CN1056099A - 化学组合物及其作为燃料添加剂的应用 - Google Patents

化学组合物及其作为燃料添加剂的应用 Download PDF

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CN1056099A
CN1056099A CN91102536.7A CN91102536A CN1056099A CN 1056099 A CN1056099 A CN 1056099A CN 91102536 A CN91102536 A CN 91102536A CN 1056099 A CN1056099 A CN 1056099A
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fuel
compound
additive
formula
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格拉哈母·杰克逊
罗格·佛兰克·安德鲁
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ExxonMobil Chemical Patents Inc
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Exxon Chemical Patents Inc
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Abstract

本发明公开了如下式所示的化合物，及其作为馏 出燃料的低温流动改进剂的应用，式中取代基含义详 见说明书。

Description

本发明涉及在燃料中尤其是在馏出燃料中用作蜡晶体改性剂的新化合物，这些化合物作为馏出燃料添加剂的应用，尤其是与其他添加剂联合应用，含有这些添加剂，必要时还有其他添加剂的燃料和浓缩物。
含有石蜡的矿物油在温度降低时，流动性变差。这种流动性变差的原因是石蜡结晶成板状晶体，后者最终形成海绵体，将油料截留其中。开始生成蜡晶体的温度称作浊点，而石蜡阻止油流动的温度称作倾点。在上述温度之间，蜡晶体能够阻塞过滤器，使诸如柴油机卡车和家用热暖系统无法操作。
众所周知，许多添加剂与含蜡矿物油混合作为蜡晶体改性剂。这些组合物改变蜡晶体的尺寸和形状并降低晶体之间和晶体与油之间粘合力，从而使油在低温下保持流动，并在浊点和倾点之间的温度具有良好的过滤性能。
许多倾点抑制剂已在文献中报导，其中有些有商品供应。例如，美国专利3，048，479叙述了使用亚乙基与C1-C5乙烯基酯如乙酸乙酯的共聚物，作为燃料尤其是燃料油，柴油和喷气式飞机用燃料的倾点抑制剂。基于乙烯和α-烯烃的烃聚合物倾点抑制剂也是已知的。
U.S.3，961，916叙述了使用共聚物混合物来控制蜡晶体的尺寸;英国专利1，263，152叙述了蜡晶体可通过使用具有低度侧链的共聚物加以控制。上述两种物系改进了燃料通过过滤器的能力（由低温过滤器堵塞点（CFFF）试验测试），原因是，与形成的板状晶体（不存在添加剂时）不同，所产生的蜡晶体是针状的，不会堵塞过滤器的孔隙，甚至在过滤器上形成一多孔滤饼使残存的油通过。
有人还提出过其他添加剂，例如，英国专利1，469，016公开了采用富马酸二正烷基酯与乙酸乙烯基酯的共聚物（从前用作润滑油倾点抑制剂）作为助添加剂，与乙烯/乙酸乙烯基醋共同添加剂处理具有高终沸点的馏出燃料，以改进它们低温流动性能。
美国专利3，252，771叙述了采用C16-C18α-烯烃聚合物（通过在三氯化铝/烷基卤催化剂存在下，使主要为正构C16-C18α-烯烃的烯烃混合物聚合制得）作为具有宽沸程的馏出燃料的倾点抑制剂，来处理本世纪六十年代早期在美国市场上的各种类型的燃料。
也有人建议使用基于烯烃/马来酐共聚物的添加剂。美国专利2，542，542叙述了烯烃如正十八碳烯与用醇，如月桂醇酯化的马来酐的共聚物作为倾点抑制剂。英国专利1，468，458叙述了C22-C28烯烃与用山萮醇酯化的马来酐共聚物作为馏出燃料的助添加剂。
类似地，日本专利公开5，654，037叙述了已与胺类反应的烯烃/马来酐共聚物作为倾点抑制剂，而日本专利公开5，654，038叙述了采用烯烃/马来酐共聚物的衍生物以及普通的中间馏出物流动改进剂如乙烯乙酸乙烯基酯共聚物。
日本专利公开5，540，640叙述了使用烯烃/马来酐共聚物（未酯化）并声称采用的烯烃应含有多于20个碳原子以得到CFPP活性。
英国专利2，129，012叙述了使用酯化的烯烃/马来酐共聚物和低分子量聚乙烯的混合物，酯化的共聚物作添加剂单独使用时无效。该篇专利强调说，烯烃应含有10-30个碳原子，醇应含有6-28个碳原子，醇中最长链含有22-40个碳原子。
美国专利3，444，082;4，211，534;4，375，973;和4，402，708叙述了使用某些含氮化合物。
双官能团化合物的长正烷基衍生物可以用作馏出燃料的蜡晶体改性剂，这种衍生物，尤其是胺衍生物有烯基琥珀酸（US3444082）、马来酸（US4211534）和邻苯二甲酸（GB2923645，US4375973和US4402708）的衍生物。英国专利说明书1209676叙述了使用基些烷基化的芳磺酸的胺盐作为汽轮油和液压油的防锈添加剂。
通过改变蜡晶体的尺寸和形状，产生粒径通常为10，000毫微米，或大于30，000-100，000毫微米的针状晶体，来达到通过掺加上述专利文献添加剂而改进CFPP活性的目的。在柴油机或供暖系统低温操作时，这些晶体一般不通过过滤器但在过滤器上形成一可渗透的滤饼使流体燃料通过。这些蜡晶体最终随着发动机和燃料的加热而溶解，但这却会导致蜡晶体堵塞过滤器，导致发动困难，尤其在严寒天气，并导致燃料加热系统失灵。
欧洲专利申请公开0261957，0261958和0261959叙述了使用具有一定构型化合物作为添加剂，尤其是使用基些新的化合物，使蜡晶体的尺寸显著降低，低于4，000毫微米，有时低于2000，甚至有时低于1，000毫微米。
现在发明了一些化合物，在控制馏出燃料中的蜡晶体尺寸方面，这些化合物与EP-A-0261959所述化合物是可比拟的。
一方面，本发明提供了一种通式所示化合物：
式中，X和Y相同或不同，选自SO- 3，-CO-，-C（O）O-，-R4-C（O）-，-NR3C（O）-，-R4O-，-R4OC（O）-，-R4-和-NC（O）-，其中R4为-（CH2）m，m为0-5，R如下所述;
X和Y相同或不同，选自以下基团：
N（+）R3 3R2，HN（+）R3 3R2，H2N（+）R3R2，H3N（+）R2，
N（+）R3R1，N（+）HR3 3R1，H2N（+）R3R1，H3N（+）R1，NR3R2，
-R2，-NR3R1，and R1，
R1和R2分别选自烷基，典型是C10-C40，优选C10-C30，更优选C14-C24的烷氧基烷基;多烷氧基烷基，在其主链上含有至少10个，典型的是10-40个碳原子;
R3为-烃基，优选烷基，最好是C1-C30，尤其是C10-C30的直链烷基，式（Ⅰ）中每个R可以相同或者不同。
A与碳原子一起构成式（Ⅰ）中的环结构，A为芳族，非芳族或脂族基团，每个基团可以是单环或多环和/或可包括一个或多个选自氮、硫和氧的杂原子;
Z选自硝基，羟基，烷基，烷氧基，羧基酯醚，每个烷基含有1-10个最好含有1-4个碳原子。
推荐X1和Y1共含有至少三个烷基，烷氧基烷基或多烷氧基烷基。
第二方面，本发明涉及馏出燃料组合物，含有沸程为120℃-500℃的馏出石油燃料，0.0001-0.5%（重量）的式（Ⅰ）化合物。
第三方面，本发明还涉及使用式（Ⅰ）化合物作为添加剂以改进馏出石油燃料的低温流动性能。
第四方面，本发明涉及一种浓缩物，包括式（Ⅰ）化合物和一种溶剂的混合物，所述溶剂与馏出石油燃料相容。
本发明化合物结构中的环部分可以是单环或多环芳族或脂族，多核芳族，杂芳族和杂脂族。环结构可以是饱和的或是不饱和的。具有一个或多个不饱和键，至少一个环含有4个或更多原子，它可以是多环，桥连的并可被取代。
适宜的单环结构的例子有苯，环己烷，环己烯，环戊烷，吡啶和呋喃。环结构可以含有另外的取代基。适宜的多环化合物，即具有两个或更多环结构的多环化合物，可具有多种形式。它们可以是（a）稠合芳族结构，（b）稠合的部分氢化的芳环结构，其中至少一个但并非所有环是芳族的，（c）脂环，包括稠合脂环，桥接脂环，螺脂环化合物，（d）相同或不同环的烃环组合物，可是芳族的，脂环族的或二者混合，（e）含有至少一个杂原子的（a）-（d）任何之一。
可以衍生成上述化合物的稠合芳族结构的例子有萘、蒽、菲、芴，芘和茚。适宜的稠合环结构（其中所有环均不是苯或并非所有环是苯）的例子有：
Figure 911025367_IMG5
，氢化萘，氢化茚，氢化芴，联二亚苯。适宜的桥接脂环结构包括双环戊烷和双环戊烯。
适宜的环组合物包括联苯和环正基苯。
适宜的杂多环结构包括奎宁环和吲哚环。
从中可衍生出本发明化合物的适宜的杂环化合物包括喹啉，吲哚，2，3-二氢吲哚，苯并呋喃，香豆素和异香豆素，苯并噻吩，咔唑，硫代二苯胺。
适宜的非芳族或部分饱和的环体系包括萘烷（十氢化萘），d-蒎烯，杜松烯，冰片烯。适宜的桥连化合物包括降冰片烯，双环戊烷（降冰片烷），双环辛烷和双环辛烯。
若环结构是多环结构，则X和Y最好完全座落在一个环内的环原子。例如，若环结构为萘，则这些取代基最好连在1，2-，2，3-，3，4-，5，6-，6，7-，或7，8-位，而不是连在1，8-或4，5-位。
现已惊奇地发现，用式（Ⅰ）环结构所示位置的基团Z的存在，可明显改进，当产品用作馏出燃料添加剂时，控制当燃料冷却时蜡晶体的尺寸的能力。当式（Ⅰ）化合物用作馏出物添加剂时，基团Z最好为硝基。为了使燃料添加剂具有良好的性能，Z最好是在相对X1和/或Y1（若有一个存在）中的阳离子氮的环3一位上。因此，式（Ⅱ）化合物比式Ⅲ化合物的活度大许多：
Figure 911025367_IMG7
影响添加剂性能的一个因素可能是由于取代基位置的不同，使其在燃料中的溶解度不同。
本发明优选的化合物是式（Ⅵ）化合物
Figure 911025367_IMG8
更优选的是式Ⅶ化合物：
Figure 911025367_IMG9
式中R1和R3分别推荐为C16/18烷基或C17/18烷基。
现已发现，通过使用本发明新化合物作为馏出燃料添加剂，当燃料降温时形成的蜡晶体足够小，使其能通过典型柴油机和加热系统的过滤器，而不在过滤器上形成滤并。
现已发现，根据本发明降低蜡晶体尺寸可以减少在燃料贮存时蜡晶体的沉淀，同时还可改善燃料的CFPP性能。
燃料的蜡表观温度（WAT）可借助差式扫描测热计（DSC）来测量。在该试验中，少量燃料样品（25ΛΛ）与具有类似热含量的参比样品以2℃/分钟冷却，该参比样品在有关温度范围内不沉淀出蜡（如煤油）。当样品中开始有结晶时，观察到有放热现象。
蜡含量值助DSC图推算：对由基线包围的面积求积分，放热至某特定温度，已在已知量的晶体蜡上进行校正。
蜡晶体的平均粒径按如下测定：分析燃料样品在放大4000-8000倍下的扫描片子显微照片，在一个预先确定的格子上测量50个晶体的最长的轴，我们发现，如果平均粒径小于4000毫微米，那么蜡晶体便可随燃料一道，通过柴油机中典型使用的纸过滤器，尽管我们推荐尺寸小于3000毫微米，优选低于2000，最好低于1000毫微米。实际上可达到的尺寸取决于燃料的最初性质以及添加剂用量，但我们发现上述尺寸以及比其更小的尺寸是可以达到的。
与用普通添加剂改善其低温流动性的馏出燃料相比，含有式（Ⅰ）化合物作为添加剂的燃料具有突出的优点。例如，燃料在接近倾点的温度下仍可工作，而不受未能通过CFPP试验的限制。因此，这些燃料或者能在明显低的温度下通过CFPP试验或者不必通过上述试验。上述燃料在低温下还具有良好的发动性能，原因是它们不依赖于热燃料的再循环来溶解不希望有的蜡沉淀。该燃料还减少了贮存燃料中蜡晶体的沉淀，减少了蜡在贮存容器底部的凝聚而堵塞过滤器等。
通过向馏出燃料油中加入本发明化合物可以得到小的晶体，基于燃料重，加入的化合物的量较好为0.001-0.5%（重量），例如0.01-0.10%（重量）。
本发明化合物还可以方便地溶解在适当的溶剂中，得到浓缩物，例如在溶剂中占30-80%（重量）。适宜的溶剂包括煤油，芳族石脑油，矿物润滑油。
当本发明化合物用作馏出燃料的添加剂时，R1，R2和R3最好含有10-24个碳原子，例如14-22个，优选18-22个碳原子，并最好是直链的或在1或2位有支链。适宜的烷基包括癸基，十二烷基，十四烷基，十六烷基，octadouse，二十烷基和二十二烷基（山萮基）此外，上述基团还可以是聚氧化乙烯或聚氧化丙烯，上述基团的主链是最长的直链片断。
尤其优选的式（Ⅰ）化合物，是仲胺的酰胺或胺盐。
尽管两个取代基是必需的，如通式所示，但应明白，本发明化合物可以具有连接在环化合物中的环原子上的一个或更多个取代基。
本发明化合物最好由或式（Ⅳ）所述的反应物来制备：
Figure 911025367_IMG10
式中X和Y如在式（Ⅰ）中所述，此外还可共同形成环酐结构的一部分，其中氧基（
Figure 911025367_IMG11
）为X和Y共有。
优选的式（Ⅳ）反应物是X和Y选自-C（O）O-和-SO- 3-，尤其优选的反应物是式（Ⅴ）所示化合物：
Figure 911025367_IMG12
本发明化合物通过式（Ⅳ）Y-H基和X-H基与例如胺、醇、季铵盐或其混合物反应来制备，已经发现，紧接着酸酐环存在Z基团（如式Ⅴ所示），有助于在邻接载有的碳Z原子上形成酰胺基团，从而主要生成优选的化合物，当然也生成一些不太优选的化合物，即，酰胺基团远离Z。如果最终化合物是酰胺或胺盐，则它们最好是具有含氢和碳基团的仲胺，该含氢和碳基团含有至少10个碳原子，优选10-30个，最好16-24个碳原子，并最好是直链烷基。这种酰胺或盐可以通过使酸或酸酐与仲胺反应来制备，或者通过与胺的衍生物反应来制备。从酸制备酰胺一般需要免去水份和加热。此外，Y-H和X-H基可与含有至少10个碳原子的醇或醇的混合物以及胺反应，或者按胺和醇的顺序反应，或按相反顺序反应。
因此，根据X-X1和Y-Y1的性质，最终化合物包括例如酯，酰胺，醚，伯、仲或叔胺盐，氨基酰按和氨基醚。
尽管本发明化合物作为添加剂可以单独使用，但是若与用于改进馏出燃料油低温流动性能的其他已知添加剂联合使用则可获得最佳效果。
本发明化合物最好是与如下式所示的称作梳状聚合物联合使用：
式中D＝R，C（O）.OR，OC（O）.R，R1C（O）.OR或OR;
E＝H或CH3或D或R1
G＝H或D
m＝1.0（均聚物）-0.4（摩尔比）
J＝H，R1，芳基或杂环茎，R1CO.OR
K＝H.C（O）.OR1，OC（O）.R1，OR1，C（O）OH
L＝H，R1，C（O）OR1，OC（O）R1，芳基，C（O）OH
n＝0.0-0.6（摩尔比）
R是含有多于10个碳原子，最好含有10-30个碳原子的烃基。
R1是C1-C30的烃基。
必要时另一单体可进行三聚
适宜的梳状聚合物的例子有富马酯/乙酸乙烯基酯，尤其是如欧洲专利公开0153176和0153177所述的那些和酯化烯烃/马来酸酐共聚物以及α-烯烃与酯化的苯乙烯与马来酐共聚物的聚合物和共聚物。
可以与本发明化合物一起使用的其他添加剂的例子有：聚环氧烷酯，醚，酯/醚和其混合物，尤其是含有至少一个最好是两个C10-C30直链饱和烷基和分子量为100-5，000最好是200-5，000的聚氧烷二醇的那些，聚氧烷二醇中的烷基含有1-4个碳原子。上述物质是欧洲专利公开0，061，895A2的主题。美国专利4，491，455叙述了其他此类添加剂。
可以采用的优选的酯，醚或酯/醚具有如下式所示的结构：
R-O（A）-O-R11
其中R和R11相同或不同，并可以是：
其中的烷基是直链的和饱和的并含有10-30个碳原子，A代表乙二醇上的聚环氧烷片断。其中的亚烷基具有-4个碳原子，如聚甲醛、聚环氧乙烷、或聚三甲醛部分，其基本是直链的。可容许一些低级烷基支链存在（如在聚氧丙二醇中），但乙二醇中最好基本是直链的，A也可含有氮。
适宜的二醇通常是基本为直链的分子量为约100-5，000，最好约200-2，000的聚乙二醇（PEG）和聚丙二醇（PPG）。与二醇反应生成酯添加剂最好采用酯和含有10-30个碳原子的脂肪酸，最好采用C18-C24脂肪酸，尤其是山萮酸。酯也可通过酯化聚乙氧基化脂肪酸或聚乙氧基化醇来制备。
聚氧烷二酯，二醚，醚/酯和它们的混合物也适宜作添加剂，在具有窄沸程的馏出燃料中，优选使用二酯，并可存在有少量的单醚和单酯。存在少量的二烷基化合物对添加剂性质是重要的。特别是优选聚乙二醇、聚丙二醇或聚乙二醇/聚丙二醇混合物的硬脂酸二酯或山萮酸二酯。
本发明化合物也可以与烯属不饱和酯共聚物流动改进剂一起使用。可与乙烯共聚合的不饱和单体包括如下式所示的不饱和单酯和二酯：
式中R6为氢或甲基，R5是-OOCR8，其中R8是甲酸或为一个C1-C28、优选C1-C17、最好为C1-C8的直链或支链烷基;或者R5是-COOR8，其中R8如上所述，但不为氢，R7为氢或-COOR8，如上所述。
当R6和R7为氢，R5为-OOCR8时，单体包括单元羧酸的乙烯醇酯，所述的单元羧酸具有C2-C29，一般具有C2-C5个碳原子，所述的乙烯醇酯含有C1-C29一般含有C1-C5个碳原子，可与乙烯共聚的乙烯基酯包括乙酸乙烯基酯，丙酸乙烯基酯，和丁酸乙烯基酯或异丁酸乙烯基酯。共聚物中最好含有5-40%（重量）的乙烯基酯，尤其是10-35%（重量）的乙烯基酯。也可以是如US3，961，916所述共聚物中心两种共聚物混合物。这些共聚物的数均分子量最好为1，000-10，000，尤其为1，000-5，000（气相渗透色谱）。
本发明化合物还可以与其他极性化合物一同在馏出燃料中使用，这些极性化合物或是离子型的或是非离子型的，并在燃料中具有晶体生长抑制剂的作用，我们惊奇地发现，本发明化合物与其他含氮极性化合物共同使用具有协同作用。极性的含氮化合物与二醇酯，醚或酯/醚联合使用尤为有效。上述三种组分的混合物也在本发明的范围之内。这些极性化合物通常是胺盐和/或酰胺，它们的制备是，至少一摩尔量的烃基取代的胺与一摩尔量的含有1-4个羧酸基的烃基酸或其酸酐反应。含有30-300，最好是含有50-150个总碳原子的酯/酰胺也可以使用，这些含氮化合物在US4，211，534中有叙述。适宜的胺通常是长链的C12-C40伯，仲，叔或季胺或它们的混合物，但也可使用短链胺，只要求所得含氮化合物是油溶性，因此通常具有约30-300个总碳原子数。这些含氮化合物含有至少一个C8-C40的直链，最好是C14-C24的烷基片断。
适宜的胺包括伯、仲、叔或季胺，但以仲胺为佳。叔胺和季胺只能形成胺盐。胺的例子有十四烷基胺，可可胺，氢化的脂胺等。仲胺的例子有二（十八烷基）胺，甲基-山萮基胺等。胺的混合物也是适宜的，许多从天然物质得到的胺都是混合物。优选的胺是式为HNR1R2的仲氢化脂胺，式中R1和R2为烷基，所述的仲氢化脂胺是从具有如下组成的氢化牛脂脂肪中衍生的：4%C14，31%/C16，59%C18。
用以制备上述含氮化合物的适宜的羧酸和它们的酸酐的例子有：环己烷-1，2-二羧酸，环己烯-1，2-二羧酸，环戊烷-1，2-二羧酸，萘二羧酸等。一般地讲，上述酸在环部分具有约5-13个碳原子。优选的用于本发明的酸有苯二羧酸如邻苯二甲酸，间苯二甲酸和对苯二甲酸。邻苯二甲酸及其酸酐尤佳。尤其优选的化合物是酰胺一胺盐，它是通过1摩尔量的邻苯二甲酸酐与2摩尔量的二氢化脂胺反应生成的。其他优选化合物是二酰胺，它是通过水解上述酰胺一胺盐生成的。
具有下列通式的烃聚合物也可作为添加剂组合物的组分：
式中T＝H或R1
U＝H，T或芳基
v＝1.0-0.0（摩尔比）
w＝0.0-1.0（摩尔比）
其中R是烷基。
这些聚合物可直接从烯属不饱和单体制备，也可以通过氢化由单体如异戊二烯、丁二烯等制成的聚合物，间接地制备。
尤其优选的烃聚合物是乙烯与丙烯聚合物，其中乙烯含量最好在20和60%（重量）之间，通常在均相催化下制备。
本发明化合物也可与类似于欧洲专利申请0261959所述化合物联合使用，它们具有以下通式：
Figure 911025367_IMG17
式中A和B相同或不同，可以是烷基、烯基或芳基;
L选自以下基团：
Figure 911025367_IMG18
而A、B和L共同所构成环结构的一部分，其中的环可以是芳香环，脂族环或混合的芳香环/脂族环，条件是，基团-X-X1和Y-Y1位于构成L的不同的碳原子上，并且若A、B和L未构成环结构的一部分，则A或B之一可为氢;若L为非环乙烯型，则所述的X-X1和Y-Y1基团以顺式构型存在。
X选自以下基团：
SO3（-），-C（O）-，-C（O）O（-），-R4-C（O）O-，-NR3C（O）-
-R4O-，-R4OC（O）-，-R4-and-NC（O）-;
X1选自以下基团
N（+）R3 3R2，HN（+）R3 2R2，H2N（+）R3R2，H3N（+）R2，N（+）R3 3R1，N+HR3 2R1，H2N（+）R3 3R1，H3N（+）R1，NR3R2，
-R2，-NR3R1，and R1;
Y为-SO- 3或-SO2
若Y为SO- 3，则Y1选自以下基因：
若Y为-SO2，则Y1为OR2，-NR3R2或-R2，其中R2和R3分别选自在主链上含有至少10个碳原子的烷基，烷氧基或多烷氧基烷基，
R3是烃基并且每个R3可以相同或不同，以及
R4是-（CH2）n式中为0-5。
以下参照附图和实施例进一步说明本发明。
图1是添加剂A的红外光谱图;
图2是添加剂A的质子核磁共振谱图;
图3是添加剂H的质子核磁共振谱图。
添加剂A和D是本发明化合物。
添加剂A
3-硝基邻苯二甲酸酐（有商品）与两摩尔二氢化脂胺以50%（重量）浓度在甲苯溶剂中反应。反应混合物在60℃下搅拌15分钟，并于50℃减压蒸除溶剂，得到一半酰胺/半氨盐如式（Ⅸ）所示的结构：
Figure 911025367_IMG19
式中R为C16/18烷基，上述结构经图1和图2所示的红外和质子核磁共振图所确定。
该产品标记为添加剂A，
添加剂B
1∶1摩尔比的苯乙烯-马来酐共聚物用2摩尔C14H29OH（对每摩尔酐基）酯化，所用醇约过量5%，酯化反应以对甲苯磺酸（1/10摩尔）作催化剂，在二甲苯溶剂中进行。产品（标记为添加剂B）的数均分子量（Mn）为50，000，并含有3%（W/W）未反应的醇。
添加剂C
制备方法类似于添加剂B，但使用2摩尔C12H25OH和C14H29OH的1∶1摩尔混合物来酯化苯乙烯/马来酐共聚物。所得共聚物的数均分子量为50，000并含有3.3%（重量）的游离醇。
添加剂D
乙烯-乙酸乙烯酯共聚物的数均分子量为3，500，乙酸乙烯酯的含量为1.3%，侧支链度为8甲基/100亚甲基。
添加剂E
邻苯二甲酸酐与两摩尔二氢化脂胺反应生成半酰胺/半胺盐化合物。
添加剂F
1，2，4，5-苯四酸二酐与四摩尔二氢化脂胺反应，生成二（半酰胺/半胺盐）。
添加剂G
1摩尔邻磺基苯甲酸环酐与2摩尔二（氢化）脂胺以50%（重量）浓度在二甲苯溶剂反应。反应混合物在100℃-回流温度下搅拌，尽量保持溶剂和反应剂干燥以防酸酐水解。
产物（标记为添加剂G）经500兆赫的NMR谱证明，为2-二烷基氨基苯磺酸的N，N-二烷基铵盐，其中烷基是正C16-18H33-37，即具有如下式（Ⅹ）结构：
Figure 911025367_IMG20
添加剂H
本发明另一化合物添加剂H的制备如下：
3-羧甲基邻苯二甲酸酐用2摩尔二氢化脂胺在二甲苯溶剂中以50%（重量）浓度处理，反应混合物在60℃下搅拌得到式（Ⅹ1）所示的半酰胺/半氨盐：
Figure 911025367_IMG21
式中R为C16/18。上式结构由图3所示的质子核磁共振谱图确定。
按如下方法测定添加剂A以及在馏出燃料油中含有作为过滤改进剂的添加剂A的添加剂物系的有效性：
一种测定油对添加剂响应的方法，按下述文献所述的“低温过滤器堵塞点试验（CFPP）”进行：“Journal  of  the  lnstitute  of  Petroleum”卷52，号510，1966年6月，173-285页。该试验与汽车柴油机中馏出燃料油的低温流动性有关。
简单地讲，将40ml待处理油样在温度约为-34℃的浴池中冷却，以约1℃/分进行非线性冷却。周期测定（每次从高于浊点1摄氏度开始）冷却油在规定时间内通过细筛网的能力，使用的测试器为一吸管，其底端与逆向漏斗相连，其漏斗位置低于待测油的表面。横向漏斗嘴拉伸一个350目的筛网，其面积由12毫米直径定义。每次周期试验开始时，将吸管上端抽真空，油通过筛网吸入管内，标记油为20ml。每次顺利通过后，油立即反回CFPP管。温度每降低一度重复一次该试验，直至在60秒内油不能充满吸管。该温度称作CFPP温度。不含添加剂的燃料的和含有添加剂的相同燃料的CFPP差称作添加剂CFPP抑制，在相同温度下，好的流动改进剂具有大的CFPP抑制值。
测定流动改进剂效率的另一个方法，是在流动改进剂的程序冷却试验的试验下进行，该试验是一种缓慢冷动试验，用来表示燃料中的蜡是否能通过诸如加热油分配器中的过滤器。
在该试验中，按如下方法测定含有添加剂的所述燃料的低温流动性能。将300ml燃料以1℃/小时线性冷却至试验温度，然后保持该温度恒定。沉积在底部的蜡通过b轻度搅拌而分散，然后插入一个CFPP过滤器件，打开塞子施加-500毫米汞柱的真空，留有200ml燃料通过过滤器进入刻度接受器时关闭塞子。若在2分钟内通过给定目数的筛子收集200ml燃料，则记录“通过，若流动速率太慢则记录“失败”表示过滤器已堵塞。
采用过滤器筛目数为20，30，40，60，80，100，120，150，200，250，350和500的CFPP过滤器件以及孔径为25um，20um，15um和10um的过滤器件，此外，使用一个大众罐式筛（称为vw）和一个LTFT过滤器，以确定燃料通过的最细目（最大目数值）。含有燃料的蜡通过的目数值愈大，蜡晶体尺寸愈小，添加剂流动改进剂的效率愈好。以下按孔径增加的顺序给出采用的过滤器的顺序：
10μm，15μm，20μm，500，LTFT，VW，350，250，200，150，120，100，80，60，40，30，20
其中无单位的数值表示目数。
实施例1
表1给出在具有ASTM  D-86分配性能的燃料中试验的上述添加剂：
蜡含量是以在低于蜡表观温度10℃时蜡沉积的%（重量）表示。
试验中，采用了另外成分250ppm。组成含量在添加剂A或添加剂G之间变化。
表1
Figure 911025367_IMG22
XPCT结果给出含有添加剂A和G的产品性能的比较。
试验温度，采用各种组分的含量及结果列于下表
Figure 911025367_IMG23
实施例2
在PCT试验中，测试了许多添加剂组合物，步骤是在-14℃下，加入添加剂即含有50ppm乙烯/乙酸乙烯酯共聚物的燃料6的物质，得到如下结果：
添加剂  浓度  通过的目数
A  250ppm  10μ
A  500ppm  10μ
H  500ppm  10μ
A  125ppm  15μ
H  250ppm  15μ
Figure 911025367_IMG25

Claims (11)

1、通式(Ⅰ)所示的化合物：
式中X和Y相同或不同，并选自以下基团：
SO3(-)，-CO-，
-C(O)O(-)，-R4-C(O)O-，-NR3C(O)-，-R4O-，
-R4OC(O)-，-R4-and-NC(O)-，
其中m为0-5，而R3如下定义。
X1和Y1相同或不同选自以下基团：
N(+)R3 3R2，HN(+)R3 2R2，H2N(+)R3R2，H3N(+)R2，
N(+)R3 3R1，N(+)HR3 2R1，H2N(+)R3R1，H3N(+)R1，NR3R2，
-R2，-NR3R1，and R1，
R1和R2分别选自在它们主链上至少含有10个碳原子的烷基，烷氧基烷基或多烷氧基烷基，R3为烃基，式(Ⅰ)化合物中的每个R3相同或不同；
A与构成式(Ⅰ)环结构的碳原子一起，为一芳族，非芳族或脂族基，其中任何一种上述基团可以是单环或多环和/或包括一个或多个选自氮，硫和氧的杂原子；
Z选自硝基，烃基，烷基，烷氧基和羧基酯醚。
2、权利要求1的化合物，其中X1和Y1共同含有至少三个烷基、烷氧基烷基或多烷氧基烷基。
3、权利要求1或2的化合物，其中R1和R2分别是含有10-40个碳原子的烷基，R3是含有1-30个碳原子的烷基，Z中的每个烷基具有1-10个碳原子，式（Ⅰ）环结构为单环芳香族。
4、上述权利要求任何之一所述的化合物，具有通式（Ⅵ）：
5、权利要求3的化合物，其中Y1为HN2（+）R3R1，X1为NR3R1，每个R1和R3是具有14-22个碳原子的直链烷基。
6、权利要求6的化合物，其中Z是NO2基。
7、沸程为120℃-500℃的馏出石油燃料，含有0.0001-0.5%（重量）的权利要求1-6任何之一所述的化合物。
8、添加剂在馏出燃料中控制其冷却过程中形成的蜡晶体尺寸的应用，添加剂包括权利要求1-6中任一项所述的化合物。
9、一种浓缩物，包括添加剂和与馏出石油燃料相容的溶剂的混合物，所述添加剂包括权利要求1-6任何之一所述的化合物。
10、改进馏出石油燃料的低温流动性能的方法。该方法包括，向燃料中掺加包括权利要求1-6任何之一所述化合物的添加剂。
11、权利要求7-9任何之一所要求的发明，其添加剂与一种或多种其他馏出燃料的低温流动改进剂联合使用。
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RU2101276C1 (ru) 1998-01-10
GB9008811D0 (en) 1990-06-13
EP0525079A1 (en) 1993-02-03
DE69121093T2 (de) 1997-01-02
FI924712A (fi) 1992-10-16
FI924712A0 (fi) 1992-10-16
EP0525079B1 (en) 1996-07-24
AU649036B2 (en) 1994-05-12
PL166818B1 (pl) 1995-06-30
BR9106352A (pt) 1993-04-20
KR930700415A (ko) 1993-03-15
AU7657091A (en) 1991-11-11
WO1991016297A1 (en) 1991-10-31
ATE140695T1 (de) 1996-08-15
DE69121093D1 (de) 1996-08-29
JPH05506220A (ja) 1993-09-16
JP2828774B2 (ja) 1998-11-25
CA2080337A1 (en) 1991-10-20
US5578091A (en) 1996-11-26
KR100200446B1 (ko) 1999-06-15

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