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Multi-block copolymer of polyester amide and aniline oligomer and preparation method thereof

A technology of multi-block copolymers and aniline oligomers, which can be used in catheters and other directions, can solve problems such as low molecular weight and poor mechanical properties, and achieve the effects of simple synthesis method, promotion of growth and repair, and easy adjustment of physical and chemical properties.

Inactive Publication Date: 2014-05-07
NORTHEAST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Another advantage of aniline oligomers is that they can be phagocytized by macrophages in vivo or directly excreted from the body, but the disadvantage is that due to their low molecular weight, their mechanical properties are not good

Method used

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  • Multi-block copolymer of polyester amide and aniline oligomer and preparation method thereof
  • Multi-block copolymer of polyester amide and aniline oligomer and preparation method thereof
  • Multi-block copolymer of polyester amide and aniline oligomer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1, the synthesis of diamino-terminated aniline pentamer.

[0025] The bisamino-terminated aniline pentamer is synthesized by the synthetic route shown below. The specific synthesis method is:

[0026]

[0027]Dissolve 18.42 g of N-phenyl-1,4-p-phenylenediamine and 10.00 g of succinic anhydride in 700 mL of dichloromethane, and stir the reaction continuously for 4 hours under nitrogen protection. After the reaction is completed, filter and use the product It was washed with ether until it was colorless, and dried in vacuum at 40°C to constant weight to obtain a carboxyl-terminated aniline dimer with a yield of 75%. 5.70 g of carboxy-terminated aniline dimer and 1.08 g of p-phenylenediamine were dissolved in a mixed solution of 60 mL of dimethylformamide and 60 mL of 2 M HCl. Add 4.56 g of ammonium persulfate to the solution, add 500 mL of distilled water after the reaction lasts for 1 hour, filter, dissolve the product in 500 mL of 1 M ammonia water, add ...

Embodiment 2

[0029] Embodiment 2, the synthesis of bisamino-terminated aniline trimer.

[0030] Dissolve 1.72 g of p-phenylenediamine in a mixed solution of 200 mL of 1 M HCl and 40 mL of ethanol, and place the solution in an ice-salt bath at -5°C to cool. After p-phenylenediamine was dissolved, 3.6 g of ammonium persulfate was added to the solution. After 5 minutes, the reaction solution turned dark brown, and 3 mL of aniline was added at this time. After 10 minutes, small blue suspended particles appeared in the reaction system and continued vigorous stirring for 30 minutes. After the reaction was completed, it was suction-filtered with a Buchner funnel, washed with 60 mL of 1 M HCl, and then washed with 160 mL of distilled water until neutral. The product was treated with 1 M ammonia water for 1-2 hours, filtered with suction, washed, and vacuum-dried at 40°C to constant weight. The yield was 31%.

Embodiment 3

[0031] Example 3. Synthesis of p-nitrophenol sebacate (electrophilic monomer).

[0032] Sebacic acid p-nitrophenol ester (electrophilic monomer) is synthesized according to the synthetic route shown below. The specific synthesis method is:

[0033]

[0034] Dissolve 43.00 g of p-nitrophenol and 44.00 mL of triethylamine in 500 mL of acetone, and cool the solution in an ice-water bath at 0°C. Dissolve 28.00 mL of sebacoyl chloride in 100 mL of acetone, drop it into the p-nitrophenol solution, and gradually raise the temperature to room temperature for 12 hours with stirring. After the reaction, pour into 2000 mL of distilled water to precipitate the product, filter it with suction, recrystallize three times with ethyl acetate, and dry it under vacuum at 40°C to constant weight, with a yield of 75%.

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Abstract

The invention belongs to the technical field of biomedical polymer materials and particularly relates to a multi-block copolymer of polyester amide and an aniline oligomer and a preparation method thereof. Natural alpha-amino acid, aliphatic diol, diacid (or diacyl chloride) and a bis-amino capped aniline oligomer are taken as raw materials, and the reparation method comprises the following steps: firstly, synthesizing diol diamino acid ester p-toluene sulfonate (a nucleophilic monomer) and diacid p-nitrophenol ester (an electrophilic monomer); and in the polycondensation process of a solution, preparing an irregular or alternate multi-block copolymer of the polyester amide and the aniline oligomer by changing the molar ratio of the two monomers as well as the adding sequence of the aniline oligomer. The prepared copolymer is a biodegradable material with electrically activity; physical and chemical properties of the copolymer can be effectively regulated by changing chemical structures of the monomers and the aniline oligomer; and as an ideal tissue engineering material, the multi-block copolymer is particularly applicable to preparation of a nerve conduit.

Description

technical field [0001] The invention belongs to the field of biomedical polymer materials, and relates to a multi-block copolymer of polyester amide and aniline oligomer and a preparation method thereof. Background technique [0002] Peripheral nerve injury is a common disease. When injured, the normal function (motor and sensory functions) of the organs controlled by it can be seriously affected. At present, an ideal means of nerve restoration clinically adopted is to bridge the two stumps of damaged nerves by using nerve conduits to promote the growth of nerves in the conduits and eventually restore the normal function of the nerves. [0003] The materials used for nerve repair mainly fall into three categories: bio-derived materials, non-biodegradable materials, and biodegradable materials. Among them, nerve conduits made of biologically derived materials contain basement membranes, which contain fibronectin, fibronectin, and collagen, all of which can promote axon grow...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G69/48C08G69/44A61L29/06A61L29/14D01F6/82
Inventor 邓明虓宋丽杜保国
Owner NORTHEAST NORMAL UNIVERSITY
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