Personal care compositions comprising a pH tuneable gellant and methods of using

• US 9,271,912 B2
• Filed: 06/13/2012
• Issued: 03/01/2016
• Est. Priority Date: 06/13/2012
• Status: Active Grant

• Current Assignee: The Procter & Gamble Company
• Original Assignee: The Procter & Gamble Company
• Inventors: Fernandez Prieto, Susana, Smets, Johan, Escuder Gil, Beatriu, Miravet Celades, Juan Felipe, Tanner, Paul Robert, Nebot Carda, Vicent Josep
• Primary Examiner(s): Wax, Robert A
• Assistant Examiner(s): MERCIER, MELISSA S
• Application Number:
  US13/495,400
• Publication Number:
  US 20130336903A1
• Time in Patent Office: 1,357 Days
• Field of Search: None
• US Class Current: 1/1
• CPC Class Codes: A61K 2800/10 General cosmetic use
• CPC Class Codes: A61K 8/42 Amides
• CPC Class Codes: A61K 8/44 Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
• CPC Class Codes: A61K 8/4926 having six membered rings
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 19/08 for bone diseases, e.g. rachitism, Paget's disease
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 31/04 Antibacterial agents
• CPC Class Codes: A61P 31/10 Antimycotics
• CPC Class Codes: A61Q 19/00 Preparations for care of the skin

Abstract

A personal care composition is disclosed comprising a pH tuneable gellant. The pH tuneable gellant has a formula of:

wherein R₁ and R₂ are aminofunctional end-groups; L₁ is a backbone moiety having molecular weight from 14 to 500 g/mol; and at least one of L₁, R₁ or R₂ comprises a pH-sensitive group;

wherein R₅ is an aminofunctional moiety; L₂ is a backbone moiety having molecular weight from 14 to 500 g/mol; and at least one of L₂ or R₅ comprises a pH-sensitive group; and mixtures of [I] and [II]. The personal care composition may take a variety of forms such as a leave-on composition or an emulsion or may comprise one or more actives or agents.

Claims

1. A personal care composition comprising a pH tuneable gellant, wherein the pH tuneable gellant has a formula selected from the group consisting of:

a.

4. The personal care composition of claim 1, 2, or 3, wherein the pH tuneable gellant has a pKa of from 1.5 to 14.

5. The personal care composition of claim 1, 2, or 3, wherein the pH tuneable gellant has a molecular weight from 150 to 1500 g/mol.

6. The personal care composition of claim 1, 2, or 3, wherein the pH tuneable gellant has a minimum gelling concentration (MGC) of from 0.1 to 100 mg/mL, at the pH of the composition.

7. The personal care composition of claim 1, 2, or 3, wherein the pH tuneable amido gellant is selected from the group:

N,N′

-(2S,2′

S)-1,1′

-(ethane-1,2-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(propane-1,3-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(butane-1,4-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(pentane-1,5-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(hexane-1,6-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(heptane-1,7-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(octane-1,8-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)diisonicotinamide;

(6S,13S′

)-6,13-diisopropyl-4,7,12,15-tetraoxo-5,8,11,14-tetraazaoctadecane-1,18-dioic acid;

(6S,14S′

)-6,14-diisopropyl-4,7,13,16-tetraoxo-5,8,12,15-tetraazanonadecane-1,19-dioic acid;

(6S,15S′

)-6,15-diisopropyl-4,7,14,17-tetraoxo-5,8,13,16-tetraazaeicosane-1,20-dioic acid;

(6S,16S′

)-6,16-diisopropyl-4,7,15,18-tetraoxo-5,8,14,17-tetraazaheneicosane-1,21-dioic acid;

(6S,17S′

)-6,17-diisopropyl-4,7,16,19-tetraoxo-5,8,15,18-tetraazadocosane-1,22-dioic acid;

(6S,18S′

)-6,18-diisopropyl-4,7,17,20-tetraoxo-5,8,16,19-tetraazatricosane-1,23-dioic acid;

(6S,19S′

)-6,19-diisopropyl-4,7,18,21-tetraoxo-5,8,17,20-tetraazatetracosane-1,24-dioic acid;

(6S,20S′

)-6,20-diisopropyl-4,7,19,22-tetraoxo-5,8,18,21-tetraazapentacosane-1,25-dioic acid;

(6S,21S′

)-6,21-diisopropyl-4,7,20,23-tetraoxo-5,8,19,22-tetraazahexacosane-1,26-dioic acid;

(6S,22S′

)-6,22-diisopropyl-4,7,21,24-tetraoxo-5,8,20,23-tetraazaheptacosane-1,27-dioic acid;

(6S,23S′

)-6,23-diisopropyl-4,7,22,25-tetraoxo-5,8,21,24-tetraazaoctacosane-1,28-dioic acid;

N,N′

-(2S,2′

S)-1,1′

-(ethane-1,2-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)bis(4-(1H-imidazol-5-yl)benzamide);

N,N′

-(2S,2′

S)-1,1′

-(propane-1,3-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)bis(4-(1H-imidazol-5-yl)benzamide N,N′

-(2S,2′

S)-1,1′

-(butane-1,4-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)bis(4-(1H-imidazol-5-yl)benzamide);

N,N′

-(2S,2′

S)-1,1′

-(pentane-1,5-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)bis(4-(1H-imidazol-5-yl)benzamide);

N,N′

-(2S,2′

S)-1,1′

-(hexane-1,6-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)bis(4-(1H-imidazol-5-yl)benzamide);

N,N′

-(2S,2′

S)-1,1′

-(heptane-1,7-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)bis(4-(1H-imidazol-5-yl)benzamide);

N,N′

-(2S,2′

S)-1,1′

-(octane-1,8-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)bis(4-(1H-imidazol-5-yl)benzamide);

N,N′

-(2S,2′

S)-1,1′

-(nonane-1,9-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)bis(4-(1H-imidazol-5-yl)benzamide);

N,N′

-(2S,2′

S)-1,1′

-(decane-1,10-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)bis(4-(1H-imidazol-5-yl)benzamide);

N,N′

-(2S,2′

S)-1,1′

-(undecane-1,11-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)bis(4-(1H-imidazol-5-yl)benzamide);

N,N′

-(2S,2′

S)-1,1′

-(dodecane-1,12-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)bis(4-(1H-imidazol-5-yl)benzamide);

N,N′

-(2S,2′

S)-1,1′

-(nonane-1,9-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(decane-1,10-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(undecane-1,11-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(dodecane-1,12-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(tridecane-1,13-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(tetradecane-1,14-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(hexadecane-1,16-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(octadecane-1,18-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(ethane-1,2-diylbis(azanediyl))bis(1-oxopropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(propane-1,3-diylbis(azanediyl))bis(1-oxopropane-2,1-diyediisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(butane-1,4-diylbis(azanediyl))bis(1-oxopropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(pentane-1,5-diylbis(azanediyl))bis(1-oxopropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(hexane-1,6-diylbis(azanediyl))bis(1-oxopropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(heptane-1,7-diylbis(azanediyl))bis(1-oxopropane-2,1-diyediisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(octane-1,8-diylbis(azanediyl))bis(1-oxopropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(nonane-1,9-diylbis(azanediyl))bis(1-oxopropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(decane-1,10-diylbis(azanediyl))bis(1-oxopropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(undecane-1,11-diylbis(azanediyl))bis(1-oxopropane-2,1-diyediisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(dodecane-1,12-diylbis(azanediyl))bis(1-oxopropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(tridecane-1,13-diylbis(azanediyl))bis(1-oxopropane-2,1-diyediisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(tetradecane-1,14-diylbis(azanediyl))bis(1-oxopropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(hexadecane-1,16-diylbis(azanediyl))bis(1-oxopropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(octadecane-1,18-diylbis(azanediyl))bis(1-oxopropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(ethane-1,2-diylbis(azanediyl))bis(1-oxo-3-phenylpropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(propane-1,3-diylbis(azanediyl))bis(1-oxo-3-phenylpropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(butane-1,4-diylbis(azanediyl))bis(1-oxo-3-phenylpropane-2,1-diyediisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(pentane-1,5-diylbis(azanediyl))bis(1-oxo-3-phenylpropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(hexane-1,6-diylbis(azanediyl))bis(1-oxo-3-phenylpropane-2,1-diyl)diisonicotinamide N,N′

-(2S,2′

S)-1,1′

-(heptane-1,7-diylbis(azanediyl))bis(1-oxo-3-phenylpropane-2,1-diyediisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(octane-1,8-diylbis(azanediyl))bis(1-oxo-3-phenylpropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(nonane-1,9-diylbis(azanediyl))bis(1-oxo-3-phenylpropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(decane-1,10-diylbis(azanediyl))bis(1-oxo-3-phenylpropane-2,1-diyediisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(undecane-1,11-diylbis(azanediyl))bis(1-oxo-3-phenylpropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(dodecane-1,12-diylbis(azanediyl))bis(1-oxo-3-phenylpropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(tridecane-1,13-diylbis(azanediyl))bis(1-oxo-3-phenylpropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(tetradecane-1,14-diylbis(azanediyl))bis(1-oxo-3-phenylpropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(hexadecane-1,16-diylbis(azanediyl))bis(1-oxo-3-phenylpropane-2,1-diyl)diisonicotinamide;

N,N′

-(2S,2′

S)-1,1′

-(octadecane-1,18-diylbis(azanediyl))bis(1-oxo-3-phenylpropane-2,1-diyl)diisonicotinamide;

(2S)-2-[[2-(dodecanoylamino)acetyl]amino]propanoic acid;

(2S)-2-[[2-[[2-(dodecanoylamino)acetyl]amino]acetyl]amino]propanoic acid;

(2S)-2-[[2-(dodecanoylamino)acetyl]amino]-2-phenyl-acetic acid;

(2S)-2-[[2-(dodecanoylamino)acetyl]amino]-3-methyl-butanoic acid;

2-[[2-(dodecanoylamino)acetyl]amino]acetic acid;

(2S)-2-[[2-(hexadecanoylamino)acetyl]amino]propanoic acid; and

mixtures thereof.

13. The personal care composition of claim 1, 2, or 3 further comprising from about 1% to about 95%, by weight of the composition, water.

14. The personal care composition of claim 1, 2, or 3 further comprising from about 1% to about 95%, by weight of the composition, oil.

15. The personal care composition of claim 14 wherein the oil is selected from a group consisting of linear silicones, cyclic silicones, paraffinic hydrocarbons, fatty esters, hydrocarbon oils, cationic silicone fluids, and combinations thereof.

16. The personal care composition of claim 1, 2, or 3 further comprising an additional structuring agent selected from a group consisting of polysaccharides, gums, carboxylic acid polymers, sulfonated polymers, acrylamide polymers, polyalkylglycols, polyglycerins, silicone elastomers, silicone gums, silicone waxes, polyamides, polysilicone-polyamide copolymers, natural and synthetic waxes, natural and synthetic montmorillonite minerals, silicas, silicates, derivatives thereof, and combinations thereof.

17. The personal care composition of claim 1 or 2 further comprising an active or agent selected from a group consisting of sugar amines, vitamins, dehydroacetic acid and salts, photosterols, hexamidine compounds, dialkanoyl hydroxyproline and salts, flavonoids, N-acyl amino acid compounds, retinoids, peptides, particulates, UV actives, anti-cellulite agents, butylated hydroxytoluene, butylated hydroxyanisole, desquamation actives, anti-acne actives, anti-wrinkle actives, anti-atrophy actives, conditioning agents, anti-oxidants, radical scavengers, anti-inflammatory agents, tanning actives, skin lightening agents, botanical extracts, antimicrobial actives, antifungal actives, antibacterial actives, antiperspirant actives, anti-dandruff actives, humectants, terpene alcohols, and combinations thereof.

18. The personal care composition of claim 3 or 17 wherein the vitamins are selected from vitamin B3 compound, ascorbic acid, tocopherol acetate, panthenol, dexpanthenol, magnesium ascorbyl phosphate, sodium ascorbyl phosphate, retinyl propionate, and combinations thereof.

19. The personal care composition of claim 3 or 17 wherein the active or agent is selected from glucosamine, glucosamine derivatives, salts of dehydroacetic acid, salicylic acid, hexamidine diisethionate, salts of dialkanoyl hydroxyproline, N-acyl phenylalanine, dipeptides, pentapeptides, titanium dioxide, iron oxide, zinc oxide, butylated hydroxytoluene, dihydroxyacetone, and combinations thereof.

20. The personal care composition of claim 1, 2, or 3 wherein the composition is paraben free.

21. The personal care composition of claim 1 or 3 wherein the composition comprises less than 1% of a detersive surfactant.

22. The personal care composition of claim 1, 2, or 3 wherein the composition comprises no detersive surfactant.

2. A personal care composition in the form of an emulsion comprising an aqueous phase, an oil phase, and a pH tuneable gellant, has a formula selected from the group consisting of:

a.

9. The personal care composition of claim 2 or 8 wherein the pH tuneable gellant structures the aqueous phase.

10. The personal care composition of claim 2 or 8 wherein the pH tuneable gellant structures the oil phase.

11. The personal care composition of claim 2 or 8 further comprising an emulsifier.

12. The personal care composition of claim 11, wherein the emulsifier is selected from ethers or esters of glycerol, polyglycerol, sucrose, glucose, and sorbitol.

3. A personal care composition comprising

a. a pH tuneable gellant, has a formula selected from the group consisting of:

i.

8. The personal care composition of claim 3 wherein the personal care composition is an emulsion having an aqueous phase and an oil phase.