IP Library Granted Patent US 7,629,394
Granted Patent B2
US 7,629,394 · App. 11/358,817 · Granted Dec 8, 2009

UV curable coating material of encapsulated water dispersed core material

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Quick Facts
Patent No.
US 7,629,394
App. No.
11/358,817
Granted
Dec 8, 2009
Kind
B2
Abstract

The present invention describes a process of preparing microcapsules in a UV curable water immiscible phase. The microcapsules formed according to the invention contain an aqueous phase core. The process comprises dispersing a water soluble or dispersible core material along with at least one wall forming prepolymer and a polycondensation polymerization catalyst into an aqueous solution. The aqueous phase is then dispersed into the water immiscible phase comprising UV curable monomers or oligomers forming droplets of the aqueous phase solution in the water immiscible phase. Polycondensation of the prepolymers is initiated to form polymeric wall material or microcapsules at or near the interface of the water immiscible solvent and droplets of aqueous phase solution. Following capsule formation, a UV initiator is dispersed in the water immiscible phase. The UV curable dispersion containing aqueous microcapsules can be coated on a substrate. The coating is then cured by UV irradiation forming a gelled, solidified, or dry coating of aqueous microcapsules.

Claims (50)

1. A process of preparing a UV curable coating material of microcapsules with an aqueous internal phase along with core material, the process comprising:

providing an aqueous phase comprising a dissolved or dispersed core material:

dissolving or dispersing wall-forming water-soluble or water-dispersible prepolymers, oligomers or monomers into the aqueous phase;

providing a water-immiscible phase comprising a UV curable monomer or oligomer and at least one emulsifier;

dispersing the aqueous phase into an excess of the water immiscible phase, nonreactive with the wall forming prepolymers, oligomers or monomers, under high shear agitation to form droplets of the aqueous phase dispersed in the water immiscible phase, a water-oil interphase resulting at the interphase of the aqueous and water-immiscible phases;

then adding at least one water insoluble polycondensation polymerization catalyst reactive with the wall forming prepolymers, oligomers or monomers present in the aqueous phase;

forming microcapsules by initiating polycondensation of the monomers, oligomers or prepolymers in the dispersed aqueous phase by heating to precipitate the monomers, oligomers and prepolymers from the aqueous phase at the water-oil interphase thereby forming wall material encapsulating the droplets of the aqueous phase;

adding a UV free radical initiator to the water immiscible phase containing the formed microcapsules thereby forming a coating mixture,

irradiating the coating mixture with ultra violet light to decompose the UV free radical initiator and to cure the UV-curable monomers or oligomers of the water immiscible phase thereby forming a cured coating containing the microcapsules having an encapsulated aqueous internal phase along with the core material.

2. The process according to claim 1 including in addition the step of applying the coating mixture onto a substrate.

3. The process according to claim 1 wherein the polymerization catalyst is selected from an acid, a phase transfer catalyst, and a proton transfer catalyst.

4. The process according to claim 3 wherein the polymerization catalyst is a sulfonic acid.

5. The process according to claim 3 wherein the polymerization catalyst is a liquid or solid dispersible in the water immiscible phase.

6. The process according to claim 5 wherein the polymerization catalyst is a fluorinated sulfonic acid copolymer particle or acid cation ion exchange particle.

7. The process according to claim 1 wherein at least one wall-forming prepolymer is also dispersed into the water immiscible solvent.

8. The process according to claim 1 wherein the wall forming prepolymer is selected from urea formaldehyde, melamine formaldehyde, novolac, and phenolic resin.

9. The process according to claim 1 wherein the water immiscible phase includes in addition an organic solvent.

10. A process of preparing a UV curable coating material of microcapsules with an aqueous internal phase along with core material, the process comprising:

providing an aqueous phase comprising a dissolved or dispersed core material;

dissolving or dispersing wall-forming water-soluble or water-dispersible prepolymers, oligomers or monomers into the aqueous phase;

providing a water-immiscible phase comprising at least one organic solvent, nonreactive with the wall forming prepolymers, oligomers or monomers, and at least one emulsifier;

dispersing the aqueous phase into an excess of the water immiscible phase under high shear agitation to form droplets of the aqueous phase dispersed in the water immiscible phase, a water-oil interphase resulting at the interphase of the aqueous and water-immiscible phases;

then adding at least one water insoluble polycondensation polymerization catalyst reactive with the wall forming prepolymers, oligomers or monomers present in the aqueous phase;

forming microcapsules by initiating polycondensation of the monomers, oligomers or prepolymers in the dispersed aqueous phase by heating to precipitate the monomers, oligomers and prepolymers from the aqueous phase at the water-oil interphase thereby forming wall material encapsulating the droplets of the aqueous phase;

forming a coating mixture by dispersing UV-curable monomers or oligomers into the water immiscible phase along with a UV free radical initiator;

irradiating the coating mixture with ultra violet light to decompose the UV free radical initiator and to cure the UV-curable monomers or oligomers thereby forming a cured coating containing the microcapsules having an encapsulated aqueous internal phase along with the core material.

11. The process according to claim 10 including in addition the step of applying the coating mixture onto a substrate.

12. The process according to claim 10 wherein the polymerization catalyst is selected from an acid, a phase transfer catalyst, and a proton transfer catalyst.

13. The process according to claim 12 wherein the polymerization catalyst is a sulfonic acid.

14. The process according to claim 12 wherein the polymerization catalyst is a liquid or solid dispersible in the water immiscible phase.

15. The process according to claim 14 wherein the polymerization catalyst is a fluorinated sulfonic acid copolymer particle or acid cation ion exchange particle.

16. The process according to claim 10 wherein at least one wall-forming prepolymer is also dispersed into the water immiscible solvent.

17. The process according to claim 10 wherein the wall forming prepolymer is selected from urea formaldehyde, melamine formaldehyde, novolac, and phenolic resin.

18. A process of preparing a UV curable coating material of microcapsules with an aqueous internal phase along with core material, the process comprising:

providing an aqueous phase comprising a dissolved or dispersed core material;

dissolving or dispersing wall-forming water-soluble or water-dispersible prepolymers, oligomers or monomers into the aqueous phase;

providing a water-immiscible phase comprising at least one organic solvent and at least one emulsifier;

dispersing the aqueous phase into an excess of the water immiscible phase, nonreactive with the wall-forming prepolymers, oligomers or monomers, under high shear agitation to form droplets of the aqueous phase dispersed in the water immiscible phase, a water-oil interphase resulting at the interphase of the aqueous and water-immiscible phases;

then adding at least one water insoluble polycondensation polymerization catalyst reactive with the wall forming polymers, oligomers or monomers present in the aqueous phase;

forming microcapsules by initiating polycondensation of the monomers, oligomers or prepolymers in the dispersed aqueous phase by heating to precipitate the monomers, oligomers and prepolymers from the aqueous phase at the water-oil interphase thereby forming wall material encapsulating the droplets of the aqueous phase;

decanting the formed microcapsules from the water immiscible phase;

forming a coating mixture by dispersing the microcapsules into UV-curable monomers or oligomers along with a UV free radical initiator;

irradiating the coating mixture with ultra violet light to decompose the UV free radical initiator and to cure the UV-curable monomers or oligomers thereby forming a cured coating containing the microcapsules having an encapsulated aqueous internal phase along with the core material.

19. The process according to claim 18 including in addition the step of applying the coating mixture onto a substrate.

20. The process according to claim 18 wherein the polymerization catalyst is selected from an acid, a phase transfer catalyst, and a proton transfer catalyst.

21. The process according to claim 18 wherein the polymerization catalyst is a sulfonic acid.

22. The process according to claim 20 wherein the polymerization catalyst is a liquid or solid dispersible in the water immiscible phase.

23. The process according to claim 22 wherein the polymerization catalyst is a fluorinated sulfonic acid copolymer particle or acid cation ion exchange particle.

24. The process according to claim 18 wherein at least one wall-forming prepolymer is also dispersed into the water immiscible solvent.

25. The process according to claim 18 wherein the wall forming prepolymer is selected from urea formaldehyde, melamine formaldehyde, novolac, and phenolic resin.

Assignments (29)
RELEASE OF SECURITY INTEREST Recorded Oct 7, 2021
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
To: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
Reel/Frame 057750/0945 →
CORRECTIVE ASSIGNMENT TO CORRECT THE APPLICATION NUMBER SERIAL NUMBER PREVIOUSLY RECORDED AT REEL: 44444 FRAME: 0905. ASSIGNOR(S) HEREBY CONFIRMS THE FIRST LIEN SECURITY AGREEMENT. Recorded Aug 8, 2019
From: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS FIRST LIEN COLLATERAL AGENT
Reel/Frame 050021/0307 →
CORRECTIVE ASSIGNMENT TO CORRECT THE APPLICATION NUMBER SERIAL NUMBER PREVIOUSLY RECORDED AT REEL: 44444 FRAME: 0932. ASSIGNOR(S) HEREBY CONFIRMS THE SECOND LIEN SECURITY AGREEMENT. Recorded Aug 8, 2019
From: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS SECOND LIEN COLLATERAL AGENT
Reel/Frame 050021/0359 →
CORRECTIVE ASSIGNMENT TO CORRECT THE PROPERTY NUMBER PREVIOUSLY RECORDED AT REEL: 49891 FRAME: 807. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Aug 8, 2019
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS ADMINISTRATIVE AGENT
To: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
Reel/Frame 050003/0400 →
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Jul 1, 2019
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS ADMINISTRATIVE AGENT
To: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
Reel/Frame 049891/0807 →
RELEASE OF SECOND LIEN PATENT COLLATERAL AGREEMENT Recorded Jun 17, 2018
From: U.S. BANK NATIONAL ASSOCIATION, AS COLLATERAL AGENT
To: APPVION, INC.; PAPERWEIGHT DEVELOPMENT CORP.
Reel/Frame 046377/0179 →
RELEASE OF SECURITY INTEREST Recorded Jun 17, 2018
From: JEFFERIES FINANCE LLC, AS ADMINISTRATIVE AGENT
To: APPVION, INC.; PAPERWEIGHT DEVELOPMENT CORP.
Reel/Frame 046392/0438 →
FIRST LIEN SECURITY AGREEMENT Recorded Nov 14, 2017
From: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS FIRST LIEN COLLATERAL AGENT
Reel/Frame 044444/0905 →
RELEASE OF SECURITY INTEREST Recorded Nov 14, 2017
From: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
To: ENCAPSYS, LLC
Reel/Frame 044123/0160 →
SECOND LIEN SECURITY AGREEMENT Recorded Nov 14, 2017
From: ENCAPSYS, LLC; IPS STRUCTURAL ADHESIVES, INC.; IPS CORPORATION; WATERTITE PRODUCTS, INC.; WELD-ON ADHESIVES, INC.; IPS ADHESIVES LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS SECOND LIEN COLLATERAL AGENT
Reel/Frame 044444/0932 →
RELEASE OF SECURITY INTEREST Recorded Feb 1, 2017
From: WILMINGTON TRUST, NATIONAL ASSOCIATION
To: ENCAPSYS, LLC
Reel/Frame 041144/0570 →
SECURITY INTEREST Recorded Aug 27, 2015
From: ENCAPSYS, LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS ADMINISTRATIVE AGENT
Reel/Frame 036437/0821 →
SECURITY INTEREST Recorded Aug 7, 2015
From: ENCAPSYS, LLC
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 036275/0792 →
CHANGE OF NAME Recorded Aug 6, 2015
From: RISE ACQUISTION, LLC
To: ENCAPSYS, LLC
Reel/Frame 036303/0617 →
RELEASE OF SECURITY INTEREST Recorded Aug 4, 2015
From: JEFFERIES FINANCE LLC, AS ADMINISTRATIVE AGENT
To: APPVION, INC.; PAPERWEIGHT DEVELOPMENT CORP.
Reel/Frame 036251/0893 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 4, 2015
From: APPVION, INC.
To: RISE ACQUISTION, LLC
Reel/Frame 036245/0688 →
RELEASE OF SECURITY INTEREST Recorded Aug 4, 2015
From: U.S. BANK NATIONAL ASSOCIATION, AS COLLATERAL AGENT
To: APPVION, INC.; PAPERWEIGHT DEVELOPMENT CORP.
Reel/Frame 036249/0419 →
RELEASE OF SECURITY INTEREST Recorded Aug 4, 2015
From: JEFFERIES FINANCE LLC, AS ADMINISTRATIVE AGENT
To: APPVION, INC.; PAPERWEIGHT DEVELOPMENT CORP.
Reel/Frame 036250/0466 →
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2013
From: U.S. BANK NATIONAL ASSOCIATION
To: APPLETON PAPERS INC.
Reel/Frame 031690/0774 →
SECOND LIEN PATENT COLLATERAL AGREEMENT Recorded Nov 19, 2013
From: APPVION, INC.; PAPERWEIGHT DEVELOPMENT CORP.
To: U.S. BANK NATIONAL ASSOCIATION
Reel/Frame 031689/0593 →
SECURITY AGREEMENT Recorded Jul 3, 2013
From: APPVION, INC.; PAPERWEIGHT DEVELOPMENT CORP.
To: JEFFERIES FINANCE LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 030740/0153 →
RELEASE OF SECURITY INTEREST Recorded Jul 1, 2013
From: U.S. BANK NATIONAL ASSOCIATION
To: APPLETON PAPERS, INC.; PAPERWEIGHT DEVELOPMENT CORP.; AMERICAN PLASTICS COMPANY; NEW ENGLAND EXTRUSIONS, INC.
Reel/Frame 030724/0312 →
RELEASE OF SECURITY INTEREST Recorded Jun 28, 2013
From: FIFTH THIRD BANK
To: APPLETON PAPERS, INC.
Reel/Frame 030712/0054 →
CHANGE OF NAME Recorded Jun 17, 2013
From: APPLETON PAPERS INC.
To: APPVION, INC.
Reel/Frame 030641/0381 →
RELEASE OF SECURITY INTEREST Recorded Feb 11, 2010
From: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
To: APPLETON PAPERS INC.
Reel/Frame 023915/0760 →
SECURITY AGREEMENT Recorded Feb 9, 2010
From: PAPERWEIGHT DEVELOPMENT CORP.; APPLETON PAPERS INC.; AMERICAN PLASTICS COMPANY, INC.; NEW ENGLAND EXTRUSION INC.
To: U.S. BANK NATIONAL ASSOCIATION
Reel/Frame 023905/0953 →
SECURITY AGREEMENT Recorded Feb 8, 2010
From: APPLETON PAPERS INC.
To: FIFTH THIRD BANK, AS ADMINISTRATIVE AGENT
Reel/Frame 023905/0532 →
NOTICE OF GRANT OF SECURITY INTEREST Recorded Jun 29, 2007
From: APPLETON PAPERS INC.
To: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 019489/0751 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 21, 2006
From: YAN, NIANXI
To: APPLETON PAPERS INC.
Reel/Frame 017610/0110 →