IP Library Granted Patent US 9,944,886
Granted Patent B2
US 9,944,886 · App. 14/971,645 · Granted Apr 17, 2018

Coated microcapsules

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Quick Facts
Patent No.
US 9,944,886
App. No.
14/971,645
Granted
Apr 17, 2018
Kind
B2
Abstract

Accordingly, there are provided coated microcapsules including a microcapsule, said microcapsules including a polymeric shell and a liquid core material encapsulated therein; and a metallic coating surrounding said microcapsules; wherein the metallic coating includes particles of a first metal adsorbed on said polymeric shell and a film of a second metal formed thereon; and wherein the metallic coating has a maximum thickness of 1000 nm; and methods and formulations related thereto.

Claims (31)

1. A coated microcapsule comprising:

a microcapsule comprising a polymeric shell and a liquid core material encapsulated therein; and

a metallic coating surrounding said microcapsule;

wherein the liquid core material comprises a volatile perfume oil comprising one or more volatile perfume raw materials;

wherein the metallic coating comprises sterically stabilized nanoparticles of a first metal having a nanoparticle size of less than 100 nm adsorbed on said polymeric shell to form a discontinuous layer and a continuous film of a second metal overlaid onto the discontinuous layer by electroless plating catalyzed by the nanoparticles of the first metal;

wherein the sterically stabilized nanoparticles of the first metal are first neutral metal nanoparticles having a surface on which are adsorbed and coated a polymeric stabilizer;

wherein the metallic coating has a maximum thickness of 1000 nm;

wherein the continuous film of the second metal is substantially uniform; and

the coated microcapsules retain more than 50% by weight of the liquid core material as shown by an ethanol stability leakage test comprising combining the coated microcapsules in an aqueous solution of one part water and four parts ethanol to form a test mixture, exposing the text mixture to heat at 40° C. for seven days, thereafter separating the text mixture into the coated microcapsules and an aqueous test solution, and analyzing the aqueous test solution to determine the amount of liquid core material that has leached from the coated microcapsules.

2. A coated microcapsule according to claim 1 , wherein the liquid core material comprises one or more compounds selected from isopropyl myristate, tri-esters of C 4 -C 24 fatty acids, soybean oil, hexadecanoic acid methyl ester, isododecane, and combinations thereof.

3. A coated microcapsule according to claim 1 , wherein the polymeric shell comprises a polymeric material selected from the group consisting of polyacrylates, polyethylenes, polyamides, polystyrenes, polyisoprenes, polycarbonates, polyesters, polyureas, polyurethanes, polyolefins, polysaccharides, epoxy resins, vinyl polymers, urea cross-linked with formaldehyde or gluteraldehyde, melamine cross-linked with formaldehyde, gelatin-polyphosphate coacervates optionally cross-linked with gluteraldehyde, gelatin-gum arabic coacervates, cross-linked silicone fluids, polyamines reacted with polyisocyanates, acrylate monomers polymerised via free radical polymerization, silk, wool, gelatine, cellulose, alginate, proteins, and combinations thereof.

4. A coated microcapsule according to claim 3 , wherein the polymeric shell comprises a polyacrylate.

5. A coated microcapsule according to claim 4 , wherein the polyacrylate is poly(methyl methacrylate) or poly(ethyl methacrylate).

6. A coated microcapsule according to claim 1 , wherein the polymeric shell comprises a surface-modifying agent.

7. A coated microcapsule according to claim 6 , wherein at least some of said nanoparticles are adsorbed on said surface-modifying agent.

8. A coated microcapsule according to claim 6 , wherein the surface-modifying agent is selected from cetyl trimethylammonium bromide (CTAB), poly(vinyl alcohol) (PVA), poly(vinyl pyrrolidone) (PVP), and mixtures thereof.

9. A coated microcapsule according to claim 1 , wherein the first metal is palladium, platinum, silver, gold, copper, nickel, tin or a combination thereof, and wherein the second metal is silver, gold, nickel, copper or a combination thereof.

10. A coated microcapsule according to claim 1 , wherein the density of said nanoparticles on the polymeric shell is such that said nanoparticles cover from 0.1 to 80% of the surface area of the polymeric shell.

11. A coated microcapsule according to claim 1 , wherein (i) the first metal is platinum and the second metal is gold; (ii) the first metal is gold and the second metal is silver; or (iii) the first metal is gold and the second metal is copper.

12. A coated microcapsule according to claim 1 , wherein the metallic coating has a maximum thickness of 500 nm, and wherein the metallic coating has a minimum thickness of 1 nm.

13. A coated microcapsule according to claim 1 , wherein the coated microcapsule has a particle size of from 0.1 micron to 500 microns.

14. A coated microcapsule according to claim 1 , wherein the coated microcapsule has a fracture strength of from 0.1 MPa to 25 MPa.

15. A coated microcapsule according to claim 1 , wherein:

i) the liquid core material comprises a perfume oil comprising one or more perfume raw materials;

ii) the polymeric shell comprises a polyacrylate, wherein the polyacrylate is selected from poly(methyl methacrylate), poly(ethyl methacrylate), or combinations thereof;

iii) the polymeric shell further comprises a surface-modifying agent, wherein the surface-modifying agent is selected from cetyl trimethylammonium bromide (CTAB), poly(vinyl alcohol) (PVA), polyvinyl pyrrolidone) (PVP), and mixtures thereof;

iv) (a) the first metal is platinum and the second metal is gold; (b) the first metal is gold and the second metal is silver; or (c) the first metal is gold and the second metal is copper;

v) the metallic coating has a maximum thickness of 500 nm and a minimum thickness of 1 nm;

vi) the coated microcapsule has a particle size of from 0.1 micron to 500 microns;

vii) the coated microcapsule retains more than 70% by weight of the liquid core material when tested under the Ethanol Stability Test; and

viii) the coated microcapsule has a fracture strength of from 0.1 MPa to 25 MPa.

Assignments (12)
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 22, 2023
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 065016/0676 →
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 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT (PATENTS) Recorded Dec 29, 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 058610/0645 →
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 Sep 26, 2017
From: THE PROCTER & GAMBLE COMPANY
To: NOXELL CORPORATION
Reel/Frame 043704/0606 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 18, 2016
From: BAXTER, ELAINE ALICE MARIE; DYTER, ZOE NMN; HOLLAND, LYNETTE ANNE MAKINS; KHANOLKAR, MADHURI JAYANT; RODRIGO GOMEZ, RAUL NMN; YORK, DAVID WILLIAM
To: THE PROCTER & GAMBLE COMPANY
Reel/Frame 037766/0700 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 18, 2016
From: BIGGS, SIMON RICHARD; CAYRE, OLIVIER JEAN; HITCHCOCK, JAMES PAUL; TASKER, ALISON LOUISE
To: UNIVERSITY OF LEEDS
Reel/Frame 037766/0863 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 18, 2016
From: UNIVERSITY OF LEEDS
To: THE PROCTER & GAMBLE COMPANY
Reel/Frame 037766/0944 →