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Hydroxyl telechelic polyester material based on piperazine block and preparation method thereof

A technology of hydroxyl-terminated polyester and piperazine, which is applied in the field of piperazine-based block hydroxyl-terminated polyester materials and their preparation, can solve the problem that the properties of polyester materials have little influence, the initiator has no biological activity, and the co-initiating In order to achieve the effect of controllable molecular weight, slowing down the effect of acid-induced autocatalytic degradation, good biocompatibility and biodegradability

Inactive Publication Date: 2010-12-01
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, in the synthesis of oligomers with terminal functional groups, the selection of co-initiators is the most important thing. The activity of co-initiators will affect the synthesis process; since co-initiators will be blocked into the final material, it will also affect the quality of materials. physical chemistry of
Currently commonly used co-initiators are polyol small molecules, such as ethylene glycol, butylene glycol, glycerol, pentaerythritol, etc., but such initiators themselves do not have biological activity and have little effect on the properties of polyester materials.
However, there are few reports on the use of highly reactive polyamine small molecules as initiators.

Method used

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  • Hydroxyl telechelic polyester material based on piperazine block and preparation method thereof
  • Hydroxyl telechelic polyester material based on piperazine block and preparation method thereof
  • Hydroxyl telechelic polyester material based on piperazine block and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Weigh 5.000 g (0.03472 mol, molecular weight: 144) of D, L-lactide that has been distilled and recrystallized three times from ethyl acetate, and 0.5979 g (0.5979 g) of anhydrous piperazine ( 0.00694mol, molecular weight: 86.1), were added to a 25ml round bottom flask, and stannous octoate was added as an initiator according to 1 / 5000 of the molar weight of D, L-lactide, and then vacuumed 2 to 3 times, respectively After 15 minutes, seal the flask, place it in an oil bath to heat, control the temperature at 150°C, and react for 24 hours. After the reaction product was dissolved in dichloromethane, it was purified with n-hexane and dried at room temperature to obtain 3.512g polylactic acid with hydroxypiperazine block at the end, glass transition temperature T g =13.14°C, its molecular weight was determined to be 830 (theoretical molecular weight was 144×5+86.1=805.1) by the hydroxyl end titration analysis method.

[0024] The synthetic route of embodiment 1 is as follo...

Embodiment 2

[0027] Weigh 5.000 g (0.03472 mol, molecular weight: 144) of D, L-lactide that has been distilled and recrystallized three times from ethyl acetate, and 0.2988 g (0.2988 g) of anhydrous piperazine ( 0.00347mol, molecular weight: 86.1), were added to a 25ml round bottom flask, according to 1 / 5000 of the molar weight of D, L-lactide, stannous octoate was added as an initiator, and then vacuumed 2 to 3 times, respectively After 15 minutes, seal the flask, place it in an oil bath to heat, control the temperature at 150°C, and react for 24 hours. After the reaction product was dissolved in dichloromethane, it was purified with n-hexane and dried at room temperature to obtain 3.823g polylactic acid with hydroxypiperazine block, glass transition temperature T g =20.54°C, its molecular weight was determined to be 1132 (theoretical molecular weight was 144×10+86.1=1526.1) as determined by terminal hydroxyl titration analysis.

Embodiment 3

[0029] Weigh 5.000 g (0.03472 mol, molecular weight: 144) of D, L-lactide that has been distilled and recrystallized three times from ethyl acetate, and 0.1495 g (0.1495 g) of anhydrous piperazine ( 0.00173mol, molecular weight: 86.1), respectively added to a 25ml round bottom flask, added stannous octoate as an initiator according to 1 / 5000 of the molar weight of D, L-lactide, and then evacuated 2 to 3 times, respectively After 15 minutes, seal the flask, place it in an oil bath to heat, control the temperature at 150°C, and react for 24 hours. After the reaction product was dissolved in dichloromethane, it was purified with n-hexane and dried at room temperature to obtain 3.901 g of polylactic acid with a hydroxypiperazine block, with a glass transition temperature of T g =28.45°C, its molecular weight was determined to be 2576 (theoretical molecular weight was 144×20+86.1=2966.1) as determined by terminal hydroxyl titration analysis.

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Abstract

The invention relates to a hydroxyl telechelic polyester material based on piperazine block and a preparation method thereof. Piperazine serves as an assistant initiator, and stannous octoate serves as an initiator; at the temperature of 130-170 DEG C, an annular esters monomer (annular diester such as lactide, glycolide, epsilon-caprolactone, ixoxanone and the like or lactone) is initiated for fusion and ring-opening polymerization to obtain the hydroxyl telechelic polyester material. The main chain of the hydroxyl telechelic polyester material based on the piperazine block of the invention is inserted with piperazine micromolecule rigid rings, and the mechanical property of the material is correspondingly improved; piperzaine is a common drug intermediate, has a certain bioactivity and can fill up the deficiency of insufficient polyester material activity; meanwhile, the molar ratio of the piperaztine and the annular esters monomer is controlled to control the molecular weight of the polyester material, so that the hydroxyl telechelic polyester material is convenient to apply in different areas; in addition, the polyester has biodegradability and favourable biocompatibility, has important application value on the aspect of drug slow release carriers and tissue engineering biological materials and can serve as the ultra high molecular weight polymers or the prepolymers of the polyester biological materials.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and in particular relates to a polyester material based on piperazine block-terminated hydroxyl groups and a preparation method thereof Background technique [0002] Aliphatic polyester polymer materials, such as polylactic acid, polyglycolide, polycaprolactone or their copolymers, have been widely used in biomedical engineering due to their good biocompatibility and biodegradability. Fields, such as biodegradable surgical sutures, drug-controlled slow-release carriers, fracture fixation components, and tissue repair scaffolds. [0003] At present, there are three main methods for synthesizing high-molecular-weight aliphatic polyester materials: direct polymerization of corresponding monomers, ring-opening polymerization of corresponding lactones, and formation of functional group-terminated prepolymerization followed by chain extension (such as hydroxyl-terminated). The first method h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/685C08G63/08C08G63/78A61K47/34A61L27/18C08G18/42
Inventor 王远亮阮长顺魏小娅张兵兵付春华张茂兰窦庶华
Owner CHONGQING UNIV
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