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Biodegradable polyurethane with amino on side chain and preparation method and application thereof

A biodegradable, polyurethane technology, applied in the field of biomedical materials, to achieve the effects of low physiological toxicity, regular structure, high availability and stability

Inactive Publication Date: 2013-06-26
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] So far, the application of biodegradable polyurethane materials with active targeting as drug carriers has not been reported

Method used

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  • Biodegradable polyurethane with amino on side chain and preparation method and application thereof
  • Biodegradable polyurethane with amino on side chain and preparation method and application thereof
  • Biodegradable polyurethane with amino on side chain and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] Example 1: Preparation of polyester polyurethane with polylactide diol as soft segment with protected amino group in side chain

[0081] Put dry 0.01mol of polylactic acid diol (Mn=0.3kg / mol) in a dry 50ml reaction bottle, add 10ml of anhydrous toluene, wait until it is completely dissolved, add 0.015mol of lysine methyl diisocyanate and 0.15g stannous octoate, 70 ℃, reacted for 0.5 hours, then added 0.005mol chain extender 2,2-(2-chlorobenzyloxycarbonyl) diaminomethyl-1,3-propanediol to the reaction flask, reaction 1 Hours, the product was precipitated in ethanol to obtain polyester polyurethane with polylactide diol as the soft segment.

Embodiment 2

[0082] Embodiment 2: Preparation of polyester polyurethane with polycaprolactone diol as soft segment with protected amino group in side chain

[0083] Put dry 0.02mol of polycaprolactone diol (Mn=5kg / mol) in a dry 500ml reaction bottle, add 250ml of anhydrous tetrahydrofuran, wait until it is completely dissolved, add 0.04mol of isophorone diisocyanate and 0.015g dibutyltin dilaurate, 80°C, react for 2 hours, then add 0.02mol of chain extender 2,2-benzyloxycarbonyl diaminomethyl-1,3-propanediol to the reaction flask, react for 4 hours, the product Precipitate in ethanol to obtain polyester polyurethane with polycaprolactone diol as the soft segment.

Embodiment 3

[0084] Example 3: Preparation of Polyester Polyurethane with Polycarbonate Diol as Soft Segment with Protected Amino in Side Chain

[0085] Put dry 0.02mol polycarbonate diol (Mn=3.5kg / mol) in a dry 500ml reaction bottle, add 300ml of anhydrous dimethylformamide, wait until it is completely dissolved, add 0.045mol of isophor Ketone diisocyanate and 0.015g triethanolamine were reacted at 75°C for 3 hours, then 0.025mol of chain extender 2,2-benzyloxycarbonyldiaminomethyl-1,3-propanediol was added to the reaction flask, and reacted for 4.5 hours. The product is precipitated in ethanol to obtain polyester polyurethane with polycarbonate diol as the soft segment.

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Abstract

The invention provides biodegradable polyurethane with an amino on the side chain and a preparation method and application thereof, belonging to the field of biomedical materials. Polyurethane is formed by a soft segment and a hard segment, wherein the soft segment is biodegradable polyester diol or biodegradable polyether diol; the hard segment is formed by aliphatic diisocyanate and a chain extender; and the hard segment is provided with the free or protected amino. The biodegradable polyurethane serves as a drug carrier, can wrap drug molecules to form drug carrying microspheres in the nanometer or micrometer scale and can be used for bonding drug molecules, fluorescent molecules and targeted molecules to prepare polyurethane bonded drugs, polyurethane fluorescent probes or polyurethane targeting carriers.

Description

technical field [0001] The invention belongs to the field of biomedical materials, and in particular relates to biodegradable polyurethane with amino groups in side chains, a preparation method and application thereof. Background technique [0002] Medical polyurethane is composed of soft segment and hard segment, and the structure contains a large number of polar carbamate groups. At the same time, its unique microphase separation structure endows medical polyurethane with excellent mechanical properties and biocompatibility, which can be widely used In artificial heart, heart valve, artificial blood vessel, tissue engineering scaffold and other medical fields. Although medical polyurethane has good biocompatibility, it is not convenient to further improve the properties of polyurethane due to the lack of active groups in the molecular structure. In order to better meet specific medical needs, such as protein fixation, tissue engineering, and shape memory built-in devices,...

Claims

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Application Information

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IPC IPC(8): C08G18/66C08G18/32C08G18/48C08G18/42C08G18/83A61K47/34A61K47/48A61K45/00A61K31/704A61K31/337A61K31/4745A61K49/00A61P35/00
Inventor 景遐斌杨立新谢志刚黄宇彬肖海华
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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