CN101528895A - 曼尼希化合物的季铵盐 - Google Patents
曼尼希化合物的季铵盐 Download PDFInfo
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- CN101528895A CN101528895A CNA2007800397917A CN200780039791A CN101528895A CN 101528895 A CN101528895 A CN 101528895A CN A2007800397917 A CNA2007800397917 A CN A2007800397917A CN 200780039791 A CN200780039791 A CN 200780039791A CN 101528895 A CN101528895 A CN 101528895A
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- agent
- amino
- uncle
- ammonium salt
- Prior art date
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
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- 108090000623 proteins and genes Proteins 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000992 solvent dye Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
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- 229920002994 synthetic fiber Polymers 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
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- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
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Abstract
由下列材料的反应的反应产物制成的季铵盐清净剂：(a)具有叔氨基的曼尼希反应产物，所述曼尼希反应产物由烃基取代酚、醛和胺的反应制备；和(b)适用于将叔氨基转化成季氮的季化剂；和这类季铵盐清净剂在燃料组合物中用于减少进气阀沉积物的用途。
Description
发明背景
本发明的组合物涉及季铵盐清净剂和这类季铵盐清净剂在燃料组合物中用于减少进气阀沉积物和除去或清除进气阀上的已有沉积物的用途；和该季铵盐在如油墨、涂料、研磨基料(mill-bases)、塑料和漆料之类的介质中的用途。对于本申请，术语清净剂和分散剂可互换使用并具有相同含义。
公知的是，液体燃料含有在发动机运行过程中可降解并形成沉积物的组分。这些沉积物会导致燃料的不完全燃烧以造成更高的排放和更差的燃料经济性。燃料添加剂，如清净剂，是液体燃料中的公知添加剂以助于控制或尽可能减少沉积物形成。随着发动机的动力学和力学的持续进步，对燃料的要求必须发展以跟上发动机进展。例如，现今的发动机包括具有较小公差并在较高压力下运行的喷射器系统以增强喷入压缩或燃烧室的燃料喷射。对于现今发动机的最佳运行，这些新型发动机中的沉积物预防和沉积物减少是至关重要的。燃料添加剂技术，如清净剂的进步能使燃料跟上这些发动机的进步。因此，需要能在液体燃料中提供可接受的性能以促进现今发动机的最佳运行的清净剂。
US 5,000,792公开了可通过使2份聚羟基羧酸与1份二亚烷基三胺反应而得的聚酯胺清净剂。
US 4,171,959公开了含有琥珀酰亚胺的季铵盐的发动机燃料组合物。该季铵盐具有抗衡离子，如卤素离子、磺酸根或羧酸根。
US 4,338,206和US 4,326,973公开了含有琥珀酰亚胺的季铵盐的燃料组合物，其中铵离子是杂环芳族的(吡啶鎓离子)。
US 4,108,858公开了含有用吡啶鎓盐处理的Mw为800至1400的C2至C4聚烯烃的燃料或润滑油组合物。
US 5,254,138公开了含有聚烷基琥珀酸酐与聚氨基羟烷基季铵盐的反应产物的燃料组合物。
US 4,056,531公开了含有键合到三亚乙基二胺上的Mw为350至3000的烃季铵盐的润滑油或燃料。该季铵盐的抗衡离子选自卤素离子、磷酸根、烷基磷酸根、二烷基磷酸根、硼酸根、烷基硼酸根、亚硝酸根、硝酸根、碳酸根、碳酸氢根、链烷酸根和O，O-二烷基二硫代磷酸根。
US 4,253,980和US 4,306,070公开了含有酯-内酯的季铵盐的燃料组合物。
US 3,778,371公开了含有Mw为350至3000的烃季铵盐的润滑油或燃料；且连接到季氮上的其余基团选自C1至C20烷基、C2至C8羟烷基、C2至C20链烯基或环状基团。
本发明因此通过降低、最小化和控制沉积物形成来促进最佳发动机运行，即提高的燃料经济性、更好的车辆操纵性能、降低的排放和更少的发动机维护。
许多配方，如油墨、漆料、研磨基料和塑料材料需要有效分散剂来将微粒固体均匀分布在有机介质中。有机介质可以从极性到非极性有机介质不等。含末端碱性基团，如聚(低碳亚烷基)亚胺链的分散剂是公知的并通常通过聚亚胺与含末端酸基的聚酯链的反应制备，该反应产生酰胺与盐形式的混合物。但是，这些分散剂中的许多在粘性和稳定性方面具有有限性能，其在掺入印刷油墨或漆料中时产生具有差流动特性的油墨和漆料。因此，需要能够提供可接受的流动特性并具有稳定性的分散剂。
US 5,721,358公开了使用由非盐化琥珀酰亚胺分散剂生成的分散剂制造铜酞菁的方法。该琥珀酰亚胺分散剂由亚烷基胺和聚异丁烯琥珀酸酐生成。
美国申请2003/0213410公开了包含带有至少一个羧基或其盐的聚合物和至少一种偶联剂的聚合物改性颜料。该聚合物包括已经与酰化剂如乙酸酐或琥珀酸酐反应的聚胺的衍生物。
GB 1,373,660公开了可通过聚羟基羧酸与二胺，尤其是亚烷基二胺及其盐的反应获得的聚酯胺分散剂。
因此，在掺入油墨、涂料、研磨基料、塑料和漆料中时赋予该油墨、涂料、研磨基料、塑料或漆料可接受的流动特性的具有可接受的性能的分散剂是有利的。
发明概述
本发明提供了包含季铵盐的组合物，该季铵盐包含下列材料的反应产物：
a.具有叔氨基的曼尼希反应产物，所述曼尼希反应产物由烃基取代酚、醛和胺的反应制备；和
b.适用于将叔氨基转化成季氮的季化剂。
本发明还提供了向内燃机供应燃料的方法，包括：
A.向所述发动机供应：
i.在室温下是液体的燃料；和
ii.包含下列材料的反应产物的季铵盐：
a.具有叔氨基的曼尼希反应产物，所述曼尼希反应产物由烃基取代酚、醛和胺的反应制备；和
b.适用于将叔氨基转化成季氮的季化剂。
本发明另外提供了润滑内燃机的方法，包括：
A.向所述发动机的曲轴箱供应：
i.润滑粘度的油；和
ii.包含下列材料的反应产物的季铵盐：
a.具有叔氨基的曼尼希反应产物，所述曼尼希反应产物由烃基取代酚、醛和胺的反应制备；和
b.适用于将叔氨基转化成季氮的季化剂。
本发明还提供了一种组合物，其包含：(i)微粒固体；(ii)有机介质；和(iii)包含下列材料的反应产物的季铵盐：
a.具有叔氨基的曼尼希反应产物，所述曼尼希反应产物由烃基取代酚、醛和胺的反应制备；和
b.适用于将叔氨基转化成季氮的季化剂。
本发明还提供了包含微粒固体、有机液体、粘结剂和季铵盐的漆料或油墨组合物，所述季铵盐包含下列材料的反应产物：
a.具有叔氨基的曼尼希反应产物，所述曼尼希反应产物由烃基取代酚、醛和胺的反应制备；和
b.适用于将叔氨基转化成季氮的季化剂。
本发明还提供了包含微粒固体、有机液体和季铵盐的研磨基料，该季铵盐包含下列材料的反应产物：
a.具有叔氨基的曼尼希反应产物，所述曼尼希反应产物由烃基取代酚、醛和胺的反应制备；和
b.适用于将叔氨基转化成季氮的季化剂。
发明详述
下面通过非限制性实例描述各种优选特征和实施方案。
发明领域
本发明涉及季铵盐、包括季铵盐的燃料组合物和用该燃料组合物运行内燃机的方法。本发明的组合物和方法最小化、降低和控制发动机中的沉积物形成，这降低了燃料消耗、有利于操纵性能、车辆维护和减少排放，这能够实现最佳发动机运行。
燃料
本发明的组合物可以包含在室温下是液体的燃料并可用于向发动机供应燃料。所述燃料通常在环境条件，例如室温(20至30℃)下是液体。燃料可以是烃燃料、非烃燃料、或其混合物。烃燃料可以是石油馏出物，包括如ASTM规格D4814所定义的汽油或如ASTM规格D975所定义的柴油燃料。在本发明的一个实施方案中，燃料是汽油，在另一些实施方案中，燃料是含铅汽油，或无铅汽油。在本发明的另一实施方案中，燃料是柴油。烃燃料可以是通过气至液法制成的烃，包括例如通过费托法之类的方法制成的烃。非烃燃料可以是含氧组合物，通常被称作含氧物(oxygenate)，包括醇、醚、酮、羧酸的酯、硝基链烷、或其混合物。非烃燃料可以包括，例如，甲醇、乙醇、甲基叔丁基醚、甲乙酮、酯交换油和/或来自植物和动物的脂肪，例如油菜籽甲酯和大豆甲酯，以及硝基甲烷。在本发明的若干实施方案中，燃料可以具有按重量计1重量％或10重量％或50重量％或最多85重量％的含氧物含量。烃和非烃燃料的混合物可以包括，例如，汽油和甲醇和/或乙醇、柴油燃料和乙醇、以及柴油燃料和酯交换植物油(如油菜籽甲酯)。在本发明的一个实施方案中，液体燃料可以是水在烃燃料、非烃燃料或其混合物中的乳液。在本发明的若干实施方案中，燃料可以具有按重量计5000ppm或更小，1000ppm或更小，300ppm或更小，200ppm或更小，30ppm或更小，或10ppm或更小的硫含量。在另一实施方案中，燃料可以具有按重量计1至100ppm的硫含量。在一个实施方案中，燃料含有0ppm至1000ppm，或0至500ppm，或0至100ppm，或0至50ppm，或0至25ppm，或0至10ppm，或0至5ppm的碱金属、碱土金属、过渡金属或其混合物。在另一实施方案中，燃料含有按重量计1至10ppm的碱金属、碱土金属、过渡金属或其混合物。本领域中公知的是，含有碱金属、碱土金属、过渡金属或其混合物的燃料具有更大的形成沉积物并因此弄脏或堵塞喷射器的趋势。本发明的燃料可以在燃料组合物中以通常大于50重量％的主要量存在，在另一些实施方案中以大于90重量％，大于95重量％，大于99.5重量％或大于99.8重量％的量存在。
季铵盐
本发明的组合物包含季铵盐，该季铵盐包含下列材料的反应产物：(a)具有叔氨基的曼尼希反应产物，所述曼尼希反应产物由烃基取代酚、醛和胺的反应制备；和(b)适用于将叔氨基转化成季氮的季化剂，其中季化剂选自硫酸二烷基酯、烷基卤、烃基取代的碳酸酯；与酸组合的烃基环氧化物或它们的混合物。
在下列专利中描述了季铵盐的实例及其制备方法，这些专利经此引用并入本文：US 4,253,980、US 3,778,371、US 4,171,959、US 4,326,973、US4,338,206和US 5,254,138。
曼尼希反应产物
本发明的曼尼希反应产物具有叔氨基并由烃基取代酚、醛和胺的反应产物制成。
烃基取代酚的烃基取代基可以具有10至400个碳原子，在另一情况下30至180个碳原子，在再一情况下10或40至110个碳原子。这种烃基取代基可以衍生自烯烃或聚烯烃。可用的烯烃包括α-烯烃，如1-癸烯，其可市购。
可以形成烃基取代基的聚烯烃可以通过以公知聚合方法使烯烃单体聚合来制备并且也可购得。烯烃单体包括单烯烃，包括具有2至10个碳原子的单烯烃，例如乙烯、丙烯、1-丁烯、异丁烯、和1-癸烯。尤其可用的单烯烃源是具有35至75重量％丁烯含量和30至60重量％异丁烯含量的C4炼油厂物流。可用的烯烃单体还包括二烯烃，如异戊二烯和1，3-丁二烯。烯烃单体也可以包括两种或更多单烯烃的混合物、两种或更多二烯烃的混合物、或一种或更多单烯烃与一种或更多二烯烃的混合物。可用的聚烯烃包括数均分子量为400至3000，在另一情况下为400至2500，在再一情况下为400或500至1500的聚异丁烯。聚异丁烯可以具有5至69％，在第二情况下50至69％，在第三情况下50至95％的亚乙烯基双键含量。聚烯烃可以是由单种烯烃单体制成的均聚物或由两种或更多烯烃单体的混合物制成的共聚物。同样可作为烃基取代基源的是两种或更多均聚物的混合物、两种或更多共聚物的混合物、或一种或更多均聚物与一种或更多共聚物的混合物。
烃基取代酚可以通过使用公知的烷基化方法用上述烯烃或聚烯烃，如聚异丁烯或聚丙烯将酚烷基化来制备。
用于形成曼尼希清净剂的醛可以具有1至10个碳原子，并通常是甲醛或其反应性等同物，如福尔马林或低聚甲醛。
用于形成曼尼希清净剂的胺可以是单胺或多胺。在任一情况下，它们以式R4R5NH为特征，其中R4和R5各自独立地为氢、烃、氨基取代的烃、羟基取代的烃、烷氧基取代的烃、或acylimidoyl(酰基亚氨基)，只要R4和R5中不超过一个是氢。因此，在所有情况下，它们的特征在于，在其结构内存在至少一个H-N＜基团。因此，它们具有至少一个伯氨基(即H2N-)或仲氨基(即H-N＜)。单胺的实例包括乙胺、二甲胺、二乙胺、正丁胺、二丁胺、烯丙基胺、异丁胺、椰油基胺、硬脂基胺、月桂基胺、甲基月桂基胺、油基胺、N-甲基-辛基胺、十二烷基胺、二乙醇胺、吗啉和十八烷基胺。
生成清净剂用的多胺主要包括大致符合下式的亚烷基胺
其中t是通常小于10的整数，A是氢或通常具有最多30个碳原子的烃基，亚烷基通常是具有少于8个碳原子的亚烷基。亚烷基胺主要包括亚乙基胺、亚己基胺、亚庚基胺、亚辛基胺、其它多亚甲基胺。它们的具体实例是：乙二胺、二亚乙基三胺、三亚乙基四胺、丙二胺、十亚甲基二胺、八亚甲基二胺、二(七亚甲基)三胺、三亚丙基四胺、四亚乙基五胺、三亚甲基二胺、五亚乙基六胺、二(-三亚甲基)三胺、氨基丙基吗啉和二甲基氨基丙基胺。通过使两种或更多上述亚烷基胺缩合而得的更高级同系物同样可用。四亚乙基五胺特别有用。
亚乙基胺，也称作多亚乙基多胺，尤其有用。它们在Encyclopedia ofChcmical Technology，Kirk和Othmer，第5卷，第898-905页，IntersciencePublishers，Nw York(1950)中的标题“Ethylene Amines”下详细描述。
在一个实施方案中，曼尼希清净剂可以通过如美国专利No.5,697,988中所述使烃基取代酚、醛和胺反应来制备。在一个实施方案中，曼尼希反应产物可以由源自聚异丁烯的烷基酚、甲醛和胺(其是伯单胺、仲单胺、或亚烷基二胺，特别是乙二胺或二甲胺)制成。
在另一实施方案中，本发明的曼尼希反应产物可以通过使烷基取代的羟基芳族化合物、醛和多胺通过公知方法，包括美国专利5,876,468中所述的方法反应来制备。
在再一实施方案中，曼尼希反应产物可以通过公知方法制备，该方法通常包括使烃基取代的羟基芳族化合物、醛和胺在50至200℃在溶剂或稀释剂存在下反应，同时除去反应水，如美国专利5,876,468中所述。
对于一些胺，可能必须进一步使曼尼希反应产物与环氧化物或碳酸酯或其它烷基化剂反应以得到叔氨基。
季化剂
本发明的组合物含有适用于将叔氨基转化成季氮的季化剂，其中该季化剂选自硫酸二烷基酯、烷基卤、烃基取代的碳酸酯；与酸组合的烃基环氧化物和它们的混合物。
在一个实施方案中，季化剂可以包括：卤化物，如氯化物、碘化物或溴化物；氢氧化物、磺酸酯；硫酸烷基酯，如硫酸二甲酯；磺内酯；磷酸酯；C1-12烷基磷酸酯；二C1-12烷基磷酸酯；硼酸酯；C1-12烷基硼酸酯；亚硝酸酯；硝酸酯；碳酸酯；碳酸氢酯；链烷酸酯；O，O-二C1-12烷基二硫代磷酸酯；或其混合物。
在一个实施方案中，季化剂可以衍生自硫酸二烷基酯，如硫酸二甲酯；N-氧化物；磺内酯，如丙磺酸内酯和丁磺酸内酯；烷基卤或芳基烷基卤，如甲基和乙基氯、溴或碘、或苄基氯；和烃基(或烷基)取代的碳酸酯。如果烷基卤是苄基氯，则芳环任选被烷基或烯基进一步取代。
烃基取代的碳酸酯的烃基(或烷基)可以每基团含有1至50，1至20，1至10，或1至5个碳原子。在一个实施方案中，烃基取代的碳酸酯含有两个可以相同或不同的烃基。合适的烃基取代的碳酸酯的实例包括碳酸二甲酯或碳酸二乙酯。
在另一实施方案中，季化剂可以是与酸组合的如下式所示的烃基环氧化物：
其中R1、R2、R3和Rs可以独立地为H或C1-50烃基。
烃基环氧化物的实例可以包括：氧化苯乙烯、环氧乙烷、环氧丙烷、环氧丁烷、氧化均二苯代乙烯和C2-50环氧化物。
流化剂
本发明的组合物可以另外含有流化剂。
在一个实施方案中，流化剂可以是聚醚胺，其可以表示为式R[OCH2CH(R1)]nA，其中R是烃基，R1选自氢、具有1至16个碳原子的烃基、及其混合物，n是2至大约50的数，且A选自-OCH2CH2CH2NR2R2和-NR3R3，其中各R2独立地为氢或烃基，且各R3独立地为氢、烃基或-[R4N(R5)]PR6，其中R4是C2-C10亚烷基，R5和R6独立地为氢或烃基，且p是1-7的数。这些聚醚胺可以通过先使醇或烷基酚与环氧烷、环氧烷混合物缩合或与几种环氧烷以相继方式缩合(其中含氢(hydric)化合物与环氧烷的摩尔比为1∶2-50)以形成聚醚中间体来制备。美国专利5,094,667提供了制备聚醚中间体的反应条件，其公开内容经此引用并入本文。在一个实施方案中，醇可以是直链或带支链的，具有1至30个碳原子，在另一实施方案中6至20个碳原子，在再一实施方案中10至16个碳原子。烷基酚的烷基可以具有1至30个碳原子，在另一实施方案中10至20个碳原子。环氧烷的实例包括环氧乙烷、环氧丙烷或环氧丁烷。聚醚中间体中环氧烷单元的数量可以为10-35或18-27。可以通过用氨、胺或聚胺胺化来将聚醚中间体转化成聚醚胺，从而形成其中A为-NR3R3的类型的聚醚胺。公开专利申请EP310875提供了胺化反应的反应条件，其公开内容经此引用并入本文。或者，也可以通过与丙烯腈反应然后氢化来将聚醚中间体转化成其中A为-OCH2CH2CH2NR2R2的类型的聚醚胺。美国专利5,094,667提供了氰基乙基化和随后氢化的反应条件，其公开内容经此引用并入本文。其中A为-OCH2CH2CH2NH2的聚醚胺通常是优选的。聚醚胺的商业实例是来自Chevron的系列和来自Huntsman的
系列。
在另一实施方案中，流化剂可以是聚醚，其可以表示为式R7O[CH2CH(R8)O ]qH，其中R7是烃基，R8选自氢、具有1至16个碳原子的烃基及其混合物，且q是2至大约50的数。上文在聚醚中间体的聚醚胺描述中阐述了聚醚的制备反应条件以及各种实施方案。聚醚的商业实例是Lyondell
系列。其它合适的聚醚也可获自Dow Chemicals，Huntsman和ICI。
在再一实施方案中，流化剂可以是如美国专利No.5,503,644中所述的烃基封端的聚(氧化烯)氨基氨基甲酸酯。
在再一实施方案中，流化剂可以是烷氧基化物，其中该烷氧基化物可以包含：(i)含有两个或更多酯端基的聚醚；或(ii)含有一个或更多酯基团和一个或更多醚端基的聚醚；或(iii)含有一个或更多酯基团和一个或更多氨基端基的聚醚，其中端基是指位于从聚合物末端起的五个连接碳或氧原子之内的基团。连接是指聚合物或端基中连接的碳和氧原子的总和。
烷氧基化物可以表示为下式：
其中R10是H、TC(O)-或C1-36烃基，其中T是在牛油脂肪酸或不含松香酸的脂肪酸中的C1-36脂肪酸烃基混合物；R20是H、A、WC(O)-或其混合物，其中A选自-OCH2CH2CH2NR2R2和-NR3R3，其中各R2独立地为氢或烃基，且各R3独立地为氢、烃基或-[R4N(R5)]PR6，其中R4是C2-C10亚烷基，R5和R6独立地为氢或烃基，且p是1-7的数，W是C1-36烃基；R1选自氢、具有1至16个碳原子的烃基；X是1至36的整数；Z是1至3的整数；Q可以是O或N；条件是如果Q是N，则d可以是0至2的整数，且Z是3-d的整数；如果Q是O，则d可以是整数0至1，且Z是整数2-d，且如果Q是O且R1是C1-36烃基，则R2是WC(O)-。
烷氧基化物的实例可以包括：C12-15醇引发的聚环氧丙烷(22-24)醚胺、Bayer ACTACLEAR ND21-ATM(C12-15醇引发的聚环氧丙烷(22-24)醚醇)、妥尔油脂肪酸引发的聚环氧丙烷(22-24)酯醇、丁醇引发的聚环氧丙烷(23-25)醚-牛油脂肪酸酯、二油酸甘油酯引发的聚环氧丙烷(23-25)醚醇、丙二醇引发的聚环氧丙烷(33-34)醚牛油脂肪酸酯、牛油脂肪酸引发的聚环氧丙烷(22-24)酯醇和C12-15醇引发的聚环氧丙烷(22-24)醚牛油脂肪酸酯。
这些烷氧基化物可以由脂肪酸，例如妥尔油脂肪酸(TOFA)(其是主要为油酸和亚油酸的脂肪酸混合物，并含有残留松香酸或牛油酸，即主要为硬脂酸、棕榈酸和油酸的脂肪酸混合物)与醇封端的聚醚(如聚丙二醇)在酸性催化剂，通常甲磺酸存在下的反应制成。这些烷氧基化物也可以由二油酸甘油酯和环氧丙烷在催化剂存在下的反应制成。
润滑粘度的油
本发明的组合物可以含有润滑粘度的油。润滑粘度的油包括润滑粘度的天然或合成油、由加氢裂化、氢化、加氢精制产生的油、未精制、精制和再精制的油、或其混合物。在一个实施方案中，润滑粘度的油是分散剂和/或其它性能添加剂的载液。
天然油包括动物油、植物油、矿物油、或其混合物。合成油包括烃油、基于硅的油、含磷的酸的液态酯。合成油可以通过费托反应制造且通常可以是加氢异构化的费托烃或蜡。
润滑粘度的油也可以如American Petroleum Institute(API)Base OilInterchangeability Guidelines中规定的那样进行定义。在一个实施方案中，润滑粘度的油包括API第I类、第II类、第III类、第IV类、第V类或其混合物，在另一实施方案中，包括API第I类、第II类、第III类或其混合物。
其他
组合物任选包含一种或多种另外的性能添加剂。性能添加剂可以包括：金属钝化剂、清净剂、分散剂、粘度改进剂、摩擦改进剂、分散剂粘度改进剂、特压剂、抗磨剂、抗氧化剂、缓蚀剂、泡沫抑制剂、破乳剂、倾点下降剂、密封溶胀剂、蜡控制聚合物、污垢抑制剂、气体-水合物抑制剂、及其混合物。
在无油基础上，所存在的另外的性能添加剂化合物的总量为组合物的0重量％至25重量％，或0.01重量％至20重量％。尽管可以存在一种或多种其它性能添加剂，但其它性能添加剂通常以彼此不同的量存在。
在一个实施方案中，组合物可以为形成浓缩物的量。如果本发明可以是浓缩物形式(其可以与另外的油合并以完全或部分形成最终润滑剂和/或液体燃料)，润滑粘度的油和/或液体燃料中的本发明的添加剂和/或其它另外的性能添加剂与稀释油的比率按重量计为80∶20至10∶90。
抗氧化剂包括二硫代氨基甲酸钼、硫化烯烃、受阻酚、二苯胺；清净剂包括碱金属、碱土金属和过渡金属与苯酚根、硫化苯酚根、磺酸根、羧酸、含磷酸、单-和/或二-硫代磷酸、水杨苷(saligenin)、烷基水杨酸根、salixarates中的一种或更多种的中性或高碱性、Newtonian或non-Newtonian碱性盐。
分散剂包括N-取代的长链链烯基琥珀酰亚胺以及其后处理形式，后处理的分散剂包括通过与脲、硫脲、二巯基噻二唑类、二硫化碳、醛、酮、羧酸、烃取代的琥珀酸酐、腈、环氧化物、硼化合物和磷化合物反应而得到的那些。
抗磨剂包括：金属硫代磷酸盐，尤其是二烷基二硫代磷酸锌；磷酸酯或其盐；亚磷酸酯；和含磷的羧酸酯、醚和酰胺。
抗划伤剂包括：有机硫化物和多硫化物，如苄基二硫化物、二(氯苄基)二硫化物、二丁基四硫化物、二叔丁基多硫化物、二叔丁基硫、硫化的狄尔斯-阿德耳加成物或二硫代氨基甲酸烷基亚磺酰基N’，N-二烷基酯。
特压(EP)剂包括：氯化蜡、有机硫化物和多硫化物，如苄基二硫化物、二(氯苄基)二硫化物、二丁基四硫化物、硫化的油酸甲酯、硫化的烷基酚、硫化二戊烯、硫化萜烯和硫化的狄尔斯-阿德耳加成物；磷硫化烃；和硫代氨基甲酸的金属盐，如二辛基二硫代氨基甲酸锌。
摩擦改进剂包括：脂肪胺；酯，如硼酸化甘油酯；甘油的部分酯，如单油酸甘油酯；脂肪亚磷酸酯；脂肪酸酰胺；脂肪环氧化物；硼酸化脂肪环氧化物；烷氧基化脂肪胺；硼酸化烷氧基化脂肪胺；脂肪酸的金属盐；脂肪咪唑啉；羧酸和多亚烷基多胺的缩合产物；和烷基磷酸的胺盐。
粘度改进剂包括：苯乙烯-丁二烯的氢化共聚物、乙烯-丙烯聚合物、聚异丁烯、氢化苯乙烯-异戊二烯聚合物、氢化异戊二烯聚合物、聚甲基丙烯酸酯、聚丙烯酸酯、聚烷基苯乙烯、链烯基芳基共轭二烯共聚物、聚烯烃、聚甲基丙烯酸烷基酯、和马来酸酐-苯乙烯共聚物的酯。
分散剂粘度改进剂(通常被称作DVM)包括：官能化聚烯烃，例如已经用马来酸酐与胺的反应产物官能化的乙烯-丙烯共聚物；用胺官能化的聚甲基丙烯酸酯；和与胺反应的苯乙烯-马来酸酐共聚物。
缓蚀剂包括：辛酸辛基胺；十二烯基琥珀酸或酐和脂肪酸(如油酸)与聚胺的缩合产物。
金属钝化剂包括：二巯基噻二唑、1，2，4-三唑、苯并咪唑、2-烷基二硫代苯并咪唑或2-烷基二硫代苯并噻唑的衍生物。
泡沫抑制剂包括丙烯酸乙酯和丙烯酸2-乙基己酯和任选乙酸乙烯酯的共聚物。
破乳剂包括聚乙二醇、聚环氧乙烷、聚环氧丙烷和(环氧乙烷-环氧丙烷)聚合物；倾点下降剂包括马来酸酐-苯乙烯的酯、聚甲基丙烯酸酯、聚丙烯酸酯或聚丙烯酰胺。
密封溶胀剂包括Exxon Necton-37TM(FN 1380)和Exxon Mineral SealOil。
工业应用
在一个实施方案中，本发明可用作内燃机的液体燃料。内燃机包括火花点火和压缩点火发动机；2-冲程或4-冲程；经由直接喷射、间接喷射、气口喷射和汽化器供应的液体燃料；共轨喷射和组合式喷射系统；轻型(例如客车)和重型(例如商用卡车)发动机；和以烃和非烃燃料及其混合物为燃料的发动机。发动机可以是综合排放系统的一部分，所述系统包括如下元件：EGR系统，后处理(包括三效催化剂、氧化催化剂、NOx吸收剂和催化剂)，任选使用燃料载催化剂的催化和未催化的微粒捕集器；可变气门正时、和喷油正时和速率形态(rate shaping)。
在另一实施方案中，本发明可用于涂料、油墨、研磨基料、塑料和漆料，尤其是高固含量漆料；油墨，尤其是胶版印刷、凹版印刷和丝网印刷油墨、可辐射固化油墨；非水陶瓷工艺，尤其是带涂、刮刀、挤塑和注塑型工艺；复合材料、化妆品、粘合剂和塑料材料。另外，本发明的组合物是用于将微粒固体均匀分布在有机介质中的有效分散剂。合适的微粒固体的实例是溶剂油墨的颜料；漆料和塑料用颜料、增量剂和填料；分散染料；用于溶剂染料浴、油墨和其它溶剂应用系统的荧光增白剂和织物助剂；用于油基和反相乳液钻探泥浆的固体；干洗液中的粉尘和固体粒子；微粒陶瓷材料；磁性材料和磁记录介质；复合材料用的纤维，如玻璃、钢、碳和硼；以在有机介质中的分散体形式施用的生物杀伤剂、农业化学品和药物。
在一个实施方案中，本发明提供了一种组合物，其包含：(i)微粒固体；(ii)有机介质；和(iii)包含下列材料的反应产物的季铵盐：
a.具有叔氨基的曼尼希反应产物，所述曼尼希反应产物由烃基取代酚、醛和胺的反应制备；和
b.适用于将叔氨基转化成季氮的季化剂。
在一个实施方案中，有机介质是有机液体或塑料材料。
在一个实施方案中，如权利要求1所述的组合物，其中有机液体包含基于有机液体总量为至少0.1重量％的极性有机液体。
在一个实施方案中，微粒固体是颜料。
在一个实施方案中，本发明提供了包含微粒固体、有机液体、粘结剂和季铵盐的漆料或油墨组合物，所述季铵盐包含下列材料的反应产物：
a.具有叔氨基的曼尼希反应产物，所述曼尼希反应产物由烃基取代酚、醛和胺的反应制备；和
b.适用于将叔氨基转化成季氮的季化剂。
粘结剂是能在有机液体挥发后粘结所述组合物的高分子材料。粘结剂是高分子材料，包括天然和合成材料。在一个实施方案中，粘结剂包括聚(甲基)丙烯酸酯类、聚苯乙烯类、聚酯类、聚氨酯类、醇酸树脂类、多糖类如纤维素，和天然蛋白质如酪蛋白。在一个实施方案中，粘结剂可以在组合物中基于微粒固体量为多于100％，多于200％，多于300％或多于400％的量存在。
在一个实施方案中，本发明提供了包含微粒固体、有机液体和季铵盐的研磨基料，所述季铵盐包含下列材料的反应产物：
a.具有叔氨基的曼尼希反应产物，所述曼尼希反应产物由烃基取代酚、醛和胺的反应制备；和
b.适用于将叔氨基转化成季氮的季化剂。
在一个实施方案中，固体是来自例如Colour Index第三版(1971)及其后继修订版和增刊中的标题为“颜料(pigments)”的章节中所述的任何公认颜料类型的有机颜料。有机颜料的实例是选自偶氮、双偶氮、缩合型偶氮、硫靛、阴丹酮、异吲哚啉酮颜料、三苯并[cd，jk]芘-5，10-二酮颜料、蒽醌、异二苯并蒽醌、三苯并二噁嗪(triphendioxazine)、喹吖啶酮和酞菁系列，尤其是铜酞菁及其环卤化衍生物，以及酸性、碱性和媒染料的色淀的那些。炭黑，尽管严格说来是无机的，但在其分散性能方面表现得更像有机颜料。在一个实施方案中，有机颜料是酞菁，尤其是铜酞菁、单偶氮、双偶氮、阴丹酮、三苯并[cd，jk]芘-5，10-二酮颜料、喹吖啶酮和炭黑。
无机固体包括：增量剂和填料，例如滑石、高岭土、硅石、重晶石和白垩；微粒陶瓷材料，例如氧化铝、硅石、氧化锆、二氧化钛、氮化硅、氮化硼、碳化硅、碳化硼、混合硅-铝氮化物和金属钛酸盐；微粒磁性材料，例如过渡金属，尤其是铁和铬的磁性氧化物，例如γ-Fe2O3、Fe3O4和掺钴氧化铁、氧化钙、铁氧体，尤其是钡铁氧体；和金属粒子，尤其是金属铁、镍、钴、铜及其合金。
在一个实施方案中，可以与本发明的反应产物和微粒固体的组合物一起存在的有机介质是塑料材料。在另一实施方案中有机介质可以是有机液体。有机液体可以是非极性或极性有机液体。在一个实施方案中，非极性有机液体是含脂族基团、芳族基团或其组合的化合物。非极性有机液体包括非卤化芳烃(例如甲苯和二甲苯)、卤化芳烃(例如氯苯、二氯苯、氯甲苯)、非卤化脂族烃(例如完全和部分饱和的含有6个或更多碳原子的直链和带支链脂族烃)、卤化脂族烃(例如二氯甲烷、四氯化碳、氯仿、三氯乙烷)和天然非极性有机物(例如植物油、葵花油、亚麻籽油、萜烯和甘油酯)。在一个实施方案中，热塑性树脂包括：聚烯烃类、聚酯类、聚酰胺类、聚碳酸酯类、聚氨酯类、聚苯乙烯类、聚(甲基)丙烯酸酯类、纤维素和纤维素衍生物。组合物可以以许多方式制备，但熔体混合和干固体掺合是典型方法。如果需要，组合物可以含有其它成分，例如树脂(在这些还没有构成有机介质的情况下)、粘结剂、流化剂、抗沉降剂、增塑剂、表面活性剂、防沫剂、流变改性剂、匀平剂、光泽改进剂和防腐剂。
分散体可以通过已知用于制备分散体的任何传统方法制备。因此，微粒固体、有机介质和分散剂可以以任意顺序混合，随后例如通过球磨、珠磨、卵石研磨或塑磨(plastic milling)对该混合物施以机械处理以将固体粒子降至适当的尺寸，直至形成分散体。或者，固体可以独立地或与有机介质或分散剂混合地处理以降低其粒度，随后添加其它成分并搅拌该混合物以提供组合物。
本发明的组合物特别适用于液体分散体。在一个实施方案中，这类分散体组合物包含：
(a)0.5至70份微粒固体；
(b)0.5至30份上述季铵盐的化合物；和
(c)20至99份有机液体；
其中所有份数均按重量计且量(a)+(b)+(c)＝100，且这类组合物可用作(液体)油墨、漆料和研磨基料。
本文所用的术语“烃基取代基”或“烃基”以本领域技术人员公知的其普通含义使用。具体地，其是指具有直接连接到分子其余部分上的碳原子并主要具有烃性质的基团。烃基的实例包括：烃取代基，即脂族(例如烷基或链烯基)、脂环族(例如环烷基、环烯基)取代基、和芳族-、脂族-和脂环族-取代的芳族取代基，以及环状取代基，其中环经由分子的另一部分完成(例如，两个取代基一起构成环)；取代烃取代基，即，含有在本发明中不改变所述取代基的主要烃性质的非烃基团的取代基(例如卤素(尤其是氯和氟)、羟基、烷氧基、巯基、烷基巯基、硝基、亚硝基和亚硫酰基)；杂取代基，在本发明中，即在具有主要烃性质的同时，在本来由碳原子构成的环或链中含有非碳的取代基。杂原子包括硫、氧、氮并包括取代基，如吡啶基、呋喃基、噻吩基和咪唑基。一般而言，相对于烃基中的每10个碳原子，存在不多于2个，优选不多于1个非烃取代基；通常，在烃基中没有非烃取代基。
已知的是，上述一些材料可以在最终制剂中相互作用，因此最终制剂的组分可能与一开始添加的不同。例如，金属离子(例如清净剂的金属离子)可迁移到其它分子的其它酸性或阴离子位点。由此形成的产物，包括本发明的组合物在其预计用途中使用时形成的产物可能不能简单描述。不过，所有这类改性和反应产物均包含在本发明的范围内；本发明包括通过混合上述组分制成的组合物。
实施例
通过下列实施例进一步阐述本发明，其列出了特别有利的实施方案。尽管提供了实施例以例证本发明，但它们不是要限制本发明。
在改性ASTM D5500行驶周期试验中评测本发明的清净剂。该试验中所用的车辆是带有1.8L 4循环发动机的BMWTM 318i汽车。燃料是与10％乙醇掺混的常规无铅subgrade 85辛烷。该组合物中包含聚醚基流化剂。进气阀是BMWTM进气阀，型号11-34-1-254-625。
试验中所用的清净剂包括：1000Mn聚异丁烯酚、甲醛和二甲胺的市售曼尼希反应产物(对比例1)和如下所述的本发明的实验清净剂(实施例1)。
制备例A：
制备例A由用1000Mn聚异丁烯制成的烷基化酚混合物(800克)制备并施加稀释油-SO-44(240克)，并在100rpm下搅拌该混合物。经50分钟向该混合物中(逐滴)加入福尔马林(55.9克)。此后，经过接下来的50分钟(逐滴)加入二甲胺(73.3克)。将整个混合物加热至68℃并在68℃下保持1小时。1小时后，将该混合物加热至106℃并再保持2小时。使该混合物的温度升至130℃并保持30分钟，此后冷却过夜。通过真空蒸馏(130℃，-0.9巴)提纯该混合物以除去任何残留水。所得化合物是DMA曼尼希。
实施例1
将制备例A的反应产物(1700克)、氧化苯乙烯(263克)、乙酸(66克)和甲醇(4564克)在氮气氛下在搅拌下加热至回流(～75℃)6.5小时。通过蒸馏(30℃，-0.8巴)提纯该反应。所得化合物为氧化苯乙烯季铵盐。
备注：对于对比例1，活性化学品与惰性稀释油相伴，活性化学品与稀释油的比率按重量计为大约75∶25。
备注：对于实施例1，活性化学品与惰性稀释油相伴，活性化学品与稀释油的比率按重量计为大约75∶25。
表1：ASTM D5500行驶周期试验中的结果
| 清净剂 | 剂量率活性物(PTB) | 毫克/阀 |
| 对比例1 | 12.5 | 55.0 |
| 对比例1 | 12.5 | 84.0 |
| 对比例1 | 25.0 | 18.7 |
| 实施例1 | 12.5 | 5.0 |
| 实施例1 | 12.5 | 48.0 |
| 实施例1 | 8.4 | 64.0 |
试验结果表明，本发明的使用季铵盐清净剂的制剂(实施例1)与市售清净剂(对比例1)相比表现出相当或更优异的进气阀喷射器沉积物形成的减少。
上文引用的各文献经此引用并入本文。除了在实施例中或除非另行明确指明，本说明书中规定材料量、反应条件、分子量、碳原子数和类似物的所有数量均被理解为用词语“大约”修饰。除非另行指明，本文提到的各化学品或组合物应该被解释为商业级材料，其可能含有异构体、副产物、衍生物和通常认为在商业级中存在的其它这类材料。但是，除非另行指明，排除商业材料中常规存在的任何溶剂或稀释油来表示各化学组分的量。要理解的是，本文所列的上限和下限量、范围和比率极限可以独立地结合。类似地，本发明的各元素的范围和量可以与任何其它元素的范围或量一起使用。本文所用的术语“基本由...构成”允许包括不会实质影响所述组合物的基本和新型特性的物质。
Claims (21)
1.包含季铵盐的组合物，该季铵盐包含下列材料的反应产物：
a.具有叔氨基的曼尼希反应产物，所述曼尼希反应产物由烃基取代酚、醛和胺的反应制备；和
b.适用于将叔氨基转化成季氮的季化剂。
2.权利要求1的组合物，其中季化剂选自硫酸二烷基酯、烷基卤、烃基取代的碳酸酯；与酸组合的烃基环氧化物；和它们的混合物。
3.权利要求1的组合物，其中组分(a)的烃基取代酚的烃基取代基是数均分子量为400至3000的聚烯烃。
4.权利要求1的组合物，其中组分(a)的醛是甲醛或其反应性等同物。
5.权利要求1的组合物，其中组分(a)的胺选自二甲胺、乙二胺、二甲基氨基丙基胺、二亚乙基三胺、二丁胺、及其混合物。
6.权利要求1的组合物，其中(a)的胺化合物是二甲胺。
7.权利要求1的组合物，还包含在室温下是液体的燃料。
8.权利要求1的组合物，还包含流化剂。
9.权利要求1的组合物，还包含润滑粘度的油。
10.权利要求9的组合物，还包含选自金属钝化剂、权利要求1的那些以外的清净剂、分散剂、粘度改进剂、摩擦改进剂、分散剂粘度改进剂、特压剂、抗磨剂、抗氧化剂、缓蚀剂、泡沫抑制剂、破乳剂、倾点下降剂、密封溶胀剂、蜡控制聚合物、污垢抑制剂、气体-水合物抑制剂、及其混合物的组分。
11.权利要求10的组合物，其中所述组分是高碱性的含金属清净剂、二烷基二硫代磷酸锌或其混合物。
12.向内燃机供应燃料的方法，包括：
A.向所述发动机供应：
i.在室温下是液体的燃料；和
ii.包含下列材料的反应产物的季铵盐：
a.具有叔氨基的曼尼希反应产物，所述曼尼希反应产物由烃基取代酚、醛和胺的反应制备；和
b.适用于将叔氨基转化成季氮的季化剂。
13.权利要求12的方法，其中季化剂选自硫酸二烷基酯；烷基卤；烃基取代的碳酸酯；与酸组合的烃基环氧化物；或它们的混合物。
14.润滑内燃机的方法，包括：
A.向所述发动机的曲轴箱供应：
i.润滑粘度的油；和
ii.包含下列材料的反应产物的季铵盐：
a.具有叔氨基的曼尼希反应产物，所述曼尼希反应产物由烃基取代酚、醛和胺的反应制备；和
b.适用于将叔氨基转化成季氮的季化剂。
15.权利要求14的方法，其中季化剂选自硫酸二烷基酯；烷基卤；烃基取代的碳酸酯；与酸组合的烃基环氧化物；和它们的混合物。
16.一种组合物，其包含：(i)微粒固体；(ii)有机介质；和(iii)包含下列材料的反应产物的季铵盐：
a.具有叔氨基的曼尼希反应产物，所述曼尼希反应产物由烃基取代酚、醛和胺的反应制备；和
b.适用于将叔氨基转化成季氮的季化剂。
17.权利要求16的组合物，其中有机介质是有机液体或塑料材料。
18.权利要求16的组合物，其中有机液体包含基于有机液体总量为至少0.1重量％的极性有机液体。
19.权利要求16的组合物，其中微粒固体是颜料。
20.包含微粒固体、有机液体、粘结剂和季铵盐的漆料或油墨组合物，所述季铵盐包含下列材料的反应产物：
a.具有叔氨基的曼尼希反应产物，所述曼尼希反应产物由烃基取代酚、醛和胺的反应制备；和
b.适用于将叔氨基转化成季氮的季化剂。
21.包含微粒固体、有机液体和季铵盐的研磨基料，所述季铵盐包含下列材料的反应产物：
a.具有叔氨基的曼尼希反应产物，所述曼尼希反应产物由烃基取代酚、醛和胺的反应制备；和
b.适用于将叔氨基转化成季氮的季化剂。
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| US11/469,690 US7906470B2 (en) | 2006-09-01 | 2006-09-01 | Quaternary ammonium salt of a Mannich compound |
| PCT/US2007/076978 WO2008027881A2 (en) | 2006-09-01 | 2007-08-28 | Quaternary ammonium salt of a mannich compound |
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| EP (2) | EP2076582A2 (zh) |
| JP (3) | JP2010502787A (zh) |
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2006
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2007
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- 2007-08-28 EP EP07841457A patent/EP2076582A2/en not_active Ceased
- 2007-08-28 JP JP2009526864A patent/JP2010502787A/ja active Pending
- 2007-08-28 CA CA002662310A patent/CA2662310A1/en not_active Abandoned
- 2007-08-28 CN CN2007800397917A patent/CN101528895B/zh not_active Expired - Fee Related
- 2007-08-28 EP EP12154759A patent/EP2457981A1/en not_active Withdrawn
-
2011
- 2011-01-31 US US13/017,066 patent/US8083814B2/en active Active
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2013
- 2013-01-24 JP JP2013010901A patent/JP5793517B2/ja not_active Expired - Fee Related
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2015
- 2015-08-10 JP JP2015158122A patent/JP2015214712A/ja active Pending
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103589413A (zh) * | 2012-08-13 | 2014-02-19 | 中国石油天然气股份有限公司 | 一种油井酸化缓蚀剂及其制备和应用 |
| CN103589413B (zh) * | 2012-08-13 | 2016-11-02 | 中国石油天然气股份有限公司 | 一种油井酸化缓蚀剂及其制备和应用 |
| CN103589479A (zh) * | 2012-08-17 | 2014-02-19 | 雅富顿化学公司 | 发动机油润滑剂的清净剂的钙中性和高碱性曼尼希和酐加合物 |
| CN103589479B (zh) * | 2012-08-17 | 2017-06-09 | 雅富顿化学公司 | 发动机油润滑剂的清净剂的钙中性和高碱性曼尼希和酐加合物 |
| CN104513686A (zh) * | 2013-10-08 | 2015-04-15 | 雅富顿化学公司 | 季铵清洁剂燃料添加剂 |
| CN106029845A (zh) * | 2014-02-24 | 2016-10-12 | 道达尔销售服务公司 | 添加剂组合物和包含该组合物的高性能燃料 |
| CN106029845B (zh) * | 2014-02-24 | 2018-12-14 | 道达尔销售服务公司 | 添加剂组合物和包含该组合物的高性能燃料 |
| CN113412283A (zh) * | 2018-12-10 | 2021-09-17 | 索理思科技开曼公司 | 用于反相乳液聚合过程的稳定剂 |
| CN113412283B (zh) * | 2018-12-10 | 2023-07-14 | 索理思科技开曼公司 | 用于反相乳液聚合过程的稳定剂 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008027881A3 (en) | 2008-05-29 |
| WO2008027881A2 (en) | 2008-03-06 |
| JP5793517B2 (ja) | 2015-10-14 |
| CN101528895B (zh) | 2013-07-31 |
| JP2013079284A (ja) | 2013-05-02 |
| US7906470B2 (en) | 2011-03-15 |
| EP2076582A2 (en) | 2009-07-08 |
| JP2015214712A (ja) | 2015-12-03 |
| CA2662310A1 (en) | 2008-03-06 |
| US20080052985A1 (en) | 2008-03-06 |
| US8083814B2 (en) | 2011-12-27 |
| EP2457981A1 (en) | 2012-05-30 |
| US20110130317A1 (en) | 2011-06-02 |
| JP2010502787A (ja) | 2010-01-28 |
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