IP Library Granted Patent US 11,166,901
Granted Patent B2
US 11,166,901 · App. 16/349,480 · Granted Nov 9, 2021

Photopolymerizable coating for nails

Inventors: Elizabeta Pavlovic (Los Angeles, CA); Sunan Yuvavanich (Thousand Oaks, CA)
A61K8/8147A61K8/44A61K8/731A61Q3/02A61Q3/04
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Quick Facts
Patent No.
US 11,166,901
App. No.
16/349,480
Granted
Nov 9, 2021
Kind
B2
Abstract

A photopolymerizable composition for forming a photopolymerized nail top coating of a substantially uniform mixture of ethyl cellulose and crosslinked (meth)acrylate polymer is disclosed.

Claims (22)

1. A composition suitable for formation of a polymerized coating on a nail, comprising: a non-solvent mixture of one or more (meth)acrylate monomers, ethyl cellulose and a combination of two di-(hydroxyethylmethacryloyl) trimethylhexyl dicarbamates, the first dicarbamate having a weight average molecular weight in the range of 13 kDa to 17 kDa and the second dicarbamate having a weight average molecular weight in the range of 500 Da to 700 Da.

2. A composition according to claim 1 wherein the one or more (meth)acrylate monomers are at least hydroxypropyl (meth)acrylate.

3. A composition according to claim 1 wherein the one or more (meth)acrylate monomers are at least hydroxypropyl (meth)acrylate and hydroxyethyl (meth)acrylate.

4. A composition according to claim 1 wherein the one or more (meth)acrylate monomers consist essentially of hydroxypropyl (meth)acrylate, hydroxyethyl (meth)acrylate, isobornyl (meth)acrylate and acrylic acid.

5. A composition according to claim 1 wherein the one or more (meth)acrylate monomers consist essentially of hydroxypropyl (meth)acrylate.

6. A composition according to claim 1 wherein the weight percentage ranges of ingredients relative to the total weight of the composition are about 40 wt % to about 60 wt % for the (meth)acrylate monomers, about 2 wt % to about 4 wt % for the ethyl cellulose, about 25 wt % to about 35 wt % for the first dicarbamate and about 10 wt % to about 20 wt % for the second dicarbamate.

7. A composition according to claim 4 wherein the weight percentage ranges relative to the total weight of the composition are about 25 wt % to about 60 wt % for hydroxypropyl (meth)acrylate; about 0 wt % to about 15 wt % for hydroxyethyl (meth)acrylate, about 0 wt % to about 25 wt % for isobornyl (meth)acrylate and about 0 wt % to about 2 wt % for acrylic acid.

8. A photopolymerized composition of a non-solvent mixture of one or more (meth)acrylate monomers, ethyl cellulose, a phosphine oxide photoinitiator, and a combination of two dihydroxyethyl methacryloyl trimethylhexyl dicarbamates, the first dicarbamate having a weight average molecular weight in the range of 13 kDa to 17 kDa and the second dicarbamate having a weight average molecular weight in the range of 500 Da to 700 Da.

9. A photopolymerized composition of claim 8 wherein the one or more (meth)acrylate monomers and two dicarbamates form a crosslinked poly(meth)acrylate network.

10. A photopolymerized composition according to claim 9 wherein the (meth)acrylate monomers include at least hydroxyethyl (meth)acrylate.

11. A photopolymerized composition according to claim 9 wherein the (meth)acrylate monomers include at least hydroxyethyl (meth)acrylate and hydroxypropyl (meth)acrylate.

12. A photopolymerized composition according to claim 9 wherein the (meth)acrylate monomers consist essentially of hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, isobornyl (meth)acrylate and acrylic acid.

13. A polymerized coating suitable for covering a nail comprising a photopolymerized composition of a non-solvent mixture comprising hydroxypropyl (meth)acrylate, ethyl cellulose, a phosphine oxide photoinitiator, and a combination of two dihydroxyethyl methacryloyl trimethylhexyl dicarbamates, the first dicarbamate having a weight average molecular weight in the range of 13 kDa to 17 kDa and the second dicarbamate having a weight average molecular weight in the range of 500 Da to 700 Da.

14. A polymerized coating according to claim 13 comprising a photopolymerized composition wherein the mixture further comprises hydroxyethyl (meth)acrylate.

15. A polymerized coating according to claim 13 comprising a photopolymerized composition wherein the mixture further comprises acrylic acid and isobornyl (meth)acrylate.

16. A method for forming a polymerized coating on a nail comprising the steps of:

coating a nail with a photopolymerizable composition of a non-solvent mixture of one or more (meth)acrylate monomers, ethyl cellulose, a phosphine oxide photoinitiator, and a combination of two dihydroxyethyl methacryloyl trimethylhexyl dicarbamates, the first dicarbamate having a weight average molecular weight in the range of 13 kDa to 17 kDa and the second dicarbamate having a weight average molecular weight in the range of 500 Da to 700, and

exposing the photopolymerizable composition with UV radiation for a sufficient time to cure the composition and produce a polymerized coating.

17. A method for removal of a polymerized coating of a photopolymerized composition of a non-solvent mixture of one or more (meth)acrylate monomers, ethyl cellulose, a phosphine oxide photoinitiator, and a combination of two dihydroxyethyl methacryloyl trimethylhexyl dicarbamates, the first dicarbamate having a weight average molecular weight in the range of 13 kDa to 17 kDa and the second dicarbamate having a weight average molecular weight in the range of 500 Da to 700, comprising: soaking the polymerized coating in an organic solvent to swell the polymerized coating.

18. A method of removal according to claim 17 wherein the polymerized coating completely peels in one or a few pieces and leaves essentially no residual particles.

19. A composition according to claim 1 wherein the weight average molecular weight of the first dicarbamate is about 15 kDa and the weight average molecular weight of the second dicarbamate is about 600 Da.

20. A composition according to claim 1 wherein the (meth)acrylate monomer or monomers and di(meth)acrylate crosslinker are methacrylate monomer or monomers and dimethacrylate crosslinker.

Assignments (9)
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Oct 22, 2024
From: COTY US LLC; COTY BRANDS MANAGEMENT INC.; CALVIN KLEIN COSMETIC CORPORATION; NOXELL CORPORATION
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 069215/0826 →
SECURITY INTEREST Recorded Jun 4, 2024
From: COTY INC.; CALVIN KLEIN COSMETIC CORPORATION; COTY US LLC; COTY US HOLDINGS INC.; COTY BRANDS MANAGEMENT INC.; O P I PRODUCTS, INC.; NOXELL CORPORATION; THE WELLA CORPORATION
To: DEUTSCHE BANK TRUST COMPANY AMERICAS, AS COLLATERAL AGENT
Reel/Frame 067621/0361 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Sep 1, 2023
From: COTY INC.; CALVIN KLEIN COSMETIC CORPORATION; COTY US LLC; COTY US HOLDINGS, INC.; COTY BRANDS MANAGEMENT INC.; O P I PRODUCTS, INC.; NOXELL CORPORATION; THE WELLA CORPORATION
To: DEUTSCHE BANK TRUST COMPANY AMERICAS, AS COLLATERAL AGENT
Reel/Frame 064803/0001 →
RELEASE OF SECURITY INTEREST Recorded Jan 19, 2023
From: DEUTSCHE BANK TRUST COMPANY AMERICAS
To: COTY, INC.
Reel/Frame 064310/0178 →
CORRECTIVE NOTICE REGARDING SECURITY INTEREST IN SPECIFIED PATENTS Recorded Aug 2, 2022
From: DEUTSCHE BANK TRUST COMPANY AMERICAS
To: COTY, INC.
Reel/Frame 061055/0376 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT (PATENTS) Recorded Aug 6, 2021
From: COTY INC.; CALVIN KLEIN COSMETIC CORPORATION; COTY US LLC; COTY BRANDS MANAGEMENT INC.; O P I PRODUCTS, INC.; NOXELL CORPORATION; THE WELLA CORPORATION
To: DEUTSCHE BANK TRUST COMPANY AMERICAS, AS COLLATERAL AGENT
Reel/Frame 057112/0639 →
SECURITY INTEREST Recorded Jun 17, 2021
From: COTY INC.; CALVIN KLEIN COSMETIC CORPORATION; COTY US LLC; COTY BRANDS MANAGEMENT INC.; O P I PRODUCTS, INC.; NOXELL CORPORATION; THE WELLA CORPORATION
To: DEUTSCHE BANK TRUST COMPANY AMERICAS
Reel/Frame 057261/0788 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded May 7, 2021
From: COTY INC.; CALVIN KLEIN COSMETIC CORPORATION; COTY US LLC; COTY BRANDS MANAGEMENT INC.; O P I PRODUCTS, INC.; GRAHAM WEBB INTERNATIONAL, INC.; NOXELL CORPORATION; THE WELLA CORPORATION
To: DEUTSCHE BANK TRUST COMPANY AMERICAS, AS COLLATERAL AGENT
Reel/Frame 056179/0322 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 13, 2019
From: PAVLOVIC, ELIZABETA; YUVAVANICH, SUNAN
To: COTY INC.
Reel/Frame 049160/0931 →