新一代表面活性剂_Geminis_赵剑曦

新型阴离子Gemini表面活性剂的发展探究-高分子材料论文-化学论文——文章均为WORD文档，下载后可直接编辑使用亦可打印——摘要：阴离子Gemini表面活性剂具有优良的乳化性、发泡性、去污能力、耐盐性、分散性、易生物降解性，在日用化工、三次采油、金属防护、环境保护、新型材料等领域具有广泛的用途。

研究综述了磺酸盐型和羧酸盐型Gemini表面活性剂的分类、合成及应用，展望了新型阴离子Gemini表面活性剂的发展前景。

关键词：阴离子；Gemini; 表面活性剂；合成；Abstract: Anionic Gemini surfactants have excellent emulsifying, foaming, stain removal, salt tolerance, dispersion and biodegradability, which are used widely in daily chemicals, tertiary oil recovery, metal protection, environmental protection, new materials and other fields. This review summarized the classification, synthesis and applications of sulfonate and carboxylate-based anionic Gemini surfactants, and the development of new anionic Gemini surfactants was prospected.Keyword: anionic; Gemini; surfactants; synthesis;双生表面活性剂、孪连表面活性剂又称双子表面活性剂（Gemini surfactant）, 常见Gemini表面活性剂是通过一个桥联基将两个疏水链、两个亲水基或接近亲水基连接在一起而形成的一类新型表面活性剂[1].Gemini表面活性剂分子中至少含有两条疏水基、两个亲水基和桥联基团，Gemini表面活性剂可以竖直紧密排列于界面之间，具有高表面活性和界面性能，抗盐、抗沉积、耐温耐盐性好，在石油开采方面具有广泛的应用[2];此外Gemini表面活性剂溶液具有良好的增溶和增流作用、湿润性能好、Kraff点低以及吸附量低等优点，可作为洗涤剂、柔软剂、分散剂、印染固色剂、乳化剂、润湿剂等广泛应用于日化、皮革、纺织、造纸、农业及新型材料等领域[3-5].阴离子Gemini表面活性剂是一类具有阴离子亲水性基团的双子表面活性剂，具有乳化能力强、润湿反转能力强、界面活性高、吸附量少、易生物降解等特殊优势，且阴离子Gemini表面活性剂种类多、生产原料易得可以广泛用作洗涤剂、起泡剂、润湿剂、乳化剂和分散剂使用[6-9].常见阴离子Gemini表面活性剂的主要有磺酸盐型、羧酸盐型、磷酸盐性、硫酸酯盐型等，文章主要对磺酸盐型和羧酸盐型阴离子Gemini表面活性剂的合成和应用进行了综述，对新型阴离子Gemini表面活性剂的发展趋势进行了分析和展望。

表面活性剂发展方向1. 新一代表面活性剂Gemini 目前已经合成的低聚表面活性剂有二聚体、三聚体和四聚体等，其中最引人注目的是二聚体，结构示意图见图1，二聚表面活性剂最早被合成于1971 年[4-5] ，后因其结构上的特点而被形象地命名为Gemini （英文是双子星之意）表面活性剂。

表面活性剂Gemini （或称dimeric ）是由两个单链单头基普通表面活性剂在离子头基处通过化学键联接而成，因而阻抑了表面活性剂有序聚集过程中的头基分离力，极大地提高了表面活性。

与当前为提高表面活性而进行的大量尝试，如添加盐类、提高温度或将阴离子表面活性剂与阴离子表面活性剂混合相比较，Gemini 表面活性剂是概念上的突破，因而被誉为新一代的表面括性剂。

在Gemini 表面活性剂中，两个离子头基是靠联接基团通过化学键而连接的，由此造成了两个表面活性剂单体离子相当紧密的连接，致使其碳氢链间更容易产生强相互作用，即加强了碳氢链问的疏水结合力，而且离子头基间的排斥倾向受制于化学键力而被大大削弱，这就是Gemlrd 表面活性剂和单链单头基表面括性剂相比较，具有高表面括性的根本原因。

另一方面。

在两个离子头基问的化学键联接不破坏其亲水性，从而为高表面活性的C~mini 表面活性剂的广泛应用提供了基础。

通过化学键联接方法提高表面活性和以往通常应用的物理方法不同，在概念上是一个突破。

图2炔醇类Gemini表面活性剂Genfini 表面活性剂的优良性质：实验表明，在保持每个亲水基团联接的碳原子数相等条件下，与单烷烃链和单离子头基组成的普通表面活性剂相比，离子型Gemini 表面活性剂具有如下特征性质：（1）更易吸附在气/ 液表面，从而更有效地降低水溶液表面张力。

（2）更易聚集生成胶团。

（3）Gemini 降低水溶液表面张力的倾向远大于聚集生成胶团的倾向，降低水溶液表面张力的效率是相当突出的。

（4）具有很低的Krat~ 相转移点。

两种系列新型季铵盐Gemini表面活性剂的杀菌活性王贻杰;毛宁;赵剑曦【期刊名称】《集美大学学报（自然科学版）》【年(卷),期】2004(009)002【摘要】考察系列季铵盐Gemini表面活性剂C12-S2En-C12·2Br(n=1,3)和C12-S5-C12·2Br(s=2,3,4,6)对大肠杆菌、金黄色葡萄球菌和白色念珠菌的悬液定量杀菌效果,并与十二烷基三甲基溴化铵(C12TABr)的效果比较.结果表明,C12-S2En-C12·2Br和C12-S5-C12·2Br具有比C12TABr优良得多的杀灭大肠杆菌、金黄色葡萄球菌和白色念珠菌的能力.作用10 min后,对这3种菌均达到杀灭99.9%以上的效果.【总页数】5页(P100-104)【作者】王贻杰;毛宁;赵剑曦【作者单位】福建师范大学生物工程学院,福建,福州,350007;福建师范大学生物工程学院,福建,福州,350007;福州大学化学系,福建,福州,350002【正文语种】中文【中图分类】O626【相关文献】1.新型双苯基型季铵盐Gemini表面活性剂的合成及其表面活性 [J], 祝勃勃;贾朝霞;马丽华;邹专政;都伟超2.新型多羟基季铵盐Gemini表面活性剂的合成及其表面活性 [J], 裴晓梅;宋冰蕾;许宗会;安文;崔正刚3.新型不对称季铵盐Gemini表面活性剂的合成及其表面活性 [J], 许宗会;裴晓梅;宋冰蕾;史慧;崔正刚4.一系列新型季铵盐表面活性剂的杀菌性能研究 [J], 吕雅娟;蒋晓慧;陈志5.季铵盐Gemini表面活性剂杀菌活性及其与分子结构的关联 [J], 赵剑曦;毛宁;游毅;王贻杰因版权原因，仅展示原文概要，查看原文内容请购买。

收稿日期:2004206224;修回日期:2004209205联系人简介:史俊(1963-),男,副教授,主要从事有机分析教学及精细化学品的合成。

Email :qdli @文章编号:100421656(2005)0320293206G emini 表面活性剂的研究进展史俊,李谦定,夏小春(西安石油大学化学化工学院,陕西　西安　710065)摘要:G emini 型表面活性剂是一类双亲油基双亲水基的两亲物,因其特殊的二聚结构从而具有许多特殊的物化性质。

综述了G emini 型表面活性剂的研究进展、合成方法、物化性质及其应用。

关键词:G emini 型表面活性剂;合成;性质;应用中图分类号:O623.731 文献标识码:A传统表面活性剂是具有单头基(亲水基)单尾基(疏水基团,一般为长的碳链)的一类两亲物,其结构如图1a 所示。

近三十年来,许多特殊结构的新型表面活性剂引起了科研工作者的兴趣。

如:双端基型(bola 型,如图1b )表面活性剂在生物膜图1　表面活性剂的结构Fig.1　The structure of sur factants模拟方面具有良好的前景[1];双头双尾型(G emini型,如图1c )表面活性剂因其特殊的化学性质而引发研究热潮;另外,双头三尾(如图1d )、三头三尾(trimeric 型,如图1e )以及三个以上头三个以上尾型表面活性剂也见诸报道[2]。

G emini 型表面活性剂是一类双亲油基双亲水基的两亲物。

“G emini ”在天文上的意思为双子星座,用在这里形象地表达了这类表面活性剂的分子结构特点。

从分子结构看,它又相似于两个传统表面活性剂分子的聚结,故有时又称之为二聚(dimeric )表面活性剂,国内有人[3,4]将它翻译为双子型或孪二型表面活性剂。

G emini 型表面活性剂同三头三尾以及三个以上头三个以上尾型表面活性剂应该统称为低聚表面活性剂(olig omeric surfactants )[5]。

新型Gemini表面活性剂及其研究进展摘要Gemini 型表面活性剂是一种具有特殊结构的新型表面活性剂, 被称为第三代表面活性剂，且其优良的性能受到越来越多的关注。

总结了近几年来国内外Gemini 型表面活性剂的最新研究成果,对其结构、性能和应用作了较全面的评述。

AbstractThe specific properties of Gemini surfactants was known as“The Third Generation”and its excellent functions we re being taken into consideration .in this paper,the recent progress of Gemini surfanctants In side and out are summarized ,in the meantime ,its strctur e﹑property and application integrity assessment are discussed.前言表面活性剂是重要的工业助剂之一，可显著改变物质表(界)面的物理化学性质，具有乳化、分散、絮凝、润湿、发泡、铺展、渗透、润滑、抗静电以及杀菌等功能。

传统的表面活性剂分子由一条疏水链和一个亲水头基组成。

由于分子结构不对称而产生自组织行为和降低水溶液表(界)面张力的能力。

1991年Menger 合成了以刚性基团联接离子头基的双烷烃链表面活性剂，并给这类顺序排列的两亲分子命名为：Gemini（双子）表面活性剂[1]。

该表面活性剂是一族性能优异的新型表面活性剂，其分子中含有两条疏水链、两个亲水基和一个间隔基团，间隔基团可以是柔性基团或刚性基团。

( I 为疏水链; R 为亲水基; Y 为联接链)A ,B 为 Gemini 型表面活性剂C 为普通型表面活性剂根据亲水基所带电荷种类可分为阳离子型（胺盐型、季铵盐型）、阴离子型（磺酸盐型、羧酸盐型、磷酸盐型、硫酸盐型）、非离子型（聚氧乙烯型、脂肪酸多元醇酯型）、混合型（阴阳离子、离子对、阴离子-非离子、阳离子-非离子）等[6]。

文献综述题目：新型表面活性剂Gemini性能及其研究进展姓名：XXX学号：XXXXXXXXX专业：有机化学二零一二年十二月一日新型表面活性剂Gemini性能及其研究进展摘要Gemini是一种新型表面活性剂，它以联结基团联结在头基或靠近头基处，使得表面活性剂的表面活性大幅度提高。

与一般的表面活性剂相比, Gemini表面活性剂是概念上的突破，被誉为新一代的表面活性剂。

本篇综述详细介绍了Gemini表面活性剂的性能以及研究进展。

关键词Gemini；双子；联结基团；高表面活性传统表面活性剂分子中只有1 个亲水基和1 个亲油基，由于这种表面活性剂疏水链之间的缔合作用，离子头基间电荷斥力和水化作用引起的分离作用存在平衡，使得它们在界面或分子聚集体中不能更紧密排列，因而降低表面张力的能力有限。

近年，一种新型表面活性剂引起重视，即用化学键将2个或2 个以上的相同或不同的两亲成分联结起来，成为具有多个亲水基和多个疏水长链的表面活性剂，统称为多聚表面活性剂，其中以二聚体研究较多。

由于该类表面活性剂的亲水基团是以共价键结构连接，可实现亲水基之间的更紧密排列，因而具有更高的表面活性，同时还有许多特殊性能。

1结构和性能1.1 Gemini表面活性剂特殊结构示于图1[1]Gemini表面活性剂的疏水基有两类：一类为纯碳链，另一类是碳链中有其它基团如酯基、酰胺基、氟等。

亲水基可以是阳离子型（主要是季铵盐），阴离子型（主要有羧酸盐、磷酸酯盐、磺酸盐及硫酸酯盐），非离子型（主要是多羟基和环氧甲烷缩合基团）。

1.2 Gemini表面活性剂优良性能Gemini表面活性剂由于其特殊结构，有许多传统表面活性剂所不具备的特性[2~3]，现列举如下：①易吸附在气液表面，从而更有效地降低表面张力。

②极易聚集成胶团，cmc 值比传统表面活性剂溶液低。

③具有较低的表面活性剂应用温度下限(Krafft点) 。

④具有优良的润湿性，洗涤去污能力强。

⑤与传统非离子型表面活性剂复配时产生更大的协同效应，可大幅度降低体系的表(界)面张力。

专利名称：一种季铵盐型Gemini表面活性剂及其制备、产品和应用
专利类型：发明专利
发明人：胡智渊,杨春鹏,蒋庆哲,赵晶晶,宋昭峥
申请号：CN201610313056.1
申请日：20160512
公开号：CN106008255A
公开日：
20161012
专利内容由知识产权出版社提供
摘要：本发明提供了一种季铵盐型Gemini表面活性剂及其制备、产品和应用。

所述表面活性剂如式(I)所示，其中，R为饱和或不饱和的主链碳原子数为16-26的烷基、或饱和或不饱和的主链碳原子数为16-26的含有酰胺基的烷基；R为甲基、乙基或羟乙基；R选自和亚乙基中的一种；X为氯或溴。

本发明合成的Gemini表面活性剂，耐温最高可达160℃，比现有常规的双子表面活性剂耐温性能更佳。

申请人：中国石油大学(北京)
地址：102249 北京市昌平区府学路18号
国籍：CN
代理机构：北京三友知识产权代理有限公司
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Gemini表面活性剂乙烷基-α,ω-双十四烷基二甲基溴化铵产生的高稳定泡沫吴晓娜;邹文生;赵剑曦【摘要】报道了由gemini表面活性剂乙烷基-α,ω-双十四烷基二甲基溴化铵(14-2-14)产生的高稳定泡沫体系泡沫塌陷到初始高度一半所对应的时间(t1/2)用来表征泡沫的稳定性.测得14-2-14体系的t1/2高达961 min,远大于乙烷基-α,ω-双十二烷基二甲基溴化铵(12-2-12)产生泡沫的t1/2(754 min),表明带有一根短联接链和两条长尾链的gemini表面活性剂是高效的泡沫稳定剂.为了揭示界面弹性与泡沫稳定性之间的关联,测量了表面活性剂吸附膜的扩张流变行为.在指定的表面过剩量下,吸附膜的高频极限弹性再一次被发现与泡沫稳定性相关,较大的极限弹性很好地对应更加稳定的泡沫.%This paper reports a highly stable foam system generated by the gemini surfactant ethanediylα,ω-bis(tetradecyldimethylammonium bromide) (referred to as 14-2-14).The time measured for the collapse of the foam to half its initial height was used to characterize the foam stability; it was as high as 961 min for this system and significantly longer than that (754 min) for ethanediyl-o,ω-bis(dodecyldimethylammonium bromide) (12-2-12) foams.Thus the gemini surfactant structure of a short spacer together with two long tails enabled it to be a highly efficient foam stabilizer.The dilational rheology of the adsorbed films revealed the relationship between the interfacial elasticity and the foam stability.The high-frequency limit of elasticity of the adsorbed film at a specific surface coverage was again found to indicate foam stability.A larger limit of elasticity indicated a more stable foam.【期刊名称】《物理化学学报》【年(卷),期】2012(028)005【总页数】5页(P1213-1217)【关键词】泡沫稳定剂;Gemini表面活性剂;短联接链;长尾链;高界面弹性【作者】吴晓娜;邹文生;赵剑曦【作者单位】福州大学化学化工学院,胶体与界面化学研究所,福州350108;福州大学化学化工学院,胶体与界面化学研究所,福州350108;福州大学化学化工学院,胶体与界面化学研究所,福州350108【正文语种】中文【中图分类】O646Recently we reported stable foam systems generated by cationic gemini surfactants,2-hydroxyl-propanediyl-α,ω-bis(dimethyldodecylammonium bromide),2-hydroxyl-butanediyl-α, ω-bis(dimethyldodecylammonium bromide)or 2,3-hydroxylbutanediyl-α,ω-bis(dimethyldodecylammonium bromide)(referred to as 12-3(OH)-12,12-4(OH)-12,and 12-4(OH)2-12,respectively).1These surfactants all contained a hydroxyl-substituted spacer and thus produced the intermolecular hydrogen bonding for those adsorbed at the air/water interface,2which made the packing of molecules tighter and increased the cohesion of surfactant within the monolayer and enhanced the foam stability.1,3 Among these surfactants,12-3(OH)-12 can more efficiently stabilized the foam than 12-4(OH)-12 or 12-4(OH)2-12.This result suggests that even though there exists the intermolecular hydrogen bonding,the spacer length may still dominate the packing of surfactant at the air/water interface.Indeed,ethanediyl-α,ω-bis(dimethyldodecylammonium bromide)(12-2-12) has been found to efficiently stabilize soap film even at very low concentrations.4Illuminated by these results,we expanded the study to ethanediyl-α,ω-bis(dimethyltetradecyl-ammonium bromide)(14-2-14).14-2-14 has longer alkyl tails than 12-2-12 and therefore is expected to increase the cohesion of surfactant within the monolayer and better to stabilize foam.In the present work,the foam stability generated by 14-2-14 and the dilational rheology of the adsorption films were studied in detail. For comparison,12-2-12 was also examined.2.1 MaterialsGemini surfactants,ethanediyl-α,ω-bis(tetradecyldimethylammonium bromide)and ethanediyl-α,ω-bis(dodecyldimethylammonium bromide),the chemical structures of which are shown in Scheme 1,were synthesized in our laboratory according to the method reported by Zana et al.5The products were confirmed by1H NMR and elemental analysis.All the solutions were prepared with Milli-Q water(resistivity:18.2 MΩ· cm).2.2 MeasurementsFoam stability was determined using a setup reported in literature.1The test solution of 5 mL was filled in a cylindrical glass container(25-mm internal diameter,140-mm height),at the bottom of which a porous glass disc was fixed.The cylindrical glass container was put in a water bath with aconstant temperature of(25.0±0.1)°C.The so lution was bubbled by air with a constant flow rate of 68 mL·min-1,and foam was generated until a designed 40 mm height that corresponded to a volume of 20 cm3and then the valve was shut immediately.Foam stability was characterized by time,t1/2,needed for the collapse of foam to half its initial height.The experiments were repeated at least three times,and the average value was adopted as t1/2.Interfacial dilational rheology was measured in an optical angle meter OCA-20 with oscillating drop accessory ODG-20. The equilibrated interface as indicated by a constant surface tension value was disturbed by sinusoidal oscillations produced by a function generator,which resulted in interfacial periodic expansion and contraction.The accessible frequency range was 0.01-1 Hz and the variation of the relative area(A) was～6%.These conditions followed the range of linear viscoelasticity.The changes in drop shape were monitored by CCD camera with a minimum of 50 frames per second.At the end of the experiment,the software retrieved the images and calculated the changes in both interface tension(dγ)and area(dA), which gave the interface dilatational modulus ε*=dγ/ing a Fourier transform analysis,the phase angle(θ)was determined.Thus,the dilational elasticity ε and dilational viscosity η could be calculated by the following relations:where ω=2πv,v is the frequency of sinusoidal oscillation.3.1 Foam stabilityFig.1 shows the apparent pictures where both 12-2-12 and 14-2-14generate foams with many gas bubbles separated by liquid films.Fig.2 illustrates the semi-logarithmic plots of the foam stability,represented as the time t1/2needed for the collapse of foam to half its initial height,as a function of surfactant concentration.As the surfactant concentration increases,t1/2rises rapidly to a plateau at respective critical micelle concentration (cmc)as shown by arrow.The maximum tmax1/2for 12-2-12(754 min)is greatly larger than that of 12-3(OH)-12(406 min)as reported previously,1verifying our inference that the gemini with a short spacer could more efficiently stabilize the foams. Significantly,14-2-14 produces tmax1/2as high as 961 min.This tmax1/2 is 4-folds that of traditional cationic surfactant,tetradecyltrimethylammonium bromide(C14TABr,240 min),which is generally considered as the corresponding monomer of 14-2-14, and is also considerably larger than that of 14-3(OH)-14(660 min).6This means that a highly stable foam system is found.Here we would like to mention another homologue,ethanediyl-α,ω-bis(hexadecyldimethylammonium bromide)(16-2-16) which has longer alkyl tails than 14-2-14.Unfortunately,16-2-16 cannot form normal foams due to the reason of adsorption kinetics analogous to 16-3(OH)-16 as discussed in our previous study.63.2 Interfacial dilational rheologyIn general,foam stability is relevant to the interfacial elasticity of the adsorption film.3,7-13In this section,we discuss the dilational rheology of the adsorption films.Fig.3 shows the frequency-dependent variation of interfacial dilational elasticity (ε)and dilational viscosity(η)at different 14-2-14 concentrations(the similar results of 12-2-12 are not shown).At a fixed working frequency,both ε and η clearly exhibit concentration dependence(Fig.4)analogous to the observations for other surfactant systems.7,14The maximum in the concentration-dependent plot of ε has been explained by different effects induced by increased surfactant concentration,7which results in gradual increase in the surface excess Γ and noticeable enhancement in the molecular exchange between bulk and surface.The fast exchanges can even the surface tension gradient out rapidly. Thus,at low concentrations ε is governed by increased surface excess,whereas at high concentrations the molecular exchange plays a dominant role.The competition of the both determines a maximum in the ε(c)curve.Lucassen-van den Tempel(LVT)model describes the viscoelastic behavior of soluble monolayer over the range of low frequencies.15,16This model assumed that the material transport involved in the adsorption kinetics is governed only by diffusion without energy barriers and considered the instantaneous cou-pling between the interface rheology and the adsorption kinetics.The model predicted the viscoelastic moduli through the following equations:withwhere ε0is th e theoretical high-frequency limit of the surface elasticity and ω0is the molecular exchange parameter.Fig.5 shows some typical results for 14-2-14 fitted by Eqs.(3)and (4),in which the LVT model well describes the experimental data.Since the high-frequency limit is not experimentallyincluded,the fitting values of ε0,fitwere adopted as ε0by the procedure suggested by Stubenrauch and Miller,7in which the couples of ε0,fitandω0,fitthat best describe both the experimental ε(v,c)and η(v,c)curves,were determin ed.Similarly,ε0,fitis also concentration-dependent as seen in Fig.6. In our recent study,we stressed that the relation between foam stability and interfacial elasticity of adsorption film is tenable only on the basis of high-frequency limit ε0(or ε0,fit)wh ich excludes the influence of frequency as well as of identical surface excesses rather than the same bulk concentrations.1Analogous to the previous work,here we also adopted 80%of the surface excess as the comparison level for 12-2-12 and 14-2-14.The corr esponding ε0,fitcan be obtained by combining Fig.6 and Fig.7,the latter represents the adsorption isotherms of Frumkin form obtained through fitting the surface tension data by Szyszkowski formula and then calculating the surface excesses by Gibbs equation.17Thus,the ε0,fitat 80%surface excess is 117.2 mN·m-1for 12-2-12 and 145.3 mN·m-1for 14-2-14. 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