CA1098108A - Polymeric additives for fuels and lubricants - Google Patents
Polymeric additives for fuels and lubricantsInfo
- Publication number
- CA1098108A CA1098108A CA299,852A CA299852A CA1098108A CA 1098108 A CA1098108 A CA 1098108A CA 299852 A CA299852 A CA 299852A CA 1098108 A CA1098108 A CA 1098108A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- ethylene
- oil
- composition
- haze
- 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.)
- Expired
Links
- 239000000654 additive Substances 0.000 title description 26
- 239000000446 fuel Substances 0.000 title description 6
- 239000000314 lubricant Substances 0.000 title description 2
- 239000002253 acid Substances 0.000 claims abstract description 87
- 239000000203 mixture Substances 0.000 claims abstract description 66
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 46
- -1 alkyl carboxylic acids Chemical class 0.000 claims abstract description 44
- 239000000463 material Substances 0.000 claims abstract description 41
- 239000005977 Ethylene Substances 0.000 claims abstract description 38
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 37
- 229920001577 copolymer Polymers 0.000 claims abstract description 33
- 229920001038 ethylene copolymer Polymers 0.000 claims abstract description 27
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 24
- 239000010687 lubricating oil Substances 0.000 claims abstract description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 24
- 229920000768 polyamine Polymers 0.000 claims abstract description 21
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 19
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 17
- 239000004711 α-olefin Substances 0.000 claims abstract description 16
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000178 monomer Substances 0.000 claims abstract description 10
- 229920005862 polyol Polymers 0.000 claims abstract description 9
- 150000003077 polyols Chemical class 0.000 claims abstract description 9
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 8
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 7
- 239000000376 reactant Substances 0.000 claims abstract description 6
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 5
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims abstract description 5
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229920000642 polymer Polymers 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 229920000578 graft copolymer Polymers 0.000 claims description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 239000003999 initiator Substances 0.000 claims description 9
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 8
- 150000003460 sulfonic acids Chemical class 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 239000010688 mineral lubricating oil Substances 0.000 claims description 6
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical group C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 4
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical group NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 3
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000002780 morpholines Chemical class 0.000 claims description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 2
- 150000008107 benzenesulfonic acids Chemical class 0.000 claims 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003921 oil Substances 0.000 description 63
- 238000006243 chemical reaction Methods 0.000 description 27
- 239000010802 sludge Substances 0.000 description 25
- 150000007513 acids Chemical class 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 239000012141 concentrate Substances 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- 239000002270 dispersing agent Substances 0.000 description 14
- 230000000996 additive effect Effects 0.000 description 13
- 230000008569 process Effects 0.000 description 13
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 229920001897 terpolymer Polymers 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 238000006277 sulfonation reaction Methods 0.000 description 5
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical group CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000001050 lubricating effect Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 230000003381 solubilizing effect Effects 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 230000008719 thickening Effects 0.000 description 3
- 150000003582 thiophosphoric acids Chemical class 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 239000010913 used oil Substances 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000000994 depressogenic effect Effects 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N iso-butene Natural products CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 150000002689 maleic acids Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N octan-3-ol Chemical compound CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 238000002103 osmometry Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 150000003016 phosphoric acids Chemical class 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 description 1
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- DHPWGEOXBYBHOY-YPKPFQOOSA-N (z)-2-dodecylbut-2-enedioic acid Chemical compound CCCCCCCCCCCC\C(C(O)=O)=C\C(O)=O DHPWGEOXBYBHOY-YPKPFQOOSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical class CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- FBPVUBVZRPURIU-UHFFFAOYSA-N 1-hexylpyrrole-2,5-dione Chemical compound CCCCCCN1C(=O)C=CC1=O FBPVUBVZRPURIU-UHFFFAOYSA-N 0.000 description 1
- YNMMWBZMXPMOJL-UHFFFAOYSA-N 1-pentadecyl-4,5-dihydroimidazole Chemical compound CCCCCCCCCCCCCCCN1CCN=C1 YNMMWBZMXPMOJL-UHFFFAOYSA-N 0.000 description 1
- NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-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
- DEGZUQBZHACZKW-UHFFFAOYSA-N 2-(methylamino)ethyl 2-methylprop-2-enoate Chemical compound CNCCOC(=O)C(C)=C DEGZUQBZHACZKW-UHFFFAOYSA-N 0.000 description 1
- RZUDZAJRBFRQLS-UHFFFAOYSA-N 2-dodecylpropanedioic acid Chemical compound CCCCCCCCCCCCC(C(O)=O)C(O)=O RZUDZAJRBFRQLS-UHFFFAOYSA-N 0.000 description 1
- KQLHMARFTGBJHY-UHFFFAOYSA-N 2-octacosylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O KQLHMARFTGBJHY-UHFFFAOYSA-N 0.000 description 1
- MEEKGULDSDXFCN-UHFFFAOYSA-N 2-pentylphenol Chemical compound CCCCCC1=CC=CC=C1O MEEKGULDSDXFCN-UHFFFAOYSA-N 0.000 description 1
- SMTKGALBDOEZCA-UHFFFAOYSA-N 2-tetradecylpropanedioic acid Chemical compound CCCCCCCCCCCCCCC(C(O)=O)C(O)=O SMTKGALBDOEZCA-UHFFFAOYSA-N 0.000 description 1
- CXJAFLQWMOMYOW-UHFFFAOYSA-N 3-chlorofuran-2,5-dione Chemical compound ClC1=CC(=O)OC1=O CXJAFLQWMOMYOW-UHFFFAOYSA-N 0.000 description 1
- UVLSCMIEPPWCHZ-UHFFFAOYSA-N 3-piperazin-1-ylpropan-1-amine Chemical compound NCCCN1CCNCC1 UVLSCMIEPPWCHZ-UHFFFAOYSA-N 0.000 description 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- WTQBISBWKRKLIJ-UHFFFAOYSA-N 5-methylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C)CC1C=C2 WTQBISBWKRKLIJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 241000726103 Atta Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical compound COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 241000237074 Centris Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
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Classifications
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- C10M143/00—Lubricating compositions characterised by the additive being a macromolecular hydrocarbon or such hydrocarbon modified by oxidation
- C10M143/02—Polyethene
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- C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/792,199 US4144181A (en) | 1977-04-29 | 1977-04-29 | Polymeric additives for fuels and lubricants |
| US792,199 | 1977-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1098108A true CA1098108A (en) | 1981-03-24 |
Family
ID=25156099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA299,852A Expired CA1098108A (en) | 1977-04-29 | 1978-03-28 | Polymeric additives for fuels and lubricants |
Country Status (10)
Families Citing this family (89)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5162526A (en) * | 1976-09-24 | 1992-11-10 | Exxon Chemical Patents Inc. | Macrocyclic polyamine and polycyclic polyamine multifunctional lubricating oil |
| US4637886A (en) * | 1982-12-27 | 1987-01-20 | Exxon Research & Engineering Co. | Macrocyclic polyamine and polycyclic polyamine multifunctional lubricating oil additives |
| US4880923A (en) * | 1976-09-24 | 1989-11-14 | Exxon Research & Engineering Company | Macrocyclic polyamine and polycyclic polyamine multifunctional lubricating oil additives |
| US4283293A (en) * | 1978-08-07 | 1981-08-11 | Mobil Oil Corporation | Metal working lubricant compositions |
| US4219432A (en) * | 1979-02-14 | 1980-08-26 | Exxon Research & Engineering Co. | Stabilized amide-imide graft of ethylene copolymeric additives for lubricants |
| GB2055852B (en) * | 1979-07-03 | 1983-11-02 | Exxon Research Engineering Co | Ethylene copolymers |
| US4338205A (en) * | 1980-08-25 | 1982-07-06 | Exxon Research & Engineering Co. | Lubricating oil with improved diesel dispersancy |
| CA1180850A (en) * | 1980-10-10 | 1985-01-08 | Harold N. Miller | Oil-soluble nitrogen containing sulfonated polymers useful as oil additives |
| US4517104A (en) * | 1981-05-06 | 1985-05-14 | Exxon Research & Engineering Co. | Ethylene copolymer viscosity index improver-dispersant additive useful in oil compositions |
| US4707285A (en) * | 1981-06-29 | 1987-11-17 | Exxon Research & Engineering Co. | Haze-free polymer additives for fuels and lubricants |
| US4734213A (en) * | 1981-06-29 | 1988-03-29 | Exxon Research & Engineering Co. | Haze-free polymer additives for fuels and lubricants |
| GB2123429A (en) * | 1982-05-22 | 1984-02-01 | Orobis Ltd | Phosphorus-containing polymeric lubricant additives |
| US4659491A (en) * | 1982-08-06 | 1987-04-21 | Texaco Inc. | Lubricating oil containing a polymer having a functionalized backbone which contains an electron withdrawing group |
| US4564460A (en) | 1982-08-09 | 1986-01-14 | The Lubrizol Corporation | Hydrocarbyl-substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
| US4623684A (en) | 1982-08-09 | 1986-11-18 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
| US4613342A (en) | 1982-08-09 | 1986-09-23 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same |
| US4575526A (en) | 1982-08-09 | 1986-03-11 | The Lubrizol Corporation | Hydrocarbyl substituted carboxylic acylaging agent derivative containing combinations, and fuels containing same |
| US4557847A (en) * | 1983-11-21 | 1985-12-10 | Exxon Research & Engineering Co. | Ethylene copolymer viscosity index improver-dispersant additive useful in oil compositions |
| US4810754A (en) * | 1983-12-02 | 1989-03-07 | Exxon Research & Engineering Company | High temperature peroxide induced telomerization processes for grafting vinyl nitrogen containing monomers onto olefin polymers |
| US4507515A (en) * | 1983-12-21 | 1985-03-26 | Exxon Research & Engineering Co. | Lubricating oil compositions containing ethylene-alpha-olefin polymers of controlled sequence distribution and molecular heterogeneity |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL302077A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1962-12-19 | |||
| US3272743A (en) * | 1964-08-05 | 1966-09-13 | Lubrizol Corp | Lubricants containing metal-free dispersants and metallic dispersants |
| US3624115A (en) * | 1966-10-10 | 1971-11-30 | Mobil Oil Corp | Coordinated complexes of nitrogenous compounds |
| US3846316A (en) * | 1968-12-03 | 1974-11-05 | Phillips Petroleum Co | Lubricants containing reaction products of petroleum sulfonic acids and organic nitrogen polymers |
| US3634241A (en) * | 1969-10-10 | 1972-01-11 | Chevron Res | Sulfonate salts of alkenyl succinimides |
| US3808131A (en) * | 1970-03-24 | 1974-04-30 | Mobil Oil Corp | Coordinated metal complexes in lubricating oils and hydrocarbon fuels |
| US3649661A (en) * | 1970-03-24 | 1972-03-14 | Mobil Oil Corp | Coordinated complexes of nitrogenous compounds |
| AU498559B2 (en) * | 1975-06-25 | 1979-03-15 | Exxon Research And Engineering Company | Lubricating oil concentrate |
| CA1088694A (en) * | 1975-07-31 | 1980-10-28 | Robert L. Stambaugh | Polyolefin grafted with polymers of nitrogen containing monomers and lubricants and fuel compositions containing same |
| US4069162A (en) * | 1975-11-03 | 1978-01-17 | Exxon Research & Engineering Co. | Haze free oil additive compositions containing polymeric viscosity index improver and process for producing said compositions |
| US4011380A (en) * | 1975-12-05 | 1977-03-08 | Standard Oil Company (Indiana) | Oxidation of polymers in presence of benzene sulfonic acid or salt thereof |
-
1977
- 1977-04-29 US US05/792,199 patent/US4144181A/en not_active Expired - Lifetime
-
1978
- 1978-03-28 CA CA299,852A patent/CA1098108A/en not_active Expired
- 1978-04-20 AU AU35288/78A patent/AU515939B2/en not_active Expired
- 1978-04-25 DE DE2818012A patent/DE2818012C2/de not_active Expired - Fee Related
- 1978-04-26 IT IT22728/78A patent/IT1094516B/it active
- 1978-04-27 BR BR7802640A patent/BR7802640A/pt unknown
- 1978-04-27 GB GB16765/78A patent/GB1603707A/en not_active Expired
- 1978-04-28 BE BE187243A patent/BE866535A/xx not_active IP Right Cessation
- 1978-04-28 FR FR7812669A patent/FR2388879A1/fr active Granted
- 1978-04-28 JP JP5020578A patent/JPS53136006A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1603707A (en) | 1981-11-25 |
| JPS53136006A (en) | 1978-11-28 |
| IT1094516B (it) | 1985-08-02 |
| FR2388879B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-02-15 |
| US4144181A (en) | 1979-03-13 |
| AU515939B2 (en) | 1981-05-07 |
| BR7802640A (pt) | 1978-12-19 |
| FR2388879A1 (fr) | 1978-11-24 |
| BE866535A (fr) | 1978-10-30 |
| IT7822728A0 (it) | 1978-04-26 |
| DE2818012A1 (de) | 1978-11-09 |
| DE2818012C2 (de) | 1994-09-29 |
| AU3528878A (en) | 1979-10-25 |
| JPH0232313B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-07-19 |
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