CN103261482B - 聚酯聚胺和聚酯聚季铵腐蚀抑制剂 - Google Patents
聚酯聚胺和聚酯聚季铵腐蚀抑制剂 Download PDFInfo
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- CN103261482B CN103261482B CN201180060587.XA CN201180060587A CN103261482B CN 103261482 B CN103261482 B CN 103261482B CN 201180060587 A CN201180060587 A CN 201180060587A CN 103261482 B CN103261482 B CN 103261482B
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- 238000004448 titration Methods 0.000 description 1
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Abstract
本发明涉及可通过如下反应获得的产物作为金属表面的腐蚀抑制剂的用途：使式R1COOH(I)的脂肪酸或酸混合物，和式(IIa)或(IIb)的二羧酸或其衍生物与式(III)的烷氧基化脂肪胺或其部分或完全季化的衍生物反应；任选在所述脂肪酸、二羧酸与烷氧基化脂肪胺的反应之后，存在另一反应步骤，在所述反应步骤中通过与烷基化试剂R5X反应而使部分或全部氮原子季化。本发明还涉及该产物及其制备方法。
Description
本发明的技术领域
本发明涉及一种聚酯胺或聚酯聚季铵化合物作为金属表面腐蚀抑制剂的用途，以及一种保护金属表面以免腐蚀的方法，包括使所述金属表面与所述腐蚀抑制剂接触。本发明进一步涉及所述聚酯胺或聚酯聚季铵化合物本身及其制备方法。
本发明的背景技术
在油气田工艺(例如在输送原油)以及油或气井中，腐蚀通常是一个严重的问题。这可能是由于溶解的气体如二氧化碳或硫化氢所导致的，其分别在含铁金属表面上导致所谓的无硫腐蚀和二氧化硫腐蚀。另一种严重的腐蚀提高剂通常为与油气一起产生的于水中的高电解质浓缩物。此外，当将无机或有机酸用于所遇到的所谓酸增产或压裂操作中以提高油气井的生产率时，很明显会产生严重的腐蚀风险。此外，在钻井操作中，通常需要使用腐蚀抑制剂，例如在钻井流体中。在下游工艺如精炼中，腐蚀问题通常也是一个难题，例如当加工中的原油的盐或酸组分导致含铁金属腐蚀。
不同类型的含氮化合物，如脂肪胺、烷氧基化的脂肪胺、酰胺基胺和季铵化合物是公知的用于各类体系中的腐蚀抑制剂配制剂的碱。
例如，US5352377和US5456731公开了烃基取代的羧酸酐，更特别地为烃基取代的琥珀酸酐与氨基链烷醇的反应产物，例如乙氧基化的脂肪烷基单胺或乙氧基化的脂肪烷基丙二胺，其可在润滑剂和燃料油应用中提供有效的抗磨损、防锈和腐蚀抑制性能。
US5178786涉及腐蚀抑制组合物及其在功能流体，尤其是水性液压液中的用途。这些组合物包含至少4种组分A、B、C和D，其中组分D为由烷基或烯基琥珀酸酐与链烷醇胺的反应所形成的酯盐。优选的链烷醇胺例如为二甲基乙醇胺、二乙基乙醇胺和甲基乙基乙醇胺。
还存在许多公开专利，其中将基于二羧酸/酐和乙氧基化(脂肪烷基)胺的低聚/聚合含氮且酯连接的化合物用于其它应用场合/体系中。例如，EP0572881公开了用于分离油包水型石油乳液的方法中且获自氧烷基化的脂肪族伯胺与二羧酸的产物。US4781730公开了多元酸与聚羟基链烷醇胺的反应产物，其为用于减少机动车中的阀座缩陷的燃料添加剂组合物的组分。US5034444公开了一种用于非水性涂料组合物中的流变添加剂，其可为烷氧基化脂族含氮化合物与有机多元羧酸酐或酸的反应产物。EP0035263A2公开了由二羧酸与烷氧基化叔胺之间的反应制备的聚酯化合物及其作为织物软化剂的用途。US5284495公开了可通过聚合酸酐(例如邻苯二甲酸酐)与含长链胺的二醇(例如乙氧基化的十八烷基胺)而制备的低聚物/聚合物。将这些产物用作提高馏出燃料油低温性能的添加剂。US5710110公开了包含油井流体抗沉降添加剂的钻井流体组合物，所述抗沉降添加剂为其中反应物为一种或多种烷氧基化脂族氨基化合物和有机多元羧酸酐或酸的反应产物。
US6432895和EP1949963A1涉及为链烷醇胺酯的产物，其基于任选烷氧基化的链烷醇胺、二羧酸和脂肪酸以及阳离子表面活性剂和可由其获得的酯季铵化物。
尽管已开发了各种可在淡水、海水或盐水存在下使用的腐蚀抑制剂，仍需要更有效的腐蚀抑制剂，特别是当这些腐蚀抑制剂也可显示出满足严格的环境适应性的法规要求时。因此，非常需要具有可接受的生物降解性且兼具低生物富集处置和优异工业性能的新型腐蚀抑制剂。
发明简述
本发明的一个目的是至少部分满足上述本领域的需求且提供一种显示出高功效的腐蚀抑制化合物。
本发明的另一目的是提供具有有利的环境性能的腐蚀抑制化合物。
本发明人发现这些目的可通过特定的聚酯聚胺或聚酯聚季铵化合物实现，其可通过缩合脂肪酸、二羧酸或其衍生物和烷氧基化脂肪胺而获得，其中任选借助合适的烷基化试剂使所述缩合产物季化。
因此，在第一方面中，本发明涉及上述产物作为金属表面的腐蚀抑制剂的用途。
在第二方面中，本发明涉及一种保护金属表面以免腐蚀的方法，包括使所述金属表面与有效量的上述腐蚀抑制剂接触。
本发明的这些以及其他方面由下文的本发明详述显而易见。
本发明详述
本发明涉及可通过如下反应获得的产物作为金属表面的腐蚀抑制剂的用途：使式R1COOH(I)的脂肪酸或酸混合物，其中R1CO为具有8-24个，优选12-24个，更优选14-24个，最优选16-24个碳原子且可为饱和或不饱和的、直链或支化的酰基；和式(IIa)或(IIb)的二羧酸或其衍生物：
其中D为-OH、-Cl或-OR3，其中R3为C1-C4烷基；R2选自单键，式-(CH2)z-的亚烷基，其中z为1-10的整数，优选为2-4的整数，最优选为4，其中所述亚烷基被1或2个-OH基取代的取代亚烷基、亚环烷基、亚环烯基或亚芳基；
与式(III)的烷氧基化脂肪胺或者可通过部分或完全季化式(III)的烷氧基化脂肪胺而获得的产物缩合：
其中R4为具有8-24个碳原子，优选12-24个碳原子的烃基；AO为包含2-4个碳原子，优选2个碳原子的亚烷氧基；各B独立地为具有1-4个碳原子的烷基，或苄基；各n独立地至少为1，且所有n之和为2-30，优选为2-15，更优选为2-10，最优选为2-5；s为2或3；且y为0或1；任选在所述脂肪酸、二羧酸与烷氧基化脂肪胺的反应之后，存在另一反应步骤，在所述反应步骤中通过与烷基化试剂R5X反应而使部分或全部氮原子季化，其中R5为烃基，优选为C1-C4烷基或苄基；且X-为衍生自所述烷基化试剂R5X的阴离子。
在一个实施方案中，所述烷氧基化脂肪胺或其部分或完全季化的衍生物具有下式且可作为金属表面的腐蚀抑制剂：
其中各x独立地为1-5的数，且∑x的摩尔平均值为2-10的数；AO为具有2-4个碳原子，优选2个碳原子的亚烷氧基；R4为具有8-24个碳原子，优选12-24个碳原子的烃基；任选在所述脂肪酸、二羧酸和烷氧基化脂肪胺的反应之后，存在另一反应步骤，在所述反应步骤中通过与烷基化试剂R5X反应而使部分或全部氮原子季化，其中R5为烃基，优选为C1-C4烷基或苄基；且X-为衍生自所述烷基化试剂R5X的阴离子。
对其中上述缩合产物获自式(IIIA)的烷氧基化脂肪胺的实施方案而言，所述产物可由如下通式表示：
其中R1、AO、x、R2和R4具有与上文相同的含义；R5为烃基，优选为C1-C4烷基或苄基；X-为衍生自所述烷基化试剂R5X的阴离子；t为0或1的数，优选为1；p通常为1-15的数，且平均至少为1，优选至少为2，最优选至少为3。p的平均值取决于所述反应混合物中的化合物(I)、(IIa)或(IIb)和(III)的摩尔比，且取决于反应条件。
应理解的是，所述产物混合物中可存在未完全被脂肪酸酯化的分子，但式IV的产物为关键化合物。
式(I)脂肪酸的合适实例为2-乙基己酸、正辛酸、正癸酸、正十二烷酸、正十四烷酸、正十六烷酸、棕榈油酸、正十八烷酸、油酸、亚油酸、亚麻酸、二十烷酸、二十二烷酸、二十四烷酸、椰油脂肪酸、油菜籽脂肪酸、大豆脂肪酸、牛油脂肪酸、妥尔油脂肪酸、顺-9-二十碳烯酸和芥酸。
通式(IIa)或(IIb)的二羧酸衍生物可为二羧酸本身、二羧酰氯、二羧酸的二酯或二羧酸的环状酸酐。最合适的衍生物为二羧酸及其相应的环状酸酐。二羧酸衍生物的示意性实例包括草酸、丙二酸、琥珀酸、戊二酸、己二酸、庚二酸、邻苯二甲酸、四氢邻苯二甲酸、苹果酸、酒石酸、其相应的酰氯、其相应的甲酯或乙酯及其相应的环状酸酐。
用作烷氧基化脂肪胺(III)的原料的合适脂肪胺的示意性实例包括但不限于式R4NH2的(脂肪烷基)单胺，其中R4为具有8-24个，优选12-24个碳原子的脂族基团；和式R4N(CH3)CH2CH2CH2NH2的(脂肪烷基)甲基二胺。上述胺的更具体的实例包括但不限于2-乙基己胺、2-丙基庚胺、正辛胺、正癸胺、正十二烷基胺、(椰油烷基)胺、正十四烷基胺、正十六烷基胺、正十八烷基胺、油胺、(牛油烷基)胺、(氢化牛油烷基)胺、(油菜籽烷基)胺、(大豆烷基)胺、芥酸基(erucyl)胺、N-正癸基-N-甲基三亚甲基二胺、N-正十二烷基-N-甲基三亚甲基二胺、N-(椰油烷基)-N-甲基三亚甲基二胺、N-(油菜籽烷基)-N-甲基三亚甲基二胺、N-(大豆烷基)-N-甲基三亚甲基二胺、N-(牛油烷基)-N-甲基三亚甲基二胺、N-(氢化牛油烷基)-N-甲基三亚甲基二胺和N-芥酸基-N-甲基三亚甲基二胺。
然后，通常用如下单元将这些脂肪胺烷氧基化：2-20个，优选2-10个EO(亚乙氧基单元)，2-20个，优选2-10个PO(亚丙氧基单元)，2-20个，优选2-10个BO(亚丁氧基单元)，首先加成EO且最后加成PO和/或BO的嵌段，首先加成PO和/或BO且最后加成EO的嵌段，或者EO和PO和/或BO的混合物以制备通式(III)的无规烷氧基化产物。所述烷氧基化可通过本领域已知的任何合适方法通过使用例如碱性催化剂如KOH或酸催化剂而进行。
获自AkzoNobel的市售式(III)产品的实例包括Ethomeen C/12、Ethomeen C/15、Ethomeen C/25、Ethomeen T/12、Ethomeen T/15、Ethomeen T/20、Ethomeen T/25、Ethomeen HT/12、Ethomeen O/12、Ethomeen OV/12、Ethomeen S/12、Ethomeen S/17和Ethomeen S/22。
制备本发明主题产品的合适方法包括如下步骤：将上文所定义的式(I)化合物与上文所定义的式(IIa)或(IIb)化合物以及上文所定义的式(III)化合物混合，使所述混合物中的各化合物之间发生酯化缩合反应，且如果希望获得季化产物，则向所述缩合反应产物中添加烷基化试剂并使所述缩合产物发生季化反应。
化合物(I)、(IIa)或(IIb)与(III)之间的酯化缩合反应本身是本领域所公知的。所述反应优选在酯化催化剂，如布朗斯台德酸或路易斯酸，例如甲烷磺酸、对甲苯磺酸、柠檬酸或BF3存在下进行。当使用其中D为O-R3的式(IIa)二羧酸衍生物时，所述反应为酯交换反应，其替代地可在碱性催化剂存在下进行。也可添加羧酸(I)，例如以其甲酯形式。或者，可使用本领域技术人员所已知的其他常规技术由所述二羧酸的其他衍生物，例如其酸酐或其酰氯起始。
本领域技术人员还清楚的是，或者可在多于一个步骤中实施不同的酯化反应，例如首先使二羧酸衍生物(IIa)或(IIb)与烷氧基化脂肪胺(III)缩合，然后在下一步骤中添加羧酸(I)。所述反应可在添加或不添加溶剂下进行。如果在反应过程中存在溶剂，则所述溶剂应对酯化呈惰性，例如甲苯或二甲苯。
组分(I)、(IIa)或(IIb)与(III)之间的酯化缩合反应合适地通过将所述混合物在适当地为120-220°C的温度下加热2-20小时，任选在5-200毫巴的减压下进行。
当式(IV)中的t为0时，则产物为聚酯叔胺化合物；且当t为1时，产物为聚酯聚季铵化合物。季化为本领域所公知的一类反应。对季化步骤而言，所述烷基化试剂R5X合适地选自甲基氯、甲基溴、硫酸二甲酯、硫酸二乙酯、碳酸二甲酯和苄基氯，最优选的烷基化试剂为甲基氯、硫酸二甲酯、碳酸二甲酯或苄基氯。如上所述，季化可适当地在所述脂肪酸、烷氧基化脂肪胺和二酸之间的缩合产物上进行。原则上，按照替代的合成路线，可作为第一步骤实施烷氧基化脂肪胺(III)的季化，然后为(I)、(IIa)或(IIb)与季化的(III)的酯化反应。部分或者全部氮原子可被季化。作为另一选择，如果希望获得季化衍生物，则可使烷氧基化脂肪叔胺(III)与二羧酸衍生物(IIa)或(IIb)的反应产物与烷基化试剂，例如甲基氯或硫酸二甲酯反应以获得部分或完全季化的产物，然后与羧酸(I)反应。还可将所述两种方法组合，从而使得首先使部分季化的化合物酯化，并使所得聚酯进一步季化。
季化反应通常在水或溶剂，如异丙醇(IPA)或乙醇或其混合物中进行。其他替代的溶剂可为乙二醇单丁醚、二甘醇单丁醚(BDG)，以及其他乙二醇类和丙二醇类如单乙二醇(MEG)和二甘醇(DEG)。季化反应的反应温度合适地为20-100°C，优选为至少40°C，更优选为至少50°C，最优选为至少55°C，且优选至多90°C。当通过用处于冰醋酸中的0.1M高氯酸滴定测得的碱性氮的量≤0.1mmol/g时，优选停止加热。
优选其中该产物中的所有氮原子均为季氮原子的本发明产物。
在所述反应混合物中，式R1COOH(I)的脂肪酸或酸混合物与烷氧基化脂肪胺(III)的摩尔比合适地为1:1.2-1:10，更优选为1:1.5-1:5，仍更优选为1:2-1:4，最优选为1:2-1:3；且脂肪酸(I)与二羧酸或衍生物(IIa)或(IIb)之比合适地为2:1-1:8，1:1-1:8，更优选为1:1.2-1:6，仍更优选为1:1.5-1:5，仍更优选为1:1.5-1:4，仍更优选为1:1.5-1:3，最优选为1:1.5-1:2.5。
在非在先公开的专利申请PCT/EP2010/059325中描述了可通过使烷氧基化脂肪胺与任选季化的二羧酸衍生物反应而获得的聚合物型产物。所述产物用于腐蚀抑制，但具有不同于本发明产物的结构和性能。
式(IV)聚合物的一个实例具有下示结构：
其中RC=O为具有8-24个碳原子，优选12-24个碳原子的酰基；p为至少1，优选至少2，最优选至少3的数；且R4为具有8-24个碳原子的烃基。
为了制备其中p为3的上述实例的产物，使已用2摩尔EO乙氧基化的4摩尔C8-C24脂肪胺与2摩尔C8-C24羧酸和3摩尔己二酸反应。
实验部分的实施例中所公开的产物具有聚合物特性，且在下文中将可通过上述缩合和任选的进一步季化而获得的产物分别称为“聚合物酯胺产物”或“聚合物季铵酯产物”。本发明的聚合物酯胺或聚合物季铵酯产物可用于保护优选用于处于上述所有条件下的油气田或精炼中的管、泵、槽和其他设备的金属表面，优选含铁金属或合金，如铁和钢以免腐蚀。
就所述聚合物酯胺或聚合物季铵酯产物作为各种流动管中的腐蚀抑制剂的用途而言，流体含量可在宽范围内变化，例如油含量可为1(在野外情况下)-100%(例如在精炼厂中)，且当具有溶解的固体和盐含量时，可能一起输送的水的组成可在很大范围内变化。例如，绝大多数海水的盐度为3.1-3.8重量%，其中世界海洋的平均值为约3.5%，但流动管中的水(当存在时)可能具有甚至高达7重量%，例如高达6%，如高达4%的盐含量。另一方面，所述水也可为淡水或具有较低盐含量微咸水，例如低至0.3%，甚至低至0.05%且低至≤0.01%；微咸水的盐含量可不时发生很大变化，约0.05-约3%。
如上所例示，待保护的金属表面通常与具有不同盐含量的水接触。
在本发明的优选程序中，将所述聚合物酯胺或聚合物季铵酯产物在意欲保护的点或管的上游流动管中的任意点处添加至可包含油和水的流动液体中。获得足够保护所需的本发明腐蚀抑制产品的剂量率随应用场合而变化，但合适地以在保护点的浓度为1-2000ppm(重量)，优选1-500ppm，最优选1-150ppm的量计量添加。尽管优选连续计量使用本发明的化合物，但另一种可能的模式是间歇处理，其中优选的剂量率为1-5000ppm。
除了本发明的聚合物酯胺或聚合物季铵酯产物之外，也可在所述腐蚀抑制组合物中添加其他成分以(例如)改善不同气候条件下的操作性能或者进一步改善不同条件下的性能。这类成分的实例为有机或无机酸，如乙酸、柠檬酸和盐酸，此时所述胺主要以盐形式存在；分散或清洁表面活性剂，如非离子氧化乙烯加合物；水溶混性溶剂，如甲醇、乙醇、异丙醇、丁醇或二醇类如丁基二甘醇、乙二醇单丁醚、单乙二醇；阻垢剂；抗微生物剂如烷基苄基二甲基氯化铵、二烷基二甲基氯化铵、烷基酰胺基丙基二甲基氧化胺或季铵盐，例如烷基双(羟乙基)甲基氯化季铵盐；以及其他腐蚀抑制剂，如其他胺、酰胺、咪唑类或两性离子类。为了进一步改善腐蚀抑制功效，可添加增效剂如硫代硫酸钠或2-巯基乙醇。
实施例1
合成腐蚀抑制剂
将牛油脂肪酸(Tefacid2005-11091，获自Karlshamn；120.0g，0.43摩尔)、获自AkzoNobel的Ethomeen T/12E(370.0g，1.07摩尔)和获自DFS FineChemicals的琥珀酸酐(85.6g，0.86摩尔)添加至装备有冷凝器、温度计、加热套、氮气入口和机械搅拌器的圆底烧瓶中。将所述反应混合物缓慢加热至170°C。从156°C起始，开始蒸出反应过程中产生的水。在大气压和156-168°C下持续除水达1小时。随后，逐渐施加真空以更完全地除水。在1小时内，达到22毫巴的最终真空度。再继续在真空下除水达6小时。反应进程通过滴定酸值以及1H-NMR色谱法监控。在所述真空蒸馏后，产物的酸值为0.086meq/g，停止反应。获得541g产物。
实施例2
在盐水中的腐蚀抑制性能
使用公知的“鼓泡”法进行测试，参见例如NACE International，第46卷第5期，第46-51页(2007年5月)的论述，其中腐蚀速率通过线性极化电阻(LPR)监控。首先建立在所述介质中的基线腐蚀速率，然后测定在添加不同量的抑制剂下的腐蚀速率。
所述测试的详细条件如下：
由下述方程计算%保护：
%保护=(1-(x/y))*100
其中
x=在腐蚀抑制剂存在下的腐蚀速率(mm/年)
y=在不存在腐蚀抑制剂下的腐蚀速率(mm/年)
结果示于表1中。
表1
物质 在如下剂量下的%保护
31ppm 80ppm
季铵*(对照) - 89.6
实施例1的产物 80.0 -
*C12-C16椰油烷基二甲基苄基季胺
这些数据证实，实施例1的产物在代表性的条件下以及低剂量率下获得了显著的腐蚀防护效果。
尽管在本实施例中未示出，但先前进行的类似试验(尤其是非在先公开的专利申请PCT/EP2010/059325的实施例6)显示用作对照化合物的季胺的腐蚀抑制性能严重依赖于浓度。在非在先公开的专利申请PCT/EP2010/059325的实施例6中，在使用基本上相同的测试参数下，在50ppm下测得为38，在20ppm下测得为-28。
实施例3
生物降解性
目前一个公知的事实是，社会和官方通常要求用于最终可排至环境中的应用场合的人造有机化合物具有合理的生物降解性。此外，对特定地理和/或应用区域而言，监管机构还设有特定的最低水平的生物降解性。
按照GLP标准，根据OECD化学品测试指南，第3部分；降解和累积，第306期：在海水中的生物降解性，密闭瓶测试，测试实施例1中合成的产物在海水中的生物降解性。28天后的生物降解性>60%。本实施例表明本发明的化合物通常具有良好的生物降解性。
Claims (16)
1.可通过如下反应获得的产物作为金属表面的腐蚀抑制剂的用途：使式R1COOH(I)的脂肪酸或酸混合物，其中R1CO为具有8-24个碳原子且可为饱和或不饱和的、直链或支化的酰基；和
式(IIa)或(IIb)的二羧酸或其衍生物：
其中D为-OH、-Cl或-OR3，其中R3为C1-C4烷基；R2选自单键，式-(CH2)z-的亚烷基，其中z为1-10的整数，其中所述亚烷基被1或2个-OH基取代的取代亚烷基，亚环烷基、亚环烯基和亚芳基；
与式(III)的烷氧基化脂肪胺或者可通过部分或完全季化式(III)的烷氧基化脂肪胺而获得的产物反应：
其中R4为具有8-24个碳原子的烃基；AO为包含2-4个碳原子的亚烷氧基；各B独立地为具有1-4个碳原子的烷基，或苄基；各n独立地至少为1，且所有n之和为2-30；s为2或3；且y为0或1；任选在所述脂肪酸、二羧酸与烷氧基化脂肪胺的反应之后，存在另一反应步骤，在所述反应步骤中通过与烷基化试剂R5X反应而使部分或全部氮原子季化，其中R5为烃基，且X-为衍生自所述烷基化试剂R5X的阴离子。
2.根据权利要求1的用途，其中所述烷氧基化脂肪胺具有下式；
其中各x独立地为1-5的数，且∑x的摩尔平均值为2-10的数；AO为具有2-4个碳原子的亚烷氧基；R4为C8-C24烷基；任选在所述脂肪酸、二羧酸和烷氧基化脂肪胺的反应之后，存在另一反应步骤，在所述反应步骤中通过与烷基化试剂R5X反应而使部分或全部氮原子季化，其中R5为烃基，且X-为衍生自所述烷基化试剂R5X的阴离子。
3.根据权利要求2的用途，其中所述产物具有下式：
其中R1、AO、x、R2和R4具有与权利要求2相同的含义；R5为烃基；X-为衍生自所述烷基化试剂R5X的阴离子；t为0或1的数；p为1-15的数，且平均至少为1。
4.根据权利要求3的用途，其中t＝1。
5.根据权利要求4的用途，其中R5为C1-C4烷基或苄基。
6.根据权利要求4的用途，其中所述烷基化试剂R5X选自甲基氯、甲基溴、硫酸二甲酯、硫酸二乙酯、碳酸二甲酯和苄基氯。
7.根据权利要求5的用途，其中所述烷基化试剂R5X选自甲基氯、甲基溴、硫酸二甲酯、硫酸二乙酯、碳酸二甲酯和苄基氯。
8.根据前述权利要求中任一项的用途，其中R1CO为具有16-24个碳原子的酰基。
9.根据权利要求1-7中任一项的用途，其中R2为式-(CH2)z-的亚烷基，其中z为4。
10.根据权利要求2-7中任一项的用途，其中x＝1。
11.根据权利要求1-7中任一项的用途，其中在所述反应混合物中，结构(I)的脂肪酸或酸混合物与烷氧基化脂肪胺(III)的摩尔比为1:1.2-1:10，且结构(I)的脂肪酸或酸混合物与二羧酸或衍生物(IIa)或(IIb)的摩尔比为2:1-1:8。
12.根据权利要求1-7中任一项的用途，其中所述金属表面为用于油气田或油精炼中的管、泵、槽和其他设备的一部分。
13.根据权利要求1-7中任一项的用途，其中在意欲保护的点或管的上游流动管中的任意点处将所述腐蚀抑制产物添加至流动液体中。
14.一种可通过如下反应获得的产物：使式R1COOH(I)的脂肪酸或酸混合物，其中R1CO为具有8-24个碳原子且可为饱和或不饱和的、直链或支化的酰基；和
式(IIa)或(IIb)的二羧酸或其衍生物：
其中D为-OH、-Cl或-OR3，其中R3为C1-C4烷基；R2选自单键，式-(CH2)z-的亚烷基，其中z为1-10的整数，其中所述亚烷基被1或2个-OH基取代的取代亚烷基，亚环烷基、亚环烯基和亚芳基；
与式(III)的烷氧基化脂肪胺或者可通过部分或完全季化式(III)的烷氧基化脂肪胺而获得的产物反应：
其中R4为具有8-24个碳原子的烃基；AO为包含2-4个碳原子的亚烷氧基；各B独立地为具有1-4个碳原子的烷基，或苄基；各n独立地至少为1，且所有n之和为2-30；s为2或3；且y为0或1；任选在所述脂肪酸、二羧酸与烷氧基化脂肪胺的反应之后，存在另一反应步骤，在所述反应步骤中通过与烷基化试剂R5X反应而使部分或全部氮原子季化，其中R5为烃基，且X-为衍生自所述烷基化试剂R5X的阴离子。
15.一种制备根据权利要求14的产物的方法，包括使式(I)和(IIa)或(IIb)与(III)的化合物反应，且任选使由此获得的产物与烷基化试剂R5X反应，其中R5为烃基，且X-为衍生自所述烷基化试剂R5X的阴离子。
16.一种保护金属表面以免腐蚀的方法，包括使所述金属表面与根据权利要求14的产物或者可通过根据权利要求15的方法获得的产物接触。
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| EP10197172 | 2010-12-28 | ||
| PCT/EP2011/073922 WO2012089649A1 (en) | 2010-12-28 | 2011-12-23 | Polyester polyamine and polyester polyquaternary ammonium corrosion inhibitors |
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| EP (1) | EP2659028B1 (zh) |
| CN (1) | CN103261482B (zh) |
| AU (1) | AU2011351524B2 (zh) |
| BR (1) | BR112013015812B1 (zh) |
| CA (1) | CA2822517A1 (zh) |
| EA (1) | EA026287B1 (zh) |
| WO (1) | WO2012089649A1 (zh) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013092440A1 (en) * | 2011-12-19 | 2013-06-27 | Akzo Nobel Chemicals International B.V. | Compositions comprising polyester polyamine and polyester polyquaternary ammonium corrosion inhibitors and chelating agents |
| WO2015091308A1 (en) | 2013-12-18 | 2015-06-25 | Akzo Nobel Chemicals International B.V. | Polyester polyquaternary ammonium compound collectors for reverse froth flotation of silicates from nonsulfidic ores |
| GB2527640B (en) * | 2014-04-21 | 2022-09-21 | Wilhelm Wieland Friedrich | Corrosion inhibitors, improved paint and corrosion protection coating |
| AT515756B1 (de) * | 2014-04-21 | 2018-03-15 | Wieland Kg | Korrosions-Inhibitoren, verbesserte Farbe und korrosionsschützende Beschichtung |
| CN104893691B (zh) * | 2015-05-27 | 2016-02-10 | 中国石油大学(北京) | 二聚酸-有机胺共聚物及其制备方法和应用以及油包水乳化钻井液提切剂及钻井液 |
| GB2543488B (en) | 2015-10-14 | 2022-02-02 | Hexigone Inhibitors Ltd | Corrosion inhibitor |
| FR3047675B1 (fr) | 2016-02-16 | 2018-02-16 | Arkema France | Utilisation d'amines alkoxylees en tant qu'agents collecteurs pour l'enrichissement de minerai |
| EP3208314B1 (en) | 2016-02-16 | 2018-08-15 | Omya International AG | Process for manufacturing white pigment containing products |
| FR3047674B1 (fr) * | 2016-02-16 | 2018-02-16 | Arkema France | Utilisation d'amines alkoxylees en tant qu'agents collecteurs pour l'enrichissement de minerai |
| EP3208315A1 (en) | 2016-02-16 | 2017-08-23 | Omya International AG | Process for manufacturing white pigment containing products |
| CN108118353B (zh) * | 2016-11-30 | 2020-02-14 | 中国石油天然气股份有限公司 | 一种清除乳胶状沉积物的清洗剂及其制备方法和应用 |
| US10927289B2 (en) | 2017-04-03 | 2021-02-23 | Halliburton Energy Services, Inc. | Water-soluble corrosion inhibitor for subterranean treatments |
| EP3444036A1 (en) | 2017-08-16 | 2019-02-20 | Omya International AG | Indirect flotation process for manufacturing white pigment containing products |
| CN108659708B (zh) * | 2018-05-11 | 2020-08-25 | 深圳市鸿美特科技有限公司 | 一种满足喷涂附着力的金属防锈剂及其制备方法 |
| CN108485617A (zh) * | 2018-05-14 | 2018-09-04 | 中国石油集团西部钻探工程有限公司 | 一种钻井液用页岩抑制剂多枝化聚胺及其制备方法 |
| US11286571B2 (en) * | 2019-05-21 | 2022-03-29 | Indian Oil Corporation Limited | Mitigating internal corrosion of crude oil transportation pipeline |
| AR119523A1 (es) | 2019-07-29 | 2021-12-22 | Stepan Co | Surfactantes que inhiben la corrosión |
| US20240247209A1 (en) | 2021-05-18 | 2024-07-25 | Nouryon Chemicals International B.V. | Polyester polyquats in cleaning applications |
| AU2022323378A1 (en) * | 2021-08-05 | 2024-02-08 | Ecolab Usa Inc. | Polyamine-polyesters as corrosion inhibition |
| US11845892B2 (en) * | 2021-08-05 | 2023-12-19 | Clariant International Ltd | Use of complex polyesteramines and polyester polyquaternary ammonium compounds as corrosion inhibitors |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2902499A (en) * | 1955-04-21 | 1959-09-01 | Gulf Oil Corp | New chemical compounds and mineral oil compositions containing the same |
| US2975133A (en) * | 1955-04-21 | 1961-03-14 | Gulf Oil Corp | Corrosion-inhibiting mineral oil compositions |
| EP0846193B1 (en) * | 1995-08-24 | 2001-06-20 | Petrolite Corporation | Corrosion inhibition by ethoxylated fatty amine salts of maleated unsaturated acids |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3014864A (en) * | 1958-03-03 | 1961-12-26 | Petrolite Corp | Process of inhibiting corrosion |
| DE3007930A1 (de) | 1980-03-01 | 1981-09-24 | Henkel KGaA, 4000 Düsseldorf | Neue polyesterverbindungen, ein verfahren zu ihrer herstellung und ihre verwendung als textilweichmacher |
| US4560497A (en) | 1984-05-21 | 1985-12-24 | National Distillers And Chemical Corporation | Amino ester and amino amide-ester corrosion inhibitors for aqueous systems |
| DE3526600A1 (de) | 1985-07-25 | 1987-01-29 | Hoechst Ag | Quaternaere oxalkylierte polykondensate, verfahren zu deren herstellung und deren verwendung |
| DE3638744A1 (de) * | 1986-11-13 | 1988-05-26 | Hoechst Ag | Verzweigte, quaternaere polyoxalkylenmischpolyester, verfahren zu ihrer herstellung und ihre verwendung |
| US4781730A (en) | 1987-06-05 | 1988-11-01 | The Lubrizol Corporation | Fuel additive comprising a hydrocarbon soluble alkali or alkaline earth metal compound and a demulsifier |
| DE3809065A1 (de) * | 1988-03-18 | 1989-09-28 | Hoechst Ag | Veresterte glycidylether-additionsprodukte und deren verwendung |
| US5034444A (en) | 1988-08-26 | 1991-07-23 | Rheox, Inc. | Rheological additive for coating compositions |
| US5178786A (en) | 1989-08-04 | 1993-01-12 | The Lubrizol Corporation | Corrosion-inhibiting compositions and functional fluids containing same |
| DE4217985A1 (de) | 1992-05-30 | 1993-12-02 | Hoechst Ag | Verfahren zum Trennen von Erdölemulsionen vom Wasser-in-Öl-Typ |
| FI933763A (fi) | 1992-08-29 | 1994-03-01 | Hoechst Ag | Graensytaktiva foereningar baserade pao alkoxylerade fettaminer |
| US5284495A (en) | 1992-09-17 | 1994-02-08 | Mobil Oil Corporation | Oligomeric/polymeric multifunctional additives to improve the low-temperature properties of distillate fuels |
| WO1995034616A1 (en) | 1993-02-08 | 1995-12-21 | Mobil Oil Corporation | Carboxylic acid/ester products as multifunctional additives for lubricants |
| US5352377A (en) | 1993-02-08 | 1994-10-04 | Mobil Oil Corporation | Carboxylic acid/ester products as multifunctional additives for lubricants |
| US5775425A (en) | 1995-03-29 | 1998-07-07 | Halliburton Energy Services, Inc. | Control of fine particulate flowback in subterranean wells |
| US5710110A (en) | 1995-05-15 | 1998-01-20 | Rheox, Inc. | Oil well drilling fluids, oil well drilling fluid anti-settling and method of providing anti-setting properties to oil well drilling fluids |
| DE19743687C1 (de) | 1997-10-06 | 1998-11-26 | Henkel Kgaa | Detergensgemische und deren Verwendung |
| ES2354119T5 (es) | 2007-01-26 | 2014-05-16 | Cognis Ip Management Gmbh | Uso de esterquats poliméricos para la flotación de minerales y menas no sulfurosos |
-
2011
- 2011-12-23 BR BR112013015812-3A patent/BR112013015812B1/pt not_active IP Right Cessation
- 2011-12-23 US US13/976,585 patent/US9228089B2/en active Active
- 2011-12-23 EA EA201390922A patent/EA026287B1/ru not_active IP Right Cessation
- 2011-12-23 CN CN201180060587.XA patent/CN103261482B/zh not_active Expired - Fee Related
- 2011-12-23 CA CA2822517A patent/CA2822517A1/en not_active Abandoned
- 2011-12-23 EP EP11804701.8A patent/EP2659028B1/en active Active
- 2011-12-23 AU AU2011351524A patent/AU2011351524B2/en not_active Ceased
- 2011-12-23 WO PCT/EP2011/073922 patent/WO2012089649A1/en active Application Filing
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2902499A (en) * | 1955-04-21 | 1959-09-01 | Gulf Oil Corp | New chemical compounds and mineral oil compositions containing the same |
| US2975133A (en) * | 1955-04-21 | 1961-03-14 | Gulf Oil Corp | Corrosion-inhibiting mineral oil compositions |
| EP0846193B1 (en) * | 1995-08-24 | 2001-06-20 | Petrolite Corporation | Corrosion inhibition by ethoxylated fatty amine salts of maleated unsaturated acids |
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| Publication number | Publication date |
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| EP2659028B1 (en) | 2020-03-25 |
| CN103261482A (zh) | 2013-08-21 |
| CA2822517A1 (en) | 2012-07-05 |
| EA026287B1 (ru) | 2017-03-31 |
| BR112013015812B1 (pt) | 2020-03-24 |
| EA201390922A1 (ru) | 2013-11-29 |
| BR112013015812A2 (pt) | 2018-05-29 |
| EP2659028A1 (en) | 2013-11-06 |
| US20130274492A1 (en) | 2013-10-17 |
| US9228089B2 (en) | 2016-01-05 |
| AU2011351524A1 (en) | 2013-06-27 |
| AU2011351524B2 (en) | 2016-05-19 |
| WO2012089649A1 (en) | 2012-07-05 |
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