IP Library Granted Patent US 8,399,537
Granted Patent B2
US 8,399,537 · App. 13/079,261 · Granted Mar 19, 2013

Compositions and methods for nail coatings

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Quick Facts
Patent No.
US 8,399,537
App. No.
13/079,261
Granted
Mar 19, 2013
Kind
B2
Abstract

The present disclosure relates generally to compositions for natural and artificial nail coatings, and particularly, but not by way of limitation, to polymerizable compositions and adhesion-promoting basecoats polymerized therefrom. The disclosure further relates to methods of making a polymerized basecoat that are more easily removed than artificial nail enhancements and more durable and long lasting than nail polish coatings.

Claims (71)

1. A system for covering a nail surface comprising:

a coating curable to an acrylic thermoset lattice layer conforming over the nail surface upon exposure to actinic radiation,

wherein the coating comprises

a polymerizable (meth)acrylate,

a polypropylene glycol (meth)acrylated monomer or polyethylene glycol (meth)acrylated monomer,

a non-reactive solvent, and

a non-reactive, solvent-dissolvable polymer.

2. The nail covering system of claim 1 , wherein said non-reactive, solvent-dissolvable polymer is selected from the group consisting of: cellulose esters, polyvinylbutyral resins, tosylamide (toluensulfonamide) formaldehyde resins, and mixtures thereof.

3. The nail covering system of claim 2 , wherein said cellulose ester is selected from the group consisting of cellulose acetate butyrate, cellulose acetate propionate, and mixtures thereof.

4. The nail covering system of claim 1 , further comprising an adhesion promoter.

5. The nail covering system of claim 4 , wherein said adhesion promoter is selected from the group consisting of:

hydroxypropyl methacrylate (HPMA),

hydroxyethyl methacrylate (HEMA),

ethyl methacrylate (EMA),

tetrahydrofurfuryl methacrylate THFMA,

pyromellitic dianhydride di(meth)acrylate,

pyromellitic dianhydride glyceryl dimethacrylate (PMGDM),

pyromellitic dimethacrylate,

methacroyloxyethyl maleate,

2-hydroxyethyl methacrylate/succinate,

1,3-glycerol dimethacrylate/succinate adduct,

phthalic acid monoethyl methacrylate,

methacroyloxyethyl maleate,

2-hydroxyethyl methacrylate/succinate,

1,3-glycerol dimethacrylate/succinate adduct,

butyl methacrylate,

isobutyl methacrylate,

PEG-4 dimethacrylate,

PPG monomethacrylate,

trimethylolpropane trimethacrylate,

isopropylidenediphenyl bisglycidyl methacrylate,

lauryl methacrylate,

cyclohexyl methacrylate,

hexyl methacrylate,

urethane methacrylate,

triethylene glycol dimethacrylate,

ethylene glycol dimethacrylate,

tetraethylene glycol dimethacrylate,

trimethylolpropane trimethacrylate,

neopentylglycol dimethacylate,

acetoacetoxy methacrylate,

hydroxybutylmethacrylate,

acetoacetoxyethylmethacrylate (AAEMA),

and mixtures thereof.

6. The nail covering system of claim 1 , further comprising at least one PMMA-PMAA copolymer.

7. The nail covering system of claim 1 , further comprising at least one PMGDM.

8. The nail covering system of claim 1 , further comprising a urethane (meth)acrylate.

9. The nail covering system of claim 1 , further comprising up to 5 wt % of a plasticizer.

10. The nail covering system of claim 9 , wherein said plasticizer is diisobutyl adipate.

11. The nail covering system of claim 1 , further comprising up to 10 wt % of a photoinitiator.

12. The nail covering system of claim 11 , wherein said photoinitiator is selected from the group consisting of 2,4,6-trimethylbenzoyldiphenylphosphinate, hydroxycyclohexyl phenyl ketone, benzil dimethyl ketal, and mixtures thereof.

13. The nail covering system of claim 1 , further comprising up to 10 wt % of a colorant.

14. The nail covering system of claim 13 , wherein said colorant is selected from the group consisting of dyes, pigments, effects pigments, and mixtures thereof.

15. The nail covering system of claim 1 , comprising a polypropylene glycol (meth)acrylated monomer.

16. The nail covering system of claim 1 , comprising a polyethylene glycol (meth)acrylated monomer.

17. The system of claim 1 , wherein the non-reactive, solvent-dissolvable polymer and non-reactive solvent are present in sufficient amounts such that, when the coating is cured onto the surface of the nail, the coating cures to an acrylic thermoset lattice layer that is removable from the nail surface within 20 minutes of exposure to organic solvent.

18. The nail covering system of claim 17 , wherein the organic solvent is acetone.

19. The nail covering system of claim 1 , wherein said at least one non-reactive, solvent-dissolvable polymer is a cellulose ester.

20. The nail covering system of claim 19 , wherein said cellulose ester is a cellulose acetate alkylate.

21. The nail covering system of claim 1 , wherein said at least one non-reactive solvent is selected from the group consisting of ketones, alkyl acetates, alcohols, alkanes, alkenes, and mixtures thereof.

22. The nail covering system of claim 8 , wherein said at least one non-reactive solvent is selected from the group consisting of acetone, ethyl acetate, butyl acetate, isopropyl alcohol, ethanol, methyl ethyl ketone, toluene, hexane, and mixtures thereof.

23. A multilayer system for covering a nail surface comprising:

at least a first layer and a second layer,

wherein at least one of the first layer and the second layer comprises a coating curable to an acrylic thermoset lattice layer conforming over the nail surface upon exposure to actinic radiation, and

wherein the coating comprises

a polymerizable (meth)acrylate,

a polypropylene glycol (meth)acrylated monomer or polyethylene glycol (meth)acrylated monomer,

a non-reactive solvent, and

a non-reactive, solvent-dissolvable polymer.

24. The system of claim 1 , wherein the coating when cured comprises an interpenetrating network of the non-reactive solvent-dissolvable polymer.

25. The system of claim 1 , wherein the coating when cured comprises an interconnected network of voids.

Assignments (24)
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 →
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 →
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 →
FIRST LIEN PATENT SECURITY AGREEMENT Recorded May 11, 2020
From: BRANDCO CND 2020 LLC
To: JEFFERIES FINANCE LLC
Reel/Frame 052621/0125 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 9, 2020
From: BEAUTYGE I
To: BRANDCO CND 2020 LLC
Reel/Frame 052618/0740 →
BACK-UP PATENT SECURITY AGREEMENT Recorded May 9, 2020
From: BEAUTYGE I
To: BRANDCO CND 2020 LLC
Reel/Frame 052619/0476 →
BACK-UP PATENT SECURITY AGREEMENT Recorded May 8, 2020
From: CREATIVE NAIL DESIGN, INC.
To: BEAUTYGE I
Reel/Frame 052618/0405 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 8, 2020
From: CREATIVE NAIL DESIGN, INC.
To: BEAUTYGE I
Reel/Frame 052614/0654 →
RELEASE OF SECURITY INTEREST IN CERTAIN PATENTS AT R/F 040223/0526 Recorded May 7, 2020
From: CITIBANK N.A., AS COLLATERAL AGENT
To: CREATIVE NAIL DESIGN, INC.
Reel/Frame 052598/0978 →
RELEASE OF SECURITY INTEREST IN CERTAIN PATENTS AT R/F 040219/0025 Recorded May 7, 2020
From: CITIBANK N.A., AS COLLATERAL AGENT
To: CREATIVE NAIL DESIGN, INC.
Reel/Frame 052599/0044 →
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 →
PATENT SECURITY AGREEMENT (TERM) Recorded Oct 4, 2016
From: CREATIVE NAIL DESIGN, INC.
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 040223/0526 →
PATENT SECURITY AGREEMENT Recorded Oct 4, 2016
From: CREATIVE NAIL DESIGN, INC.
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 040219/0025 →
NOTICE OF RELEASE OF SECURITY INTEREST IN PATENTS Recorded Sep 8, 2016
From: CITICORP USA, INC.
To: REVLON CONSUMER PRODUCTS CORPORATION
Reel/Frame 039970/0487 →
NOTICE OF RELEASE OF SECURITY INTEREST IN PATENTS Recorded Sep 8, 2016
From: CITICORP USA, INC.
To: CREATIVE NAIL DESIGN, INC.; ROUX LABORATORIES, INC.
Reel/Frame 039970/0508 →
PATENT SECURITY AGREEMENT Recorded Jan 29, 2016
From: REVLON CONSUMER PRODUCTS CORPORATION
To: CITICORP USA, INC.
Reel/Frame 037640/0607 →
SECURITY AGREEMENT Recorded Jan 29, 2014
From: CREATIVE NAIL DESIGN, INC.; ROUX LABORATORIES, INC.
To: CITICORP USA, INC., AS COLLATERAL AGENT
Reel/Frame 032154/0401 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 31, 2012
From: CONGER, CHAD; VU, THONG
To: CREATIVE NAIL DESIGN, INC.
Reel/Frame 029546/0040 →