Polymers prepared from functionalized dimethoxyphenol monomers

Patent metadata

Field	Value
Publication number	US-10253131-B2
Application number	US-201615208135-A
Country	US
Kind code	B2
Filing date	Jul 12, 2016
Priority date	Jul 13, 2015
Publication date	Apr 9, 2019
Grant date	Apr 9, 2019

Abstract

Dimethoxyphenol-based monomers containing polymerizable functional groups such as [meth]acrylate groups are useful for the preparation of polymers, wherein one or more dimethoxyphenyl moieties are part of side chains pendant to the backbones of the polymers. The polymers thereby obtained may have different, improved properties, such as higher glass transition temperatures, thermal stability and solvent resistance, as compared to polymers based on other types of lignin-derived monomers.

First claim

What is claimed is:

1. A polymer comprising, in polymerized form, at least one polymerizable monomer comprised of a phenyl ring, two methoxy groups substituted on the phenyl ring, and at least one substituent on the phenyl ring comprised of at least one polymerizable functional group which is an ethylenically unsaturated functional group, wherein the ethylenically unsaturated functional group has been polymerized in the polymer, wherein the at least one polymerizable monomer has a structure corresponding to formula (I):

wherein R1 is a heteroatom-containing organic moiety selected from the group consisting of aldehyde-containing groups, ketone-containing groups, carboxylic acid-containing groups, and hydroxyl-containing groups; and
wherein R2 is the substituent comprised of at least one polymerizable functional group which is an ethylenically unsaturated functional group.

2. The polymer of claim 1 additionally comprising, in polymerized form, one or more polymerizable co-monomers other than polymerizable monomers having structures corresponding to formula (I).

3. The polymer of claim 2 , wherein the one or more polymerizable co-monomers are selected from the group consisting of lignin-based monomers, styrenes, phenyl [meth]acrylates, alkyl [meth]acrylates, [meth]acrylates other than alkyl [meth]acrylates and phenyl [meth]acrylates, terephthalates, amides, amines, diamides, diamines, dichlorides, nitriles, carboxylic acids, lactones, lactams, maleates, fumarates, malonates, maleinates, vinyls, vinyl esters, vinyl amides, [meth]acrylamides, thiols, dithiols, polythiols, enes, dienes, olefins, allyl monomers, azides, diazides, phosgene, carbonates, carbamates, succinates, alcohols, silanes, silicones, siloxanes, ethers, vinyl ethers, vinyl sulfides, isocyanates, epoxides, norbornenes, anhydrides, and combinations thereof.

4. The polymer of claim 2 , wherein the polymer is a block copolymer, random copolymer, star polymer, brush polymer, or gradient copolymer.

5. A polymer comprising, in polymerized form, at least one polymerizable monomer comprised of a phenyl ring, two methoxy groups substituted on the phenyl ring, and at least one substituent on the phenyl ring comprised of at least one polymerizable functional group which is an ethylenically unsaturated functional group, wherein the ethylenically unsaturated functional group has been polymerized in the polymer, wherein the at least one polymerizable monomer has a structure corresponding to formula (I):

wherein R 1 is hydrogen or formyl and R 2 is [meth]acrylate.

6. The polymer of claim 5 additionally comprising, in polymerized form, one or more polymerizable co-monomers other than polymerizable monomers having structures corresponding to formula (I).

7. The polymer of claim 6 , wherein the one or more polymerizable co-monomers are selected from the group consisting of lignin-based monomers, styrenes, phenyl [meth]acrylates, alkyl [meth]acrylates, [meth]acrylates other than alkyl [meth]acrylates and phenyl [meth]acrylates, terephthalates, amides, amines, diamides, diamines, dichlorides, nitriles, carboxylic acids, lactones, lactams, maleates, fumarates, malonates, maleinates, vinyls, vinyl esters, vinyl amides, [meth]acrylamides, thiols, dithiols, polythiols, enes, dienes, olefins, allyl monomers, azides, diazides, phosgene, carbonates, carbamates, succinates, alcohols, silanes, silicones, siloxanes, ethers, vinyl ethers, vinyl sulfides, isocyanates, epoxides, norbornenes, anhydrides, and combinations thereof.

8. The polymer of claim 6 , wherein the polymer is a block copolymer, random copolymer, star polymer, brush polymer, or gradient copolymer.

Assignees

• Holmberg Angela L
• Reno Kaleigh H
• Epps Iii Thomas H
• Univ Delaware

Inventors

• Holmberg Angela L
• Reno Kaleigh H
• Epps Iii Thomas H

Classifications

• C07C39/19

  containing carbon-to-carbon double bonds but no carbon-to-carbon triple bonds · CPC title

• C08F12/24

  Phenols or alcohols · CPC title

• C08F12/22

  Oxygen · CPC title

• C07C39/20

  Hydroxy-styrenes · CPC title

• C07C63/04

  Monocyclic monocarboxylic acids · CPC title