JP2014523471A - 過塩基性摩擦調整剤およびその使用方法 - Google Patents
過塩基性摩擦調整剤およびその使用方法 Download PDFInfo
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- JP2014523471A JP2014523471A JP2014521751A JP2014521751A JP2014523471A JP 2014523471 A JP2014523471 A JP 2014523471A JP 2014521751 A JP2014521751 A JP 2014521751A JP 2014521751 A JP2014521751 A JP 2014521751A JP 2014523471 A JP2014523471 A JP 2014523471A
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- overbased
- friction
- metal salt
- substituted
- lubricating
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- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000003336 secondary aromatic amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical class O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000010729 system oil Substances 0.000 description 1
- 150000003899 tartaric acid esters Chemical class 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical group CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- PZXFWBWBWODQCS-UHFFFAOYSA-L zinc;2-carboxyphenolate Chemical compound [Zn+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O PZXFWBWBWODQCS-UHFFFAOYSA-L 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
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- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
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- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
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- C10M159/12—Reaction products
- C10M159/20—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/106—Thiadiazoles
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Abstract
Description
の種々のイミダゾリンまたはオキサゾリンであってもよい種々の生成物のうちの少なくとも1つを含む潤滑油を開示する。
(i)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、ならびに芳香族で、脂肪族で、および脂環式で置換された芳香族置換基、ならびに環が分子の別の部分によって完成する環状置換基(例えば、2個の置換基が一緒になって環を形成する)、
(ii)置換された炭化水素置換基、すなわち、非炭化水素基(本発明の内容では、置換基の主な炭化水素性を変えない基)を含む置換基(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)、
(iii)ヘテロ置換基、すなわち、主な炭化水素の特徴を有しつつも、本発明の内容では、炭素原子で構成される環または鎖に炭素以外を含む置換基であり、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、そして、
(iv)硫黄、酸素および窒素を含むヘテロ原子。一般的に、2個以下、好ましくは1個以下の非炭化水素置換基が、ヒドロカルビル基の10個の炭素原子ごとに存在し、典型的には、ヒドロカルビル基には、非炭化水素置換基が存在しないだろう。
潤滑組成物は、本明細書に記載する生成物に、場合により他の性能添加剤(本明細書で以下に記載するような)を付加することによって調製されてもよい。他の性能添加剤としては、金属不活性化剤、粘度調整剤、清浄剤、耐摩耗剤、腐食阻害剤、分散剤、分散粘度調整剤、極圧剤、酸化防止剤、泡阻害剤(foam inhibitor)、抗乳化剤、流動点降下剤、シール膨潤剤およびこれらの混合物のうち、少なくとも1つが挙げられる。典型的には、完全に配合された潤滑油は、これらの性能添加剤の1つ以上を含むだろう。
本発明の潤滑組成物は、駆動系デバイス、内燃機関、油圧システム、グリース、タービン、または冷却剤または任意の他の機能性流体で有用な添加剤であってもよい。
サンプル1の調製;N,N−ジアルキルジアミンとイタコン酸ジメチルとの反応生成物の過塩基性塩
第1部
Duomeen(登録商標)2HT(AkzoNobel)とイタコン酸ジメチルを溶媒中で混合し、加熱して、環化した生成物を形成する。得られた反応物から溶媒を除去する。
第1部の環化した反応生成物を溶媒に加え、加熱する。石灰(Ca(OH)2)を加え、その後、二酸化炭素を吹き込む。合計で3回の石灰の添加、3回の二酸化炭素の吹き込みを終了する。次いで、反応物を150℃まで加熱することによってすべての溶媒を除去し、次いで、生成物の混合物を濾過助剤によって濾過する。粘性である場合、濾過を補助するために溶媒を加え、その後に蒸留によって溶媒を除去する。
サンプル2の調製;アルキルテトラアミンとイタコン酸ジメチルとの反応生成物の過塩基性塩
Tetrameen(登録商標)T(AkzoNobel)とイタコン酸ジメチルを、実施例1で使用したのと同じ手順にしたがって反応させ、サンプル2の過塩基性生成物を生成する。
オートマチックトランスミッションにおけるシャダー防止の耐久性のためのスクリーニング試験
実施例1〜3の過塩基性化合物を、以下に示す標準的なオートマチックトランスミッション流体(ATF)ブレンドにおける摩擦調整性能について試験する。配合物は、他の清浄剤または摩擦調整剤といった構成要素を含まない。このことは、本発明の過塩基性化合物の性能試験に対し、標準的なATFよりももっと激しい流体をあらわす。スクリーニングは、Raybestos 4211摩擦物質およびBW6100摩擦物質で、VSFT−JASOを用いて行われる。VSFT−JASOは、シャダー防止の耐久性を予測する。以下の配合物中の成分は、活性分基準(すなわち、希釈油を含まない)で存在する。配合物を100%になるように加えない場合、他の典型的なATF成分、例えば、染料、香料、消泡剤などと組み合わせる希釈油が差を補うことが推測され得る。
マニュアルトランスミッションの耐摩耗耐久性のためのスクリーニング試験
以下の表3に示す添加剤を含むベースラインマニュアルトランスミッション配合物を使用し、本発明の有効性を評価した。ベースライン配合物は、清浄剤または摩擦調整剤を含んでいない。
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) ヒドロカルビル置換されたアミンとイタコネートとの反応生成物の過塩基性金属塩。
(項目2) 前記反応生成物が、N置換4−カルボキシピロリジン−2−オン、およびそのエステルまたは塩を含み、ここで、このN置換基が、少なくとも約8個の炭素原子を含むヒドロカルビル基またはヘテロ原子を含有するヒドロカルビル基を含む、項目1に記載の過塩基性金属塩。
(項目3) 前記置換基が、約8〜約24個の炭素原子のアルキル基を含む、項目2に記載の過塩基性金属塩。
(項目4) 前記置換基が、少なくとも1個の窒素原子を含む基を含む、項目2に記載の過塩基性金属塩。
(項目5) 前記置換基は、1個以上のアミノ基を有する基を含み、この置換基の少なくとも1個のアミノ基は、約8〜約20個の炭素原子の少なくとも1個のアルキル基でさらに置換されている、項目2または項目4に記載の過塩基性金属塩。
(項目6) 前記置換基の少なくとも1個のアミノ基が、ジメルカプトチアジアゾールまたはジメルカプトチアジアゾールの誘導体と反応される、項目5に記載の過塩基性金属塩。
(項目7) 前記塩は、ASTM D2896によって測定した場合、油を含まないものを基準として、TBNが約10〜約500mg KOH/gである、項目1〜6のいずれかに記載の過塩基性金属塩。
(項目8) 前記金属がカルシウムまたはマグネシウムを含む、項目1〜7のいずれかに記載の過塩基性金属塩。
(項目9) 前記塩が炭酸化されている、項目1〜8のいずれかに記載の過塩基性金属塩。
(項目10) 潤滑粘度の油と、項目1〜9のいずれかに記載の過塩基性金属塩とを含む、潤滑組成物。
(項目11) 項目10に記載の潤滑剤を機械デバイスに供給することによって機械デバイスを潤滑する方法。
(項目12) 前記機械デバイスがオートマチックトランスミッションまたはマニュアルトランスミッションを含む、項目11に記載の方法。
(項目13) 前記機械デバイスがエンジンを含む、項目11に記載の方法。
(項目14) 機能性流体の添加剤としての項目1に記載の化合物の使用。
(項目15) 前記添加剤が、摩擦調整剤、耐摩耗剤および清浄剤のうち少なくとも1つから選択される、項目14に記載の使用。
Claims (15)
- ヒドロカルビル置換されたアミンとイタコネートとの反応生成物の過塩基性金属塩。
- 前記反応生成物が、N置換4−カルボキシピロリジン−2−オン、およびそのエステルまたは塩を含み、ここで、このN置換基が、少なくとも約8個の炭素原子を含むヒドロカルビル基またはヘテロ原子を含有するヒドロカルビル基を含む、請求項1に記載の過塩基性金属塩。
- 前記置換基が、約8〜約24個の炭素原子のアルキル基を含む、請求項2に記載の過塩基性金属塩。
- 前記置換基が、少なくとも1個の窒素原子を含む基を含む、請求項2に記載の過塩基性金属塩。
- 前記置換基は、1個以上のアミノ基を有する基を含み、この置換基の少なくとも1個のアミノ基は、約8〜約20個の炭素原子の少なくとも1個のアルキル基でさらに置換されている、請求項2または請求項4に記載の過塩基性金属塩。
- 前記置換基の少なくとも1個のアミノ基が、ジメルカプトチアジアゾールまたはジメルカプトチアジアゾールの誘導体と反応される、請求項5に記載の過塩基性金属塩。
- 前記塩は、ASTM D2896によって測定した場合、油を含まないものを基準として、TBNが約10〜約500mg KOH/gである、請求項1〜6のいずれかに記載の過塩基性金属塩。
- 前記金属がカルシウムまたはマグネシウムを含む、請求項1〜7のいずれかに記載の過塩基性金属塩。
- 前記塩が炭酸化されている、請求項1〜8のいずれかに記載の過塩基性金属塩。
- 潤滑粘度の油と、請求項1〜9のいずれかに記載の過塩基性金属塩とを含む、潤滑組成物。
- 請求項10に記載の潤滑剤を機械デバイスに供給することによって機械デバイスを潤滑する方法。
- 前記機械デバイスがオートマチックトランスミッションまたはマニュアルトランスミッションを含む、請求項11に記載の方法。
- 前記機械デバイスがエンジンを含む、請求項11に記載の方法。
- 機能性流体の添加剤としての請求項1に記載の化合物の使用。
- 前記添加剤が、摩擦調整剤、耐摩耗剤および清浄剤のうち少なくとも1つから選択される、請求項14に記載の使用。
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US61/510,227 | 2011-07-21 | ||
PCT/US2012/047301 WO2013012987A1 (en) | 2011-07-21 | 2012-07-19 | Overbased friction modifiers and methods of use thereof |
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EP (1) | EP2734502B1 (ja) |
JP (1) | JP5940663B2 (ja) |
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CN (1) | CN103814011B (ja) |
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JP2018145361A (ja) * | 2017-03-08 | 2018-09-20 | 出光興産株式会社 | タービン油、及びタービン油の使用方法 |
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US10301569B2 (en) * | 2013-09-30 | 2019-05-28 | The Lubrizol Corporation | Method of friction control |
EP3310871B1 (en) | 2015-06-16 | 2020-01-08 | Carrier Corporation | Heat transfer system with tribofilm on bearing surface |
RU2019142330A (ru) | 2017-06-30 | 2021-07-30 | Займворкс, Инк. | Стабилизированные химерные fab |
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- 2012-07-19 CN CN201280045614.0A patent/CN103814011B/zh not_active Expired - Fee Related
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JP2018145361A (ja) * | 2017-03-08 | 2018-09-20 | 出光興産株式会社 | タービン油、及びタービン油の使用方法 |
US11034907B2 (en) | 2017-03-08 | 2021-06-15 | Idemitsu Kosan Co., Ltd. | Turbine oil, and method for using turbine oil |
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CN103814011B (zh) | 2017-02-08 |
JP5940663B2 (ja) | 2016-06-29 |
CN103814011A (zh) | 2014-05-21 |
US9512379B2 (en) | 2016-12-06 |
EP2734502A1 (en) | 2014-05-28 |
CA2842669A1 (en) | 2013-01-24 |
US20140179574A1 (en) | 2014-06-26 |
AU2012284000A1 (en) | 2014-02-06 |
KR20140067007A (ko) | 2014-06-03 |
EP2734502B1 (en) | 2017-07-05 |
WO2013012987A1 (en) | 2013-01-24 |
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