CN103827086A - 羧酸吡咯烷酮及其使用方法 - Google Patents
羧酸吡咯烷酮及其使用方法 Download PDFInfo
- Publication number
- CN103827086A CN103827086A CN201280045805.7A CN201280045805A CN103827086A CN 103827086 A CN103827086 A CN 103827086A CN 201280045805 A CN201280045805 A CN 201280045805A CN 103827086 A CN103827086 A CN 103827086A
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- China
- Prior art keywords
- compound
- alkyl
- amine
- oil
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 238000000034 method Methods 0.000 title claims abstract description 15
- 150000004040 pyrrolidinones Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 108
- 150000001412 amines Chemical class 0.000 claims abstract description 42
- 230000001050 lubricating effect Effects 0.000 claims abstract description 35
- 230000005540 biological transmission Effects 0.000 claims abstract description 29
- 239000000314 lubricant Substances 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 72
- 239000003921 oil Substances 0.000 claims description 67
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 150000002148 esters Chemical class 0.000 claims description 31
- 239000000654 additive Substances 0.000 claims description 18
- 230000000996 additive effect Effects 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 10
- DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Chemical compound OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 230000007246 mechanism Effects 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- -1 N-substituted 4-carboxypyrrolidin-2-one Chemical class 0.000 abstract description 70
- 239000012530 fluid Substances 0.000 abstract description 26
- 239000010705 motor oil Substances 0.000 abstract description 8
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 description 29
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 28
- 239000000463 material Substances 0.000 description 27
- 229910052751 metal Inorganic materials 0.000 description 25
- 239000002184 metal Substances 0.000 description 25
- 238000000746 purification Methods 0.000 description 21
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 20
- 239000003963 antioxidant agent Substances 0.000 description 19
- 230000003078 antioxidant effect Effects 0.000 description 19
- 229910052799 carbon Inorganic materials 0.000 description 19
- 239000002270 dispersing agent Substances 0.000 description 18
- 229920000768 polyamine Polymers 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 239000004034 viscosity adjusting agent Substances 0.000 description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 15
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 14
- 150000001721 carbon Chemical group 0.000 description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 229930195733 hydrocarbon Natural products 0.000 description 12
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 12
- 239000004215 Carbon black (E152) Substances 0.000 description 11
- 238000005885 boration reaction Methods 0.000 description 11
- 229960002317 succinimide Drugs 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 125000001931 aliphatic group Chemical group 0.000 description 10
- 239000003599 detergent Substances 0.000 description 10
- ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 description 10
- 150000002430 hydrocarbons Chemical class 0.000 description 10
- 229910052698 phosphorus Inorganic materials 0.000 description 10
- 239000011574 phosphorus Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000005864 Sulphur Substances 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 229920013639 polyalphaolefin Polymers 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000011701 zinc Substances 0.000 description 9
- 229910052725 zinc Inorganic materials 0.000 description 9
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 8
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 8
- 230000029936 alkylation Effects 0.000 description 8
- 238000005804 alkylation reaction Methods 0.000 description 8
- 239000011575 calcium Substances 0.000 description 8
- 229910052791 calcium Inorganic materials 0.000 description 8
- 239000003925 fat Substances 0.000 description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 description 8
- 150000002632 lipids Chemical class 0.000 description 8
- 229960001860 salicylate Drugs 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 239000003760 tallow Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 229910019142 PO4 Inorganic materials 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- 238000002485 combustion reaction Methods 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 235000021317 phosphate Nutrition 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- 230000008719 thickening Effects 0.000 description 7
- 239000010936 titanium Substances 0.000 description 7
- 229910052719 titanium Inorganic materials 0.000 description 7
- 150000003609 titanium compounds Chemical class 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000004996 alkyl benzenes Chemical class 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 239000002783 friction material Substances 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- 229920000098 polyolefin Polymers 0.000 description 6
- 238000005987 sulfurization reaction Methods 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 125000005266 diarylamine group Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 5
- QVXGKJYMVLJYCL-UHFFFAOYSA-N 2,3-di(nonyl)-N-phenylaniline Chemical compound C(CCCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCCC QVXGKJYMVLJYCL-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 229920002367 Polyisobutene Polymers 0.000 description 4
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- LVZUNTGFCXNQAF-UHFFFAOYSA-N n-nonyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCCC)C1=CC=CC=C1 LVZUNTGFCXNQAF-UHFFFAOYSA-N 0.000 description 4
- 150000002924 oxiranes Chemical class 0.000 description 4
- 229920001281 polyalkylene Polymers 0.000 description 4
- 229920000193 polymethacrylate Polymers 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 230000003068 static effect Effects 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 150000003751 zinc Chemical class 0.000 description 4
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 229940077388 benzenesulfonate Drugs 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000012612 commercial material Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- BVXOPEOQUQWRHQ-UHFFFAOYSA-N dibutyl phosphite Chemical compound CCCCOP([O-])OCCCC BVXOPEOQUQWRHQ-UHFFFAOYSA-N 0.000 description 3
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 3
- 239000003502 gasoline Substances 0.000 description 3
- 239000004519 grease Substances 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000010687 lubricating oil Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 3
- 229940095064 tartrate Drugs 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UUNBFTCKFYBASS-UHFFFAOYSA-N C(CCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCC Chemical class C(CCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCC UUNBFTCKFYBASS-UHFFFAOYSA-N 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical group OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical compound [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000008431 aliphatic amides Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 239000002199 base oil Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001639 boron compounds Chemical class 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 239000012208 gear oil Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 2
- 239000010688 mineral lubricating oil Substances 0.000 description 2
- 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 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- XIFJZJPMHNUGRA-UHFFFAOYSA-N n-methyl-4-nitroaniline Chemical compound CNC1=CC=C([N+]([O-])=O)C=C1 XIFJZJPMHNUGRA-UHFFFAOYSA-N 0.000 description 2
- RQVGZVZFVNMBGS-UHFFFAOYSA-N n-octyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCC)C1=CC=CC=C1 RQVGZVZFVNMBGS-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 229940059574 pentaerithrityl Drugs 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 230000026731 phosphorylation Effects 0.000 description 2
- 238000006366 phosphorylation reaction Methods 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229920001021 polysulfide Polymers 0.000 description 2
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- 238000010408 sweeping Methods 0.000 description 1
- 239000010729 system oil Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical group CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- BWPNIANVWARHPR-UHFFFAOYSA-N tridecyl dihydrogen phosphite Chemical compound CCCCCCCCCCCCCOP(O)O BWPNIANVWARHPR-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- PZXFWBWBWODQCS-UHFFFAOYSA-L zinc;2-carboxyphenolate Chemical compound [Zn+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O PZXFWBWBWODQCS-UHFFFAOYSA-L 0.000 description 1
- 229940043798 zincon Drugs 0.000 description 1
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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/44—Five-membered ring containing nitrogen and carbon only
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
-
- 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
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- 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
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
-
- 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
Abstract
Description
添加剂 | 实施方案(重量% | ) | |
A | B | C | |
本发明化合物 | 0.25-2.5 | 0.1-5 | 0.01-10 |
分散剂 | 1-4 | 2-7 | 0-5 |
特压剂 | 3-6 | 0-6 | 0-3 |
过碱性清净剂 | 0-1 | 0.01-2 | 0.5-6 |
抗氧化剂 | 0-5 | 0.01-2 | 0-3 |
抗磨剂 | 0.5-5 | 0.01-3 | 0.5-3 |
粘度改进剂 | 0.1-70 | 0.1-15 | 1-60 |
任何其它性能添加剂 | 0-10 | 0-8 | 0-6 |
具有润滑粘度的油 | 至100%的余量 | 至100%的余量 | 至100%的余量 |
添加剂 | 实施方案(重量%) | ||
A | B | C | |
本发明化合物 | 0.25-2.5 | 0.1-5 | 0.01-10 |
分散剂 | 0-12 | 0-8 | 0.5-6 |
分散剂粘度改进剂 | 0-5 | 0-4 | 0.05-2 |
过碱性清净剂 | 0.1-15 | 0.1-10 | 0.2-8 |
抗氧化剂 | 0.1-13 | 0.1-10 | 0.5-5 |
抗磨剂 | 0.1-15 | 0.1-10 | 0.3-5 |
粘度改进剂 | 0-10 | 0.5-8 | 1-6 |
任何其它性能添加剂 | 0-10 | 0-8 | 0-6 |
具有润滑粘度的油 | 至100%的余量 | 至100%的余量 | 至100%的余量 |
ATF配制剂 | 100% |
油 | 84.24 |
分散剂 | 1.95 |
抗磨剂 | 0.20 |
磷酸 | 0.08 |
抗氧化剂 | 0.89 |
密封溶胀剂 | 0.40 |
倾点下降剂 | 0.10 |
粘度改进剂 | 2.38 |
本技术的摩擦改进剂 | n% |
Claims (14)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161510174P | 2011-07-21 | 2011-07-21 | |
US61/510,174 | 2011-07-21 | ||
PCT/US2012/047371 WO2013013026A1 (en) | 2011-07-21 | 2012-07-19 | Carboxylic pyrrolidinones and methods of use thereof |
Publications (2)
Publication Number | Publication Date |
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CN103827086A true CN103827086A (zh) | 2014-05-28 |
CN103827086B CN103827086B (zh) | 2016-04-13 |
Family
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Application Number | Title | Priority Date | Filing Date |
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CN201280045805.7A Active CN103827086B (zh) | 2011-07-21 | 2012-07-19 | 羧酸吡咯烷酮及其使用方法 |
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Country | Link |
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US (2) | US9481848B2 (zh) |
EP (1) | EP2734501A1 (zh) |
JP (1) | JP6054390B2 (zh) |
KR (1) | KR20140066709A (zh) |
CN (1) | CN103827086B (zh) |
AU (1) | AU2012283952B2 (zh) |
BR (1) | BR112014001289A2 (zh) |
CA (1) | CA2842660C (zh) |
WO (1) | WO2013013026A1 (zh) |
Cited By (1)
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---|---|---|---|---|
CN106574202A (zh) * | 2014-05-06 | 2017-04-19 | 路博润公司 | 碱性无灰添加剂 |
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WO2014074335A1 (en) * | 2012-11-07 | 2014-05-15 | The Lubrizol Corporation | Basic ashless additives |
CN106661484B (zh) * | 2014-05-06 | 2020-01-03 | 路博润公司 | 包含抗磨剂的润滑剂组合物 |
WO2015171676A1 (en) * | 2014-05-06 | 2015-11-12 | The Lubrizol Corporation | Lubricant composition containing an antiwear agent |
WO2015171364A1 (en) * | 2014-05-06 | 2015-11-12 | The Lubrizol Corporation | Anti-corrosion additives |
WO2017079575A1 (en) * | 2015-11-06 | 2017-05-11 | The Lubrizol Corporation | Lubricant composition containing an antiwear agent |
EP3371284A1 (en) * | 2015-11-06 | 2018-09-12 | The Lubrizol Corporation | Lubricant composition containing an antiwear agent |
WO2019018326A1 (en) * | 2017-07-17 | 2019-01-24 | The Lubrizol Corporation | LOW-ZINC LUBRICANT COMPOSITION |
JP7301017B2 (ja) * | 2020-03-31 | 2023-06-30 | 出光興産株式会社 | 潤滑油用添加剤及び駆動系用潤滑油組成物 |
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FR2961101B1 (fr) * | 2010-06-09 | 2013-01-25 | Oreal | Composition comprenant au moins une 2-pyrrolidone fonctionnalisee par un radical ester ou amide, et au moins un pigment ou un colorant direct pour la teinture des matieres keratiniques |
DE102010046680A1 (de) * | 2010-09-16 | 2012-03-22 | Clariant International Limited | Verwendung von N-substituierten 2-Pyrrolidon-4-carbonsäureestern als Lösemittel |
-
2012
- 2012-07-19 AU AU2012283952A patent/AU2012283952B2/en not_active Ceased
- 2012-07-19 CN CN201280045805.7A patent/CN103827086B/zh active Active
- 2012-07-19 EP EP12740837.5A patent/EP2734501A1/en not_active Withdrawn
- 2012-07-19 JP JP2014521781A patent/JP6054390B2/ja active Active
- 2012-07-19 BR BR112014001289A patent/BR112014001289A2/pt not_active Application Discontinuation
- 2012-07-19 WO PCT/US2012/047371 patent/WO2013013026A1/en active Application Filing
- 2012-07-19 KR KR1020147004424A patent/KR20140066709A/ko active IP Right Grant
- 2012-07-19 US US14/233,394 patent/US9481848B2/en active Active
- 2012-07-19 CA CA2842660A patent/CA2842660C/en not_active Expired - Fee Related
-
2016
- 2016-06-16 US US15/183,864 patent/US20160298051A1/en not_active Abandoned
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US3218264A (en) * | 1961-10-24 | 1965-11-16 | Katz Jacob | Lubricants containing amine salts of n-substituted pyrrolidone carboxylic acids |
US3644375A (en) * | 1968-10-18 | 1972-02-22 | Toray Industries | Lactam dicarboxylic acids and process for producing them |
GB1483457A (en) * | 1973-09-18 | 1977-08-17 | Cooper Ltd Ethyl | Lubricant additives their preparation and compositions containing them |
US6093829A (en) * | 1997-08-14 | 2000-07-25 | Mona Industries, Inc. | Silicone monomers and oligomers having a carboxyl functional group thereon |
WO2006015818A1 (de) * | 2004-08-06 | 2006-02-16 | Basf Aktiengesellschaft | Polyamin-additive für kraft-und schmierstoffe |
WO2010033447A2 (en) * | 2008-09-16 | 2010-03-25 | The Lubrizol Corporation | Composition containing heterocyclic compounds and a method of lubricating an internal combustion engine |
WO2010149250A1 (de) * | 2009-06-25 | 2010-12-29 | Clariant International Ltd | Wassergemischte metallbearbeitungsflüssigkeiten, enthaltend etherpyrrolidoncarbonsäuren |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106574202A (zh) * | 2014-05-06 | 2017-04-19 | 路博润公司 | 碱性无灰添加剂 |
CN106574202B (zh) * | 2014-05-06 | 2020-05-29 | 路博润公司 | 碱性无灰添加剂 |
Also Published As
Publication number | Publication date |
---|---|
KR20140066709A (ko) | 2014-06-02 |
US9481848B2 (en) | 2016-11-01 |
WO2013013026A1 (en) | 2013-01-24 |
AU2012283952A1 (en) | 2014-02-06 |
JP6054390B2 (ja) | 2016-12-27 |
CA2842660A1 (en) | 2013-01-24 |
US20160298051A1 (en) | 2016-10-13 |
US20140162920A1 (en) | 2014-06-12 |
CN103827086B (zh) | 2016-04-13 |
JP2014520891A (ja) | 2014-08-25 |
EP2734501A1 (en) | 2014-05-28 |
BR112014001289A2 (pt) | 2017-01-10 |
CA2842660C (en) | 2019-05-28 |
AU2012283952B2 (en) | 2016-05-19 |
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