CA3038157C - Benzotriazole derivative and molybdenum dithiocarbamate-containing lubricating oil compositions for friction reduction and fuel consumption reduction - Google Patents

Benzotriazole derivative and molybdenum dithiocarbamate-containing lubricating oil compositions for friction reduction and fuel consumption reduction Download PDF

Info

Publication number: CA3038157C
Authority: CA; Canada
Prior art keywords: lubricating oil; oil composition; automotive engine; molybdenum; molybdenum dithiocarbamate
Prior art date: 2018-03-27
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.): Active

Application number

CA3038157A

Other languages

English (en)

French (fr)

Other versions

CA3038157A1 (en

Inventor

Shunsuke MATSUMOTO

Kunihiro Kouno

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Infineum International Ltd

Original Assignee

Infineum International Ltd

Priority date (The priority date 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 date listed.)

2018-03-27

Filing date

2019-03-27

Publication date

2023-11-07

2019-03-27 Application filed by Infineum International Ltd filed Critical Infineum International Ltd

2019-09-27 Publication of CA3038157A1 publication Critical patent/CA3038157A1/en

2023-11-07 Application granted granted Critical

2023-11-07 Publication of CA3038157C publication Critical patent/CA3038157C/en

Status Active legal-status Critical Current

2039-03-27 Anticipated expiration legal-status Critical

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239000010687 lubricating oil Substances 0.000 title claims abstract description 132
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 title claims abstract description 15
125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 title claims abstract 8
239000000203 mixture Substances 0.000 title claims description 168
239000000446 fuel Substances 0.000 title claims description 7
239000000654 additive Substances 0.000 claims abstract description 63
239000003112 inhibitor Substances 0.000 claims abstract description 15
238000005260 corrosion Methods 0.000 claims abstract description 9
230000007797 corrosion Effects 0.000 claims abstract description 9
230000001603 reducing effect Effects 0.000 claims abstract description 7
-1 molybdenum dithiocarbamate compound Chemical class 0.000 claims description 79
239000003921 oil Substances 0.000 claims description 64
125000004432 carbon atom Chemical group C* 0.000 claims description 41
239000002270 dispersing agent Substances 0.000 claims description 40
229910052751 metal Inorganic materials 0.000 claims description 38
239000002184 metal Substances 0.000 claims description 38
230000000996 additive effect Effects 0.000 claims description 37
239000003599 detergent Substances 0.000 claims description 37
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 29
239000011733 molybdenum Substances 0.000 claims description 28
229910052750 molybdenum Inorganic materials 0.000 claims description 28
150000001875 compounds Chemical class 0.000 claims description 27
125000000217 alkyl group Chemical group 0.000 claims description 24
239000002199 base oil Substances 0.000 claims description 23
125000001183 hydrocarbyl group Chemical group 0.000 claims description 23
239000003446 ligand Substances 0.000 claims description 23
230000001050 lubricating effect Effects 0.000 claims description 23
239000003963 antioxidant agent Substances 0.000 claims description 21
150000001412 amines Chemical class 0.000 claims description 17
238000000034 method Methods 0.000 claims description 16
229910052717 sulfur Inorganic materials 0.000 claims description 15
230000007935 neutral effect Effects 0.000 claims description 14
125000003118 aryl group Chemical group 0.000 claims description 12
125000000962 organic group Chemical group 0.000 claims description 10
239000011701 zinc Substances 0.000 claims description 10
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 9
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 9
239000003607 modifier Substances 0.000 claims description 9
229910052725 zinc Inorganic materials 0.000 claims description 9
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 6
238000005461 lubrication Methods 0.000 claims description 6
150000001298 alcohols Chemical class 0.000 claims description 5
239000007866 anti-wear additive Substances 0.000 claims description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 4
AVVIDTZRJBSXML-UHFFFAOYSA-L calcium;2-carboxyphenolate;dihydrate Chemical compound O.O.[Ca+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O AVVIDTZRJBSXML-UHFFFAOYSA-L 0.000 claims description 4
150000002170 ethers Chemical class 0.000 claims description 4
239000011777 magnesium Substances 0.000 claims description 4
229910052749 magnesium Inorganic materials 0.000 claims description 4
150000003003 phosphines Chemical class 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
244000126002 Ziziphus vulgaris Species 0.000 claims 1
125000001302 tertiary amino group Chemical group 0.000 claims 1
235000019198 oils Nutrition 0.000 description 63
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 30
229920000642 polymer Polymers 0.000 description 30
239000002585 base Substances 0.000 description 25
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 22
235000006708 antioxidants Nutrition 0.000 description 20
239000004034 viscosity adjusting agent Substances 0.000 description 19
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 16
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
150000001565 benzotriazoles Chemical class 0.000 description 14
239000002253 acid Substances 0.000 description 13
229920001577 copolymer Polymers 0.000 description 12
229920000098 polyolefin Polymers 0.000 description 12
239000011593 sulfur Substances 0.000 description 12
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
150000002148 esters Chemical class 0.000 description 11
239000005864 Sulphur Substances 0.000 description 10
239000000314 lubricant Substances 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
239000000047 product Substances 0.000 description 9
150000003839 salts Chemical class 0.000 description 9
239000004480 active ingredient Substances 0.000 description 8
239000005078 molybdenum compound Substances 0.000 description 8
239000000178 monomer Substances 0.000 description 8
VQTUBCCKSQIDNK-UHFFFAOYSA-N iso-butene Natural products CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 7
239000007788 liquid Substances 0.000 description 7
150000002752 molybdenum compounds Chemical class 0.000 description 7
229910052698 phosphorus Inorganic materials 0.000 description 7
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
229910052796 boron Inorganic materials 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
150000001993 dienes Chemical class 0.000 description 6
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
239000000463 material Substances 0.000 description 6
150000002736 metal compounds Chemical class 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
239000011574 phosphorus Substances 0.000 description 6
229920005862 polyol Polymers 0.000 description 6
239000000376 reactant Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 6
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
238000002485 combustion reaction Methods 0.000 description 5
229920001519 homopolymer Polymers 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
150000002430 hydrocarbons Chemical class 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
150000002989 phenols Chemical class 0.000 description 5
150000003077 polyols Chemical class 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
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
229920002367 Polyisobutene Polymers 0.000 description 4
230000003078 antioxidant effect Effects 0.000 description 4
229920001400 block copolymer Polymers 0.000 description 4
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 4
229910052802 copper Inorganic materials 0.000 description 4
239000010949 copper Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 4
230000000269 nucleophilic effect Effects 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
229920000768 polyamine Polymers 0.000 description 4
150000003871 sulfonates Chemical class 0.000 description 4
238000010998 test method Methods 0.000 description 4
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
MQHWFIOJQSCFNM-UHFFFAOYSA-L Magnesium salicylate Chemical compound [Mg+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O MQHWFIOJQSCFNM-UHFFFAOYSA-L 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000002015 acyclic group Chemical group 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
150000004982 aromatic amines Chemical class 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
239000011575 calcium Substances 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
150000007942 carboxylates Chemical class 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000000151 deposition Methods 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
238000005227 gel permeation chromatography Methods 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
229940072082 magnesium salicylate Drugs 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000010705 motor oil Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
239000002530 phenolic antioxidant Substances 0.000 description 3
229920000193 polymethacrylate Polymers 0.000 description 3
238000000746 purification Methods 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 3
229960001860 salicylate Drugs 0.000 description 3
239000010802 sludge Substances 0.000 description 3
229960002317 succinimide Drugs 0.000 description 3
239000010689 synthetic lubricating oil Substances 0.000 description 3
239000004711 α-olefin Substances 0.000 description 3
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
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical class COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
239000002518 antifoaming agent Substances 0.000 description 2
HYZHPAXFOXQGMV-UHFFFAOYSA-N benzotriazol-1-ylmethanamine Chemical compound C1=CC=C2N(CN)N=NC2=C1 HYZHPAXFOXQGMV-UHFFFAOYSA-N 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
238000005885 boration reaction Methods 0.000 description 2
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150000001639 boron compounds Chemical class 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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125000004122 cyclic group Chemical group 0.000 description 2
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 2
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230000000994 depressogenic effect Effects 0.000 description 2
150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
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238000004821 distillation Methods 0.000 description 2
238000009826 distribution Methods 0.000 description 2
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230000014509 gene expression Effects 0.000 description 2
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238000010348 incorporation Methods 0.000 description 2
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
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VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
239000011572 manganese Substances 0.000 description 2
239000011707 mineral Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
229910017464 nitrogen compound Inorganic materials 0.000 description 2
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
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238000005325 percolation Methods 0.000 description 1
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229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
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239000005077 polysulfide Substances 0.000 description 1
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239000011541 reaction mixture Substances 0.000 description 1
238000009877 rendering Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
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150000003333 secondary alcohols Chemical class 0.000 description 1
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239000002002 slurry Substances 0.000 description 1
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239000007787 solid Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000001911 terphenyls Chemical class 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 0.000 description 1
150000000000 tetracarboxylic acids Chemical class 0.000 description 1
JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical class CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
125000003396 thiol group Chemical class [H]S* 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000011135 tin Substances 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
150000003628 tricarboxylic acids Chemical class 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
229960001124 trientine Drugs 0.000 description 1
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
125000002948 undecyl 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])[H] 0.000 description 1
238000000214 vapour pressure osmometry Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

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- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/44—Five-membered ring containing nitrogen and carbon only
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- C10M169/04—Mixtures of base-materials and additives
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- C10M125/22—Compounds containing sulfur, selenium or tellurium
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- C10M2215/223—Five-membered rings containing nitrogen and carbon only
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/54—Fuel economy
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/255—Gasoline engines

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Chemistry (AREA)
Inorganic Chemistry (AREA)
Lubricants (AREA)

CA3038157A 2018-03-27 2019-03-27 Benzotriazole derivative and molybdenum dithiocarbamate-containing lubricating oil compositions for friction reduction and fuel consumption reduction Active CA3038157C (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP18164161		2018-03-27
EP18164161.4		2018-03-27

Publications (2)

Publication Number	Publication Date
CA3038157A1 CA3038157A1 (en)	2019-09-27
CA3038157C true CA3038157C (en)	2023-11-07

Family

ID=61827561

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA3038157A Active CA3038157C (en)	2018-03-27	2019-03-27	Benzotriazole derivative and molybdenum dithiocarbamate-containing lubricating oil compositions for friction reduction and fuel consumption reduction

Country Status (7)

Country	Link
US (1)	US20190300810A1 (ja)
EP (1)	EP3546549B1 (ja)
JP (1)	JP7149887B2 (ja)
KR (1)	KR102706017B1 (ja)
CN (1)	CN110305717A (ja)
CA (1)	CA3038157C (ja)
SG (1)	SG10201902658WA (ja)

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JP7104200B1 (ja) *	2021-03-17	2022-07-20	出光興産株式会社	潤滑油組成物

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2019
- 2019-02-18 EP EP19157843.4A patent/EP3546549B1/en active Active
- 2019-03-19 US US16/357,925 patent/US20190300810A1/en not_active Abandoned
- 2019-03-26 KR KR1020190033983A patent/KR102706017B1/ko active Active
- 2019-03-26 CN CN201910230614.1A patent/CN110305717A/zh active Pending
- 2019-03-26 SG SG10201902658W patent/SG10201902658WA/en unknown
- 2019-03-27 JP JP2019059804A patent/JP7149887B2/ja active Active
- 2019-03-27 CA CA3038157A patent/CA3038157C/en active Active

Also Published As

Publication number	Publication date
CN110305717A (zh)	2019-10-08
EP3546549B1 (en)	2022-11-09
US20190300810A1 (en)	2019-10-03
JP2019173000A (ja)	2019-10-10
EP3546549A1 (en)	2019-10-02
KR102706017B1 (ko)	2024-09-19
CA3038157A1 (en)	2019-09-27
JP7149887B2 (ja)	2022-10-07
KR20190113613A (ko)	2019-10-08
SG10201902658WA (en)	2019-10-30

Publication	Publication Date	Title
JP7377913B2 (ja)	2023-11-10	潤滑油組成物
CA3012205C (en)	2024-06-25	Motorcycle lubricant
CA2759639C (en)	2018-08-07	A lubricating oil composition
CA3038157C (en)	2023-11-07	Benzotriazole derivative and molybdenum dithiocarbamate-containing lubricating oil compositions for friction reduction and fuel consumption reduction
CA2883416C (en)	2022-04-19	A lubricating oil composition
CA2893404A1 (en)	2015-12-02	Lubricating oil composition containing polymeric friction modifiers having, functionalized polyolefin, polyalkylene glycol, polyol, and polycarboxylic acid therein
CA2549517C (en)	2014-01-21	Lubricating oil composition comprising non-hydrogenated polymer
CA2893426C (en)	2022-05-03	Lubricating oil compositions of base oil, dihydrocarbyl dithiophosphate metal salt, and polymeric friction modifiers derived from functionalized polyolefin, polyalkylene glycol,polyol, and polycarboxylic acid
CA2897619C (en)	2023-01-03	Lubricating compositions comprising polymeric friction modifiers
EP1728848B1 (en)	2013-08-07	Use of unsaturated olefin polymers to improve the compatibility between nitrile rubber seals and lubricating oil compositions

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