CN1236845C - 作为极端环境用表面活性剂/添加剂的二(全氟烷基磺酰基)酰亚胺及其盐,以及使用方法 - Google Patents
作为极端环境用表面活性剂/添加剂的二(全氟烷基磺酰基)酰亚胺及其盐,以及使用方法 Download PDFInfo
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- CN1236845C CN1236845C CNB028094905A CN02809490A CN1236845C CN 1236845 C CN1236845 C CN 1236845C CN B028094905 A CNB028094905 A CN B028094905A CN 02809490 A CN02809490 A CN 02809490A CN 1236845 C CN1236845 C CN 1236845C
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Abstract
本发明提供了二(全氟烷基磺酰基)酰亚胺及其盐作为极端环境用表面活性剂或添加剂的用途。
Description
发明领域
本发明涉及二(全氟烷基磺酰基)酰亚胺及其盐作为水性或非水性(或有机)溶液中的表面活性剂或添加剂的用途。更具体的是,本发明涉及在溶液中作为极端环境用表面活性剂或添加剂的二(全氟烷基磺酰基)酰亚胺及其盐。
发明背景
表面活性剂通常认为是当溶解在溶液(例如,水)中时任何能降低表面张力或者降低两液体或液体和固体之间界面张力的化合物。本文所述的添加剂是当加到基础水力流体时任何能改善水力流体腐蚀性能的化合物。表面活性剂/添加剂的选用随应用、体系或者所用的溶液而改变。当评价表面活性剂/添加剂的实用性时,还要考虑一些其它因素,包括:表面活性剂/添加剂在所用体系中的溶解性、pH、铺展和/或流平所需的最终表面张力、所述体系组分的腐蚀性、所需的导电性以及表面活性剂的挥发性。
表面活性剂可以用于各种应用中,包括水性或非水性(即有机)溶液中。涉及极端或恶劣环境的应用包括,但不限于,在制备半导体器件中使用的蚀刻溶液、电化学电镀液和抛光液、晶片清洁和抛光溶液、各向异性蚀刻溶液、用于碱性电池的电解液、以及用于半导体制造的显影液。“极端”或“恶劣”环境定义为在其中常规烃基表面活性剂/添加剂会降解的应用。本文中,降解定义为阴离子表面活性剂质子化作用、或者所述表面活性剂化学结构的降解或者改变(例如,聚合),后者会导致表面张力改变并由此降低表面活性剂的性能。
对水性溶液来说,极端环境条件包括,但不限于,热、光、辐射、氧化/还原势、高压、高剪切、高pH或低pH、或者存在腐蚀试剂。所述pH通常为低(即,酸性)或者高(即,碱性)。通常,对水性溶液来说,这些应用在最低限度上也具有极端的pH和腐蚀性。
对非水性溶液来说,极端环境条件包括,但不限于高压、高温(即,至少200℃)、高剪切、环境条件(微量水)、或者腐蚀试剂等。
在这些条件下,大多数的烃表面活性剂要么会化学降解,要么会物理降解。因此,需要在极端环境中不会降解的非烃基表面活性剂。
已经使用碳氟化合物表面活性剂如全氟辛磺酰氟(POSF),来自如K+-OSO2C8F17的表面活性剂。但是,这些表面活性剂在所述环境中持续或者最终降解成其它含全氟辛基的化合物。据报道,某些包含全氟辛基的化合物在活生物体内的生物消除速度低。这一趋势已经成为一些含氟化合物潜在的关注点。可见,例如美国专利No.5,688,884(Baker等)。由于与使用表面活性剂本身或者与来自其制造的废液/排出物有关的流体会发生将表面活性剂及其降解产物加入所述环境中的情况。
因此,需要含氟组合物能有效地提供所需的表面活性剂性能,并能更快地从活的生物体中消除(包括所述组合物及其降解产物)。
因此,需要在极端环境应用中有效地起作用、能更快地从活的生物体中消除并且能经济有效制备的表面活性剂或添加剂。这些表面活性剂前体的生物累积性要求比所述来自POSF的物质低,防止可能从制造液中引入会生物累积的物质。
发明概述
本发明提供了作为极端或恶劣环境用表面活性剂或添加剂的二(全氟烷基磺酰基)酰亚胺及其盐。有利的是,本发明的表面活性剂或添加剂包含全氟化酰亚胺阴离子,-N(SO2CnF2n+1)2,它物理稳定,并化学稳定,同时在化学上恶劣或者极端的条件下提供杰出的表面活性。而且,由于所述全氟化阴离子碱性很低,本发明表面活性剂或添加剂在通常所需的许多极端的应用中不容易质子化(即使在低pH的水溶液中)。此外,相比由C8F17SO2F(POSF)通过ECF以相对较低产率制备的表面活性剂,本发明表面活性剂可由成本更低的中间体,如CF3SO3F和C4F9SO2F制备。令人惊奇的是,可用本发明表面活性剂代替全氟辛基类表面活性剂而不会牺牲表面活性或者表面活性剂的性能。而且,本发明的表面活性剂多半能更快地生物消除。
一方面,本发明包括降低溶液表面张力的方法,所述方法包括:(a)提供会降解烃基表面活性剂的水溶液,(b)将包含二(全氟烷基磺酰基)酰亚胺或其一种盐的表面活性剂加入所述水溶液中。
本发明的另一实施方式是水力流体,它包含一种或多种磷酸酯、至少一种二(全氟烷基磺酰基)酰亚胺盐添加剂、以及任选地包含助剂,所述助剂选自粘度指数改进剂、酸控制组分、抗氧化剂组分、润滑剂、染料、缓蚀剂、消泡剂以及它们的混合物。
本发明另一方面是具有极端环境的应用,其中所述应用包括一种水溶液,所述水溶液包含二(全氟丁磺酰基)酰亚胺或其一种盐。
附图简要说明
图1是全氟丁磺酸钾和全氟辛磺酸钾(PFOS)在水中的表面张力(达因/厘米)与浓度(ppm)的图。
图2是所述一系列酰亚胺的锂盐在水中的表面张力(达因/厘米)与浓度(ppm)的关系曲线图。
图3是全氟辛磺酸铵(II,FC-93,从Minnesota Mining and ManufacturingCompany,St.Paul,MN购得)、二(全氟丁磺酰基)酰亚胺的酸形式(当溶解在水中时,实际上是以具有作为反离子的质子化水(H3O+)的二(全氟丁磺酰基)酰亚胺阴离子存在)以及其带有NH4 +、Li+和K+的盐的表面张力(达因/厘米)与浓度(ppm)的关系曲线图。
图4是二(全氟丁磺酰基)酰亚胺的酸形式及其铵盐在10/1缓冲氧化物蚀刻溶液中表面张力与浓度的图,该图具有对照物(FC-93)。
图5是两种二(全氟丁磺酰基)酰亚胺的JEFFAMINETM盐和二(全氟丁磺酰基)酰亚胺的钾盐以及所述全氟烷基磺酸盐的表面张力与浓度的关系曲线图
图6是二(全氟丁磺酰基)酰亚胺的Mg2+、Li+和NH4 +盐的表面张力(达因/厘米)与浓度的图。
这些图仅仅是用于说明的,并不是进行限定。
说明性实施方式的详细说明
本发明涉及作为极端或恶劣环境用表面活性剂或添加剂的二(全氟烷基磺酰基)酰亚胺及其盐。具有水溶液的极端或恶劣环境定义为一些综合条件,如热、光、辐射、氧化/还原势、高压、高剪切、高pH(9-14)或者低pH(-2-5)、或者存在腐蚀试剂,它们会导致常规烃基表面活性剂或添加剂降解或质子化。
所述表面活性剂(本文中定义为聚集在所溶解的液体表面,或者聚集在液体和另一种不混溶的液体或固体的界面处,并降低所述表面张力或者界面张力的物质)用在本发明应用中的水溶液中。这种水溶液的例子包括,但不限于包含氟化铵和氟化氢的缓冲氧化物蚀刻液,氢氧化四甲基铵,包含硫酸铜和硫酸的酸性镀铜溶液,包含选自氧化铝、二氧化硅和铈的磨粒、氧化剂、蚀刻剂和缓蚀剂的用于化学机械抛光(CMP)铜的浆液,单独或混合包含H2O2、O3、H2SO4、NH4OH或HCl的晶片清洁溶液、氢氧化铵、氢氧化钠、氢氧化钾、季铵氢氧化物、乙二胺或者乙醇胺和三氧化铬、或者其它铬(VI)离子,以及硫酸。
而且,本发明的表面活性剂或添加剂在非水性(或有机)水力流体中也有用。
虽然,在常规商业应用的相当短的时间内稳定存在,但是预计本发明的二(全氟烷基磺酰基)酰亚胺表面活性剂或添加剂,当暴露在环境中存在的生物作用、热、氧化、水解和光解条件下时,将逐渐降解成各种降解产物。例如,预计包含二(全氟丁磺酰基)酰亚胺阴离子的组合物会缓慢但是最终降解成全氟丁磺酸盐(即,C4F9SO3-的盐)。已令人惊奇地发现,以其钾盐的形式测定,全氟丁磺酸根比全氟己磺酸根更快地从体内消除,且比全氟辛磺酸根更加快得多地从体内消除。
本发明一方面包括通过往所述水溶液中加入二(全氟烷基磺酰基)酰亚胺或其盐来降低水溶液的表面张力的方法。本文中,所述表面张力/表面能定义为断开或破坏溶液表面所需的能量。高表面张力会制约液体流动或者润湿邻近的液体或固体基材。通常,使用DuNuoy环表面张力计或者Wilhelmy板式表面张力计来测量溶液的表面张力。
另一方面,本发明包括有机水力流体,它包含一种或多种磷酸酯、二(全氟烷基磺酰基)酰亚胺盐添加剂、以及任选的其它用于优化水力流体性能而加入的助剂或组分,如粘度指数改进剂、酸控制组分、抗氧化剂组分、润滑剂、染料、缓蚀剂、消泡剂等,以及它们的混合物。
表面活性剂
本发明的表面活性剂或添加剂包括二(全氟烷基磺酰基)酰亚胺及其盐。这些酰亚胺可以由下式表示:
式中,Rf 1和Rf 2分别为包含1-12个碳原子,并在碳链上任选包含连接的杂原子如O、N的全氟烷基。Rf 1和Rf 2较好包含2-6个碳原子,为了便于更快的环境生物消除,更好是包含3-5个碳原子。M是H或者无机或有机阳离子。
二(全氟丁磺酰基)酰亚胺尤其适用于这些应用。
二(全氟烷磺酰基)酰亚胺及其盐可以通过本领域已知的方法由全氟烷基磺酰卤制备,如美国专利No.5,874,616、5,723,664和ZA9804155所述的。通常,这些阴离子可以在Et3N(或类似的碱)存在下,通过使2RfSO2X和NH3反应,或者在Et3N(或类似的碱)存在下,通过使RfSO2X和RfSO2NH2反应来制备。
这些表面活性剂/添加剂可以包含各种金属和非金属阳离子,包括但不限于任何碱金属阳离子、任何碱土金属阳离子(例如,Li+、K+、Na+、Ca2+、Mg2+)、H+、H3O+、NH4 +、Zn2+、Cu2+以及各种有机氮、有机醚和磷鎓阳离子(例如,从Huntsman Corporation,Salt Lake City,UT购得的JEFFAMINETM聚亚烷基胺的质子化形式,以及从Akzo Nobel Surface Chemisity LLC.,Chicago,IL购得的ETHOQUADTM)。
在水溶液中,合适的表面活性剂包括,但不限于具有阳离子H+、NH4 +、H3O+、Na+、K+、Li+、Mg2+、Ca2+、Zn2+、Cu2+和各种来自市售JEFFAMINETM聚亚烷基胺质子化的铵阳离子和以下所示任何阴离子的结合的盐:
在非水性溶液或水力流体溶液中,合适的添加剂包括,但不限于具有阳离子Na+、K+、Mg2+、Ca2+、Me4N+、Bu4N+、Bu4P+、1,3-乙基甲基咪唑鎓和N-丁基吡啶鎓和以下所示任何阴离子的结合的盐:
根据本技术,本领域的技术人员可以预期来自较短的含氟化学链的表面活性剂或添加剂会不如来自较长的含氟化学链的那样有效。即使在烃基表面活性剂中,烃链的链长增加,则CMC(临界胶束浓度)降低。对于在链上每增加一个CH2CH2-,CMC的降低大概为一个数量级(Amphoteric Surfactants,EricG.Lomax编著,Marcel Dekker Inc.(1996),第13页)。在来自全氟羧酸和磺酸的表面活性剂中也存在相同的趋势(Organofluorine Chemicais and theirIndustrial Applications,R.E.banks编著,Ellis Horwood Ltd.(1979),第56页;J.O.Hendrichs编著的Ind.Eng Chem,45,1953,第103页;M.K.Bernett和W.A.Zisman编著的J.Phys.Chem.,63,1959,第1912页)。由于所述用于解释表面活性剂作用的模型通常引用单层表面活性剂在空气/液体界面上,所以可以预期所述氟化表面活性剂的情况也是一样的,并且所述表面活性剂的活性与其链长紧密相关。这样例如在图1中,描述了所述全氟丁磺酸钾和全氟辛磺酸钾(PFOS)的表面张力与浓度的曲线,在降低水表面张力的方面,全氟丁磺酸盐不如全氟辛磺酸盐有效。
从本技术领域可以预期,所述分子形状也会影响其作为表面活性剂的能力。Zisman和其他人已经发现,对于金属板上的长链羧酸单层而言,所述直链物质相比支链相似物来说提供较低的表面能。所述表面活性剂在溶液中如何起作用的理想模型通过定向在金属表面上的单层极性分子来表示。基于这一信息,认为所述支链物质,二(全氟丁磺酰基)酰亚胺钾盐显示比全氟丁磺酸钾(PBSK)更高的表面张力值。但是,图5表明二(全氟丁磺酰基)酰亚胺钾盐相比PBSK显示明显较低的表面张力,并且该表面张力和相等浓度的全氟辛磺酸钾相当。
此外,由于在电化学氟化中全氟丁磺酰氟的产率(58%)高于全氟辛磺酰氟的产率(31%),所以使用全氟丁磺酰氟(PBSF)作为表面活性剂前体而不是POSF将尤其有利(Preparation,Properties,and Industial Applications ofOrganofluorine Compounds,R.E.Banks编著,Ellis Horwood Ltd.(1982),第37页)。因此,PBSF衍生的表面活性剂可以每单位重量成本较低来制备,这是因为其产率更高,并且仍旧保持和相同重量百分数的表面活性剂一样的能力。
若考虑它们的表面活性剂性能,二(全氟丁磺酰基)酰亚胺及其盐比所述其它酰亚胺系列低级同系物优越。这在显示一系列酰亚胺的锂盐在水中的表面张力(达因/厘米)与浓度(ppm)的关系曲线的图2中有说明。在图2中,MBI是[C4F9SO2N(-)SO2CF3]Li、BETI-Li是[C2F5SO2N(-)SO2C2F5]Li,且HQ-115是Li+N(SO2CF3)2,从Minnesota Mining and Manufacturing Company,St.Paul,MN购得。二(全氟丁磺酰基)酰亚胺锂相比更短链同系物、MBI-Li、BETI-Li、HQ-115来说,表面张力明显更低,证实链长的增加会显著降低表面张力。
图3显示了全氟辛基磺酸铵(II,F6-93)和二(全氟丁磺酰基)酰亚胺的酸形式(在水中,实际上是以水合氢离子盐H3O+-N(SO2C4F9)2存在)以及二(全氟丁磺酰基)酰亚胺的NH4 +、Li+和K+盐的表面张力(达因/厘米)与与浓度(ppm)的关系曲线。
在图3中,在浓度高达1000ppm时,相比NH4 +-OSO2C8F17(FC-93,从MinnesotaMining and Manufacturing Company,St.Paul,MN购得),二(全氟丁磺酰基)酰亚胺的非金属盐如H3O+-N(SO2C4F9)2和NH4 +-N(SO2C4F9)2是更好的表面活性剂。FC-93在水中推荐使用的含量为100-1000ppm(Technicai Service BulletinFLUORADTM Etching Bath Additive FC-93,Issued 10/90)。
图4是二(全氟丁磺酰基)酰亚胺酸形式及其铵盐(NH4 +)在10/1缓冲氧化物蚀刻溶液中表面张力(达因/厘米)与浓度(ppm)的图。在图中还包括了对照物FC-93,但是在所有浓度下,所述FC-93沉淀。所述二(全氟丁磺酰基)酰亚胺及其盐在所有浓度下可以溶解。所述二(全氟丁磺酰基)酰亚胺的1000ppm溶液对肉眼来说略微混浊。
所述二(全氟丁磺酰基)酰亚胺的质子化JEFFAMINETM盐((DBI)2JEFFAMINETMED-600和(DBI)3T-403)起到表面活性剂的作用。在图5中,显示了两种二(全氟丁磺酰基)酰亚胺的JEFFAMINETM盐在水中的表面能(达因/厘米)与浓度的关系曲线,并和和全氟烷基磺酸钾盐比较。两种JEFFAMINETM盐产生的表面张力明显比C4F9SO3K低。(DBI)3JEFFAMINETMT-403显示的表面张力明显比图5中所有的钾盐(C8F17SO3K、C4F9SO3K、C4F9SO2NKSO2C4F9)以及(DBI)2JEFFAMINETM低。
通常,往溶液中加入10-50,000ppm,较好是10-5,000ppm本发明的表面活性剂或添加剂。
应用
具有包括水溶液的极端环境的应用包括,但不限于用于制备半导体器件的蚀刻溶液、光致抗蚀剂的显影剂和除去溶液、电化学电镀和抛光溶液、晶片清洁和抛光(化学/机械或者化学)溶液,以及各向异性蚀刻溶液。这些应用各自使用可以降解许多烃表面活性剂的水溶液。对于用在半导体加工中,表面活性剂不是必须包含金属反离子。碱金属被认为是流动的杂质。其存在导致半导体的临界电压和平带电压移位。这会显著改变所述半导体的电子性能,可能导致所述器件短路。(D.C.Burkman、C.A.Peterson、L.A.Zazzera和R.J.Kopp,Microcontamination,1988年11月)。因此,通常使用铵盐。
使用HF水溶液蚀刻二氧化硅来清洁晶片或者在硅晶片上将氧化物薄膜形成图案。在蚀刻过程中,用酸蚀刻剂润湿所述晶片表面差,这会导致夹入空气,形成小气泡。这些气泡会导致桥接所述形成图案的表面中细小的开孔,在器件中可能导致通电短路。这样就需要稳定的表面活性剂来降低用于半导体器件制备的蚀刻溶液的表面张力,并能均匀润湿并蚀刻,而不会夹入空气。
可以使用氟化氢(HF)水溶液或者缓冲氧化物蚀刻(BOE)溶液,通过除去未被光致抗蚀剂保护的二氧化硅区域(即,光活性薄膜)并由此暴露下面的硅来将氧化物薄膜形成图案。典型的BOE为1份49%的HF和7份40%的氟化铵。所述BOE并不能侵蚀所述光致抗蚀剂。硅表面的表面能比二氧化硅表面的低。因此,水介质并不能润湿所暴露的硅以及二氧化硅。因此,需要表面活性剂帮助润湿所暴露的硅。所述烃表面活性剂在用于蚀刻的HF溶液中的稳定性是争论的问题。通常,比较不稳定的烃表面活性剂降解成不溶的片段,在连续过滤蚀刻浴中被滤去。表面张力必须会快速升高,并伴随着更高的报废率(K.M.Shah,P.MiKKelson,W.Cummings,Semiconductor International,1988年10月)。
将相对低浓度(10-1000ppm)的氟化表面活性剂加入HF和BOE的水溶液中,来降低所述溶液的表面张力并提高润湿能力。由此,提高晶片清洁或者氧化物形成图案的工艺效率。由于所述表面活性剂的稳定性和次品率降低(次品率较高是由于夹入空气所致的),其净效果就是延长所述蚀刻浴的使用寿命。
光刻法是在硅片上制造微型电路图的工艺。将已知为光致抗蚀剂或“抗蚀剂”的光活性薄膜施加到晶片上,形成均匀的薄膜。这一工艺通常通过旋涂所述光活性薄膜来进行的。然后,将所述光活性薄膜软烘(soft bake)(在烘箱中温和地加热),来除去所述涂覆溶剂。之后,将所述光活性薄膜暴露在透过有图案的掩模投射的光能中,在晶片、读写头或者其它器件上形成电路或者组件图案。在正型光致抗蚀剂中,所述光会引发和产生酸的光致酸产生剂的光致反应,再在所述光致抗蚀剂中催化化学变形,由此提高其在显影剂中的溶解性。然后,所述包含碱(例如,氢氧化四甲基铵,TMAH)水溶液的显影剂溶液选择性除去低分子量的物质,并在光致抗蚀剂中形成所需的图像。
在一些情况下,由于所述光致抗蚀剂图案的垂直壁坍塌,导致微电子器件的产率下降。所述显影剂水溶液的高表面张力是导致所述成像区域中光致抗蚀剂壁坍塌的重要因素。包含本发明相对低浓度(10-1000ppm)氟化表面活性剂的显影剂水溶液可以降低表面张力,并使图案坍塌的最小,使线边缘粗糙度最小,同时也提供在高pH条件下的稳定性。
本发明的表面活性剂和添加剂尤其适用于金属薄膜如铜的电化学电镀和抛光。已经认为铜是高性能微处理器芯片优选的互联材料,这是因为其电阻率低。在制造中,向铜双镶嵌过渡要求严格控制铜的电镀和抛光。在制造集成电路中,优选使用电镀来进行铜互联沉积,这是由于其沟槽填充能力以及其成本相对较低。由于其稳定性及其低成本,由酸化硫酸铜来电镀铜是最流行的电镀化学方法。
酸性镀铜水溶液通常由三种主要组分组成:1)硫酸铜(铜的来源,通常为0.2-0.6M),2)硫酸,为电解液提供导电性(通常为1-2M),3)各种添加剂,包括表面活性剂,通常为10-10000ppm。
由于其成本较低,且使用干等离子体难以蚀刻铜,所以在制造集成电路时使用化学机械抛光(CMP)来平整铜互连处。铜CMP浆液包含磨粒、氧化剂、蚀刻剂和缓蚀剂。在铜CMP中广泛使用在酸性溶液中的氧化铝基浆液。对镀铜和抛光铜过程中所需的严格控制来说,添加剂是关键。在电镀和抛光水溶液中使用浓度相对较低(10-1000ppm)的本发明的表面活性剂和添加剂,来降低所述溶液的表面张力,并提高润湿能力,这会提高电镀和抛光作用的速率和均匀性。本发明的表面活性剂和添加剂还提供经受这些工艺中常用的恶劣条件(包括低pH、腐蚀试剂)所需的稳定性,和还原和氧化电化学势。
半导体芯片制造中最普通的加工步骤是晶片清洁。在晶片清洁过程中,使用氧化清洁步骤来氧化所述硅片的表面,并氧化、溶解和除去有机杂质。通常,所述晶片与H2O2或O3、H2SO4、NH4OH或HCl的水性混合物接触。蚀刻清洁步骤通过将晶片和稀的HF水溶液接触来除去硅表面上自然存在以及沉积其上的二氧化硅薄膜。在半导体芯片制造中其它重要的氧化和蚀刻清洁工艺包括除去等离子灰化或者介电体、光致抗蚀剂或金属蚀刻之后留下的残留物,并后CMP清洁除去氧化物抛光之后留下的二氧化硅残留物。
所述晶片清洁和抛光溶液可以包含相对低浓度(10-1000ppm)的本发明的氟化表面活性剂,来降低所述溶液的表面张力并提高润湿能力。因此,所述清洁和抛光作用的速率和均匀性提高了。不像大多数的烃基表面活性剂,本发明的氟化表面活性剂对于在晶片清洁和抛光应用中所用的高腐蚀性的酸性或碱性试剂来说是稳定的。
使用各向异性蚀刻单晶硅来制造用于集成电路、光学器件以及微电子机械器件的沟槽、沟道、膜和衍射光栅。由于在Si(100)平面的反应速度比Si(111)平面的快大约75倍,所以导致各向异性。各向异性蚀刻形成侧壁和Si(100)平面成54°的V形凹槽。用于各向异性蚀刻工艺的蚀刻溶液通常是碱性水溶液,它以氢氧化纳或者氢氧化钾、氢氧化季铵、乙二胺或者乙醇胺为基础。所述蚀刻溶液可以包含相对低浓度(10-1000ppm)本发明的氟化表面活性剂,来降低所述溶液的表面张力并提高润湿能力,由此提高所述各向异性蚀刻作用的速率和均匀性,同时提供在恶劣条件下的稳定性。
所述二(全氟丁磺酰基)酰亚胺的钾盐可以用在钾离子的存在无关紧要的极端应用中,如镀铬浴、转化涂宵以及金属和塑料蚀刻剂。如图5所示,虽然其一般使用范围是10-1000ppm,但是二(全氟丁磺酰基)酰亚胺钾在水中具有和C8F17SO3K(FC-95,从Minnesota Mining and Manufacturing Company,St.Paul,MN购得)相同或更好的表面张力。
水力流体
本发明的表面活性剂或添加剂也可以用在有机溶液中,如具有极端环境的水力流体。本发明合适的添加剂可溶于基础水力流体,具有表面活性,并提供必需的导电性。
当溶解在航空水力流体如磷酸酯(例如,SKYDROLSTM,从Solutia,St.Louis,MO购得)时,已经显示全氟辛基磺酸钾或者全氟乙基环己基磺酸钾可用作缓蚀剂。
本发明的水力流体包含液体磷酸酯类及其混合物,其中,所述磷酸酯由下式表示:
式中,各R分别为包含2-12个碳原子的烷基或者烷氧基烷基、包含多达20个碳原子的苯基和取代苯基,其中所述取代基为烷基、苯基或苯基烷基,而且所述烷基包含1-10个碳原子。
所述水力流体包含至少50+重量%的磷酸酯。较好是,所述磷酸酯包含65-99.999重量%水力流体。本发明水力流体也包含其它润滑剂,例如聚酯、聚苯醚等。
本发明水力流体组合物所用的添加剂量至少为每100份磷酸酯0.001份,至多为5.0份。若可溶于所述水力流体,可以使用大于5.0份的量。
通常,工业上使用全氟乙基环己基磺酸钾(FC-98,从Minnesota Mining andManufacturing Company,St.Paul,MN购得),这是因为它在航空水力流体市售配方中所用的磷酸酯中的导电性较好、可溶性高,具有合适的表面活性。在这些应用中,需要使用提高导电性的添加剂,来进行电化学腐蚀控制(例如,可见WO00/24848)。所述二(全氟丁磺酰基)酰亚胺的钾盐在磷酸酯中具有足够的溶解性,可以作为抗蚀添加剂,并提供高导电性。二(全氟丁磺酰基)酰亚胺钾溶解在SKYDROLSTM LD-4(一种由Solutia,St.Louis,Mo制造的市售航空水力流体)中,其浓度高达2重量%。
可以往所述磷酸酯中加入其它助剂,例如(但不限于):粘度指数改进剂、酸控制组分、抗氧化剂、润滑剂、染料、缓蚀剂、消泡剂等。
本发明水力流体中通常使用能有效降低温度对水力流体粘度影响的量的粘度指数改进剂(通常约为2-10重量%)。合适粘度指数改进剂的例子在例如美国专利No.5,464,551和3,718,596中有揭示。优选的粘度指数改进剂包括美国专利No.3,718,596中所揭示的、以及从Rohm & Haas,Philadelphia,PA购得的聚(丙烯酸烷基酯)和聚(甲基丙烯酸烷基酯)类。
通常,本发明水力流体还包含酸控制组分或者酸清除剂,其量(通常约为4-10重量%)能有效中和在水力流体中形成的酸,如磷酸及其部分酯。在美国专利No.5,464,551、3,723,320和4,206,067中说明了合适的酸控制剂组分。
在另一实施方式中,本发明水力流体还包含抗氧化剂或者抗氧化剂的混合物,其量能有效地抑制所述水力流体或者其任何组分的氧化(通常约为0.5-3重量%)。在美国专利No.5,464,551和其它水力流体专利和出版物中说明了合适的抗氧化剂。
在另一实施方式中,本发明的水力流体还包含润滑剂、染料、缓蚀剂、消泡剂以及其它助剂,或者它们的混合物,用来进一步提高所述水力流体的性能。
实施例
还参考以下非限制性实施例和测试方法来说明本发明。除非另有所述,所有的份、百分数以及比率均以重量计。
测试方法
测试方法I-测定表面张力
使用Kruss K12张力计测定所有的表面张力。使用动态接触角(K121)用软件包,将张力计和自动放射剂量计(dosimat)以及计算机结合。使用Wilhelmy铂盘(PL12)以及玻璃样品容器(GL7)来进行所述程序。上述所有的部件包括仪器和计算机均来自Kruss USA,Charlotte,NC。
按如下所述制备所述作比较的盐:
从Minnesota Mining and Manufacturing Company,St.Paul,MN购得全氟丁磺酸钾(PBSK)FR2025。
基本上按照美国专利No.2,732,398,实施例5所述制备全氟辛磺酸钾,除了使用CH3(CH2)7SO2F代替CH3(CH2)7SO2Cl作为原料外。
如美国专利No.2,732,398所述,通过在无水HF中电化学氟化p-C2H5-C6H4-SO2F来制备C2F5-C6F10-SO2F,之后使用含水K2CO3水解来制备全氟乙基环己基磺酸钾(FC-98)。
实施例1,(C2H5)3NH+-N(SO2C4F9)2:
将187.2g无水三乙胺和362.5g高纯度全氟丁磺酰氟(从Aldrich ChemicalCo.Milwaukee,WI购得)真空加入烘箱干燥的600ML Parr反应器中,所述反应器由Hastalloy和Monel制成,并装有磁控管搅拌器、Parr 4843控制器(ParrInstrument Company,Moline,IL)、用于加入气态NH3的针型阀、用于除去液体产物的浸入管、600psi(4.1MPa)压力计、热电偶探头和加热套。然后,在干冰浴中骤冷所述反应器主体,至约-20℃。一旦冷却之后,将9.0g无水氨气加入所述反应器中,所述氨气通过接到所述反应器头部组件上的针型阀引入,以从安装在邻近天平上的气体钢瓶精确计量加入气体。一旦加入所有的氨,所述反应器直立安装上加热套板,开始全速(700RPM)搅拌,并且反应器温度迅速升至90℃。在温度上升过程中在约20℃时达到最大压力100psi(690KPa)。所述反应器温度升至大于40℃会导致压力迅速降低,这是由于NH3被迅速消耗掉。一旦达到设定温度90℃,将温度保持在这一值下19小时(过夜)。在加热循环结束时,通过在搅拌过程中,在90℃、40托下由反应器中的气孔真空抽提约1小时来除去残留的C4F9SO2F和三乙胺。挥发物收集在干冰B#中。然后,冷却所述反应器至接近室温,并通过使用约10psi(69KPa)氮气对反应器加压,将所述反应器内液体物质压出浸入管,将所述粗产物收集在聚乙烯瓶中。无需拆除或清洁所述反应器,可以第二次重复这一完整步骤,制得第二批粗产物。从第一批和第二批收集的粗产物的总量为976.9g。虽然开始时是液体,但是,粗产物在室温下静置长时间后会部分固化。
在50℃的烘箱中熔化总共为975g的物质,并在烧瓶中用1800g 44℃的水洗涤。在接到抽气机上的黑色橡胶管一端使用TEFLONTM管除去上层水相,再用1800ml 57℃下的水洗涤下层深褐色的氟化试剂相,然后冷却至17℃,这时停止搅拌,所述物质固化。然后在接到抽气机上的黑色橡胶管一端使用TEFLONTM管除去上层水相。如上所述,用水洗涤所述褐色氟化化学试剂相三次以上。在77℃下将总共744g液体(C2H5)3NH+-N(SO2C4F9)2从烧瓶中倒出,并称重。
实施例2,合成HN(SO2C4F9)2
将上述用水洗涤过的(C2H5)3NH+盐倒回烧瓶中,并在77℃、10mmHg(1.3KPa)的真空条件下加热所述物质1小时,除去溶解的水(49g)。真空条件破坏之后,在搅拌下往所述干燥的(C2H5)3NH+-N(SO2C4F9)2中加入419g 94-96%硫酸。温度升至93℃。在4mmHg下从硫酸中蒸馏所述酸性物质,提到551g能在110-125℃下蒸馏的HN(SO2C4F9)2。进行水份分析,可知产物中包含4重量%水。
实施例3,合成NH4 +-N(SO2C4F9)2
将来自实施例2的总共174g HN(SO2C4F9)2溶解在1540g水中。溶液的pH为0-1。在搅拌条件下,加入总共17g30%氢氧化铵。所述溶液的pH仍旧保持在0-1的范围内。再加入额外的6.7g 30%氢氧化铵,发现pH为7-8。将此批料加热至40℃,并吹氮气通过所述溶液2小时。当烧瓶冷却至室温时,将其倒入塑料瓶中。分离出总共1738g NH4 +-N(SO2C4F9)2溶液,并且发现含有9.8%固体。
实施例4,合成K+-N(SO2C4F9)2
将来自实施例2的总共58.6g HN(SO2C4F9)2溶解在250g水中。溶液的pH为0-1。在搅拌条件下,加入总共6.9g碳酸钾。在58℃下加热所述批料2小时。测得pH约为6。这时,烧瓶冷却至室温。过滤烧瓶中白色固体,并用75ml水洗涤两次。在烘箱中干燥之后,分离出总共47g K+-N(SO2C4F9)2。再重复用水洗出烧瓶中残留的白色固体,并干燥,得到另外的9.6g K+-N(SO2C4F9)2。
实施例5,[-N(SO2C4F9)2]2
(+)H3NCH(CH3)CH2[OCH(CH3)CH2]a[OCH2CH2]8.5[OCH(CH3)CH2]cNH3(+)(a+c=2.5)
在安装有顶部搅拌器、热电偶以及进料漏斗的3升烧瓶中,将总共760g(MW=581,1.26mol,实施例2制备)HN(SO2C4F9)2(96%活性物质和4%水)溶解在760ghplc级水中。在70℃下,在搅拌的过程中在30分钟内往所述批料中加入398g从Huntsman Corporation,Salt Lake City,UT购得的JEFFAMINETM XJT-500(MW600,0.66mol)。再搅拌所述批料15分钟,pH测量为7-8。所述批料凝结点设定在70℃,并该烧瓶装有顶部蒸馏设备。通过接受器将批料上的真空度缓慢降低。将所述接受器预先冷却至-78℃。将水汽提到接受器中,直到真空达到13mmHg(1.7KPa)。将所述批料保持在70℃、13mmHg(1.7KPa)下1小时。将琥珀色蜂蜜状液体倒入广口瓶中并称重。分离出总共1042g物质。
表1详细说明了这种物质和相比较的全氟烷基磺酸盐物质(DBI)2JEFFAMINETM ED-600的表面能与浓度的关系曲线。
实施例6,CH3CH2C[CH2(OCH2CH(CH3))xNH3 +][CH2(OCH2CH(CH3))yNH3 +][CH2(OCH2CH(CH3))z]NH3 +][-N(SO2C4F9)2]3,其中(x+y+z=5.3)
在安装有顶部搅拌器、热电偶以及进料漏斗的1升烧瓶中,将总共100g(MW=581,0.165mol)HN(SO2C4F9)2(96%活性物质和4%水)溶解在175g甲基叔丁基醚中。在70℃下,在搅拌的过程中在30分钟内往所述批料中加入49g从Huntsman Corporation,SaltLake City,UT购得的JEFFAMINETM T-403(MW440,0.11mol)。再搅拌所述批料15分钟,pH测量为7-8。所述批料凝结点设定在70℃,并该烧瓶装有顶部蒸馏设备。在大气压下汽提所述甲基叔丁基醚,直到容器温度达到80℃。将残留的溶剂和水汽提到接受器中,直到真空达到13mmHg(1.7KPa)。将所述批料保持在70℃、13mmHg(1.7KPa)下1小时。将琥珀色很稠的液体倒入广口瓶中并称重。分离出总共116g物质。
表1详细说明了这种物质和相比较的全氟烷基磺酸盐物质(DBI)3T-403的表面能和浓度的关系曲线。之前所示的图5的数据和表显示的数据相同。
表1
0ppm | 10ppm | 100ppm | 1000ppm | |
C8F17SO3K-比较 | 72 | 67.68 | 54.09 | 33.17 |
C4F9SO3K-比较 | 72 | 70 | 67.5 | 53 |
C4F9SO2NKSO2C4F9 | 72 | 61.85 | 41.61 | 34.02 |
(DBI)2JEFFAMINETM ED-600 | 72 | 57.4 | 40.7 | 32.7 |
实施例6 | 72 | 34.3 | 33.4 | 28.6 |
实施例7,Mg+2[-N(SO2C4F9)2]2
将总共36g来自实施例2的HN(SO2C4F9)2溶解在36g水中。溶液的pH为0-1。在搅拌条件下,加入总共2.4g碳酸镁(Mallinckrodt,St.Louis,MO)。pH测得约为6。然后将烧瓶冷却至室温。过滤烧瓶中沉淀的白色固体,并重复用水洗出,然后烘箱干燥得到13.1g所需的干燥钾盐。在表2中显示了在水中测得的表面张力(达因/厘米)。
表2
0ppm | 200ppm | 450ppm | 960ppm | 1300ppm | 1700ppm | 2600ppm | |
Mg(DBI)2 | 71.0 | 46.6 | 40.2 | 35.0 | 32.0 | 29.0 | 26.3 |
DBI-NH4 | 71.0 | 48.6 | 44.1 | 40.1 | 38.7 | 35.9 | 31.5 |
DBI-Li | 71.0 | 53.2 | 48.1 | 42.8 | 41.5 | 39.1 | 36.0 |
图6显示了列表的数据,并将它和DBI的铵盐和锂盐比较。
实施例8,水力流体
按照表3所述的组成制备本发明包含抗蚀剂(K[N(SO2C4F9)2]))的水力流体(采用WO93/25641,实施例1所述的)。
表3
物质 | % | 供应 |
磷酸三丁酯 | 49.0135 | Aldrich Chemical Co.Milwaukee,WI |
磷酸二丁基苯基酯 | 26.34 | Exchange Chemical Inc Center Ossipee,NH |
甲基丙烯酸酯,粘度指数改进剂(PA6477,磷酸三丁酯中45.3%固体) | 16.56 | Rohm & Haas,Philadelphia,PA |
羧酸3,4-环氧环己酯 | 6.3 | 在美国专利3,723,320中有述 |
K[N(SO2C4F9)2] | 0.05 | 实施例4 |
苯并三唑型铜缓蚀剂P57068,50%活性EXI 663 | 0.05 | Baker Petrolite,Sugarland,TX |
铁缓蚀剂(90-31001 50%活性) | 0.05 | Baker Petrolite,Sugarland,TX |
可溶染料 | 0.001 | |
苯氧基钾 | 0.035 | Organomettalics,Inc East Hampstead,NH |
二(3,5-二叔丁基-4-羟苯基)甲烷(Ethanox 702) | 0.90 | Albemarle Corporation,Baton Rouge,LA |
二(对辛基苯基)胺(VanlubeTM 81) | 0.45 | R.T.Vanderbilt,Norwalk,Connecticut |
2,6-叔丁基-4-甲基苯酚 | 0.25 | Aldrich Chemical Co.Milwaukee,WI |
消泡剂DC 200 | 0.0005 | Dow Corning,Midland,MI |
实施例9,钾盐在磷酸三丁酯中的电导率
本实施例说明了当溶解在常用航空水力流体,磷酸三丁酯中时,相比已有技术和腐蚀添加剂(PBSK和FC-98),二(全氟丁磺酰基)酰亚胺钾盐提供的高电导率。
测量四种磷酸三丁酯样品的DC电导率,不论是否溶解有抗蚀添加剂。所述四种样品是纯净的磷酸三丁酯(对照物)、具有3000ppmFC-98的磷酸三丁酯、具有3000ppm PBSK的磷酸三丁酯以及具有3000ppm二(全氟丁磺酰基)酰亚胺钾盐(DBIK)的磷酸三丁酯。
使用Orion 122DC型电导计,用具有从ThermoOrion,Beverly,MA购得的温度传感和补偿的4-电极导电探针(环氧主体,碳电极、012210型)测量电导率。
用EM Science OMNISOLVTM级甲醇仔细清洁所述导电探针,并在清洁氮气流中干燥,而且样品之间平衡返回室温。
表4
样品 | 观察的导电率(uS/cm) |
磷酸三丁酯(对照样品) | 在21.6℃下为0.1uS/cm |
具有3000ppm FC-98的磷酸三丁酯,比较 | 在21.9℃下为3.2uS/cm |
具有3000ppm PBSK的磷酸三丁酯,比较 | 在21.6℃下为3.5uS/cm |
具有3000ppm DBIK的磷酸三丁酯 | 在21.7℃下为13.8uS/cm |
当通过全AC阻抗测量相同样品的电导率时,结果和这些值一致。
实施例10
如上所述,测量表面张力,除了所述测量是在磷酸三丁酯中进行以外。
表5
物质 | 在2000ppm下的表面张力(达因/厘米) |
磷酸三丁酯-比较 | 28.37 |
Mg(C8F17SO3)2-比较 | 27.36 |
FC-98-比较 | 26.94 |
K[N(SO2C4F9)2] | 27.34 |
FC-95-比较 | 26.96 |
Mg[N(SO2C4F9)2] | 27.04 |
Ca(C8F17SO3)2-比较 | 26.15 |
Mg(SO3C4F9)2·6H2O-比较 | 26.93 |
K(SO3C4F9)-比较 | 27.32 |
实施例11,用全氟丁磺酸盐进行生物消除研究
比较研究全氟丁磺酸钾(剂量为30mg/kg体重/天)、全氟己磺酸钾(剂量为10mg/kg体重/天)以及全氟辛磺酸钾(剂量为3mg/kg体重/天)。在表6中显示了在雄性大鼠肝脏组织样品中存在的氟化磺酸根的量。
表6
磺酸盐 | 磺酸根的量(ppm) | |||||
1天 | 1天N* | 14天 | 14天N* | 28天 | 28天N* | |
C8F17SO3 - | 419±86 | 419 | 309±34 | 309 | 237±25 | 237 |
C6F13SO3 - | 327±52 | 98 | 61.9±11.7 | 19 | 36.3±7.4 | 11 |
C4F9SO3 - | 3.09±1.58 | 0.31 | 0.126±0.084 | 0.0126 | 0.025±0.015 | 0.0025 |
*归一化为每天注入量为3mg/kg体重。
表6中显示的结果表明,如所发现极少的量所证实的,C4F9SO3 -能出乎意料地迅速而且有效地的消除,,尤其是相对于C6F13SO3和C8F17SO3 -来说。当刚刚完成注入后,C6F13SO3 -比C8F17SO3 -低1.3倍,但是C4F9SO3 -比C6F13SO3 -低100倍。在完成注入后的28天,C6F13SO3 -比C8F17SO3 -低6.5倍,但是C4F9SO3 -比C6F13SO3 -低1400倍。当归一化到相同的注入量后,在完成注入后的28天,C6F13SO3 -比C8F17SO3 -低21.5倍,但是C4F9SO3 -比C6F13SO3 -低4400倍。
Claims (5)
1.一种降低溶液表面张力的方法,所述方法包括:
(a)提供一种水溶液,所述水溶液选自:
氟化铵和氟化氢溶液;
氢氧化四甲基铵溶液;
包含硫酸铜和硫酸的酸性镀铜溶液;
包含选自氧化铝、二氧化硅和铈的磨粒、氧化剂、蚀刻剂和缓蚀剂的CMP浆液;
单独或混合包含H2O2、O3、H2SO4、NH4OH或HCl的晶片清洁溶液;
氢氧化铵溶液、氢氧化钠溶液、氢氧化钾溶液、季铵氢氧化物、乙二胺或者乙醇胺溶液;以及
三氧化铬、或者其它铬(VI)离子,以及硫酸;
(b)将包含二(全氟烷基磺酰基)酰亚胺或其盐的表面活性剂加入所述水溶液中。
2.如权利要求1所述降低溶液表面张力的方法,其特征在于,所述二(全氟烷基磺酰基)酰亚胺由下式表示:
式中,Rf 1和Rf 2分别为包含1-12个碳原子的全氟烷基,M是H或者无机或有机阳离子。
3.如权利要求1所述降低溶液表面张力的方法,其特征在于,所述二(全氟烷基磺酰基)酰亚胺是二(全氟丁磺酰基)酰亚胺。
4.如权利要求1所述降低溶液表面张力的方法,其特征在于,所述二(全氟烷基磺酰基)酰亚胺盐包含选自碱金属阳离子、碱土金属阳离子、H+、H3O+、NH4 +、Cu2+、Zn2+以及有机氮、有机氧和有机磷鎓阳离子的阳离子。
5.如权利要求4所述降低溶液表面张力的方法,其特征在于,所述阳离子选自H+、NH4 +、H3O+、Na+、K+、Li+、Mg2+、Ca2+、Zn2+和Cu2+。
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US09/853,065 US6555510B2 (en) | 2001-05-10 | 2001-05-10 | Bis(perfluoroalkanesulfonyl)imides and their salts as surfactants/additives for applications having extreme environments and methods therefor |
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EP (1) | EP1390134A2 (zh) |
JP (1) | JP2004533511A (zh) |
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CN (2) | CN1236845C (zh) |
AU (1) | AU2002257047A1 (zh) |
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CN100355491C (zh) | 2007-12-19 |
US7030067B2 (en) | 2006-04-18 |
US6555510B2 (en) | 2003-04-29 |
WO2002092211A3 (en) | 2003-05-30 |
US20040033366A1 (en) | 2004-02-19 |
WO2002092211A2 (en) | 2002-11-21 |
US20030036569A1 (en) | 2003-02-20 |
CA2446063C (en) | 2011-01-04 |
CN1721052A (zh) | 2006-01-18 |
CN1509204A (zh) | 2004-06-30 |
JP2004533511A (ja) | 2004-11-04 |
CA2446063A1 (en) | 2002-11-21 |
KR20040029972A (ko) | 2004-04-08 |
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AU2002257047A1 (en) | 2002-11-25 |
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