Poly(propylene fumarate)-based copolymers for 3D printing applications

A 3D, polymer technology, applied in 3D object support structure, processing and manufacturing, manufacturing tools, etc., can solve problems such as limited production volume, high light source, 3D printing failure, etc.

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

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Problems solved by technology

However, in some cases, it was also found that Mg(BHT) 2 (THF) 2 Catalyst-polymerized PPF has high absorbance at wavelengths where 3D printing is performed, which increases 3D printing time
The high absorbance of these PPF polymers can lead to problems such as extended production times, limited throughput, potential for 3D printing failures during fabrication, higher light source requirements, and increased energy consumption

Method used

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  • Poly(propylene fumarate)-based copolymers for 3D printing applications
  • Poly(propylene fumarate)-based copolymers for 3D printing applications
  • Poly(propylene fumarate)-based copolymers for 3D printing applications

Examples

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example

[0148] The following examples are provided to more fully illustrate the invention, but should not be construed as limiting the scope of the invention. Further, while some of the examples may contain conclusions about the manner in which the invention may function, the inventors do not wish to be bound by these conclusions, but merely present them 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 weight average molecular weight, temperature is in degrees Centigrade, and pressure is at or near atmospheric.

[0149] Material

[0150] All materials were purchased from...

example 1

[0162] Copolymer synthesis of DP 20 polymer with 5 mol% succinic anhydride feed ratio

[0163] A DP 20 polymer having a 5 mol% succinic anhydride feed ratio was synthesized following the same procedure shown in Comparative Example 1, except that, instead of 2.80 g maleic anhydride, 2.664 g maleic anhydride and 143.2 mg succinic anhydride were added (i.e. , 2.664g maleic anhydride, 0.143g succinic anhydride, 2mL propylene oxide, 148.6uL benzyl alcohol, 174mg Mg(BHT) 2 (THF) 2 ), 4.42 g (99.0%) of copolymer were recovered. The resulting copolymer passed 1 H NMR characterization ((300MHz, 298K, CDCl 3 ): 7.36(s, 5.0H, Ar), 6.36-6.18(m, 49.0H, C=OCHCHC=O), 5.35-5.14(m, 26.9H, CH 2 CHCH 3 O), 4.37-4.00 (m, 52.7H, OCH 2 CHCH 3 ),2.67-2.55(m,2.7H,C=OCH 2 CH 2 C=O), 1.40-1.08(m, 77.9, CHCH 3 )). DP 20 copolymer with 5mol% succinic anhydride 1 H NMR spectrum as Figure 14 shown. The degree of polymerization was confirmed by NMR, and the number average molecular weight (M)...

example 2

[0165] Polymerization with DP 20 and 10 mol% succinic anhydride feed ratio

[0166] A DP 20 copolymer having a 10 mol% succinic anhydride feed ratio was synthesized following the procedure shown in Comparative Example 1, except that, instead of 2.80 g maleic anhydride, 2.524 g maleic anhydride and 286 mg succinic anhydride were used (i.e., using 2.524g maleic anhydride, 0.286g succinic anhydride, 2mL propylene oxide, 148.6uL benzyl alcohol, 174mg Mg(BHT) 2 (THF) 2 ). 4.46 g (99.8%) of copolymer were recovered. The resulting copolymer passed 1 H NMR characterization ((300MHz, 298K, CDCl 3 ): 7.36(s, 5.0H, Ar), 6.36-6.18(m, 43.0H, C=OCHCHC=0), 5.35-5.14(m, 25.0H, CH 2 CHCH 3 O),4.37-4.00(m,48.2H,OCH 2 CHCH 3 ),2.67-2.55(m,5.8H,C=OCH 2 CH 2 C=O),1.40-1.08(m,72.0,CHCH 3 )). Attached here is DP 20, 10mol% succinic anhydride copolymer 1 H NMR spectroscopy, such as Figure 15 shown. The degree of polymerization was confirmed by NMR, and the number average molecular wei...

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Abstract

In various embodiments, the present invention is directed to a PPF-based copolymer for 3D printing applications and methods for its making and use. These copolymers have a viscosity in a printable viscosity range and allow light transmittance at curing wavelengths. In various embodiments, a lower viscosity copolymers are obtained by substitution of a portion of maleic anhydride with succinic anhydride and then forming a poly(propylene fumarate-co-succinate) copolymer by the copolymerization of maleic anhydride and succinic anhydride with propylene oxide via Mg(BHT)2(THF)2 catalyzed ring opening copolymerization (ROCOP). Because of their lower viscosities, these copolymers require less, if any, diethyl fumarate (DEF) to prepare the 3D printing resin, while the mechanical properties can still be adjusted as with a PPF polymer prepared without the succinic anhydride.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of U.S. Provisional Patent Application Serial No. 62 / 697,613, entitled "Poly(trimethylene fumarate)-based copolymers for 3D printing applications," filed July 13, 2019, and said provisional patent The application is hereby incorporated by reference in its entirety. [0003] Name of the parties to the joint research agreement [0004] This application is derived from work performed under a joint research agreement between the University of Akron, Akron, Ohio, and 3D BioActives, LLC, Akron, Ohio. technical field [0005] One or more embodiments of the invention relate to a 3D printable and degradable polymer for use in medical devices and applications. In certain embodiments, the present invention relates to poly(trimethylene fumarate) (PPF)-based polymers and copolymers for use as medical devices or tissue scaffolds whose viscosity is in the 3D printable viscosity range and which a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G81/02C09D7/65
CPCB33Y70/00C08G63/58C08G63/83B29C64/106B29C64/124B29C64/314B33Y40/10B29K2105/0002
Inventor M·贝克Y·申G·勒·费尔
Owner THE UNIVERSITY OF AKRON
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