thickeners; hydrophilic antioxidants such as vitamin C; lipophilic antioxidants such as tocopherol; volatile or non-volatile organic solvents; silicones; natural extracts derived from animals or plants, etc., to the extent that they do not impair the effects of the present invention.

[0350] The composition according to the present invention may contain the above-mentioned optional additives in an amount of 0.01% to 30% by mass, preferably 0.05% to 20% by mass, and more preferably 0.1% to 10% by mass, based on the total mass of the composition.

[0351] The composition according to the present invention may contain a very limited amount of surfactant or emulsifier, taking environmental compatibility into consideration.

[0352] The amount of surfactant or emulsifier in the composition according to the present invention may be 1% by mass or less, preferably 0.1% by mass or less, and more preferably 0.01% by mass or less, based on the total mass of the composition. It is particularly preferable that the composition according to the present invention does not contain surfactant or emulsifier.

[0353] The composition according to the present invention may contain a very limited amount of silicone, taking environmental compatibility into consideration.

[0354] The amount of silicone in the composition according to the present invention may be 1% by mass or less, preferably 0.1% by mass or less, and more preferably 0.01% by mass or less, based on the total mass of the composition. It is particularly preferable that the composition according to the present invention does not contain silicone.

[0355] [Preparation] The composition according to the present invention can be prepared by mixing the essential components described above with the optional components (if necessary) described above.

[0356] The methods and means for mixing the above-mentioned essential components and optional components are not limited. Any conventional methods and means may be used to mix the above-mentioned essential components and optional components to prepare the compositions according to the present invention.

[0357] The compositions according to the present invention can be prepared by simply or easily mixing using conventional mixing means such as a stirrer and a homogenizer. Heating may not be necessary. Therefore, the method for preparing the compositions according to the present invention may be environmentally friendly.

[0358] In one embodiment, the composition according to the present invention is (1) A step of preparing a diol solution by mixing (a) at least one ceramide-type compound, (b) at least one O-acyl product derived from glucose, (c) at least one first compound selected from the group consisting of (c1) fatty acids, (c2) aliphatic alcohols, and (c3) mixtures thereof, and (e) a diol having at least one carbon chain containing three or more carbon atoms and having a total number of five or six carbon atoms. (2)(d)(d1) polysaccharides, (d2) amino acids, their derivatives and salts, (d3) polyamino acids and their salts, (d4) proteins, and (d5) mixtures thereof, at least one second compound selected from the group, (f) A step of mixing with water to prepare an aqueous solution, (3) A step of adding the diol solution obtained in step (1) to an aqueous solution to prepare the composition. It can be prepared by [method].

[0359] [Beauty use] The compositions according to the present invention may be intended for use as cosmetic compositions. Therefore, the cosmetic compositions according to the present invention may be intended for application to keratinous substances. In this specification, keratinous substances mean substances that contain keratin as a main component, and examples include skin, scalp, nails, lips, and hair. For this reason, it is preferable that the cosmetic compositions according to the present invention be used in cosmetic methods for keratinous substances, particularly skin and hair.

[0360] The compositions according to the present invention can preferably be used as cosmetic compositions, more preferably as cosmetic compositions for keratin substances, and even more preferably as cosmetic compositions for skin care, scalp care, and hair care.

[0361] [form] The composition according to the present invention may exist in any form.

[0362] For example, the composition according to the present invention may be in the form of a solution, particularly an aqueous solution, or a dispersion, particularly an aqueous dispersion.

[0363] [Beauty methods and usage] The present invention also, A cosmetic method for keratinous substances such as skin, scalp, and hair, comprising the step of applying a composition according to the present invention to the keratinous substance, or Use of the composition according to the present invention for preparing a cosmetic film on keratinous substances such as skin, scalp, and hair. This also relates to that.

[0364] In this specification, "beauty method" refers to a non-therapeutic beauty method for beautifying keratinous substances such as skin, scalp, and hair.

[0365] The beauty method according to the present invention involves applying the composition according to the present invention onto a keratinous substance and drying the composition to form a film on keratinous substances such as skin, scalp, and hair.

[0366] The coating is (a) at least one ceramide-type compound, (b) At least one O-acyl product derived from glucose, which can be obtained by partial or complete esterification of vitamin F with the hydroxyl group of glucose, (c) At least one first compound selected from the group consisting of (c1) fatty acids, (c2) aliphatic alcohols, and (c3) mixtures thereof, (d) At least one second compound selected from the group consisting of (d1) polysaccharides, (d2) amino acids, their derivatives and salts, (d3) polyamino acids and their salts, (d4) proteins, and (d5) mixtures thereof. It may include.

[0367] The coating can impart a smooth feel and ease of combing to keratinous substances such as skin and hair.

[0368] The present invention may also relate to the use of the compositions according to the present invention as cosmetics, or in cosmetics, such as skin, scalp, or hair care products.

[0369] In other words, the composition according to the present invention can be used as a cosmetic as is. Alternatively, the composition according to the present invention can be used as an element of a cosmetic. For example, the composition according to the present invention can be added to or combined with any other element to form a cosmetic.

[0370] For example, skin care products may include lotions, serums, etc. Scalp care products may include hair tonics, etc. Hair care products may include hair treatments, etc.

[0371] The present invention also, (a) at least one ceramide-type compound, (b) At least one O-acyl product derived from glucose, which can be obtained by partial or complete esterification of vitamin F with the hydroxyl group of glucose, (d) At least one second compound selected from the group consisting of (d1) polysaccharides, (d2) amino acids, their derivatives and salts, (d3) polyamino acids and their salts, (d4) proteins, and (d5) mixtures thereof. The use of at least one first compound selected from the group consisting of (c)(c1) fatty acids, (c2) aliphatic alcohols, and (c3) mixtures thereof in a composition comprising, The invention may also relate to uses for stabilizing the composition, particularly preferably for stably dissolving or dispersing (a) the ceramide-type compound and (b) the glucose-derived O-acyl product in the composition without agglomerating them.

[0372] The present invention also, (a) at least one ceramide-type compound, (b) At least one O-acyl product derived from glucose, which can be obtained by partial or complete esterification of vitamin F with the hydroxyl group of glucose, (c) At least one first compound selected from the group consisting of (c1) fatty acids, (c2) aliphatic alcohols, and (c3) mixtures thereof The use of at least one second compound selected from the group consisting of (d)(d1) polysaccharides, (d2) amino acids, their derivatives and salts, (d3) polyamino acids and their salts, (d4) proteins, and (d5) mixtures thereof, in a composition comprising: The invention may also relate to uses for stabilizing the composition, particularly preferably for stably dissolving or dispersing (a) the ceramide-type compound and (b) the glucose-derived O-acyl product in the composition without agglomerating or precipitating them.

[0373] The present invention also, (a) at least one ceramide-type compound, (b) At least one O-acyl product derived from glucose, which can be obtained by partial or complete esterification of vitamin F with the hydroxyl group of glucose. The use of at least one first compound selected from the group consisting of (c)(c1) fatty acids, (c2) aliphatic alcohols, and (c3) mixtures thereof, in a composition comprising, The invention may also relate to uses for stabilizing the composition, particularly preferably for stably dissolving or dispersing (a) the ceramide-type compound and (b) the glucose-derived O-acyl product in the composition without agglomerating or precipitating them.

[0374] The above method and composition in use according to the present invention may further comprise (e) at least one diol having at least one carbon chain having a total number of carbon atoms of five or six, and / or (f) water.

[0375] The above descriptions relating to (a) ceramide-type compounds, (b) glucose-derived O-acyl products, (c) the first compound, and (d) the second compound in the composition according to the present invention can be applied to those in the composition in the above methods and uses according to the present invention. [Examples]

[0376] The present invention will be described in more detail by reference to examples. However, these should not be construed as limiting the scope of the present invention.

[0377] (See Example 1) Preparation of glucose esters of vitamin F (primarily esterification at the 6-position) In a 500 ml three-necked flask, 17 ml of trimethylacetyl chloride is diluted in 100 ml of tetrahydrofuran. Under an inert atmosphere at 0°C, a mixture of 37.3 g of vitamin F and 19.3 ml of triethylamine, pre-dissolved in 100 ml of tetrahydrofuran, is added. The mixture is stirred for 1 hour, and the resulting salt is then filtered off to obtain the solution.

[0378] In a 2-liter three-necked flask, dissolve 96 g of D-glucose in 1.15 liters of pyridine, and add the above solution under an inert atmosphere at room temperature. Stir the mixture overnight.

[0379] The reaction medium is evaporated to dryness under vacuum to remove pyridine, the resulting paste is extracted (water / organic solvent mixture), the recovered organic phase is dried, filtered, and evaporated. A 49 g yellow paste of vitamin F ester (yield: 83% by mass) is obtained, containing 72 wt% monoester (mixture) at position 6. 1 ¹H NMR spectrum (DMSO) 200MHz: δ(ppm): 0.85;1.23;1.50;2.00;2.26;2.73;3.03;3.13;3.40;3.76;3.97;4.25;4.53;4.76;4.89;5.04;5.32;6.34. 13 ¹³C NMR spectrum (DMSO) 200MHz: δ(ppm): 13.95;22.12;24.48;25.23;26.62;28.46~29.08;31.32;33.44;63.91;69.14;70.57;72.19;72.86;92.30;127.77;129.73;172.92.

[0380] 1 H and 13 The 13C NMR spectrum (DMSO) at 200 MHz is consistent with the expected structure.

[0381] (Examples 1-15 and Comparative Examples 1-2) [Preparation] Each composition according to Examples 1-15 and Comparative Examples 1-2 was prepared by mixing the components shown in Tables 1-2. All numerical values ​​for the amounts of components in Tables 1-2 are based on the "mass%" of the raw materials.

[0382] The details of the preparation are as follows:

[0383] A pentylene glycol solution was prepared by mixing the glucose ester, ceramide, and fatty acid or aliphatic alcohol (if present) according to Reference Example 1 with pentylene glycol using a magnetic stirrer at 80°C for 15 minutes. Meanwhile, aqueous solutions were prepared by mixing the other components with water.

[0384] The pentylene glycol solution was added dropwise to the aqueous solution using a dispenser at 2000 rpm for 10 minutes while stirring at 80°C, and then cooled to room temperature (25°C) to obtain the compositions according to Examples 1-15 and Comparative Examples 1-2.

[0385] [Table 1]

[0386] [Table 2]

[0387] [evaluation] (stability) Each composition prepared in Examples 1-15 and Comparative Examples 1-2 was stored in a transparent container at room temperature (25°C) immediately after preparation. The stability of each composition was observed visually and evaluated according to the following criteria. Good: No aggregation or precipitation was observed, or only slight aggregation or precipitation was observed. Poor performance: Aggregation or precipitation was observed.

[0388] The results are shown in Tables 1 and 2.

[0389] (exterior) Each composition prepared in Examples 1-15 and Comparative Examples 1-2 was stored in a transparent container at room temperature (25°C) immediately after preparation. The appearance of each composition was observed visually. The appearance of each composition was characterized by the following symbols. P: Pearlescent F: Foam MW: Milky white

[0390] The results are shown in Tables 1 and 2.

[0391] (Microscopic observation) The compositions from Examples 1-15 and Comparative Examples 1-2 were subjected to microscopic observation at room temperature (25°C) immediately after preparation. Microscopic images of each composition from Examples 1-15 and Comparative Examples 1-2 were obtained and observed. The complexes in each microscopic image were identified and characterized by the following symbols. S: Seat A: Aggregate P: Particle

[0392] The results are shown in Tables 1 and 2.

[0393] Figure 1 shows a micrograph obtained by microscopic observation of the composition according to Example 1. It is clear that a sheet-like composite structure has been formed.

[0394] (summary) The compositions from Examples 1 to 15 were so stable that no aggregation or precipitation was observed.

[0395] The composition according to Comparative Example 1, which did not contain any fatty acids or any aliphatic alcohols, was unstable.

[0396] The composition according to Comparative Example 2, which did not contain any fatty acids or any polysaccharides (chitosan or hyaluronic acid), was unstable.

Claims

1. (a) at least one ceramide-type compound, (b) At least one O-acyl product derived from glucose, which can be obtained by partial or complete esterification of vitamin F with the hydroxyl group of glucose, (c) At least one first compound selected from the group consisting of (c1) fatty acids, (c2) aliphatic alcohols, and (c3) mixtures thereof, (d) At least one second compound selected from the group consisting of (d1) polysaccharides, (d2) amino acids, their derivatives and salts, (d3) polyamino acids and their salts, (d4) proteins, and (d5) mixtures thereof. A composition containing the following:

2. (a) The ceramide-type compound is given by the following formula (I): 【Chemistry 1】 [In the formula, - R 1 C is a linear or branched saturated or unsaturated hydrocarbon group. 1 ~C 50 Preferably C 5 ~C 50 This group may be substituted with one or more hydroxyl groups and / or optionally interrupted with one or more oxycarbonyl (-O-CO-) groups or carbonyloxy (-CO-O-) groups. - R 2 is a linear or branched, saturated or unsaturated hydrocarbon group C 1 to C 50 , preferably C 5 to C 50 , which group may be substituted by one or more hydroxyl groups, and / or may optionally be interrupted by one or more oxycarbonyl (-O-CO-) groups or carbonyloxy (-CO-O-) groups] The composition according to claim 1, as represented by [the specified figure].

3. The composition according to claim 1 or 2, wherein the amount of (a) ceramide-type compound in the composition is 0.001% to 10% by mass, preferably 0.005% to 5% by mass, and more preferably 0.01% to 1% by mass, based on the total mass of the composition.

4. (b) The O-acyl product is given by the following formula (1): 【Chemistry 2】 [In the formula, R 1 , R 2 , R 3 , R 4 and R 5 These may be the same or different, and are selected from hydrogen and a -CO-R group (wherein R is selected from saturated and unsaturated linear hydrocarbon chains containing 11 to 21 carbon atoms), however, R 1 ~R 5 At least one of the groups is not hydrogen. The composition according to any one of claims 1 to 3, which is a mixture of compounds represented by

5. (b) The composition according to any one of claims 1 to 4, wherein the O-acyl product comprises at least one ester of glucose and linoleic acid, particularly a monoester; at least one ester of glucose and oleic acid, particularly a monoester; at least one ester of glucose and palmitic acid, particularly a monoester; and at least one ester of glucose and stearic acid, particularly a monoester.

6. The composition according to any one of claims 1 to 5, wherein the amount of (b)O-acyl product in the composition is 0.01% to 15% by mass, preferably 0.05% to 10% by mass, and more preferably 0.1% to 5% by mass, based on the total mass of the composition.

7. (c1) Fatty acids, C 4 ~C 24 Preferably C 6 ~C 22 , more C 8 ~C 20 A composition according to any one of claims 1 to 6, selected from saturated or unsaturated linear or branched fatty acids.

8. (c2) The composition according to any one of claims 1 to 6, wherein the aliphatic alcohol is selected from the group consisting of cetyl alcohol, cetearyl alcohol, stearyl alcohol, behenyl alcohol, oleyl alcohol, and mixtures thereof.

9. The composition according to any one of claims 1 to 8, wherein the amount of (c) the first compound in the composition is 0.01% to 15% by mass, preferably 0.05% to 10% by mass, and more preferably 0.1% to 5% by mass, based on the total mass of the composition.

10. (d1) The composition according to any one of claims 1 to 9, wherein the polysaccharide is selected from the group consisting of chitosan, hyaluronic acid and its derivatives, polysaccharides derived from microorganisms, and mixtures thereof, preferably selected from the group consisting of chitosan, hyaluronic acid and its salts, xanthan gum, and mixtures thereof.

11. (d2) The composition according to any one of claims 1 to 10, wherein the amino acid derivative is selected from amino acid surfactants.

12. (d3) The composition according to any one of claims 1 to 11, wherein the polyamino acid is selected from polyglutamic acid.

13. (d4) The composition according to any one of claims 1 to 12, wherein the protein is of plant origin.

14. The composition according to any one of claims 1 to 13, wherein the amount of (d) the second compound in the composition is 0.001% to 15% by mass, preferably 0.005% to 10% by mass, and more preferably 0.01% to 5% by mass, based on the total mass of the composition.

15. This is a beauty method for keratin substances, A step of applying the composition according to any one of claims 1 to 14 to a keratin substance. Beauty methods, including

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