IP Library Granted Patent US 10,603,264
Granted Patent B2
US 10,603,264 · App. 16/230,724 · Granted Mar 31, 2020

Silsesquioxanes and use in nail coatings thereof

Inventors: Jamie Welton (Carlsbad, CA); Kaleb Dixon (San Diego, CA); Joseph Lichtenhan (Petal, MS); Sukhendu Hait (Hattiesburg, MS); Joseph Schwab (Huntington Beach, CA)
Assignee: Revlon Consumer Products Corporation
A61K8/585A61K8/25A61K8/375A61K8/8147A61K8/8152A61K8/87A61K8/891A61Q3/00A61Q3/02
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,603,264
App. No.
16/230,724
Granted
Mar 31, 2020
Kind
B2
Abstract

Polyhedral oligomeric silsesquioxanes (POSS) and formulations for nail coating are disclosed. By including a POSS in the nail coating topcoat formulation, gloss and hardness of the cured nail coating are improved without compromising removability. If included in the color layer formulation, the POSS provides improved adhesion to the nail such that a base layer is not needed. Incorporating a fatty alcohol methacrylate in the topcoat formulation also improves gloss and hardness. Polyurethane copolymers can provide the cured nail coating with good solvent removability without compromising adhesion to the nail, gloss or hardness.

Claims (19)

1. A nail coating formulation comprising a compound of formula (I):

wherein at least one R group is a group comprising polyethylene glycol units and the R groups, other than the at least one R group, are alkyl groups.

2. The nail coating formulation of claim 1 , wherein the formulation comprises about 0.1-10 wt % of the compound of formula (I).

3. The nail coating formulation of claim 1 , wherein the formulation comprises a fatty alcohol methacrylate.

4. The nail coating formulation of claim 3 , wherein the fatty alcohol methacrylate is stearyl methacrylate or cetyl methacrylate or a mixture thereof.

5. The nail coating formulation of claim 4 , wherein the formulation comprises about 0.1-10 wt % fatty alcohol methacrylate.

6. The nail coating formulation of claim 1 , wherein the formulation comprises a polyurethane.

7. The nail coating formulation of claim 6 , wherein the polyurethane is selected from the group consisting of bis-HEMA poly(1,4-butanediol)/IPDI copolymer, bis-HEMA poly(caprolactone/neopentyl glycol)/IPDI copolymer, bis-HEMA poly(caprolactone/neopentyl glycol)/1,4-butanediol/IPDI copolymer, bis-ethylhexyl poly(caprolactone neopentyl glycol)/IPDI copolymer, bis-HEMA poly(caprolactone/pentaerythritol)/IPDI copolymer, bis-ethylhexyl poly(caprolactone/pentaerythritol)/IPDI copolymer, bis-HEMA poly(caprolactone/pentaerythritol)/IPDI copolymer succinate, or bis-ethylhexyl poly(caprolactone/pentaerythritol)/IPDI copolymer succinate, and mixtures thereof.

8. The nail coating formulation of claim 1 , wherein the formulation comprises trimethylolpropane trimethacrylate.

9. The nail coating formulation of claim 8 , wherein the formulation comprises about 0.1-10 wt % of trimethylolpropane trimethacrylate.

10. The nail coating formulation of claim 1 , wherein the formulation comprises about 0.5 wt % of the compound of formula (I) and about 0.5 wt % of stearyl methacrylate.

11. The nail coating formulation of claim 1 , wherein only one R group of the compound of formula (I) is a group comprising polyethylene glycol units.

12. The nail coating formulation of claim 11 , wherein the alkyl groups of the compound of formula (I) have from 1 to 20 carbon atoms.

13. The nail coating formulation of claim 12 , wherein the alkyl groups of the compound of formula (I) are —CH 2 CH(CH 3 )CH 2 C(CH 3 ) 3 groups.

14. The nail coating formulation of claim 11 , wherein the group of the compound of formula (I) comprising polyethylene glycol units has the formula —(CH 2 ) 3 (OCH 2 CH 2 ) m OCH 3 , wherein the average value of m ranges from 1 to 50.

15. The nail coating formulation of claim 1 , wherein the compound of formula (I) is

16. A method of coating a nail comprising applying the formulation of claim 1 to a nail surface.

17. The method of claim 16 , wherein the formulation is applied directly to the nail surface.

18. The method of claim 16 , wherein the formulation is applied onto a layer of another nail coating.

Assignments (22)
SECURITY INTEREST Recorded Oct 2, 2024
From: BRANDCO ALMAY 2020 LLC; BRANDCO CND 2020 LLC; BRANDCO ELIZABETH ARDEN 2020 LLC; BRANDCO MITCHUM 2020 LLC; REVLON CONSUMER PRODUCTS LLC
To: MUFG BANK LTD. AS AGENT
Reel/Frame 069102/0838 →
RELEASE OF SECURITY INTEREST Recorded Oct 1, 2024
From: MIDCAP FUNDING IV TRUST, AS COLLATERAL AGENT
To: BRANDCO ALMAY 2020 LLC; BRANDCO CND 2020 LLC; BRANDCO ELIZABETH ARDEN 2020 LLC; BRANDCO MITCHUM 2020 LLC; REVLON CONSUMER PRODUCTS LLC; CREATIVE NAIL DESIGN, INC.; SINFULCOLORS, INC.
Reel/Frame 069084/0092 →
ABL PATENT SECURITY AGREEMENT Recorded May 4, 2023
From: BRANDCO ALMAY 2020 LLC; BRANDCO CND 2020 LLC; BRANDCO ELIZABETH ARDEN 2020 LLC; BRANDCO MITCHUM 2020 LLC; REVLON CONSUMER PRODUCTS LLC; CREATIVE NAIL DESIGN, INC.; SINFULCOLORS, INC.
To: MIDCAP FUNDING IV TRUST
Reel/Frame 063548/0557 →
TERM LOAN PATENT SECURITY AGREEMENT Recorded May 4, 2023
From: BRANDCO ALMAY 2020 LLC; BRANDCO CND 2020 LLC; BRANDCO ELIZABETH ARDEN 2020 LLC; BRANDCO MITCHUM 2020 LLC; REVLON CONSUMER PRODUCTS LLC; CREATIVE NAIL DESIGN, INC.; SINFULCOLORS, INC.
To: JEFFERIES FINANCE LLC
Reel/Frame 063548/0575 →
STATEMENT REGARDING RELEASE OF LIENS ON COPYRIGHTS, TRADEMARKS AND PATENTS Recorded May 3, 2023
From: REVLON GROUP HOLDINGS LLC
To: ALMAY, INC.; ART & SCIENCE, LTD.; BARI COSMETICS, LTD.; BEAUTYGE BRANDS USA, INC.; BEAUTYGE I; BEAUTYGE II, LLC; BEAUTYGE USA, INC.; BRANDCO ALMAY 2020 LLC; BRANDCO CHARLIE 2020 LLC; BRANDCO CND 2020 LLC; BRANDCO CURVE 2020 LLC; BRANDCO ELIZABETH ARDEN 2020 LLC; BRANDCO GIORGIO BEVERLY HILLS 2020 LLC; BRANDCO HALSTON 2020 LLC; BRANDCO JEAN NATE 2020 LLC; BRANDCO MITCHUM 2020 LLC; BRANDCO MULTICULTURAL GROUP 2020 LLC; BRANDCO PS 2020 LLC; BRANDCO WHITE SHOULDERS 2020 LLC; CHARLES REVSON INC.; CREATIVE NAIL DESIGN, INC.; CUTEX, INC.; DF ENTERPRISES, INC.; ELIZABETH ARDEN (CANADA) LIMITED; ELIZABETH ARDEN (FINANCING), INC.; ELIZABETH ARDEN (UK) LTD.; ELIZABETH ARDEN INVESTMENTS, LLC; ELIZABETH ARDEN NM, LLC; ELIZABETH ARDEN TRAVEL RETAIL, INC.; ELIZABETH ARDEN USC, LLC; ELIZABETH ARDEN, INC.; FD MANAGEMENT, INC.; NORTH AMERICA REVSALE INC.; OPP PRODUCTS, INC.; PPI TWO CORPORATION; RDEN MANAGEMENT, INC.; REALISTIC ROUX PROFESSIONAL PRODUCTS INC.; REVLON (PUERTO RICO) INC.; REVLON CANADA INC.; REVLON CONSUMER PRODUCTS CORPORATION; REVLON DEVELOPMENT CORP.; REVLON GOVERNMENT SALES, INC.; REVLON INTERNATIONAL CORPORATION; REVLON PROFESSIONAL HOLDING COMPANY LLC; REVLON, INC.; RIROS CORPORATION; RIROS GROUP INC.; RML, LLC; ROUX LABORATORIES, INC.; ROUX PROPERTIES JACKSONVILLE, LLC; SINFULCOLORS INC.
Reel/Frame 063530/0396 →
SECURITY INTEREST Recorded Jul 1, 2022
From: BRANDCO CND 2020 LLC
To: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 060427/0006 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 6, 2021
From: REVLON CONSUMER PRODUCTS CORPORATION
To: BEAUTYGE I
Reel/Frame 057099/0744 →
BACK-UP PATENT SECURITY AGREEMENT Recorded Aug 6, 2021
From: REVLON CONSUMER PRODUCTS CORPORATION
To: BEAUTYGE I
Reel/Frame 057108/0540 →
RELEASE OF SECURITY INTEREST Recorded May 18, 2020
From: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
To: CREATIVE NAIL DESIGN, INC.; ELIZABETH ARDEN, INC.; FD MANAGEMENT, INC.; REVLON CONSUMER PRODUCTS CORPORATION; ROUX LABORATORIES, INC.; SINFULCOLORS INC.
Reel/Frame 052694/0508 →
FIRST LIEN PATENT SECURITY AGREEMENT Recorded May 11, 2020
From: BRANDCO CND 2020 LLC
To: JEFFERIES FINANCE LLC
Reel/Frame 052621/0125 →
THIRD LIEN PATENT SECURITY AGREEMENT Recorded May 11, 2020
From: BRANDCO CND 2020 LLC
To: JEFFERIES FINANCE LLC
Reel/Frame 052620/0492 →
SECOND LIEN PATENT SECURITY AGREEMENT Recorded May 11, 2020
From: BRANDCO CND 2020 LLC
To: JEFFERIES FINANCE LLC
Reel/Frame 052620/0506 →
BACK-UP PATENT SECURITY AGREEMENT Recorded May 9, 2020
From: BEAUTYGE I
To: BRANDCO CND 2020 LLC
Reel/Frame 052619/0476 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 9, 2020
From: BEAUTYGE I
To: BRANDCO CND 2020 LLC
Reel/Frame 052618/0740 →
RELEASE OF SECURITY INTEREST IN CERTAIN PATENTS AT R/F 050592/0350 Recorded May 7, 2020
From: CITIBANK N.A., AS COLLATERAL AGENT
To: REVLON CONSUMER PRODUCTS CORPORATION
Reel/Frame 052600/0282 →
RELEASE OF SECURITY INTEREST IN CERTAIN PATENTS AT R/F 050592/0368 Recorded May 7, 2020
From: CITIBANK N.A., AS COLLATERAL AGENT
To: REVLON CONSUMER PRODUCTS CORPORATION
Reel/Frame 052599/0427 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 6, 2020
From: HYBRID PLASTICS, INC.
To: REVLON CONSUMER PRODUCTS CORPORATION
Reel/Frame 051428/0171 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 6, 2020
From: LICHTENHAN, JOSEPH; HAIT, SUKHENDU; SCHWAB, JOSEPH
To: HYBRID PLASTICS, INC.
Reel/Frame 051427/0346 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 17, 2019
From: WELTON, JAMIE; DIXON, KALEB
To: REVLON CONSUMER PRODUCTS CORPORATION
Reel/Frame 051303/0065 →
PATENT SECURITY AGREEMENT (TERM) Recorded Sep 30, 2019
From: REVLON CONSUMER PRODUCTS CORPORATION
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 050592/0368 →
PATENT SECURITY AGREEMENT (ABL) Recorded Sep 30, 2019
From: REVLON CONSUMER PRODUCTS CORPORATION
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 050592/0350 →
SECURITY INTEREST Recorded Aug 6, 2019
From: CREATIVE NAIL DESIGN, INC.; ELIZABETH ARDEN, INC.; FD MANAGEMENT, INC.; REVLON CONSUMER PRODUCTS CORPORATION; ROUX LABORATORIES, INC.; SINFULCOLORS INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 049969/0038 →
Continuity (2)
Provisional Application 62608796 · Dec 21, 2017
Related Publication 20190192411A1 · Jun 27, 2019