CN1993449A - 用于燃料和润滑剂的多胺添加剂 - Google Patents
用于燃料和润滑剂的多胺添加剂 Download PDFInfo
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- CN1993449A CN1993449A CNA2005800265887A CN200580026588A CN1993449A CN 1993449 A CN1993449 A CN 1993449A CN A2005800265887 A CNA2005800265887 A CN A2005800265887A CN 200580026588 A CN200580026588 A CN 200580026588A CN 1993449 A CN1993449 A CN 1993449A
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- Prior art keywords
- purposes
- additive
- fuel
- alkyl
- formula
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- 239000000654 additive Substances 0.000 title claims abstract description 81
- 239000000446 fuel Substances 0.000 title claims abstract description 73
- 229920000768 polyamine Polymers 0.000 title claims abstract description 45
- 239000000314 lubricant Substances 0.000 title claims abstract description 24
- 230000000996 additive effect Effects 0.000 claims abstract description 71
- 239000000203 mixture Substances 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 38
- -1 imide compound Chemical class 0.000 claims description 36
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 238000004140 cleaning Methods 0.000 claims description 29
- 239000002283 diesel fuel Substances 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 238000003763 carbonization Methods 0.000 claims description 8
- 238000012360 testing method Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000010687 lubricating oil Substances 0.000 claims description 7
- 239000003921 oil Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 238000010000 carbonizing Methods 0.000 claims description 6
- 239000002199 base oil Substances 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 239000003879 lubricant additive Substances 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 230000003078 antioxidant effect Effects 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 239000013530 defoamer Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 230000009885 systemic effect Effects 0.000 claims description 2
- 238000005299 abrasion Methods 0.000 claims 1
- 239000003599 detergent Substances 0.000 abstract description 5
- 239000012141 concentrate Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 1
- 125000001302 tertiary amino group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 description 41
- 229920002367 Polyisobutene Polymers 0.000 description 35
- 125000000217 alkyl group Chemical group 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- 239000002253 acid Substances 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 16
- 150000001721 carbon Chemical group 0.000 description 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 150000003335 secondary amines Chemical group 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 150000002830 nitrogen compounds Chemical class 0.000 description 8
- 150000003512 tertiary amines Chemical class 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 125000003368 amide group Chemical group 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 229910017464 nitrogen compound Inorganic materials 0.000 description 7
- 229960002317 succinimide Drugs 0.000 description 7
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 6
- 230000002209 hydrophobic effect Effects 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 230000009257 reactivity Effects 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 238000005461 lubrication Methods 0.000 description 5
- 239000003607 modifier Substances 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000004711 α-olefin Substances 0.000 description 5
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000003350 kerosene Substances 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 150000003141 primary amines Chemical group 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 4
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229920002368 Glissopal ® Polymers 0.000 description 3
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 238000005576 amination reaction Methods 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 229920001281 polyalkylene Polymers 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000009183 running Effects 0.000 description 3
- 229940014800 succinic anhydride Drugs 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-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
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000006683 Mannich reaction Methods 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
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- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000007942 carboxylates Chemical group 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 125000005393 dicarboximide group Chemical group 0.000 description 2
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
- 239000006280 diesel fuel additive Substances 0.000 description 2
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
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- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- 238000007037 hydroformylation reaction Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- OMKZWUPRGQMQJC-UHFFFAOYSA-N n'-[3-(dimethylamino)propyl]propane-1,3-diamine Chemical compound CN(C)CCCNCCCN OMKZWUPRGQMQJC-UHFFFAOYSA-N 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
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- 238000005457 optimization Methods 0.000 description 2
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- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
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- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical group CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
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- KUKRLSJNTMLPPK-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[2.2.1]hept-2-ene Chemical group C1CC2(C)C=CC1C2(C)C KUKRLSJNTMLPPK-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
- C10M133/56—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- 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
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/234—Macromolecular compounds
- C10L1/238—Macromolecular compounds obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
- C10L1/2383—Polyamines or polyimines, or derivatives thereof (poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C)
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/18—Use of additives to fuels or fires for particular purposes use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/16—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/12—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M149/14—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds a condensation reaction being involved
- C10M149/22—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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Abstract
本发明涉及具有至少一个末端仲胺或叔胺官能的多胺作为清洁添加剂用于燃料和润滑剂的用途。本发明还涉及含有这种多胺的添加剂浓缩物、添加有多胺的燃料和润滑剂以及一种制备它们的方法。
Description
本发明涉及具有至少一个末端仲胺或叔胺官能的多胺作为清洁添加剂在燃料和润滑剂中的用途;涉及包含这种多胺的添加剂浓缩物;涉及添加有这些多胺的燃料和润滑剂以及制备它们的方法。
背景技术
在内燃的运转过程中,在燃烧室和燃料供入系统的区域中可能形成不希望的沉积物。在柴油燃料的情况下,在喷射喷嘴和喷射孔区域发现碳沉积物,它们可削弱细碎燃料雾在直喷式高性能系统如共轨、泵-喷嘴或泵-管-喷嘴中的最佳形成,因此导致燃料消耗和排放增加。为了最小化或完全避免与出现这种沉积物相关的破坏,在燃料中加入清洁添加剂。
这种清洁添加剂的实例尤其包括聚链烯基琥珀酰亚胺。这些添加剂在燃料和润滑剂中有许多用途,且通常与其它添加剂结合;例如参见EP-A-0264247、EP-A-0271937和WO-A-98/42808。
例如,WO-A-98/42808描述了将单烯属不饱和C4-C10二羧酸的聚链烯基衍生物与具有伯胺端基的多胺的特定反应产物作为清洁添加剂用于低硫的柴油燃料。
DE-A-101 23 553公开了一种制备聚链烯基琥珀酰亚胺的方法,其中使PIBSA例如与低聚胺或多胺在醇存在下反应。所用低聚胺或多胺同样具有伯胺端基。
WO 2004/024851描述了用于润滑剂和燃料的协同增效活性添加剂混合物,其由具有去垢作用的添加剂和部分或完全中和的脂肪酸组成。清洁添加剂具体包括具有Mn为85-20 000的疏水烃基,其极性端基选自衍生于羧酸酐的结构部分且具有羟基和/或氨基和/或酰氨基和/或亚氨基的化合物。其中并没有研究在最终产物中具有仲胺或叔胺端基的聚亚烷基多胺的二羧酰亚胺。
现有技术中所述的添加剂和添加剂混合物的缺点在于获取清洁效果或保持清洁效果所需的剂量较高。
发明概述
因此,本发明的目的是提供用于燃料和润滑组合物,尤其是柴油燃料的改进的清洁添加剂,其甚至在低剂量下有效并且尤其有效地降低喷嘴碳化。
已经令人惊讶地发现上述目的通过提供具有至少一个末端仲胺或叔胺官能的线性多胺作为清洁添加剂用于燃料和润滑剂而实现。
本发明首先提供通式I的化合物作为清洁添加剂在燃料和润滑剂中的用途:
R1R2N((CH2)xNH)y(CH2)zNR3R4 (I)
其中
R1、R2、R3和R4各自独立地为H或C1-C10烷基,但R1和R2不同时为H,R3和R4也不同时为H;或R1和R2与它们所键接的氮原子一起形成C4-C6二羧酰亚胺环,所述环由至少一个数均分子量Mn为100-2500的聚链烯基R取代,且其中优选R3和R4同时为C1-C10烷基;
y为1-100的整数,例如1-50,1-20或1-10如1、2、3、4、5、6、7、8、9或10,和
x和z独立地为2-12的整数,例如2-10,2-8,2-6或2、3或4。
尤其应提及其在柴油燃料中的用途,以及在该情况下在柴油机中降低喷嘴碳化的用途。例如,本发明添加剂适用于在具有直接燃料喷射的柴油机,以及基于“共轨”、“泵-喷嘴”或“泵-管-喷嘴”原理的那些柴油机中降低喷嘴碳化。
“降低喷嘴碳化”应理解为与不含添加剂的燃料(即在燃料中不存在式I化合物时)发生的喷嘴碳化程度相比,部分或完全降低喷嘴碳化的程度,这在标准化的测试发动机中测量,尤其是根据用于测量下述空气限流的标准化测试发动机进行测量。
第一组优选的化合物包括如下通式II的化合物:
其中x、y、z、R、R3和R4各自如上所定义。因此,这类化合物由仲胺或叔胺官能封端。尤其提及其中R3和R4相同或不同且为C1-C10烷基、C1-C8烷基、C1-C6烷基、C1-C5烷基或C1-C4烷基的式II化合物。
根据本发明优选的聚链烯基R的实施方案在后面的C2)部分说明。尤其优选R为聚异丁烯基。聚异丁烯基的Mn尤其为约500-1000。
第二组优选的化合物包括其中R1、R2、R3和R4各自独立地为H或C1-C10烷基,但R1和R2不同时为H,R3和R4也不同时为H且x、y和z各自如上所定义的式I化合物。因此,这类化合物由两个仲胺和/或叔胺官能封端。
尤其优选其中x和z各自独立地为2、3或4的整数且y为1、2或3的式I和II的那些化合物。
进一步特别优选其中R3和R4各自独立地为H或C1-C8烷基、C1-C6烷基、C1-C5烷基或C1-C4烷基,但R3和R4不同时为H;或其中R3和R4同时为C1-C8烷基、C1-C6烷基、C1-C5烷基或C1-C4烷基的式I和II的那些化合物。优选R3和R4具有相同含义。
特别优选其中R1、R2、R3和R4各自同时为C1-C4烷基的式I化合物。
在另一优选实施方案中,使用在制备式I化合物中得到的反应产物或混合物,合适的话部分提纯。
根据本发明例如还可以使用包含式I酰亚胺化合物如式II化合物的反应产物,其中所述反应产物可通过使被至少一个数均分子量Mn为100-2500的聚链烯基R取代的环状C4-C6二羧酸酐与式III多胺反应,合适的话随后除去反应混合物的挥发性成分而得到:
H2N((CH2)xNH)y(CH2)zNR3R4 (III)
其中x、y、z、R3和R4各自如上所定义。反应可根据DE-A-101 23 553的公开内容进行。
上述清洁添加剂通常与至少一种下文中更确切描述的其它常规燃料或润滑剂添加剂组合使用。
式I添加剂的加入量为约1-200mg/kg燃料,更优选以1-100,1-50,1-30,2-20或2-16mg/kg燃料的剂量加入。
式I添加剂优选以导致最大碳化程度的80%,优选70%如0-65%,2-50%或5-40%的量加入,碳化程度根据CEC F23 A 01(在XUD9测试发动机中以0.1mm的针距(needle stroke))经由空气限流百分数测量。
本发明进一步提供包含大部分的沸程为100-500℃,例如150-400℃或160-360℃的烃燃料,尤其是中间馏分燃料如柴油燃料,有效量的至少一种如上所定义的式I清洁添加剂的燃料组合物。
本发明还提供包含常规润滑剂,至少有效量的至少一种如上所定义的式I清洁添加剂的润滑剂组合物。
本发明还涉及包含与至少一种其它常规燃料或润滑剂添加剂结合的至少一种如上所定义的式I清洁添加剂的添加剂浓缩物。本发明添加剂在浓缩物中的存在量基于浓缩物的总重量优选为0.1-80重量%,更优选1-70重量%,尤其是20-60重量%。
本发明还提供一种制备具有改进的清洁燃料进入系统作用的燃料组合物的方法,其中将有效量的至少一种如上所定义的化合物或如上所定义的添加剂浓缩物加入市售燃料组合物中。
最后,本发明提供了一种制备具有改进的清洁作用的润滑剂组合物的方法,其中将有效量的至少一种如上所定义的化合物或如上所定义的添加剂浓缩物加入市售润滑剂组合物中。
发明详述
A)本发明多胺的优选实施方案
在上述基团R1、R2、R3和R4的定义中,C1-C10烷基尤其代表C1-C4烷基如甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基,以及长链戊基、己基、庚基、辛基、壬基和癸基,及其单支化或多支化,例如单支化、双支化或三支化的类似物。
C4-C6二羧酰亚胺环尤其衍生于单烯属不饱和C4-C6二羧酸及其衍生物,尤其是酸酐。合适的二羧酸为琥珀酸、戊二酸和己二酸的单不饱和形式。
A1)组1的二羧酰亚胺衍生物
这些化合物例如可通过使被疏水烃基取代的二羧酸或被疏水烃基取代的二羧酸衍生物与具有至少一个NH2基团的胺反应而得到。优选使羧酸酐反应。
二羧酸(衍生物)基团与烃基的摩尔比为0.8∶2或0.9∶1.5或0.9∶1.05,例如同样如EP-A-0 355 895和0 587 381中所述。
这类二羧酸或其衍生物,尤其是二羧酸酐与胺的反应可导致包含二羧酸单酰胺、二羧酸二酰胺、二羧酸单酰胺的铵盐、二羧酸单酰胺单酯、脒、二羧酸单酰亚胺和二羧酸二酰亚胺的产物混合物。适合作为本发明添加剂的是单个所述的酰化产物及其混合物。
然而,优选二羧酰亚胺,尤其是二羧酸单酰亚胺和包含它们的混合物。亚酰胺含量尤其为1-100摩尔%,例如10-95摩尔%或30-90摩尔%。
结合比例(PIBSA/AMINE)基于琥珀酸基团与胺的比例为0.5-2如0.8-1.2,更优选0.9-1.05。
适合与二羧酸或二羧酸衍生物反应的胺为上述式III的多胺。
合适的多胺例如为二亚乙基三胺、三亚乙基四胺、四亚乙基五胺、五亚乙基六胺、二亚丙基三胺、三亚丙基四胺、四亚丙基五胺、五亚丙基六胺、二亚丁基三胺、三亚丁基四胺、四亚丁基五胺、五亚丁基六胺的单-N,N-二烷基衍生物。
实例包括:N,N-二甲基二亚甲基三胺、N,N-二乙基二亚甲基三胺、N,N-二丙基二亚甲基三胺、N,N-二甲基二亚乙基-1,2-三胺、N,N-二乙基二亚乙基-1,2-三胺、N,N-二丙基二亚乙基-1,2-三胺、N,N-二甲基二亚丙基-1,3-三胺(即DMAPAPA)、N,N-二乙基二亚丙基-1,3-三胺、N,N-二丙基二亚丙基-1,3-三胺、N,N-二甲基二亚丁基-1,4-三胺、N,N-二乙基二亚丁基-1,4-三胺、N,N-二丙基二亚丁基-1,4-三胺、N,N-二甲基二亚戊基-1,5-三胺、N,N-二乙基二亚戊基-1,5-三胺、N,N-二丙基二亚戊基-1,5-三胺、N,N-二甲基二亚己基-1,6-三胺、N,N-二乙基二亚己基-1,6-三胺和N,N-二丙基二亚己基-1,6-三胺。
A2)由两个仲胺和/或叔胺官能封端的组2的多胺
非限制性实例包括:由相同的N,N-二烷基氨基封端的线性多胺,例如二[2-(N,N-二甲基氨基)乙基]胺、二[2-(N,N-二乙基氨基)乙基]胺、二[2-(N,N-二丙基氨基)乙基]胺、二[3-(N,N-二甲基氨基)丙基]胺、二[3-(N,N-二乙基氨基)丙基]胺、二[3-(N,N-二丙基氨基)丙基]胺、二[4-(N,N-二甲基氨基)丁基]胺、二[4-(N,N-二乙基氨基)丁基]胺、二[4-(N,N-二丙基氨基)丁基]胺、二[5-(N,N-二甲基氨基)戊基]胺、二[5-(N,N-二乙基氨基)戊基]胺、二[5-(N,N-二丙基氨基)戊基]胺、二[6-(N,N-二甲基氨基)己基]胺、二[6-(N,N-二乙基氨基)己基]胺、二[6-(N,N-二丙基氨基)己基]胺和对应的由相同的单烷基氨基封端的类似物。也可使用由不同单烷基氨基或二烷基氨基封端的对应多胺以及这些化合物的混合物。
上述类型的多胺描述于Kirk-Othmer″Encyclopedia of ChemicalTechnology″,第2版,第7卷,第22-37页,Interscience Publishers,NewYork(1965,″Ethylenamines″章)中。
B)制备本发明添加剂
B1)组1的二羧酰亚胺添加剂
制备这些化合物的方法对本领域熟练技术人员是已知的。制备聚链烯基琥珀酰亚胺的特别合适的方法描述于德国专利申请DE-A-10123553.4中,此处完全引入作为参考。在该方法中,首先使聚链烯基琥珀酸酐与醇或酚反应,随后与胺反应。或者,使聚链烯基琥珀酸酐在醇或酚存在下与胺反应。
适用于制备聚链烯基琥珀酰亚胺的醇优选为一元醇;然而多元醇也是合适的。
优选使用具有1-16个碳原子的一元醇,例如甲醇、乙醇、丙醇、异丙醇、丁醇、仲丁醇、异丁醇、叔丁醇、2-羟基甲基呋喃、戊醇、异戊醇、乙烯基甲醇、环己醇、正己醇、6-辛醇、2-乙基己醇、正癸醇、月桂醇、异辛醇及其混合物。优选的醇为具有6-16个碳原子的那些醇。特别优选2-乙基己醇。
合适的酚包括苯酚、萘酚、(邻,对)-烷基苯酚和水杨酸。
制备聚链烯基取代的二羧酸或其衍生物的方法是已知的。例如,德国专利申请DE-A-10123553.4描述了通过使聚烯烃与单不饱和酸或其衍生物反应而制备聚烯烃取代的羧酸或其衍生物,其中在该反应过程中聚烯烃在反应中加成到酸组分的双键上。其它方法还例如描述于WO-A-98/42808中,此处引入作为参考。
B2)具有两个末端仲胺或叔胺官能的组2的多胺
它们如Ullmann′s Encyclopedia of Industrial Chemistry,第6版,2000,电子版,第8.2章,Oligo-and Polyamines中所述制备。
以类似的方式制备式III的多胺。
C)本发明多胺的不同应用
本发明多胺产物可作为添加剂(通常以添加剂包或浓缩物形式)用于燃料,尤其是柴油燃料、燃料油、煤油,或者通常为中间馏分,和汽油燃料,或润滑剂。
当本发明多胺用作柴油燃料添加剂时,它们含有有效量的多胺。合适的是柴油燃料基于柴油燃料的总重量含有约1-5000ppm或约5-1000ppm,例如约5-200或10-100ppm的比例。
所用柴油燃料添加剂混合物包含至少一种选自如下的其它添加剂:其它常规清洁剂、缓蚀剂、去浊剂(dehazer)、反乳化剂、消泡剂、抗氧化剂、金属减活剂、多官能的稳定剂、十六烷值改进剂、助燃剂、染料、标记物、加溶剂、抗静电剂、润滑改进剂。
本发明多胺也可作为添加剂用于燃料油。基于燃料油的总重量,它们以有效量使用,合适的是以10-1000ppm,优选50-500ppm的量使用。其可包含至少一种可选自缓蚀剂、反乳化剂、消泡剂、抗氧化剂、金属减活剂、二茂铁和除臭剂的其它添加剂。
本发明多胺也可作为添加剂用于汽油燃料。基于汽油燃料的总重量,它们含有有效量的本发明多胺,合适的是含有1-5000ppm或约5-1000ppm,例如约5-200或10-100ppm本发明多胺。
汽油燃料添加剂混合物可以包含至少一种选自其它常规清洁添加剂、载体油(carrier oil)、润滑改进剂、溶剂和缓蚀剂的其它添加剂。
最后,本发明多胺也适合用于润滑剂组合物,该润滑剂组合物基于其总重量含有有效量的本发明产物,合适的是含有0.1-10重量%,优选0.5-5重量%本发明产物。
润滑剂组合物也可包含尤其选自润滑改进剂、防磨添加剂、缓蚀剂、VI改进剂的其它添加剂。
可用作辅助添加剂的一些添加剂如下所述:
C1)清洁添加剂
有去垢作用的添加剂具有至少一个数均分子量(Mn)为85-20 000的疏水烃基和至少一个选自如下的极性结构部分:
(a)单氨基或具有至多6个氮原子,并且其中至少一个氮原子具有碱性的多氨基;
(b)硝基,任选与羟基结合;
(c)与单氨基或其中至少一个氮原子具有碱性的多氨基结合的羟基;
(d)由羟基、单氨基或其中至少一个氮原子具有碱性的多氨基,或氨基甲酸酯基团封端的聚C2-C4氧化烯基;
(e)羧酸酯基团;
(f)通过使取代酚与醛和单胺或多胺进行曼尼希反应而得到的结构部分;
(g)衍生于羧酸酐且具有羟基和/或氨基和/或酰氨基和/或亚氨基的结构部分,
与式I的本发明多胺类似,这些含有亚氨基的清洁剂不具有仲胺或叔胺端基。
含有单氨基或多氨基(a)的添加剂优选为基于MN=300-5000的聚丙烯或者反应性(即主要具有末端双键,通常在β-和γ-位)或常规(即主要具有内部双键)聚丁烯或聚异丁烯的聚亚烷基单胺或聚亚烷基多胺。这类基于反应性聚异丁烯的添加剂尤其公开于EP-A 244 616中,它们可由含有至多20重量%正丁烯单元的聚异丁烯通过加氢甲酰基化并用氨,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还原性胺化而制备。当在添加剂的制备中使用主要具有内部双键(通常在β-和γ-位)的聚丁烯或聚异丁烯作为原料时,可能的制备路线为通过氯化,随后胺化,或者通过用空气或臭氧使双键氧化而得到羰基或羧基化合物,随后在还原性(加氢)条件下胺化。此处用于胺化的胺可以与上述用于使加氢甲酰基化的高反应性聚异丁烯还原性胺化的那些胺相同。基于聚丙烯的对应添加剂尤其描述于WO-A 94/24231中,此处完全引入作为参考。
含有单氨基(a)的其它优选添加剂为平均聚合度P=5-100的聚异丁烯与氮氧化物或者氮氧化物与氧气的混合物的反应产物的加氢产物,尤其如WO-A 97/03946中所述,此处完全引入作为参考。
含有单氨基(a)的其它优选添加剂为可由聚异丁烯环氧化物通过与胺反应,随后使氨基醇脱水并还原而得到的化合物,尤其如DE-A 196 20 262中所述,此处完全引入作为参考。
含有任选与羟基结合的硝基(b)的添加剂优选为平均聚合度P=5-100或10-100的聚异丁烯与氮氧化物或者氮氧化物与氧气的混合物的反应产物,尤其如WO-A 96/03367和WO-A 96/03479中所述,此处完全引入作为参考。这些反应产物通常为纯硝基聚异丁烯(如α,β-二硝基聚异丁烯)和混合的羟基硝基聚异丁烯(如α-硝基-β-羟基聚异丁烯)的混合物。
含有任选与单氨基或多氨基结合的羟基(c)的添加剂尤其为可由优选主要具有末端双键且MN=300-5000的聚异丁烯得到的聚异丁烯环氧化物与氨或单胺或多胺的反应产物,如EP-A 476 485中所述,此处完全引入作为参考。
含有聚C2-C4氧化烯结构部分(d)的添加剂优选为可通过使C2-C60链烷醇、C6-C30链烷二醇、单C2-C30烷基胺、二C2-C30烷基胺、C1-C30烷基环己醇或C1-C30烷基酚与每羟基或氨基1-30摩尔氧化乙烯和/或氧化丙烯和/或氧化丁烯反应,并且在聚醚胺的情况下,通过随后与氨、单胺或多胺还原胺化而得到的聚醚或聚醚胺。这类产物尤其描述于EP-A 310 875、EP-A356 725、EP-A 700 985和US-A 4 877 416中,此处完全引入作为参考。在聚醚的情况下,这类产物也具有载体油性能。这些产物的典型实例为十三醇丁氧基化物、异十三醇丁氧基化物、异壬基苯酚丁氧基化物和聚异丁烯醇丁氧基化物及聚异丁烯醇丙氧基化物以及对应的与氨的反应产物。
含有羧酸酯基团(e)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的那些,尤其如DE-A38 38 918中所述,此处完全引入作为参考。所用单-、二-或三羧酸可以为脂族或芳族酸,特别合适的酯醇或酯多元醇为例如具有6-24个碳原子的长链代表。酯的典型代表为异辛醇、异壬醇、异癸醇和异十三醇的己二酸酯、邻苯二甲酸酯、间苯二甲酸酯、对苯二甲酸酯和偏苯三酸酯。这类产物也可具有载体油性能。
含有通常通过使酚羟基与醛和单胺或多胺进行常规的曼尼希反应而得到的结构部分(f)的添加剂优选为聚异丁烯取代的酚与甲醛和伯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可源于Mn=300-5000的常规或高反应性聚异丁烯。这类“聚异丁烯-曼尼希碱”尤其描述于EP-A 831 141中,此处完全引入作为参考。
含有衍生于羧酸酐且具有羟基和/或氨基和/或酰氨基和/或亚氨基的结构部分(g)的添加剂优选为二羧酸酐,更优选琥珀酸酐的对应衍生物。不言而喻,术语“衍生于羧酸酐的结构部分...”不必要求原料真正必须为羧酸酐。应理解的是这类结构部分也可通过使具有所需活性的其它羧酸衍生物如碳酰氯反应而得到,或者通过采取合适的活化措施使羧酸本身反应而得到。然而,羧酸酐是转化为所述结构部分的特别适合的衍生物。
组分A的极性结构部分更优选为衍生于羧酸酐且具有羟基和/或氨基和/或酰氨基和/或亚氨基的结构部分(g),尤其是具有酰氨基和/或亚氨基的结构部分,即N-酰基结构部分。
上述清洁添加剂的疏水烃基(a)-(g)以及式I和II的本发明多胺清洁剂的疏水烃基R优选为其重复单元衍生于选自丙烯、正丁烯和异丁烯及其混合物的单体的均聚物或共聚物基团。
均聚物或共聚物基团更优选为聚异丁烯基团。均聚物或共聚物基团尤其为衍生于“反应性”聚异丁烯的基团,其中“反应性”聚异丁烯与“低反应性”聚异丁烯的区别之处在于末端双键的含量。其中“反应性”聚异丁烯与“低反应性”聚异丁烯的区别之处在于它们基于聚异丁烯大分子的总数含有至少50摩尔%,优选至少60摩尔%,更优选至少80摩尔%末端双键。末端双键可以为乙烯基双键[-CH=C(CH3)2]或者亚乙烯基双键[-CH2-C(=CH2)-CH3]。特别优选具有均匀聚合物骨架的聚异丁烯。均匀聚合物骨架尤其为由至少85重量%,优选至少90重量%,更优选至少95重量%程度的异丁烯单元组成的那些聚异丁烯。例如,这类反应性聚异丁烯的数均分子量为100-20000。适合制备燃料添加剂的反应性聚异丁烯尤其是数均分子量为100-3000,例如200-2500或500-1500如约550、约800或约1000数均分子量的那些。
适合制备润滑剂添加剂的反应性聚异丁烯尤其是数均分子量为1000-15000,更优选1300-12500,最优选2000-10000,如约1500、约2000或约2300数均分子量的那些。
额外优选反应性聚异丁烯的多分散性小于3.0,尤其是小于1.9,更优选小于1.7或小于1.5。多分散性是指重均分子量MW除以数均分子量MN的商。
特别适合的反应性聚异丁烯例如为BASF AG的Glissopal牌,尤其是Glissopal 1000(MN=1000)和Glissopal V 33(MN=550)和Glissopal2300(MN=2300)及其混合物。其它数均分子量可通过原则上已知的方式通过混合不同数均分子量的聚异丁烯或通过萃取富集某一分子量范围的聚异丁烯而得到。
C2)冷流改进剂
改进低温性能的添加剂(冷流改进剂)包括中间馏分流动改进剂(″MDFI″)、链烷烃分散剂(″WASA″)和两种添加剂的组合(″WAFI″)。
合适的冷流改进剂尤其包括如下组的活性物质,例如如WO 95/33805中所述:
aa)乙烯与至少一种其它烯属不饱和单体的共聚物,该共聚物不同于根据本发明使用的聚合物;
ab)梳形聚合物;
ac)聚氧化烯;
ad)极性氮化合物;
ae)磺基羧酸或磺酸或其衍生物;和
af)聚(甲基)丙烯酸酯。
在乙烯与至少一种其它烯属不饱和单体的共聚物(aa)的情况下,所述单体优选选自链烯基羧酸酯、(甲基)丙烯酸酯和烯烃。
合适烯烃的实例为具有3-10个碳原子且具有1-3,优选1或2,尤其是1个碳-碳双键的那些。在具有1个碳-碳双键的情况下,碳-碳双键可以在末端(α-烯烃)或在中间。然而,优选α-烯烃,更优选具有3-6个碳原子的α-烯烃,如丙烯、1-丁烯、1-戊烯和1-己烯。
合适的(甲基)丙烯酸酯的实例为(甲基)丙烯酸与C1-C10链烷醇,尤其是与甲醇、乙醇、丙醇、异丙醇、正丁醇、仲丁醇、异丁醇、叔丁醇、戊醇、己醇、庚醇、辛醇、2-乙基己醇、壬醇和癸醇的酯。
合适的链烯基羧酸酯的实例为具有2-20个碳原子且其烃基可以为线性或支化的羧酸的乙烯基和丙烯基酯。其中优选乙烯基酯。在具有支化烃基的羧酸中,优选其支链在羧基的α-位的那些,特别优选α-碳原子为叔碳原子,即优选羧酸为新羧酸。然而,优选羧酸的烃基为线性。
合适的链烯基羧酸酯的实例为乙酸乙烯酯、丙酸乙烯酯、丁酸乙烯酯、2-乙基己酸乙烯酯、新戊酸乙烯酯、己酸乙烯酯、新壬酸乙烯酯、新癸酸乙烯酯和对应的丙烯基酯,然而优选乙烯基酯。特别优选的链烯基羧酸酯为乙酸乙烯酯。
特别优选从链烯基羧酸酯中选择烯属不饱和单体。
含有两个或更多个不同的共聚的链烯基羧酸酯的共聚物也是合适的,并且这些聚合物的区别在于链烯基官能和/或羧基。除链烯基羧酸酯外还含有至少一种共聚的烯烃和/或至少一种共聚的(甲基)丙烯酸酯的共聚物同样适合。
烯属不饱和单体基于整个共聚物优选以1-50摩尔%,更优选10-50摩尔%,尤其是5-20摩尔%的量共聚于聚合物中。
共聚物(aa)的数均分子量Mn优选为1000-20000,更优选1000-10000,尤其是1000-6000。
梳形聚合物(ab)的实例为描述于″Comb-Like Polymers.Structure andProperties″,N.A.Platéand V.P.Shibaev,J.PoIy.Sci.MacromolecularRevs.8,第117-253页(1974)中的那些。在其中描述的那些中,合适的梳形聚合物的实例为式II的那些:
其中
D为R17、COOR17、OCOR17、R18、OCOR17或OR17,
E为H、CH3、D或R18,
G为H或D,
J为H、R18、R18COOR17、芳基或杂环,
K为H、COOR18、OCOR18、OR18或COOH,
L为H、R18、COOR18、OCOR18、COOH或芳基,
其中
R17为具有至少10个碳原子,优选具有10-30个碳原子的烃基,
R18为具有至少1个碳原子,优选具有1-30个碳原子的烃基,
m为1.0-0.4的摩尔分数,和
n为0-0.6的摩尔分数。
优选的梳形聚合物例如可通过使马来酸酐或富马酸与另一烯属不饱和单体如α-烯烃或不饱和酯如乙酸乙烯酯共聚,然后用具有至少10个碳原子的醇酯化酸酐或酸官能而得到。进一步优选的梳形聚合物为α-烯烃与酯化的共聚单体的共聚物,例如苯乙烯与马来酸酐的酯化的共聚物或苯乙烯与富马酸的酯化的共聚物。梳形聚合物的混合物也是合适的。梳形聚合物也可以为聚富马酸酯或聚马来酸酯。乙烯基醚的均聚物和共聚物也是合适的梳形聚合物。
合适的聚氧化烯(ac)的实例为聚氧化烯酯、醚、酯/醚及其混合物。聚氧化烯化合物优选含有至少一个线性烷基,更优选至少两个线性烷基,其中所述线性烷基具有10-30个碳原子且聚氧化烯基团的分子量至多为5000。聚氧化烯基团的烷基优选含有1-4个碳原子。这类聚氧化烯化合物例如描述于EP-A-0 061 895以及US 4,491,455中,此处完全引入作为参考。优选的聚氧化烯酯、醚和酯/醚具有通式III:
其中
R19和R20各自独立地为R21、R21-CO-、R21-O-CO(CH2)z-或R21-O-CO(CH2)z-CO,其中R21为线性C1-C30烷基,
y为1-4的数
x为2-200的数,和
z为1-4的数。
优选其中R19和R20均为R21的式III的聚氧化烯化合物为数均分子量为100-5000的聚乙二醇和聚丙二醇。优选其中基团R19和R20中的一个为R21且另一个为R21-CO-的式III的聚氧化烯为具有10-30个碳原子的脂肪酸如硬脂酸或山萮酸的聚氧化烯酯。优选其中R19和R20均为基团R21-CO-的式III的聚氧化烯化合物为具有10-30个碳原子的脂肪酸,优选硬脂酸或山萮酸的二酯。
合适的是油溶性的极性氮化合物(ad)可以为阴离子性或非离子性,且优选具有至少一个,更优选至少两个式>NR22的取代基,其中R22为C8-C40烃基。氮取代基也可以为季铵化形式,即以阳离子形式。这类氮化合物的实例包括可通过使至少一种被至少一个烃基取代的胺与具有1-4个羧基的羧酸或与其合适的衍生物反应而得到的铵盐和/或酰胺。胺优选含有至少一个线性C8-C40烷基。合适的伯胺的实例包括辛胺、壬胺、癸胺、十一烷胺、十二烷胺、十四烷胺和高级的线性同系物。合适的仲胺的实例包括双十八烷基胺和甲基山蓊基胺。胺混合物,尤其是可在工业规模上得到的胺混合物,如脂肪胺或氢化牛油脂肪胺(tallamine)也是合适的,例如如UllmannsEncyclopedia of Industrial Chemistry,第6版,2000电子版,″Amines,aliphatic″章中所述。适合反应的酸的实例包括被长链烃基取代的环己烷-1,2-二甲酸、环己烯-1,2-二甲酸、环戊烷-1,2-二甲酸、萘二甲酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸和琥珀酸。
极性氮化合物的其它实例为带有至少两个式-A-NR23R24的取代基的环体系,其中A为任选插入一个或多个选自O、S、NR35和CO的基团的线性或支化的脂族烃基,且R23和R24各自为任选插入一个或多个选自O、S、NR35和CO的基团,和/或被一个或多个选自OH、SH和NR35R36的基团取代的C9-C40烃基,其中R35为任选插入一个或多个选自CO、NR35、O和S的结构部分,和/或被一个或多个选自NR37R38、OR37、SR37、COR37、COOR37、CONR37R38、芳基或杂环基的基团取代的C1-C40烷基,其中R37和R38各自独立地选自H或C1-C4烷基;且R36为H或R35。
A优选为亚甲基或具有2-20个亚甲基单元的聚亚甲基。合适的R23和R24基团的实例包括2-羟基乙基、3-羟基丙基、4-羟基丁基、2-酮丙基、乙氧基乙基和丙氧基丙基。环状体系可以为同素环、杂环、稠合多环或非稠合多环体系。环体系优选为碳芳族或杂芳族,尤其是碳芳族。这种多环体系的实例包括稠合的苯型结构如萘、蒽、菲和芘,稠合的非苯型结构如甘菊环、茚、二氢化茚和芴,非稠合的多环如联苯,杂环如喹啉、吲哚、二氢吲哚、苯并呋喃、香豆素、异香豆素、苯并噻酚、咔唑、二苯并呋喃和硫化二苯撑,非芳族或部分饱和的环体系如萘烷,以及三维结构如α-蒎烯、莰烯、冰片烯、降冰片烷、降冰片烯、双环辛烷和双环辛烯。
合适的极性氮化合物的其它实例为长链伯胺或仲胺与含羧基聚合物的缩合物。
上述极性氮化合物描述于WO 00/44857以及其中引用的参考文献中,此处完全引入作为参考。
合适的极性氮化合物还例如描述于DE-A-198 48 621、DE-A-196 22052和EP-B-398 101中,此处引入作为参考。
合适的磺基羧酸/磺酸及其衍生物(ae)的实例为通式IV的那些:
其中
Y为SO3 -(NR25 3R26)+、SO3 -(NHR25 2R26)+、SO3 -(NH2R25R26)、SO3 -(NH3R26)或SO2NR25R26,
X为Y、CONR25R27、CO2 -(NR25 3R27)+、CO2 -(NHR52 2R27)+、R28-COOR27、NR25COR27、R28OR27、R28OCOR27、R28R27、N(COR25)R27或Z-(NR25 3R27)+,
其中
R25为烃基
R26和R27各自为烷基、烷氧基烷基或在主链中具有至少10个碳原子的聚烷氧基烷基,
R28为C2-C5亚烷基,
Z-为一个阴离子等价物,和
A和B各自为烷基、链烯基或二取代的烃基,或者与它们键接的碳原子一起形成芳族或脂环族环体系。
这类磺基羧酸和磺酸及其衍生物描述于EP-A-0 261 957中,此处完全引入作为参考。
合适的聚(甲基)丙烯酸酯(af)为丙烯酸酯和甲基丙烯酸酯的均聚物和共聚物。优选衍生于C1-C40醇的丙烯酸酯/均聚物。还优选至少两种不同(甲基)丙烯酸的共聚物,所述不同在于酯化的醇。共聚物也可含有其它不同的共聚的烯属不饱和单体。聚合物的重均分子量优选为50000-500000。特别优选的聚合物为甲基丙烯酸和饱和C14醇和C15醇的甲基丙烯酸酯的共聚物,其中酸基被氢化的牛油脂肪胺中和。合适的聚(甲基)丙烯酸酯例如描述于WO 00/44857中,此处完全引入作为参考。
C2)润滑改进剂
常规的润滑改进剂例如包括羧酸,尤其是脂肪酸及其酯,尤其是与多元醇的酯,这些酸和酯的混合物,无灰燃烧的N-酰基化合物如聚链烯基琥珀酰胺,所述酸和/或酯与这些N-酰基化合物的混合物,例如如WO96/23855中所述,二(羟基烷基)脂肪胺或羟基乙酰胺。
C3)稀释剂
本发明添加剂经常与溶剂或稀释剂一起配制。合适的稀释剂例如为在原油加工中得到的馏分如煤油、石脑油或光亮油。另外合适的是芳族和脂族烃和烷氧基链烷醇。优选用于中间馏分,尤其是用于柴油燃料的稀释剂为石脑油、煤油、柴油燃料、芳烃,例如Solvent Naphtha heavy,SolvessoR或ShellsolR以及这些溶剂和稀释剂的混合物。
D)燃料和润滑剂
根据本发明优选被添加的燃料为汽油燃料和柴油如柴油燃料、燃料油或煤油,其中特别优选柴油燃料。
柴油燃料例如是沸程通常为100-400℃的矿物油提余液,这些柴油燃料通常是95%点高达360℃或甚至更高的蒸馏物。这些也可以为″Ultra LowSulphur Diesel″或″City Diesel″,其特征在于最大95%点例如为345℃且最大硫含量为0.005重量%,或95%点例如为285℃且最大硫含量为0.001重量%。除可通过精炼得到的柴油燃料外,合适的还有可通过煤气化或气体液化(“气转液”(GTL)燃料)而得到的那些。同样合适的是上述柴油燃料与可再生燃料如生物柴油或生物乙醇的混合物。
特别优选将本发明添加剂用于添加低硫含量的柴油燃料,即硫含量低于0.05重量%,优选低于0.02重量%,尤其是低于0.005重量%,特别是低于0.001重量%。
下列实施例阐述本发明,而不是限制本发明。
实施例
制备实施例1:
制备式II的聚异丁烯基琥珀酰亚胺
(R3,R4=甲基,x,z=3,y=1,R=聚异丁烯,Mn=550)
在装有氮气开关、内接触式热传感器和具有冷凝器的蒸馏头的四颈烧瓶中首先在氮气和140℃下装入聚异丁烯基琥珀酸酐(PIBSA)(聚异丁烯基链的Mn=550)在2-乙基己醇中的混合物。在强烈搅拌下迅速滴加入N,N-二甲基二亚丙基三胺(DMAPAPA)。PIBSA与所用胺的摩尔比为1∶1.05(琥珀酸基团∶胺)。观察到放热反应且温度升至151℃。随后,将反应混合物加热至170℃,并在氮气下搅拌2.5小时。然后,施用500毫巴的真空30分钟,除去所存在的醇。最后,用Solvesso150将混合物稀释为50%的溶液。
制备实施例2:
制备式II的聚异丁烯基琥珀酰亚胺
(R3,R4=甲基,x,z=3,y=1,R=聚异丁烯基,Mn=1000)
重复实施例1的程序,不同之处在于使用相应摩尔量的PIBSA 1000(聚异丁烯基链的Mn=1000)代替PIBSA 550。
应用实施例:
测定本发明多胺的清洁活性
在标准化测试发动机XUD9(Peugeot发动机)中使用CEC F23 A 01测试方法且测定了本发明多胺相比于市售清洁添加剂的清洁能力。在该测试中,喷嘴的碳化程度在注射喷嘴中经由空气限流以0.1mm的针距测定。100%的限流是指完全碳化;0%是指没有碳化。
使用下列燃料:
-Haltermann RF 93
-根据EN 590的柴油燃料(S含量<50ppm)
-根据EN 590的柴油燃料(S含量<10ppm)
使用具有去垢作用的下列添加剂:
-Kerocom PIBSI:通过使聚异丁烯琥珀酸酐(聚异丁烯基链的Mn=1000)和四亚乙基五胺以1∶1.05的摩尔比(琥珀酸∶胺)反应而得到的聚异丁烯琥珀酰亚胺
-PIBSI I:根据制备实施例1
-PIBSI II:根据制备实施例2
-多胺:二[3-(N,N-二甲基氨基)丙基]胺(式I化合物,其中R1,R2,R3,R4=甲基,x,z=3且y=1)
对于所有使用的PIBSI,使用具有可比的琥珀酰化程度的PIBSA。
在上述测试中,对以不同剂量在不同柴油燃料中的这些添加剂的去垢作用进行了检测。所测定的限流百分数值汇集在下表1中:
清洁剂 | 剂量[ppm] | 燃料 | 限流[%] |
Kerocom PIBSI(对比) | 52 | RF 93 | 75 |
70 | EN 590 S<50ppm | 68 | |
66 | EN 590 S<10ppm | 67 | |
PIBSI I | 30 | RF 93 | 37 |
PIBSI II | 30 | RF 93 | 7 |
15 | RF 93 | 37 | |
15 | EN 590 S<10ppm | 61 | |
15 | EN 590 S<50ppm | 61 | |
多胺 | 15 | RF 93 | 56 |
相对于所使用的对比物质,在同样较低的剂量下本发明添加剂明显表现出更好的清洁活性。
Claims (22)
1.通式I的化合物作为清洁添加剂在燃料和润滑剂中的用途:
R1R2N((CH2)xNH)y(CH2)zNR3R4 (I)
其中
R1、R2、R3和R4各自独立地为H或C1-C10烷基,但R1和R2不同时为H,R3和R4也不同时为H;或R1和R2与它们所键接的氮原子一起形成C4-C6二羧酰亚胺环,所述环由至少一个数均分子量Mn为100-2500的聚链烯基R取代;
y为1-100的整数,和
x和z独立地为2-12的整数。
2.根据权利要求1的用途,作为清洁添加剂用于柴油燃料。
3.根据权利要求1或2的用途,用于在柴油发动机中降低喷嘴碳化。
4.根据前述权利要求中任一项的用途,其中所述化合物具有如下通式II:
其中x、y、z、R、R3和R4各自如上所定义。
5.根据前述权利要求1-4中任一项的用途,其中R为聚异丁烯基。
6.根据权利要求5的用途,其中所述聚异丁烯基的Mn为约500-1000。
7.根据权利要求1的式I化合物的用途,其中R1、R2、R3和R4各自独立地为H或C1-C10烷基,但R1和R2不同时为H,R3和R4也不同时为H且x、y和z各自如上所定义。
8.根据前述权利要求中任一项的用途,其中x和z各自独立地为2-4的整数且y为1、2或3。
9.根据前述权利要求中任一项的用途,其中R3和R4各自独立地为H或C1-C4烷基,但R3和R4不同时为H。
10.根据前述权利要求中任一项的用途,其中R3和R4同时为C1-C10烷基。
11.根据前述权利要求中任一项的用途,其中R3和R4各自为C1-C4烷基。
12.根据权利要求7的用途,其中R1、R2、R3和R4各自为C1-C4烷基。
13.包含式I酰亚胺化合物的反应产物作为清洁添加剂在根据权利要求1-3中任一项的用途,其中所述反应产物可通过使被至少一个数均分子量Mn为100-2500的聚链烯基R取代的环状C4-C6二羧酸酐与式III的多胺反应,合适的话随后除去反应混合物的挥发性成分而得到:
H2N((CH2)xNH)y(CH2)zNR3R4 (III)
其中x、y、z、R3和R4各自如上所定义。
14.根据权利要求13的用途,包含至少一种式II化合物。
15.根据前述权利要求中任一项的用途,与式I化合物外的至少一种选自如下的其它常规添加剂结合:清洁添加剂、载体油、缓蚀剂、磨耗降低添加剂、十六烷值改进剂、反乳化剂、消泡剂、溶剂、加溶剂、抗氧化剂、金属减活剂、除臭剂和冷流改进剂以及包含一种或多种这些添加剂的混合物。
16.根据前述权利要求中任一项的用途,其中式I添加剂以导致80%的最大碳化程度的量加入,所述碳化程度根据CEC F23 A 01(在XUD9测试发动机中以0.1mm的针距)经由空气限流百分数测量。
17.一种燃料组合物,包含大部分的沸程为100-500℃的烃燃料,有效量的至少一种如权利要求1-14中任一项所定义的式I清洁添加剂。
18.根据前述权利要求中任一项的组合物或用途,其中所述燃料包括中间馏分燃料。
19.一种润滑剂组合物,在常规润滑剂中包含至少有效量的至少一种如权利要求1-14中任一项所定义的式I清洁添加剂。
20.一种添加剂浓缩物,包含与至少一种其它常规燃料或润滑剂添加剂结合的至少一种如权利要求1-14中任一项所定义的式I清洁添加剂。
21.一种制备具有改进的清洁燃料进入系统作用的燃料组合物的方法,其中将有效量的至少一种如权利要求1-14中任一项所定义的化合物或根据权利要求20的添加剂浓缩物加入市售燃料组合物中。
22.一种制备具有改进的清洁作用的润滑剂组合物的方法,其中将有效量的至少一种如权利要求1-14中任一项所定义的化合物或根据权利要求20的添加剂浓缩物加入市售润滑剂组合物中。
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-
2005
- 2005-08-05 EP EP05771862A patent/EP1789520A1/de not_active Withdrawn
- 2005-08-05 AU AU2005270367A patent/AU2005270367A1/en not_active Abandoned
- 2005-08-05 BR BRPI0514160-5A patent/BRPI0514160A/pt not_active IP Right Cessation
- 2005-08-05 CA CA002576014A patent/CA2576014A1/en not_active Abandoned
- 2005-08-05 MX MX2007000844A patent/MX2007000844A/es unknown
- 2005-08-05 US US11/573,274 patent/US20070214713A1/en not_active Abandoned
- 2005-08-05 KR KR1020077004596A patent/KR20070049178A/ko not_active Application Discontinuation
- 2005-08-05 WO PCT/EP2005/008533 patent/WO2006015818A1/de active Application Filing
- 2005-08-05 JP JP2007524294A patent/JP2008509236A/ja not_active Withdrawn
- 2005-08-05 CN CNA2005800265887A patent/CN1993449A/zh active Pending
-
2007
- 2007-02-19 NO NO20070929A patent/NO20070929L/no not_active Application Discontinuation
-
2010
- 2010-01-29 US US12/696,213 patent/US20100205852A1/en not_active Abandoned
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103484176A (zh) * | 2012-06-13 | 2014-01-01 | 雅富顿化学公司 | 用于改善燃料喷射发动机性能的燃料添加剂 |
CN103484176B (zh) * | 2012-06-13 | 2016-02-03 | 雅富顿化学公司 | 用于改善燃料喷射发动机性能的燃料添加剂 |
CN103923712A (zh) * | 2013-01-16 | 2014-07-16 | 雅富顿化学公司 | 用于改进在燃料喷射发动机中的性能的汽油燃料组合物 |
CN103923712B (zh) * | 2013-01-16 | 2016-05-04 | 雅富顿化学公司 | 用于改进在燃料喷射发动机中的性能的汽油燃料组合物 |
CN106459811A (zh) * | 2014-01-29 | 2017-02-22 | 巴斯夫欧洲公司 | 用于燃料和润滑剂的缓蚀剂 |
CN107922876A (zh) * | 2015-08-03 | 2018-04-17 | 道达尔销售服务公司 | 脂肪胺用于预防和/或减少发动机中的部件的金属损失的用途 |
CN107922876B (zh) * | 2015-08-03 | 2020-11-03 | 道达尔销售服务公司 | 脂肪胺用于预防和/或减少发动机中的部件的金属损失的用途 |
CN108779413A (zh) * | 2016-02-29 | 2018-11-09 | 道达尔销售服务公司 | 用于二冲程船用发动机的润滑剂 |
CN114901789A (zh) * | 2019-11-07 | 2022-08-12 | 道达尔能量联动技术公司 | 用于船用发动机的润滑剂 |
CN114901789B (zh) * | 2019-11-07 | 2022-12-30 | 道达尔能量联动技术公司 | 用于船用发动机的润滑剂 |
Also Published As
Publication number | Publication date |
---|---|
US20070214713A1 (en) | 2007-09-20 |
CA2576014A1 (en) | 2006-02-16 |
AU2005270367A1 (en) | 2006-02-16 |
KR20070049178A (ko) | 2007-05-10 |
JP2008509236A (ja) | 2008-03-27 |
US20100205852A1 (en) | 2010-08-19 |
MX2007000844A (es) | 2007-04-17 |
WO2006015818A1 (de) | 2006-02-16 |
NO20070929L (no) | 2007-05-04 |
BRPI0514160A (pt) | 2008-06-03 |
EP1789520A1 (de) | 2007-05-30 |
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