NO318504B1 - Fremgangsmate for a forhindre oksydativ nedbrytning eller gummilignende rester i bensin, stabilisert sammensetning samt anvendelse av blanding for stabilisering av bensin - Google Patents
Fremgangsmate for a forhindre oksydativ nedbrytning eller gummilignende rester i bensin, stabilisert sammensetning samt anvendelse av blanding for stabilisering av bensin Download PDFInfo
- Publication number
- NO318504B1 NO318504B1 NO19973218A NO973218A NO318504B1 NO 318504 B1 NO318504 B1 NO 318504B1 NO 19973218 A NO19973218 A NO 19973218A NO 973218 A NO973218 A NO 973218A NO 318504 B1 NO318504 B1 NO 318504B1
- Authority
- NO
- Norway
- Prior art keywords
- tert
- oxyl
- butyl
- tetramethylpiperidin
- phenylenediamine
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 51
- 238000000034 method Methods 0.000 title claims description 24
- 230000000087 stabilizing effect Effects 0.000 title claims description 12
- 238000010525 oxidative degradation reaction Methods 0.000 title claims description 9
- -1 aliphatic nitroxide compound Chemical class 0.000 claims description 49
- 239000002530 phenolic antioxidant Substances 0.000 claims description 40
- 150000004982 aromatic amines Chemical class 0.000 claims description 32
- 230000015572 biosynthetic process Effects 0.000 claims description 18
- 150000004986 phenylenediamines Chemical class 0.000 claims description 14
- 230000002195 synergetic effect Effects 0.000 claims description 14
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 12
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 238000000197 pyrolysis Methods 0.000 claims description 8
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 claims description 6
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 claims description 6
- DIPUOCQXXYYIJO-UHFFFAOYSA-N 1-n,2-n-bis(5-methylhexan-2-yl)benzene-1,2-diamine Chemical compound CC(C)CCC(C)NC1=CC=CC=C1NC(C)CCC(C)C DIPUOCQXXYYIJO-UHFFFAOYSA-N 0.000 claims description 5
- PXMJCECEFTYEKE-UHFFFAOYSA-N Benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, methyl ester Chemical compound COC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PXMJCECEFTYEKE-UHFFFAOYSA-N 0.000 claims description 5
- CFXCGWWYIDZIMU-UHFFFAOYSA-N Octyl-3,5-di-tert-butyl-4-hydroxy-hydrocinnamate Chemical compound CCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 CFXCGWWYIDZIMU-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- ZJNLYGOUHDJHMG-UHFFFAOYSA-N 1-n,4-n-bis(5-methylhexan-2-yl)benzene-1,4-diamine Chemical compound CC(C)CCC(C)NC1=CC=C(NC(C)CCC(C)C)C=C1 ZJNLYGOUHDJHMG-UHFFFAOYSA-N 0.000 claims description 4
- DXCHWXWXYPEZKM-UHFFFAOYSA-N 2,4-ditert-butyl-6-[1-(3,5-ditert-butyl-2-hydroxyphenyl)ethyl]phenol Chemical compound C=1C(C(C)(C)C)=CC(C(C)(C)C)=C(O)C=1C(C)C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O DXCHWXWXYPEZKM-UHFFFAOYSA-N 0.000 claims description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 4
- SXPLGYBFGPYAHS-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 SXPLGYBFGPYAHS-UHFFFAOYSA-N 0.000 claims description 4
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 4
- FLZYQMOKBVFXJS-UHFFFAOYSA-N 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoic acid Chemical compound CC1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O FLZYQMOKBVFXJS-UHFFFAOYSA-N 0.000 claims description 3
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 claims description 3
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- JURKUHPHNMPLCP-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) 4-tert-butylbenzoate Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)OC1CC(C)(C)N(O)C(C)(C)C1 JURKUHPHNMPLCP-UHFFFAOYSA-N 0.000 claims description 2
- CRGBPDJWOLULDY-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) acetate Chemical compound CC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 CRGBPDJWOLULDY-UHFFFAOYSA-N 0.000 claims description 2
- DRFYZAIGLPMIOS-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) benzoate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)C1=CC=CC=C1 DRFYZAIGLPMIOS-UHFFFAOYSA-N 0.000 claims description 2
- DSSWUSNSRXWFBO-UHFFFAOYSA-N 1-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)azepan-2-one Chemical compound C1C(C)(C)N(O)C(C)(C)CC1N1C(=O)CCCCC1 DSSWUSNSRXWFBO-UHFFFAOYSA-N 0.000 claims description 2
- WZLXKEPEPXWCBR-UHFFFAOYSA-N 1-[12-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)dodecyl]pyrrolidine-2,5-dione Chemical compound C1C(C)(C)N(O)C(C)(C)CC1CCCCCCCCCCCCN1C(=O)CCC1=O WZLXKEPEPXWCBR-UHFFFAOYSA-N 0.000 claims description 2
- KMEUSKGEUADGET-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)N1O KMEUSKGEUADGET-UHFFFAOYSA-N 0.000 claims description 2
- ZGDGVGVOFIGJIE-UHFFFAOYSA-N 1-n,2-n-di(butan-2-yl)benzene-1,2-diamine Chemical compound CCC(C)NC1=CC=CC=C1NC(C)CC ZGDGVGVOFIGJIE-UHFFFAOYSA-N 0.000 claims description 2
- JUHXTONDLXIGGK-UHFFFAOYSA-N 1-n,4-n-bis(5-methylheptan-3-yl)benzene-1,4-diamine Chemical compound CCC(C)CC(CC)NC1=CC=C(NC(CC)CC(C)CC)C=C1 JUHXTONDLXIGGK-UHFFFAOYSA-N 0.000 claims description 2
- BJLNXEQCTFMBTH-UHFFFAOYSA-N 1-n,4-n-di(butan-2-yl)-1-n,4-n-dimethylbenzene-1,4-diamine Chemical compound CCC(C)N(C)C1=CC=C(N(C)C(C)CC)C=C1 BJLNXEQCTFMBTH-UHFFFAOYSA-N 0.000 claims description 2
- APTGHASZJUAUCP-UHFFFAOYSA-N 1-n,4-n-di(octan-2-yl)benzene-1,4-diamine Chemical compound CCCCCCC(C)NC1=CC=C(NC(C)CCCCCC)C=C1 APTGHASZJUAUCP-UHFFFAOYSA-N 0.000 claims description 2
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical compound CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 claims description 2
- WICNVDWKCYMTQT-UHFFFAOYSA-N 2-N-butan-2-yl-2-N-phenylbenzene-1,2-diamine Chemical compound C1(=CC=CC=C1)N(C1=C(C=CC=C1)N)C(C)CC WICNVDWKCYMTQT-UHFFFAOYSA-N 0.000 claims description 2
- XILVRJJRCJMOAB-UHFFFAOYSA-N 2-[4,4-bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)butyl]propanedioic acid Chemical compound C1C(C)(C)N(O)C(C)(C)CC1C(CCCC(C(O)=O)C(O)=O)C1CC(C)(C)N(O)C(C)(C)C1 XILVRJJRCJMOAB-UHFFFAOYSA-N 0.000 claims description 2
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical group CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 claims description 2
- GQBHYWDCHSZDQU-UHFFFAOYSA-N 4-(2,4,4-trimethylpentan-2-yl)-n-[4-(2,4,4-trimethylpentan-2-yl)phenyl]aniline Chemical compound C1=CC(C(C)(C)CC(C)(C)C)=CC=C1NC1=CC=C(C(C)(C)CC(C)(C)C)C=C1 GQBHYWDCHSZDQU-UHFFFAOYSA-N 0.000 claims description 2
- BGLKXHNUOPUFCL-UHFFFAOYSA-N 4-hydroxy-1-[2-(4-hydroxy-3,3,5,5-tetramethyl-2-oxopiperazin-1-yl)ethyl]-3,3,5,5-tetramethylpiperazin-2-one Chemical compound O=C1C(C)(C)N(O)C(C)(C)CN1CCN1C(=O)C(C)(C)N(O)C(C)(C)C1 BGLKXHNUOPUFCL-UHFFFAOYSA-N 0.000 claims description 2
- VCOONNWIINSFBA-UHFFFAOYSA-N 4-methoxy-n-(4-methoxyphenyl)aniline Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(OC)C=C1 VCOONNWIINSFBA-UHFFFAOYSA-N 0.000 claims description 2
- ZZMVLMVFYMGSMY-UHFFFAOYSA-N 4-n-(4-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)C)=CC=C1NC1=CC=CC=C1 ZZMVLMVFYMGSMY-UHFFFAOYSA-N 0.000 claims description 2
- JQTYAZKTBXWQOM-UHFFFAOYSA-N 4-n-octan-2-yl-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CCCCCC)=CC=C1NC1=CC=CC=C1 JQTYAZKTBXWQOM-UHFFFAOYSA-N 0.000 claims description 2
- MZFCDWPEDQCRJM-UHFFFAOYSA-N 4-propan-2-yloxy-n-(4-propan-2-yloxyphenyl)aniline Chemical compound C1=CC(OC(C)C)=CC=C1NC1=CC=C(OC(C)C)C=C1 MZFCDWPEDQCRJM-UHFFFAOYSA-N 0.000 claims description 2
- OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical compound C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 claims description 2
- WJZRRMYMGWLZDY-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) benzene-1,2-dicarboxylate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)C1=CC=CC=C1C(=O)OC1CC(C)(C)N(O)C(C)(C)C1 WJZRRMYMGWLZDY-UHFFFAOYSA-N 0.000 claims description 2
- YJLOZVIELWKSNE-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) benzene-1,3-dicarboxylate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)C1=CC=CC(C(=O)OC2CC(C)(C)N(O)C(C)(C)C2)=C1 YJLOZVIELWKSNE-UHFFFAOYSA-N 0.000 claims description 2
- ZXDIQRGIYADNBI-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) butanedioate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)CCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 ZXDIQRGIYADNBI-UHFFFAOYSA-N 0.000 claims description 2
- GITLFISGTYWQIU-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) cyclohexane-1,4-dicarboxylate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)C1CCC(C(=O)OC2CC(C)(C)N(O)C(C)(C)C2)CC1 GITLFISGTYWQIU-UHFFFAOYSA-N 0.000 claims description 2
- SIXHNVLZVKYFOR-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) hexanedioate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)CCCCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 SIXHNVLZVKYFOR-UHFFFAOYSA-N 0.000 claims description 2
- CKJMHSMEPSUICM-UHFFFAOYSA-N di-tert-butyl nitroxide Chemical group CC(C)(C)N([O])C(C)(C)C CKJMHSMEPSUICM-UHFFFAOYSA-N 0.000 claims description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 2
- KXQXILJJTWHMRW-UHFFFAOYSA-N n,n'-bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)hexanediamide Chemical compound C1C(C)(C)N(O)C(C)(C)CC1NC(=O)CCCCC(=O)NC1CC(C)(C)N(O)C(C)(C)C1 KXQXILJJTWHMRW-UHFFFAOYSA-N 0.000 claims description 2
- FSWDLYNGJBGFJH-UHFFFAOYSA-N n,n'-di-2-butyl-1,4-phenylenediamine Chemical compound CCC(C)NC1=CC=C(NC(C)CC)C=C1 FSWDLYNGJBGFJH-UHFFFAOYSA-N 0.000 claims description 2
- NYLGUNUDTDWXQE-UHFFFAOYSA-N n-phenyl-n-prop-2-enylaniline Chemical compound C=1C=CC=CC=1N(CC=C)C1=CC=CC=C1 NYLGUNUDTDWXQE-UHFFFAOYSA-N 0.000 claims description 2
- RVWJIVLFXACVCQ-UHFFFAOYSA-N (1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OC1CC(C)(C)N(O)C(C)(C)C1 RVWJIVLFXACVCQ-UHFFFAOYSA-N 0.000 claims 1
- PWNBRRGFUVBTQG-UHFFFAOYSA-N 1-n,4-n-di(propan-2-yl)benzene-1,4-diamine Chemical group CC(C)NC1=CC=C(NC(C)C)C=C1 PWNBRRGFUVBTQG-UHFFFAOYSA-N 0.000 claims 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims 1
- KZNDXCVEWRZEEU-UHFFFAOYSA-N 4-n-cyclohexyl-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=CC=CC=1)C1CCCCC1 KZNDXCVEWRZEEU-UHFFFAOYSA-N 0.000 claims 1
- MYKPPUUOBUFFML-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) benzene-1,4-dicarboxylate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)C1=CC=C(C(=O)OC2CC(C)(C)N(O)C(C)(C)C2)C=C1 MYKPPUUOBUFFML-UHFFFAOYSA-N 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 description 15
- 239000000446 fuel Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
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- 238000011105 stabilization Methods 0.000 description 4
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
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- 238000012360 testing method Methods 0.000 description 3
- CSGAUKGQUCHWDP-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1O CSGAUKGQUCHWDP-UHFFFAOYSA-N 0.000 description 2
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- GPNYZBKIGXGYNU-UHFFFAOYSA-N 2-tert-butyl-6-[(3-tert-butyl-5-ethyl-2-hydroxyphenyl)methyl]-4-ethylphenol Chemical compound CC(C)(C)C1=CC(CC)=CC(CC=2C(=C(C=C(CC)C=2)C(C)(C)C)O)=C1O GPNYZBKIGXGYNU-UHFFFAOYSA-N 0.000 description 1
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 1
- 239000010771 distillate fuel oil Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000012184 mineral wax Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical class ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 238000003860 storage Methods 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
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical group C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
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- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/23—Organic compounds containing nitrogen containing at least one nitrogen-to-oxygen bond, e.g. nitro-compounds, nitrates, nitrites
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- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
- C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
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- C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
- C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
- C10L1/1832—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom mono-hydroxy
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- C10L1/182—Organic compounds containing oxygen containing hydroxy groups; Salts thereof
- C10L1/183—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom
- C10L1/1835—Organic compounds containing oxygen containing hydroxy groups; Salts thereof at least one hydroxy group bound to an aromatic carbon atom having at least two hydroxy substituted non condensed benzene rings
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- 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
- C10L1/222—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
- C10L1/2235—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 hydroxy containing
-
- 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
- C10L1/224—Amides; Imides carboxylic acid amides, imides
-
- 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
- C10L1/226—Organic compounds containing nitrogen containing at least one nitrogen-to-nitrogen bond, e.g. azo compounds, azides, hydrazines
-
- 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
- C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
- C10L1/2406—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides
-
- 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
- C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
- C10L1/2406—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides
- C10L1/2412—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides sulfur bond to an aromatic radical
-
- 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
- C10L1/24—Organic compounds containing sulfur, selenium and/or tellurium
- C10L1/2406—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides
- C10L1/2418—Organic compounds containing sulfur, selenium and/or tellurium mercaptans; hydrocarbon sulfides containing a carboxylic substituted; derivatives thereof, e.g. esters
-
- 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
- C10L1/26—Organic compounds containing phosphorus
- C10L1/2608—Organic compounds containing phosphorus containing a phosphorus-carbon bond
-
- 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
- C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
- C10L2230/08—Inhibitors
- C10L2230/081—Anti-oxidants
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/678,165 US5711767A (en) | 1996-07-11 | 1996-07-11 | Stabilizers for the prevention of gum formation in gasoline |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO973218D0 NO973218D0 (no) | 1997-07-10 |
| NO973218L NO973218L (no) | 1998-01-12 |
| NO318504B1 true NO318504B1 (no) | 2005-04-18 |
Family
ID=24721668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19973218A NO318504B1 (no) | 1996-07-11 | 1997-07-10 | Fremgangsmate for a forhindre oksydativ nedbrytning eller gummilignende rester i bensin, stabilisert sammensetning samt anvendelse av blanding for stabilisering av bensin |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5711767A (es) |
| EP (1) | EP0818526B1 (es) |
| JP (1) | JP3843380B2 (es) |
| KR (1) | KR100476032B1 (es) |
| CN (1) | CN1064992C (es) |
| BR (1) | BR9703956A (es) |
| CA (1) | CA2210055C (es) |
| CZ (1) | CZ295427B6 (es) |
| DE (1) | DE69718969T2 (es) |
| ES (1) | ES2190515T3 (es) |
| NO (1) | NO318504B1 (es) |
| RU (1) | RU2174998C2 (es) |
| SA (1) | SA97180688B1 (es) |
| SG (1) | SG50028A1 (es) |
| SK (1) | SK284713B6 (es) |
| TW (1) | TW399091B (es) |
| ZA (1) | ZA976130B (es) |
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| JP2000044969A (ja) | 1998-07-27 | 2000-02-15 | Tonen Corp | 無鉛高オクタン価ガソリン組成物 |
| US6337426B1 (en) | 1998-11-23 | 2002-01-08 | Nalco/Exxon Energy Chemicals, L.P. | Antifoulant compositions and processes |
| US6472486B2 (en) | 1999-03-09 | 2002-10-29 | Symyx Technologies, Inc. | Controlled stable free radical emulsion polymerization processes |
| US6716948B1 (en) | 1999-07-31 | 2004-04-06 | Symyx Technologies, Inc. | Controlled-architecture polymers and use thereof as separation media |
| DE19946136A1 (de) * | 1999-09-27 | 2001-03-29 | Basf Ag | Inhibitorzusammensetzung |
| IT1307306B1 (it) * | 1999-12-24 | 2001-10-30 | Chimec Spa | Procedimento per impedire la formazione di fouling polimerico neltrattamento di cariche idrocarburiche contenenti olefine. |
| US6403850B1 (en) | 2000-01-18 | 2002-06-11 | Uniroyal Chemical Company, Inc. | Inhibition of polymerization of unsaturated monomers |
| US6344560B1 (en) | 2000-05-03 | 2002-02-05 | Uniroyal Chemical Company, Inc. | Nitroaromatic solubilizer for nitroxyls in aromatic solvents |
| WO2002033026A1 (en) | 2000-10-16 | 2002-04-25 | Uniroyal Chemical Company, Inc. | Blends of quinone alkide and nitroxyl compounds as polymerization inhibitors |
| US6685823B2 (en) * | 2000-10-16 | 2004-02-03 | Uniroyal Chemical Company, Inc. | C-nitrosoaniline compounds and their blends as polymerization inhibitors |
| US6579442B2 (en) | 2001-05-22 | 2003-06-17 | Ge Betz, Inc. | Methods and compositions for inhibiting polymerization of vinyl monomers |
| US6639026B2 (en) | 2001-05-22 | 2003-10-28 | Ge Betz, Inc. | Methods and compositions for inhibiting polymerization of vinyl monomers |
| ES2308038T3 (es) * | 2002-11-13 | 2008-12-01 | Lanxess Deutschland Gmbh | Uso de 2,6-di-terc-butil-p-cresol para el aumento de la estabilidad al almacenamiento de biodiesel. |
| EP1606372A1 (en) * | 2003-03-31 | 2005-12-21 | Ciba SC Holding AG | Diesel fuel composition and a method to improve filterability of diesel fuel |
| JP5078614B2 (ja) * | 2004-08-18 | 2012-11-21 | チバ ホールディング インコーポレーテッド | 改善された性能を有する潤滑油組成物 |
| US7704931B2 (en) * | 2004-12-10 | 2010-04-27 | Chemtura Corporation | Lubricant compositions stabilized with multiple antioxidants |
| JP5143357B2 (ja) * | 2006-01-24 | 2013-02-13 | 株式会社Ａｄｅｋａ | インドール化合物を含有する潤滑油組成物 |
| US7964002B2 (en) * | 2006-06-14 | 2011-06-21 | Chemtura Corporation | Antioxidant additive for biodiesel fuels |
| ITRM20060581A1 (it) * | 2006-10-26 | 2008-04-27 | Chimec Spa | Additivo stabilizzante per olio combustibile |
| RU2009139760A (ru) * | 2007-03-28 | 2011-05-10 | Альбемарл Корпорейшн (Us) | Смеси антиоксидантов для метиловых эфиров жирных кислот (биодизельное топливо) |
| US20090156441A1 (en) * | 2007-12-12 | 2009-06-18 | Rowland Robert G | Cycloalkyl phenylenediamines as deposit control agents for lubricants |
| US8563489B2 (en) * | 2007-12-12 | 2013-10-22 | Chemtura Corporation | Alkylated 1,3-benzenediamine compounds and methods for producing same |
| BRPI0917345A2 (pt) * | 2008-08-28 | 2015-11-17 | Taminco | composição, e, método para produzir uma composição estabilizada. |
| US8187346B2 (en) * | 2008-12-29 | 2012-05-29 | Fina Technology, Inc. | Stabilization of pygas for storage |
| EP3689436A1 (en) | 2010-02-12 | 2020-08-05 | Donaldson Company, Inc. | Liquid filtration media |
| RU2443668C1 (ru) * | 2010-11-26 | 2012-02-27 | Федеральное государственное автономное образовательное учреждение высшего профессионального образования Сибирский федеральный университет (СФУ) | Способ стабилизации углеводородных топлив от окислительной деструкции |
| US8987515B2 (en) | 2011-12-13 | 2015-03-24 | Chemtura Corporation | Cross products and co-oligomers of phenylenediamines and aromatic amines as antioxidants for lubricants |
| WO2013090051A1 (en) | 2011-12-13 | 2013-06-20 | Chemtura Corporation | Cross products and co-oligomers of phenylenediamines and aromatic amines as antioxidants for lubricants |
| CN103351893B (zh) * | 2013-06-25 | 2015-06-03 | 黄河三角洲京博化工研究院有限公司 | 一种汽油多效复合抗氧阻胶剂 |
| US10077410B2 (en) | 2016-07-13 | 2018-09-18 | Chevron Oronite Company Llc | Synergistic lubricating oil composition containing mixture of antioxidants |
| WO2018044644A1 (en) * | 2016-08-31 | 2018-03-08 | Ecolab USA, Inc. | Method to inhibit polymerization in a process water |
| DE102016116348A1 (de) | 2016-09-01 | 2018-03-01 | Tunap Gmbh & Co. Kg | Kraftstoffadditiv zur reinigung eines verbrennungsmotors |
| CN107099357A (zh) * | 2017-04-28 | 2017-08-29 | 马健 | 汽油燃料抗氧防胶剂 |
| US10597597B1 (en) * | 2018-09-12 | 2020-03-24 | Exxonmobil Research And Engineering Company | Fuel high temperature antioxidant additive |
| CN110878033B (zh) * | 2019-12-05 | 2022-04-22 | 万华化学集团股份有限公司 | 一种功能型降色剂以及稳定二异氰酸酯产品的色号的方法 |
| FR3104607B1 (fr) * | 2019-12-17 | 2022-10-21 | Total Sa | Marquage de composition |
| CN116134118A (zh) | 2020-09-14 | 2023-05-16 | 埃科莱布美国股份有限公司 | 用于塑料衍生的合成原料的冷流添加剂 |
| CN116917441A (zh) * | 2021-03-10 | 2023-10-20 | 埃科莱布美国股份有限公司 | 用于塑料衍生的合成原料的稳定剂添加剂 |
| US20240199965A1 (en) * | 2021-04-26 | 2024-06-20 | Shell Usa Inc. | Fuel compositions |
| GB2619256A (en) | 2022-02-25 | 2023-12-06 | Plastic Energy Ltd | A method for the storage or transport of pyrolysis oil |
| CN114685854A (zh) * | 2022-04-25 | 2022-07-01 | 萧县新秀新材料有限公司 | 一种用于反式异戊橡胶的稳定剂及应用 |
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| US1940445A (en) * | 1929-08-07 | 1933-12-19 | Du Pont | Gum inhibitor for gasoline |
| US2305676A (en) * | 1940-02-29 | 1942-12-22 | Universal Oil Prod Co | Treatment of gasoline |
| US2333294A (en) * | 1940-05-31 | 1943-11-02 | Universal Oil Prod Co | Treatment of gasoline |
| FR1360030A (fr) * | 1962-06-13 | 1964-04-30 | American Cyanamid Co | Procédé de préparation de nitroxydes cycliques et composés obtenus |
| FR1325521A (fr) * | 1962-06-20 | 1963-04-26 | American Cyanamid Co | Nouveaux dérivés oxygénés nu,nu-disubstitués par des groupes tertiaires et procédés pour les préparer |
| US3322520A (en) * | 1964-03-23 | 1967-05-30 | Eastman Kodak Co | Gasoline inhibitor |
| US3556748A (en) * | 1966-07-05 | 1971-01-19 | Universal Oil Prod Co | Antioxidant mixture of n-phenyl-n'-sec-alkyl-ortho-phenylene-diamine and n,n'-di-sec-alkyl-ortho-phenylenediamine,and use thereof |
| GB1316342A (en) * | 1970-03-07 | 1973-05-09 | Ciba Geigy Uk Ltd | Diaryl nitroxides |
| GB1325775A (en) * | 1970-06-10 | 1973-08-08 | Ciba Geigy Uk Ltd | Phosphorus-containing piperidine derivatives and their use as stabilisers for polymerica material |
| DE2459331A1 (de) * | 1973-12-28 | 1975-07-10 | Ciba Geigy Ag | Pyrrolidin-dicarbonsaeuren und ihre ester als lichtstabilisatoren |
| US4616051A (en) * | 1981-05-04 | 1986-10-07 | Uniroyal Chemical Company, Inc. | Combination of phenolic antioxidant and stabilizer for use in organic material |
| US4398505A (en) * | 1981-10-22 | 1983-08-16 | Standard Oil Company (Indiana) | Diesel fuel composition |
| GB8332797D0 (en) * | 1983-12-08 | 1984-01-18 | Ciba Geigy Ag | Antioxidant production |
| US4670131A (en) * | 1986-01-13 | 1987-06-02 | Exxon Chemical Patents Inc. | Method for controlling fouling of hydrocarbon compositions containing olefinic compounds |
| US4648885A (en) * | 1986-06-13 | 1987-03-10 | Betz Laboratories, Inc. | Process and composition for stabilized distillate fuel oils |
| US5246469A (en) * | 1986-07-25 | 1993-09-21 | The Commonwealth Of Australia | Fuel stabilization |
| US5290888A (en) * | 1990-07-20 | 1994-03-01 | Ciba-Geigy Corporation | Process for stabilizing ethylenically unsaturated compounds and stabilized monomer compositions |
| GB9114237D0 (en) * | 1991-07-02 | 1991-08-21 | Exxon Chemical Patents Inc | Fuel oil treatment |
| US5169410A (en) * | 1991-09-24 | 1992-12-08 | Betz Laboratories, Inc. | Methods for stabilizing gasoline mixtures |
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| US5169401A (en) * | 1991-12-20 | 1992-12-08 | Zimmer, Inc. | Surgical reamer assembly |
| US5254760A (en) * | 1992-07-29 | 1993-10-19 | Ciba-Geigy Corporation | Inhibiting polymerization of vinyl aromatic monomers |
| US5322960A (en) * | 1993-04-15 | 1994-06-21 | Nippon Shokubai Co., Ltd. | Method for inhibiting polymerization of (meth) acrylic acid and esters thereof |
| IT1264946B1 (it) * | 1993-07-16 | 1996-10-17 | Ciba Geigy Spa | Derivati del 2,2,6,6-tetrametil-4-piperidinolo utili come stabilizzanti alla luce ed all'ossidazione per materiali organici. |
| US5412047A (en) * | 1994-05-13 | 1995-05-02 | Xerox Corporation | Homoacrylate polymerization processes with oxonitroxides |
| US5509944A (en) * | 1994-08-09 | 1996-04-23 | Exxon Chemical Patents Inc. | Stabilization of gasoline and gasoline mixtures |
| US5495045A (en) * | 1994-12-22 | 1996-02-27 | Shell Oil Company | Process for the preparation of alkoxyalkanoic acids |
-
1996
- 1996-07-11 US US08/678,165 patent/US5711767A/en not_active Expired - Lifetime
-
1997
- 1997-07-02 EP EP97810426A patent/EP0818526B1/en not_active Expired - Lifetime
- 1997-07-02 ES ES97810426T patent/ES2190515T3/es not_active Expired - Lifetime
- 1997-07-02 DE DE69718969T patent/DE69718969T2/de not_active Expired - Lifetime
- 1997-07-07 SG SG1997002375A patent/SG50028A1/en unknown
- 1997-07-09 RU RU97111833/04A patent/RU2174998C2/ru not_active IP Right Cessation
- 1997-07-09 CZ CZ19972177A patent/CZ295427B6/cs not_active IP Right Cessation
- 1997-07-09 SK SK940-97A patent/SK284713B6/sk not_active IP Right Cessation
- 1997-07-09 CA CA002210055A patent/CA2210055C/en not_active Expired - Fee Related
- 1997-07-10 CN CN971146608A patent/CN1064992C/zh not_active Expired - Fee Related
- 1997-07-10 NO NO19973218A patent/NO318504B1/no not_active IP Right Cessation
- 1997-07-10 JP JP20090297A patent/JP3843380B2/ja not_active Expired - Fee Related
- 1997-07-10 KR KR1019970031868A patent/KR100476032B1/ko not_active IP Right Cessation
- 1997-07-10 ZA ZA9706130A patent/ZA976130B/xx unknown
- 1997-07-11 BR BR9703956A patent/BR9703956A/pt not_active IP Right Cessation
- 1997-07-11 TW TW086109881A patent/TW399091B/zh not_active IP Right Cessation
- 1997-12-07 SA SA97180688A patent/SA97180688B1/ar unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TW399091B (en) | 2000-07-21 |
| ZA976130B (en) | 1998-01-12 |
| CN1172149A (zh) | 1998-02-04 |
| DE69718969D1 (de) | 2003-03-20 |
| BR9703956A (pt) | 1998-11-03 |
| CZ217797A3 (cs) | 1998-02-18 |
| SK284713B6 (sk) | 2005-09-08 |
| DE69718969T2 (de) | 2003-07-17 |
| NO973218D0 (no) | 1997-07-10 |
| SG50028A1 (en) | 1998-06-15 |
| US5711767A (en) | 1998-01-27 |
| SK94097A3 (en) | 1998-01-14 |
| KR100476032B1 (ko) | 2005-07-04 |
| NO973218L (no) | 1998-01-12 |
| CN1064992C (zh) | 2001-04-25 |
| ES2190515T3 (es) | 2003-08-01 |
| JPH1077486A (ja) | 1998-03-24 |
| JP3843380B2 (ja) | 2006-11-08 |
| EP0818526B1 (en) | 2003-02-12 |
| KR980009429A (ko) | 1998-04-30 |
| CA2210055A1 (en) | 1998-01-11 |
| RU2174998C2 (ru) | 2001-10-20 |
| SA97180688B1 (ar) | 2006-04-04 |
| CA2210055C (en) | 2001-05-01 |
| CZ295427B6 (cs) | 2005-08-17 |
| EP0818526A1 (en) | 1998-01-14 |
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