Preparation and performance of carboxyl⁃terminated tannic acid/gallic acid⁃based epoxy composite

doi:10.19491/j.issn.1001-9278.2022.07.007

Abstract

Abstract:

A bio?based hyperbranched polymer （CTMTA） and a gallic acid?based epoxy resin （GAER） were prepared through an A₂+B₃ one?step method and a polycondensation reaction， respectively. The GAER/MTHPA/2?MI/CTMTA composites were prepared using a melt blending method. The effects of CTMTA content on the properties of the GAER/MTHPA/2?MI composites were investigated using by FTIR， ¹H?NMR， DSC， SEM， mechanical measurement， and water absorption. The results indicated that the addition of CTMTA improved the mechanical properties and water absorption rate of the composites but reduced their curing temperature. The composites exhibited maximum mechanical properties and water absorption rate at a CTMTA content of 1.5 wt%. Compared to the GAER/MTHPA/2?MI composite system， the GAER/MTHPA/2?MI/CTMTA composites presented an increase in tensile strength， elongation at break， impact strength， and water absorption rate by 33 %， 37 %， 47.6 %， and 45.5 %， respectively. The optimum curing parameter of the GAER/MTHPA/2?MI/CTMTA composite system was determined to be 110 oC/20 min.

Key words: gallic acid?based epoxy resin, tannic acid, mechanical property, curing reaction

CLC Number:

TQ323.5

XU Jie, ZHONG Jinfu, TONG Xiaoqian, LI Guangfu, FU Dongliang, LI Chengcheng. Preparation and performance of carboxyl⁃terminated tannic acid/gallic acid⁃based epoxy composite[J]. China Plastics, 2022, 36(7): 44-50.

Figures/Tables 8

Fig.1. FTIR spectra of TA， CTMTA，GA and GAER

Fig.2. Synthetic route of GAER and CTMTA

Fig.3. 1H?NMR spectra of CTMTA and GAER

Fig.4. Mechanical properties of GAER/MTHPA/2?MI/CTMTA systems with different CTMTA contents

Fig.5. SEM of impact fracture surfaces of GAER/MTHPA systems modified with different CTMTA contents

Fig.6. DSC curves of curing process of GAER/MTHPA/2?MI and GAER/MTHPA/2?MI/CTMTA composites

β/（℃·min^-1）	T_i /℃	T_p /℃	T_f /℃	1/T_p ·℃^-1	lnβ/℃·min^-1	-ln（β/T_p²）/（ ℃^-1·min^-1）
5	59.4	112.1	180.5	0.008 92	1.609	10.298
10	66.5	125.5	193.7	0.007 97	2.079	9.674
20	72.1	129.6	201.6	0.007 72	2.398	9.289
30	77.3	134.5	224.3	0.007 43	2.639	9.025

Tab.1. DSC parameters of the first exothermic peak of GAER/MTHPA/2?MI/CTMTA system

Fig.7. Water absorption of GAER/MTHPA/2?MI/CTMTA systems with different CTMTA contents

References 20

1	WAN J， GAN B， LI C， et al. A novel biobased epoxy resin with high mechanical stiffness and low flammability： synthesis， characterization and properties［J］. Journal of Materials Chemistry A， 2015， 3（43）： 21 907⁃21 921.
2	XU J， YANG J， LIU X， et al. Preparation and characterization of fast⁃curing powder epoxy adhesive at middle temperature［J］. Royal Society Open Science， 2018， 5（8）： 180566.
3	QI Y， WENG Z， KOU Y， et al. Synthesize and introduce bio⁃based aromatic s⁃triazine in epoxy resin： enabling extremely high thermal stability， mechanical properties， and flame retardancy to achieve high⁃performance sustainable polymers［J］. Chemical Engineering Journal， 2021， 406： 126881.
4	ZHAO Y， HUANG R， WU Z， et al. Effect of free volume on cryogenic mechanical properties of epoxy resin reinforced by hyperbranched polymers［J］. Materials & Design， 2021， 202： 109565.
5	NAVEIRA C， RODRIGUES N， SANTOS F S， et al. Acute toxicity of Bisphenol A （BPA） to tropical marine and estuarine species from different trophic groups［J］. Environmental Pollution， 2021， 268： 115911.
6	CAO L， LIU X， NA H， et al. How a bio⁃based epoxy monomer enhanced the properties of diglycidyl ether of bisphenol A （DGEBA）/graphene composites［J］. Journal of Materials Chemistry A， 2013， 1（16）： 5 081⁃5 088.
7	AOUF C， NOUAILHAS H， FACHE M， et al. Multi⁃functionalization of gallic acid. Synthesis of a novel bio⁃based epoxy resin［J］. European Polymer Journal， 2013， 49（6）： 1 185⁃1 195.
8	KHALIL A， GERARDIN⁃CHARBONNIER C， CHAPUIS H， et al. Original bio⁃based antioxidant poly （meth） acrylate from gallic acid⁃based monomers［J］. ACS Sustainable Chemistry & Engineering， 2021， 9（34）： 11 458⁃11 468.
9	LIU J， ZHANG L， SHUN W， et al. Recent development on bio‐based thermosetting resins［J］. Journal of Polymer Science， 2021， 59（14）： 1 474⁃1 490.
10	LIU T， NIE Y， CHEN R， et al. Hyperbranched polyether as an all⁃purpose epoxy modifier： controlled synthesis and toughening mechanisms［J］. Journal of Materials Chemistry A， 2015， 3（3）： 1 188⁃1 198.
11	WANG K， CHEN L， WU J， et al. Epoxy nanocompo⁃sites with highly exfoliated clay： mechanical properties and fracture mechanisms［J］. Macromolecules， 2005， 38（3）： 788⁃800.
12	XU J， LIU X， FU S. Bio⁃based epoxy resin from gallic acid and its thermosets toughened with renewable tannic acid derivatives ［J］. Journal of Materials Science， 2022， 57： 9 493⁃9 507.
13	ZHANG T， TAN J， HAN X， et al. Novel epoxy⁃ended hyperbranched polyether derived from xylitol as sustainable tougheners for epoxy resin［J］. Polymer Testing， 2021， 94： 107053.
14	BORO U， KARAK N. Tannic acid based hyperbranched epoxy/reduced graphene oxide nanocomposites as surface coating materials［J］. Progress in Organic Coatings， 2017， 104： 180⁃187.
15	XU J， YANG J， WANG H， et al. Bio⁃based hyperbranched toughener from tannic acid and its enhanced solvent⁃free epoxy resin with high performance［J］. Journal of Renewable Materials， 2019， 7（12）： 1 333⁃1 346.
16	ZHOU Y， TAWIAH B， NOOR N， et al. A facile and sustainable approach for simultaneously flame retarded， UV protective and reinforced poly （lactic acid） composites using fully bio⁃based complexing couples［J］. Composites Part B： Engineering， 2021， 215： 108833.
17	LIU Y， ZHANG Z， WANG J， et al. Renewable tannic acid based self⁃healing polyurethane with dynamic phenol⁃carbamate network： simultaneously showing robust mechanical properties， reprocessing ability and shape memory［J］. Polymer， 2021，228： 123860.
18	SHNAWA H A. Curing and thermal properties of tannin⁃based epoxy and its blends with commercial epoxy resin［J］. Polymer Bulletin， 2021， 78（4）： 1 925⁃1 940.
19	FEI X， WEI W， ZHAO F， et al. Efficient toughening of epoxy⁃anhydride thermosets with a biobased tannic acid derivative［J］. ACS Sustainable Chemistry & Engineering， 2016， 5（1）： 596⁃603.
20	LUO L， MENG Y， QIU T， et al. An epoxy⁃ended hyperbranched polymer as a new modifier for toughening and reinforcing in epoxy resin［J］. Journal of Applied Polymer Science， 2013， 130（2）： 1 064⁃1 073.

[1]	JIAO Zhiwei, WANG Kechen, ZHANG Yang, YANG Weimin. Performance of PVC/ABS composites filled with carbon black and talc powders based on carbon nano coating deposition [J]. China Plastics, 2022, 36(8): 10-15.
[2]	ZHANG Taozhong, CHEN Xiaolong, HAO Xiaoyu, YU Fujia. Comparison of mechanical properties and interfacial interactions of polypropylene composites filled with talc， calcium carbonate， and barium sulfate [J]. China Plastics, 2022, 36(8): 36-41.
[3]	YU Changyong, XIN Zhong. Effect of α/β complex nucleating agent based on hexahydrophthalate on properties of polypropylene [J]. China Plastics, 2022, 36(7): 121-128.
[4]	TAN Liqin, LIU Weiqu, LIANG Liyan, WANG Shuo, FENG Zhiqiang, LIN Jiaming. Preparation and performance of epoxy resin modified with mercaptan polysiloxane [J]. China Plastics, 2022, 36(7): 21-29.
[5]	LI Kaize, XIN Yong. Properties of thermoplastic polyurethane composites modified with carbon nanotubes [J]. China Plastics, 2022, 36(6): 1-5.
[6]	WANG Shuai, ZHANG Yudi, YANG Fukai, XU Xinyu. Preparation and properties of polyimide/multi⁃walled carbon nanotubes composite foams [J]. China Plastics, 2022, 36(6): 39-45.
[7]	WANG Jinye, TANG Bohu, YANG Lining, XIE Meng, GUO Zechao, YANG Guang. Study on multi⁃jet⁃fusion forming process of PA12 parts [J]. China Plastics, 2022, 36(6): 81-86.
[8]	SUN Wenbo, XIN Chunling, HE Yadong, ZHAI Yujiao, YAN Baorui. Influence of micro⁃foaming injection molding process on cell structure of glass⁃fiber⁃reinforced PBT products [J]. China Plastics, 2022, 36(5): 1-7.
[9]	WANG Ke, LONG Chunguang. Mechanical and tribological properties of ultra⁃high molecular weight polyethylene/sepiolite fiber composites [J]. China Plastics, 2022, 36(5): 19-23.
[10]	CHEN Sheng, LIANG Yingchao, WU Fangjuan, FANG Hui, FAN Xinfeng, CHEN Hui, WANG Yonggang. Preparation and interfacial modification of polyamide 6/bidirectional warp⁃knitted glass fiber composites [J]. China Plastics, 2022, 36(5): 24-28.
[11]	HE Hezhi, XU Li, YANG Yike. Effect of prestress on mechanical properties of PC/CF laminates [J]. China Plastics, 2022, 36(4): 1-5.
[12]	LI Suyuan, LIU Huipeng, GONG Shun, HUANG Guotao, LI Yucai, WU Xin, DENG Jianping, PAN Kai. Preparation and characterization of EVA foaming materials modified with thermoplastic polyamide elastomer [J]. China Plastics, 2022, 36(4): 6-14.
[13]	ZHANG Jiufu, LUO Kaiqiang, XU Jun, GUO Baohua. Study on comprehensive properties and influencing factors of long glass fiber reinforced PA66 composites [J]. China Plastics, 2022, 36(3): 1-8.
[14]	WANG Fuyu, GUO Jinqiang, ZHANG Yuxia. In⁃situ fibrillation methods of polymer blends and their application in PP⁃based blends [J]. China Plastics, 2022, 36(3): 146-156.
[15]	LI Zeyang, CEN Lan, CHEN Sheng, CHEN Weijie, DU Binghua, ZHANG Ershuai. Preparation and properties of XNBR/PA12 thermoplastic elastomer [J]. China Plastics, 2022, 36(3): 15-20.