基于动态酯键的烷二胺基Vitrimer的制备及其性能研究

doi:10.3969/j.issn.0253-2417.2023.02.010

Abstract

Abstract:

Bio-based glass-like polymer(vitrimers) materials based on dynamic transesterification mechanism were prepared by the adduct of eleostearic acid and maleic anhydride(EMA) and epoxidizing menthane diamine(EMDA) derived from menthane diamine(MDA). The obtained materials were characterized and tested by Fourier transform infrared spectroscopy(FT-IR), dynamic thermomechanical analysis(DMA), thermogravimetric(TG) analysis, universal testing machine and other testing methods. The experimental results showed that the tensile strength of the materials was up to 35 MPa, the elongation at break was up to 12%, the 5% weight loss temperature was up to 264℃, and the glass transition temperature(T_g) was up to 119℃. The crossliking density increased first and then decreased with the increasing content of epoxidized menthane diamine. The materials had T_g-based shape memory ability and under went topological rearrangement of cross-linked structure at 180℃.The degradation of the material was achieved by the reaction of ethanolamine with the ester bond in the materials, and it was proved by gel permeation chromatography(GPC) that the materials could be degraded into oligomers with M_n of 2 594 and PDI of 1.09 at 130℃ for 8 h.

Key words: bio-based, glass-like polymers, dynamic ester exchange, shape memory, degradable

CLC Number:

TQ35

Songlin DAI, Yazhou XU, Haibo ZHANG, Zhendong ZHAO, Jing WANG, Yuxiang CHEN. Preparation and Properties of Menthane Diamine Vitrimer Based on Dynamic Ester Bonds[J]. Chemistry and Industry of Forest Products, 2023, 43(2): 73-79.

Figures/Tables 11

Fig.1

Fig.2

Table 1

Fig.3

Fig.4

Fig.5

Table 2

Fig.7

Fig.8

Fig.9

Table 3

References 18

1	FU Q, YAN Q M, JIANG X, et al.Heat driven self-healing isocyanate-based crosslinked three-arm Star-shaped polyglycolide based on dynamic transesterification[J/OL]. Reactive and Functional Polymers, 2020, 146: 104440[2022-01-11].http://doi.org/10.1016/j.reactfunctpolym.2019.104440.
2	LIU T , HAO C , ZHANG S , et al. A self-healable high glass transition temperature bioepoxy material based on vitrimer chemistry[J]. Macromolecules, 2018, 51 (15): 5577- 5585. doi: 10.1021/acs.macromol.8b01010
3	LIU T , HAO C , WANG L W , et al. Eugenol-derived biobased epoxy: Shape memory, repairing, and recyclability[J]. Macromolecules, 2017, 50 (21): 8588- 8597. doi: 10.1021/acs.macromol.7b01889
4	DHERS S , VANTOMME G , AVÉROUS L . A fully bio-based polyimine vitrimer derived from fructose[J]. Green Chemistry, 2019, 21 (7): 1596- 1601. doi: 10.1039/C9GC00540D
5	MONTARNAL D , CAPELOT M , TOURNILHAC F , et al. Silica-like malleable materials from permanent organic networks[J]. Science, 2011, 334 (6058): 965- 968. doi: 10.1126/science.1212648
6	HE C F , SHI S W , WANG D , et al. Poly(oxime-ester) vitrimers with catalyst-free bond exchange[J]. Journal of the American Chemical Society, 2019, 141 (35): 13753- 13757. doi: 10.1021/jacs.9b06668
7	ZHAO X L , LIU Y Y , WENG Y X , et al. Sustainable epoxy vitrimers from epoxidized soybean oil and vanillin[J]. ACS Sustainable Chemistry & Engineering, 2020, 8 (39): 15020- 15029.
8	DEBNATH S , KAUSHAL S , OJHA U . Catalyst-free partially bio-based polyester vitrimers[J]. ACS Applied Polymer Materials, 2020, 2 (2): 1006- 1013. doi: 10.1021/acsapm.0c00016
9	BIERMANN U , BORNSCHEUER U T , FEUSSNER I , et al. Fettsäuren und fettsäurederivate als nachwachsende plattformmoleküle für die chemische industrie[J]. Angewandte Chemie, 2021, 133 (37): 20304- 20326. doi: 10.1002/ange.202100778
10	FERDOSIAN F , YUAN Z S , ANDERSON M , et al. Synthesis and characterization of hydrolysis lignin-based epoxy resins[J]. Industrial Crops & Products, 2016, 91, 295- 301.
11	HERNANDEZ E D , BASSETT A W , SADLER J M , et al. Synthesis and characterization of bio-based epoxy resins derived from vanillyl alcohol[J]. Acs Sustainable Chemistry & Engineering, 2016, 4 (8): 4328- 4339.
12	WANG Z Y , GNANASEKAR P , NAIR S S , et al. Biobased epoxy synthesized from a vanillin derivative and its reinforcement using lignin-containing cellulose nanofibrils[J]. ACS Sustainable Chemistry & Engineering, 2020, 8 (30): 11215- 11223.
13	XU Y Z, DAI S L, BI L W, et al.Catalyst-free self-healing bio-based vitrimer for a recyclable, reprocessable, and self-adhered carbon fiber reinforced composite[J/OL]. Chemical Engineering Journal, 2022, 429: 132518[2022-01-11].http://doi.org/10.1016/j.cej.2021.132518.
14	XU Y Z, FU P, DAI S L, et al.Catalyst-free self-healing fully bio-based vitrimers derived from tung oil: Strong mechanical properties, shape memory, and recyclability[J/OL]. Industrial Crops and Products, 2021, 171: 113978[2022-01-11].http://doi.org/10.1016/j.indcrop.2021.113978.
15	LANGE J , LUISIER A , HULT A . Influence of crosslink density, glass transition temperature and addition of pigment and wax on the scratch resistance of an epoxy coating[J]. Journal of Coatings Technology, 1997, 69 (872): 77- 82.
16	HUANG K , ZHANG J W , LI M , et al. Exploration of the complementary properties of biobased epoxies derived from rosin diacid and dimer fatty acid for balanced performance[J]. Industrial Crops Products, 2013, 49, 497- 506. doi: 10.1016/j.indcrop.2013.05.024
17	MANTZARIDIS C , BROCAS A L , LLEVOT A , et al. Rosin acid oligomers as precursors of DGEBA-free epoxy resins[J]. Green Chemistry, 2013, 15 (11): 3091- 3098. doi: 10.1039/c3gc41004h
18	WANG H H , LIU B , LIU X Q , et al. Synthesis of biobased epoxy and curing agents using rosin and the study of cure reactions[J]. Green Chemistry, 2008, 10 (11): 1190- 1196. doi: 10.1039/b803295e

样品 sample	EMDA/g	EMA/g	n_环氧/n_{羧基+酸酐} n_epoxy/n_{carboxyl+anhydride}
EMDA-EMA-1	1.31	1.0	5∶3
EMDA-EMA-2	1.05	1.0	5∶4
EMDA-EMA-3	0.79	1.0	5∶5

样品 sample	T_g/℃	T_5%/℃	T_50%/℃	最大拉伸强度/MPa maximum tensile strength	交联密度(d_c)/(mol·cm^-3) crosslink density
EMDA-EMA-1	119	264	372	35±1.35	720
EMDA-EMA-2	116	247	382	33±0.32	1 080
EMDA-EMA-3	99	202	368	24±1.63	635

降解条件 degradation conditions		M_n	PDI
反应时间 time	1 h	2 813	1.15
	2 h	3 012	1.20
	4 h	2 989	1.14
	8 h	2 644	1.10
温度 temperature	70 ℃	4 588	1.91
	90 ℃	4 328	1.74
	110 ℃	3 409	1.42
	130 ℃	2 785	1.16
n_乙醇胺/n_酯键 n_ethanolamine/ n_{ester bond}	10	2 870	1.21
	15	3 020	1.19
	20	2 594	1.09
	25	2 729	1.10

[1]	Songlin DAI, Yazhou XU, Huiru MA, Haibo ZHANG, Zhendong ZHAO, Yuxiang CHEN. Preparation and Performance Study of Degradable Turpentine-based Polymer Materials [J]. Chemistry and Industry of Forest Products, 2023, 43(1): 57-62.
[2]	Yaocang LI, Jiawei SHAO, Hongxia MA. Properties of Rosin-modified Cardanol Coatings [J]. Chemistry and Industry of Forest Products, 2022, 42(5): 56-60.
[3]	ZHANG Kaiqiang, TANG Gongwen, YAN Zhishan, MA Linrong, HUANG Xin. Effects of Liquid Crystalline Epoxy Resin on the Properties of Bio-based Cardanol-furfural Resin [J]. Chemistry and Industry of Forest Products, 2018, 38(4): 41-46.
[4]	SHAO Siqi, JIANG Minjie, ZHAO Xinghua, ZHANG Haiyan, LUO Lixin. Highly Porous KGM Sponge by an Electrothermic Process at High Temperature [J]. Chemistry and Industry of Forest Products, 2017, 37(4): 40-44.
[5]	DENG Kun-ming, MA Yan, WANG Hong-xiao, SHEN Juan-zhang, TAN Wei-hong. Identification of the Bio-based and Petroleum Based Foam [J]. Chemistry and Industry of Forest Products, 2016, 36(1): 49-54.
[6]	HANG Fei, LUO Yan-qing, HONG Jian-guo. Modification of Wood Powder by Esterification for the Production of Bio-based Plastic Material [J]. Chemistry and Industry of Forest Products, 2015, 35(6): 27-32.

Preparation and Properties of Menthane Diamine Vitrimer Based on Dynamic Ester Bonds

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 11

References 18

Related Articles 6

Recommended Articles

Metrics

Comments