CN1062752A - 汽油组合物 - Google Patents
汽油组合物 Download PDFInfo
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Abstract
本发明提供汽油组合物。包括主要量适用于火花
点火发动机的汽油和小量通式(I)与琥珀酸衍生物
的烷基聚醚醇偏碱金属盐,琥珀酸衍生物在其一个
α-碳原子上有一15—200个碳原子的未取代或取代
的脂肪烃基,还可以通过1—6个碳原子的烃部分与
另一α-碳原子相边形成环状结构,以及含此类偏酯
盐的浓缩物。此类偏酯盐在汽油组合物中用作火药
助剂和抗气门粘附剂。
Description
本发明涉及包括主要量的适用于火花点火发动机的汽油和小量的至少一种添加剂的汽油组合物。
US.3,632,510公开了包括主要量的润滑油和小比例的烃取代的琥珀酸酯衍生物(包括混合酯金属盐)的润滑和燃料组合物,其中烃取代物含有至少约50个脂族碳原子和不多于约5%的烯烃键合,基于取代物碳-碳共价键合的总数计算。烃取代源基本上包括饱和的烯烃聚合物,特别是有2-30个碳原子的单烯烃聚合物。聚异丁烯被认为是最优先选择的烃取代源。醇被认为在制备包括通式
的化合物的酯衍生物中是有用的(式中R3为氢,芳基,低级烷基如乙基、丙基、叔丁基、戊基等;或者芳烷基;n为0-150左右;R1和R2为多至8个碳原子的低级亚烷基。当加入燃料中,酯衍生物据说由于阻止了油箱、油路、化油器、喷油装置中沉积物的形成,可以促进油路系统的清洁作用,并且在许多例子中减少了燃烧室沉积、火花塞结垢和排气阀沉积、它们也是有效的防筛孔堵塞剂。
U.S.4,846,848公开了含小量100℃时粘度为2-20厘沲(2×10-6-2×10-5m2/s)的聚α-烯烃。还可以有脂族多胺、琥珀酸衍生物的碱金属或碱土金属盐作为火焰速度改进剂和/或聚烯烃的组合物。琥珀酸衍生物在至少一个α-碳原子上具有一未取代或取代的2-200碳原子的脂肪烃作为取代物,或者在它的一个α-碳原子上有一未取代或取代20-200碳原子的烃基作为取代物,并通过1-6个碳原子的烃部分与另一α-碳原子相连形成环状结构。琥珀酸衍生物的盐可以是单盐,而另一羧基是胺化的或是酯化的。但没有叙述用于胺化和酯化的适合的胺或醇。优先选择的盐是二元盐。
UK2,177,418A(申请人案号K6240GBR)公开了含主要量汽油(适合于火花点火发动机)和小量琥珀酸衍生物碱金属或碱土金属盐作为火焰改进剂(在其至少一个α-碳原子上有作为取代物的20-200碳原子的未取代或取代的脂肪烃,或在其一个α-碳原子上有20-200个碳原子的未取代或取代的脂肪烃作为取代物的琥珀酸衍生物,并通过1-6个碳原子的烃部分与另一α-碳原子相连形成环状结构。琥珀酸衍生物的盐可以是一元的,另一羧基是胺化或酯化的,但没有叙述用于胺化或酯化的适合的胺或醇。所述的优先选择的盐是二元盐。
UK1,306,233公开了用于燃料的一种组合物,包括油溶性羧酸分散剂和一热稳定的相对说来不挥发的石油馏份。羧酸分散剂是一羧酸或酸酐、酯、金属盐或其酰化的氮衍生物。基本上饱和的脂肪烃取代的琥珀酸和酸酐是特别优先选择的分散剂。
现已发现,某些琥珀酸衍生物的碱金属盐是用的火花助剂(火焰速度改进剂),与本领域已知的火花助剂相比。它们有粘性较小、不易附聚的优点,后者由于可导致气门粘接,是一特别的问题。
因此本发明提供一种汽油组合物,它包括主要量的适合于火花点火发动机的汽油和小量的通式(Ⅰ)与琥珀酸衍生物的烷基聚醚醇偏酯碱金属盐,
(式中n为4-25的整数,R代表C6-20烷基,R1各自代表一氢原子或C1-10烷基),琥珀酸衍生物至少在其一个α-碳原子上有15-200个碳原子的未取代或取代的脂肪烃基作为取代物,还可以通过有1-6个碳原子的烃部分与另一α-碳原子相连形成环状结构。
本发明进一步提供使火花点火内燃机工作的方法,该方法包括向该内燃机引入上述的汽油组合物。
偏酯碱金属盐最好是钠盐,特别是钾盐。
烷基或脂肪烃取代基可以是直链或支链的。
优先选择的n为4-20的整数,较好的是4-15,特别是5或6。
优先选择的R含至少6个碳原子,最好是至少7个碳原子。R代表C9-15或较好的是C12-15烷基比较有利。
每一R1最好分别代表氢原子或C1-5烷基,特别是甲基或乙基。
通式(Ⅰ)的化合物是已知化合物,它们可用类似于已知的方法来制备。
在琥珀酸衍生物的至少一个α-碳原子上的取代基的性质是很重要的,因为它在很大程度上决定了偏酯碱金属盐在汽油中的溶解度。
脂肪烃基可以方便地自一聚烯烃衍生。聚烯烃的单体具有2-6个碳原子,例如聚乙烯、聚丙烯、聚丁烯、聚戊烯、聚己烯或混合聚合物。特别优先选择的是衍生自聚异丁烯的脂肪烃基。
优先选择的脂肪烃基有15-150、比较优先选择15-100,有利的是15-45个碳原子。具有20-30个碳原子的脂肪烃基已被发现是非常有效的。
脂肪烃基可含取代物,例如一个或多个氢原子可被另外的原子所取代,例如卤原子,或被一非脂族有机基团取代,例如取代或未取代的苯基,或羟基、醚、酮、醛或酯基。
琥珀酸衍生物可有多于一个的C15-200脂肪烃基连接到一个或二个α-碳原子上。最好是琥珀酸有一个C15-200脂肪烃基在一个α-碳原子上,而在另一α-碳原子上方便的是没有取代物或仅有一个很短的烃基,例如C1-6基,相连接。后者可与C15-200脂肪烃基连接,形成环状结构。
取代琥珀酸衍生物的制备是本领域已知的。如以聚烯烃用作取代物。取代的琥珀酸衍生物可以方便地制备,方法是将聚烯烃(例如聚异丁烯)与马来酸或马来酸酐混合,并在混合物中通以氯气,得到氢氯酸和聚烯烃取代的琥珀酸,如UK949,981所述。
从例如UK1,483,729可知用聚烯烃与马来酐进行热反应制备烃取代琥珀酐。
聚烯烃取代的琥珀酸偏酯可方便地用已知方法将聚烯烃取代琥珀酸与通式(Ⅰ)的烷基聚醚醇(例如n为5,R为C12-15烷基混合物,R1为甲基的醇,以Royal Dutch/Shell集团成员公司商标“Oxilube-500”供市)反应。偏酯与碱金属氢氧化物如氢氧化钾反应可以方便地制备相应的碱金属盐。
本发明的汽油组合物可方便地含1-1000ppmw、最好是100-400ppmw的偏酯碱金属盐,最优先选择地是得到碱金属(特别是钾)的浓度在4-16ppmw。
本领域技术熟练者将会知道,本发明汽油组合物中存在碱金属能够期望对发动机气门座凹进给予保护。
本发明的汽油组合物也可含其它添加剂,因此可含铅化合物作为抗爆添加剂。所以本发明的汽油组合物包括含铅和不含铅的汽油。汽油组合物也可含如酚类之抗氧化剂(例如2,6-二叔丁基苯酚)或亚苯基二胺类抗氧化剂(例如N,N′-二仲丁基-对-亚苯基二胺)或非铅化合物的抗爆添加剂,或聚醚氨基添加剂,例如U.S.4,477,261和欧洲专利申请№.151,621所述。
本发明的汽油组合物除了偏酯碱金属盐外,一特别适合的添加剂是衍生自C2-6单体的聚烯烃。优先选择的聚烯烃是具有20-175个碳原子、特别是35-150个碳原子的聚异丁烯。本发明汽油组合物中的聚烯烃的量最好是100-1200ppmw。
另外,自C2-6单体衍生的一些或所有的聚烯烃可以被通式(Ⅱ)的聚亚氧烷基二醇半醚取代,
(式中EO代表乙烯氧基,PO代表丙烯氧基,R2为C1-20烷基,m和t代表每一半醚分子中乙烯氧和丙烯氧部分的平均数使m/(m+t)在0-0.5的范围内、t/(m+t)在0.5-1的范围内),半醚的数均分子量(Mn)在500-3000,最好在式(Ⅱ)中R2是C12-15烷基混合物,半醚的运动粘度约为80mm2/s(20℃,按ASTM D445)。这种半醚以Royal Dutch/Shell集团成员公司商标“Oxilube-949”供市。本发明汽油组合物中的半醚量最好是100-1200ppmw。
本发明的汽油组合物除了偏酯碱金属盐外,另一特别适合的添加剂是含C20-150烷基或链烯基多胺。优先选择的多胺是N-聚异丁烯-N,N′-二甲基-1,3-二氨基丙烷。本发明的汽油组合物中多胺的量最好是5-200ppmw。
本发明的汽油组合物除偏酯碱金属盐外,一非常适合的添加剂组合于U.S.4,357,148中有所叙述。此添加剂组合包括油溶性脂族多胺和烃聚合物。此添加剂组合减少了对辛烷值要求的增加(ORI)。ORI-减少是与火花点火发动机燃烧室和邻近表面预防沉积形成和/或沉积的去除有关。虽然可以使用各种类型的多胺和各种类型的聚合物,但优先选择使用其单体有2-6个碳原子的聚烯烃和含C20-150烷基或链烯基多胺。因此本发明的汽油组合物最好含有这样的组合。上述烯烃的一非常有利的种类是20-175个碳原子的聚异丁烯、特别是35-150个碳原子的聚异丁烯。所用的多胺最好是N-聚异丁烯-N′,N′-二甲基-1,3-二胺基丙烷。本发明的汽油组合物中聚烯烃和含烷基或链烯基的多胺的含量最好分别为100-1200ppmw和5-200ppmw。组合物可进一步含有非离子型表面活性剂,如烷基苯酚或烷氧化烷基。这种表面活性剂适合的例子包括C4-18烷基苯酚和C2-6烷基乙氧化物或C2-6烷基丙氧化物或它们的混合物。表面活性剂的用量最好是10-1000ppmw,组合物还可进一步含如聚烯烃取代的琥珀酰亚胺之类的清洁剂。这种清洁剂适合的例子包括EP-A-271937中所述的聚烯烃取代的琥珀酰亚胺,清洁剂的用量为10-1000ppmw较好。
本发明的汽油组合物包括主要量的适用于火花点火发动机的汽油(基燃料)。它包括沸程基本在30-230℃的汽油沸程的烃基燃料。基燃料可包括饱和烃、烯属烃和芳烃的混合物,它们可来自直馏汽油、用合成方法生产的芳烃混合物,热裂解烃原料或催化裂解烃原料、氢裂解石油馏份或催化重整烃,基燃料的辛烷数不是关键问题,但一般在65以上。在汽油中,烃可以用相当量的醇、醚、酮或酯来置换。当然,适合的基燃料是基本上无水的,因为水妨碍平稳地燃烧。
偏酯碱金属盐可以分别加入汽油或与其它添加剂混合后再一起加入汽油。优先选择的加这些盐的方法是首先制备盐的浓缩物,然后再以计算的所需量的浓缩物加入汽油。
因此,本发明进一步提供适于加入汽油的浓缩物,包括一与汽油相容的稀释剂和10-50%(重量)的通式(Ⅰ)与琥珀酸衍生物的烷基聚醚醇偏酯碱金属盐(以稀释剂为基础计算)。
(式中n为4-25的整数,R代表C6-20烷基,每一R1分别代表氢原子或C1-10烷基),琥珀酸衍生物至少在一个α-碳原子上有一未取代或取代的15-200个碳原子的脂肪烃基作为取代物,也可通过1-6个碳原子的烃部分与另一α-碳原子相连形成环状结构。
适合的与汽油相容的稀释剂有烃(如庚烷),醇或醚(如甲醇、乙醇、丙醇、2-丁氧基乙醇或甲基叔丁基醚)。优先选择的稀释剂是芳烃溶剂如甲苯、二甲苯、它们的混合物,或甲苯或二甲苯与某醇的混合物。浓缩物还可以含一去浊雾剂,特别是一聚醚型乙氧化的烷基苯酚/甲醛树脂。如采用去浊雾剂,其浓度最好在0.01-1%(重量)(以稀释剂为基础计算)。
本发明进一步提供通式(Ⅰ)与琥珀酸衍生物的烷基聚醚醇偏酯碱金属盐的应用,
(n为4-25的整数,R代表C6-20烷基,每一R1分别代表氢原子或C1-10烷基,琥珀酸衍生物在其至少一个α-碳原子上有一15-200碳原子的未取代或取代的脂肪烃基作为取代物,也可通过1-6个碳原子的烃部分与另一α-碳原子相连形成环状结构)作为含主要部分的适用于火花点火发动机的汽油的汽油组合物中的火花助剂和抗气门粘附剂。
本发明将从下面的实例得到进一步的了解。
实例1
将Mn为280(凝胶渗透色谱法测定)的聚异丁烯和马来酐的混合物在氮气氛中搅拌加热至180℃,然后在反应混合物中通氯,历时5小时,反应混合物在180℃再维持4小时。反应混合物中聚异丁烯/马来酐/氯的摩尔比为1.0/1.5/1.12。蒸除过量的马来酐,得到酸值为5.9mmol/g的聚异丁烯基琥珀酐。
将得到的聚异丁烯琥珀酐(100g)和148g通式Ⅰ的烷基聚醚醇(n为5,R为C12-15烷基混合物,R1代表甲基)(由Royal Dutch/Shell集团成员公司以“Oxilube-500”商标提供)的混合物在200℃于大气压下加热5小时,并在20mmHg压力下加热1小时,得到酸值为2.1mmol/g的偏酯。冷却后,将得到的偏酯(100g)溶于二甲苯(50g),并将得到的溶液与氢氧化钾在甲醇中的溶液(8.5g 83%(重量)的氢氧化钾溶于21.2g甲醇)相混合。反应混合物加热至60℃3小时,加热完毕,反应混合物过滤,保留滤液。滤液纯化后得到所需之盐(钾含量:4.4%m)。
实例2
将Mn为340(凝胶渗透色谱法测定)的聚异丁烯(280g)和马来酐(196g)的混合物于200℃下加热16小时,加热完毕后,蒸除过量的马来酐,得到酸值为5.3mmol/g的聚异丁烯基琥珀酸酐。
将得到的聚异丁烯琥珀酸酐(303.9g)和实例1中所说的通式(Ⅰ)的烷基聚醚醇(405.5g)在200℃、大气压下加热3.5小时,并在20mmHg压力下加热1小时。所得到的偏酯的酸值为1.04mmol/g。将得到的偏酯(681g)溶于二甲苯(500ml)与氢氧化钾于甲醇中的溶液(8.5g83%(重量)的氢氧化钾溶于21.2g甲醇)在65℃反应3小时,过滤,纯化,得到所需要的盐,钾含量为4.0%m。
实例3
用与实例2类似的方法制备通式(Ⅰ)的烷基聚醚醇偏酯钾盐,通式(Ⅰ)中n为5,R为C8-11烷基混合物,R1代表氢原子,其数均分子量(Mn)为380(凝胶渗透色谱测定)(以Royal Dutch/Shell集团成员公司商标“Dcbanol91-5”提供)和聚异丁烯基琥珀酸,用上述的烷基聚醚醇代替实例2中的烷基聚醚醇。
实例4
用类似于实例2的方法,制备C12-15烷醇混合物、1,2环氧丙烷、环氧乙烷(按烷醇/1,2-环氧丙烷/环氧乙烷摩尔比1∶4.2∶5.6)的缩合物(20℃ASTM D1298密度为0.98;ASTM D2270粘度指数186,Mn为700,以Royal Dutch/Shell集团成员公司商标“Oxilube-501”提供)的偏酯钾盐和聚异丁烯基琥珀酸,使用上述缩合物代替实例2中的烷基聚醚醇。
实例5
将Mn为353(凝胶渗透色谱法测定)的聚丁烯(45Kg)和马来酐(25Kg)的混合物在200℃下加热16小时,加热完毕后,蒸除过量的马来酐,得到酸值为4.04mmol/g的聚异丁烯基琥珀酐(剩余马来酐<0.1%(重量),剩余聚异丁烯21.7%(重量))。
将得到的聚异丁烯基琥珀酐(35Kg)和35.2Kg实例1中的烷基聚醚醇于200℃和大气压下加热4.5小时,得到的偏酯产品的酸值为1.04mmol/g。所得到的偏酯(69Kg)溶于二甲苯(30Kg)与氢氧化钾于甲醇中的溶液(17Kg25%(重量)的溶液)于65℃反应3小时,然后过滤,纯化,得到含钾量2.10%(重量)的所需之盐。非挥发物浓度为61.1%(重量)。
实例6
在某些驾驶条件下预测车辆发动机发生的情况的方法是研究添加剂整套配方(混合物)在所有较轻成分即沸点低于350℃的成分除去后的外观和粘度特性。
因此,将表1中的添加剂配方A-H用旋转蒸发器于140℃和1.3帕下蒸发1小时除去较轻的成分,残留物按ASTM D455测定它们的粘度,结果示于表Ⅰ。所用的添加剂是:添加剂Ⅰ∶N-聚异丁烯-N′,N′-二甲基-1,3-二氨基丙烷(聚异丁烯用气相渗透压测定法测定的平均分子量为1350);添加剂Ⅱ∶聚异丁烯基琥珀酸钾(用气相渗透压测定的聚异丁烯平均分子量为950添加剂Ⅲ∶数均分子量为650的聚异丁烯(凝胶渗透色谱法测定的分子量),添加剂Ⅳ∶式(Ⅱ)的聚亚氧烷基二醇半醚(式中R2为C12-15烷基混合物,按ASTM D 445测定的半醚的运动粘度约为80mm2/s,20℃)(由Royal Dutch/Shell集团成员公司以“Oxilube-949”商标提供)。
添加剂整套配方残留物与添加剂整套配方的气门粘附趋向直接相关,这是常识。所以添加剂整套配方残留物的粘度愈大,气门粘附趋向愈大,表Ⅰ清楚地表明:与先有技术中的添加剂整套配方A和B相比,含有实例1,2和4产品的添加剂整套配方C-H的残留物具有较低的粘度。因此,可以得出结论:与添加剂整套配方A和B相比,添加剂整套配方C-H必定也有较低的气门粘附趋向。
实例7
按下述方法在Volkswagen Transporter(译注-德国大众汽车厂制造车辆)上对添加剂整套配方A,B和C进行进气阀粘附试验。
先以基油行车50公里,以冲刷油路系统,然后以基油和添加剂整套配方A,B和C中的一种混合行驶112公里进行试验,在这段距离中,车子经受热烤阶段、怠速阶段和分别为2、3和4档的最大速度24、40和56公里/小时。在热烤阶段,关闭发动机停车10分钟。相反,在怠速阶段,不关发动机停车30分钟。
试车完毕后,将车子停放于-16℃的冷冻拖车中过夜。次日早晨测定每一汽缸的最大压缩压力评定气门粘附。
按照类似方法在Vauxhall Cavalier车中测试添加剂整套配方A、B和C。
现将结果示于表Ⅱ中。从结果可知,添加剂整套配方C的平均最大压缩压力高于先有技术添加剂整套配方A的平均最大压缩压力(Volkswagen Transporter和Vauxhall Cavalier),并且高于添加剂整套配方B(Volkswagen Transporter)
实例8
用1.3升的Astra发动机进行试验,估价火火助剂的性能。此Astra发动机进行了改装使其中一个汽缸的燃烧室提供透视性。试验汽缸的压缩比为5.8∶1。在每一试验中,发动机以2000rpm工作2小时,在此期间连续进行测定。从收集的数据可能测定各被试的各火花助剂的指示平均有效压力(IMEP)周期变化的降低。试验是对没有钾添加剂的无铅汽油和有2、4和8ppmw钾添加剂的无铅汽油进行的。钾的加入是以聚异丁烯取代的琥珀酸(凝胶渗透色谱法测定的聚异丁烯平均分子量为280)偏酯盐的形式和式(Ⅰ)的烷基聚醚醇(式中n为5,R为C12-15烷基混合物,R1代表甲基)(以Royal Dutch/Shell集团成员公司的商标“Oxilube-500”提供)。
试验结果示于表Ⅲ。
Claims (10)
2、(式中n为4-25的整数,R代表C6-20的烷基,每一R1分别代表氢原子或C1-10烷基)与琥珀酸衍生物的烷基聚醚醇偏酯盐,琥珀酸衍生物至少在其一个α-碳原子上有一个15-200个碳原子的未取代或取代的脂肪烃基作为取代物,还可以通过具有1-6个碳原子与另一α-碳原子相连接形成一环状结构。
3、权利要求1或2所述的汽油组合物,其中脂肪烃基衍生自聚烯烃,其单体有2-6个碳原子。
4、前述权利要求任一项所述的组合物,其中脂肪烃基有15-45个碳原子。
5、前述权利要求任一项所述的组合物,其中R代表C9-15烷基。
6、前述权利要求任一项所述的组合物,该组合物另外还包括小量C2-6单体衍生的聚烯烃和/或通式
(式中EO代表亚乙氧基,PO代表亚丙氧基,R2为C1-20烷基,m和t代表每个半醚分子中亚乙氧基和亚丙氧基部分的平均数,使m/(m+t)在0-0.5的范围、t/(m+t)在0.5-1的范围)的聚亚氧烷基二醇半醚,半醚的数均分子量(Mn)为500-3000,以及小量的含C20-150烷基或链烯基的多胺。
7、权利要求6所述的汽油组合物,该组合物含100-1200ppmw的聚烯烃和/或聚亚氧烷基二醇半醚和5-200ppmw含烷基或链烯基的多胺。
9、操作火花点火内燃机的方法,该方法包括将权利要求1-7任一项的汽油组合物引入所说的发动机。
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US5405419A (en) * | 1994-05-02 | 1995-04-11 | Chevron Chemical Company | Fuel additive compositions containing an aliphatic amine, a polyolefin and a poly(oxyalkylene) monool |
KR100256336B1 (ko) * | 1995-12-05 | 2000-05-15 | 이구택 | 자기적특성이 우수한 방향성 규소강의 제조방법 |
KR100256343B1 (ko) * | 1995-12-21 | 2000-05-15 | 이구택 | 저온 스라브 가열방식에의한 방향성 전기강판의 제조방법 |
EP1137745B1 (en) | 1998-12-04 | 2003-08-27 | Infineum Holdings BV | Fuel additive and fuel composition containing the same |
WO2001048121A1 (fr) * | 1999-12-24 | 2001-07-05 | Sanyo Chemical Industries, Ltd. | Additif pour mazout et composition de mazout |
WO2001051593A1 (en) | 2000-01-12 | 2001-07-19 | Cam Tecnologie S.P.A. | Fuel comprising an emulsion between water and a liquid hydrocarbon |
MY155314A (en) * | 2007-11-28 | 2015-09-30 | Shell Int Research | Gasoline compositions |
GB201705088D0 (en) * | 2017-03-30 | 2017-05-17 | Innospec Ltd | Composition, method and use |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2929696A (en) * | 1957-09-06 | 1960-03-22 | California Research Corp | Rust inhibited fuels |
DE1271877B (de) * | 1963-04-23 | 1968-07-04 | Lubrizol Corp | Schmieroel |
US3632570A (en) * | 1968-09-19 | 1972-01-04 | Hercules Inc | Polysaccharide process |
GB1346765A (en) * | 1970-06-16 | 1974-02-13 | Shell Int Research | Fuel compositions |
CA959263A (en) * | 1971-04-29 | 1974-12-17 | Robert L. Cohen | Polyoxyalkylene anti-icing agents |
GB1588067A (en) * | 1977-10-13 | 1981-04-15 | Lubrizol Corp | Lubricants and fuels and concentrates containing demulsifier additive compositions |
GB8515974D0 (en) * | 1985-06-24 | 1985-07-24 | Shell Int Research | Gasoline composition |
GB8710955D0 (en) * | 1987-05-08 | 1987-06-10 | Shell Int Research | Gasoline composition |
US4877416A (en) * | 1987-11-18 | 1989-10-31 | Chevron Research Company | Synergistic fuel compositions |
JP2644602B2 (ja) * | 1988-01-27 | 1997-08-25 | ザ ルブリゾル コーポレーション | 燃料組成物 |
-
1990
- 1990-12-18 GB GB909027389A patent/GB9027389D0/en active Pending
-
1991
- 1991-12-13 ES ES91203301T patent/ES2055520T3/es not_active Expired - Lifetime
- 1991-12-13 BR BR919105409A patent/BR9105409A/pt not_active Application Discontinuation
- 1991-12-13 ZA ZA919836A patent/ZA919836B/xx unknown
- 1991-12-13 EP EP91203301A patent/EP0491439B1/en not_active Expired - Lifetime
- 1991-12-13 DE DE69101966T patent/DE69101966T2/de not_active Expired - Fee Related
- 1991-12-14 KR KR1019910023004A patent/KR920012401A/ko not_active Application Discontinuation
- 1991-12-16 RU SU915010492A patent/RU2036953C1/ru active
- 1991-12-16 JP JP3332077A patent/JPH04296393A/ja active Pending
- 1991-12-16 HU HU913966A patent/HU210915B/hu not_active IP Right Cessation
- 1991-12-16 AU AU89748/91A patent/AU643347B2/en not_active Ceased
- 1991-12-16 CN CN91108017A patent/CN1062752A/zh not_active Withdrawn
- 1991-12-16 CA CA002057705A patent/CA2057705A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
GB9027389D0 (en) | 1991-02-06 |
JPH04296393A (ja) | 1992-10-20 |
HU210915B (en) | 1995-09-28 |
AU8974891A (en) | 1992-06-25 |
AU643347B2 (en) | 1993-11-11 |
BR9105409A (pt) | 1992-08-25 |
KR920012401A (ko) | 1992-07-27 |
DE69101966D1 (de) | 1994-06-16 |
EP0491439A1 (en) | 1992-06-24 |
RU2036953C1 (ru) | 1995-06-09 |
DE69101966T2 (de) | 1994-09-01 |
HU913966D0 (en) | 1992-02-28 |
HUT60759A (en) | 1992-10-28 |
ES2055520T3 (es) | 1994-08-16 |
CA2057705A1 (en) | 1992-06-19 |
EP0491439B1 (en) | 1994-05-11 |
ZA919836B (en) | 1992-09-30 |
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