CA2559746C - Alkylated pana and dpa compositions - Google Patents
Alkylated pana and dpa compositions Download PDFInfo
- Publication number
- CA2559746C CA2559746C CA2559746A CA2559746A CA2559746C CA 2559746 C CA2559746 C CA 2559746C CA 2559746 A CA2559746 A CA 2559746A CA 2559746 A CA2559746 A CA 2559746A CA 2559746 C CA2559746 C CA 2559746C
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- group
- propyl
- hydrocarbon radical
- heptyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 139
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims abstract description 105
- 238000000034 method Methods 0.000 claims abstract description 51
- 230000002152 alkylating effect Effects 0.000 claims abstract description 21
- 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 abstract description 14
- -1 2,4-dimethyl-2-heptyl Chemical group 0.000 claims description 205
- 239000004215 Carbon black (E152) Substances 0.000 claims description 86
- 229930195733 hydrocarbon Natural products 0.000 claims description 86
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 61
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 56
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 50
- 239000012530 fluid Substances 0.000 claims description 43
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 40
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 40
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 34
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 33
- 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 claims description 32
- 239000000654 additive Substances 0.000 claims description 30
- 239000003054 catalyst Substances 0.000 claims description 28
- 239000000314 lubricant Substances 0.000 claims description 19
- 239000011541 reaction mixture Substances 0.000 claims description 18
- 230000000996 additive effect Effects 0.000 claims description 16
- 230000002378 acidificating effect Effects 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 13
- 230000001050 lubricating effect Effects 0.000 claims description 12
- 239000002199 base oil Substances 0.000 claims description 11
- 230000015556 catabolic process Effects 0.000 claims description 11
- 238000006731 degradation reaction Methods 0.000 claims description 11
- 230000001590 oxidative effect Effects 0.000 claims description 11
- 238000005555 metalworking Methods 0.000 claims description 9
- 239000003381 stabilizer Substances 0.000 claims description 5
- 229920001059 synthetic polymer Polymers 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000012208 gear oil Substances 0.000 claims description 2
- 238000003754 machining Methods 0.000 claims description 2
- 239000010705 motor oil Substances 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 239000010723 turbine oil Substances 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 abstract description 14
- 230000003078 antioxidant effect Effects 0.000 abstract description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 2
- 238000010998 test method Methods 0.000 abstract description 2
- 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 57
- 238000006243 chemical reaction Methods 0.000 description 55
- 229940035422 diphenylamine Drugs 0.000 description 41
- 239000002253 acid Substances 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 125000001424 substituent group Chemical group 0.000 description 26
- 239000000047 product Substances 0.000 description 25
- 150000001412 amines Chemical class 0.000 description 22
- 229920001577 copolymer Polymers 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 239000003921 oil Substances 0.000 description 19
- 235000019198 oils Nutrition 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 150000007513 acids Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 229940093470 ethylene Drugs 0.000 description 8
- 229920001684 low density polyethylene Polymers 0.000 description 8
- 239000004702 low-density polyethylene Substances 0.000 description 8
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000005804 alkylation reaction Methods 0.000 description 7
- 239000010949 copper Substances 0.000 description 7
- 239000000539 dimer Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 150000004760 silicates Chemical class 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000004700 high-density polyethylene Substances 0.000 description 6
- 150000002431 hydrogen Chemical group 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 241000871495 Heeria argentea Species 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 230000029936 alkylation Effects 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 235000006708 antioxidants Nutrition 0.000 description 5
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 5
- 238000003965 capillary gas chromatography Methods 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000005260 corrosion Methods 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 5
- 229920001903 high density polyethylene Polymers 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000010802 sludge Substances 0.000 description 5
- 239000001117 sulphuric acid Substances 0.000 description 5
- 235000011149 sulphuric acid Nutrition 0.000 description 5
- 239000010457 zeolite Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910021536 Zeolite Inorganic materials 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229910000323 aluminium silicate Inorganic materials 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 235000019197 fats Nutrition 0.000 description 4
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 235000011167 hydrochloric acid Nutrition 0.000 description 4
- 229960000443 hydrochloric acid Drugs 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 150000003440 styrenes Chemical class 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 3
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- LRUDIIUSNGCQKF-UHFFFAOYSA-N 5-methyl-1H-benzotriazole Chemical compound C1=C(C)C=CC2=NNN=C21 LRUDIIUSNGCQKF-UHFFFAOYSA-N 0.000 description 3
- 239000007848 Bronsted acid Substances 0.000 description 3
- TUSUWHFYKZZRIG-JQWMYKLHSA-N C([C@@H](NC(=O)[C@@H](C(C)C)NC(=O)[C@@H](CC(C)C)NC)C(=O)N[C@H](CC=1C=CC=CC=1)C(=O)N[C@H](CC(C)C)C(N)=O)C1=CC=CC=C1 Chemical compound C([C@@H](NC(=O)[C@@H](C(C)C)NC(=O)[C@@H](CC(C)C)NC)C(=O)N[C@H](CC=1C=CC=CC=1)C(=O)N[C@H](CC(C)C)C(N)=O)C1=CC=CC=C1 TUSUWHFYKZZRIG-JQWMYKLHSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 235000019484 Rapeseed oil Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- 239000011651 chromium Substances 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 239000003549 soybean oil Substances 0.000 description 3
- 235000012424 soybean oil Nutrition 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 150000003918 triazines Chemical class 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- 150000000178 1,2,4-triazoles Chemical class 0.000 description 2
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 2
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 2
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 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 description 2
- FCQAFXHLHBGGSK-UHFFFAOYSA-N 4-nonyl-n-(4-nonylphenyl)aniline Chemical class C1=CC(CCCCCCCCC)=CC=C1NC1=CC=C(CCCCCCCCC)C=C1 FCQAFXHLHBGGSK-UHFFFAOYSA-N 0.000 description 2
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 2
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 2
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 229920010126 Linear Low Density Polyethylene (LLDPE) Polymers 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
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- 239000013535 sea water Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229960003504 silicones Drugs 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000003930 superacid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 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
- 229920001897 terpolymer Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 229930003799 tocopherol Chemical class 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000563 toxic property Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic 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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/06—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
-
- 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
- C10M2215/064—Di- and triaryl amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
- C10M2215/065—Phenyl-Naphthyl amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/04—Detergent property or dispersant property
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/08—Resistance to extreme temperature
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55880104P | 2004-04-01 | 2004-04-01 | |
| US60/558,801 | 2004-04-01 | ||
| PCT/EP2005/051324 WO2005097728A1 (en) | 2004-04-01 | 2005-03-23 | Alkylated pana and dpa compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2559746A1 CA2559746A1 (en) | 2005-10-20 |
| CA2559746C true CA2559746C (en) | 2013-06-25 |
Family
ID=34966295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2559746A Expired - Fee Related CA2559746C (en) | 2004-04-01 | 2005-03-23 | Alkylated pana and dpa compositions |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8030259B2 (enExample) |
| EP (1) | EP1730101B1 (enExample) |
| JP (1) | JP5080969B2 (enExample) |
| KR (2) | KR101239143B1 (enExample) |
| CN (1) | CN1938260B (enExample) |
| BR (1) | BRPI0509521B1 (enExample) |
| CA (1) | CA2559746C (enExample) |
| ES (1) | ES2560658T3 (enExample) |
| PL (1) | PL1730101T3 (enExample) |
| SG (1) | SG154437A1 (enExample) |
| TW (1) | TW200536813A (enExample) |
| WO (1) | WO2005097728A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2559746C (en) | 2004-04-01 | 2013-06-25 | Ciba Specialty Chemicals Holding Inc. | Alkylated pana and dpa compositions |
| EP2055763A1 (en) * | 2007-10-23 | 2009-05-06 | Shell Internationale Research Maatschappij B.V. | Lubricating oil composition |
| US7838703B2 (en) * | 2007-11-16 | 2010-11-23 | Chemtura Corporation | Diaromatic amine derivatives as antioxidants |
| US7847125B2 (en) * | 2007-11-16 | 2010-12-07 | Chemtura Corporation | Acridan derivatives as antioxidants |
| FR2924122B1 (fr) * | 2007-11-28 | 2009-12-25 | Nyco Sa | Agent anti-oxydant et/ou anti-corrosion, composition lubrifiante contenant ledit agent et procede pour preparer celui-ci |
| CN102112434A (zh) * | 2008-08-08 | 2011-06-29 | 雅宝公司 | 辛基化苯基-α-萘胺产物混合物及具有高辛基化苯基-α-萘胺含量的该等混合物的制备 |
| US8227391B2 (en) | 2008-10-17 | 2012-07-24 | Afton Chemical Corporation | Lubricating composition with good oxidative stability and reduced deposit formation |
| US8110532B2 (en) * | 2008-11-24 | 2012-02-07 | Chemtura Corporation | Antioxidant compositions |
| JP5537912B2 (ja) * | 2009-11-27 | 2014-07-02 | Ｊｘ日鉱日石エネルギー株式会社 | 表面処理剤及び表面処理方法 |
| ES2377688B1 (es) * | 2010-04-12 | 2013-02-15 | Bautista Santillana Fernández | Aceite hidráulico biodegradable. |
| US8236205B1 (en) | 2011-03-11 | 2012-08-07 | Wincom, Inc. | Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles and other triazoles and methods for using same |
| US8236204B1 (en) | 2011-03-11 | 2012-08-07 | Wincom, Inc. | Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles solubilized in activating solvents and methods for using same |
| RU2493242C1 (ru) * | 2012-08-09 | 2013-09-20 | Общество с ограниченной ответственностью "ВМПАВТО" | Пластичная смазка |
| JP6324383B2 (ja) | 2012-08-14 | 2018-05-16 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 潤滑剤組成物用のポリマー及びその形成方法 |
| EP2703421A1 (en) | 2012-08-28 | 2014-03-05 | Huntsman Petrochemical LLC | A composition for making foams with reduced aldehyde emission |
| KR101628538B1 (ko) * | 2014-11-21 | 2016-06-08 | 황규택 | 기능성 김의 제조방법 |
| WO2017011159A1 (en) * | 2015-07-15 | 2017-01-19 | Chemtura Corporation | Diaryl amine antioxidants prepared from branched olefins |
| KR101659318B1 (ko) * | 2015-11-24 | 2016-09-23 | 주식회사 루브캠코리아 | 윤활 그리스 조성물 및 이의 제조 방법 |
| JP6677413B2 (ja) * | 2016-01-26 | 2020-04-08 | 出光興産株式会社 | 潤滑油組成物 |
| US10077410B2 (en) * | 2016-07-13 | 2018-09-18 | Chevron Oronite Company Llc | Synergistic lubricating oil composition containing mixture of antioxidants |
| EP3768808A4 (en) * | 2018-03-20 | 2021-12-22 | Basf Se | LUBRICANT COMPOSITION |
| CN120574619A (zh) | 2020-11-17 | 2025-09-02 | 松原实业有限公司 | 性能提高的包含烷基化二苯胺的组合物 |
| CA3203263A1 (en) | 2020-12-23 | 2022-06-30 | Scott Capitosti | Benzazepine compounds as antioxidants for lubricant compositions |
| EP4326842B1 (en) * | 2021-04-21 | 2025-01-15 | LANXESS Corporation | Liquid mono-alkylated n-phenyl-alpha-napthylamine compositions and methods of manufacturing the same |
| TW202311225A (zh) | 2021-06-25 | 2023-03-16 | 韓商松原產業股份有限公司 | O-烷基化位阻抗氧化劑 |
| EP4381032A1 (de) | 2021-08-03 | 2024-06-12 | LANXESS Deutschland GmbH | Neue additivmischung |
| PL4130207T3 (pl) | 2021-08-03 | 2024-07-22 | Lanxess Deutschland Gmbh | Mieszanina dodatków do olejów turbinowych |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US394492A (en) * | 1888-12-11 | Step-ladder | ||
| US2530769A (en) * | 1950-01-12 | 1950-11-21 | Goodrich Co B F | Diphenyl amine derivatives |
| US2943112A (en) | 1957-11-06 | 1960-06-28 | Pennsalt Chemicals Corp | Alkylation of diphenylamine |
| US3944492A (en) | 1966-04-07 | 1976-03-16 | Uniroyal, Inc. | Lubricant compositions containing N-substituted naphthylamines as antioxidants |
| JP2510088B2 (ja) * | 1986-06-05 | 1996-06-26 | 日本石油株式会社 | 潤滑油組成物 |
| JP2539677B2 (ja) * | 1989-01-13 | 1996-10-02 | 日本石油株式会社 | 潤滑油組成物 |
| DE4300892A1 (de) | 1993-01-15 | 1994-07-21 | Hoechst Ag | Verfahren zur thermooxidativen Stabilisierung von Glykolverbindungen und thermooxidativ stabilisierte Mischungen davon |
| SG65759A1 (en) | 1997-06-06 | 1999-06-22 | Ciba Sc Holding Ag | Nonylated diphenylamines |
| DE19756146A1 (de) * | 1997-12-17 | 1999-06-24 | Bayer Ag | Herstellung von N-Phenyl-1-naphthylamin |
| DE60029049T2 (de) * | 1999-05-19 | 2007-06-21 | Ciba Speciality Chemicals Holding Inc. | Stabilisierte hydroraffinierte und hydroentparaffinierte Schmiermittelzusammensetzungen |
| GB2368848B (en) * | 2000-09-21 | 2002-11-27 | Ciba Sc Holding Ag | Lubricants with 5-tert.-butyl-hydroxy-3-methylphenyl substituted fatty acid esters |
| CA2403540A1 (en) * | 2001-11-20 | 2003-05-20 | Bp Corporation North America Inc. | Synergystic combination of aryl amine antioxidants in aviation turbine oils |
| CA2559746C (en) | 2004-04-01 | 2013-06-25 | Ciba Specialty Chemicals Holding Inc. | Alkylated pana and dpa compositions |
| EP2055763A1 (en) | 2007-10-23 | 2009-05-06 | Shell Internationale Research Maatschappij B.V. | Lubricating oil composition |
| CN102112434A (zh) | 2008-08-08 | 2011-06-29 | 雅宝公司 | 辛基化苯基-α-萘胺产物混合物及具有高辛基化苯基-α-萘胺含量的该等混合物的制备 |
| US8227391B2 (en) | 2008-10-17 | 2012-07-24 | Afton Chemical Corporation | Lubricating composition with good oxidative stability and reduced deposit formation |
-
2005
- 2005-03-23 CA CA2559746A patent/CA2559746C/en not_active Expired - Fee Related
- 2005-03-23 SG SG200904460-3A patent/SG154437A1/en unknown
- 2005-03-23 CN CN2005800103558A patent/CN1938260B/zh not_active Expired - Fee Related
- 2005-03-23 BR BRPI0509521A patent/BRPI0509521B1/pt not_active IP Right Cessation
- 2005-03-23 ES ES05740135.8T patent/ES2560658T3/es not_active Expired - Lifetime
- 2005-03-23 PL PL05740135T patent/PL1730101T3/pl unknown
- 2005-03-23 KR KR1020067018672A patent/KR101239143B1/ko not_active Expired - Fee Related
- 2005-03-23 US US10/594,379 patent/US8030259B2/en active Active
- 2005-03-23 WO PCT/EP2005/051324 patent/WO2005097728A1/en not_active Ceased
- 2005-03-23 EP EP05740135.8A patent/EP1730101B1/en not_active Expired - Lifetime
- 2005-03-23 KR KR1020127030576A patent/KR20120133398A/ko not_active Withdrawn
- 2005-03-23 JP JP2007505544A patent/JP5080969B2/ja not_active Expired - Fee Related
- 2005-03-30 TW TW094109926A patent/TW200536813A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0509521A (pt) | 2007-09-18 |
| SG154437A1 (en) | 2009-08-28 |
| KR101239143B1 (ko) | 2013-03-11 |
| KR20120133398A (ko) | 2012-12-10 |
| CN1938260B (zh) | 2010-06-16 |
| PL1730101T3 (pl) | 2016-05-31 |
| KR20060127187A (ko) | 2006-12-11 |
| WO2005097728A1 (en) | 2005-10-20 |
| JP2007530636A (ja) | 2007-11-01 |
| US8030259B2 (en) | 2011-10-04 |
| CA2559746A1 (en) | 2005-10-20 |
| ES2560658T3 (es) | 2016-02-22 |
| US20080274925A1 (en) | 2008-11-06 |
| EP1730101B1 (en) | 2015-11-18 |
| JP5080969B2 (ja) | 2012-11-21 |
| BRPI0509521B1 (pt) | 2015-09-29 |
| CN1938260A (zh) | 2007-03-28 |
| EP1730101A1 (en) | 2006-12-13 |
| TW200536813A (en) | 2005-11-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20170323 |