CN103228769B - 烃基取代的二羧酸和氮化合物的反应产物在降低燃料消耗中的用途 - Google Patents
烃基取代的二羧酸和氮化合物的反应产物在降低燃料消耗中的用途 Download PDFInfo
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- CN103228769B CN103228769B CN201180057828.5A CN201180057828A CN103228769B CN 103228769 B CN103228769 B CN 103228769B CN 201180057828 A CN201180057828 A CN 201180057828A CN 103228769 B CN103228769 B CN 103228769B
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- 239000000446 fuel Substances 0.000 title claims abstract description 106
- 239000007795 chemical reaction product Substances 0.000 title claims abstract description 50
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 47
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 229910017464 nitrogen compound Inorganic materials 0.000 title claims abstract description 21
- 150000002830 nitrogen compounds Chemical class 0.000 title claims abstract description 21
- 239000000654 additive Substances 0.000 claims abstract description 58
- 230000000996 additive effect Effects 0.000 claims abstract description 52
- 150000008065 acid anhydrides Chemical class 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims description 31
- 239000003599 detergent Substances 0.000 claims description 24
- 239000003208 petroleum Substances 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 229920000768 polyamine Polymers 0.000 claims description 16
- 239000002199 base oil Substances 0.000 claims description 15
- 239000010687 lubricating oil Substances 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 238000002485 combustion reaction Methods 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 239000003112 inhibitor Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- OTXHZHQQWQTQMW-UHFFFAOYSA-N (diaminomethylideneamino)azanium;hydrogen carbonate Chemical class OC([O-])=O.N[NH2+]C(N)=N OTXHZHQQWQTQMW-UHFFFAOYSA-N 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 5
- 229910052728 basic metal Inorganic materials 0.000 claims description 5
- 150000003818 basic metals Chemical class 0.000 claims description 5
- 150000007942 carboxylates Chemical group 0.000 claims description 5
- 230000007797 corrosion Effects 0.000 claims description 5
- 238000005260 corrosion Methods 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 230000002269 spontaneous effect Effects 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- 125000005462 imide group Chemical group 0.000 claims 1
- -1 glycol ethers Chemical class 0.000 description 47
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
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- 229920000570 polyether Polymers 0.000 description 9
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 7
- 229940014800 succinic anhydride Drugs 0.000 description 7
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- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 5
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- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
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- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
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- 238000005406 washing Methods 0.000 description 4
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000005466 alkylenyl group Chemical group 0.000 description 3
- 238000005576 amination reaction Methods 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003495 polar organic solvent Substances 0.000 description 3
- 229920001083 polybutene Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- SZOLUXDHHKCYKT-ONEGZZNKSA-N (e)-but-1-en-1-amine Chemical compound CC\C=C\N SZOLUXDHHKCYKT-ONEGZZNKSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 2
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- 239000004593 Epoxy Substances 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 239000004440 Isodecyl alcohol Substances 0.000 description 2
- 239000004439 Isononyl alcohol Substances 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
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- 125000002877 alkyl aryl group Chemical group 0.000 description 2
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- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 2
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
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- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/226—Organic compounds containing nitrogen containing at least one nitrogen-to-nitrogen bond, e.g. azo compounds, azides, hydrazines
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- C10L1/00—Liquid carbonaceous fuels
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- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/224—Amides; Imides carboxylic acid amides, imides
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- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/228—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen double bond, e.g. guanidines, hydrazones, semicarbazones, imines; containing at least one carbon-to-nitrogen triple bond, e.g. nitriles
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- C10L1/234—Macromolecular compounds
- C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
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- C10L1/18—Organic compounds containing oxygen
- C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
- C10L1/1822—Organic compounds containing oxygen containing hydroxy groups; Salts thereof hydroxy group directly attached to (cyclo)aliphatic carbon atoms
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- C10L1/1985—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds homo- or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon to carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid polyethers, e.g. di- polygylcols and derivatives; ethers - esters
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Abstract
烃基取代的二羧酸或其酸酐和氮化合物I或其盐的反应产物在燃料中作为添加剂以降低内燃机中的燃料消耗的用途。
Description
本发明涉及由(a)其烃基具有8-250个碳原子的烃基取代的二羧酸或其酸酐和(b)通式I的氮化合物或氮化合物I的盐形成的反应产物在燃料中作为添加剂以在使用该燃料的火花点火式内燃机操作中降低燃料消耗或者在汽油燃料中作为添加剂以在使用该燃料的自点火式内燃机操作中降低燃料消耗的用途:
其中R1和R2各自独立地为氢或C1-C20烃基。
本发明进一步涉及一种燃料组合物,其包含汽油燃料、所述反应产物和至少一种具有去垢作用的燃料添加剂。
本发明进一步涉及一种添加剂浓缩物,其包含所述反应产物和至少一种具有去垢作用的燃料添加剂。
已知在燃料中的特定物质降低内燃机,尤其是汽油机中的内摩擦,并因此有助于节省燃料。该类物质也称为润滑性改进剂、减摩剂或摩擦改进剂。市场上常用于汽油燃料的润滑性改进剂通常为天然存在的羧酸如脂肪酸与多元醇如甘油或与链烷醇胺的缩合产物,例如甘油单油酸酯。
所述现有技术的润滑性改进剂的缺点是与其他常用燃料添加剂,尤其是去垢添加剂如聚异丁烯胺和/或载体油如聚氧化烯的不良溶混性。实践中的重要要求是所提供的组分混合物或添加剂浓缩物甚至在较低温度下,尤其是在例如低至-20℃的户外冬季温度下易于泵送且长时间内保持均匀稳定,即不出现相分离和/或沉淀物。
所示溶混性问题通常通过向组分混合物或添加剂浓缩物中加入较大量的烷属烃或芳族烃与醇如叔丁醇或2-乙基己醇的混合物作为加溶剂而避免。然而,在一些情况下需要显著量的这些昂贵加溶剂以实现所需均匀性,并且因此对该问题的这种解决方案变得不经济。
在WO2007/053787中推荐作为该类组分混合物或添加剂浓缩物的加溶剂的低分子量羧酸和羧酸衍生物、二醇醚和烷基化酚也因其原料成本高而不经济,并且除了它们作为加溶剂的功能外不具有任何其他正面效果。相反,它们隐藏了引起不利效果的风险,例如不希望的油稀释和燃烧室沉积物的形成增加。
此外,所述现有技术的润滑性改进剂通常具有与组分混合物或添加剂浓缩物中或燃料本身中的水形成乳液的倾向,从而仅能困难地或者至少仅非常缓慢地经由相分离再次除去已经渗透的水。
例如,EP-A1424322和WO03/070860中所述的润滑性改进剂—基于具有单-或多胺或链烷醇胺如丁基胺、二亚乙基三胺、四亚乙基五胺或氨基亚乙基乙醇胺的聚异丁烯基琥珀酰亚胺—与相应混合物或浓缩物中的其他添加剂组分呈现良好的溶混性,但具有与水形成稳定乳液的明显倾向,这可能导致将水和污垢颗粒夹带进燃料供应链中并且最终也可能进入发动机中的效果。水可能引起腐蚀;污垢颗粒可能导致燃料泵、燃料过滤器和喷油嘴受损。
本发明的目的是提供燃料添加剂,其首先在火花点火式内燃机操作中有效节省燃料,其次不再具有现有技术的所示缺点,即更具体为与其他燃料添加剂的不良溶混性和与水形成乳液的倾向。此外,它们不应使通过现代燃料添加剂实现的进气阀的高清洁度变差。
因此,已经发现了开头所定义的由(a)烃基取代的二羧酸或其酸酐与(b)通式I的氮化合物形成的反应产物的用途。可以假定通过所述反应产物引起燃料节省主要是基于其作为在内燃机中,尤其是在汽油机中降低内摩擦的添加剂的效果。所述反应产物因此在本发明上下文中主要用作润滑性改进剂。
由烃基取代的二羧酸或其酸酐和氨基胍或其盐形成的反应产物在美国公开说明书US2009/0282731A1和US2010/0037514A1中作为改善柴油机性能和在柴油机中清洁喷油嘴的添加剂描述。
英国专利GB998869和GB1020059公开了由聚异丁烯基琥珀酸酐和碳酸氢氨基胍形成的反应产物也适合在汽油燃料中作为去垢添加剂。
欧洲公开说明书EP0310367A1描述了由聚异丁烯基琥珀酸酐和碳酸氢氨基胍形成的反应产物在存在于马达油中时保护柴油机中的铜和铜合金。
火花点火式内燃机优选应理解为指通常由火花塞点火的汽油机。除了常规四冲程和二冲程汽油机外,火花点火式内燃机还包括其他发动机类型,例如Wankel发动机。这些通常为用常规汽油类型,尤其是根据EN228的汽油类型,汽油-酒精混合物如具有75-85体积%乙醇的Flex燃料,液压气(“LPG”)或压缩天然气(“CNG”)作为燃料操作的发动机。
然而,由(a)烃基取代的二羧酸或其酸酐与(b)通式I的氮化合物形成的反应产物的本发明用途还涉及新开发的内燃机如“HCCI”发动机,其为自点火的且用汽油燃料操作。
用于反应组分(a)的通式I的氮化合物是胍、取代胍或其盐。在这些化合物中的可能烃基包含1-20个,尤其是1-12个,特别是1-8个碳原子。烃基在这里应理解为指具有任何结构的烃基,但还可以少量包含杂原子如氧和/或氮原子和/或卤原子和/或带有官能基团如羟基、羧基、羧酸酯基团、氰基、硝基和/或磺基,条件是不因此改变该基团的显著烃性质。所述烃基在性质上可以是饱和或不饱和的;它可以具有线性或支化结构;它可以包含芳族和/或杂环亚结构。
氮化合物I可以具有两个对于R1和R2的该类烃基,或者仅具有一个对于R1和R2的该类烃基,在后一情况下另一取代基为氢。然而,优选两个取代基R1和R2为氢,即该化合物是未被取代的氨基胍。
对于R1和/或R2可能的烃基优选为线性或支化烷基或链烯基,尤其是具有1-8个,优选1-4个碳原子的那些,如甲基、乙基、乙烯基、正丙基、异丙基、1-丙烯基、2-丙烯基、正丁基、仲丁基、异丁基、叔丁基、戊基、新戊基、己基、庚基、辛基、2-乙基己基、新辛基、壬基、新壬基、异壬基、癸基、新癸基、2-丙基庚基、十一烷基、新十一烷基、十二烷基、十三烷基、异十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基(硬脂基)、油基、亚油基、亚麻基、十九烷基、二十烷基或其结构异构体。
此外,对于R1和/或R2可能的烃基还可以涉及环烷基,例如环戊基,环己基,2-、3-或4-甲基环己基或环庚基。
此外,对于R1和/或R2可能的烃基还可以是芳基、烷芳基或芳烷基,例如苯基、萘基、苄基、2-苯基乙基、3-苯基丙基、4-苯基丁基、甲苯基或邻-、间-或对二甲苯基。
当氮化合物I以其盐之一的形式使用时,这尤其为卤化物如氯化物或溴化物、碳酸盐、碳酸氢盐、硝酸盐或正磷酸盐。优选使用碳酸氢盐。
在优选实施方案中,组分(b)的氮化合物是未被取代的碳酸氢氨基胍。
组分(a)的烃基取代的二羧酸或其酸酐通常具有饱和C2-C10二羧酸或其酸酐作为基础骨架。该二羧酸或其酸酐可以带有多个,例如2或3个烃基取代基,但优选仅一个烃基取代基。当该酸酐以分子内方式形成时,该酸酐通常呈环状形式。然而,通过分子间酸酐形成所形成的开链酸酐也合适。该类二羧酸的实例是草酸、丙二酸、琥珀酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸和癸二酸。芳族二羧酸如邻苯二甲酸或对苯二甲酸同样合适。
在优选实施方案中,用作反应组分(a)的烃基取代的二羧酸基于琥珀酸或其酸酐。更具体而言,式II的对应琥珀酸酐在这里是合适的:
其中R3表示具有8-250个碳原子的烃基。烃基在这里还应理解为指具有任何结构的烃基,但还可以少量包含杂原子如氧和/或氮原子和/或卤原子和/或带有官能基团如羟基、羧基、羧酸酯基团、氰基、硝基和/或磺基,条件是不因此改变该基团的显著烃性质。该烃基通常为烷基、链烯基、环烷基、芳基、杂芳基、芳烷基或烷芳基。在更长链烃基的情况下,它可以基于烯烃聚合物,例如基于聚乙烯、聚丙烯或聚异丁烯。
组分(a)中的烃基,即基团R3在优选实施方案中为线性或支化C8-C40烷基或链烯基或具有24-250个碳原子的聚异丁烯基。
线性或支化C8-C40链烯基和聚异丁烯基通常通过未被取代的二羧酸或其酸酐和长链α-烯烃之间的热烯反应以在烃基侧链的α,β位得到烯属双键而得到。为此,通常将反应物加热至150-250℃的温度。链烯基随后可以被氢化成相应的饱和烷基。
有用的C8-C40链烯基,尤其是C10-C24链烯基例如为1-壬烯基、1-癸烯基、1-十一碳烯基、1-十二碳烯基、1-十三碳烯基、1-十四碳烯基、1-十五碳烯基、1-十六碳烯基、1-十八碳烯基、1-二十碳烯基以及由低聚异丁烯如二-、三-、四-或五异丁烯形成的相应链烯基或由工业α-烯烃混合物如C20-C24-α-烯烃形成的相应链烯基。
在存在聚异丁烯基的情况下,它优选包含24-250个,尤其是28-180个,特别是36-80个碳原子,或者因此具有优选为330-3500,尤其是390-2500,尤其是500-1100的数均分子量Mn。该类聚异丁烯基通常由高反应性聚异丁烯,即由具有高比例,通常是至少60%,尤其是至少70%,特别是至少80%端亚乙烯基双键的聚异丁烯制备。
如此得到的聚异丁烯基琥珀酰亚胺(“PIBSA”)通常具有的琥珀酰化程度,即琥珀酸酐单元与聚异丁烯单元的摩尔比,为0.8-2.0,尤其是1.0-1.3。因此,两个琥珀酸酐单元也可以与一个聚异丁烯链键合。
由(a)烃基取代的二羧酸或其酸酐和(b)氮化合物I得到的反应产物通常为不同结构的几种化合物的混合物。该混合物的成分尤其可以为由I的伯氨基形成的酰亚胺,例如化合物IIIa,和/或包含一个或两个氨基三唑结构部分的化合物,例如在R1=R2=H情况下的化合物IIIb:
由(a)烃基取代的二羧酸或其酸酐和(b)氮化合物I形成的本发明反应产物非常适合作为燃料添加剂,其在火花点火式内燃机,尤其是汽油发动机的操作中有效节省燃料,与其他燃料添加剂具有良好溶混性并且不具有与水形成乳液的明显倾向。所述有利性能在额外使用具有去垢作用的燃料添加剂下用于汽油燃料中的情况下以特定程度显示。
因此,本发明还提供了一种燃料组合物,其以主要量包含汽油燃料并以次要量包含至少一种由(a)烃基取代的二羧酸和(b)通式I的氮化合物形成的本发明反应产物,以及至少一种不同于所述反应产物且具有去垢作用的燃料添加剂。
该至少一种本发明反应产物在汽油燃料中的量通常为10-5000重量ppm,更优选20-2000重量ppm,甚至更优选30-1000重量ppm,尤其是40-500重量ppm,例如50-300重量ppm。
有用的汽油燃料包括所有常规汽油燃料组合物。在这里应提及的典型代表是市场上常见的根据EN228的Eurosuper基础燃料。此外,根据WO00/47698的说明书的汽油燃料组合物对本发明而言也是可能的应用领域。此外,在本发明上下文中,汽油燃料还应理解为指含酒精的汽油燃料,尤其是含乙醇的汽油燃料,例如如WO2004/090079所述,例如乙醇含量为75-85体积%的Flex燃料,或包含85体积%乙醇的汽油燃料(“E85”),但还有“E100”燃料类型,其通常为共沸蒸馏的乙醇且因此由约96体积%C2H5OH和约4体积%H2O构成。
由(a)烃基取代的二羧酸或其酸酐和(b)氮化合物I形成的本发明反应产物可以单独或以燃料添加剂包装形式加入特定基础燃料中。该类包装是燃料添加剂浓缩物且除了溶剂外以及除了至少一种不同于本发明反应产物且具有去垢作用的燃料添加剂外通常还包含一系列其他组分作为辅助添加剂,辅助添加剂尤其为载体油、腐蚀抑制剂、破乳剂、去雾剂、消泡剂、燃烧改进剂、抗氧化剂或稳定剂、抗静电剂、茂金属、金属去活化剂、加溶剂、标记剂和/或染料。
下文称为组分(D)的去垢剂或去垢添加剂通常是指用于燃料的沉积抑制剂。去垢添加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的疏水性烃基和至少一个极性结构部分的两亲性物质。
在优选实施方案中,本发明燃料组合物包含至少一种选自如下的代表作为至少一种不同于本发明反应产物且具有去垢作用的燃料添加剂(D):
(Da)具有至多6个氮原子的单-或多氨基,其中至少一个氮原子具有碱性;
(Db)硝基,任选与羟基组合;
(Dc)与单-或多氨基组合的羟基,其中至少一个氮原子具有碱性;
(Dd)羧基或其碱金属或碱土金属盐;
(De)磺基或其碱金属或碱土金属盐;
(Df)由羟基、其中至少一个氮原子具有碱性的单-或多氨基或氨基甲酸酯基封端的聚-C2-C4氧化烯结构部分;
(Dg)羧酸酯基团;
(Dh)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
(Di)通过取代酚与醛和单-或多胺的Mannich反应得到的结构部分。
上述去垢添加剂中的确保在该燃料组合物中足够溶解度的疏水性烃基具有的数均分子量(Mn)为85-20000,尤其是300-5000,特别是500-2500。有用的典型疏水性烃基,尤其是与极性结构部分(Da)、(Dc)、(Dh)和(Di)结合,为相对长链烷基或链烯基,尤其是各自具有Mn=300-5000,尤其是500-2500,特别是700-2300的聚丙烯基、聚丁烯基和聚异丁烯基。
上述组的去垢添加剂实例包括下列:
包含单-或多氨基的添加剂(Da)优选为基于Mn=300-5000的聚丙烯或常规(即主要具有内双键的)聚丁烯或聚异丁烯的聚链烯烃单胺或聚链烯烃多胺。当该类添加剂的制备由主要具有内双键(通常在β和γ位)的聚丁烯或聚异丁烯开始时,一种可能的制备途径是通过氯化并随后胺化或者通过用空气或臭氧氧化双键而得到羰基或羧基化合物并随后在还原性(氢化)条件下胺化。在这里用于胺化的胺例如可以是氨、单胺或多胺,如二甲氨基丙基胺、乙二胺、二亚乙基三胺、三亚乙基四胺或四亚乙基五胺。基于聚丙烯的相应添加剂尤其描述于WO-A-94/24231中。
进一步优选的包含单氨基的添加剂(Da)是平均聚合度P=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。
进一步优选的包含单氨基的添加剂(Da)是可以通过与胺反应并随后脱水和还原氨基醇而由聚异丁烯环氧化物得到的化合物,尤其如DE-A-19620262所述。
任选与羟基组合的包含硝基的添加剂(Db)优选为平均聚合度P=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-A96/03479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-或多氨基组合的羟基的添加剂(Dc)尤其为可以由优选主要具有端双键且Mn=300-5000的聚异丁烯得到的聚异丁烯环氧化物与氨或单-或多胺的反应产物,尤其如EP-A-476485所述。
包含羧基或其碱金属或碱土金属盐的添加剂(Dd)优选为C2-C40烯烃与马来酸酐的共聚物,该共聚物的总摩尔质量为500-20000以及其中一些或所有羧基已经转化成碱金属盐或碱土金属盐并且任何剩余的羧基已经与醇或胺反应。该类添加剂尤其由EP-A-307815公开。该类添加剂主要用于防止阀座磨损并且如WO-A-87/01126所述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。
包含磺基或其碱金属盐或碱土金属盐的添加剂(De)优选为磺基琥珀酸烷基酯的碱金属盐或碱土金属盐,尤其如EP-A-639632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-C2-C4氧化烯结构部分的添加剂(Df)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1-30mol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的聚醚或聚醚胺。该类产物尤其描述于EP-A-310875,EP-A-356725,EP-A-700985和US-A-4877416中。在聚醚的情况下,该类产物也具有载体油性能。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以及丙氧基化物,还有与氨的相应反应产物。
包含羧酸酯基团的添加剂(Dg)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-3838918所述。所用单-、二-或三羧酸可以是脂族或芳族酸,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。该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的添加剂(Dh)优选为烷基-或链烯基取代的琥珀酸酐的相应衍生物,尤其是可以通过使Mn=300-5000的常规或高反应性聚异丁烯与马来酸酐以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相应衍生物。就此而言特别令人感兴趣的是具有脂族多胺如乙二胺、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的与二-胺或多胺的羧酰亚胺,或者由二胺或多胺与两种琥珀酸衍生物反应形成的二酰亚胺。该类燃料添加剂尤其描述于US-A-4849572中。
选自(Dh)组的去垢添加剂优选为烷基-或链烯基取代的琥珀酸酐,尤其是聚异丁烯基琥珀酸酐(“PIBSA”)与胺和/或醇的反应产物。这些因此为衍生于烷基-、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。不言而喻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。
加有添加剂的燃料优选包含至少一种基于聚异丁烯基取代琥珀酰亚胺的去垢剂。尤其令人感兴趣的是与脂族多胺的酰亚胺。特别优选的多胺是乙二胺、二亚乙基三胺、三亚乙基四胺、五亚乙基六胺以及尤其是四亚乙基五胺。聚异丁烯基的数均分子量Mn优选为500-5000,更优选500-2000,尤其是约1000。
包含通过取代酚与醛和单-或多胺的Mannich反应得到的结构部分的添加剂(Di)优选为聚异丁烯取代的酚与甲醛和单-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基胺的反应产物。聚异丁烯基取代的酚可以源于Mn=300-5000的常规或高反应性聚异丁烯。该类“聚异丁烯Mannich碱”尤其描述于EP-A-831141中。
本发明燃料组合物以通常为10-5000重量ppm,更优选20-2000重量ppm,甚至更优选30-1000重量ppm,尤其是40-500重量ppm,例如50-250重量ppm的量包含至少一种不同于本发明反应产物且具有去垢作用的通常选自上述(Da)-(Di)组的燃料添加剂。
所述去垢添加剂(D)优选与至少一种载体油结合使用。在优选实施方案中,本发明燃料组合物除了至少一种本发明反应产物和至少一种不同于本发明反应产物且具有去垢作用的燃料添加剂外还少量包含至少一种载体油作为其他燃料添加剂。
合适的矿物载体油是原油加工中得到的馏分,如粘度例如为SN500-2000等级的重质高粘度润滑油料或基础油;但还有芳族烃,烷属烃和烷氧基链烷醇。同样有用的是在矿物油精炼中得到且已知为“氢化裂解油”的馏分(沸程为约360-500℃的真空馏出液馏分,可以由已经在高压下催化氢化且异构化以及还脱蜡的天然矿物油得到)。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=400-1800的烯烃聚合物,尤其基于聚丁烯或聚异丁烯(氢化或未氢化)。
合适聚醚或聚醚胺的实例优选为可以通过使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1-30mol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的包含聚-C2-C4氧化烯结构部分的化合物。该类产物尤其描述于EP-A-310875,EP-A-356725,EP-A-700985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还有聚异丁烯酚丁氧基化物和丙氧基化物,还有与氨的相应反应产物。
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-3838918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为例如具有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-3826608,DE-A-4142241,DE-A-4309074,EP-A-0452328和EP-A-0548617中。
特别合适的合成载体油实例是具有约5-35个,例如约5-30个例如选自氧化丙烯单元、氧化正丁烯单元和氧化异丁烯单元或其混合物的C3-C6氧化烯单元的醇起始的聚醚。合适起始剂醇的非限制性实例是长链链烷醇或被长链烷基取代的酚,其中长链烷基尤其为直链或支化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-10102913所述。
优选的载体油是合成载体油,特别优选聚醚。
当还使用载体油时,将它以优选为1-1000重量ppm,更优选10-500重量ppm,尤其是20-100重量ppm的量加入本发明加有添加剂的燃料中。
在优选实施方案中,本发明燃料组合物除了至少一种本发明反应产物、至少一种不同于本发明反应产物且具有去垢作用的燃料添加剂和任选至少一种载体油外还以少量包含至少一种腐蚀抑制剂作为其他燃料添加剂。
适合作为该类辅助添加剂的腐蚀抑制剂例如为琥珀酸酯,尤其是与多元醇的酯,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酚-和萘磺酸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,例如醇乙氧基化物,苯酚烷氧基化物,例如叔丁基酚乙氧基化物或叔戊基酚乙氧基化物,脂肪酸,烷基酚,氧化乙烯和氧化丙烯的缩合产物,例如氧化乙烯-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抗氧化剂例如为取代酚,例如2,6-二叔丁基苯酚和2,6-二叔丁基-3-甲基苯酚,还有苯二胺,例如N,N’-二仲丁基对苯二胺。
适合作为其他辅助添加剂的金属去活化剂例如为水杨酸衍生物,例如N,N’-二亚水杨基-1,2-丙二胺。
合适的溶剂,尤其也适合燃料添加剂包装的溶剂,例如为非极性有机溶剂,尤其是芳族和脂族烃类,例如甲苯、二甲苯类、“石油溶剂”以及牌号(制造商:RoyalDutch/ShellGroup),(制造商:ExxonMobil)和溶剂石脑油的工业溶剂混合物。在这里还有用的是尤其以与所述非极性有机溶剂的共混物使用的极性有机溶剂,尤其是醇类如叔丁醇、异戊醇、2-乙基己醇和2-丙基庚醇。
当还将所述辅助添加剂和/或溶剂用于汽油燃料中时,它们以常用于此的量使用。
本发明还提供了包含至少一种由(a)烃基取代的二羧酸或其酸酐和(b)通式I的氮化合物形成的本发明反应产物以及至少一种不同于所述反应产物且具有去垢作用的燃料添加剂的添加剂浓缩物。然而,本发明添加剂浓缩物可以包含上述其他辅助添加剂。
本发明反应产物优选以1-99重量%,更优选15-95重量%,尤其是30-90重量%的量存在于本发明添加剂浓缩物中,在每种情况下基于该浓缩物的总重量。至少一种不同于所述反应产物且具有去垢作用的燃料添加剂优选以1-99重量%,更优选5-85重量%,尤其是10-70重量%的量存在于本发明添加剂浓缩物中,在每种情况下基于该浓缩物的总重量。
下列实施例用来进一步说明而不限制本发明。
实施例1:混合性能
由马来酸酐与数均分子量Mn为1000且端亚乙烯基双键含量为85%的聚异丁烯通过热烯反应(200℃)得到的聚异丁烯基琥珀酸酐和碳酸氢氨基胍形成的反应产物(“RP1”)类似于US2009/0282731A1的实施例1使用SolvessoTM150(制造商:ExxonMobil)作为稀释剂制备。
通过简单混入下面所列组分使用如此制备的反应产物(“RP1”)来制备添加剂浓缩物(“AC1”):
●400重量份本发明反应产物RP1(50重量%,在Solvesso150中)
●390重量份(聚合物含量)常规去垢添加剂组分(基于Mn=1000的聚异丁烯的聚异丁烯单胺)
●310重量份基于醇起始的聚醚的市售载体油
●270重量份作为稀释剂的溶剂石脑油
●470重量份作为其他稀释剂的2-丙基庚醇
●4重量份常规去雾剂组分(基于烷氧基化苯酚-甲醛缩合物)
可以没有任何问题地相互混合所述组分而得到透明液体,其稠度在几天内保持稳定。
为了对比,制备添加剂浓缩物“AC2”,其与AC1的不同仅在于本发明反应产物RP1被相同量的市售现有技术润滑性改进剂的活性成分(“RP2”),即由聚异丁烯基琥珀酸酐(基于Mn=1000的聚异丁烯)和四亚乙基五胺形成的酰亚胺替代。混合在一起之后,RP2以浑浊液体存在,在几天之后由浑浊液体分离出沉淀物。
实施例2:乳液性能
在每种情况下对市场上常见的根据EN228的典型Eurosuper基础燃料以使得润滑性改进剂RP1(本发明)和RP2(用于对比)的剂量在每种情况下为390重量ppm的量添加添加剂浓缩物AC1(本发明)和AC2(用于对比)作为汽油燃料。根据ASTMD1094相分离测试,向体系中加入水并评价相分离行为。5分钟后AC1给出两各个透明且清晰分开的相(根据ASTMD1094:1的相分离评价),而5分钟后AC2得到在水相和浑浊燃料相中的乳液(根据ASTMD1094:4的相分离评价)。
实施例3:燃料经济性
基于美国市场上常见的基础燃料通过以实施例2所述剂量率向其中添加AC1而生产的汽油燃料用于在实用性测试(fleettest)中使用3辆不同汽车根据U.S.EnvironmentalProtectionAgencyTestProtocol,C.F.R.Title40,Part600,SubpartB测定燃料经济性。对于各辆汽车首先用未加添加剂的燃料测定燃料消耗,然后用相同燃料测定燃料消耗,然而,该燃料在此以实施例2中所述剂量包含添加剂浓缩物AC1。对所有所用汽车求平均,结果是燃料平均节省1.3%。
实施例4:进气阀清洁度
在MercedesBenzM111发动机中用两种加有AC1(本发明)或AC2(用于对比)的汽油燃料根据CECF-20-98测定进气阀沉积物(“IVD”)。对未加添加剂的汽油燃料给定每阀94mg的基础值,加有AC1(本发明)的汽油燃料给出每阀2mg的值,而加有AC2(用于对比)的汽油燃料给出每阀6mg的值。
Claims (9)
1.由(a)其烃基为线性或支化C8-C40烷基或-链烯基或具有24-250个碳原子的聚异丁烯基的烃基取代的二羧酸或其酸酐和(b)通式I的氮化合物或氮化合物I的盐形成的反应产物,以及至少一种不同于所述反应产物且具有去垢作用并为具有至少一个数均分子量(Mn)为85-20000的疏水性烃基和至少一个极性结构部分的两亲性物质的燃料添加剂在燃料中作为添加剂以在使用该燃料的火花点火式内燃机操作中降低燃料消耗或者在汽油燃料中作为添加剂以在使用该燃料的自点火式内燃机操作中降低燃料消耗的用途:
其中R1和R2各自独立地为氢或C1-C20烃基。
2.根据权利要求1的用途,其中组分(a)的烃基取代的二羧酸基于琥珀酸或其酸酐。
3.根据权利要求1或2的用途,其中组分(b)的氮化合物是未取代的碳酸氢氨基胍。
4.一种燃料组合物,其以主要量包含汽油燃料并以次要量包含至少一种根据权利要求1-3中任一项的由(a)烃基取代的二羧酸和(b)通式I的氮化合物形成的本发明反应产物,以及至少一种不同于所述反应产物且具有去垢作用并为具有至少一个数均分子量(Mn)为85-20000的疏水性烃基和至少一个极性结构部分的两亲性物质的燃料添加剂。
5.根据权利要求4的燃料组合物,包含至少一种选自如下的代表作为不同于所述反应产物且具有去垢作用的所述燃料添加剂:
(Da)具有至多6个氮原子的单-或多氨基,其中至少一个氮原子具有碱性;
(Db)硝基,任选与羟基组合;
(Dc)与单-或多氨基组合的羟基,其中至少一个氮原子具有碱性;
(Dd)羧基或其碱金属或碱土金属盐;
(De)磺基或其碱金属或碱土金属盐;
(Df)由羟基、其中至少一个氮原子具有碱性的单-或多氨基或氨基甲酸酯基封端的聚-C2-C4氧化烯结构部分;
(Dg)羧酸酯基团;
(Dh)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
(Di)通过取代酚与醛和单-或多胺的Mannich反应得到的结构部分。
6.根据权利要求4的燃料组合物,额外少量包含至少一种载体油作为其他燃料添加剂。
7.根据权利要求5的燃料组合物,额外少量包含至少一种载体油作为其他燃料添加剂。
8.根据权利要求4-7中任一项的燃料组合物,额外少量包含至少一种腐蚀抑制剂作为其他燃料添加剂。
9.一种添加剂浓缩物,包含至少一种根据权利要求1-3中任一项的由(a)烃基取代的二羧酸或其酸酐和(b)通式I的氮化合物形成的反应产物,以及至少一种不同于所述反应产物且具有去垢作用并为具有至少一个数均分子量(Mn)为85-20000的疏水性烃基和至少一个极性结构部分的两亲性物质的燃料添加剂。
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EP2646530A2 (de) | 2013-10-09 |
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CN103228769A (zh) | 2013-07-31 |
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