CN102076834A - 润滑油添加剂和含此添加剂的润滑油组合物 - Google Patents
润滑油添加剂和含此添加剂的润滑油组合物 Download PDFInfo
- Publication number
- CN102076834A CN102076834A CN200980124988XA CN200980124988A CN102076834A CN 102076834 A CN102076834 A CN 102076834A CN 200980124988X A CN200980124988X A CN 200980124988XA CN 200980124988 A CN200980124988 A CN 200980124988A CN 102076834 A CN102076834 A CN 102076834A
- Authority
- CN
- China
- Prior art keywords
- acid
- succimide
- oil
- ethylenically unsaturated
- lubricating oil
- 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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- 239000010687 lubricating oil Substances 0.000 title claims description 87
- 239000000203 mixture Substances 0.000 title claims description 82
- 239000000654 additive Substances 0.000 title description 63
- 230000000996 additive effect Effects 0.000 title description 58
- 238000000034 method Methods 0.000 claims abstract description 34
- 239000002253 acid Substances 0.000 claims abstract description 24
- 239000005078 molybdenum compound Substances 0.000 claims abstract description 24
- 150000002752 molybdenum compounds Chemical class 0.000 claims abstract description 24
- 229920000768 polyamine Polymers 0.000 claims abstract description 21
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 239000002199 base oil Substances 0.000 claims description 91
- 150000008065 acid anhydrides Chemical class 0.000 claims description 35
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 claims description 31
- 238000002360 preparation method Methods 0.000 claims description 24
- 150000001735 carboxylic acids Chemical class 0.000 claims description 23
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 19
- 239000000314 lubricant Substances 0.000 claims description 13
- 125000005466 alkylenyl group Chemical group 0.000 claims description 7
- 238000002485 combustion reaction Methods 0.000 claims description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 2
- 150000002763 monocarboxylic acids Chemical class 0.000 claims 2
- -1 alkenyl succinimide Chemical compound 0.000 abstract description 48
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 6
- 230000008569 process Effects 0.000 abstract description 6
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 abstract 7
- 150000008064 anhydrides Chemical class 0.000 abstract 5
- 229960002317 succinimide Drugs 0.000 abstract 4
- 230000002378 acidificating effect Effects 0.000 abstract 1
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- 239000003921 oil Substances 0.000 description 69
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- 238000012360 testing method Methods 0.000 description 29
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- 238000012545 processing Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 18
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 18
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- 239000002585 base Substances 0.000 description 15
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- 238000007254 oxidation reaction Methods 0.000 description 10
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- 239000010705 motor oil Substances 0.000 description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 8
- 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 8
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- 239000000243 solution Substances 0.000 description 6
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- 230000000052 comparative effect Effects 0.000 description 5
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 5
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- OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical class OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 4
- 239000011609 ammonium molybdate Substances 0.000 description 4
- 229940010552 ammonium molybdate Drugs 0.000 description 4
- 235000018660 ammonium molybdate Nutrition 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 238000010907 mechanical stirring Methods 0.000 description 4
- KHYKFSXXGRUKRE-UHFFFAOYSA-J molybdenum(4+) tetracarbamodithioate Chemical compound C(N)([S-])=S.[Mo+4].C(N)([S-])=S.C(N)([S-])=S.C(N)([S-])=S KHYKFSXXGRUKRE-UHFFFAOYSA-J 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
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- 238000000746 purification Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 229920002367 Polyisobutene Polymers 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
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- 150000001875 compounds Chemical class 0.000 description 3
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- 239000000194 fatty acid Substances 0.000 description 3
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- 150000002632 lipids Chemical class 0.000 description 3
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- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 3
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- TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
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- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/34—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 two double bonds between ring members or between ring members and non-ring members 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
-
- 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
- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
- C07F11/005—Compounds containing elements of Groups 6 or 16 of the Periodic Table compounds without a metal-carbon linkage
-
- 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
-
- 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
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/18—Complexes with metals
-
- 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
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
- C10M169/048—Mixtures of base-materials and additives the additives being a mixture of compounds of unknown or incompletely defined constitution, non-macromolecular and macromolecular 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/028—Overbased salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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Abstract
公开了钼酸化丁二酰亚胺配合物,其制备方法包括(a)将式I的多胺的烷基或烯基丁二酰亚胺与烯属不饱和羧酸或酸酐进行反应,其中R是约C12-约C30的烷基或烯基,a和b独立地为2或3,x为0-10;和(b)将步骤(a)的产物与酸性钼化合物进行反应。2,权利要求1的钼酸化丁二酰亚胺配合物,其中R是约C12-C24烷基或烯基,a和b均为2,且x为2-5。3,权利要求1或2的钼酸化丁二酰亚胺配合物,其中所述烯属不饱和羧酸或其酸酐是烯属不饱和一元羧酸或其酸酐。4,权利要求1或2的钼酸化丁二酰亚胺配合物,其中所述烯属不饱和羧酸或酸酐是烯属不饱和二元羧酸或其酸酐。
Description
发明背景
技术领域
本发明广义涉及润滑油添加剂和含此添加剂的润滑油组合物。
相关工艺描述
通常,有机钼化合物能改进发动机油的润滑性能是众所周知的。例如,二硫代氨基甲酸钼典型地用于减小摩擦。但是,二硫代氨基甲酸钼含有硫且会慢慢失去减摩的能力,除非在润滑油中有替代性的硫源。有机钼化合物另一例子是硫化的聚异丁烯基丁二酰亚胺钼配合物,参见美国专利号4,259,194、4,265,773、4,283,295、4,285,822和6,962,896以及美国专利申请号2005/0209111。润滑油中使用硫所带来的问题是硫可能会与排放控制设备不相容且会导致腐蚀问题。
美国专利号4,357,149和4,500,439公开了钼酸化C15-C20烯基丁二酰亚胺。在两个专利的实施例XI中,钼酸化丁二酰亚胺是通过将C15-C20烯基丁二酸酐与三乙四胺反应,接着用钼酸溶液进行处理制备的。
俄国专利2201433公开了用马来酸酐后处理的钼酸化丁二酰亚胺作为内燃机的机油添加剂。俄国专利2201433进一步公开了所属添加剂是通过在以水为促进剂存在下将多亚乙基多胺的烯基丁二酰亚胺与钼酸铵进行反应,然后将得到的反应产物按每摩尔多亚乙基多胺的烯基丁二酰亚胺与0.2与1.0摩尔马来酸酐的量进行反应制备的。俄国专利2201433中公开的所有实施例在制备多亚乙基多胺的烯基丁二酰亚胺时使用了高分子量的聚异丁烯(950M.W.)丁二酸酐(PIBSA)。
因此,希望开发出能呈现改进的摩擦性及抗磨和抗氧性的改良型含钼润滑油组合物。
发明概述
按照本发明的一个实施方案,提供钼酸化丁二酰亚胺配合物,其通过包括下列步骤的方法制备:(a)将式I的多胺的烷基或烯基丁二酰亚胺与烯属不饱和羧酸或酸酐进行反应:
其中R是约C12-约C30的烷基或烯基,a和b独立地为2或3,x为0-10;和(b)将步骤(a)的丁二酰亚胺产物与酸性钼化合物进行反应。
按照本发明的第二个实施方案,提供制备钼酸化丁二酰亚胺配合物的方法,所述方法包括(a)将式I的多胺的烷基或烯基丁二酰亚胺与烯属不饱和羧酸或酸酐进行反应:
其中R,a,b和x的定义同上;和(b)将步骤(a)的丁二酰亚胺产物与酸性钼化合物进行反应。
按照本发明的第三个实施方案中,提供润滑油组合物,其包括(a)主要量的润滑粘度基础油和(b)次要量的通过包括如下步骤的方法制备的钼酸化丁二酰亚胺配合物:(i)将式I的多胺的烷基或烯基丁二酰亚胺与烯属不饱和羧酸或酸酐进行反应:
其中R,a,b和x的定义同上;和(ii)将步骤(i)的丁二酰亚胺产物与酸性钼化合物进行反应。
按照本发明的第四个实施方案中,提供操作内燃机的方法,包括用包含如下组分的润滑油组合物操作内燃机:(a)主要量的润滑粘度基础油和(b)次要量的通过包括如下步骤的方法制备的钼酸化丁二酰亚胺配合物:(i)将式I的多胺的烷基或烯基丁二酰亚胺与烯属不饱和羧酸或酸酐进行反应:
其中R,a,b和x的定义同上;和(ii)将步骤(i)的丁二酰亚胺产物与酸性钼化合物进行反应。
按照本发明的第五个实施方案中,提供添加剂包组合物或浓缩液,其包括(a)约20-约80wt%惰性有机稀释剂和(b)一或多种通过包括如下步骤的方法制备的钼酸化丁二酰亚胺配合物:(i)将式I的多胺的烷基或烯基丁二酰亚胺与烯属不饱和羧酸或酸酐进行反应:
其中R,a,b和x的定义同上;和(ii)将步骤(i)的丁二酰亚胺产物与酸性钼化合物进行反应。
本发明的钼酸化丁二酰亚胺配合物在掺入润滑油组合物并用于内燃机时很好地提供高减摩性和抗磨及抗氧化性。
优选实施方案的详述
一般来说,本发明的钼酸化丁二酰亚胺配合物是通过如下方法制备的,所述方法至少包括a)将式I的多胺的烷基或烯基丁二酰亚胺与烯属不饱和羧酸和/或酸酐进行反应:
其中R是约C12-约C30的烷基或烯基,a和b独立地为2或3,x为0-10,优选为1-6且更优选为2-5;和(b)将步骤(a)的丁二酰亚胺产物与酸性钼化合物进行反应。在一个实施方案中,R取代基的数均分子量范围约为167-约419且优选约223-约279。在另一个实施方案中,R是约C12-约C24烷基或烯基,a和b各为2,和x为2-5。
在步骤(a)中,式I的丁二酰亚胺与烯属不饱和羧酸进行反应:
其中R,a,b和x的定义同上。式I的起始丁二酰亚胺可通过式II的酸酐与多胺反应来获得:
其中R的定义同上。式II的酸酐或是从例如Sigma AldrichCorporation(St.Louis,Mo.,U.S.A.)的来源市购或是通过任何本领域众所周知的方法制备。
适宜用来制备式I丁二酰亚胺的多胺是多亚烷基多胺,包括多亚烷基二胺。这类多亚烷基多胺一般包含约2-约12个氮原子和约2-24个碳原子。特别适用的多亚烷基多胺是具有式H2N-(R1NH)c-H的多亚烷基多胺,其中R1是有2或3个碳原子的直链或支链亚烷基且c为1-9。适宜的多亚烷基多胺的代表性例子包括乙二胺、二乙三胺、三乙四胺、四乙五胺和它们的混合物。最优选地,多亚烷基多胺是四乙五胺。
许多适用于本发明的多胺是市购的或者看通过本领域众所周知的方法来制备。例如制备胺的方法和它们的反应详见Sidgewick的″氮的有机化学″(Clarendon Press,Oxford,1966)、Noller的″有机化合物的化学″(Saunders,Philadelphia,2nd Ed.,1957)和Kirk-Othmer的″化学技术大全″(第2版,特别是第2卷99116)。
通常,式II的酸酐是在约130-约220℃且优选约145-约175℃的温度下与多胺进行反应的。反应可在惰性气氛如氮气或氩气下进行。以反应混合物总重量计,反应中式II酸酐的用量可在约30-约95wt%范围且优选约40-约60wt%。
适用的烯属不饱和羧酸或它们的酸酐包括烯属不饱和一元羧酸或它们的酸酐、烯属不饱和二羧酸或它们的酸酐等和它们的混合物。适用的一元羧酸或它们的酸酐包括但不限于丙烯酸、甲基丙烯酸及类似物和它们的混合物。适用的烯属不饱和二羧酸或其酸酐包括但不限于富马酸、马来酸酐、甲基富马酸、柠康酸、柠康酸酐、衣康酸、衣康酸酐及类似物和它们的混合物。优选的烯属不饱和羧酸或其酸酐是马来酸酐或其衍生物。此或类似酸酐键连到丁二酰亚胺起始化合物上以提供羧酸官能团。式I的丁二酰亚胺用烯属不饱和羧酸或其酸酐处理的方法使得能有利地有足量的钼化合物并入配合物。
通常,将烯属不饱和羧酸或其酸酐在约50-约100℃范围的温度下加热至熔融条件,之后与式I的丁二酰亚胺混合。烯属不饱和羧酸或其酸酐与式I的丁二酰亚胺的摩尔比可宽范围变动,例如在约0.1∶1-约2∶1范围变动。在一个实施方案中,烯属不饱和羧酸或其酸酐与式I的丁二酰亚胺的装料摩尔比在约0.9∶1-约1.05∶1。
用来制备本发明钼酸化丁二酰亚胺配合物的钼化合物是酸性钼化合物或酸性钼化合物的盐。通常,这些钼化合物是六价的。适用的钼化合物的代表性例子包括但不限于氧化钼、三氧化钼、钼酸、钼酸铵、钼酸钠、钼酸钾和其它碱金属钼酸盐及其它钼盐如氢盐例如钼酸氢钠、MoOCl4、MoO2Br2、Mo2O3Cl6或类似酸性钼化合物。优选的酸性钼化合物是三氧化钼、钼酸、钼酸铵和碱金属钼酸盐。特别优选的是三氧化钼。
步骤(b)中,将步骤(a)的丁二酰亚胺产物与酸性钼化合物的混合物在有或没有稀释剂条件下制成混合物。若需要的话,使用稀释剂来提供易于搅拌的粘度。适用的稀释剂是润滑油和仅含碳和氢的液体化合物。若希望的话,也可向反应混合物中加入氢氧化铵来提供钼酸铵溶液。
通常,将反应混合物在低于或等于约100℃且优选约80-约100℃的温度下加热至钼充分反应。此步骤的反应时间一般在约15分钟到约5小时且优选约1-约2小时范围。钼化合物与步骤(a)丁二酰亚胺产物的摩尔比约为0.1∶1-2∶1、优选约0.5∶1-约1.5∶1且最优选为约1∶1。钼化合物与步骤(a)丁二酰亚胺产物的反应之后可将通过将反应混合物加热到高于约100℃且优选约120-约160℃的温度来移出任何存在的水。
本发明的另一实施方案涉及润滑油组合物,其包含至少(a)主要量的润滑粘度基础油和(b)次要量的用作润滑油添加剂的本发明钼酸化丁二酰亚胺配合物。润滑油组合物可通过采用常规技术将适当量的本发明润滑油添加剂与润滑粘度基础油混合来制备。具体选用何种基础油取决于润滑剂预期用途和存在的其它添加剂。通常,以润滑油组合物总重量计,少量的本发明钼酸化丁二酰亚胺配合物将在约0.001-约10wt%范围变动且优选约0.5-约2wt.%。
以组合物总重量计,用于本发明润滑油组合物的润滑粘度基础油一般以主要量存在如大于50wt%、优选大于约70wt%、更优选约80-约99.5wt%且最优选约85-约98wt%的量存在。这里所用的术语“基础油”应该理解为意指基础油料或是基础油料调和物,是由单一制造商按相同的规格(与原料来源或厂商的地点无关)生产的、满足同一厂商的规格要求和通过唯一配方、产品识别号或二者兼备进行识别的润滑剂组分。本文所使用的基础油可以是任何目前已知的或以后发现的配制润滑油组合物用润滑粘度基础油,所述润滑油组合物用于诸如发动机油、船用汽缸油、功能流体如液压油、齿轮油、传动液等之类的任何和所有应用。另外,本文使用的基础油可任选含有粘度指数改进剂如聚合的甲基丙烯酸烷基酯;烯烃共聚物如乙烯一丙烯共聚物或苯乙烯一丁二烯共聚物以及其它等等和它们的混合物。
如本领域技术人员所容易理解的那样,基础油的粘度取决于用途。因此,本文使用的基础油在100℃下粘度的常规范围为约2-约2000厘沲(cSt)。通常,具体到用作发动机油的基础油,其100℃下运动粘度范围约为2-约30cSt、优选约3-约16cSt且最优选约4-约12cSt,并且根据所期望的最终用途和成品油中的添加剂来选择或调和,以获得所期望等级的发动机油,例如具有SAE粘度等级0W、0W-20、0W-30、0W-40、0W-_50、0W-60、5W、5W-20、5W--30、5W-40、5W-50、5W-60、10W、10W-20、10W-30、10W-40、10W-50、15W、15W-20、15W-30或15W-40的润滑油组合物。用作齿轮油的油在100℃下粘度范围约为2-约2000cSt。
可以使用各种不同方法来生产基础油料,包括但不限于蒸馏、溶剂精制、加氢处理、低聚、酯化和再精制。再精制油料应该基本上不含通过生产、污染和先前使用所引入的材料。本发明润滑油组合物的基础油可以是任何天然或合成润滑基础油。适合的烃合成油包括但不限于由乙烯聚合或由1-烯烃聚合来提供如聚α-烯烃或称PAO油的聚合物所制成的油或由使用一氧化碳和氢气的烃合成法如在费托过程中制备的油。例如,适用的基础油是包括即使有也很少的重质馏分如即使有也很少的100℃下粘度等于或高于20cSt的润滑油馏分的基础油。
基础油可以衍生自天然润滑油、合成润滑油或它们的混合物。适用的基础油包括通过将合成蜡和疏松石蜡异构化获得的基础油料,以及通过原油的芳族和极性组分的加氢裂化(而非溶剂萃取)所生产的加氢裂化基础油料。适用的基础油包括如在API Publication 1509(第14版,Addendum I,199812月)中所定义的所有API I、II、III、IV和V类基础油。IV类基础油是聚α-烯烃(PAO)。V类基础油包括所有不包括在I、II、III或IV类的其它基础油。虽然II、III和IV组基础油优选用于本发明,但这些基础油可以通过将一种或多种I、II、III、IV和V类基础油料或基础油进行组合来制备。
有用的天然油包括矿物润滑油,例如液态石油、溶剂处理或酸处理的链烷烃、环烷烃或混合的链烷烃-环烷烃类的矿物润滑油,来源于煤或页岩的油,动物油、植物油(例如菜籽油,蓖麻油和猪油)等等。
有用的合成润滑油包括但不限于烃油和卤代烃油,例如聚合和共聚的烯烃如聚丁烯、聚丙烯、丙烯-异丁烯共聚物、氯化聚丁烯、聚(1-己烯)、聚(1-辛烯)、聚(1-癸烯)等和它们的混合物;烷基苯类如十二烷基苯、十四烷基苯、二壬基苯、二(2-乙基己基)苯等;聚苯如联苯,三联苯、烷基化聚苯等;烷基化二苯基醚和烷基化二苯基硫以及它们的衍生物、类似物和同系物等。
其它有用的合成润滑油包括但不限于通过将小于5个碳原子的烯烃如乙烯、丙烯、丁烯、异丁烯、戊烯和它们的混合物聚合所制备的油。制备此类聚合物油的方法是本领域技术人员众所周知的。
另一些有用的合成烃油包括具有适当粘度的α-烯烃液体聚合物。尤其适用的合成烃油是C6-C12α-烯烃的氢化液体低聚物如1-癸烯三聚物。
另一类适用的合成润滑油包括但不限于环氧烷聚合物,即均聚物、互聚物和它们的衍生物,其中末端羟基已通过例如酯化或醚化反应进行了改性。这些油例如是通过环氧乙烷或环氧丙烷聚合所制成的油,这些聚环氧烷聚合物的烷基和苯基醚(如平均分子量为1000的甲基聚丙二醇醚,分子量为500-1000的聚乙二醇的二苯基醚,分子量为1000-1500的聚丙二醇的二乙醚等)或它们的一元和多元羧酸酯如四甘醇的乙酸酯、混合C3-C8脂肪酸酯或C13含氧酸二酯。
还有一类适用的合成润滑油包括但不限于二羧酸的酯,例如邻苯二甲酸、丁二酸、烷基丁二酸、烯基丁二酸、马来酸、壬二酸、辛二酸、癸二酸、富马酸、己二酸、亚油酸二聚体、丙二酸、烷基丙二酸、烯基丙二酸等与各种醇如丁醇、己醇、十二烷醇、2-乙基己醇、乙二醇、二甘醇单醚、丙二醇等的酯。这些酯的具体例子包括己二酸二丁酯、癸二酸二(2-乙基己基)酯、富马酸二正己酯、癸二酸二辛酯、壬二酸二异辛酯、壬二酸二异癸酯、邻苯二甲酸二辛酯、邻苯二甲酸二癸酯、癸二酸二(二十烷基)酯、亚油酸二聚体的2-乙基己二酯、将1mol癸二酸与2mol四甘醇和2mol 2-乙基己酸反应所形成的复合酯等。
可用作合成油的酯还包括但不限于约5-约12个碳原子的羧酸与醇如甲醇,乙醇等、多元醇和多元醇醚如新戊二醇、三羟甲基丙烷、季戊四醇、二季戊四醇、三季戊四醇所制成的酯等。
硅基油,例如像聚烷基-,聚芳基-,聚烷氧基-或聚芳氧基-硅氧烷油和硅酸酯油,构成另一类适用的合成润滑油。它们的具体例子包括但不限于硅酸四乙酯、硅酸四异丙酯、硅酸四(2-乙基己基)酯、硅酸四(4-甲基己基)酯、硅酸四(对叔丁基苯基)酯、己基-(4-甲基-2-戊氧基)二硅氧烷、聚(甲基)硅氧烷、聚(甲基苯基)硅氧烷等。还有其它适用的合成润滑油包括但不限于含磷酸的液体酯如磷酸三甲苯酯、磷酸三辛酯、癸烷膦酸二乙酯等、聚合的四氢呋喃等等。
润滑油可衍生自未精制的,精制的和再精制的油,天然的、合成的或任何两或多种上文公开类型的这些油的混合物。未精制油是未经进一步提纯或处理的直接由天然或合成来源(例如煤、页岩或焦油砂沥青)获得的油。未精制油的实例包括但不限于直接由干馏操作获得的页岩油、直接由蒸馏获得的石油或直接由酯化工艺获得的酯油,之后都不用进一步处理而直接使用。精制油与未精制油类似,只是它们已在一或多个提纯步骤中进一步处理以改进一或多个性能。这些提纯技术是本领域技术人员熟知的,例如包括溶剂萃取、二次蒸馏、酸或碱萃取、过滤、渗透、加氢处理、脱蜡等等。再精制油是通过将用过的油在类似于获取精制油的工艺过程中进行处理来获得的。此类再精制油也称为再生油或再加工油且常常要采用针对除去废添加剂和油分解产物的技术来补加处理。
也可单独或与上述天然和/或合成基础油料组合使用从蜡的加氢异构化得到的润滑油基础油料。这种蜡异构化油是通过将天然或合成蜡或它们的混合物在加氢异构化催化剂上进行加氢异构化处理来生产的。
天然蜡一般是通过将矿物油进行溶剂脱蜡所回收的疏松蜡,合成蜡一般是通过费托法生产的蜡。
本发明润滑油组合物还可含有能赋予辅助功能的其它常规添加剂,所述添加剂分散或溶解其中来获得最终润滑油组合物。例如,润滑油组合物可与抗氧化剂、抗磨剂、清净剂、如金属清净剂、锈抑制剂、去浊剂、破乳剂、金属钝化剂、摩擦改性剂、倾点下降剂、消泡剂、助溶剂、添加剂包增容剂、腐蚀抑制剂、无灰分散剂、染料、极压添加剂等和它们的混合物进行调混。各种添加剂是众所周知的且市场可购。这些添加剂或它们的类似化合物可采用常规调混工序来制备本发明的润滑油组合物。
抗氧化剂的实例包括但不限于胺类抗氧剂如二苯胺、苯基-α-萘基胺、N,N-二(烷基苯基)胺和烷基化苯二胺,酚类抗氧剂如BHT、位阻酚型烷基苯酚如2,6-二叔丁基苯酚、2,6-二叔丁基对甲酚和2,6-二叔丁基-4-(2-辛基-3-丙酰)苯酚和它们的混合物。
无灰分散剂的实例包括但不限于聚亚烷基丁二酸酐;聚亚烷基丁二酸酐的不含氮衍生物;选自丁二酰亚胺、羧酸酰胺、烃基单胺、烃基多胺、曼尼希碱、膦酰胺、硫代膦酰胺和磷酰胺的碱性氮化合物;三唑如烷基三唑和苯并三唑;含羧酸酯及一或多个包括胺、酰胺、亚胺、酰亚胺、羟基、羧基等其它极性官能团的共聚物,例如通过将丙烯酸或甲基丙烯酸长链烷基酯与上述功能的单体进行共聚所制备的产物;和类似物及它们的混合物。还可以使用这些分散剂的衍生物,例如硼酸化分散剂如硼酸化丁二酰亚胺。
锈抑制剂的实例包括但不限于非离子型聚氧化烯试剂,例如聚氧化乙烯月桂基醚、聚氧化乙烯高级醇醚、聚氧化乙烯壬基苯基醚、聚氧化乙烯辛基苯基醚、聚氧化乙烯辛基硬脂基醚、聚氧化乙烯油基醚、聚氧化乙烯山梨醇单硬脂酸酯、聚氧化乙烯山梨醇单油酸酯和聚乙二醇单油酸酯;硬脂酸和其它脂肪酸;二元羧酸;金属皂;脂肪酸胺盐;重质磺酸的金属盐;多元醇的部分羧酸酯;磷酸酯;(短链)烯基丁二酸;它们的部分酯和它们的含氮衍生物;合成烷芳基磺酸盐如二壬基萘磺酸金属盐;和类似物及它们的混合物。
摩擦改性剂的实例包括但不限于烷氧基化脂肪胺;硼酸化脂肪环氧化物;脂肪亚磷酸酯,脂肪环氧化物,脂肪胺,硼酸化烷氧基化脂肪胺,脂肪酸的金属盐,脂肪酸酰胺,甘油酯,硼酸化甘油酯;和如US专利号6,372,696(该专利的内容引入本文供参考)中所公开的脂肪咪唑啉;由C4-C75、优选C6-C24且最优选C6-C20脂肪酸酯与选自氨和链烷醇胺的含氮化合物的反应产物以及类似物和它们的混合物获得的摩擦改性剂。
消泡剂的实例包括但不限于甲基丙烯酸烷基酯的聚合物、二甲基硅氧烷的聚合物等和它们的混合物。
上述每种添加剂在使用时是按功能有效量使用以赋予润滑剂所期望的性能。因此,例如若添加剂是摩擦改进剂,此摩擦改进剂的功能有效量为足以赋予润滑剂理想的摩擦改进特性的量。通常,使用时每种这些添加剂的浓度范围为约0.001-约20wt%,在一个实施方案中,以润滑油组合物总重量计,范围约为0.01-约10wt%。
本发明润滑油组合物例如最终可应用于船用十字头柴油机汽缸润滑剂、汽车和铁路等曲柄轴箱润滑剂、重型机械如钢厂等用的润滑剂或作为轴承等的润滑脂润。润滑油组合物是流体或固体通常取决于是否存在增稠剂。典型的增稠剂包括聚脲乙酸酯、硬脂酸锂等。
在本发明的另一实施方案中,本发明的润滑油添加剂可以添加剂包或浓缩液形式提供,其中将所述添加剂加入基本惰性的、常规液体有机稀释剂例如像矿物油、石脑油、苯、甲苯或二甲苯中来形成添加剂浓缩液。这些浓缩液通常含约20%-约80wt%的这些稀释剂。一般使用100℃粘度约4-约8.5cSt且优选100℃粘度约4-约6cSt的中性油作为稀释剂,尽管也可使用合成油以及与添加剂和成品润滑油相容的其它有机液体。添加剂包一般还含有期望量和比例的一或多种不同的上述其它添加剂以便于直接与必须量基础油合并。
下面的非限定实施例用来说明本发明。
实施例1
向一个配有顶部机械搅拌、带氮气管线和Dean-Stark分水器的水冷凝器、温控器、加热套和热电偶的1L三颈圆底烧瓶中加入245g十八烯基丁二酸酐(ODSA)(得自Sigma Aldrich Corporation,St.Louis,Mo.,U.S.A.)、242g Exxon 150中性油和两滴抑泡剂(200-350cSt,得自Dow Corning)。将混合物加热到100℃并借助加料漏斗向混合物中滴加入132.64g四乙五胺(TEPA,相对ODSA 1.0摩尔当量)。最初加料阶段有轻微起泡。加完TEPA后,经约60分钟将温度提高到160℃然后维持160℃过夜。
将物料冷却到100℃并转移到一个3L圆底烧瓶中。将烧瓶在80℃下加热以加入马来酸酐。接着,在一个烧杯中将67g马来酸酐(相对TEPA 1摩尔当量)加热到固体熔融。将液化的马来酸酐转移到一个预热的有玻璃活塞的加料漏斗中。然后滴加入马来酸酐来控制过量泡沫并维持温度在80-110℃之间。在加料漏斗上使用热风枪以防止加料过程中马来酸酐固态化。加完马来酸酐后,将Dean-Stark分水器接到圆底烧瓶。经1小时将反应器温度升到160℃并维持此温度过夜。
将混合物冷却到80℃,然后将100g转移到一个配有机械搅拌板、带冷凝器的Dean-Stark分水器和氮气管线的250mL三颈圆底烧瓶中。接着,加入17.34g三氧化钼(相对TEPA 1mole当量)、50g甲苯、17g蒸馏水和2滴抑泡剂。将混合物搅拌并在100℃下加热过夜。然后将产物经带布氏漏斗的Celite 512于真空80℃-140℃条件下进行过滤。收集滤液并用旋转蒸发器浓缩(140℃最高温度下全开真空泵)来移除甲苯和残留水。产物为非常粘稠的棕色油,具有如下性质:
Mo=8.16wt.%
N=5.88wt%
总碱值=74.5mg KOH/g
实施例2
向CHEVRON 100中性油中加入1wt%实施例1的润滑油添加剂来形成润滑油组合物。
比较实施例A
向CHEVRON 100中性油中加入1.5wt.%二硫代磷酸锌来形成润滑油组合物
测试
磨损和摩擦性能
(A)微牵引力试验台(MTM)评价
使用微牵引力试验台(MTM)摩擦磨损试验机(tribometer)(PCSInstruments Ltd.,London UK)对实施例1的润滑油添加剂进行评价。MTM摩擦磨损试验机设定为以销盘模式运行,使用购自PCS Instruments的52100钢制抛光圆盘和一个购自Falex Corporation也是52100钢制的0.25英寸固定滚珠轴承代替销。试验在100℃下以7牛顿负荷和200mm/s滑动速度进行40分钟,然后是在0.1牛顿和2000mm/s滑动速度下5分钟走合期。在光学显微镜上人工测量球的磨斑并记录下来。试验结果是4次试验运行的平均磨斑数据。MTM磨损性能数据列于表1。
表1
MTM磨损性能结果
如上面的数据所示,用实施例1的润滑油添加剂处理的实施例2润滑油组合物在较低处理比率下提供了与用二硫代磷酸锌处理的比较实施例A的润滑油组合物类似的磨损性能。
实施例3
采用与实施例1所述相同的通用程序和组分制备钼酸化丁二酰亚胺配合物,不同处在于马来酸酐∶TEPA加料摩尔比为0.25∶1。钼酸化丁二酰亚胺配合物的钼含量为1.035wt%.。
实施例4
采用与实施例1所述相同的通用程序和组分制备钼酸化丁二酰亚胺配合物,不同处在于马来酸酐∶TEPA加料摩尔比为0.5∶1。钼酸化丁二酰亚胺配合物的钼含量为1.624wt%.。
实施例5
采用与实施例1所述相同的通用程序和组分制备钼酸化丁二酰亚胺配合物,不同处在于马来酸酐∶TEPA加料摩尔比为0.83∶1。钼酸化丁二酰亚胺配合物的钼含量为3.078wt%。
比较实施例B
向一个配有磁力搅拌器、带氮气管线和Dean-Stark分水器的水冷凝器、温控器、加热套和热电偶的100mL三颈圆底烧瓶中加入25.1g市购的氧化钼处理的单-丁二酰亚胺分散剂(含4.6wt%钼和2.2wt%氮),所述单-丁二酰亚胺分散剂是由聚异丁烯基(1000M.W.)丁二酸酐(PIBSA)和每分子约有5个胺基的多胺制成的,多胺∶PIBSA的加料摩尔比约为0.8∶1。将氧化钼处理的单-丁二酰亚胺分散剂搅拌并加热到110℃,加入1.68g马来酸酐(1摩尔当量)。将混合物在约160℃下搅拌1小时,得到黑色粘性油。
比较实施例C
向一个配有磁力搅拌器、带氮气管线和Dean-Stark分水器的水冷凝器、温控器、加热套和热电偶的100mL三颈圆底烧瓶中加入25.1g市购的氧化钼处理的单-丁二酰亚胺分散剂(含4.6wt%钼和2.2wt%氮),所述单-丁二酰亚胺分散剂是由聚异丁烯基(1000M.W.)丁二酸酐(PIBSA)和每分子约有5个胺基的多胺制成的,多胺∶PIBSA的加料摩尔比约为0.8∶1。将氧化钼处理的单-丁二酰亚胺分散剂搅拌并加热到110℃,加入1.68g马来酸酐(2摩尔当量)。将混合物在约160℃下搅拌1小时,得到黑色粘性油。
比较实施例D
配制II类基础油中含5wt%丁二酰亚胺分散剂、3wt%硼酸化丁二酰亚胺分散剂、4mM/kg低含量过碱值磺酸钙、58mM/kg羧酸盐清净剂、8mM/kg二硫代磷酸锌、0.5wt%二苯胺抗氧剂、0.5wt%位阻酚抗氧剂、0.3wt%倾点下降剂、9.85wt%烯烃共聚物粘度指数改进剂和5ppm抑泡剂的基础配方。
比较实施例E
配制含与比较实施例D相同的添加剂、基础油和处理比率(treatrate)的基础润滑油配方。将市购的二硫代氨基甲酸钼(得自Adeka asSakura505)以1wt%的量配入此基础润滑油配方。
比较实施例F
配制含与比较实施例D相同的添加剂、基础油和处理比率的基础润滑油配方。将市购的二硫代氨基甲酸钼(得自Adeka as Sakura505)配入此基础润滑油配方,使配方中总钼含量为500ppm。
比较实施例G
比较实施例H
比较实施例I
配制含与比较实施例D相同的添加剂、基础油和处理比率的基础润滑油配方。将市购的由聚异丁烯(1000M.W.)衍生的氧化钼丁二酰亚胺配合物以1wt%的量配入此基础润滑油配方。
比较实施例J
配制含与比较实施例D相同的添加剂、基础油和处理比率的基础润滑油配方。将市购的由聚异丁烯(1000M.W.)衍生的氧化钼丁二酰亚胺配合物以1wt%的量配入此基础润滑油配方,使配方中总Mo含量为500ppm。
比较实施例K
配制含与比较实施例D相同的添加剂、基础油和处理比率的基础润滑油配方。将比较实施例B的润滑油添加剂以1wt%的量配入此基础润滑油配方中。
比较实施例L
配制含与比较实施例D相同的添加剂、基础油和处理比率的基础润滑油配方。将比较实施例B的润滑油添加剂配入此基础润滑油配方中,使配方中总Mo含量为500ppm。
比较实施例M
配制含与比较实施例D相同的添加剂、基础油和处理比率的基础润滑油配方。将比较实施例C的润滑油添加剂以1wt%的量配入此基础润滑油配方中。
比较实施例N
配制含与比较实施例D相同的添加剂、基础油和处理比率的基础润滑油配方。将比较实施例C的润滑油添加剂配入此基础润滑油配方中,使配方中总Mo含量为500ppm。
实施例6
配制含与比较实施例D相同的添加剂、基础油和处理比率的基础润滑油配方。将实施例1的润滑油添加剂以1wt%的量配入此基础润滑油配方中。
实施例7
配制含与比较实施例D相同的添加剂、基础油和处理比率的基础润滑油配方。将实施例1的润滑油添加剂配入此基础润滑油配方中,使配方中总Mo含量为500ppm。
实施例8
配制含与比较实施例D相同的添加剂、基础油和处理比率的基础润滑油配方。将实施例3的润滑油添加剂以1wt%的量配入此基础润滑油配方中。
实施例9
配制含与比较实施例D相同的添加剂、基础油和处理比率的基础润滑油配方。将实施例4的润滑油添加剂以1wt%的量配入此基础润滑油配方中。
实施例10
配制含与比较实施例D相同的添加剂、基础油和处理比率的基础润滑油配方。将实施例5的润滑油添加剂以1wt%的量配入此基础润滑油配方中。
(B)高频往复试验机(HFRR)评价
分别对含实施例1润滑油添加剂的实施例6和7的润滑油组合物和含实施例3-5润滑油添加剂的实施例8-10的润滑油组合物的HFRR磨损和摩擦性能进行评价并与比较实施例D的基础润滑油配方和比较实施例E-N的润滑油组合物进行对比。HFRR试验是工业上公认的用来候选润滑油中气阀机构磨损性能的架台试验。PCS仪使用一个电磁振动器以小振幅摆动试样(球),同时向一个固定的试样(平盘)推压。摆动的振幅和频率及负荷可变。测定球与平板间的摩擦力和接触电阻(ECR)。平板、固定的试样放在装有润滑油的浴中且可加热。润滑油用约6wt%(基于润滑油总重量计)碳黑进行预处理。将碳黑搅拌入油中并使其浸湿,然后测试前均化15分钟。在光学显微镜上人工测定磨斑并记录下来。在此试验中,磨斑越小则对应于抗磨剂越有效,摩擦系数越小则对应于摩擦改进剂越有效。HFRR磨损和摩擦性能数据列于表2。
表2
HFRR磨损和摩擦性能结果
如数据所示,本发明的润滑油组合物相当于且在某些情况下显著好于本发明范围之外的润滑油组合物。
比较实施例O
配制II类基础油中含1.4wt%硼酸化丁二酰亚胺分散剂、2.75wt%丁二酰亚胺分散剂、55mM/kg过碱值苯酚钙、7.3mM/kg(~0.6wt%)二硫代磷酸锌、1wt%位阻酚抗氧剂、0.3wt%倾点下降剂和4wt%烯烃共聚物粘度指数改进剂的基础润滑油配方。
比较实施例P
配制II类基础油中含1.4wt%硼酸化丁二酰亚胺分散剂、2.75wt%丁二酰亚胺分散剂、55mM/kg过碱值苯酚钙、17mM/kg(1.4wt%)二硫代磷酸锌、1wt%位阻酚抗氧剂、0.3wt%倾点下降剂和4wt%烯烃共聚物粘度指数改进剂的基础润滑油配方。
实施例11
配制含与比较实施例O相同的添加剂、基础油和处理比率的基础润滑油配方。将实施例1的润滑油添加剂以1wt%的量配入此基础润滑油配方中。
(C)小型发动机磨损试验
使用小型发动机磨损试验对含实施例1的润滑油添加剂的实施例11的润滑油组合物抗磨性能进行评价并与比较实施例O和P的基础润滑油配方进行对比。测试油样在一个连接固定负荷如测功器或加速器的4000rpm转速的小型发动机上演示约60小时。发动机是Briggs andStratton生产的气冷单缸顶置气阀发动机,经改造来加速凸轮轴磨损。通过用一套双弹簧代替工厂的阀簧来提高气阀机构的负荷。对每一个试验,发动机配一个新的工厂曲柄轴和推杆。使用发动机直到视觉检测曲柄轴、汽缸内衬和汽化器显示异常磨损或接近破坏为止。任何试验前,用常规发动机油以3000rpm转速和规定的负荷运行每一发动机10小时。用测试油装备发动机,在每次用改造的发动机开始进行试验时先是约1小时的走合期,然后在负荷下进行剩余试验时间的操作。通过比较试验前后凸轮轮廓来量度曲柄轴磨损。结果示于表3。
表3
小型发动机磨损试验结果
数据显示,与比较实施例O的润滑油组合物相比,在小型发动机磨损试验中用实施例1润滑油添加剂处理的实施例11的润滑油组合物在抗磨性上有显著改进。为提供与实施例11润滑油组合物相当的抗磨性,必须要向基础润滑油配方里加入更多量的二硫代磷酸锌,如比较实施例P所示。因此,本发明的润滑油组合物可很好地提供对抗磨性的显著改进同时二硫代磷酸锌的用量少。这又使得润滑油组合物中磷和硫的含量降低到符合发动机油的要求。因此,本发明的润滑油添加剂不仅能为润滑油组合物提供显著改进的抗磨性,还能够降低润滑油组合物中锌、磷和硫的水平。
比较实施例Q
配制II类基础油中含3.8wt%丁二酰亚胺分散剂、3.5mM/kg低过碱值磺酸钙、45mM/kg高过碱值苯酚钙、5mM/kg仲醇衍生的二硫代磷酸锌、2mM/kg伯醇衍生的二硫代磷酸锌、1.0wt%二苯胺抗氧剂、0.3wt%倾点下降剂、4.8wt%烯烃共聚物粘度指数改进剂和10ppm抑泡剂的基础润滑油配方。
实施例12
配制含与比较实施例Q相同的添加剂、基础油和处理比率的基础润滑油配方。将实施例1的润滑油添加剂配入此基础润滑油配方中,使得配方中总Mo含量为500ppm。
氧化性能
在氧化台架试验中分析氧化作用对含实施例1润滑油添加剂的实施例12的润滑油组合物的影响并与氧化作用对比较实施例Q的基础润滑油配方的影响进行对比。氧化作用研究是在E.S.Yamaguchi等人在Tribology Transactions,Vol 42(4),895-901(1999)中描述的散装油氧化台架试验中进行。在此试验中,检测给定重量油于170℃和恒定压力下的氧吸收率。达到快速吸氧时间即称作自动氧化所需要的时间定为诱导时间。台架试验通常再现性在±0.5小时。在此试验中,诱导时间越长对应于越能有效抗氧化。氧化台架试验列于表4。
表4
氧化台架试验结果
数据显示,与比较实施例Q的润滑油组合物相比,用实施例1润滑油添加剂处理的实施例12的润滑油组合物的氧化性能方面有显著的改进。此外,本发明的润滑油组合物很好地提供氧化性能的改进同时二硫代磷酸锌的用量少。这又使得润滑油组合物中磷和硫的含量降低到符合发动机油的要求。因此,本发明的润滑油添加剂不仅能为润滑油组合物提供显著改进的氧化性能,还能够降低润滑油组合物中锌、磷和硫的水平。
比较实施例R
向一个配有顶部机械搅拌、带氮气管线和Dean-Stark分水器的水冷凝器、温控器、加热套和热电偶的500mL三颈圆底烧瓶中加入60.07g十八烯基丁二酸酐(ODSA)(得自Sigma Aldrich Corporation,St.Louis,Mo.,U.S.A.)、60.08g Exxon 150中性油和三滴抑泡剂(200-350cSt,得自Dow Corning)。将混合物加热到100℃并借助加料漏斗向混合物中滴加入32.88g四乙五胺(TEPA,相对ODSA 1.0摩尔当量)。最初加料阶段有轻微起泡。加完TEPA后,经约60分钟将温度提高到160℃然后维持160℃三小时。
将物料冷却到100℃以下,加入25.01g三氧化钼(相对TEPA 1摩尔当量)、69g甲苯、17g蒸馏水和0.1g抑泡剂。将混合物加热到100℃并在搅动条件下发泡形成凝胶。加入116g Exxon 100N油并将混合物搅拌过夜,得到一茶绿色凝胶。因此,不再试图将所述凝胶与马来酸酐反应。
比较实施例S
向一个配有顶部机械搅拌、带氮气管线和Dean-Stark分水器的水冷凝器、温控器、加热套和热电偶的500mL三颈圆底烧瓶中加入60.6gSAP值为120.3mgKOH/g的聚异丁烯基(1000M.W.)丁二酸酐。将混合物加热到100℃并加入10.45g四乙五胺(TEPA,1.0摩尔当量)。加完TEPA后,经约60分钟将温度提高到180℃然后维持160℃一小时。冷却过夜后加入12.2g Exxon 100N油,得到一粘性的棕色油。
将物料加热到约90℃,加入82g甲苯来形成溶液,然后加入7.9g三氧化钼(相对TEPA 1摩尔当量)和8.3g蒸馏水。将混合物90℃下搅拌1.5小时,然后升温至160℃,经约4小时移除甲苯和水。产物为粘性棕色油。接着,加入64g甲苯并将混合物加热到95℃以降低粘度便于过滤。几次试图将产物通过Whatman brand #1和#4滤纸(有或没有硅藻土助滤剂)过滤,但都没成功。产物重复用Exxon 100N油稀释后,产物还是不能过滤。因此,不再试图将产物与马来酸酐反应。
应该理解,本文所公开的实施方案可做各种改动。因此,以上说明书不应视为限制而仅仅是例举优选方案。例如,上文描述和作为本发明操作的最佳模式所实现的功能仅仅出于说明的目的。其它安排和方法可由本领域技术人员在不背离本发明精神的前提下实施。并且,本领域技术人员将能预想到所附权利要求书精神和范围内的其它改进。
Claims (15)
2.权利要求1的钼酸化丁二酰亚胺配合物,其中R是约C12-约C24烷基或烯基,a和b均为2,且x为2-5。
3.权利要求1或2的钼酸化丁二酰亚胺配合物,其中所述烯属不饱和羧酸或其酸酐是烯属不饱和一元羧酸或其酸酐。
4.权利要求1或2的钼酸化丁二酰亚胺配合物,其中所述烯属不饱和羧酸或其酸酐是烯属不饱和二元羧酸或其酸酐。
5.权利要求1或2的钼酸化丁二酰亚胺配合物,其中所述烯属不饱和羧酸或其酸酐是马来酸酐且所述酸性钼化合物是三氧化钼。
6.权利要求1-5任一项的钼酸化丁二酰亚胺配合物,其中所述烯属不饱和羧酸或其酸酐与式I的丁二酰亚胺的摩尔比为约0.9∶1-约1.05∶1。
7.权利要求1-6任一项的钼酸化丁二酰亚胺配合物,其中所述钼化合物与步骤(a)的丁二酰亚胺产物的摩尔比为约0.5∶1-约1.5∶1。
8.制备钼酸化丁二酰亚胺配合物的方法,所述方法包括(a)将式I的多胺的烷基或烯基丁二酰亚胺与烯属不饱和羧酸或其酸酐进行反应:
其中R是约C12-约C30的烷基或烯基,a和b独立地为2或3,x为0-10;和(b)将步骤(a)的产物与酸性钼化合物进行反应。
9.权利要求8的方法,其中R是约C12-约C24烷基或烯基,a和b均为2,且x为2-5。
10.权利要求8或9的方法,其中所述烯属不饱和羧酸或其酸酐是烯属不饱和一元羧酸或其酸酐。
11.权利要求8或9的方法,其中所述烯属不饱和羧酸或其酸酐是烯属不饱和二元羧酸或其酸酐。
12.权利要求8或9的方法,其中所述烯属不饱和羧酸或其酸酐是马来酸酐且所述酸性钼化合物是三氧化钼。
13.权利要求8-12任一项的方法,其中所述烯属不饱和羧酸或其酸酐与式I的丁二酰亚胺的摩尔比为约0.1∶1-约2∶1,且所述钼化合物与步骤(a)的丁二酰亚胺产物的摩尔比为约0.1∶1-约2∶1。
14.润滑油组合物,包括(a)主要量的润滑粘度基础油;和(b)次要量的权利要求1-7任一项的钼酸化丁二酰亚胺配合物。
15.操作内燃机的方法,包括用权利要求14的润滑油组合物操作内燃机的步骤。
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PCT/US2009/049217 WO2010002865A2 (en) | 2008-06-30 | 2009-06-30 | Lubricating oil additive and lubricating oil composition containing same |
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CN109196079A (zh) * | 2016-07-13 | 2019-01-11 | 雪佛龙奥伦耐有限责任公司 | 含有抗氧化剂混合物的协同润滑油组合物 |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20120077719A1 (en) * | 2010-09-24 | 2012-03-29 | Chevron Oronite Company Llc | Preparation of a molybdenum imide additive composition and lubricating oil compositions containing same |
US8426608B2 (en) * | 2011-01-21 | 2013-04-23 | Chevron Oronite Company Llc | Process for preparation of high molecular weight molybdenum succinimide complexes |
US8476460B2 (en) * | 2011-01-21 | 2013-07-02 | Chevron Oronite Company Llc | Process for preparation of low molecular weight molybdenum succinimide complexes |
US20140018269A1 (en) * | 2012-07-13 | 2014-01-16 | Chevron Oronite Company Llc | Post-treated molybdenum imide additive composition, methods of making same and lubricating oil compositions containing same |
EP2935543A4 (en) * | 2012-12-21 | 2016-01-27 | Chevron Oronite Co | POST-TREATED IMIDE AND MOLYBDENIDE ADDITIVE COMPOSITION, PROCESSES FOR PRODUCING THE SAME, AND LUBRICATING OIL COMPOSITIONS CONTAINING THE SAME |
US9393512B2 (en) | 2014-04-25 | 2016-07-19 | Pall Corporation | Processes for removing entrained particulates from a gas |
US9168499B1 (en) | 2014-04-25 | 2015-10-27 | Pall Corporation | Arrangements for removing entrained catalyst particulates from a gas |
US10329512B2 (en) | 2017-02-28 | 2019-06-25 | Chevron Oronite Company Llc | Lubrication oil composition with enhanced wear and low speed pre-ignition properties |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1085901A (en) | 1964-01-15 | 1967-10-04 | Courtaulds Ltd | Fermentation apparatus |
GB1085903A (en) | 1964-11-19 | 1967-10-04 | Castrol Ltd | Additives for lubricating compositions |
US4272387A (en) | 1979-06-28 | 1981-06-09 | Chevron Research Company | Process of preparing molybdenum complexes, the complexes so-produced and lubricants containing same |
US4283295A (en) | 1979-06-28 | 1981-08-11 | Chevron Research Company | Process for preparing a sulfurized molybdenum-containing composition and lubricating oil containing said composition |
US4265773A (en) | 1979-06-28 | 1981-05-05 | Chevron Research Company | Process of preparing molybdenum complexes, the complexes so-produced and lubricants containing same |
US4259194A (en) | 1979-06-28 | 1981-03-31 | Chevron Research Company | Reaction product of ammonium tetrathiomolybdate with basic nitrogen compounds and lubricants containing same |
US4285822A (en) | 1979-06-28 | 1981-08-25 | Chevron Research Company | Process for preparing a sulfurized molybdenum-containing composition and lubricating oil containing the composition |
US4259195A (en) | 1979-06-28 | 1981-03-31 | Chevron Research Company | Reaction product of acidic molybdenum compound with basic nitrogen compound and lubricants containing same |
US4263152A (en) | 1979-06-28 | 1981-04-21 | Chevron Research Company | Process of preparing molybdenum complexes, the complexes so-produced and lubricants containing same |
JPS5716095A (en) * | 1980-06-13 | 1982-01-27 | Texaco Development Corp | Production of lubricant additive |
US4324672A (en) | 1980-06-25 | 1982-04-13 | Texaco, Inc. | Dispersant alkenylsuccinimides containing oxy-reduced molybdenum and lubricants containing same |
US4500439A (en) | 1980-09-25 | 1985-02-19 | Standard Oil Company (Indiana) | Hydrocarbon-soluble polyamine-molybdenum compositions, lubricants and gasoline containing same |
US4357149A (en) | 1980-09-25 | 1982-11-02 | Standard Oil Company (Indiana) | Hydrocarbon-soluble oxidized, sulfurized polyamine-molbdenum compositions and gasoline containing same |
US6372696B1 (en) | 1999-11-09 | 2002-04-16 | The Lubrizol Corporation | Traction fluid formulation |
US6451920B1 (en) * | 1999-11-09 | 2002-09-17 | Chevron Chemical Company Llc | Process for making polyalkylene/maleic anhydride copolymer |
RU2201433C1 (ru) | 2001-06-27 | 2003-03-27 | Левин Александр Яковлевич | Способ получения присадки к моторным смазочным маслам |
US20040038833A1 (en) * | 2002-01-31 | 2004-02-26 | Deckman Douglas E. | Lubricating oil compositions for internal combustion engines with improved wear performance |
US6962896B2 (en) * | 2002-05-31 | 2005-11-08 | Chevron Oronite Company Llc | Reduced color molybdenum-containing composition and a method of making same |
US6696393B1 (en) * | 2002-08-01 | 2004-02-24 | Chevron Oronite Company Llc | Methods and compositions for reducing wear in internal combustion engines lubricated with a low phosphorus content lubricating oil |
US20080020952A1 (en) * | 2004-10-19 | 2008-01-24 | Kazuhiro Yagishita | Lubricant Composition |
JP4663288B2 (ja) * | 2004-10-19 | 2011-04-06 | Jx日鉱日石エネルギー株式会社 | 鉛含有金属材料と接触する潤滑油組成物 |
JP5300007B2 (ja) * | 2005-10-11 | 2013-09-25 | ザ ルブリゾル コーポレイション | 自動トランスミッション液に適した摩擦調整剤としての、ヒドロキシ酸を含むアミン製品 |
CN100510036C (zh) * | 2006-02-28 | 2009-07-08 | 中国石油化工股份有限公司 | 一种有机钼润滑油添加剂及其制备方法 |
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CN109196079A (zh) * | 2016-07-13 | 2019-01-11 | 雪佛龙奥伦耐有限责任公司 | 含有抗氧化剂混合物的协同润滑油组合物 |
CN109196079B (zh) * | 2016-07-13 | 2022-04-05 | 雪佛龙奥伦耐有限责任公司 | 含有抗氧化剂混合物的协同润滑油组合物 |
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WO2010002865A8 (en) | 2010-09-10 |
JP5438762B2 (ja) | 2014-03-12 |
EP2300579A4 (en) | 2012-05-23 |
US20110312862A1 (en) | 2011-12-22 |
US8022022B2 (en) | 2011-09-20 |
US20090325832A1 (en) | 2009-12-31 |
JP2011526959A (ja) | 2011-10-20 |
EP2300579B1 (en) | 2016-05-04 |
US8193132B2 (en) | 2012-06-05 |
CA2727739C (en) | 2017-04-18 |
CA2727739A1 (en) | 2010-01-07 |
WO2010002865A2 (en) | 2010-01-07 |
CN102076834B (zh) | 2016-07-06 |
EP2300579A2 (en) | 2011-03-30 |
WO2010002865A3 (en) | 2010-04-08 |
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