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Star-shaped poly(propylene fumarate) copolymers for 3D printing applications

A technology of propylene glycol fumarate and star-shaped copolymer, which can be used in prosthesis, additive processing, medical science, etc., and can solve problems such as low viscosity

Active Publication Date: 2021-06-25
THE UNIVERSITY OF AKRON
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] What is needed in the art is a 3D printable PPF polymer with sufficiently high molecular weight for a wide range of applications, but with a lower viscosity than comparable linear PPF

Method used

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  • Star-shaped poly(propylene fumarate) copolymers for 3D printing applications
  • Star-shaped poly(propylene fumarate) copolymers for 3D printing applications
  • Star-shaped poly(propylene fumarate) copolymers for 3D printing applications

Examples

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example

[0137] The following examples are provided to more fully illustrate the invention but should not be construed as limiting its scope. Furthermore, while some of the examples may include conclusions about the manner in which the invention may function, the inventors do not intend to be bound by these conclusions, but set them out only as possible explanations. Also, unless indicated by use of the past tense, the representation of an example does not imply that an experiment or procedure has or has not been performed or that a result has or was not actually obtained. Efforts have been made to ensure accuracy with respect to numbers used (eg, amounts, temperature) but some experimental errors and deviations may be present. Unless indicated otherwise, parts are parts by weight, molecular weight is number average molecular weight, temperature is in degrees Centigrade, viscosity is in Pa.s, and pressure is at or near atmospheric.

[0138] In the first set of experiments (Examples 1-...

example 1

[0146]Synthesis of 4-armed star poly(trimethylene maleate) of total DP20 with a meso-erythritol core

[0147] Meso-erythritol (112.12g.mol -1 , 249.1mg, 2.04mmol), Mg(BHT) 2 (THF) 2 (604.95g.mol -1 , 246.8mg, 4.08×10 -1 mmol), anhydrous toluene (10.2mL), MAn (98.06g.mol -1 , 4.0g, 40.8mmol) and PO (58.08g.mol -1 , 2.85 mL, 40.8 mmol) were introduced into a flame-dried Schlenk bottle in this order. The Schlenk bottle was sealed with a PTFE stopper and removed from the glove box. The solution was stirred at 80°C for 24 hours. The resulting copolymer was recovered by precipitation in diethyl ether and dried under vacuum to give a sticky beige powder. Yield: 88%.

[0148] pass 1 H NMR (500MHz, 298K, CDCl 3 ) to characterize the resulting 4-arm star poly(trimethylene maleate) copolymer: 6.42-6.18 (m, 42.1H, C=OCHCHC=O), 5.44 (m, 2H, CH(OR)CH 2 OR), 5.36-5.17 (m, 21.2H, CH 2 CHCH 3 O), 4.55-4.47(d, 1.7H, CH(OR)CHHOR), 4.45-4.00(m, 44.9H, OCH 2 CHCH 3 ), 1.41-1.23(m, ...

example 2

[0150] Synthesis of 4-armed star poly(trimethylene maleate) of total DP40 with a meso-erythritol core

[0151] Meso-erythritol (112.12g.mol -1 , 124.5mg, 1.02mmol), Mg(BHT) 2 (THF) 2 (604.95g.mol -1 , 123.4mg, 2.04×10 -1 mmol), anhydrous toluene (10.2mL), MAn (98.06g.mol -1 , 4.0g, 40.8mmol) and PO (58.08g.mol -1 , 2.85 mL, 40.8 mmol) were introduced into a flame-dried Schlenk bottle in this order. The Schlenk bottle was sealed with a PTFE stopper and removed from the glove box. The solution was stirred at 80°C for 48 hours. The resulting copolymer was recovered by precipitation in diethyl ether and dried under vacuum to give a sticky beige powder. Yield: 78%

[0152] pass 1 H NMR (500MHz, 298K, CDCl 3 ) to characterize the resulting 4-arm star poly(trimethylene maleate) copolymer: 6.42-6.18 (m, 79.3H, C=OCHCHC=O), 5.44 (m, 2H, CH(OR)CH 2 OR), 5.36-5.17(m, 37.5H, CH 2 CHCH 3 O), 4.55-4.47(d, 2.1H, CH(OR)CHHOR), 4.45-4.00(m, 86.5H, OCH 2 CHCH 3 ), 1.41-1.25(m, 1...

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Abstract

In various embodiments, the invention relates to poly(propylene fumarate) (PPF)-based star-shaped copolymers synthesized using a core-first approach that uses a multi-functional alcohols as an initiator, and Mg(BHT)2(THF)2 as catalyst for controlled ring opening copolymerization (ROCOP) of maleic anhydride (MAn) with propylene oxide (PO). In some embodiments, these star-PPF copolymers have lower viscosities than their linear analogs, allowing a decrease in DEF fraction in resin formulation, as well as the use of higher molecular weights. These star-shape PPF can be used to prepare PPF:DEF resins containing as much as 70% by weight of the multi-arm PPF star copolymers, and have a low complex viscosity of high Mn star PPF resin that affords rapid printing with a Mn nearly eight times larger than the largest linear PPF oligomer printed previously.

Description

[0001] Cross References to Related Applications [0002] This application claims the title of "Star-Shaped Poly(Propylene Fumarate) Copolymers for 3D Printing Applications," filed September 10, 2018. The benefit of US Provisional Patent Application No. 62 / 729,126, which is hereby incorporated by reference in its entirety. [0003] Name of the parties to the joint research agreement [0004] This application is made under a joint venture between The University of Akron of Akron, Ohio and 3D BioActives, LLC of Akron, Ohio Research protocol for work done. technical field [0005] One or more examples of the present invention report illustrations related to the preparation of copolymers for 3D printable resins for biomedical applications. In certain embodiments, the present invention describes the synthesis of star poly(propylene fumarate) (PPF) copolymers. In other embodiments, the present invention reports the use of these radial PPF copolymers for the preparation of resi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61L27/52C08G63/08C08J3/075
CPCB33Y70/00B33Y80/00A61L27/58A61L27/18C08G63/52C08G63/83C08G63/58C08L67/07
Inventor M·L·贝克G·勒·费尔
Owner THE UNIVERSITY OF AKRON
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