# US 11,298,444 B2 · Non-degradable, low swelling, water soluble radiopaque hydrogel polymer > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,298,444 B2 - Document ID: US11298444B2 - Status: Granted - Kind: B2 - Application number: 15/068,415 - Filed: 2016-03-11 - Published: 2016-07-07 - Granted: 2022-04-12 - Earliest claimed: 2005-04-01 - Assignees: TriVascular, Inc. - Applicants: Trivascular, Inc. - Inventors: Syed H. Askari; Robert G. Whirley - Web page: https://patentgrep.com/patent/US11298444B2 ## CPC - A61L 31/06: obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds {(A61L31/041 takes precedence)} - A61K 49/0457: {Semi-solid forms, ointments, gels, hydrogels} - A61L 24/0031: {Hydrogels or hydrocolloids} - A61L 31/145: {Hydrogels or hydrocolloids} - A61L 31/18: Materials at least partially X-ray or laser opaque - A61K 49/0404: {containing barium sulfate} - A61L 2430/36: for embolization or occlusion, e.g. vaso-occlusive compositions or devices - A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K) - A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D) ## Abstract Hydrogel compositions prepared from amine components and glycidyl ether components are provided which are biocompatible and suitable for use in vivo due, in part, to their excellent stability. ## Claims ### Claim 1 A method of forming a material in situ comprising: introducing within a patient a mixture of a first water soluble reactive component having a molecular weight between about 200 and about 10,000 and a second water soluble reactive component having a molecular weight between about 100 and about 2500, solubilized in a flowable aqueous solution, the mixture having a viscosity between about 20 cp and about 100 cp such that it maintains fluidity upon introduction into a delivery tube in order to travel through the length of the delivery tube to fill one or more inflatable members of an implantable device comprising a stent graft, wherein the mixture retains the viscosity between about 20 cp and about 100 cp at the stent graft at the stent graft in order to continue to flow within the volume of the one or more inflatable members and conform to morphology of the walls of the one or more inflatable members, said method further comprising the initiation of the formation of a solid material in the mixture, wherein said initiation of the formation of a solid material consists essentially of initiating a chemical reaction of functional groups on said first water soluble reactive component with functional groups on said second water soluble reactive component, said chemical reaction consisting essentially of chemical covalent bonding, to form said solid material, said solid material being formed and having a swellability less than about 10% within about 3 minutes to about 30 minutes of initiating the chemical reaction of the functional groups to form the solid material. ### Claim 2 (depends on 1) The method of claim 1, wherein the mixture reacts at a pH of at least about 7.4 to form the solid. ### Claim 3 (depends on 2) The method of claim 2, wherein the mixture remains less rigid for more than about 3 minutes. ### Claim 4 A method of forming a material in situ comprising: introducing within a patient a mixture of a first water soluble reactive component having a molecular weight of between about 200 and about 10,000 and a second water soluble reactive component having a molecular weight between about 100 and about 2500, solubilized in a flowable solution, the mixture having a first pH and having a viscosity between about 20 cp and about 100 cp such that it maintains fluidity in order to travel through a delivery tube to fill one or more inflatable members of an implantable device comprising a stent graft, wherein the mixture retains the viscosity between about 20 cp and about 100 cp at the stent graft at the stent graft in order to continue to flow within the volume of the one or more inflatable members and conform to morphology of the walls of the one or more inflatable members, said method further comprising the initiation of the formation of a material, wherein said initiation of the formation of a material consists essentially of initiating at said first pH, a chemical reaction of functional groups on said first water soluble reactive component with functional groups on said second water soluble reactive component, said chemical reaction consisting essentially of chemical covalent bonding, to form said material, said material being formed and having a swellability less than about 20% within about 3 minutes to about 30 minutes of initiating the chemical reaction of the functional groups to form the material. ### Claim 5 (depends on 4) The method of claim 4, wherein the mixture remains less rigid for more than about 3 minutes. ### Claim 6 (depends on 5) The method of claim 5, wherein the first pH is at least about 7.4. ### Claim 7 (depends on 6) The method of claim 6, wherein the second water soluble reactive component comprises functional groups which are different from the functional groups on the first water soluble reactive component. ### Claim 8 (depends on 4) The method of claim 4, further comprising adding an additive to the mixture to increase the cure rate of the material. ### Claim 9 A method of forming a material in situ comprising: introducing within a patient a mixture of a first water soluble reactive component and a second water soluble reactive component solubilized in a flowable aqueous solution, the mixture having a viscosity between about 20 cp and about 100 cp such that it maintains fluidity in order to travel through a delivery tube to fill one or more inflatable members of an implantable device comprising a stent graft, wherein the mixture retains the viscosity between about 20 cp and about 100 cp at the stent graft at the stent graft in order to continue to flow within the volume of the one or more inflatable members and conform to morphology of the walls of the one or more inflatable members, wherein the first water soluble reactive component has a molecular weight between about 200 and about 10,000, said method further comprising the initiation of the formation of a solid and non-degradable material, wherein said initiation of the formation of a solid and non-degradable material consists essentially of initiating a chemical reaction of functional groups on said first water soluble reactive component with functional groups on said second water soluble reactive component, by thoroughly mixing together, at a first pH, said first water soluble reactive component with said second water soluble reactive component and transferring the mixture to a syringe for injection into the delivery tube at said first pH, said chemical reaction consisting essentially of chemical covalent bonding, to form said solid and non-degradable material, said solid and non-degradable material being formed and having a swellability less than about 30% and an elastic modulus of at least about 30 psi within about 3 minutes to about 30 minutes after completing mixing of the components. ### Claim 10 (depends on 9) The method of claim 9, wherein the mixture reacts at a pH of at least about 7.4 to form the solid. ### Claim 11 (depends on 9) The method of claim 9, wherein the molecular weight of the second component is between about 100 and about 2500. ### Claim 12 (depends on 9) The method of claim 9, further comprising adding an additive to increase the cure rate of the material. ### Claim 13 (depends on 1) The method of claim 1, wherein the second water soluble reactive component comprises functional groups which are different from the functional groups on the first water soluble reactive component. ### Claim 14 (depends on 1) The method of claim 1, wherein the solid material is non-degradable. ### Claim 15 (depends on 1) The method of claim 1, wherein the flowable solution has a cure time of about 5 to about 20 minutes. ### Claim 16 (depends on 1) The method of claim 1, wherein the mixture forms a hard gel in about 12 minutes or less. ### Claim 17 (depends on 9) The method of claim 9, wherein the first pH is about 7.4 or greater.