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Preparation method of shape memory polyurethane based on lactide and 1, 4-p-dioxanone

A technology for dioxanone and lactide, which is applied in the field of preparation of shape memory polymers, can solve the problems of difficulty in obtaining high molecular weight chain shape memory polyurethane, low yield of final products, poor reaction controllability and the like , to prevent the initiation of cross-linking reaction, improve the controllability of the reaction, and improve the product yield.

Inactive Publication Date: 2012-01-18
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
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Problems solved by technology

[0005] But the above-mentioned preparation method has the following deficiencies: (1) adopt one-step method to prepare hydroxyl-terminated poly(lactide-co-1,4-dioxanone), which is easy to generate by-products, namely polylactic acid or poly(polylactic acid) containing carboxyl group at one end. For dioxanone, resulting in a lower yield of the final product; (2) diisocyanate can react rapidly with water at a higher temperature (60-80° C.) to generate by-products and reduce the reaction yield, and hydroxyl-terminated poly(propylene The reaction of lactide-co-1,4-dioxanone) and diisocyanate is carried out in solvent N,N-dimethylformamide, because N,N-dimethylformamide is compatible with water Therefore, the trace moisture in the air and the reaction system has a great influence on the reaction, and the controllability of the reaction is poor; (3) N, N-dimethylformamide is used as a cosolvent for the chain extension reaction, because the isocyanate There is a hydrogen bond between the base and the chain extender, and the presence of excess chain extender can trigger a crosslinking reaction, resulting in the formation of a gel-like substance, making it difficult to obtain high molecular weight chain shape memory polyurethane

Method used

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  • Preparation method of shape memory polyurethane based on lactide and 1, 4-p-dioxanone
  • Preparation method of shape memory polyurethane based on lactide and 1, 4-p-dioxanone
  • Preparation method of shape memory polyurethane based on lactide and 1, 4-p-dioxanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] a, the preparation of hydroxyl-terminated poly(lactide-co-1,4-dioxanone)

[0031] First, 16 μL (5.36×10 -6 mol) and ethylene glycol 32μL (5.73×10 -4mol) mixed evenly, evacuated for 10-20 minutes, sealed, and reacted at 80°C for 24 hours (use gas chromatography to detect the remaining amount of monomer to monitor the reaction process), cool, break the vacuum, and then add D, L-lactide 5.000 g (0.03472mol) (the molar ratio of D,L-lactide to 1,4-dioxanone is 0.7:1) and stannous octoate T-9 at a concentration of 0.1347g / mL in dichloromethane Solution 16μL (5.36×10 -6 mol), mix evenly, vacuumize for 10-20 minutes, seal, react at 140°C for 24 hours, cool, break the vacuum, dissolve the reaction product in dichloromethane, purify with absolute ethanol, and dry in vacuum at room temperature to obtain hydroxyl-terminated poly( Lactide-co-1,4-dioxanone) 3.8g, the average molecular weight recorded by the terminal hydroxyl analysis method is 5000, and the T is recorded by the DS...

Embodiment 2

[0041] The main difference between this example and Example 1 is that in step a, by adjusting the molar ratio of D, L-lactide to 1,4-dioxanone, the hydroxyl-terminated poly(lactide) Ester-co-1,4-dioxanone) average molecular weight and glass transition temperature.

[0042] a, the preparation of hydroxyl-terminated poly(lactide-co-1,4-dioxanone)

[0043] First, 1.25 mL (0.01551 mol) of 1,4-dioxanone and 16 μL (5.36×10 -6 mol) and ethylene glycol 32μL (5.73×10 -4 mol) mixed evenly, evacuated for 10-20 minutes, sealed, reacted at 80°C for 12 hours, cooled, broke the vacuum, and then added D, L-lactide 5.000g (0.03472mol) (D, L-lactide and 1 , the molar ratio of 4-dioxanone is 2.24:1) and 16 μL (5.36×10 -6 mol), mix evenly, vacuumize for 10-20 minutes, seal, react at 130°C for 24 hours, cool, break the vacuum, dissolve the reaction product in dichloromethane, purify with absolute ethanol, and dry in vacuum at room temperature to obtain hydroxyl-terminated poly( Lactide-co-1,4-...

Embodiment 3

[0047] The main difference between this example and Example 2 is that in step b, by adjusting hydroxyl-terminated poly(lactide-co-1,4-dioxanone), 1,6-hexamethylene The molar ratio of diisocyanate to stannous octoate and the molar ratio of butanediamine to hydroxyl-terminated poly(lactide-co-1,4-dioxanone), thereby adjusting the hydroxyl-terminated poly(lactide-co - the glass transition temperature of 1,4-dioxanone)-based block polyurethane.

[0048] a, the preparation of hydroxyl-terminated poly(lactide-co-1,4-dioxanone) (same as Example 2)

[0049] b, preparation of hydroxyl-terminated poly(lactide-co-1,4-dioxanone)-based block polyurethane

[0050] First, 5 g (0.001 mol) of hydroxyl-terminated poly(lactide-co-1,4-dioxanone) obtained in step a, 184 μL (0.0015 mol) of 1,6-hexamethylene diisocyanate and a concentration of 30μL of 0.1347g / mL stannous octoate T-9 in dichloromethane -5 mol) (the molar ratio of the three is 1:1.5:0.01) dissolved in 15mL of toluene that has been ...

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Abstract

The invention discloses a preparation method of shape memory polyurethane based on lactide and 1, 4-p-dioxanone. The preparation method comprises the following steps of: firstly carrying out vacuum melting reaction on the 1, 4-p-dioxanone, stannous octoate and small molecule diol to generate hydroxyl-terminated polybutadiene (1, 4-p-dioxanone), carrying out vacuum melting reaction on the hydroxyl-terminated polybutadiene and the lactide as well as the stannous octoate to prepare the hydroxyl-terminated polybutadiene (lactide-co-1, 4-p-dioxanone), then reacting the hydroxyl-terminated polybutadiene with diisocyanate as well as the stannous octoate in a benzene solvent to generate prepolymer, and then reacting the prepolymer with an isopropyl alcohol solution of chain extender small molecule diol or small molecule diamine to prepare shape memory polyurethane. The invention adopts a tow-step method to prepare hydroxyl-terminated polybutadiene (lactide-co-1, 4-p-dioxanone), takes the benzene solvent as a pre-polymerization reaction solvent, introduces isopropanol as a cosolvent in the chain extension reaction, and can enhance reaction controllability, reduce by-product production, enhance product yield and obtain high molecular weight chain-shaped shape memory polyurethane with excellent shape memory performance.

Description

technical field [0001] The invention relates to a preparation method of a shape-memory polymer, in particular to a preparation method of a shape-memory polyurethane based on lactide (LA) and 1,4-dioxanone (PDO). Background technique [0002] Shape memory material refers to a product with a certain original shape. After being deformed and finalized, it will change under specific external conditions (physical factors such as heat energy, light energy, electric energy, and chemical factors such as pH, ionic strength, phase transition reaction, and chelation reaction). ) stimulation can automatically restore the original shape of a class of functional materials, in aviation, aerospace, medical, construction, packaging, automotive, electronics, machinery and other fields have broad application prospects. Shape memory materials include shape memory alloys (SMA), shape memory ceramics (SMC) and shape memory polymers (SMP). Among them, shape memory polymer has become a vigorously d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G18/66C08G18/42C08G18/10C08G63/664
Inventor 罗彦凤王远亮黄美娜
Owner CHONGQING UNIV
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