Evaluation of Some Nonionic Surfactants Derived from Tannic Acid as Additives for Water‐Based Mud

Water‐based mud is the most‐used mud for oil and gas exploration and is generally considered to be more environmentally friendly than oil‐based or synthetic‐based mud. Therefore in this study we focused on water‐based mud and a series of nonionic surfactants derived from tannic acid was evaluated as additives for water‐based muds. The rheological properties for formulated water‐based muds contain nonionic additives at different temperatures were investigated including: apparent viscosity, plastic viscosity, yield point, gel strength, thixotropy and filtration properties. In addition to the relation between shear stress and shear rate were presented at different temperatures. The results of the studied nonionic surfactant showed improvements in the rheological properties when used as additives for water‐based mud formulation.     

Synthesis and Evaluation of Novel Amido-Amine Cationic Gemini Surfactants Containing Flexible and Rigid Spacers

New amido‐amine‐based cationic gemini surfactants with flexible and rigid spacers and different hydrophobic tails were synthesized and characterized. These gemini surfactants were prepared by a modified procedure through amidation of long chain carboxylic acids using 3‐(dimethylamino)‐1‐propylamine followed by treatment with halohydrocarbons. The effect of the trans and cis conformation of the spacer double bond was investigated by means of critical micelle concentration, surface tension reduction, and thermal stability. The short‐term thermal stability of the gemini surfactants was assessed using thermogravimetric analysis (TGA) and the long‐term thermal stability was examined by a unique approach based on structure characterization techniques including NMR (¹H and ¹³C) and FTIR analysis. TGA results demonstrated excellent short‐term thermal stability since no structure degradation was observed up to 200 °C. Structural characterization revealed impressive long‐term thermal stability of the gemini surfactants with no structure decomposition after exposing them to 90 °C for 10 days. The critical micelle concentration of gemini surfactants was found to be in the range of 0.77 × 10^?4–3.61 × 10^?4 mol L^?1 and corresponding surface tension (γ_CMC) ranged from 30.34 to 38.12 mN m^?1. The surfactant with the trans conformation of spacer double bond showed better surface properties compared to the surfactant with the cis conformation of spacer double bond. Similarly, increasing surfactant tail length and spacer length resulted in decreasing CMC values. Moreover, bromide counterion showed improved surface properties compared to chloride counterion.     

Synthesis and Micellization of Organosilicon Gemini Quaternary Ammonium Surfactants

A novel class of organosilicon gemini quaternary ammonium surfactant alkyl‐α, ω‐bis(diethyl‐methyl‐dimethoxy‐silopropyl ammonium bromide) (α, ω = 1,4; 1,6; 1,8) was synthesized and characterized by ¹H‐nuclear magnetic resonance (NMR) and elemental analysis. It is found that the quaternization reaction has two steps: first single quaternization and then double quaternization. The effect of solvent on convert ratio has the following sequence: polar aprotic solvents > polar protic solvents > aromatic solvents. The electrical conductivity of aqueous solution was measured at 20, 25, 30 and 35 °C, and the thermodynamic properties of , and were calculated according to the mass action model and Gibbs equation. It is shown that the enthalpy driven and entropy driven are almost equal in the micellization of [SiC₃‐4‐SiC₃]Br₂ and [SiC₃‐6‐SiC₃]Br₂, but in the micellization of [SiC₃‐8‐SiC₃]Br₂, the enthalpic contribution becomes significant and the effect of thermal is greater than the degree of order in the micellization.     

Gemini型表面活性剂的合成进展

综述了Gemini型表面活性剂,包括阴离子型、阳离子型、非离子型、两性型及一些特殊类型Gemini表面活性剂的合成方法研究进展。有参考文献23篇。     

Synthesis and Properties of Novel Phenylenediamine Gemini Surfactants

In the present work, a two-step method was adopted to synthesize a series of novel Gemini surfactants using N,N-dimethylalkyl amines (alkyl length = C₁₂, C₁₆ and C₁₈), epichlorohydrin, and n-phenyllenediamine as starting materials. The products were characterized using mass spectroscopy (MS) and nuclear magnetic resonance spectroscopy (¹H NMR). Systematic experiments were conducted to evaluate their surface activity, foaming properties, and antibacterial performance. Results showed the critical micelle concentrations (CMC) of the C₁₂-based, C₁₆-based, and C₁₈-based phenylenediamine surfactants were 3.295 × 10⁻³, 2.532 × 10⁻⁴, and 3.140 × 10⁻⁴ mol L⁻¹ at 298 K, respectively, with corresponding surface tension (γ_cmc) values of 28.24, 31.95, and 35.06 mN m⁻¹ under the same conditions. The Gemini surfactants showed not only good surface activity and foaming properties, but also demonstrated good antimicrobial performance against Gram-positive and Gram-negative bacteria and fungi.     

Synthesis,Surface Activity,and Antimicrobial Efficacy of Hydrogenated Cardanol-Derived Positively Charged Asymmetric Gemini Surfactants

Nine different hydrogenated cardanol-based quaternary ammonium compounds including one conventional single-tale single-head surfactant, one bicephalic single-tale double-head surfactant, and seven asymmetric Gemini surfactants were synthetized using a simple process with high yields. Their structures were characterized using ¹H NMR, ¹³C NMR, and high-resolution mass spectral studies. Their surface active properties were evaluated by the wilhelmy plate method at 25 °C and physical parameters like CMC, γ_CMC, π_CMC, C₂₀, τ_CMC, and A_min were calculated. The Krafft temperature values of C-BP-1, C-BP-4, and C-BP-6 are lower than 0 °C, suggesting high-potential industrial application. All synthesized compounds but C-BP-F exhibit great antimicrobial ability against Gram-positive bacteria (S. aureus [ATCC 25923] and C. glutamicum [ATCC 13032]) while inadequate antimicrobial ability against Gram negative strains (E. coli [ATCC 25922] and P. aeruginosa [ATCC 27853]).     

Synthesis and Properties of New Cleavable Cationic Surfactants Containing Carbonate Groups

A novel series of cleavable alkyltrimethylammonium surfactants with different hydrocarbon chain lengths (C8–16) were synthesized. A carbonate break site inserted between the polar head and the hydrocarbon chain makes these compounds hydrolyzable. The reagents used are renewable, (bio)degradable, or reusable. The hydrolysis of these cleavable surfactants will lead to the generation of fatty alcohols and choline, which is an essential biological nutrient. The surface activities in aqueous solution of the synthesized carbonates fulfill the requirement of being good surfactants. In addition, the cleavable compounds containing n-decyl and n-dodecyl chains showed similar or higher antimicrobial activities when compared to a non-cleavable analog.     

磺酸盐表面活性剂研究进展

综述了磺酸盐表面活性剂的研究现状和正在开发的新品种,并对其合成技术路线和方法进行了概述,尤其是对链烃磺酸盐、脂肪酸酯磺酸盐、双芳环醚磺酸盐、二聚磺酸盐表面活性剂的合成和性质进行了重点介绍。我国应大力开发原料易得、活性高的脂肪酸磺酸盐、脂肪醇醚磺酸盐表面活性剂,注重结构新颖、性能独特的Gem in i表面活性剂的基础研究以适应各行业的需求。引用文献41篇。     

Novel Imidazolium-Based Gemini Surfactants: Synthesis, Surface Properties, Corrosion Inhibition and Biocidal Activity Against Sulfate-Reducing Bacteria

Three novel imidazolium-based gemini surfactants had been synthesized and characterized using different spectroscopic techniques. The surface properties of the synthesized surfactants were determined using surface tension measurements at 20 °C. The surface parameters including critical micelle concentration (CMC), π _CMC, Pc₂₀, Γ_max and A _min were determined. The synthesized compounds were evaluated as corrosion inhibitors for carbon steel in 0.5 M HCl solution using the weight loss and polarization techniques. The biological activity of these surfactants was evaluated against sulfate reducing bacteria using most probable number method. The results indicate that the synthesized compounds have good surface properties and are proper corrosion inhibitors for low carbon steel, with a high inhibition efficiency observed around their CMC. These compounds exhibit a significant biocidal activity against sulfate reducing bacteria.     

Gemini表面活性剂的研究进展

Gemini表面活性剂是一类新型的双亲水基双疏水基的两亲表面活性剂,其独特的结构使其具有许多特殊性质和良好性能。综述了Gemini表面活性剂的研究进展、合成概况以及物化性质的研究。     

Synthesis,Characterization and Evaluation of the Surface Active Properties of Novel Cationic Imidazolium Gemini Surfactants

New imidazolium gemini surfactants were synthesized by reaction of epichlorohydrin with long chain fatty alcohols furnishing products 2-(alkoxymethyl)oxirane followed by their subsequent treatment with imidazole resulting in the formation of 1-(1H-imidazol-1-yl-3 alkoxy)propane-2-ol which on subsequent treatment with 1,2-dibromoethane and 1,3-dibromopropane resulted in the formation of title gemini surfactants:1,2-bis(1(3-alkoxy-2-hydroxypropyl)-1H-imidazol-3-ium)ethane bromide (7), 1,3-bis(1(3-alkoxy-2-hydroxypropyl)-1H-imidazol-3-ium)propane bromide (8), 1,2-bis(1(3-alkoxy-2-hydroxypropyl)-1H-imidazol-3-ium)ethane bromide (9), 1,3-bis(1(3-alkoxy-2-hydroxypropyl)-1H-imidazol-3-ium)propane bromide (10), 1,2-bis (1(3-alkoxy-2-hydroxypropyl)-1H-imidazol-3-ium)ethane bromide (11) and 1,3-bis (1(3-alkoxy-2-hydroxypropyl)-1H-imidazol-3-ium)propane bromide (12). Their identification was based on IR, ¹H-, ¹³C-NMR, DEPT, COSY and mass spectral studies. Their surface active properties were also evaluated on the basis of surface tension and conductivity measurements.     

酯基型双子表面活性剂的合成及驱油性能

采用丁二酸酐、N,N-二甲基乙醇胺和溴代烷C_nH_(2n+1)Br(n=10、12、14、16、18)通过两步反应制备了含酯基的阳离子双子表面活性剂[简称为GSn-EG-n(n=10、12、14、16、18)]。利用FTIR、~1HNMR对GS14-EG-14结构进行表征,用表面张力仪、电导率仪、荧光光谱仪(FLD)、光学接触角测量仪和界面张力仪对GSn-EG-n的溶液性质进行测定。结果表明,随着碳链长度的增加,表面活性剂越易聚集缔合成胶束,GS18-EG-18临界胶束浓度(CMC)最低达到2.14×10~(-5)mol/L,GS14-EG-14溶液的表面张力最低降至33.50 m N/m。通过测定不同温度下溶液的电导率,发现其电导率随着温度的升高而增大。乳化性和润湿性测试结果表明,GS14-EG-14乳化系统中,油/水分离时间达到180 min,且在聚四氟乙烯板(简称PTFE)上的接触角为69.3°,说明GS14-EG-14具有很好的乳化性能和润湿性能。GS18-EG-18仅用28 min可以将油/水界面张力降低至8.6×10~(-3)m N/m。GSn-EG-n的最终驱油效率达54.2%。     

Waste Cooking Oil-Based Novel Gemini Imidazolinium Surfactants With Carbonate Linkage: Green Synthesis,Characterization and Properties Evaluation

Imidazolinium surfactants belong to the category of cationic surfactants that have already gained the great interest of researchers due to their varied range of commercial applications. With the advancement in the field of surfactants research, imidazolinium surfactants are being converted into their corresponding gemini surfactants. Gemini surfactants are known to have exceptional self‐assembling characteristics and exclusive interfacial activity that include much lower CMC and better ability to reduce surface tension than their conventional monomeric counterparts. Long reaction time associated with conventional thermal synthetic procedures and high production costs are the two major issues involved in the synthesis of gemini surfactants. The present research work involves the microwave synthesis of novel gemini imidazolinium surfactants with carbonate linkage. In order to synthesize cost effective gemini surfactants, waste cooking oils have been used as raw materials. Structural characterization of synthesized gemini surfactants has been achieved through ¹H‐NMR, ¹³C‐NMR and FT‐IR.     

新型Gemini阳离子表面活性剂的合成和性能（3）—在烷基链中引入易水解基团促进生物降解

概述了烷基链中含有酰受基和酯基的Gemini阳离子表面活性剂的合成,表面活性和生物降解性,含有酰胺基的Gemini阳离子具有优良的表面活性,但几乎不能生物降解,而含有酯基的Gemini阳离子不仅具有优良的表面活性,而且具有良好的生物降解性。     

Clay Swelling Inhibition Using Novel Cationic Gemini Surfactants with Different Spacers

Hydration of shale formation by water-based drilling fluids leads to several problems, such as the collapse of boreholes, tight holes, and stuck pipe, which may impede further drilling and time loss in rectifying the problems, leading to heavy economic losses. This study reports the development of new gemini cationic surfactants as shale-swelling inhibitors. These gemini surfactants are structurally similar but differ in terms of the spacer group. Saturated butyl group ( GS1 ) and unsaturated 2-butenyl ( GS2 ) and 2-butynyl ( GS3 ) were introduced as spacer groups of gemini surfactants. To assess the performance of new gemini cationic surfactants, two reliable clay sources were considered. The first clay is from an unconventional formation and the second clay is sodium bentonite. The inhibition characteristics of gemini surfactants were evaluated using dynamic swelling, hot rolling, rheology, and filtration experiments. Different formulations based on commercially available solutions for shale-swelling inhibitors were applied and compared with cationic shale inhibitors. It was observed that the new gemini cationic surfactants with different spacers (saturated and unsaturated) reduced the shale swelling by different percentages. The GS2 surfactant, containing an unsaturated double bond proved to be a good swelling inhibitor as compared to GS1 and GS3 . It also showed acceptable performance compared with the common shale inhibitor (KCl) used in the industry. The addition of surfactant has less impact on the rheological properties as compared to KCl. The filtration properties of the base mud were unchanged when surfactants were used. However, the commercial inhibitor, KCl, significantly increased the filtration volume that is associated with the disintegration of the clay. In summary, unlike commercial inhibitors, the synthesized surfactants reduced the clay swelling without affecting the other properties of the drilling fluids.     

以金刚烷为联接链的Gemini表面活性剂合成与性能

以1,3-金刚烷二甲酸为起始原料,合成了3种以金刚烷为联接链的具不同疏水链长的Gemini表面活性剂（nP-Ad-Pn,n=12,14,16）。用FTIR、1HNMR、ESI-MS对目标化合物的结构进行了表征。采用表面张力、电导率和稳态荧光光谱测定了金刚烷Gemini表面活性剂的表面活性、胶束化热力学参数和胶束微极性。结果显示：白金环法测得nP-Ad-Pn在25℃下的临界胶束浓度分别为6×10-4、1×10-4和2.5×10-5 mol·L-1,∆G0m和∆H0m均为负值说明表面活性剂胶束形成是一个自发且放热的过程。化合物对金黄色葡萄球菌、枯草杆菌、大肠杆菌、绿脓杆菌、副溶血性弧菌抑菌活性的测定结果表明,12P-Ad-P12对5种菌株的MIC值在0.2～4.2 mg/L,显示出很强的抑菌活性。     

Gemini Surfactants Foam Formation Ability and Foam Stability Depends on Spacer Length

A series of cationic gemini surfactants containing different spacer length were synthesized and analyzed structurally. It was shown that the surface tension (σ) and critical micelle concentration (CMC), which had a maximum for the n-C₄H₈ spacer depended on the spacer length. The foaming ability and foam stability are high for the gemini surfactants with short spacers (C₂H₄ to n-C₄H₈), while longer spacers lead to a distinct decrease of these foam parameters. Foaming properties are discussed in terms of configuration and conformation of a surfactant molecule and in relation to micellization state kinetic.     

新型Gemini阳离子表面活性剂的合成和性能（1）：从长链烷基二甲基胺及其盐酸盐和环氧氯丙烷合成双烷基双季铵盐阳离子

概述了从长链烷基二甲基叔胺及其盐酸盐和环氧氯丙烷或其他连接剂在温和条件下合成新型双烷基双季铵盐型阳离子表面活性剂的方法,产品的表面活性以及烷基链长、连接基团结构对产物表面活性的影响。     

唑型双子表面活性剂的合成和性能研究

以咪唑、以咪唑,溴乙酸,溴代十四烷和二元醇为主要原料,采用三步法合成了三种新的咪唑型双子表面活性剂,简记[C_(14)-n-C_(14)]Br_2。通过核磁氢谱和红外光谱对三种产物的结构进行表征,证明合成的产物为目标产物。并采用表面张力法得出三种表面活性剂的表面张力曲线,进而计算临界胶束浓度(CMC)等一系列表面性能参数,结果表明,连接基越短的咪唑型双子表面活性剂拥有更低的CMC,更高的界面活性。     

m-s-m-s-m型三联新型季铵盐表面活性剂的合成与性能测定

Gemini新型表面活性剂是当今科学研究的热点。本研究采用二乙烯三胺与甲醛、甲酸进行甲基化反应合成了中间体五甲基二乙烯三胺,并通过红外光谱分析及电位滴定法分析测定其纯度。然后,在碳酸钠的催化作用下,与溴代十二烷在乙醇体系中发生季铵化反应生成最终产物m-s-m-s-m型三联新型季铵盐表面活性剂。在此基础上,通过单因素实验考察了原料摩尔比、反应温度、反应时间等因素对反应产率的影响。最后确定最佳摩尔比为溴代十二烷过量5%～10%、最佳温度为87℃、最佳反应时间为5 h。最后对提纯后产品的最低胶束浓度(cmc)、γcmc、克拉夫(Krafft)、熔点等性能进行了测定。