Synthesis and characterization of well defined poly(propylene fumarate) and poly(ethylene glycol) block copolymers

    公开(公告)号:AU2018313090A1

    公开(公告)日:2020-02-27

    申请号:AU2018313090

    申请日:2018-08-07

    Applicant: UNIV AKRON

    Abstract: In one or more embodiments, the present invention provides a low molecular weight, non-toxic, resorbable poly(ethylene glycol)(PEG) -block- poly(propylene fumarate) (PPF) diblock copolymers and poly(propylene fumarate) (PPF) -block- poly(ethylene glycol)(PEG) -block- poly(propylene fumarate) (PPF) triblock copolymers (and related methods for their making and use) that permits hydration for the formation of such things as hydrogels and has constrained and predictable material properties suitable for 3D printing and drug delivery applications. Using continuous digital light processing (cDLP) hydrogels the diblock and triblock copolymers can be photochemically printed from an aqueous solution into structures having a 10-fold increase in elongation at break compared to traditional diethyl fumarate (DEF) based printing. Furthermore, PPF-PEG-PPF triblock hydrogels have also been found in vitro to be biocompatible across a number of engineered MC3T3, NIH3T3, and primary Schwann cells.

    SYNTHESIS AND CHARACTERIZATION OF WELL DEFINED POLY(PROPYLENE FUMARATE) AND POLY(ETHYLENE GLYCOL) BLOCK COPOLYMERS

    公开(公告)号:CA3072503A1

    公开(公告)日:2019-02-14

    申请号:CA3072503

    申请日:2018-08-07

    Applicant: UNIV AKRON

    Abstract: In one or more embodiments, the present invention provides a low molecular weight, non-toxic, resorbable poly(ethylene glycol)(PEG) -block- poly(propylene fumarate) (PPF) diblock copolymers and poly(propylene fumarate) (PPF) -block- poly(ethylene glycol)(PEG) -block- poly(propylene fumarate) (PPF) triblock copolymers (and related methods for their making and use) that permits hydration for the formation of such things as hydrogels and has constrained and predictable material properties suitable for 3D printing and drug delivery applications. Using continuous digital light processing (cDLP) hydrogels the diblock and triblock copolymers can be photochemically printed from an aqueous solution into structures having a 10-fold increase in elongation at break compared to traditional diethyl fumarate (DEF) based printing. Furthermore, PPF-PEG-PPF triblock hydrogels have also been found in vitro to be biocompatible across a number of engineered MC3T3, NIH3T3, and primary Schwann cells.

    BLOCK COPOLYMERS OF LACTONES AND POLY(PROPYLENE FUMARATE)

    公开(公告)号:CA3012937A1

    公开(公告)日:2018-08-02

    申请号:CA3012937

    申请日:2018-03-20

    Applicant: UNIV AKRON

    Abstract: In various embodiments, the present invention provides well-defined biodegradable poly(lactone-b-propylene fumarate) diblock and triblock polymers formed using a novel one-pot, scalable ring-opening block-order copolymerization (ROBOCOP) technique that utilizes magnesium 2,6-di-tert-butyl-4-methylphenoxide (Mg(BHT)2(THF)2) to "switch" from the ROP of cyclic esters to the ROCOP of maleic anhydride (MAn) and propylene oxide (PO) to produce PPF based block copolymers for application in additive manufacturing and patient specific regenerative medicine. These block copolymers are fully resorbable and can be photochemically crosslinked in a number of applications, including 3D printing. By adding the lactone block to the PPF polymer, the viscosity of the resulting block copolymer at working temperatures can be precisely controlled and the quantity of the reactive diluent in printable resins can be reduced or eliminated.

    PHOSPHORYLATED POLY(ESTER-UREA) BASED DEGRADABLE BONE ADHESIVES

    公开(公告)号:CA3022412A1

    公开(公告)日:2017-11-02

    申请号:CA3022412

    申请日:2017-04-25

    Applicant: UNIV AKRON

    Abstract: In various aspects, the present invention provides a degradable and resorbable novel phosphate functionalized amino acid-based poly(ester urea) adhesive and related methods for its synthesis and use. These adhesives are formed from phosphate functionalized PEU polymers and copolymers crosslinked using one or more divalent metal crosslinking agents. The phosphate functionalized amino acid-based poly(ester urea) adhesives of various embodiments of the present invention have been found particularly effective in bonding bone to either bone or metal and have demonstrated adhesive strengths on bone samples that were significant and comparable to commercially available poly(methyl methacrylate) bone cement.

    WELL-DEFINED DEGRADABLE POLY(PROPYLENE FUMARATE) POLYMERS AND SCALABLE METHODS FOR THE SYNTHESIS THEREOF

    公开(公告)号:CA2967949A1

    公开(公告)日:2016-05-26

    申请号:CA2967949

    申请日:2015-11-18

    Abstract: The present invention provides a low molecular mass PPF polymer (and related methods) that is suitable for 3D printing and other polymer device fabrication modalities and can be made inexpensively in commercially reasonable quantities. These novel low molecular mass PPF polymers have a low molecular mass distribution (Ðm) and a wide variety of potential uses, particularly as a component in resins for 3D printing of medical devices. The ability to produce low Ðm PPF creates a new opportunity for reliable GMP production of PPF. It provides low cost synthesis and scalability of synthesis, blending of well-defined mass and viscosity PPF, and reduced reliance on solvents or heat to (a) achieve mixing of 3D printable resins or (b) and flowability during 3D printing. These PPF polymers are non-toxic, degradable, and resorbable and can be used in tissue scaffolds and medical devices that are implanted within a living organism.

    RADIOOPAQUE, IODINE FUNCTIONALIZED PHENYLALANINE-BASED POLY(ESTER UREA)S

    公开(公告)号:CA2948154A1

    公开(公告)日:2015-11-12

    申请号:CA2948154

    申请日:2015-05-07

    Applicant: UNIV AKRON

    Abstract: In one or more embodiments, the present invention provides iodine-functionalized phenylalanine-based poly(ester urea)s (PEUs) (and related methods for their synthesis and use) that are metal free, degradable, radiopaque and suitable for use in surgical implants and other medical devices used within a patient. In one or more embodiment of the present invention 4-Iodo-L-phenylalanine and L-phenylalanine are separately reacted with 1,6-hexanediol to produce two monomers, bis-4-I-L-phenylalanine-1,6-hexanediol-diester (1-IPHE-6 monomer) and bis-L-phenylalanine-1,6-hexanediol-diester (1-PHE-6 monomer). It has been found that by varying the feed ratio of the 1-IPHE-6 and 1-PHE-6 monomers, the copolymer composition may be modulated to predictably create phenylalanine-based PEUs having a wide variation in thermal, mechanical and radiopacity properties. As most medical device procedures require placement verification via fluoroscopic imaging, materials that possess inherent X-ray contrast are valuable for a number of applications.

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