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Biodegradable polycarbonate amide polymer and its preparation method

A polycarbonate amide, biodegradation technology, applied in the field of chemistry, can solve the problems of high local acidity, weakening the acidity of degradation products, and poor controllability of product structure

Inactive Publication Date: 2017-02-01
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In order to reduce the acidity of its degradation products, it has been reported that weakly alkaline acetylated chitin, calcium carbonate or calcium hydrogen phosphate, hydroxyapatite (HPA) or β-tricalcium phosphate (β-TCP) were mixed into PLA. , trying to overcome this shortcoming of polylactic acid, but the effect is not ideal
We have covalently grafted basic diamines to PLA, which can weaken the acidity of the degradation products to a certain extent, but the modification process is more complicated and the controllability of the product structure is poor (ZL200910104290.3, ZL02133814.0)
[0005] Therefore, there is an urgent need for a degradable polymer material whose degradation product is alkaline or neutral, so as to solve the problem of non-infectious inflammation due to excessive local acidity due to the degradation of existing implant materials

Method used

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  • Biodegradable polycarbonate amide polymer and its preparation method
  • Biodegradable polycarbonate amide polymer and its preparation method
  • Biodegradable polycarbonate amide polymer and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1, solution method prepares HO-LA-PPZ-LA-OH monomer

[0034] Dissolve 8.6g of piperazine (0.1mol) and 14.4g of lactide (0.1mol) in 20mL and 30mL of tetrahydrofuran (THF) solvents respectively, slowly drop the THF solution of lactide into the THF solution of piperazine under stirring , react at a temperature of 60-70°C, stop the reaction when the pH of the solution is constant (about 2h), then lower the temperature of the reaction solution to 0-4°C and cool for 24h to completely precipitate the product; then wash with cold THF The product was dried 2-3 times in vacuum at room temperature (25° C.) for 48 hours to obtain the product HO-LA-PPZ-LA-OH. In this example, the HO-LA-PPZ-LA-OH yield rate is 80%, and the melting point is 171°C (detected by DSC-TGA), and the infrared spectrogram is as follows figure 2 shown. The results show that the infrared spectrum of HO-LA-PPZ-LA-OH is compared with the infrared spectrum of lactide, and lactide is at 1730cm -1 The...

Embodiment 2

[0037] Embodiment 2, melting method prepares HO-LA-PPZ-LA-OH monomer

[0038] Put 8.6g of piperazine (0.1mol) and 14.4g of lactide (0.1mol) in a 100mL flask, raise the temperature to 140°C under the protection of nitrogen, and react for 12h under stirring, then add ethyl acetate while hot, at 70-80°C Dissolve the product, lower the temperature, and cool at 0-4°C for 12h, filter with suction, wash with cold tetrahydrofuran three times, and dry in vacuum at 40°C for 24h to obtain the product HO-LA-PPZ-LA-OH. The present embodiment HO-LA-PPZ-LA-OH productive rate is 92%, 170 ℃ of fusing points (DSC-TGA detects), and infrared spectrogram and figure 2 resemblance, 1 H NMR spectrum and 13 The C NMR spectra were compared with image 3 with Figure 4 resemblance.

[0039] In this embodiment, both lactide and piperazine can be realized under the condition of the same molar weight; when lactide and piperazine react, stirring reaction at 80-150° C. for 2-24 hours under nitrogen pro...

Embodiment 3

[0041] Embodiment 3, the synthesis of novel polycarbonate amide (CDI-LA-PPZ-LA)

[0042] Dissolve 0.01mol (2.3014g) of HO-LA-PPZ-LA-OH monomer and 0.01mol (1.6215g) of N,N'-carbonyldiimidazole (CDI) in 20mL of dimethyl sulfoxide, and raise the temperature to 40°C, constant temperature reaction for 48 hours, then lowered to room temperature, then the reaction mixture was added dropwise into excess tetrahydrofuran, the solid was collected, and the collected solid was vacuum-dried at room temperature for 48 hours to obtain the product CDI-LA-PPZ-LA. After testing, the number average molecular weight of CDI-LA-PPZ-LA is 8900 (hydroxyl terminal method); the static water antenna of the film is 58±5°. Then detection of CDI-LA-PPZ-LA 1 H NMR spectrum and 13 C NMR spectrum, 1 H NMR spectrum detection condition is: solvent is DMSO-d6 (Fluka Chemica, deuterium content is not less than 99.8%); Internal standard is tetramethylsilane (TMS); Instrument is AV-500 type nuclear magnetic reso...

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Abstract

The invention discloses a biodegradable polycarbonate amide polymer and a preparation method thereof. The polymer is synthesized by taking piperazine, lactide and N, N'-carbonyldiimidazole as raw materials so as to be expected to have favorable mechanical properties; in addition, alkaline binary cyclic secondary amine piperazine generated during degradation can be used for neutralizing lactic acid generated during degradation, so that the degradation product is basically neutral, and furthermore the defect that an adverse effect for cells and tissues is generated because of accumulation of acidic degradation products of polylactic acid is fundamentally overcome. The invention also discloses the preparation method of the biodegradable polycarbonate amide polymer. The preparation method is simple, low in cost, capable of realizing industrial production and favorable in market prospect.

Description

technical field [0001] The invention belongs to the field of chemistry, and in particular relates to a biodegradable polycarbonate amide polymer and a preparation method of the polycarbonate amide polymer. Background technique [0002] Poly(lactic acid), PLA) includes poly(L-lactic acid) (PLLA), poly(D-lactic acid) (PDLA), poly(D, L-lactic acid) (PDLLA) and poly(meso- Lactic acid) (meso-PLA), currently the main research is PLLA and PDLLA. Because of its good biocompatibility and biodegradability, PLA has a wide range of applications in surgical sutures, bone fixators, drug delivery systems, tissue engineering scaffold materials and general-purpose fully degradable plastics. . The final product of PLA metabolism in the body is CO 2 and H 2 O, the intermediate product lactic acid is also a product of normal metabolism in the body, so it will not accumulate in vital organs. It is precisely because of the above advantages of polylactic acid that PLA has become one of the mo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G69/44
Inventor 罗彦凤王远亮徐维龙姚璇潘美玲
Owner CHONGQING UNIV