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Bi-tellurium-containing biodegradable polymer and preparation method thereof

A technology for degrading polymers and biology, which is applied in the direction of fermentation, etc., can solve the problems of limiting the application of ditellurium compounds, few polymers containing ditellurium, and non-biodegradable, etc., to achieve excellent light environment response performance, high yield, and by-products little effect

Inactive Publication Date: 2018-01-05
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, ditellurium compounds or intermediates are unstable and prone to decomposition or agglomeration under light and oxygen conditions, which makes the preparation of ditellurium compounds difficult and limits the application of ditellurium compounds
Very little research has been done on ditellurium-containing polymers, and these polymers are not biodegradable (Al-Rubaiee et al. Applied Organometallic Chemistry 2002; 16:649-54.)

Method used

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  • Bi-tellurium-containing biodegradable polymer and preparation method thereof
  • Bi-tellurium-containing biodegradable polymer and preparation method thereof
  • Bi-tellurium-containing biodegradable polymer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1 contains ditelluric polycaprolactone (PCLTe) 2 (I-1a)

[0032] Synthesis of 2,2'-Ditelluridedipropanol (II-1)

[0033]

[0034] Weigh (2.2698g, 60mmol) sodium borohydride and deionized water (150mL) into a 500mL reaction bulb and stir until the sodium borohydride is completely dissolved, then add tellurium powder (7.26g, 60mmol) and react at 70°C for 30min, to get the magenta Na 2 Te 2 solution. Then, under nitrogen protection, bromopropanol (8.34 g, 60 mmol) in tetrahydrofuran (150 mL) was added, and reacted at 50° C. in the dark for 5 hours. After the reaction was completed, it was extracted with anaerobic dichloromethane, dried over anhydrous magnesium sulfate, and separated by column chromatography (eluent: dichloromethane: ethyl acetate = 1:2 (v / v)) to obtain a purple-red compound, That is, 2,2'-ditelluridedipropanol (II-1). 1 H NMR (400MHz, CDCl 3 )δ(ppm):3.72(4H,t,HOCH 2 ),3.19(4H,t,TeTeCH 2 ),2.00(4H,m,HOCH 2 CH 2 CH 2 TeTe) and 1.70(...

Embodiment 2

[0041] Embodiment 2 contains two tellurium polycarbonates (PTMCTe) 2 (I-1b)

[0042]

[0043] Add 2,2'-ditelluridedipropanol (0.372g, 1mmol), trimethylene carbonate (TMC) (4.08g, 40mmol) into a pre-baked eggplant-shaped reaction bottle, and vacuumize at 40°C A small amount of moisture was removed for 3 hours, then Novozymes lipase 435 (0.408 g) and anhydrous oxygen-free toluene (10 mL) were added under nitrogen protection, and the reaction was carried out at 60° C. for 24 hours. After the reaction was completed, the enzyme was removed by filtration, settled in glacial ether, and vacuum-dried to obtain the target product ditellurium-containing polycarbonate (I-1b), with a yield of 91%.

[0044] 1 H NMR (400MHz, CDCl 3 )δ(ppm) (such as Figure 4 shown): a (4.24), b (2.05), c (4.10), e (3.10), d (2.07).

[0045] 125 Te NMR (189MHz, CDCl 3 ) δ (ppm): 388.4.

Embodiment 3

[0046] Embodiment 3 contains ditelluric polycaprolactone (PCLTe) 2 (I-2a)

[0047] Synthesis of 2,2'-Ditelluridediethanol (II-2)

[0048]

[0049] Weigh sodium borohydride (2.2698g, 60mmol) and deionized water (150mL) into a 500mL reaction ball bottle and stir until sodium borohydride is completely dissolved, then add tellurium powder (7.26g, 60mmol) and react at 70°C for 30min , to obtain the purple-red Na 2 Te 2 solution. Then, under nitrogen protection, bromoethanol (7.49 g, 60 mmol) in tetrahydrofuran (150 mL) was added, and reacted at 50° C. in the dark for 6 hours. After the reaction was completed, it was extracted with anaerobic dichloromethane, dried over anhydrous magnesium sulfate, and separated by column chromatography (eluent was dichloromethane:ethyl acetate=1:1 (v / v)) to obtain a purple-red compound, That is, 2,2'-ditelluridediethanol. 1 HNMR (400MHz, CDCl 3 )δ(ppm):3.87(4H,t,HOCH 2 ),3.32 (4H,t,TeTeCH 2 ), and 2.11 (2H,s,HOCH 2 ). 13 C NMR (125MHz,...

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Abstract

The invention discloses a bi-tellurium-containing biodegradable polymer shown as a formula (I), wherein m is an integer of 1 to 20; n is an integer of 1-20; p is an integer of 1-10; m' is an integer of 10-1000; n' is an integer of 10-1000; R is carbon or oxygen. The invention further discloses a method for preparing the bi-tellurium-containing biodegradable polymer. The bi-tellurium-containing biodegradable polymer and the preparation method thereof disclosed by the invention have the benefits that functionalized di-tellurium small molecules and lactones are taken as raw materials, a bi-tellurium bond is successfully introduced into the biodegradable polymer in a manner of enzymatic catalysis ring-opening reaction under mild reaction conditions, by-products in the reaction process are less, the yield is high, and the prepared bi-tellurium-containing biodegradable polymer has excellent light environment response performance.

Description

technical field [0001] The invention belongs to the technical field of biodegradable materials, and relates to a bitellurium-containing biodegradable polymer and a preparation method thereof. Background technique [0002] Polycarbonate (PTMC) and polycaprolactone (PCL) are biodegradable materials approved by the FDA for use in the biomedical field. These polyesters have good biocompatibility and excellent mechanical properties, and are widely used in the fields of tissue engineering, drug sustained release, gene therapy, implantable devices, and regenerative medicine. [0003] Recently, disulfide and diselenium compounds have been widely used in self-healing polymers and environmental responsiveness due to their ability to break and recombine under specific circumstances (Otsuka H, ​​Nagano Setal . Chemical communications 2010; 46:1150-2; Ji S et al. Advanced materials 2015; 27:7740-5). [0004] The bond energy of ditellurium bond is low (127KJ / mol) (Kildahl NK.Journal of ...

Claims

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Application Information

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IPC IPC(8): C12P7/62
Inventor 郎美东刘佳
Owner EAST CHINA UNIV OF SCI & TECH
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