CA2017819A1 - Compositions et concentres a base d'huile lubrifiante - Google Patents
Compositions et concentres a base d'huile lubrifianteInfo
- Publication number
- CA2017819A1 CA2017819A1 CA002017819A CA2017819A CA2017819A1 CA 2017819 A1 CA2017819 A1 CA 2017819A1 CA 002017819 A CA002017819 A CA 002017819A CA 2017819 A CA2017819 A CA 2017819A CA 2017819 A1 CA2017819 A1 CA 2017819A1
- Authority
- CA
- Canada
- Prior art keywords
- groups
- lubricating oil
- manganese
- acid
- oil
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 344
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 91
- 239000012141 concentrate Substances 0.000 title claims abstract description 11
- 239000003921 oil Substances 0.000 claims abstract description 165
- -1 amine compound Chemical class 0.000 claims abstract description 151
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 130
- 229910052751 metal Inorganic materials 0.000 claims abstract description 100
- 239000002184 metal Substances 0.000 claims abstract description 100
- 239000011572 manganese Substances 0.000 claims abstract description 89
- 125000001424 substituent group Chemical group 0.000 claims abstract description 63
- 229920000098 polyolefin Polymers 0.000 claims abstract description 62
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 36
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims abstract description 32
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 29
- 150000002697 manganese compounds Chemical class 0.000 claims abstract description 27
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 25
- 150000001733 carboxylic acid esters Chemical class 0.000 claims abstract description 25
- 230000007935 neutral effect Effects 0.000 claims abstract description 21
- 239000003599 detergent Substances 0.000 claims abstract description 16
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 claims abstract description 16
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 13
- 230000001050 lubricating effect Effects 0.000 claims abstract description 12
- 238000002485 combustion reaction Methods 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims description 102
- 150000003839 salts Chemical class 0.000 claims description 72
- 125000004432 carbon atom Chemical group C* 0.000 claims description 62
- 150000003460 sulfonic acids Chemical class 0.000 claims description 52
- 150000007513 acids Chemical class 0.000 claims description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- 150000001412 amines Chemical class 0.000 claims description 37
- 239000000463 material Substances 0.000 claims description 35
- 235000002908 manganese Nutrition 0.000 claims description 32
- 150000002989 phenols Chemical class 0.000 claims description 28
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 26
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
- 150000002696 manganese Chemical class 0.000 claims description 24
- 230000002378 acidificating effect Effects 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 150000001735 carboxylic acids Chemical class 0.000 claims description 19
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 13
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 10
- 150000001340 alkali metals Chemical class 0.000 claims description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000010949 copper Substances 0.000 claims description 8
- 229910052802 copper Inorganic materials 0.000 claims description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 239000011133 lead Substances 0.000 claims description 3
- 238000005461 lubrication Methods 0.000 claims description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 239000011135 tin Substances 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 1
- 229910052750 molybdenum Inorganic materials 0.000 claims 1
- 239000011733 molybdenum Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 abstract description 24
- 230000000996 additive effect Effects 0.000 abstract description 11
- 239000008186 active pharmaceutical agent Substances 0.000 abstract description 8
- 230000003647 oxidation Effects 0.000 abstract description 5
- 238000007254 oxidation reaction Methods 0.000 abstract description 5
- 235000019198 oils Nutrition 0.000 description 158
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 71
- 229920000768 polyamine Polymers 0.000 description 69
- 239000000306 component Substances 0.000 description 68
- 235000019441 ethanol Nutrition 0.000 description 57
- 238000006243 chemical reaction Methods 0.000 description 53
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 47
- 238000000034 method Methods 0.000 description 47
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 45
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 43
- 239000002480 mineral oil Substances 0.000 description 42
- 229940042472 mineral oil Drugs 0.000 description 42
- 235000010446 mineral oil Nutrition 0.000 description 42
- 238000012360 testing method Methods 0.000 description 41
- 239000000047 product Substances 0.000 description 39
- 150000002148 esters Chemical class 0.000 description 38
- 229910052757 nitrogen Inorganic materials 0.000 description 37
- 229960005419 nitrogen Drugs 0.000 description 35
- 239000000243 solution Substances 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000005977 Ethylene Substances 0.000 description 31
- 229940093470 ethylene Drugs 0.000 description 31
- 238000002360 preparation method Methods 0.000 description 31
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 29
- 150000001336 alkenes Chemical class 0.000 description 28
- 239000000314 lubricant Substances 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 26
- 125000000217 alkyl group Chemical group 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 26
- 239000000376 reactant Substances 0.000 description 26
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 25
- 150000001298 alcohols Chemical class 0.000 description 25
- 239000000706 filtrate Substances 0.000 description 25
- 239000002270 dispersing agent Substances 0.000 description 23
- 235000014113 dietary fatty acids Nutrition 0.000 description 22
- 239000000194 fatty acid Substances 0.000 description 22
- 229930195729 fatty acid Natural products 0.000 description 22
- 229930195733 hydrocarbon Natural products 0.000 description 22
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 21
- 125000001931 aliphatic group Chemical group 0.000 description 21
- 125000002947 alkylene group Chemical group 0.000 description 20
- 239000003153 chemical reaction reagent Substances 0.000 description 20
- 150000002430 hydrocarbons Chemical class 0.000 description 20
- 239000000178 monomer Substances 0.000 description 20
- 239000004215 Carbon black (E152) Substances 0.000 description 19
- 229910052698 phosphorus Inorganic materials 0.000 description 19
- 239000000126 substance Substances 0.000 description 19
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 235000014786 phosphorus Nutrition 0.000 description 18
- 239000011574 phosphorus Substances 0.000 description 18
- 239000011701 zinc Substances 0.000 description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 17
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 16
- 229960004592 isopropanol Drugs 0.000 description 16
- 235000011044 succinic acid Nutrition 0.000 description 16
- 239000011593 sulfur Substances 0.000 description 16
- 229910052717 sulfur Inorganic materials 0.000 description 16
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 15
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 14
- 229940044600 maleic anhydride Drugs 0.000 description 14
- 239000004034 viscosity adjusting agent Substances 0.000 description 14
- 238000007664 blowing Methods 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 12
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- 235000017168 chlorine Nutrition 0.000 description 12
- 229940060038 chlorine Drugs 0.000 description 12
- 229910052801 chlorine Inorganic materials 0.000 description 12
- 230000006870 function Effects 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 230000036961 partial effect Effects 0.000 description 12
- 235000019271 petrolatum Nutrition 0.000 description 12
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 12
- 238000007127 saponification reaction Methods 0.000 description 12
- 229940014800 succinic anhydride Drugs 0.000 description 12
- 150000005846 sugar alcohols Polymers 0.000 description 12
- 229910052725 zinc Inorganic materials 0.000 description 12
- 239000011787 zinc oxide Substances 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
- 229920002367 Polyisobutene Polymers 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 11
- 150000004665 fatty acids Chemical class 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 10
- 150000008064 anhydrides Chemical class 0.000 description 10
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 10
- 239000010705 motor oil Substances 0.000 description 10
- 239000012188 paraffin wax Substances 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 10
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 9
- 229940076134 benzene Drugs 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- 239000000446 fuel Substances 0.000 description 9
- 150000007524 organic acids Chemical class 0.000 description 9
- 235000019809 paraffin wax Nutrition 0.000 description 9
- 229940059574 pentaerithrityl Drugs 0.000 description 9
- 150000003444 succinic acids Chemical class 0.000 description 9
- 239000001569 carbon dioxide Substances 0.000 description 8
- 229960004424 carbon dioxide Drugs 0.000 description 8
- 229910002092 carbon dioxide Inorganic materials 0.000 description 8
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000003607 modifier Substances 0.000 description 8
- 235000005985 organic acids Nutrition 0.000 description 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- 150000003751 zinc Chemical class 0.000 description 8
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 230000032050 esterification Effects 0.000 description 7
- 238000005886 esterification reaction Methods 0.000 description 7
- 238000005755 formation reaction Methods 0.000 description 7
- 235000011187 glycerol Nutrition 0.000 description 7
- 229960005150 glycerol Drugs 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 150000002894 organic compounds Chemical class 0.000 description 7
- 150000003017 phosphorus Chemical class 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 150000001447 alkali salts Chemical class 0.000 description 6
- 150000001342 alkaline earth metals Chemical class 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 150000005690 diesters Chemical class 0.000 description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- 150000003949 imides Chemical class 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 6
- 235000021313 oleic acid Nutrition 0.000 description 6
- 150000002924 oxiranes Chemical class 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 150000003138 primary alcohols 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
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000010802 sludge Substances 0.000 description 6
- 229940083608 sodium hydroxide Drugs 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 239000001384 succinic acid Substances 0.000 description 6
- 229910052723 transition metal Inorganic materials 0.000 description 6
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 5
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 239000005642 Oleic acid Substances 0.000 description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 5
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 5
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 5
- 229960004756 ethanol Drugs 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 5
- 150000002763 monocarboxylic acids Chemical class 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000010689 synthetic lubricating oil Substances 0.000 description 5
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 5
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 4
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- 125000001400 nonyl 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])[H] 0.000 description 1
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- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
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- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 1
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- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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- OSMTZRGOBRHZNO-UHFFFAOYSA-N pentyl phenyl hydrogen phosphite Chemical compound CCCCCOP(O)OC1=CC=CC=C1 OSMTZRGOBRHZNO-UHFFFAOYSA-N 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- XNQULTQRGBXLIA-UHFFFAOYSA-O phosphonic anhydride Chemical compound O[P+](O)=O XNQULTQRGBXLIA-UHFFFAOYSA-O 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
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- 229920000151 polyglycol Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
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- 239000005060 rubber Substances 0.000 description 1
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- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
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- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- 229920006029 tetra-polymer Polymers 0.000 description 1
- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical class CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- MQHSFMJHURNQIE-UHFFFAOYSA-N tetrakis(2-ethylhexyl) silicate Chemical compound CCCCC(CC)CO[Si](OCC(CC)CCCC)(OCC(CC)CCCC)OCC(CC)CCCC MQHSFMJHURNQIE-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000007056 transamidation reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 229940113165 trimethylolpropane Drugs 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical class C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229960001296 zinc oxide Drugs 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- USEBTXRETYRZKO-UHFFFAOYSA-L zinc;n,n-dioctylcarbamodithioate Chemical compound [Zn+2].CCCCCCCCN(C([S-])=S)CCCCCCCC.CCCCCCCCN(C([S-])=S)CCCCCCCC USEBTXRETYRZKO-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C10M163/00—Lubricating compositions characterised by the additive being a mixture of a compound of unknown or incompletely defined constitution and a non-macromolecular compound, each of these compounds being essential
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- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
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- C10M129/38—Carboxylic acids; Salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having 8 or more carbon atoms
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- C10M129/92—Carboxylic acids
- C10M129/93—Carboxylic acids having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
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- C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
- C10M129/95—Esters
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- C10M135/10—Sulfonic acids or derivatives thereof
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- C10M137/04—Phosphate esters
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- C10M159/22—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing phenol radicals
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- C10M159/24—Reaction mixtures having an excess of neutralising base, e.g. so-called overbasic or highly basic products containing sulfonic radicals
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- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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- C10M2207/028—Overbased salts thereof
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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
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- C10M2207/122—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms monocarboxylic
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US35959389A | 1989-06-01 | 1989-06-01 | |
US07/359,593 | 1989-06-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2017819A1 true CA2017819A1 (fr) | 1990-12-01 |
Family
ID=23414490
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002017819A Abandoned CA2017819A1 (fr) | 1989-06-01 | 1990-05-30 | Compositions et concentres a base d'huile lubrifiante |
Country Status (14)
Country | Link |
---|---|
EP (1) | EP0433409B1 (fr) |
JP (1) | JPH04500234A (fr) |
CN (1) | CN1024563C (fr) |
AT (1) | ATE124443T1 (fr) |
AU (1) | AU636354B2 (fr) |
BR (1) | BR9006788A (fr) |
CA (1) | CA2017819A1 (fr) |
DE (1) | DE69020516T2 (fr) |
ES (1) | ES2076367T3 (fr) |
FI (1) | FI910472A0 (fr) |
HK (1) | HK12896A (fr) |
IL (1) | IL94555A0 (fr) |
WO (1) | WO1990015124A1 (fr) |
ZA (1) | ZA904214B (fr) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5232616A (en) * | 1990-08-21 | 1993-08-03 | Chevron Research And Technology Company | Lubricating compositions |
US6235688B1 (en) | 1996-05-14 | 2001-05-22 | Chevron Chemical Company Llc | Detergent containing lithium metal having improved dispersancy and deposit control |
US7341447B2 (en) * | 2002-12-06 | 2008-03-11 | Afton Chemical Intangibles | Delivering manganese from a lubricant source into a fuel combustion system |
JP2010285475A (ja) * | 2009-06-09 | 2010-12-24 | Yushiro Chem Ind Co Ltd | 潤滑油組成物 |
JP5875612B2 (ja) * | 2013-02-28 | 2016-03-02 | ミネベア株式会社 | 樹脂潤滑用グリース組成物を塗布した樹脂歯車装置 |
CN107312031B (zh) * | 2017-06-22 | 2020-03-10 | 新乡市瑞丰新材料股份有限公司 | 一种二异辛基二硫代磷酸锌盐的制备方法 |
WO2019224647A1 (fr) * | 2018-05-25 | 2019-11-28 | Chevron U.S.A. Inc. | Procédé de prévention ou de réduction de pré-allumage à faible vitesse dans des moteurs à allumage commandé à injection directe avec un lubrifiant contenant du manganèse |
GB2585388B (en) * | 2019-07-08 | 2023-11-15 | Cataclean Global Ltd | Composition for cleaning combustion engine systems |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4234435A (en) * | 1979-02-23 | 1980-11-18 | The Lubrizol Corporation | Novel carboxylic acid acylating agents, derivatives thereof, concentrate and lubricant compositions containing the same, and processes for their preparation |
FR2469449A1 (fr) * | 1979-11-07 | 1981-05-22 | Lubrizol Corp | Additifs de lubrification comprenant un alkylphenol sulfure et un agent dispersant de haut poids moleculaire |
CA1284145C (fr) * | 1985-09-19 | 1991-05-14 | David E. Ripple | Produits et methodes de lubrification pour moteurs diesel |
CA1290314C (fr) * | 1986-01-21 | 1991-10-08 | David E. Ripple | Composition lubrifiante a teneur de metaux de transition regulateurs de l'indice de viscosite |
-
1990
- 1990-05-17 AU AU57465/90A patent/AU636354B2/en not_active Ceased
- 1990-05-17 BR BR909006788A patent/BR9006788A/pt unknown
- 1990-05-17 DE DE69020516T patent/DE69020516T2/de not_active Expired - Fee Related
- 1990-05-17 ES ES90908812T patent/ES2076367T3/es not_active Expired - Lifetime
- 1990-05-17 EP EP90908812A patent/EP0433409B1/fr not_active Expired - Lifetime
- 1990-05-17 WO PCT/US1990/002815 patent/WO1990015124A1/fr active IP Right Grant
- 1990-05-17 AT AT90908812T patent/ATE124443T1/de not_active IP Right Cessation
- 1990-05-17 JP JP2508523A patent/JPH04500234A/ja active Pending
- 1990-05-29 IL IL94555A patent/IL94555A0/xx not_active IP Right Cessation
- 1990-05-30 CA CA002017819A patent/CA2017819A1/fr not_active Abandoned
- 1990-06-01 ZA ZA904214A patent/ZA904214B/xx unknown
- 1990-06-01 CN CN90104063A patent/CN1024563C/zh not_active Expired - Fee Related
-
1991
- 1991-01-31 FI FI910472A patent/FI910472A0/fi not_active Application Discontinuation
-
1996
- 1996-01-25 HK HK12896A patent/HK12896A/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
WO1990015124A1 (fr) | 1990-12-13 |
ZA904214B (en) | 1991-05-29 |
CN1049679A (zh) | 1991-03-06 |
JPH04500234A (ja) | 1992-01-16 |
DE69020516T2 (de) | 1995-11-30 |
ES2076367T3 (es) | 1995-11-01 |
AU5746590A (en) | 1991-01-07 |
DE69020516D1 (de) | 1995-08-03 |
FI910472A0 (fi) | 1991-01-31 |
CN1024563C (zh) | 1994-05-18 |
EP0433409B1 (fr) | 1995-06-28 |
BR9006788A (pt) | 1991-08-06 |
ATE124443T1 (de) | 1995-07-15 |
AU636354B2 (en) | 1993-04-29 |
IL94555A0 (en) | 1991-03-10 |
EP0433409A1 (fr) | 1991-06-26 |
HK12896A (en) | 1996-02-02 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FZDE | Discontinued |