IP Library › Granted Patent US 8,278,332
Granted Patent B2
US 8,278,332 · App. 13/282,667 · Granted Oct 2, 2012

Photostabilization of retinoids with alkoxycrylene compounds

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Quick Facts
Patent No.
US 8,278,332
App. No.
13/282,667
Granted
Oct 2, 2012
Kind
B2
Abstract

The photostabilizing electronic excited state energy—particularly singlet state energy from retinoid compounds—has been found to be readily transferred to (accepted by) α-cyanodiphenylacrylate compounds having an alkoxy radical in the four (para) position (hereinafter “alkoxycrylenes”) on one of the phenyl rings having the formula (I): wherein one of R 1 and R 2 is a straight or branched chain C 1 -C 30 alkoxy radical, preferably C 1 -C 8 , more preferably methoxy, and the non-alkoxy radical R 1 or R 2 is hydrogen; and R 3 is a straight or branched chain C 1 -C 30 alkyl radical, preferably C 2 -C 20 . The alkoxycrylene compounds of formula (I) significantly increase the photostability of retinoid compounds in a composition by at least 3-fold.

Claims (27)

1. A method for the anti-acne, anti-aging, wrinkle reducing, sunscreen, cosmetic or dermatological treatment of skin or hair comprising contacting the skin with a photostabilized composition comprising about 0.001% to about 5% by weight of a retinoid compound, and a compound of formula (I) in an amount of at least 0.1%, to about 20% by weight, based on the total weight of the composition, in a sunscreen, cosmetic or dermatological composition, wherein the compound formula (I) is

wherein one of R 1 and R 2 is a straight or branched chain C 1 -C 30 alkoxy radical, and the non-alkoxy R 1 and R 2 is hydrogen; and R 3 is a straight or branched chain C 1 -C 30 alkyl radical.

2. The method of claim 1 , wherein R1 is methoxy and R2 is hydrogen.

3. The method of claim 1 , wherein R1 is hydrogen and R2 is methoxy.

4. The method of claim 1 , wherein R3 is a C12-C24 straight chain or branched alkyl.

5. The method of claim 4 , wherein R3 is a 2-butyloctyl radical.

6. The method of claim 4 , wherein R3 is an 2-ethylhexyl radical.

7. The method of claim 4 , wherein the compound of formula (I) is present in an amount in the weight range of about 0.1% to about 15%, based on the total weight of the composition.

8. The method of claim 7 , wherein the compound of formula (I) is present in an amount in this weight range of about 0.1% to about 10%, based on the total weight of the composition.

9. The method of claim 7 , wherein the compound of formula (I) is present in an amount in this weight range of about 0.1% to about 5%, based on the total weight of the composition.

10. The method of claim 1 , wherein the retinoid compound is present in an amount in the weight range of about 0.001% to about 1%, based on the total weight of the composition.

11. The method of claim 10 , wherein the retinoid compound is present in this weight range of about 0.005% to about 1%, based on the total weight of the composition.

12. The method of claim 10 , wherein the retinoid compound is present in this weight range of about 0.01% to about 0.5%, based on the total weight of the composition.

13. The method of claim 1 , wherein a molar ratio of the retinoid compound to the compound of formula (I) is about 0.001 to about 1.

14. The method of claim 13 , wherein this molar ratio of the retinoid compound to the compound of formula (I) is about 0.005 to about 0.1.

15. The method of claim 13 , wherein the molar ratio of the retinoid compound to the compound of formula (I) is about 0.01 to about 0.06.

16. The method of claim 1 , wherein the retinoid compound is selected from the group consisting of retinol, retinal, tretinoin, isotretinoin, alitretinoin, etretinate, acitretin, bexarotene, tazarotene, and adapalene.

17. The method of claim 16 , wherein the retinoid compound is retinol.

18. The method of claim 16 , wherein the retinoid compound is isotretinoin.

19. The method of claim 16 , wherein the retinoid compound is tretinoin.

20. The method of claim 16 , wherein the retinoid compound is retinal.

21. The method of claim 16 , wherein the retinoid compound is alitretinoin.

22. The method of claim 16 , wherein the retinoid compound is etretinate.

23. The method of claim 16 , wherein the retinoid compound is acitretin.

24. The method of claim 16 , wherein the retinoid compound is bexarotene.

25. The method of claim 16 , wherein the retinoid compound is tazarotene.

26. The method of claim 16 , wherein the retinoid compound is adapalene.

Assignments (5)
THIRD AMENDED AND RESTATED INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Dec 20, 2024
From: THE HALLSTAR COMPANY; HALLSTAR INNOVATIONS CORP.; HALLSTAR BEAUTY AND PERSONAL CARE INNOVATIONS COMPANY; UNIPLEX COMPANY
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 069747/0045 →
THIRD AMENDED AND RESTATED INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Nov 3, 2023
From: THE HALLSTAR COMPANY; HALLSTAR INNOVATIONS CORP.; HALLSTAR BEAUTY AND PERSONAL CARE INNOVATIONS COMPANY; UNIPLEX COMPANY
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 065448/0262 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 28, 2018
From: HALLSTAR INNOVATIONS CORP.
To: HALLSTAR BEAUTY AND PERSONAL CARE INNOVATIONS COMPANY
Reel/Frame 046977/0359 →
SECOND AMENDED AND RESTATED INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Nov 25, 2014
From: HALLSTAR INNOVATIONS CORP.
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 034468/0854 →
AMENDED AND RESTATED INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Feb 21, 2012
From: HALLSTAR INNOVATIONS CORP.
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 027742/0917 →