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

A technology of polytrimethylene fumarate and diblock copolymer, which is applied in prosthesis, medical science, etc., and can solve problems that have not yet been discovered or developed

Active Publication Date: 2020-08-25
THE UNIVERSITY OF AKRON
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, well-ordered PEG and PPF block copolymers suitable for 3D printing have not been discovered or developed yet.

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0150] Synthetic Mg(BHT) 2 (THF) 2 catalyst

[0151] In a nitrogen-filled, oven-dried anti-bump Schlenk flask, 13.22 g (0.06 mol) of 2,6-di-tert-butyl-4-methylphenol (BHT) was dried under high vacuum for 40 min. The flask was backfilled with nitrogen and then injected with 20 mL of anhydrous THF (0.31 mol). After the BHT was dissolved, 30 mL of 1.0 M dibutylmagnesium in heptane (0.03 mol) was added dropwise within 1 hour, and the flask was cooled on ice. The reaction was stirred on ice for another 2 hours before a white precipitate formed. The solvent was removed by vacuum transfer, and the catalyst was dried overnight before being stored in a glove box. (17.5 g, 96% yield)

Embodiment 2

[0153] Dried polyethylene glycol raw material

[0154]Polyethylene glycol diol and methyl ether polyethylene glycol starting materials were purchased from Sigma (2 kDa and 4 kDa PEG-diol and methyl ether PEG) and TCI (1 kDa PEG-diol and methyl ether PEG) and dried according to previous literature. (See, Kinard, L.; Kasper, K.; Mikos, A. Drying Poly(Ethylene Glycol). Protoc. Exch. 2012, the disclosure of which is incorporated herein by reference in its entirety.) Briefly, 10.00 g Each PEG derivative was dissolved in anhydrous toluene and refluxed overnight using a Dean-Stark apparatus. The solution is then transferred through the cannula to a Molecular sieves in a dry round bottom flask overnight and then transferred to another dry round bottom flask with vacuum dried molecular sieves overnight. The toluene was then removed under vacuum and the PEG was transferred to a glove box. For scale-up polymerizations, the sieve drying step was omitted as the reaction was found to be...

Embodiment 3

[0156] Synthesis of Poly(Ethylene Glycol-Chemo-Trimethylene Maleate), DP 20 Using Methyl Ether PEG (MW 750)

[0157] Initiated by methyl ether PEG (MW 750) and induced by Mg(BHT) 2 (THF) 2 Catalyzed, poly(ethylene glycol-block-trimethylene maleate) was synthesized by the copolymerization of maleic anhydride and propylene oxide to a degree of polymerization (DP) of 20. As shown in Scheme 3 below.

[0158] Option 3

[0159]

[0160] Fill ampoules with Mg(BHT) using standard Schlenk line technology 2 (THF) 2 (57.8 mg, 0.095 mmol), methyl ether polyethylene glycol MW 750 (0.3573 g, 0.4764 mmol), propylene oxide (0.683 mL, 9.76 mmol) and maleic anhydride (0.9571 g, 9.76 mmol). The solution was dissolved in toluene so that the total monomer concentration was 2M. The ampoule was sealed and heated at 100°C for 72 hours. The resulting polymer was recovered by precipitation in excess diethyl ether and characterized by: 1 H NMR ((300MHz,303K,CDCl 3 ): δ=6.28-6.24(t,OC(=O)CH...

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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 formationof 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) hydrogelsthe 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.

Description

[0001] Cross References to Related Applications [0002] This application claims U.S. Provisional Patent Application Serial No. 62 / 541,889, filed August 7, 2017, entitled "Synthesis and Characterization of Well-Defined Block Copolymers of Polytrimethylene Fumarate and Polyethylene Glycol" , which application is incorporated herein by reference in its entirety. [0003] Statement Regarding Federally Funded Research or Development Support [0004] This invention was made with Government support under Contract No. P41EB001046 awarded by the National Institutes of Health. The government has certain rights in this invention. [0005] Names of parties to the collaborative research agreement [0006] This application is derived from work performed under a collaborative research agreement between the University of Akron, Akron, Ohio, and 3DBioActives LLC, Pepper Pike, Ohio. technical field [0007] In one or more embodiments, the present invention relates to block copolymers of po...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61L27/52C08G63/08C08J3/075
CPCC08J3/075C08G63/676C08G63/81C08J2353/00C08G63/42C08G63/826C08G65/10C08L67/025C08L67/06
Inventor M·贝克J·A·威尔逊R·A·迪利亚
Owner THE UNIVERSITY OF AKRON
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