JP6062364B2 - 潤滑組成物における使用のためのリン含有耐摩耗化合物の調製 - Google Patents
潤滑組成物における使用のためのリン含有耐摩耗化合物の調製 Download PDFInfo
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- JP6062364B2 JP6062364B2 JP2013527114A JP2013527114A JP6062364B2 JP 6062364 B2 JP6062364 B2 JP 6062364B2 JP 2013527114 A JP2013527114 A JP 2013527114A JP 2013527114 A JP2013527114 A JP 2013527114A JP 6062364 B2 JP6062364 B2 JP 6062364B2
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- WNBGUYXVNNDNEH-UHFFFAOYSA-L zinc;2-methylpropoxy-(2-methylpropylsulfanyl)-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CC(C)COP([O-])(=S)SCC(C)C.CC(C)COP([O-])(=S)SCC(C)C WNBGUYXVNNDNEH-UHFFFAOYSA-L 0.000 description 1
- UXHYTRGVMSDNEI-UHFFFAOYSA-L zinc;4-methylpentan-2-yloxy-(4-methylpentan-2-ylsulfanyl)-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CC(C)CC(C)OP([O-])(=S)SC(C)CC(C)C.CC(C)CC(C)OP([O-])(=S)SC(C)CC(C)C UXHYTRGVMSDNEI-UHFFFAOYSA-L 0.000 description 1
- OECQDNKCDGGPFY-UHFFFAOYSA-L zinc;bis(2-ethylhexoxy)-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].CCCCC(CC)COP([S-])(=S)OCC(CC)CCCC.CCCCC(CC)COP([S-])(=S)OCC(CC)CCCC OECQDNKCDGGPFY-UHFFFAOYSA-L 0.000 description 1
- BCLLIVNRSGTXBX-UHFFFAOYSA-L zinc;decoxy-decylsulfanyl-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CCCCCCCCCCOP([O-])(=S)SCCCCCCCCCC.CCCCCCCCCCOP([O-])(=S)SCCCCCCCCCC BCLLIVNRSGTXBX-UHFFFAOYSA-L 0.000 description 1
- VYEHCXHIPZIYIJ-UHFFFAOYSA-L zinc;dodecoxy-dodecylsulfanyl-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CCCCCCCCCCCCOP([O-])(=S)SCCCCCCCCCCCC.CCCCCCCCCCCCOP([O-])(=S)SCCCCCCCCCCCC VYEHCXHIPZIYIJ-UHFFFAOYSA-L 0.000 description 1
- CWARVPYFLMQZPG-UHFFFAOYSA-L zinc;heptoxy-heptylsulfanyl-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CCCCCCCOP([O-])(=S)SCCCCCCC.CCCCCCCOP([O-])(=S)SCCCCCCC CWARVPYFLMQZPG-UHFFFAOYSA-L 0.000 description 1
- SMHSUQSYYIPZSI-UHFFFAOYSA-L zinc;nonoxy-nonylsulfanyl-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CCCCCCCCCOP([O-])(=S)SCCCCCCCCC.CCCCCCCCCOP([O-])(=S)SCCCCCCCCC SMHSUQSYYIPZSI-UHFFFAOYSA-L 0.000 description 1
- GBEDXBRGRSPHRI-UHFFFAOYSA-L zinc;octoxy-octylsulfanyl-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CCCCCCCCOP([O-])(=S)SCCCCCCCC.CCCCCCCCOP([O-])(=S)SCCCCCCCC GBEDXBRGRSPHRI-UHFFFAOYSA-L 0.000 description 1
- HHMFJIHYTYQNJP-UHFFFAOYSA-L zinc;oxido-pentoxy-pentylsulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CCCCCOP([O-])(=S)SCCCCC.CCCCCOP([O-])(=S)SCCCCC HHMFJIHYTYQNJP-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/093—Polyol derivatives esterified at least twice by phosphoric acid 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/08—Ammonium or amine salts
-
- 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
- C10M2223/043—Ammonium or amine salts thereof
-
- 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
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- 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
- C10N2070/00—Specific manufacturing methods for lubricant compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
一実施形態において、例えば、以下の項目が提供される。
(項目1)
リン酸のヒドロキシ置換エステルの塩を調製するためのプロセスであって、
(a)リン酸ジエステルをアルキレンオキシドと反応させる工程、
(b)工程(a)の生成物混合物をリン酸処理剤と反応させる工程;および
(c)工程(b)の生成物混合物をアミンと反応させる工程
を含み、
前記リン酸ジエステルは、リン酸モノエステルの実質的に非存在下で前記工程(a)のアルキレンオキシドと反応させ、前記リン酸モノエステルの量は、存在するリン酸モノエステルおよびリン酸ジエステルの合計の0から10重量パーセントである、プロセス。
(項目2)
前記工程(a)の反応中に存在する場合、前記存在するリン酸モノエステルの量が、前記存在するリン酸モノエステルおよびリン酸ジエステルの合計の量に基づいて0から2重量パーセントである、項目1に記載のプロセス。
(項目3)
前記リン酸ジエステルが、式(RO) 2 P(=O)−OH(式中、それぞれのRは、独立して、4から約20個の炭素原子を有するヒドロカルビル基である)で表される、項目1または項目2に記載のプロセス。
(項目4)
前記R基が、2−エチルヘキシル基を含む、項目3に記載のプロセス。
(項目5)
前記アルキレンオキシドが、1,2−プロピレンオキシドを含む、項目1から4までのいずれかに記載のプロセス。
(項目6)
前記工程(a)の反応が、約40から約60℃で約0.5から約4時間行われる、項目1から5までのいずれかに記載のプロセス。
(項目7)
前記工程(a)により調製される生成物混合物が、式
(式中、それぞれのRは、独立してアルキル基である)
で表される分子を含む、項目1から6までのいずれかに記載のプロセス。
(項目8)
前記工程(b)のリン酸処理剤が、五酸化リンを含む、項目1から7までのいずれかに記載のプロセス。
(項目9)
前記工程(b)の生成物が、少なくとも1個の酸基を含むリン酸エステルを含む、項目1から8までのいずれかに記載のプロセス。
(項目10)
前記工程(b)により調製される生成物混合物が、式
で表される分子、またはその、式
(式中、それぞれのRは、独立してアルキル基である)
で表される分子との混合物を含む、項目1から9までのいずれかに記載のプロセス。
(項目11)
前記工程(c)のアミンが、約10から約22個の炭素原子を有する少なくとも1種の第二級アミンを含む、項目1から10までのいずれかに記載のプロセス。
(項目12)
項目1から11までのいずれかに記載のプロセスにより調製される生成物。
(項目13)
潤滑粘度の油および項目12に記載の生成物を含む潤滑剤。
(項目14)
ギア、車軸、またはトランスミッションを潤滑する方法であって、それらに、項目13に記載の潤滑剤を供給する工程を含む方法。
炭化水素置換基、すなわち、脂肪族(例えば、アルキルまたはアルケニル)、脂環式(例えば、シクロアルキル、シクロアルケニル)置換基、ならびに芳香族−、脂肪族−、および脂環式−置換芳香族置換基、ならびに環が分子の別の部分を介して完成される(例えば、2つの置換基が一緒になって環を形成する)環状置換基;
置換炭化水素置換基、すなわち、本発明の文脈において、その置換基の主に炭化水素の性質を変更しない、非炭化水素基を含有する置換基[例えば、ハロ(特に、クロロおよびフルオロ)、ヒドロキシ、アルコキシ、メルカプト、アルキルメルカプト、ニトロ、ニトロソ、およびスルホキシ];
ヘテロ置換基、すなわち、本発明の文脈において、主に炭化水素の特性を有するが、それ以外は炭素原子から構成される環または鎖中に炭素以外を含有し、ピリジル、フリル、チエニルおよびイミダゾリルのような置換基を包含する置換基。ヘテロ原子には、硫黄、酸素、および窒素が含まれる。ヒドロカルビル基中に炭素原子10個当たり、一般に、2個以下、または1個以下の非炭化水素置換基が存在し;あるいは、ヒドロカルビル基中に非炭化水素置換基が存在していなくてもよい。
で表される少なくともいくつかの分子を含む生成物混合物をもたらす。アルキレンオキシドがプロピレンオキシドである場合、存在する少なくともいくつかの分子は、構造
300gのジ−(2−エチルヘキシル)リン酸(そのジエステル)を、窒素の穏やかな流れ下で混合しながら40℃に加熱する。この酸に、51.0gのプロピレンオキシドを、液面下の管を介して2時間かけて添加する。反応混合物を70℃に加温し、この温度で2時間維持し、その後、それを<4kPa(<30トール)で1時間真空ストリッピングする。得られた混合物を窒素の穏やかな流れ下で撹拌しながら50℃に冷却し、この時点で35.5gの五酸化リンを2時間かけて添加する。反応混合物を80℃に加温し、この温度で3時間維持し、ろ過する。次いで、反応混合物を窒素の穏やかな流れ下で撹拌しながら48℃に再度加温し、この時点で109gのビス−2−エチルヘキシルアミンを2〜2.5時間かけて滴下する。反応混合物を75℃に加温し、この温度で2.5時間維持する。反応生成物は、さらに精製することなく用いる。
ジ−(2−エチルヘキシル)リン酸と2−エチルヘキシルリン酸との混合物300gを、窒素の穏やかな流れ下で混合しながら40℃に加熱する。この酸に、62.0gのプロピレンオキシドを、液面下の管を介して2時間かけて添加する。反応混合物を70℃に加温し、この温度で2時間維持し、その後、それを<4kPa(<30トール)で1時間真空ストリッピングする。得られた混合物を窒素の穏やかな流れ下で撹拌しながら50℃に冷却し、この時点で39.3gの五酸化リンを2時間かけて添加する。反応混合物を80℃に加温し、この温度で3時間維持し、ろ過する。次いで、反応混合物を窒素の穏やかな流れ下で撹拌しながら48℃に再度加温し、この時点で、反応混合物に138gのビス−2−エチルヘキシルアミンを2〜2.5時間かけて滴下する。反応混合物を75℃に加温し、この温度で2.5時間維持する。反応生成物は、さらに精製することなく用いる。
潤滑粘度の合成ポリアルファオレフィン油(100%に等しくする)
ポリメタクリレート粘度調整剤、20.4%(22%の希釈油を含む)
ポリイソブチレン粘度調整剤、11.5%
硫化オレフィン耐摩耗剤(単数または複数)、4%
腐食防止剤、2.5%
スクシンイミド分散剤、1.25%(33%の油を含む)
市販用消泡剤、0.15%
長鎖アミン、0.5%
実施例1の物質:1.46%。
Claims (10)
- リン酸のヒドロキシ置換エステルの塩を調製するためのプロセスであって、
(a)式(RO)2P(=O)−OH(式中、それぞれのRは、独立して、4から30個の炭素原子を有するヒドロカルビル基である)で表されるリン酸ジエステルを1,2−アルキレンオキシドと反応させる工程、
(b)工程(a)の生成物混合物をリン酸処理剤と反応させる工程;および
(c)工程(b)の生成物混合物をアミンと反応させる工程
を含み、
前記リン酸ジエステルは、リン酸モノエステルの実質的に非存在下で前記工程(a)のアルキレンオキシドと反応させ、前記リン酸モノエステルの量は、存在するリン酸モノエステルおよびリン酸ジエステルの合計の0から10重量パーセントである、プロセス。 - 前記工程(a)の反応中に存在する場合、前記存在するリン酸モノエステルの量が、前記存在するリン酸モノエステルおよびリン酸ジエステルの合計の量に基づいて0から2重量パーセントである、請求項1に記載のプロセス。
- 前記R基が、2−エチルヘキシル基を含む、請求項1または請求項2に記載のプロセス。
- 前記1,2−アルキレンオキシドが、1,2−プロピレンオキシドを含む、請求項1から3までのいずれかに記載のプロセス。
- 前記工程(a)の反応が、40から60℃で0.5から4時間行われる、請求項1から4までのいずれかに記載のプロセス。
- 前記工程(b)のリン酸処理剤が、五酸化リンを含む、請求項1から6までのいずれかに記載のプロセス。
- 前記工程(b)の生成物が、少なくとも1個の酸基を含むリン酸エステルを含む、請求項1から7までのいずれかに記載のプロセス。
- 前記工程(c)のアミンが、約10から約22個の炭素原子を有する少なくとも1種の第二級アミンを含む、請求項1から9までのいずれかに記載のプロセス。
Applications Claiming Priority (3)
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US37843010P | 2010-08-31 | 2010-08-31 | |
US61/378,430 | 2010-08-31 | ||
PCT/US2011/048757 WO2012030581A1 (en) | 2010-08-31 | 2011-08-23 | Preparation of phosphorus - containing antiwear compounds for use in lubricant compositions |
Publications (3)
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JP2013536840A JP2013536840A (ja) | 2013-09-26 |
JP2013536840A5 JP2013536840A5 (ja) | 2014-09-18 |
JP6062364B2 true JP6062364B2 (ja) | 2017-01-18 |
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US (1) | US9550799B2 (ja) |
EP (1) | EP2611817B1 (ja) |
JP (1) | JP6062364B2 (ja) |
KR (1) | KR20130102570A (ja) |
CN (1) | CN103180330B (ja) |
AU (1) | AU2011296344B2 (ja) |
CA (1) | CA2809810A1 (ja) |
WO (1) | WO2012030581A1 (ja) |
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US8088130B2 (en) | 2006-02-03 | 2012-01-03 | Biomet Sports Medicine, Llc | Method and apparatus for coupling soft tissue to a bone |
WO2017079016A1 (en) * | 2015-11-06 | 2017-05-11 | The Lubrizol Corporation | Lubricant with high pyrophosphate level |
WO2018017449A1 (en) * | 2016-07-20 | 2018-01-25 | The Lubrizol Corporation | Alkyl phosphate amine salts for use in lubricants |
CN109715766B (zh) | 2016-07-20 | 2022-06-28 | 路博润公司 | 用于润滑剂中的烷基磷酸酯胺盐 |
CN110573599B (zh) * | 2017-04-27 | 2022-04-26 | 路博润公司 | 用高焦磷酸酯含量的润滑剂润滑机械装置的方法 |
SG11201911708TA (en) * | 2017-06-20 | 2020-01-30 | Lubrizol Corp | Lubricating composition |
CA3072459A1 (en) * | 2017-08-17 | 2019-02-21 | The Lubrizol Company | Nitrogen-functionalized olefin polymers for driveline lubricants |
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US2411671A (en) | 1945-03-12 | 1946-11-26 | Gulf Oil Corp | Mineral oil composition resistant to foaming |
US3197405A (en) | 1962-07-09 | 1965-07-27 | Lubrizol Corp | Phosphorus-and nitrogen-containing compositions and process for preparing the same |
DE3622440A1 (de) * | 1986-07-04 | 1988-01-07 | Henkel Kgaa | Alkyl-hydroxyalkyl-phosphorsaeureester |
IN172215B (ja) | 1987-03-25 | 1993-05-08 | Lubrizol Corp | |
US5157088A (en) | 1987-11-19 | 1992-10-20 | Dishong Dennis M | Nitrogen-containing esters of carboxy-containing interpolymers |
WO1990004625A2 (en) | 1988-10-24 | 1990-05-03 | Exxon Chemical Company | Amide containing friction modifier for use in power transmission fluids |
US5500140A (en) * | 1995-03-31 | 1996-03-19 | Ethyl Corporation | Oil-soluble phosphorus- and nitrogen-containing additives |
JP2894551B2 (ja) * | 1996-02-29 | 1999-05-24 | エチル・コーポレーシヨン | 油溶性の燐窒素含有添加剤 |
WO2002102945A1 (en) * | 2001-06-14 | 2002-12-27 | Ciba Specialty Chemicals Holding Inc. | Improved antiwear performance of engine oils with $g(b)-dithiophosphorylated propionic acids |
US6573223B1 (en) * | 2002-03-04 | 2003-06-03 | The Lubrizol Corporation | Lubricating compositions with good thermal stability and demulsibility properties |
US20080182770A1 (en) * | 2007-01-26 | 2008-07-31 | The Lubrizol Corporation | Antiwear Agent and Lubricating Compositions Thereof |
US20110046029A1 (en) * | 2009-08-20 | 2011-02-24 | Milner Jeffrey L | Combinations of Phosphorus-Containing Compounds For Use As Anti-Wear Additives In Lubricant Compositions |
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2011
- 2011-08-23 WO PCT/US2011/048757 patent/WO2012030581A1/en active Application Filing
- 2011-08-23 JP JP2013527114A patent/JP6062364B2/ja not_active Expired - Fee Related
- 2011-08-23 EP EP11754958.4A patent/EP2611817B1/en active Active
- 2011-08-23 US US13/819,457 patent/US9550799B2/en active Active
- 2011-08-23 CN CN201180051766.7A patent/CN103180330B/zh not_active Expired - Fee Related
- 2011-08-23 AU AU2011296344A patent/AU2011296344B2/en not_active Ceased
- 2011-08-23 KR KR1020137008036A patent/KR20130102570A/ko not_active Application Discontinuation
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US9550799B2 (en) | 2017-01-24 |
US20130252864A1 (en) | 2013-09-26 |
KR20130102570A (ko) | 2013-09-17 |
EP2611817B1 (en) | 2017-03-22 |
JP2013536840A (ja) | 2013-09-26 |
AU2011296344A1 (en) | 2013-03-14 |
WO2012030581A1 (en) | 2012-03-08 |
CA2809810A1 (en) | 2012-03-08 |
EP2611817A1 (en) | 2013-07-10 |
CN103180330B (zh) | 2017-05-10 |
AU2011296344B2 (en) | 2017-01-12 |
CN103180330A (zh) | 2013-06-26 |
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