IP Library Granted Patent US 9,192,908
Granted Patent B2
US 9,192,908 · App. 13/864,667 · Granted Nov 24, 2015

Encapsulated solid hydrophilic particles

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Quick Facts
Patent No.
US 9,192,908
App. No.
13/864,667
Granted
Nov 24, 2015
Kind
B2
Abstract

A process of forming microcapsules is described. The microcapsule population is formed by providing an anionic or cationic, solid hydrophilic core material; providing an oil continuous phase, the oil continuous phase comprising one or more esters with chain length up to about 18 carbons. Emulsification is achieved by subjecting the mixture to high shear agitation and heating the mixture for a time sufficient to enable acid or amine acrylate or methacrylate and multifunctional acrylate or methacrylate to form a prepolymer which migrates to the anionic or cationic solid hydrophilic material, thereby forming prepolymers adhered to the hydrophilic core materials. Temperature is held or heating continued for a time sufficient to enable the prepolymer to flow onto and coalesce into a continuous film surface coating on the hydrophilic core material. Heating is carried out or light exposure or both for a time and temperature sufficient to cross link the prepolymers.

Claims (24)

1. A process of forming a population of microcapsules comprising a solid hydrophilic core material and a wall material at least partially surrounding the core material, the microcapsule population being formed by:

providing particles of a solid hydrophilic core material;

providing an oil continuous phase which is low boiling, the oil continuous phase comprising esters or one or more hydrocarbons with chain length up to about 18 carbons;

forming a mixture by:

adding an oil soluble or dispersible amine acrylate or methacrylate;

adding a multifunctional acrylate or methacrylate monomer or oligomer;

adding an acid and an initiator;

optionally adding a surfactant;

dispersing the mixture in the continuous phase by subjecting the mixture to agitation; heating the mixture for a time sufficient to enable the amine acrylate or methacrylate and the multifunctional acrylate or methacrylate to form a cationic prepolymer;

dispersing the solid hydrophilic material in the oil continuous phase whereby the cationic prepolymer migrates to the solid hydrophilic material, thereby forming prepolymer adhered to the hydrophilic core materials;

holding the temperature for a time sufficient to enable the cationic prepolymer to flow onto and coalesce into a continuous film surface coating on the hydrophilic core material;

heating for a time and temperature sufficient to cross link the prepolymer continuous film surface coating on the particles.

2. The process of forming a population of microcapsules according to claim 1 wherein the acid and the amine acrylate or methacrylate have a percent by weight as compared to weight of the we material of from 0.1 to 25 percent.

3. The process of forming a population of microcapsules according to claim 1 wherein the weight ratio of the amine to the multifunctional acrylate or methacrylate is from 0.1:99.9 to 10:90.

4. The process of forming a population of microcapsules according to claim 1 wherein the acid and the amine acrylate or methacrylate have a molar proportion of from 1.5/1 to about 1/1.5.

5. The process of forming a population of microcapsules according to claim 1 wherein the solid hydrophilic core material is selected from the group consisting of anionic, cationic, or neutral but polar material.

6. The process of forming a population of microcapsules according to claim 1 wherein the amine acrylate or methacrylate is selected from a monofunctional amine acrylate or a monofunctional amine methacrylate with a nitrogen content of 5% by weight or greater.

7. The process of forming a population of microcapsules according to claim 1 wherein the amine acrylate is selected from the group consisting of alkyl amino acrylate and alkylaminomethacrylate having a nitrogen content of 5% by weight or greater.

8. The process of forming a population of microcapsules according to claim 1 wherein the acid is a carboxylic acid acrylate or carboxylic acid methacrylate having a —COOH content of 20% or greater by weight.

9. The process according to claim 1 wherein the wail material is selected to be a water permeable, partially water permeable, water soluble, partially water soluble, water fracturable, water disintegratable, semi-porous or an osmotic material.

10. The process according to claim 1 wherein the oil continuous phase comprises in addition sucrose octyl stearate, a polysaccharide, polyethylene glycol, esters of polyethylene glycol, esterified polyol, saccharide ester, or wax.

11. The process according to claim 1 wherein a water soluble polymer is added in addition to the multifunctional acrylate.

12. The process of forming a population of microcapsules according to claim 1 wherein the oil continuous phase is selected from the group consisting of isoamyl benzoate, capric triglyceride, caprylic triglyceride and blends thereof.

13. The process of forming a population of microcapsuies according to claim 1 wherein forming or crosslinking the prepolymers is accomplished by heating the mixture or exposing the mixture to actinic radiation or both.

Assignments (22)
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 →
RELEASE OF SECURITY INTEREST Recorded Nov 14, 2017
From: BANK OF AMERICA, N.A., AS ADMINISTRATIVE AGENT
To: ENCAPSYS, LLC
Reel/Frame 044123/0160 →
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 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 4, 2015
From: APPVION, INC.
To: RISE ACQUISITION, LLC
Reel/Frame 036246/0945 →
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 Aug 4, 2015
From: JEFFERIES FINANCE LLC, AS ADMINISTRATIVE AGENT
To: APPVION, INC.; PAPERWEIGHT DEVELOPMENT CORP.
Reel/Frame 036251/0893 →
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 →
CHANGE OF NAME Recorded Jun 17, 2013
From: APPLETON PAPERS INC.
To: APPVION, INC.
Reel/Frame 030641/0381 →