IP Library Granted Patent US 12,059,486
Granted Patent B2
US 12,059,486 · App. 17/647,877 · Granted Aug 13, 2024

Cosmetic compositions

Inventors: George P. Majewski (San Francisco, CA); Christine Crane (San Francisco, CA); John Simon Craw (San Francisco, CA); Gabriele Di Fiore (San Francisco, CA); Dzung Q. Le (San Francisco, CA); Olga Dueva-Koganov (San Francisco, CA); Robert Bianchini (San Francisco, CA); Angela M. Rivera (San Francisco, CA)
Assignee: Rodan &Fields, LLC
A61K8/14A61K8/345A61K8/41A61K8/44A61K8/671A61K8/676A61K8/678A61K8/73A61Q19/08A61K2800/805
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Quick Facts
Patent No.
US 12,059,486
App. No.
17/647,877
Granted
Aug 13, 2024
Kind
B2
Abstract

The compositions of various embodiments include a tocopherol phosphate mixture (TPM) comprising a liposome having a lipid bilayer and an internal aqueous compartment, a lipophilic ingredient, a polar solvent system, an alcohol, a base, and a water soluble phase, wherein the liposome is made of a tocopherol phosphate derivative, wherein the lipophilic ingredients are entrapped in the lipophilic bilayer of the liposome, and wherein a water soluble ingredient is dissolved in the water soluble phase and is in the internal compartment of the liposome. The methods include improving the look of skin particularly of the neck and décolletage, increasing expression of an extracellular matrix proteins in skin, improving a keloid scar in a subject, and improving aging skin. Additionally, methods for preparing the compositions are described herein.

Claims (28)

1. A method for preparing a tocopherol phosphate mixture (TPM) liposomal composition comprising:

a) mixing a lipophilic ingredient with a polar solvent system and heating the resulting mixture to a temperature of at least about 60° C.;

b) adding a mixture of tocopherol phosphate derivative ingredients to the mixture from step a) once temperature reaches about 57.9° C. and maintaining the temperature sufficient to melt all contents, wherein the mixture of tocopherol phosphate derivative ingredients are selected from alpha-tocopheryl phosphate (TP), di-alpha-tocopheryl phosphate (T2P), beta tocopherol phosphate, gamma tocopherol phosphate, delta tocopherol phosphate, or a combination thereof;

c) cooling the mixture from step b) to a temperature of about 32° C. to about 35° C., adding one or more lipophilic ingredients and ethanol into the cooled mixture, and mixing the mixture until complete dissolution to form Phase A;

d) mixing, in a separate container, one or more water soluble ingredients, and water thoroughly at a temperature of about 38° C. to about 40° C. to form Phase B;

e) adding Phase A into Phase B and mixing at a temperature of about 38° C. to about 40° C. for at least 20 minutes;

f) adding a neutralizing base to the mixture of step e);

g) dispersing xanthan gum into glycerin to form Phase C and mixing Phase C into the mixture of step f); and

h) turning off the heat to the mixture of step g) and stirring the mixture until the temperature of the mixture reaches room temperature, thereby forming the TPM liposomal composition.

2. The method of claim 1 , wherein the polar solvent system comprises a polar solvent 1 and a polar solvent 2 each selected from the group consisting of a polyol, a mono-isosorbide ether, a di-alkyl isosorbide ether, and combinations thereof.

3. The method of claim 2 , wherein the polar solvent 1 is a polyol and the polar solvent 2 is a di-alkyl isosorbide ether.

4. The method of claim 3 , wherein the polyol is pentylene glycol and the di-alkyl isosorbide ether is dimethyl isosorbide (DMI).

5. The method of claim 2 , wherein the polar solvent 1 is present in an amount of about 5% to about 10% by weight of the TPM liposomal composition and the polar solvent 2 is present in an amount of about 2% to about 6% by weight of the TPM liposomal composition.

6. The method of claim 1 , wherein the ethanol is about 5% to about 10% by weight of the TPM liposomal composition.

7. The method of claim 1 , wherein the mixture of tocopherol phosphate derivative ingredients is a mixture of TP and T2P.

8. The method of claim 7 , wherein the mixture of TP and T2P is in a ratio of about 4:1 to about 1:1 (TP:T2P).

9. The method of claim 1 , wherein the mixture of tocopherol phosphate derivative ingredients is about 1.5% to about 5% by weight of the TPM liposomal composition.

10. The method of claim 1 , wherein the neutralizing base is about 0.1% to about 1% by weight of the TPM liposomal composition.

11. The method of claim 1 , wherein the neutralizing base is tromethamine or sodium hydroxide.

12. The method of claim 1 , wherein the temperature of step a) is about 60° C. to about 65° C.

13. The method of claim 1 , wherein the temperature of step b) is about 57.9° C. to about 61° C.

14. The method of claim 1 , wherein the one or more lipophilic ingredients is selected from the group consisting of a hydrophobically modified amino acid, a hydrophobically modified vitamin, a retinoid, a resveratrol derivative, a fatty acid, a fatty ester, and combinations thereof.

15. The method of claim 14 , wherein the hydrophobically modified amino acid is hydrophobically modified proline, wherein the hydrophobically modified proline is dipalmitoyl hydroxyproline, and wherein the hydrophobically modified vitamin is a hydrophobically modified ascorbic acid.

16. The method of claim 14 , wherein the retinoid is selected from the group consisting of retinaldehyde, ester of retinoic acid, retinyl palmitate, alitretinoin (9-cis-retinoic acid), tretinoin (all-trans-retinoic acid), isotretinoin (13-cis-retinoic acid), etretinate, acitretin, adapalene, bexarotene, tazarotene, hydroxypinacolone retinoate, and combinations thereof.

17. The method of claim 14 , wherein the fatty ester is a blend of pterostilbene (resveratrol dimethyl ether) and xymenynic acid dissolved in glyceryl linoleate and glyceryl linolenate.

18. The method of claim 1 , wherein one or more water soluble ingredients and the water are about 70% to 85% by weight of the TPM liposomal composition.

19. The method of claim 1 , wherein the one or more water soluble ingredients is a water soluble amino acid, a water soluble vitamin, xanthine, or combinations thereof.

20. The method of claim 1 , wherein the TPM liposomal composition has a pH of about 4.5 to about 5.

Assignments (10)
ASSIGNMENT OF SECURITY INTERESTS IN PATENT COLLATERAL Recorded Feb 2, 2026
From: CITIBANK, N.A., IN ITS CAPACITY AS THE WITHDRAWING AGENT
To: ANKURA TRUST COMPANY, LLC, IN ITS CAPACITY AS SUCCESSOR AGENT
Reel/Frame 074643/0097 →
MERGER Recorded Oct 9, 2024
From: RODAN & FIELDS, LLC
To: RODAN & FIELDS BEAUTY, LLC
Reel/Frame 068844/0351 →
PATENT SECURITY AGREEMENT Recorded Sep 27, 2024
From: RODAN & FIELDS BEAUTY, LLC
To: ANKURA TRUST COMPANY, LLC, AS COLLATERAL AGENT
Reel/Frame 069066/0818 →
RELEASE OF SECURITY INTEREST IN PATENT COLLATERAL RECORDED ON APRIL 28, 2023, AT REEL/FRAME 063480/0786 Recorded Sep 27, 2024
From: ANKURA TRUST COMPANY, LLC, AS COLLATERAL AGENT
To: RODAN & FIELDS, LLC
Reel/Frame 069066/0803 →
PATENT SECURITY AGREEMENT Recorded Sep 27, 2024
From: RODAN & FIELDS BEAUTY, LLC
To: ANKURA TRUST COMPANY, LLC, AS COLLATERAL AGENT
Reel/Frame 069066/0810 →
SECURITY INTEREST Recorded May 2, 2023
From: RODAN & FIELDS, LLC
To: CITIBANK, N.A.
Reel/Frame 063501/0785 →
SECURITY INTEREST Recorded May 2, 2023
From: RODAN & FIELDS, LLC
To: ANKURA TRUST COMPANY, LLC
Reel/Frame 063501/0804 →
SECURITY INTEREST Recorded Apr 28, 2023
From: RODAN & FIELDS, LLC
To: ANKURA TRUST COMPANY, LLC
Reel/Frame 063480/0786 →
SECURITY INTEREST Recorded Apr 28, 2023
From: RODAN & FIELDS, LLC
To: ANKURA TRUST COMPANY, LLC
Reel/Frame 063480/0179 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 28, 2022
From: BIANCHINI, ROBERT; CRANE, CHRISTINE; CRAW, JOHN SIMON; DI FIORE, GABRIELE; DUEVA-KOGANOV, OLGA; LE, DZUNG Q.; MAJEWSKI, GEORGE P.; RIVERA, ANGELA M.
To: RODAN & FIELDS, LLC
Reel/Frame 061568/0915 →
Continuity (2)
Provisional Application 63136722 · Jan 13, 2021
Related Publication 20220218574A1 · Jul 14, 2022