CN103215107B - 洗净分散剂、润滑油用添加剂组合物和润滑油组合物 - Google Patents
洗净分散剂、润滑油用添加剂组合物和润滑油组合物 Download PDFInfo
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- CN103215107B CN103215107B CN201310058584.3A CN201310058584A CN103215107B CN 103215107 B CN103215107 B CN 103215107B CN 201310058584 A CN201310058584 A CN 201310058584A CN 103215107 B CN103215107 B CN 103215107B
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- Prior art keywords
- detergent
- dispersant
- lubricating oil
- quality
- ring compound
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- JVAQVYKSURQMBE-UHFFFAOYSA-N 11-(bromomethyl)tricosane Chemical compound CCCCCCCCCCCCC(CBr)CCCCCCCCCC JVAQVYKSURQMBE-UHFFFAOYSA-N 0.000 claims description 5
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 claims description 3
- VQARVVLEWMTCDJ-UHFFFAOYSA-N 1-(2-decyltetradecyl)benzimidazol-2-amine Chemical compound C1=CC=C2N(CC(CCCCCCCCCC)CCCCCCCCCCCC)C(N)=NC2=C1 VQARVVLEWMTCDJ-UHFFFAOYSA-N 0.000 claims 8
- 238000002360 preparation method Methods 0.000 claims 2
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- RWEKWRQKAHQYNE-UHFFFAOYSA-N 7-(bromomethyl)pentadecane Chemical compound CCCCCCCCC(CBr)CCCCCC RWEKWRQKAHQYNE-UHFFFAOYSA-N 0.000 description 1
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- NULAIENJMUZXFQ-UHFFFAOYSA-N CCCCCCCCCCCCC(CCCCCCCCCC)CC1=C2C(=CC=C1)NC(=N2)N Chemical compound CCCCCCCCCCCCC(CCCCCCCCCC)CC1=C2C(=CC=C1)NC(=N2)N NULAIENJMUZXFQ-UHFFFAOYSA-N 0.000 description 1
- DIXGRQMWKSYIBF-UHFFFAOYSA-N CCCCCCCCCCCCCCCC.[Br] Chemical compound CCCCCCCCCCCCCCCC.[Br] DIXGRQMWKSYIBF-UHFFFAOYSA-N 0.000 description 1
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- ZWYAVGUHWPLBGT-UHFFFAOYSA-N bis(6-methylheptyl) decanedioate Chemical compound CC(C)CCCCCOC(=O)CCCCCCCCC(=O)OCCCCCC(C)C ZWYAVGUHWPLBGT-UHFFFAOYSA-N 0.000 description 1
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- 239000013530 defoamer Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 150000002497 iodine compounds Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000005339 levitation Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000005054 naphthyridines Chemical class 0.000 description 1
- FBUKVWPVBMHYJY-UHFFFAOYSA-M nonanoate Chemical compound CCCCCCCCC([O-])=O FBUKVWPVBMHYJY-UHFFFAOYSA-M 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 229920000768 polyamine Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- POOSGDOYLQNASK-UHFFFAOYSA-N tetracosan acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC POOSGDOYLQNASK-UHFFFAOYSA-N 0.000 description 1
- TYWMIZZBOVGFOV-UHFFFAOYSA-N tetracosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCO TYWMIZZBOVGFOV-UHFFFAOYSA-N 0.000 description 1
- XJPANWOKBWZVHC-UHFFFAOYSA-N tetrazol-2-amine Chemical compound NN1N=CN=N1 XJPANWOKBWZVHC-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
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- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/16—Ethers
- C10M129/20—Cyclic ethers having 4 or more ring atoms, e.g. furans, dioxolanes
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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
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- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/40—Six-membered ring containing nitrogen and carbon only
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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
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- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/40—Six-membered ring containing nitrogen and carbon only
- C10M133/42—Triazines
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- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/44—Five-membered ring containing nitrogen and carbon only
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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
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- C10M133/38—Heterocyclic nitrogen compounds
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- C10M133/46—Imidazoles
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- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
- C10M135/34—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon only
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- C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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- C10M2207/044—Cyclic ethers having four or more ring atoms, e.g. furans, dioxolanes
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
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- 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
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- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/221—Six-membered rings containing nitrogen and carbon only
- C10M2215/222—Triazines
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
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- C10M2215/224—Imidazoles
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- C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
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Abstract
本发明的目的在于提供洗净分散效果优异的润滑油用洗净分散剂,并通过由如下杂环化合物组成的洗净分散剂、包含所述洗净分散剂的润滑油用添加剂组合物以及润滑油组合物来实现,所述杂环化合物具有衍生自选自以下化合物的杂环骨架:吡啶类、吡咯类、嘧啶类、吡唑类、哒嗪类、咪唑类、吡嗪类、三嗪类、三唑类、四唑类、唑类、二唑类、噻唑类、噻二唑类、呋喃类、二
Description
本申请是国际申请日为2008年6月10日、国际申请号为PCT/JP2008/060594、进入国家阶段的申请号为200880019416.0、发明名称为“洗净分散剂、润滑油用添加剂组合物和润滑油组合物”的PCT申请的分案申请。
技术领域
本发明涉及洗净分散剂和包含该洗净分散剂的润滑油组合物。更具体而言,本发明涉及在高温稳定性、高温洗净性、碱值保持性方面优异且具有微粒分散性的无灰类洗净分散剂、润滑油用添加剂组合物以及包含所述无灰类洗净分散剂、润滑油用添加剂组合物的润滑油组合物。
背景技术
以往的无灰类洗净分散剂通常为琥珀酰亚胺类和羟基苄胺类等,其因显著的微粒分散作用而受到重视,从而广泛用作汽油发动机油、柴油发动机油、二冲程发动机油等的润滑油添加剂。而且还认识到它们与二烷基二硫代磷酸锌、金属洗净剂等的协同效应,因而将其作为极重要的润滑油用添加剂之一而加以应用。然而,所述无灰类洗净分散剂在高温下的稳定性和在高温下的洗净性屡受指摘。
以往的无灰类洗净分散剂通常为琥珀酰亚胺类和羟基苄胺类等,其在高温下的洗净性和稳定性不足。
将杂环化合物适用于润滑油的实例记载于下述专利文献中。
专利文献1中使用苯并三唑作为防蚀剂。专利文献2中记载了将三唑衍生物适用于冷冻机油组合物,并认为其具有耐摩耗性效果。专利文献3中使用咪唑氟衍生物作为表面处理剂。专利文献4中记载了采用聚苯并咪唑作为具有内部润滑剂的聚合物。专利文献5中记载了涉及包含噻二唑或苯并三唑且耐摩耗性优异的主动悬浮用的流体组合物。专利文献6中记载了采用三嗪衍生物作为用于润滑剂和燃料的分散剂。专利文献7中记载了作为润滑剂用的吲唑硫酮(イミダゾ一ルチオン)添加剂。专利文献8中记载了具有三嗪结构的低摩擦性流体。此外,专利文献9中记载了包含三嗪衍生物的润滑剂组合物。
然而,上述任一专利文献中均未记载无灰类洗净分散剂,特别是并未提出洗净性。
专利文献1:日本特开平01-29497号公报
专利文献2:日本特开平06-100881号公报
专利文献3:日本特开平06-157471号公报
专利文献4:日本特表平07-506860号公报
专利文献5:日本特开平08-165483号公报
专利文献6:日本特表2002-534436号公报
专利文献7:日本特表2003-505577号公报
专利文献8:日本特开2004-315703号公报
专利文献9:日本特开2004-331950号公报
发明内容
本发明的目的在于提供用作高温稳定性、高温洗净性、碱值保持性优异且微粒分散性优异的无灰类洗净分散剂的杂环化合物、润滑油用添加剂组合物以及包含所述所述杂环化合物、润滑油用添加剂组合物的润滑油组合物。
本发明人鉴于上述现有技术的现状,为开发洗净分散性提高了的润滑油组合物而进行研究,结果发现具有特定化学结构的杂环化合物显示出作为无灰类洗净分散剂的优异特性,可在内燃机或驱动系统传送装置中赋予润滑油高温稳定性等,从而完成本发明。
即本发明提供下述(1)-(7),
(1)洗净分散剂,所述洗净分散剂由下述通式(I)所表示的环状部分任选具有双键的杂环化合物组成,
通式(I)中,X1、X2、X3和X4各自独立地表示N或NH、O或S,p表示0或1;x和y各自独立地表示0-2的整数,u和r各自独立地表示0-4的整数,t和w各自独立地表示0-3的整数;当p为0时,v表示0-5的整数,当p为1时,v表示0-3的整数;n和m各自独立地表示0-3的整数,k表示0-3的整数,当p为0时,x、y、n、m和v不同时为0;R1-R4各自独立地表示与碳原子结合的氢原子,或者表示任选具有选自氨基、酰胺基、醚基和羧基的至少一种取代基的总碳原子数为10-200的烃基,当p为0时,R1和R2不同时为氢原子,当p为1时,R1-R4不同时为氢原子;Y1和Y2各自独立地表示氢原子、卤原子,或者选自氨基、酰胺基、羟基、羰基、醛基、羧基、酯基和醚基的官能团,或者任选具有选自所述官能团的至少一种官能团的总碳原子数为1-30的烃基。
(2)上述(1)的洗净分散剂,其中,通式(I)中的p为1,且X1、X2、X3和X4各自独立地为N或NH。
(3)上述(1)的洗净分散剂,其中,通式(I)具有衍生自选自以下的化合物的杂环骨架:吡啶类、吡咯类、嘧啶类、吡唑类、哒嗪类、咪唑类、吡嗪类、三嗪类、三唑类、四唑类、唑类、二唑类、噻唑类、噻二唑类、呋喃类、二烷类、吡喃类、噻吩类。
(4)上述(1)的洗净分散剂,其中,所述杂环化合物是硼化物。
(5)润滑油用添加剂组合物,其特征在于,包含(1)的洗净分散剂。
(6)润滑油组合物,其特征在于,包含上述(1)的洗净分散剂。
(7)上述(6)的润滑油组合物,所述润滑油组合物为内燃机用。
发明效果
通过采用包含本发明洗净分散剂的润滑油组合物,上述杂环化合物在例如内燃机中的汽油发动机油、柴油发动机油、二冲程发动机油等中显示优异的高温稳定性、高温洗净性、碱值保持性、微粒分散性。
具体实施方式
下文将详细说明本发明。
本发明的洗净分散剂由上述通式(I)所表示的杂环化合物组成。
在上述通式(I)中,
(1)当p为0时,
X1、X2和X3各自独立地表示N或NH、O或S。x和y各自独立地表示0-2的整数,v表示0-5的整数。n和m各自独立地表示0-3的整数,x、y、n、m和v不同时为0。R1和R2各自独立地表示与碳原子结合的氢原子,或者表示任选具有选自氨基、酰胺基、醚基和羧基的至少一种取代基的总碳原子数为10-200的烃残基,R1和R2不同时为氢原子。
在上述通式(I)中,
(2)当p为1时,
X1、X2、X3和X4各自独立地表示N或NH、O或S。x和y各自独立地表示0-2的整数,u和r各自独立地表示0-4的整数,t和w各自独立地表示0-3的整数。v表示0-3的整数。n和m各自独立地表示0-3的整数,k表示0-3的整数,R1-R4各自独立地表示与碳原子结合的氢原子,或者表示任选具有选自氨基、酰胺基、醚基和羧基的至少一种取代基的总碳原子数为10-200的烃残基,R1-R4不同时为氢原子。
Y1和Y2各自独立地表示氢原子、卤原子,或者选自氨基、酰胺基、羟基、羰基、醛基、羧基、酯基和醚基的官能团,或者任选具有选自所述官能团的至少一种官能团的总碳原子数为1-30的烃基。
在作为上述通式(I)所表示的杂环化合物的本发明洗净分散剂的烃基中,通过使碳原子数为10以上而使其为对润滑油基油具有充分溶解性的化合物,并通过使碳原子数为200以下而使其为具有优异洗净分散性的化合物,也可确保高温稳定性、碱值保持性等。
R1-R4优选为氢原子或12-150的烃基,具体而言,为十二烷基、十二烯基、十四碳烯、十四烯基、十六碳烯、十六烯基、十八烷基、十八烯基、油烯基、硬脂基、异硬脂基、癸烯三聚体、聚丁烯基等烃基,这些既可以是直链状也可以是支链状。
通式(I)所表示的杂环化合物是使如下化合物及其衍生物(a)与具有碳原子数为10-200的烷基、烯基、环烷基的卤素化合物、胺化合物、醇类、环氧化合物和具有羧基的化合物(b)以摩尔比(a)∶(b)为1∶5-5∶1,优选1∶2-2∶1的比例进行反应而获得的反应生成物,所述化合物及其衍生物(a)以例如作为杂环基本骨架的吡啶、吡咯、嘧啶、吡唑、哒嗪、咪唑、吡嗪、三嗪、三唑、苯并三唑、四唑、唑、二唑、噻唑、噻二唑、呋喃、噻吩作为基本骨架。
通过使摩尔比(a)∶(b)为1∶5以上和5∶1以下来防止本发明洗净分散剂的有效成分量减少,并防止产生大量添加以显示高温稳定性、高温洗净性、碱值保持性的必要。
(a)与(b)的反应于室温-250℃、优选于50℃-220℃进行。反应可以在无催化剂或存在催化剂的条件下进行。此外,进行反应时的溶剂能够使用例如己烷、甲苯、二甲苯、THF、DMF等有机溶剂。
在通式(I)所表示的杂环化合物为杂环基本骨架是一个环且氮和/或氧和/或硫的数目总计为1-4的饱和或不饱和化合物。作为这样的环状化合物,可以列举出吡啶、吡咯、嘧啶、吡唑、哒嗪、咪唑、吡嗪、三嗪、三唑、四唑、唑、二唑、噻唑、噻二唑、呋喃、噻吩及其衍生物。优选为吡啶、吡咯、嘧啶、吡唑、哒嗪、咪唑、吡嗪、三唑、四唑、二唑、噻唑、噻二唑,更优选列举出吡啶、嘧啶、吡咯、吡唑、咪唑、三唑及其衍生物。这些化合物既可以是上述单环环状化合物也可以是如下多环环状化合物,例如吲哚、吲唑、苯并三唑、苯并咪唑、嘌呤、喹啉、异喹啉、萘啶、咔唑、萘并咪唑等。此外,杂环化合物中可以附加烃基或胺、酰胺、醇、酮、醛、羧酸、酯、醚、卤素以及包含它们的烃作为官能团。
作为附加在杂环化合物上的官能团的实例,可以列举出甲基、乙基、丙基、丁基、戊基、己基、胺、酰胺、醇、甲基羧基、乙基羧基、醛、羧酸、乙酰氧基、丙酰氧基(プロピオキシル)、丁酰氧基(ブチロイルキシル)、卤素、乙氧基、丙氧基、乙胺、甲胺、二甲胺、二乙胺、多亚乙基多胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺、氨基乙基哌嗪等。
作为化合物(b),可以列举出溴类化合物,例如2-癸基-1-溴十四烷、2-丁基-1-溴辛烷、2-戊基-1-溴壬烷、2-己基-1-溴癸烷、2-庚基-1-溴十一烷、2-辛基-1-溴十二烷、2-壬基-1-溴十三烷、2,4-二辛基-1-溴十四烷、溴聚丁烯(ブロモポリブテン)、溴十二烷、溴十二烷、溴十四烷、溴十六烷、溴十八烷、溴二十烷、溴二十二烷、溴二十四烷、异硬脂基溴(ブロモイソステアリル);氯类化合物,例如2-癸基-1-氯十四烷、2-丁基-1-氯辛烷、2,4-二辛基-1-氯十四烷、氯聚丁烷、氯十二烷、氯二十四烷;碘类化合物,例如2-癸基-1-碘十四烷、2-丁基-1-碘辛烷、2,4-二辛基-1-碘十四烷、碘聚丁烯、碘十二烷、碘二十四烷;环氧化合物,例如2-癸基-1,2-环氧十四烷、2-丁基-1,2-环氧辛烷、2,4-二辛基-1,2-环氧十四烷、聚丁烯环氧化物、1,2-环氧十二烷、1,2-环氧二十四烷;胺化合物,例如2-癸基-十四烷胺、2-丁基-辛胺、2,4-二辛基1-十四烷胺、聚丁烯胺、十二烷胺、二十四烷胺;醇类,例如2-癸基-十四烷醇、2-丁基-辛醇、2,4-二辛基-1-十四烷醇、聚丁烯醇、十二烷醇、二十四烷醇;具有羧基的化合物,例如2-癸基-十四烷酸、2-丁基-辛酸、2,4-二辛基-1-十四烷酸、聚丁烯羧酸、十二烷酸、二十四烷酸。这些化合物既可以单独使用也可以将两种以上组合使用。
在通式(I)所表示的杂环化合物中,p为0时的环状结构部分或p为1时的两个环状结构部分衍生自上述化合物(a)。R1-R4中的至少一个衍生自化合物(b)。
通过将作为如上所述地获得的本发明洗净分散剂的通式(I)所表示的杂环化合物与各种润滑油用添加剂混合,可获得润滑油用添加剂组合物,通过将上述洗净分散剂单独与润滑油基油混合或者将上述润滑油用添加剂组合物与润滑油基油混合,可获得本发明的润滑油组合物。
此外,作为本发明洗净分散剂的一种形式的杂环化合物的硼化物是如下获得的反应生成物:使含硼化合物以相对于如上所述获得的杂环化合物的摩尔比为1∶0.01-10的比例、优选1∶0.05-5的比例与杂环化合物反应。杂环化合物与含硼化合物的反应于50℃-250℃、优选于100℃-200℃进行。进行反应时的溶剂能够使用例如烃油等有机溶剂。作为含硼化合物能够使用例如氧化硼、卤化硼、硼酸、硼酸酐、硼酸酯等。
需说明的是,上述反应获得的杂环化合物的硼化物具有以下结构:当上述通式(I)中的X1、X2、X3和X4,R1-R4,Y1和Y2的部分各自独立地为N、NH或氨基时,将硼酸加成或置换NH的氢。
作为各种润滑油用添加剂,具有下述物质(括号内记载有下述包含润滑油基油的润滑油组合物总量中的优选含量和更优选含量)。
可以列举出聚甲基丙烯酸酯类等粘度指数改进剂(优选1%质量-12%质量、更优选1%质量-4%质量)、苯并三唑类等防蚀剂(优选0.01%质量-3%质量、更优选0.01%质量-1.5%质量)、烷基化联苯胺等抗氧化剂(优选0.01%质量-5%质量、更优选0.01%质量-1.5%质量)、聚丁烯琥珀酰亚胺等分散剂(0.1%质量-10%质量、更优选0.1%质量-5%质量)、润滑油流动性改进剂(优选0.01%质量-2%质量、更优选0.01%质量-1.5%质量)、烯基琥珀酸酯类等防锈剂(优选0.01%质量-6%质量、更优选0.01%质量-3%质量)、聚甲基丙烯酸酯等倾点下降剂(优选0.01%质量-1.5%质量、更优选0.01%质量-0.5%质量)、消泡剂(优选0.001%质量-0.1%质量、更优选0.001%质量-0.01%质量)、亚磷酸酯类等抗磨耗剂(优选0.001%质量-5%质量、更优选0.001%质量-1.5%质量)、密封膨润剂(シ一ル膨潤剤)(优选0.1%质量-8%质量、更优选0.1%质量-4%质量)、脂肪酰胺等摩擦调整剂(优选0.01%质量-3%质量、更优选0.01%质量-1.5%质量)等。
需说明的是,如下使用本发明洗净分散剂:使其在与润滑油基油的总量中为0.01%质量-15%质量、优选0.05%质量-10%质量。通过使所述洗净分散剂的量为0.01%质量以上,可发挥洗净分散效果,通过使所述洗净分散剂的量为15%质量以下避免成本增加,并能够防止使润滑油基油的固有特性降低。
作为润滑油基油没有特别限制,能够使用矿物油类和合成油类的各种润滑油基油。
作为矿物油类润滑油基油,具体而言,可以列举出将原油常压蒸馏和减压蒸馏所获得的润滑油馏分如下纯化而获得的烃油:将溶剂脱沥青(溶剤脱れき)、溶剂萃取、加氢裂解、溶剂脱蜡、催化脱蜡、加氢纯化、硫酸洗净、白土处理等纯化处理适当组合,进行纯化。
本文中,作为烃油,能够使用例如链烷烃类矿物油、环烷烃类矿物油、芳族矿物油等润滑油的任何一种。
此外,作为合成油类润滑油基油,具体而言,能够使用苯基醚类合成油,例如聚苯基醚;聚烯烃类合成油,例如聚α-烯烃(聚丁烯、1-辛烯低聚物、1-癸烯低聚物等或它们的加氢产物);苯类合成油,例如烷基苯;萘类合成油,例如烷基萘;酯类合成油,例如二酯(戊二酸二(十三烷基)酯、己二酸二-2-乙基己酯、己二酸二异癸酯、己二酸二(十三烷基)酯、癸二酸二-2-乙基己酯等)、多元醇酯(三羟甲基丙烷癸酸酯、三羟甲基丙烷壬酸酯、季戊四醇2-乙基己酸酯、季戊四醇壬酸酯等);二醇类合成油,例如聚氧化亚烷基二醇;醚类合成油,例如聚苯基醚;硅酮类合成油,例如硅酮氟化油等。这些基油既可以单独使用也可以将两种以上组合使用。
将本发明的洗净分散剂掺混至烃油或合成油的润滑油馏分或它们的混合物所得的物质能够用作内燃机用润滑油组合物(例如,柴油发动机用润滑油组合物)、齿轮油、轴承油、变速机油、减震器油和工业用润滑油。
将上述杂环化类化合物掺混至烃的燃料油所得的物质洗净分散效果显著,能够用作防止杂质附着于内燃机的汽化器并除去附着物的洗净剂。
实施例
下文将基于本发明的实施例和比较例进行更详细地说明,但是本发明不限于这些实施例。
合成例1
向500ml的烧瓶中加入1.4g(0.037mol)NaH(60%)、20ml二甲基甲酰胺(DMF)。向其中滴加溶解于30ml DMF中的4.2g(0.036mol)苯并咪唑,在室温下反应30分钟。然后,向反应混合物中滴加溶解于15ml甲苯中的12.6g(0.03mol)2-癸基-1-溴十四烷,在100℃下反应7小时。蒸馏除去溶剂后,溶解于300ml己烷中并用水洗净。用硫酸镁干燥后,蒸馏除去己烷,用硅胶柱色谱法纯化,获得11.2g目标产物杂环化合物。所述杂环化合物的结构式如下:在通式(I)中,p为1,n为1,y为1,u为4,m、w、v、k、r为0,X2和X3为N,R1为2-癸基十四烷基,R2、R3、R4为氢,Y1、Y2也为氢。
将该杂环化合物作为“洗净分散剂1”。
合成例2
除了使用3.1g(0.036mol)2-氨基四唑代替苯并咪唑以外,与合成例1同样地进行反应,获得6.3g目标产物杂环化合物。所述杂环化合物的结构式如下:在通式(I)中,m为3,v为1,x、n、p、u、r、k为0,X1和X3为N,R1为2-癸基十四烷基,R2为氢,Y1为氨基。
将该杂环化合物作为“洗净分散剂2”。
合成例3
除了使用2.5g(0.036mol)咪唑代替苯并咪唑以外,与合成例1同样地进行反应,获得8.5g目标产物杂环化合物。所述杂环化合物的结构式如下:在通式(I)中,m为1,v为2,x为1,n、p、u、r、k为0,X1和X3为N,R1为2-癸基十四烷基,R2为氢,Y1为氢。将该杂环化合物作为“洗净分散剂3”。
合成例4
除了使用3.1g(0.036mol)2-氨基苯并咪唑代替苯并咪唑以外,与合成例1同样地进行反应,获得9.3g目标产物杂环化合物。所述杂环化合物的结构式如下:在通式(I)中,p为1,n为1,y为1,u为4,m、w、v、k、r为0,X2和X3为N,R1为2-癸基十四烷基,R2、R3、R4为氢,Y1为氨基,Y2为氢。
将该杂环化合物作为“洗净分散剂4”。
合成例5
除了使用3.1g(0.036mol)氨基吡嗪代替苯并咪唑以外,与合成例1同样地进行反应,获得4.1g目标产物杂环化合物。所述杂环化合物的结构式如下:在通式(I)中,p为0,m为1,v为2,x为2,n、u、r、k为0,X1和X3为N,R1为1-氨基-2-癸基十四烷基,R2为氢,Y1为氢。
将该杂环化合物作为“洗净分散剂5”。
合成例6
在1L的烧瓶中加入7.4g(0.073mol)二异丙胺(iPr2NH)、100ml四氢呋喃(THF)。在-30℃下向其中滴加44ml正丁基锂(nBuLi)(1.67M己烷溶液;0.073mol),并在该温度下搅拌30分钟。然后加入5.1g(0.055mol)γ-皮考啉的THF溶液(80ml),在-10℃下搅拌15分钟。然后,滴加15.0g(0.036mol)2-癸基-1-溴十四烷的THF溶液(80ml),并在室温下反应1小时,然后在40℃下反应4小时。
向反应混合物中添加300ml饱和氯化铵水溶液,然后用500ml己烷提取,用硫酸镁干燥有机层。蒸馏除去溶剂后,用硅胶柱色谱法纯化,获得5.6g目标产物杂环化合物。所述杂环化合物的结构式如下:在通式(I)中,p为0,v为5,m、n、u、r、k为0,X3为N,R1为3-癸基十五烷基,R2为氢,Y1为氢。将该杂环化合物作为“洗净分散剂6”。
合成例7
除了使用5.1g(0.055mol)α-皮考啉代替γ-皮考啉以外,与合成例6同样地进行反应,获得5.6g目标产物杂环化合物。所述杂环化合物的结构式如下:在通式(I)中,p为0,v为5,m、n、u、r、k为0,X3为N,R1为3-癸基十五烷基,R2为氢,Y1为氢。
将该杂环化合物作为“洗净分散剂7”。
合成例8
向300ml的4颈烧瓶中加入93g(0.22mol)由合成例2所合成的(2-癸基-1-十四烷基)-2-氨基四唑、6.3g(0.102mol)硼酸,边搅拌边于150℃在氮气流下反应4小时。在150℃下减压蒸馏除去生成的水,将反应物过滤,获得96g目标产物杂环化合物的硼化物。所述硼化物的结构式如下:在通式(I)中,m为3,v为1,x、n、p、u、r、k为0,X1和X3为N,R1为2-癸基十四烷基,R2为氢,Y1为(二羟基硼烷基)氨基。
将该杂环化合物作为“洗净分散剂8”。
合成例9
向300ml的4颈烧瓶中加入105g(0.22mol)由合成例4所合成的1-(2-癸基-1-十四烷基)-2-氨基苯并咪唑、6.3g(0.102mol)硼酸,于150℃在氮气流下反应4小时。
在150℃下减压蒸馏除去生成的水,将反应物过滤,获得108g目标产物杂环化合物的硼化物。所述硼化物的结构式如下:在通式(I)中,p为1,n为1,y为1,u为4,m、w、v、k、r为0,X2和X3为N,R1为2-癸基十四烷基,R2、R3、R4为氢,Y1为(二羟基硼烷基)氨基,Y2为氢。
将该杂环化合物作为“洗净分散剂9”。
比较合成例1
向2L的高压灭菌器中加入1,100g聚丁烯(Mw:987)、6.4g(0.021mol)鲸蜡基溴、115g(1.2mol)马来酸酐,进行氮气置换,于240℃反应5小时。降温至215℃,减压蒸馏除去未反应的马来酸酐和鲸蜡基溴,降温至140℃并过滤。所得聚丁烯琥珀酸酐的产量为1,100g。向2L的可拆式烧瓶中加入500g所得聚丁烯琥珀酸酐、64g(0.34mol)四亚乙基五胺(TEPA)、300g150中性馏分的矿物油,于150℃在氮气流下反应2小时。通过升温至200℃减压蒸馏除去未反应的TEPA和生成的水,降温至140℃并过滤,由此获得790g用于比较的杂环化合物(聚丁烯琥珀酰亚胺)。所述用于比较的杂环化合物的结构式如下:通式(I)中的Y1为氧双键。因此,其不属于本发明的洗净分散剂的范围。
将该用于比较的杂环化合物作为“用于比较的洗净分散剂1”。
比较合成例2
除了使用915g聚丁烯(Mw:800)代替聚丁烯(Mw:987)以外,与比较合成例1同样地进行反应。所得聚丁烯琥珀酸酐的产量为940g。然后,使用500g所得聚丁烯琥珀酸酐、76g(0.40mol)四亚乙基五胺(TEPA)、300g150中性馏分的矿物油,与比较合成例1同样地进行反应,获得810g用于比较的杂环化合物(聚丁烯琥珀酰亚胺)。所述用于比较的杂环化合物的结构式如下:通式(I)中的Y1为氧双键。因此,其不属于本发明洗净分散剂的范围。
将该用于比较的杂环化合物作为“用于比较的洗净分散剂2”。
比较合成例3
除了使用890g聚丁烯(Mw:445)代替聚丁烯(Mw:987)、11g(0.036mol)鲸蜡基溴、397g(2.1mol)马来酸酐以外,与比较合成例1同样地进行反应。所得聚丁烯琥珀酸酐的产量为990g。然后,使用500g所得聚丁烯琥珀酸酐、88g(0.60mol)三亚乙基四胺(TETA)、300g150中性馏分的矿物油,与比较合成例1同样地进行反应,获得820g用于比较的杂环化合物(聚丁烯琥珀酰亚胺)。所述用于比较的杂环化合物的结构式如下:通式(I)中的Y1为氧双键。因此,其不属于本发明洗净分散剂的范围。
将该用于比较的杂环化合物作为“用于比较的洗净分散剂3”。
实施例1-9和比较例1-3
向90质量份500中性馏分的矿物油中分别混合10质量份由合成例1-9和比较合成例1-3获得的“洗净分散剂1-9”和“用于比较的洗净分散剂1-3”,以配制润滑油组合物。
在下述条件下,通过热管试验评价这些润滑油组合物的性能。
结果示于表1。
[热管试验]
向保持于250℃的内径为2mm的玻璃管中,将润滑油组合物以0.3毫升/小时、将空气以10毫升/分钟连续通入16小时。将玻璃管中附着的漆与比色卡进行比较,将透明的情况作为10点,将黑的情况作为0点,进行11等级的评价,同时测定玻璃管附着的漆的质量。评价越高或者附着的漆越少表示性能越高。本试验按照JPI-5S-55-99进行。
[碱值保持性能试验]
回收上述热管试验后的试验油,通过基于JISK2501的盐酸法测定碱值。将试验后的碱值(剩余碱值)和试验前的碱值(初始碱值)进行比较,并以剩余碱值率(%)表示以评价碱值保持性能[剩余碱值率(%)=(剩余碱值/初始碱值)×100]。剩余碱值率越高表示碱值保持性能越好。
[表1]
工业实用性
将本发明洗净分散剂掺混至矿物油类烃油或合成类润滑油基油或它们的混合物中所得物质能够提高内燃机或驱动传送机的洗净分散性,并发挥优异的降低燃料消耗的效果。而且,由于其为无灰类的,因而适合作为将来的环境协调型洗净分散剂。
Claims (6)
1. 润滑油用添加剂组合物的制备方法,包括:
使(a)2-氨基苯并咪唑和(b)2-癸基-1-溴十四烷以摩尔比(a):(b)为1:5-5:1的比例进行反应而获得1-(2-癸基-1-十四烷基)-2-氨基苯并咪唑的步骤(1),和
将润滑油用添加剂与1-(2-癸基-1-十四烷基)-2-氨基苯并咪唑混合的步骤(2)。
2. 润滑油组合物的制备方法,包括:
使(a)2-氨基苯并咪唑和(b)2-癸基-1-溴十四烷以摩尔比(a):(b)为1:5-5:1的比例进行反应而获得1-(2-癸基-1-十四烷基)-2-氨基苯并咪唑的步骤(1),和
将润滑油基油与1-(2-癸基-1-十四烷基)-2-氨基苯并咪唑混合的步骤(2)。
3. 润滑油用添加剂组合物,其包含1-(2-癸基-1-十四烷基)-2-氨基苯并咪唑以及润滑油用添加剂。
4. 润滑油组合物,其包含1-(2-癸基-1-十四烷基)-2-氨基苯并咪唑以及润滑油基油。
5. 润滑油用添加剂组合物,其包含1-(2-癸基-1-十四烷基)-2-氨基苯并咪唑的硼化物以及润滑油用添加剂。
6. 润滑油组合物,其包含1-(2-癸基-1-十四烷基)-2-氨基苯并咪唑的硼化物以及润滑油基油。
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- 2008-06-10 US US12/602,499 patent/US20100184982A1/en not_active Abandoned
- 2008-06-10 EP EP08765383.8A patent/EP2161324A4/en not_active Withdrawn
- 2008-06-10 WO PCT/JP2008/060594 patent/WO2008153015A1/ja active Application Filing
- 2008-06-10 CN CN200880019416A patent/CN101679898A/zh active Pending
- 2008-06-10 CN CN201310058584.3A patent/CN103215107B/zh not_active Expired - Fee Related
- 2008-06-10 JP JP2009519252A patent/JP5400612B2/ja not_active Expired - Fee Related
- 2008-06-10 KR KR1020097025590A patent/KR101554749B1/ko not_active IP Right Cessation
-
2012
- 2012-10-19 US US13/656,031 patent/US8853139B2/en not_active Expired - Fee Related
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2014
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Also Published As
Publication number | Publication date |
---|---|
CN103215107A (zh) | 2013-07-24 |
KR101554749B1 (ko) | 2015-09-21 |
EP2161324A4 (en) | 2016-02-10 |
WO2008153015A1 (ja) | 2008-12-18 |
US20140296115A1 (en) | 2014-10-02 |
US9074158B2 (en) | 2015-07-07 |
KR20100017709A (ko) | 2010-02-16 |
US20100184982A1 (en) | 2010-07-22 |
EP2161324A1 (en) | 2010-03-10 |
CN101679898A (zh) | 2010-03-24 |
US20130045904A1 (en) | 2013-02-21 |
US8853139B2 (en) | 2014-10-07 |
JPWO2008153015A1 (ja) | 2010-08-26 |
JP5400612B2 (ja) | 2014-01-29 |
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