IP Library Granted Patent US 8,901,199
Granted Patent B2
US 8,901,199 · App. 13/042,436 · Granted Dec 2, 2014

Compositions and methods for UV-curable cosmetic nail coatings

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Quick Facts
Patent No.
US 8,901,199
App. No.
13/042,436
Granted
Dec 2, 2014
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 that provide improved adhesion-promoting and improved solvent-susceptibility.

Claims (155)

1. The removable, adhesion-promoting nail coating composition comprising a polymerizable (meth)acrylate, a urethane (meth)acrylate resin and an adhesion promoter 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,

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,

acetoacetoxyethyl methacrylate, (AAEMA)

polyetheramine,

glycidyl methacrylates,

maleic anhydride,

terpolymers containing vinyl acetate,

organosilanes,

organotitanates,

chlorinated polyolefins,

sucrose acetate isobutyrate,

caprylic/capric triglyceride,

glyceryl hydrogenated rosinate,

pentaerythryl hydrogenated rosinate,

styrene/methyl styrene/indene copolymer,

blocked isocyanate PVC,

polyamidoamine PVC,

and mixtures thereof;

wherein the polymerizable (meth)acrylate is different from the adhesion promoter, and the urethane (meth)acrylate resin is different from the adhesion promoter,

wherein said composition cures to a thermoset, and

removal of the cured coating from a nail surface upon exposure to an organic solvent is achieved in less than 20 minutes without abrading the coating or nail surface.

2. The removable, adhesion-promoting nail coating composition according to claim 1 , further comprising a solvent-sensitivity enhancing monomer or oligomer and a non-reactive, solvent-dissolvable polymer.

3. The removable, adhesion-promoting nail coating composition of claim 2 , wherein said non-reactive, solvent-dissolvable polymer is selected from the group consisting of:

cellulose esters,

polyvinylbutyral resins,

tosylamide (toluensulfonamide) formaldehyde resins,

ethyl tosylamide,

adipic acid/fumaric acid/phthalic acid/tricyclodecane dimethanol copolymer,

adipic acid/neopentyl glycol/trimellitic anhydride copolymer,

phthalic anhydride/trimellitic anhydride/glycols copolymer,

polyethyl cellulose,

polyhydroxypropyl cellulose,

polyethyl acrylate oxide,

poly lactic acid,

nitrocellulose,

and mixtures thereof.

4. The removable, adhesion-promoting nail coating composition of claim 3 , wherein said cellulose ester is selected from the group consisting of cellulose acetate butyrate, cellulose acetate propionate, and mixtures thereof.

5. The removable, adhesion-promoting nail coating composition of claim 1 , wherein said polymerizable (meth)acrylate is a polyol modified (meth)acrylate.

6. The removable, adhesion-promoting nail coating composition of claim 5 , wherein said polyol modified (meth)acrylate is a polyol modified urethane (meth)acrylate.

7. The removable, adhesion-promoting nail coating composition of claim 1 , wherein said polymerizable (meth)acrylate is a polyalkyleneglycol modified (meth)acrylate.

8. The removable, adhesion-promoting nail coating composition of claim 1 , further comprising at least one PMMA-PMAA copolymer.

9. The removable, adhesion-promoting nail coating composition of claim 1 , wherein the adhesion promoter comprises at least one PMGDM.

10. The removable, adhesion-promoting nail coating composition of claim 1 , wherein said thermoset remains intact to at least 150 acetone double rubs.

11. The removable, adhesion-promoting nail coating composition of claim 1 , further comprising a non-reactive solvent.

12. The removable, adhesion-promoting nail coating composition of claim 2 , wherein said solvent-sensitivity enhancing monomer or oligomer is selected from the group consisting of:

polyethylene glycol (meth)acrylates,

polypropylene glycol (meth)acrylates,

polybutylene glycol (meth)acrylates,

propoxylated allyl methacrylate

methoxy polyethylene glycol (350) monomethacrylate,

polyethylene glycol (600) monomethacrylate,

stearyl methacrylate,

tridecyl methacrylate,

hydroxyethyl methacrylate acetate,

and mixtures thereof;

wherein the solvent-sensitivity enhancing monomer or oligomer is different from the adhesion promoter.

13. The removable, adhesion-promoting nail coating composition of claim 1 , further comprising up to 5 wt % of a plasticizer.

14. The removable, adhesion-promoting nail coating composition of claim 13 , wherein said plasticizer is selected from the group consisting of:

esters,

low volatility solvents

paraffinic hydrocarbons

butyrolactone,

xylene,

methyl isobutyl ketone,

non-ionic surfactants,

non-ionic silicones,

isostearyl isononanoate,

silicones,

diisobutyl adipate,

trimethyl pentanyl diiisobutyrate,

acetyl tributyl citrate,

and mixtures thereof.

15. The removable, adhesion-promoting nail coating composition of claim 1 , further comprising up to 10 wt % of a photoinitiator.

16. The removable, adhesion-promoting nail coating composition of claim 15 , wherein said photoinitiator is selected from the group consisting of ethyl trimethylbenzoyl phenylphosphinate, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, hydroxycyclohexyl phenyl ketone, benzyl dimethyl ketal, and mixtures thereof.

17. The removable, adhesion-promoting nail coating composition of claim 1 , further comprising up to 5 wt % of a UV-absorber.

18. The removable, adhesion-promoting nail coating composition of claim 17 , wherein said UV-absorber is selected from the group consisting of:

hydroxy benzotriazole compounds,

2-(2-hydroxy-5′-methylphenyl)benzotriazole,

benzophenones 1-12,

3-benzylidene camphor,

benzyl salicylate,

borneolone,

bumetrizole,

PABA,

butyl PABA,

butyl methoxydibenzoymethane,

cinoxate,

DEA-methoxycinnamate,

dibenzoxazoyl naphthalene,

digalloyl trioleate,

diisopropyl methyl cinnamate,

and mixtures thereof.

19. The removable, adhesion-promoting nail coating composition of claim 1 , further comprising a filler.

20. The removable, adhesion-promoting nail coating composition of claim 19 , wherein said filler is selected from the group consisting of silica, metal oxide, nanosilica, nanoalumina, and mixtures thereof.

21. The removable, adhesion-promoting nail coating composition of claim 1 , further comprising up to 10 wt % of a colorant.

22. The removable, adhesion-promoting nail coating composition of claim 21 , wherein said colorant is selected from the group consisting of dyes, pigments, effects pigments and mixtures thereof.

23. The removable, adhesion-promoting nail coating composition of claim 1 , further comprising a rheology modifier.

24. The removable, adhesion-promoting nail coating composition of claim 23 , wherein said rheology modifier is selected from the group consisting of:

stearalkonium hectorite,

calcium aluminum borosilicate,

calcium sodium borosilicate,

synthetic fluorphlogopite,

silica,

titanium oxide,

tin oxide,

and mixtures thereof.

25. A method of providing ease of removal of a cured nail coating comprising adding at least one solvent-sensitivity enhancing monomer or oligomer that is an acrylated or methacrylated monomer of polyethyleneglycol (PEG), polypropyleneglycol (PPG), or polybutyleneglycol (PBG) to the nail coating composition of claim 1 before curing.

26. The removable, adhesion-promoting nail coating composition of claim 1 , wherein the polymerizable (meth)acrylate is selected from the group consisting of hydroxypropyl methacrylate and hydroxyethyl methacrylate.

27. The removable, adhesion-promoting nail coating composition of claim 1 , wherein the polymerizable (meth)acrylate is hydroxypropyl methacrylate.

28. The removable, adhesion-promoting nail coating composition of claim 1 , wherein the polymerizable (meth)acrylate is hydroxyethyl methacrylate.

29. The removable, adhesion-promoting nail coating composition of claim 1 , wherein the adhesion promoter is selected from the group consisting of hydroxypropyl methacrylate, hydroxyethyl methacrylate and tetrahydrofurfuryl methacrylate (THFMA).

30. The removable, adhesion-promoting nail coating composition of claim 1 , wherein the adhesion promoter is tetrahydrofurfuryl methacrylate (THFMA).

31. The removable, adhesion-promoting nail coating composition of claim 1 , wherein the polymerizable (meth)acrylate and the adhesion promoter are hydroxypropyl methacrylate and hydroxyethyl methacrylate, respectively.

32. The removable, adhesion-promoting nail coating composition according to claim 1 , further comprising a non-reactive, solvent-dissolvable polymer.

33. The removable, adhesion-promoting nail coating composition of claim 32 , wherein said non-reactive, solvent-dissolvable polymer is selected from the group consisting of:

cellulose esters,

polyvinylbutyral resins,

tosylamide (toluensulfonamide) formaldehyde resins,

ethyl tosylamide,

adipic acid/fumaric acid/phthalic acid/tricyclodecane dimethanol copolymer,

adipic acid/neopentyl glycol/trimellitic anhydride copolymer,

phthalic anhydride/trimellitic anhydride/glycols copolymer,

polyethyl cellulose,

polyhydroxypropyl cellulose,

polyethyl acrylate oxide,

poly lactic acid,

nitrocellulose,

and mixtures thereof.

34. The removable, adhesion-promoting nail coating composition of claim 33 , wherein said cellulose ester is selected from the group consisting of cellulose acetate butyrate, cellulose acetate propionate, and mixtures thereof.

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 12, 2012
From: VU, THONG; CONGER, CHAD; LARSEN, DIANE MARIE; VALIA, DAVID; SCHOON, DOUGLAS D.
To: CREATIVE NAIL DESIGN, INC.
Reel/Frame 028035/0960 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 5, 2012
From: SCHOON, DOUGLAS D.
To: CREATIVE NAIL DESIGN, INC.
Reel/Frame 027998/0339 →