Formaldehyde free microspheres and encapsulation

Patent metadata

Field	Value
Publication number	US-11560447-B2
Application number	US-201816636514-A
Country	US
Kind code	B2
Filing date	Aug 3, 2018
Priority date	Aug 4, 2017
Publication date	Jan 24, 2023
Grant date	Jan 24, 2023

Abstract

Processes for producing polymer microcapsules using vicinal functional oligomers are also described. The vicinal functional oligomers can be made by polymerizing an acrylate monomer, a styrene monomer, or both in the presence of a chain transfer agent. The vicinal functional oligomers can be reacted with epichlorohydrin to form vicinal epoxies. The vicinal epoxies can be reacted with polyamines to form epoxy polymer microspheres. The vicinal epoxies can be reacted with carbon dioxide in the presence of a catalyst to form vicinal cyclic carbonates. The vicinal cyclic carbonates can be reacted with polyamines to form isocyanate-free polymer microspheres. Polymer microspheres made by the processes are also described.

First claim

The invention claimed is:

1. A process of making polyurethane microspheres consisting essentially of:
polymerizing a monomer selected from the group consisting of an acrylate monomer, or a styrene monomer, or both, and thioglycerol to form a vicinal functional diol; and
reacting reactants selected from the group consisting of the vicinal functional diol, an isocyanate, and a polyol to form polyurethane polymer microspheres.

2. The process of claim 1 wherein the acrylate monomer comprises acrylic acid, methacrylic acid, methyl methacrylate, t-butyl methacrylate, butyl methacrylate, lauryl methacrylate, stearyl methacrylate, N,N′-dimethyl amino ethyl methacrylate, acetoacetoxy ethyl methacrylate, or combinations thereof.

3. The process of claim 1 wherein the isocyanate comprises toluene diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, methylene bisphenyl isocyanate, or combinations thereof.

4. The process of claim 1 wherein the polyol comprises ethylene glycol, 1,4-butane diol, 1,6-hexane diol, 1,3,6-hexane triol, trimethylol propane, poly(tetramethylene) glycol, poly caprolactone diol, poly ethyleneglycol adipate, poly ethyleneglycol succinate, poly ethyleneglycol sebacate, poly ethyleneglycol itoconate, or combinations thereof.

5. The process of claim 1 wherein the vicinal functional oligomer is a polystearyl methacrylate vicinal diol, and the isocyanate is a polyisocyanate.

6. The process of claim 1 wherein the polymer microspheres are spherical and have a particle size between about 0.01 microns and about 500 microns.

7. The process of claim 1 wherein the polymer microspheres encapsulate a solid or liquid active ingredient.

8. The process of claim 7 wherein the active ingredient comprises, benzisothiazolinone, quaternary ammonium salts, epoxy oligomers, acrylic oligomers, isocyanate oligomers, 2,4-dichlorophenoxyacetic acid, sulfentrazone, or combinations thereof.

9. The process of claim 1 wherein the monomer is styrene.

Assignees

• Battelle Memorial Institute

Inventors

• Lalgudi Ramanathan S
• Cain Robert J

Classifications

• C08F220/18

  with acrylic or methacrylic acids · CPC title

• C08F2/38 Primary

  Polymerisation using regulators, e.g. chain terminating agents {, e.g. telomerisation} · CPC title

• C08G18/73

  acyclic · CPC title

• C08G18/6225 Primary

  Polymers of esters of acrylic or methacrylic acid · CPC title

• C08K5/37

  Thiols · CPC title