IP Library Granted Patent US 8,541,482
Granted Patent B2
US 8,541,482 · App. 12/573,640 · Granted Sep 24, 2013

Removable multilayer nail coating system and methods therefore

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Quick Facts
Patent No.
US 8,541,482
App. No.
12/573,640
Granted
Sep 24, 2013
Kind
B2
Abstract

The present disclosure relates generally to compositions for nail coatings, and particularly, but not by way of limitation, to polymerizable compositions. The disclosure further relates to methods of making a polymerizable, protective and scratch resistant topcoat layer that can be easily removed.

Claims (36)

1. A multilayer nail covering system comprising at least a first layer and a second layer,

wherein at least one of the first and second layer is curable to an acrylic thermoset lattice layer covering a nail surface upon exposure to actinic radiation;

wherein at least one of the first or second layer comprises:

hydroxypropyl methacrylate (HPMA),

at least one reactive urethane (meth)acrylate, and

a sufficient amount of a non-reactive, solvent-dissolvable polymer and a non-reactive solvent such that, when cured to the nail surface, the system is removable from the nail surface within 20 minutes of exposure to organic solvent.

2. The nail covering system of claim 1 , wherein the at least one layer further comprises hydroxyethylmethacrylate (HEMA).

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

4. The nail covering system of claim 3 , wherein said cellulose ester is a cellulose acetate alkylate.

5. The nail covering system of claim 4 , wherein said cellulose acetate alkylate is selected from the group consisting of cellulose acetate butyrate, cellulose acetate propionate, and mixtures thereof.

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

7. The nail covering system of claim 1 , wherein said 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.

8. The nail covering system of claim 1 , wherein the at least one layer further comprises at least one photoinitiator.

9. The nail covering system of claim 8 , wherein said at least one photoinitiator is selected from the group consisting of benzoylphenylphosphinates, cyclohexylphenyl ketones, benzyl ketals, and mixtures thereof.

10. The nail covering system of claim 9 , wherein said at least one photoinitiator is selected from the group consisting of 2,4,6-trimethylbenzoyldiphenylphosphinate, hydroxycyclohexyl phenyl ketone, benzyl dimethyl ketal, and mixtures thereof.

11. The nail covering system of claim 1 , wherein the at least one layer further comprises at least one addition-polymerizable, ethylenically-unsaturated monomer.

12. The nail covering system of claim 1 , wherein upon exposure to actinic radiation, the at least one layer cures to an acrylic thermoset lattice layer having voids defined therein, wherein at least a portion of said voids contain said at least one non-reactive, solvent-dissolvable polymer.

13. The nail covering system of claim 1 , wherein said non-reactive, solvent-dissolvable polymer is present at from about 5 to about 90 wt %.

14. The nail covering system of claim 1 , wherein said non-reactive, solvent-dissolvable polymer is present at from about 20 to about 80 wt %.

15. The nail covering system of claim 1 , wherein said non-reactive, solvent-dissolvable polymer is present at from about 30 to about 70 wt %.

16. The nail covering system of claim 1 , wherein the organic solvent is acetone.

17. The nail covering system according to claim 1 , wherein the at least one layer further comprises an adhesion-promoting (meth)acrylate.

18. The nail covering system according to claim 17 , wherein said adhesion-promoting (meth)acrylate is selected from the group consisting of tetrahydrofurfural methacrylate, ethyl methacrylate, pyromellitic dianhydride glyceryl dimethacrylate, and mixtures thereof.

19. The nail covering system according to claim 1 , wherein the at least one layer further comprises pyromellitic glyceryl dimethacrylate.

20. The nail covering system according to claim 1 , wherein the at least one layer further comprises at least one polyalkylene glycol mono(meth)acrylate.

21. The nail covering system according to claim 20 , wherein said at least one polyalkylene glycol mono(meth)acrylate is a compound selected from the group consisting of polypropylene glycol monomethacrylates, polyethylene glycol monomethacrylates, and mixtures thereof.

22. The nail covering system of claim 1 , wherein said at least one urethane (meth)acrylate has a molecular weight of from about 300 to about 1,000.

23. The nail covering system of claim 1 , wherein the at least one layer further comprises at least one plasticizer having the general structure RCO—OR′ where RCO— represents a carboxylic acid radical, where —OR′ is an alcohol residue, and where R and R′ are fatty radicals having 6 to 30 saturated or unsaturated carbon atoms.

24. The nail covering system according to claim 1 , wherein the at least one layer further comprises a reactive (meth)acrylate monomer or polymer selected from the group consisting of: hydroxyethylmethacrylate (HEMA), ethyl methacrylate (EMA), tetrahydrofurfuryl methacrylate (THFMA), pyromellitic dianhydride di(meth)acrylate, pyromellitic dianhydride glyceryl dimethacrylate, pyromellitic dimethacrylate, methacroyloxyethyl maleate, 2-hydroxyethyl methacrylate/succinate, 1,3-glycerol dimethacrylate/succinate adduct, phthalic acid monoethyl methacrylate, acetoacetoxy ethyl methacylate (AAEMA), and mixtures thereof.

25. The nail covering system according to claim 1 , having a hardness of at least 3H on the pencil hardness test.

26. A nail covering system comprising: a basecoat layer; an intermediate layer; and a topcoat layer; wherein at least one layer comprises:

(a) hydroxypropyl methacrylate (HPMA);

(b) at least one reactive urethane (meth)acrylate;

(c) at least one non-reactive, solvent-dissolvable polymer; and

(d) at least one non-reactive solvent; and

wherein, upon exposure to actinic radiation, the at least one layer cures to an acrylic thermoset lattice layer covering a nail surface.

Assignments (25)
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 Apr 5, 2012
From: SCHOON, DOUGLAS D.
To: CREATIVE NAIL DESIGN, INC.
Reel/Frame 027998/0285 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 28, 2010
From: VU, THONG
To: CREATIVE NAIL DESIGN, INC.
Reel/Frame 023863/0383 →