可降解松节油基高分子材料的制备及性能研究

doi:10.3969/j.issn.0253-2417.2023.01.007

林产化学与工业 ›› 2023, Vol. 43 ›› Issue (1): 57-62.doi: 10.3969/j.issn.0253-2417.2023.01.007

可降解松节油基高分子材料的制备及性能研究

代松林¹^,²(), 徐亚洲¹^,², 马慧茹¹^,², 张海波¹^,², 赵振东¹^,², 陈玉湘¹^,²^,*()

1. 中国林业科学研究院林产化学工业研究所；江苏省生物质能源与材料重点实验室；国家林业和草原局林产化学工程重点实验室；林木生物质低碳高效利用国家工程研究中心，江苏南京 210042
2. 南京林业大学江苏省林业资源高效加工利用协同创新中心，江苏南京 210037

收稿日期:2021-11-19 出版日期:2023-02-28 发布日期:2023-02-28
通讯作者: 陈玉湘 E-mail:dsl17302550339@163.com;cyxlhs@126.com
作者简介:陈玉湘, 研究员, 硕士生导师, 研究领域为芳香植物资源化学利用; E-mail: cyxlhs@126.com
代松林(1996-), 男, 四川宜宾人, 硕士生, 从事芳香植物资源化学利用方面研究; E-mail: dsl17302550339@163.com
基金资助:
国家自然科学基金资助项目(31870557)

Preparation and Performance Study of Degradable Turpentine-based Polymer Materials

Songlin DAI¹^,²(), Yazhou XU¹^,², Huiru MA¹^,², Haibo ZHANG¹^,², Zhendong ZHAO¹^,², Yuxiang CHEN¹^,²^,*()

1. Institute of Chemical Industry of Forest Products, CAF; Key Lab. of Biomass Energy and Material, Jiangsu Province; Key Lab. of Chemical Engineering of Forest Products, National Forestry and Grassland Administration; National Engineering Research Center of Low-Carbon Processing and Utilization of Forest Biomass, Nanjing 210042, China
2. Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Najing Forestry University, Nanjing 210037, China

Received:2021-11-19 Online:2023-02-28 Published:2023-02-28
Contact: Yuxiang CHEN E-mail:dsl17302550339@163.com;cyxlhs@126.com

摘要/Abstract

摘要：

以环氧大豆油(ESO)、N, N'-(二呋喃基)-1, 8-对烷二胺(FMDA)、6-马来酰亚胺己酸(MA)和己二酸为原料，合成了一种含有酯键和D-A键的生物基材料(FMDA-ESO)。通过傅里叶变换红外光谱(FT-IR)、差示扫描量热(DSC)、热重(TG)、万能试验测试机等测试方法对材料进行表征及测试。实验结果表明：酯键及D-A键的存在使FMDA-ESO材料形成了交联结构，FMDA的刚性结构可提高所得材料的力学性能。随着FMDA-ESO固化配方中FMDA含量增加，材料的热稳定性增加。在乙醇胺的作用下，可实现材料FMDA-ESO快速降解，可在135 ℃，30 min下降解为数均相对分子质量为2 691的低聚物。

关键词: 烷二胺, 生物基, 动态键, 热降解

Abstract:

A bio-based polymer material FMDA-ESO containing ester and D-A bonds was synthesized from epoxidized soybean oil(ESO), N, N'-(difuranyl)-1, 8-p-menthane diamine(FMDA), maleimidic caproic acid and adipic acid. The materials were characterized and tested by Fourier transform infrared spectroscopy(FT-IR), differential scanning calorimetry(DSC), thermogravimetric analysis(TG) and universal test tester. The results showed that the cross-linked structure was formed in FMDA-ESO with the presence of ester and D-A bonds, and the rigid structure of FMDA could improve the mechanical properties of the obtained materials. With the amount increasement of FMDA in the FMDA-ESO cured formulation, the thermal stability of the material increased. Rapid degradation of FMDA-ESO could be achieved in the presence of ethanolamine, which could be degraded to oligomers with a number-average molecular weight of 2 691 at 135 ℃ for 30 min.

Key words: menthane diamine, bio-based, dynamic bond, thermal degradation

中图分类号:

TQ35

代松林, 徐亚洲, 马慧茹, 张海波, 赵振东, 陈玉湘. 可降解松节油基高分子材料的制备及性能研究[J]. 林产化学与工业, 2023, 43(1): 57-62.

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.

图/表 11

图1

表1

图2

图3

图4

图5

图6

图7

图8

图9

图10

参考文献 21

1	XU S C , LAMM M E , RAHMAN M A , et al. Renewable atom-efficient polyesters and thermosetting resins derived from high oleic soybean oil[J]. Green Chemistry, 2018, 20 (5): 1106- 1113. doi: 10.1039/C7GC03774K
2	MA S Q , WEBSTER D C . Degradable thermosets based on labile bonds or linkages: A review[J]. Progress in Polymer Science, 2017, 76, 65- 110.
3	DEBNATH S , KAUSHAL S , OJHA U . Catalyst-free partially bio-based polyester vitrimers[J]. ACS Applied Energy Materials, 2019, 2 (2): 1006- 1013. doi: 10.1021/acsaem.8b02229
4	LU L , PAN J , LI G Q . Recyclable high performance epoxy based on transesterification reaction[J]. Journal of Materials Chemistry A, 2017, 5 (40): 21505- 21513. doi: 10.1039/C7TA06397K
5	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
6	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
7	YANG X T , GUO Y Q , LUO X , et al. Self-healing, recoverable epoxy elastomers and their composites with desirable thermal conductivities by incorporating BN fillers via in-situ polymerization[J]. Composites Science and Technology, 2018, 164, 59- 64. doi: 10.1016/j.compscitech.2018.05.038
8	CHEN X C , CHEN S F , XU Z J , et al. Degradable and recyclable bio-based thermoset epoxy resins[J]. Green Chemistry, 2020, 22 (13): 4187- 4198. doi: 10.1039/D0GC01250E
9	BAI N , SAITO K , SIMON G P . Synthesis of a diamine cross-linker containing Diels-Alder adducts to produce self-healing thermosetting epoxy polymer from a widely used epoxy monomer[J]. Polymer Chemistry, 2013, 4 (3): 724- 730. doi: 10.1039/C2PY20611K
10	GUO H S , HAN Y , ZHAO W Q , et al. Universally autonomous self-healing elastomer with high stretchability[J]. Nature Communications, 2020, 11 (1): 2037- 2046. doi: 10.1038/s41467-020-15949-8
11	LEE S H , SHIN S R , LEE D S . Self-healing of cross-linked PU via dual-dynamic covalent bonds of a Schiff base from cystine and vanillin[J]. Materials & Design, 2019, 172, 107774- 107783.
12	JOUYANDEH M, TIKHANI F, HAMPP N, et al. Highly curable self-healing vitrimer-like cellulose-modified halloysite nanotube/epoxy nanocomposite coatings[J/OL]. Chemical Engineering Journal, 2020, 396: 125196[2021-11-10]. https://doi.org/10.1016/j.cej.2020.125196.
13	SYRETT J A , BECER C R , HADDLETON D M . Self-healing and self-mendable polymers[J]. Polymer Chemistry, 2010, 1 (7): 978- 987. doi: 10.1039/c0py00104j
14	WU P X , CHENG H Y , WANG X C , et al. A self-healing and recyclable polyurethane-urea Diels-Alder adduct synthesized from carbon dioxide and furfuryl amine[J]. Green Chemistry, 2021, 23 (1): 552- 560. doi: 10.1039/D0GC03695A
15	WANG J F , LU C W , LIU Y P , et al. Preparation and characterization of natural rosin stabilized nanoparticles via miniemulsion polymerization and their pressure-sensitive adhesive applications[J]. Industrial Crops and Products, 2018, 124, 244- 253. doi: 10.1016/j.indcrop.2018.07.079
16	LIU X Q , ZHANG J W . High-performance biobased epoxy derived from rosin[J]. Polymer International, 2010, 59 (5): 607- 609.
17	LU C W, GUO X L, WNAG C P, et al. Integration of metal-free ATRP and Diels-Alder reaction toward sustainable and recyclable cellulose-based thermoset elastomers[J/OL]. Carbohydrate Polymers, 2020, 242: 116404[2021-11-10]. https://doi.org/10.1016/j.carbpol.2020.116404.
18	VENDAMME R , EEVERS W . Sticky degradable bioelastomers[J]. Chemistry of Materials, 2017, 29 (12): 5353- 5363. doi: 10.1021/acs.chemmater.7b01635
19	GANDINI A , LACERDA T M , CARVALHO A J F , et al. Progress of polymers from renewable resources: Furans, vegetable oils, and polysaccharides[J]. Chemical Reviews, 2016, 116 (3): 1637- 1669. doi: 10.1021/acs.chemrev.5b00264
20	WEI K , ZHU G M , TANG Y S , et al. Shape-memory effects of a hydro-epoxy resin system[J]. Journal of Polymer Research, 2013, 20 (5): 123- 130. doi: 10.1007/s10965-013-0123-7
21	XU S C , ZENG X J , DAI S L , et al. Turpentine derived secondary amines for sustainable crop protection: Synthesis, activity evaluation and QSAR study[J]. Journal of Agricultural and Food Chemistry, 2020, 68 (42): 11829- 11838. doi: 10.1021/acs.jafc.0c01909

名称 name	FMDA用量/g FMDA amount	MA用量/g MA amount	己二酸用量/g adipic acid amount	ESO用量/g ESO amount
FMDA-ESO-1.2	1.00	1.26	0.44	1.92
FMDA-ESO-1.3	1.00	1.26	0.44	2.08
FMDA-ESO-1.4	1.00	1.26	0.44	2.24

[1]	郑云武, 王继大, 李冬华, 刘灿, 丁章帅, 郑志锋. 生物质催化转化制备生物基航空燃料的研究进展[J]. 林产化学与工业, 2023, 43(1): 140-154.
[2]	李耀仓, 邵嘉薇, 马红霞. 松香改性腰果酚漆膜性能的研究[J]. 林产化学与工业, 2022, 42(5): 56-60.
[3]	潘政, 李卓, 薄采颖, 冯国东, 杨晓慧, 胡立红. 生物基本征型阻燃环氧树脂的制备及其性能研究[J]. 林产化学与工业, 2022, 42(1): 71-78.
[4]	李梦雨, 杨鹏, 常春, 陈志勇, 宋建德. 糠醛渣高值化利用的研究进展[J]. 林产化学与工业, 2021, 41(6): 117-126.
[5]	王婧, 徐士超, 曾小静, 董欢欢, 蒋建新, 赵振东. 1,8-对孟烷二胺高效制备工艺[J]. 林产化学与工业, 2018, 38(6): 59-66.
[6]	张凯强, 唐功文, 闫志山, 马林荣, 黄鑫. 液晶环氧树脂对生物基腰果酚-糠醛树脂性能的影响[J]. 林产化学与工业, 2018, 38(4): 41-46.
[7]	张浩然, 艾涛, 张东辉, 魏俊奇. 生物油的氨基甲酸酯化改性及其酚醛树脂的制备[J]. 林产化学与工业, 2018, 38(3): 109-114.
[8]	朱守记, 杨学兵, 徐士超, 赵振东, 蒋建新. 顺-1,8-对烷二胺双酰胺杂环类衍生物的合成及抑菌活性研究[J]. 林产化学与工业, 2017, 37(2): 79-84.
[9]	杭飞, 罗彦卿, 洪建国. 木粉酯化改性制备生物基塑料[J]. 林产化学与工业, 2015, 35(6): 27-32.
[10]	肖卓炳, 郭满满, 郭瑞轲. 熊果酸和咖啡酸的热降解机理及其分解动力学研究[J]. 林产化学与工业, 2014, 34(2): 33-39.
[11]	冯志勇;李冬梅;赵振东;毕良武;王婧;古研. 松节油水合萜二醇合成对(艹孟)烷二胺反应的研究[J]. 林产化学与工业, 2008, 28(2): 16-20.
[12]	黄彪;高尚愚. 杉木间伐材热降解处理制取吸油材料的研究[J]. 林产化学与工业, 2004, 24(1): 69-72.
[13]	戴燕;石淑兰;欧义芳;潘学军. 浅谈木质生物原料的综合利用途径[J]. 林产化学与工业, 2001, 21(2): 75-81.

可降解松节油基高分子材料的制备及性能研究

Preparation and Performance Study of Degradable Turpentine-based Polymer Materials

RichHTML

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

图/表 11

参考文献 21

相关文章 13

编辑推荐

Metrics

本文评价

关于本刊

投稿指南

在线期刊

相关单位

联系我们