IP Library Granted Patent US 9,713,585
Granted Patent B2
US 9,713,585 · App. 14/786,491 · Granted Jul 25, 2017

Nail coatings having enhanced adhesion

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Quick Facts
Patent No.
US 9,713,585
App. No.
14/786,491
Granted
Jul 25, 2017
Kind
B2
Abstract

Adhesion of a composition for nail coatings be improved by addition of a polyhedral oligomeric silsesquioxane (POSS). Nail coating compositions that benefit from the addition of a POSS include enamels, reactive composition such as those containing acrylates, solventless compositions and water-based compositions.

Claims (17)

1. A method of improving adhesion of a nail coating comprising:

providing a nail coating composition comprising at least one reactive monomer, oligomer or polymer selected from the group consisting of reactive (meth)acrylates and mixture thereof;

adding at least one polyhedral oligomeric silsesquioxane to the nail coating composition, wherein the at least one polyhedral oligomeric silsesquioxane has the formula (C 6 H 11 O 2 ) n (SiO 1.5 ) n , where n is 8, 10, or 12, and wherein (C 6 H 11 O 2 ) represents:

2. The method of claim 1 , wherein the at least one reactive monomer, oligomer or polymer is a reactive (meth)acrylate.

3. The method of claim 2 , wherein the reactive (meth)acrylate is selected from the group consisting of hydroxypropyl methacrylate, hydroxyethyl methacrylate, ethyl methacrylate, tetrahydrofurfuryl methacrylate, pyromellitic dianhydride di(meth)acrylate, pyromellitic dianhydride glyceryl di methacrylate, pyromellitic dimethacrylate, methacroyloxyethyl maleate, 2-hydroxyethyl methacrylate/succinate, 1,3-glycerol dimethacrylate/succinate adduct, phthalic acid monoethyl methacrylate, and a mixture thereof.

4. The method of claim 1 , wherein the nail coating composition further comprises a film-forming polymer or a non-reactive solvent-dissolvable polymer.

5. The method of claim 4 , wherein the non-reactive, solvent-dissolvable polymer or film-forming polymer is selected from the group consisting of a cellulose ester, a cellulose acetate alkylate, a cellulose acetate butyrate, a cellulose acetate propionate, 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, polylactic acid, nitrocellulose, and mixtures thereof.

6. The method of claim 1 , wherein the nail coating composition further comprises a high-molecular weight (meth)acrylate polymer or copolymer.

7. The method of claim 1 , wherein the nail coating composition further comprises a polymethylmethacrylate-polymethylacrylic acid copolymer.

8. The method of claim 1 , wherein the nail coating composition further comprises a solvent.

9. The method of claim 8 , wherein the solvent is a non-aqueous solvent.

10. The method of claim 8 , wherein the solvent is water.

11. The method of claim 1 , wherein the nail coating composition further comprises a reactive polypropylene glycol (meth)acrylated monomer or a reactive polyethylene glycol (meth)acrylated monomer.

12. The method of claim 1 , wherein the nail coating composition further comprises a polymerization accelerator, a polymerization initiator, or a combination thereof.

13. The method of claim 1 , wherein the nail coating composition further comprises an adhesion promoter selected from the group consisting of hydroxypropyl methacrylate, hydroxyethyl methacrylate, ethyl methacrylate, tetrahydrofurfuryl methacrylate, 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, 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, acetoacetoxyethyl methacrylate, 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, and a mixture thereof.

14. The method of claim 1 , wherein the nail coating composition further comprises at least one non-reactive, solvent dissolvable polymer and the reactive monomer, oligomer or polymer is a reactive (meth)acrylate.

15. The method of claim 1 , wherein the nail coating composition further comprises at least one polymethylmethacrylate-polymethylacrylic acid copolymer; at least one non-reactive, solvent dissolvable polymer; and at least one non-reactive solvent; and wherein the reactive monomer, oligomer or polymer is a reactive (meth)acrylate.

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 →
FIRST LIEN PATENT SECURITY AGREEMENT Recorded May 11, 2020
From: BRANDCO CND 2020 LLC
To: JEFFERIES FINANCE LLC
Reel/Frame 052621/0125 →
SECOND LIEN PATENT SECURITY AGREEMENT Recorded May 11, 2020
From: BRANDCO CND 2020 LLC
To: JEFFERIES FINANCE LLC
Reel/Frame 052620/0506 →
THIRD LIEN PATENT SECURITY AGREEMENT Recorded May 11, 2020
From: BRANDCO CND 2020 LLC
To: JEFFERIES FINANCE LLC
Reel/Frame 052620/0492 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 8, 2020
From: CREATIVE NAIL DESIGN, INC.
To: BEAUTYGE I
Reel/Frame 052614/0654 →
BACK-UP PATENT SECURITY AGREEMENT Recorded May 8, 2020
From: CREATIVE NAIL DESIGN, INC.
To: BEAUTYGE I
Reel/Frame 052618/0405 →
RELEASE OF SECURITY INTEREST IN CERTAIN PATENTS AT R/F 044203/0934 Recorded May 7, 2020
From: CITIBANK N.A., AS COLLATERAL AGENT
To: CREATIVE NAIL DESIGN, INC.
Reel/Frame 052600/0486 →
RELEASE OF SECURITY INTEREST IN CERTAIN PATENTS AT R/F 044203/0882 Recorded May 7, 2020
From: CITIBANK N.A., AS COLLATERAL AGENT
To: CREATIVE NAIL DESIGN, INC.
Reel/Frame 052600/0321 →
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 →
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 →
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 (ABL) Recorded Oct 12, 2017
From: CREATIVE NAIL DESIGN, INC.
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 044203/0882 →
PATENT SECURITY AGREEMENT (TERM) Recorded Oct 12, 2017
From: CREATIVE NAIL DESIGN, INC.
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 044203/0934 →
PATENT SECURITY AGREEMENT Recorded Oct 4, 2016
From: CREATIVE NAIL DESIGN, INC.
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 040219/0025 →
PATENT SECURITY AGREEMENT (TERM) Recorded Oct 4, 2016
From: CREATIVE NAIL DESIGN, INC.
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 040223/0526 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 5, 2015
From: VALIA, DAVID; ELLIS, JAMIE
To: CREATIVE NAIL DESIGN, INC.
Reel/Frame 036971/0479 →