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Polyamideimide-polyethylene glycol copolymer derived from L-phenylalanine and preparation method of polyamideimide-polyethylene glycol copolymer

A technology of polyamide-imide and phenylalanine, applied in tissue regeneration, medical science, prosthesis, etc., can solve problems such as degradation, limited biological activity, and low cytotoxicity, and achieve good mechanical properties and biocompatibility Good performance and mild reaction conditions

Active Publication Date: 2019-12-13
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the clinical application of PEEK materials still faces many limitations: 1) Although polyether ether ketone materials have excellent biocompatibility, their surface is water-absorbing and biologically inert. The ability of integration and bone conduction is poor, and it cannot be firmly combined with the surrounding tissue within a certain period of time; 2) Although polyether ether ketone has an elastic modulus close to that of human bone tissue, it is used as a non-absorbable implant when it is implanted. In the later stage, it cannot be degraded with the gradual absorption of the internal bone graft, which has an obvious stress shielding effect on the fusion of the bone graft, affecting the fusion of the bone graft and the repair of the damaged spine
The applicant has developed a polyamideimide / silicon dioxide nanocomposite material derived from L-amino acid and its preparation method (CN107141489). The composite material has good hydrophilicity and degradability, but the cell phase Capacitance and mechanical properties are not ideal enough. On this basis, the applicant has developed a new polyamideimide-polyethylene glycol copolymer derived from L-phenylalanine and its preparation method. Good biodegradability, low cytotoxicity, good biocompatibility, moderate flexibility, and potential application value in the fields of biomedicine and hard tissue surgery implantation

Method used

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  • Polyamideimide-polyethylene glycol copolymer derived from L-phenylalanine and preparation method of polyamideimide-polyethylene glycol copolymer
  • Polyamideimide-polyethylene glycol copolymer derived from L-phenylalanine and preparation method of polyamideimide-polyethylene glycol copolymer
  • Polyamideimide-polyethylene glycol copolymer derived from L-phenylalanine and preparation method of polyamideimide-polyethylene glycol copolymer

Examples

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Embodiment 1

[0030] A kind of polyamideimide-polyethylene glycol copolymer derived from L-phenylalanine, its preparation method step is as follows:

[0031] 1) 5.8844 grams (0.02mol) of BPDA and 6.6741 grams (0.0404mol) of L-phenylalanine were uniformly dispersed in 75ml of glacial acetic acid to form a homogeneous solution, stirred and reacted at room temperature (25° C.) for 12 hours, and then Heat up to 118°C in an oil bath, and reflux for 5 hours; after the reaction, carry out vacuum distillation to remove the reaction solvent, the distillation temperature is 63°C, and the flow rate is 1-2 drops / second; finally wash the reaction with 5% hydrochloric acid aqueous solution The product was suction filtered three times, and the filter cake was vacuum-dried at 30° C. for 12 hours to obtain an imide diacid monomer based on L-phenylalanine;

[0032] 2) 1.8 g (9.0 mmol) of ODA and 2 g (1 mmol) of polyoxyethylene diamine (Mn=2000), 5.97 g (10 mmol) of the L-phenylalanine-based imide diamine pre...

Embodiment 2

[0065] A kind of polyamideimide-polyethylene glycol copolymer derived from L-phenylalanine, its preparation method step is as follows:

[0066] 1) 5.8844 grams (0.02mol) of BPDA and 6.5750 grams (0.0398mol) of L-phenylalanine were uniformly dispersed in 75ml of glacial acetic acid to form a homogeneous solution, stirred at room temperature (25° C.) for 10 hours, and then Heat up to 125°C in an oil bath, and reflux for 4 hours; after the reaction, carry out vacuum distillation to distill off the reaction solvent at a distillation temperature of 63°C, and finally wash the reaction product 3 times with 5% aqueous hydrochloric acid, and filter it with suction for 30 ℃ vacuum drying for 12 hours to obtain the imide diacid monomer based on L-phenylalanine;

[0067] 2) 1.748 g (9.5 mmol) of BD and 2 g (0.5 mmol) of polyoxyethylene diamine (Mn=4000), 5.97 g (10 mmol) of the L-phenylalanine-based imide prepared in step 1) Diacid monomers in N 2 Add it to 32.2370 g (0.10 mol) of molte...

Embodiment 3

[0076] A kind of polyamideimide-polyethylene glycol copolymer derived from L-phenylalanine, its preparation method step is as follows:

[0077] 1) 5.8844 grams (0.02mol) of BPDA and 6.6113 grams (0.04mol) of L-phenylalanine were uniformly dispersed in 75ml of glacial acetic acid to form a homogeneous solution, stirred and reacted at room temperature (25°C) for 12 hours, and then Heat up to 125°C in an oil bath, and reflux for 4 hours; after the reaction, carry out vacuum distillation to remove the reaction solvent, and the distillation temperature is 63°C; finally wash the reaction product 3 times with 5% aqueous hydrochloric acid, and filter it with suction for 30 ℃ vacuum drying for 12 hours to obtain the imide diacid monomer based on L-phenylalanine;

[0078]2) 2.014 grams (9.5 mmol) of DMMDA and 1 gram (0.5 mmol) of polyoxyethylene diamine (Mn=2000), 5.97 grams (10 mmol) of the imide based on L-phenylalanine prepared in step 1) Diacid monomers in N 2 Add it to 32.2370 g ...

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Abstract

The invention relates to a polyamideimide-polyethylene glycol copolymer derived from L-phenylalanine and a preparation method of the polyamideimide-polyethylene glycol copolymer. The molecular structural formula is shown as a formula I, the copolymer has both degradability and hydrophilicity, good biocompatibility, a moderate degradation rate and good mechanical properties, can solve the practicalproblems of nondegradability and surface hydrophobicity of polyetheretherketone which is mostly used clinically at present, has potential application value in the fields of biomedicine, hard tissue surgical implantation and the like, and is particularly suitable for the field of spine repair.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and in particular relates to a polyamideimide-polyethylene glycol copolymer derived from L-phenylalanine and a preparation method thereof. Background technique [0002] Spinal fusion cages currently in use are mainly made of metal materials or polymer materials with good biocompatibility. Metal spinal fusion materials are currently mainly made of titanium alloy, but it is non-degradable, and it is prone to metal corrosion if it exists in the human body for a long time, and it is impermeable to X-rays, which affects the observation of bone graft fusion; on the other hand, titanium alloy The elastic modulus of bone does not match that of human bone, and the obvious stress shielding effect will affect the fusion speed and effect of bone grafting. In recent years, medical polymer materials, mainly polyetheretherketone (PEEK) materials, have attracted attention because their elastic modulus...

Claims

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Application Information

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IPC IPC(8): C08G73/14A61L27/18A61L27/58A61L27/50
CPCC08G73/14A61L27/18A61L27/58A61L27/50C08G2230/00A61L2430/38
Inventor 戴红莲胡亚萍张杰克
Owner WUHAN UNIV OF TECH