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US 12,234,314 B2Granted
Zwitterionic polymers for biomedical applications
AssigneeThe Board of Trustees of the University of Illinois
InventorsGang Cheng, Huifeng Wang
Life of this patent
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Abstract
Provided herein are polymers having a polymer backbone including a zwitterionic precursor monomeric unit having a secondary or tertiary amine in the polymer backbone, as well as methods of making and using the same.
Claims12
A polymer, comprising:
- a polymer backbone:
- comprising a first monomeric unit, wherein the first monomeric unit is derived from a combination consisting of an isocyanate and a diol or polyol;
- and
- one or more second monomeric units, wherein the one or more second monomeric units comprise a zwitterionic precursor monomeric unit having a structure according to one or more of Formula (A1) and (B1):
- wherein in Formulas (A1) and (B1):
- each X is independently O, NRa, S or Se;
- and,
- each R1, R2, and R3 is independently selected from —(CH2)n—, —(CH2)nO(CH2)m—, —(CH2CH2OCH2CH2)n—, —(CH2CH2O)nCH2CH2—, —((CH2)1-8C(O)O)n(CH2)m—, —((CH2)1-8C(O)O)n(CH2CH2O)m(OC(O)(CH2)1-8)p—, —((CH2)1-8C(O)O)n(CH2CH2)m(OC(O)(CH2)1-8)p—, —(CH2C(O)O)m(CH2CH2)n(OC(O)CH2)m—, —(CH(CH3)C(O)O)m(CH2CH2)n(OC(O)CH(CH3))m—, —(CH(CH3)C(O)O)m(CH2CH2)n(OC(O)CH(CH3))m—, —((CH2)nOC(O)O)(CH2CH2)m, —(CH2)nNHC(O)(CH2)m—, and —(CH2)nC(O)NH(CH2)m;
- each Ra and R4 is independently selected from —H, —(CH2CH2O)nCH3, —(CH2CH2O)n(CH2)mCH3, —(CH2CH2O)n(CH2)mOH, —((CH2)nO)m((CH2)pO)q(CH2)rOH, —(CH2CH2O)nH, —(CH2)nOH, —(CH2)nO(CH2)mOH, —(CH2CH2OCH2CH2)nOH, —(CH2CH2O)nCH2CH2OH, —((CH2)1-8C(O)O)n(CH2)mOH, —((CH2)1-8C(O)O)n(CH2CH2O)m(OC(O)(CH2)1-8)pOH, —((CH2)1-8C(O)O)n(CH2CH2)m(OC(O)(CH2)1-8)mOH, —(CH2C(O)O)n(CH2CH2)m(OC(O)CH2)pOH, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))pOH, —((CH2)nOC(O)O)(CH2CH2)mOH, —(CH2)nNHC(O)(CH2)mOH, and —(CH2)nC(O)NH(CH2)mOH, C1-n alkyl, C1-n alkenyl, C1-n alkynyl, C6-10 aryl, and succinimidyl, wherein any one or more H atoms of Ra or R4 can optionally be replaced with an F atom;
- and
- each n, m, p, q, r, and s is independently 1 to 10,000.
8 more elements
A polymer comprising:
- a polymer backbone comprising:
- a first monomeric unit derived from a compound consisting of an isocyanate and a diol or a polyol, and
- one or more second monomeric units, the one or more second monomeric units comprising a zwitterionic precursor monomeric unit, wherein the zwitterionic precursor monomeric unit comprises a secondary or a tertiary amine within the polymer backbone;
- and wherein the polymer backbone comprises repeating units of Formula (I):
- wherein
- each R1 and R2 is independently selected from —(CH2)n—, —(CH2)nO(CH2)m—, —(CH2CH2OCH2CH2)n—, —(CH2CH2O)nCH2CH2—, —((CH2)1-8C(O)O)n(CH2)m—, —((CH2)1-8C(O)O)n(CH2CH2O)m(OC(O)(CH2)1-8)p—, —((CH2)1-8C(O)O)n(CH2CH2)m(OC(O)(CH2)1-8)p—, —(CH2C(O)O)m(CH2CH2)n(OC(O)CH2)m—, —(CH(CH3)C(O)O)m(CH2CH2)n(OC(O)CH(CH3))m—, —(CH(CH3)C(O)O)m(CH2CH2)n(OC(O)CH(CH3))m—, —((CH2)nOC(O)O)(CH2CH2)m, —(CH2)nNHC(O)(CH2)m—, and —(CH2)nC(O)NH(CH2)m;
- R3 is —(CH2)1-5—;
- each R4 is independently selected from —H, —(CH2CH2O)nCH3, —(CH2CH2O)n(CH2)mCH3, —(CH2CH2O)n(CH2)mOH, —((CH2)nO)m((CH2)pO)q(CH2)rOH, —(CH2CH2O)nH, —(CH2)nOH, —(CH2)nO(CH2)mOH, —(CH2CH2OCH2CH2)nOH, —(CH2CH2O)nCH2CH2OH, —((CH2)1-8C(O)O)n(CH2)mOH, —((CH2)1-8C(O)O)n(CH2CH2O)m(OC(O)(CH2)1-8)pOH, —((CH2)1-8C(O)O)n(CH2CH2)m(OC(O)(CH2)1-8)mOH, —(CH2C(O)O)n(CH2CH2)m(OC(O)CH2)pOH, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))pOH, —((CH2)nOC(O)O)(CH2CH2)mOH, —(CH2)nNHC(O)(CH2)mOH, and —(CH2)nC(O)NH(CH2)mOH, C1-n alkyl, C1-n alkenyl, C1-n alkynyl, C6-10 aryl, and succinimidyl, wherein any one or more H atoms of Ra or R4 can optionally be replaced with an F atom;
- each of R5 and R6 is independently —(CH2)n—, —(CH2)nO(CH2)m—, —(CH2CH2O)nCH2CH2—, —(CH2CH2)n(CH2)m—, —(CH2)n(CH2CH2O))n(CH2)p—, —((CH2)1-8C(O)O)n(CH2)m—, —((CH2)1-8C(O)O)n(CH2CH2O)m(OC(O)(CH2)1-8)p—, —((CH2)1-8 C(O)O)n(CH2CH2)m(OC(O)(CH2)1-8)p—, —(CH2C(O)O)n(CH2CH2)m(OC(O)CH2)p—, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))p—, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))p—, —((CH2)nOC(O)O)(CH2CH2)m—, —(CH2)nNHC(O)(CH2)m—, —(CH2)nC(O)NH(CH2)m, or —(CH2)nCH(OH)(CH2)m—
- each n, m, p, q, and r is independently 1 to 10,000;
- a is 1 to 100,000;
- and,
- b is 0 to 100,000.
10 more elements
A polymer comprising:
- a polymer backbone comprising:
- a first monomeric unit derived from a compound consisting of an isocyanate and a diol or a polyol, and
- one or more second monomeric units, the one or more second monomeric units comprising a zwitterionic precursor monomeric unit, wherein the zwitterionic precursor monomeric unit comprises a secondary or a tertiary amine within the polymer backbone;
- and
- wherein the polymer backbone comprises repeating units of Formula (II):
- wherein each R4 is independently selected from —H, —(CH2CH2O)nCH3, —(CH2CH2O)n(CH2)mCH3, —(CH2CH2O)n(CH2)mOH, —((CH2)nO)m((CH2)pO)q(CH2)rOH, —(CH2CH2O)nH, —(CH2)nOH, —(CH2)nO(CH2)mOH, —(CH2CH2OCH2CH2)nOH, —(CH2CH2O)nCH2CH2OH, —((CH2)1-8C(O)O)n(CH2)mOH, —((CH2)1-8—C(O)O)n(CH2CH2O)m(OC(O)(CH2)1-8)pOH, —((CH2)1-8C(O)O)n(CH2CH2)m(OC(O)(CH2)1-8)mOH, —(CH2C(O)O)n(CH2CH2)m(OC(O)CH2)pOH, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))pOH, —((CH2)nOC(O)O)(CH2CH2)mOH, —(CH2)nNHC(O)(CH2)mOH, and —(CH2)n(C(O)NH(CH2)mOH, C1-n alkyl, C1-n alkenyl, C1-n alkynyl, C6-10 aryl, and succinimidyl, wherein any one or more H atom of R4 can optionally be replaced with an F atom;
- R5 is —(CH2)n—, —(CH2)nO(CH2)m—, —(CH2CH2OCH2CH2)n—, —(CH2CH2O)nCH2CH2—, —(CH2CH2)n(CH2)m—, —(CH2)n(CH2CH2O)n(CH2)p—, —((CH2)1-8C(O)O)n(CH2)m—, —((CH2)1- 8C(O)O)n(CH2CH2O)m(OC(O)(CH2)1-8)p—, —((CH2)1-8C(O)O)n(CH2CH2)m(OC(O)(CH2)1-8)p—, —(CH2C(O)O)n(CH2CH2)m(OC(O)CH2)p—, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))p—, —(CH(CH3)C(O)O)n(CH2CH2)m(OC(O)CH(CH3))p—, —((CH2)nOC(O)O)(CH2CH2) m, —(CH2)nNHC(O)(CH2)m—, —(CH2)nC(O)NH(CH2)m—, or —(CH2)nCH(OH)(CH2)m—;
- and
- each n, m, p, q, and r is independently 1 to 10,000;
- or wherein the polymer backbone comprises repeating units of Formula (III), (IV), or (VI):
- wherein x is 1 to 1,000,000;
- or wherein the polymer backbone comprises repeating units of Formula (V):
- or wherein the polymer backbone comprises repeating units of Formula (VII):
- wherein Z is O or NH, and x is 1 to 30.
11 more elements
Dependencies are inferred from the claim text.