JP5286271B2 - 高分子アミン−フェノール系抗酸化剤組成物、それの製造技術および使用 - Google Patents
高分子アミン−フェノール系抗酸化剤組成物、それの製造技術および使用 Download PDFInfo
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- JP5286271B2 JP5286271B2 JP2009533498A JP2009533498A JP5286271B2 JP 5286271 B2 JP5286271 B2 JP 5286271B2 JP 2009533498 A JP2009533498 A JP 2009533498A JP 2009533498 A JP2009533498 A JP 2009533498A JP 5286271 B2 JP5286271 B2 JP 5286271B2
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- Prior art keywords
- hydrocarbyl
- weight
- substituted
- range
- hydroxylbenzyl
- 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.)
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- 238000005516 engineering process Methods 0.000 title description 2
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- 239000007795 chemical reaction product Substances 0.000 claims description 59
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 57
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 25
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- -1 hydroxylbenzyl group Chemical group 0.000 claims description 20
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 5
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- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
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- 235000006708 antioxidants Nutrition 0.000 claims 29
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 238000000034 method Methods 0.000 description 19
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- 239000002199 base oil Substances 0.000 description 12
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- MDWVSAYEQPLWMX-UHFFFAOYSA-N 4,4'-Methylenebis(2,6-di-tert-butylphenol) Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MDWVSAYEQPLWMX-UHFFFAOYSA-N 0.000 description 9
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- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 9
- 238000007792 addition Methods 0.000 description 9
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- 239000003054 catalyst Substances 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 238000005804 alkylation reaction Methods 0.000 description 7
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- LVZUNTGFCXNQAF-UHFFFAOYSA-N n-nonyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCCC)C1=CC=CC=C1 LVZUNTGFCXNQAF-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000010525 oxidative degradation reaction Methods 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- HNURKXXMYARGAY-UHFFFAOYSA-N 2,6-Di-tert-butyl-4-hydroxymethylphenol Chemical compound CC(C)(C)C1=CC(CO)=CC(C(C)(C)C)=C1O HNURKXXMYARGAY-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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- 125000003545 alkoxy group Chemical group 0.000 description 4
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- 229910052698 phosphorus Inorganic materials 0.000 description 3
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- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 2
- XPFFETROZDUIOL-UHFFFAOYSA-N 2-tert-butyl-4-(hydroxymethyl)-6-methylphenol Chemical compound CC1=CC(CO)=CC(C(C)(C)C)=C1O XPFFETROZDUIOL-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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
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- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
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- 150000001412 amines Chemical class 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
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- 238000011068 loading method Methods 0.000 description 2
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- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
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- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
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- WKBALTUBRZPIPZ-UHFFFAOYSA-N 2,6-di(propan-2-yl)aniline Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N WKBALTUBRZPIPZ-UHFFFAOYSA-N 0.000 description 1
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- DIYUQYILDNYKSU-UHFFFAOYSA-N 2-benzyl-6-propan-2-yl-4-(propoxymethyl)phenol Chemical compound CC(C)C1=CC(COCCC)=CC(CC=2C=CC=CC=2)=C1O DIYUQYILDNYKSU-UHFFFAOYSA-N 0.000 description 1
- ONMGLBSQQKJNLN-UHFFFAOYSA-N 2-cyclohexyl-6-ethyl-4-(hydroxymethyl)phenol Chemical compound CCC1=CC(CO)=CC(C2CCCCC2)=C1O ONMGLBSQQKJNLN-UHFFFAOYSA-N 0.000 description 1
- JJVKJJNCIILLRP-UHFFFAOYSA-N 2-ethyl-6-methylaniline Chemical compound CCC1=CC=CC(C)=C1N JJVKJJNCIILLRP-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 description 1
- UPDWTBUVWFFFLT-UHFFFAOYSA-N 2-tert-butyl-4-(hexadecoxymethyl)-6-methylphenol Chemical compound CCCCCCCCCCCCCCCCOCC1=CC(C)=C(O)C(C(C)(C)C)=C1 UPDWTBUVWFFFLT-UHFFFAOYSA-N 0.000 description 1
- UZCYNSOPTHFEBK-UHFFFAOYSA-N 2-tert-butyl-4-(hydroxymethyl)-6-phenylphenol Chemical compound CC(C)(C)C1=CC(CO)=CC(C=2C=CC=CC=2)=C1O UZCYNSOPTHFEBK-UHFFFAOYSA-N 0.000 description 1
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- IEWCKTWDZYPKSZ-UHFFFAOYSA-N 2-tert-butyl-4-(methoxymethyl)-6-methylphenol Chemical compound COCC1=CC(C)=C(O)C(C(C)(C)C)=C1 IEWCKTWDZYPKSZ-UHFFFAOYSA-N 0.000 description 1
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- MUNOBADFTHUUFG-UHFFFAOYSA-N 3-phenylaniline Chemical group NC1=CC=CC(C=2C=CC=CC=2)=C1 MUNOBADFTHUUFG-UHFFFAOYSA-N 0.000 description 1
- NQVLOHKMEASTMW-UHFFFAOYSA-N 4-(4-methylphenyl)aniline Chemical group C1=CC(C)=CC=C1C1=CC=C(N)C=C1 NQVLOHKMEASTMW-UHFFFAOYSA-N 0.000 description 1
- XCSJNCBKRFGJKY-UHFFFAOYSA-N 4-(ethoxymethyl)-2,6-di(propan-2-yl)phenol Chemical compound CCOCC1=CC(C(C)C)=C(O)C(C(C)C)=C1 XCSJNCBKRFGJKY-UHFFFAOYSA-N 0.000 description 1
- VYUAKHHQSWENSJ-UHFFFAOYSA-N 4-(hydroxymethyl)-2,6-di(propan-2-yl)phenol Chemical compound CC(C)C1=CC(CO)=CC(C(C)C)=C1O VYUAKHHQSWENSJ-UHFFFAOYSA-N 0.000 description 1
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 1
- BFVOBXSKECUHSW-UHFFFAOYSA-N 4-n,4-n-di(butan-2-yl)benzene-1,4-diamine Chemical compound CCC(C)N(C(C)CC)C1=CC=C(N)C=C1 BFVOBXSKECUHSW-UHFFFAOYSA-N 0.000 description 1
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- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
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- 238000006731 degradation reaction Methods 0.000 description 1
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- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
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- 239000002816 fuel additive Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
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- 230000008018 melting Effects 0.000 description 1
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- 239000011707 mineral Substances 0.000 description 1
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- JDEJGVSZUIJWBM-UHFFFAOYSA-N n,n,2-trimethylaniline Chemical compound CN(C)C1=CC=CC=C1C JDEJGVSZUIJWBM-UHFFFAOYSA-N 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- AJUXDFHPVZQOGF-UHFFFAOYSA-N n,n-dimethyl-1-naphthylamine Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1 AJUXDFHPVZQOGF-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- AKEYUWUEAXIBTF-UHFFFAOYSA-N n-methylnaphthalen-1-amine Chemical compound C1=CC=C2C(NC)=CC=CC2=C1 AKEYUWUEAXIBTF-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 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 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 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 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000010689 synthetic lubricating oil Substances 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- OVKHEVLQASDMFJ-UHFFFAOYSA-N triazanium trichloride Chemical compound [NH4+].[NH4+].[NH4+].[Cl-].[Cl-].[Cl-] OVKHEVLQASDMFJ-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
- C07C215/82—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the amino groups further bound to a carbon atom of another six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
- C07C39/16—Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
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- 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
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
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- 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
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/16—Ethers
- C10M129/20—Cyclic ethers having 4 or more ring atoms, e.g. furans, dioxolanes
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- 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
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/44—Five-membered ring containing nitrogen and carbon only
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- 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
- C10M135/34—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur 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
- 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
-
- 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
- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/12—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M149/14—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds a condensation reaction being involved
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- 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
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
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- 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
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- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
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- 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
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
-
- 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
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Lubricants (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Polyethers (AREA)
Applications Claiming Priority (3)
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| US82983806P | 2006-10-17 | 2006-10-17 | |
| US60/829,838 | 2006-10-17 | ||
| PCT/US2007/081604 WO2008048989A2 (en) | 2006-10-17 | 2007-10-17 | Macromolecular amine-phenolic antioxidant compositions, process technology thereof, and uses thereof |
Publications (2)
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| JP2010507012A JP2010507012A (ja) | 2010-03-04 |
| JP5286271B2 true JP5286271B2 (ja) | 2013-09-11 |
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| JP2009533497A Withdrawn JP2010522136A (ja) | 2006-10-17 | 2007-10-17 | 抗酸化剤として有用なアルキル置換複素環式反応生成物 |
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| JP (2) | JP5286271B2 (enExample) |
| KR (2) | KR101520880B1 (enExample) |
| CN (2) | CN101528668B (enExample) |
| AU (4) | AU2007311084A1 (enExample) |
| BR (2) | BRPI0717811A2 (enExample) |
| CA (2) | CA2665011C (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2009073378A1 (en) * | 2007-11-29 | 2009-06-11 | Albemarle Corporation | Industrial oil formulations containing macromolecular antioxidants |
| EP2331493A1 (en) * | 2008-08-08 | 2011-06-15 | Albemarle Corporation | Octylated phenyl-alpha-naphthylamine product mixtures and production of such mixtures having a high content of octylated phenyl-alpha-naphthylamine |
| TW201031621A (en) | 2009-01-14 | 2010-09-01 | Albemarle Corp | Processes for production of macromolecular amine-phenolic antioxidant compositions containing low amounts of non-macromolecular byproducts |
| IT1393117B1 (it) * | 2009-03-04 | 2012-04-11 | Eni Spa | Lubrificanti di elevate caratteristiche prestazionali formulati con basi di gruppo ii per applicazioni motoristiche |
| KR101121922B1 (ko) * | 2011-10-20 | 2012-03-20 | 남성환 | 차체의 부식을 방지하기 위한 처리방법 |
| US20150052804A1 (en) * | 2013-08-23 | 2015-02-26 | Chevron U.S.A. Inc. | Diesel fuel composition |
| CN103450379B (zh) * | 2013-09-06 | 2016-01-20 | 中国科学院化学研究所 | 一类高效、抗迁移受阻酚抗氧剂及其制备方法 |
| CN105585536B (zh) * | 2014-10-23 | 2018-05-18 | 中国石油化工股份有限公司 | 一种抗氧剂及其制备方法和应用 |
| CN106318536B (zh) * | 2015-06-16 | 2019-06-14 | 中国石油化工股份有限公司 | 一种液压润滑油组合物及其制备方法 |
| CN106318519B (zh) * | 2015-06-16 | 2019-05-21 | 中国石油化工股份有限公司 | 一种汽油机油润滑油组合物及其制备方法 |
| CN106318534B (zh) * | 2015-06-16 | 2019-06-14 | 中国石油化工股份有限公司 | 一种金属加工润滑油组合物及其制备方法 |
| CN106318557B (zh) * | 2015-06-16 | 2019-05-21 | 中国石油化工股份有限公司 | 一种甲醇燃料发动机润滑油组合物及其制备方法 |
| CN106318518B (zh) * | 2015-06-16 | 2019-06-14 | 中国石油化工股份有限公司 | 一种自动传动液润滑油组合物及其制备方法 |
| CN106318521B (zh) * | 2015-06-16 | 2019-04-16 | 中国石油化工股份有限公司 | 一种曲轴箱系统润滑油组合物及其制备方法 |
| CN106318520B (zh) * | 2015-06-16 | 2019-06-14 | 中国石油化工股份有限公司 | 一种润滑油组合物及其制备方法 |
| CN106318522B (zh) * | 2015-06-16 | 2019-05-17 | 中国石油化工股份有限公司 | 一种燃气发动机润滑油组合物及其制备方法 |
| CN106318558B (zh) * | 2015-06-16 | 2019-04-16 | 中国石油化工股份有限公司 | 一种摩托车发动机润滑油组合物及其制备方法 |
| CN106318545B (zh) * | 2015-06-16 | 2019-04-16 | 中国石油化工股份有限公司 | 一种柴油发动机润滑油组合物及其制备方法 |
| CN106318556B (zh) * | 2015-06-16 | 2019-05-21 | 中国石油化工股份有限公司 | 一种车辆齿轮润滑油组合物及其制备方法 |
| KR20170018718A (ko) | 2015-08-10 | 2017-02-20 | 삼성전자주식회사 | 비정질 합금을 이용한 투명 전극 및 그 제조 방법 |
| HUE064128T2 (hu) * | 2015-09-02 | 2024-02-28 | Basf Se | Kenõanyag-készítmény |
| CN106753700B (zh) * | 2015-11-23 | 2019-07-23 | 中国石油化工股份有限公司 | 汽油发动机润滑油组合物及其制备方法、用途 |
| CN105505532B (zh) * | 2015-11-30 | 2018-05-25 | 江阴市苏达塑业有限公司 | 一种高温模具润滑颗粒及其制备方法 |
| JP2019518090A (ja) * | 2016-04-13 | 2019-06-27 | カストロール リミテッド | 炭化水素流体からの芳香族化合物の除去 |
| CN107304377B (zh) * | 2016-04-18 | 2019-08-16 | 中国石油化工股份有限公司 | 一种高温链条油组合物及其制备方法 |
| CN107304382B (zh) * | 2016-04-18 | 2019-08-16 | 中国石油化工股份有限公司 | 一种空气压缩机油组合物及其制备方法 |
| CN107304379B (zh) * | 2016-04-18 | 2019-08-16 | 中国石油化工股份有限公司 | 一种燃气汽轮机油组合物及其制备方法 |
| KR102363081B1 (ko) * | 2016-06-03 | 2022-02-16 | 디아이씨 가부시끼가이샤 | 다환 방향족 아미노페놀 화합물 및 수지 조성물의 제조 방법, 그리고 상기 다환 방향족 아미노페놀 화합물, 수지 조성물, 및 경화물 |
| US11084909B2 (en) * | 2016-08-30 | 2021-08-10 | Basf Se | Liquid antioxidant composition for raw rubbers |
| CN113293046B (zh) * | 2021-05-26 | 2021-11-30 | 安徽博洋润滑科技有限公司 | 一种低发尘润滑脂及其制备方法 |
| CN113831592B (zh) * | 2021-08-26 | 2023-02-28 | 贵州省材料产业技术研究院 | 一种酚胺类抗氧剂及其制备方法和应用 |
| CN117626102B (zh) * | 2024-01-26 | 2024-05-10 | 钢铁研究总院有限公司 | 一种高强韧超高强度钢及其制备方法 |
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| US2528769A (en) * | 1947-05-28 | 1950-11-07 | Socony Vacuum Oil Co Inc | Reaction product of haloalkylthiophenes and hydroxyaryl compounds |
| CH533097A (de) * | 1970-03-13 | 1973-01-31 | Sandoz Ag | Verfahren zur Herstellung von neuen heterocyclischen Verbindungen |
| US3673091A (en) * | 1970-07-16 | 1972-06-27 | Shell Oil Co | Lubricants containing oxidation inhibitors |
| US3822284A (en) * | 1970-07-16 | 1974-07-02 | Shell Oil Co | 1-and 3-substituted (3,5-di-t-butyl-4-hydroxybenzyl)carbazole |
| US3989738A (en) | 1975-07-21 | 1976-11-02 | The Goodyear Tire & Rubber Company | Method of preparing phenolic antioxidants by condensing active methylene compounds with 3,5-di-tert alkyl-4-hydroxybenzylpyridinium salts |
| SU572457A1 (ru) | 1976-03-09 | 1977-09-15 | Предприятие П/Я А-7253 | 1-3,5-Дитрет бутил-4-оксибензил-3метилпиразолон-5 в качестве противостарител светлых резин |
| US4833155A (en) | 1986-11-25 | 1989-05-23 | Syntex (U.S.A.) Inc. | 3-(ω-(3,5,-di-t-butyl-4-hydroxyphenyl)-alkanoyl)pyrroles, and anti-inflammatory uses thereof |
| ES2028130T3 (es) * | 1986-12-31 | 1992-07-01 | Ciba-Geigy Ag | Fenotiacinas substituidas como estabilizadores de lubricantes. |
| GB8804457D0 (en) * | 1988-02-25 | 1988-03-23 | Ciba Geigy Ag | Compositions |
| US4994628A (en) * | 1989-09-25 | 1991-02-19 | Ethyl Corporation | Phenolic antioxidant process |
| JP3269658B2 (ja) | 1992-06-02 | 2002-03-25 | エーザイ株式会社 | フェノール誘導体 |
| JP2002062673A (ja) * | 2000-08-14 | 2002-02-28 | Fuji Denki Gazo Device Kk | 電子写真用感光体 |
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