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US 11,732,141 B2Granted
Functionalized dimethoxyphenol monomers and methods for preparing such monomers
AssigneeUniversity of Delaware
InventorsAngela L. Holmberg, Kaleigh H. Reno, Thomas H. Epps, III
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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.
Claims8
A polymerizable monomer having a structure corresponding to formula (I):
- wherein R1 is hydrogen, methyl, ethyl, n-propyl, i-propyl, formyl, acetyl, —CH2C(═O)CH3, —CH2CH2OH, —CH2CH2CH2OH, —CH2CHO, —CH2CH2CHO, —C(═O)CH2CH3, —C(═O)C(═O)CH3, —CO2H, —CH2CO2H, —C(═O)CH(OH)CH3, —C(═O)CH(OCH2CH3)C(═O)CH3, —CH(OCH2CH3)C(═O)CH3, —CH═CHCHO, —CH═CHCH2OH, —CH═CH2, —CH═CHCH3 or —CH2CH═CH2;
- and R2 is a substituent comprised of at least one polymerizable functional group selected from the group consisting of methacrylate, maleinate, maleate, fumarate, [meth]acrylamide, vinyl ester, and vinyl amide.
A polymerizable monomer having a structure corresponding to formula (I):
- wherein R1 is hydrogen, methyl, ethyl, n-propyl, i-propyl, formyl, acetyl, —CH2C(═O)CH3, —CH2CH2OH, —CH2CH2CH2OH, —CH2CHO, —CH2CH2CHO, —C(═O)CH2CH3, —C(═O)C(═O)CH3, —CO2H, —CH2CO2H, —C(═O)CH(OH)CH3, —C(═O)CH(OCH2CH3)C(═O)CH3, —CH(OCH2CH3)C(═O)CH3, —CH═CHCHO, —CH═CHCH2OH, —CH═CHCO2H, —CH═CH2, —CH═CHCH3 or —CH2CH═CH2;
- and
- wherein R2 is methacrylate.
A polymerizable monomer having a structure corresponding to formula (I):
- (i) wherein R1 is ethyl, n-propyl, 1-propyl, acetyl, —CH2C(═O)CH3, —CH2CH2OH, —CH2CH2CH2OH, —CH2CHO, —CH2CH2CHO, —C(═O)CH2CH3, —C(═O)C(═O)CH3, —CH2CO2H, —C(═O)CH(OH)CH3, —C(═O)CH(OCH2CH3)C(═O)CH3, —CH(OCH2CH3)C(═O)CH3, —CH═CHCHO, —CH═CHCH2OH, —CH═CH2, —CH═CHCH3 or —CH2CH═CH2;
- and R2 is a substituent comprised of at least one polymerizable functional group selected from the group consisting of [meth]acrylate, maleinate, maleate, fumarate, [meth]acrylamide, vinyl, vinyl ester, and vinyl amide;
- or
- (ii) wherein R1 is methyl, ethyl, n-propyl, i-propyl, acetyl, —CH2C(═O)CH3, —CH2CH2OH, —CH2CH2CH2OH, —CH2CHO, —CH2CH2CHO, —C(═O)CH2CH3, —C(═O)C(═O)CH3, —CO2H, —CH2CO2H, —C(═O)CH(OH)CH3, —C(═O)CH(OCH2CHS)C(═O)CH3, —CH(OCH2CH3)C(═O)CH3, —CH═CHCHO, —CH═CHCH2OH, —CH═CH2, —CH═CHCH3 or —CH2CH═CH2;
- and R2 is a substituent comprised of at least one polymerizable functional group selected from the group consisting of [meth]acrylate, maleinate, maleate, fumarate, [meth]acrylamide, vinyl ester, and vinyl amide;
- or
- (iii) wherein R1 is methyl, ethyl, n-prolyl, i-propyl, acetyl, —CH2C(═O)CH3, —CH2CH2OH, —CH2CH2CH2OH, —CH2CHO, —CH2CH2CHO, —C(═O)CH2CH3, —C(═O)C(═O)CH3, —CH2CO2H, —C(═O)CH(OH)CH1, —C(═O)CH(OCH2CH3)C(═O)CH1, —CH(OCH2CH3)C(═O)CH3, —CH═CHCHO, —CH═CHCH2OH, —CH═CH2, —CH═CHCH3 or —CH2CH═CH2;
- and R2 is a substituent comprised of at least one polymerizable functional group selected from the group consisting of [meth]acrylate, maleinate, maleate, fumarate, [meth]acrylamide, vinyl ester, and vinyl amide.
5 more elements
A polymerizable monomer having a structure corresponding to formula (I):
- wherein R1 is methyl, ethyl, n-propyl, i-propyl, acetyl, —CH2C(═O)CH3, —CH2CH2OH, —CH2CH2CH2OH, —CH2CHO, —CH2CH2CHO, —C(═O)CH2CH3, —C(═O)C(═O)CH3, —CO2H, —CH2CO2H, —C(═O)CH(OH)CH3, —C(═O)CH(OCH2CH3)C(═O)CH3, —CH(OCH2CH3)C(═O)CH3, —CH═CHCHO, —CH═CHCH2OH, —CH═CH2, —CH═CHCH3 or —CH2CH═CH2;
- and
- wherein R2 is [meth]acrylate.
A polymerizable monomer having a structure corresponding to formula (I):
- (i) wherein R1 is ethyl, n-propyl, i-propyl, acetyl, —CH2C(═O)CH3, —CH2CH2OH, —CH2CH2CH2OH, —CH2CHO, —CH2CH2CHO, —C(═O)CH2CH3, —C(═O)C(═O)CH3, —CH2CO2H, —C(═O)CH(OH)CH3, —C(═O)CH(OCH2CH3)C(═O)CH3, —CH(OCH2CH3)C(═O)CH3, —CH═CHCHO, —CH═CHCH2OH, —CH═CH2, —CH═CHCH3 or —CH2CH═CH2;
- and R2 is a substituent comprised of at least one polymerizable functional group selected from the group consisting of methacrylate, maleinate, maleate, fumarate, [meth]acrylamide, allyl, vinyl ester, and vinyl amide;
- or
- (ii) wherein R1 is ethyl, n-propyl, i-propyl, formyl, acetyl, —CH2C(═O)CH3, —CH2CH2OH, —CH2CH2CH2OH, —CH2CHO, —CH2CH2CHO, —C(═O)CH2CH3, —C(═O)C(═O)CH3, —CO2H, —CH2CO2H, —C(═O)CH(OH)CH3, —C(═O)CH(OCH2CH3)C(═O)CH3, —CH(OCH2CH3)C(═O)CH3, —CH═CHCHO, —CH═CHCH2OH, —CH═CH2, —CH═CHCH3 or —CH2CH═CH2;
- and R2 is a substituent comprised of at least one polymerizable functional group selected from the group consisting of methacrylate, maleinate, maleate, fumarate, [meth]acrylamide, vinyl ester, and vinyl amide.
2 more elements
A polymerizable monomer having a structure corresponding to formula (I):
- (i) wherein R1 is ethyl, n-propyl, 1-propyl, acetyl, —CH2C(═O)CH3, —CH2CH2OH, —CH2CH2CH2OH, —CH2CHO, —CH2CH2CHO, —C(═O)CH2CH3, —C(═O)C(═O)CH3, CH2CO2H, —C(═O)CH(OH)CH3, —C(═O)CH(OCH2CH3)C(═O)CH3, —CH(OCH2CH3)C(═O)CH3, —CH═CHCHO, —CH═CHCH2OH, —CH═CH2, —CH═CHCH3 or —CH2CH═CH2;
- and R2 is a substituent comprised of at least one polymerizable functional group selected from the group consisting of [meth]acrylate, maleinate, maleate, fumarate, [meth]acrylamide, vinyl, allyl, vinyl ester, and vinyl amide;
- or
- (ii) wherein R, is ethyl, n-propyl, i-propyl, acetyl, —CH2C(═O)CH3, —CH2CH2OH, —CH2CH2CH2OH, —CH2CHO, —CH2CH2CHO, —C(═O)CH2CH3, —C(═O)C(═O)CH3, —CH2CO2H, —C(═O)CH(OH)CH3, —C(═O)CH(OCH2CH3)C(═O)CH3, —CH(OCH2CH3)C(═O)CH3, —CH═CHCHO, —CH═CHCH2OH, —CH═CH2, —CH═CHCH3 or —CH2CH═CH2;
- and R2 is a substituent comprised of at least one polymerizable functional group selected from the group consisting of [meth]acrylate, maleinate, maleate, fumarate, [meth]acrylamide, vinyl, vinyl ester, and vinyl amide;
- or
- (iii) wherein R1 is ethyl, n-propyl, i-propyl, formyl, acetyl, —CH2C(═O)CH3, —CH2CH2OH, —CH2CH2CH2OH, —CH2CHO, —CH2CH2CHO, —C(═O)CH2CH3, —C(═O)C(═O)CH3, —CO2H, —CH2CO2H, —C(═O)CH(OH)CH3, —C(═O)CH(OCH2CH3)C(═O)CH3, —CH(OCH2CH3)C(═O)CH3, —CH═CHCHO, —CH═CHCH2OH, —CH═CH2, —CH═CHCH3 or —CH2CH═CH2;
- and R2 is a substituent comprised of at least one polymerizable functional group selected from the group consisting of methacrylate, maleinate, maleate, fumarate, [meth]acrylamide, vinyl ester, and vinyl amide.
5 more elements
Dependencies are inferred from the claim text.