松香基双子表面活性剂合成及应用进展

doi:10.3969/j.issn.1001-1803.2022.08.015

摘要/Abstract

摘要：

松香是一种重要的天然化工原料,无毒、可再生,应用十分广泛。松香系列双子表面活性剂主要是以松香酸及其衍生物合成,属于生物基表面活性剂,具有天然松香绿色环保、良好的表面性能以及良好的生物降解性能等特点,其分子设计合成、性能检测及应用开发成为研究热点。根据松香基双子表面活性剂亲水基的解离性质不同,按照阴离子型、阳离子型、两性型和非离子型对松香基双子表面活性剂进行分类,概括了近年来松香基双子表面活性剂的研究进展,探讨了松香基双子表面活性剂的各种性能,简述了各类松香基双子表面活性剂的合成方法、性能特点及应用领域,展望了松香基型双子表面活性剂的发展趋势。

关键词: 松香基, 双子表面活性剂, 绿色, 合成, 应用

Abstract:

It is necessary to develop environment-friendly and sustainable surfactants owing to the more and more attention to environment, ecology and sustainable development and the rapid reduction of petroleum resources. Rosin is an important natural chemical raw material, which is non-toxic, renewable, and widely used. Rosin-based gemini surfactants are mainly synthesized from abietic acid and its derivatives, which belong to bio-based surfactants. They are green, environment-friendly and have good surface activity and good biodegradability. Their design and synthesis, performance test and application development have become research hotspots. According to the different properties of headgroups, rosin-based gemini surfactants are classified into anionic, cationic, amphoteric and non-ionic types. In this review, the research progress of rosin-based gemini surfactants in recent years is summarized. The performance of rosin-based gemini surfactants is discussed. The synthetic methods, performance characteristics and application of various rosin-based gemini surfactants are briefly described. The development trend of rosin-based gemini surfactants is also prospected.

Key words: rosin base, gemini surfactant, green, synthesis, application

中图分类号:

TQ423

赵淑芬,郑丹苗,刘华溪,宋松林,陈站,杨泞源,韦星船. 松香基双子表面活性剂合成及应用进展[J]. 日用化学工业, 2022, 52(8): 892-903.

Zhao Shufen,Zheng Danmiao,Liu Huaxi,Song Songlin,Chen Zhan,Yang Ningyuan,Wei Xingchuan. Progress in synthesis and application of rosin based gemini surfactants[J]. China Surfactant Detergent & Cosmetics, 2022, 52(8): 892-903.

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参考文献 31

[1]	Bois R, Abdellahi B, Mika B, et al. Physicochemical, foaming and biological properties of lowly irritant anionic sugar-based surfactants[J]. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2020, 607: 125525. doi: 10.1016/j.colsurfa.2020.125525
[2]	Ma Xiaolin, Hu Linli, Li Shuiqing, et al. Advances in the application of rosin and its derivatives[J]. Guangzhou Chemical Industry, 2019, 47 (24) : 37-40.
[3]	Tian C, Liang Y L, Lin H X, et al. Surface properties and doxorubicin delivery in mixed systems comprising a natural rosin-based ester tertiary amine and an anionic surfactant[J]. Journal of Dispersion Science and Technology, 2019, 40 (6) : 892-900. doi: 10.1080/01932691.2018.1489274
[4]	Zhai Z, Yan X, Song Z, et al. Annular and threadlike wormlike micelles formed by a bio-based surfactant containing an extremely large hydrophobic group[J]. Soft Matter, 2018, 14 (4) : 499-507. doi: 10.1039/C7SM02163A
[5]	Atta A M, Ramadan A M, Shaffei K A, et al. Synthesis and properties of nonionic surfactants from rosin-imides maleic anhydride adduct[J]. Journal of Dispersion Science and Technology, 2009, 30 (7) : 1100-1110. doi: 10.1080/01932690802597806
[6]	Yan X, Zhai Z, Song Z, et al. Synthesis and properties of polyester-based polymeric surfactants from diterpenic rosin[J]. Industrial Crops & Products, 2017, 108: 371-378.
[7]	Kugler S, Ossowicz P, Malarczyk-Matusiak K, et al. Advances in rosin-based chemicals: the latest recipes, applications and future trends[J]. Molecules, 2019, 24 (9) : 1651. doi: 10.3390/molecules24091651
[8]	Zhang Jiayu. Synthesis and properties of a new rosin-sulfonyl betaine amphoteric surfactant[J]. Petrochemical Technology, 2020, 49 (2) : 166-169.
[9]	Jia H, Leng X, Wang Q, et al. Controllable emulsion phase behaviour via the selective host-guest recognition of mixed surfactants at the water/octane interface[J]. Chemical Engineering Science, 2019, 202: 75-83. doi: 10.1016/j.ces.2019.03.036
[10]	Pisárčik M, Polakovičová M, Markuliak M, et al. Self-assembly properties of cationic gemini surfactants with biodegradable groups in the spacer[J]. Molecules, 2019, 24 (8) : 1481. doi: 10.3390/molecules24081481
[11]	Jia Weihong. Synthesi and properties of rosin-based sulfonate gemini surfactants[J]. Petrochemical Technology, 2009, 38 (6) : 651-655.
[12]	Rao Xiaoping, Song Zhanqian, Shang Shibin. Synthesis and properties of rosin-based dicarboxylic gemini surfactant[J]. Biomass Chemical Engineering, 2011, 45 (6) : 1-4.
[13]	Li Juan. Synthesis and application of decomposable functional rosin based surfactants[D]. Beijing: Beijing Forestry University, 2017.
[14]	Li J, Lin H, Chen X, 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
[15]	Zhan S H, Jiang X H, Li J, et al. Controlled synthesis of hydroxyapatite using a novel natural rosin-based surfactant[J]. Nano, 2017, 12 (8) : 1750098. doi: 10.1142/S1793292017500989
[16]	Li Juan, Yang Mingsheng, Tian Chao, et al. Synthesis and properties of rosin based decomposable surfactants[J]. Fine Chemicals, 2018, 35 (6) : 964-969.
[17]	Wang Juan. Synthesis, structure and characterization of rosin based gemini surfactants[D]. Beijing: Chinese Academy of Forestry, 2014.
[18]	Jia Weihong. Synthesis and properties of rosin based gemini surfactants[D]. Beijing: Chinese Academy of Forestry, 2009.
[19]	Han Shiyan. Synthesis of rosin based gemini surfactants and prepration of nanometer materials[D]. Heilongjiang: Northeast Forestry University, 2012.
[20]	Wang Jinpeng, Shi Xiaomeng, Yu Zhe, et al. Characterization of cuprous oxide prepared by bisquaternary ammonium salt based on bisrosin as template[J]. Guangdong Chemical Industry, 2015, 42 (16) : 20-21.
[21]	Zhang Yongchang. Study on synthesis and properties of multi-hydroxy quaternary ammonium gemini surfactant containing modified rosin[D]. Guangxi: Guilin University of Technology, 2012.
[22]	Deng W, Zhang Y, Zhong Y, et al. Synthesis and thermodynamic properties of rosin based cationic gemini surfactants[J]. Journal of Surfactants and Detergents, 2014, 17 (3) : 453-458. doi: 10.1007/s11743-013-1559-9
[23]	Song Binglei, Yu Xiaona, Chen Yan, et al. Synthesis and properties of rosin based gemini surfactants with amide group[J]. Chemistry and Industry of Forest Products, 2015, 35 (6) : 39-46.
[24]	Li W, Xie D, Song B, 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
[25]	Rao Xianxian, Wu Chenyu, Luo Qingli, et al. Synthesis and properties of a rosin-based gemini surfactant containing a long spacer[J]. Journal of Forestry Engineering, 2019, 4 (6) : 83-90. doi: 10.12737/8444
[26]	Wang Juan, Wang Dan, Shang Shibin, et al. Synthesis and properties of rosin based quaternary ammonium salt heterogemini surfactant[J]. Chemistry and Industry of Forest Products, 2014, 34 (6) : 111-116.
[27]	Chen Z, Li S, 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
[28]	Liang T, Zhang Y, Li S, et al. Synthesis, characterization, and bioactivity of rosin quaternary ammonium salt derivatives[J]. Bioresources, 2012, 8 (1) : 735-742.
[29]	Lin H X, Yang M S, Li J, et al. A novel bola-type rosin-based functional surfactant and its synergistic effect with natural surfactant saponin[J]. Journal of Surfactants and Detergents, 2017, 20 (5) : 1205-1212. doi: 10.1007/s11743-017-1994-0
[30]	Feng Lin. Study on the synthesis and self-assembly of rosin-based oligomeric surfactants[D]. Jiangsu: Jannan University, 2018.
[31]	Wang Juan, Wang Dan, Shang Shibin, et al. Synthesis and properties of rosin based polyoxyethylene amine gemini surfactants[J]. Chemistry and Industry of Forest Products, 2014, 34 (5) : 109-114.

化合物	cmc/（mol/L）	γ_cmc/（mN/m）	Krafft/℃	泡沫高度H₀/H_{5 min}	乳化时间/min	HLB
1	1.3×10^-4	28.1	<0	2/0	0.3	14.9
2	1.1×10^-4	33.6		5/3	>30	12.21
5	1.38×10^-3	31.8	50~60	19/3.5	2.55	9.9
6	1.71×10^-3	33.2	50~60	23/11.5	1.6	7.6
7	8.63×10^-5	23.5	19	115/97	55
K12	8.1×10^-3	33	10	175/170	12

化合物	cmc/（mol/L）	γ_cmc/（mN/m）	泡沫高度H₀/H_{5 min}	乳化时间
8	2×10^-5	23.7	40/2	4 d
9	6.7×10^-6	24	115/110	8 min
10	1.42×10^-4	36.69	200/150	16 min
11	4×10^-4	37.35	255/250	20 min
12	6×10^-4	36.63	252/250	25 min
15	2.3×10^-5	32	70/53	47 min
16	2.3×10^-5	32	60/52	34 min
17	4.1×10^-4	38.4
18	1.1×10^-4	36.4
19	3.32×10^-5	24.7	137/125	42 min
22	3.9×10^-4	39.18		36 min
23	7.5×10^-4	45.02		245 s
26	4.4×10^-4	34.3
CTAB	9.8×10^-4	37.3	122/116	159 s

化合物	cmc/（mol/L）	γ_cmc/（mN/m）	泡沫高度H₀/H_{5 min}	乳化时间/s	浊点/℃	HLB
28	6.5×10^-4	34.3	2/0	50	76.9	18.1
29	1.9×10^-4	22.2		200	>90
30	1×10^-4	37.8	105/41			16.8
31	3.46×10^-3	48.2	16/6	11	>90	5.8
TX-10	2.03×10^-3	31.6		165	63