JP2016536378A - 摩擦制御方法 - Google Patents
摩擦制御方法 Download PDFInfo
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- JP2016536378A JP2016536378A JP2016518073A JP2016518073A JP2016536378A JP 2016536378 A JP2016536378 A JP 2016536378A JP 2016518073 A JP2016518073 A JP 2016518073A JP 2016518073 A JP2016518073 A JP 2016518073A JP 2016536378 A JP2016536378 A JP 2016536378A
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- JP
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- Prior art keywords
- acid
- hydrocarbyl
- crankcase
- lubricating
- gear
- 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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- 238000000034 method Methods 0.000 title claims abstract description 60
- 239000000203 mixture Substances 0.000 claims abstract description 82
- -1 amine compound Chemical class 0.000 claims abstract description 59
- 230000001050 lubricating effect Effects 0.000 claims abstract description 51
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 36
- 238000002485 combustion reaction Methods 0.000 claims abstract description 33
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000002253 acid Chemical class 0.000 claims abstract description 19
- 229940014800 succinic anhydride Drugs 0.000 claims abstract description 19
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 40
- 239000002270 dispersing agent Substances 0.000 claims description 27
- 239000003599 detergent Substances 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 14
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- 239000003607 modifier Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 230000003068 static effect Effects 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical group NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 claims description 5
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
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- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 4
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 claims description 3
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- 239000000654 additive Substances 0.000 abstract description 21
- 230000000996 additive effect Effects 0.000 abstract description 12
- 230000005540 biological transmission Effects 0.000 abstract description 6
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- 239000000314 lubricant Substances 0.000 description 32
- 229920002367 Polyisobutene Polymers 0.000 description 18
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 17
- 229910052725 zinc Inorganic materials 0.000 description 17
- 239000011701 zinc Substances 0.000 description 17
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 13
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- 229910052796 boron Inorganic materials 0.000 description 12
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- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 10
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 10
- 229920000098 polyolefin Polymers 0.000 description 10
- 150000001336 alkenes Chemical class 0.000 description 9
- 239000002199 base oil Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 150000001412 amines Chemical group 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 6
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- 239000000463 material Substances 0.000 description 6
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- 239000000194 fatty acid Substances 0.000 description 5
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- 239000010959 steel Substances 0.000 description 5
- 229960002317 succinimide Drugs 0.000 description 5
- 229910000851 Alloy steel Inorganic materials 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical class C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 125000005266 diarylamine group Chemical group 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000002646 long chain fatty acid esters Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 239000000788 chromium alloy Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- KHYKFSXXGRUKRE-UHFFFAOYSA-J molybdenum(4+) tetracarbamodithioate Chemical class C(N)([S-])=S.[Mo+4].C(N)([S-])=S.C(N)([S-])=S.C(N)([S-])=S KHYKFSXXGRUKRE-UHFFFAOYSA-J 0.000 description 3
- 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 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 2
- QVXGKJYMVLJYCL-UHFFFAOYSA-N 2,3-di(nonyl)-N-phenylaniline Chemical compound C(CCCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCCC QVXGKJYMVLJYCL-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- IQGMRVWUTCYCST-UHFFFAOYSA-N 3-Aminosalicylic acid Chemical compound NC1=CC=CC(C(O)=O)=C1O IQGMRVWUTCYCST-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 229910000760 Hardened steel Inorganic materials 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 229910001182 Mo alloy Inorganic materials 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical class O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
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- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 1
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Classifications
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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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
- C10M133/58—Heterocyclic compounds
-
- 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
- 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
- C10M133/16—Amides; Imides
-
- 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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
- C10M133/56—Amides; Imides
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- C—CHEMISTRY; METALLURGY
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Abstract
Description
本発明は、クランクケースとギアおよびウェットクラッチの少なくとも1つとを含む内燃機関を潤滑組成物で潤滑させることによる摩擦制御方法に関する。
2−ストロークおよび/または4−ストローク内燃機関に普遍的に適合する潤滑剤を製造する試みがなされていることは知られている。これらの潤滑剤は、一般に、多数の異なる性能添加剤を含有し、これらは、例えば、4−ストロークのオートバイエンジン(この場合、クランクケース油の粘度が要求される一方、また、ギアボックス、変速機またはクラッチに関連した極圧および温度に適合する特性も要求される)における用途には、必ずしも設計されていない。結果的に、多くの添加剤は、エンジン性能または燃料節約に悪影響を及ぼす特性を有する。
米国特許第6,525,004号は、2−サイクルおよび小エンジン4−サイクルエンジンで使用するためのホウ酸化ヒドロカルビルスクシンイミド分散剤およびリン化合物を含有する組成物を開示している。
本発明は、クランクケースとギアおよびウェットクラッチの少なくとも1つとを含む内燃機関を潤滑させる方法であって、前記方法は、前記クランクケースと該ギアおよびウェットクラッチの少なくとも1つとに、以下:
(a)潤滑粘性のある油;および
(b)ヒドロカルビル置換無水コハク酸と酸官能化アミン化合物との反応生成物である摩擦調整用添加剤
を含有する潤滑組成物を供給する工程を含む、方法を提供する。
本発明はさらに、アリール化合物がアミン置換安息香酸またはその誘導体である、本明細書に開示された方法を提供する。
本発明は、クランクケースとギアおよびウェットクラッチの少なくとも1つとを含む内燃機関を潤滑させる方法であって、前記方法は、前記クランクケースと該ギアおよびウェットクラッチの少なくとも1つとに、以下:
(a)潤滑粘性のある油;および
(b)ヒドロカルビル置換無水コハク酸と酸官能化アミン化合物との反応生成物である摩擦調整用添加剤
を含有する潤滑組成物を供給する工程を含む、方法を提供する。
本発明の内燃機関は、クランクケース、ギアおよびウェットクラッチを含む。任意選択に、この内燃機関は、さらに手動または自動変速機を含む。一実施形態では、このギアは、ギアボックスに由来する。
この潤滑組成物には、潤滑粘性のある天然油または合成油;水素化分解、水素化、またはハイドロフィニッシングから誘導された油;および未精製油、精製油および再精製油、およびそれらの混合物が挙げられる。
本発明の摩擦調整用添加剤化合物は、酸官能化アミン化合物(すなわち、アミノ酸)をヒドロカルビルコハク酸アシル化剤と反応させてスクシンイミド酸を生成させることにより調製される。
一実施形態では、潤滑剤組成物または潤滑剤濃縮物は、本発明のスクシンイミド酸摩擦調整剤以外の少なくとも1つの性能添加剤を含む。この性能添加剤(単数または複数)は、金属不活性化剤、清浄剤、分散剤、極圧剤、耐摩耗剤、酸化防止剤、腐食防止剤、発泡防止剤、解乳化剤、流動点降下剤、粘度調整剤、他の摩擦調整剤、シール膨潤剤およびそれらの混合物の少なくとも1つを含むことができる。一実施形態では、この性能添加剤は、単独で、または併用して使用され得る。
例示的な実施形態の一態様では、動摩擦を上昇させず、または動摩擦を最小にせず、または少なくとも動摩擦を維持して内燃機関の静摩擦を増大させる方法は、内燃機関の接触表面を例示的な潤滑剤組成物に接触させることを含んでよい。接触表面としては、鋼表面と鋼合金表面の少なくとも1つ、またはアルミニウム表面もしくはアルミニウム合金表面を挙げることができる。潤滑剤組成物は、内燃機関の運転中には、接触表面と接触表面に対して移動する第2の表面との間に介在させてよい。
機械攪拌機、サーモウェル、表面下窒素入口、および冷却器付きディーン・スタークトラップを備えた2Lの4ッ口フラスコに、1000Mnポリイソブチレンを投入し、無水コハク酸(600g)と希釈油(600g)で置換した(substituted with)。この混合物を次いで攪拌し、150℃に加熱する。5−アミノサリチル(aminosalicyclic)酸(79.6g)を1.5時間かけて添加した後、反応温度を170℃まで上昇させ、さらに5.5時間保持する。この時点で、反応混合物を、さらに精製することなく冷却して使用する。
潤滑剤組成物について、SAE#2摩擦試験機を用いてJASO T904:2006に記載されるようにクラッチ機構の摩擦試験を行った。ウェットクラッチ性能を、オートバイ用途のための改変したSAE#2摩擦試験として、高摩擦(JAFRE A)基準油および低摩擦(JAFRE B)基準油に対する潤滑組成物の摩擦挙動を評価することにより測定する。試験は、3つの主なクラッチパラメータ:クラッチの滑りに関する静摩擦;クラッチの感触/取り込み(uptake)に関する動摩擦;および同期時間に関する停止時間を評価する。次いで、クラッチ性能指標を潤滑組成物に割り当て、JASO MA、MA1、またはMA2(ウェットクラッチの用途に適した高摩擦、またはJASO MB(ドライクラッチの用途により適した低摩擦として分類することができる。JASO MA2仕様(claim)の潤滑組成物について、以下の表2に記載されるように、すべての指標はカテゴリーについて特定された値の範囲内になければならない。
Claims (17)
- クランクケースとギアおよびウェットクラッチの少なくとも1つとを含む内燃機関の静摩擦を維持する方法であって、該方法が該クランクケースと該ギアおよびウェットクラッチの少なくとも1つとに、以下:
(a)潤滑粘性のある油;および
(b)ヒドロカルビル置換無水コハク酸と酸官能化アミン化合物との反応生成物
を含有する潤滑組成物を供給する工程を含む、方法。 - 前記反応生成物がスクシンイミド酸である、請求項1に記載の方法。
- 前記ヒドロカルビル置換無水コハク酸のヒドロカルビル置換基が、ポリイソブチル基を含む、請求項3に記載の方法。
- 前記ポリイソブチル基の数平均分子量が少なくとも400、または500または800、800〜3000、または800〜1,500である、請求項4に記載の方法。
- 前記アミン化合物がアリール化合物である、請求項1に記載の方法。
- 前記アリール化合物がアミン置換安息香酸またはその誘導体である、請求項6に記載の方法。
- 前記アミン化合物がアミノサリチル酸である、請求項6に記載の方法。
- 前記アミノサリチル酸が5−アミノサリチル酸である、請求項9に記載の方法。
- 前記反応生成物が、前記潤滑組成物の0.5重量%〜1.2重量%、または0.1重量%〜4重量%または0.25重量%〜2重量%で存在する、請求項1に記載の方法。
- 前記潤滑組成物が、前記クランクケースと前記ギア(または多数のギア)に供給される、請求項1に記載の方法。
- 前記潤滑組成物が、前記クランクケースと前記ウェットクラッチに供給される、請求項1に記載の方法。
- 前記潤滑組成物が、前記クランクケースと前記ギア(または複数のギア)および前記ウェットクラッチの両方に供給される、請求項1に記載の方法。
- 前記潤滑組成物がさらに、1つまたは複数の耐摩耗剤、分散剤、金属含有清浄剤、粘度指数向上剤、酸化防止剤、消泡剤、および流動点降下剤を含む、動摩擦の低減のための追加的な摩擦調整剤を含む、請求項1に記載の方法。
- 前記内燃機関が4ストロークエンジンである、請求項1に記載の方法。
- 前記4ストロークエンジンがオートバイのエンジンである、請求項1に記載の方法。
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2014
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JP2021502437A (ja) * | 2017-11-09 | 2021-01-28 | クローダ インターナショナル パブリック リミティド カンパニー | 潤滑剤配合物及び摩擦調整添加剤 |
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SG11201601919SA (en) | 2016-04-28 |
US10301569B2 (en) | 2019-05-28 |
CN113881477A (zh) | 2022-01-04 |
WO2015048719A1 (en) | 2015-04-02 |
CN105829510B (zh) | 2021-09-28 |
CN113881477B (zh) | 2022-12-27 |
EP3052599B1 (en) | 2020-09-16 |
EP3039104B1 (en) | 2019-12-04 |
US20160222311A1 (en) | 2016-08-04 |
CN105829510A (zh) | 2016-08-03 |
BR112016006956A2 (pt) | 2017-08-01 |
US20160237369A1 (en) | 2016-08-18 |
WO2015048722A1 (en) | 2015-04-02 |
BR112016006956B1 (pt) | 2021-04-06 |
CA2925578A1 (en) | 2015-04-02 |
JP6650869B2 (ja) | 2020-02-19 |
EP3039104A1 (en) | 2016-07-06 |
JP2020059861A (ja) | 2020-04-16 |
EP3052599A1 (en) | 2016-08-10 |
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