Switchable antimicrobial and antifouling carboxybetaine-based hydrogels and elastomers with enhanced mechanical properties
AssigneeThe University of Akron
InventorsGang CHENG, Bin CAO
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Abstract
Various embodiments of the present invention are directed to switchable carboxybetaine-based polymers, hydrogels, and/or elastomers, along with novel related monomers, crosslinkers, and methods. Under acidic conditions, the materials undergo self-cyclization and can catch and kill bacteria. Under neutral/basic conditions, these materials undergo ring-opening and can release killed bacterial cells and resist protein adsorption and bacterial attachment. These smart polymers, hydrogels and elastomers also show excellent mechanical properties making them highly desirable for many biomedical applications.
Claims35
A zwitterionic composition having excellent anti-fouling and antimicrobial properties and improved mechanical properties comprising:
- a polymer backbone formed from monomers selected from the group consisting of acrylates, methacrylates, acrylamides, methacrylamides, vinyl alcohols, serines and combinations thereof;
- one or more zwitterionic moieties chemically bonded to said polymer backbone, said zwitterionic moieties further comprising a carboxybetaine group having at least one ethanol, propanol, butanol or pentanol group bonded to the nitrogen atom of said carboxybetaine group;
- and
- a crosslinking compound.
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A carboxybetaine-based composition having excellent anti-fouling and antimicrobial properties and improved mechanical properties comprising:
- a zwitterionic polymer selected from the group consisting of poly(2-((2-hydroxyethyl)(2-methacrylamidoethyl)(methyl)ammonio)acetate), poly(3-((2-hydroxyethyl)(2-methacrylamidoethyl)(methyl)ammonio)propanoate), poly(2-((2-hydroxyethyl)(2-(methacryloyloxy)ethyl)(methyl)ammonio)acetate) and poly(2-(bis(2-hydroxyethyl)(2-(methacryloyloxy)ethyl)ammonio)acetate) and combinations and/or analogs thereof;
- and
- a crosslinker.
A zwitterionic monomer having the formula:
- wherein R1 is —H, —CH3, or —CH2CH3, R2 is O or NH;
- R3 is —CH2—, —CH2CH2—, —CH2CH2CH2—, —CH2CH2CH2CH2—, or —CH2CH2CH2CH2CH2—;
- R4 is —CH2CH2OH, —CH2CH2CH2OH, —CH2CH2CH2CH2OH, or —CH2CH2CH2CH2CH2OH;
- R5 is —H, —CH3, —CH2CH3, —CH2CH2CH3, —CH2CH2CH2CH3, —CH2CH2OH, —CH2CH2CH2OH, —CH2CH2CH2CH2OH, or —CH2CH2CH2CH2CH2OH;
- and R6 is —CH2CH2—, —CH2CH2CH2—, —CH2CH2CH2CH2—, or —CH2CH2CH2CH2CH2—.
A zwitterionic monomer having the formula:
- wherein R1 is —H, —CH3, —CH2CH3;
- R2 is O or NH;
- R3 is —CH2CH2OH, —CH2CH2CH2OH, —CH2CH2CH2CH2OK or —CH2CH2CH2CH2CH2OH;
- R4 is —H, —CH3, —CH2CH3, —CH2CH2CH3, —CH2CH2CH2CH3, —CH2CH2OH, —CH2CH2CH2OH, —CH2CH2CH2CH2OH, or —CH2CH2CH2CH2CH2OH;
- and R5 is —CH2CH2—, —CH2CH2CH2—, —CH2CH2CH2CH2—, or —CH2CH2CH2CH2CH2—.
A zwitterionic composition having the formula:
A method for forming a novel zwitterionic monomer comprising:
- A. dissolving N-methyl diethanol amine in an anhydrous organic solvent and an anhydrous base;
- B. reacting the solution of step A with a stoichiometric quantity of methacryloyl chloride to produce 2-((2-hydroxyethyl)(methyl)amino)ethyl methacrylate;
- C. dissolving the 2-((2-hydroxyethyl)(methyl)amino)ethyl methacrylate of step B in a suitable organic solvent and reacting it with tert-butyl bromoacetate to produce 2-(tert-butoxy)-N-(2-hydroxyethyl)-N-(2-methacryloyloxy)ethyl)-N-methyl-2-oxoethanaminium bromide;
- D. dissolving the 2-(tert-butoxy)-N,N-bis(2-hydroxyethyl)-N-(2-(methacryloyloxy)ethyl)-2-oxoethanaminium bromide of step C in a suitable organic solvent and reacting it with trifluoroacetic acid and recovering the reaction product;
- and
- E. dissolving the reaction product of step D in an suitable solvent and neutralizing it over a basic ionic exchange resin to produce 2-((2-hydroxyethyl)(2-(methacryloyloxy)ethyl) (methyl)ammonio)acetate.
A method for forming the novel zwitterionic monomer comprising:
- A. dissolving a base in a suitable solvent and adding 2-((2-aminoethyl)amino)ethanol;
- B. cooling the product of step A and reacting it with a stoichiometric quantity of methacrylic anhydride under a dry gas atmosphere to produce N-(2-((2-hydroxyethyl) amino)ethyl)methacrylamide.
- C. dissolving the N-(2-((2-hydroxyethyl)amino)ethyl)methacrylamide of step B in a suitable solvent and reacting it with tert-butyl bromoacetate or tert-butyl acrylate to produce tert-butyl N-(2-hydroxyethyl)-N-(2-methacrylamidoethyl)glycinate or tert-butyl 3-((2-hydroxyethyl)(2-methacrylamidoethyl) amino)propanoate;
- D. dissolving the reaction product of step C in a suitable solvent and reacting it with methyl iodide under a dry gas atmosphere;
- E. the reaction product of step D is then reacted with trifluoroacetic acid (TFA) in a suitable solvent and the reaction product collected;
- and
- F. re-dissolving the reaction product of step E in a suitable solvent and neutralizing it over a basic ionic exchange resin to produce 2-((2 hydroxyethyl)(2-methacrylamidoethyl)(methyl)ammonio)acetate or 3-((2-hydroxyethyl)(2-methacrylamidoethyl)(methyl)ammonio)propanoate.
Dependencies are inferred from the claim text.