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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

AI Technical Summary

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 deprotect, resulting in low degree of polymerization, too many by-products, low molecular weight of the product, generally only about 10,000, and the color of the product is dark, which cannot meet the requirements of application as a biological material
[0011] The mechanical properties of polymorpholine-2,5-dione derivatives with low molecular weight and their copolymers are far from meeting the application requirements of medical polymer materials, which severely limits the derivatives of polymorpholine-2,5-dione. The use of substances or their copolymers

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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Embodiment 1

[0033] Synthesis of polymorpholine-2,5-dione derivatives of double-terminal hydroxyl groups (poly 3(S)-isopropylmorpholine-2,5-dione of double-terminal hydroxyl groups):

[0034] Install a thermometer, vacuum tube and nitrogen inlet on a 250 ml three-necked flask; mix 100 grams of 3(S)-isopropyl-morpholine-2,5-dione (IPMD) and 2 grams of 1,2-ethanedione Alcohol was added to the reaction bottle, and 0.2 grams of stannous octoate was added as a catalyst; after the reaction bottle was repeatedly evacuated and nitrogen gased three times, under the protection of nitrogen, the temperature of the oil bath was raised to 140 ° C, and the reaction was carried out for 8 hours; cooling Finally, add chloroform to dissolve, and then precipitate in ether; filter, wash, and vacuum-dry at room temperature; obtain poly 3(S)-isopropylmorpholine-2,5-dione with double-terminal hydroxyl groups.

[0035] The chemical structure of the poly-3(S)-isopropylmorpholine-2,5-diketone of double-terminal hydr...

Embodiment 2

[0041] Synthesis of High Molecular Weight Polymorpholine-2,5-dione Derivatives (High Molecular Weight Poly 3(S)-isopropylmorpholine-2,5-dione)

[0042] On a 250 milliliter there-necked flask, a thermometer, a vacuum tube and a nitrogen inlet are installed; the poly 3(S)-isopropylmorpholine-2,5-dione (hydroxyl value) of the two-terminal hydroxyl prepared by 10 grams of embodiment 1 Measure and confirm that molecular weight is 2850) and 40 milliliters of chloroform, add simultaneously the stannous octoate of 0.02 gram as catalyst; Under nitrogen protection, add 736 milligrams of trimethylhexamethylene diisocyanate (TMDI), oil bath temperature is raised to 60° C. for 8 hours to make the reaction complete. The obtained polymer solution was cooled, supplemented with 40 ml of chloroform, and then precipitated in ether. Filter, wash, and dry under vacuum at room temperature. High molecular weight poly 3(S)-isopropylmorpholine-2,5-dione is obtained.

[0043] The chemical structure ...

Embodiment 3

[0050] Copolymer of polymorpholine-2,5-dione derivatives with double-terminal hydroxyl groups (poly(3(S)-isopropylmorpholine-2,5-dione-co-lactide) with double-terminal hydroxyl groups synthesis

[0051] Install a thermometer, a vacuum tube and a nitrogen inlet on a 250 ml three-necked flask; 100 grams of 3(S)-isopropyl-morpholine-2,5-dione (IPMD) and 100 grams of D,L-propane Lactide and 6 grams of 1,4-butanediol were added to the reaction flask, and 0.4 grams of stannous octoate was added as a catalyst; after the reaction flask was repeatedly evacuated and nitrogen gas flowed three times, under nitrogen protection, the temperature of the oil bath was raised to High to 140 ° C, react for 8 hours, after cooling, add chloroform to dissolve, and then precipitate in ether. Filter, wash, and dry under vacuum at room temperature. Poly(3(S)-isopropylmorpholine-2,5-dione-co-lactide) with double-terminated hydroxyl groups is obtained.

[0052] The molecular weight determined by gel p...

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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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