Hydrophilic polyarylene ether ketone polymer and methods of forming same

A medical device comprising a surface coating comprising a polyarylene ether ketone polymer having a plurality of repeating units, wherein a ketone group in one or more units of the plurality of repeating units comprises a hydrophilic N-substituted imine, wherein the device is an implant,

• wherein the one or more units comprising the hydrophilic N-substituted imine are independently represented by Formula I,
• wherein:
• Ar1, Ar2, Ar3, and Ar4 are each an optionally substituted aryl;
• each of X1 and X2 is independently selected from the group consisting of O,
• wherein:
• Y is a C1-C10 alkylene, wherein one or more carbons in the C1-C10 alkylene are independently and optionally replaced with a heteroatom, a carbonyl, or NR1R2,
• Ra is selected from the group consisting of OR1, NR1R2, C1-C5 alkyl, a primary, secondary, tertiary, or quaternary ammonium salt moiety, a pyridinium salt moiety, a guanidino or guanidinium salt moiety, a peptide, an amino acid, and a zwitterionic species, wherein R1 and R2 are independently an H or a C1-C5 alkyl, and
• provided that at least one of all the X1s and all the X2s in each of the one or more units is not O;
• m and n are each an integer of 1, 2, or 3;
• and
• o and p are each an integer of 0, 1, or 2.

A medical device comprising a surface coating comprising a polyarylene ether ketone polymer having a plurality of repeating units, wherein a ketone group in one or more units of the plurality of repeating units comprises a hydrophilic N-substituted imine, wherein the one or more units comprising the hydrophilic N-substituted imine are independently represented by Formula I,

• wherein:
• Ar1, Ar2, Ar3, and Ar4 are each an optionally substituted aryl;
• each of X1 and X2 is independently selected from the group consisting of O,
• wherein:
• Y is a C1-C10 alkylene, wherein one or more carbons in the C1-C10 alkylene are independently and optionally replaced with a heteroatom, a carbonyl, or NR1R2,
• Ra is selected from the group consisting of OR1, NR1R2, C1-C5 alkyl, a primary, secondary, tertiary, or quaternary ammonium salt moiety, a pyridinium salt moiety, a guanidino or guanidinium salt moiety, a peptide, an amino acid, and a zwitterionic species, wherein R1 and R2 are independently an H or a C1-C5 alkyl, and
• provided that at least one of all the X1s and all the X2s in each of the one or more units is not O;
• m and n are each an integer of 1, 2, or 3;
• and
• o and p are each an integer of 0, 1, or 2.

A method of modifying a medical device comprising a surface polymer comprising a plurality of repeating units, comprising

• (a) contacting the surface polymer with an agent selected from the group consisting of
• in a reaction medium
• wherein:
• Y is a C1-C10 alkylene, wherein one or more carbons in the C1-C10 alkylene is optionally replaced with a heteroatom or a carbonyl;
• and
• Ra is selected from the group consisting of OR1, NR1R2, C1-C5 alkyl, a primary, secondary, tertiary, or quaternary ammonium moiety, a pyridinium salt moiety, a guanidino or guanidinium salt moiety, a peptide, an amino acid, and a zwitterionic species, wherein R1 and R2 are each an H or a C1-C5 alkyl;
• and
• (b) allowing a ketone group of one or more units of the plurality of repeating units to react with the agent, whereby the ketone group of the one or more units is converted to a hydrophilic derivative group;
• wherein each of the plurality of repeating units in the hydrophilic derivative group is independently represented by Formula I,
• wherein:
• Ar1, Ar2, Ar3, and Ar4 are each an optionally substituted aryl;
• each of X1 and X2 is independently selected from O,
• wherein:
• Y is a C1-C10 alkylene, wherein one or more carbons in the C1-C10 alkylene is optionally replaced with a heteroatom, a carbonyl or NR1R2,
• Ra is selected from the group consisting of OR1, NR1R2, C1-C5 alkyl, a primary, secondary, tertiary, or quaternary ammonium salt moiety, a pyridinium salt moiety, a guanidino or guanidinium salt moiety, a peptide, an amino acid, or a zwitterionic species, wherein R1 and R2 are independently an H or a C1-C5 alkyl, and
• provided that at least one of all the X1s and all the X2s in each of the one or more units is not O;
• m and n are each an integer of 1, 2, or 3;
• and
• o and p are each an integer of 0, 1, or 2.