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US 12,616,773 B2Granted
Bioadhesive compositions and methods of making the same
AssigneeThe Penn State Research Foundation
InventorsJian Yang, Jinshan Guo
Life of this patent
Estimating the term…
Abstract
Disclosed herein are citrate-based mussel-inspired bioadhesives and methods of making and using the same. Also disclosed herein are methods of treating wounds.
Claims19
A crosslinked composition comprising:
- a) a polymerization product of:
- one or more monomers of Formula (I), one or more units of a block copolymer of Formula (V) or Formula (V′), one or more monomers of Formula (III), and optionally one or more compounds of Formula (IV):
- wherein
- R1, R2, and R3 are, independently, selected from hydrogen, —CH3, and CH2CH3;
- R4 is selected from hydrogen, a hydroxyl group, —NH2, —OCH3, —OCH2CH3, —CH3, —CH2CH3, a C3 to C22 alkyl or alkenyl group, —CH2CH2OH, and —CH2CH2NH2;
- R5 is selected from hydrogen, a hydroxyl group, —NH2, —CH3, —CH2CH3, a C3 to C22 alkyl or alkenyl group, —CH2CH2OH, and —CH2CH2NH2;
- R6 is selected from —CH3, —CH2CH3, —CH2CH2OH, and —CH2CH2NH2;
- R8, R9, R10, and R11 are, independently, selected from hydrogen, —CH2 (CH2)xNH2, —CH2 (CHR13) NH2, and —CH2 (CH2)xCOOH groups;
- wherein at least one of R8, R9, R10, and
- R11 is not hydrogen;
- R12 is an amino acid side chain;
- R13 is —COOH or —(CH2)yCOOH;
- x is an integer from 0 to 20;
- y is an integer from 1 to 20;
- and
- a and b are independently chosen from n=1-20;
- wherein the polymerization product does not comprise metal cations;
- and
- b) a first crosslinking initiator having a formula Ab′Oa′, wherein A is a monovalent, divalent, or trivalent metallic cation and wherein a′ and b′ are dependent on the valency of A;
- wherein A is not a transition metal cation and wherein the first crosslinking initiator is configured to crosslink the polymerization product to form the crosslinked composition;
- and
- wherein the crosslinked composition is a polymer network having at least one crosslink comprising two catechol moieties directly and covalently coupled to each other;
- and
- wherein the crosslinked composition is a hydrogel or an organogel and is an adhesive composition.
21 more elements
A crosslinked composition formed by
- a) forming a polymerization product by reacting one or more monomers of Formula (I) with:
- a block copolymer of Formula (V) or Formula (V′),
- one or more monomers of Formula (III), and
- optionally one or more compounds of Formula (IV):
- wherein
- R1, R2, and R3 are, independently, selected from hydrogen, —CH3, and —CH2CH3;
- R4 is selected from hydrogen, a hydroxyl group, —NH2, —OCH3, —OCH2CH3, —CH3, —CH2CH3, a C3 to C22 alkyl or alkenyl group, —CH2CH2OH, and —CH2CH2NH2;
- R5 is selected from hydrogen, a hydroxyl group, —NH2, —CH3, —CH2CH3, a C3 to C22 alkyl or alkenyl group, —CH2CH2OH, and —CH2CH2NH2;
- R6 is selected from —CH3, —CH2CH3, —CH2CH2OH, and —CH2CH2NH2;
- R8, R9, R10, and R11 are, independently, selected from
- R12 is an amino acid side chain;
- R13 is —COOH or —(CH2)yCOOH;
- x is an integer from 0 to 20;
- y is an integer from 1 to 20;
- and
- a and b are independently chosen from n=1-20;
- wherein the polymerization product does not comprise metal cations;
- b) crosslinking the polymerization product with a first crosslinking initiator having a formula Ab′Oa′, wherein A is a monovalent, divalent, or trivalent metallic cation and wherein a′ and b′ are defined by the valency of A;
- wherein A is not a transition metal cation;
- wherein the crosslinked composition is a polymer network having at least one crosslink comprising two catechol moieties directly and covalently coupled to each other;
- and
- wherein the crosslinked composition is a hydrogel or organogel and is an adhesive composition.
19 more elements
Dependencies are inferred from the claim text.