Research Progress on Preparation and Properties of Bio-Based Polyurethanes from Amino Acid and Its Derivatives

doi:10.19894/j.issn.1000-0518.240294

Chinese Journal of Applied Chemistry ›› 2025, Vol. 42 ›› Issue (1): 42-57.DOI: 10.19894/j.issn.1000-0518.240294

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Research Progress on Preparation and Properties of Bio-Based Polyurethanes from Amino Acid and Its Derivatives

Guo-Hong TANG¹^,², Zhen ZHAO³, Jia-Hui ZHONG¹^,², Xiao-Ling XU¹^,², Ying-Lu SUN¹, De-Kun SHENG¹, Yu-Ming YANG¹^,²()

^1.CAS Key Laboratory of High-Performance Synthetic Rubber and Its Composite Material，Changchun Institute of Applied Chemistry，Chinese Academy of Science，Changchun 130022，China
^2.University of Science and Technology of China，Hefei 230026，China
^3.Military Representative Office of the Air Force Armament Department in Changchun，Changchun 130000，China

Received:2024-09-06 Accepted:2024-11-27 Published:2025-01-01 Online:2025-01-24
Contact: Yu-Ming YANG
About author:ymyang@ciac.ac.cn
Supported by:
the National Natural Science Foundation of China(22175171);the Natural Science Foundation of Jilin Province of China(SKL202302036)

Abstract

Abstract:

As a kind of renewable resource， bio-based raw materials have the characteristics of less pollution and easy recyclability compared to petroleum-based raw materials. The research on polyurethanes synthesized by bio-based feedstocks has been quite extensive， while a wide range of bio-based materials can be chosen. Amino acid as a kind of bio-based raw material， has various structures and high reactivity with easy access to obtain， whose degradation products are non-toxic and harmless. There are versatile methods to synthesize polyurethanes using amino acid as different components. The application of amino acid and its derivates in bio-based polyurethanes synthesis is reviewed； The relationship between structure and performance of the polyurethanes is expounded. The prospect and directions of future development of amino acid and bio-based polyurethanes is envisioned.

Key words: Polyurethane, Bio-based material, Amino acids, Structure and performance

CLC Number:

O631

Guo-Hong TANG, Zhen ZHAO, Jia-Hui ZHONG, Xiao-Ling XU, Ying-Lu SUN, De-Kun SHENG, Yu-Ming YANG. Research Progress on Preparation and Properties of Bio-Based Polyurethanes from Amino Acid and Its Derivatives[J]. Chinese Journal of Applied Chemistry, 2025, 42(1): 42-57.

Figures/Tables 14

Fig.1 Structural formula of amino acid

Fig.2 Synthesis of the PEG-AAPU（SS）-PEG triblock copolymer［20］

Fig.3 MTT assays of blank PEG-AAPU（SS）-PEG micelles in RAW264.7 and MCF-7/ADR cells. Results are presented as the mean±SD （n=4）［20］

Fig.4 Chemical rearrangements for bio-based isocyanates：（a） Curtius rearrangements，（b） Hoffman rearrangements， and （c） Lossen rearrangements［32］

Fig.5 The mechanism of the reaction between TA and LDI［39］

Table 1 Mechanical properties and Tg of BWPU［40］

Sample	T_g/℃	Tensile strength/MPa	Elongation at break/%	Toughness/（MJ·m^-3）	Young′s modulus/MPa
LBWPU-32%	-14.7	4.80±2.1	1 033±25	34.3±3.4	10.3±2.3
LBWPU-38%	-13.8	11.3±3.5	1 015±16	61.0±2.7	19.7±3.1
LBWPU-44%	-13.0	13.7±1.3	973±12	66.8±2.6	25.4±3.9
LBWPU-48%	-12.1	21.5±2.9	802±31	82.5±4.9	51.2±2.9
CBWPU-0.5%	-11.9	30.1±3.7	702±57	111±2.1	61.5±2.4
CBWPU-1%	-11.0	41.5±1.7	663±35	131±1.0	87.6±3.7
CBWPU-2%	-10.3	38.9±2.3	619±27	123±1.2	108±4.9

Fig.6 （A） Structure of cholic acid［41］；（B） The percentage of residual mass of polyurethanes （PURs） during the course of enzymatic degradation in the presence of porcine pancreatic lipase［42］；（C） Hydrolytic degradation behaviors of PCL-PU and CA-PCL-PU［43］；（D） Enzymatic degradation of PCL-PU and CA-PCL-PUs［43］

Table 2 Melt temperature and mechanical properties of the materials［43］

Sample	T_m/℃	Tensile strength/MPa	Elongation at break/%	Young′s modulus/MPa
PCL-PU	65	18.68	11.66	171.61
CA-PCL-PU-1	53	9.37	243.29	121.48
CA-PCL-PU-2	50	10.85	313.50	138.67
CA-PCL-PU-3	45	11.57	327.26	157.71

Fig.7 Scheme of the synthesis of model compounds［52］

Table 3 Relative Molecular mass， Tg and mechanical properties of PU［52］

Sample	Molecular mass			T_g/℃	Mechanical properties
Sample	10^-4M_n	10^-4M_w	PDI	T_g/℃	Tensile strength/MPa	Elongation at break/%	Young′s modulus/MPa
PU-BDA-530	30.45	65.17	2.14	3	2.4±0.1	327±28	1.8±0.5
PU-R-530	7.22	16.33	2.26	3	1.6±0.5	667±84	0.6±0.2
PU-G-530	12.16	16.57	1.36	5	2.1±0.5	571±73	0.8±0.2
PU-D-530	3.06	15.00	4.90	5	0.9±0.1	116±8	0.9±0.1

Fig.8 Skeletal myoblast growth on polystyrene cell culture plates （positive control） and the PURs. Optical absorbance at 490 nm is directly proportional to the amount of viable cells［56］

Fig.9 Actin cytoskeleton of myoblasts cultured for 7 days on the synthesised polyurethanes. Samples were stained with phalloidin-TRITC conjugated which specifically binds actin filaments and DAPI， a blue fluorescent dye specific for DNA［56］

Fig.10 （A） Visual appearance of PU film samples after different days of degradation under composting conditions；（B） SEM observations of PU and lys-PU recovered films at different degradation time under composting conditions［57］

Fig.11 （A） Cyclic shape fixity ratios （Rf） and （B） shape recovery ratios （Rr） of the SMPU［59］

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Research Progress on Preparation and Properties of Bio-Based Polyurethanes from Amino Acid and Its Derivatives

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