Modification of Polyurethane by “Click” Chemistry†

doi:10.7503/cjcu20131089

Abstract

Abstract:

In this study, 2,2-propargyl-1,3-propanediol(DPPD) was synthesized and used as the chain extender for getting a biodegradable polyurethane(PU) containing alkynyl. The structure of the PU containing alkynyl is confirmed by the characteristic ¹H NMR chemical shift at δ 2.03 and Fourier transform infrared spectrum(FTIR) absorption band at 2138 cm^-1. When the DPPD chain extender and PU prepolymer were polymerized with the molar ratio of 1, 0.7 and 1(70%DPPD+30%1,3-propanediol), the obtained alkynyl grafting ratio were 0.396, 0.235 and 0.197 mmol/g, respectively. The “click” coupling of the PU alkynyl group with the model molecular benzyl azide is proved by the chemical shift at δ 7.91 of the ¹H NMR test result. Cell viability experiments reveal that alkynyl grafted on the PU has no influence on the cells viability. This method provides a convenient way for bioactive modification of biodegradable polyurethane.

Key words: Polyurethane, “Click”, chemistry, Modification

CLC Number:

O633

TrendMD:

CHEN Long, WU Gang, HUANG Chao, WANG Jiahui. Modification of Polyurethane by “Click” Chemistry^†[J]. Chem. J. Chinese Universities, 2014, 35(4): 853.

Figures/Tables 9

Scheme 1 Synthetic route of DPPD

Fig.1 1H NMR spectra of S1(A) and DPPD(B)

Fig.2 FTIR spectra of S1(A) and DPPD(B)

Table 1 Synthesis of polyurethane containing alkynyl group

Polymer	n(PCL)∶n(HMDI)∶ n(DPPD)∶n(PDO)	M_w	PDI	Alkynyl content/(mmol·g^-1)
Polymer	n(PCL)∶n(HMDI)∶ n(DPPD)∶n(PDO)	M_w	PDI	Theoretically^a	Measured^b
Alky-PU-1	1:2:1:0	47783	2.443	0.402	0.396
Alky-PU-2	1:2:0.7:0	41728	1.828	0.281	0.235
Alky-PU-3	1:2:0.7:0.3	20991	1.745	0.281	0.197

Scheme 2 Synthetic route of Alky-PU

Fig.3 1H NMR spectrum of Alky-PU-1

Fig.4 FTIR spectrum of Alky-PU-1

Fig.5 1H NMR spectrum of Alky-PU-Bn

Fig.6 Cell viability of the synthesized Alky-PU with CCK8

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