CN1289327A - 氟化物苯并三唑 - Google Patents
氟化物苯并三唑 Download PDFInfo
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- CN1289327A CN1289327A CN99802361A CN99802361A CN1289327A CN 1289327 A CN1289327 A CN 1289327A CN 99802361 A CN99802361 A CN 99802361A CN 99802361 A CN99802361 A CN 99802361A CN 1289327 A CN1289327 A CN 1289327A
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- fluorochemical benzotriazoles
- fluorochemical
- benzotriazoles
- metal
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- 229910052799 carbon Inorganic materials 0.000 claims description 11
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- 229910052802 copper Inorganic materials 0.000 description 31
- -1 Benzotriazoles compound Chemical class 0.000 description 20
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 20
- 239000012964 benzotriazole Substances 0.000 description 20
- SQASHPHWVSAHDM-UHFFFAOYSA-N 4h-benzotriazole-5-carboxylic acid Chemical compound C1C(C(=O)O)=CC=C2N=NN=C21 SQASHPHWVSAHDM-UHFFFAOYSA-N 0.000 description 14
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Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C33/00—Moulds or cores; Details thereof or accessories therefor
- B29C33/56—Coatings, e.g. enameled or galvanised; Releasing, lubricating or separating agents
- B29C33/60—Releasing, lubricating or separating agents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/44—Five-membered ring containing nitrogen and carbon only
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- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
- C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
- C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
- C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
- C23F11/14—Nitrogen-containing compounds
- C23F11/149—Heterocyclic compounds containing nitrogen as hetero atom
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/26—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
- Y10T428/261—In terms of molecular thickness or light wave length
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- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
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- Chemical Kinetics & Catalysis (AREA)
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- Oil, Petroleum & Natural Gas (AREA)
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Abstract
本发明提供了具有化学式(Ⅰ)的化合物,式中,Rf是CnF2n+1－(CH2)m－，其中n是1—22,m是0或者1—3的整数;X是－CO2－、－SO3－、－CONH－、－O－、－S－、共价键、－SO2NR－或－NR－,其中R是H或C1－C5亚烷基；Y是－CH2－,其中Z是0或1;R1是H,低级烷基或Rf－X－Yz－,条件是当X为－S－或－O－时,m是0,z是0,n≥1,当X是共价键时,m或z至少为1,以及该化合物的用途。
Description
发明领域
本发明涉及氟化物苯并三唑化合物及其用途。
发明背景
迄今为止，有许多方法用来加强一种材料从另一种材料或底材表面上的分离或剥离。例如，有机材料(如油类、蜡和聚硅氧烷)已被用作剥离剂用来向表面提供剥离性能。这些剥离剂的缺点之一是它们通常需要经常地重新施涂到表面上，以提供充足的剥离性能。聚合物剥离涂料(如由聚四氟乙烯制得的涂料)能克服油类、蜡、聚硅氧烷和其它临时涂料的一些缺点，且通常更耐久。然而，聚合物剥离涂料通常需要比非耐久处理更厚的涂层，它们会经历厚度变化，会使应用困难。
发明概述
本发明提供了氟化物苯并三唑(fluorochemical benzotriazole)，它与金属和准金属表面化学键合，向那些表面提供例如剥离和/或防腐蚀性能。本发明化合物的特征是具有首基和尾部，所述首基与金属或准金属表面键合，所述尾部的极性和/或官能度恰当地不同于待剥离的材料。本发明的化合物当施用在金属或准金属表面上时，形成耐久的自组装(self-assembled)膜，它是单层或基本上是单层的。本发明的氟化物苯并三唑包含那些具有以下化学式的化合物：式中，Rf是CnF2n+1-(CH2)m-，其中n是1-22的整数，m是0或者1-3的整数；X是-CO2-、-SO3-、-CONH-、-O-、-S-、共价键、-SO2NR-或-NR-，其中R是H或C1-C5亚烷基；Y是-CH2-，其中z是0或1；R1是H，低级烷基或Rf-X-Yz-，条件是当X为-S-或-O-时，m是0,z是0,n≥7，当X是共价键时，m或z至少为1。较好的是，n+m等于8-20的整数。
本发明还提供了包含一种或多种氟化物苯并三唑的组合物。
本发明还提供了一种用本发明化合物处理金属或准金属表面的方法，该方法包括用含有本发明氟化物苯并三唑的组合物与金属或准金属表面接触的步骤。可通过使表面与液态或气相形式的氟化物苯并三唑接触而在该表面上形成一层超薄膜。
本发明还提供了用作剥离剂的氟化物苯并三唑组合物，它包含一种或多种下式化合物：
式中，Rf是CnF2n+1-(CH2)m-，其中n是1-22,m是0或者1-3的整数；X是-CO2-、-SO3-、-S-、-O-、-CONH-、共价键、-SO2NR-或-NR-，其中R是H或C1-C5亚烷基；q是0或1；Y是C1-C4亚烷基，z是0或1；R1是H，低级烷基或Rf-X-Yz。
本发明化合物的一些优点包括：向表面上施用本发明的化合物较迅速且简单，这使成本和对环境的影响最小；用非常少量的化合物可形成致密的膜或层；本发明化合物能自组装形成保护层；该保护层可以非常耐久，这取决于表面类型和所用化合物。
附图的简要说明
图1是ScotchTM牌号MagicTM胶带的表1中所示剥离粘合力值的图解说明。
图2是HighlandTM牌号包装胶带的表1中所示剥离粘合力值的图解说明。
发明的详细说明
“金属表面”是指由金属或金属合金(它也可含有准金属)涂覆或形成的表面。“金属”是指如铁、金、铝等元素，通常具有以下特性：延性、展性、光泽、导热和导电性、能与羟基基团形成碱、能取代酸中的氢原子形成盐。“准金属”是指具有金属的一些性能和/或与金属形成合金的非金属元素(如半导体)，还包括含有金属和/或准金属掺杂剂的非金属元素。“剥离剂”是指赋予表面剥离性能的化合物或组合物。“低级烷基”是指含1-5个碳原子的烷基。
氟代脂族基团Rf是氟化的、稳定、惰性、非极性的单价基团，它既疏油又疏水。尽管Rf可具有大量碳原子，但较好的是Rf不超过22个碳原子的化合物，因为大基团中氟的有效利用率要比使用较小Rf基团能得到的低。Rf的骨架链可以是直链或支链，可以仅由碳、氢和氟组成，或者仅由碳和氟组成。一般来说，Rf可具有1-22个碳原子，较好是至少3个，更好是约6-12的碳原子，它可含有约40-83％(重量)、较好约40-74％(重量)的氟。较好是Rf的末端部分是全氟化部分，它较好是含有至少3个碳原子。较佳的化合物是那些其中R1基本上被完全氟化的化合物，例如其中Rf是CnF2n+1-(CH2)m-，其中m是2的化合物。
X可以是共价键、-CO2-、-SO3-、-CONH-、-SO2NR-、-O-、-S-或-NR-，其中R是H或C1-C5亚烷基。Y可以是亚甲基或共价键。R1可以是氢原子、低级烷基或如上所述的Rf-X-Y-，较好是氢原子。Rf-X-Y-部分较好是位于苯并三唑分子的第5个碳原子上。
本发明的化合物通常可通过苯并三唑与氟代醇反应而获得。该反应通常在溶液中进行，其中三唑和醇溶解于合适的溶剂。有用的三唑溶剂包括三氟甲烷磺酸和甲苯。反应在惰性气氛中于约100-120℃的温度下进行。冷却反应混合物，将分离得到的沉淀物再溶解于合适的溶剂，调节pH值至碱性并使溶剂蒸发。材料还可任选地用已知技术(如分级升华)提纯。
通过将本发明化合物与待处理的金属或准金属表面简单地接触，本发明的化合物会在金属或准金属表面上形成大致连续的单层膜。该分子形成“大致连续的单层”膜是指各分子以其分子结构允许的致密程度堆积(pack)在一起。这些膜被认为能自组装，原因是本发明分子的三唑基团与金属/准金属表面的可得区域连接，侧接的碳氟尾部基本上朝着外部界面排列。
单层膜的有效性和单层膜形成在表面上的程度通常取决于化合物和特定的金属或准金属表面之间的键合强度以及使用涂有膜的表面的条件。例如，一些金属或准金属表面需要高度韧性的单层膜，而其它这类表面需要具有低得多的键合强度的单层膜。有用的金属和准金属表面包括可与本发明化合物形成键合的任何表面，较好是形成单层膜或大致连续的单层膜。适用于形成所述单层膜的表面的例子包括那些含铜、镍、铬、锌、银、锗及其合金的表面。
本发明的单层膜或大致连续的单层膜可如下形成：使表面与足以涂覆整个表面的用量的本发明的一种或多种化合物接触。化合物可溶解在合适的溶剂中，将所得组合物施涂到表面上，使其干燥。合适的溶剂包括乙酸乙酯、2-丙醇、丙酮、水，以及它们的混合物。或者，本发明的化合物可以从气相淀积到表面上。任何过量的化合物可通过用溶剂漂洗底材和/或通过使用经处理的底材而除去。
本发明的氟化物苯并三唑特别可用作金属或准金属的表面或底材的剥离剂。具体用途包括作为用于压敏胶粘带剥离背衬的剥离剂和用于模具的脱模剂。本发明的组合物还可作为用于金属或准金属表面的防腐剂。
实施例
以下实施例阐述了本发明的特点和优点，这些实施例包括特定的材料及用量，但不应被认为是对本发明不恰当的限制。除非另外指出或显而易见，所有的材料均是市售的。除非另外指出，实施例中的所有份数、百分数、比率等都是以重量计的。
实施例1
如下制备苯并三唑-5-甲酸1H,1H,2H,2H-全氟十二烷基酯：
将苯并三唑-5-甲酸(3.5克，得自Aldrich Chemical Co.,Inc.,Milwaukee,WI)和三氟甲烷磺酸(″Triflic″酸，约12克，得自美国3M公司，St.Paul,MN)的混合物于约90℃加热并搅拌，直至得到均相溶液(约1小时)。将1H,1H,2H,2H-全氟十二烷基醇(11.58克，得自PCR Chemicals,Gainesville,FL)熔融并与18毫升无水甲苯一起加入反应混合物中。将所得的反应混合物在氮气气氛下加热至105-110℃约14个小时，然后冷却至环境温度。将经冷却的反应混合物倒在碎冰(约400克)上，剧烈搅拌所得混合物，以打破较大块的沉淀产物，在冰融化之后通过过滤分离出固态产物。将分离出的产物溶解在四氢呋喃(THF,500毫升)中，向该溶液中加入约50毫升水，以快速滴加方式加入氢氧化钾甲醇溶液(1N)，以使溶液的pH值上升至约8-9(用pH试纸确定)。用水(约100-150毫升)冲洗反应容器的侧壁，在氮气流下搅拌所得混合物，以蒸发THF。在大多数THF蒸发之后(约2.5小时)，该产物以泡沫状沉淀物的形式存在于约200毫升水中。通过过滤分离出固态产物，用数份(约100毫升)水洗涤，空气干燥过夜。于约115℃和10-6乇(133×10-6Pa)通过分级升华提纯粗材料。除去3-5小时后在升华器的指状部分(finger)上收集的蜡状固体(它由未反应的醇与痕量的水和溶剂的混合物组成)，于167-171℃继续进行升华，以制得经提纯的苯并三唑-5-甲酸1H,1H,2H,2H-全氟十二烷基酯(BTA-FCE-12)的淡粉红色/白色的固体，其熔点为171℃。该经提纯材料的NMR(H1,C13,F19)、红外光谱和GC/MS谱与以下结构一致：BTA-FCE-12
实施例2
基本上使用实施例1中所述的制备苯并三唑-5-甲酸1H,1H,2H,2H-全氟十二烷基酯的方法,制备苯并三唑-5-甲酸1H,1H,2H,2H-全氟十四烷基酯(BTA-FCE-14)、苯并三唑-5-甲酸1H,1H,2H,2H-全氟十二烷基酯(BTA-FCE-12)和苯并三唑-5-甲酸1H,1H,2H,2H-全氟癸基酯(BTA-FCE-10)的约4∶3∶1的混合物。不同的是，用1H,1H,2H,2H-全氟十四烷基醇、1H,1H,2H,2H-全氟十二烷基醇和1H,1H,2H,2H-全氟癸基醇的约4∶3∶1的混合物(12克，得自Daikin Chemical,Tokyo,Japan)代替1H,1H,2H,2H-全氟十二烷基醇。得到BTA-FCE-14、BTA-FCE-12和BTA-FCE-10的上述混合物的粉红色/白色固体。该经提纯材料的NMR(H1,C13,F19)和GC/MS谱与以下结构一致：BTA-FCE-14BTA-FCE-12BTA-FCE-10
实施例3
基本上使用实施例1中所述的制备苯并三唑-5-甲酸1H,1H,2H,2H-全氟十二烷基酯的方法，制备苯并三唑-5-甲酸1H,1H,2H,2H-全氟癸基酯，不同的是用1H,1H,2H,2H-全氟癸基醇(9.3克，得自PCR Chemicals)代替1H,1H,2H,2H-全氟十二烷基醇。得到苯并三唑-5-甲酸1H,1H,2H,2H-全氟癸基酯(BTA-FCE-10)的粉红色/白色固体，其熔点为143-145℃。该经提纯材料的NMR(H1,C13,F19)、红外光谱和GC/MS谱与以下结构一致：
BTA-FCE-10
实施例4
基本上使用实施例1中所述的制备苯并三唑-5-甲酸1H,1H,2H,2H-全氟十二烷基酯的方法，制备苯并三唑-5-甲酸1H,1H,2H,2H-全氟辛基酯，不同的是用1H,1H,2H,2H-全氟辛基醇(7.3克，得自PCR Chemicals)代替1H,1H,2H,2H-全氟十二烷基醇。得到苯并三唑-5-甲酸1H,1H,2H,2H-全氟辛基酯(BTA-FCE-8)的粉红色/白色固体，其熔点为118-122℃。该经提纯材料的NMR(H1,C13,F19)、红外光谱和GC/MS谱与以下结构一致：
BTA-FCE-8
实施例5
基本上使用实施例1中所述的制备苯并三唑-5-甲酸1H,1H,2H,2H-全氟十二烷基酯的方法，制备苯并三唑-5-甲酸1H,1H,2H,2H-全氟己基酯，不同的是用1H,1H,2H,2H-全氟己基醇(5.3克，得自PCR Chemicals)代替1H,1H,2H,2H-全氟十二烷基醇。得到苯并三唑-5-甲酸1H,1H,2H,2H-全氟己基酯(BTA-FCE-6)的粉红色/白色固体，其熔点为105-107C。该经提纯材料的NMR(H1,C13,F19)、红外光谱和GC/MS谱与以下结构一致：
BTA-FCE-6
实施例6
使用ASTM D3330-96的测量剥离粘合力的标准试验研究苯并三唑-5-甲酸1H,1H,2H,2H-全氟十二烷基酯与铜反应并改变铜表面性能的能力，不同的是将胶带样品反复地施用在试样片的相同区域，用剥离强度作为对铜表面剥离处理的附着性(substantivity)的指标。
用3.2 mm厚的铜板(热轧铜板，ASTM B152 Alloy110，软M20回火，CentralSteel & Wire Co.,Chicago,IL)制备粘合力试样片(20.3×5.1cm)。用手持打磨器，再逐渐地用更细的砂纸(3M WETORDRYTM TRI-M-ITETM280,600和1200粗砂，得自美国3M公司，St.Paul,MN)研磨，每个阶段3分钟，如此对每块试样片进行表面抛光。紧接在对试样片进行剥离处理之前，用浸透庚烷的抹布(KimwipesExtra Low Lint Wiper#34256，得自Kimberley Clark Corp,Roswell,GA)擦拭试样片，然后用浸透乙醇的抹布擦拭，如此对试样片进行清洁。将如上制得的BTA-FCE-12如下施用到两块清洁的试样片的表面上：将试样片与29mgBTA-FCE-12一起放置在10.2cm直径×25.4cm高的可抽真空的玻璃室中，将该仪器抽真空至10-7乇(133×10-7Pa)，将该被抽真空的室放在保持于150℃循环空气炉中中3.5小时。
将处于真空(10-7乇(133×10-7Pa))的第三块试样片与50.3mg苯并三唑(BTA)于150℃加热1.5小时，如此将BTA施用到第三块试样片上，提供比较用的反应性表面处理。
用线型聚(二甲基硅氧烷)脱模剂，IMS S312-A(得自IMS,Chagrin Falls,OH)喷涂第四块试样片，如此用聚硅氧烷剥离材料处理第四块试样片，提供与非反应性表面处理的比较。
将用上述浸透溶剂的擦拭技术清洁过的试样片用作对比例。
在ASTM标准D3330-96中所述的条件下，直接测量压敏胶粘带条对上述经处理的铜试样片和对比例的粘合力。按试验方法中的规定将胶粘带施用到试样片上，随后用Instrumentors Inc.,Strongsville,OH制造的恒定伸长速率的粘合力试验机以38.1毫米/秒的速率以180°从表面上剥离。在试验之前将所有的胶粘带和铜试样片置于50％的相对湿度和23℃下适应24小时，所有的剥离试验是在这些环境条件下进行的。
将两种市售压敏胶粘带，具有丙烯酸酯基粘合剂的ScotchTM牌号MagicTM胶带#810(得自美国3M公司)和具有KratonTM剂粘合剂的HighlandTM牌号包装胶带#371(得自美国3M公司)用于粘合力试验。
代表性的剥离粘合剂数据总结于表1。该表中数据的图解示于图1和图2。曲线1-1和2-1表示经BTA-FCE-12处理的铜的剥离粘合剂数据；曲线1-2和2-2表示经聚硅氧烷处理的铜的剥离粘合力数据；曲线1-3和2-3表示未经处理的铜的剥离粘合力数据；曲线1-4和2-4表示经BTA处理的铜的剥离粘合力数据。BTA-FCE-12改性铜表面得到的剥离粘合力值明显地低于对比例铜表面或经聚硅氧烷剥离剂处理的铜或经母体苯并三唑处理的铜。
表1剥离粘合力值
| 底材 | ScotchTM牌号MagicTM胶带 | HighlandTM牌号包装胶带 | ||
| 剥离# | 剥离力(N/100mm) | 剥离# | 剥离力(N/100mm) | |
| 未经处理的铜 | 1 | 40.4 | 1 | 19.3 |
| 2 | 40.6 | 2 | 24.2 | |
| 3 | 40.0 | 3 | 25.2 | |
| 4 | 37.5 | 4 | 25.8 | |
| 5 | 37.5 | 5 | 32.1 | |
| 6 | 37.7 | 6 | 30.2 | |
| 7 | 34.3 | |||
| 经BTA-FCE-12处理的铜 | 1 | 7.9 | 1 | 3.1 |
| 2 | 8.6 | 2 | 2.9 | |
| 3 | 7.2 | 3 | 3.1 | |
| 4 | 7.7 | 4 | 2.6 | |
| 5 | 8.2 | 5 | 2.5 | |
| 6 | 8.0 | 6 | 2.6 | |
| 7 | 8.3 | 7 | 2.6 | |
| 经聚硅氧烷脱模剂处理的铜 | 1 | 16.6 | 1 | 20.4 |
| 2 | 17.1 | 2 | 24.7 | |
| 3 | 20.0 | 3 | 29.5 | |
| 4 | 22.5 | 4 | 38.8 | |
| 5 | 22.0 | 5 | 42.2 | |
| 6 | 47.7 | |||
| 经BTA处理的铜 | 1 | 56.2 | 1 | 13.4 |
| 2 | 67.7 | 2 | 49.9 | |
| 3 | 63.5 | 3 | 72.5 | |
| 4 | 57.1 | 4 | 71.7 | |
| 5 | 57.8 | 5 | 70.8 | |
| 6 | 52.4 | 6 | 68.7 | |
| 7 | 52.5 | 7 | 68.4 | |
实施例7
通过试验铜表面的防腐能力来研究苯并三唑-5-甲酸1H,1H,2H,2H-全氟十二烷基酯与铜反应并改变铜表面性能的能力。
将软轧合金110铜箔(厚度为0.00343cm，纯度高于99.90％)用于防腐试验。如上所述用浸透溶剂的抹布对铜进行清洁，并切割成5cm×10cm的试样片。
将一块试样片与35.4mgBTA-FCE-12一起放入6.0cm直径×22.0cm高的可抽真空的玻璃室，将该室抽真空至1×10-7乇(133×10-7Pa)，将该抽真空的室放在保持于150℃的循环空气炉中1小时，如此用BTA-FCE-12处理试样片。
按大致相同的方法用44.0mg苯并三唑(BTA)处理第二块试样片，不同的是炉子保持于100℃，提供比较用的反应性表面处理。
将用上述浸透溶剂的擦拭技术清洁过的铜箔用作对比例。
将经BTA-FCE-12和BTA处理的铜和对比例的5厘米×3厘米的样品以非重叠的位置放在12.7cm×20.3cm的聚乙烯袋中，将该袋密封，将100微升硫化氢气体透过袋壁直接注入，穿孔用胶粘带密封，观察样品表面由于形成硫化物而引起的颜色变化。只有对比例发现颜色在1小时内从暗红色变成紫色。
1小时后从袋中取出这些样品并对每个样品表面进行分析，该分析测量x射线光电子能谱(XPS或ESCA)，使用型号为SSX-100-01M-ProbeTM ESCA的分光计(得自表面科学实验室，Mountain View,CA)，该仪器使用AlKα单色x射线激发源和半球形能量分析仪。对于所有记录的光谱，光电子的发射角(take-offangle)是与表面垂直方向成38°角。每个样品上的分析面积为200微米×750微米。分析过程中真空体系中的压力保持在2.7×10-7Pa或更低。
记录在每个样品表面上的测量光谱(0eV-1100eV结合能/2200数据点/每个数据点每次扫描100毫秒停留时间×8次扫描)。测量每个测量光谱中C(1s1/2)、O(1s1/2)、N(1s1/2)、Cu(2P3/2)、F(1s1/2)和S(2p3/2,1/2)光电子峰的面积，将每个面积值除以仪器制造商提供的数据处理软件中规定的合适的相对敏感因数，计算得到每个表面上的碳、氧、氮、铜、氟和硫的原子百分数浓度。所有的计算值均忽略了本技术无法检测到的氢的存在。由这些分析得到的信息总结于表2中。
数据表明，经BTA-FCE-12处理的表面上不存在可检测含量的硫，而经BTA处理和未经处理的铜表面在暴露于H2S之后显示存在硫的证据。这类表而上对硫的检测限度约为0.08％(原子)(信噪比为2.0)。暴露于H2S之后，未经处理和经BTA处理的铜样品上S(2p3/2)峰的结合能为162-163eV，与NIST XPS数据库中给出的Cu2S的结合能匹配(NIST标准参考数据库#20-2.0版，美国商业部，国家标准与技术研究会，Gaithersburg,MD)。
表2
用XPS(ESCA)测得的每个铜表面上以可检测含量存在的元素
| 样品说明 | 原子％浓度 | |||||
| C | O | N | Cu | F | S | |
| 对比例-未暴露于H2S | ||||||
| 未经处理的铜 | 50.5 | 22.9 | n.d. | 26.6 | n.d. | n.d. |
| 经BTA-FCE-12处理的铜 | 39.0 | 3.1 | 3.8 | 0.9 | 53.2 | n.d. |
| 经BTA处理的铜 | 65.4 | 0.9 | 24.8 | 8.9 | n.d. | n.d. |
| 暴露于100μlH2S中1小时 | ||||||
| 未经处理的铜 | 58.8 | 7.0 | n.d. | 19.6 | n.d. | 14.6 |
| 经BTA-FCE-12处理的铜 | 39.1 | 3.3 | 3.9 | 0.9 | 52.8 | n.d. |
| 经BTA处理的铜 | 63.2 | 2.1 | 25.3 | 8.6 | n.d. | 0.8 |
n.d.未检测到
在不偏离本发明精神和范围的情况下本领域技术人员显然可对本发明作出各种改动和变化，本发明不应局限于本文中所列的用于说明目的的例子。
Claims (24)
1．一种氟化物苯并三唑，它具有以下化学式：
式中，Rf是CnF2n+1-(CH2)m-，其中n是1-22,m是0或者1-3的整数；X是-CO2-、-SO3-、-CONH-、-O-、-S-、共价键、-SO2NR-或-NR-，其中R是H或C1-C5亚烷基；Y是-CH2-，其中z是0或1；R1是H，低级烷基或Rf-X-Yz-，条件是当X为-S-或-O-时，m是0,z是0,n≥7，当X是共价键时，m或z至少为1。
2．如权利要求1所述的氟化物苯并三唑，其特征在于R1是H。
3．如权利要求1所述的氟化物苯并三唑，其特征在于n是3-12。
4．如权利要求3所述的氟化物苯并三唑，其特征在于z是0。
5．如权利要求4所述的氟化物苯并三唑，其特征在于X是-CO2-、-SO3-、-O-、-NR-、-SO2NR-、-NR-或-S-。
6．如权利要求5所述的氟化物苯并三唑，其特征在于n至少是3。
7．如权利要求1所述的氟化物苯并三唑，其特征在于n是6-12。
8．如权利要求7所述的氟化物苯并三唑，其特征在于m是2,z是0。
9．如权利要求8所述的氟化物苯并三唑，其特征在于X是-CO2-。
10．如权利要求9所述的氟化物苯并三唑，其特征在于n是10。
11．如权利要求1所述的氟化物苯并三唑，其特征在于n至少是6，其中n+m为8-20。
12．一种赋予金属或准金属表面剥离性能或防腐性能的组合物，它包含一种或多种权利要求1所述的化合物。
13．如权利要求12所述的组合物，其特征在于所述组合物包含两种或多种具有权利要求1化学式的化合物。
14．如权利要求12所述的组合物，其特征在于该组合物还含有溶剂。
15．一种在金属或准金属表面上形成粘合的超薄膜的方法，该方法包括使包含权利要求1的氟化物苯并三唑的组合物与所述表面接触的步骤。
16．如权利要求15所述的方法，其特征在于所述组合物还包含溶剂。
17．如权利要求15所述的方法，其特征在于所述组合物是溶液或蒸气形式。
18．一种超薄膜，它包含一种或多种权利要求1的氟化物苯并三唑的许多分子与金属或非金属表面键合，所述许多分子形成大致连续的单层自组装膜。
19．一种制品，它包含粘合有自组装超薄膜的金属或准金属表面，所述膜包含粘合在所述表面上的一种或多种权利要求1的氟化物苯并三唑的许多分子。
20．将权利要求12的组合物用作剥离剂或防腐剂。
21．用作剥离剂的组合物，所述组合物包含具有以下化学式的一种或多种氟化物苯并三唑：
式中，Rf是CnF2n+1-(CH2)m-，其中n是1-22,m是0或者1-3的整数；X是-CO2-、-SO3-、-S-、-O-、-CONH-、共价键、-SO2NR-或-NR-，其中R是H或C1-C5亚烷基；q是0或1；Y是C1-C4亚烷基，z是0或1；R1是H，低级烷基或Rf-X-Yz。
22．一种制品，它具有剥离表面，该剥离表面包含粘合有自组装超薄膜的金属或准金属表面，所述膜包含粘合在所述表面上的一种或多种权利要求19的氟化物苯并三唑的许多分子。
23．一种在金属或准金属表面上以粘合的超薄膜形式形成剥离剂的方法，该方法包括使包含权利要求19的氟化物苯并三唑的组合物与所述表面接触的步骤。
24．一种剥离剂，其形式是超薄膜，包含一种或多种权利要求19的氟化物苯并三唑的许多分子与金属或非金属表面键合，其中所述许多分子形成大致连续的单层自组装膜。
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101189363B (zh) * | 2005-05-06 | 2013-02-06 | 威士伯采购公司 | 改进金属表面的耐蚀性的方法 |
Families Citing this family (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100302479A1 (en) * | 1996-03-21 | 2010-12-02 | Aronson Joseph T | Optical article |
| US6166218A (en) * | 1996-11-07 | 2000-12-26 | Ciba Specialty Chemicals Corporation | Benzotriazole UV absorbers having enhanced durability |
| EP1051408B1 (en) * | 1998-01-27 | 2003-08-27 | Minnesota Mining And Manufacturing Company | Fluorochemical benzotriazoles |
| CA2353506A1 (en) * | 1998-11-02 | 2000-05-11 | 3M Innovative Properties Company | Transparent conductive oxides for plastic flat panel displays |
| US6632872B1 (en) | 2000-09-19 | 2003-10-14 | 3M Innovative Properties Company | Adhesive compositions including self-assembling molecules, adhesives, articles, and methods |
| US6824882B2 (en) | 2002-05-31 | 2004-11-30 | 3M Innovative Properties Company | Fluorinated phosphonic acids |
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| US7189479B2 (en) * | 2003-08-21 | 2007-03-13 | 3M Innovative Properties Company | Phototool coating |
| US7148360B2 (en) | 2004-01-30 | 2006-12-12 | 3M Innovative Properties Company | Perfluoropolyether benzotriazole compounds |
| US20060141220A1 (en) * | 2004-12-23 | 2006-06-29 | Merrill William W | Uniaxially oriented article having a structured surface |
| US20060138694A1 (en) * | 2004-12-23 | 2006-06-29 | Biernath Rolf W | Method of making a polymeric film having structured surfaces via replication |
| US20060138702A1 (en) * | 2004-12-23 | 2006-06-29 | Biernath Rolf W | Method of making uniaxially oriented articles having structured surfaces |
| US20060204720A1 (en) * | 2004-12-23 | 2006-09-14 | Biernath Rolf W | Uniaxially oriented birefringent article having a structured surface |
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| US20060138686A1 (en) * | 2004-12-23 | 2006-06-29 | Ouderkirk Andrew J | Method of making a uniaxially stretched polymeric film having structured surface |
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| US20060141219A1 (en) * | 2004-12-23 | 2006-06-29 | Benson Olester Jr | Roll of a uniaxially oriented article having a structured surface |
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| US20070066762A1 (en) * | 2005-09-22 | 2007-03-22 | Acosta Erick J | Triazole-containing fluorinated polymers |
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| WO2009088604A1 (en) * | 2007-12-31 | 2009-07-16 | 3M Innovative Properties Company | Method for applying a coatable material |
| CN102036758B (zh) * | 2008-03-26 | 2013-10-30 | 3M创新有限公司 | 坡流涂布两种或更多种流体的方法 |
| KR20110000665A (ko) * | 2008-03-26 | 2011-01-04 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 다중 단위 중합체성 전구체를 포함하는 유체를 슬라이드 코팅하는 방법 |
| KR20110000664A (ko) * | 2008-03-26 | 2011-01-04 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 둘 이상의 유체를 슬라이드 코팅하는 방법 |
| US8350451B2 (en) * | 2008-06-05 | 2013-01-08 | 3M Innovative Properties Company | Ultrathin transparent EMI shielding film comprising a polymer basecoat and crosslinked polymer transparent dielectric layer |
| WO2010002788A1 (en) * | 2008-06-30 | 2010-01-07 | 3M Innovative Properties Company | Solvent assisted method of microcontact printing |
| US20100252961A1 (en) * | 2009-04-06 | 2010-10-07 | 3M Innovative Properties Company | Optical film replication on low thermal diffusivity tooling with conformal coating |
| US20120127578A1 (en) | 2009-08-03 | 2012-05-24 | Bright Clark I | Antireflective transparent emi shielding optical filter |
| JP2013510734A (ja) | 2009-11-10 | 2013-03-28 | スリーエム イノベイティブ プロパティズ カンパニー | ポリラクチドフィルムの製造方法 |
| WO2012061457A2 (en) | 2010-11-02 | 2012-05-10 | 3M Innovative Properties Company | Siloxane graft co-polymers for mold release |
| EP2851376B1 (en) | 2010-11-04 | 2016-04-20 | 3M Innovative Properties Company | Fluorinated composition comprising phosphorus containing acid group and alkoxy silane group |
| EP2500009A1 (en) | 2011-03-17 | 2012-09-19 | 3M Innovative Properties Company | Dental ceramic article, process of production and use thereof |
| US8628869B2 (en) | 2012-01-30 | 2014-01-14 | HGST Netherlands B.V. | Magnetic media and magnetic recording devices using fluorine compounds |
| JP5993779B2 (ja) * | 2013-03-29 | 2016-09-14 | 富士フイルム株式会社 | 導電膜形成用組成物、導電膜、配線基板 |
| US10407778B2 (en) | 2016-06-09 | 2019-09-10 | Chemtreat, Inc | Corrosion inhibition for aqueous systems using a halogenated triazole |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1130282B (de) * | 1960-01-16 | 1962-05-24 | Agfa Ag | Verfahren zur Klarhaltung von photographischen Halogensilber-emulsionen bei hoeherenEntwicklertemperaturen |
| JPS4826012B1 (zh) * | 1969-12-26 | 1973-08-03 | ||
| JPS5494319A (en) * | 1978-01-09 | 1979-07-26 | Konishiroku Photo Ind Co Ltd | Silver halide photographic material |
| US4187186A (en) * | 1978-04-12 | 1980-02-05 | Mobil Oil Corporation | Lubricant compositions containing esters of benzotriazolecarboxylic acid |
| JPS62103640A (ja) * | 1985-07-18 | 1987-05-14 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
| JPH0778186B2 (ja) * | 1986-05-23 | 1995-08-23 | 旭硝子株式会社 | 硬化性組成物 |
| DE3767605D1 (de) * | 1986-07-31 | 1991-02-28 | Ciba Geigy Ag | Verfahren zur inhibierung von metalloberflaechenkorrosion durch verwendung von perfluoralkyl enthaltenden triazolen. |
| US4788292A (en) * | 1986-07-31 | 1988-11-29 | Ciba-Geigy Corporation | Perfluoroalkyl substituted benzotriazoles |
| JPS63295630A (ja) * | 1987-05-27 | 1988-12-02 | Asahi Glass Co Ltd | 含フツ素ポリエ−テル−エステル交互共重合体の製造方法 |
| JP2986513B2 (ja) * | 1990-06-15 | 1999-12-06 | 克嘉 蓼沼 | 固体材料及びその表面処理方法 |
| JP3035672B2 (ja) * | 1991-06-10 | 2000-04-24 | 株式会社ネオス | 含フッ素芳香族エステル |
| CA2071596A1 (en) * | 1991-07-10 | 1993-01-11 | Frederick E. Behr | Perfluoroalkyl halides and derivatives |
| JPH05320957A (ja) * | 1992-05-15 | 1993-12-07 | Union Chem Kk | 防錆材料 |
| JPH0641011A (ja) * | 1992-07-24 | 1994-02-15 | Fuji Photo Film Co Ltd | カルボキシル基含有フッ素系エステル化合物及びその製造方法 |
| US5250698A (en) * | 1992-08-05 | 1993-10-05 | Ciba-Geigy Corporation | 2-(2-hydroxy-3-perfluoroalkyl thiomethyl-5-alkylphenyl)2H-benzotriazoles and stabilized compositions thereof |
| DE4302461A1 (de) * | 1993-01-29 | 1994-08-04 | Bayer Ag | Fluorierte Benzotriazole |
| JPH07228575A (ja) * | 1994-02-18 | 1995-08-29 | Japan Energy Corp | 新規ベンゾトリアゾールフッ素誘導体及びその製造方法並びにそれを用いる金属表面処理剤 |
| JPH07309847A (ja) * | 1994-05-20 | 1995-11-28 | Japan Energy Corp | 新規ベンゾトリアゾールフッ素メタクリルイソシアネート誘導体及びその製造方法並びにそれを用いる表面処理剤 |
| JP3605868B2 (ja) * | 1995-03-01 | 2004-12-22 | 日本油脂株式会社 | 撥水・撥油性材料 |
| MY129257A (en) * | 1995-03-21 | 2007-03-30 | Betz Laboratories | Methods of inhibiting corrosion using halo-benzotriazoles |
| TW399094B (en) * | 1995-04-11 | 2000-07-21 | Ciba Sc Holding Ag | Compounds with (benzo)triazole radicals |
| DE69720943D1 (de) * | 1996-12-30 | 2003-05-22 | Agfa Gevaert Nv | Verfahren zur Verarbeitung eines photographischen lichtempfindlichen Silberhalogenidmaterials |
| EP1051408B1 (en) * | 1998-01-27 | 2003-08-27 | Minnesota Mining And Manufacturing Company | Fluorochemical benzotriazoles |
-
1999
- 1999-01-15 EP EP99902286A patent/EP1051408B1/en not_active Expired - Lifetime
- 1999-01-15 DE DE69910732T patent/DE69910732T2/de not_active Expired - Lifetime
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-
2000
- 2000-09-20 US US09/666,359 patent/US6376065B1/en not_active Expired - Lifetime
-
2010
- 2010-07-27 JP JP2010167658A patent/JP2011016805A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101189363B (zh) * | 2005-05-06 | 2013-02-06 | 威士伯采购公司 | 改进金属表面的耐蚀性的方法 |
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| EP1051408B1 (en) | 2003-08-27 |
| JP2002501057A (ja) | 2002-01-15 |
| KR100530819B1 (ko) | 2005-11-24 |
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