CN101622329A - 适合无生命有机材料的抗静电改性和导电性改善的添加剂配制剂 - Google Patents
适合无生命有机材料的抗静电改性和导电性改善的添加剂配制剂 Download PDFInfo
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- CN101622329A CN101622329A CN200880006889A CN200880006889A CN101622329A CN 101622329 A CN101622329 A CN 101622329A CN 200880006889 A CN200880006889 A CN 200880006889A CN 200880006889 A CN200880006889 A CN 200880006889A CN 101622329 A CN101622329 A CN 101622329A
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Classifications
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- Lubricants (AREA)
Abstract
本发明涉及一种用于无生命有机材料的抗静电改性和导电性改善的添加剂配制剂,其由如下组分组成:(A)1-50重量%的烯烃-二氧化硫共聚物,(B)1-50重量%的包含碱性氮原子且具有含至少4个碳原子的较长链烃基或确保(B)在无生命有机材料中的溶解性的等价结构单元的化合物,(C)0.1-30重量%的油溶性酸,和(D)1-80重量%的高沸点有机溶剂,其中这些分子类型的至少80重量%在标准压力下的沸点大于150℃。
Description
本发明涉及一种适合无生命有机材料的抗静电改性和导电性改善并且适合在化学和物理方法过程中防止静电荷的新型和改进添加剂配制剂。本发明进一步涉及一种制备该添加剂配制剂的方法。本发明进一步涉及该添加剂配制剂的用途以及使用该添加剂配制剂静电改性的无生命有机材料。本发明进一步涉及一种制备具有低残留烯烃含量的烯烃-二氧化硫共聚物的方法,该共聚物可以有利地在该添加剂配制剂中作为组分使用。
无生命有机材料如燃料通常是非常差的导体。因此,电荷倾向于局部积聚在这种有机材料中并且作为火花以不受控制的方式放电,这可能导致通常可燃且常常高度易燃的该有机材料与空气或氧气接触时产生爆炸或火灾。合适的抗静电添加剂允许增加无生命有机材料的导电性,从而不再形成静电荷并且降低爆炸和火灾危险。
US-A 3 917 466(1)公开了用于抗静电改性和改善导电性的添加剂配制剂,其由烯烃-二氧化硫共聚物、可以通过表氯醇与脂族单胺或多胺如N-动物脂肪-1,3-二氨基丙烷反应得到的聚合多胺、油溶性磺酸和低沸点溶剂如甲苯和/或异丙醇组成。
US-A 4 416 668(2)描述了α-烯烃-马来酰亚胺共聚物和烯烃-二氧化硫共聚物的混合物作为有机液体如燃料的抗静电剂。这些混合物可以包含溶剂如苯、甲苯或二甲苯。
然而,现有技术中所述抗静电剂的效力仍不令人满意。在无生命有机材料中需要甚至更有效且持续时间更长的导电性增加。此外,抗静电剂应具有甚至更高的热稳定性。由于毒性和环境原因,它们应尽可能不含金属和卤素。它们尤其应具有最大闪点,从而使它们能够在用于无生命有机材料之前在其制备、运输和储存过程中安全地处理,即没有爆炸和火灾危险。
因此,本发明的目的是提供用于增加无生命有机材料,尤其是燃料和矿物油产品的导电性且具有有效作用、高热稳定性和最大闪点的抗静电剂,其从毒性和环境观点看没有问题。
因此,发现了适合无生命有机材料的抗静电改性和导电性改善的添加剂配制剂,其基本由如下组分组成:
(A)1-50重量%的烯烃-二氧化硫共聚物,
(B)1-50重量%的包含一个或多个碱性氮原子且具有至少一个具有至少4个碳原子的较长链线性或支化烃基或确保组分(B)在无生命有机材料中的溶解性的等价结构单元的化合物,
(C)0.1-30重量%的油溶性酸,和
(D)1-80重量%的由一种或多种分子类型组成的高沸点有机溶剂,其中这些分子类型的至少80重量%在标准压力下的沸点大于150℃,
其中所有组分(包括可能存在的次级组分和/或非破坏性杂质)的总和加起来为100重量%。
本发明的添加剂配制剂可能-通常作为生产的结果-包含至多10重量%,尤其是至多5重量%,特别是至多2重量%的其他成分作为次级组分和/或非破坏性杂质。
在优选实施方案中,本发明的添加剂配制剂基本由如下组分组成:
(A)10-30重量%,尤其是13-25重量%的组分(A),
(B)10-30重量%,尤其是13-25重量%的组分(B),
(C)2-15重量%,尤其是4-10重量%的组分(C),和
(D)40-78重量%,尤其是50-70重量%的组分(D)。
所述的本发明添加剂配制剂呈实际活性组分(A)、(B)和(C)在高沸点有机溶剂(D)中的浓缩物,其高度适合产品的安全运输和安全储存。
组分(A)的烯烃-二氧化硫共聚物的结构和已知制备方法描述于文献(1)和(2)中。组分(A)优选为二氧化硫与一种或多种具有2-24个碳原子的线性或支化1-烯烃的共聚物。组分(A)的共聚物(聚砜)通常为其中一个砜单元通常跟在一个烯烃单元之后的交替1∶1共聚物;还可以少量存在两个或更多个烯烃单元的序列。一些烯烃单体可以被烯属不饱和羧酸(例如丙烯酸、甲基丙烯酸或乙烯基乙酸)或烯属不饱和二羧酸(例如马来酸或富马酸)或其衍生物(例如马来酸酐)代替,从而使组分(A)的共聚物尤其由50mol%二氧化硫或砜单元,40-50mol%烯烃单元和0-10mol%来自所述烯属不饱和羧酸、烯属不饱和二羧酸或其衍生物的单元形成。
对制备组分(A)有用的具有2-24个碳原子的支化和尤其是线性1-烯烃例如包括乙烯、丙烯、1-丁烯、2-丁烯、异丁烯、1-戊烯、1-己烯、1-庚烯、1-辛烯、1-壬烯、1-癸烯、1-十一碳烯、1-十二碳烯、1-十三碳烯、1-十四碳烯、1-十五碳烯、1-十六碳烯、1-十七碳烯、1-十八碳烯、1-十九碳烯、1-二十碳烯、1-二十一碳烯、1-二十二碳烯、1-二十三碳烯、1-二十四碳烯或其混合物。特别优选具有6-16个碳原子,尤其是8-14个碳原子的线性1-烯烃,或具有12-22个碳原子,尤其是14-20个碳原子的线性1-烯烃,以及它们的混合物,例如1-十二碳烯和1-十四碳烯的混合物。还可能有利的是使用低分子量和高分子量1-烯烃的混合物,即具有双峰分布的1-烯烃混合物来制备组分(A),例如具有6-13个碳原子的1-烯烃和具有14-20个碳原子的1-烯烃的混合物,或具有6-10个碳原子的1-烯烃和具有11-15个碳原子的1-烯烃的混合物或具有2-24个碳原子的1-烯烃和具有4-10个碳原子的单一1-烯烃的混合物。当使用工业或其他1-烯烃混合物时,在上述范围内的碳原子指标基于这些混合物的平均碳原子数,其中平均碳原子数是混合物中存在的所有1-烯烃的重量分数与相应碳原子数的数学乘积之和。
组分(A)的烯烃-二氧化硫共聚物通常具有的数均分子量Mn为2000-1000000,尤其是4000-100000,特别是6000-25000。多分散性(PDI=Mw/Mn)通常为1.1-30,尤其是1.5-20,特别是2-10,最优选2.3-5。
文献(1)推荐通过合适的自由基聚合方法在0-50℃的温度范围内制备烯烃-二氧化硫共聚物;要使用的溶剂为苯、甲苯或二甲苯;仅使用低摩尔过量的二氧化硫(最多1.5倍摩尔量);推荐自由基引发剂如过氧化物或偶氮化合物和使用光合光的额外辐照。根据文献(2),烯烃-二氧化硫共聚物可以通过在含水介质中的乳液聚合方法制备。然而,这两种制备方法需要改进且如此得到的烯烃-二氧化硫共聚物在本发明添加剂配制剂中的使用导致处理和效力上的缺点。尤其是挥发性和可燃性起始烯烃的含量仍然太高,从而使所得抗静电剂添加剂配制剂的闪点太低。因此需要烯烃-二氧化硫共聚物的改进制备方法,以使它们能够无问题地用于本发明添加剂配制剂。
因此,在本发明上下文中,发现了一种制备烯烃-二氧化硫共聚物的方法,该共聚物包含小于15mol%,优选小于10mol%,尤其小于7mol%,特别是小于5mol%未在与二氧化硫的共聚中转化的烯烃,该方法包括以至少1.4倍摩尔过量,尤其是1.6倍摩尔过量使用二氧化硫并且在由一种或多种分子类型组成的高沸点惰性有机溶剂中进行聚合,其中这些分子类型中至少50重量%具有8个以上碳原子。优选以至少1.8倍摩尔过量,尤其是1.8-2.5倍摩尔过量使用二氧化硫并且在由一种或多种分子类型组成的高沸点惰性有机溶剂中进行聚合,其中这些分子类型中至少80重量%具有9-30个碳原子。有利的是在这里使用高沸点有机溶剂,尤其是具有9-30个碳原子的高沸点芳烃或该类高沸点芳烃的混合物,正如对本发明中组分(D)所定义的。优选在10-40℃,尤其是15-29℃下在0.5-24小时内进行反应。
因此,在本发明上下文中,发现了另一种制备烯烃-二氧化硫共聚物的方法,该共聚物包含小于15mol%,优选小于10mol%,尤其小于7mol%,特别是小于5mol%未在与二氧化硫的共聚中转化的烯烃,该方法包括以至少1.1倍摩尔过量使用二氧化硫并且在15-38℃,尤其是20-30℃下于自生压力下进行聚合。优选以至少1.4倍摩尔过量,尤其是至少1.6倍摩尔过量,特别是至少1.8倍摩尔过量,更优选1.8-2.5倍或1.4-2.5倍摩尔过量使用二氧化硫并且在由一种或多种分子类型组成的高沸点惰性有机溶剂中进行聚合,其中这些分子类型中至少80重量%具有9-30个碳原子。有利的是在这里也使用高沸点有机溶剂,尤其是具有9-30个碳原子的高沸点芳烃或该类高沸点芳烃的混合物,正如对本发明中组分(D)所定义的。
在制备烯烃-二氧化硫共聚物的后一方法的优选实施方案中,聚合在第一步中在0.5-5小时内在30-38℃和自生压力下进行,然后在第二步中在1-5小时内在20-29℃和自生压力下进行。
在许多情况下,用于制备烯烃-二氧化硫共聚物的前一或后一方法的备选制备足以在该方法中实现所需改进,尤其是就所得抗静电剂添加剂配制剂的闪点提高而言。然而,还可以将这两种方法结合,即以至少1.6倍摩尔过量使用二氧化硫且聚合可以在由一种或多种分子类型组成的高沸点惰性有机溶剂中在15-38℃和自生压力下进行,其中这些分子类型中的至少50重量%具有8个以上碳原子。在所述的所有方案中,可以省略光合光辐照,该辐照尤其仅能以高成本和大不便在工业规模上进行。
二氧化硫与烯烃的所述聚合通常通过自由基机理进行。该自由基聚合通过常规方法进行。为此,使用常规自由基引发剂,尤其是基于过氧化物或偶氮化合物的那些,例如过氧化二叔丁基、过新戊酸叔丁酯或偶氮二异丁腈。为了控制所要实现的分子量,还可以使用调节剂,例如硫醇如十二烷基硫醇。
制备烯烃-二氧化硫共聚物的所述改进方法基本实现了烯烃的完全转化。
包含一个或多个碱性氮原子的组分(B)化合物必须在要用本发明添加剂配制剂处理的无生命有机材料中可溶,但至少可均匀分布。组分(B)在许多情况下同样是聚合物。它具有至少一个具有至少4个碳原子,优选至少8个碳原子,尤其至少12个碳原子,特别是12-30个碳原子的较长链支化或尤其是线性烃基,条件是在无生命有机材料中的溶解性不能由等价的结构单元确保。组分(B)的化合物优选不包含任何游离羟基,因为它们在某些情况下可能损害本发明添加剂配制剂的效力。
在组分(B)的化合物中,所述较长链的支化或线性烃基可以在碱性氮原子上或在碱性氮原子之一上或者在碳原子上,尤其是在聚合结构中的聚合物主链的碳原子上。典型的较长链的支化或线性烃基例如为脂肪酸中存在的线性烷基,以及聚异丁基,尤其是具有20-150个碳原子,特别是35-100个碳原子的那些。
对具有该类较长链烃基的组分(B)合适的低聚或聚合结构类型例如为低聚乙烯胺或低聚乙烯亚胺与烷基卤的反应产物、聚乙烯亚胺与聚异丁烯基琥珀酸酐的反应产物、乙烯-乙酸乙烯酯-氨基(甲基)丙烯酸酯三元共聚物和尤其是用胺或多胺衍生的烯烃-马来酸酐共聚物,特别是具有至少一个碱性氮原子的α-烯烃-马来酰亚胺共聚物。
低聚乙烯胺与烷基卤的反应产物的典型实例是由十亚乙基十一胺和多倍摩尔过量的正十六烷基氯形成的具有梳状结构的反应产物。
对具有该较长链烃基的组分(B)合适的非聚合结构类型例如为三烷基脂肪酸铵盐如三烷基油酸铵和聚异丁烯基琥珀酰亚胺。
对没有较长链烃基的组分(B)合适的结构类型例如为聚乙烯亚胺和聚乙烯胺,其中特定的通常交联的聚合物结构确保所需溶解度性能。
组分(B)的具有至少一个碱性氮原子的特别优选的α-烯烃-马来酰亚胺共聚物的结构和制备方法原则上如文献(2)所述。在优选实施方案中,这些α-烯烃-马来酰亚胺共聚物可以通过一种或多种具有6-50个碳原子的线性或支化α-烯烃与马来酸酐的自由基聚合以及随后与一种或多种脂族多胺反应而得到。α-烯烃-马来酸酐共聚物和由其制备的α-烯烃-马来酰亚胺共聚物通常为在聚合物主链中交替的1∶1共聚物,其中一个马来酸单元之后总是跟在一个α-烯烃单元之后。作为较长链的支化或线性烃基的结果,通常产生梳状结构。
对制备组分(B)的α-烯烃-马来酰亚胺共聚物有用的具有6-50个碳原子的支化和尤其是线性1-烯烃例如为1-己烯、1-庚烯、1-辛烯、1-壬烯、1-癸烯、1-十一碳烯、1-十二碳烯、1-十三碳烯、1-十四碳烯、1-十五碳烯、1-十六碳烯、1-十七碳烯、1-十八碳烯、1-十九碳烯、1-二十碳烯、1-二十一碳烯、1-二十二碳烯、1-二十三碳烯、1-二十四碳烯、1-三十碳烯、1-四十碳烯、1-五十碳烯或其混合物。特别优选具有12-30个碳原子,尤其是16-24个碳原子的线性1-烯烃及其混合物。
1-烯烃与马来酸酐的自由基聚合通过常规方法进行。为此,使用常规自由基引发剂,尤其是基于过氧化物或偶氮化合物的那些,例如过氧化二叔丁基、过新戊酸叔丁酯或偶氮二异丁腈,使用常规温度和压力范围,例如在50-150℃和标准压力下,并且反应在常规溶剂如芳烃中进行。所用溶剂优选为本发明组分(D)的高沸点有机溶剂。
在聚合完成时,使所得α-烯烃-马来酸酐共聚物与一种或多种脂族多胺反应而得到对应的酰亚胺。形成酰亚胺要求具有伯氨基的多胺并且对于碱性氮原子要求至少一个另外的伯、仲或叔氨基。就此而言合适的实例是较短链的二胺如乙二胺、1,3-丙二胺、3-(N,N-二甲氨基)丙胺(“DMAPA”)或二[3-(N,N-二甲氨基)丙基]胺(“二-DMAPA”)或较长链的二胺如动物脂肪-1,3-二氨基丙烷。用于该酰亚胺形成的常规反应条件对本领域熟练技术人员是已知的。当额外将溶剂用于该酰亚胺形成时,优选使用本发明组分(D)的高沸点有机溶剂。
与脂族多胺反应的α-烯烃-马来酸酐共聚物的典型实例是由C20/24-α-烯烃-马来酸酐共聚物和3-(N,N-二甲氨基)丙胺(“DMAPA”)或二[3-(N,N-二甲氨基)丙基]胺(“二-DMAPA”)形成的具有梳状结构的反应产物。
组分(B)的具有至少一个碱性氮原子的所述α-烯烃-马来酰亚胺共聚物通常具有的重均分子量Mw为500-50000,尤其是1000-10000。典型的α-烯烃-马来酰亚胺共聚物是已经与动物脂肪-1,3-二氨基丙烷反应而得到酰亚胺且重均分子量Mw为1000-10000的α-烯烃-马来酸酐共聚物。
组分(C)的油溶性酸优选为有机磺酸,为了实现油溶性,该有机磺酸合适地具有较长链或较庞大的烃基,尤其是具有6-40个碳原子,特别是8-32个碳原子,更优选10-24个碳原子的烃基。合适的该类烃基为线性或支化烷基或链烯基如正己基、正庚基、正辛基、2-乙基己基、正壬基、正癸基、2-丙基庚基、正十一烷基、正十二烷基、正十三烷基、异十三烷基、正十四烷基、正十五烷基、正十六烷基、正十七烷基、正十八烷基、正十九烷基、正二十烷基、正二十一烷基、正二十二烷基、正二十三烷基、正二十四烷基、油基、亚油基或亚麻基,环烷基如环己基、甲基环己基或二甲基环己基,芳基如苯基或萘基,芳烷基如苄基或2-苯基乙基,或更优选烷芳基,尤其是被线性或支化C1-C18烷基取代的苯基或萘基如甲苯基、二甲苯基、正壬基苯基、正癸基苯基、正十二烷基苯基、异十三烷基苯基、正壬基萘基、二正壬基萘基、正癸基萘基、二正癸基萘基、正十二烷基萘基、二正十二烷基萘基、异十三烷基萘基或二异十三烷基萘基。在后面的单取代苯基中,烷基可以位于磺酸基团的邻、间或对位,优选对位取向。组分(C)的典型实例因此是正壬基苯磺酸、正癸基苯磺酸、正十二烷基苯磺酸、异十三烷基苯磺酸、正壬基萘磺酸、二正壬基萘磺酸、正癸基萘磺酸、二正癸基萘磺酸、正十二烷基萘磺酸、二正十二烷基萘磺酸、异十三烷基萘磺酸和二异十三烷基萘磺酸。
除了所述有机磺酸外,作为组分(C)原则上还可以使用例如油溶性有机亚磺酸或有机膦酸,它们同样合适地具有较长链或较庞大的烃基,尤其是具有6-40个碳原子,特别是8-32个碳原子,更优选10-24个碳原子的那些。
组分(D)的高沸点有机溶剂在本发明添加剂配制剂中不是用于无生命有机材料的抗静电改性和导电性改善的实际活性组分,而是通过其与组分(A)、(B)和(C)相互作用促进其作用的改进,有助于配制剂的热稳定性并确保高闪点。此外,组分(D)还用于更好地确定本发明添加剂配制剂的所需粘度,所述粘度对该配制剂的可用性构成重要标准。
在优选实施方案中,组分(D)由至少80重量%,尤其是至少90重量%的具有9-30个碳原子的高沸点有芳烃或该类高沸点芳烃的混合物组成。最优选组分(D)中至少80重量%,尤其是至少90重量%,特别是100重量%为具有9-20个碳原子,尤其是9-14个碳原子的高沸点芳烃的混合物。该类芳烃尤其是双环、三环或多环芳烃,例如萘、联苯、蒽或菲,或具有脂族侧链的单环、双环、三环或多环芳烃,例如被C7-C14烷基侧链,尤其是C7-C12烷基侧链取代的苯如正十二烷基苯或正十四烷基苯,但特别是被C1-C6烷基侧链取代的苯如正丙基苯、异丙基苯、乙基甲基苯、三甲基苯、乙基二甲基苯、二乙基苯、正丁基苯、异丁基苯、仲丁基苯、叔丁基苯、正戊基苯、叔戊基苯、正己基苯、甲基萘、二甲基萘或C2-C6烷基萘。所有的所述芳烃在标准压力下具有的沸点高于150℃,通常在标准压力下为大于150℃至330℃。
具有9个或更多个碳原子的所述芳烃的混合物可以作为工业溶剂馏分例如由ExxonMobil Chemical以名称100(C9-C10芳族馏分)、150(C10-C11芳族馏分)和200(C10-C14芳族馏分)市购;该C10-C11芳族馏分也称为“重质溶剂石脑油(Solvent Naphtha Heavy)”。
除了具有9个或更多个碳原子的所述芳烃外,在所述优选实施方案中的组分(D)可以包含0至小于20重量%的非芳族有机溶剂组分(例如在每种情况下沸点大于100℃,尤其大于130℃的长链石蜡和/或脂环族化合物和/或杂环化合物)和/或具有小于9个碳原子的芳族溶剂组分(例如甲苯或二甲苯)。
本发明的添加剂配制剂适当地由组分(A)、B)、(C)和(D)通过混合而制备。原则上可以由任何可以想到的混合顺序得到本发明添加剂配制剂。然而,已经发现就混合的实际进行而言优选的是首先在至少一部分高沸点有机溶剂(D)存在下将组分(A)和(C)相互均匀混合,然后引入组分(B)。还可能有利的是在稍微升高的温度,例如20-80℃,尤其是25-50℃下进行混合操作。在特别优选的实施方案中,首先在至少一些高沸点有机溶剂(D)存在下将组分(A)和(C)在30-60℃,尤其是40-55℃下相互均匀混合,然后引入组分(B),其中将组分(A)和(C)与一些高沸点有机溶剂(D)的混合物保持在上述温度范围内优选至少1分钟,尤其是1-120分钟,特别是1-30分钟,然后引入组分(B)。还可能有利的是完全或部分在减压,合适的是100毫巴至小于1巴,尤其是10毫巴至小于1巴下进行混合操作。可以使用所有常见混合技术和混合单元。
本发明的添加剂配制剂就本发明而言用于无生命有机材料的抗静电改性和导电性改善并用于在化学和物理方法中防止静电荷。
为此,将本发明的添加剂配制剂在要以抗静电方式改性并因此可以变得更导电的无生命有机材料的生产过程中或其生产之后引入或混入其中并在其中基本均匀分布。本发明添加剂配制剂在无生命有机材料中的浓度基于无生命有机材料通常为0.01-2000重量ppm,优选0.1-1000重量ppm,特别是0.5-500重量ppm,尤其是1-350重量ppm。尤其在用于燃料中的情况下,本发明添加剂配制剂的浓度可能更低;此时的典型剂量基于燃料为0.01-1000重量ppm,优选0.1-500重量ppm,特别是0.5-100重量ppm,尤其是1-10重量ppm。
无生命有机材料应理解为尤其指化妆品制剂如霜和洗剂,药物配制剂如药片和栓剂,照相记录材料如照相乳剂,油漆和清漆,塑料,蜡类,溶剂以及矿物油产品和燃料,尤其是柴油机燃料、燃料油、汽油燃料、航空汽油和汽轮机燃料,还有润滑剂,即马达油、润滑油、液压油、汽轮机油、调节器油、包括手动和自动油在内的传动油、压延油、热载体油、金属加工油、减震油和润滑脂。
可以用本发明添加剂配制剂抗静电改性的塑料的实例包括:
单-或二烯烃的聚合物如低密度或高密度聚乙烯、聚丙烯、线性聚丁烯-1、聚异戊二烯、聚丁二烯和单-或二烯烃的共聚物或所述聚合物的混合物;聚苯乙烯和苯乙烯或α-甲基苯乙烯与二烯和/或丙烯酸衍生物的共聚物,例如苯乙烯-丁二烯、苯乙烯-丙烯腈(SAN)、苯乙烯-甲基丙烯酸乙酯、苯乙烯-丁二烯-丙烯酸乙酯、苯乙烯-丙烯腈-甲基丙烯酸酯、丙烯腈-丁二烯-苯乙烯(ABS)或甲基丙烯酸甲酯-丁二烯-苯乙烯(MBS);
卤化聚合物,例如聚氯乙烯、聚氟乙烯、聚偏二氟乙烯及其共聚物;
衍生于α,β-不饱和酸及其衍生物的聚合物,例如聚丙烯酸酯、聚甲基丙烯酸酯、聚丙烯酰胺和聚丙烯腈;
衍生于不饱和醇和胺或其酰基衍生物或缩醛的聚合物,例如聚乙烯醇和聚乙酸乙烯酯;
聚氨酯(例如作为鞋底用材料),尤其是热塑性聚氨酯,聚酰胺,聚脲,聚苯醚,聚酯,聚碳酸酯,聚砜,聚醚砜,聚醚酮和乙烯-乙酸乙烯酯共聚物(例如也作为鞋底用材料)。
可以用本发明的添加剂配制剂抗静电改性的油漆和清漆包括油漆如醇酸树脂漆、分散漆、环氧树脂漆、聚氨酯漆、丙烯酸树脂漆和硝酸纤维素漆,或清漆如木材保护清漆。
可以用本发明的添加剂配制剂抗静电改性的蜡包括乙烯-乙酸乙烯酯共聚物蜡。
可以用本发明的添加剂配制剂抗静电改性并因此可以更导电的溶剂实例包括:链烷烃如正戊烷、正己烷或正庚烷,链烯烃如己烯、庚烯、辛烯、壬烯、十一碳烯或十二碳烯,芳烃如甲苯或二甲苯,环烷,醇如甲醇、乙醇、异丙醇或叔丁醇,醛如乙醛、丙醛或丁醛,酮如丙酮或丁酮,羧酸如甲酸、乙酸或丙酸,羧酸酯如乙酸甲酯或乙酸乙酯,羧酰胺如N,N-二甲基甲酰胺,以及它们的混合物。
本发明的添加剂配制剂以特别有利的方式适合汽轮机燃料(喷气燃料)的抗静电改性和导电性改善。汽轮机燃料尤其用于操作飞机汽轮机。
常规汽轮机燃料组合物包含大部分的液态汽轮机燃料,其例如为常用于民用或军用航空的汽轮机燃料。这例如包括标号为Jet Fuel A、Jet FuelA-1、Jet Fuel B、Jet Fuel JP-4、JP-5、JP-7、JP-8和JP-8+100的燃料。Jet A和Jet A-1是市售的煤油基汽轮机燃料规格。对应的标准是ASTM D1655和DEF STAN 91-91。Jet B是基于石脑油和煤油馏分的更窄馏分燃料。JP-4等同于Jet B。JP-5、JP-7、JP-8和JP-8+100为军用汽轮机燃料,例如由海军和空军使用。这些标准中的一些表示已经包含其他添加剂,例如缓蚀剂、防冻剂、其他抗静电剂如静电耗散剂等的配制剂。
本发明的添加剂配制剂可以与其他本身已知的添加剂结合加入汽轮机燃料或汽轮机燃料组合物中。可以存在于汽轮机燃料组合物中的合适添加剂通常包括去垢剂,缓蚀剂,抗氧化剂如空间位阻叔丁基酚、N-丁基苯二胺或N,N’-二苯胺及其衍生物,金属减活剂如N,N’-二亚水杨基-1,2-二氨基丙烷,加溶剂,其他标准抗静电剂如450,生物杀伤剂,防冻剂如二甘醇甲基醚,以及所述添加剂的混合物。
优选用于汽轮机燃料或汽轮机燃料组合物的添加剂是下列具体化合物类别(E)、(F)和(G):
优选添加剂(E)是衍生于琥珀酸酐且具有通常含15-700个碳原子,尤其是30-200个碳原子的长链烃基的化合物。这些化合物可以具有优选选自羟基、氨基、酰胺基和/或酰亚胺基的其他官能团。优选的添加剂是聚链烯基琥珀酸酐的对应衍生物,其例如可以通过使聚链烯烃与马来酸酐通过热途径或经由氯化烃反应而得到。长链烃的数均分子量优选为约200-10000,更优选400-5000,特别是600-3000,尤其是650-2000。这些长链烃基优选衍生于常规聚异丁烯,尤其是上述反应性聚异丁烯。作为添加剂(E)特别令人感兴趣的是聚链烯基琥珀酸酐与氨、单胺、多胺、一元醇和多元醇的衍生物。对于衍生而言优选的多胺包括乙二胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺、丙二胺等。合适的醇包括一元醇如乙醇、烯丙醇、十二烷醇和苄醇,多元醇如乙二醇、二甘醇、丙二醇、1,2-丁二醇、新戊二醇、甘油、三羟甲基丙烷、赤藓醇、季戊四醇、甘露糖醇和山梨醇。
适合作为添加剂的琥珀酸酐衍生物(E)例如描述于US 3 522 179、US 4234 435、US 4 849 572、US 4 904 401、US 5 569 644和US 6 165 235中,它们全部作为参考引入本文。
优选的添加剂(F)是聚链烯基硫代膦酸酯。这些酯的聚链烯基优选具有的数均分子量为约300-5000,更优选400-2000,尤其是500-1500。如上面已经对于组分(E)作为长链烃基所述,聚链烯基优选衍生于聚烯烃。这些尤其是衍生于常规或反应性聚异丁烯的聚链烯基。通过使聚烯烃与硫代磷酰化试剂反应而制备合适聚链烯基硫代膦酸酯的合适方法例如描述于US 5725 611中,其作为参考引入本文。
优选的添加剂(G)是Mannich加合物。该类加合物原则上通过芳族羟基化合物,尤其是苯酚和苯酚衍生物,与醛和单胺或多胺的Mannich反应而得到。它们优选是聚异丁烯取代的酚与甲醛和单胺或多胺如乙二胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺、二甲氨基丙胺等的反应产物。合适的Mannich加合物及其制备方法例如描述于US 5 876 468、EP-A 831141、EP-A 1 233 990和EP-A 1 226 188中,它们全部作为参考引入本文。
用于汽轮机燃料或汽轮机燃料组合物的其他可能添加剂是WO2007/012580中所述的四氢苯并噁嗪稳定剂和/或国际专利申请PCT/EP2007/051632中所述的多环酚类稳定剂,它们全部作为参考引入本文。
上述添加剂(E)-(G)和任何其他添加剂通常各自可以基于汽轮机燃料组合物的总量在每种情况下以0.0001-1重量%,优选0.001-0.6重量%,尤其是0.0015-0.4重量%的量使用。
本发明的添加剂配制剂可以是汽轮机燃料(喷气燃料)用添加剂浓缩物的一部分,该浓缩物除了本发明添加剂配制剂外还包含至少一种稀释剂和至少一种优选选自上述那些的其他添加剂。该添加剂浓缩物以及因此还有添加了该浓缩物的汽轮机燃料组合物优选包含一种或多种来自(E)、(F)和(G)组的添加剂,尤其还有其混合物如(E)+(F)、(E)+(G)、(F)+(G)和(E)+(F)+(G)。
本发明的添加剂配制剂在所述汽轮机燃料用添加剂浓缩物中优选基于浓缩物总重量以0.01-70重量%,更优选0.05-25重量%,尤其是0.1-5重量%的量存在。
所述本发明添加剂配制剂还有利地适合航空汽油、汽油燃料和矿物馏出燃料及这里尤其是柴油机燃料和燃料油的抗静电改性和导电性改善。
航空汽油是尤其对航空发动机,尤其是螺旋桨式飞行器用汽油机开发的燃料,其类似于用于操作陆路交通工具的市售汽油燃料。
有用的汽油燃料包括所有市售汽油燃料组合物。这里应提到的典型代表是根据EN 228的Eurosuper基础燃料,其在市场上常见。此外,具有根据WO 00/47698的规格的汽油燃料组合物也是本发明的可能应用领域。所述汽油燃料还可以进一步包含生物乙醇。
有用的中间馏出燃料包括所有市售柴油机燃料和燃料油组合物。这里应提到的典型代表是根据EN 590的欧洲柴油机燃料,其在市场上常见。柴油机燃料通常为矿物油萃余液,其沸程通常为100-400℃。这些通常为95%高达360℃或甚至更高的馏出物。它们还可以是所谓的“超低硫柴油”或“城市柴油”,其特征在于95%例如不超过345℃且硫含量不超过0.005重量%,或95%例如为285℃且硫含量不超过0.001重量%。除了可以通过精炼得到的其主要成分为相对长链石蜡的柴油机燃料外,合适的柴油机燃料是可以通过煤气化得到的那些[“煤变油”(CTL)燃料]或通过气体液化得到的那些[“气变油”(GTL)燃料]。还合适的是上述柴油机燃料与可再生燃料如生物柴油的混合物。还合适的是由生物质得到的柴油机燃料[“生物质变油”(BTL)燃料]。现在特别令人感兴趣的是具有低硫含量,即小于0.05重量%,优选小于0.02重量%,特别是小于0.005重量%,尤其小于0.001重量%的硫含量的柴油机燃料。柴油机燃料还可以例如以至多20重量%的量包含水,例如以柴油-水微乳液或所谓的“无铅柴油(white diesel)”形式。
燃料油例如为低硫或富硫矿物油萃余液或沥青质煤馏出物或棕色煤馏出物,其沸程通常为150-400℃。燃料油可以是根据DIN 51603-1的标准燃料油,其硫含量为0.005-0.2重量%,或者它们是硫含量为0-0.005重量%的低硫燃料油。燃料油的实例尤其包括用于家用燃油锅炉的燃料油或EL燃料油。
本发明的添加剂配制剂可单独或以燃料添加剂包装如所谓的汽油或柴油操作包装形式加入特定基础燃料,尤其是汽油燃料或柴油机燃料中。该类包装为燃料添加剂浓缩物并且除了溶剂外通常还包含一系列其他组分作为辅助添加剂,例如载体油、冷流改进剂、缓蚀剂、破乳剂、去雾剂、消泡剂、十六烷值改进剂、燃烧改进剂、抗氧化剂或稳定剂、其他抗静电剂、茂金属、金属减活剂、加溶剂、标记剂和/或染料。
在优选实施方案中,加有添加剂的汽油或柴油机燃料除了本发明添加剂配制剂外还包含至少一种下文称为组分(H)的去垢剂作为其他燃料添加剂。
去垢剂或去垢剂添加剂(H)通常指燃料用沉积抑制剂。去垢剂优选为具有至少一个数均分子量(Mn)为85-20000,尤其是300-5000,特别是500-2500的疏水性烃基且具有至少一个选自如下的极性结构部分的两亲性物质:
(Ha)具有至多6个氮原子的单氨基或多氨基,其中至少一个氮原子呈碱性;
(Hb)硝基,合适的话与羟基结合;
(Hc)与单氨基或多氨基结合的羟基,其中至少一个氮原子呈碱性;
(Hd)羧基或其碱金属或碱土金属盐;
(He)磺酸基团或其碱金属或碱土金属盐;
(Hf)由羟基、单氨基或多氨基(其中至少一个氮原子呈碱性)或氨基甲酸盐基团封端的聚氧基-C2-C4亚烷基结构部分;
(Hg)羧酸酯基团;
(Hh)衍生于琥珀酸酐且具有羟基和/或氨基和/或酰胺基和/或酰亚胺基的结构部分;和/或
(Hi)通过取代酚与醛和单胺或多胺的Mannich反应得到的结构部分。
在上述去垢剂添加剂中的疏水性烃基确保在燃料油组合物中的足够溶解性,其数均分子量(Mn)为85-20000,尤其是300-5000,特别是500-2500。典型的疏水性烃基,尤其是与极性结构部分(Ha)、(Hc)、(Hh)和(Hi)结合,包括较长链的烷基或链烯基,尤其是聚丙烯基、聚丁烯基和聚异丁烯基,各自的Mn为300-5000,尤其是500-2500,特别是700-2300。
上组的去垢剂添加剂实例包括下列:
包含单氨基或多氨基(Ha)的添加剂优选为基于Mn为300-5000的聚丙烯或常规(即主要具有内双键)聚丁烯或聚异丁烯的聚亚烷基单胺或聚亚烷基多胺。该类基于高反应性聚异丁烯的添加剂可以由可包含至多20重量%正丁烯单元的聚异丁烯通过加氢甲酰化和用氨、单胺或多胺如3-(N,N-二甲氨基)丙胺、乙二胺、二亚乙基三胺、三亚乙基四胺或四亚乙基五胺还原性胺化而制备,尤其公开于EP-A 244 616中。当将主要具有内双键(通常在β-和γ-位)的聚丁烯或聚异丁烯在添加剂的制备中用作原料时,可能的制备途径是通过氯化和随后胺化或通过用空气或臭氧氧化双键得到羰基或羧基化合物和随后在还原(氢化)条件下胺化。这里用于胺化的胺例如可以是氨,单胺或多胺如二甲氨基丙胺、乙二胺、二亚乙基三胺、三亚乙基四胺或四亚乙基五胺。对应的基于聚丙烯的添加剂尤其描述于WO-A-94/24231中。
包含单氨基(Ha)的其他优选添加剂是平均聚合度P为5-100的聚异丁烯与氮氧化物或氮氧化物和氧气的混合物的反应产物的氢化产物,尤其如WO-A-97/03946所述。
包含单氨基(Ha)的其他优选添加剂是可以通过与胺反应和随后将氨基醇脱氢并还原而由聚异丁烯环氧化物得到的化合物,尤其如DE-A-196 20 262所述。
包含合适的话与羟基结合的硝基(Hb)的添加剂优选为平均聚合度P为5-100或10-100的聚异丁烯与氮氧化物或氮氧化物和氧气的混合物的反应产物,尤其如WO-A-96/03367和WO-A-96/03479所述。这些反应产物通常为纯硝基聚异丁烯(例如α,β-二硝基聚异丁烯)和混合羟基硝基聚异丁烯(例如α-硝基-β-羟基聚异丁烯)的混合物。
包含与单氨基或多氨基结合的羟基(Hc)的添加剂尤其为可以由优选主要具有端双键且Mn为300-5000的聚异丁烯得到的聚异丁烯环氧化物与氨或单胺或多胺的反应产物,尤其如EP-A 476 485所述。
包含羧基或其碱金属或碱土金属盐(Hd)的添加剂优选为C2-C40烯烃与马来酸酐的共聚物,其总摩尔质量为500-20000且其羧基已经部分或全部转化成碱金属或碱土金属盐并且任何剩余的羧基已经与醇或胺反应。这类添加剂尤其由EP-A-307 815公开。这类添加剂主要用于防止阀座磨损并且可以如WO-A-87/01126所述有利地与常规燃料去垢剂如聚(异)丁烯胺或聚醚胺结合使用。
包含磺酸基团或其碱金属或碱土金属盐(He)的添加剂优选为磺基琥珀酸烷基酯的碱金属或碱土金属盐,尤其如EP-A-639 632所述。该类添加剂主要用于防止阀座磨损并且可以有利地与常规燃料去垢剂如聚(异)丁烯胺或聚醚胺结合使用。
包含聚氧基-C2-C4亚烷基结构部分(Hf)的添加剂优选为可以通过使C2-C60链烷醇、C6-C30链烷二醇、单-或二-C2-C30烷基胺、C1-C30烷基环己醇或C1-C30烷基酚与每个羟基或氨基为1-30mol的氧化乙烯和/或氧化丙烯和/或氧化丁烯反应并且在聚醚胺的情况下随后用氨、单胺或多胺还原性胺化而得到的聚醚或聚醚胺。这类产物尤其如EP-A-310 875、EP-A-356 725、EP-A-700 985和US-A-4 877 416所述。在聚醚的情况下,该类产物还具有载体油性能。这些的典型实例是十三烷醇丁氧基化物、异十三烷醇丁氧基化物、异壬基酚丁氧基化物和聚异丁烯醇丁氧基化物和丙氧基化物以及与氨的对应反应产物。
包含羧酸酯基团(Hg)的添加剂优选为单-、二-或三羧酸与长链链烷醇或多元醇的酯,尤其是在100℃下的最小粘度为2mm2/s的那些,尤其如DE-A-38 38 918所述。所用单-、二-或三羧酸可以是脂族或芳族酸,并且特别合适的酯醇或酯多元醇是具有例如6-24个碳原子的长链代表。酯的典型代表是异辛醇、异壬醇、异癸醇和异十三烷醇的己二酸酯、邻苯二甲酸酯、间苯二甲酸酯、对苯二甲酸酯和偏苯三酸酯。这类产物也具有载体油性能。
包含衍生于琥珀酸酐且具有羟基和/或氨基和/或酰胺基和/或酰亚胺基的结构部分(Hh)的添加剂优选为烷基-或链烯基取代的琥珀酸酐的对应衍生物,尤其是可以通过使Mn为300-5000的常规或高反应性聚异丁烯与马来酸酐通过热途径或经由氯化聚异丁烯反应而得到的聚异丁烯基琥珀酸酐的对应衍生物。特别令人感兴趣的是与脂族多胺如乙二胺、二亚乙基三胺、三亚乙基四胺或四亚乙基五胺的衍生物。具有羟基和/或氨基和/或酰胺基和/或酰亚胺基的结构部分例如为羧酸基团、单胺的酰胺、除了酰胺官能团外还具有游离胺基团的二胺或多胺的酰胺、具有酸和酰胺官能团的琥珀酸衍生物、与单胺的羧酰亚胺、除了酰亚胺官能团外还具有游离胺基团的与二胺或多胺的羧酰亚胺或通过二胺或多胺与两种琥珀酸衍生物反应而形成的二酰亚胺。该类燃料添加剂尤其如US-A-4 849 572所述。
(Hh)组的去垢剂添加剂优选为烷基-或链烯基取代的琥珀酸酐,尤其是聚异丁烯基琥珀酸酐与胺和/或醇的反应产物。这些因此是衍生于烷基-、链烯基-或聚异丁烯基琥珀酸酐且具有氨基和/或酰胺基和/或酰亚胺基和/或羟基的衍生物。应理解的是这些反应产物不仅可以在使用取代琥珀酸酐时得到,而且可以在使用取代琥珀酸或合适的酸衍生物如琥珀酰卤或琥珀酸酯时得到。
当加有添加剂的燃料包含基于聚异丁烯基取代的琥珀酰亚胺的去垢剂时,与脂族多胺的酰亚胺尤其令人感兴趣。特别优选的多胺是乙二胺、二亚乙基三胺、三亚乙基四胺、五亚乙基六胺和尤其是四亚乙五胺。聚异丁烯基的数均分子量Mn优选为500-5000,更优选500-2000,尤其为约1000。
包含通过取代酚与醛和单胺或多胺的Mannich反应得到的结构部分(Hi)的添加剂优选为聚异丁烯取代的酚与甲醛和单胺或多胺如乙二胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺或二甲氨基丙胺的反应产物。聚异丁烯基取代的酚类可以来源于Mn为300-5000的常规或高度反应性聚异丁烯。该类“聚异丁烯-Mannich碱”尤其描述于EP-A-831 141中。
优选将所述去垢剂添加剂(H)和本发明添加剂配制剂一起与至少一种载体油结合使用。
合适的矿物载体油是原油加工中得到的馏分如重质高粘度润滑油料或粘度例如为SN 500-2000等级的基础油;还有芳烃、链烷烃和烷氧基链烷醇。同样有用的是在矿物油精炼中得到且已知为“加氢裂解油”的馏分(沸程为约360-500℃的真空馏出物,可以由已经在高压下催化氢化并且异构化和脱烷烃的天然矿物油得到)。同样合适的是上述矿物载体油的混合物。
合适的合成载体油的实例选自聚烯烃(聚-α-烯烃或聚(内烯烃))、(聚)酯、(聚)烷氧基化物、聚醚、脂族聚醚胺、烷基酚起始的聚醚、烷基酚起始的聚醚胺和长链链烷醇的羧酸酯。
合适聚烯烃的实例是Mn为400-1800的烯烃聚合物,尤其是基于聚丁烯或聚异丁烯(氢化或未氢化)的烯烃聚合物。
合适的聚醚或聚醚胺的实例优选为包含聚氧基-C2-C4亚烷基结构部分的化合物,其可以通过使C2-C60链烷醇、C6-C30链烷二醇、单-或二-C2-C30烷基胺、C1-C30烷基环己醇或C1-C30烷基酚与每个羟基或氨基为1-30mol的氧化乙烯和/或氧化丙烯和/或氧化丁烯反应并且在聚醚胺的情况下通过随后用氨、单胺或多胺还原性胺化而得到。该类产物尤其描述于EP-A-310875、EP-A-356 725、P-A-700 985和US-A-4,877,416中。例如,所用聚醚胺可以是聚-C2-C6氧化烯胺或其官能衍生物。其典型实例是十三烷醇丁氧基化物或异十三烷醇丁氧基化物、异壬基酚丁氧基化物以及聚异丁烯醇丁氧基化物和丙氧基化物,还有对应的与氨的反应产物。
长链链烷醇的羧酸酯实例尤其是单-、二-或三羧酸与长链链烷醇或多元醇的酯,尤其如DE-A-38 38 918所述。所用单-、二-或三羧酸可以是脂族或芳族酸;合适的酯醇或多元醇尤其是例如具有6-24个碳原子的长链代表。酯的典型代表是异辛醇、异壬醇、异癸醇和异十三烷醇的己二酸酯、邻苯二甲酸酯、间苯二甲酸酯、对苯二甲酸酯和偏苯三酸酯,例如邻苯二甲酸二(正-或异十三烷基)酯。
其他合适的载体油体系例如描述于DE-A-38 26 608、DE-A-41 42 241、DE-A-43 09 074、EP-A-0 452 328和EP-A-0 548 617中。
特别合适的合成载体油的实例是醇起始的聚醚,其具有约5-35,例如约5-30个C3-C6氧化烯单元,例如选自氧化丙烯、氧化正丁烯和氧化异丁烯单元,或其混合物。合适起始剂醇的非限制性实例是长链链烷醇或长链烷基取代的酚,其中长链烷基尤其是直链或支化C6-C18烷基。优选实例包括十三烷醇和壬基酚。
其他合适的合成载体油是烷氧基化烷基酚,如DE-A-101 02 913所述。
优选的载体油是合成载体油,特别优选聚醚。
去垢剂添加剂(H)或不同的该类去垢剂添加剂的混合物优选以10-2000重量ppm,更优选20-1000重量ppm,甚至更优选50-500重量ppm,尤其是50-200重量ppm,例如70-150重量ppm的总量加入加有添加剂的燃料中。
当额外使用载体油时,其优选以1-1000重量ppm,更优选10-500重量ppm,尤其是20-100重量ppm的量加入本发明的加有添加剂的燃料中。
适合作为其他辅助添加剂的冷流改进剂例如为乙烯与至少一种其他不饱和单体的共聚物,例如乙烯-乙酸乙烯酯共聚物。
适合作为其他辅助添加剂的缓蚀剂例如为琥珀酸酯,尤其是与多元醇的琥珀酸酯,脂肪酸衍生物,例如油酸酯,低聚脂肪酸和取代乙醇胺。
适合作为其他辅助添加剂的破乳剂例如为烷基取代的苯酚-和萘磺酸酯的碱金属和碱土金属盐以及脂肪酸的碱金属和碱土金属盐,还有醇烷氧基化物如醇乙氧基化物,酚烷氧基化物如叔丁基苯酚乙氧基化物或叔戊基苯酚乙氧基化物,脂肪酸,烷基酚,氧化乙烯和氧化丙烯的缩合产物如氧化乙烯-氧化丙烯嵌段共聚物,聚乙烯亚胺和聚硅氧烷。
适合作为其他辅助添加剂的去雾剂例如为烷氧基化苯酚-甲醛缩合物。
适合作为其他辅助添加剂的消泡剂例如为聚醚改性的聚硅氧烷。
适合作为其他辅助添加剂的十六烷值和燃烧改进剂例如为硝酸烷基酯,例如硝酸环己基酯,尤其是硝酸2-乙基己基酯,以及过氧化物,例如过氧化二叔丁基。
适合作为其他辅助添加剂的抗氧化剂例如为取代酚类,例如2,6-二叔丁基苯酚和2,6-二叔丁基-3-甲基苯酚,以及苯二胺如N,N’-二仲丁基对苯二胺。
适合作为其他辅助添加剂的金属减活剂例如为水杨酸衍生物,例如N,N’-二亚水杨基-1,2-丙二胺。
尤其对柴油添加剂包装合适的溶剂例如为非极性有机溶剂,尤其是芳族和脂族烃类,例如甲苯,二甲苯,“石油溶剂”以及名称(制造商:Royal Dutch/Shell Group)、(制造商:ExxonMobil)和溶剂石脑油的工业溶剂混合物。这里尤其在与所述非极性有机溶剂的共混物中还有用的是极性有机溶剂,尤其是醇类如2-乙基己醇、2-丙基庚醇、癸醇和异十三烷醇。
当在汽油燃料或柴油机燃料中额外使用所述辅助添加剂和/或溶剂时,它们以常规量使用。
此外,所述本发明的添加剂配制剂还以有利的方式适合润滑剂的抗静电改性和润滑性改善。润滑剂或润滑剂组合物在这里应指马达油、润滑油、液压油、汽轮机油、调节器油、包括手动和自动油在内的传动油、压延油、热载体油、金属加工油、减震油以及用于润滑机械移动部件-通常为金属的相关液体组合物。此外,润滑脂也应包括在润滑剂内。
经济上最重要的润滑剂组合物是马达油,以及包括手动和自动油在内的传动油。马达油通常由矿物基础油组成,其主要包含链烷成分且通过昂贵不便的后处理和提纯方法在炼油厂生产,含约2-10重量%添加剂(基于活性物质含量)。对于特定应用如高温应用,矿物基础油可以部分或全部被合成组分如有机酯,合成烃如烯烃低聚体、聚-α-烯烃或加氢裂解油的聚烯烃代替。马达油还应在高温下具有足够高的粘度以确保无瑕疵的润滑效果以及汽缸和活塞之间的良好密封。此外,马达油的流动性能必须使得发动机可以在低温下没有任何问题地启动。马达油必须是氧化稳定的且甚至在困难加工条件下必须仅产生少量液体或固体形式的分解产物和沉积物。马达油分散固体(分散剂性能)、防止沉积(去垢剂性能)、中和酸性反应产物并在发动机内的金属表面上形成磨损保护膜。马达油通常由粘度等级(SAE等级)表征。
对于其基础组分和添加剂,包括手动和自动油在内的传动油具有与马达油相类似的组成。在齿轮箱的齿轮系统中力很大程度上通过齿之间的传动油中的液体压力传递。因此,传动油必须能够长时间耐高压而不分解。除了粘度性能外,磨耗、耐压性、摩擦、剪切稳定性、牵引和运转性能在这里是重要参数。
除了在本发明上下文中要使用的本发明添加剂配制剂外,马达油以及包括手动和自动油在内的传动油通常还以常规量(在括号中以重量%表示,基于整个润滑剂组合物)包含至少一种下列添加剂,但通常是其中的一些或全部:
(a)抗氧化剂(0.1-5%):
硫化合物,例如萜烯(α-蒎烯)、树脂油或低分子量聚丁烯与硫、二烷基硫化物、二烷基三硫化物、多硫化物、二芳基硫化物、改性硫醇、巯基苯并咪唑、巯基三嗪、噻吩衍生物、黄原酸酯、二烷基二硫代氨基甲酸锌、硫代乙二醇、硫醛、二苄基二硫化物、烷基酚硫化物、二烷基酚硫化物或含硫羧酸的反应产物
磷化合物,例如亚磷酸三芳基和三烷基酯,3,5-二-叔丁基-4-羟基苄基膦酸二烷基酯或膦酸哌嗪化物
硫-磷化合物,例如二烷基二硫代磷酸锌(二烷基二硫代磷酸金属盐也在润滑油中用作缓蚀剂和高压添加剂)或五硫化磷与萜烯(α-蒎烯、二聚戊烯)、聚丁烯、烯烃或不饱和酯的反应产物
苯酚衍生物,例如空间位阻的单-、二-或三酚,空间位阻的多环酚,多烷基酚,2,6-二叔丁基-4-甲基苯酚或亚甲基-4,4’-二(2,6-二叔丁基苯酚)(苯酚衍生物通常与硫基或胺基抗氧化剂结合使用)
胺类,例如芳基胺如二苯胺、苯基-α-萘基胺或4,4’-四甲基二氨基二苯甲烷
较窄意义上的金属减活剂,例如N-亚水杨基乙胺、N,N’-二亚水杨基乙二胺、N,N’-二亚水杨基-1,2-丙二胺、三亚乙基二胺、乙二胺四乙酸、磷酸、柠檬酸、乙醇酸、卵磷脂、噻二唑、咪唑或吡唑衍生物
(b)粘度指数改进剂(00.05-10%),例如分子量通常为10000-45000的聚异丁烯,分子量通常为15000-100000的聚甲基丙烯酸酯,分子量通常为80000-100000的1,3-二烯如丁二烯或异戊二烯的均聚物和共聚物,分子量通常为80000-100000的1,3-二烯-苯乙烯共聚物,分子量通常为60000-120000的酯化形式的马来酸酐-苯乙烯聚合物,因由共轭二烯烃和芳族单体组成的单元而具有嵌段状结构的分子量通常为200000-500000的星形聚合物,分子量通常为80000-150000的聚烷基苯乙烯,由乙烯和丙烯组成的聚烯烃或分子量通常为60000-140000的苯乙烯-环戊二烯-降冰片烯三元共聚物
(c)倾点降低剂(冷流改进剂)(0.03-1%),例如双环芳烃如具有不同长链烷基的萘,在醇基中具有12-18个碳原子、支化度为10-30mol%且平均分子量为5000-500000的聚甲基丙烯酸酯,长链烷基酚和邻苯二甲酸二烷基芳基酯或不同烯烃的共聚物
(d)去垢剂(HD添加剂)(0.2-4%),例如环烷酸钙、环烷酸铅、环烷酸锌和环烷酸锰,二氯硬脂酸钙,苯基硬脂酸钙,氯苯基硬脂酸钙,烷基芳烃如十二烷基苯的磺化产物,石油磺酸盐,磺酸钠,磺酸钙,磺酸钡或磺酸镁,中性、碱性和高碱性磺酸盐、酚盐和羧酸盐、水杨酸盐,烷基酚和烷基酚硫化物的金属盐,磷酸盐,硫代磷酸盐或链烯基膦酸衍生物
(e)无灰分散剂(0.5-10%),例如烷基酚、甲醛和多亚烷基多胺的Mannich缩合物,聚异丁烯基琥珀酸酐与多羟基化合物或多胺的反应产物,甲基丙烯酸烷基酯与甲基丙烯酸二乙氨基乙酯、N-乙烯基吡咯烷酮、N-乙烯基吡啶或甲基丙烯酸2-羟基乙基酯的共聚物或乙酸乙烯酯-富马酸酯共聚物
(f)高压添加剂(极端压力添加剂)(0.2-2.5%),例如氯含量为40-70重量%的氯化石蜡,氯化脂肪酸(尤其具有三氯甲基端基),亚磷酸氢二烷基酯,亚磷酸三芳基酯,磷酸芳基酯如磷酸三甲苯酯,磷酸二烷基酯,磷酸三烷基酯如磷酸三丁基酯,三烷基膦,二磷酸酯,硝基芳烃,环烷酸的氨基酚衍生物,氨基甲酸酯,二硫代氨基甲酸衍生物,取代的1,2,3-三唑,苯并三唑和烷基琥珀酸酐或烷基马来酸酐的混合物,1,2,4-噻二唑聚合物,吗啉代苯并噻二唑二硫化物,氯化烷基硫化物,硫化烯烃,硫化氯萘,氯化硫代碳酸烷基酯,有机硫化物和多硫化物如二(4-氯苄基)二硫化物和四氯二苯硫醚,三氯丙烯醛缩硫醛或尤其是二烷基二硫代磷酸锌(ZDDP)
(g)摩擦改性剂(0.05-1%),尤其是在摩擦表面通过吸附产生薄层的极性油溶性化合物,例如脂肪醇、脂肪酰胺、脂肪酸盐、脂肪酸烷基酯或脂肪酸甘油酯
(h)消泡剂添加剂(0.0001-0.2%),例如液态聚硅氧烷如聚二甲基硅氧烷或聚乙二醇醚和硫化物
(i)破乳剂(0.1-1%),例如碱金属和碱土金属盐形式的二壬基萘磺酸盐
(j)缓蚀剂(也称为金属减活剂)(0.01-2%),例如叔胺及其盐,亚氨基酯,酰胺肟,二氨基甲烷类,饱和或不饱和脂肪酸与链烷醇胺的衍生物,烷基胺,肌氨酸,咪唑啉,烷基苯并三唑,二巯基噻二唑衍生物,磷酸二芳基酯,硫代磷酸酯,正C8-C18烷基伯胺或环烷基胺与具有支化C5-C12烷基的磷酸二烷基酯的中性盐,中性或碱性碱土金属磺酸盐,环烷酸锌,单-和二烷基芳基磺酸盐,二壬基萘磺酸钡,羊毛脂,环烷酸的重金属盐,二羧酸,不饱和脂肪酸,羟基脂肪酸,脂肪酸酯,季戊四醇单油酸酯和脱水山梨醇单油酸酯,O-硬脂酰基链烷醇胺,聚异丁烯基琥珀酸衍生物或二烷基二硫代磷酸锌和二烷基二硫代氨基甲酸锌
(k)乳化剂(0.01-1%),例如长链不饱和天然羧酸、环烷酸、合成羧酸、磺酰胺、N-油基肌氨酸、链烷磺酰胺基乙酸、十二烷基苯磺酸盐、长链烷基化铵盐如二甲基十二烷基苄基氯化铵,咪唑鎓盐,烷基-、烷基芳基-、酰基-、烷基氨基-和酰基氨基聚乙二醇或长链酰化单-和二乙醇胺
(l)染料和荧光添加剂(0.001-0.2%)
(m)防腐剂(0.001-0.5%)
(n)臭味改进剂(0.001-0.2%)。
典型的即用马达油组合物以及包括手动和自动油在内的传动油、本发明范围内的组合物具有下列组成,关于添加剂的数据涉及活性物质含量且所有组分之和总是加起来为100重量%:
●80-99.3重量%,尤其是90-98重量%的马达基础油或包括手动和自动油在内的传动油、包括这些添加剂用溶剂和稀释剂级分在内的基质(矿物基础油和/或合成组分)
●0.01-2000重量ppm,优选0.1-1000重量ppm,特别是0.5-500重量ppm,尤其是1-350重量ppm的本发明添加剂配制剂
●0.2-4重量%,尤其是1.3-2.5重量%的(d)组去垢剂
●0.5-10重量%,尤其是1.3-6.5重量%的(e)组分散剂
●0.1-5重量%,尤其是0.4-2.0重量%的(a)组抗氧化剂和/或(f)组高压添加剂和/或(g)组摩擦改性剂
●0.05-10重量%,尤其是0.2-1.0重量%的(b)组粘度指数改进剂
●0-2重量%的(c)和(h)-(n)组其他添加剂。
其中可以使用本发明添加剂配制剂防止静电荷的化学或物理方法的一个实例是聚乙烯气相流化床方法。在该方法中,乙烯或乙烯与共聚单体如1-丁烯、1-己烯或1-辛烯的混合物配位聚合。所形成的聚乙烯的密度关键取决于掺入的共聚单体的量和类型。例如,高密度HDPE优先由没有共聚单体的乙烯得到,而低密度LLDPE在显著量上述共聚单体存在下得到。所用催化剂优选为二氧化硅负载的Ziegler或茂金属催化剂。在每种情况下,聚合在流化床中在低于聚乙烯的熔点的温度下进行,这就是固体产物颗粒在塔式流化床反应器的内壁上引起摩擦的原因。本发明添加剂配制剂用于在整个反应器体系中防止静电荷并因此对抗在反应器内壁上和换热器中的聚合物沉积物形成。
本发明还提供具有改进导电性的抗静电改性的无生命有机材料,其选自化妆品制剂、药物配制剂、照相记录材料、油漆和清漆、塑料、蜡、溶剂、矿物油产品和燃料并且包含0.01-2000重量ppm,优选0.1-1000重量ppm,特别是0.5-500重量ppm,尤其是1-350重量ppm的本发明添加剂配制剂。
与已知组合物相比,本发明添加剂配制剂允许无生命有机材料的导电性甚至更有效和持续增加,尤其是在矿物油产品和燃料中,特别是在汽轮机燃料、汽油燃料和柴油机燃料以及润滑剂中。在许多情况下,甚至在储存后的导电性保持在恒定的高水平,而使用对应的现有技术添加剂配制剂可以在储存过程中观察到明显降低。甚至使用几个重量ppm范围内的极小量,通常在燃料中实现至少50-100pS/m的导电率。
本发明的添加剂配制剂具有高热稳定性。它不含金属和卤素。它还具有高闪点,并且因此在用于无生命有机材料中之前在制备、运输和储存过程中安全,即可以没有爆炸和火灾危险地处理它。
本发明参考下列非限制性实施例详细说明。
实施例1:在25℃下制备1-癸烯-二氧化硫共聚物
首先向5L高压釜中加入在350g重质溶剂石脑油(150)中的1122g(7.90mol)1-癸烯和28g十二烷基硫醇。在10-20℃下引入950g(14.84mol)二氧化硫。然后将反应混合物调节到25℃并在该温度下在3小时内引入72g过新戊酸叔丁酯(浓度为75重量%)在700g重质溶剂石脑油中的溶液。然后将该混合物在20℃下再搅拌5小时。为了进行后处理,将高压釜减压并首先在标准压力下脱气,然后在减压(200-10毫巴)下脱气。得到2.4kg清澈粘稠聚合物溶液。转化率为95%(由1H NMR波谱基于在5.8ppm/4.9ppm处的残留烯烃的3个烯烃质子与在4.3-3.0ppm处的聚合物主链中的3个质子的积分比测定)。如此得到的1-癸烯-二氧化硫共聚物的数均分子量Mn为19600且多分散性PDI为3.2。
实施例2:在35℃下制备1-癸烯-二氧化硫共聚物
首先向5L高压釜中加入在350g重质溶剂石脑油(150)中的1122g(7.90mol)1-癸烯和28g十二烷基硫醇。在10-20℃下引入950g(14.84mol)二氧化硫。然后将反应混合物调节到35℃并在该温度下在2小时内引入72g过新戊酸叔丁酯(浓度为75重量%)在700g重质溶剂石脑油中的溶液。然后将该混合物在20℃下再搅拌4小时。为了进行后处理,将高压釜减压并首先在标准压力下脱气,然后在减压(200-10毫巴)下脱气。得到2.5kg清澈粘稠聚合物溶液。转化率为97%(由1H NMR波谱基于在5.8ppm/4.9ppm处的残留烯烃的3个烯烃质子与在4.3-3.0ppm处的聚合物主链中的3个质子的积分比测定)。如此得到的1-癸烯-二氧化硫共聚物的数均分子量Mn为13400且多分散性PDI为2.9。
实施例3:在33℃下制备1-癸烯-二氧化硫共聚物
首先向5L高压釜中加入在630g重质溶剂石脑油(150)中1122g(7.90mol)1-癸烯和28g十二烷基硫醇。在10-20℃下引入720g(11.25mol)二氧化硫。然后将反应混合物调节到33℃并在该温度下在2小时内引入88g过新戊酸叔丁基酯(浓度为75重量%)在420g重质溶剂石脑油中的溶液。然后将该混合物在20℃下再搅拌4小时。为了进行后处理,将高压釜减压并首先在标准压力下进行脱气,然后在减压(200-10毫巴)下脱气。得到2.5kg清澈粘稠聚合物溶液。转化率为92%(由1H NMR波谱基于在5.8ppm/4.9ppm处的残留烯烃的3个烯烃质子与在4.3-3.0ppm处的聚合物主链中的3个质子的积分比测定)。如此得到的1-癸烯-二氧化硫共聚物的数均分子量Mn为12500且多分散性PDI为2.5。
实施例4:由1-癸烯-二氧化硫共聚物、C20/24烯烃-马来酰亚胺共聚物、十二烷基苯磺酸和重质溶剂石脑油制备添加剂配制剂
在25-35℃下将1kg来自实施例2的1-癸烯-二氧化硫共聚物溶液(在重质溶剂石脑油中浓度为50重量%)[组分(A)]与另外1.1kg重质溶剂石脑油在搅拌下混合。然后在相同温度下在搅拌下加入160g十二烷基苯磺酸[组分(C)]并均匀混合。将该混合物在40-50℃下搅拌10分钟。然后在40-50℃的温度下加入1kg已经用动物脂肪-1,3-二氨基丙烷转化成酰亚胺且重均分子量Mw为2000-5000的C20/24烯烃-马来酸酐共聚物[组分(B)]在重质溶剂石脑油中的溶液(浓度为50重量%)并均匀混合。所得添加剂配制剂的组成为15.3重量%(A)、15.3重量%(B)、4.9重量%(C)和64.4重量%重质溶剂石脑油[组分(D)]。
实施例5:由1-癸烯-二氧化硫共聚物、C20/24烯烃-马来酰亚胺共聚物、十二烷基苯磺酸和重质溶剂石脑油制备添加剂配制剂
类似于实施例4中的配方将相同组分(A)、(B)、(C)和(D)以使得添加剂配制剂组成为21重量%(A)、18重量%(B)、7重量%(C)和54重量%(D)的比例混合。
实施例6:由1-癸烯-二氧化硫共聚物、C20/24烯烃-马来酰亚胺共聚物、十二烷基苯磺酸和重质溶剂石脑油制备添加剂配制剂
类似于实施例4中的配方将相同组分(A)、(B)、(C)和(D)以使得添加剂配制剂组成为14重量%(A)、13重量%(B)、5重量%(C)和68重量%(D)的比例混合。
实施例7(对比):由1-癸烯-二氧化硫共聚物、N-动物脂肪胺/1,3-二氨基丙烷-表氯醇反应产物、十二烷基苯磺酸和重质溶剂石脑油制备添加剂配制剂
制备四种组分的比例类似于实施例6的配方的配制剂,唯一的不同在于代替50重量%C20/24烯烃-马来酰亚胺共聚物溶液使用相同量的N-动物脂肪胺-1,3-二氨基丙烷和表氯醇的聚合缩合产物在芳烃混合物中的市售50重量%溶液-根据文献(1)的教导。
实施例8:测量添加剂配制剂的导电性
导电性的测量根据DIN标准51412-2(电场法)进行。为此,将浸渍测试池浸入待分析液体中。在相同的液体温度(具体为25℃)下各自在浸渍测试池的显示器上读取以pS/m表示的导电性值。待分析液体是市售石油、市售柴油机燃料、市售燃料油、市售汽轮机燃料和市售液压油,其中在每种情况下已经事先加入特定量的添加剂配制剂作为导电性改进剂。下列总结说明测量结果。
a)在市售石油中(剂量:在每种情况下为3mg/l):
实施例5的添加剂配制剂(本发明)给出890pS/m;
实施例6的添加剂配制剂(本发明)给出750pS/m;
实施例7的添加剂配制剂(对比)给出540pS/m;
市售抗静电剂配制剂(AF1)给出760pS/m;
b)在市售柴油机燃料中(剂量:在每种情况下为3mg/l):
实施例5的添加剂配制剂(本发明)给出670pS/m;
实施例6的添加剂配制剂(本发明)给出440pS/m;
市售抗静电剂配制剂(AF1)给出415pS/m;
c)在市售燃料油中(剂量:在每种情况下为3mg/l):
实施例5的添加剂配制剂(本发明)给出690pS/m;
实施例6的添加剂配制剂(本发明)给出520pS/m;
市售抗静电剂配制剂(AF1)给出505pS/m;
d)在市售汽轮机燃料中(剂量:在每种情况下为1、3或5mg/l):
实施例5的添加剂配制剂(本发明)在1mg/l下给出174pS/m,在3mg/l下给出750pS/m且在5mg/l下给出1275pS/m;在每种情况下储存4天后重复导电性测量,得到的值为230pS/m(在1mg/l下)、735pS/m(在3mg/l下)和1205pS/m(在5mg/l下);
市售抗静电剂配制剂(AF2)在1mg/l下给出205pS/m,在3mg/l下给出723pS/m且在5mg/l下给出1230pS/m;在每种情况下储存4天后重复导电性测量,得到的值为150pS/m(在1mg/l下)、677pS/m(在3mg/l下)和1034pS/m(在5mg/l下);
e)在市售液压油中(剂量:在每种情况下为130mg/l):
实施例5的添加剂配制剂(本发明)给出167pS/m;
市售抗静电剂配制剂(AF1)给出120pS/m。
对于用于在有机液体中改进导电性的市售抗静电剂配制剂(AF1和AF2),采用根据文献(1)的教导的组合物。
测试结果表明本发明添加剂配制剂至少等同于对应的现有技术添加剂配制剂-经验表明在约±10-20pS/m的测量精度内;然而,在大多数情况下,它们优于后者且提供了所需的显著更高的导电性,尤其是也与对比例7直接比较时。这对于本发明实施例6也适用,该实施例具有较高含量的溶剂(D),即被相对高度稀释,但提供了也由市售抗静电剂配制剂实现的足够高的导电性。在汽轮机燃料中的测量中,作为本发明添加剂配制剂的另一优点应注意的是汽轮机燃料的导电性甚至在一定储存时间之后在高水平上保持恒定,而不像市售抗静电剂配制剂处理的汽轮机燃料那样在所述储存时间之后导电性显著下降。
实施例9:检测添加剂配制剂的储存稳定性和闪点
在恒定的40℃下长期储存之后对于实施例5和6的本发明添加剂配制剂以及市售抗静电剂配制剂(AF1和AF2)的储存稳定性通过肉眼检查评价浑浊和沉淀的可能形成。在所有情况下,样品在储存3个月后没有浑浊或沉淀。所用样品的闪点事先根据EN ISO标准2719:2002(根据Pensky-Martens在封闭坩埚中测量)测定:在本发明样品的情况下,它们为62℃(实施例5)和63℃(实施例6),但对于市售抗静电剂配制剂显著更低,为21℃(AF1)和<20℃(AF2)。
Claims (18)
1.一种适合无生命有机材料的抗静电改性和导电性改善的添加剂配制剂,基本由如下组分组成:
(A)1-50重量%的烯烃-二氧化硫共聚物,
(B)1-50重量%的包含一个或多个碱性氮原子且具有至少一个具有至少4个碳原子的较长链线性或支化烃基或确保组分(B)在无生命有机材料中的溶解性的等价结构单元的化合物,
(C)0.1-30重量%的油溶性酸,和
(D)1-80重量%的由一种或多种分子类型组成的高沸点有机溶剂,其中这些分子类型的至少80重量%在标准压力下的沸点大于150℃,
其中所有组分的总和加起来为100重量%。
2.根据权利要求1的添加剂配制剂,基本由如下组分组成:
(A)10-30重量%的组分(A),
(B)10-30重量%的组分(B),
(C)2-15重量%的组分(C),和
(D)40-78重量%的组分(D)。
3.根据权利要求1或2的添加剂配制剂,其中组分(A)为二氧化硫与一种或多种具有2-24个碳原子的线性或支化1-烯烃的共聚物。
4.根据权利要求1-3中任一项的添加剂配制剂,其中组分(A)的数均分子量Mn为2000-1000000。
5.根据权利要求1-4中任一项的添加剂配制剂,其中组分(A)包含小于15mol%的未在与二氧化硫的共聚中转化的烯烃。
6.根据权利要求1-5中任一项的添加剂配制剂,其中组分(B)为具有至少一个碱性氮原子的α-烯烃-马来酰亚胺共聚物。
7.根据权利要求6的添加剂配制剂,其中组分(B)通过一种或多种具有6-50个碳原子的线性或支化α-烯烃与马来酸酐自由基聚合并随后与一种或多种脂族多胺反应而得到。
8.根据权利要求6或7的添加剂配制剂,其中组分(B)的重均分子量Mw为500-50000。
9.根据权利要求1-8中任一项的添加剂配制剂,其中组分(C)为具有含6-40个碳原子的烃基的有机磺酸。
10.根据权利要求1-9中任一项的添加剂配制剂,其中组分(D)由至少80重量%的具有9-30个碳原子的高沸点芳烃或该类高沸点芳烃的混合物组成。
11.根据权利要求10的添加剂配制剂,其中组分(D)为具有9-20个碳原子的高沸点芳烃的混合物。
12.一种制备根据权利要求1-11中任一项的添加剂配制剂的方法,包括首先在至少部分高沸点有机溶剂(D)存在下将组分(A)和(C)相互均匀混合,然后掺入组分(B)。
13.根据权利要求1-11中任一项的添加剂配制剂在无生命有机材料的抗静电改性和导电性改善以及在化学和物理方法过程中防止静电荷的用途。
14.根据权利要求13的用途,用于化妆品制剂、药物配制剂、照相记录材料、油漆和清漆、塑料、蜡、溶剂、矿物油产品和燃料的抗静电改性和导电性改善。
15.具有改进导电性的抗静电改性的无生命有机材料,选自化妆品制剂、药物配制剂、照相记录材料、油漆和清漆、塑料、蜡、溶剂、矿物油产品和燃料,包含0.01-2000重量ppm根据权利要求1-11中任一项的添加剂配制剂。
16.一种制备包含小于15mol%的未在与二氧化硫的共聚中转化的烯烃的烯烃-二氧化硫共聚物的方法,包括以至少1.4倍摩尔过量使用二氧化硫并在由一种或多种分子类型组成的高沸点惰性有机溶剂中进行聚合,其中这些分子类型中至少50重量%具有8个以上碳原子。
17.一种制备包含小于15mol%的未在与二氧化硫的共聚中转化的烯烃的烯烃-二氧化硫共聚物的方法,包括以至少1.1倍摩尔过量使用二氧化硫并在自生压力和15-38℃,尤其是20-30℃下进行聚合。
18.根据权利要求17的制备烯烃-二氧化硫共聚物的方法,其中聚合在第一步中在0.5-5小时内在30-38℃和自生压力下进行,然后在第二步中在1-5小时内在20-29℃和自生压力下进行。
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2008
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- 2008-02-28 AT AT08717233T patent/ATE490299T1/de active
- 2008-02-28 PL PL08717233T patent/PL2132284T3/pl unknown
- 2008-02-28 RU RU2009136262/05A patent/RU2462504C2/ru active
- 2008-02-28 SG SG2012015145A patent/SG179434A1/en unknown
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- 2008-02-28 DK DK08717233.4T patent/DK2132284T3/da active
- 2008-02-28 CN CN2008800068897A patent/CN101622329B/zh active Active
- 2008-02-28 ES ES08717233T patent/ES2356029T3/es active Active
- 2008-02-28 PT PT08717233T patent/PT2132284E/pt unknown
- 2008-02-28 AU AU2008223857A patent/AU2008223857B2/en active Active
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109929158A (zh) * | 2019-02-20 | 2019-06-25 | 湖南铭弘体育产业股份有限公司 | 一种可提高跑道耐候性耐臭氧性的橡胶材料及其双重硫化工艺 |
Also Published As
Publication number | Publication date |
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ATE490299T1 (de) | 2010-12-15 |
KR101527238B1 (ko) | 2015-06-09 |
US20130296207A1 (en) | 2013-11-07 |
EP2132284B1 (de) | 2010-12-01 |
RU2462504C2 (ru) | 2012-09-27 |
WO2008107371A2 (de) | 2008-09-12 |
DE502008001942D1 (de) | 2011-01-13 |
MY150788A (en) | 2014-02-28 |
DK2132284T3 (da) | 2011-02-28 |
US20140318002A1 (en) | 2014-10-30 |
US8551365B2 (en) | 2013-10-08 |
CA2679490C (en) | 2016-02-09 |
EP2132284A2 (de) | 2009-12-16 |
SI2132284T1 (sl) | 2011-05-31 |
US10062471B2 (en) | 2018-08-28 |
ES2356029T3 (es) | 2011-04-04 |
CN101622329B (zh) | 2013-03-13 |
PL2132284T3 (pl) | 2011-05-31 |
PT2132284E (pt) | 2010-12-20 |
KR20090125808A (ko) | 2009-12-07 |
WO2008107371A3 (de) | 2008-12-11 |
SG179434A1 (en) | 2012-04-27 |
AR065574A1 (es) | 2009-06-17 |
US8858838B2 (en) | 2014-10-14 |
AU2008223857A1 (en) | 2008-09-12 |
JP2010520343A (ja) | 2010-06-10 |
RU2009136262A (ru) | 2011-04-10 |
JP5409396B2 (ja) | 2014-02-05 |
AU2008223857B2 (en) | 2012-04-12 |
CA2679490A1 (en) | 2008-09-12 |
US20100072427A1 (en) | 2010-03-25 |
BRPI0808388A2 (pt) | 2014-07-08 |
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