Patents Assigned to The Secant Group, LLC
  • Patent number: 12221618
    Abstract: A pH-modulating poly(glycerol sebacate) composition includes poly(glycerol sebacate) and at least one pH-modulating agent associated with the poly(glycerol sebacate). A process of making a pH-modulating poly(glycerol sebacate) composition includes forming a poly(glycerol sebacate) by a water-mediated reaction from glycerol and sebacic acid and associating at least one pH-modulating agent with the poly(glycerol sebacate). A process of modulating a pH of a buffered aqueous solution includes placing a pH-modulating poly(glycerol sebacate) composition in a buffered aqueous solution. The pH-modulating agent is released into the buffered aqueous solution during degradation of the poly(glycerol sebacate) to reduce a decrease in pH of the buffered aqueous solution caused by degradation of the poly(glycerol sebacate).
    Type: Grant
    Filed: August 18, 2021
    Date of Patent: February 11, 2025
    Assignee: THE SECANT GROUP, LLC
    Inventors: Peter D. Gabriele, Jeremy J. Harris, Charles Brendan Nicholson, Steven Lu, Brian Ginn
  • Patent number: 12144894
    Abstract: A delivery system is described that includes a controlled release device that includes a crosslinked poly(glycerol sebacate) (PGS) or other glycerol ester and a controlled release compound, the controlled release device being provided in a contracted state and being expandable to a three-dimensional expanded state in a target location. The delivery systems provides an expandible, flexible biodegradable elastomer loaded with an active ingredient to allow for extended release for different dosage forms for either human or animal health products in vivo, delivered through the gastrointestinal tract.
    Type: Grant
    Filed: July 1, 2021
    Date of Patent: November 19, 2024
    Assignee: THE SECANT GROUP, LLC
    Inventors: Stephanie Reed, Alexander M. Stahl, Manasi Chawathe Baker, Peter D. Gabriele, Amanda K. Weber
  • Patent number: 11980665
    Abstract: A method of cancer hyperthermia therapy includes placing a device including an exogenously-excitable polymeric material at a cancer hyperthermia therapy site of a patient. The method also includes supplying an exogenous energy to the device such that the exogenous energy excites the exogenously-excitable polymeric material at the cancer hyperthermia therapy site to heat the cancer hyperthermia therapy site to a hyperthermia temperature. A method of preparing a polymeric material includes combining an alcohol monomer, a seed of the polymeric material, and an aqueous liquid in a vessel. The method also includes adding an acid monomer to the vessel and supplying an exogenous energy to the vessel. The polymeric material is exogenously excited by the exogenous energy to heat the polymeric material. The method further includes removing water from the vessel and producing the polymeric material, which is a polyester, in the vessel.
    Type: Grant
    Filed: February 3, 2020
    Date of Patent: May 14, 2024
    Assignee: THE SECANT GROUP, LLC
    Inventors: Peter D. Gabriele, Jared Ely, Jeremy J. Harris
  • Patent number: 11939444
    Abstract: In some embodiments, a polymer film includes a base composition of poly(ethylene-vinyl acetate) and a surface composition comprising hydroxy groups. In some embodiments, a polymer film includes a base layer of a first composition of poly(ethylene-vinyl acetate), a surface layer at a surface of the base layer, and a coating layer of a second composition of a copolymer of glycerol and sebacic acid. The surface layer includes surface hydroxy groups converted from acetate groups of the poly(ethylene-vinyl acetate). The second composition is attached to the surface layer by ester bonds between carboxyl groups of the copolymer and the hydroxy groups. A single-use bioreactor bag includes a polymer film including a base composition of poly(ethylene-vinyl acetate) and a surface composition comprising hydroxy groups. A method of modifying a poly(ethylene-vinyl acetate) film includes converting acetate groups at a first surface of the poly(ethylene-vinyl acetate) film to hydroxy groups.
    Type: Grant
    Filed: April 9, 2021
    Date of Patent: March 26, 2024
    Assignee: THE SECANT GROUP, LLC
    Inventors: Peter D. Gabriele, Jeremy J. Harris, Scott Radzinski, Brian Ginn, Ryan R. Smalley
  • Patent number: 11883557
    Abstract: A process forms an implantable product including poly(glycerol sebacate) urethane (PGSU) loaded with an active pharmaceutical ingredient (API). The process includes homogeneously mixing a flowable poly(glycerol sebacate) (PGS) resin with the API and a catalyst to form a resin blend. The process also includes homogeneously combining the resin blend with an isocyanate to form a reaction mixture and injecting the reaction mixture to form the PGSU loaded with the API. An implantable product includes a PGSU loaded with an API. In some embodiments, the implantable product includes at least 40% w/w of the API, and the implantable product releases the API by surface degradation of the PGSU at a predetermined release rate for at least three months under physiological conditions. In some embodiments, the PGSU is formed from a PGS reacted with an isocyanate at an isocyanate-to-hydroxyl stoichiometric (crosslinking) ratio in the range of 1:0.25 to 1:1.25.
    Type: Grant
    Filed: May 9, 2022
    Date of Patent: January 30, 2024
    Assignee: THE SECANT GROUP, LLC
    Inventors: Stephanie Reed, Carissa Smoot, Dennis Shull, Todd Crumbling, John D'Ottavio, Peter D. Gabriele, Jeremy J. Harris, Charles Brendan Nicholson, Jared Ely
  • Patent number: 11866523
    Abstract: A water-mediated process prepares a polymeric (meth)acrylation composition. In some embodiments, the process includes providing a stabilized aqueous solution including a (meth)acrylation component and a polyol monomer in a vessel under an inert atmosphere and adding a diacid monomer to the vessel under the inert atmosphere. In some embodiments, the process includes providing a stabilized aqueous solution including a (meth)acrylation component and a copolymer of a polyol monomer and a diacid monomer in a vessel under an inert atmosphere. The process further includes heating and removing water from the vessel under the inert atmosphere to produce the polymeric (meth)acrylation composition. The polymeric (meth)acrylation composition includes a (meth)acrylation polyester copolymer of the diacid monomer and the polyol monomer with the (meth)acrylation component conjugated to the (meth)acrylation polyester copolymer.
    Type: Grant
    Filed: April 6, 2021
    Date of Patent: January 9, 2024
    Assignee: THE SECANT GROUP, LLC
    Inventors: Peter D. Gabriele, Scott Radzinski, Jeremy J. Harris, Brian Ginn
  • Patent number: 11686015
    Abstract: A manufacturing process includes spinning at least one continuous poly(glycerol sebacate) (PGS)/alginate fiber from a polymeric solution comprising PGS and alginate in water, drafting the at least one continuous PGS/alginate fiber in at least one coagulation bath, and drawing the at least one continuous PGS/alginate fiber from the at least one coagulation bath. A yarn includes at least one continuous PGS fiber. A continuous poly(glycerol sebacate) (PGS)/alginate fiber forming system includes a feeding tank holding a polymeric solution of alginate and PGS, a pump, a spinneret, a first coagulation bath, a first winder, a second coagulation bath, a second winder, and a bobbin winder, the system forming at least one continuous PGS/alginate fiber from the polymeric solution of alginate and PGS.
    Type: Grant
    Filed: October 21, 2021
    Date of Patent: June 27, 2023
    Assignee: THE SECANT GROUP, LLC
    Inventors: Mevlut Tascan, Kayla Wroblesky, Todd Crumbling, Michael S. Flemmens
  • Patent number: 11602721
    Abstract: A method of forming cured microparticles includes providing a poly(glycerol sebacate) resin in an uncured state. The method also includes forming the composition into a plurality of uncured microparticles and curing the uncured microparticles to form the plurality of cured microparticles. The uncured microparticles are free of a photo-induced crosslinker. A method of forming a scaffold includes providing microparticles including poly(glycerol sebacate) in a three-dimensional arrangement. The method also includes stimulating the microparticles in the three-dimensional arrangement to sinter the microparticles, thereby forming the scaffold having a plurality of pores. A scaffold is formed of a plurality of microparticles including a poly(glycerol sebacate) thermoset resin in a three-dimensional arrangement. The scaffold has a plurality of pores.
    Type: Grant
    Filed: January 6, 2020
    Date of Patent: March 14, 2023
    Assignee: THE SECANT GROUP, LLC
    Inventors: Steven Lu, Peter D. Gabriele, Julia Donnelly, Brian Ginn, Charles Brendan Nicholson, Jeremy J. Harris, Michael S. Flemmens
  • Patent number: 11576797
    Abstract: A manufacturing process forms a bored hollow lumen. The manufacturing process includes providing a solid rod of a bioresorbable material and boring a hole axially through the solid rod. The manufacturing process also includes modifying surface defects formed on a luminal surface by the boring, the luminal surface defining the hole, thereby forming the bored hollow lumen. A bored hollow lumen includes a lumen wall including a bioresorbable material. The lumen wall has an abluminal surface and a luminal surface. The luminal surface defines a bore through the bored hollow lumen. The bioresorbable material has a uniform crosslinking density.
    Type: Grant
    Filed: October 12, 2018
    Date of Patent: February 14, 2023
    Assignee: THE SECANT GROUP, LLC
    Inventors: Peter D. Gabriele, Steven Lu
  • Patent number: 11406732
    Abstract: A process forms an implantable product including poly(glycerol sebacate) urethane (PGSU) loaded with an active pharmaceutical ingredient (API). The process includes homogeneously mixing a flowable poly(glycerol sebacate) (PGS) resin with the API and a catalyst to form a resin blend. The process also includes homogeneously combining the resin blend with an isocyanate to form a reaction mixture and injecting the reaction mixture to form the PGSU loaded with the API. An implantable product includes a PGSU loaded with an API. In some embodiments, the implantable product includes at least 40% w/w of the API, and the implantable product releases the API by surface degradation of the PGSU at a predetermined release rate for at least three months under physiological conditions. In some embodiments, the PGSU is formed from a PGS reacted with an isocyanate at an isocyanate-to-hydroxyl stoichiometric (crosslinking) ratio in the range of 1:0.25 to 1:1.25.
    Type: Grant
    Filed: January 13, 2021
    Date of Patent: August 9, 2022
    Assignee: THE SECANT GROUP, LLC
    Inventors: Stephanie Reed, Carissa Smoot, Dennis Shull, Todd Crumbling, John D'Ottavio, Peter D. Gabriele, Jeremy J. Harris, Charles Brendan Nicholson, Jared Ely
  • Patent number: 11208627
    Abstract: A biocontainment vessel includes a vessel structure including a structural composition and an enhancement composition associated with the structural composition. The enhancement composition includes a co-polymer. The co-polymer is a poly(glycerol sebacate) or a poly(glycerol sebacate urethane). The enhancement composition may also include an augmentation agent associated with the co-polymer. The enhancement composition is located with respect to the structural composition such that the enhancement composition benefits biological cells contained in the biocontainment vessel. A composition includes a co-polymer and an augmentation agent contained by the co-polymer. A method of containing biological cells includes placing the biological cells in an augmented biocontainment vessel and storing them in the augmented biocontainment vessel under predetermined conditions. An augmented substrate includes a substrate and an enhancement composition coating a surface of the substrate.
    Type: Grant
    Filed: January 17, 2019
    Date of Patent: December 28, 2021
    Assignee: THE SECANT GROUP, LLC
    Inventors: Peter D. Gabriele, Jeremy J. Harris, Charles Brendan Nicholson, Steven Lu, Jeffrey H. Robertson, Gael Peron
  • Patent number: 11186926
    Abstract: A manufacturing process includes spinning at least one continuous poly(glycerol sebacate) (PGS)/alginate fiber from a polymeric solution comprising PGS and alginate in water, drafting the at least one continuous PGS/alginate fiber in at least one coagulation bath, and drawing the at least one continuous PGS/alginate fiber from the at least one coagulation bath. A yarn includes at least one continuous PGS fiber. A continuous poly(glycerol sebacate) (PGS)/alginate fiber forming system includes a feeding tank holding a polymeric solution of alginate and PGS, a pump, a spinneret, a first coagulation bath, a first winder, a second coagulation bath, a second winder, and a bobbin winder, the system forming at least one continuous PGS/alginate fiber from the polymeric solution of alginate and PGS.
    Type: Grant
    Filed: November 1, 2018
    Date of Patent: November 30, 2021
    Assignee: THE SECANT GROUP, LLC
    Inventors: Mevlut Tascan, Kayla Wroblesky, Todd Crumbling, Michael S. Flemmens
  • Patent number: 11124762
    Abstract: A pH-modulating poly(glycerol sebacate) composition includes poly(glycerol sebacate) and at least one pH-modulating agent associated with the poly(glycerol sebacate). A process of making a pH-modulating poly(glycerol sebacate) composition includes forming a poly(glycerol sebacate) by a water-mediated reaction from glycerol and sebacic acid and associating at least one pH-modulating agent with the poly(glycerol sebacate). A process of modulating a pH of a buffered aqueous solution includes placing a pH-modulating poly(glycerol sebacate) composition in a buffered aqueous solution. The pH-modulating agent is released into the buffered aqueous solution during degradation of the poly(glycerol sebacate) to reduce a decrease in pH of the buffered aqueous solution caused by degradation of the poly(glycerol sebacate).
    Type: Grant
    Filed: January 17, 2019
    Date of Patent: September 21, 2021
    Assignee: THE SECANT GROUP, LLC
    Inventors: Peter D. Gabriele, Jeremy J. Harris, Charles Brendan Nicholson, Steven Lu, Brian Ginn
  • Patent number: 11065099
    Abstract: A composite lumen includes an extruded tube of a composite including a poly(glycerol sebacate) (PGS) matrix mixed with a PGS thermoset filler. The composite lumen also includes an overbraid structure overlying an outer surface of the extruded tube. A method of forming a composite lumen includes extruding a PGS tube of a composite including a PGS matrix mixed with a PGS thermoset filler. The method also includes applying an overbraid structure over an outer surface of the extruded tube.
    Type: Grant
    Filed: October 5, 2018
    Date of Patent: July 20, 2021
    Assignee: THE SECANT GROUP, LLC
    Inventors: Steven Lu, Peter D. Gabriele, Jeremy J. Harris, Seth A. Winner, Andrew Metzger
  • Patent number: 10918724
    Abstract: A method of forming a skin care product includes combining at least one additive including at least one active ingredient with at least one glycerol-sebacate component having repeating units of (glycerol sebacate), water, a co-solvent, and at least one of an emulsifier, a surfactant, and a bodying agent to form the skin care product. A dermocosmetic composition includes at least one additive including at least one active ingredient and at least one glycerol-sebacate component having repeating units of (glycerol sebacate). A method of skin care includes applying a dermocosmetic composition to a skin surface.
    Type: Grant
    Filed: February 21, 2019
    Date of Patent: February 16, 2021
    Assignee: THE SECANT GROUP, LLC
    Inventors: Peter D. Gabriele, Jeremy J. Harris, Carissa Smoot, Charles Brendan Nicholson, Stephanie Reed, Ryan R. Smalley
  • Patent number: 10918729
    Abstract: A bone filling composition includes a bone filler. The bone filler includes microparticles of at least one elastomeric material. The at least one elastomeric material includes a poly(glycerol sebacate)-based thermoset. The poly(glycerol sebacate)-based thermoset may be porous thermoset poly(glycerol sebacate) flour, thermoset poly(glycerol sebacate) microspheres, or a combination thereof. In some embodiments, the bone filling composition is a bone filling composite that further includes a carrier material including a poly(glycerol sebacate) resin. A method of forming a bone filling composite includes selecting a bone filler and mixing the bone filler with a carrier material to form the bone filling composite. A method of treating a bony defect includes molding a bone filling composite and placing the bone filling composite in the bony defect. The bone filling composite includes a bone filler mixed with a carrier material.
    Type: Grant
    Filed: January 31, 2019
    Date of Patent: February 16, 2021
    Assignee: THE SECANT GROUP, LLC
    Inventors: Jeremy J. Harris, Charles Brendan Nicholson, Peter D. Gabriele, Jared Ely, Brian Ginn
  • Patent number: 10918764
    Abstract: A process forms an implantable product including poly(glycerol sebacate) urethane (PGSU) loaded with an active pharmaceutical ingredient (API). The process includes homogeneously mixing a flowable poly(glycerol sebacate) (PGS) resin with the API and a catalyst to form a resin blend. The process also includes homogeneously combining the resin blend with an isocyanate to form a reaction mixture and injecting the reaction mixture to form the PGSU loaded with the API. An implantable product includes a PGSU loaded with an API. In some embodiments, the implantable product includes at least 40% w/w of the API, and the implantable product releases the API by surface degradation of the PGSU at a predetermined release rate for at least three months under physiological conditions. In some embodiments, the PGSU is formed from a PGS reacted with an isocyanate at an isocyanate-to-hydroxyl stoichiometric (crosslinking) ratio in the range of 1:0.25 to 1:1.25.
    Type: Grant
    Filed: August 21, 2019
    Date of Patent: February 16, 2021
    Assignee: THE SECANT GROUP, LLC
    Inventors: Stephanie Reed, Carissa Smoot, Dennis Shull, Todd Crumbling, John D'Ottavio, Peter D. Gabriele, Jeremy J. Harris, Charles Brendan Nicholson, Jared Ely
  • Patent number: 10822450
    Abstract: A method of preparing a polymeric material includes combining a glycerol-pharmaceutical conjugate, glycerol, and water in a vessel. The glycerol-pharmaceutical conjugate includes a pharmaceutical compound, for example, salicylic acid, having at least one carboxyl group attached to glycerol by an ester bond. The method also includes adding sebacic acid to the vessel and removing water from the vessel and reacting the glycerol, glycerol-pharmaceutical conjugate, and sebacic acid in the vessel at atmospheric pressure in the presence of an inert gas. The method further includes applying a sub-atmospheric pressure to the vessel after the step of reacting, to form the polymeric material in the vessel. The polymeric material includes a polyester copolymer of the sebacic acid and the glycerol and the pharmaceutical compound.
    Type: Grant
    Filed: July 11, 2018
    Date of Patent: November 3, 2020
    Assignee: THE SECANT GROUP LLC
    Inventors: Peter D. Gabriele, Carissa Smoot, Charles Brendan Nicholson, Jeremy J. Harris
  • Patent number: 10793743
    Abstract: The application is directed to aqueous dispersible biodegradable compositions of esters which are the condensation reaction product of a polyol and a diacid which are within a matrix of hydrated polypeptide. The compositions are useful in additive manufacturing and other applications for use with implantable articles. In some embodiments, the ester in the compositions is the product of a glyercol-sebacic acid condensation reaction.
    Type: Grant
    Filed: October 4, 2018
    Date of Patent: October 6, 2020
    Assignee: THE SECANT GROUP, LLC
    Inventors: Kayla Wroblesky, Peter D. Gabriele, Jeremy J. Harris, Carissa Smoot, Charles Brendan Nicholson, Austin Robertson, Julia Donnelly
  • Patent number: 10610347
    Abstract: A textile engineered prosthetic includes a continuous tube and at least one band of increased thickness formed over a portion of the continuous tube. The continuous tube includes a body portion and a bifurcated portion. The band of increased thickness forms a biomimetic surface. A bioreactor system includes a bioreactor container including a first compartment, a second compartment, a first membrane separating the first and second compartments, a third compartment, and a second membrane separating the second and third compartments. The bioreactor system also includes a woven textile prosthetic integrated with the bioreactor container in the second compartment to form a single bioreactor unit. A furcated textile article includes a continuous tube having a body portion and a furcated portion bifurcated N times from the body portion. The furcated textile article is a continuous woven piece formed from N shuttles of a shuttle loom, where N is at least two.
    Type: Grant
    Filed: March 18, 2016
    Date of Patent: April 7, 2020
    Assignee: THE SECANT GROUP, LLC
    Inventors: Eric H. Whiting, Seth A. Winner, Emily Y. Ho, Peter Gabriele, Jeremy J. Harris