Free-standing non-fouling polymers, their compositions, and related monomers

A bulk material comprising a crosslinked polymer

• having tensile and compressive strengths greater than about 0.5 MPa and a fibrinogen adsorption of less than about 30 ng/cm2 in a fibrinogen binding assay when the material is incubated at 37° C. for 90 minutes with a 1.0 mg/ml fibrinogen solution that is 0.15 M phosphate buffered saline at pH 7.4,
• the crosslinked polymer having a hydrophobic interior comprising (a) a polymer backbone, (b) a plurality of nitrogen centers, each nitrogen center covalently coupled to a polymer backbone by a first linker, (c) optionally a counter ion associated with each nitrogen center, and (d) a hydrolyzable group covalently coupled to each nitrogen center through a second linker, wherein the hydrolyzable group is hydrolyzable to an anionic center to provide a polymer having the anionic center covalently coupled to the nitrogen center through the second linker,
• the crosslinked polymer having a hydrophilic exterior comprising (a) a polymer backbone, (b) a plurality of nitrogen centers, each nitrogen center covalently coupled to a polymer backbone by a first linker, and (c) an anionic center covalently coupled to each nitrogen center through a second linker, wherein the anionic center is provided via hydrolysis of the hydrolyzable group,
• wherein the crosslinked polymer comprises a repeating unit having the formula:
• R1 is selected from the group consisting of hydrogen, fluorine, trifluoromethyl, C1-C20 alkyl, C6-C12 aryl, and CN groups;
• R4 is selected from the group consisting of hydrogen, C1-C20 alkyl, C6-C12 aryl, cyclic alkyl, fluoroalkyl, and void;
• R5 is selected from the group consisting of hydrogen, C1-C20 alkyl, C6-C12 aryl, cyclic alkyl, and fluoroalkyl;
• R7 is C1-C20 alkyl, C6-C12 aryl, cyclic alkyl, or fluoroalkyl,
• L is C or Si;
• L1 at each occurrence is selected from —(CH2)x—, —(CH(CN))x—, —C(═O)NH(CH2)x—, —C(═O)O(CH2)x—, —C(═O)OC(═O)O(CH2)x—, —(CH2)x—O—(CH2)x—, or —(CH2)x—S—S—(CH2)x—, where x at each occurrence is an integer independently selected from 0 to 20;
• L2 at each occurrence is selected from —(CH2)x— or —(CH(CN))x—, where x is an integer from 1 to 20;
• A1 is N;
• B2 is C;
• and
• M is selected from Cl, Br, I, SO4, NO3, ClO4, BF4, PF6, N(SO2CF3)2, SO3CF3, RCOO (R is C1-C20 alkyl), lactate, benzoate, salicylate, or void.