Surface activity and cleaning performance of rosin-based quaternary ammonium salt type asymmetric Gemini surfactants

doi:10.1016/j.cjche.2024.05.004

中国化学工程学报 ›› 2024, Vol. 73 ›› Issue (9): 70-80.DOI: 10.1016/j.cjche.2024.05.004

Surface activity and cleaning performance of rosin-based quaternary ammonium salt type asymmetric Gemini surfactants

Haoyu Feng¹, Yaoqi Pan¹, Yijia Zhang¹, Zhuofan Zhang¹, Yunye Huang¹, Linxi Hou^1,2,3, Longqiang Xiao^1,2

1. Department of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Fuzhou University, Fuzhou 350116, China;
2. Qingyuan Innovation Laboratory, Quanzhou 362801, China;
3. Fujian Key Laboratory of Advanced Manufacturing Technology of Specialty Chemicals, Fuzhou University, Fuzhou 350116, China

收稿日期:2023-11-06 修回日期:2024-02-25 接受日期:2024-05-06 出版日期:2024-11-21 发布日期:2024-05-23
通讯作者: Linxi Hou,E-mail:lxhou@fzu.edu.cn;Longqiang Xiao,E-mail:xiaolq@fzu.edu.cn
基金资助:
This work was supported by National Natural Science Foundation of China (U21A200313), Key Program of Qingyuan Innovation Laboratory (00221003), and ‘111’ program of Fuzhou University.

Surface activity and cleaning performance of rosin-based quaternary ammonium salt type asymmetric Gemini surfactants

Haoyu Feng¹, Yaoqi Pan¹, Yijia Zhang¹, Zhuofan Zhang¹, Yunye Huang¹, Linxi Hou^1,2,3, Longqiang Xiao^1,2

1. Department of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Fuzhou University, Fuzhou 350116, China;
2. Qingyuan Innovation Laboratory, Quanzhou 362801, China;
3. Fujian Key Laboratory of Advanced Manufacturing Technology of Specialty Chemicals, Fuzhou University, Fuzhou 350116, China

Received:2023-11-06 Revised:2024-02-25 Accepted:2024-05-06 Online:2024-11-21 Published:2024-05-23
Contact: Linxi Hou,E-mail:lxhou@fzu.edu.cn;Longqiang Xiao,E-mail:xiaolq@fzu.edu.cn
Supported by:
This work was supported by National Natural Science Foundation of China (U21A200313), Key Program of Qingyuan Innovation Laboratory (00221003), and ‘111’ program of Fuzhou University.

摘要/Abstract

摘要： Rosin, a renewable and abundant resource, has been extensively processed and chemically modified to endow it with special properties, especially in the surfactant industry. In this study, four rosin-based quaternary ammonium asymmetric gemini surfactants (RGS-2-n) with different alkyl chain lengths (n = 12, 14, 16, 18) were synthesized using a simple two-step method based on dehydroabietylamine as the raw material. The feasibility of these surfactants for cleaning purposes was comprehensively evaluated, suggesting that the surfactants own high surface activity and good cleaning performance. Furthermore, by successfully introducing the amine group of dehydroabietylamine into the hydrophilic group of the surfactants, we avoided its potential harm to the environment and water pollution. Density functional theory proves rosin-based gemini surfactants with asymmetric structure can further improve cleaning efficiency. Overall, our findings suggests that RGS-2-n surfactants are promising and sustainable candidates for cleaning electric plates, and provide new opportunities for rosin application in the electric industry.

关键词: Electronic components, Asymmetric gemini surfactants, Cleaning performance, Rosin

Abstract: Rosin, a renewable and abundant resource, has been extensively processed and chemically modified to endow it with special properties, especially in the surfactant industry. In this study, four rosin-based quaternary ammonium asymmetric gemini surfactants (RGS-2-n) with different alkyl chain lengths (n = 12, 14, 16, 18) were synthesized using a simple two-step method based on dehydroabietylamine as the raw material. The feasibility of these surfactants for cleaning purposes was comprehensively evaluated, suggesting that the surfactants own high surface activity and good cleaning performance. Furthermore, by successfully introducing the amine group of dehydroabietylamine into the hydrophilic group of the surfactants, we avoided its potential harm to the environment and water pollution. Density functional theory proves rosin-based gemini surfactants with asymmetric structure can further improve cleaning efficiency. Overall, our findings suggests that RGS-2-n surfactants are promising and sustainable candidates for cleaning electric plates, and provide new opportunities for rosin application in the electric industry.

Key words: Electronic components, Asymmetric gemini surfactants, Cleaning performance, Rosin

Haoyu Feng, Yaoqi Pan, Yijia Zhang, Zhuofan Zhang, Yunye Huang, Linxi Hou, Longqiang Xiao. Surface activity and cleaning performance of rosin-based quaternary ammonium salt type asymmetric Gemini surfactants[J]. 中国化学工程学报, 2024, 73(9): 70-80.

参考文献

[1] N. Korf, A.N. Loevik, R. Figi, C. Schreiner, C. Kuntz, P.M. Mahlitz, M. Rosslein, P. Wager, V.S. Rotter, Multi-element chemical analysis of printed circuit boards-challenges and pitfalls, Waste Manag. 92 (2019) 124-136.
[2] W.F. Chen, Y.J. Chen, Y.K. Shu, Y.N. He, J.B. Wei, Characterization of solid, liquid and gaseous products from waste printed circuit board pyrolysis, J. Clean. Prod. 313 (2021) 127881.
[3] H. Shamkhalichenar, C.J. Bueche, J.W. Choi, Printed circuit board (PCB) technology for electrochemical sensors and sensing platforms, Biosensors 10 (11) (2020) 159.
[4] Q.Y. Tan, L.L. Liu, M. Yu, J.H. Li, An innovative method of recycling metals in printed circuit board (PCB) using solutions from PCB production, J. Hazard. Mater. 390 (2020) 121892.
[5] A. Ravi Shankar, K. Praveen, S.R. Polaki, S.C. Vanithakumari, N.G. Krishna, L. Srivani, R.P. George, J. Philip, Failure of printed circuit boards during storage and service: leaked capacitors and white residue, J. Mater. Eng. Perform. 29 (10) (2020) 6402-6411.
[6] C.M. Tan, H.H. Chen, J.P. Wu, V. Sangwan, K.Y. Tsai, W.C. Huang, Root cause analysis of a printed circuit board (PCB) failure in a public transport communication system, Appl. Sci. 12 (2) (2022) 640.
[7] S. Zhan, M.H. Azarian, M. Pecht, Reliability of printed circuit boards processed using No-clean flux technology in temperature-humidity-bias conditions, IEEE Trans. Device Mater. Reliab. 8 (2) (2008) 426-434.
[8] S.Svetsky, Testing and long-term monitoring within printed circuit board cleaning technology, Circuit World 37 (2) (2011) 27-32.
[9] N. Ismail, R. Ismail, A. Jalar, G. Omar, E.M. Salleh, N. Kamil, I.A. Rahman, Comparative study of interfacial interaction between aromatic and aliphatic functional group in solder wettability, J. Mater. Sci. Mater. Electron. 29 (15) (2018) 12910-12916.
[10] T-H. Tseng, A.T. Wu, Microelectronics Reliability, Corrosion on automobile printed circuit broad, Microelectron. Reliab. 98 (2019) 19-23.
[11] W.D. Song, M.H. Hong, Y.F. Lu, T.C. Chong, Laser cleaning of printed circuit boards, Appl. Surf. Sci. 208 (2003) 463-467.
[12] Z. Toth, A. Lukacs, I. Szalai, Ionic contamination reduction with dry ice cleaning, IOP Conf. Ser.: Mater. Sci. Eng. 1246 (1) (2022) 012015.
[13] Y.J. Zhan, H.Y. Wu, L.F. Liu, J. Lin, S.W. Zhang, Organic solvent-based tissue clearing techniques and their applications, J. Biophotonics 14 (6) (2021) e202000413.
[14] L. Tmakova, S. Sekretar, S. Schmidt, Plant-derived surfactants as an alternative to synthetic surfactants: surface and antioxidant activities, Chem. Pap. 70 (2) (2016) 188-196.
[15] M.Y. Fan, W.J. Kim, D.R. Heldman, Influence of cleaning agent reuse on cleaning effectiveness, J. Food Eng. 320 (2022) 110926.
[16] M.K. Cui, S.L. Xu, W.Q. Song, H.B. Ye, J.L. Huang, B.H. Liu, B. Dong, Z.X. Xu, Trace metals, polycyclic aromatic hydrocarbons and polychlorinated biphenyls in the surface sediments from Sanya River, China: Distribution, sources and ecological risk, Environ. Pollut. 294 (2022) 118614.
[17] W.Y. Kwon, J.H. Lee, Y.E. Jeon, K.S. Park, Cellulose-based eco-friendly wafer-cleaning reagent, Cellulose 27 (6) (2020) 3405-3412.
[18] W.Q. Jia, R. Zhen, B. Liang, Y. Du, K. Yang, M. Zhang, F. Liu, Preparation technology of water based detergent for Q235 carbon steel, IOP Conf. Ser.: Earth Environ. Sci. 714 (3) (2021) 032031.
[19] J.N. Yin, G.H. Huang, C.J. An, P. Zhang, X.Y. Xin, R.F. Feng, Exploration of nanocellulose washing agent for the green remediation of phenanthrene-contaminated soil, J. Hazard. Mater. 403 (2021) 123861.
[20] J.Y. Guo, Y. Kim, Z.K. Chong, A. Alassali, J.P. Chacon, D. Gottschalk, M. Kitzberger, K. Kuchta, Quality changes of low-density polyethylene (LDPE) recyclates from the pretreatment process with a cationic surfactant and a nonionic surfactant as cleaning agents upstream of extrusion, Processes 10 (11) (2022) 2174.
[21] H. Nakahara, H. Nishizaka, K. Iwasaki, Y. Otsuji, M. Sato, K. Matsuoka, O. Shibata, Role of the spacer of Gemini surfactants in solubilization into their micelles, J. Mol. Liq. 244 (2017) 499-505.
[22] N. Yekeen, M.A. Manan, A.K. Idris, A.M. Samin, Influence of surfactant and electrolyte concentrations on surfactant Adsorption and foaming characteristics, J. Petrol. Sci. Eng. 149 (2017) 612-622.
[23] Y.Q. Cheng, L.N. Xue, C.R. Niu, T.T. Du, Y. Yang, Z. Feng, Synthesis and properties of a novel asymmetric gemini surfactant based on siloxane skeleton, J. Mol. Liq. 296 (2019) 112073.
[24] S.M. Rajput, K. Mondal, M. Kuddushi, M. Jain, D. Ray, V.K. Aswal, N.I. Malek, Formation of hydrotropic drug/gemini surfactant based catanionic vesicles as efficient nano drug delivery vehicles, Colloid Interface Sci. Commun. 37 (2020) 100273.
[25] S.M.S. Hussain, M.S. Kamal, L.T. Fogang, Synthesis and physicochemical investigation of betaine type polyoxyethylene zwitterionic surfactants containing different ionic headgroups, J. Mol. Struct. 1178 (2019) 83-88.
[26] G.L. Cao, M.L. Gao, T. Shen, S.X. Guo, B.B. Zhao, Q. Zhao, Asymmetric gemini surfactants modified vermiculite- and silica nanosheets-based adsorbents for removing methyl orange and crystal violet, Colloids Surf. A Physicochem. Eng. Aspects 596 (2020) 124735.
[27] I. Ahmad Bhat, T. Kausar, A. Ahmad Dar, S.M. Nayeem, M. Akram, Kabir-ud-Din, Exclusive behaviour of asymmetric zwitterionic gemini surfactants towards lysozyme, J. Mol. Liq. 336 (2021) 116583.
[28] P. Li, A.X. Li, R.J. Ruan, Y.X. Guo, Q. He, W.H. Zou, L.X. Hou, Asymmetrical gemini surfactants directed synthesis of hierarchical ZSM-5 zeolites and their immobilization of molybdenum complex for the catalytic epoxidation of alkenes, ChemCatChem 13 (20) (2021) 4442-4452.
[29] Y.Q. Pan, B.Q. Ge, Y.L. Zhang, P. Li, B.G. Guo, X.Y. Zeng, J.G. Pan, S. Lin, P. Yuan, L.X. Hou, Surface activity and cleaning performance of Gemini surfactants with rosin groups, J. Mol. Liq. 336 (2021) 116222.
[30] Z.L. Zhai, X.Y. Yan, J. Xu, Z.Q. Song, S.B. Shang, X.P. Rao, Phase behavior and aggregation in a catanionic system dominated by an anionic surfactant containing a large rigid group, Chemistry 24 (36) (2018) 9033-9040.
[31] X.Y. Yan, Z.L. Zhai, Z.Q. Song, S.B. Shang, X.P. Rao, Synthesis and properties of polyester-based polymeric surfactants from diterpenic rosin, Ind. Crops Prod. 108 (2017) 371-378.
[32] G.C. Han, Y. Han, X.Y. Wang, S.J. Liu, R.C. Sun, Synthesis of organic rectorite with novel Gemini surfactants for copper removal, Appl. Surf. Sci. 317 (2014) 35-42.
[33] Z.L. Zhai, X.Y. Yan, J. Xu, Z.Q. Song, S.B. Shang, X.P. Rao, Reversible dispersion and precipitation of single-walled carbon nanotubes using a pH-responsive rigid surfactant, Chem. Commun. 54 (86) (2018) 12171-12173.
[34] A. Zdziennicka, J. Krawczyk, K. Szymczyk, B. Janczuk, Macroscopic and microscopic properties of some surfactants and biosurfactants, Int. J. Mol. Sci. 19 (7) (2018) 1934.
[35] A.M. Atta, A.M. Ramadan, K.A. Shaffei, A.M. Nassar, N.S. Ahmed, M. Fekry, Synthesis and properties of nonionic surfactants from rosin-imides maleic anhydride adduct, J. Dispers. Sci. Technol. 30 (7) (2009) 1100-1110.
[36] M. Ishtikhar, Rahisuddin, M.V. Khan, R.H. Khan, Anti-aggregation property of thymoquinone induced by copper-nanoparticles: a biophysical approach, Int. J. Biol. Macromol. 93 (Pt A) (2016) 1174-1182.
[37] Q. Zhao, Y.J. Li, X.L. Chai, L.F. Zhang, L.Z. Xu, J.H. Huang, P. Ning, S.L. Tian, Interaction of nano carbon particles and anthracene with pulmonary surfactant: The potential hazards of inhaled nanoparticles, Chemosphere 215 (2019) 746-752.
[38] X.K. Li, M. Yoneda, Y. Shimada, Y. Matsui, Effect of surfactants on the aggregation and stability of TiO₂ nanomaterial in environmental aqueous matrices, Sci. Total Environ. 574 (2017) 176-182.
[39] T. Okada, N. Arimura, C. Ono, M. Yuasa, Electro-oxidation of methanol on mixed catalysts based on platinum and organic metal complexes in acidic media, Electrochim. Acta 51 (6) (2005) 1130-1139.
[40] X.P. Wu, C.L. Dai, S.S. Fang, H. Li, Y.N. Wu, X. Sun, M.W. Zhao, The effect of hydroxyl on the solution behavior of a quaternary ammonium gemini surfactant, Phys. Chem. Chem. Phys. 19 (24) (2017) 16047-16056.
[41] Y. Khambhaty, Applications of enzymes in leather processing, Environ. Chem. Lett. 18 (3) (2020) 747-769.
[42] C.P. Chen, F. Lu, Q.X. Tong, Three tetrasiloxane-tailed cationic gemini surfactants: The effect of different spacer rigidity on surface properties and aggregation behaviors, J. Mol. Liq. 266 (2018) 504-513.
[43] R. Zana, Alkanediyl-alpha, omega-bis(dimethylalkylammonium bromide) surfactants: II. Krafft temperature and melting temperature, J. Colloid Interface Sci. 252 (1) (2002) 259-261.
[44] N.A. Negm, N.G. Kandile, I.A. Aiad, M.A. Mohammad, New eco-friendly cationic surfactants: Synthesis, characterization and applicability as corrosion inhibitors for carbon steel in 1N HCl, Colloids Surf. A Physicochem. Eng. Aspects 391 (1-3) (2011) 224-233.
[45] Q.X. Mei, L. Lai, S.J. Li, P. Mei, Y.Q. Wang, Q.L. Ma, Y. Liu, Surface properties and phase behavior of Gemini/conventional surfactant mixtures based on multiple quaternary ammonium salts, J. Mol. Liq. 281 (2019) 506-516.
[46] P. Li, Y.X. Guo, Z. Lu, W.Z. Zhang, L.X. Hou, Syntheses, surface activities and aggregation morphologies of a series of novel itaconic acid based asymmetrical gemini surfactants, J. Mol. Liq. 290 (2019) 111218.
[47] G.Y. Zeng, C.R. Zhong, X.C. Wang, X.G. He, E.Z. Pu, Micellization thermodynamics, interfacial behavior, salt-resistance and wettability alteration of gemini hybrid fluorinated surfactant, Colloids Surf. A Physicochem. Eng. Aspects 660 (2023) 130859.
[48] J.L. Ma, P.W. Xiao, P.M. Wang, X. Han, J.H. Luo, R.F. Shi, X. Wang, X.Y. Song, S.L. Zhao, Molecular dynamics simulation study on π-π stacking of Gemini surfactants in oil/water systems, Chin. J. Chem. Eng. 50 (2022) 335-346.
[49] B. Cai, X.F. Li, Y. Yang, J.F. Dong, Surface properties of Gemini surfactants with pyrrolidinium head groups, J. Colloid Interface Sci. 370 (1) (2012) 111-116.
[50] M. Kamel, M. Hegazy, S. Rashwan, M. El Kotb, Innovative surfactant of Gemini-type for dissolution mitigation of steel in pickling HCl medium, Chin. J. Chem. Eng. 34 (2021) 125-133.
[51] A. Fromm, C. van Wullen, D. Hackenberger, L.J. Goossen, Mechanism of Cu/Pd-catalyzed decarboxylative cross-couplings: ADFT investigation, J. Am. Chem. Soc. 136 (28) (2014) 10007-10023.
[52] Z.H. Asadov, G.A. Ahmadova, R.A. Rahimov, S.Z F. Hashimzade, Y. Abdullayev, E.H. Ismailov, S.A. Suleymanova, N.Z. Asadova, F.I. Zubkov, J. Autschbach, Aggregation and antimicrobial properties of gemini surfactants with mono- and di-(2-hydroxypropyl)ammonium head-groups: Effect of the spacer length and computational studies, J. Mol. Liq. 302 (2020) 112579.
[53] Q.Z. Chen, W.X. Liu, H.J. Liu, X.R. Huang, Y.Z. Shang, H.L. Liu, Molecular dynamics simulations and density functional theory on unraveling photoresponsive behavior of wormlike micelles constructed by 12-2-12·2Br^- and trans- ortho-methoxy cinnamate, Langmuir 36 (32) (2020) 9499-9509.
[54] S.S. Khire, N. Sahu, S.R. Gadre, MTASpec software for calculating the vibrational IR and Raman spectra of large molecules at ab initio level, Comput. Phys. Commun. 270 (2022) 108175.
[55] V. Ramakrishna, B.J. Duke, Extension of complete basis set model chemistries to molecules containing third row atoms Ga-Kr, J. Chem. Phys. 118 (14) (2003) 6137-6143.
[56] Z. Mitrinova, S. Tcholakova, N. Denkov, Control of surfactant solution rheology using medium-chain cosurfactants, Colloids Surf. A Physicochem. Eng. Aspects 537 (2018) 173-184.
[57] D. Bajani, D. Gharai, J. Dey, A comparison of the self-assembly behaviour of sodium N-lauroyl sarcosinate and sodium N-lauroyl glycinate surfactants in aqueous and aqueo-organic media, J. Colloid Interface Sci. 529 (2018) 314-324.
[58] Y. Xu, J. Feng, Y.Z. Shang, H.L. Liu, Molecular dynamics simulation for the effect of chain length of spacer and tail of cationic gemini surfactant on the complex with anionic polyelectrolyte, Chin. J. Chem. Eng. 15 (4) (2007) 560-565.
[59] M.J. Yi, Z.H. Huang, J.C. Hao, Magnetic gemini surfactants, Langmuir 35 (29) (2019) 9538-9545.
[60] R. Abdel-Rahem, The influence of hydrophobic counterions on micellar growth of ionic surfactants, Adv. Colloid Interface Sci. 141 (1-2) (2008) 24-36.
[61] Y. Guo, Q.S. Wu, C. Yao, Aggregation behavior of a pH-responsive cationic-nonionic silicone surfactant in aqueous solution, Colloid Interface Sci. Commun. 42 (2021) 100401.
[62] R.G. Wang, X.X. Xu, X.D. Shi, J.J. Kou, H.J. Song, Y.X. Liu, J.J. Zhang, Q.M. Wang, Promoting efficacy and environmental safety of pesticide synergists via non-ionic gemini surfactants with short fluorocarbon chains, Molecules 27 (19) (2022) 6753.
[63] L.R. Liao, Z.J. Ke, X. Wang, S.C. Li, S.J. Wang, X.P. Rao, Recyclable ethyl cellulose film modified by rosin based quaternary ammonium salt for antimicrobial packaging, Ind. Crops Prod. 198 (2023) 116692.
[64] W.Q. Lin, D.F. Chen, Q. Yong, C.X. Huang, S.L. Huang, Improving enzymatic hydrolysis of acid-pretreated bamboo residues using amphiphilic surfactant derived from dehydroabietic acid, Bioresour. Technol. 293 (2019) 122055.
[65] K. Urata, N. Takaishi, A perspective on the contribution of surfactants and lipids toward “Green Chemistry”: Present states and future potential, J. Surfactants Deterg. 4 (2) (2001) 191-200.

Surface activity and cleaning performance of rosin-based quaternary ammonium salt type asymmetric Gemini surfactants

Surface activity and cleaning performance of rosin-based quaternary ammonium salt type asymmetric Gemini surfactants

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[3]	聂园梅, 姚兴东, 雷福厚. Sonochemical Synthesis of Maleated Rosin[J]. , 2008, 16(3): 365-368.