松香及其衍生物在无机功能材料中的应用研究进展

doi:10.3969/j.issn.0253-2417.2022.01.016

摘要/Abstract

摘要：

松香是我国重要的生物质资源，其主要成分树脂酸含有三环菲骨架强疏水刚性基团和羧基弱亲水基团，可用于无机纳米材料的分散，降低无机纳米材料的聚集。通过对松香树脂酸双键和羧基等位点进行化学改性，增强亲水性能，可获得亲水亲油性能优异的表面活性剂，与无机材料具有更好的“融合性”，作为模板剂和分散剂，可控辅助制备多种无机功能材料。而设计功能性松香衍生物与无机材料发生化学键合作用，可获得松香基小分子/无机杂化材料和松香改性高分子/无机杂化材料。结合松香及其衍生物的结构特点及化学性质，综述了松香及其衍生物在无机功能材料中的应用，并展望了松香衍生物在无机功能材料开发中的应用前景。

关键词: 松香, 衍生物, 无机材料, 表面活性剂

Abstract:

Rosin is an important biomass resource in China, and its main component resin acid contains tricyclophenylene skeleton strong hydrophobic rigid group and carboxyl weak hydrophilic group. Rosin can be used to disperse inorganic nano materials and reduce the aggregation of inorganic nano materials. The surfactant with excellent hydrophilic and lipophilic properties can be obtained by chemical modification of acid double bond and carboxyl group of rosin resin, which has better "fusion" with inorganic materials. Rosin based surfactant can be used as template and dispersing agent to prepare a variety of inorganic functional materials. The rosin based small molecule/inorganic hybrid materials and rosin modified polymer/inorganic hybrid materials can be obtained by designing functional rosin derivatives to bond with inorganic materials. Based on the structural characteristics and chemical properties of rosin and its derivatives, the application of rosin and its derivatives in inorganic functional materials was reviewed, and the application prospect of rosin derivatives in the development of inorganic functional materials was prospected.

Key words: rosin, derivative, inorganic material, surfactant

中图分类号:

TQ35

刘彤, 董雨萱, 谷婉婷, 韩冰, 韩春蕊. 松香及其衍生物在无机功能材料中的应用研究进展[J]. 林产化学与工业, 2022, 42(1): 123-130.

Tong LIU, Yuxuan DONG, Wanting GU, Bing HAN, Chunrui HAN. Research Progress on Application of Rosin and Its Derivatives in Inorganic Functional Materials[J]. Chemistry and Industry of Forest Products, 2022, 42(1): 123-130.

图/表 6

图1

图2

图3

图4

图5

图6

参考文献 50

1	ATTA A M , ELSAEED A M . Use of rosin-based nonionic surfactants as petroleum crude oil sludge dispersants[J]. Journal of Applied Polymer Sciece, 2011, 122 (1): 183- 192. doi: 10.1002/app.34052
2	NIU X , LIU Y T , SONG Y , et al. Rosin modified cellulose nanofiber as a reinforcing and co-antimicrobial agents in polylactic acid/chitosan composite film for food packaging[J]. Carbohydrate Polymers, 2018, 183, 102- 109. doi: 10.1016/j.carbpol.2017.11.079
3	ISHTIKHAR M , ALI M S , ATTA A M , et al. Interaction of biocompatible natural rosin-based surfactants with human serum albumin: A biophysical study[J]. Journal of Luminescence, 2015, 167, 399- 407. doi: 10.1016/j.jlumin.2015.06.012
4	VARSHOSAZ J , JAVANMARD S H , SOGHRATI S , et al. Magnetic chondroitin targeted nanoparticles for dual targeting of montelukast in prevention of in-stent restenosis[J]. RSC Advances, 2016, 6 (15): 12337- 12347. doi: 10.1039/C5RA20966H
5	MORKHADE D M , NANDE V S , BARABDE U V , et al. Design and evaluation of dental films of PEGylated rosin derivatives containing sparfloxacin for periodontitis[J]. Drug Development and Industrial Pharmacy, 2018, 44 (6): 914- 922. doi: 10.1080/03639045.2017.1421660
6	YADAV B K , GIDWANI B , VYAS A . Rosin: Recent advances and potential applications in novel drug delivery system[J]. Journal of Bioactive and Compatible Polymers, 2016, 31 (2): 111- 126. doi: 10.1177/0883911515601867
7	HARUHISA K , AYAKO N , KEI M . Dynamics and role of rosin acid molecules for preparation of well-dispersed CaCO₃ colloidal suspensions[J]. Journal of Nanoparticle Research, 2012, 14 (6): 1- 11.
8	周文英, 刘曦曦, 黎声鹏, 等. 氢化松香改性轻质纺锤体碳酸钙和KH-550增韧环氧树脂胶粘剂的研究[J]. 中国胶粘剂, 2021, 30 (3): 41- 45.
	ZHOU W Y , LIU X X , LI S P , et al. Study on epoxy resin adhesive by modification of light-weight spindle calcium carbonate with hydrogenated rosin and toughening of KH-550[J]. China Adhesives, 2021, 30 (3): 41- 45.
9	TATARCHUK V V , SERGIEVSKAYA A P , ZAIKOVSKY V I , et al. Preparation and properties of gold nanoparticles stabilized by abietic acid[J]. Russian Journal of Inorganic Chemistry, 2015, 60 (2): 244- 251. doi: 10.1134/S0036023615020175
10	ZHANG Z K, DU J H, ZHANG D D, et al. Rosin-enabled ultraclean and damage-free transfer of graphene for large-area flexible organic light-emitting diodes[J/OL]. Nature Communications, 2017, 8: 1-9[2020-03-03]. https://doi.org/10.1038/ncomms14560.
11	ZHANG D D , DU J H , HONG Y L , et al. A double support layer for facile clean transfer of two-dimensional materials for high-performance electronic and optoelectronic devices[J]. ACS Nano, 2019, 13 (5): 5513- 5522. doi: 10.1021/acsnano.9b00330
12	YAN X Y , ZHAI Z L , SONG Z Q , et al. Polymeric surfactants with tricyclic rigidity from natural rosin: Synthesis and dispersion of single-walled carbon nanotubes in aqueous solution[J]. Journal of Dispersion Science and Technology, 2019, 40 (12): 1687- 1695. doi: 10.1080/01932691.2018.1534592
13	LI J , LIN H X , CHEN X Y , et al. Self-assembled structures and excellent surface properties of a novel anionic phosphate diester surfactant derived from natural rosin acids[J]. Journal of Colloid and Interface Science, 2017, 486, 67- 74. doi: 10.1016/j.jcis.2016.09.061
14	ZHAI Z L , YAN X Y , XU J , et al. Phase behavior and aggregation in a catanionic system dominated by an anionic surfactant containing a large rigid group[J]. Chemistry-A European Journal, 2018, 24 (36): 9033- 9040. doi: 10.1002/chem.201800628
15	ZOU X X , WANG P , WANG Z D , et al. Effects of chlorides on the phase transformation of alumina[J]. Ceramics International, 2018, 44 (9): 10847- 10851. doi: 10.1016/j.ceramint.2018.03.133
16	YAN X Y , ZHAI Z L , XU J , et al. CO₂-responsive pickering emulsions stabilized by a bio-based rigid surfactant with nanosilica[J]. Journal of Agricultural and Food Chemistry, 2018, 66 (41): 10769- 10776. doi: 10.1021/acs.jafc.8b03458
17	AN S Y , HONG S H , TANG C B , et al. Rosin-based block copolymer intracellular delivery nanocarriers with reduction-responsive sheddable coronas for cancer therapy[J]. Polymer Chemistry, 2016, 7 (29): 4751- 4760. doi: 10.1039/C6PY00914J
18	CHEN J J , SONG B L , PEI X M , et al. Rheological behavior of environmentally friendly viscoelastic solutions formed by a rosin-based anionic surfactant[J]. Journal of Agricultural and Food Chemistry, 2019, 67 (7): 2004- 2011. doi: 10.1021/acs.jafc.8b06985
19	韩春蕊, 朱莉伟, 刘六军, 等. 微波溶剂热法松香基表面活性剂控制合成氢氧化镍材料[J]. 林产化学与工业, 2009, 29 (增刊): 149- 153.
	HAN C R , ZHU L W , LIU L J , et al. Controlled synthesis of Ni(OH)₂ materials with rosin-based surfactant by microwave solvothermal method[J]. Chemistry and Industry of Forest Products, 2009, 29 (S1): 149- 153.
20	XU Y X , LI B T , LI J , et al. Controlled hydrothermal synthesis of ball-flower Ni(OH)₂/NiOOH composites assisted by rosin-based betaine zwitterionic surfactant[J]. Journal of Materials Science: Materials in Electronics, 2015, 26 (10): 8040- 8046. doi: 10.1007/s10854-015-3461-x
21	徐永霞, 刘泽学, 詹舒辉, 等. 松香基甜菜碱两亲分子构筑多维Ni(OH)₂/NiOOH微纳米复合材料[J]. 无机化学学报, 2016, 32 (4): 595- 601.
	XU Y X , LIU Z X , ZHAN S H , et al. Construction of multidimensional Ni(OH)₂/NiOOH nanocomposites by rosin-based betaine amphiphilic molecules[J]. Chinese Journal of Inorganic Chemistry, 2016, 32 (4): 595- 601.
22	韩世岩, 李淑君, 方桂珍, 等. 松香改性物用于中空疏水性碳酸钙的制备及分析[J]. 东北林业大学学报, 2013, 41 (6): 144- 145. doi: 10.3969/j.issn.1000-5382.2013.06.034
	HAN S Y , LI S J , FANG G Z , et al. Preparation and analysis of hollow hydrophobic calcium carbonate with modified rosin[J]. Journal of Northeast Forestry University, 2013, 41 (6): 144- 145. doi: 10.3969/j.issn.1000-5382.2013.06.034
23	CHEN Z J , LI S J , TIAN B , et al. Synthesis of a rosin gemini surfactant and its properties[J]. Environmental Engineering Science, 2012, 29 (7): 606- 610. doi: 10.1089/ees.2011.0043
24	JIANG X M , GUO Q J , HE Y Y , et al. Using light to control the floatability of solid particles in aqueous solution of a Gemini surfactant[J]. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2018, 553, 218- 224.
25	SARIKAYA I , BILGEN S , AKBAS H . Investigation of mixing behavior of both a conventional surfactant and different inorganic salts with a cationic gemini surfactant in aqueous solution[J]. Journal of Surfactants and Detergents, 2019, 22 (6): 1319- 1330. doi: 10.1002/jsde.12346
26	LI W K , XIE D H , SONG B L , et al. Synthesis and characterization of ordered mesoporous silica using rosin-based Gemini surfactants[J]. Journal of Materials Science, 2018, 53 (4): 2434- 2442. doi: 10.1007/s10853-017-1709-y
27	马玉玲, 商旭婷, 崔淑芬, 等. 以松香改性物为模板制备多孔二氧化硅的表征[J]. 林产化学与工业, 2013, 33 (6): 37- 40.
	MA Y L , SHANG X T , CUI S F , et al. Preparation of porous silica using a modified rosin as template[J]. Chemistry and Industry of Forest Products, 2013, 33 (6): 37- 40.
28	王鹏, 赵振东, 毕良武, 等. 以松香基季铵盐为模板剂合成介孔γ-Al₂O₃[J]. 林产化学与工业, 2012, 32 (2): 87- 91.
	WANG P , ZHAO Z D , BI L W , et al. Synthesis of mesoporous γ-Al₂O₃ using rosin-based quaternary ammonium salt as template agent[J]. Chemistry and Industry of Forest Products, 2012, 32 (2): 87- 91.
29	王鹏, 陈尚钘, 黄敏, 等. 松香基季铵盐为模板剂有序超微孔二氧化硅的合成[J]. 无机化学学报, 2015, 31 (4): 767- 773.
	WANG P , CHEN S X , HUANG M , et al. Synthesis of ordered super microporous silica using rosin-based quaternary ammonium salt[J]. Chinese Journal of Inorganic Chemistry, 2015, 31 (4): 767- 773.
30	SONG F, WANG P, CHEN S X, et al. Ordered lamellar supermicroporous titania templating by rosin-derived quaternary ammonium salt[J/OL]. PLoS ONE, 2017, 12(6): 1-12[2020-03-03]. https://doi.org/10.1371/journal.pone.0180178.
31	ZHAN S H , JIANG X H , LI J , et al. Controlled synthesis of hydroxyapatite using a novol natural rosin-based surfactant[J]. Nano, 2017, 12 (8): 71- 77.
32	YANG M S , TIAN C , HAN C R , et al. Hierarchical self-assembled hollow hydroxyapatite flower microspheres containing terpene functional groups for efficient drug loading and pH-responsive drug release[J]. Ceramics International, 2018, 44 (17): 20913- 20920. doi: 10.1016/j.ceramint.2018.05.264
33	FEI B L , TU S Y , WEI Z Z , et al. Optically pure chiral copper(II) complexes of rosin derivative as attractive anticancer agents with potential anti-metastatic and anti-angiogenic activities[J]. European Journal of Medicinal Chemistry, 2019, 176, 175- 186. doi: 10.1016/j.ejmech.2019.05.030
34	FEI B L , YIN B , LI D D , et al. Enantiopure copper(II) complex of natural product rosin derivative: DNA binding, DNA cleavage and cytotoxicity[J]. Journal of Biological Inorganic Chemistry, 2016, 21 (8): 987- 996. doi: 10.1007/s00775-016-1394-3
35	费宝丽, 燕庆玲, 李雯, 等. Schiff碱单核与双核配合物的抗菌及催化活性研究[J]. 东北师大学报: 自然科学版, 2011, 43 (2): 91- 95.
	FEI B L , YAN Q L , LI W , et al. Studies on the antibacterial and catalytic activity of Schiff base mono- and di-nudear complexes[J]. Journal of Northeast Normal University(Natural Science Edition), 2011, 43 (2): 91- 95.
36	NGUYEN T T H , LI S J , LI J , et al. Micro-distribution and fixation of a rosin-based micronized-copper preservative in poplar wood[J]. International Biodeterioration & Biodegradation, 2013, 83, 63- 70.
37	CHEN Y X , WEI W , ZHU Y , et al. Synthesis of temperature/pH dual-stimuli-response multicompartmental microcapsules via pickering emulsion for preprogrammable payload release[J]. ACS Applied Materials & Interfaces, 2020, 12 (4): 4821- 4832.
38	YU H , SABETTI M , HÄNER R . Formation of supramolecular nanotubes by self-assembly of a phosphate-linked dimeric anthracene in water[J]. Chemistry-An Asian Journal, 2018, 13 (8): 968- 971. doi: 10.1002/asia.201800275
39	XU Q S , LI S L , YU C Y , et al. Self-assembly of amphiphilic alternating copolymers[J]. Chemistry-A European Journal, 2019, 25 (17): 4255- 4264. doi: 10.1002/chem.201804067
40	ZAOUI A , MAHENDRA V , MITCHELL G , et al. Design, synthesis and thermo-chemical properties of rosin vinyl imidazolium based compounds as potential advanced biocompatible materials[J]. Waste and Biomass Valorization, 2020, 11 (7): 3723- 3730. doi: 10.1007/s12649-019-00691-0
41	WILBON P A , CHU F X , TANG C B . Progress in renewable polymers from natural terpenes, terpenoids, and rosin[J]. Macromolecular Rapid Communications, 2013, 34 (1): 8- 37. doi: 10.1002/marc.201200513
42	RAJEEV J , RACHNA S , MITHU M , et al. Synthesis and characterization of novel reduced Gum rosin-acrylamide copolymer-based nanogel and their investigation for antibacterial activity[J]. Polymer Bulletin, 2017, 74 (8): 2995- 3014. doi: 10.1007/s00289-016-1877-y
43	HUO L , WANG D , LIU H M , et al. Cytoxicity, dynamic and thermal properties of bio-based rosin-epoxy resin/castor oil polyurethane/carbon nanotubes bio-nanocomposites[J]. Journal of Biomaterials Science: Polymer Edition, 2016, 27 (11): 1100- 1114. doi: 10.1080/09205063.2016.1183332
44	LI G X , DENG J , ZENG L , et al. High performance separation of gastrodin by SiO₂/rosin cashew core-shell HPLC stationary phase[J]. Chinese Journal of Analytical Chemistry, 2019, 47 (12): 1946- 1950.
45	SUN Y , LI P F , WANG T , et al. Alkaloid purification using rosin-based polymer-bonded silica stationary phase in HPLC[J]. Journal of Separation Science, 2019, 42 (24): 3646- 3652. doi: 10.1002/jssc.201900835
46	KHAN I , SAEED K , KHAN I . Nanoparticles: Properties, applications and toxicities[J]. Arabian Journal of Chemistry, 2019, 12 (7): 908- 931. doi: 10.1016/j.arabjc.2017.05.011
47	SHARIF H M A , CHENG H Y , HAIDER M R , et al. NO removal with efficient recovery of N₂O by using recyclable Fe₃O₄@EDTA@Fe(Ⅱ) complex: A novel approach toward resource recovery from flue gas[J]. Environmental Science & Technology, 2019, 53 (2): 1004- 1013.
48	BI J T , HUANG X , WANG J K , et al. Oil-phase cyclic magnetic adsorption to synthesize Fe₃O₄@C@TiO₂-nanotube composites for simultaneous removal of Pb(II) and Rhodamine B[J]. Chemical Engineering Journal, 2019, 366, 50- 61. doi: 10.1016/j.cej.2019.02.017
49	SONG H Q , QUAN F F , YU Z Q , et al. Carboplatin prodrug conjugated Fe₃O₄ nanoparticles for magnetically targeted drug delivery in ovarian cancer cells[J]. Journal of Materials Chemistry B, 2019, 7 (3): 433- 442. doi: 10.1039/C8TB02574F
50	ATTA A M , EL-MAHDY G A , AL-LOHEDAN H A , et al. Synthesis of environmentally friendly highly dispersed magnetite nanoparticles based on rosin cationic surfactants as thin film coatings of steel[J]. International Journal of Molecular Sciences, 2014, 15 (4): 6974- 6989. doi: 10.3390/ijms15046974

[1]	张红梅, 陈玉湘, 徐士超, 王婧, 蒋建新, 赵振东. 3-对烯-1-磺酰胺类化合物的合成及其除草活性[J]. 林产化学与工业, 2022, 42(1): 43-50.
[2]	庞淑敬, 陈豪, 宋冰蕾. 一种松香基阴离子表面活性剂的合成与性能研究[J]. 林产化学与工业, 2022, 42(1): 51-56.
[3]	易冯梅, 谢文博, 李浩, 曾磊, 李文, 雷福厚. 核壳型SiO₂@松香基高分子高效液相制备柱的制备及其对喜树碱的分离纯化[J]. 林产化学与工业, 2021, 41(6): 67-75.
[4]	郭晓亮, 祁思迈, 王春鹏, 王基夫, 储富祥. 松香接枝纳米纤维素增强天然橡胶复合材料的制备及性能研究[J]. 林产化学与工业, 2021, 41(5): 72-78.
[5]	鄂羽羽, 李文, 蒋建新, 李伟源, 韦伟, 雷福厚. 松香基阴离子交换树脂对类黑精的吸附性能初探[J]. 林产化学与工业, 2021, 41(5): 79-84.
[6]	侯文彪, 江文夺, 吴嘉超, 梁杰珍, 王琳琳, 陈小鹏. 松脂气液平衡特性及其N₂/CO₂循环活气法蒸馏过程分析[J]. 林产化学与工业, 2021, 41(5): 93-99.
[7]	杨欣欣, 姜兆宇, 刘鹤, 黄旭娟, 蔡照胜, 商士斌. TiO₂改性脱氢枞酸交联室温硫化硅橡胶的制备及性能表征[J]. 林产化学与工业, 2021, 41(4): 42-50.
[8]	姚姝凤, 许嘉琍, 高宏, 汪春学, 张海波, 商士斌. 开口箭根状茎提取物对椪柑贮藏品质的影响[J]. 林产化学与工业, 2021, 41(3): 26-32.
[9]	陶潘, 吴程宇, 毛世英, 王美鑫, 李健. 马来海松基环氧纳米复合材料的制备及性能研究[J]. 林产化学与工业, 2021, 41(1): 7-14.
[10]	于世涛, 邹昊学, 李娅娅, 张慧敏, 王宇婧. Fe₃O₄负载ZnO催化剂的制备及其催化合成松香甘油酯的研究[J]. 林产化学与工业, 2020, 40(6): 8-14.
[11]	张海波, 许嘉琍, 姚姝凤, 高宏, 商士斌. 马来松香季戊四醇酯对椪柑保鲜效果的研究[J]. 林产化学与工业, 2020, 40(6): 15-22.
[12]	童天娇,刘军海,刘艳,曹瑞,魏玲玲. 杨梅叶中杨梅素的提取及抗氧化性研究[J]. 林产化学与工业, 2020, 40(5): 114-120.
[13]	丘雨玲,郭晓亮,卢传巍,王春鹏,王基夫,储富祥. 基于乙基纤维素-马来海松酸酯的酸酐类环氧固化剂的固化及性能研究[J]. 林产化学与工业, 2020, 40(4): 57-62.
[14]	丘雨玲,郭晓亮,卢传巍,王春鹏,王基夫,储富祥. 功能性乙基纤维素-松香复合膜的合成与性能表征[J]. 林产化学与工业, 2020, 40(2): 42-48.
[15]	许吉,翟兆兰,闫鑫焱,宋湛谦,商士斌,饶小平. 改性松香对速生杨木性能提升的研究[J]. 林产化学与工业, 2020, 40(2): 55-62.