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Iodine-containing polycarbonate/polyester material for X-ray development and preparation method and application thereof

A technology of polycarbonates and carbonates, which is applied in the field of iodine-containing polycarbonate/polyester polymers and its preparation, can solve problems such as easy decomposition of iodine-containing monomers, limited practical applications, and harsh storage conditions. Achieve excellent X-ray imaging performance, strong shape selectivity, and good thermal stability

Active Publication Date: 2018-04-17
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation conditions of such a monomer itself are relatively harsh, requiring a low temperature of -80°C; at the same time, the direct introduction of iodine atoms at the α position makes its structure unstable for two reasons: 1) due to the electron-withdrawing effect of the adjacent carbonyl group , making it easy to undergo nucleophilic substitution at the α position, and the iodine atom itself is a good leaving group; 2) The iodo product at the α position of the carbonyl group is also prone to elimination reactions, resulting in more stable α, β-unsaturated lactones ; These factors all cause this iodine-containing monomer to decompose easily, and it is difficult to store for a long time
Even short-term storage requires very harsh storage conditions: dark storage at -15°C, this shortcoming greatly limits its practical application

Method used

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  • Iodine-containing polycarbonate/polyester material for X-ray development and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1, take 1.5g of serinol and dissolve it in 40mL of 10% sodium carbonate aqueous solution, add 15mL of 1,4-dioxane, and after 15min in ice-water bath, slowly add 4.47g of 4-iodo-benzoyl chloride solution (containing 7.5mL 1,4-dioxane), react in an ice-water bath for 1h, then react overnight at room temperature. Suction filtration, take the filter cake into 60mL aqueous solution and stir for 2h, then suction filtration again, and dry the filter cake at 80°C for 2h to obtain white powder N-(1,3-dihydroxy-2-propyl)-4-iodobenzene Formamide 4.76g, recorded as compound a, yield 90%.

Embodiment 2

[0038] Example 2, take 0.5g of N-(1,3-dihydroxy-2-propyl)-4-iodobenzamide and add 25mL of anhydrous THF, add 0.3mL of ethyl chloroformate after ice-water bath for 10min, add dropwise 0.43 mL of triethylamine was added dropwise in 20 minutes. Suction filtration, the filter cake was added to 50 mL of tetrahydrofuran and stirred for 2 hours, then suction filtration, and the filter cake was dried at 80°C for 2 hours to obtain white powder 4-iodo-N-(2-oxo-1,3-dioxin-5- Base)-benzamide, denoted as compound b, yield 87%. figure 1 is it 1 H NMR spectrum.

Embodiment 3

[0039] Example 3, 3 g of 2,2 dibromomethyl-1,3-propanediol and 8 g of sodium iodide were added to 60 mL of acetone for dissolution, heated to reflux for 30 h, and the solvent was distilled off under reduced pressure, and sodium thiosulfate 10% (w / v) After 60mL, suction filtration, the filter cake was vacuum-dried at 60°C for 6h to obtain 3.7g of white powder 2,2-diiodomethyl-1,3-propanediol, which was designated as compound c, with a yield of 90%.

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Abstract

The invention belongs to the field of biomedical polymer materials, and particularly relates to an iodine-containing polycarbonate / polyester polymer for X-ray development and a preparation method andapplication thereof. The iodine-containing polycarbonate / polyester polymer disclosed by the invention has excellent X-ray radiopacity or property of weakening X-rays. Under the existence of a catalyst, with a small-molecule hydroxyl compound as an initiator, through the ring-opening homopolymerization of an iodine-containing carbonate monomer or the ring-opening copolymerization of the iodine-containing carbonate monomer and other lactone, lactide and / or carbonate monomers, the iodine-containing polycarbonate / polyester material is obtained. The iodine-containing polycarbonate / polyester polymercan be applied in fields such as visualized embolization materials, anti-counterfeit labels, contrast media, antibacterial materials, prevention or treatment of iodine deficiency disorders, flame-retardant materials, tissue engineering and drug delivery systems.

Description

technical field [0001] The invention belongs to the field of biomedical polymer materials, and in particular relates to an iodine-containing polycarbonate / polyester polymer with X-ray imaging function and its preparation method and application. Background technique [0002] Biomedical polymer materials have many advantages such as good biocompatibility and easy-to-adjust degradability, and are an important content of biomedical material research. They have broad application prospects in the fields of medical imaging, tissue engineering, and drug delivery systems. . Among them, degradable polycarbonate / polyester material is one of the most widely used medical degradable polymer materials. At present, many products and devices based on such materials have been approved by the FDA and widely used in clinical practice. However, due to the complex physiological environment in the body, it is still difficult to conveniently and accurately evaluate the degradation behavior of suc...

Claims

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Application Information

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IPC IPC(8): C08G63/08C08G63/78C08G64/30C08G64/38A61L24/00A61L24/04A61L24/02A61K49/04A61K47/59A61K33/18A61P3/02A61L27/50A61L27/18A61L27/02
CPCA61K33/18A61K49/04A61L24/001A61L24/02A61L24/046A61L27/025A61L27/18A61L27/50C08G63/08C08G63/78C08G64/30C08G64/305C08G64/38C08L69/00C08L67/04
Inventor 俞麟马前丁建东
Owner FUDAN UNIV
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