Non-Isocyanate Urethane Acrylate Derived from Isophorone Diamine: Synthesis, Characterization and Its Application in 3D Printing

被引:2
作者
Zhang, Xinqi [1 ]
Zan, Xinxin [1 ]
Yin, Jiangdi [1 ]
Wang, Jiaxi [1 ,2 ]
机构
[1] Hebei Univ Technol, Sch Chem Engn & Technol, Tianjin 300130, Peoples R China
[2] Hebei Univ Technol, Hebei Prov Key Lab Green Chem Technol & High Effic, Tianjin 300130, Peoples R China
来源
MOLECULES | 2024年 / 29卷 / 11期
基金
英国科研创新办公室;
关键词
non-isocyanate; urethane acrylate; isophorone diamine; UV curing; 3D printing; POLYURETHANE COATINGS; SOYBEAN OIL; PHOTOPOLYMERIZATION; PHOTOINITIATOR;
D O I
10.3390/molecules29112639
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
In this paper, urethane-based acrylates (UA) were prepared via an environmentally friendly non-isocyanate route. Isophorone diamine (IPDA) reacted with ethylene carbonate (EC), producing carbamate containing amine and hydroxyl groups, which further reacted with neopentyl glycol diacrylate (NPGDA) by aza Michael addition, forming UA. The structures of the obtained intermediates and UA were characterized by 1H NMR and electrospray ionization high-resolution mass spectrometry (ESI-HRMS). The photopolymerization kinetics of UA were investigated by infrared spectroscopy. The composite with obtained UA can be UV cured quickly to form a transparent film with a tensile strength of 21 MPa and elongation at break of 16%. After UV curing, the mono-functional urethane acrylate was copolymerized into the cross-linked network in the form of side chains. The hydroxyl and carbamate bonds on the side chains have high mobility, which make them easy to form stronger dynamic hydrogen bonds during the tensile process, giving the material a higher tensile strength and elongation at break. Therefore, the hydrogen bonding model of a cross-linked network is proposed. The composite with UA can be 3D printed into models.
引用
收藏
页数:15
相关论文
共 50 条
[21]   Food 3D Printing Technology and Its Application in Meat Processing: A Review [J].
Yang G. ;
Huang M. ;
Xu X. .
Shipin Kexue/Food Science, 2021, 42 (21) :308-314
[22]   Synthesis and characterization of photopolymerizable triblocks for 3D printing tissue engineering scaffolds [J].
Cheng, Yih-Lin ;
Hsu, Yi-Jue .
JOURNAL OF THE CHINESE INSTITUTE OF ENGINEERS, 2018, 41 (03) :259-267
[23]   3D printing using plant-derived cellulose and its derivatives: A review [J].
Dai, Lei ;
Cheng, Ting ;
Duan, Chao ;
Zhao, Wei ;
Zhang, Weipeng ;
Zou, Xuejun ;
Aspler, Joseph ;
Ni, Yonghao .
CARBOHYDRATE POLYMERS, 2019, 203 :71-86
[24]   Biocompatible tissue-engineered scaffold polymers for 3D printing and its application for 4D printing [J].
Hasanzadeh, Rezgar ;
Mihankhah, Peyman ;
Azdast, Taher ;
Rasouli, Asghar ;
Shamkhali, Mohadese ;
Park, Chul B. .
CHEMICAL ENGINEERING JOURNAL, 2023, 476
[25]   Micro 3D Printing Using a Digital Projector and its Application in the Study of Soft Materials Mechanics [J].
Lee, Howon ;
Fang, Nicholas X. .
JOVE-JOURNAL OF VISUALIZED EXPERIMENTS, 2012, (69) :e4457
[26]   Synthesis of carbon from waste coconutshell and their application as filler in bioplast polymer filaments for 3D printing [J].
Umerah, Chibu O. ;
Kodali, Deepa ;
Head, Sydnei ;
Jeelani, Shaik ;
Rangari, Vijaya K. .
COMPOSITES PART B-ENGINEERING, 2020, 202
[27]   Thermal stability of UV-cured vegetable oil epoxidized acrylate-based polymer system for 3D printing application [J].
Barkane, Anda ;
Platnieks, Oskars ;
Jurinovs, Maksims ;
Gaidukovs, Sergejs .
POLYMER DEGRADATION AND STABILITY, 2020, 181
[28]   DLP 3D printing and characterization of PEEK-acrylate composite biomaterials for hip-joint implants [J].
Dama, Yogiraj ;
Jogi, Bhagwan ;
Pawade, Raju ;
Pal, Shibam ;
Gaikwad, Yogesh .
OBRABOTKA METALLOV-METAL WORKING AND MATERIAL SCIENCE, 2025, 27 (01) :172-191
[29]   Preparation of high thermal stability gelatin emulsion and its application in 3D printing [J].
Du, Jie ;
Dai, Hongjie ;
Wang, Hongxia ;
Yu, Yong ;
Zhu, Hankun ;
Fu, Yu ;
Ma, Liang ;
Peng, Lin ;
Li, Lin ;
Wang, Qiang ;
Zhang, Yuhao .
FOOD HYDROCOLLOIDS, 2021, 113
[30]   Bioinspired Adhesive Manufactured by Projection Microstereolithography 3D Printing Technology and Its Application [J].
He, Qingsong ;
Zhao, Zefang ;
Zhang, Hao ;
Duan, Jinjun ;
Zhang, Ning ;
Cui, Kunkun ;
Zhong, Qiyun ;
Yang, Changli .
ADVANCED MATERIALS INTERFACES, 2023, 10 (14)