CN1898365A - Power and lubricant additive concentrates containing at least one anthrachinone derivative as a marking substance - Google Patents
Power and lubricant additive concentrates containing at least one anthrachinone derivative as a marking substance Download PDFInfo
- Publication number
- CN1898365A CN1898365A CNA200480038844XA CN200480038844A CN1898365A CN 1898365 A CN1898365 A CN 1898365A CN A200480038844X A CNA200480038844X A CN A200480038844XA CN 200480038844 A CN200480038844 A CN 200480038844A CN 1898365 A CN1898365 A CN 1898365A
- Authority
- CN
- China
- Prior art keywords
- optional
- alkyl
- sauerstoffatom
- official energy
- ether official
- 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.)
- Pending
Links
- 239000000126 substance Substances 0.000 title abstract description 3
- 239000012141 concentrate Substances 0.000 title abstract 4
- 239000003879 lubricant additive Substances 0.000 title abstract 2
- 239000002480 mineral oil Substances 0.000 claims abstract description 17
- -1 nitro, hydroxyl Chemical group 0.000 claims description 164
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 122
- 150000001875 compounds Chemical class 0.000 claims description 41
- 239000000654 additive Substances 0.000 claims description 40
- 230000000996 additive effect Effects 0.000 claims description 39
- 125000003368 amide group Chemical group 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 239000000446 fuel Substances 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 16
- 150000004056 anthraquinones Chemical class 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 239000010687 lubricating oil Substances 0.000 claims description 16
- 235000010446 mineral oil Nutrition 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 239000000314 lubricant Substances 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 229920002367 Polyisobutene Polymers 0.000 description 26
- 239000002199 base oil Substances 0.000 description 24
- 238000012856 packing Methods 0.000 description 22
- 238000003860 storage Methods 0.000 description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 229920000768 polyamine Polymers 0.000 description 13
- 239000003550 marker Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 10
- 238000005576 amination reaction Methods 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- 229920002552 poly(isobornyl acrylate) polymer Polymers 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 5
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 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 5
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 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 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 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 5
- 125000002958 pentadecyl 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])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 5
- 229920001083 polybutene Polymers 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- SZOLUXDHHKCYKT-ONEGZZNKSA-N (e)-but-1-en-1-amine Chemical compound CC\C=C\N SZOLUXDHHKCYKT-ONEGZZNKSA-N 0.000 description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000003851 azoles Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003502 gasoline Substances 0.000 description 3
- 238000007037 hydroformylation reaction Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 2
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 2
- GDSLUYKCPYECNN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[(4-fluorophenyl)methyl]benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC=C(C=C2)F)C=CC=1 GDSLUYKCPYECNN-UHFFFAOYSA-N 0.000 description 2
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 238000006683 Mannich reaction Methods 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 229940125773 compound 10 Drugs 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000002816 fuel additive Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920005652 polyisobutylene succinic anhydride Polymers 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 150000003628 tricarboxylic acids Chemical class 0.000 description 2
- 239000006200 vaporizer Substances 0.000 description 2
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- VUQVGKNLSOSINI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1.C1=CC=C2SC=CC2=C1 VUQVGKNLSOSINI-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 1
- FANGQVKSFHFPBY-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FANGQVKSFHFPBY-UHFFFAOYSA-N 0.000 description 1
- NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical compound CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- BKOWRYQHXXBRPV-UHFFFAOYSA-N 2-ethylpiperidine Chemical compound [CH2]CC1CCCCN1 BKOWRYQHXXBRPV-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- SZTRCMOSUUQMBM-UHFFFAOYSA-N 2h-azepine Chemical compound C1C=CC=CC=N1 SZTRCMOSUUQMBM-UHFFFAOYSA-N 0.000 description 1
- GTDYINNWQOHUAH-UHFFFAOYSA-N 3-ethyl-2,4-dimethylpyrrolidine Chemical compound CCC1C(C)CNC1C GTDYINNWQOHUAH-UHFFFAOYSA-N 0.000 description 1
- YLUDSYGJHAQGOD-UHFFFAOYSA-N 3-ethylpiperidine Chemical compound CCC1CCCNC1 YLUDSYGJHAQGOD-UHFFFAOYSA-N 0.000 description 1
- JDFDHBSESGTDAL-UHFFFAOYSA-N 3-methoxypropan-1-ol Chemical compound COCCCO JDFDHBSESGTDAL-UHFFFAOYSA-N 0.000 description 1
- JEGMWWXJUXDNJN-UHFFFAOYSA-N 3-methylpiperidine Chemical compound CC1CCCNC1 JEGMWWXJUXDNJN-UHFFFAOYSA-N 0.000 description 1
- KWHPWBXOLZTZMJ-UHFFFAOYSA-N 4-ethylpiperidine Chemical compound CCC1CCNCC1 KWHPWBXOLZTZMJ-UHFFFAOYSA-N 0.000 description 1
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 1
- XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 1
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 1
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 description 1
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 239000004440 Isodecyl alcohol Substances 0.000 description 1
- 239000004439 Isononyl alcohol Substances 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000008431 aliphatic amides Chemical class 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 125000001204 arachidyl 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])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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 238000009835 boiling Methods 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
- 229940043232 butyl acetate Drugs 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- RIKMMFOAQPJVMX-UHFFFAOYSA-N fomepizole Chemical compound CC=1C=NNC=1 RIKMMFOAQPJVMX-UHFFFAOYSA-N 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002960 margaryl 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])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])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001196 nonadecyl 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])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])C([H])([H])[H] 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl 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])C([H])([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 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 125000004079 stearyl 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])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])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C10L1/003—Marking, e.g. coloration by addition of pigments
-
- 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
- C10L1/18—Organic compounds containing oxygen
- C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
- C10L1/1857—Aldehydes; Ketones
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
-
- 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
- C10L1/232—Organic compounds containing nitrogen containing nitrogen in a heterocyclic ring
-
- 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
- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
- C10M171/007—Coloured or dyes-containing lubricant compositions
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/08—Aldehydes; Ketones
-
- 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
- C10M2215/068—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings having amino groups bound to polycyclic aromatic ring systems, i.e. systems with three or more condensed rings
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/42—Flashing oils or marking oils
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
Abstract
The invention relates to power and lubricant additive concentrates which contain at least one anthrachinone derivative as a marking substance, to the use of said types of concentrates for adding mineral oils in addition to mineral oils which contain said concentrates.
Description
The present invention relates to a kind of serve as a mark fuel and lubricant multifunctional additive for lubricating oils of thing of at least a anthraquinone derivative that comprises, the mineral oil that this class enriched material is added into the purposes in the mineral oil and comprises this class enriched material.
For adding, use in mineral oil multifunctional additive for lubricating oils (according to relevant name, below be also referred to as packing), it is except the mixture of base oil (carrier oil) and different fuel additive, also comprises dyestuff usually and for invisible inspection or manufacturers's distinctive mark and comprise marker in addition.These packings make and can be supplied to different mineral oil dealers from un-added mineral oil groove, wherein add for company's difference, for example only when the transport container of packing into mineral oil suitable, by they separately packing and give color and marker.
Marker is generally from mineral oil extraction, is converted into the material of colored compound subsequently by deriving, perhaps visible or nonvisible wavelength is regional (for example at NIR) the material that performance absorbs at spectrographic.It was suggested and marker that discovery itself is useful, promptly also not only after carrying out derivatize, comprise high differentiation compound class, for example ammonium compound, methine dyes and azulene squaric acid (azulenesquaric acid) dyestuff of phthalocyanine, naphthalene phthalocyanine, nickel-two thiol-ene title complex, arylamine (for example WO 94/02570 A1, WO 96/10620 A1) and disazo dyes (for example EP 256 460 A1).The anthraquinone derivative that is used for dyed gasoline or mineral oil is described in document US 2,611, and 772, among US 2,068,372, EP 1,001 003 A1 and EP 1 323 811 A2.
Experience shows that many existing markers are stable in mineral oil under diluting condition, but then unstable in packing under the condition of concentrating; Packing composition act on the characteristic (as delustring) that has changed marker in the very short time.
Therefore, the purpose of this invention is to provide the fuel and lubricant multifunctional additive for lubricating oils, its characteristics are extraordinary extended storage stability, especially for the stability of the marker that wherein exists to the remaining ingredient effect of these enriched materials.
Therefore, had been found that to start mentioned fuel and lubricant multifunctional additive for lubricating oils (packing) that it comprises at least a anthraquinone derivative thing that serves as a mark.
The component of the present invention's packing especially is:
A) at least a anthraquinone derivative,
B) at least a base oil,
C) at least a additive that is selected from sanitising agent, dispersion agent and prooving of valve seat suppressant additive,
D) and if suitable other additive and auxiliary agent.
The component of using is a) especially for being selected from the anthraquinone derivative of following compound:
Formula I compound
Formula II compound
The formula III compound
Wherein
Z
1, Z
2Be hydrogen, hydroxyl, OR, NHR or NR independently of one another
2,
R
1, R
2Be R or COR independently of one another,
X is hydrogen, cyano group, nitro, hydroxyl, OR, amino, NHR, R or CH (R
9) (R
10),
N, m respectively do for oneself 0,1,2,3 or 4, and n or m greater than every kind of situation of 1 under, radicals R or radicals X separately can be identical or different,
R
9, R
10Be cyano group, COOH or COOR independently of one another,
R
3Be hydrogen, R or NHR,
R
4-R
8Be hydrogen, R or NHR independently of one another, and
R is the optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Alkyl, optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
20The C that alkyl replaces
5-C
7Cycloalkyl, optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Five yuan or hexa-atomic saturated heterocyclyl that alkyl replaces are perhaps for choosing wantonly by one or more halogens, cyano group, nitro, hydroxyl, amino, the optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Alkyl, C
1-C
20Alkoxyl group, C
1-C
20Alkylamino or C
1-C
20The C that dialkyl amido replaces
6-C
10Aryl is perhaps for choosing wantonly by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Alkyl, C
1-C
20Alkoxyl group, C
1-C
20Alkylamino or C
1-C
20The heteroaryl with 3-12 carbon atom that dialkyl amido replaces is perhaps for wherein aryl is optional by one or more halogens, cyano group, nitro, hydroxyl, amino, the optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Alkyl, C
1-C
20Alkoxyl group, C
1-C
20Alkylamino or C
1-C
20The C that dialkyl amido replaces
6-C
10Aryl-C
1-C
4Alkyl is perhaps for wherein heteroaryl is optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Alkyl, C
1-C
20Alkoxyl group, C
1-C
20Alkylamino or C
1-C
20Dialkyl amido replaces and has the heteroaryl-C of 3-12 carbon atom
1-C
4Alkyl.
The optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Alkyl for example comprises: methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, sec-butyl, the tertiary butyl, amyl group, isopentyl, neo-pentyl, tert-pentyl, hexyl, the 2-methyl amyl, heptyl, heptan-the 3-base, octyl group, the 2-ethylhexyl, iso-octyl, nonyl, different nonyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethyl-nonyl, isotridecyl (above-mentioned term iso-octyl, different nonyl, isodecyl and isotridecyl are popular name and come from alcohol by the oxo synthesis gained-about this problem referring to UllmannsEncyklop die der technischen Chemie, the 4th edition, the 7th volume, the 215-217 page or leaf, and the 11st the volume, the the 435th and 436 page), tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, methoxymethyl, 2-ethyl hexyl oxy methyl, the 2-methoxy ethyl, the 2-ethoxyethyl group, 2-propoxy-ethyl, 2-isopropoxy ethyl, the 2-butoxyethyl group, 2-or 3-methoxy-propyl, 2-or 3-ethoxycarbonyl propyl, 2-or 3-propoxy-propyl group, 2-or 3-butoxy propyl group, 2-or 4-methoxyl group butyl, 2-or 4-oxyethyl group butyl, 2-or 4-propoxy-butyl, 2-or 4-butoxy butyl, 3, the 6-dioxaheptyl, 3,6-two oxa-octyl groups, 4,8-two oxa-nonyls, 3,7-two oxa-octyl groups, 3,7-two oxa-nonyls, 4,7-two oxa-octyl groups, 4,7-two oxa-nonyls, 4,8-two oxa-decyls, 3,6,8-trioxa decyl, 3,6,9-trioxa undecyl, 3,6,9,12-four oxa-tridecyls or 3,6,9,12-four oxa-tetradecyls.
Useful C
5-C
7Cycloalkyl comprises cyclopentyl, cyclohexyl and suberyl.These cycloalkyl are optional by one or more, especially at the most three C
1-C
20Alkyl replaces, and the latter can choose wantonly and is inserted with 1-4 ether official energy Sauerstoffatom.The optional C that is inserted with Sauerstoffatom of this class
1-C
20Alkyl is listed in the above.
Optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Five yuan of replacing of alkyl or hexa-atomic saturated heterocyclyl for example are derived from tetramethyleneimine, 2-or 3-crassitude, 2,4-dimethyl-3-ethyl pyrrolidine, pyrazolidine, 2-, 3-, 4-or 5-methylpyrazole alkane, imidazolidine, 2-, 3-, 4-or 5-Methylimidazole alkane, azoles alkane, 2-, 4-or 5-methyl azoles alkane, different azoles alkane, 3-, 4-or the different azoles of 5-methyl alkane, piperidines, 2-, 3-or 4-methyl piperidine, 2-, 3-or 4-ethyl piperidine, 2, the 6-lupetidine, piperazine, 4-(C
1-C
4Alkyl) piperazine such as 4-methylpiperazine or 4-ethyl piperazidine, morpholine, thiomorpholine or thiomorpholine S, S-dioxide.
When R at defined variable Z
1And/or Z
2Group OR, NHR and NR
2In, in the group OR and NHR of defined variable X, in the definition radicals R
9And R
10Group COOR in, at defined variable R
3And R
4-R
8Group NHR in during corresponding to five yuan of suitable optional replacement or hexa-atomic saturated heterocyclyl, it is keyed to the specific heteroatoms of described group via the carbon atom of five yuan or hexa-member heterocycle.This is applied to work as R equally separately in variable R
1And R
2Definition in and in variable R
3Definition in corresponding to five yuan of suitable optional replacement-or during hexa-atomic saturated heterocyclyl.In other cases, can be via the carbon atom or the heteroatoms keyed jointing of the suitable keyed jointing of five yuan or hexa-member heterocycle base.
C
6-C
10Aryl especially comprises phenyl and naphthyl.These groups can be chosen wantonly by one or more halogens such as fluorine, chlorine or bromine, cyano group, nitro, hydroxyl, amino, the optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Alkyl, C
1-C
20Alkoxyl group, C
1-C
20Alkylamino or C
1-C
20Dialkyl amido replaces.The suitable optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Alkyl and at C
1-C
20Alkoxyl group, C
1-C
20Alkylamino or C
1-C
20The C that exists in the dialkyl amido
1-C
20Alkyl is enumerated by above-mentioned example.
Optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Alkyl, C
1-C
20Alkoxyl group, C
1-C
20Alkylamino or C
1-C
20The heteroaryl with 3-12 carbon atom that dialkyl amido replaces for example is derived from pyrroles, furans, thiophene, pyrazoles, different azoles, isothiazole, imidazoles, 1H-1,2, the 3-triazole, 1H-1,2, the 4-triazole, pyridine, pyrazine, pyridazine, 1H-azepine, 2H-azepine, the azoles, thiazole, 1,2,3-, 1,2,4-or 1,3,4- diazole, 1,2,3-, 1,2,4-or 1,3,4-thiadiazoles and optional fused benzo ring or dibenzo condensed ring, for example quinoline, isoquinoline 99.9, indoles, benzo [b] furans (cumarone), benzo [b] thiophene (benzo-thiophene), carbazole, dibenzofuran, dibenzothiophen, the 1H-indazole, indoxazole, benzo [d] isothiazole, anthranil (anthranil), benzoglyoxaline, benzoxazol, benzothiazole, cinnolines, 2, quinazoline, quinoxaline or azophenlyene.The optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Alkyl substituent is enumerated by above-mentioned example.
When R at defined variable Z
1And/or Z
2Group OR, NHR and NR
2In, in the group OR and NHR of defined variable X, in the definition radicals R
9And R
10Group COOR in, at defined variable R
3And R
4To R
8Group NHR in during corresponding to the heteroaryl of suitable optional replacement, it is keyed to the specific heteroatoms of described group via the carbon atom of heteroaryl.This is applied to work as R equally separately in variable R
1And/or R
2Definition in and in variable R
3Definition in during corresponding to the heteroaryl of suitable optional replacement.In other cases, can be via the carbon atom or the heteroatoms keyed jointing of the suitable keyed jointing of heteroaryl.
Wherein aryl is optional by one or more halogens, cyano group, nitro, hydroxyl, amino, the optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Alkyl, C
1-C
20Alkoxyl group, C
1-C
20Alkylamino or C
1-C
20The C that dialkyl amido replaces
6-C
10Aryl-C
1-C
4Alkyl especially comprises benzyl, styroyl, 3-hydrocinnamyl and 4-benzene butyl.The suitable optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Alkyl and at C
1-C
20Alkoxyl group, C
1-C
20Alkylamino or C
1-C
20The C that exists in the dialkyl amido
1-C
20Alkyl is enumerated by above-mentioned example.
Wherein heteroaryl is optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Alkyl, C
1-C
20Alkoxyl group, C
1-C
20Alkylamino or C
1-C
20Dialkyl amido replaces and has the heteroaryl-C of 3-12 carbon atom
1-C
4Alkyl for example is derived from the heteroaryl of as above enumerating, and it is via carbon atom or the heteroatoms and the C of the suitable keyed jointing of heteroaryl
1-C
4The alkyl keyed jointing.The suitable optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Alkyl and at C
1-C
20Alkoxyl group, C
1-C
20Alkylamino or C
1-C
20The C that exists in the dialkyl amido
1-C
20Alkyl is enumerated by above-mentioned example.
Preferred fuel and lubricant multifunctional additive for lubricating oils of the present invention comprises formula I, II and III anthraquinone derivative, wherein
Z
1, Z
2Be hydrogen or NHR independently of one another,
R
1, R
2Be R independently of one another,
X is hydrogen, cyano group or CH (R
9) (R
10),
N, m are 0,1,2,3 or 4, and when n or m greater than 1 the time, radicals R or X are identical or different,
R
9, R
10Be cyano group or COOR independently of one another,
R
3Be hydrogen, R or NHR,
R
4-R
7Be hydrogen or NHR,
R
8Be NHR, and
R is the optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Alkyl, optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15The cyclohexyl that alkyl replaces, optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Five yuan or hexa-atomic saturated heterocyclyl that alkyl replaces, or for choosing wantonly by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Alkyl, C
1-C
15Alkoxyl group, C
1-C
15Alkylamino or C
1-C
15The C that dialkyl amido replaces
6-C
10Aryl, or for choosing wantonly by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Alkyl, C
1-C
15Alkoxyl group, C
1-C
15Alkylamino or C
1-C
15The heteroaryl that dialkyl amido replaces with 3-5 carbon atom, or for wherein phenyl is optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Alkyl, C
1-C
15Alkoxyl group, C
1-C
15Alkylamino or C
1-C
15The phenyl C that dialkyl amido replaces
1-C
4Alkyl, or for wherein heteroaryl is optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Alkyl, C
1-C
15Alkoxyl group, C
1-C
15Alkylamino or C
1-C
15Dialkyl amido replaces and has the heteroaryl-C of 3-5 carbon atom
1-C
4Alkyl,
Preferred radicals R is enumerated by above-mentioned example.
Formula I anthraquinone derivative especially is the compound of formula Ia-If as follows:
In formula Ia-Ie, variable R in each case independently and in formula If variable R be the optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Alkyl, and optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15The C that alkyl replaces
6-C
10Aryl.
At the optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
15In the definition of alkyl, variable R is preferably selected from methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, sec-butyl, the tertiary butyl, amyl group, isopentyl, neo-pentyl, tert-pentyl, hexyl, the 2-methyl amyl, heptyl, heptan-the 3-base, octyl group, the 2-ethylhexyl, iso-octyl, nonyl, different nonyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethyl-nonyl, isotridecyl, tetradecyl, pentadecyl, methoxymethyl, 2-ethyl hexyl oxy methyl, the 2-methoxy ethyl, the 2-ethoxyethyl group, 2-propoxy-ethyl, 2-isopropoxy ethyl, the 2-butoxyethyl group, 2-and 3-methoxy-propyl, 2-and 3-ethoxycarbonyl propyl, 2-and 3-propoxy-propyl group, 2-and 3-butoxy propyl group, 2-and 4-methoxyl group butyl, 2-and 4-oxyethyl group butyl, 2-and 4-propoxy-butyl, 2-and 4-butoxy butyl, 3, the 6-dioxaheptyl, 3,6-two oxa-octyl groups, 4,8-two oxa-nonyls, 3,7-two oxa-octyl groups, 3,7-two oxa-nonyls, 4,7-two oxa-octyl groups, 4,7-two oxa-nonyls, 4,8-two oxa-decyls, 3,6,8-trioxa decyl, 3,6,9-trioxa undecyl, 3,6,9,12-four oxa-tridecyls and 3,6,9,12-four oxa-tetradecyls.
Choosing wantonly by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15The C that alkyl replaces
6-C
10In the definition of aryl, variable R is preferably selected from unsubstituted phenyl; By the listed optional C that is inserted with ether official energy Sauerstoffatom of above-mentioned example
1-C
152-, 3-that alkyl replaces and 4-are single to be replaced, and 2,3-, 2,4-and 3,4-two replacements and 2,3,4-, 2,3,5-, 2,3,6-, 2,4,5-, 2,4,6-and 3,4,5-trisubstd phenyl.
In the compound of formula Ia-Ie, special radicals R is preferably identical.
Formula II anthraquinone derivative especially is the compound of formula IIa-IIc as follows:
In formula IIa-IIc, variable R, R
1And R
2Be the optional C that is inserted with 1-4 ether official energy Sauerstoffatom independently of one another
1-C
15Alkyl, and optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15The C that alkyl replaces
6-C
10Aryl.
In formula IIa to IIc, X is meant two hydrogen atoms, at 2 of anthraquinone ring, and 3-arrangement or 6, two cyano group that 7-arranges, perhaps at 2 of anthraquinone ring, 3-arrangement or 6, two identical group CH (R that 7-arranges
9) (R
10).Latter two group CH (R
9) (R
10) be two group CH (COOR)
2, CH (CN) COOR or CH (CN)
2, wherein R is preferably the optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Alkyl, perhaps optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15The C that alkyl replaces
6-C
10Aryl.
At the optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
15In the definition of alkyl, variable R, R
1And R
2Be preferably selected from methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, sec-butyl, the tertiary butyl, amyl group, isopentyl, neo-pentyl, tert-pentyl, hexyl, the 2-methyl amyl, heptyl, heptan-the 3-base, octyl group, the 2-ethylhexyl, iso-octyl, nonyl, different nonyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethyl-nonyl, isotridecyl, tetradecyl, pentadecyl, methoxymethyl, 2-ethyl hexyl oxy methyl, the 2-methoxy ethyl, the 2-ethoxyethyl group, 2-propoxy-ethyl, 2-isopropoxy ethyl, the 2-butoxyethyl group, 2-and 3-methoxy-propyl, 2-and 3-ethoxycarbonyl propyl, 2-and 3-propoxy-propyl group, 2-and 3-butoxy propyl group, 2-and 4-methoxyl group butyl, 2-and 4-oxyethyl group butyl, 2-and 4-propoxy-butyl, 2-and 4-butoxy butyl, 3, the 6-dioxaheptyl, 3,6-two oxa-octyl groups, 4,8-two oxa-nonyls, 3,7-two oxa-octyl groups, 3,7-two oxa-nonyls, 4,7-two oxa-octyl groups, 4,7-two oxa-nonyls, 4,8-two oxa-decyls, 3,6,8-trioxa decyl, 3,6,9-trioxa undecyl, 3,6,9,12-four oxa-tridecyls and 3,6,9,12-four oxa-tetradecyls.
Choosing wantonly by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15The C that alkyl replaces
6-C
10In the definition of aryl, variable R, R
1And R
2Be preferably selected from unsubstituted phenyl; By the listed optional C that is inserted with ether official energy Sauerstoffatom of above-mentioned example
1-C
152-, 3-that alkyl replaces and 4-are single to be replaced, and 2,3-, 2,4-and 3,4-two replacements and 2,3,4-, 2,3,5-, 2,3,6-, 2,4,5-, 2,4,6-and 3,4,5-trisubstd phenyl.
Especially preferably wherein variable R, R
1And R
2Perhaps R, R
1And R
2Perhaps R
1And R
2Identical mutually formula IIa, IIb and the compound of IIc, promptly Dui Ying compound comprises:
And by cyano group or group CH (R
9) (R
10) 6, the corresponding compound that 7-replaces, wherein variable R is corresponding to top listed selection.
Formula III anthraquinone derivative used according to the invention especially is the compound of formula III a to IIId as follows:
Wherein
R
3Be R or NHR,
R
8Be NHR
W is radicals R in the definition of hydrogen or NHR
4To R
7,
P is 1,2,3 or 4, and when p greater than 1 the time, group is identical, and
R is the optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Alkyl, optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15The cyclohexyl that alkyl replaces, optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Five yuan or hexa-atomic saturated heterocyclyl that alkyl replaces, or for choosing wantonly by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Alkyl, C
1-C
15Alkoxyl group, C
1-C
15Alkylamino or C
1-C
15The C that dialkyl amido replaces
6-C
10Aryl, or for choosing wantonly by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Alkyl, C
1-C
15Alkoxyl group, C
1-C
15Alkylamino or C
1-C
15The heteroaryl that dialkyl amido replaces with 3-5 carbon atom, or for wherein phenyl is optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Alkyl, C
1-C
15Alkoxyl group, C
1-C
15Alkylamino or C
1-C
15The phenyl C that dialkyl amido replaces
1-C
4Alkyl, or for wherein heteroaryl is optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Alkyl, C
1-C
15Alkoxyl group, C
1-C
15Alkylamino or C
1-C
15Dialkyl amido replaces and has the heteroaryl-C of 3-5 carbon atom
1-C
4Alkyl,
Preferred radicals R is enumerated by the example in the generic definition of above-mentioned radicals R.
In formula III a to IIId, the more preferably optional C that is inserted with 1-4 ether official energy Sauerstoffatom of R
1-C
15Alkyl, and optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15The C that alkyl replaces
6-C
10Aryl.
In formula III a to IIId, R especially is selected from methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, sec-butyl, the tertiary butyl, amyl group, isopentyl, neo-pentyl, tert-pentyl, hexyl, the 2-methyl amyl, heptyl, heptan-the 3-base, octyl group, the 2-ethylhexyl, iso-octyl, nonyl, different nonyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethyl-nonyl, isotridecyl, tetradecyl, pentadecyl, methoxymethyl, 2-ethyl hexyl oxy methyl, the 2-methoxy ethyl, the 2-ethoxyethyl group, 2-propoxy-ethyl, 2-isopropoxy ethyl, the 2-butoxyethyl group, 2-and 3-methoxy-propyl, 2-and 3-ethoxycarbonyl propyl, 2-and 3-propoxy-propyl group, 2-and 3-butoxy propyl group, 2-and 4-methoxyl group butyl, 2-and 4-oxyethyl group butyl, 2-and 4-propoxy-butyl, 2-and 4-butoxy butyl, 3, the 6-dioxaheptyl, 3,6-two oxa-octyl groups, 4,8-two oxa-nonyls, 3,7-two oxa-octyl groups, 3,7-two oxa-nonyls, 4,7-two oxa-octyl groups, 4,7-two oxa-nonyls, 4,8-two oxa-decyls, 3,6,8-trioxa decyl, 3,6,9-trioxa undecyl, 3,6,9,12-four oxa-tridecyls, 3,6,9,12-four oxa-tetradecyls, unsubstituted phenyl, by optional be inserted with the ether official can Sauerstoffatom and by the listed C of above-mentioned example
1-C
152-, 3-that alkyl replaces and 4-are single to be replaced, and 2,3-, 2,4-and 3,4-two replacements and 2,3,4-, 2,3,5-, 2,3,6-, 2,4,5-, 2,4,6-and 3,4,5-trisubstd phenyl, this C
1-C
15Alkyl is selected from methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, sec-butyl, the tertiary butyl, amyl group, isopentyl, neo-pentyl, tert-pentyl, hexyl, the 2-methyl amyl, heptyl, heptan-the 3-base, octyl group, the 2-ethylhexyl, iso-octyl, nonyl, different nonyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethyl-nonyl, isotridecyl, tetradecyl, pentadecyl, methoxymethyl, 2-ethyl hexyl oxy methyl, the 2-methoxy ethyl, the 2-ethoxyethyl group, 2-propoxy-ethyl, 2-isopropoxy ethyl, the 2-butoxyethyl group, 2-and 3-methoxy-propyl, 2-and 3-ethoxycarbonyl propyl, 2-and 3-propoxy-propyl group, 2-and 3-butoxy propyl group, 2-and 4-methoxyl group butyl, 2-and 4-oxyethyl group butyl, 2-and 4-propoxy-butyl, 2-and 4-butoxy butyl, 3, the 6-dioxaheptyl, 3,6-two oxa-octyl groups, 4,8-two oxa-nonyls, 3,7-two oxa-octyl groups, 3,7-two oxa-nonyls, 4,7-two oxa-octyl groups, 4,7-two oxa-nonyls, 4,8-two oxa-decyls, 3,6,8-trioxa decyl, 3,6,9-trioxa undecyl, 3,6,9,12-four oxa-tridecyls and 3,6,9,12-four oxa-tetradecyls.
Normally used base oil is viscosity, high boiling point and especially heat-staple liquid.Therefore they have covered hot metal surface such as intake valve with thin liquid film, prevent or delay formation and the deposition of degradation production in the metallic surface.
As fuel and lubricant multifunctional additive for lubricating oils components b of the present invention) base oil for example be mineral base oil (crude oil), solvent those of (SN) 500-2000 viscosity grade that neutralize especially are based on M
NThe olefin polymer of=400-1800 is especially based on polybutene or polyisobutene (hydrogenation or not hydrogenation), based on the synthetic base oil of poly-(alpha-olefin) or poly-internal olefin and based on the synthetic base oil of alkoxylate long-chain alcohol or phenol.According to the present invention, the adducts as base oil of ethylene oxide, propylene oxide and/or oxybutylene and polybutene alcohol or polyisobutene alcohol for example is described among EP 277 345 A1; Other polyalkylene alcohol poly-alkoxylation thing used according to the invention is described among WO 00/50543 A1.Other base oil used according to the invention also comprises the polyolefine alcohol polyetheramine as describing in detail in WO 00/61708.
Be to be understood that the mixture that also can use different base oils, as long as they are compatible mutually and compatible with the remaining ingredient of the present invention's packing.
For example by from the dust granules of air with from the impurity that the unburned hydrocarbon of combustion chamber produces the vaporizer of oil engine and the pollution level of inlet system being increased, also being used in the pollution level that metering infeeds the injection system of fuel increases.
For reducing or preventing these pollutions, in fuel, add additive (" sanitising agent ") so that valve and vaporizer or injection system keep clean.This class sanitising agent is used in combination with one or more base oils usually.Base oil has been brought into play extra " washing function ", support and often promote sanitising agent in cleaning with the effect aspect keeping a public place clean, so they can help to reduce the aequum of sanitising agent.
Should further be mentioned that manyly usually to show additional effect the latter's the ratio reason that can reduce why in this case that Here it is as sanitising agent and/or dispersion agent as the materials of base oil at this.The base oil that this class has sanitising agent and/or dispersion agent effect for example is described in detail in the WO document of just having mentioned.
Often can not determine clearly also that sanitising agent, dispersion agent and valve seat suppress the mode of wearing and tearing additive effect, why Here it is comes together in amount of component b with these compounds) under reason.The conventional sanitising agent that is applied in the present invention's packing is for example listed among WO 00/50543 A1 and WO 00/61708 A1 and is comprised:
Can be according to EP-A 244 616 by making the highly reactive polyisobutenes hydroformylation; and use ammonia subsequently; the amino propylamine of monoamine or polyamines such as dimethylene; quadrol; diethylenetriamine; Triethylenetetramine (TETA) or tetren reduction amination and the PIBA that obtains; can be by making mainly polybutene or the polyisobutene chlorination that has two keys in b position and g position; and use ammonia subsequently; monoamine or above-mentioned polyamines amination and poly-(different) butenylamine of obtaining; can be by make two key oxidations in poly-(different) butylene with air or ozone to obtain carbonyl compound or carboxylic compound; and amination and poly-(different) butenylamine of obtaining under reduction (hydrogenation) condition subsequently
Can be according to DE-A 196 20 262 by making the reaction of polyisobutylene epoxies thing and amine, and make amino alcohol dehydration and reduction subsequently and the PIBA that obtains,
Can be the polyisobutene of 5-100 and the mixture reaction of oxynitride or oxynitride and oxygen by making mean polymerisation degree P according to WO-A 97/03946, and make these reaction product hydrogenations subsequently and the optional PIBA that contains hydroxyl that obtains,
Can be according to the PIBA of EP-A 476 485 by the hydroxyl that makes the reaction of polyisobutylene epoxies thing and ammonia, monoamine or above-mentioned polyamines and obtain,
Can be by making C
2-C
30Alkanol, C
6-C
30Alkanediol, single C
2-C
30Alkylamine, two C
2-C
30Alkylamine, C
1-C
30Alkyl cyclohexanol or C
1-C
30Alkylphenol and every hydroxyl or amino 1-30mol ethylene oxide and/or propylene oxide and/or oxybutylene reaction, and the polyetheramine that obtains with ammonia, monoamine or above-mentioned polyamines reduction amination subsequently, and
Can react " the polyisobutene Mannich base " that obtains by the phenol that makes polyisobutene and replace and aldehyde and monoamine or above-mentioned polyamines according to EP-A 831 141.
Other sanitising agent used according to the present invention and/or valve seat inhibition wearing and tearing additive are for example listed among WO 00/47698 A1 and are comprised the number-average molecular weight (M with at least one hydrophobic alkyl
N) being 85-20 000 and compound with at least one polar structure part, this polar structure partly is selected from:
(i) mono amino or have the polyamino of 6 nitrogen-atoms at the most, wherein at least one nitrogen-atoms has alkalescence;
(ii) choose wantonly and hydroxyl bonded nitro;
(iii) with mono amino or wherein at least one nitrogen-atoms have alkalescence polyamino bonded hydroxyl;
(iv) carboxyl or their an alkali metal salt or their alkaline earth salt;
(v) sulfonic group or their an alkali metal salt or their alkaline earth salt;
(vi) by hydroxyl, mono amino or the polyamino of at least one nitrogen-atoms wherein, perhaps by the end capped polyoxygenated C of carbamate groups with alkalescence
2-C
4Thiazolinyl;
(vii) carboxylic acid ester groups;
(viii) be derived from succinyl oxide and have hydroxyl and/or the structure division of amino and/or amide group and/or imino-; And/or
(ix) structure division that obtains of phenol by making replacement and aldehyde and monoamine or polyamines Mannich reaction.
The additive that contains mono amino or polyamino (i) is preferably based on polypropylene or based on M
NThe hyperergy of=300-5000 (promptly mainly have terminal double link, usually β-and γ-position) or conventional (promptly mainly the having internal double bond) polybutene or the polyolefine monoamine or the polyolefine polyamines of polyisobutene.Can be by making polyisobutene (it can contain 20 weight % n-butene unit at the most) hydroformylation; and use ammonia, monoamine or polyamines such as dimethylaminopropylamine, quadrol, diethylenetriamine, Triethylenetetramine (TETA) or tetren reduction amination and this class additive based on highly reactive polyisobutenes of preparing especially are disclosed among EP 244 616 A2.When will mainly have internal double bond (usually β-and γ-position) polybutene or polyisobutene when being used to prepare additive as raw material, the preparation route can be for by also amination subsequently of chlorination, perhaps by making two key oxidations obtaining carbonyl or carboxylic compound with air or ozone, and amination under reduction (hydrogenation) condition subsequently.Being used for aminating amine herein can be identical with those of the top highly reactive polyisobutenes reduction amination that is used to make hydroformylation.Especially be described among WO 94/24231 A1 based on polyacrylic additive accordingly.
Other preferable additives that contains mono amino (i) is the hydrogenated products of reaction product of the mixture of the polyisobutene of mean polymerisation degree P=5-100 and oxynitride or oxynitride and oxygen, especially as be described among WO 97/03946 A1.
Other preferable additives that contains mono amino (i) is for can be by making the reaction of polyisobutylene epoxies thing and amine, and makes amino alcohol dehydration and reduction subsequently and the compound that obtains, especially as being described among DE 196 20 262 A1.
The optional reaction product that nitro additive (ii) is preferably polyisobutene that mean polymerisation degree P is 5-100 or 10-100 and the mixture of oxynitride or oxynitride and oxygen that contains that is combined with hydroxyl is especially as being described among WO 96/03367 A1 and WO 96/03479 A1.These reaction product are generally the mixture of pure nitro vistac (as α, β-dinitrobenzene vistac) and blended hydroxyl nitro vistac (as α-nitro-beta-hydroxy vistac).
The hydroxyl additive (iii) that contains that is combined with mono amino or polyamino especially can be by preferably mainly having terminal double link and M
NThe polyisobutylene epoxies thing that the polyisobutene of=300-5000 obtains and the reaction product of ammonia, monoamine or polyamines are especially as being described among EP 476 485 A1.
Contain carboxyl or their an alkali metal salt or alkaline earth salt additive (iv) is preferably C
2-C
40Total molar mass of alkene and maleic anhydride is the multipolymer of 500-20 000, and its part or all of carboxyl be converted into an alkali metal salt or alkaline earth salt and any remaining carboxyl with the reaction of alcohol or amine.This class additive especially is disclosed among EP 307 815 A1.This class additive is mainly used to prevent the prooving of valve seat and can advantageously be used in combination as poly-(different) butenylamine or polyetheramine with conventional sanitising agent described in WO 87/01126 A1.
(additive v) is preferably an alkali metal salt or the alkaline earth salt of sulfosuccinic acid alkyl ester, especially described in EP 639 632 A1 to contain sulfonic group or their an alkali metal salt or alkaline earth salt.This class additive is mainly used to prevent the prooving of valve seat and can advantageously be used in combination as poly-(different) butenylamine or polyetheramine with conventional sanitising agent.
Contain polyoxygenated C
2-C
4(additive vi) is preferably polyethers or polyetheramine to the alkylidene group structure division, and it can be by making C
2-C
60Alkanol, C
6-C
30Alkanediol, single C
2-C
30Alkylamine, two C
2-C
30Alkylamine, C
1-C
30Alkyl cyclohexanol or C
1-C
30Alkylphenol and every hydroxyl or amino 1-30mol ethylene oxide and/or propylene oxide and/or oxybutylene reaction, and under the situation of polyetheramine, obtain with ammonia, monoamine or polyamines reduction amination subsequently.This class product especially is described among EP 310 875 A1, EP 356 725 A1, EP 700 985 A1 and the US 4,877,416.Under the situation of polyethers, this class product also has the performance of base oil.The representative instance of these compounds be tridecanol butoxy thing, different tridecanol butoxy thing, different nonyl phenol butoxy thing, polyisobutene alcohol butoxy thing and polyisobutene alcohol propoxylated glycerine and with the corresponding reaction product of ammonia.
(additive vii) is preferably the ester of monocarboxylic acid, dicarboxylic acid or tricarboxylic acid and long-chain alkanol or polyvalent alcohol, is 2mm 100 ℃ of following minimal viscosity especially to contain the carboxylate group
2Those of/s are especially as being described among DE 38 38 918 A1.Spendable monocarboxylic acid, dicarboxylic acid or tricarboxylic acid are aliphatic acid or aromatic acid, and particularly suitable ester alcohol or ester polyol are for example for having the long-chain representative of 6-24 carbon atom.The typical case of ester is represented as adipic acid ester, phthalic ester, isophthalic acid ester, terephthalate and the trimellitate of isooctyl alcohol, isononyl alcohol, isodecyl alcohol and different tridecanol.This class product also has the performance of base oil.
Contain be derived from succinyl oxide and have hydroxyl and/or the structure division of amino and/or amide group and/or imino-(additive viii) is preferably can be by making M conventional or hyperergy
NThe polyisobutene of=300-5000 and maleic anhydride are by hot route or the corresponding polyisobutylene succinic anhydride derivative that obtains via the reaction of chlorating polyisobutene.Useful especially is the derivative of aliphatic polyamines such as quadrol, diethylenetriamine, Triethylenetetramine (TETA) or tetren.This class gasoline fuel additive especially is described in US 4,849, in 572.
Contain by the additive that makes the structure division (ix) that phenolic hydroxyl group and aldehyde and monoamine or polyamines Mannich reaction obtain and be preferably the phenol that polyisobutene replaces and the reaction product of formaldehyde and monoamine or polyamines such as quadrol, diethylenetriamine, Triethylenetetramine (TETA), tetren or dimethylaminopropylamine.The phenol that polyisobutene replaces can come from M conventional or hyperergy
NThe polyisobutene of=300-5000.This class " polyisobutene-Mannich base " especially is described among EP 831 141 A1.
For each detailed more precise definition of additive, this obvious disclosing with reference to above-mentioned prior art document.
As amount of component b) dispersion agent for example be imide, acid amides, ester, ammonium salt and an alkali metal salt of polyisobutylene succinic anhydride.These compounds are particularly useful in the lubricating oil, but also are used for fuel composition as sanitising agent sometimes.
Can be used as packing composition d of the present invention if necessary) other additive and the auxiliary agent that exist be:
Organic solvent, for example alcohols such as methyl alcohol, ethanol, propyl alcohol, Virahol, butanols, isopropylcarbinol, sec-butyl alcohol, amylalcohol, primary isoamyl alcohol, neopentyl alcohol or hexanol, for example di-alcohols is as 1,2-ethylene glycol, 1, the 2-propylene glycol, 1, ammediol, 1, the 2-butyleneglycol, 2, the 3-butyleneglycol, 1, the 4-butyleneglycol, glycol ether, triglycol, dipropylene glycol or tripropylene glycol, for example ethers such as methyl tertiary butyl ether, 1, the 2-methyl glycol, 1, the 2-glycol dimethyl ether, 1, the 2-glycol monoethyl ether, 1, the 2-ethylene glycol diethyl ether, the 3-methoxypropanol, 3-isopropoxy propyl alcohol, tetrahydrofuran (THF) or two alkane, for example ketone such as acetone, methyl ethyl ketone or Pyranton, for example ester class such as methyl acetate, ethyl acetate, propyl acetate or butylacetate, for example lactams such as N-Methyl pyrrolidone (NMP), for example aliphatic hydrocrbon or aromatic hydrocarbons and composition thereof are as pentane, hexane, heptane, octane, octane-iso, sherwood oil, toluene, dimethylbenzene, ethylbenzene, 1,2,3, the 4-tetraline, naphthalane, dimethylnaphthalene or petroleum solvent, and for example mineral oil such as gasoline, kerosene, diesel oil or oil fuel
Inhibiter, for example under ferrous metal rot-resistant situation, based on the ammonium salt of organic carboxyl acid or the ammonium salt of heterocyclic aromatic with film forming tendency,
Antioxidant or stablizer, for example based on amine such as Ursol D, dicyclohexylamine or derivatives thereof, perhaps based on phenol as 2,4-di-tert-butylphenol or 3,5-di-t-butyl-4-hydroxyphenylpropionic acid,
Emulsion splitter,
Static inhibitor,
Metallocene such as ferrocene or methyl cyclopentadienyl tricarbonyl manganese,
Improver for lubricating performance (slip additive) is as some lipid acid, alkenyl succinate, two (hydroxyalkyl) aliphatic amide, hydroxyl acetamide or Viscotrol C,
Reduce the amine of fuel pH,
Other marker except that anthraquinone derivative, and
Dyestuff.
Usually selecting component is the concentration of at least a anthraquinone derivative in the present invention's packing a), adds after the mineral oil so that will pack, and required marker concentrations is present in wherein.Marker common concentration in mineral oil for example is that 0.01 ppm by weight is to tens of ppm by weight.
Components b) be that the concentration that at least a base oil is present in the present invention packing is generally 1-50 weight %, especially 5-30 weight % and
Amount of component b) be that the concentration of at least a sanitising agent and/or at least a dispersion agent is generally 25-90 weight %, 30-80 weight % especially,
Above-mentioned concentration in each case based on component a) to c) and d if present) total amount, component is a) to c) and d if present) concentration separately and add up to 100 weight %.
When inhibiter, antioxidant or stablizer, emulsion splitter, static inhibitor, metallocene, improver for lubricating performance and for the amine that reduces dyestuff pH as component d) when being present in the present invention's packing, their concentration and based on the gross weight (being that component is a) to c) and total amount d) of packing) be no more than 10 weight % usually, the concentration of inhibiter and emulsion splitter is generally about 0.01-0.5 weight % of packing total amount in each case.
When additional organic solvents (promptly also not introducing) with remaining ingredient as component d) when being present in the present invention's packing, their concentration and be no more than 20 weight % usually based on the total amount of packing.These solvents come from marker and/or dye solution usually, for metering more accurately, add solution rather than pure marker and/or dyestuff usually in packing.
When other marker except that anthraquinone derivative as component d) when being present in the present invention packing, their concentration is again based on they will have after will pack adding mineral oil concentration.This component a) in explanation, in addition necessary change during use.
When dyestuff as component d) when being present in the present invention packing, their concentration for example is 0.1-5 weight % based on the total amount of packing usually.
Embodiment:
Studied anthraquinone derivative as follows.By 1,4,5, the aniline of 8-tetrachloroanthraquinone and suitable replacement has synthesized compound 1-9 as raw material by the method described in document EP 0 323 184 A1.
Compound 1 (λ
Max=753nm, THF):
Compound 2 (λ
Max=750nm, THF):
Compound 3 (λ
Max=673nm, THF):
Compound 4 (λ
Max=758nm, THF):
Compound 5 (λ
Max=756nm, THF):
Compound 6 (λ
Max=756nm, THF):
Compound 7 (λ
Max=756nm, THF):
Compound 8:
Compound 9 (λ
Max=670nm, THF):
In preparation compound 8, trisubstituted compound obtains as by product.
Compound 10 (λ
Max=643nm, THF):
S.G.33 (can buy) from BASF Aktiengesellschaft
Compound 11 (λ
Max=328nm, THF):
(can buy) from BASF Aktiengesellschaft
Compound 12 (λ
Max=648nm, THF):
R: the mixture of following group
S.B.79 (can buy) from BASF Aktiengesellschaft
Contrast (λ
Max=770nm, THF):
The control compounds of using is the phthalocyanine of following formula:
(according to embodiment 1 preparation of WO 98/52950 A1)
Storage stability test:
The fuel and lubricant multifunctional additive for lubricating oils that uses is listed in the table 1 with wherein test mixing thing and their specific ratios of contained component in detail:
Table 1:
| Component | Chemical constitution | Weight % |
| Commercially available sanitising agent | PIBA (PIBA); PIBA content is the solution of 50 weight % | 70 |
| Commercially available base oil | The Fatty Alcohol(C12-C14 and C12-C18) propoxylated glycerine | 15 |
| Commercially available anticorrosive agent | Dimerization and oligomeric lipid acid | 0.1 |
| Commercially available emulsion splitter | Fatty alcohol ethoxylate | 0.1 |
| Solvent | Dimethylbenzene | 14.8 |
(sanitising agent, base oil, anticorrosive agent and emulsion splitter for example can from or buy via BASFAktiengesellschaft)
A) cited main component, sanitising agent and base oil in the table 1 studied the stability in storage of compound 1-9 and control compounds.The 50-100mg specific compound is dissolved among the 50mlShellsol AB for this reason, perhaps when the solubleness of compound in Shellsol AB is not enough, it is dissolved among about 5ml Virahol or the NMP at first at first, be diluted to 50ml with Shellsol AB then.Subsequently solution is filtered through the slot type paper filter.
With sanitising agent or base oil 1-3ml filtrate is diluted to 10ml (concentration corresponding to specific compound is 0.01-0.08%), and in the Xiao Chi of 1mm with respect to un-added corresponding reference measurement.Sample transfer to the ampoule of 10ml, is sealed and stores in 50 ℃ water-bath in the gastight mode.
The result is reproduced in table 2 and the table 3.All touchstones are turned to initial delustring.
Table 2: relatively than the stability in storage of sanitising agent under 50 ℃
| Compound | Storage time (h) | Wavelength (nm) | Delustring (stdn) |
| Contrast | 0 114 161 283 | 768 | 1.00 0.33 0.20 0.05 |
| 1 | 425 | 1.00 | |
| 2 | 451 | 752 | 0.96 |
| 3 | 475 | 681 | 0.98 |
| 4 | 500 | 758 | 0.86 |
| 5 | 500 | 756 | 1.00 |
| 6 | 500 | 756 | 0.98 |
| 7 | 500 | 756 | 1.00 |
| 9 | 500 | 670 | 1.00 |
Table 3: relatively than the stability in storage of base oil under 50 ℃
| Compound | Storage time (h) | Wavelength (nm) | Delustring (stdn) |
| 4 | 500 | 758 | 0.80 |
| 5 | 500 | 756 | 1.00 |
| 6 | 500 | 756 | 0.88 |
| 7 | 500 | 756 | 0.85 |
| 9 | 500 | 670 | 0.90 |
With compare under the situation about existing at sanitising agent, the stdn delustring of control compounds in the presence of base oil revealed obviously rapider decline as the function table of time.Therefore do not reproduce its value.
B), studied the stability in storage of compound 10-12 than sanitising agent and fuel and lubricant multifunctional additive for lubricating oils from table 1.Prepared the content of compound 10-12 in sanitising agent or fuel and lubricant multifunctional additive for lubricating oils is the solution of 1 weight % for this reason, and under room temperature and 40 ℃, has measured the stdn delustring as the storage time function.Extinction value when being standardized as (just after the preparation appropriate solution) with respect to the storage beginning.The result is following listed.
Compound 10:
Sanitising agent at room temperature: after 7 and 14 days storage time, fail to detect the variation of stdn delustring.
At the sanitising agent under 40 ℃: after 7 and 14 days storage time, fail to detect the variation of stdn delustring.
Fuel and lubricant multifunctional additive for lubricating oils at room temperature: after 7 and 14 days storage time, fail to detect the variation of stdn delustring.
At the fuel and lubricant multifunctional additive for lubricating oils under 40 ℃: after 7 and 14 days storage time, fail to detect the variation of stdn delustring.
Compound 11:
Sanitising agent at room temperature: after 4,12,28 and 42 days storage time, can detect the variation of stdn delustring.
At the sanitising agent under 40 ℃: after 4,12,28 and 42 days storage time, fail to detect the variation of stdn delustring.
Fuel and lubricant multifunctional additive for lubricating oils at room temperature: after 21 and 28 days storage time, fail to detect the variation of stdn delustring.
At the fuel and lubricant multifunctional additive for lubricating oils under 40 ℃: after 21 and 28 days storage time, fail to detect the variation of stdn delustring.
Compound 12:
Sanitising agent at room temperature: after 4,12,28 and 42 days storage time, fail to detect the variation of stdn delustring substantially.The result is as shown in the table:
| Storage time (my god) | Delustring (stdn) |
| 0 | 1.00 |
| 4 | 1.00 |
| 12 | 0.99 |
| 28 | 0.97 |
| 42 | 0.99 |
At the sanitising agent under 40 ℃: after 4,12,28 and 42 days storage time, fail to detect the variation of stdn delustring substantially.The result is as shown in the table:
| Storage time (my god) | Delustring (stdn) |
| 0 | 1.00 |
| 4 | 1.00 |
| 12 | 0.99 |
| 28 | 0.98 |
| 42 | 0.98 |
Claims (5)
1. one kind comprises the serve as a mark fuel and lubricant multifunctional additive for lubricating oils of thing of at least a anthraquinone derivative.
2. according to the enriched material of claim 1, it comprises at least a anthraquinone derivative that is selected from following compound:
Formula I compound
Formula II compound
The formula III compound
Wherein
Z
1, Z
2Be hydrogen, hydroxyl, OR, NHR or NR independently of one another
2,
R
1, R
2Be R or COR independently of one another,
X is hydrogen, cyano group, nitro, hydroxyl, OR, amino, NHR, R or CH (R
9) (R
10),
N, m respectively do for oneself 0,1,2,3 or 4, and n or m greater than every kind of situation of 1 under, radicals R or radicals X separately can be identical or different,
R
9, R
10Be cyano group, COOH or COOR independently of one another,
R
3Be hydrogen, R or NHR,
R
4-R
8Be hydrogen, R or NHR independently of one another, and
R is the optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Alkyl, optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
20The C that alkyl replaces
5-C
7Cycloalkyl, optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Five yuan or hexa-atomic saturated heterocyclyl that alkyl replaces are perhaps for choosing wantonly by one or more halogens, cyano group, nitro, hydroxyl, amino, the optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Alkyl, C
1-C
20Alkoxyl group, C
1-C
20Alkylamino or C
1-C
20The C that dialkyl amido replaces
6-C
10Aryl is perhaps for choosing wantonly by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Alkyl, C
1-C
20Alkoxyl group, C
1-C
20Alkylamino or C
1-C
20The heteroaryl with 3-12 carbon atom that dialkyl amido replaces is perhaps for wherein aryl is optional by one or more halogens, cyano group, nitro, hydroxyl, amino, the optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Alkyl, C
1-C
20Alkoxyl group, C
1-C
20Alkylamino or C
1-C
20The C that dialkyl amido replaces
6-C
10Aryl-C
1-C
4Alkyl is perhaps for wherein heteroaryl is optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
20Alkyl, C
1-C
20Alkoxyl group, C
1-C
20Alkylamino or C
1-C
20Dialkyl amido replaces and has the heteroaryl-C of 3-12 carbon atom
1-C
4Alkyl.
3. according to the enriched material of claim 2, wherein in formula I and formula II:
Z
1, Z
2Be hydrogen or NHR independently of one another,
R
1, R
2Be R independently of one another,
X is hydrogen, cyano group or CH (R
9) (R
10),
N, m are 0,1,2,3 or 4, and when n or m greater than 1 the time, radicals R or X are identical or different,
R
9, R
10Be cyano group or COOR independently of one another,
R
3Be hydrogen, R or NHR,
R
4-R
7Be hydrogen or NHR,
R
8Be NHR, and
R is the optional C that is inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Alkyl, optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15The cyclohexyl that alkyl replaces, optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Five yuan or hexa-atomic saturated heterocyclyl that alkyl replaces, or for choosing wantonly by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Alkyl, C
1-C
15Alkoxyl group, C
1-C
15Alkylamino or C
1-C
15The C that dialkyl amido replaces
6-C
10Aryl, or for choosing wantonly by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Alkyl, C
1-C
15Alkoxyl group, C
1-C
15Alkylamino or C
1-C
15The heteroaryl that dialkyl amido replaces with 3-5 carbon atom, or for wherein phenyl is optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Alkyl, C
1-C
15Alkoxyl group, C
1-C
15Alkylamino or C
1-C
15The phenyl C that dialkyl amido replaces
1-C
4Alkyl, or for wherein heteroaryl is optional by one or more optional C that are inserted with 1-4 ether official energy Sauerstoffatom
1-C
15Alkyl, C
1-C
15Alkoxyl group, C
1-C
15Alkylamino or C
1-C
15Dialkyl amido replaces and has the heteroaryl-C of 3-5 carbon atom
1-C
4Alkyl.
4. according to each the purposes of enriched material in being added into mineral oil among the 1-3.
5. mineral oil that comprises according to each enriched material among the claim 1-3.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10361504A DE10361504A1 (en) | 2003-12-23 | 2003-12-23 | Kraft and lubricant additive concentrates containing at least one anthraquinone derivative as a marker |
| DE10361504.0 | 2003-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1898365A true CN1898365A (en) | 2007-01-17 |
Family
ID=34706644
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA200480038844XA Pending CN1898365A (en) | 2003-12-23 | 2004-12-22 | Power and lubricant additive concentrates containing at least one anthrachinone derivative as a marking substance |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20070149415A1 (en) |
| EP (1) | EP1699907A1 (en) |
| JP (1) | JP2007515532A (en) |
| KR (1) | KR20060126710A (en) |
| CN (1) | CN1898365A (en) |
| AR (1) | AR048665A1 (en) |
| AU (1) | AU2004309053B2 (en) |
| BR (1) | BRPI0417837A (en) |
| CA (1) | CA2549647A1 (en) |
| DE (1) | DE10361504A1 (en) |
| MX (1) | MXPA06006135A (en) |
| MY (1) | MY143699A (en) |
| PE (1) | PE20051059A1 (en) |
| TW (1) | TW200535234A (en) |
| WO (1) | WO2005063942A1 (en) |
| ZA (1) | ZA200606004B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2635847A1 (en) * | 2006-12-20 | 2008-06-26 | Basf Se | Anthraquinone derivatives as markers for liquids |
| US8664442B2 (en) * | 2008-09-09 | 2014-03-04 | Chemtura Corporation | Anti-oxidants |
| CN101538495B (en) * | 2009-02-02 | 2012-04-25 | 王嘉兴 | Technology for preparing high-temperature industrial fuel by using loose heavy oil |
| WO2011032857A2 (en) | 2009-09-15 | 2011-03-24 | Basf Se | Use of derivatives of aromatic compounds as markers for liquids |
| FR2971254B1 (en) | 2011-02-08 | 2014-05-30 | Total Raffinage Marketing | LIQUID COMPOSITIONS FOR MARKING LIQUID HYDROCARBON FUELS AND FUELS, FUELS AND FUELS CONTAINING THEM, AND METHOD OF DETECTING MARKERS |
| WO2020239942A1 (en) * | 2019-05-31 | 2020-12-03 | Katholieke Universiteit Leuven | Multi-electron redox-active organic molecules for high-energy-density nonaqueous redox flow batteries |
| US20230250292A1 (en) * | 2020-07-29 | 2023-08-10 | Dow Global Technologies Llc | Aromatic hydrocarbon-soluble anthraquinone |
| ES2957535B2 (en) * | 2022-06-08 | 2024-06-13 | Kemegal Quim S L | FUEL ADDITIVE FOR INTERNAL COMBUSTION ENGINES |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2068372A (en) * | 1936-03-25 | 1937-01-19 | Du Pont | Preparation of aralkylamino-anthraquinone compounds |
| US2611772A (en) * | 1950-12-30 | 1952-09-23 | Eastman Kodak Co | Preparation of 1, 4, 5, 8-tetraamino-anthraquinone compounds |
| US3164449A (en) * | 1961-03-01 | 1965-01-05 | Du Pont | Anthraquinone dyes for gasoline |
| US3476500A (en) * | 1965-08-09 | 1969-11-04 | Allied Chem | Concentrated colorants |
| NL132836C (en) * | 1967-10-03 | |||
| DE2238174C3 (en) * | 1972-08-03 | 1975-08-14 | Basf Ag, 6700 Ludwigshafen | Concentrated solutions of an agent for the identification of mineral oil |
| IT1115249B (en) * | 1979-05-23 | 1986-02-03 | Acna | COLORING SOLUTIONS CONCENTRATED BLUE TONE BASED ON MIXTURES OF 1.4-DIALKYL-AMINO-ANTHRAQUINONES FOR THE COLORATION OF PETROLEUM PRODUCTS |
| IT1152195B (en) * | 1982-05-27 | 1986-12-31 | Acna | CONCENTRATED SOLUTIONS OF 1,4-DIALKYL-ARYLAMINE ANTHRACHINONES FOR COLORING PETROLEUM PRODUCTS |
| IT1200452B (en) * | 1985-04-12 | 1989-01-18 | Pigmenti Italia Spa | DENATURING AND MARKING COMPOSITION, PARTICULARLY SUITABLE FOR DIESEL |
| FR2694564A1 (en) * | 1992-08-07 | 1994-02-11 | Sepia Chim Sa | Prepn. of concn. colouring solns. based on 1,4-dialkyl amino-anthraquinone - useful in the colour identification of petroleum prods. |
| US6274381B1 (en) * | 1998-11-09 | 2001-08-14 | Rohm And Haas Company | Method for invisibly tagging petroleum products using visible dyes |
| DE19908262A1 (en) * | 1999-02-25 | 2000-08-31 | Basf Ag | Polyalkene alcohol polyalkoxylates and their use in fuels and lubricants |
| DE19916512A1 (en) * | 1999-04-13 | 2000-10-19 | Basf Ag | Polyalkene alcohol polyether amines and their use in fuels and lubricants |
| JP4201965B2 (en) * | 2000-08-10 | 2008-12-24 | 三菱樹脂株式会社 | Heat-resistant resin composition, heat-resistant film or sheet comprising the same, and laminated board based thereon |
| US6811575B2 (en) * | 2001-12-20 | 2004-11-02 | Rohm And Haas Company | Method for marking hydrocarbons with anthraquinones |
-
2003
- 2003-12-23 DE DE10361504A patent/DE10361504A1/en not_active Withdrawn
-
2004
- 2004-12-22 MY MYPI20045303A patent/MY143699A/en unknown
- 2004-12-22 KR KR1020067014028A patent/KR20060126710A/en not_active Application Discontinuation
- 2004-12-22 CA CA002549647A patent/CA2549647A1/en not_active Abandoned
- 2004-12-22 AU AU2004309053A patent/AU2004309053B2/en not_active Ceased
- 2004-12-22 MX MXPA06006135A patent/MXPA06006135A/en active IP Right Grant
- 2004-12-22 EP EP04804183A patent/EP1699907A1/en not_active Withdrawn
- 2004-12-22 JP JP2006546049A patent/JP2007515532A/en active Pending
- 2004-12-22 AR ARP040104860A patent/AR048665A1/en unknown
- 2004-12-22 WO PCT/EP2004/014587 patent/WO2005063942A1/en active Application Filing
- 2004-12-22 BR BRPI0417837-8A patent/BRPI0417837A/en not_active IP Right Cessation
- 2004-12-22 US US10/584,201 patent/US20070149415A1/en not_active Abandoned
- 2004-12-22 CN CNA200480038844XA patent/CN1898365A/en active Pending
- 2004-12-23 TW TW093140303A patent/TW200535234A/en unknown
-
2005
- 2005-01-03 PE PE2005000012A patent/PE20051059A1/en not_active Application Discontinuation
-
2006
- 2006-07-20 ZA ZA200606004A patent/ZA200606004B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20070149415A1 (en) | 2007-06-28 |
| JP2007515532A (en) | 2007-06-14 |
| MY143699A (en) | 2011-06-30 |
| PE20051059A1 (en) | 2006-01-20 |
| KR20060126710A (en) | 2006-12-08 |
| AU2004309053B2 (en) | 2010-06-10 |
| TW200535234A (en) | 2005-11-01 |
| AU2004309053A1 (en) | 2005-07-14 |
| MXPA06006135A (en) | 2006-08-11 |
| ZA200606004B (en) | 2007-12-27 |
| CA2549647A1 (en) | 2005-07-14 |
| BRPI0417837A (en) | 2007-04-10 |
| EP1699907A1 (en) | 2006-09-13 |
| DE10361504A1 (en) | 2005-07-28 |
| AR048665A1 (en) | 2006-05-17 |
| WO2005063942A1 (en) | 2005-07-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2485171C2 (en) | Functional fluids for internal combustion engines | |
| JP4940138B2 (en) | Nitrogen-containing heterocyclic compounds as friction and wear reducing additives for fuels | |
| CN1099406C (en) | Alkoxy acetic acid derivatives | |
| CN1720317A (en) | Use of amines and/or mannich adducts in fuel and lubricant compositions for direct injection spark ignition engines | |
| JP2009530427A (en) | Use of phthalocyanines substituted with aryl or alkyloxy as labeling substances for liquids | |
| CN1993449A (en) | Polyamine additives for fuels and lubricants | |
| CN1509295A (en) | Method for producing polyalkenyl succinimide products, novel polyalkenyl succinimide products with improved properties, inter mediate products and use thereof | |
| CN1271177C (en) | Method for marking mineral oil | |
| US20110162260A1 (en) | Alcohol Fuel Soluble Additive for Removing Deposits in Fueling Systems | |
| CN1898365A (en) | Power and lubricant additive concentrates containing at least one anthrachinone derivative as a marking substance | |
| US20080194446A1 (en) | Use of Dibenzanthrone and Isodibenzanthrone Derivatives as Marking Substances for Liquids | |
| WO2008082916A1 (en) | Fuel additives for use in high level alcohol-gasoline blends | |
| CN1910188A (en) | Use of phthalocyanines as marking substances for liquids | |
| CN1643115A (en) | Friction modifier for hydrocarbon fuels | |
| CN1093105A (en) | Multifunctional additive for lubricating oils | |
| CN1104486C (en) | Fuel compsns. | |
| CN1714139A (en) | Use of homopolymers of ethylenically unsaturated esters for improving the action of cold flow improvers | |
| CN1045416A (en) | The lubricating oil and the fuel that contain modified succinimides |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| AD01 | Patent right deemed abandoned |
Effective date of abandoning: 20070117 |
|
| C20 | Patent right or utility model deemed to be abandoned or is abandoned |