NO168828B - Polybutyl- eller polyisobutylaminer, fremgangsmaate for fremstilling av slike, samt drivstoff- og smoeremiddelblanding inneholdende polybutyl- eller polyisobutylaminer - Google Patents
Polybutyl- eller polyisobutylaminer, fremgangsmaate for fremstilling av slike, samt drivstoff- og smoeremiddelblanding inneholdende polybutyl- eller polyisobutylaminer Download PDFInfo
- Publication number
- NO168828B NO168828B NO871393A NO871393A NO168828B NO 168828 B NO168828 B NO 168828B NO 871393 A NO871393 A NO 871393A NO 871393 A NO871393 A NO 871393A NO 168828 B NO168828 B NO 168828B
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- Prior art keywords
- polybutyl
- residue
- general formula
- different
- same
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 21
- 239000000446 fuel Substances 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 12
- 239000000314 lubricant Substances 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 4
- 229920001083 polybutene Polymers 0.000 claims description 33
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 21
- 229920002367 Polyisobutene Polymers 0.000 claims description 14
- 238000005576 amination reaction Methods 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 238000007037 hydroformylation reaction Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 230000000887 hydrating effect Effects 0.000 claims description 6
- 229910017052 cobalt Inorganic materials 0.000 claims description 5
- 239000010941 cobalt Substances 0.000 claims description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000006294 amino alkylene group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 1
- 150000001336 alkenes Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 4
- 239000002816 fuel additive Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- -1 polybutylene Polymers 0.000 description 2
- 229920001748 polybutylene Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- 241000252073 Anguilliformes Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002044 hexane fraction Substances 0.000 description 1
- 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 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 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 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000000039 preparative column chromatography Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
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
- C10M133/58—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
-
- 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
- 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)
- C10L1/2387—Polyoxyalkyleneamines (poly)oxyalkylene amines and 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
- 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
- C10M133/54—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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
-
- 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
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- C10M2215/22—Heterocyclic nitrogen compounds
-
- 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
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
-
- 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
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
-
- 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
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/225—Heterocyclic nitrogen compounds the rings containing both nitrogen and oxygen
- C10M2215/226—Morpholines
-
- 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
- C10M2215/26—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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/30—Heterocyclic compounds
-
- 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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
-
- 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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Lubricants (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Solid Fuels And Fuel-Associated Substances (AREA)
Description
Oppfinnelsen vedrører polybutyl- eller polyisobutylaminer,
en fremgangsmåte for fremstilling av slike og drivstoff- og smøremiddelblandinger som inneholder polybutyl- eller polyisobutylaminer.
Polybutenylaminer og deres anvendelse som drivstoff- og smøre-middel-additiver har lenge vært kjent, og er eksempelvis beskrevet i US-A-3 275 554 og i DE-A-2 125 039.
Polybutenylaminene i henhold til den kjente teknikk ble fremstilt ved halogenering av polybutener og omsetning av halogenider med aminer. Ved fremstilling av disse produkter dannes ionogent halogen som må fjernes så vidtgående som mulig.
Det har på det tekniske fagområdet derfor ikke manglet på forsøk på å forbedre de kjente produkter, men fremfor alt fjerning av det ionogene halogen har ikke bare krevet kompliserte forholds-regler, men i omsetningsproduktene er det også alltid blitt igjen betydelige mengder med halogen, jfr. DE-A-2 245 918.
I DE-A-2 702 604 er det beskrevet reaktive polyisobutener som kan omsettes med maleinsyreanhydrid (MSA) og oligo- eller polyaminer til mineralolje-hjelpemidler. De således oppnåelige,mineral-oljehjelpemidler fremviser den store fordel at de er nesten fri for halogener. En ulempe er den besværlige lagring av MSA (en-reaksjon) som er forbundet med tjæredannelse, d.v.s. uønskede biprodukter.
Oppgaven ved foreliggende oppfinnelse er å tilveiebringe polybutyl- eller polyisobutylaminer og drivstoff- eller smøremiddelblandinger som forhindrer avsetting i innløpssystemet for forbrenningsmotorer, henholdsvis oppviser en spesielt god dispergeringseffekt.
Oppfinnelsen vedrører polybutyl- eller polyisobutylaminer
med den generelle formel I:
hvor ^ betyr en polybutyl- eller polyisobutylrest med 20 til 400 karbonatomer avledet fra isobuten og inntil 20 vekti n-buten, og R2 og R3' som er 1:Lke eiler forskjellige, betyr hydrogen, C1-C1Q-alkyl, fenyl, naftyl, C^-C^Q-hydroksyalkyl, en aminoalkylenrest med den generelle formel II: hvor R4 betyr en C^-C-^-alkylenrest og R5 og Rg, som er like eller forskjellige, betyr hydrogen, C-^-C^g-alkyl, fenyl, naftyl, c1~c10" hydroksyalkyl eller polybutyl eller polyisobutyl med hver gang 20 til 40 0 karbonatomer, en polyaminoalkylenrest med den generelle formel III:
hvor
restene R. hver gang er like eller forskjellige, restene R,, hver gang er like eller forskjellige, restene R^, R5 og Rg har de foranstående betydninger og m er et helt tall fra 1 til 7 , eller en polyoksyalkylenrest med den generelle formel IV:
hvor restene R4 hver gang er like eller forskjellige, og har de foranstående betydninger og n er et helt tall mellom 1 og 30, eller R2 og R3 danner sammen med det nitrogenatom som de er bundet til, en morfolinylrest, og hvor polybutyl- eller polyisobutylaminene er oppnådd ved hydroformylering av de polybutener eller polyisobutener som tilsvarer resten R^, og hydrerende aminering.
Oppfinnelsen er også rettet på fremstilling av forbindelsene med den generelle formel V ved at man hydroformylerer et tilsvarende polybuten eller polyisobuten med en rhodium- eller koboltkatalysator i nærvær av CO og H2 ved temperaturer mellom 80 og 200°C og CO/H2-trykk på inntil 600 bar, og deretter gjennomfører en hydrerende aminering av oksoproduktet. Amineringsreaksjonen blir gjennomført ved temperaturer på 80-200°C og trykk inntil 600 bar, fortrinnsvis 80-300 bar.
De således oppnådde produkter utmerker seg i forhold til de i henhold til DE-OS 1.545.487 ved halogenering og aminering oppnådde produkter ved fravær av klorforbindelser og forbedret yteevne.
Ved fremstillingen blir det hensiktsmessig anvendt et egnet, inert løsningsmiddel som nedsetter viskositeten til reaksjons-blandingen. Som løsningsmiddel egner seg fremfor alt svovelfattige alifatiske, cykloalifatiske og aromatiske hydrokarboner. Spesielt foretrukket er alifatiske løsningsmidler som er fri for svovel-forbindelser og inneholder mindre enn 1 % av aromater. De har den fordel at ved høye amineringstemperaturer frigis ikke hydrerings-varme og forbrukes ikke hydrogen. Ved aminerings- og hydroformy-leringsreaksjonen ligger innholdet av løsningsmiddel alt etter viskositeten til polymeren og løsningsmidlet mellom 0 og 70 vekt%. Større fortynning er likeså uøkonomisk som bytte av løsningsmiddel mellom oksiering og aminering.
Ved fremgangsmåten i henhold til oppfinnelsen kan det uten videre oppnås en polybutenomsetning på 80 - 90 %. Polybutenet,
som overveiende er oppbygget av isobutenenheter (isobutenandelen ligger for det meste på mer enn 80 vekt%), har eksempelvis en molekylvekt MN på 300-5000, fortrinnsvis på 500-2500. I henhold til oppfinnelsen kan man anvende såkalte reaktive polybutener, spesielt polybuten A, B, eller C. Med et reaktivt polybuten forstår man en umettet polymer med høy kjemisk enhetlighet, hvorved mer enn 10 % av dobbeltbindingene er a-stående. En måte å fremstille slikt polybuten er beskrevet i DE 2702604. En således fremstilt polymer inneholder ca. 60 % a-olefin og 30 % 6-olefin, trisubsti-tuert.
Middels reaktive polybutener oppnås for det meste ved poly-merisering av isobuten eller isobutenholdige C^-snitt med aluminium-holdige katalysatorer, de er mindre kjemiske enhetlige og inneholder bare små mengder av a-olefin, for det meste under 10 %. Signalene ved C-^-NMR viser forskjellen. Den 6-stående, trisub-stituerte, kjemiske enhetlige andel utgjør ved polybuten B ca. 40 %, a-olefinandelen ca. 10 %. Polybuten A blir endelig betegnet som mindre reaktiv og oppviser ikke mer nevneverdig kjemisk enhetlige andeler.
Spesielt egnede polybutener og polyisobutener for fremstilling av polyaminene i henhold til oppfinnelsen med den generelle formel I og alkoholene i henhold til oppfinnelsen med den generelle formel V, er slike som oppviser en midlere polymerisasjonsgrad P fra 10 til 100 og hvor andelen E av dobbeltbindinger som er skikket
for omsetning med maleinsyreanhydrid, utgjør 60 til 90 %. Her-
ved tilsvarer en verdi for E = 100 % den beregnede teoretiske verdi for det tilfellet at hvert molekyl av buten- eller isobuten-polymeren inneholder en slik reaktiv dobbeltbinding. Verdien E blir beregnet for en omsetning av polyisobutenet med maleinsyreanhydrid ved et vektforhold på 5:1 og oppvarming i 4 timer av blandingen under omrøring ved 200°C. Ytterligere enkeltheter om dette finnes i GB-A-1 592 016, hvis åpenbarelse det her utrykkelig henvises til.
Polybutenene er handelsprodukter.
Det ved hydroformyleringen dannede oksoprodukt foreligger vanligvis som aldehyd/alkohol-blanding. Det kan bearbeides videre som blanding eller det kan av hensyn til lagringsstabilitet på forhånd gjennomhydreres. Gjennomhydrerte produkter er mindre reaktive.
Ved den beskrevne hydroformylering dannes polybutyl- eller polyisobutylalkoholer med den generelle formel V:
hvor R^betyr en polybutyl- eller polyisobutylrest avledet fra isobuten og inntil 20 vekt% n-buten. Disse forbindelser er eksempelvis brukbare som mellomprodukter for fremstilling av forbindelsene med den generelle formel I. De dannes, som tidligere beskrevet, ved hydroformylering av det tidligere kommenterte polybuten. Spesielt foretrukket er polybutyl- eller polyisobutylalkoholer med formelen V, hvori resten R-j^ oppviser 20 til 400 karbon-at orne r .
Av økonomiske grunner er polybutyl- eller polyisobutylaminer med den generelle formel I hvor restene R2 og R3 hver gang betyr hydrogen spesielt egnet som ventil-renholdende eller -rensende additiv på drivstoffområdet, d.v.s. i drivstoffblandingen i henhold til oppfinnelsen. Doseringen av polybutyl- eller polyisobutylaminer med den generelle formel I som drivstofftilsetning er hensiktsmessig på 10-2000 mg/kg, hvorved et område på 50-800 mg/kg er foretrukket. Det oppnås en optimal virkning i området på 100-400 ppm som tilsetning til Otto-drivstoff for forbrenningsmotorer. Det kan doseres mindre mengder med like god virkning når nitrogen-innholdet er høyere, fremfor alt ved tilsetning av polyaminer, eksempelvis av dimetylaminopropylamin, eller ved tilsetning av polybutyl-eller polyisobutylaminer med den generelle formel I som har lav-molekylære polybutyl- eller polyisobutylandeier, og i tillegg vanlige bæresubstanser, eksempelvis polybuten, polybutylalkohol, Brightstock og andre mineraloljer, blir tildosert. Ved tilsetning ' av polyaminer, så som dietylentriamin til pentaetylenheksamin, oppnådde man tidligere forgasserrensemidler eller såkalte askefrie dispergatorer for smøreoljer.
Halogeninnholdet i polybutyl- eller polyisobutylaminene i henhold til oppfinnelsen tilsvarer det til. tilsetningsstoffene. Det ligger for det meste under 30 mg/kg.
Oppfinnelsen er videre rettet på en drivstoff- eller smøremiddelblanding som er kjennetegnet ved at den inneholder minst ett polybutylen- eller polyisobutylamin som er i samsvar med den generelle formel I:
hvor
R^ betyr en polybutyl- eller polyisobutylrest som er avledet fra isobuten og inntil 2 0 vekt% n-buten, og
R2 og R3, som er like eller forskjellige, kan bety hydrogen, Cl-<C>10~alkyl» fenyl, naf tyl,' C^-CiLQ-hydroksyalkyl» en aminoalkylenrest med den generelle formel II: hvor R4 betyr en C1-C10-alkylenrest, og R5 og R6, som er like eller forskjellige, betyr hydrogen, C1-C]_o_alkyl, fenyl, naftyl, C-L-Ciø-hydroksyalkyl eller polybutyl eller polyisobutyl med hver gang 20-400 karbonatomer, en polyaminoalkylenrest med den generelle formel III:
hvor restene R4 hver gang er like eller forskjellige, og restene R5 hver gang er like eller forskjellige, og restene R4, R5 og Rg har de foran nevnte betydninger, og m er et helt tall
fra 1 til 7, eller en polyoksyalkylenrest med den generelle formel IV:
hvor restene R4 hver gang kan være like eller forskjellige og har den foranstående betydning, og n er et helt tall mellom 1 og 30, eller R2 og R3, sammen med nitrogenatomet som de er bundet til, danner en morfolinylrest, hvorved polybutyl- eller polyisobutylaminene er oppnådd ved hydroformylering av de polybutener eller polyisobutener som tilsvarer resten , og hydrerende aminering. Ved en ytterligere foretrukket utførelsesform blir det tilveie-brakt en drivstoff- eller smøremiddelblanding med et innhold av forbindelser med de generelle formler I til IV<1> hvor resten R^ betyr en polybutyl- eller polyisobutylrest med 32 til 200 karbonatomer som er avledet fra isobuten og inntil 2 0 vekt% n-buten, og R2°9' R3 er like eller forskjellige og betyr hydrogen, metyl, etyl, n-propylen, i-propylen, n-butyl, sek.-butyl, tert.-butyl, pentyl, heksyl, fenyl,
eller danner en morfolinylrest sammen med nitrogenatomet som de er bundet til.
Siden ca. 50 % av de virksomme substanser i drivstoff additiver, uten tap av effekt, kan erstattes med polyisobuten (PiB), er til-setningen av PIB spesielt fordelaktig på grunn av omkostningene. Ved polyisobuten kan det dreie seg om en slik med en molekylvekt M,NT fra 300 til 2000, fortrinnsvis 500 til 1500.
Dersom det ved oppfinnelsen dreier seg om en drivstoffblanding, altså om et drivstoff for forbrenningsmotorer, kan polybutyl-eller polyisobutylaminet med den generelle formel I eksempelvis foreligge i en mengde på 10 - 2000 mg/kg, spesielt 100 - 400 mg/kg drivstoff.
I smøremiddelblandingen i henhold til oppfinnelsen kan polybutyl- eller polyisobutylaminet eksempelvis foreligge i en mengde av 0,5 - 5 vekt%, spesielt 1-3 vekt%, basert på den samlede vekt av blandingen.
Dersom det i forbindelsene med den generelle formel I foreligger hydroksygrupper, er disse forbindelser spesielt interessante som drivstoff-tilsetning.
Drivstoff- eller smøremiddelblandingen i henhold til oppfinnelsen fremviser en rekke fordeler overfor den kjente teknikk, så som eksempelvis den kjensgjerning at det dreier seg om mettede forbindelser, at det ikke opptrer korrosjonsproblemer, at syntesen er rimelig med hensyn til omkostninger og er miljøvennlig, og at det ikke opptrer noen produktbelastning med klor eller brom.
Oppfinnelsen blir belyst nærmere med de etterfølgende eksempler.
Eksempel 1.
500 g polybuten med molvekt MN = 950, 300 g dodekan og 2,8 g koboltoktakarbonyl blir oppvarmet under røring ved 185°C i 5 timer i en 2,5 1 slagrøreautoklav ved 280 bar CO/H2 1:1. Så avkjøler man til romtemperatur og fjerner katalysatoren med 400 ml 10 %-ig vandig eddiksyre. Deretter blir det vasket til nøytral tilstand. Man behandler så det oppnådde oksoprodukt med 1 1 ammoniakk og
med 300 g etanol og 100 g Raney-kobolt i en 5 1-valse-autoklav med 200 bar hydrogen ved 180°C i 5 timer. Etter avkjøling fraskiller man katalysatoren ved filtrering, avdamper den overskytende ammoniakk og fraskiller løsningsmidlet ved destillasjon.
Polybutenet som tilsettes i dette eksempel, er et høyreaktivt polybuten C, som ble fremstilt i samsvar med DE-A 2702604.
Polybutenomsetningen fremgår av den etterfølgende tabell.
Eksempel 2.
Man arbeider som i eksempel 1, hvorved man gjennomfører hydroformyleringen ved en temperatur på bare 120°C med 0,5 g rhodiumdikarbonyl-acetylacetonat som katalysator. Istedenfor ammoniakk anvender man dimetylaminopropylamin. Reaksjonstemperaturen ved amineringstrinnet er bare på 80°C. Siden hydroformylerings-reaksjonen overveiende forløper i retning av aldehyd, går omsetningen med dimetylaminopropylamin lettere. Det overskytende
amin blir fraskilt sammen med løsningsmidlet ved destillasjon.
Eksempler 3, 4 og 5.
Man arbeider etter den generelle forskrift i eksempel 1, hvorved man som aminkomponent anvender dimetylaminopropylamin.
Som polybuten anvender man i eksempel 3 et lite reaktivt polybuten (betegnet polybuten A), i eksempel 4 blir det anvendt et middels reaktivt polybuten B og i eksempel 5 tilsetter man et høyreaktivt polybuten C. Disse polybutener har en molekylvekt MN på 900-1000. Som i eksempel 1 blir omsetningen bestemt ved preparativ kolonne-kromatografi over kiselgel ved gravimetrisk bestemmelse av den inndampede heksanfraksjon, som bare inneholder uomsatt polybuten. Renheten for denne fraksjon blir sikret ved basetall og nitrogen-bestemmelse.
Eksempel 6
Man arbeider som beskrevet i ekempel 1, bortsett fra at man anvender 2,8 g koboltoktakarbonyl som katalysator. Med hensyn til aminokomponenten, så er denne tetraetylenpentamin.
Sammenligningseksempler A og B.
Produktene i henhold til den kjente teknikk ble fremstilt
ved klorering av polybuten C og dehydrohalogenering i samsvar med US-A-3 275 554, eksempel 1. I tilfelle av sammenligningseksempel B ble det på syntesemåten over polybutenklorid oppnådd en lavere omsetning enn i henhold til oppfinnelsen, hvilket er i overensstemmelse med DE-A-2 245 918.
Brukbarheten av de som ovenfor beskrevet fremstilte substanser i drivstoffblandinger ble undersøkt. Ved eksemplene 1 til 5 og sammenligningseksempel A dreier det seg som undersøkelse av additiv-tilsatt drivstoff, og eksempel 6 og sammenligningseksempel B vedrører smøremiddelblandinger.
Den ventilrensende virkning av de additiv-tilsatte driv-stoffer ble bedømt ved ventilavsetninger i Opel Kadet 1,2 liters-motor etter normert undersøkelse i samsvar med CEC-metode F-02-C79 etter 40 timer.
Dispergeringsvirkningen for smøreolje ble bestemt etter prikkemetoden, som er beskrevet av A. Schilling i "Les Huiles Pour Moteurs et le Graissage des Moteurs", bind 1, 1962, sidene 89-90.
Det fremgår av de data som er sammenstillet i de etterfølgende tabeller 1 og 2 at drivstoff- eller smøremiddelblandingen i henhold til oppfinnelsen er overlegen overfor den kjente teknikk med hensyn til ventilrensende virkning, respektive dispergerings-virkning.
Claims (5)
1. Polybutyl- eller polyisobutylaminer, karakterisert ved <at de har den generelle formel I:
hvor Ri betyr en polybutyl- eller polyisobutylrest med 20 til 400 karbonatomer som er avledet fra isobuten og inntil 20 vekt% n-buten, og R2 og R3, som er like eller forskjellige, betyr hydrogen, C1-<C>10-alkyl, fenyl, naftyl, C1-C10-hydroksyalkyl, en aminoalkylenrest med den generelle formel II:
hvor R4 betyr en C^-C^n-alkylenrest og R5 og R6, som er like eller forskjellige, betyr hydrogen, C1-C10-alkyl, fenyl, naftyl, C^-C^Q-hydroksyalkyl eller polybutyl eller polyisobutyl med hver gang 20 til 400 karbonatomer, en polyaminoalkylenrest med den generelle formel III:
hvor restene R4 hver gang er like eller forskjellige, restene R5 hver gang er like eller forskjellige, restene R4, R5 og R6 har de foranstående betydninger og m er et helt tall fra 1 til 7, eller en polyaksyalkenrest med den generelle formel IV:
hvor restene R4 hver gang er like eller forskjellige og har den foranstående betydning og n er et helt tall mellom 1 og 30, eller hvor R2 og R3, sammen med nitrogenatomet som de er bundet til, danner en morfolinylrest, og hvor polybutyl- eller polyisobutylaminene er oppnådd ved hydroformylering av de polybutener eller polyisobutener som tilsvarer resten R^, og hydrerende aminering.
2. Fremgangsmåte for fremstilling av polybutyl- eller polyisobutylaminer med den generelle formel I i henhold til krav 1, karakterisert ved at man hydroformylerer et polybuten eller polyisobuten med en rhodium-eller koboltkatalysator i nærvær av CO og H2 ved temperaturer mellom 80 og 2200"C og C0/H2-trykk på inntil 600 bar, og deretter utfører en hydrerende aminering av oksoproduktet.
3. Drivstoff- eller smøremiddelblanding, karakterisert ved at den inneholder minst ett polybutyl- eller polyisobutylamin som er i samsvar med den generelle formel I:
hvor R-l betyr en polybutyl- eller polyisobutylrest med 20-400 karbonatomer som er avledet fra isobuten og inntil 20 vekt% n-buten, og R2 og R3, som kan være like eller forskjellige, kan bety hydrogen, C1-C10-alkyl, f enyl, naftyl, C^<C->Lø-hydroksyalkyl, en aminoalkylenrest med den generelle formel II:
hvor R4 betyr en C1-C10-alkylenrest, og R5 og R6, som er like eller forskjellige, betyr hydrogen, C1-C10-alkyl, fenyl, naftyl, CQ^-C^^Q-hydroksyalkyl eller polybutyl eller polyisobutyl med hver gang 20-400 karbonatomer, en polyaminoalkylenrest med den generelle formel III:
hvor restene R4 hver gang er like eller forskjellige, og restene R5 hver gang er like eller forskjellige, og restene R4, R5 og R6 har de foran nevnte betydninger, og m er et helt tall fra 1 til 7, eller en polyoksyalkylenrest med den generelle formel IV:
hvor restene R4 hver gang kan være like eller forskjellige og har den foranstående betydning, og n er et helt tall mellom 1 og 30, eller R2 og R3, sammen med nitrogenatomet som de er bundet til, danner en morfolinylrest, hvorved polybutyl- eller polyisobutylaminene er oppnådd ved hydroformylering av de polybutener eller polyisobutener som tilsvarer resten R^, og hydrerende aminering.
4. Drivstoffblanding i henhold til krav 3, karakterisert ved at den inneholder polybutyl-eller polyisobutylaminet i en mengde fra 10 til 2000 ppm, spesielt 100 til 400 ppm, basert på den samlede vekt av blandingen.
5. Smøremiddelblanding i henhold til krav 3, karakterisert ved at den inneholder polybutyl-eller polyisobutylaminet i en mengde fra 0,5 til 5 vekt%, spesielt 1 til 3 vekt%, basert på den samlede vekt av blandingen.
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DE19863611230 DE3611230A1 (de) | 1986-04-04 | 1986-04-04 | Polybutyl- und polyisobutylamine, verfahren zu deren herstellung und diese enthaltende kraft- und schmierstoffzusammensetzungen |
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NO871393D0 NO871393D0 (no) | 1987-04-03 |
NO871393L NO871393L (no) | 1987-10-05 |
NO168828B true NO168828B (no) | 1991-12-30 |
NO168828C NO168828C (no) | 1992-04-08 |
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NO871393A NO168828C (no) | 1986-04-04 | 1987-04-03 | Polybutyl- eller polyisobutylaminer, fremgangsmaate for fremstilling av slike, samt drivstoff- og smoeremiddelblanding inneholdende polybutyl- eller polyisobutylaminer |
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US (1) | US4832702A (no) |
EP (1) | EP0244616B1 (no) |
JP (2) | JPH07103385B2 (no) |
DE (2) | DE3611230A1 (no) |
DK (1) | DK169584B1 (no) |
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NO (1) | NO168828C (no) |
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NL137371C (no) * | 1963-08-02 | |||
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DE2702604C2 (de) * | 1977-01-22 | 1984-08-30 | Basf Ag, 6700 Ludwigshafen | Polyisobutene |
US4134344A (en) * | 1977-04-11 | 1979-01-16 | Pullman Incorporated | Railway hopper car door lock |
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US4202784A (en) * | 1979-04-09 | 1980-05-13 | Standard Oil Company (Indiana) | Tertiary carbinamine modified mannich compositions and lubricants containing same |
US4312965A (en) * | 1980-02-22 | 1982-01-26 | W. R. Grace & Co. | Process for forming amine/amide containing polymers |
US4357148A (en) * | 1981-04-13 | 1982-11-02 | Shell Oil Company | Method and fuel composition for control or reversal of octane requirement increase and for improved fuel economy |
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US4526936A (en) * | 1983-03-18 | 1985-07-02 | W. R. Grace & Co. | Process for the preparation of polymeric amine containing products |
GB2174102A (en) * | 1985-04-24 | 1986-10-29 | Shell Int Research | Diesel fuel composition |
-
1986
- 1986-04-04 DE DE19863611230 patent/DE3611230A1/de not_active Withdrawn
-
1987
- 1987-03-25 EP EP87104371A patent/EP0244616B1/de not_active Expired - Lifetime
- 1987-03-25 DE DE8787104371T patent/DE3763421D1/de not_active Expired - Lifetime
- 1987-03-25 ES ES87104371T patent/ES2016585B3/es not_active Expired - Lifetime
- 1987-03-25 US US07/029,811 patent/US4832702A/en not_active Expired - Lifetime
- 1987-03-30 JP JP62074583A patent/JPH07103385B2/ja not_active Expired - Lifetime
- 1987-04-03 DK DK170087A patent/DK169584B1/da not_active IP Right Cessation
- 1987-04-03 NO NO871393A patent/NO168828C/no unknown
-
1995
- 1995-04-04 JP JP7079199A patent/JP2696076B2/ja not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
US4832702A (en) | 1989-05-23 |
DK170087A (da) | 1987-10-05 |
JPH07103385B2 (ja) | 1995-11-08 |
NO871393L (no) | 1987-10-05 |
NO871393D0 (no) | 1987-04-03 |
EP0244616A2 (de) | 1987-11-11 |
DK170087D0 (da) | 1987-04-03 |
ES2016585B3 (es) | 1990-11-16 |
DE3763421D1 (de) | 1990-08-02 |
EP0244616A3 (en) | 1987-12-23 |
EP0244616B1 (de) | 1990-06-27 |
DK169584B1 (da) | 1994-12-12 |
JPH08100188A (ja) | 1996-04-16 |
DE3611230A1 (de) | 1987-10-08 |
JPS62241992A (ja) | 1987-10-22 |
JP2696076B2 (ja) | 1998-01-14 |
NO168828C (no) | 1992-04-08 |
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