Oil-in-water emulsified cosmetic composition

Abstract

The present invention relates to an oil-in-water emulsified cosmetic composition, which contains an emulsion having (A) a sphingosine represented by formula (1), (B) an acid compound selected from inorganic acids and organic acids having 5 or less carbon atoms, and (C) a ceramide represented by formula (2); and another emulsion having (D) an oil component selected from polar oils and hydrocarbon oils, and (E) a surfactant. (wherein, R 1 represents a hydrocarbon group which may have a substituent; Y represents methylene, methine or O; X 1 , X 2 and X 3 each represent H, OH or acetoxy group; X 4 represents H, acetyl group or the like; R 2 and R 3 each represents H, OH or the like; R represents H, amidino group or the like; and a stands for 2 or 3) (wherein, R 7 represents a hydrocarbon group which may have a substituent, or H; Z represents methylene, methine or O; X 5 , X 6 and X 7 each represent H, OH or acetoxy group; X 4 represents H, acetyl group or the like; R 8 and R 9 each represent H, OH or the like; R 10 represents a hydrocarbon group which may have a substituent; and R 11 represents H or a hydrocarbon group which may have a substituent). The oil-in-water emulsified cosmetic composition contains a ceramide and is excellent in emulsion stability.

1 . An oil-in-water emulsified cosmetic composition comprising an emulsion containing (A) a sphingosine represented by the following formula (1):  
       
         
           
           
               
               
           
         
       
       wherein, R 1  represents a linear, branched or cyclic, saturated or unsaturated C 4-30  hydrocarbon group which may be substituted by a hydroxyl, carbonyl or amino group; Y represents a methylene group, a methine group or an oxygen atom; X 1 , X 2  and X 3  each independently represent a hydrogen atom, a hydroxyl group or an acetoxy group, X 4  represents a hydrogen atom, an acetyl group or a glyceryl group, or forms an oxo group together with the adjacent oxygen atom wherein, when Y represents a methine group, either X 1  or X 2  represents a hydrogen atom and the other one does not exist, and when X 4  forms an oxo group, X 3  does not exist; R 2  and R 3  each independently represent a hydrogen atom, a hydroxyl group, a hydroxymethyl group or an acetoxymethyl group; a pieces of R each independently represent a hydrogen atom or an amidino group, or a linear or branched, saturated or unsaturated hydrocarbon group having 1 to 8 carbon atoms in total and optionally having a substituent selected from hydroxyl, hydroxyalkoxy, alkoxy and acetoxy groups; a stands for 2 or 3; and a dashed line indicates a saturated bond or unsaturated bond, (B) an acid compound selected from inorganic acids and organic acids having carbon atoms of 5 or less, and (C) a ceramide represented by the following formula (2):  
       
         
           
           
               
               
           
         
       
       wherein, R 7  represents a linear, branched or cyclic, saturated or unsaturated C 4-30  hydrocarbon group which may be substituted by a hydroxyl, carbonyl or amino group, or a hydrogen atom; Z represents a methylene group, a methine group or an oxygen atom; X 5 , X 6  and X 7  each independently represent a hydrogen atom, a hydroxyl group or an acetoxy group, X 4  represents a hydrogen atom, an acetyl group or a glyceryl group, or forms an oxo group together with the adjacent oxygen atom wherein, when Z represents a methine group, either X 5  or X 6  represents a hydrogen atom and the other one does not exist, and when X 4  forms an oxo group, X 7  does not exist; R 8  and R 9  each independently represent a hydrogen atom, a hydroxyl group, a hydroxymethyl group or an acetoxymethyl group; R 10  represents a linear, branched or cyclic, saturated or unsaturated C 5-60  hydrocarbon group which may be substituted by a hydroxyl, carbonyl or amino group and may have an ether bond, ester bond or amide bond in the main chain; R 11  represents a hydrogen atom, or a linear or branched, saturated or unsaturated hydrocarbon group having 1 to 30 carbon atoms in total and optionally having a substituent selected from hydroxyl, hydroxyalkoxy, alkoxy and acetoxy groups wherein, when R 7  represents a hydrogen atom and Z represents an oxygen atom, R 11  represents a hydrocarbon group having 10 to 30 carbon atoms in total and when R 7  represents a hydrocarbon group, R 11  represents a hydrocarbon group having 1 to 8 carbon atoms in total; and a dashed line indicates a saturated bond or unsaturated bond, and another emulsion containing (D) an oil component selected from polar oils and hydrocarbon oils and (E) a surfactant.  
     
     
         2 . The oil-in-water emulsified cosmetic composition of  claim 1 , wherein Component (A) is a natural type sphingosine represented by formula (3):  
       
         
           
           
               
               
           
         
       
       wherein, R 12  represents a linear, branched or cyclic, saturated or unsaturated C 7-19  hydrocarbon group which may be substituted by a hydroxyl group; Y 1  represents a methylene or methine group; X 8 , X 9  and X 10  each independently represent a hydrogen atom, a hydroxyl group or an acetoxy group, X 11  represents a hydrogen atom or forms an oxo group together with the adjacent oxygen atom wherein, when Y 1  represents a methine group, either X 8  or X 9  represents a hydrogen atom and the other one does not exist, and when X 11  forms an oxo group, X 10  does not exist; R 13  represents a hydroxymethyl or acetoxymethyl group; a pieces of R 1  each independently represent a hydrogen atom or an amidino group, or a linear or branched, saturated or unsaturated hydrocarbon group having 1 to 4 carbon atoms in total and optionally having a substituent selected from hydroxyl, hydroxyalkoxy, alkoxy and acetoxy groups; a stands for 2 or 3; and a dashed line indicates a saturated bond or unsaturated bond; or a pseudo type sphingosine represented by formula (4):  
       
         
           
           
               
               
           
         
       
       wherein, R 17  represents a linear, branched or cyclic, saturated or unsaturated C 10-22  hydrocarbon group which may be substituted by a hydroxyl group; X 4  represents a hydrogen atom, an acetyl group or a glyceryl group; a pieces of R 2  each independently represent a hydrogen atom or an amidino group, or a linear or branched, saturated or unsaturated hydrocarbon group having 1 to 8 carbon atoms in total and optionally having a substituent selected from hydroxyl, hydroxyalkoxy, alkoxy and acetoxy groups, and a stands for 2 or 3.  
     
     
         3 . The oil-in-water emulsified cosmetic composition of  claim 1 , wherein Component (B) is phosphoric acid, hydrochloric acid, succinic acid, citric acid, lactic acid, glutamic acid or aspartic acid.  
     
     
         4 . The oil-in-water emulsified cosmetic composition of  claim 1 , wherein Component (C) is a natural type ceramide represented by formula (5):  
       
         
           
           
               
               
           
         
       
       wherein, R 21  represents a linear, branched or cyclic, saturated or unsaturated C 7-19  hydrocarbon group which may be substituted by a hydroxyl group; Z 1  represents a methylene or methine group; X 12 , X 13  and X 14  each independently represent a hydrogen atom, a hydroxyl group or an acetoxy group; X 15  represents a hydrogen atom or forms an oxo group together with the adjacent oxygen atom wherein, when Z 1  represents a methine group, either X 12  or X 13  represents a hydrogen atom and the other one does not exist, and when X 15  represents an oxo group, X 14  does not exist; R 22  represents a hydroxymethyl group or an acetoxymethyl group; R 23  represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms in total; R 24  represents a linear, branched or cyclic, saturated or unsaturated C 5-30  hydrocarbon group which may be substituted by a hydroxyl group, or the hydrocarbon group having, to the ω position thereof, a linear or branched, saturated or unsaturated C 8-22  fatty acid, which may be substituted by a hydroxyl group, ester-bound; and a dashed line indicates a saturated bond or unsaturated bond; or a pseudo type ceramide represented by formula (6)  
       
         
           
           
               
               
           
         
       
       wherein, R 25  represents a linear, branched or cyclic, saturated or unsaturated C 10-22  hydrocarbon group which may be substituted by a hydroxyl group, or a hydrogen atom; X 16  represents a hydrogen atom, an acetyl group or a glyceryl group; R 26  represents a linear, branched or cyclic, saturated or unsaturated C 5-22  hydrocarbon group which may be substituted by a hydroxyl or amino group, or the hydrocarbon group having, to the ω position thereof, a linear or branched, saturated or unsaturated C 8-22  fatty acid, which may be substituted by a hydroxyl group, ester-bound; and R 27  represents a hydrogen atom or an alkyl group having 1 to 30 carbon atoms in total and optionally being substituted by a hydroxyl, hydroxyalkoxy, alkoxy or acetoxy group.  
     
     
         5 . The oil-in-water emulsified cosmetic composition of  claim 1 , wherein the contents of Component (A), Component (B) and Component (C) are from 0.001 to 10 weight %, from 0.001 to 10 weight %, and from 0.001 to 20 weight %, respectively.  
     
     
         6 . The oil-in-water emulsified cosmetic composition of  claim 1 , wherein a content ratio of Components (A) and (B) to Component (C), that is, ((A)+(B))/(C), based on weight % is 0.0001 or greater.  
     
     
         7 . A preparation process of the oil-in-water emulsified cosmetic composition as claimed in  claim 1 , which comprises mixing an emulsion obtained by emulsifying (C) a ceramide represented by formula (2) with (A) a sphingosine represented by formula (1) and (B) an acid compound selected from inorganic acids and organic acids having 5 or less carbon atoms, and another emulsion obtained by emulsifying (D) an oil component selected from polar oils and hydrocarbon oils with (E) a surfactant.