CA1341005C - Compositions combustibles et compositions d'huile lubrifiante contenant de tres longues chaines d'aminocurbamate d'alkylphenyl poly(oxyalkyline) - Google Patents

Compositions combustibles et compositions d'huile lubrifiante contenant de tres longues chaines d'aminocurbamate d'alkylphenyl poly(oxyalkyline)

Info

Publication number: CA1341005C
Authority: CA; Canada
Prior art keywords: oxyalkylene; poly; aminocarbamate; carbon atoms; lubricating oil
Prior art date: 1987-10-23
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 - Fee Related

Application number

CA000580895A

Other languages

English (en)

Inventor

Thomas F. Buckley, Iii

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Chevron USA Inc

Original Assignee

Chevron Research and Technology Co

Priority date (The priority date 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 date listed.)

1987-10-23

Filing date

1988-10-21

Publication date

2000-05-30

1987-10-23 Priority claimed from US07/112,902 external-priority patent/US4933485A/en

1987-10-23 Priority claimed from US07/112,901 external-priority patent/US4881945A/en

1988-10-21 Application filed by Chevron Research and Technology Co filed Critical Chevron Research and Technology Co

2000-05-30 Application granted granted Critical

2000-05-30 Publication of CA1341005C publication Critical patent/CA1341005C/fr

2017-05-30 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

-1 poly(oxyalkylene) Polymers 0.000 title claims abstract description 244
125000005037 alkyl phenyl group Chemical group 0.000 title claims abstract description 131
239000000203 mixture Substances 0.000 title claims abstract description 121
239000010687 lubricating oil Substances 0.000 title claims abstract description 96
IVHKZGYFKJRXBD-UHFFFAOYSA-N amino carbamate Chemical compound NOC(N)=O IVHKZGYFKJRXBD-UHFFFAOYSA-N 0.000 title claims abstract description 90
239000000446 fuel Substances 0.000 title claims abstract description 80
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 98
125000000217 alkyl group Chemical group 0.000 claims abstract description 77
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 51
239000012141 concentrate Substances 0.000 claims abstract description 48
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 33
OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical class NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 claims abstract description 28
239000003502 gasoline Substances 0.000 claims abstract description 15
229930195733 hydrocarbon Natural products 0.000 claims abstract description 14
150000002430 hydrocarbons Chemical class 0.000 claims abstract description 14
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 11
238000009835 boiling Methods 0.000 claims abstract description 9
229920000642 polymer Polymers 0.000 claims description 64
229920000768 polyamine Polymers 0.000 claims description 63
239000003921 oil Substances 0.000 claims description 50
125000005702 oxyalkylene group Chemical group 0.000 claims description 49
150000001875 compounds Chemical class 0.000 claims description 45
239000002270 dispersing agent Substances 0.000 claims description 26
230000001050 lubricating effect Effects 0.000 claims description 25
229920001281 polyalkylene Polymers 0.000 claims description 24
125000002947 alkylene group Chemical group 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 20
125000006353 oxyethylene group Chemical group 0.000 claims description 19
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 16
229920001519 homopolymer Polymers 0.000 claims description 16
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 14
AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 claims description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 6
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 3
CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 claims 10
125000001183 hydrocarbyl group Chemical group 0.000 abstract description 32
239000000654 additive Substances 0.000 description 51
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 29
239000002816 fuel additive Substances 0.000 description 22
230000000996 additive effect Effects 0.000 description 21
150000001412 amines Chemical class 0.000 description 21
229910052784 alkaline earth metal Inorganic materials 0.000 description 19
229920001577 copolymer Polymers 0.000 description 17
KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 17
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 15
238000000034 method Methods 0.000 description 15
239000000047 product Substances 0.000 description 15
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
125000004429 atom Chemical group 0.000 description 11
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 11
229960002317 succinimide Drugs 0.000 description 11
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 10
125000004433 nitrogen atom Chemical group N* 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
150000003839 salts Chemical class 0.000 description 10
125000003118 aryl group Chemical group 0.000 description 9
238000002485 combustion reaction Methods 0.000 description 9
239000003599 detergent Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 8
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
239000005977 Ethylene Substances 0.000 description 8
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
150000001336 alkenes Chemical class 0.000 description 8
239000002585 base Substances 0.000 description 8
230000001965 increasing effect Effects 0.000 description 8
230000007935 neutral effect Effects 0.000 description 8
239000002904 solvent Substances 0.000 description 8
229940014800 succinic anhydride Drugs 0.000 description 8
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 7
229920002367 Polyisobutene Polymers 0.000 description 7
229920000098 polyolefin Polymers 0.000 description 7
150000001342 alkaline earth metals Chemical class 0.000 description 6
125000003277 amino group Chemical group 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 6
239000002184 metal Substances 0.000 description 6
230000008569 process Effects 0.000 description 6
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 6
150000003871 sulfonates Chemical class 0.000 description 6
239000004711 α-olefin Substances 0.000 description 6
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
125000003342 alkenyl group Chemical group 0.000 description 5
229910052791 calcium Inorganic materials 0.000 description 5
239000011575 calcium Substances 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
238000012360 testing method Methods 0.000 description 5
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
239000003513 alkali Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000001569 carbon dioxide Substances 0.000 description 4
229910002092 carbon dioxide Inorganic materials 0.000 description 4
150000004985 diamines Chemical class 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 4
239000003254 gasoline additive Substances 0.000 description 4
125000000623 heterocyclic group Chemical group 0.000 description 4
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
239000003112 inhibitor Substances 0.000 description 4
239000002480 mineral oil Substances 0.000 description 4
235000010446 mineral oil Nutrition 0.000 description 4
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
229920001083 polybutene Polymers 0.000 description 4
239000000376 reactant Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 3
238000009825 accumulation Methods 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
230000002152 alkylating effect Effects 0.000 description 3
239000003963 antioxidant agent Substances 0.000 description 3
229910052788 barium Inorganic materials 0.000 description 3
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
238000006386 neutralization reaction Methods 0.000 description 3
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
150000004885 piperazines Chemical class 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
230000000379 polymerizing effect Effects 0.000 description 3
239000002966 varnish Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
241000382928 Oxya Species 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000004721 Polyphenylene oxide Substances 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
239000002199 base oil Substances 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
239000012267 brine Substances 0.000 description 2
IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
150000004657 carbamic acid derivatives Chemical class 0.000 description 2
239000000969 carrier Substances 0.000 description 2
229920001429 chelating resin Polymers 0.000 description 2
239000000356 contaminant Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
239000002283 diesel fuel Substances 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
UPCIBFUJJLCOQG-UHFFFAOYSA-L ethyl-[2-[2-[ethyl(dimethyl)azaniumyl]ethyl-methylamino]ethyl]-dimethylazanium;dibromide Chemical compound [Br-].[Br-].CC[N+](C)(C)CCN(C)CC[N+](C)(C)CC UPCIBFUJJLCOQG-UHFFFAOYSA-L 0.000 description 2
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
239000006260 foam Substances 0.000 description 2
150000002334 glycols Chemical class 0.000 description 2
150000002431 hydrogen Chemical group 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
239000006078 metal deactivator Substances 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
238000002156 mixing Methods 0.000 description 2
150000005673 monoalkenes Chemical class 0.000 description 2
150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
239000000178 monomer Substances 0.000 description 2
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 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical class NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 description 2
RPDJEKMSFIRVII-UHFFFAOYSA-N oxomethylidenehydrazine Chemical class NN=C=O RPDJEKMSFIRVII-UHFFFAOYSA-N 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
229920000570 polyether Polymers 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 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
238000011160 research Methods 0.000 description 2
239000000523 sample Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000010802 sludge Substances 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
229910052712 strontium Inorganic materials 0.000 description 2
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
229920001897 terpolymer Polymers 0.000 description 2
MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 2
229960001124 trientine Drugs 0.000 description 2
239000013638 trimer Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
RDIXKUKVNFKCOV-UHFFFAOYSA-N (2,4-dichlorophenyl) carbonochloridate Chemical compound ClC(=O)OC1=CC=C(Cl)C=C1Cl RDIXKUKVNFKCOV-UHFFFAOYSA-N 0.000 description 1
UYABSLBMZAYXNN-UHFFFAOYSA-N (2,4-dinitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C([N+]([O-])=O)=C1 UYABSLBMZAYXNN-UHFFFAOYSA-N 0.000 description 1
ISBSSBGEYIBVTO-TYKWNDPBSA-N (20R,22R)-20,22-dihydroxycholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@](C)(O)[C@H](O)CCC(C)C)[C@@]1(C)CC2 ISBSSBGEYIBVTO-TYKWNDPBSA-N 0.000 description 1
GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 1
RYWGPCLTVXMMHO-UHFFFAOYSA-N (4-chlorophenyl) carbonochloridate Chemical compound ClC(=O)OC1=CC=C(Cl)C=C1 RYWGPCLTVXMMHO-UHFFFAOYSA-N 0.000 description 1
NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 1
PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
WJECKFZULSWXPN-UHFFFAOYSA-N 1,2-didodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1CCCCCCCCCCCC WJECKFZULSWXPN-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
BIRVLSWGSXMSDC-UHFFFAOYSA-N 1-(2-aminopropylamino)propan-2-one Chemical compound CC(N)CNCC(C)=O BIRVLSWGSXMSDC-UHFFFAOYSA-N 0.000 description 1
JOLARBFRFPHQFB-UHFFFAOYSA-N 2-(1,3-dimethyltriazinan-5-yl)ethanamine Chemical compound CN1CC(CCN)CN(C)N1 JOLARBFRFPHQFB-UHFFFAOYSA-N 0.000 description 1
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YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
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ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
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PEUGKEHLRUVPAN-UHFFFAOYSA-N piperidin-3-amine Chemical compound NC1CCCNC1 PEUGKEHLRUVPAN-UHFFFAOYSA-N 0.000 description 1
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125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
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239000000377 silicon dioxide Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000003068 static effect Effects 0.000 description 1
238000003860 storage Methods 0.000 description 1
RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
238000005987 sulfurization reaction Methods 0.000 description 1
235000012976 tarts Nutrition 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
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AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Lubricants (AREA)

CA000580895A 1987-10-23 1988-10-21 Compositions combustibles et compositions d'huile lubrifiante contenant de tres longues chaines d'aminocurbamate d'alkylphenyl poly(oxyalkyline) Expired - Fee Related CA1341005C (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US07/112,902 US4933485A (en)	1987-10-23	1987-10-23	Lubricating oil compositions containing very long chain alkylphenyl poly (oxyalkylene) aminocarbamates
US112,901		1987-10-23
US112,902		1987-10-23
US07/112,901 US4881945A (en)	1987-10-23	1987-10-23	Fuel compositions containing very long chain alkylphenyl poly(oxyalkylene) aminocarbonates
PCT/US1988/003775 WO1990004582A1 (fr)	1987-10-23	1988-10-25	Compositions de carburants et compositions d'huiles lubrifiantes contenant des alkylphenyle poly(oxyalkylene) aminocarbamates

Publications (1)

Publication Number	Publication Date
CA1341005C true CA1341005C (fr)	2000-05-30

Family

ID=33422449

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000580895A Expired - Fee Related CA1341005C (fr)	1987-10-23	1988-10-21	Compositions combustibles et compositions d'huile lubrifiante contenant de tres longues chaines d'aminocurbamate d'alkylphenyl poly(oxyalkyline)

Country Status (1)

Country	Link
CA (1)	CA1341005C (fr)

1988
- 1988-10-21 CA CA000580895A patent/CA1341005C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
2004-05-31	MKLA	Lapsed

Publication	Publication Date	Title
EP0396573B1 (fr)	1994-01-05	Compositions de carburants et compositions d'huiles lubrifiantes contenant des alkylphenyle poly(oxyalkylene) aminocarbamates
US5600025A (en)	1997-02-04	Substantially straight chain alkylphenols
CA1341202C (fr)	2001-03-06	Additifs d'hydrocarbyl amine ayant une longue chaine aliphatique et un groupement de branchement oxy-carbonyl
US4933485A (en)	1990-06-12	Lubricating oil compositions containing very long chain alkylphenyl poly (oxyalkylene) aminocarbamates
CA1324391C (fr)	1993-11-16	Additifs de type hydrocarbylamine aliphatiques a chaine aliphatique longue pourvue d'un groupe connecteur de type oxyalkylenehydroxyle
CA1341209C (fr)	2001-03-27	Compositions d'huile lubrifiante et compositions combustibles contenant des chaines sensiblement lineaires d'aminocarbamate d'alkylphenyl poly(oxypropylene)
EP0230382A2 (fr)	1987-07-29	Additif pour huiles lubrifiantes et combustibles hydrocarbonés
CA1341005C (fr)	2000-05-30	Compositions combustibles et compositions d'huile lubrifiante contenant de tres longues chaines d'aminocurbamate d'alkylphenyl poly(oxyalkyline)
EP0419488A1 (fr)	1991-04-03	Compositions lubrifiantes a base d'huile ou de carburant contenant des aminocarbamates de poly(oxypropylene) alkylphenyles de type ''a roue a aiguille'' a chaine sensiblement droite.
US5108633A (en)	1992-04-28	Long chain aliphatic hydrocarbyl amine additives having an oxyalkylene hydroxy connecting group
US5312965A (en)	1994-05-17	Lubricating oil composition containing substantially straight chain alkylphenyl poly(oxypropylene) aminocarbamates
US5312460A (en)	1994-05-17	Fuel compositions containing substantially straight chain alkylphenyl poly (oxypropylene) amino carbamates
AU633481B2 (en)	1993-02-04	Lubricating oil compositions and fuel compositions containing substantially straight chain pinwheel alkylphenyl poly(oxypropylene) aminocarbamates
CA1341045C (fr)	2000-07-04	Compositions d'huile lubrifiante et compositions combustibles contenant des chaines "pinwheel" sensiblement lineaires d'aminocarbamate d'alkylphenyl poly(oxypropylene)
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