Nanoemulsions comprising at least one amphiphilic lipid, at least one oil, and at least one cationic polymer, and uses thereof

• US 20010028887A1
• Filed: 01/22/2001
• Published: 10/11/2001
• Est. Priority Date: 01/21/2000
• Status: Abandoned Application

• Current Assignee: L'Oreal SA
• Original Assignee: L'Oreal SA
• Inventors: Decoster, Sandrine, Cazin, Benedicte, Douin, Veronique
• Application Number:
  US09/765,675
• Publication Number:
  US 20010028887A1
• Time in Patent Office: Days
• US Class Current: 424/401
• CPC Class Codes: A61K 2800/21 Emulsions characterized by droplet sizes below 1 micron
• CPC Class Codes: A61K 2800/413 Nanosized, i.e. having sizes below 100 nm
• CPC Class Codes: A61K 2800/5426 cationic
• CPC Class Codes: A61K 8/06 Emulsions
• CPC Class Codes: A61K 8/062 Oil-in-water emulsions
• CPC Class Codes: A61K 8/416 Quaternary ammonium compounds A61K8/35 takes precedence
• CPC Class Codes: A61K 8/731 Cellulose; Quaternized cellulose derivatives
• CPC Class Codes: A61K 8/737 Galactomannans, e.g. guar; Derivatives thereof
• CPC Class Codes: A61K 8/86 Polyethers
• CPC Class Codes: A61K 8/898 containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
• CPC Class Codes: A61K 8/922 of vegetable origin
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin
• CPC Class Codes: A61Q 5/00 Preparations for care of the hair
• CPC Class Codes: B82Y 5/00 Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery

Abstract

Oil-in-water nanoemulsions comprising oil globules with an average size of less than 150 nm and comprising at least one oil, at least one amphiphilc lipid, and at least one cationic polymer comprising at least one hydrophobic block and at least one hydrophilic block. Processes comprising such oil-in-water nanoemulsions.

Claims

1. An oil-in-water nanoemulsion comprising oil globules with an average size of less than 150 nm comprising at least one oil, at least one amphiphilc lipid, and at least one cationic polymer comprising at least one hydrophobic block and at least one hydrophilic block.

2. A nanoemulsion according to

claim 1

, wherein said at least one oil and said at least one amphiphilic lipid are present in amounts wherein the weight ratio of the amount of said at least one oil to the amount of said at least one amphiphilic lipid ranges from 1 :

1 to 10;

1.

3. A nanoemulsion according to

claim 2

, wherein said weight ratio ranges from 1.2:

1 to 6;

1.

4. A nanoemulsion according to

claim 1

, wherein said oil globules have an -average size ranging from 30 nm to 100 nm.

5. A nanoemulsion according to

claim 1

, wherein said at least one cationic polymer is chosen from water-soluble cationic polymers and water-dispersible cationic polymers.

6. A nanoemulsion according to

claim 1

, wherein said at least one cationic polymer comprises at least two hydrophobic blocks.

7. A nanoemulsion according to

claim 1

, wherein said at least one hydrophobic block is chosen from fatty chains comprising from 6 to 30 carbon atoms, divalent aliphatic groups, divalent cycloaliphatic groups and divalent aromatic groups.

8. A nanoemulsion according to

claim 7

, wherein said fatty chains comprising from 6 to 30 carbon atoms are chosen from alkyl chains, arylalkyl chains, alkylaryl chains and alkenyl chains.

9. A nanoemulsion according to

claim 1

, wherein said at least one hydrophilic block is chosen from polyethylene oxides, polysaccharides, polyamides, and polyesters.

10. A nanoemulsion according to

claim 9

, wherein said polyamides are chosen from polyacrylamides.

11. A nanoemulsion according to

claim 1

, wherein said at least one hydrophobic block and said at least one hydrophilic block are bonded with at least one linking group chosen from ester, ether, urea, amide and urethane linkers.

12. A nanoemulsion according to

claim 1

, wherein said at least one hydrophilic block and said at least one hydrophobic block are present in amounts wherein the weight ratio of the amount of said at least one hydrophilic block to the amount of said at least one hydrophobic block ranges from 10:

1 to 1000;

1.

13. A nanoemulsion according to

claim 1

, wherein said at least one cationic polymer is chosen from polyacrylates comprising at least one amine side group and quaternized cellulose derivatives.

14. A nanoemulsion according to

claim 1

, wherein said at least one cationic polymer is present in an amount ranging from 0.1% to 20% by weight relative to the total weight of the final composition.

15. A nanoemulsion according to

claim 14

, wherein said at least one cationic polymer is present in an amount ranging from 0.5% to 10% by relative to the total weight of the final composition weight.

16. A nanoemulsion according to

claim 15

, wherein said at least one cationic polymer is present in an amount ranging from 1% to 5% by weight relative to the total weight of the final composition.

17. A nanoemulsion according to

claim 1

, wherein said at least one amphiphilic lipid is chosen from nonionic amphiphilic lipids and anionic amphiphilic lipids.

18. A nanoemulsion according to

claim 17

, wherein said nonionic amphiphilic lipids are chosen from:

1/—

silicone surfactants,

2/—

nonionic amphiphilic lipids that are fluid at a temperature of less than or equal to 45°

C. chosen from esters formed from (i) at least one polyol chosen from polyethylene glycol comprising from 1 to 60 ethylene oxide units, sorbitan, glycerol comprising from 2 to 30 ethylene oxide units, polyglycerols comprising from 2 to 15 glycerol units, and (ii) at least one fatty acid comprising at least one alkyl chain chosen from saturated and unsaturated, linear and branched C₁-C₂₂ alkyl chains,

3/—

mixed esters derived from (i) at least one fatty acid, at least one carboxylic acid, and glycerol, and mixed esters derived from (ii) at least one fatty alcohol, at least one carboxylic acid, and glycerol, wherein said at least one carboxylic acid is chosen from α

-hydroxy acids and succinic acid,

4/—

fatty acid esters of sugars and fatty alcohol ethers of sugars,

5/—

surfactants that are solid at a temperature of less than or equal to 45°

C. chosen from fatty esters of glycerol, fatty esters of sorbitan, oxyethylenated fatty esters of sorbitan, ethoxylated fatty ethers, and ethoxylated fatty esters, and

6/—

block copolymers of ethylene oxide (A) and of propylene oxide (B).

19. A nanoemulsion according to

claim 17

, wherein said nonionic amphiphilic lipids are chosen from:

polyethylene glycol isostearate (8 mol of ethylene oxide),

diglyceryl isostearate,

polyglyceryl monolaurate, polyglyceryl monostearate, and polyglyceryl distearate which comprise 10 glycerol units,

sorbitan oleate, and

sorbitan isostearate.

20. A nanoemulsion according to

claim 17

, wherein said anionic amphiphilic lipids are chosen from:

alkyl ether citrates,

alkoxylated alkenyl succinates,

alkoxylated glucose alkenyl succinates, and

alkoxylated methylglucose alkenyl succinates.

21. A nanoemulsion according to

claim 1

, wherein said at least one amphiphilic lipid is present in an amount ranging from 0.2% to 15% by weight relative to the total weight of the nanoemulsion.

22. A nanoemulsion according to

claim 21

, wherein said at least one amphiphilic lipid is present in an amount ranging from 1% to 8% by weight relative to the total weight of the nanoemulsion.

23. A nanoemulsion according to

claim 1

further comprising at least one ionic amphiphilic lipid chosen from cationic amphiphilic lipids and anionic amphiphilic lipids chosen from:

alkaline salts of dicetyl phosphate and of dimyristyl phosphate;

alkaline salts of cholesteryl sulfate;

alkaline salts of cholesteryl phosphate;

lipoamino acids and salts thereof;

sodium salts of phosphatidic acid;

phospholipids; and

alkylsulfonic derivatives of formula;

in which R, which may be identical or different in embodiments wherein more than one of said alkylsulfonic derivative is used, is chosen from C₁₆-C₂₂ alkyl groups, and M is chosen from alkali metals and alkaline-earth metals.

24. A nanoemulsion according to

claim 23

, wherein said lipoamino acids and salts thereof are chosen from monosodium and disodium acylglutamates.

25. A nanoemulsion according to

claim 24

, wherein said lipoamino acids and salts thereof are chosen from the disodium salt of N-stearoyl-L-glutamic acid.

26. A nanoemulsion according to

claim 23

, wherein said R is chosen from C₁₆H₃₃ and C₁₈H₃₇ groups.

27. A nanoemulsion according to

claim 23

, wherein said M is sodium.

28. A nanoemulsion according to

claim 23

, wherein said at least one ionic amphiphilic lipid chosen from cationic amphiphilic lipids and anionic amphiphilic lipids is present in said nanoemulsion in an amount ranging from 0.01% to 10% by weight relative to the total weight of the nanoemulsion.

29. A nanoemulsion according to

claim 28

, wherein said at least one ionic amphiphilic lipid chosen from cationic amphiphilic lipids and anionic amphiphilic lipids is present in said nanoemulsion in an amount ranging from 0.2% to 5% by weight relative to 1.10 the total weight of the nanoemulsion.

30. A nanoemulsion according to

claim 23

, wherein said cationic amphiphilic lipids are chosen from:

A) quaternary ammonium salts of formula (IV);

in which;

R₁, R₂, R₃, and R₄, which may be identical or different, are each chosen from;

linear and branched aliphatic groups comprising from 1 to 30 carbon atoms and optionally comprising atoms chosen from hetero and halogen atoms, and

aromatic groups, and

X is an anion chosen from halides, phosphates, acetates, lactates, (C₂-C₆)alkyl sulfates, alkyl sulfonates, and alkylaryl sulfonates;

B) quaternary ammonium salts of imidazolinium of formula (V);

in which;

R₅ is chosen from alkenyl and alkyl groups comprising from 8 to 30 carbon atoms,

R6 is chosen from a hydrogen atom, C₁-C₄ alkyl groups, and alkenyl and alkyl groups comprising from 8 to 30 carbon atoms,

R₇ is chosen from C₁-C₄ alkyl groups,

R₈ is chosen from a hydrogen atom and C₁-C₄ alkyl groups, and

X⁻

is an anion chosen from halides, phosphates, acetates, lactates, alkyl sulfates, alkyl sulfonates, and alkylaryl sulfonates;

C) diquaternary ammonium salts of formula (VI);

in which;

R₉ is chosen from aliphatic groups comprising from 16 to 30 carbon atoms,

R₁₀, R₁₁, R₁₂, R₁₃ and R₁₄, which may be identical or different, are each chosen from a hydrogen atom and alkyl groups comprising from 1 to 4 carbon atoms, and

X⁻

is an anion chosen from halides, acetates, phosphates, nitrates and methyl sulfates; and

D) quaternary ammonium salts comprising at least one ester function chosen from said quaternary ammonium salts of formula (VII);

in which;

R₁₅ is chosen from C₁-C₆ alkyl groups, C₁-C₆ hydroxyalkyl groups and C₁-C₆ dihydroxyalkyl groups;

R₁₆ is chosen from;

acyl groups of the following formula;

wherein R₁₉ is defined below,

linear and branched, saturated and unsaturated, C₁-C₂₂ hydrocarbon-based 1%) groups, and

a hydrogen atom;

R₁₈ is chosen from;

acyl groups of the following formula;

wherein R₂₁ is defined below,

linear and branched, saturated and unsaturated, C₁-C₆ hydrocarbon-based groups, and

a hydrogen atom;

R₁₇, R₁₉ and R₂₁, which may be identical or different, are each chosen from linear and branched, saturated and unsaturated, C₇-C₂₁ hydrocarbon-based groups;

n, p and r, which may be identical or different, are each chosen from integers ranging from 2 to 6;

y is chosen from integers ranging from 1 to 10;

x and z, which may be identical or different, are each chosen from integers ranging from 0 to 10;

X⁻

is chosen from simple and complex, organic and inorganic anions; and

provided that the sum x+y+z is from 1 to 15, and that when x is 0, then R₁₆ is chosen from linear and branched, saturated and unsaturated, C₁-C₂₂ hydrocarbon-based groups, and that when z is 0, then R₁₈ is chosen from linear and branched, saturated and unsaturated, C₁-C₆ hydrocarbon-based groups.

31. A nanoemulsion according to

claim 30

, wherein said aromatic groups are chosen from aryl and alkylaryl groups.

32. A nanoemulsion according to

claim 30

, wherein said hetero atoms are chosen from oxygen, nitrogen, and sulfur.

33. A nanoemulsion according to

claim 30

, wherein said aliphatic groups are chosen from alkyl, alkoxy, polyoxy(C₂-C₆)alkylene, alkylamide, (C₁₂-C₂₂)alkylamido(C₂-C₆)alkyl, (C₁₂-C₂₂)alkylacetate, and hydroxyalkyl groups comprising from 1 to 30 carbon atoms.

34. A nanoemulsion according to

claim 30

, wherein said alkenyl and alkyl groups comprising from 8 to 30 carbon atoms are chosen from groups derived from tallow fatty acid.

35. A nanoemulsion according to

claim 30

, wherein said diquaternary ammonium salts of formula (VI) comprise propane tallow diammonium dichloride.

36. A nanoemulsion according to

claim 30

, wherein said R₁₅ alkyl groups are chosen from linear and branched alkyl groups.

37. A nanoemulsion according to

claim 36

, wherein said R₁₅ alkyl groups are chosen from linear alkyl groups.

38. A nanoemulsion according to

claim 37

, wherein said R₁₅ alkyl groups are chosen from methyl, ethyl, hydroxyethyl and dihydroxypropyl groups.

39. A nanoemulsion according to

claim 38

, wherein said R₁₅ alkyl groups are chosen from methyl and ethyl groups.

40. A nanoemulsion according to

claim 30

, wherein said sum of x+y+z ranges from 1 to 10.

41. A nanoemulsion according to

claim 30

, wherein when said R₁₆ is chosen from linear and branched, saturated and unsaturated, C₁-C₂₂ hydrocarbon-based groups, R₁₆ is chosen from hydrocarbon-based groups comprising from 12 to 22 carbon atoms, and hydrocarbon-based groups comprising from 1 to 3 carbon atoms.

42. A nanoemulsion according to

claim 30

, wherein when said R₁₈ is chosen from linear and branched, saturated and unsaturated, C₁-C₆ hydrocarbon-based groups, R₁₈ comprises from 1 to 3 carbon atoms.

43. A nanoemulsion according to

claim 42

, wherein said R₁₈ comprises from 1 to 3 carbon atoms.

44. A nanoemulsion according to

claim 30

, wherein said R₁₇, R₁₉ and R₂₁, which may be identical or different, are each chosen from linear and branched, saturated and unsaturated C₁₁-C₂₁ hydrocarbon-based groups.

45. A nanoemulsion according to

claim 44

, wherein said R₁₇, R₁₉ and R₂₁, which may be identical or different, are each chosen from linear and branched, saturated and unsaturated, C₁-C₂₁ alkyl and alkenyl groups.

46. A nanoemulsion according to

claim 30

, wherein said x and z, which may be identical or different, are each chosen from 0 or 1.

47. A nanoemulsion according to

claim 30

, wherein said y is equal to 1.

48. A nanoemulsion according to

claim 30

, wherein said n, p and r, which may be identical or different, are each chosen from 2 and 3.

49. A nanoemulsion according to

claim 48

, wherein said n, p and r, which may be identical or different, are each equal to 2.

50. A nanoemulsion according to

claim 30

, wherein said anion is chosen from halides and alkyl sulfates.

51. A nanoemulsion according to

claim 50

, wherein said halides are chosen from chloride, bromide, and iodide.

52. A nanoemulsion according to

claim 50

, wherein said alkyl sulfates are chosen from methyl sulfate.

53. A nanoemulsion according to

claim 30

, wherein said anion is chosen from methanesulfonate, phosphate, nitrate, and tosylate.

54. A nanoemulsion according to

claim 30

, wherein said anion is chosen from anions derived from organic acids.

55. A nanoemulsion according to

claim 30

, wherein said cationic amphiphilic lipids of formula (IV) are chosen from tetraalkyammonium chlorides.

56. A nanoemulsion according to

claim 55

, wherein said tetraalkyammonium chlorides are chosen from dialkyldimethylammonium chlorides, and alkyltrimethylammonium chlorides, wherein said alkyl portion comprises from 12 to 22 carbon atoms.

57. A nanoemulsion according to

claim 30

, wherein said cationic amphiphilic lipids of formula (IV) are chosen from behenyltrimethylammonium chloride, distearyldimethylammonium chloride, cetyltrimethylammonium chloride, benzyldimethylstearylammonium chloride and stearamidopropyldimethyl(myristyl acetate)ammonium chloride.

58. A nanoemulsion according to

claim 30

, wherein said cationic amphiphilic lipids of formula (IV) are chosen from behenyltrimethylammonium salts and stearamidopropyldimethyl(myristyl acetate)ammonium salts.

59. A nanoemulsion according to

claim 1

, wherein said at least one oil is chosen from plant oils, animal oils, synthetic oils, mineral oils, halogenated oils, esters of a mineral acid and of an alcohol, liquid carboxylic acid esters and silicones.

60. A nanoemulsion according to

claim 1

, wherein said at least one oil is present in an amount ranging from 2% to 40% by weight relative to the total weight of the nanoemulsion.

61. A nanoemulsion according to

claim 60

, wherein said at least one oil is present in an amount ranging from 4% to 30% by weight relative to the total weight of the nanoemulsion.

62. A nanoemulsion according to

claim 1

further comprising at least one active agent chosen from water-soluble, water-dispersible, and liposoluble cosmetic active agents and water-soluble, water-dispersible, and liposoluble dermopharmaceutical active agents.

63. A nanoemulsion according to

claim 1

, wherein said nanoemulsion has a turbidity ranging from 60 NTU to 600 NTU.

64. A nanoemulsion according to

claim 1

further comprising at least one aminosilicone.

65. A nanoemulsion according to

claim 64

, wherein said at least one aminosilicone is present in an amount ranging from 0.05% to 10% by weight relative to the total weight of the nanoemulsion.

66. A nanoemulsion according to

claim 65

, wherein said at least one aminosilicone is present in an amount ranging from 0.1% to 5% by weight relative to the total weight of the nanoemulsion.

67. A nanoemulsion according to

claim 66

, wherein said at least one aminosilicone is present in an amount ranging from 0.3% to 3% by weight relative to the total weight of the nanoemulsion.

83. A nanoemulsion according to

claim 54

, wherein said anions derived from organic acids are chosen from acetate and lactate.

68. A composition for topical use chosen from cosmetic compositions and dermopharmaceutical compositions, wherein said composition for topical use comprises a nanoemulsion comprising oil globules with an average size of less than 150 nm comprising at least one oil, at least one amphiphilc lipid, and at least one cationic polymer comprising at least one hydrophobic block and at least one hydrophilic block.

69. A composition for caring for a keratin material chosen from body skin, facial skin, mucous membranes, the scalp, the hair, the nails, the eyelashes, and the eyebrows comprising a nanoemulsion comprising oil globules with an average size of less than 150 nm comprising at least one oil, at least one amphiphilc lipid, and at least one cationic polymer comprising at least one hydrophobic block and at least one hydrophilic block.

70. A composition for washing a keratin material chosen from body skin, facial skin, mucous membranes, the scalp, the hair, the nails, the eyelashes, and the eyebrows comprising a nanoemulsion comprising oil globules with an average size of less than 150 nm comprising at least one oil, at least one amphiphilc lipid, and at least one cationic polymer comprising at least one hydrophobic block and at least one hydrophilic block.

71. A cosmetic make up composition for a keratin material chosen from body skin, facial skin, mucous membranes, the scalp, the hair, the nails, the eyelashes, and the eyebrows comprising a nanoemulsion comprising oil globules with an average size of less than 150 nm comprising at least one oil, at least one amphiphilc lipid, and at least one cationic polymer comprising at least one hydrophobic block and at least one hydrophilic block.

72. A cosmetic make-up-removing composition for a keratin material chosen from body skin, facial skin, mucous membranes, the scalp, the hair, the nails, the eyelashes, and the eyebrows comprising a nanoemulsion comprising oil globules with an average size of less than 150 nm comprising at least one oil, at least one amphiphilc lipid, and at least one cationic polymer comprising at least one hydrophobic block and at least one hydrophilic block.

73. A non-therapeutic care process for a keratin material comprising applying a nanoemulsion comprising oil globules with an average size of less than 150 nm and comprising at least one oil, at least one amphiphilc lipid, and at least one cationic polymer comprising at least one hydrophobic block and at least one hydrophilic block to said keratin material.

74. A process according to

claim 73

, wherein said keratin material is chosen from the skin, the hair, the eyelashes, the eyebrows, the nails, mucous membranes and the scalp.

75. A non-therapeutic care process for a keratin material comprising applying to said keratin material a composition for topical use chosen from cosmetic compositions and dermopharmaceutical compositions, wherein said composition for topical use comprises a nanoemulsion comprising oil globules with an average size of less than 150 nm and comprising at least one oil, at least one amphiphilc lipid, and at least one cationic polymer comprising at least one hydrophobic block and at least one hydrophilic block.

76. A process according to

claim 75

, wherein said keratin material is chosen from the skin, the hair, the eyelashes, the eyebrows, the nails, mucous membranes and the scalp.

77. A process for thickening oil-in-water nanoemulsions comprising including at least one cationic polymer comprising at least one hydrophobic block and at least one hydrophilic block in said nanoemulsions comprising oil globules with an average size of less than 150 nm and comprising at least one oil and at least one amphiphilc lipid.

78. An oil-in-water nanoemulsion comprising oil globules with an average size of less than 150 nm comprising at least one oily phase, at least one amphiphilc lipid, and at least one nonionic polymer comprising at least one hydrophobic block and at least one hydrophilic block.

79. A nanoemulsion according to

claim 78

, wherein said at least one oily phase and said at least one amphiphilic lipid are present in amounts wherein the weight ratio of the amount of said at least one oily phase to the amount of said at least one amphiphilic lipid ranges from 1:

1 to 10;

1.

80. A nanoemulsion according to

claim 79

, wherein said at least one oily phase and said at least one amphiphilic lipid are present in amounts wherein the weight ratio of the amount of said at least one oily phase to the amount of said at least one amphiphilic lipid ranges from 1.2:

1 to 10;

1.

81. A nanoemulsion according to

claim 80

, wherein said at least one oily phase and said at least one amphiphilic lipid are present in amounts wherein the weight ratio of the amount of said at least one oily phase to the amount of said at least one amphiphilic lipid ranges from 1.5:

1 to 6;

1.

82. A nanoemulsion according to

claim 81

, wherein said at least one oily phase and said at least one amphiphilic lipid are present in amounts wherein the weight ratio of the amount of said at least one oily phase to the amount of said at least one amphiphilic lipid ranges from 2:

1 to 5;

1.