Salicylic acid derivative as a stabilizer for an oil-in-water emulsion

{
  "publication_number": "US5667789A",
  "country": "US",
  "kind": "A",
  "title": "Salicylic acid derivative as a stabilizer for an oil-in-water emulsion",
  "abstract": "The invention relates to the use of a salicylic acid derivative salified with a base, as a stabilizer for an oil-in-water emulsion. This salified derivative has the same properties as its acidic homologue, while at the same time having a less irritating nature. This salified derivative is, in particular, an n-alkanoyl-5-salicylic acid salified with an amphoteric base such as lysine or arginine. The present compositions are more especially intended for the cosmetic and dermatological fields.",
  "claims": [
    "1. A method of stabilizing a dispersion of an oily phase in an aqueous phase, comprising mixing said oily phase and said aqueous phase with a salicylic acid derivative salified with a base, without adding any emulsifying agent, wherein said salicylic acid derivative has the following formula (I); ##STR3## in which; R represents a saturated, linear or branched aliphatic, alkoxy, alkanoyl, or alkyl carboxy group, each group having 2 to 22 carbon atoms and each optionally substituted with at least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxyl, hydroxyl esterified with a carboxylic acid having 1 to 6 carbon atoms, carboxyl, and carboxyl esterified with a lower alcohol having 1 to 6 carbon atoms; or an unsaturated, linear or branched alkenyl, alkenyloxy, alkenoyloxy, alkenoyl, or alkenyl carboxy group having one or more conjugated or non-conjugated double bonds, each group having 2 to 22 carbon atoms and each group optionally substituted with at least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxyl esterified with an carboxylic acid having 1 to 6 carbon atoms, carboxyl, and carboxyl esterified with a lower alcohol having 1 to 6 carbon atoms; R' represents a hydroxyl group or an ester function of formula: ##STR4## where R 1 is saturated or unsaturated aliphatic group having 1 to 18 carbon atoms.",
    "2. The method of claim 1, wherein R is an alkyl or alkoxy radical having 4 to 11 carbon atoms.",
    "3. The method of claim 1, wherein said salicylic acid derivative is n-octanoyl-5-salicylic acid.",
    "4. The method of claim 1, wherein said base is an organic base.",
    "5. The method of claim 1, wherein said base is an amphoteric base.",
    "6. A method of stabilizing a dispersion of an oily phase in an aqueous phase comprising mixing said oily phase and said aqueous phase with a salicylic acid derivative salified with a base, without adding any emulsifying agent; wherein said base is an amino acid, and wherein said salicylic acid derivative has the following formula (I); ##STR5## in which; R represents a saturated, linear or branched aliphatic, alkoxy, alkanoyloxy, alkanoly, or alkyl carboxy group, each group having 2 to 22 carbon atoms and each groups optionally substituted with at least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxyl, hydroxyl esterified with a carboxylic acid having 1 to 6 carbon atoms, carboxyl, and carboxyl esterified with a lower alcohol having 1 to 6 carbon atoms; or an unsaturated, linear or branches alkenyl, alkenyloxy, alkenoyloxy, alkenoyl, or alkenyl carboxy group having one or more conjugated or non-conjugated double bonds, each group having 2 to 22 carbon atoms and each group optionally substituted with at least one substituted selected from the group consisting of halogen, trifluoromethyl, hydroxyl, hydroxyl esterified with an carboxylic acid having 1 to 6 carbon atoms, carboxyl, and carboxyl esterified with a lower alcohol having 1 to 6 carbon atoms; R' represents a hydroxyl group or an ester function of formula; ##STR6## where R 1 is a saturated or unsaturated aliphatic group having 1 to 18 carbon atoms.",
    "7. A of stabilizing a dispersion of an oily phase in an aqueous phase comprising mixing said oily phase and said aqueous phase with a salicylic acid derivative salified with a base, without adding any emulsifying agent; and said base is selected from the group consisting of arginine and lysine, and wherein said salicylic acid derivative has the following formula (I); ##STR7## in which; R represents a saturated, linear or branched aliphatic, alkoxy, alkanoyloxy, alkanoyl, or alkyl carboxy group, each group having 2 to 22 carbon atoms and each group optionally substituted with at least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxyl, hydroxyl esterified with a carboxylic acid having 1 to 6 carbon atoms, carboxyl, and carboxyl esterified with a lower alcohol having 1 to 6 carbon atoms; or unsaturated, linear or branched alkenyl, alkenyloxy, alkenoyloxy, alkenoyl, or alkenyl carboxy group having one or more conjugated or non-conjugated double bonds, each group having 2 to 22 carbon atoms and each group optionally substituted with al least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxyl, hydroxyl, esterified with an carboxylic acid having 1 to 6 carbon atoms, carboxyl, and carboxyl esterified with a lower alcohol having 1 to 6 carbon atoms; R' represents a hydroxyl group or an ester function of formula: ##STR8## where R 1 is a saturated or unsaturated aliphatic group having 1 to 18 carbon atoms.",
    "8. A cosmetic and/or dermatological emulsion, free of emulsifying agent comprising: (a) an oil phase; (b) an aqueous phase; and (c) at least one salicylic acid derivative of formula (I) below, salified with a base: ##STR9## in which: R represents a saturated linear or branched aliphatic, alkoxy, alkanoyloxy, alkanoyl, or alkyl carboxy group, each group having 2 to 22 carbon atoms and each group optionally substituted with at least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxyl, hydroxyl esterified with a carboxylic acid having 1 to 6 carbon atoms, carboxyl, and carboxyl esterified with a lower alcohol having 1 to 6 carbon atoms; or an unsaturated, linear or branched alkenyl, alkenyloxy, alkenoyloxy, alkenoyl, or alkenyl carboxy group having one or more conjugated or non-conjugated double bonds, each group having 2 to 22 carbon atoms and each group optionally substituted with at least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxyl, hydroxyl esterified with a carboxylic acid having 1 to 6 carbon atoms, carboxyl, and carboxyl esterified with a lower alcohol having 1 to 6 carbon atoms; R' represents a hydroxyl group or an ester function of formula: ##STR10## wherein R 1 is a saturated or unsaturated aliphatic group having 1 to 18 carbon atoms, wherein at least a portion of said salicylic acid derivative is at the oil-water interface.",
    "9. The emulsion of claim 8, wherein R is an alkyl or alkoxy radical having 4 to 11 carbon atoms.",
    "10. The emulsion of claim 8, wherein said salicylic acid derivative is n-octanoyl-5-salicylic acid.",
    "11. The emulsion of claim 8, wherein said base is an organic base.",
    "12. The emulsion of claim 8, wherein said base is an amphoteric base.",
    "13. A cosmetic and/or dermatological emulsion, comprising: (a) an oil phase; (b) an aqueous phase; and (c) at least one salicylic acid derivative of formula (I) below, salified with a base: ##STR11## in which: R represents a saturated, linear or branched aliphatic, alkoxy, alkanoyloxy, alkanoyl, or alkyl carboxy group, each group having 2 to 22 carbon atoms and each group optionally substituted with at least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxyl, hydroxyl esterified with a carboxylic acid having 1 to 6 carbon atoms, carboxy1, and carboxy1 esterified with a lower alcohol having 1 to 6 carbon atoms; or an unsaturated, linear, or branched alkenyl, alkenyloxy, alkenoyloxy, alkenoyl, or alkenyl carboxy group having one or more conjugated or non-conjugated double bonds, each group having 2 to 22 carbon atoms and each group optionally substituted with at least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxyl, hydroxyl esterified with a carboxylic acid having 1 to 6 carbon atoms, carboxyl, and carboxy1 esterified with a lower alcohol having 1 to 6 carbon atoms; R' represents a hydroxyl group or an ester function of formula: ##STR12## wherein R 1 is a saturated or unsaturated aliphatic group having 1 to 18 carbon atoms, wherein at least a portion of said salicylic acid derivative is at the oil-water interface; and said base is an amino acid without an emulsifying agent added there to.",
    "14. A cosmetic and/or dermatological emulsion, comprising: (a) an oil phase; (b) an aqueous phase; and (c) at least one salicylic acid derivative of formula (I) below, salified with a base: ##STR13## in which: R represents a saturated, linear or branched aliphatic, alkoxy, alkanoyloxy, alkanoyl, or alkyl carboxy group, each group having 2 to 22 carbon atoms and each group optionally substituted with at least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxyl, hydroxyl esterified with a carboxylic acid having 1 to 6 carbon atoms, carboxyl, and carboxyl esterified with a lower alcohol having 1 to 6 carbon atoms; or an unsaturated, linear, or branched alkenyl, alkenyloxy, alkenoyloxy, alkenoyl, or alkenyl carboxy group having one or more conjugated or non-conjugated double bonds, each group having 2 to 22 carbon atoms and each group optionally substituted with at least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxyl, hydroxyl esterified with a carboxylic acid having 1 to 6 carbon atoms, carboxy1, and carboxyl esterified with a lower alcohol having 1 to 6 carbon atoms; R' represents a hydroxyl group or an ester function of formula: ##STR14## wherein R 1 is a saturated or unsaturated aliphatic group having 1 to 18 carbon atoms, wherein at least a portion of said salicylic acid derivative is at the oil-water interface; and said base is selected from the group consisting of arginine and lysine without an emulsifying agent added there to.",
    "15. The emulsion of claim 8, wherein said salicylic acid derivative is present in an amount of from 0.5% to 10% by weight, based on the total weight of the emulsion.",
    "16. The emulsion of claim 8, which comprises at least one polar oil.",
    "17. The emulsion of claim 16, wherein said oil is present in an amount of from 10% to 70% by weight, based on the total weight of the emulsion.",
    "18. The emulsion of claim 8, further comprising an adjuvant selected from the group consisting of ceramides, pseudoceramides, glycoceramides, and essential fatty acids.",
    "19. The emulsion of claim 8, further comprising at least one gelling agent.",
    "20. A cosmetic and/or dermatological emulsion, comprising: (a) an oil phase; (b) an aqueous phase; and (c) at least one salicylic acid derivative of formula (I) below, salified with lysine or arginine: ##STR15## in which: R represents a saturated, linear or branched aliphatic, alkoxy, alkanoyloxy, alkanoyl, or alkyl carboxy group, each group having 2 to 22 carbon atoms and each group optionally substituted with at least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxyl, hydroxyl esterified with a carboxylic acid having 1 to 6 carbon atoms, carboxyl, and carboxyl esterified with a lower alcohol having 1 to 6 carbon atoms; or an unsaturated, linear or branched alkenyl, alkenyloxy, alkenoyloxy, alkenoyl, or alkenyl carboxy group having one or more conjugated or non-conjugated double bonds, each group having 2 to 22 carbon atoms and each group optionally substituted with at least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxyl, hydroxyl esterified with a carboxylic acid having 1 to 6 carbon atoms, carboxyl, and carboxyl esterified with a lower alcohol having 1 to 6 carbon atoms; R' represents a hydroxyl group or an ester function of formula: ##STR16## wherein R 1 is a saturated or unsaturated aliphatic group having 1 to 18 carbon atoms; and at least a portion of said salicylic acid derivative is at the oil-water interface without an emulsifying agent added there to.",
    "21. A method for treating or combating acne, greasy skin, the ageing, pigmentation and combinations thereof of the skin, comprising applying an emulsion to the skin, said emulsion comprising: (a) an oil phase; (b) an aqueous phase; and (c) at least one salicylic acid derivative of formula (I) below, salified with a base: ##STR17## in which: R represents a saturated, linear or branched aliphatic, alkoxy, alkanoyloxy, alkanoyl, or alkyl carboxy group, each group having 2 to 22 carbon atoms and each group optionally substituted with at least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxyl, hydroxyl esterified with a carboxylic acid having 1 to 6 carbon atoms, carboxyl, and carboxyl esterified with a lower alcohol having 1 to 6 carbon atoms; or an unsaturated, linear or branched alkenyl, alkenyloxy, alkenoyloxy, alkenoyl, or alkenyl carboxy group having one or more conjugated or non-conjugated double bonds, each group having 2 to 22 carbon atoms and each group optionally substituted with at least one substituent selected from the group consisting of halogen, trifluoromethyl, hydroxyl, hydroxyl esterified with a carboxylic acid having 1 to 6 carbon atoms, carboxyl, and carboxyl esterified with a lower alcohol having 1 to 6 carbon atoms; R' represents a hydroxyl group or an ester function of formula: ##STR18## wherein R 1 is a saturated or unsaturated aliphatic group having 1 to 18 carbon atoms, wherein at least a portion of said salicylic acid derivative is at the oil-water interface without an emulsifying agent added there to.",
    "22. The method of claim 1 wherein said dispersion further comprises at least one gelling agent selected from the group consisting of clays, polysaccharide gums (xanthan), carboxyvinyl polymers and carbomers.",
    "23. The method of claim 1 wherein said dispersion further comprises at least one lipophilic or hydrophilic active agent selected from the group consisting of moisturizing or cicatrizing agents, β-hydroxy acids, α-hydroxy acids, hydrophilic or lipophilic screening agents and dermatological active agents."
  ],
  "cpc": [
    "A61K 8/368",
    "A61K 2800/52",
    "A61K 8/06",
    "A61K 8/062",
    "A61K 8/44",
    "A61P 17/00",
    "A61Q 19/00",
    "C07C 65/10"
  ],
  "assignees": [
    "OREAL"
  ],
  "filing_date": "1995-11-03",
  "publication_date": "1997-09-16",
  "grant_date": "1997-09-16",
  "priority_date": "1994-11-03",
  "application_number": "US-55293495-A",
  "family_id": "9468461",
  "citations": [
    "EP0378936A2",
    "EP0570230A1",
    "EP0585170A1",
    "EP0616799A1",
    "FR2607498A1",
    "GB2174906A",
    "US5001156A",
    "US5137923A",
    "US5411742A"
  ]
}