TW201247684A - Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same - Google Patents
Molybdenum dialkyldithiocarbamate compositions and lubricating compositions containing the same Download PDFInfo
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- TW201247684A TW201247684A TW101110324A TW101110324A TW201247684A TW 201247684 A TW201247684 A TW 201247684A TW 101110324 A TW101110324 A TW 101110324A TW 101110324 A TW101110324 A TW 101110324A TW 201247684 A TW201247684 A TW 201247684A
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- acid
- molybdenum
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- butene
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- 239000000203 mixture Substances 0.000 title claims abstract description 113
- 230000001050 lubricating effect Effects 0.000 title claims description 21
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 title claims description 8
- 229910052750 molybdenum Inorganic materials 0.000 title claims description 8
- 239000011733 molybdenum Substances 0.000 title claims description 8
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims abstract description 29
- 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 claims abstract description 8
- PZFYOFFTIYJCEW-UHFFFAOYSA-N n-tridecyltridecan-1-amine Chemical compound CCCCCCCCCCCCCNCCCCCCCCCCCCC PZFYOFFTIYJCEW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
- -1 dithiol bismuth citrate Chemical class 0.000 claims description 49
- 239000002253 acid Substances 0.000 claims description 30
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 13
- 239000002994 raw material Substances 0.000 claims description 11
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 10
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 5
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 5
- 239000012990 dithiocarbamate Substances 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- KVIRMZZRSGWLNY-UHFFFAOYSA-J N,N-di(tridecyl)carbamodithioate molybdenum(4+) Chemical compound C(CCCCCCCCCCCC)N(C([S-])=S)CCCCCCCCCCCCC.[Mo+4].C(CCCCCCCCCCCC)N(C([S-])=S)CCCCCCCCCCCCC.C(CCCCCCCCCCCC)N(C([S-])=S)CCCCCCCCCCCCC.C(CCCCCCCCCCCC)N(C([S-])=S)CCCCCCCCCCCCC KVIRMZZRSGWLNY-UHFFFAOYSA-J 0.000 claims 1
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 claims 1
- GKEVEJUAVWUHRF-UHFFFAOYSA-N di(tridecyl)carbamodithioic acid Chemical compound CCCCCCCCCCCCCN(C(S)=S)CCCCCCCCCCCCC GKEVEJUAVWUHRF-UHFFFAOYSA-N 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 claims 1
- 229960003495 thiamine Drugs 0.000 claims 1
- 235000019157 thiamine Nutrition 0.000 claims 1
- 239000011721 thiamine Substances 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 description 31
- 239000002270 dispersing agent Substances 0.000 description 27
- 239000003921 oil Substances 0.000 description 25
- 235000019198 oils Nutrition 0.000 description 24
- 150000003839 salts Chemical class 0.000 description 24
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 19
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 19
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 17
- 239000003963 antioxidant agent Substances 0.000 description 16
- 239000000314 lubricant Substances 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 229920000768 polyamine Polymers 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 150000001336 alkenes Chemical class 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 10
- 239000010949 copper Substances 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 10
- 229930195729 fatty acid Natural products 0.000 description 10
- 239000000194 fatty acid Substances 0.000 description 10
- 238000001556 precipitation Methods 0.000 description 10
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 9
- 239000004327 boric acid Substances 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
- 239000003607 modifier Substances 0.000 description 9
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 9
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- 239000010705 motor oil Substances 0.000 description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000000052 vinegar Substances 0.000 description 7
- 235000021419 vinegar Nutrition 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000004034 viscosity adjusting agent Substances 0.000 description 6
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000005352 clarification Methods 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000002518 antifoaming agent Substances 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 239000013530 defoamer Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 4
- 238000006146 oximation reaction Methods 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- 150000003751 zinc Chemical class 0.000 description 4
- YOFPVMWVLDSWKR-UHFFFAOYSA-N 11-methyl-n-(11-methyldodecyl)dodecan-1-amine Chemical compound CC(C)CCCCCCCCCCNCCCCCCCCCCC(C)C YOFPVMWVLDSWKR-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 239000002199 base oil Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 230000000994 depressogenic effect Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 238000007037 hydroformylation reaction Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000010687 lubricating oil Substances 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 238000006268 reductive amination reaction Methods 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229910001868 water Inorganic materials 0.000 description 3
- NGKIIKNJVVBNNE-UHFFFAOYSA-N 11-methyldodecan-1-amine Chemical compound CC(C)CCCCCCCCCCN NGKIIKNJVVBNNE-UHFFFAOYSA-N 0.000 description 2
- JLZIIHMTTRXXIN-UHFFFAOYSA-N 2-(2-hydroxy-4-methoxybenzoyl)benzoic acid Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JLZIIHMTTRXXIN-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- 102100039496 Choline transporter-like protein 4 Human genes 0.000 description 2
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 101000889282 Homo sapiens Choline transporter-like protein 4 Proteins 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 230000006315 carbonylation Effects 0.000 description 2
- 238000005810 carbonylation reaction Methods 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000005265 dialkylamine group Chemical group 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000010642 eucalyptus oil Substances 0.000 description 2
- 229940044949 eucalyptus oil Drugs 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000002530 phenolic antioxidant Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920001281 polyalkylene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229940116351 sebacate Drugs 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- JMUOXOJMXILBTE-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-4-yl) octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 JMUOXOJMXILBTE-UHFFFAOYSA-N 0.000 description 1
- ZGZUKKMFYTUYHA-HNNXBMFYSA-N (2s)-2-amino-3-(4-phenylmethoxyphenyl)propane-1-thiol Chemical group C1=CC(C[C@@H](CS)N)=CC=C1OCC1=CC=CC=C1 ZGZUKKMFYTUYHA-HNNXBMFYSA-N 0.000 description 1
- ZJGSVSYBKAZJGP-KVVVOXFISA-N (z)-octadec-9-enoic acid;zinc Chemical group [Zn].CCCCCCCC\C=C/CCCCCCCC(O)=O ZJGSVSYBKAZJGP-KVVVOXFISA-N 0.000 description 1
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- NQZZYWZJORWXCL-UHFFFAOYSA-N 1-tert-butylcyclohexa-2,4-dien-1-ol Chemical class CC(C)(C)C1(O)CC=CC=C1 NQZZYWZJORWXCL-UHFFFAOYSA-N 0.000 description 1
- GRWZFPFQSHTXHM-UHFFFAOYSA-N 11-methyldodec-1-ene Chemical group CC(C)CCCCCCCCC=C GRWZFPFQSHTXHM-UHFFFAOYSA-N 0.000 description 1
- OUFCBJZGDJFSIK-UHFFFAOYSA-N 11-methyldodecanal Chemical compound CC(C)CCCCCCCCCC=O OUFCBJZGDJFSIK-UHFFFAOYSA-N 0.000 description 1
- LUACOWBTSAPURU-UHFFFAOYSA-N 2-(2-methylbutan-2-yl)anthracene Chemical compound C1=CC=CC2=CC3=CC(C(C)(C)CC)=CC=C3C=C21 LUACOWBTSAPURU-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- QUKGVEYDVQUXJG-UHFFFAOYSA-N 2-octyl-1h-pyrrole Chemical compound CCCCCCCCC1=CC=CN1 QUKGVEYDVQUXJG-UHFFFAOYSA-N 0.000 description 1
- OCVLSHAVSIYKLI-UHFFFAOYSA-N 3h-1,3-thiazole-2-thione Chemical compound SC1=NC=CS1 OCVLSHAVSIYKLI-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- JATLSJIWVNJRMN-UHFFFAOYSA-N 4-dodecyl-2h-triazole Chemical compound CCCCCCCCCCCCC1=CNN=N1 JATLSJIWVNJRMN-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/12—Thio-acids; Thiocyanates; Derivatives thereof
- C10M135/14—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond
- C10M135/18—Thio-acids; Thiocyanates; Derivatives thereof having a carbon-to-sulfur double bond thiocarbamic type, e.g. containing the groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F11/00—Compounds containing elements of Groups 6 or 16 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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Description
v 201247684 dithiocarbamate composition from the DTDA intermediate. The resulting molybdenum di thiocarbamate composition are according to formula (1), wherein Ri to R4 are Ch-Ch isoalkyl groups, and X represents oxygen and/or sulfur atoms, and Ri to R4 comprise, on average, greater than 98% Cu:
F ,Ν· ii/ \ii
SM -Mo
Mo-S
N
R
X
3 4 R R
%)/ 1 /V 四、指定代表圖: (一) 本案指定代表圖為:第(1)圖 無 (二) 本代表圖之元件符號簡單說明 五 、本案若有化學式時,請揭示最能顯示發明特徵的化學式
R 卫,
R
X R, (1) 六、發明說明: 【發明所屬之技術領域】 硫胺基 本發明係有關於具良好油溶性之新穎二院美 曱酸鉬組成物。 【先前技術】 2 201247684 如式(1)所示之二烷基二硫 ,^ "如基甲酸鉬組成物(MoDTC) 、且成物,其中L至r4為異十= 丁 —花基或Cn-Cl4異烷基的混合 物’且X為氧及/或硫原子,立為 .^ 、馬已知的潤滑油添加劑,具 有抗摩擦、抗磨、與抗氧化的特性:
R ί
,N__u_s—M〇 Mo \ / X X X y 〇11/ \ιί s—U—n"
卫 v R (1) 4 雖然式⑴MoDTC組成物具有良好的抗摩擦、抗磨與抗 飞特性,但其在高黏度系數油及/或低溫下的溶解度很 低,導致陰霾、渾濁或沉澱物的形成,會降低潤滑劑的效 果。例如,在美國專利號5,627,146與6,245 725中,-心 ,ί.教不以一 2乙基己基胺與二-異十三烷基胺(DTM) 製備之MoDTC'組成物比起僅以DTDA製備之M〇DTQ成物, 具有更好的油溶性。 J在本文中,本發明人發現可利用特定的DTDA組成物來 製備具良好油溶性的M〇DTC組成物。特別S,本發明人發 現利用含有大量(>5G%)2_丁烯與少量卜丁稀及/或異丁稀 之丁烯原料之寡合所生產的M〇DTC組成物,其具有平均大 於98%的Cl3作為,比起利用其它習知麵所生產的 MoDTC,可提升在高黏度系數油及/或低溫下的油溶性特 別疋,二-Ch-u-異烷基、富含Cu胺類、.與bis(Cii_c]4,支 鏈與支鏈烷基)胺類。應注意的是,二_Cii異烷基、富含 Cn胺類、與bls(Cn-CH’支鏈與支鏈烷基)胺類也通常被 稱為DTDA,且具有平均大於73%的Cu,可作為R取代基。 201247684 【發明内容】 如流程1所不,DTDA組成物的基本結構為低碳烯烴原 料,其主要由丁烯或丙烯氣體所組成。為了製備dtda烷基 鏈,將s含丁烯或丙烯之低碳烯烴原料寡聚合成同分異構 之烯烴原料,其通常分別被稱為丁烯三聚體及丙烯四聚 體。此高碳烯烴組成物在鈷或鍺催化劑的存在下,經由烯 烴與一氧化碳及氩反應之氫甲醯化反應,轉換為Ci3或富含 Cu之醇及/或醛。在工業規模時,烯烴之氫甲醯化被稱為 羰基合成或羰基化過程,且獲得之醇類組成物一般被稱為 幾基醇。在傳統技術上,Cl3及富含^之幾基醇—般被稱 為異十三醇》在流程的最後步驟中,利用已知的還原胺化 反應將醇及/或醛類組成物轉換為DTDA。在本發明中,利 用含有大量(>50%)2-丁烯與少量卜丁烯及/或異丁烯之丁 烯原料進行一系列的化學轉化以形成M〇DTCs。 本發明亦有關於一種製備新穎二硫胺基甲酸鉬組成物 的方法,以及有關於含有一有效量二異十三烷基二硫胺基 ^ (molybdenum di-isotridecyIdithiocarbamate)^ 潤e組成物。本發明添加劑具有良好的溶解度特別是在 辜度系數油及/或低溫下。尤其是,本發明有關於利用丁 烯何生之DTDA所製備之新穎二烷基二硫胺基甲酸鉬,其具 有平均大於98%的c13 ’作為R基的一部分。應注意的是, 本發明之MoDTC組成物可由M〇DTC分子所組成,其R基結 構可能有所不同’但整體組成物具有平均大於98%的C13。 201247684 【實施方式】 本發明之MoDTC組成物可以任何習知方法製備例 如,但不限於,三氧化鉬、水、-护 ^ 一硫化碳與二烷胺基的反 應。其它方法可參照美國專利號3 356,7〇2、3,5〇9,〇51、 4, 098, 705 ' 4, 1 78, 258 ' 5 631 qi〇 〇,n 。a,Ddi,zid、7,3l 2,348、7,524,799 與 7, 858, 655。 本發明之特徵在於二烧胺基起始原料。特別是,此胺 基須為源自於丁烯氣體原料之DTDA,其為由cis_2_丁烯、 trans-2-丁稀、卜丁稀與異丁稀組成之C4烯烴混合物。應 注意的是’其它烯烴,例如乙烯,丙烯和戊烯可存在於 此原料中。為了形成異_十三烷基鏈(is〇七idee” chains)’首先將丁稀寡聚合為三_丁基’其為一稀烴分子 同分異構物之混合物。在丁烯烯寡聚合後,此三聚體經由 氫甲醯化反應或羰基化作用被轉換為異-十三碳醛 (1S〇-tridecanal)及/或異-十三烷基醇(iso_ tridecanol),此為化學工業之習知技術。最後步驟為利用 還原胺化反應將異-十三碳醛及/或異_十三醇轉換為 DTDA。在還原胺化反應中,醛及/或醇類組成物與氨、一級 胺或二級胺反應以形成亞胺中間產物,其接著經由催化氫 化反應分別被還原成一級、二級及三級胺。以2_烷基胺(如 二-十三烷基胺)為例,胺化劑為氨與異—十三碳醛及/或異一 十三醇,首先形成一級胺或異_十三烷基胺 (isotridecylamine)。接著,異_十三烷基胺與十三碳醛及 5 201247684 /或異-十三醇反應以形成相對應之二-異十三烷基胺 (dusotndecyamine),接著可再次與異—十三碳醛及/或 異-十三醇反應以形成三-異十三院基胺。依據反應批次與 其它反應條件,如壓力、溫度與反應時間,控制此過程以 形成DTDA。 為增加抗氧化性、抗磨性與抗摩擦性,可將有效量之 本發明組成物以習知方法合併至潤滑組成物中,以產生良 好的特在較佳實施例中,為潤滑組成物總重的約〇 . 〇 J 至3.〇重量%,較佳為約01_1%,最佳為約〇 25_5%。 被使用作為潤滑媒介的基底油(base 〇i is)為一般用 於汽車和工業的油類’例如’汽輪機油、液壓油、齒輪油、 曲轴箱機油與柴油。天然基底油包括,礦物油 oils)、礦物油(petroleum〇ils)、石蠟油與植物油。此基 底油也可選擇源自於石油烴及合成的油類。此合成油可擇 自於醋類油(如矽酸鹽醋,季戊四醇醋與羧酸醋)、氫化礦 物油、矽油、矽烷、聚矽氧烷、烯聚合物、與聚乙二醇醚: 此潤滑組成物選擇性地含有必須成分以製備此組成 物,例如,分散劑、乳化劑、與黏度改良劑 依據潤滑油 的使用目的,可添加其它功能性添加劑以促進潤滑劑某一 特定性質。此潤滑組成物也可含有下列1複數個添加劑: 1. 硼酸及/或非硼酸分散劑 2. 其他抗氧化劑 3. 密封膨脹組成物 4.摩擦調整劑 6 201247684 5.極壓/抗磨劑 6 ·黏度調整劑 7. 降凝劑(Pour p〇int depressants) 8. 界面活性劑 9. 磷酸鹽 10. 消泡劑 11 ·防錢劑 12.銅緩蝕劑 1.硼酸及/或非硼酸分散劑 非硼酸無灰分散劑可合併至最後的液體組成物中,其 含量為無油基質中的1 〇重量%以上。後文列出各種習知的 無灰分散劑,也包括硼酸無灰分散劑。 (A)幾酸類分散劑”為含至少約3 4,較佳至少約5 4 個碳原子的氫曱醯化劑(酸、酐、酯等)與含氮化合物(例 如,胺)、有機羥基(例如,含有一元醇與多元醇的脂肪族 化合物’或含有酚類與萘酚的芳香族化合物)、及/或鹼性 無機物質的反應產物。此反應產物包括羧酸醯化劑的醯亞 胺、醯胺、與酯類的反應產物。這些物質包括琥珀醯亞胺 分散劑與羧酸酯分散劑。羧酸醯化劑包括烷基琥珀酸與 酐’其中烧基為聚丁基單元、脂肪酸、異脂肪酸 (isoal iphat ic acids)(8-曱基硬脂酸)、二聚酸、額外之 二元叛酸、不飽和脂肪酸與不飽和竣酸之額外(4 + 2與2 + 2) 產物、三聚酸、額外之三羧酸(例如,Empoi® 1 040、 Hystrene® 5460與Unidyme® 60)、以及烴基經取代之羧酸 201247684 醯化劑(源自於烯烴(olefins)及/或聚烯烴 (po 1 ya 1 kenes))。在一較佳實施例中,此羧酸醯化劑為脂 肪酸。脂肪酸一般包含約8個以上至約30個,或約12個 以上至約24個碳原子。羧酸醯化劑可參照美國專利號 2, 444, 328、3, 219, 666 與 4, 234, 435,其所揭露的内容皆 屬於本發明的範鳴。胺可為單胺(monoamine)或多胺 (po 1 yamine)。單胺一般具有至少一含有1個至約24個碳 原子的烴基,其帶有1至約丨2個碳原子。單胺包括脂肪 (Cs-C3G)胺、一級鱗胺(primary ether amines)、三級脂肪 一級胺(tertiary-aliphatic primary amines)、經胺(一 級、二級或三級院醇胺)、醚_(羥烴)胺、與羥烴胺。多胺 包括烷氧基二胺,脂肪二胺' 烯多胺(乙烯多胺)、含有羥 基的多胺、5^環氧稀多胺、縮合多胺(至少一經基化合物與 至少一含有至少 級或二級胺基之多胺反應物之間的縮 合反應)、與雜環多胺。可使用的胺基酸包括如美國專利號 4, 234’435與5, 230, 714中所揭露的胺基酸,其所揭露的 内容皆屬於本發明的範疇。“羧酸類分散劑”可參照英國 專利 1,306, 529 以及美國專利號 3, 219, 666、3, 316, 177、 3,340,281、3,351,552、3,381,022 ' 3’433,744、 3,444,170、3,467,668、3,501,405、3’542,68〇、 3’ 576, 743、3, 632, 5U、4, 234, 435、與 Re 26, 433,其所 揭露的分散劑皆屬於本發明的範脅。 (B)胺類分散劑”為較高分子量脂肪族或脂環鹵化 物與胺’較佳為聚亞烷多胺的反應產物。胺類分散劑的例 8 201247684 子可參照美國專利號 3,275,554、3, 438, 757、3, 454, 與3, 5 65, 804,其所揭露的分散劑皆屬於本發明的範鳴。 (C) “Mannich分散劑”為含有至少約3〇個碳原子烷 基之烧基紛與酸類(特別是曱酸)和胺(特別是聚亞烧基多 胺)的反應產物。美國專利號3,036,003、3,236 770、 3, 414, 347、3, 448, 047、346, 172、3, 539, 633、3, 586, 629、 3’ 591’ 598、3, 634, 51 5、3, 725, 480 ' 與 3, 726, 882 中所揭 露的物質皆屬於本發明分散劑的範缚。 (D) 經處理之分散劑來自於將羧酸類、胺類或 分散劑與試劑,如尿素、硫脲、二硫化碳、乙醛、酮、羧 酸、烴經取代之丁二酸酐、腈、環氧化合物、硼化物、磷 化物、鉬化合物、鎢化合物或其類似物反應所獲得。美國 專利號 3,200,107、3,282,955、3 367 943、3 513 〇93、 3’639’242、3,649,659、3,442,808、3,455,832、 3,579,450、3’600,372、3,702,757、3, 708,422、 4, 259’ 194、4’ 259’ 195、4, 263, 152、4, 265, 773、7, 858, 565 與7, 879’777其所揭露的分散劑皆屬於本發明的範疇。 (E) 咼分子分散劑為油溶單體,如癸甲基丙烯酸、乙烯 基癸喊、與含極性取代基之單體的高分子烯㉟,如胺烧基 丙烯酸酯、或丙烯醯胺與聚氧乙烯經取代之丙烯酸酯的互 聚物。间分子分散劑揭露於美國專利號3, 329, 、 3’449’250、3’51 9,656 ' 3 666 73〇、3 687 849 與 3’702, 300,所揭露的分散劑與無灰分散劑皆屬於本發明的 範<#。 201247684 棚酸分散劑揭露於美國專利號3, 〇87, 936與 3,2 5 4,0 2 5,其揭露的硼酸分散劑皆屬於本發明的範疇。 其它可能的分散劑添加劑揭露於美國專利5,丨98, 133 與4, 857, 214 ’其所揭露的内容皆屬於本發明的範疇。這 些專利的分散劑包括烯基琥珀醯亞胺或丁二醯亞胺無灰分 散劑與磷酯或含磷無機酸或酸酐與硼化合物的反應產物。 2.其它抗氧化劑 若有需要’可於本發明中使用其它抗氧化劑。一般的 抗氧化劑包括位阻酚類抗氧化劑(hindered phen〇Hc antioxidants)、二級芳香胺抗氧化劑、位阻胺類抗氧化 劑、硫化酚類抗氧化劑、油溶性銅的化合物、含磷抗氧化 劑、有機硫化物,二硫化物與聚硫化物及其類似物。 位阻酚類抗氧化劑包括鄰烷基酚類化合物,例如,2, 6_
-苯盼、2,4- 二曱基-6-叔-苯紛、4-(N,N -二甲Jt各m «、《 Λ
個或複數個單核酚類化合物的混合物。
I bis(2-叔-戊基-〇-對曱盼)、 便用。亞甲基橋聯化合物 I 〇-對甲酚)、4,4’-亞曱 2’2亞曱基bis(4-甲基 10 201247684 +叔-苯盼)、4,4’_亞?基bis(26_二—叔一笨⑹與類似 化合物。較佳為亞甲基橋聯院基盼之混合物,如美國專利 號3, 211,652所示,其所揭露的内容皆屬於本發明的範鳴。 胺類抗氧化劑,特別是油溶性芳香族二級胺也可用於 本發明之組錢之巾。儘管較佳為芳香族二級胺,但也可 使用芳香族二級多胺。芳香族二級胺包括二苯胺、含丄或 2個大於^固碳原子之燒基取代基的貌基二苯胺、苯基 -石-萘胺、苯基-P-萘胺、含i或2個大於16個碳原子之 烷基或芳烷基之烷基或芳烷基經取代之笨基_石_萘胺、含 1或2個大於16個兔原子之烧基或芳燒基之炫基或芳烧基 經取代之苯基-P-萘胺,及其類似化合物。 較佳之芳香族胺類抗氧化劑為烷基化二苯胺,其通式 R5-C6H4-NH-C6H4-R6 (2) 其中R5為一具有8至12個碳原子(更佳為8或9碳原子) 之烷基(較佳為一支鏈烷基),XR6為一氫原子或一具有8 至12個碳原子(更佳為8或9碳原子)之烷基(較佳為一支 鏈烷基)最佳R與R6相同。一較佳化合物為市售商品, 如NaUgalube® 438L,其主要為44,_二壬基二苯胺(如, bis(4 —壬基酚)(胺)),壬基為支鏈。 党阻胺基為另一種類型的胺類抗氧化劑,其可與二種 主要類型’嘧啶和哌啶’使用於本發明之組成物中。相關 内容已詳述於前文與美國專利號5, 073, 278、5, 273, 669與 5’ 268,113 較佳之位阻胺類包括 4_stear〇y 1 〇Xy_2, 2, 6, 11 201247684 四甲基0底咬(4-stearoyloxy-2,2,6,6-tetramethylpiperidine) 與十二烧基- N- (2,2,6,6,-四甲基- 4-0底0定)琥珀酸、Cytec 公司市售之 Cyasorb® UV-3853 與 Cyasorb® UV-3581、二 (2, 2, 6, 6-四曱基哌啶-4-基)癸二酸酯與二(1,2, 2, 6, 6-五 甲基0底°定-4-yl)癸二酸酯,Songwon 公司市售之
Songlighl:® 7700 與 Songlight® 2920LQ、與 bis(l-辛氧 基_2, 2, 6,-四曱基- 4-°瓜咬)癸二酸醋,Ciba公司市售之 Tinuviη® 123。 其它較佳可使用於本發明組成物之抗氧化劑,為一或 複數個液體’特別是’硫化酚類化合物,例如,較佳將一 氯化硫與酚類液體混合物反應製備--酚類混合物至少約5〇 重量%由一或複數個反應物組成,受阻酚類—按比例提供每 莫耳反應物之約0 · 3至0 · 7 g —氣化硫’使位阻盼類產生一 液體產物。一般用於製備此液體產物之盼類混合物包括含 有約75重量%之2,6-二-叔-笨酚、約1〇重量%之2_叔_苯 酚、約13重量%之2,4,6-三_叔-苯酚、及約2重量%之24_ 二-叔-苯酚的混合物。此反應為放熱反應,因此較佳將溫 度控制在約15°C至約70°C,最佳介於約4(rc至約6〇<1(:。 其它可使用之抗氧化劑類型為2 2 4_三甲基_丨2_ 羥基喹啉(TMDQ)聚合物與含有芳香終端單元Ur〇matize terminal units)之同源物,例如可參照美國專利; 6, 235, 686,其所揭露的内容皆屬於本發明的範疇。 可使用之抗氧化劑可為含亞甲美h· , _ X τ丞bisC—烷基二硫胺; 甲酸酿)的硫化物’其中烧基含有…個碳原子之物質· 12 201247684 例如,亞甲某_ f - -p f . 一基—硫胺基甲酸酯)為R. T. Vanderbilt 股份有限公司的市售Vanlube 7723φ。 °使用不同抗氧化劑的混合物。一適合的混合物由 _。乂 3種不同位阻第三丁基一元酚之油溶混合物,其為 25C的液體;(丨丨)至少? 3種不同位阻第三丁基亞甲基橋聯 多齡·之油溶混合物.w s 、 ’乂及(in)至少bis(4-烷基苯)胺,其 中烧基為具8至12個碳原子之支鏈烧基所組成,⑴、(ii) 與(111)的重量比為,每重量份的(iii)含有3· 5至5.0份 的()〇· 9至1. 2份的g ’如美國專利號5, 328, 所 述’其所揭露的内容皆屬於本發明的範疇。 ’、匕較佳之抗氧化劑如美國專利號4, L 所示, 其所揭露的内容皆屬於本發明的範嘴。 3 _ e封膨脹組成物 以習知技術將組成物維持密封柔軟特性。較佳之密封 膨脹组成物為異癸基環丁艰。此密封膨脹組成物在組成物 (M-3wt%,取代之3 —燒氧基仙揭示於美國 專利號4,〇29,587,其所揭露的内容皆屬於本發明的範_。 4.摩擦調整劑 摩擦調整劑為此技藝人士所習知。可使用之摩擦調整 劑如美國專利號4,792,41 D所示,其所揭露的内容皆屬於 本發明的範嘴。美國專利號5,1 1 0,488揭示脂肪酸的金屬 鹽類’特別是鋅鹽’且其所揭露的内容皆屬於本發明的範 嗜…可使用的摩擦調整劑包括脂肪碌酸8旨、脂肪酸酿胺, 脂肪環氧化物’硼酸脂肪酸環氧化物、脂肪胺、甘油醋、 13 201247684 硼酸甘油酯烷氧基化脂肪胺、烷氧基硼酸脂肪胺、脂肪酸 金屬鹽類、硫化烯烴、脂肪酸咪唑啉、二硫胺基甲酸鉬(例 如,美國專利號4, 259, 254,所揭露的内容屬於本發明的 範疇)、鉬酸酯(例如,美國專利號5, 1 37, 647與 4, 889, 647,所揭露的内容皆屬於本發明的範疇)、含硫提 供者之鉬酸胺(例如,美國專利號4, 164,473),及其混合。 較佳之摩擦調整劑為一硼酸脂肪酸環氧化物,如前文 所述之硼含量。摩擦調整劑較佳在組成物中佔〇 l_i〇重量 /〇,且可為單一摩擦調整劑或二或複數個的組合。 摩擦調整劑也包括脂肪酸的金屬鹽類。可使用之之陽 離子較佳為辞,鎮’㉝’納和任何其他的驗或驗土金屬。 此鹽類可藉由在每等量胺下含有過量之陽離子為以具有高 鹼陡。此過量的陽離子接著可經二氧化碳處理以形成碳酸 ^可使用一適當鹽類與酸反應形成鹽類來製備此金屬鹽 類,且在適當情況添加二氧化碳至反應混合物中以形成任 何陽離子的碳酸鹽,陽離子含量超出形成鹽類之所需。一 較佳之摩擦調整劑為鋅油酸。 5.極壓/抗磨劑 可添加二烷基二硫代磷酸琥珀酸鹽以提供抗磨保護。 車乂佳可添加鋅鹽作為二烴基二硫代磷酸的鋅鹽,其如下式 所示: 201247684 其中R7與Re可為相同或不同的烴基,其含有1至18 個,較佳2至1 2個碳原子,且含有複數個基團,如烷基、 烯基、芳基、芳烷基、烷芳基及環狀脂肪基團。特別是, 較佳R?與R8為2至8個碳原子的烷基。因此,此基團可為, 例如,乙基、η-丙基、i-丙基、n_丁基、卜丁基、sec-丁 基、戊基、η-己基、i-己基、n_辛基、癸基、十二烷基、 十八烷基、2-乙基己基、苯基、丁基笨基、環己基、甲基 環戊基、丙烯基、丁烯基。為了獲得油溶性,二硫代磷酸 中的總碳原子(如R與R’)量一般為約5或或更多。 此外,在潤滑組成物中也包括與鋅鹽相同重量百分比 之二丁基磷酸氫(DBPH)、三苯基一硫代磷酸鹽、以及將二 丁基胺、二硫化碳與丙烯酸曱酯反應生成之硫代氨基甲醆 酯,以提供抗磨/極壓特性。硫化氨基甲酸酯揭露於美國專 利號4, 758, 362 ’且含磷金屬鹽類揭露於美國專利號 4, 466’ 894。兩專利所揭露的内容皆屬於本發明的範疇。銻 或錯鹽也可用於極壓。較佳的鹽類為二硫代氨基甲酸鹽 類,例如二硫代氨基甲酸銻。 6.黏度調整劑 黏度調整劑(VM)與分散黏度調整劑(DVM)已為習知。例 如,VMs與DVMs可為聚甲基丙烯酸酯、聚丙烯酸酯、聚烯 烴、苯乙烯-順丁烯酯共聚物,與類似的聚合物,包括同聚 物、共聚物與接枝共聚物。各種黏度調整劑可見於美國專 利號 5, 1 57, 088、5, 256, 752 與 5, 395, 539,所揭露的内容 皆屬於本發明的範疇。此VMs及/或DVMs較佳以大於} 〇重 15 201247684 量%的量合併至完整的配方組合物。 7. 降凝劑(PPD) 這些成分特別用於改善潤滑油的低溫特性。較佳之降 凝劑為烷基萘。降凝劑如美國專利號4, 與 4, 753’ 745所示’其所揭露的内容皆屬於本發明的範鳴。 PPDs —般添加至潤滑組成物中以降低低溫下的黏度與低剪 切率。降凝劑的使用量較佳為〇. h5wt%。用以達到低溫、 潤滑液之低低剪切速率流變的測試例子包括astm D97(pour point)、ASTM D2983(布氏黏度)、D4684(微型旋 轉黏度計)與 D5133(Scanning Brookfield)。 8. 界面活性劑 潤滑組成物在許多例子中也較佳含有界面活性劑。本 發明中所使用之界面活性劑較佳為有機酸之金屬鹽類。界 面活性劑之有機酸部分較佳為磺酸、缓酸、盼鹽或水揚酸Y 界面活性劑的金屬部分較佳為鹼或鹼土金屬。較佳的金屬 為納、弼、卸、與鎂。界面活性劑較佳為過驗,表示金屬 含量超出形成中性金屬鹽類所需的量。 過量之有貞鹽較佳為f質上具有冑油特性的確酸睡 類’且其由有機物質所形成。有機錢鹽類在潤滑劑及界 面活性劑領域中為習知物質。此罐酸鹽化合物較佳含有平 均約1〇至約4°個碳原子’更佳約12至約36個碳原子, 且最佳約14至3 2個碳原子。151掸、 厌原于冋樣地,酚鹽(phenates)、 草酸鹽(crates)與敌酸較佳實質上具有親油特性。 雖然本發明之碳原子可為芳 香族或石蠟類形態,其較 16 201247684 佳可使用烷基芳香故缸 甘知頬。雖然可使用萘類的物質,若 族較佳為苯基 貝1一方晋 因此,特別赵杜立、、 βο 又佳成分為過鹼單磺酸烷基苯,且較佳為 早烧基苯。炫_其 土本口P分較佳來自於底渣(still b〇u〇m sources)及單或二栌1 &入 70基化。物。應可相信,在本發明的整 體特性上,料基料族優於二烧基芳香族。 、=本發明中’較佳可使用單院基芳香族(苯)的混合物 以獲仔單烧基鹽類(苯續酸鹽)。混合物中主要部分包含丙 歸聚合物,作為燒基來源,可提升鹽類的溶解度。單一功 能物質(如,單續化)的你 平κ化)的使用可避免分子的交聯,減少濁滑 劑中鹽類的沉澱。較祛的县,#s从、 、疋 1類為過驗。此過驗金屬具 有中和酸的效果’可形成潤滑劑。第二個優點為過鹼的睡 類可增加摩擦的動力系數。此過驗金屬的量較佳可多於: 和SiL性所需要的量,在相同的基礎下 u刃丞碾下,其比例約為30 : 1, 較佳為5: 1至18: 1。 在無油的基礎下,使用於此組成物中的過驗性鹽類較 佳為約0.1至約10wt%。在無油的基礎下,此過鹼鹽類通 常由約50%的油與與1 0-600的TBN所組成。 硼酸與非硼酸過鹼性界面活性劑 丨王削可見於美國專利號 5,403,501與4, 792, 410,所揭露的内玄比 J鬥谷皆屬於本發明的範 疇。 9.磷酸鹽 此潤滑組成物較佳也可包括至少一較佳含O.OMH 〇 重量%硫類似物之磷酸、磷酸鹽、磷酸醋或其衍生物。此磷 17 201247684 酸、碟酸鹽、碟酸目旨或其衍生物包括擇自於磷酸酯及其鹽 類、填酸鹽、含峨醜胺、含磷羧酸或酯類、含磷醚類及上 述之混合物。 在實施例中碟酸、s旨或衍生物可為一鱗酸、碟酸 酯、磷酸鹽、或其衍生物。磷酸包括磷酸、膦酸、次磷酸、 與硫代碟酸’包括二硫代磷酸與單硫代磷酸、硫代次磷酸 與硫代膦酸。 其中類化合物為 〇, 0-dialky l-phosphorodi thioates 與順丁烯二酸酯或反丁烯二酸酯的加合物。這些化合物可 以習知方法製備’可參照美國專利號3, 359, 203,例如, 0, 0-二(2-乙基己基)s-(l,2-二甲酸丁氧基)二硫代磷酸 8曰(0,0 di(2-ethylhexyl)S-(l,2-dicarbobutoxyethyl) phosphorodithioate 〇 叛酸醋的二硫代磷酸酯為另一類可使用於本發明的化 合物。較佳為具2至8個碳原子的烷基酯,例如3 - [[ b i s (1 -甲基乙氧基)硫膦基]硫]丙酸乙醋。 第三類可用於本發明之無灰二硫代磷酸酯包括: (i )下列化學式 S I— C00R8 (R7-0)2—p-s—J— C00R8 其中R7與R8獨立地選自於3至8個碳原子的烷基(R. τ.
Vanderbilt股份有限公司之市售VANLUBE 7611M); (ii)缓酸之二硫代磷酸酯,如Ciba Geigy Corp公司 之市售 IRGALUBE® 63 ; 18 201247684 (i i i )三苯硫逐填酸酯’例如C i ba Ge i gy Corp公司之 市售 IRGALUBE® TPPT;以及 鋅鹽較佳添加至潤滑組成物中,其含量為三苯硫逐碟 酸酯的0·卜5 ’其中苯基可被二烷基取代。此基團例如可 為三苯基硫代碳酸酯,如市售IRGALUBE® TPPT(Ciba-Geigy 股份有限公司製造)。 磷酸化合物的較佳群組為二烷基磷酸單烷基一級胺 鹽’可參照美國專利號5, 354, 484,所揭露的内容屬於本 發明的範疇。85%的磷酸化合物可添加至完全組成atf套組 (fully formulated ATF package)中,且較佳為 ATF 重量 的約0. (U-0. 3重量%。 烧基填酸醋胺鹽可以習知方法製備,如美國專利號 4, 130, 494所述之方法,其所揭露的内容屬於本發明的範 疇。適合的磷酸單或二酯或其混合物可被胺類中和。當使 用單酯時,需要2莫耳的胺,二酯則需要丨莫取的胺。在 所有的情況下,所需胺類的量可藉由觀察反應的中和點來 控制,此時總酸值(total acid number)實質上與總鹼值 (total base number)相同。此外,也可添加中和劑,如氨 或乙二胺至此反應中。 敉住之場毆酯 —必u签、η—辛 基、己基單或二酯。此胺類可擇自於一級或二級胺。特別 是較佳為具10至24個碳原子的叔烷基胺。這些胺類可為 市售產品,例如Rohm and Haas公司的Primene(g) 81R。 石黃酸鹽已為習知物質,且可為由市而 田帀面上購得。可用作 19 201247684 製備本發明增效劑的芳香磺酸代表為烷基苯磺酸與烷基萘 磺酸,其具有8至20個碳之1至4個烷基。特別較佳為經 具9至18個之烷基取代之碳萘磺酸鹽,例如,二壬基萘續 酸鹽。 10.消泡劑 消泡劑為習知之矽膠或氟矽膠組成物。此消泡劑可由
Dow Corning Chemical 股份有限公司與 Union Carbide 股 份有限公司購得。較佳之氟矽膠消泡劑為Dow FS-1265。 較佳之石夕膠消泡劑為Dow Corning DC-200與Union Carbide UC-L45。其它可單獨或合併使用於組成物中的消泡劑為西 維吉尼亞之Monsanto Polymer Products公司的聚丙烯消
泡劑PC-1244。此外,也可包括密西根州法明頓丘〇SI
Specia 11 ies股份有限公司的矽氧烷聚醚共聚物消泡劑。 此物質如市售SILWET-L-7220。在本發明組成物中,消泡 劑產品較佳在無油基質下每百萬活性成分下具有5至8 〇部 分。 11 ·防銹劑 防銹劑的例子包括烷基萘磺酸的金屬鹽類。 12.銅緩蝕劑 可選擇性添加之銅緩蝕劑的例子包括噻唑、三唑與噻 二唑。每個化合物的例子包括苯並三唑、甲苯三唑、辛基 一唑、癸基二唑、十二烷基三唑、2_巯基噻唑、2, 5-二酼 基-1,3, 4-噻二唑、2-毓基-5-烴基硫代_;[,3, 4_噻二唑' 2_ 巯基-5-烴基二硫代噻二唑、2,5_Ms(烴基硫 20 201247684 坐、與 2,5-bis(烴基二硫代)__13,4_^ 代)-l,3,4~〇g σ虫 〇 【實施例] 下述例子為笱日日i 說月本發明,不可 有說明’所有的百八L 了用於限制發明。除了另 實施例! 刀比或部分皆以重量為基礎。 實驗例盘比赵 如表一所^在=ΛΜ("Κ組成物以嶋組成物製備, (DTDA-1)來自於含有1}中’所有的DTDA原_ 、有、、勺 70% 2-丁烯(Cis 與 trans) ' 約 2〇。 異丁烯與約1〇%異 ' 邮的丁烯原料。在比較例(m〇dtc_a ^ M〇DTC_B)中,職原料(DTDA-A與DTDA-B)來自於富含: 表一 樣本 DTDA . DTDA碳數分佈,皙量< C11 C12 C13 C14 MoDTC-1 (實施例) 95 質量% DTDA-1 ....................-......... 5 質量% DTDA-B trace 3 <1 - - - 31 >98 57 trace .…—"9........ MoDTC-A (比較例) 100 質量% DTDA-A <1 22 70 8 MoDTC-B (比較例) 100 質量% DTDA-B 3 31 57 9 實施例2 烯的原料’其同樣也分 刀引3有吳丁烯或乙烯。所有的MoDTC 組成物皆以相同的方法製備,包括將麵與三氧化钥水 與二硫化碳反應。特別是,MoDTC組成物以美國專利號 7’31 2, 348所教不的方法製備,其所揭露的内容皆屬於本 發明的範疇。 將實施例1之MoDTC組成物完全溶於4 cSt ΡΑ0合成 21 201247684 基底油,在70°C下加熱,良好地攪拌。將此溶液置於室溫 下冷卻。在置於室溫12個小時後,可在此溶液中發現沉澱 物。如表二所示,只有以實施例MoDTC]所製備的溶液無 沉澱物的產生。 實施例3 將貫施例1之MoDTC組成物完全溶解於市售之gf-4普 通 10W-30 機油(GF-4 conventional 10W-30 engine oil)。 接著將這些溶液置於維持在12〇c的冰箱中。24小時後可 在此溶液中發現沉澱物。如表二所示,只有以實施例 MoDTC-1所製備的溶液無沉澱物的產生。 實施例4 將實施例1之MoDTC組成物完全溶解於市售之GF_4合 成10W-30機油。接著將這些溶液置於維持在—^艽的冷凍 庫。在6與6 0天後,可在此溶液中發現沉澱物。如表二所 示’只有以實施例MoDTC-Ι所製備的溶液無沉澱物的產生。 表二' 不同的潤滑組成中的M〇DTC儲存穩定性 潤滑油 處理 質量讲* 溫度 時間 MoDTC*1* MoDTC-A* MoDTC-B木 4 cSt ΡΑ0 0.5 RT 12h 澄清 沉澱 沉澱 普通GF-4 10W-30機油 1.0 12t 24h 澄清 沉澱 沉澱 合成GF-4 10W-30機油 氺ΜηΓΠΤ/接翅 1.0 »、丄人 1 / -10°C 6天/ 60天 澄清/ 澄清 沉澱/ 嚴重沉澱 沉殿厂 嚴重沉澱 *、MoDTC/稀釋油混合物中含有7質量%的銦,為随^釋油混丄物的: 分 tUffTc添加至潤滑劑中,與稀釋油形成50/50質量比的混合物,最终 潤滑劑中含〇· 25-0. 5%的MoDTC 、 在每個例子中,使用大部分之丁烯原料的DTDA所製備 22 201247684 之本發明MoDTC比起以富含丙烯原料的DTJ)a所製備的
MoDTC組成物更為優良。對於此技術領域人士令人驚訝的 是,預期以具廣泛碳數分佈之二烷基胺(如丙烯dtda)所製 備之MoDTC組成物的結果比起具有非常—致碳數分佈(如 丁烯DTDA)的MoDTC組成物,其具有較佳的油溶性。如表 —所示,雖然丙烯之DTDA組成物具有U至14個的碳,但 丁烯DTDA,DTDA-1 ’實質上為所有的異_十三烷基。具有 良好油溶性之本發明MoDTC — 丨約98%的烷基鏈為Cu,^歸 類為丁烯DTDA的異構物衍生物,其歸因於丁烯原料具有大 置的異構物,包括4種異構物,丁烯、卜扣>5_2_丁 烯、1-丁烯與異丁烯,而丙烯DTDA不含有異構物物質。 實施例5 以DTDA組成物製備實施例與比較例m〇dtc,如表三所 不。在實施例(MoDTC-2)中,所有的DTDA原料(DTDA-1)來 自於含有約70% 2-丁烯(順式與反式)、ab〇ut 2〇%異丁烯 與約10%異丁烯的丁烯原料。在比較例M〇DTC_C _,Dtda 原料為70% DTDA-1與30% DTDA-B的混合。後者為源自於 田含丙烯也含有乙烯的原料。在比較例M〇DK_D中, 原料為100% DTDA-B。所有的M〇DTC組成物以相同的方法 靠-備,包括將DTDA與三氧化鉬、水與二硫化碳反應。特別 疋,MoDTC組成物以美國專利號7, 524, 799所教示的方法 製備,其所揭露的内容皆屬於本發明的範疇。 23 201247684 表三 樣本 DTDA DTDA碳數分佈,質量% C11 C12 C13 C14 MoDTC-2 (實施例) 95 質量% DTDA-1 trace <1 >98 trace 5 質量% DTDA-B 3 31 57 9 MoDTC-C (比較例) 70 質量% DTDA-1 trace <1 >98 trace 30 質量% DTDA-B 3 31 57 9 MoDTC-D (比較例) 100 質量% DTDA-B 3 31 57 9 實施例6 將實施例5之MoDTC組成物(0. 73質量%)完全溶於市 售普通GF-5 5W-30機油中。接著,將此溶液置於12°C的 冰箱,與-1 0 °C的冷凍庫。如表四所示,僅含有實施例 MoDTC-2之溶液在40天後,仍維持不具有陰霾、渾濁或沉 澱。 表四、普通GF-5 5W-30機油中MoDTC組成物林(0.73%)的儲存穩定性 溫度 MoDTC-2 MoDTC-C MoDTC-D 12t 40天時保持澄清 9天時有沉澱產生 1天時有沉澱產生 -HTC 40天時保持澄清 2天時非常陰霾 1天時呈霧狀 (Cloudy) 林將ΜοΕ)Ί 「C添加至潤滑劑中,與稀釋油形成70/30質量比的混合物,最終
潤滑劑中含約0, 51%的MoDTC 此MoDTC/稀釋油混合物含有約9. 6質量%的翻,為 MoDTC/稀釋油組成物的一部分。 實施例7 將實施例5之MoDTC組成物(0. 73質量%)完全溶解於 市售合成GF-5 5W-30機油。接著,將此溶液置於12°C的 冰箱,與-1 0 °C的冷凍庫。如表五所示,僅含有實施例 MoDTC-2之溶液在40天後,仍維持不具有陰霾、渾濁或沉 24 201247684 澱。 組-l^j3%)的^^ 1 40天後彳$g^|~ 在2天& 40天有輕微陰霾
MoDTC-C 16天時有沉澱產生 —__JjgDTC-D 有沉殿產生 1天時呈霧狀 (Cloudy) 丨一 I (hazvL — 2天時非常陰霾 丄:狀 心01'(:/稀釋油混合物中'^^^61質量%钥,為臟(:〉蘇油二7物^:: 部分
料將MoDTC添加至潤滑劑中,與稀釋油形成70/30質量比的混合物,最終 潤滑劑中含約0. 51%的MoDTC 在每一例子中,主要以丁烯原料DTDA製備之本發明 MoDTC優於以含有大於5%(>5%)丙烯DTDA製備之MoDTC組 成物。此外,由此可知,可維持一定程度地容忍MoDTC含 量超出實施例的限制(如,>98% Cu),不會造成不良的影響 (如,DTDA-B MoDTC的10%,較佳至5%)。然而,若濶滑油 中所有MoDTC組成中DTDA-B MoDTC的含量大於10%或更多 時,會對溶解度產生不良的影響。因此,本發明潤潸組成 物具有Cu-C14 MoDTC組成,其由大於90%,更佳至少95%,
更佳至少99%之具有大於98% Cu之本發明DTDA-1 MoDTC 所組成。應注意的是,此技藝人士可能會希望合併Ch-Cm 以外之額外的MoDTC ’作為本發明潤滑組成物的一部分。 例如,可添加源自於乙基己基胺或二辛基胺之MoDTCs。 【圖式簡單說明】 第1圖為製備二-異十三烷基胺(DTDA)組成物的流程 圖,由丁烯與富含兩烯的原料開始。 25 201247684 【主要元件符號說明】 無0 26
Claims (1)
- 201247684 七、申請專利範圍: 鉬組成物的方法,包括以下 1. 一種製備二硫胺基甲酸 步驟: 二一十 由一包含大於50%之2_丁烯的丁烯原料製備 三烷基胺(DTDA)中間產物;以及 由該DTDA中間產物製備—二硫胺基^ 2. 如申請專利範圍第1項所述之方法,其中該丁稀原 料更包括1-丁烯與異丁烯。 3. 如f請專利範圍第2項所述之方法,其中該丁稀原 料包括約7 0 %之2 - 丁稀、$ 2 Π %之里丁 种J ζυ/°之吳丁烯、以及約10%之異 丁稀。 4. 如申請專利範圍第3項所述之方法,其中該二硫胺 基甲酸!目組成物具有平均大於98%的Cu ’以作為取代烧基 的一部分。 5· 一種新穎二硫胺基甲酸鉬,如式(1)所示,其中L 至h為Cu-Cm異烷基,χ為氧及/或硫原子,且1至l包 括平均大於98%的Cu : R R’ X X y 11/ \|! S s X —S—II—N: ,R, (1) υ 6. 一種潤滑組成物,包括一主要之潤滑基底以及妙 〇〇卜3%如式(1)所示之二-十三烷基二硫胺基曱酸鉬,其中 1至R4為Cu-Cu異烷基,X為氧及/或硫原子,且1至R 包括平均大於98%的Cu : 27 201247684 F 1 〆 R ' 卫3、R, (1) 7. 如申請專利範圍第6項所述之潤滑組成物,其中該 二硫胺基曱酸鉬為約O 8. 如申請專利範圍第7項所述之潤滑組成物,其中該 二硫胺基甲酸鉬為約0.25-0.5%。 9. 如申請專利範圍第6項所述之_滑組成物其中該 潤滑組成物之ClI-Cl4二硫胺基曱酸鉬係由大於9〇%之二-十 三烷基二硫胺基曱酸鉬所組成,其中1至&包括平均大於 98%的 Ci3。 10. 如中請專利範圍第9項所述之潤滑組成物,其中該 潤滑組成物之Cu-Cu二硫胺基曱酸鉬係由至少95%之二-十 三烷基二硫胺基曱酸鉬所組成’其中匕至&包括平均大於 98%的 Cn。 11. -種製備潤滑組成物的方法,包括以下步驟: 由一包含大於50%之2-丁烯的丁烯原料製備一二-十 三烷基胺(DTDA)中間產物; 由該DTDA中間產物製備一二_十= 丁一况暴一硫胺基曱酸 鉬;以及 添加該二-十三院基二硫胺基甲酸翻至一潤滑基底 中,為該潤滑組成物的0.01_3%,則該潤滑組成物的 二硫胺基甲酸翻由大於90%之二’十三烷基二硫胺基甲酸翻 所組成,其中R!至L包括平均大於98%的C3。 28
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- 2012-03-21 US US13/425,560 patent/US9012383B2/en active Active
- 2012-03-21 KR KR1020137028977A patent/KR101575607B1/ko active IP Right Grant
- 2012-03-21 SG SG2013073127A patent/SG194007A1/en unknown
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- 2012-03-21 MX MX2013012048A patent/MX342410B/es active IP Right Grant
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- 2012-03-21 JP JP2014505148A patent/JP5797832B2/ja active Active
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- 2012-03-21 BR BR112013025981-7A patent/BR112013025981B1/pt active IP Right Grant
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EP2697342B1 (en) | 2016-11-16 |
KR20140003626A (ko) | 2014-01-09 |
CN103502403B (zh) | 2015-06-17 |
BR112013025981A2 (pt) | 2016-12-20 |
US9012383B2 (en) | 2015-04-21 |
JP2014514407A (ja) | 2014-06-19 |
CN103502403A (zh) | 2014-01-08 |
CA2831596C (en) | 2015-11-24 |
WO2012141855A1 (en) | 2012-10-18 |
RU2013150806A (ru) | 2015-05-20 |
EP2697342A4 (en) | 2014-10-01 |
EP2697342A1 (en) | 2014-02-19 |
MX2013012048A (es) | 2014-03-27 |
JP5797832B2 (ja) | 2015-10-21 |
RU2566744C2 (ru) | 2015-10-27 |
AR085970A1 (es) | 2013-11-06 |
SG194007A1 (en) | 2013-11-29 |
KR101575607B1 (ko) | 2015-12-08 |
ES2613527T3 (es) | 2017-05-24 |
BR112013025981B1 (pt) | 2019-01-22 |
MX342410B (es) | 2016-09-28 |
CA2831596A1 (en) | 2012-10-18 |
US20120264666A1 (en) | 2012-10-18 |
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