Preparation method of high molecular weight poly-morpholine-2,5-dione derivative and preparation method of the copolymer thereof

A high-molecular-weight polymorpholine technology, which is applied in the preparation of copolymers and high-molecular-weight polymorpholine-2, can solve the problems of low molecular weight, many by-products, restrictions, etc., and achieve the effect of large molecular weight and good mechanical properties

Inactive Publication Date: 2009-09-02
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] Although the existing synthesis methods of polymorpholine-2,5-dione derivatives are different, there is a big disadvantage, that is, the molecular weight of the synthetic material is not high, generally less than 20000, and only a few reports reach around 40000
Especially the monomers of morpholine-2,5-dione derivatives containing multifunctional groups are not high in purity. Even if the monomers are of sufficient purity, during ring-opening polymerization, under high temperature conditions for a long time, the protective group It is easy to dep

Method used

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  • Preparation method of high molecular weight poly-morpholine-2,5-dione derivative and preparation method of the copolymer thereof
  • Preparation method of high molecular weight poly-morpholine-2,5-dione derivative and preparation method of the copolymer thereof
  • Preparation method of high molecular weight poly-morpholine-2,5-dione derivative and preparation method of the copolymer thereof

Examples

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Example Embodiment

[0032] Example 1

[0033] Synthesis of double-end hydroxyl polymorpholine-2,5-dione derivative (double-end hydroxyl poly3(S)-isopropylmorpholine-2,5-dione):

[0034] A thermometer, vacuum tube and nitrogen inlet are installed on a 250ml three-necked flask; 100g of 3(S)-isopropyl-morpholine-2,5-dione (IPMD) and 2g of 1,2-ethanedione Alcohol was added to the reaction flask, while adding 0.2 g of stannous octoate as a catalyst; after the reaction flask was repeatedly evacuated and vented with nitrogen three times, under the protection of nitrogen, the temperature of the oil bath was increased to 140°C and reacted for 8 hours; After that, chloroform was added to dissolve, and then precipitated in ether; filtered, washed, and vacuum dried at room temperature to obtain double-terminal hydroxyl poly 3(S)-isopropylmorpholine-2,5-dione.

[0035] The chemical structure of poly 3(S)-isopropylmorpholine-2,5-dione with double-ended hydroxyl groups is as follows:

[0036]

[0037] The molecul...

Example Embodiment

[0040] Example 2

[0041] Synthesis of high molecular weight polymorpholine-2,5-dione derivatives (high molecular weight poly3(S)-isopropylmorpholine-2,5-dione)

[0042] A thermometer, a vacuum tube and a nitrogen inlet were installed on a 250 ml three-necked flask; 10 grams of the double-terminated poly-3(S)-isopropylmorpholine-2,5-dione (hydroxyl value) prepared in Example 1 The molecular weight is determined to be 2850) and 40 ml of chloroform. At the same time, 0.02 g of stannous octoate is added as a catalyst; under the protection of nitrogen, 736 mg of trimethylhexamethylene diisocyanate (TMDI) is added to increase the temperature of the oil bath At 60°C, react for 8 hours to complete the reaction. The polymer solution was obtained, after cooling, 40 ml of chloroform were added, and then precipitated in ether. Filter, wash, and vacuum dry at room temperature. A high molecular weight poly 3(S)-isopropylmorpholine-2,5-dione is obtained.

[0043] The chemical structure of high ...

Example Embodiment

[0049] Example 3

[0050] Double-terminated polymorpholine-2,5-dione derivatives (two-terminated poly(3(S)-isopropylmorpholine-2,5-dione-co-lactide) copolymer) synthesis

[0051] A thermometer, vacuum tube and nitrogen inlet are installed on a 250ml three-necked flask; 100g of 3(S)-isopropyl-morpholine-2,5-dione (IPMD) and 100g of D, L-propyl Lactide and 6 grams of 1,4-butanediol were added to the reaction flask, while 0.4 grams of stannous octoate was added as a catalyst; after the reaction flask was repeatedly evacuated and vented with nitrogen three times, the temperature of the oil bath was increased under the protection of nitrogen. The temperature was raised to 140°C and reacted for 8 hours. After cooling, it was dissolved by adding chloroform, and then precipitated in ether. Filter, wash, and vacuum dry at room temperature. The poly(3(S)-isopropylmorpholine-2,5-dione-co-lactide) with double-terminated hydroxyl groups is obtained.

[0052] The molecular weight determined by ...

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Abstract

The invention discloses a preparation method of a high molecular weight poly-morpholine-2,5-dione derivative and a preparation method of the copolymer thereof. The preparation method of the high molecular weight poly-morpholine-2,5-dione derivative comprises the following steps: (1) morpholine-2,5-dione derivative, organic tin catalyst and dihydric alcohol are weighted and mixed to react to obtain the dihydroxy-terminal poly-morpholine-2,5-dione derivative after separation and purification; and (2) the dihydroxy-terminal poly-morpholine-2,5-dione derivative is mixed with a chain extender in proportion to react under air-isolated conditions to obtain the high molecular weight poly-morpholine-2,5-dione derivative. The high molecular weight poly-morpholine-2,5-dione derivative and the copolymer thereof prepared by the preparation methods have high molecular weight, biodegradability and good mechanical properties owning to high molecular weight, thereby meeting the requirement of the application of high molecular materials for medical use.

Description

technical field [0001] The invention relates to a method for preparing a synthetic biodegradable polymer medical material, in particular to a method for preparing a high-molecular-weight polymorpholine-2,5-dione derivative and a high-molecular-weight polymorpholine-2,5-dione Process for the preparation of copolymers of derivatives. Background technique [0002] Synthetic biodegradable polymer medical materials are often used in biomedicine for surgical instruments, artificial blood vessels, degradable and absorbable bone plates, artificial skin, drug-controlled release carriers, and tissue engineering materials. Among them, the two most widely used synthetic biodegradable polymer medical materials are poly α-hydroxy acid and poly α-amino acid. Morpholine-2,5-dione and its derivatives are a six-membered cyclic monomer synthesized by α-hydroxy acid and α-amino acid, its structure: [0003] [0004] R 1 :—CH 3 ,—H or other aliphatic substituents; [0005] R 2 :—CH 3 ,...

Claims

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Application Information

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IPC IPC(8): C08G69/44
Inventor 冯亚凯郭锦棠赵海洋亓吉娇
Owner TIANJIN UNIV
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