JP2017533985A5 - - Google Patents
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- JP2017533985A5 JP2017533985A5 JP2017525348A JP2017525348A JP2017533985A5 JP 2017533985 A5 JP2017533985 A5 JP 2017533985A5 JP 2017525348 A JP2017525348 A JP 2017525348A JP 2017525348 A JP2017525348 A JP 2017525348A JP 2017533985 A5 JP2017533985 A5 JP 2017533985A5
- Authority
- JP
- Japan
- Prior art keywords
- lubricant composition
- diol
- phosphite
- composition according
- amount
- 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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- 239000000203 mixture Substances 0.000 claims description 73
- 239000000314 lubricant Substances 0.000 claims description 49
- -1 alkylene diols Chemical class 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 239000002270 dispersing agent Substances 0.000 claims description 17
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 16
- 229910052698 phosphorus Inorganic materials 0.000 claims description 13
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical class OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 10
- 239000011574 phosphorus Substances 0.000 claims description 9
- 239000003599 detergent Substances 0.000 claims description 8
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 7
- 239000011575 calcium Substances 0.000 claims description 7
- 229910052791 calcium Inorganic materials 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 238000005260 corrosion Methods 0.000 claims description 6
- 230000007797 corrosion Effects 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 230000001050 lubricating effect Effects 0.000 claims description 6
- 125000004437 phosphorous atom Chemical group 0.000 claims description 6
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- OJMJOSRCBAXSAQ-UHFFFAOYSA-N 2,2-dibutylpropane-1,3-diol Chemical compound CCCCC(CO)(CO)CCCC OJMJOSRCBAXSAQ-UHFFFAOYSA-N 0.000 claims description 2
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 claims description 2
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 claims description 2
- FZHZPYGRGQZBCV-UHFFFAOYSA-N 2-propylpropane-1,3-diol Chemical compound CCCC(CO)CO FZHZPYGRGQZBCV-UHFFFAOYSA-N 0.000 claims description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 150000003751 zinc Chemical class 0.000 claims description 2
- 150000008301 phosphite esters Chemical class 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 1
- 239000003607 modifier Substances 0.000 description 8
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 description 6
- 229920002367 Polyisobutene Polymers 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229960002317 succinimide Drugs 0.000 description 4
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- ZMRQTIAUOLVKOX-UHFFFAOYSA-L calcium;diphenoxide Chemical compound [Ca+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 ZMRQTIAUOLVKOX-UHFFFAOYSA-L 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- BVXOPEOQUQWRHQ-UHFFFAOYSA-N dibutyl phosphite Chemical compound CCCCOP([O-])OCCCC BVXOPEOQUQWRHQ-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000003580 thiophosphoric acid esters Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462078607P | 2014-11-12 | 2014-11-12 | |
| US62/078,607 | 2014-11-12 | ||
| PCT/US2015/060106 WO2016089565A1 (en) | 2014-11-12 | 2015-11-11 | Mixed phosphorus esters for lubricant applications |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019213463A Division JP2020023725A (ja) | 2014-11-12 | 2019-11-26 | 潤滑剤用途のための混合リン含有酸エステル |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017533985A JP2017533985A (ja) | 2017-11-16 |
| JP2017533985A5 true JP2017533985A5 (https=) | 2018-12-13 |
| JP6806676B2 JP6806676B2 (ja) | 2021-01-06 |
Family
ID=55543027
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017525348A Active JP6806676B2 (ja) | 2014-11-12 | 2015-11-11 | 潤滑剤用途のための混合リン含有酸エステル |
| JP2019213463A Withdrawn JP2020023725A (ja) | 2014-11-12 | 2019-11-26 | 潤滑剤用途のための混合リン含有酸エステル |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019213463A Withdrawn JP2020023725A (ja) | 2014-11-12 | 2019-11-26 | 潤滑剤用途のための混合リン含有酸エステル |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US10793802B2 (https=) |
| EP (1) | EP3218454B1 (https=) |
| JP (2) | JP6806676B2 (https=) |
| KR (1) | KR102586697B1 (https=) |
| CN (1) | CN107109281B (https=) |
| BR (1) | BR112017009936B1 (https=) |
| CA (1) | CA2967334C (https=) |
| WO (1) | WO2016089565A1 (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6405217B2 (ja) * | 2014-12-09 | 2018-10-17 | シェルルブリカンツジャパン株式会社 | すべり案内面用潤滑油組成物 |
| JP6533689B2 (ja) * | 2015-04-22 | 2019-06-19 | 出光興産株式会社 | 自動変速機油 |
| CA3030950C (en) | 2016-07-15 | 2024-11-12 | The Lubrizol Corporation | ENGINE LUBRICANTS FOR FIGHTING SILOXANE DEPOSITS |
| JP6753608B2 (ja) * | 2016-10-19 | 2020-09-09 | 出光興産株式会社 | 潤滑油組成物、潤滑方法、及び変速機 |
| CA3045129A1 (en) | 2016-12-16 | 2018-06-21 | The Lubrizol Corporation | Lubrication of an automatic transmission with reduced wear on a needle bearing |
| CA3072337A1 (en) * | 2017-08-16 | 2019-02-21 | The Lubrizol Corporation | Lubricating composition for a hybrid electric vehicle transmission |
| CN111417704A (zh) * | 2017-10-02 | 2020-07-14 | 路博润公司 | 含磷抗磨添加剂 |
| WO2019136052A1 (en) * | 2018-01-04 | 2019-07-11 | The Lubrizol Corporation | Boron containing automotive gear oil |
| EP3752588B1 (en) * | 2018-02-12 | 2023-06-14 | LANXESS Corporation | Anti-wear composition for lubricants |
| US10640723B2 (en) * | 2018-03-16 | 2020-05-05 | Afton Chemical Corporation | Lubricants containing amine salt of acid phosphate and hydrocarbyl borate |
| FR3111639B1 (fr) * | 2020-06-22 | 2022-08-19 | Total Marketing Services | Composition aqueuse pour la lubrification des systèmes mécaniques |
| EP4632052A3 (en) | 2020-06-25 | 2025-12-31 | The Lubrizol Corporation | CYCLIC PHOSPHONATE ESTERS FOR LUBRICATING APPLICATIONS |
| FR3112791B1 (fr) * | 2020-07-22 | 2023-04-28 | Total Marketing Services | Composition lubrifiante pour transmission automobile aux propriétés anticorrosion améliorées. |
| FR3112793B1 (fr) * | 2020-07-22 | 2023-04-28 | Total Marketing Services | Composition lubrifiante pour transmission automobile. |
| FR3112792B1 (fr) * | 2020-07-22 | 2023-04-28 | Total Marketing Services | Composition lubrifiante pour transmission automobile stable à l’oxydation. |
| WO2023196116A1 (en) | 2022-04-06 | 2023-10-12 | The Lubrizol Corporation | Method to minimize conductive deposits |
| US11639480B1 (en) * | 2022-06-20 | 2023-05-02 | Afton Chemical Corporation | Phosphorus antiwear system for improved gear protection |
| US12187819B1 (en) | 2023-11-15 | 2025-01-07 | Tpc Group, Llc | Compound, its preparation and use |
| US12565625B2 (en) | 2023-12-18 | 2026-03-03 | Afton Chemical Corporation | Thiophosphate esters as antiwear additives for lubricants |
| WO2025213291A1 (en) * | 2024-04-07 | 2025-10-16 | The Lubrizol Corporation | Boron containing automotive gear oil |
| JP2026009797A (ja) * | 2024-07-08 | 2026-01-21 | アフトン・ケミカル・コーポレーション | 改善されたピストン清浄性のための清浄剤系 |
| US12460150B1 (en) | 2024-09-27 | 2025-11-04 | Afton Chemical Corporation | Low-ash lubricating compositions |
| US20260092151A1 (en) | 2024-10-02 | 2026-04-02 | Tpc Group Llc | Compounds, their Preparation and Use |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3228998A (en) | 1960-10-17 | 1966-01-11 | Union Oil Co | Liquid polyphosphate esters |
| US3328360A (en) | 1962-07-06 | 1967-06-27 | Exxon Research Engineering Co | Polymers containing phosphorus |
| US3381022A (en) | 1963-04-23 | 1968-04-30 | Lubrizol Corp | Polymerized olefin substituted succinic acid esters |
| FR1500821A (fr) | 1966-05-05 | 1967-11-10 | Prod Chim Et De Synthese Soc D | Nouveaux phosphites organiques |
| US4298481A (en) | 1979-02-23 | 1981-11-03 | Tenneco Chemicals, Inc. | High temperature grease compositions |
| US4549976A (en) | 1983-10-06 | 1985-10-29 | Mobil Oil Corporation | Lubricant composition containing reaction products of vicinal diols and phosphorus oxyhalides |
| US4557845A (en) | 1983-12-14 | 1985-12-10 | Mobil Oil Corporation | Alkoxylated amine-phosphite reaction product and lubricant and fuel containing same |
| US4612129A (en) | 1985-01-31 | 1986-09-16 | The Lubrizol Corporation | Sulfur-containing compositions, and additive concentrates and lubricating oils containing same |
| US4704218A (en) | 1985-12-16 | 1987-11-03 | Horodysky Andrew G | Reaction products of sulfur containing vicinal diols and hydrogen phosphites as lubricant and fuel additives |
| EP0309481B1 (en) | 1986-06-13 | 1994-03-16 | The Lubrizol Corporation | Phosphorus-containing lubricant and functional fluid compositions |
| US4792410A (en) | 1986-12-22 | 1988-12-20 | The Lubrizol Corporation | Lubricant composition suitable for manual transmission fluids |
| ES2086534T3 (es) | 1990-01-05 | 1996-07-01 | Lubrizol Corp | Fluido de transmision universal. |
| BR9509885A (pt) | 1994-12-09 | 1997-10-21 | Exxon Chemical Patents Inc | Aditivo solúvel em óleo composição de óleo lubrificante composição concentrada e processo para formar o aditivo |
| US5544744A (en) | 1995-05-01 | 1996-08-13 | Oman; John I. | Engine parts organizer |
| AU710294B2 (en) | 1995-09-12 | 1999-09-16 | Lubrizol Corporation, The | Lubrication fluids for reduced air entrainment and improved gear protection |
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| JP4199945B2 (ja) * | 2001-10-02 | 2008-12-24 | 新日本石油株式会社 | 潤滑油組成物 |
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| WO2005012468A1 (en) | 2003-08-01 | 2005-02-10 | The Lubrizol Corporation | Mixed dispersants for lubricants |
| US7053254B2 (en) | 2003-11-07 | 2006-05-30 | Chevron U.S.A, Inc. | Process for improving the lubricating properties of base oils using a Fischer-Tropsch derived bottoms |
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| CA2584744C (en) | 2004-10-25 | 2013-09-24 | The Lubrizol Corporation | Star polymers and compositions thereof |
| US8299003B2 (en) * | 2005-11-09 | 2012-10-30 | Afton Chemical Corporation | Composition comprising a sulfur-containing, phosphorus-containing compound, and/or its salt, and uses thereof |
| JP5230605B2 (ja) | 2006-04-24 | 2013-07-10 | ザ ルブリゾル コーポレイション | 星形ポリマー潤滑組成物 |
| US20080119378A1 (en) | 2006-11-21 | 2008-05-22 | Chevron Oronite Company Llc | Functional fluids comprising alkyl toluene sulfonates |
| CA2671911C (en) | 2006-12-18 | 2015-04-21 | The Lubrizol Corporation | Functional fluid comprising a detergent and friction modifier |
| US7786057B2 (en) | 2007-02-08 | 2010-08-31 | Infineum International Limited | Soot dispersants and lubricating oil compositions containing same |
| CA2705274A1 (en) | 2007-11-13 | 2009-05-22 | The Lubrizol Corporation | Lubricating composition containing a polymer |
| JP5459875B2 (ja) | 2008-11-26 | 2014-04-02 | ザ ルブリゾル コーポレイション | カルボン酸および芳香族ポリアミンで官能基化されたポリマーを含有する潤滑組成物 |
| EP2367917A1 (en) | 2008-12-09 | 2011-09-28 | The Lubrizol Corporation | Lubricating composition containing a compound derived from a hydroxy-carboxylic acid |
| KR101720812B1 (ko) * | 2009-02-18 | 2017-03-28 | 더루우브리졸코오포레이션 | 윤활제에 마찰 조정제로서의 옥살산 비스-아미드 또는 아미드-에스테르 |
| WO2010126760A2 (en) * | 2009-04-30 | 2010-11-04 | The Lubrizol Corporation | Polymeric phosphorus esters for lubricant applications |
| WO2012154708A1 (en) | 2011-05-12 | 2012-11-15 | The Lubrizol Corporation | Aromatic imides and esters as lubricant additives |
-
2015
- 2015-11-11 US US15/525,691 patent/US10793802B2/en active Active
- 2015-11-11 CN CN201580073036.5A patent/CN107109281B/zh active Active
- 2015-11-11 BR BR112017009936-5A patent/BR112017009936B1/pt active IP Right Grant
- 2015-11-11 JP JP2017525348A patent/JP6806676B2/ja active Active
- 2015-11-11 WO PCT/US2015/060106 patent/WO2016089565A1/en not_active Ceased
- 2015-11-11 CA CA2967334A patent/CA2967334C/en active Active
- 2015-11-11 EP EP15843102.3A patent/EP3218454B1/en active Active
- 2015-11-11 KR KR1020177016044A patent/KR102586697B1/ko active Active
-
2019
- 2019-11-26 JP JP2019213463A patent/JP2020023725A/ja not_active Withdrawn
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