JP2019143126A - 煤取り扱い特性を有するグラフト化ポリマー - Google Patents
煤取り扱い特性を有するグラフト化ポリマー Download PDFInfo
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- JP2019143126A JP2019143126A JP2019020498A JP2019020498A JP2019143126A JP 2019143126 A JP2019143126 A JP 2019143126A JP 2019020498 A JP2019020498 A JP 2019020498A JP 2019020498 A JP2019020498 A JP 2019020498A JP 2019143126 A JP2019143126 A JP 2019143126A
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- Prior art keywords
- olefin copolymer
- alkylene
- moiety
- group
- formula
- Prior art date
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- 239000004071 soot Substances 0.000 title abstract description 20
- 229920000578 graft copolymer Polymers 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 82
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims abstract description 77
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 29
- 229920000768 polyamine Polymers 0.000 claims abstract description 27
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 25
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims abstract description 11
- -1 carbocycle Chemical group 0.000 claims description 92
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000002947 alkylene group Chemical group 0.000 claims description 36
- 239000000654 additive Substances 0.000 claims description 32
- 239000002199 base oil Substances 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000002252 acyl group Chemical group 0.000 claims description 25
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 24
- 230000000996 additive effect Effects 0.000 claims description 23
- 239000012141 concentrate Substances 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000001931 aliphatic group Chemical group 0.000 claims description 22
- 239000010687 lubricating oil Substances 0.000 claims description 22
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
- 229920001577 copolymer Polymers 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 12
- 239000005977 Ethylene Substances 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 7
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 239000000314 lubricant Substances 0.000 abstract description 34
- 239000002270 dispersing agent Substances 0.000 abstract description 33
- 239000003607 modifier Substances 0.000 abstract description 29
- 239000010705 motor oil Substances 0.000 abstract description 10
- 239000010802 sludge Substances 0.000 abstract description 7
- 230000006866 deterioration Effects 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 41
- 235000019198 oils Nutrition 0.000 description 41
- 229920000642 polymer Polymers 0.000 description 33
- 238000013459 approach Methods 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 26
- 229910052751 metal Inorganic materials 0.000 description 23
- 239000002184 metal Substances 0.000 description 23
- 238000000034 method Methods 0.000 description 20
- 125000003118 aryl group Chemical group 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 18
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 17
- 125000001183 hydrocarbyl group Chemical group 0.000 description 17
- 229910052717 sulfur Inorganic materials 0.000 description 17
- 150000001336 alkenes Chemical class 0.000 description 16
- 150000003141 primary amines Chemical class 0.000 description 16
- 239000004711 α-olefin Substances 0.000 description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 14
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 13
- 125000005843 halogen group Chemical group 0.000 description 13
- 239000011593 sulfur Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- 229930195733 hydrocarbon Natural products 0.000 description 12
- 125000003342 alkenyl group Chemical group 0.000 description 11
- 125000000753 cycloalkyl group Chemical group 0.000 description 11
- 239000003599 detergent Substances 0.000 description 11
- 229920001971 elastomer Polymers 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 230000001050 lubricating effect Effects 0.000 description 11
- 150000002430 hydrocarbons Chemical class 0.000 description 10
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 10
- 239000005078 molybdenum compound Substances 0.000 description 10
- 150000002752 molybdenum compounds Chemical class 0.000 description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 10
- 229920013639 polyalphaolefin Polymers 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 239000000376 reactant Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 9
- 125000002723 alicyclic group Chemical group 0.000 description 9
- 239000003963 antioxidant agent Substances 0.000 description 9
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 229910052750 molybdenum Inorganic materials 0.000 description 9
- 239000011733 molybdenum Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229910052698 phosphorus Inorganic materials 0.000 description 9
- 239000011574 phosphorus Substances 0.000 description 9
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 125000002541 furyl group Chemical group 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 238000012545 processing Methods 0.000 description 8
- 150000001993 dienes Chemical class 0.000 description 7
- 239000012530 fluid Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 150000001342 alkaline earth metals Chemical class 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- 229910052791 calcium Inorganic materials 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- 125000005266 diarylamine group Chemical group 0.000 description 6
- 239000000806 elastomer Substances 0.000 description 6
- 239000000446 fuel Substances 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000001544 thienyl group Chemical group 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 230000002776 aggregation Effects 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 125000005605 benzo group Chemical group 0.000 description 5
- 125000002619 bicyclic group Chemical group 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 239000010685 fatty oil Substances 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 5
- 229920001897 terpolymer Polymers 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 238000005054 agglomeration Methods 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 229920001038 ethylene copolymer Polymers 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000002480 mineral oil Substances 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
- 230000007935 neutral effect Effects 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 125000003226 pyrazolyl group Chemical group 0.000 description 4
- 125000000168 pyrrolyl group Chemical group 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- 150000005671 trienes Chemical class 0.000 description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 125000003435 aroyl group Chemical group 0.000 description 3
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 3
- 125000004658 aryl carbonyl amino group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 125000005390 cinnolyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 125000002704 decyl 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])* 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 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 3
- 239000012467 final product Substances 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000003827 glycol group Chemical group 0.000 description 3
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 description 3
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 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 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 3
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 3
- 238000005987 sulfurization reaction Methods 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 2
- NWGPLYYBECWONP-UHFFFAOYSA-N (carbamoylamino) hydrogen sulfate Chemical compound NC(=O)NOS(O)(=O)=O NWGPLYYBECWONP-UHFFFAOYSA-N 0.000 description 2
- OTXHZHQQWQTQMW-UHFFFAOYSA-N (diaminomethylideneamino)azanium;hydrogen carbonate Chemical compound OC([O-])=O.N[NH2+]C(N)=N OTXHZHQQWQTQMW-UHFFFAOYSA-N 0.000 description 2
- CIRMGZKUSBCWRL-LHLOQNFPSA-N (e)-10-[2-(7-carboxyheptyl)-5,6-dihexylcyclohex-3-en-1-yl]dec-9-enoic acid Chemical compound CCCCCCC1C=CC(CCCCCCCC(O)=O)C(\C=C\CCCCCCCC(O)=O)C1CCCCCC CIRMGZKUSBCWRL-LHLOQNFPSA-N 0.000 description 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 2
- XWJBRBSPAODJER-UHFFFAOYSA-N 1,7-octadiene Chemical compound C=CCCCCC=C XWJBRBSPAODJER-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical class CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical class CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
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- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- KKSDGJDHHZEWEP-SNAWJCMRSA-N trans-3-coumaric acid Chemical compound OC(=O)\C=C\C1=CC=CC(O)=C1 KKSDGJDHHZEWEP-SNAWJCMRSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
- C08F255/04—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms on to ethene-propene copolymers
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- C10M149/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
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- C08F8/10—Acylation
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- C08F8/12—Hydrolysis
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- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
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- C10M167/00—Lubricating compositions characterised by the additive being a mixture of a macromolecular compound, a non-macromolecular compound and a compound of unknown or incompletely defined constitution, each of these compounds being essential
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- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
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- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/022—Ethene
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- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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- C10M2207/121—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms
- C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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Abstract
Description
本明細書で使用されるとき、用語「有効濃度」は、ニュートン挙動を示すために煤化基油に必要な粘度調整剤の濃度を意味し、これは、基油中の煤粒子が十分に分散されていることを示す。
本開示の分散剤粘度指数調整剤は、潤滑剤濃縮物または添加剤濃縮物のいずれかにおいて、大部分の基油とブレンドすることができる。エンジン潤滑油組成物および/または金属加工組成物(または他の潤滑組成物)および/または添加剤濃縮物の配合に使用するのに好適な基油は、任意の好適な合成油、動物油、植物油、鉱油またはそれらの混合物から選択できる。動物油および植物油(例えばラード油、ヒマシ油)、ならびに液体石油および溶媒処理または酸処理されたパラフィン系、ナフテン系または混合パラフィン−ナフテン型の鉱物潤滑油などの鉱物潤滑油を使用することができる。石炭またはシェール由来の油もまた好適であり得る。基油は、典型的には、100℃で約2〜約15cSt、またはさらなる例として約2〜約10cStの粘度を有してもよい。さらに、気液プロセスから誘導された油も好適である。
上記の分散剤反応生成物と共に使用することができる金属清浄剤は、一般に、極性ヘッドが酸性有機化合物の金属塩を含む、長い疎水性尾部を有する極性ヘッドを含む。塩は、実質的に化学量論量の金属を含有していてもよく、その場合それらは通常は通常のまたは中性の塩として記載され、典型的には約0〜約150未満の全塩基価またはTBN(ASTM D2896により測定)を有する。酸化物または水酸化物のような過剰の金属化合物を、二酸化炭素のような酸性ガスと反応させることによって大量の金属塩基を含ませることができる。得られる過塩基化洗浄剤は、無機金属塩基(例えば、水和炭酸塩)のコアを取り囲む中和された洗浄剤のミセルを含む。そのような過塩基性洗浄剤は、約150以上、例えば約150〜約450以上のTBNを有することができる。
リン系磨耗防止剤を使用することができ、ジヒドロカルビルジチオリン酸亜鉛化合物、これに限定されないが、例えばジヒドロカルビルジチオリン酸亜鉛化合物を含むことができる。好適な金属ジヒドロカルビルジチオホスフェートは、ジヒドロカルビルジチオホスフェート金属塩を含むことができ、ここで金属は、アルカリもしくはアルカリ土類金属、またはアルミニウム、鉛、スズ、モリブデン、マンガン、ニッケル、銅もしくは亜鉛であり得る。
本開示の実施形態は、1つ以上の摩擦調整剤を含み得る。好適な摩擦調整剤は、金属含有および金属非含有摩擦調整剤を含み得、これらに限定されないが、イミダゾリンアミド類、アミン類、スクシンイミド類、アルコキシル化アミン類、アルコキシル化エーテルアミン類、アミンオキシド類、アミドアミン類、ニトリル類、ベタイン類、四級アミン類、イミン類、アミン塩類、アミノグアナジン類、アルカノールアミド類、ホスホネート類、金属含有化合物、グリセリンエステル類などを含み得る。
いくつかの実施形態において、泡抑制剤は、組成物中での使用に適した他の成分を形成し得る。泡抑制剤は、シリコーン、ポリアクリレートなどから選択することができる。本明細書に記載のエンジン潤滑剤配合物中の消泡剤の量は、配合物の総重量に基づいて約0.001重量%〜約0.1重量%の範囲であり得る。さらなる例として、消泡剤は、約0.004重量%〜約0.008重量%の量で存在してもよい。
酸化抑制剤または酸化防止剤は、使用中にベースストックが劣化する傾向を低減し、その劣化は、金属表面に堆積するスラッジおよびワニス状堆積物などの酸化生成物によっておよび完成潤滑剤の粘度増大によって証明され得る。そのような酸化抑制剤には、障害フェノール、硫化障害フェノール、C5〜C12アルキル側鎖を有するアルキルフェノールチオエステルのアルカリ土類金属塩、カルシウムノニルフェノールスルフィド、無灰油溶性フェネート類および硫化フェネート類などの硫化アルキルフェノール類、硫化または非硫化アルキルフェノールの金属塩、リン硫化または硫化炭化水素類、リンエステル類、金属チオカルバメート類、および米国特許4,867,890号に記載のような油溶性銅化合物が含まれる。
本明細書に記載されている反応は、オーバーヘッド攪拌、水分除去凝縮器、温度プローブ、および窒素供給を備えた500mLフラスコ中で行われた。必要ならば、イソマントルを用いて反応物を加熱した。
エチレンプロピレンコポリマー(Mn=5,400、45.54重量%の反応生成量)、および無水マレイン酸(Sigma Aldrich、1.21重量%の反応生成量)を、凝縮器および窒素ブランケット下のDean Stark装置を備えた2つ口丸底フラスコに投入した。フラスコを165℃に加熱し、1時間保持してポリマーの良好な溶解を確実にした。完全に溶解した後、過酸化ジクミル(Sigma Aldrich、0.19重量%の反応生成量)をフラスコに投入し、1時間保持し、続いてさらに別の過酸化ジクミルを添加した(0.20重量%の反応生成量)。得られた混合物を1時間反応させた。反応が完了した後、フラスコを真空下(25mmHg)で230℃に4時間加熱して未反応の無水マレイン酸を除去した。群II基油(Phillip 66 110 N、44.07重量%の反応生成量)をフラスコに添加し、反応温度を165℃に設定した。テトラエチレンペンタラミン(Sigma Aldrich、TEPA、1.21質量%の反応生成量)、任意のSurfonic L24−2(Huntsman、7.00質量%の反応生成量)、およびナフタル酸無水物(Sigma Aldrich、0.57質量%の反応質量)の混合物を165℃のフラスコに投入し、4時間反応させて最終生成物を得、これは100℃で176.8cStの動粘度を有していた。この実施例のために、反応物の1つの混合物を調製した。
エチレンプロピレンコポリマー(Mn=22,000、20.10重量%の反応生成量)、110N基油(9.03重量%の反応生成量)および無水マレイン酸(0.51重量%の反応生成量)を、凝縮器および窒素ブランケット下のDean Stark装置を備えた2つ口丸底フラスコに投入した。フラスコを165℃に加熱し、1時間保持してポリマーの良好な溶解を確実にした。完全に溶解した後、過酸化ジクミル(0.077重量%の反応生成量)をフラスコに投入し、30分間保持し、続いてさらに別の過酸化ジクミルを添加した(0.077重量%の反応生成量)。得られた混合物を1時間反応させた。反応が完了した後、フラスコを25Hgの真空下で4時間230℃に加熱して未反応の無水マレイン酸を除去した。I群基油(Phillip 66 110 N、50.72重量%反応生成量)をフラスコに添加し、反応温度を165℃に設定した。次にポリエーテルジアミン(Jeffamine D2000、Huntsman)をフラスコに添加し、フラスコを165℃の温度に2時間保った。110N基油(8.42重量%反応生成量)およびナフタル酸無水物(1.08重量%反応生成量)の分散液を調製し、反応混合物に添加した。得られた混合物を165℃で4時間保持して、100℃で383.5cStの動粘度を有する最終生成物を得た。この実施例は反応物の逐次添加を使用する方法を示す。
Claims (15)
- オレフィンコポリマー粘度調整剤であって、
a)オレフィンコポリマーの1,000の数平均分子量単位当たり0.10〜0.80のアシル基をグラフト化したオレフィンコポリマーを含むアシル化オレフィンコポリマーであって、前記オレフィンコポリマーが、約500〜40,000の数平均分子量を有する、アシル化オレフィンコポリマーと、
b)式Iのポリアミン化合物と、
環部分Aが、最大3つの環が縮合している5、6、または7員複素環であり、縮合している前記環(1つもしくは複数)が、フェニル、炭素環、複素環、ヘテロアリール、またはそれらの組み合わせから選択され、環Aが、ハロ、−CN、オキソ、ヒドロキシル、ハロアルキル、C1−4アルキル、C1−4アルキルカルボニル、C1−4アルコキシ、C1−4アルコキシカルボニル、−NH2、−NH(C1−4アルキル)、およびN(C1−4アルキル)2から選択された1つ以上の置換基で任意選択で置換され、
Xが、C2〜C50アルキレンリンカー単位であり、1つ以上の炭素単位が、−O−、−NR’−、−NR’NR’−、−C(O)−、−C(O)O−、−C(O)NR’からなる群から選択される二価部分で任意選択でかつ独立して置き換えられ、各Xが、1つ以上のR”置換基で任意選択でかつ独立して置換され、
各R’が、水素、C1−6脂肪族、フェニル、またはアルキルフェニルからなる群から選択され、
各R”が、C1−6脂肪族、C3−7シクロアルキル、3〜7員ヘテロシクロアルキル、ヘテロアリール、およびフェニルからなる群から独立して選択され、R”は、ハロ、シアノ、アミノ、ヒドロキシル、−OR’、−C(O)R’、−C(O)OR’、または−C(O)NR’2で任意選択で置換される、ジカルボン酸またはその無水物と、の反応生成物を含む、粘度調整剤。 - Xが、式−(アルキレン−NR’)n−アルキレン−のポリアルキルアミン単位であり、前記アルキレン部分が、C1−C6分岐または直鎖アルキレン部分であり、nが、1〜20の整数である、請求項1に記載の粘度調整剤。
- Xが、式−(アルキレン−O)m−アルキレン−のポリアルキルアミン単位であり、前記アルキレン部分が、C1−C6分岐または直鎖アルキレン部分であり、mが、1〜50の整数である、請求項1に記載の粘度調整剤。
- 環部分Aが、次式である、請求項1に記載の粘度調整剤
- 前記オレフィンコポリマーが、エチレンと、3〜18個の炭素原子を有するアルキレンとのコポリマーである、請求項1に記載の粘度調整剤。
- 添加剤濃縮物であって、
基油希釈剤と、
高度にグラフト化された多官能性オレフィンコポリマー粘度調整剤であって、
a)オレフィンコポリマーの1,000の数平均分子量単位当たり0.10〜0.80のアシル基をグラフト化したオレフィンコポリマーを含むアシル化オレフィンコポリマーであって、前記オレフィンコポリマーが、約500〜40,000の数平均分子量を有する、アシル化オレフィンコポリマーと、
b)式Iのポリアミン化合物と、
環部分Aが、最大3つの環が縮合している5、6、または7員複素環であり、縮合している前記環(1つもしくは複数)が、フェニル、炭素環、複素環、ヘテロアリール、またはそれらの組み合わせから選択され、環Aが、ハロ、−CN、オキソ、ヒドロキシル、ハロアルキル、C1−4アルキル、C1−4アルキルカルボニル、C1−4アルコキシ、C1−4アルコキシカルボニル、−NH2、−NH(C1−4アルキル)、およびN(C1−4アルキル)2から選択された1つ以上の置換基で任意選択で置換され、
Xが、C2〜C50アルキレンリンカー単位であり、1つ以上の炭素単位が、−O−、−NR’−、−NR’NR’−、−C(O)−、−C(O)O−、−C(O)NR’からなる群から選択される二価部分で任意選択でかつ独立して置き換えられ、各Xが、1つ以上のR”置換基で任意選択でかつ独立して置換され、
各R’が、水素、C1−6脂肪族、フェニル、またはアルキルフェニルからなる群から選択され、
各R”が、C1−6脂肪族、C3−7シクロアルキル、3〜7員ヘテロシクロアルキル、ヘテロアリール、およびフェニルからなる群から独立して選択され、R”は、ハロ、シアノ、アミノ、ヒドロキシル、−OR’、−C(O)R’、−C(O)OR’、または−C(O)NR’2で任意選択で置換される、ジカルボン酸またはその無水物と、の反応生成物を含む、粘度調整剤と、を含む、添加剤濃縮物。 - Xが、式−(アルキレン−NR’)n−アルキレン−のポリアルキルアミン単位であり、前記アルキレン部分が、C1−C6分岐または直鎖アルキレン部分であり、nが、1〜20の整数である、請求項6に記載の添加剤濃縮物。
- Xが、式−(アルキレン−O)m−アルキレン−のポリアルキルアミン単位であり、前記アルキレン部分が、C1−C6分岐または直鎖アルキレン部分であり、mが、1〜50の整数である、請求項6に記載の添加剤濃縮物。
- 環部分Aが、次式である、請求項6に記載の添加剤濃縮物
- 前記濃縮物が、前記基油希釈剤中に約10〜約60重量パーセントの前記高度にグラフト化された多官能性オレフィンコポリマー粘度調整剤を含む、請求項6に記載の添加剤濃縮物。
- 潤滑油組成物であって、
主要量の基油と、
高度にグラフト化された多官能性オレフィンコポリマー粘度調整剤であって、
a)オレフィンコポリマーの1,000の数平均分子量単位当たり0.10〜0.80のアシル基をグラフト化したオレフィンコポリマーを含むアシル化オレフィンコポリマーであって、前記オレフィンコポリマーが、約500〜40,000の数平均分子量を有する、アシル化オレフィンコポリマーと、
b)式Iのポリアミン化合物と、
環部分Aが、最大3つの環が縮合している5、6、または7員複素環であり、縮合している前記環(1つもしくは複数)が、フェニル、炭素環、複素環、ヘテロアリール、またはそれらの組み合わせから選択され、環Aが、ハロ、−CN、オキソ、ヒドロキシル、ハロアルキル、C1−4アルキル、C1−4アルキルカルボニル、C1−4アルコキシ、C1−4アルコキシカルボニル、−NH2、−NH(C1−4アルキル)、およびN(C1−4アルキル)2から選択された1つ以上の置換基で任意選択で置換され、
Xが、C2〜C50アルキレンリンカー単位であり、1つ以上の炭素単位が、−O−、−NR’−、−NR’NR’−、−C(O)−、−C(O)O−、−C(O)NR’からなる群から選択される二価部分で任意選択でかつ独立して置き換えられ、各Xが、1つ以上のR”置換基で任意選択でかつ独立して置換され、
各R’が、水素、C1−6脂肪族、フェニル、またはアルキルフェニルからなる群から選択され、
各R”が、C1−6脂肪族、C3−7シクロアルキル、3〜7員ヘテロシクロアルキル、ヘテロアリール、およびフェニルからなる群から独立して選択され、R”は、ハロ、シアノ、アミノ、ヒドロキシル、−OR’、−C(O)R’、−C(O)OR’、または−C(O)NR’2で任意選択で置換される、ジカルボン酸またはその無水物と、の反応生成物を含む、粘度調整剤と、を含む、潤滑油組成物。 - Xが、式−(アルキレン−NR’)n−アルキレン−のポリアルキルアミン単位であり、前記アルキレン部分が、C1−C6分岐または直鎖アルキレン部分であり、nが、1〜20の整数である、請求項11に記載の潤滑油組成物。
- Xが、式−(アルキレン−O)m−アルキレン−のポリアルキルアミン単位であり、前記アルキレン部分が、C1−C6分岐または直鎖アルキレン部分であり、mが、1〜50の整数である、請求項11に記載の潤滑油組成物。
- 環部分Aが、
- 前記潤滑油組成物が、約0.01〜約10重量%の前記高度にグラフト化された多官能オレフィンコポリマー粘度調整剤を含む、請求項11に記載の潤滑油組成物。
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