漆酚聚合固化技术及其功能聚合物应用研究进展

doi:10.3969/j.issn.0253-2417.2024.01.017

Abstract

Abstract:

Urushiol was the common plant polyphenol in China. It was isolated and purified from the lacquer by lacquer tree secretion. The structure contained active groups such as benzene ring, ortho/meta bisphenol hydroxyl group and long(unsaturated) alkane side chain(C₁₅-C₂₀). In recent years, the application of urushiol in membrane functional material technology had made rapid progress. In particular, the preparation of urushiol functional polymers by chemical polymerization and curing technology had been widely used in membrane surface/interface engineering, adhesives, hemostatic agents, and other fields. It was one of the important ways to realize the resource utilization and quality improvement of raw lacquer. This article reviewed the recent domestic and foreign research on the polymerization and curing mechanism of urushiol, as well as heating curing, ultraviolet curing, laccase biomimetic catalysis, metal coordination chelation, organic blend cross-linking, sol-gel reaction, electrospinning and other urushiol curing polymerization technologies. The research progress and main problems of urushiol functional polymers in the application of functional materials such as anti-corrosion coatings, hydrophobic coatings, hemostatic and antibacterial coatings were summarized, which provided theoretical basis and development direction for the commercial application of urushiol functional materials.

Key words: lacquer urushiol, polymerization curing, mechanism and technology, functional material

CLC Number:

TQ35

Dongxu LI, Juanni ZHANG, Tingting ZHANG, Yan LI, Xingying XUE, Zhiwen QI. Research Progress on Polymerization and Curing Technology of Urushiol and Its Application in Functional Polymers[J]. Chemistry and Industry of Forest Products, 2024, 44(1): 129-137.

Figures/Tables 4

References 52

1	工业和信息化部. "十四五"工业绿色发展规划[EB/OL]. (2021-11-15)[2022-11-10]. https://www.gov.cn/zhengce/zhengceku/2021-12/03/content_5655701.htm.
	Ministry of Industry and Information Technology. '14th Five-Year' industrial green development[EB/OL]. (2021-11-15)[2022-11-10]. https://www.gov.cn/zhengce/zhengceku/2021-12/03/content_5655701.htm.
2	张飞龙. 中国髹漆工艺与漆器保护[M]. 北京: 科学出版社, 2010: 282- 284.
	ZHANG F L . Chinese lacquer painting technology and lacquer ware protection[M]. Beijing: Science Press, 2010: 282- 284.
3	齐志文, 王成章, 蒋建新. 漆酚的生物化学活性及其应用进展[J]. 生物质化学工程, 2018, 52 (4): 60- 66. doi: 10.3969/j.issn.1673-5854.2018.04.010
	QI Z W , WANG C Z , JIANG J X . Research progress on biochemical activity and application of urushiol[J]. Biomass Chemical Engineering, 2018, 52 (4): 60- 66. doi: 10.3969/j.issn.1673-5854.2018.04.010
4	YANG J H , DENG J P , ZHU J F , et al. Thermal polymerization of lacquer sap and its effects on the properties of lacquer film[J]. Progress in Organic Coatings, 2016, 94, 41- 48. doi: 10.1016/j.porgcoat.2016.01.021
5	TYMAN J H P , MATHEWS A J . Long-chain phenols: XXⅡ. Compositional studies on Japanese lac(Rhus vernicifera) by chromatography and mass spectrometry[J]. Journal of Chromatography A, 1982, 235 (1): 149- 164. doi: 10.1016/S0021-9673(00)95796-0
6	KUMANOTANI J . Urushi(oriental lacquer) a natural aesthetic durable and future-promising coating[J]. Progress in Organic Coatings, 1995, 26 (2/3/4): 163- 195.
7	TOSHIO E , MATASHIGE T . Paint film forming by hardening of urushiol at high temperature[J]. Kobunshi Ronbunshu, 2012, 69 (2): 71- 76. doi: 10.1295/koron.69.71
8	WU H T, HAN X T, ZHAO W, et al. Mechanical and electrochemical properties of UV-curable nanocellulose/urushiol epoxy acrylate anti-corrosive composite coatings[J/OL]. Industrial Crops and Products, 2022, 181: 114805[2022-11-21]. https://doi.org/10.1016/j.indcrop.2022.114805.
9	XIA J R , XU Y L , LIN J H , et al. UV-induced polymerization of urushiol without photoinitiator[J]. Progress in Organic Coatings, 2008, 61 (1): 7- 10. doi: 10.1016/j.porgcoat.2007.08.007
10	KAZUHIRO T , SHIGEO H , YASUHITO A . Photo-curing composite paint containing urushi(Oriental lacquer), and wrinkled coating caused by phase separation[J]. Progress in Organic Coatings, 2007, 58 (4): 290- 295. doi: 10.1016/j.porgcoat.2007.01.001
11	CHANG C W , LIAO J Y , LU K T . Syntheses and characteristics of urushiol-based waterborne UV-cured wood coatings[J]. Polymers, 2021, 13 (22): 4005- 4019. doi: 10.3390/polym13224005
12	LIU Y Z , XIA J R , LIN J H . Characterization and conductive property of polyurushiol/silver conductive coatings prepared under UV irradiation[J]. Progress in Organic Coatings, 2011, 71 (1): 117- 120. doi: 10.1016/j.porgcoat.2010.11.019
13	XUE H Y , ZHANG Y C , LI X Z , et al. Degradation urushiol coating composition crosslinked by diallyl trisulfide[J]. Journal of Polymers and the Environment, 2020, 28, 3192- 3200. doi: 10.1007/s10924-020-01845-1
14	YANG J H , ZHU J F , SHEN F Q , et al. Promotion by copper(Ⅱ)-modified montmorillonite of the drying property of oriental lacquer sap[J]. Progress in Organic Coatings, 2018, 118, 72- 81. doi: 10.1016/j.porgcoat.2018.01.023
15	蔡昇佑. 缩短生漆干燥时间之研究[D]. 中国台湾: 中国中兴大学, 2016.
	CAI S Y. Reduction of drying time for raw oriental lacquer[D]. Taiwan Province of China: Chung Hsing University of China, 2016.
16	BAI W B , CAI L F , ZHUO D X , et al. Resurrection of dead lacquer—Cupric potassium chloride dehydrate(K₂CuCl₄·2H₂O) used as the mimic laccase[J]. Progress in Organic Coatings, 2014, 77, 431- 438. doi: 10.1016/j.porgcoat.2013.11.007
17	李春森. 金属离子催化漆酚聚合反应[D]. 中国台湾: 中国台湾大学, 1998: 59-60.
	LI C S. Urushiol polymerization catalyzed by metal ions[D]. Taiwan Province of China: Taiwan University of China, 1998: 59-60.
18	黄道战, 蓝虹云, 邓加彦, 等. Cu(Ⅱ)-胺配合物催化漆酚氧化聚合成膜性能研究[J]. 化学与生物工程, 2005, 6 (2): 18- 20.
	HUANG D Z , LAN H Y , DENG J Y , et al. Study on the coating film of oxidative polymerization of urushiol with copper(Ⅱ)-amine complexes as catalyst[J]. Chemistry & Bioengineering, 2005, 6 (2): 18- 20.
19	郭庆宇. 铜类催化漆酚氧化聚合成膜的红外研究[J]. 中南民族大学学报(自然科学版), 2003, 22 (增刊): 103- 105.
	GUO Q Y . IR research of the oxidative polymerization of urushiol to coating catalyzed by cupric complexes with models of laccase[J]. Journal of South-Central University for Nationalities(Natural Science Edition), 2003, 22 (Suppl.): 103- 105.
20	郭庆宇. 铜与聚4-乙烯吡啶模拟漆酶催化漆酚氧化成膜红外分析[J]. 西北民族大学学报(自然科学版), 2004, 25 (4): 13- 17.
	GUO Q Y . The oxidative polymerization of urushiol to coating catalyzed by Cu-PVPy complexes in IR analysis[J]. Journal of Northwest University for Nationalities(Natural Science), 2004, 25 (4): 13- 17.
21	黄金城, 林翰谦, 黄俊杰. 生漆干燥时间之改善[J]. 嘉义大学学报, 2003, 74 (2): 53- 66.
	HUANG J C , LIN H Q , HUANG J J . Improvement of drying time of raw lacquer[J]. Journal of National Chiayi University, 2003, 74 (2): 53- 66.
22	OSAMU W , KATSUTOSHI N . Chemical modification of lacquer tree paint using primary amines[J]. Bulletin of the Chemical Society of Japan, 2003, 21 (9): 542- 556.
23	夏建荣. 紫外光固化天然生漆及其复合体系的研究[D]. 福州: 福建师范大学, 2011: 17-19.
	XIA J R. Study on UV-curing Chinese lacquer and its composites[D]. Fuzhou: Fujian Normal University, 2011: 17-19.
24	XIA J R , XUE H Y , GAO R J , et al. Sustainable phenolic thermosets coatings derived from urushiol[J]. Polymer Engineering & Science, 2021, 61 (2): 489- 496.
25	张娟妮, 任红艳, 张婷婷. 漆酚类衍生物研究进展[J]. 中国生漆, 2017, 36 (2): 38- 42.
	ZHANG J N , REN H Y , ZHANG T T . Research progress of urushiol derivatives[J]. Journal of Chinese Lacquer, 2017, 36 (2): 38- 42.
26	LU R , WAN Y Y , HONDA T , et al. Design and characterization of modified urethane lacquer coating[J]. Progress in Organic Coatings, 2006, 57 (3): 215- 222. doi: 10.1016/j.porgcoat.2006.08.014
27	ZHANG W Z , JIANG N , ZHANG T T . Synthesis and properties of corresponding polymers of urushiol-based benzoxazine monomers modified by silane[J]. International Journal of Polymer Analysis and Characterization, 2021, 26 (3): 265- 276. doi: 10.1080/1023666X.2021.1883233
28	CHI S X, ZHANG D, FANG R, et al. Preparation and properties of polyamido-amine dendrimer/polyurushiol composite coatings by stepwise electrophoresis deposition[J/OL]. Progress in Organic Coatings, 2022, 166: 106779[2022-11-10]. https://doi.org/10.1016/j.porgcoat.2022.106779.
29	ISHIMURA T , LU R , MIYAKOSHI T . Studies on the reaction mechanismbetween urushiol and organic silane[J]. Progress in Organic Coatings, 2006, 55, 66- 69. doi: 10.1016/j.porgcoat.2005.10.003
30	CHEN Y X, ZHANG G L, ZHANG G Z, et al. Rapid curing and self-stratifying lacquer coating with antifouling and anticorrosive properties[J/OL]. Chemical Engineering Journal, 2021, 421: 129755[2022-11-10]. https://doi.org/10.1016/j.cej.2021.129755.
31	KO M, JUNG J, HWANG S S, et al. Design and development of trivalent Fe ion-induced novel urushi organogels[J/OL]. Polymer, 2020, 205: 122835[2022-11-10]. https://doi.org/10.1016/j.polymer.2020.122835.
32	KANEHASHI S , OYAGI H , LU R , et al. Development of bio-based hybrid resin, from natural lacquer[J]. Progress in Organic Coatings, 2014, 77 (1): 24- 29. doi: 10.1016/j.porgcoat.2013.07.013
33	DENG Y J , BAI W B , ZHANG X M , et al. Effect of silane on the active aging resistance and anticorrosive behaviors of natural lacquer[J]. ACS Omega, 2018, 3 (4): 4129- 4140. doi: 10.1021/acsomega.8b00050
34	许炳铨, 吴坤林, 林棋. 利用电纺技术将漆酚制成具有纳米纤维结构薄膜的方法: CN112267208A[P]. 2021-01-26.
	XU B Q, WU K L, LIN Q. Method for preparing urushiol film with nanofiber structure by electrospinning technology: CN112267208A[P]. 2021-01-26.
35	方润, 陈派锋, 洪永进, 等. 一种阳离子纳米纤维膜的制法及所得纳米纤维膜和应用: CN113622084A[P]. 2021-11-09.
	FANG R, CHEN P F, HONG Y J, et al. The invention relates to a cationic nanofiber film preparation method, the nanofiber film obtained and the application thereof: CN113622084A[P]. 2021-11-09.
36	WU K , SHIU B C , ZHANG D , et al. Preparation of nanoscale urushiol/PAN films to evaluate their acid resistance and protection of functional PVP films[J]. Nanomaterials, 2021, 11 (4): 957- 972. doi: 10.3390/nano11040957
37	ZHANG Y, LI T T, SHIU B C, et al. Multifunctional sodium Alginate@urushiol fiber with targeted antibacterial, acid corrosion resistance and flame retardant properties for personal protection based on wet spinning[J/OL]. Applied Surface Science, 2022, 584(5): 152573[2022-11-10]. https://doi.org/10.1016/j.apsusc.2022.152573.
38	ZHANG L , WANG W P , WU H T , et al. Corrosion-resistant composite coatings based on a graphene oxide-metal oxide/urushiol formaldehyde polymer system[J]. Journal of Coatings Technology and Research, 2021, 18, 1209- 1225. doi: 10.1007/s11998-021-00480-2
39	ZHANG L , WU H T , ZHENG Z Y , et al. Fabrication of graphene oxide/multi-walled carbon nanotube/urushiol formaldehyde polymer composite coatings and evaluation of their physico-mechanical properties and corrosion resistance[J]. Progress in Organic Coatings, 2019, 127, 131- 139. doi: 10.1016/j.porgcoat.2018.10.026
40	CHEN Y X, BAI W B, CHEN J P, et al. In-situ intercalation of montmorillonite/urushiol titanium polymer nanocomposite for anti-corrosion and anti-aging of epoxy coatings[J/OL]. Progress in Organic Coatings, 2022, 165: 106738[2022-11-10]. https://doi.org/10.1016/j.porgcoat.2022.106738.
41	YANG K, CHEN J P, ZHENG L, et al. Urushiol titanium polymer-based composites coatings for anti-corrosion and antifouling in marine spray splash zones[J/OL]. Applied Polymer, 2021, 138(34): 50861[2022-11-10]. https://doi.org/10.1002/app.50861.
42	FANG Y , YAN L Y , LIU H Q . Facile preparation of hydrophobic melamine sponges using naturally derived urushiol for efficient oil/water separation[J]. ACS Applied Polymer Materials, 2020, 2 (9): 3781- 3788. doi: 10.1021/acsapm.0c00393
43	ZHENG X L , WENG J B , HU B H , et al. Fabrication of a stable superhydrophobic film constructed by poly(vinylpyrrolidone)/poly(urushiol)-CuS through layer-by-layer assembly[J]. Materials Chemistry and Physics, 2011, 130 (3): 1054- 1060. doi: 10.1016/j.matchemphys.2011.08.032
44	JEONG H , HEO J , SON B , et al. Intrinsic hydrophobic cairnlike multilayer films for antibacterial effect with enhanced durability[J]. ACS Applied Materials & Interfaces, 2015, 47, 26117- 26123.
45	JEONG H , CHO Y A , CHO Y , et al. Durable urushiol-based nanofilm with water repellency for clear overlay appliances in dentistry[J]. ACS Biomaterials Science & Engineering, 2016, 2 (3): 344- 348.
46	QI Z W, ZHOU H, XUE X Y, et al. Fabrication of epoxy sustained-release coatings loaded with urushiol microcapsules containing essential oil for inhibition on drug-resistant Helicobacter pylori and Staphylococcus aureus[J/OL]. Progress in Organic Coatings, 2021, 161: 106459[2022-11-10]. https://doi.org/10.1016/j.porgcoat.2021.106459.
47	ZHENG L , LIN Y C , WANG D H , et al. Facile one-pot synthesis of silver nanoparticles encapsulated in natural polymeric urushiol for marine antifouling[J]. RSC Advances, 2020, 24, 13936- 13943.
48	CHEN J P, JIAN R K, YANG K, et al. Urushiol-based benzoxazine copper polymer with low surface energy, strong substrate adhesion and antibacterial for marine antifouling application[J/OL]. Journal of Cleaner Production, 2021, 318: 128527[2022-11-10]. https://doi.org/10.1016/j.jclepro.2021.128527.
49	刘淑琼, 许祯毅, 刘瑞来, 等. 一种壳聚糖接枝漆酚/氧化石墨烯复合材料的制备方法: CN114832143A[P]. 2022-08-02.
	LIU S Q, XU Z Y, LIU R L, et al. The invention relates to a preparation method of chitosan grafted urushiol/graphene oxide composite material: CN114832143A[P]. 2022-08-02.
50	CHEN J W , CHENG W , CHEN S N , et al. Urushiol-functionalized mesoporous silica nanoparticles and their self-assembly into a Janus membrane as a highly efficient hemostatic material[J]. Nanoscale, 2018, 10, 22818- 22829. doi: 10.1039/C8NR05882B
51	齐志文, 周昊, 王成章. 漆酚基BPAU-NH2-Gal紫杉醇载药胶束的pH响应性及其体外性能[J]. 林产化学与工业, 2020, 40 (5): 121- 128. doi: 10.3969/j.issn.0253-2417.2020.05.017
	QI Z W , ZHOU H , WANG C Z . pH Responsiveness and their in vitro properties of urushiol-based BPAU-NH₂-gal paclitaxel-loaded micelle[J]. Chemistry and Industry of Forest Products, 2020, 40 (5): 121- 128. doi: 10.3969/j.issn.0253-2417.2020.05.017
52	JE H, WON J. Natural urushiol as a novel under-water adhesive[J/OL]. Chemical Engineering Journal, 2021, 404: 126424[2022-11-10]. https://doi.org/10.1016/j.cej.2020.126424.

[1]	CHEN Qijie, KANG Meicun, ZHENG Xueming, ZHOU Liling, WANG Ping. Application Progress of Nano-cellulose in Paper-based Functional Materials [J]. Chemistry and Industry of Forest Products, 2018, 38(4): 1-8.
[2]	JIANG Jianxin, LIU Yantao, ZHOU Ziyuan, DUAN Jiufang, SUN Dafeng. Research Progress and Applications of Macromolecular Polysaccharide-based Hydrogels for Functional Materials [J]. Chemistry and Industry of Forest Products, 2017, 37(2): 1-10.
[3]	ZHUANG Zhi-liang, ZHU Li, WU Wei-bing, DAI Hong-qi. Progress on the Heterogeneous Cellulose Grafting Polymerization by ATRP [J]. Chemistry and Industry of Forest Products, 2014, 34(3): 121-129.

Research Progress on Polymerization and Curing Technology of Urushiol and Its Application in Functional Polymers

RichHTML

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

Figures/Tables 4

References 52

Related Articles 3

Recommended Articles

Metrics

Comments