Preparation and Characterization of Thermoresponsive Hyperbranched Polyethylenimine with Plenty of Reactive Primary Amine Groups

Hua-ji Liu; Run-hua Dong; Yu Chen

doi:10.1007/s10118-014-1471-4

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Preparation and Characterization of Thermoresponsive Hyperbranched Polyethylenimine with Plenty of Reactive Primary Amine Groups

Note | Updated：2021-06-21

- Preparation and Characterization of Thermoresponsive Hyperbranched Polyethylenimine with Plenty of Reactive Primary Amine Groups
- Chinese Journal of Polymer Science Vol. 32, Issue 7, Pages: 961-968(2014)
- Affiliations：
  
  Department of Chemistry, School of Sciences, Tianjin University; Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072, China
- Author bio：
  
  **Yu Chen (陈宇), E-mail: chenyu@tju.edu.cn
- Funds：
- DOI：10.1007/s10118-014-1471-4
  CLC：
- Received：13 March 2014，
  
  Revised：2014-04-09，
  
  Accepted：14 April 2014，
  
  Published：2014-07
- Accepted：
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Hua-ji Liu, Run-hua Dong, Yu Chen. Preparation and Characterization of Thermoresponsive Hyperbranched Polyethylenimine with Plenty of Reactive Primary Amine Groups[J]. Chinese Journal of Polymer Science, 2014, 32(7): 961-968.
DOI：

Hua-ji Liu, Run-hua Dong, Yu Chen. Preparation and Characterization of Thermoresponsive Hyperbranched Polyethylenimine with Plenty of Reactive Primary Amine Groups[J]. Chinese Journal of Polymer Science, 2014, 32(7): 961-968. DOI： 10.1007/s10118-014-1471-4.

摘要

Abstract

Certain amount of primary amine (NH

) groups of hyperbranched polyethylenimine (HPEI) was first protected by Boc groups. Subsequently

the residual reactive amine groups were reacted with isobutyric anhydride to introduce isobutyramide (IBAm) groups to HPEI. Finally

Boc groups were deprotected to result in HPEI-IBAm-NH

with 18% of primary amine terminals on the periphery and 80% of IBAm terminal groups (abbreviated as HPEI-IBAm

0.80

-NH

H-NMR characterization proved the successful preparation of the product in each step. Compared with its spatial isomer HPEI-IBAm

0.80

without primary amine groups

H-NMR spectra verified that more IBAm groups were located in the interior of HPEI-IBAm

0.80

-NH

. The further modification of HPEI-IBAm

0.80

-NH

and HPEI-IBAm

0.80

with p-nitrobenzaldehyde demonstrated that HPEI-IBAm

0.80

-NH

was more reactive than HPEI-IBAm

0.80

due to its possession of primary amines. Turbidimetry measurements showed that HPEI-IBAm

0.80

-NH

was thermoresponsive in water. In the pH range of 9.5−10 its cloud point temperature (

) was constant

and it increased obviously upon decreasing the pH below 9.5. The thermoresponsive HPEI-IBAm

0.8

exhibited the similar trend

but the pH threshold to achieve the constant

was around 8.5. Moreover

HPEI-IBAm

0.8

-NH

showed higher

and broader phase transition than HPEI-IBAm

0.8

. The mechanism leading to the different thermoresponsive properties between HPEI-IBAm

0.8

-NH

and its spatial isomer HPEI-IBAm

0.8

was discussed.

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Related Institution

Department of Chemistry, School of Sciences, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin)

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Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Sciences, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering(Tianjin)

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