JP2008510053A5 - - Google Patents
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- Publication number
- JP2008510053A5 JP2008510053A5 JP2007526448A JP2007526448A JP2008510053A5 JP 2008510053 A5 JP2008510053 A5 JP 2008510053A5 JP 2007526448 A JP2007526448 A JP 2007526448A JP 2007526448 A JP2007526448 A JP 2007526448A JP 2008510053 A5 JP2008510053 A5 JP 2008510053A5
- Authority
- JP
- Japan
- Prior art keywords
- tert
- butyl
- hydroxyhydrocinnamate
- tris
- bis
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 7
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 239000002530 phenolic antioxidant Substances 0.000 claims 6
- -1 3,5-di-tert-butyl-4-hydroxyhydrocinnamoyloxy Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 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 3
- YJBOLABRGWKEKR-UHFFFAOYSA-N 3,3-bis[1-carboxy-2-(3,5-ditert-butyl-4-hydroxyphenyl)ethyl]-2,6-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-4,4-dimethylheptanedioic acid Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC(CC(C)(C)C(C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(O)=O)(C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(O)=O)C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(O)=O)C(O)=O)=C1 YJBOLABRGWKEKR-UHFFFAOYSA-N 0.000 claims 3
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 claims 3
- NBPOOCGXISZKSX-UHFFFAOYSA-N 6-methylheptyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)CCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NBPOOCGXISZKSX-UHFFFAOYSA-N 0.000 claims 3
- 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 3
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 claims 3
- PLTOWUBLEPQHQC-UHFFFAOYSA-N [2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]-3-hydroxypropyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(CO)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 PLTOWUBLEPQHQC-UHFFFAOYSA-N 0.000 claims 3
- MFSAJLWSXLIOHZ-UHFFFAOYSA-N [2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]-3-hydroxy-2-(hydroxymethyl)propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(CO)(CO)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MFSAJLWSXLIOHZ-UHFFFAOYSA-N 0.000 claims 3
- 239000003963 antioxidant agent Substances 0.000 claims 3
- 230000003078 antioxidant effect Effects 0.000 claims 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 3
- 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 2
- LRYDMYPWXGPTAU-UHFFFAOYSA-N 2,5-bis[1,1-bis(3-tert-butyl-4-hydroxyphenyl)ethyl]hexanedioic acid Chemical compound C1=C(O)C(C(C)(C)C)=CC(C(C)(C(CCC(C(O)=O)C(C)(C=2C=C(C(O)=CC=2)C(C)(C)C)C=2C=C(C(O)=CC=2)C(C)(C)C)C(O)=O)C=2C=C(C(O)=CC=2)C(C)(C)C)=C1 LRYDMYPWXGPTAU-UHFFFAOYSA-N 0.000 claims 2
- PRWJPWSKLXYEPD-UHFFFAOYSA-N 4-[4,4-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butan-2-yl]-2-tert-butyl-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(C)CC(C=1C(=CC(O)=C(C=1)C(C)(C)C)C)C1=CC(C(C)(C)C)=C(O)C=C1C PRWJPWSKLXYEPD-UHFFFAOYSA-N 0.000 claims 2
- ZVVFVKJZNVSANF-UHFFFAOYSA-N 6-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]hexyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCCCCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 ZVVFVKJZNVSANF-UHFFFAOYSA-N 0.000 claims 2
- OKOBUGCCXMIKDM-UHFFFAOYSA-N Irganox 1098 Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)NCCCCCCNC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 OKOBUGCCXMIKDM-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 claims 1
- XYXJKPCGSGVSBO-UHFFFAOYSA-N 1,3,5-tris[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CN1C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C1=O XYXJKPCGSGVSBO-UHFFFAOYSA-N 0.000 claims 1
- SAJFQHPVIYPPEY-UHFFFAOYSA-N 2,6-ditert-butyl-4-(dioctadecoxyphosphorylmethyl)phenol Chemical compound CCCCCCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCCCCCC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SAJFQHPVIYPPEY-UHFFFAOYSA-N 0.000 claims 1
- BUZQSUSEQHVGCB-UHFFFAOYSA-N 2,6-ditert-butyl-4-[[5-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-4-hydroxy-1,3,5-trimethylcyclohex-2-en-1-yl]methyl]phenol Chemical compound C1C(C)(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(O)C(C)=CC1(C)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BUZQSUSEQHVGCB-UHFFFAOYSA-N 0.000 claims 1
- OXWDLAHVJDUQJM-UHFFFAOYSA-N 2-[[2-[2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]ethylamino]-2-oxoacetyl]amino]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCNC(=O)C(=O)NCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 OXWDLAHVJDUQJM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- BXULGGYCPFDQON-UHFFFAOYSA-N 4-[[3,5-bis(octylsulfanyl)-1,3,5-triazinan-1-yl]amino]-2,6-ditert-butylphenol Chemical compound C1N(SCCCCCCCC)CN(SCCCCCCCC)CN1NC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BXULGGYCPFDQON-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- 239000002199 base oil Substances 0.000 claims 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims 1
- SJEZDMHBMZPMME-UHFFFAOYSA-L calcium;(3,5-ditert-butyl-4-hydroxyphenyl)methyl-ethoxyphosphinate Chemical compound [Ca+2].CCOP([O-])(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1.CCOP([O-])(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SJEZDMHBMZPMME-UHFFFAOYSA-L 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims 1
- 239000010687 lubricating oil Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 239000003760 tallow Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60259304P | 2004-08-18 | 2004-08-18 | |
| US60/602,593 | 2004-08-18 | ||
| PCT/EP2005/053883 WO2006018403A1 (en) | 2004-08-18 | 2005-08-08 | Lubricating oil compositions with improved performance |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008510053A JP2008510053A (ja) | 2008-04-03 |
| JP2008510053A5 true JP2008510053A5 (https=) | 2008-09-25 |
| JP5078614B2 JP5078614B2 (ja) | 2012-11-21 |
Family
ID=34973243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007526448A Expired - Fee Related JP5078614B2 (ja) | 2004-08-18 | 2005-08-08 | 改善された性能を有する潤滑油組成物 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7531487B2 (https=) |
| EP (1) | EP1776441A1 (https=) |
| JP (1) | JP5078614B2 (https=) |
| KR (1) | KR101223000B1 (https=) |
| CN (1) | CN101006165B (https=) |
| AU (1) | AU2005273923B2 (https=) |
| BR (1) | BRPI0514457B1 (https=) |
| CA (1) | CA2575502C (https=) |
| MX (1) | MX2007001788A (https=) |
| TW (1) | TWI383042B (https=) |
| WO (1) | WO2006018403A1 (https=) |
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| EP1492856A4 (en) | 2002-04-05 | 2010-11-10 | Univ Massachusetts Lowell | POLYMER ANTIOXIDANTS |
| ATE442426T1 (de) | 2004-07-23 | 2009-09-15 | Polnox Corp | Antioxidative makromonomere, deren herstellung und verwendung |
| EP1817393A2 (en) | 2004-12-03 | 2007-08-15 | Polnox Corporation | Process for the synthesis of polyalkylphenol antioxidants |
| US7902317B2 (en) | 2004-12-03 | 2011-03-08 | Polnox Corporation | Synthesis of aniline and phenol-based antioxidant macromonomers and corresponding polymers |
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| US7705176B2 (en) | 2005-10-27 | 2010-04-27 | Polnox Corporation | Macromolecular antioxidants based on sterically hindered phenols and phosphites |
| US20070106059A1 (en) * | 2005-10-27 | 2007-05-10 | Cholli Ashok L | Macromolecular antioxidants and polymeric macromolecular antioxidants |
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| CN102937581A (zh) * | 2012-11-08 | 2013-02-20 | 中国人民解放军空军勤务学院 | 润滑脂高温抗氧化性能的快速评定方法 |
| EP3071544B1 (en) | 2013-11-22 | 2022-07-06 | Polnox Corporation | Macromolecular antioxidants based on dual type moiety per molecule: structures methods of making and using the same |
| CN104152214A (zh) * | 2014-08-15 | 2014-11-19 | 天津利安隆新材料股份有限公司 | 一种润滑油组合物 |
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| EP1227145B1 (en) | 2001-01-24 | 2013-03-13 | Nippon Mitsubishi Oil Corporation | Lubricating oil compositions |
| EP1439217B1 (en) | 2001-10-12 | 2012-06-20 | Nippon Oil Corporation | Lubricating oil composition for internal combustion engine |
| JP4011967B2 (ja) | 2002-05-07 | 2007-11-21 | シェブロンジャパン株式会社 | 潤滑油組成物 |
| CN100497560C (zh) | 2002-06-28 | 2009-06-10 | 新日本石油株式会社 | 润滑油组合物 |
| US7667066B2 (en) * | 2004-02-27 | 2010-02-23 | Albemarle Corporation | Preparation of sterically hindered hydroxyphenylcarboxylic acid esters |
-
2005
- 2005-08-08 EP EP05773928A patent/EP1776441A1/en not_active Withdrawn
- 2005-08-08 CN CN2005800280321A patent/CN101006165B/zh not_active Expired - Fee Related
- 2005-08-08 CA CA2575502A patent/CA2575502C/en not_active Expired - Fee Related
- 2005-08-08 MX MX2007001788A patent/MX2007001788A/es active IP Right Grant
- 2005-08-08 JP JP2007526448A patent/JP5078614B2/ja not_active Expired - Fee Related
- 2005-08-08 WO PCT/EP2005/053883 patent/WO2006018403A1/en not_active Ceased
- 2005-08-08 KR KR1020077002212A patent/KR101223000B1/ko not_active Expired - Fee Related
- 2005-08-08 AU AU2005273923A patent/AU2005273923B2/en not_active Ceased
- 2005-08-08 BR BRPI0514457-4A patent/BRPI0514457B1/pt not_active IP Right Cessation
- 2005-08-10 US US11/201,389 patent/US7531487B2/en active Active
- 2005-08-16 TW TW094127833A patent/TWI383042B/zh not_active IP Right Cessation
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