IP Library Granted Patent US 9,267,009
Granted Patent B2
US 9,267,009 · App. 14/342,213 · Granted Feb 23, 2016

Methods and systems of graft polymerization on a functionalized substrate

Inventors: John A. Spevacek (Woodbury, MN); Roger Pearson (Minneapolis, MN); Kenneth W. Richards (Plymouth, MN); Kenneth D. Zigrino (Eden Prairie, MN)
Assignee: Aspen Research Corporation
C08J7/16C08F273/00C08G63/688C08H1/00C08J7/18C08F220/06C08L89/00
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Quick Facts
Patent No.
US 9,267,009
App. No.
14/342,213
Granted
Feb 23, 2016
Kind
B2
Abstract

Graft polymerization is fullfiled on a functionalized substrate. The functionalized substrate is prepared from a disulfide bond-containing feedstock and has been prepared for polymerization through the introduction of one or more polyfunctional monomers containing a disulfide bond breaking material functional group.

Claims (29)

1. A process of graft polymerization to generate a graft polymerization composition, comprising:

introducing a disulfide-bond-containing material to a polyfunctional monomer, the disulfide-bond-containing material including a disulfide bond connecting a first portion and a second portion, the polyfunctional monomer including at least one first functional group and at least one second functional group, the first functional group including a disulfide bond breaking material for breaking the disulfide bond and forming a second bond between the first portion and the polyfunctional monomer, the second functional group including a thiol group;

introducing an ene monomer to the disulfide-bond-containing material and a polyfunctional monomer to form a mixture;

initiating a thiol-ene polymerization reaction of the mixture; and

performing a solids reaction without the use of water, aqueous solvents or non-aqueous solvents.

2. The process of claim 1 , wherein the disulfide bond breaking material includes a thiol group, and the second bond is a disulfide bond.

3. The process of claim 1 , further comprising:

initiating the thiol-ene polymerization reaction of the mixture using an initiator that includes at least one of a UV light, a thermal initiator, and/or a catalyst.

4. The process of claim 1 , further comprising initiating a second polymerization reaction to the graft polymerization composition.

5. The process of claim 4 , wherein the initiating the second polymerization reaction to the graft polymerization composition includes using an initiator that includes at least one of a UV light, a thermal initiator, and/or a catalyst.

6. The process of claim 4 , wherein the initiating the second polymerization reaction to the graft polymerization composition includes introducing a third monomer or macromer to the mixture, and self-initiating, via the third monomer or macromer, a second polymerization reaction.

7. The process of claim 1 , wherein the second functional group includes at least one ring, the ring being adapted to be opened to form at least a third functional group.

8. The process of claim 2 , wherein a molar ratio of the thiol groups and the ene monomer is not greater than 1:1.

9. The process of claim 1 , wherein the first and second portions connected by the disulfide bond are cysteine residues.

10. A graft polymer composition, the composition comprising:

a substrate and a thiol-ene polymer, the substrate and the thiol-ene polymer being bonded via a disulfide-bond;

the substrate including a disulfide-bond-containing material, the disulfide-bond-containing material including a disulfide bond connecting a first portion and a second portion; and

the thiol-ene polymer including a polyfunctional monomer and an ene monomer, the polyfunctional monomer including at least one first functional group and at least one second functional group, the first functional group including a disulfide bond breaking material, and the second functional group including a thiol group configured to react with the ene monomer,

wherein the second functional group includes at least one ring, the ring being adapted to be opened to form at least a third functional group.

11. The graft polymer composition of claim 10 , wherein the disulfide bond breaking material includes a thiol group.

12. The graft polymer composition of claim 10 , wherein the second functional group includes at least one of an acid anhydride, an acyl halide, an alcohol, an aldehyde, an alkene, an alkyne, an amine, a carboxylic acid, an ester and/or a thiol.

13. The composition of claim 11 , wherein a molar ratio of the thiol groups and the ene monomer is not greater than 1:1.

14. A process of graft polymerization to generate a graft polymerization composition, comprising:

introducing a disulfide-bond-containing material to a polyfunctional monomer, the disulfide-bond-containing material including a disulfide bond connecting a first portion and a second portion, the polyfunctional monomer including at least one first functional group and at least one second functional group, the first functional group including a disulfide bond breaking material for breaking the disulfide bond and forming a second bond between the first portion and the polyfunctional monomer, the second functional group including a thiol group;

introducing an ene monomer to the disulfide-bond-containing material and a polyfunctional monomer to form a mixture;

initiating a thiol-ene polymerization reaction of the mixture;

performing a solids reaction without the use of water, aqueous solvents or non-aqueous solvents, wherein performing the solids reaction includes:

breaking, via the disulfide bond breaking material of the first functional group, the disulfide bond; and

forming the second bond between the first portion and the polyfunctional monomer.

Continuity (3)
Provisional Application 61530012 · Sep 1, 2011
Provisional Application 61530016 · Sep 1, 2011
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