EP0698656A1 - Produits de réaction de polyènes solubles dans l'huile - Google Patents
Produits de réaction de polyènes solubles dans l'huile Download PDFInfo
- Publication number
- EP0698656A1 EP0698656A1 EP95202242A EP95202242A EP0698656A1 EP 0698656 A1 EP0698656 A1 EP 0698656A1 EP 95202242 A EP95202242 A EP 95202242A EP 95202242 A EP95202242 A EP 95202242A EP 0698656 A1 EP0698656 A1 EP 0698656A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- reagent
- reaction product
- product according
- unsaturated carboxylic
- ethylenically unsaturated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000007795 chemical reaction product Substances 0.000 title claims abstract description 46
- 150000004291 polyenes Chemical class 0.000 title description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 67
- 239000000203 mixture Substances 0.000 claims abstract description 28
- 239000000654 additive Substances 0.000 claims abstract description 19
- 239000010687 lubricating oil Substances 0.000 claims abstract description 19
- 229920000768 polyamine Polymers 0.000 claims abstract description 16
- 239000000047 product Substances 0.000 claims abstract description 15
- 239000000446 fuel Substances 0.000 claims abstract description 13
- 230000000996 additive effect Effects 0.000 claims abstract description 10
- 239000002270 dispersing agent Substances 0.000 claims abstract description 9
- 239000012141 concentrate Substances 0.000 claims abstract description 8
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 229920000098 polyolefin Polymers 0.000 claims description 10
- 239000012530 fluid Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 5
- 101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 101150113676 chr1 gene Proteins 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000005673 monoalkenes Chemical class 0.000 claims description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000004642 Polyimide Substances 0.000 description 17
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 17
- 229920001721 polyimide Polymers 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 15
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 14
- 239000008096 xylene Substances 0.000 description 14
- 229920002732 Polyanhydride Polymers 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 239000002585 base Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- 239000011572 manganese Substances 0.000 description 10
- 238000010183 spectrum analysis Methods 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 229920002367 Polyisobutene Polymers 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000003444 phase transfer catalyst Substances 0.000 description 6
- 229960002317 succinimide Drugs 0.000 description 6
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000002199 base oil Substances 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 5
- 229920005652 polyisobutylene succinic anhydride Polymers 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229940014800 succinic anhydride Drugs 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- FMGGHNGKHRCJLL-UHFFFAOYSA-N 1,2-bis(chloromethyl)benzene Chemical group ClCC1=CC=CC=C1CCl FMGGHNGKHRCJLL-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000010688 mineral lubricating oil Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- PAHUTFPWSUWSCR-BHPSOXLSSA-N (z)-2-methylbut-2-enedioic acid Chemical compound OC(=O)C(/C)=C\C(O)=O.OC(=O)C(/C)=C\C(O)=O PAHUTFPWSUWSCR-BHPSOXLSSA-N 0.000 description 2
- KGKAYWMGPDWLQZ-UHFFFAOYSA-N 1,2-bis(bromomethyl)benzene Chemical group BrCC1=CC=CC=C1CBr KGKAYWMGPDWLQZ-UHFFFAOYSA-N 0.000 description 2
- OYSVBCSOQFXYHK-UHFFFAOYSA-N 1,3-dibromo-2,2-bis(bromomethyl)propane Chemical compound BrCC(CBr)(CBr)CBr OYSVBCSOQFXYHK-UHFFFAOYSA-N 0.000 description 2
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 2
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000007866 anti-wear additive Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229920001973 fluoroelastomer Polymers 0.000 description 2
- 239000003502 gasoline Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 150000002611 lead compounds Chemical class 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- -1 polysiloxanes Polymers 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 150000003443 succinic acid derivatives Chemical class 0.000 description 2
- 239000010689 synthetic lubricating oil Substances 0.000 description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 description 1
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- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 1
- RBBNTRDPSVZESY-UHFFFAOYSA-N 1,10-dichlorodecane Chemical compound ClCCCCCCCCCCCl RBBNTRDPSVZESY-UHFFFAOYSA-N 0.000 description 1
- SIBVHGAPHVRHMJ-UHFFFAOYSA-N 1,11-dibromoundecane Chemical compound BrCCCCCCCCCCCBr SIBVHGAPHVRHMJ-UHFFFAOYSA-N 0.000 description 1
- ZJJATABWMGVVRZ-UHFFFAOYSA-N 1,12-dibromododecane Chemical compound BrCCCCCCCCCCCCBr ZJJATABWMGVVRZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 1
- OVISMSJCKCDOPU-UHFFFAOYSA-N 1,6-dichlorohexane Chemical compound ClCCCCCCCl OVISMSJCKCDOPU-UHFFFAOYSA-N 0.000 description 1
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- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- WXYMNDFVLNUAIA-UHFFFAOYSA-N 1,8-dichlorooctane Chemical compound ClCCCCCCCCCl WXYMNDFVLNUAIA-UHFFFAOYSA-N 0.000 description 1
- WGAXVZXBFBHLMC-UHFFFAOYSA-N 1,9-dibromononane Chemical compound BrCCCCCCCCCBr WGAXVZXBFBHLMC-UHFFFAOYSA-N 0.000 description 1
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- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
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- ONPJWQSDZCGSQM-UHFFFAOYSA-N 2-phenylprop-2-enoic acid Chemical compound OC(=O)C(=C)C1=CC=CC=C1 ONPJWQSDZCGSQM-UHFFFAOYSA-N 0.000 description 1
- SYIUWAVTBADRJG-UHFFFAOYSA-N 2H-pyran-2,6(3H)-dione Chemical compound O=C1CC=CC(=O)O1 SYIUWAVTBADRJG-UHFFFAOYSA-N 0.000 description 1
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- 150000001266 acyl halides Chemical class 0.000 description 1
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- 229910052783 alkali metal Inorganic materials 0.000 description 1
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- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
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- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000013556 antirust agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
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- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
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- PDEDQSAFHNADLV-UHFFFAOYSA-M potassium;disodium;dinitrate;nitrite Chemical compound [Na+].[Na+].[K+].[O-]N=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PDEDQSAFHNADLV-UHFFFAOYSA-M 0.000 description 1
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- 150000003440 styrenes Chemical class 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 150000005671 trienes Chemical class 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- OFLNOEMLSXBOFY-UHFFFAOYSA-K trisodium;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical class [Na+].[Na+].[Na+].[O-]P([O-])([S-])=S OFLNOEMLSXBOFY-UHFFFAOYSA-K 0.000 description 1
- BICRHLFMOFSTTN-UHFFFAOYSA-N undeca-1,9-diene Chemical compound CC=CCCCCCCC=C BICRHLFMOFSTTN-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
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- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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Definitions
- the present invention relates to reaction products of polyenes, a process for their preparation, lubricating oil compositions, fuel compositions and additive concentrates containing them and their use as dispersant additives.
- European Patent Application No. 94200496.1 describes the use, as dispersant additives in lubricating oils (luboils), of mono- and bis-cyclopentadiene derivatives of the general formula in which R1 and R2 each represent a hydrogen atom, or together represent a carbon-carbon single bond; each of R4 and R5 independently represents a hydrogen atom, or a C1-C20 alkyl or phenyl group, each of which may be optionally substituted; R6 represents a hydrogen atom, or a C1-C20 alkyl or phenyl group, each of which may be optionally substituted and R7 represents a group -CH2-NHR8 in which R8 represents an optionally substituted alkyl group, or a group -COX wherein X represents an optionally substituted alkoxy group or -NHR8 where R8 is as defined above; or R6 and R7 together represent a group where R8 is as defined above; x is 1 to 6, preferably 1 to 4; and each R3
- the acylating reagent (A) is the reaction product of (B) a C4-C20 polyene or oligomer prepared therefrom and (C) an ethylenically unsaturated carboxylic reagent.
- the reaction is conveniently carried out in the presence of a suitable solvent at elevated temperature (i.e. above ambient temperature (20°C)), e.g. in the temperature range 25 to 200°C, often under reflux conditions and, where necessary, at elevated pressure, e.g. in the range from 2 to 100 x 105 Pa .
- solvents examples include hydrocarbon solvents such as hexane, cyclohexane, toluene and xylene; ether solvents such as diethyl ether, tetrahydrofuran and 1,4-dioxane; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile; alcohols such as 1-pentanol (amyl alcohol) and 2-methyl-2-propanol (tert-butyl alcohol); and chlorohydrocarbons such as dichloromethane.
- hydrocarbon solvents such as hexane, cyclohexane, toluene and xylene
- ether solvents such as diethyl ether, tetrahydrofuran and 1,4-dioxane
- amides such as dimethylformamide and dimethylacetamide
- nitriles such as acetonitrile
- alcohols such as 1-pentano
- Reagent (B) is a C4-C20, preferably C4-C18, more preferably C4-C16 and especially C5-C12, polyene or oligomer prepared therefrom.
- the polyene contains two or more, preferably two (2) to four (4) carbon-carbon double bonds.
- Particularly preferred polyenes are those containing three (3) carbon-carbon double bonds (trienes), and especially two (2) carbon-carbon double bonds (dienes).
- C4-C20 polyenes include 1,5-hexadiene, 1,7-octadiene, 1,9-undecadiene, (di)cyclopentadiene, norbornadiene, 1,2,4-trivinylcylcohexane, 1,3,5,7-cyclooctatetraene and 1,5,9-cyclododecatriene; (di)cyclopentadiene is the most preferred polyene.
- the polyenes may be used as such or in the form of oligomers.
- oligomer denotes a homooligomer or co-oligomer of a diene, comprising at least two diene monomer units.
- the oligomers may have number average molecular weights (M n ) up to 3000, e.g. in the range from 100 to 3000, preferably from 200 to 2500, more preferably from 300 to 2000 and especially from 400 to 1500.
- Preferred oligomers are co-oligomers obtainable by reacting (di)cyclopentadiene or a cyclopentadienylide, e.g. an alkali metal, preferably sodium, cyclopentadienylide, with a compound of the general formula RL m (i) wherein m is an integer from 2 to 6, R represents a hydrocarbyl group or a polyoxyalkylene group, each of which contains from 2 to 30, preferably from 4 to 22, more preferably from 4 to 12 and advantageously from 5 to 8, carbon atoms and L represents a leaving group.
- the group R is preferably an alkyl or xylyl group.
- the leaving group, L may, for example, be a mesylate, tosylate or hydroxyl group but is preferably a halogen atom, particularly a chlorine atom.
- Examples of compounds of formula (i) include ⁇ , ⁇ '-dihaloxylenes (e.g. ⁇ , ⁇ '-dibromoxylene, ⁇ , ⁇ '-dichloroxylene), ⁇ , ⁇ ', ⁇ '-trihalomesitylenes (e.g. ⁇ , ⁇ ', ⁇ ''-trichloromesitylene), pentaerythrityl tetrabromide, C6 or higher dihaloalkanes (e.g.
- Preparation of the oligomers may conveniently be carried out at low temperature, e.g. from -5 to 5°C, in the presence of a suitable solvent, e.g. a hydrocarbon solvent such as toluene or xylene, or an ether solvent such as tetrahydrofuran.
- a suitable solvent e.g. a hydrocarbon solvent such as toluene or xylene, or an ether solvent such as tetrahydrofuran.
- a suitable solvent e.g. a hydrocarbon solvent such as toluene or xylene, or an ether solvent such as tetrahydrofuran.
- a phase transfer catalyst such as that commercially available under the trade mark "Adogen 464".
- the ethylenically unsaturated carboxylic reagent (C) contains a total of at least 3 carbon atoms, preferably a total of from 3 to 50, more preferably from 3 to 30, still more preferably from 4 to 20, and even more preferably from 4 to 10, carbon atoms.
- the ethylenically unsaturated carboxylic reagent (C) may be an alpha-beta olefinic unsaturated carboxylic reagent as described in Page 6, lines 15 to 48 of EP-B-0285609 or Page 6, lines 11 to 39 of EP-B-0287569, e.g.
- anhydrides e.g. maleic anhydride (C4), glutaconic anhydride (C5), itaconic anhydride (C5), citraconic anhydride (
- the ethylenically unsaturated carboxylic reagent (C) is selected from monoethylenically unsaturated C4-C10 dicarboxylic acids and anhydrides, of which maleic anhydride is most preferred.
- the same or different ethylenically unsaturated carboxylic reagents (C) may be used.
- maleic anhydride is used in the preparation of both reagents (A) and (D).
- Reagent (D) is a polyalkenyl derivative of an ethylenically unsaturated carboxylic reagent (C), the preparation of which is known in the art.
- reagent (D) is a polyalkenyl derivative of an ethylenically unsaturated carboxylic reagent such as maleic anhydride
- it may conveniently be prepared by mixing a polyalkene with a specified amount of maleic anhydride and passing chlorine through the mixture, e.g. as described in GB-A-949,981.
- the derivative may be prepared by reacting thermally, at an appropriate temperature, the polyalkene with a specified amount of maleic anhydride, e.g.
- a particularly preferred process for preparing such a derivative involves reacting the polyalkene with maleic anhydride in a mol ratio maleic anhydride to polyalkene of greater than 1:1, at a temperature in the range from 150 to 260°C and in the presence of a polyaddition-inhibiting amount of a sulphonic acid.
- the polyalkene from which reagent (D) is derived may be a homopolymer or copolymer, for example of at least one C2-C10 monoolefin.
- the polyalkene is a polymer of at least one C2-C5 monoolefin, e.g. an ethylene-propylene copolymer.
- the monoolefin is preferably a C3-C4 olefin, in particular propylene or isobutylene, and preferred polyalkenes derived therefrom include polyisobutylenes and atactic or isotactic propylene oligomers.
- Polyisobutylenes such as that sold by BASF under the trade mark “GLISSOPAL” and those sold by the British Petroleum Company under the trade marks "Ultravis”, “Hyvis” and “Napvis”, e.g. "Hyvis 75", “Hyvis 120", “Hyvis 200” and “Napvis 120" polyisobutylenes,.are especially preferred for use in the present invention.
- the polyalkene has a number average molecular weight (M n ) preferably in the range from 300 to 7000, more preferably from 500 to 5000, still more preferably from 1000 to 4000 and advantageously from 2000 to 3000.
- M n number average molecular weight
- the polyamine (E) contains at least two -NH2 and/or -NH groups, the groups each having at least one active hydrogen thereon.
- Examples of polyamines useful in the present invention are those described in the text from Page 16, line 21 to Page 19, line 53 of EP-B-0287569.
- the polyamine (E) is a compound of the general formula H2N-(CHR1) x -CH2-[A-CH2-(CHR1) x ] y -NH2 (ii) wherein A is -NH or -O-, each R1 independently represents a hydrogen atom or a methyl group, x is in the range 1 to 3, and y is in the range 1 to 10 when A is -NH or y is in the range 1 to 200 when A is -O-.
- each R1 represents a hydrogen atom, and y is in the range 1 to 8; or when A is -O-, then x is 1, each R1 represents a methyl group and y is in the range 1 to 50.
- Reagent (F) is the pre-formed product of reagents (D) and (E) and is prepared according to techniques conventional in the art.
- reagent (D) is a polyalkenyl derivative of maleic anhydride
- reagent (E) is an ethylene polyamine
- they may conveniently be reacted together in a molar ratio of (D) to (E) from 1 - 4:1, in a hydrocarbon solvent at a temperature in the range from 100 to 250°C, e.g. as described in EP-A-0587250.
- the present invention further provides a process for the preparation of a reaction product according to the invention which comprises reacting
- the process may be carried out in the absence of a solvent but is conveniently carried out in the presence of a solvent, e.g. any of those mentioned above, and at elevated temperature (i.e. above ambient temperature (20°C)), for example, in the temperature range 30 to 200°C.
- a solvent e.g. any of those mentioned above
- elevated temperature i.e. above ambient temperature (20°C)
- the process is preferably carried out under reflux conditions.
- the weight ratio of reagent (A) to reagent (D) used in the present process is preferably in the range from 1:2 to 1:1000, more preferably from 1:4 to 1:500, still more preferably from 1:5 to 1:100 and especially from 1:5 to 1:50.
- the weight ratio of reagents (A) plus (D) to reagent (E) (i.e. the ratio of the total combined weight of reagents (A) and (D) to the weight of reagent (E)) used in the present process is preferably in the range from 0.5:1 to 200:1, more preferably from 2:1 to 100:1, still more preferably from 2:1 to 50:1 and especially from 5:1 to 30:1.
- the weight ratio of reagent (A) to reagent (F) used in the present process is preferably in the range from 1:2 to 1:1000, more preferably from 1:4 to 1:500, still more preferably from 1:5 to 1:200 and, advantageously, from 1:10 to 1:100.
- the reaction product of reagents (A), (D) and (E) or reagents (A) and (F) may be used as a dispersant additive in lubricating oils.
- the present invention provides a lubricating oil composition comprising a major amount (more than 50%w) of a lubricating oil and a minor amount (less than 50%w), preferably from 0.1 to 10%w, especially from 0.5 to 5%w (active matter), of a reaction product according to the invention, the percentages by weight being based on the total weight of the composition.
- Suitable lubricating oils are natural, mineral or synthetic lubricating oils.
- Natural lubricating oils include animal and vegetable oils, such as castor oil.
- Mineral oils comprise the lubricating oil fractions derived from crude oils, coal or shale, which fractions may have been subjected to certain treatments such as clay-acid, solvent or hydrogenation treatments.
- Synthetic lubricating oils include synthetic polymers of hydrocarbons, modified alkylene oxide polymers, and ester lubricants, which are known in the art. These lubricating oils are preferably crankcase lubricating oils for spark-ignition and compression-ignition engines, but include also hydraulic lubricants, metal-working fluids and automatic transmission fluids.
- the lubricating base oil component of the compositions according to the present invention is a mineral lubricating oil or a mixture of mineral lubricating oils, such as those sold by member companies of the Royal Dutch/Shell Group under the designations "HVI", or "XHVI” (trade mark).
- the viscosity of the lubricating base oils present in the compositions according to the present invention may vary within wide ranges, and is generally from 3 to 35 mm2/s at 100°C.
- the lubricating oil compositions according to the present invention may contain various other additives, known in the art, such as viscosity index improvers, e.g. linear or star-shaped polymers of a diene such as isoprene or butadiene, or a copolymer of such a diene with optionally substituted styrene. These copolymers are suitably block copolymers and are preferably hydrogenated to such an extent as to saturate most of the olefinic unsaturation.
- Other suitable additives include dispersant V.I.
- detergents such as those based on block copolymers, or polymethacrylates, extreme pressure/anti-wear additives such as zinc or sodium dithiophosphates, ashless dispersants such as polyolefin-substituted succinimides, e.g. those described in GB-A-2 231 873, anti-oxidants, friction modifiers or metal-containing detergents such as phenates, sulphonates, alkylsalicylates or naphthenates, all of which detergents may be overbased.
- extreme pressure/anti-wear additives such as zinc or sodium dithiophosphates
- ashless dispersants such as polyolefin-substituted succinimides, e.g. those described in GB-A-2 231 873
- anti-oxidants such as phenates, sulphonates, alkylsalicylates or naphthenates, all of which detergents may be overbased.
- the reaction product of reagents (A), (D) and (E) or reagents (A) and (F) may also be used as a dispersant additive in fuels.
- the present invention further provides a fuel composition comprising a major amount (more than 50%w) of a fuel and a minor amount (less than 50%w), preferably from 0.001 to 2%w, more preferably from 0.001 to 0.5%w and especially from 0.002 to 0.2%w (active matter), of a reaction product according to the invention, the percentages by weight being based on the total weight of the composition.
- Suitable fuels include gasoline and diesel fuel. These base fuels may comprise mixtures of saturated, olefinic and aromatic hydrocarbons. They can be derived from straight-run gasoline, synthetically produced aromatic hydrocarbon mixtures, thermally catalytically cracked hydrocarbon feedstocks, hydrocracked petroleum fractions or catalytically reformed hydrocarbons.
- the fuel compositions according to the present invention may contain various other additives known in the art such as a lead compound as anti-knock additive; antiknock additives other than lead compounds such as methyl cyclopentadienyl-manganese tricarbonyl or ortho-azidophenyl; co-antiknock additives such as benzoylacetone; dehazers (e.g.
- ethoxylated glycerols such as that commercially available as “SURDYNE” (trade mark) M155 (ex Shell Chemicals, UK) or alkoxylated phenol formaldehyde polymers such as those commercially available as “NALCO” (trade mark) 7DO7 (ex Nalco), “TOLAD” (trade mark) 2683 (ex Petrolite) or “SURDYNE” (trade mark) D265, M153, M154 or M156 (ex Shell Chemicals, UK)); anti-foaming agents (e.g.
- succinic acid derivative that commercially sold by Rhein Chemie, Mannheim, Germany as "RC 4801", or polyhydric alcohol esters of a succinic acid derivative, the succinic acid derivative having on at least one of its alpha carbon atoms an unsubstituted or substituted aliphatic hydrocarbon group containing from 20 to 500 carbon atoms, e.g. the pentaerythritol diester of polyisobutylene-substituted succinic acid); reodorants; anti-wear additives; anti-oxidants (e.g.
- phenolics such as 2,6-di-tert-butylphenol, or phenylenediamines such as N,N'-di-sec-butyl-p-phenylenediamine); metal deactivators; lubricity agents (e.g. those commercially available as EC831 (ex Paramins) or "HITEC” (trade mark) 580 (ex Ethyl Corporation)); or carrier fluids such as a polyether e.g.
- polyisobutylene having from 20 to 175, particularly 35 to 150, carbon atoms, or a polyalphaolefin having a viscosity at 100°C in the range 2 x 10 ⁇ 6 to 2 x 10 ⁇ 5 m2/s (2 to 20 centistokes), being a hydrogenated oligomer containing 18 to 80 carbon atoms derived from at least one alphaolefinic monomer containing from 8 to 18 carbon atoms.
- the lubricating oil and fuel compositions of the invention may be prepared by adding the reaction product of reagents (A), (D) and (E) or reagents (A) and (F) separately to a lubricating oil or fuel.
- an additive concentrate is blended with the lubricating oil or fuel.
- Such a concentrate generally comprises an inert carrier fluid and one or more additives in a concentrated form.
- the present invention also provides an additive concentrate comprising an inert carrier fluid and from 10 to 80%w (active matter) of a reaction product according to the invention, the percentages by weight being based on the total weight of the concentrate.
- inert carrier fluids include hydrocarbons and mixtures of hydrocarbons with alcohols or ethers, such as methanol, ethanol, propanol, 2-butoxyethanol or methyl tert-butyl ether.
- the carrier fuid may be an aromatic hydrocarbon solvent such as toluene, xylene, mixtures thereof or mixtures of toluene or xylene with an alcohol.
- the carrier fluid may be a mineral base oil, such as those sold by member companies of the Royal Dutch/Shell Group under the designations "HVI” or "XHVI” (trade mark), e.g. "HVI 60" base oil.
- the present invention still further provides the use of a reaction product according to the invention as a dispersant additive.
- the present invention will be further understood from the following illustrative examples.
- M n the number average molecular weights specified for the polyisobutenyl moieties in the polyisobutenyl succinic anhydride/succinimide were determined by quantitative reaction with ozone, on the assumption that each oligomer chain contains one double bond, as will be readily understood by those skilled in the art.
- the number average molecular weights quoted were determined by modern gel permeation chromatography using polystyrene standards, e.g. as described in W.W. Yau, J.J. Kirkland and D.D. Bly, "Modern Size Exclusion Liquid Chromatography", John Wiley and Sons, New York, 1979.
- Active matter content was determined by separating inactive material from the desired active matter on an aluminium oxide column using diethyl ether as eluant; acid value was determined according to ASTM D 664; and Total Base Number (adjusted to 100% active matter) was determined in accordance with ASTM D 2896.
- a xylene solution 2454 g of a polyisobutenyl succinic anhydride (PIBSA; polyisobutenyl M n 2400) prepared by the process described in EP-A-0542380.
- PIBSA polyisobutenyl succinic anhydride
- the PIBSA/xylene solution contained 42.3%w xylene and 37.6%w active matter PIBSA.
- the acid value of the PIBSA (after removal of the xylene) was found to be 0.486 meq/g.)
- the mixture so formed was stirred with toluene (4.5 l) until it was homogeneous.
- a polyamine mixture (92.81 g) containing tetraethylene pentamine, pentaethylene hexamine and higher ethylene polyamines in a weight ratio of 1:2:1 (commercially available from Delamine B.V., Netherlands) was then added and the resulting composition heated to 120°C for four hours, with removal of water and tetrahydro-furan using a Dean and Stark trap.
- the polyanhydride derivatives obtained in (i) above (0.8g) were added, with stirring, to a reaction vessel containing toluene (300 ml), tetrahydrofuran (50 ml), triethylene tetramine (0.6 g, 4.1 mmol), and a polyisobutenyl succinic anhydride (22 g) (65%w active matter; polyisobutenyl M n 2400; acid value of 0.486 meq/g) prepared by the process described in EP-A-0542380.
- the reaction mixture was refluxed for an hour and a half, with removal of water using a Dean and Stark trap.
- Example 8 (ii) The procedure described in Example 8 (ii) was repeated using 0.72 g of the polyanhydride derivatives, 0.9 g pentaethylene hexamine and 19 g of the polyisobutenyl succinic anhydride. Infrared spectral analysis of the end product showed v max at 1770 cm ⁇ 1 (m) and 1700 cm ⁇ 1 (vs). The end product had an active matter of 65%, a total base number of 0.73 mg KOH/g and a nitrogen content of 1.3%w.
- Example 10 was repeated using different amounts of the polyanhydride derivatives and/or polyisobutylene succinimide as detailed in Table II below. Table II also shows the total base number and nitrogen content of the polyimide derivatives obtained. Table II Ex. No. Reagents Polyimide Derivatives Product of Example 1(i) (g) PIB Succinimide (g) Total Base Number (mg KOH/g) Nitrogen content (%w) 11 3 62.7 0.27 1.16 12 0.88 29.3 0.51 1.18 13 1.5 62.7 0.49 1.17 14 1.5 62.7 0.58 1.17 15 0.31 31 0.35 1.13
- Example 16 (ii) was repeated using different amounts of the polyanhydride derivatives, as indicated in Table III below.
- the end products also both had an active matter of 48%.
- the total base number and nitrogen content of the polyimide derivatives obtained are also shown in Table III.
- Table III Ex. No. Reagents Polyimide Derivatives Product of Example 16(i) (g) PIB Succinimide (g) Total Base Number (mg KOH/g) Nitrogen content (%w) 17 3 62.7 0.66 1.16 18 1.5 62.7 0.7 1.18
- 1,5-hexadiene (10 g, 0.122 mol) and maleic anhydride (50 g, 0.51 mol) in toluene (20 ml) were heated in a sealed autoclave at 180°C for 24 hours. Solvent and any unreacted maleic anhydride were removed under reduced pressure (140°C, 500 Pa) to give the crude double-ene, Diels-alder adduct (15 g). Infrared spectral analysis of the product showed v max at 1858 cm ⁇ 1 (s) and 1777 cm ⁇ 1 (s).
- polyimide derivatives of Examples 1 and 8 to 18 were incorporated in lubricating oils to give concentrations of 1.5%w active matter and tested for compatibility with fluoroelastomer seal materials according to the method of DIN 53504 and, specifically, Daimler Benz specification DB 6615. Percentage reduction in tensile strength (TS) and elongation at break (EB) were assessed. The test results depend upon the particular seal materials used, and therefore comparative series should be tested with seals from consistent batches. A low result indicates good performance.
- TS tensile strength
- EB elongation at break
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Lubricants (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP95202242A EP0698656B1 (fr) | 1994-08-24 | 1995-08-18 | Produits de réaction de polyènes solubles dans l'huile |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP94306237 | 1994-08-24 | ||
| EP94306237 | 1994-08-24 | ||
| EP95202242A EP0698656B1 (fr) | 1994-08-24 | 1995-08-18 | Produits de réaction de polyènes solubles dans l'huile |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0698656A1 true EP0698656A1 (fr) | 1996-02-28 |
| EP0698656B1 EP0698656B1 (fr) | 2000-10-18 |
Family
ID=26137257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP95202242A Expired - Lifetime EP0698656B1 (fr) | 1994-08-24 | 1995-08-18 | Produits de réaction de polyènes solubles dans l'huile |
Country Status (1)
| Country | Link |
|---|---|
| EP (1) | EP0698656B1 (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0859040A1 (fr) * | 1997-02-17 | 1998-08-19 | Ethyl Petroleum Additives Limited | L'utilisation d'additifs lubrifiants pour diminuer le mousse dans les fuels |
| EP0884375A1 (fr) * | 1997-06-05 | 1998-12-16 | The Lubrizol Corporation | Produits de réaction d'agents d'acylation carboxyliques substitués et réactifs carboxyliques à utilisation dans des combustibles et des lubrifiants |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4670173A (en) * | 1985-12-19 | 1987-06-02 | The Lubrizol Corporation | Oil-soluble reaction products of an acylated reaction product, a polyamine, and mono-functional acid |
| EP0331397A2 (fr) * | 1988-02-29 | 1989-09-06 | Exxon Chemical Patents Inc. | Additifs dispersants solubles dans des huiles et utiles dans des compositions huileuses |
| EP0556915A2 (fr) * | 1992-02-19 | 1993-08-25 | Shell Internationale Researchmaatschappij B.V. | Dispersants polymères |
| EP0613887A1 (fr) * | 1993-03-01 | 1994-09-07 | Shell Internationale Researchmaatschappij B.V. | Concentré d'additifs contenant des dérivés de cyclopentadiène pour des huiles de graissage et pour des carburants |
-
1995
- 1995-08-18 EP EP95202242A patent/EP0698656B1/fr not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4670173A (en) * | 1985-12-19 | 1987-06-02 | The Lubrizol Corporation | Oil-soluble reaction products of an acylated reaction product, a polyamine, and mono-functional acid |
| EP0331397A2 (fr) * | 1988-02-29 | 1989-09-06 | Exxon Chemical Patents Inc. | Additifs dispersants solubles dans des huiles et utiles dans des compositions huileuses |
| EP0556915A2 (fr) * | 1992-02-19 | 1993-08-25 | Shell Internationale Researchmaatschappij B.V. | Dispersants polymères |
| EP0613887A1 (fr) * | 1993-03-01 | 1994-09-07 | Shell Internationale Researchmaatschappij B.V. | Concentré d'additifs contenant des dérivés de cyclopentadiène pour des huiles de graissage et pour des carburants |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0859040A1 (fr) * | 1997-02-17 | 1998-08-19 | Ethyl Petroleum Additives Limited | L'utilisation d'additifs lubrifiants pour diminuer le mousse dans les fuels |
| EP0884375A1 (fr) * | 1997-06-05 | 1998-12-16 | The Lubrizol Corporation | Produits de réaction d'agents d'acylation carboxyliques substitués et réactifs carboxyliques à utilisation dans des combustibles et des lubrifiants |
| US5851966A (en) * | 1997-06-05 | 1998-12-22 | The Lubrizol Corporation | Reaction products of substituted carboxylic acylating agents and carboxylic reactants for use in fuels and lubricants |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0698656B1 (fr) | 2000-10-18 |
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