IP Library Granted Patent US 8,367,742
Granted Patent B2
US 8,367,742 · App. 13/303,584 · Granted Feb 5, 2013

Removable color layer for artificial nail coatings and methods therefore

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Quick Facts
Patent No.
US 8,367,742
App. No.
13/303,584
Granted
Feb 5, 2013
Kind
B2
Abstract

The present disclosure relates to a nail coating system comprising a basecoat, a color layer, and a topcoat. The system of the present disclosure may be applied to natural and/or pre-existing artificial nail coatings. 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 color layers polymerized therefrom. The disclosure further relates to methods of making a polymerized color layer.

Claims (75)

1. A polymerizable composition comprising:

at least one first reactive (meth)acrylate monomer comprising HPMA;

at least one second reactive (meth)acrylate monomer selected from the group consisting of hydroxyethylmethacrylate (HEMA), hydroxypropylmethacrylate (HPMA), 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;

at least one reactive urethane (meth)acrylate;

at least one addition-polymerizable, ethylenically-unsaturated monomer;

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

at least one non-reactive solvent;

wherein upon exposure to a polymerization accelerant, said polymerizable composition cures to an acrylic thermoset having voids defined therein.

2. The polymerizable composition according to claim 1 , further comprising at least one compound selected from the group consisting of polypropylene glycol monomethacrylates, polyethylene glycol monomethacrylates, and mixtures thereof.

3. The polymerizable composition according to claim 1 , wherein said polymerization accelerant is selected from the group consisting of thermal conduction and/or radiation, visible radiation, UV radiation, electron beam radiation, amines, peroxides, and combinations thereof.

4. The polymerizable composition of claim 1 , wherein said at least one non-reactive, solvent-dissolvable polymer is a cellulose ester.

5. The polymerizable composition of claim 4 , wherein said cellulose ester is a cellulose acetate alkylate.

6. The polymerizable composition of claim 5 , wherein said cellulose acetate alkylate is selected from the group consisting of cellulose acetate butyrate, cellulose acetate propionate, and mixtures thereof.

7. The polymerizable composition of claim 1 , wherein said at least one non-reactive, solvent-dissolvable polymer is present at from about 5 to about 70 wt %.

8. The polymerizable composition of claim 1 , wherein said at least one non-reactive, solvent-dissolvable polymer is present at from about 10 to about 60 wt %.

9. The polymerizable composition of claim 1 , wherein said at least one non-reactive, solvent-dissolvable polymer is present at from about 20 to about 50 wt %.

10. The polymerizable composition according to claim 1 , further comprising an adhesion-promoting (meth)acrylate.

11. The polymerizable composition according to claim 10 , wherein said adhesion-promoting (meth)acrylate is selected from the group consisting of tetrahydrofurfural methacrylate, ethyl methacrylate, hydroxypropyl methacrylate, pyromellitic dianhydride glyceryl dimethacrylate, and mixtures thereof.

12. The polymerizable composition according to claim 1 , further comprising pyromellitic glyceryl dimethacrylate.

13. The polymerizable composition of claim 1 , further comprising at least one colorant.

14. The polymerizable composition of claim 1 , further comprising at least one rheology agent.

15. The polymerizable composition of claim 14 , wherein said at least one rheology agent is a fumed silica.

16. The polymerizable composition of claim 15 , wherein a surface of said fumed silica is modified with polydimethylsiloxane.

17. The polymerizable composition of claim 5 , wherein said at least one rheology agent is a polyamide.

18. The polymerizable composition of claim 14 , wherein said at least one rheology agent present at up to about 10 wt %.

19. The polymerizable composition of claim 1 , wherein said at least one at least one urethane (meth)acrylate has a molecular weight of from about 300 to about 1,000.

20. The polymerizable composition 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.

21. The polymerizable composition of claim 1 , 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.

22. The polymerizable composition of claim 1 , wherein said at least one non-reactive solvent is acetone.

23. The polymerizable composition of claim 1 , wherein said at least one non-reactive solvent is included at up to about 70 weight percent.

24. The polymerizable composition of claim 1 , further comprising at least one photoinitiator.

25. The polymerizable composition of claim 24 , wherein said at least one photoinitiator is selected from the group consisting of benzoylphenylphosphinates, cyclohexylphenyl ketones, benzyl ketals, and mixtures thereof.

26. A polymerizable composition comprising:

at least one first reactive (meth)acrylate monomer selected from the group consisting of ethyl methacrylate (EMA), hydroxypropyl methacrylates (HPMA), pyromellitic dianhydride glyceryl dimethacrylate, and mixtures thereof;

at least one second reactive (meth)acrylate comprising HEMA;

at least one reactive urethane (meth)acrylate;

at least one addition-polymerizable, ethylenically-unsaturated monomer;

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

at least one non-reactive solvent;

wherein upon exposure to a polymerization accelerant, said polymerizable composition cures to an acrylic thermoset having voids defined therein.

27. The polymerizable composition of claim 1 , wherein the at least one second reactive (meth)acrylate is HEMA.

28. The polymerizable composition of claim 27 , wherein the addition-polymerizable ethylenically unsaturated monomer has the formula:

wherein R1 is H, a C1-30 straight or branched chain alkyl, aryl, aralkyl; R2 is a pyrrolidone, or a substituted or unsubstituted aromatic, alicyclic, or bicyclic ring where the substituents are C1-30 straight or branched chain alkyl, or COOM wherein M is H, a C1-30 straight or branched chain alkyl, pyrrolidone, or a substituted or unsubstituted aromatic, alicyclic, or bicyclic ring where the substituents are C1-30 straight or branched chain alkyl which may be substituted with one or more hydroxyl groups, or [(CH2)mO]nH wherein m is 1-20, and n is 1-200.

29. The polymerizable composition of claim 27 , wherein the addition-polymerizable ethylenically unsaturated monomer is a difunctional monomer having the formula:

wherein R3 and R4 are each independently H, a C1-30 straight or branch chain alkyl, aryl, or aralkyl; and X is [(CH2)xOy]z wherein x is 1-20, and y is 1-20, and z is 1-100.

30. The polymerizable composition of claim 27 , wherein the addition-polymerizable ethylenically unsaturated monomer is selected from the group consisting of trifunctional acrylates, trifunctional methacrylates, polyfunctional acrylates and polyfunctional methacrylates.

31. The polymerizable composition according to claim 26 , further comprising at least one compound selected from the group consisting of polypropylene glycol monomethacrylates, polyethylene glycol monomethacrylates, and mixtures thereof.

32. The polymerizable composition according to claim 26 , wherein said polymerization accelerant is selected from the group consisting of thermal conduction and/or radiation, visible radiation, UV radiation, electron beam radiation, amines, peroxides, and combinations thereof.

33. The polymerizable composition of claim 26 , wherein said at least one non-reactive, solvent-dissolvable polymer is a cellulose ester.

34. The polymerizable composition of claim 33 , wherein said cellulose ester is a cellulose acetate alkylate.

35. The polymerizable composition of claim 34 , wherein said cellulose acetate alkylate is selected from the group consisting of cellulose acetate butyrate, cellulose acetate propionate, and mixtures thereof.

36. The polymerizable composition of claim 26 , wherein said at least one non-reactive, solvent-dissolvable polymer is present at from about 5 to about 70 wt %.

37. The polymerizable composition of claim 26 , wherein said at least one non-reactive, solvent-dissolvable polymer is present at from about 10 to about 60 wt %.

38. The polymerizable composition of claim 26 , wherein said at least one non-reactive, solvent-dissolvable polymer is present at from about 20 to about 50 wt %.

39. The polymerizable composition according to claim 26 , further comprising an adhesion-promoting (meth)acrylate.

40. The polymerizable composition according to claim 39 , wherein said adhesion-promoting (meth)acrylate is selected from the group consisting of tetrahydrofurfural methacrylate, ethyl methacrylate, hydroxypropyl methacrylate, pyromellitic dianhydride glyceryl dimethacrylate, and mixtures thereof.

41. The polymerizable composition according to claim 26 , further comprising pyromellitic glyceryl dimethacrylate.

42. The polymerizable composition of claim 26 , further comprising at least one colorant.

43. The polymerizable composition of claim 26 , further comprising at least one rheology agent.

44. The polymerizable composition of claim 43 , wherein said at least one rheology agent is a fumed silica.

45. The polymerizable composition of claim 44 , wherein a surface of said fumed silica is modified with polydimethylsiloxane.

46. The polymerizable composition of claim 44 , wherein said at least one rheology agent is a polyamide.

47. The polymerizable composition of claim 43 , wherein said at least one rheology agent present at up to about 10 wt %.

48. The polymerizable composition of claim 26 , wherein said at least one at least one urethane (meth)acrylate has a molecular weight of from about 300 to about 1,000.

49. The polymerizable composition of claim 26 , wherein said at least one non-reactive solvent is selected from the group consisting of ketones, alkyl acetates, alcohols, alkanes, alkenes, and mixtures thereof.

50. The polymerizable composition of claim 26 , 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.

51. The polymerizable composition of claim 26 , wherein said at least one non-reactive solvent is acetone.

52. The polymerizable composition of claim 26 , wherein said at least one non-reactive solvent is included at up to about 70 weight percent.

53. The polymerizable composition of claim 26 , further comprising at least one photoinitiator.

54. The polymerizable composition of claim 53 , wherein said at least one photoinitiator is selected from the group consisting of benzoylphenylphosphinates, cyclohexylphenyl ketones, benzyl ketals, and mixtures thereof.

55. The polymerizable composition of claim 26 , wherein the addition-polymerizable ethylenically unsaturated monomer has the formula:

wherein R1 is H, a C1-30 straight or branched chain alkyl, aryl, aralkyl; R2 is a pyrrolidone, or a substituted or unsubstituted aromatic, alicyclic, or bicyclic ring where the substituents are C1-30 straight or branched chain alkyl, or COOM wherein M is H, a C1-30 straight or branched chain alkyl, pyrrolidone, or a substituted or unsubstituted aromatic, alicyclic, or bicyclic ring where the substituents are C1-30 straight or branched chain alkyl which may be substituted with one or more hydroxyl groups, or [(CH2)mO]nH wherein m is 1-20, and n is 1-200.

56. The polymerizable composition of claim 26 , wherein the addition-polymerizable ethylenically unsaturated monomer is a difunctional monomer having the formula:

wherein R3 and R4 are each independently H, a C1-30 straight or branch chain alkyl, aryl, or aralkyl; and X is [(CH 2 )xOy]z wherein x is 1-20, and y is 1-20, and z is 1-100.

57. The polymerizable composition of claim 26 , wherein the addition-polymerizable ethylenically unsaturated monomer is selected from the group consisting of trifunctional acrylates, trifunctional methacrylates, polyfunctional acrylates and polyfunctional methacrylates.

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 Dec 13, 2012
From: SCHOON, DOUGLAS D.
To: CREATIVE NAIL DESIGN, INC.
Reel/Frame 029463/0771 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 13, 2012
From: VU, THONG; LARSEN, DIANE MARIE; CONGER, CHAD
To: CREATIVE NAIL DESIGN, INC.
Reel/Frame 029463/0877 →