EP3209756B1 - Dispergiermittelviskositätsmodifikatoren mit sulfonatfunktionalität - Google Patents
Dispergiermittelviskositätsmodifikatoren mit sulfonatfunktionalität Download PDFInfo
- Publication number
- EP3209756B1 EP3209756B1 EP15778794.6A EP15778794A EP3209756B1 EP 3209756 B1 EP3209756 B1 EP 3209756B1 EP 15778794 A EP15778794 A EP 15778794A EP 3209756 B1 EP3209756 B1 EP 3209756B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- lubricating composition
- olefin
- polymer backbone
- alkyl
- 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.)
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- 239000002270 dispersing agent Substances 0.000 title claims description 100
- 239000004034 viscosity adjusting agent Substances 0.000 title claims description 97
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 title claims description 36
- 239000000203 mixture Substances 0.000 claims description 129
- 229920000642 polymer Polymers 0.000 claims description 113
- 230000001050 lubricating effect Effects 0.000 claims description 99
- -1 aryl sulfonic acids Chemical class 0.000 claims description 74
- 125000005647 linker group Chemical group 0.000 claims description 59
- 239000003921 oil Substances 0.000 claims description 58
- 150000001336 alkenes Chemical class 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 37
- 229920001577 copolymer Polymers 0.000 claims description 36
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 35
- 229920000768 polyamine Polymers 0.000 claims description 23
- 239000003599 detergent Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 19
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 18
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 17
- 239000003963 antioxidant agent Substances 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 239000000178 monomer Substances 0.000 claims description 15
- 239000003607 modifier Substances 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 13
- 150000001768 cations Chemical class 0.000 claims description 13
- 125000000524 functional group Chemical group 0.000 claims description 12
- 239000003112 inhibitor Substances 0.000 claims description 12
- 239000005977 Ethylene Substances 0.000 claims description 11
- 229920005862 polyol Polymers 0.000 claims description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 10
- 230000003078 antioxidant effect Effects 0.000 claims description 10
- 150000003077 polyols Chemical class 0.000 claims description 9
- 238000005260 corrosion Methods 0.000 claims description 7
- 230000007797 corrosion Effects 0.000 claims description 7
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 238000005227 gel permeation chromatography Methods 0.000 claims description 5
- 150000008054 sulfonate salts Chemical class 0.000 claims description 5
- 239000004793 Polystyrene Substances 0.000 claims description 4
- 229920002223 polystyrene Polymers 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 230000000994 depressogenic effect Effects 0.000 claims description 3
- 150000003460 sulfonic acids Chemical class 0.000 claims description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 2
- 235000019198 oils Nutrition 0.000 description 57
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 23
- 239000000654 additive Substances 0.000 description 22
- 238000002485 combustion reaction Methods 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000376 reactant Substances 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 239000010705 motor oil Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 229960002317 succinimide Drugs 0.000 description 12
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 10
- 239000002199 base oil Substances 0.000 description 10
- 229910052698 phosphorus Inorganic materials 0.000 description 10
- 239000011574 phosphorus Substances 0.000 description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
- 239000003085 diluting agent Substances 0.000 description 9
- 239000000314 lubricant Substances 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 239000011593 sulfur Substances 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 150000001993 dienes Chemical class 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 7
- 229920000193 polymethacrylate Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- 150000003873 salicylate salts Chemical class 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000003502 gasoline Substances 0.000 description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 5
- 239000005078 molybdenum compound Substances 0.000 description 5
- 150000002752 molybdenum compounds Chemical class 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 4
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 229920002367 Polyisobutene Polymers 0.000 description 4
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000010687 lubricating oil Substances 0.000 description 4
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 description 4
- 229920013639 polyalphaolefin Polymers 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 238000007655 standard test method Methods 0.000 description 4
- 229920001897 terpolymer Polymers 0.000 description 4
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- 229910006069 SO3H Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-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
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 150000002646 long chain fatty acid esters Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- KHYKFSXXGRUKRE-UHFFFAOYSA-J molybdenum(4+) tetracarbamodithioate Chemical class C(N)([S-])=S.[Mo+4].C(N)([S-])=S.C(N)([S-])=S.C(N)([S-])=S KHYKFSXXGRUKRE-UHFFFAOYSA-J 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000008053 sultones Chemical class 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- 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
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- GLOYGJPNNKTDIG-UHFFFAOYSA-N SC=1N=NSC=1S Chemical class SC=1N=NSC=1S GLOYGJPNNKTDIG-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000002537 cosmetic Substances 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
- 238000009826 distribution Methods 0.000 description 2
- 229920001038 ethylene copolymer Polymers 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002194 fatty esters Chemical class 0.000 description 2
- 239000013020 final formulation Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- WOLATMHLPFJRGC-UHFFFAOYSA-N furan-2,5-dione;styrene Chemical compound O=C1OC(=O)C=C1.C=CC1=CC=CC=C1 WOLATMHLPFJRGC-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002462 imidazolines Chemical class 0.000 description 2
- 229920000554 ionomer Polymers 0.000 description 2
- 150000004668 long chain fatty acids Chemical class 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000006078 metal deactivator Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000010688 mineral lubricating oil Substances 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920006389 polyphenyl polymer Polymers 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- 125000000542 sulfonic acid group Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000010689 synthetic lubricating oil Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 125000005270 trialkylamine group Chemical group 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 2
- 150000005671 trienes Chemical class 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- OJOWICOBYCXEKR-APPZFPTMSA-N (1S,4R)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound CC=C1C[C@@H]2C[C@@H]1C=C2 OJOWICOBYCXEKR-APPZFPTMSA-N 0.000 description 1
- LZXHHNKULPHARO-UHFFFAOYSA-M (3,4-dichlorophenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].C1=C(Cl)C(Cl)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 LZXHHNKULPHARO-UHFFFAOYSA-M 0.000 description 1
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- ZGXMNEKDFYUNDQ-GQCTYLIASA-N (5e)-hepta-1,5-diene Chemical compound C\C=C\CCC=C ZGXMNEKDFYUNDQ-GQCTYLIASA-N 0.000 description 1
- RJUCIROUEDJQIB-GQCTYLIASA-N (6e)-octa-1,6-diene Chemical compound C\C=C\CCCC=C RJUCIROUEDJQIB-GQCTYLIASA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- IQDWOGOLRVLAKY-IUPFWZBJSA-N (z)-n,n-bis[(z)-octadec-9-enyl]octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN(CCCCCCCC\C=C/CCCCCCCC)CCCCCCCC\C=C/CCCCCCCC IQDWOGOLRVLAKY-IUPFWZBJSA-N 0.000 description 1
- JTQQDDNCCLCMER-CLFAGFIQSA-N (z)-n-[(z)-octadec-9-enyl]octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCNCCCCCCCC\C=C/CCCCCCCC JTQQDDNCCLCMER-CLFAGFIQSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 150000000178 1,2,4-triazoles Chemical class 0.000 description 1
- RDAGYWUMBWNXIC-UHFFFAOYSA-N 1,2-bis(2-ethylhexyl)benzene Chemical class CCCCC(CC)CC1=CC=CC=C1CC(CC)CCCC RDAGYWUMBWNXIC-UHFFFAOYSA-N 0.000 description 1
- YEYQUBZGSWAPGE-UHFFFAOYSA-N 1,2-di(nonyl)benzene Chemical class CCCCCCCCCC1=CC=CC=C1CCCCCCCCC YEYQUBZGSWAPGE-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- 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 1
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- SZATXRHXOOLEFV-UHFFFAOYSA-N 2,6-ditert-butyl-4-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SZATXRHXOOLEFV-UHFFFAOYSA-N 0.000 description 1
- STHGHFNAPPFPQV-UHFFFAOYSA-N 2,6-ditert-butyl-4-propylphenol Chemical compound CCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 STHGHFNAPPFPQV-UHFFFAOYSA-N 0.000 description 1
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- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Images
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M151/00—Lubricating compositions characterised by the additive being a macromolecular compound containing sulfur, selenium or tellurium
- C10M151/02—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
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- C10M151/00—Lubricating compositions characterised by the additive being a macromolecular compound containing sulfur, selenium or tellurium
- C10M151/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/102—Aliphatic fractions
- C10M2203/1025—Aliphatic fractions used as base material
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- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/022—Ethene
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
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- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2221/02—Macromolecular compounds obtained by reactions of monomers involving only carbon-to-carbon unsaturated bonds
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- 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/02—Viscosity; Viscosity index
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- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/04—Molecular weight; Molecular weight distribution
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/02—Pour-point; Viscosity index
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- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/04—Detergent property or dispersant property
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- 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
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- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/40—Low content or no content compositions
- C10N2030/42—Phosphor free or low phosphor content compositions
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/40—Low content or no content compositions
- C10N2030/45—Ash-less or low ash content
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- 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
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/252—Diesel engines
- C10N2040/253—Small diesel engines
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2070/00—Specific manufacturing methods for lubricant compositions
Definitions
- aspects of the exemplary embodiment relate to a dispersant viscosity modifier, and more specifically to a sulfonated dispersant viscosity modifier and to a lubricating composition, such as an engine oil, which includes the described dispersant viscosity modifier. Aspects of the exemplary embodiment also relate to a method for use of the described dispersant viscosity modifier to improve the film thickness and/or antiwear performance of such a lubricating composition.
- Lubricating oil compositions desirably maintain a relatively stable viscosity over a wide range of temperatures.
- Viscosity modifiers are often used to reduce the extent of the decrease in viscosity as the temperature is raised or to reduce the extent of the increase in viscosity as the temperature is lowered, or both.
- a viscosity modifier ameliorates the change of viscosity of an oil containing it with changes in temperature. The fluidity characteristics of the oil are thereby improved.
- DVMs dispersant viscosity modifiers
- U.S. Pat. No. 3,642,728, issued February 15, 1972 , entitled SULFONATE POLYMERS, by Canter, discloses sulfonated polymers, such as polymers with low unsaturation formed by the polymerization of ethylene or propylene, particularly polymers with 0.2-10 mole % remaining unsaturation. Sulfonation can be carried out at an aromatic ring within the backbone or pendent therefrom.
- U.S. Pub. No. 20130303418 published November 14, 2013, entitled HIGH MOLECULAR WEIGHT POLYMERS AS VISCOSITY MODIFIERS, by FALENDER, et al. , discloses a lubricating composition which comprises a base oil and between 10 ppm and 1000 ppm by mass of a viscosity modifier, the viscosity modifier comprising an olefin copolymer.
- a viscosity modifier comprising an olefin copolymer.
- additional monomers is anticipated to allow the inventive polymer to have the properties of dispersants, antioxidants, pour point depressants and other additive chemistry.
- U.S. Pub. Nos. 20120178656 and 20120178659, entitled DISPERSANT VISCOSITY MODIFIERS, by Sutton, et al. , and Price, et al. disclose a grafted polymer useful as a dispersant viscosity modifier in lubricating compositions.
- the polymer backbone includes an olefin block and a vinyl aromatic block.
- the polymer is grafted with a pendant carbonyl containing group, which may be substituted to provide ester, imide and/or amide functionality.
- U.S. Pat. No. 3,749,695 by de Vries discloses a lubricating oil additive derived from polyisobutylene ethylene diamine with propane sultone.
- GB 1,121,641 to Castrol Ltd. describes preparation of an additive for a lubricating composition from hydroxy tetraethylene tetramine, polyisobutenyl succinic anhydride and propane sultone.
- a lubricating composition includes an oil of lubricating viscosity and at least 0.05 wt. % of an oil-soluble dispersant viscosity modifier which includes an olefin-based polymer backbone and at least one pendent functional group selected from alkyl and aryl sulfonate salts, alkyl and aryl sulfonic acids, and combinations thereof, the olefin-based polymer backbone comprising an ethylene-olefin-based copolymer.
- Each of the at least one pendent functional group is independently attached to the olefin-based polymer backbone by a linking group.
- the at least one pendent functional group includes a sulfonate moiety.
- a process for making a lubricating composition includes: (i) providing an olefin-based polymer backbone with one or more acylating linking groups, each independently attached along the polymer backbone; (ii) optionally, reacting each acylating group with a hydroxy alkyl amine, an alkylene polyamine, a polyol, or a combination thereof, resulting in an olefin-based polymer with one or more linker units each independently attached along the polymer backbone; and (iii) reacting each linking group or linker unit with a hydrocarbyl sulfonate compound selected from sulfonate salts and sulfonic acids, resulting in a dispersant viscosity modifier comprising one or more pendent hydrocarbyl sulfonate groups each independently attached to the olefin-based polymer.
- the exemplary embodiment relates to a lubricating composition which includes an oil of lubricating viscosity and a sulfonated dispersant viscosity modifier that includes an olefin-based polymer with pendent groups having sulfonate functionality.
- the exemplary sulfonated dispersant viscosity modifier has improved performance in engine tests, providing a good viscosity index, good soot dispersion and/or toleration properties, while also providing good antiwear protection and/or film thickness performance.
- the exemplary lubricating composition finds particular application as an engine oil for passenger vehicles and heavy duty diesel vehicles.
- additives present in the lubricating composition disclosed herein are expressed on an oil free basis, i.e., amount of actives, unless otherwise noted.
- the exemplary sulfonated dispersant viscosity modifier is a material that provides viscosity modifier performance in a lubricating composition while also providing dispersant functionality.
- the dispersant viscosity modifier may provide additional and or other benefits to a lubricating composition.
- the exemplary dispersant viscosity modifier is an oil-soluble polymer, which includes a polymer backbone, such as an olefin-based polymer, and one or more pendent hydrocarbyl sulfonate groups each independently attached to the olefin-based polymer.
- the pendent hydrocarbyl sulfonate groups each include a sulfonate moiety, which can be in the form of a sulfonate salt or a sulfonic acid group, and a hydrocarbyl group, such as an alkyl and/or aryl group, which spaces the sulfonate moiety from the polymer backbone and connects it thereto
- oil soluble it is meant that the dispersion viscosity modifier is soluble in oil at least to the amounts described herein for desirable for serving its intended purpose.
- Each of the pendent groups is attached to the polymer chain by a linking group that is grafted onto the olefin-based polymer or forms a part of the polymer backbone.
- the linking group thus links the pendent group to the olefin-based polymer.
- Each linking group may be derived from a dicarboxylic acid, such as maleic anhydride, that can be linked to the pendent group directly or indirectly, via a linker unit.
- the linking group may be grafted to the polymer backbone by first reacting a dicarboxylic acid, such as maleic anhydride, to the polymer backbone using a peroxide catalyst to form the linking group and then attaching the linker unit by esterification, imidation or amidation.
- a dicarboxylic acid such as maleic anhydride
- the sulfonated dispersant viscosity modifier can be represented by a molecule of the general formula (I): P-(X-Y-Z) x (I), where P represents the olefin-based polymer, X represents the linking group, Y represents an optional intermediate linker unit, Z represents the pendent hydrocarbyl sulfonate group, and x is at least 1, such as from 1 to 20, or 1 to 10, or 1 to 8, e.g., at least 2.
- P represents the olefin-based polymer
- X represents the linking group
- Y represents an optional intermediate linker unit
- Z represents the pendent hydrocarbyl sulfonate group
- x is at least 1, such as from 1 to 20, or 1 to 10, or 1 to 8, e.g., at least 2.
- the values of x may be considered number average values over all the molecules present.
- a ratio by weight of linking groups X to the polymer backbone P in the dispersant viscosity modifier may be at least 1:100, or at least 2:100, such as at least 3:100, and in some embodiments, is up to up to 20:100 or up to 10:100.
- P in Formula (I) may contain a range of molecular weights, commonly characterized by a molecular weight distribution, so the values of x may be considered number average values over all the molecules present.
- P is an ethylene-olefin-based copolymer and the viscosity modifier of Formula (I) is represented by Formula (II) or (III): -[[(CH 2 ) m -(CHR 1 -CH 2 ) n )] p-q -[(CH 2 ) m -(CR 1 (X-Y-Z)-CH 2 ) n ] q ] k - (II) -[[(CH 2 ) m -(CHR 1 -CH 2 ) n ] p -[X(Y-Z)] q ] k - (III) where each R 1 represents H or an alkyl group containing from 1 to 8 carbon atoms,
- a ratio of m:n may be from 1 to 6.
- the ratio of m:n may be 1.5 to 2.3, or 2.3 to 3.5, or 3.5 to 6.
- a ratio of the number of hydrocarbyl sulfonate groups q : number ethylene olefin units p in the molecules of Formulas (II) and (III) is at least 0.01.
- the ratio of q:p may be at least 0.02, or at least 0.03, or at least 0.1, or at least 0.2 and may be up to 0.9, or up to 0.5.
- Formula (II) represents a viscosity modifier in which the linking group X is grafted onto the polymer backbone P, which can be of the general form -[(CH 2 ) m -(CHR 1 -CH 2 ) n ] p - prior to grafting.
- Formula (III) represents a viscosity modifier in which the linking group X is integral with the polymer backbone P.
- linking groups X may be linked to a hydrocarbyl sulfonate group Z, although in one embodiment, a majority (at least 50%), or substantially all (at least 80%, or at least 90%, or at least 95%), or all of the linking groups X are linked to a respective hydrocarbyl sulfonate group Z.
- the hydrocarbyl sulfonate group Z may be derived from a hydrocarbyl sulfonate compound, such as an alkyl or aryl sulfonic acid, source thereof, or salt thereof.
- the hydrocarbyl sulfonate group Z can be represented by the general formula -[R 2 (SO 3 ) - ] r M r+ , where R 2 represents a hydrocarbyl group, and M r+ represents a cation, where r is at least 1.
- the sulfonate moiety in the hydrocarbyl sulfonate group Z can thus be represented by -[(SO 3 ) - ] r M r+ .
- M r+ may be selected from H + (the acid form) and other cations, such as metal cations and aliphatic amine cations of the form -(NR 3 R 4 R 5 ), where R 3 , R 4 , and R 5 are independently selected from H and C 1 to C 30 hydrocarbyl groups, such as aliphatic groups, e.g., C 1 to C 30 alkyl groups.
- R 3 , R 4 , and R 5 are independently selected from H and C 1 to C 30 hydrocarbyl groups, such as aliphatic groups, e.g., C 1 to C 30 alkyl groups.
- at least one or at least two of R 3 , R 4 , and R 5 is an alkyl group and in another embodiment, each of R 3 , R 4 , and R 5 is an alkyl group.
- the alkyl groups have at least 2, or at least 3, or up to 20, or up to 10 carbon atoms.
- Example metal cations include alkali metals, such as K + , Na + , Mg +2 , Ca 2+ , and mixture thereof.
- the dispersant viscosity modifier is metal free, and the cation is a non-metal cation.
- the cation is suitably a monovalent cation, i.e., r is 1, although minor amounts of multivalent cations may be present.
- the sulfonate moiety may be selected from oil-soluble salts to avoid formation of oil-insoluble or sparingly soluble salts through reaction with the base.
- hydrocarbyl group is used herein in its ordinary sense, which is well-known to those skilled in the art. Specifically, it refers to a group having a carbon atom directly attached to the remainder of the molecule and having predominantly hydrocarbon character. Examples of hydrocarbyl groups include:
- Heteroatoms include sulfur, oxygen, nitrogen, and encompass substituents such as pyridyl, furyl, thienyl, and imidazolyl.
- substituents such as pyridyl, furyl, thienyl, and imidazolyl.
- no more than two, and in some embodiments, no more than one non-hydrocarbon substituent is present for every ten carbon atoms in the hydrocarbyl group. In one embodiment, there are no non-hydrocarbon substituents in the hydrocarbyl group.
- the hydrocarbyl group R 2 of the hydrocarbyl sulfonate group Z is or includes an alkyl group, such as a C 3 to C 24 alkyl group or C 3 -C 20 alkyl group, which spaces the sulfonate moiety from the polymer backbone by at least three carbon atoms, which may be in the form of a chain and/or ring.
- the hydrocarbyl group R 2 is or includes an aryl group, such as a C 6 to C 20 aryl group which spaces the sulfonate moiety from the polymer backbone by an aromatic ring.
- One or more of the carbons in the hydrocarbyl group R 2 may be substituted with heteroatoms.
- the sulfonated dispersant viscosity modifier includes from 1 to 50 of the described hydrocarbyl sulfonate groups Z, or from 1 to 30, or from 1 to 20, or 1 to 10, or from 1 to 6, or 1 to 4, per molecule of the dispersant viscosity modifier, on average. In some embodiments, the sulfonated dispersant viscosity modifier includes 1, 2, 3, 4, 5 or 6 hydrocarbyl sulfonate groups Z, on average.
- the exemplary linking groups X are acylating groups, each independently attached along the polymer's backbone.
- the linking group X may be derived from an ethylenically unsaturated carboxylic acid monomer, such as a dicarboxylic acid, or functional equivalent thereof, or a polyol.
- the intermediate linker unit Y may be derived from a hydroxy alkyl amine, an alkylene polyamine, or a combination thereof.
- the linking group X is derived from maleic anhydride and the linker unit Y is derived from a hydroxy alkyl amine.
- the unsaturated carboxylic reactant is grafted on to the olefin-based polymer backbone and the hydroxy alkyl amine and/or alkylene polyamine is reacted with the unsaturated carboxylic reactant group containing olefin-based polymer backbone.
- the unsaturated carboxylic reactant is present in the olefin-based polymer backbone and the hydroxy alkyl amine and/or alkylene polyamine is reacted with the unsaturated carboxylic reactant group containing olefin-based polymer backbone.
- the hydrocarbyl sulfonate compound includes an amine or -OH functional group which can serve as an intermediate linker unit Y.
- the unsaturated carboxylic reactant may be grafted on to the olefin-based polymer backbone and the amine/alcohol functional group of the hydrocarbyl sulfonate compound is reacted with the unsaturated carboxylic reactant group containing olefin-based polymer backbone.
- the unsaturated carboxylic reactant is present in the olefin-based polymer backbone the amine/alcohol functional group of the hydrocarbyl sulfonate compound is reacted with the unsaturated carboxylic reactant group containing olefin-based polymer backbone.
- the polymer backbone P employed in the sulfonated dispersant viscosity modifier is not particularly limited, provided that it can be modified with a carboxylic acid functionality or a reactive equivalent of the carboxylic acid functionality (e.g., anhydride or ester) that serves as the linking group described above.
- Suitable olefin-based polymer backbones P include ethylene, propylene, and butylene polymers, copolymers thereof, copolymers thereof further containing a non-conjugated diene, and isobutylene/conjugated diene copolymers, each of which can be subsequently supplied with, e.g. grafted with, carboxylic functionality to serve as the linking group or have carboxylic functionality in the backbone itself (such as an ethylene-co-propylene-co-maleimide copolymer).
- the polymer backbone P is a copolymer of ethylene and an ⁇ -olefin, such as propylene and/or butylene.
- Example ethylene-olefin-based polymers include ethylene propylene copolymers.
- the olefin-based polymer is a copolymer where ethylene makes up at least 10 % of the monomer used to prepare the copolymer on a molar basis, or at least 20 mole %, or at least 50 mole %.
- Ethylene-propylene or higher alpha monoolefin copolymers may consist of 15 to 80 mole % ethylene and 20 to 85 mole % propylene or higher monoolefin. In some embodiments, the mole ratio is 30 to 80 mole % ethylene and 20 to 70 mole % of at least one C 3 to C 10 alpha monoolefin, for example, 50 to 80 mole % ethylene and 20 to 50 mole % propylene.
- Terpolymer variations of the foregoing polymers may contain up to 15 mole %, or up to 10 mole % of a non-conjugated diene or triene.
- the polymer backbone e.g., the ethylene copolymer or terpolymer
- the polymer can be in forms other than substantially linear, that is, it can be a branched polymer or a star polymer.
- the polymer can also be a random copolymer or a block copolymer, including di-blocks and higher blocks, including tapered blocks and a variety of other structures.
- the polymer backbone (olefin-based polymer) may have a number average molecular weight Mn (measured by gel permeation chromatography, using a polystyrene standard), which can be up to 150,000 or higher, e.g., at least 1,000 or at least 3,000 or at least 5,000, such as up to 150,000 or up to 120,000, or up to 100,000, or up to 50,000, or up to 15,000, e.g., about 3,000 to about 15,000.
- Mn number average molecular weight measured by gel permeation chromatography, using a polystyrene standard
- the sulfonated dispersant viscosity modifier may have a number average molecular weight Mn (by gel permeation chromatography, polystyrene standard), which can be up to 150,000 or higher, e.g., at least 2,000 or at least 3,000 or at least 5,000, such as up to 150,000 or up to 120,000, or up to 100,000, or up to 50,000, or up to 18,000, e.g., about 4,000 to about 16,000.
- Mn number average molecular weight
- polymer is used generically to encompass homopolymers, i.e., polymers of a single monomer, as well as copolymers, terpolymers and/or interpolymers. These materials may contain minor amounts of other olefinic monomers so long as their basic characteristics are not materially changed.
- the exemplary sulfonated dispersant viscosity modifier is formed by reacting a carboxylic acid-modified polymer backbone with a hydroxy alkyl amine and/or alkylene polyamine and/or polyol and a hydrocarbyl sulfonate compound.
- the exemplary dispersant viscosity modifier may be formed by reacting a carboxylic acid-modified polymer backbone with an amino-substituted hydrocarbyl sulfonate compound. Where a sulfonic acid is formed, the acid may be converted to its salt through reaction with a suitable base.
- the unsaturated carboxylic acid monomer used to form the linking group X may be derived from maleic acid and/or anhydride.
- this portion of the linking group may be incorporated and/or attached to the polymer backbone during the polymerization of the polymer backbone, for example, by mixing a monomer containing the linking group in with the other monomers used to prepare the polymer backbone.
- this part of the linking group may be added by grafting the group onto an already prepared polymer backbone.
- the unsaturated carboxylic acid used to form the linking group is contained within a monomer copolymerized within the polymer backbone chain.
- the unsaturated carboxylic reactant may be present as a pendent group attached by, for example, a grafting process.
- suitable carboxylic-acid containing polymers which are representative of the polymer backbone described above with carboxylic reactant portion of the liking group attached, include maleic anhydride-ethylene-propylene copolymers, maleic anhydride-styrene copolymers, including partially esterified versions thereof, and copolymers thereof.
- Nitrogen-containing esterified carboxyl-containing interpolymers prepared from maleic anhydride and styrene-containing polymers are described in U.S. Pat. No. 6,544,935 to Vargo et al .
- Other polymer backbones which are used for preparing dispersants may also be used. For example, polymers derived from isobutylene and isoprene are described in U.S.
- suitable polymer backbones include substantially hydrogenated copolymers of vinyl aromatic materials such as styrene and unsaturated hydrocarbons such as conjugated dienes, e.g., butadiene or isoprene.
- substantially hydrogenated polymers of this type the olefinic unsaturation is typically substantially completely hydrogenated by known methods, but the aromatic unsaturation may remain.
- Such polymers can include random copolymers, block copolymers, or star copolymers.
- Suitable backbone polymers include styrene-ethylene-alpha olefin polymers, as described in PCT publication WO 2001/030947 , and polyacrylates or polymethacrylates, generically called poly(meth)acrylates.
- the (meth)acrylate monomers within the polymer chain itself may serve as the carboxylic acid functionality or reactive equivalent thereof which is used to react with the amine functionality which provides the linker unit Y.
- additional acid functionality may be copolymerized into the (meth)acrylate chain or even grafted onto it, particularly in the case of acrylate polymers.
- the polymer backbone may be prepared from ethylene and propylene or it may be prepared from ethylene and a higher olefin within the range of (C 3 to C 10 ) alpha-monoolefins, which may then in either case be grafted with a suitable carboxylic acid-containing monomer, to serve as the linking group X.
- interpolymers More complex polymer backbones, often designated as interpolymers, may also be included. Such materials are generally used to prepare an interpolymer backbone is a polyene monomer selected from conjugated or non-conjugated dienes and trienes.
- the non-conjugated diene component is one having from about 5 to about 14 carbon atoms.
- the diene monomer is characterized by the presence of a vinyl group in its structure and can include cyclic and bicyclo compounds.
- Representative dienes include 1,4-hexadiene, 1,4-cyclohexadiene, dicyclopentadiene, 5-ethylidene-2-norbornene, 5-methylene-2-norbornene, 1,5-heptadiene, and 1,6-octadiene.
- a mixture of more than one diene can be used in the preparation of the interpolymer.
- the ethylenically unsaturated carboxylic acid monomer may be grafted onto the polymer backbone in a number of ways, such that a resulting polymer intermediate with linking groups X is characterized by having carboxylic acid acylating functions within its structure.
- Such materials which are attached to the polymer typically contain at least one ethylenic bond (prior to reaction) and at least one, or at least two, carboxylic acid (or its anhydride) groups or a polar group which is convertible into the carboxyl groups by oxidation or hydrolysis.
- Maleic anhydride or an alkyl-substituted derivative thereof is suitable for forming the linking groups.
- carboxylic acid grafts onto the ethylene copolymer or terpolymer to give two carboxylic acid functionalities.
- additional unsaturated carboxylic materials include chlormaleic anhydride, itaconic anhydride, and the corresponding dicarboxylic acids, such as maleic acid, fumaric acid, acrylic acid, cinnamic acid, and their esters.
- Example intermediate polymers of this type are available from Mitsui under the tradename Lucant TM , such as Lucant TM A-5320H polymer.
- the polymer intermediate may then be reacted with the hydroxy alkyl amine, alkylene polyamine, or polyol to provide the intermediate polymer with linker units Y.
- the polymer intermediate is reacted directly with an amine-substituted hydrocarbyl sulfonate compound or other substituted hydrocarbyl sulfonate compound capable of reaction with the intermediate polymer.
- Hydroxy alkyl amines and/or alkylene polyamines suitable for forming linker units Y are not overly limited. In some embodiments, they may be represented by the general formula: R 6 R 7 N-R 8 -OH or R 6 R 7 N-R 8 -NR 6 R 7 where each R 6 and R 7 is independently hydrogen or a hydrocarbyl group containing from 1 to 6 carbon atoms and each R 8 is independently an alkylene group containing from 1 to 10 carbon atoms.
- Suitable hydroxy alkyl amines include amines having at least one amine group and at least one hydroxyl group, where the amine group is a primary, secondary, or tertiary amine group.
- the hydroxy alkyl amines may have 2 to 30 carbon atoms.
- Example hydroxy alkyl amines may include mono-, di- and tri-alkoxylates of ammonia such as mono- and di- and tri-ethanolamine, hydroxy-containing monoamines such as a diethoxylated C 16 to C 18 tallowamine, and hydroxy-containing polyamines such as 2-(2-aminoethylamino)ethanol.
- the hydroxy alkyl amine includes 3-hydroxypropyl amine.
- Suitable polyamines for forming linker units Y may have from 2 to 30 carbon atoms.
- Example polyamines include alkylenediamines, N-alkyl alkylenediamines, and polyalkylenepolyamines.
- Useful polyamines include ethylenediamine, 1,2-diaminopropane, N-methylethylenediamine, N-tallow(C 16 -C 18 )-1,3-propylenediamine, N-oleyl-1,3-propylenediamine, polyethylenepolyamines such as diethylenetriamine and triethylenetetramine and tetraethylenepentamine and polyethylenepolyamine bottoms.
- Suitable polyols for forming linker units Y are not overly limited. In some embodiments, they may be represented by the general formula: HO-R 9 -OH where R 9 is hydrocarbyl group, and in some embodiments an alkylene group, containing from 1 to 10 carbon atoms.
- the sulfonated dispersant viscosity modifier is prepared using an alkylene diol, an amino-polyol, or combinations thereof. Examples of suitable diols include butanediol, hexanediol, 2-amino-2-hydroxymethyl-propane-1,3-diol, and combinations thereof.
- reaction product of the olefin-based polymer backbone containing the unsaturated carboxylic reactant and the hydroxy alkyl amine and/or alkylene polyamine and/or polyol may then be reacted with the hydrocarbyl sulfonate compound to provide the dispersant viscosity modifier.
- the sulfonated dispersant viscosity modifier is the reaction product of (i) an olefin-based polymer, for example an ethylene propylene copolymer, that has been functionalized with a unsaturated carboxylic reactant, for example, by using maleic anhydride, and (ii) a hydroxy alkyl amine and/or an alkylene polyamine, for example, a hydroxy alkyl amine such as 3-hydroxypropylamine.
- the resulting intermediate can then be reacted with a hydrocarbyl sulfonate compound (which may thereafter be converted to a salt) to provide a dispersant viscosity modifier.
- the sulfonated dispersant viscosity modifier is the reaction product of (i) an olefin-based polymer, for example an ethylene propylene copolymer, that has been functionalized with a unsaturated carboxylic reactant, for example, by using maleic anhydride, and (ii) an amine-substituted hydrocarbyl sulfonate compound (which may thereafter be converted to a salt by reaction with a base) to provide a dispersant viscosity modifier.
- an olefin-based polymer for example an ethylene propylene copolymer
- a unsaturated carboxylic reactant for example, by using maleic anhydride
- an amine-substituted hydrocarbyl sulfonate compound which may thereafter be converted to a salt by reaction with a base
- Suitable hydrocarbyl sulfonate compounds for forming the pendent functional groups are of the general form: B-A-SO 3 M where A represents a hydrocarbyl group or a substituted hydrocarbyl group, M is a cation as described above, and B represents a functional group capable of reacting with the linker unit Y, or capable of undergoing direct acylation with the linking group X.
- B can be NH 2 (giving an amine-substituted hydrocarbyl sulfonate compound, H 2 N-A-SO 3 M) or OH.
- the hydrocarbyl sulfonate compounds can also be in the form of a ring capable of reaction with water to form B-A-SO 3 H.
- the hydrocarbyl group A may be at least 3 carbons in length and may be selected from C 3 -C 20 alkyl groups and C 6 -C 24 aryl or alkylaryl groups, as discussed for R 2 above.
- M may represent a monovalent cation.
- group B is capable of acylation by the linking group, the linker unit can be omitted, although it may still be useful for chain extension to space the lipophilic sulfonate moiety further from the backbone.
- Example alkyl hydrocarbyl sulfonate compounds suitable for forming the pendent functional groups include aliphatic sulfonic acids represented by formula (IV): where c is from 1-10,
- formula (V) examples include 3-hydroxypropane-1-sulfonic acid: and 3-amino-1-propane sulfonic acid:
- substituted alkyl sulfonate compounds include homocysteic acid:
- Example cyclic sulfonic acids known as sultones which have the sulfonyl-oxy group -OSO 2 - in a ring, can be represented by formula (V): where d is from 1-10, such as 1 or 2, and R 13 , R 14 , and R 15 are independently H or a C 1 to C 30 alkyl group.
- Sultones can react in water to form the corresponding hydroxyalkyl sulfonic acid.
- Such hydrocarbyl sulfonate compounds are capable of reaction with OH groups of the linker units Y of the intermediate polymer.
- 1,3-propanesultone yields products with a terminal -CH 2 -CH 2 -CH 2 -SO 3 H group and 1,4-butanesultone yields products with a terminal -CH 2 -CH 2 -CH 2 -SO 3 H group, where the terminal H can subsequently be converted to another cation M as described above.
- aryl sulfonate compounds include those of general formulas (VI), (VII), (VIII), (IX), and (X): where R 16 , R 17 , R 18 , and R 19 , are independently selected from H, OH, NH 2 , C 1 -C 30 (or C 1 -C 10 ) alkyl groups, and alkoxy groups,
- the NH 2 group may be positioned ortho , meta , or para to the sulfonic acid group.
- Additional substituents e.g., just one, can be positioned on the ring in the locations not occupied by the amine or sulfonic acid.
- the substituent is a methyl group, but can also be a hydroxy (-OH) group, an alkoxy (-OR) group, a nitroxy (-NO 2 ) group, or another amine.
- aryl sulfonate compounds according to formula (VI) include p -aminobenzenesulfonic acid (sulfanilic acid):
- the aryl group can be based on naphthalene.
- the sulfonic acid may occupy either the 1 or 2 position on the ring and the amine may be either on the same ring or on the adjoining ring.
- Substituents can be the same noted for single ring aryl groups and may occupy any sites not occupied by the amine or sulfonic acid.
- aryl sulfonate compounds according to formula (IX) include 7-amino-1,3-naphthene disulfonic acid:
- aryl sulfonate compounds according to formula (X) include 8-(2-aminoethylamino)-1-naphthene sulfonic acid: and substituted derivatives thereof.
- the resulting molecule includes a sulfonate moiety which is a sulfonic acid
- a suitable base for conversion of the acid form of the sulfonate moiety to the respective sulfonate salt include metal hydroxides, such as NaOH, KOH, and Ca(OH) 2 , and alkyl amines, such as di- or tri-alkyl amines of the general form NR 3 R 4 R 5 , where R 3 , R 4 , and R 5 are as described above.
- the alkyl amine may have alkyl groups having 1 to 30, or 2 to 20, or 3 to 10 carbon atoms.
- dialkyl amines include dimethylamine, diethylamine, dipropylamine, dibutylamine, dipentylamine, dihexylamine, di-(2-ethylhexyl)amine, di-decylamine, di-dodecylamine, di-stearylamine, di-oleylamine, di-eicosylamine, and mixtures thereof.
- trialkyl amines include trimethylamine, triethylamine, tripropylamine, tributylamine, tripentylamine, trihexylamine, tri-(2-ethylhexyl)amine, tri-decylamine, tridodecylamine, tri-stearylamine, tri-oleylamine, tri-eicosylamine, and mixtures thereof.
- the reaction can be carried out in a suitable solvent, such as a diluent oil and/or toluene, at a sufficient temperature, such as at least 90°C or at least 100°C, but below the boiling point of the solvent or the decomposition temperature of the product.
- a suitable solvent such as a diluent oil and/or toluene
- the reaction can be accomplished in the substantial absence of solvent, e.g., in a twin screw extruder, Banbury mixer, or similar device.
- the sulfonated dispersant viscosity modifier may be present in the lubricating composition at a concentration of at least 0.05 weight %, such as at least 0.1 weight %, or at least 0.2 weight %, or at least 0.5 weight %.
- the sulfonated dispersant viscosity modifier may be present in the lubricating composition at a concentration of up to 10 weight %, such as up to 5 weight %, or up to 3 weight %, or up to 2.3 weight %.
- HLB values reported herein are determined by the Griffin Method (see Griffin, William C. (1949), “Classification of Surface-Active Agents by 'HLB'", Journal of the Society of Cosmetic Chemists 1 (5): 311-26 and Griffin, William C. (1954), "Calculation of HLB Values of Non-Ionic Surfactants", Journal of the Society of Cosmetic Chemists 5 (4): 249-56
- HLB 20*M h /M, where M h is the molecular mass of the hydrophilic portion of the molecule and M is the molecular mass of the whole molecule. This method covers a range from 0-20.
- the exemplary sulfonated dispersant viscosity modifier may have an HLB value according to the Griffin method, of 1-10, or at least 2, or at least 2.5, or at least 3, and can be up to 9 or up to 8, or up to 7.
- a sulfonated dispersant viscosity modifier with an ethylene propylene backbone having about 240 CH 2 /CH/CH 3 groups has an molecular mass of approximately 3525, as determined by vapor phase osmometry (VPO).
- VPO vapor phase osmometry
- each polymer backbone chain has, on average, 3.5 sites which can be functionalized with the sulfonate moiety.
- the HLB for the dispersant viscosity modifier composed of an ethylenepropylene copolymer with aryl sulfonic acid pendent groups can be computed as 4.0.
- the HLB range can be up to about 6.8 or higher for the alkyl sulfonic acid and up to about 6.2 for the aryl sulfonic acid dispersion viscosity modifiers.
- the entire head group is considered as the hydrophilic portion, even though it contains some hydrocarbon portions.
- the exemplary lubricating composition includes an oil of lubricating viscosity.
- Suitable oils include both natural and synthetic oils, oil derived from hydrocracking, hydrogenation, and hydrofinishing, unrefined, refined, re-refined oils or mixtures thereof.
- Unrefined oils are those obtained directly from a natural or synthetic source generally without (or with little) further purification treatment.
- Refined oils are similar to the unrefined oils except they have been further treated in one or more purification steps to improve one or more properties.
- Purification techniques include solvent extraction, secondary distillation, acid or base extraction, filtration, percolation and the like.
- Re-refined oils are also known as reclaimed or reprocessed oils, and are obtained by processes similar to those used to obtain refined oils and often are additionally processed by techniques directed to removal of spent additives and oil breakdown products.
- Natural oils useful in making the inventive lubricants include animal oils, vegetable oils (e.g., castor oil), mineral lubricating oils such as liquid petroleum oils and solvent-treated or acid-treated mineral lubricating oils of the paraffinic, naphthenic or mixed paraffinic-naphthenic types and oils derived from coal or shale or mixtures thereof.
- animal oils e.g., castor oil
- mineral lubricating oils such as liquid petroleum oils and solvent-treated or acid-treated mineral lubricating oils of the paraffinic, naphthenic or mixed paraffinic-naphthenic types and oils derived from coal or shale or mixtures thereof.
- Synthetic lubricating oils are useful and include hydrocarbon oils such as polymerized, oligomerized, or interpolymerized olefins (e.g., polybutylenes, polypropylenes, propyleneisobutylene copolymers); poly(1-hexenes), poly(1-octenes), trimers or oligomers of 1-decene, e.g., poly(1-decenes), such materials being often referred to as poly ⁇ -olefins, and mixtures thereof; alkylbenzenes (e.g., dodecylbenzenes, tetra-decylbenzenes, dinonylbenzenes, di-(2-ethylhexyl)-benzenes); polyphenyls (e.g., biphenyls, terphenyls, alkylated polyphenyls); diphenyl alkanes, alkylated diphenyl
- oils include polyol esters (such as Priolube ® 3970), diesters, liquid esters of phosphorus-containing acids (e.g., tricresyl phosphate, trioctyl phosphate, and the diethyl ester of decane phosphonic acid), or polymeric tetrahydrofurans.
- Synthetic oils may be produced by Fischer-Tropsch reactions and typically may be hydroisomerized Fischer-Tropsch hydrocarbons or waxes. In one embodiment, oils may be prepared by a Fischer-Tropsch gas-to-liquid synthetic procedure as well as other gas-to-liquid oils.
- the base oil may be selected from any of the base oils in Groups I-V of the American Petroleum Institute (API) Base Oil Interchangeability Guidelines, namely Base Oil Category Sulfur (%) Saturates(%) Viscosity Index Group I >0.03 and/or ⁇ 90 80 to 120 Group II ⁇ 0.03 and ⁇ 90 80 to 120 Group III ⁇ 0.03 and ⁇ 90 >120 Group IV 'All polyalphaolefins (PAOs) Group V All others not included in Groups I, II, III or IV
- Oils of lubricating viscosity are mineral oil base stocks. Oils of lubricating viscosity may also be defined as specified in April 2008 version of "Appendix E - API Base Oil Interchangeability Guidelines for Passenger Car Motor Oils and Diesel Engine Oils", section 1.3 Sub-heading 1.3. "Base Stock Categories”. In one embodiment, the oil of lubricating viscosity may be an API Group II or Group III oil. In another embodiment, the oil of lubricating viscosity may be an API Group I oil.
- the oil of lubricating viscosity may have a kinematic viscosity of less than 15 mm 2 /s (cSt) at 100 °C, and in other embodiments 1-12 or 2-10 or 3-8 or 4-6 mm 2 /s.
- Kinematic viscosity is determined by ASTM D445-14, "Standard Test Method for Kinematic Viscosity of Transparent and Opaque Liquids (and Calculation of Dynamic Viscosity)," ASTM International, West Conshohocken, PA, 2003, DOI: 10.1520/D0445-14 .
- the dispersant viscosity modifier may have a kinematic viscosity at 100 °C of at least 35 mm 2 /s, or at least 100 mm 2 /s, or at least 500 mm 2 /s.
- the amount of the oil of lubricating viscosity present is typically the balance remaining after subtracting from 100 wt % the sum of the amount of the sulfonated dispersant viscosity modifier and the other performance additives.
- the oil of lubricating viscosity may be present in the lubricating composition at a concentration of at least 10 wt %, or at least 20 wt %, or at least 40 wt %, or at least 80 wt %, and may be up to 99 wt %, or up to 95 wt %, or up to 90 wt %.
- the lubricating composition may be in the form of a concentrate and/or a fully formulated lubricant. If the lubricating composition (comprising the additives disclosed herein) is in the form of a concentrate which may be combined with additional oil to form, in whole or in part, a finished lubricant), the ratio of the of these additives to the oil of lubricating viscosity and/or to diluent oil include the ranges of 1:99 to 99:1 by weight, or 80:20 to 10:90 by weight.
- the lubricating composition (comprising the additives disclosed herein) is in the form of a finished lubricant
- the ratio of these additives to the oil of lubricating viscosity and/or to diluent oil include the ranges of 1:99.9 to 50:50 by weight, or 1:99 to 30:70 by weight.
- the lubricating composition optionally includes one or more additional performance additives.
- additional performance additives may include one or more metal deactivators, viscosity modifiers, detergents, friction modifiers, antiwear agents, corrosion inhibitors, dispersants, dispersant viscosity modifiers (other than the exemplary compound), extreme pressure agents, antioxidants, foam inhibitors, demulsifiers, pour point depressants, seal swelling agents, antiwear agents, and any combination or mixture thereof.
- fully-formulated lubricating oil will contain one or more of these performance additives, and often a package of multiple performance additives.
- the lubricating composition further includes a dispersant, an antiwear agent, a friction modifier, a viscosity modifier, an antioxidant, an overbased detergent, or a combination thereof, where each of the additives listed may be a mixture of two or more of that type of additive.
- the lubricating composition further includes a polyisobutylene succinimide dispersant, an antiwear agent, a friction modifier, a viscosity modifier (typically an olefin copolymer such as an ethylene-propylene copolymer), an antioxidant (including phenolic and aminic antioxidants), an overbased detergent (including overbased sulfonates and phenates), or a combination thereof, where each of the additives listed may be a mixture of two or more of that type of additive.
- a polyisobutylene succinimide dispersant typically an antiwear agent, a friction modifier, a viscosity modifier (typically an olefin copolymer such as an ethylene-propylene copolymer), an antioxidant (including phenolic and aminic antioxidants), an overbased detergent (including overbased sulfonates and phenates), or a combination thereof, where each of the additives listed may be a mixture of two or more of that type of additive.
- the lubricating composition further includes an antiwear agent such as a metal dihydrocarbyl dithiophosphate (typically zinc dialkyldithiophosphate), wherein the metal dihydrocarbyl dithiophosphate contributes at least 100 ppm, or at least 200 ppm, or 200 ppm to 1000 ppm, or 300 ppm to 800 ppm, or 400 ppm to 600 ppm of phosphorus to the lubricating composition.
- the lubricating composition is free of or substantially free of zinc dialkyldithiophosphate (ZDDP).
- the lubricating composition further includes a dispersant.
- the dispersant may be present at a concentration of 0 wt % to 20 wt %, such as at least 0.01 wt %, or at least 0.1 wt %, or at least 0.1 wt %, or at least 1 wt %, or up to 20wt%, or up to 15 wt %, or up to 10 wt %, or up to 6 wt % of the lubricating composition.
- the dispersant may be present in the composition at a concentration of 0.2 wt % to 2 wt %.
- Suitable dispersants for use in the exemplary lubricating compositions include succinimide dispersants.
- the dispersant may be present as a single dispersant.
- the dispersant may be present as a mixture of two or three different dispersants, wherein at least one may be a succinimide dispersant.
- the succinimide dispersant may be a derivative of an aliphatic polyamine, or mixtures thereof.
- the aliphatic polyamine may be aliphatic polyamine such as an ethylenepolyamine, a propylenepolyamine, a butylenepolyamine, or mixtures thereof.
- the aliphatic polyamine may be ethylenepolyamine.
- the aliphatic polyamine may be selected from the group consisting of ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, polyamine still bottoms, and mixtures thereof.
- the dispersant may be a N-substituted long chain alkenyl succinimide.
- N-substituted long chain alkenyl succinimides include polyisobutylene succinimide.
- the polyisobutylene from which a polyisobutylene succinic anhydride is derived has a number average molecular weight of 350 to 5000, or 550 to 3000 or 750 to 2500.
- Succinimide dispersants and their preparation are disclosed, for example, in U.S. Pat. Nos.
- the dispersant may also be post-treated by conventional methods by a reaction with any of a variety of agents.
- agents include boron compounds, urea, thiourea, dimercaptothiadiazoles, carbon disulfide, aldehydes, ketones, carboxylic acids, hydrocarbon-substituted succinic anhydrides, maleic anhydride, nitriles, epoxides, and phosphorus compounds.
- the lubricating composition further includes a dispersant viscosity modifier other than the sulfonated dispersant viscosity modifier described herein.
- the additional dispersant viscosity modifier may be present at a concentration of 0 wt % to 5 wt %, such as at least 0.01 wt %, or at least 0.05 wt %, or up to 5 wt %, or up to 4 wt %, or up to 2 wt % of the lubricating composition.
- Suitable dispersant viscosity modifiers include functionalized polyolefins, for example, ethylene-propylene copolymers that have been functionalized with an acylating agent such as maleic anhydride and an amine; polymethacrylates functionalized with an amine, and esterified styrene-maleic anhydride copolymers reacted with an amine.
- exemplary dispersant viscosity modifiers are disclosed, for example, in WO2006/015130 and U.S. Pat. Nos. 4,863,623 ; 6,107,257 ; 6,107,258 ; and 6,117,825 .
- the lubricating composition further includes a phosphorus-containing antiwear agent.
- the antiwear agent may be present at a concentration of 0 wt % to 3 wt %, such as at least 0.1 wt %, or at least 0.5 wt %, or up to 3 wt %, or up to 1.5 wt %, or up to 0.9 wt % of the lubricating composition.
- the phosphorus-containing antiwear agent may be a zinc dialkyldithiophosphate, or mixture thereof.
- the lubricating composition further includes a molybdenum compound.
- the molybdenum compound may provide the lubricating composition with 0 to 1000 ppm, or 5 to 1000 ppm, or 10 to 750 ppm 5 ppm to 300 ppm, or 20 ppm to 250 ppm of molybdenum.
- the molybdenum compound may be selected from the group consisting of molybdenum dialkyldithiophosphates, molybdenum dithiocarbamates, amine salts of molybdenum compounds, and mixtures thereof.
- the lubricating composition further includes an overbased detergent.
- the overbased detergent may be present at 0 wt % to 15 wt %, or at least 0.1 wt %, or at least 0.2 wt %, or at least 0.2 wt %, or up to 15 wt %, or up to 10 wt %, or up to 8 wt %, or up to 3 wt % of the lubricating composition.
- the detergent may be present at 2 wt % to 3 wt % of the lubricating composition.
- the detergent may be present at 0.2 wt % to 1 wt % of the lubricating composition.
- the overbased detergent may be selected from the group consisting of non-sulfur containing phenates, sulfur containing phenates, sulfonates, salixarates, salicylates, and mixtures thereof.
- the overbased detergent may also include "hybrid" detergents formed with mixed surfactant systems including phenate and/or sulfonate components, e.g., phenate/salicylates, sulfonate/phenates, sulfonate/salicylates, sulfonates/phenates/salicylates, as described; for example, in U.S. Pat. Nos. 6,429,178 ; 6,429,179 ; 6,153,565 ; and 6,281,179 .
- phenate/salicylates e.g., phenate/salicylates, sulfonate/phenates, sulfonate/salicylates, as described; for example, in U.S. Pat. Nos. 6,429,178 ; 6,429,179 ; 6,153,565 ; and 6,281,179 .
- the hybrid detergent can be considered equivalent to amounts of distinct phenate and sulfonate detergents introducing like amounts of phenate and sulfonate soaps, respectively.
- Suitable overbased detergents are sodium salts, calcium salts, magnesium salts, or mixtures of the phenates, sulfur containing phenates, sulfonates, salixarates and salicylates.
- Overbased phenates and salicylates may have a total base number of 180 to 450 TBN.
- Overbased sulfonates may have a total base number of 250 to 600, or 300 to 500.
- the sulfonate detergent may be predominantly a linear alkylbenzene sulfonate detergent having a metal ratio of at least 8, as described, for example, in U.S. Pub. No. 20050065045 .
- the linear alkylbenzene sulfonate detergent may be particularly useful for assisting in improving fuel economy.
- the linear alkyl group may be attached to the benzene ring anywhere along the linear chain of the alkyl group, but often in the 2, 3, or 4 position of the linear chain, and in some instances, predominantly in the 2 position, resulting in the linear alkylbenzene sulfonate detergent.
- the lubricating composition includes an antioxidant, or mixture of antioxidants.
- the antioxidant may be present at 0 wt % to 15 wt 5, or 0.1 wt % to 10 wt %, or 0.5 wt % to 5 wt % of the lubricating composition.
- Antioxidants include sulfurized olefins, alkylated diarylamines (typically alkylated phenyl naphthyl amines for example those commercially available as Irganox ® L 06 from CIBA, or alkylated diphenylamines such as dinonyl diphenylamine, octyl diphenylamine, dioctyl diphenylamine), hindered phenols, molybdenum compounds (such as molybdenum dithiocarbamates), or mixtures thereof.
- alkylated diarylamines typically alkylated phenyl naphthyl amines for example those commercially available as Irganox ® L 06 from CIBA
- alkylated diphenylamines such as dinonyl diphenylamine, octyl diphenylamine, dioctyl diphenylamine
- hindered phenols such as molybdenum dithioc
- the hindered phenol antioxidant often contains a secondary butyl and/or a tertiary butyl group as a steric hindering group.
- the phenol group may be further substituted with a hydrocarbyl group (typically linear or branched alkyl) and/or a bridging group linking to a second aromatic group.
- hindered phenol antioxidants examples include 2,6-di-tert-butylphenol, 4-methyl-2,6-di-tert-butylphenol, 4-ethyl-2,6-di-tert-butylphenol, 4-propyl-2,6-di-tert-butylphenol or 4-butyl-2,6-di-tert-butylphenol, or 4-dodecyl-2,6-di-tert-butylphenol.
- the hindered phenol antioxidant may be an ester and may include, e.g., lrganox TM L-135 from Ciba.
- suitable ester-containing hindered phenol antioxidant chemistry is found in U.S. Patent 6,559,105 .
- the lubricating composition further includes a friction modifier.
- the friction modifier may be present at 0 wt % to 6 wt %, such as at least 0.05 wt %, or at least 0.1 wt %, or up to 6 wt %, or up to 4 wt %, or up to 2 wt % of the lubricating composition. In one embodiment, the friction modifier is present in the composition at 0.1 to 1.0 wt %.
- friction modifiers include long chain fatty acid derivatives of amines, fatty esters, or epoxides; fatty imidazolines such as condensation products of carboxylic acids and polyalkylene-polyamines; amine salts of alkylphosphoric acids; fatty alkyl tartrates; fatty alkyl tartrimides; or fatty alkyl tartramides.
- fatty as used herein, can mean having a C 8 to C 22 linear alkyl group.
- Friction modifiers may also encompass materials such as sulfurized fatty compounds and olefins, molybdenum dialkyldithiophosphates, molybdenum dithiocarbamates, sunflower oil or monoester of a polyol and an aliphatic carboxylic acid.
- the friction modifier may be selected from the group consisting of long chain fatty acid derivatives of amines, long chain fatty esters, or long chain fatty epoxides; fatty imidazolines; amine salts of alkylphosphoric acids; fatty alkyl tartrates; fatty alkyl tartrimides; and fatty alkyl tartramides.
- the friction modifier may be a long chain fatty acid ester.
- the long chain fatty acid ester may be a monoester or a diester or a mixture thereof, and in another embodiment the long chain fatty acid ester may be a triglyceride.
- corrosion inhibitors include those described in U.S. Pub. No. 20050038319 , octyl octanamide, condensation products of dodecenyl succinic acid or anhydride and a fatty acid such as oleic acid with a polyamine.
- the corrosion inhibitors include a Synalox ® corrosion inhibitor.
- the Synalox ® corrosion inhibitor may be a homopolymer or copolymer of propylene oxide.
- Synalox ® corrosion inhibitors are described in a product brochure, Form No. 118-01453-0702 AMS, entitled "SYNALOX Lubricants, High-Performance Polyglycols for Demanding Applications," published by The Dow Chemical Company.
- Metal deactivators including derivatives of benzotriazoles (such as tolyltriazole), dimercaptothiadiazole derivatives, 1,2,4-triazoles, benzimidazoles, 2-alkyldithiobenzimidazoles, or 2-alkyldithiobenzothiazoles; foam inhibitors including copolymers of ethyl acrylate and 2-ethylhexylacrylate and copolymers of ethyl acrylate and 2-ethylhexylacrylate and vinyl acetate; demulsifiers including trialkyl phosphates, polyethylene glycols, polyethylene oxides, polypropylene oxides and (ethylene oxide-propylene oxide) polymers; pour point depressants including esters of maleic anhydride-styrene, polymethacrylates, polyacrylates or polyacrylamides may be useful.
- benzotriazoles such as tolyltriazole
- dimercaptothiadiazole derivatives 1,2,4-tri
- Pour point depressants that may be useful in the compositions of the invention include polyalphaolefins, esters of maleic anhydride-styrene, poly(meth)acrylates, and polyacrylamides.
- the lubricating composition may have a composition as described in Table 1: Table 1: Example Lubricating Compositions Additive Embodiments (wt %) A B C Exemplary Sulfonated Dispersant Viscosity Modifier 0.05 to 10 0.2 to 3 0.5 to 2 Dispersant 0.05 to 12 0.75 to 8 0.5 to 6 Overbased Detergent 0 or 0.05 to 15 0.1 to 10 0.2 to 8 Antioxidant 0 or 0.05 to 15 0.1 to 10 0.5 to 5 Antiwear Agent 0 or 0.05 to 15 0.1 to 10 0.3 to 5 Friction Modifier 0 or 0.05 to 6 0.05 to 4 0.1 to 2 Viscosity Modifier 0 or 0.05 to 10 0.5 to 8 1 to 6 Any Other Performance Additiv 0 or 0.05 to 10 0 or 0.05 to 8 0 or 0.05 to 6 Oil of Lubricating Viscosity Balance to 100 Balance to 100 Balance to 100 Balance to 100
- the sulfonated dispersant viscosity modifier may be present in embodiments (D) at 0.1 to 8 wt %, or (E) 1 to 7 wt %, or (F) 2 to 6 wt %, or (G) 0.1 to 2 wt %, or (H) 0.3 to 1.2 wt % of the lubricating composition, with the amount of dispersant, overbased detergent, antioxidant, antiwear agent, friction modifier, viscosity modifier, any other performance additive and an oil of lubricating viscosity in amounts shown in the table above for embodiments (A) to (C).
- a method of lubricating an internal combustion engine includes supplying to the internal combustion engine a lubricating composition as disclosed herein.
- the lubricating composition is added to the lubricating system of the internal combustion engine, which then delivers the lubricating composition to the critical parts of the engine, during its operation, that require lubrication.
- a use of the dispersant viscosity modifier described herein to improve film thickness and/or antiwear performance of a lubricating composition is provided. These improvements can be considered in addition to the dispersancy and viscosity control performance expected from a dispersant viscosity modifier.
- the lubricating compositions described above may be utilized in an internal combustion engine.
- the engine components may have a surface of steel or aluminum (typically a surface of steel), and may also be coated for example, with a diamond like carbon (DLC) coating.
- An aluminum surface may comprise an aluminum alloy that may be a eutectic or hyper-eutectic aluminum alloy (such as those derived from aluminum silicates, aluminum oxides, or other ceramic materials).
- the aluminum surface may be present on a cylinder bore, cylinder block, or piston ring formed of an aluminum alloy or aluminum composite.
- the internal combustion engine may or may not have an Exhaust Gas Recirculation system.
- the internal combustion engine may be fitted with an emission control system or a turbocharger.
- Examples of the emission control system include diesel particulate filters (DPF), or systems employing selective catalytic reduction (SCR).
- the internal combustion engine may be a diesel fuelled engine (such as a heavy duty diesel engine), a gasoline fuelled engine, a natural gas fuelled engine or a mixed gasoline/alcohol fuelled engine.
- the internal combustion engine may be a diesel fuelled engine and in another embodiment a gasoline fuelled engine.
- the internal combustion engine may be a biodiesel fuelled engine.
- the internal combustion engine may be a 2-stroke or 4-stroke engine. Suitable internal combustion engines include marine diesel engines, aviation piston engines, low-load diesel engines, and automobile and truck engines.
- the internal combustion engine is a gasoline direct injection (GDI) engine.
- GDI gasoline direct injection
- the internal combustion engine is distinct from gas turbine.
- gas turbine which may also be referred to as a jet engine
- gas turbine it is a continuous combustion process that generates a rotational torque continuously without translation and can also develop thrust at the exhaust outlet.
- the lubricating composition for an internal combustion engine may be suitable for use as an engine lubricant irrespective of the sulfur, phosphorus or sulfated ash (ASTM D874) content.
- the sulfur content of the lubricating composition which is particularly suited to use as an engine oil lubricant, may be 1 wt % or less, or 0.8 wt % or less, or 0.5 wt % or less, or 0.3 wt % or less. In one embodiment, the sulfur content may be in the range of 0.001 wt % to 0.5 wt %, or 0.01 wt % to 0.3 wt %.
- the phosphorus content may be 0.2 wt % or less, or 0.12 wt % or less, or 0.1 wt % or less, or 0.085 wt % or less, or 0.08 wt % or less, or even 0.06 wt % or less, 0.055 wt % or less, or 0.05 wt % or less.
- the phosphorus content may be 100 ppm to 1000 ppm, or 200 ppm to 600 ppm.
- the total sulfated ash content may be 2 wt % or less, or 1.5 wt % or less, or 1.1 wt % or less, or 1 wt % or less, or 0.8 wt % or less, or 0.5 wt % or less, or 0.4 wt % or less.
- the sulfated ash content may be 0.05 wt % to 0.9 wt %, or 0.1 wt % to 0.2 wt % or to 0.45 wt %.
- the lubricating composition may be an engine oil, wherein the lubricating composition may be characterized as having at least one of (i) a sulfur content of 0.5 wt % or less, (ii) a phosphorus content of 0.1 wt % or less, (iii) a sulfated ash content of 1.5 wt % or less, or combinations thereof.
- kinematic viscosity is measured at 100°C (KV 100 ), according to the method of ASTM D445 - 12, "Standard Test Method for Kinematic Viscosity of Transparent and Opaque Liquids (and Calculation of Dynamic Viscosity)", ASTM International, West Conshohocken, PA, DOI: 10.1520/D0445-12.
- the viscosity index (VI) is determined according to ASTM D2270-10e1, "Standard Practice for Calculating Viscosity Index From Kinematic Viscosity at 40 and 100°C," DOI: 10.1520/D2270-10E01.
- the High Temperature/High Shear rate viscosity, HTHS (150°C), of a lubricating composition containing the exemplary dispersant viscosity modifier is determined herein according to the procedure defined in ASTM D4683-10, "Standard Test Method for Measuring Viscosity of New and Used Engine Oils at High Shear Rate and High Temperature by Tapered Bearing Simulator Viscometer at 150°C," ASTM International, West Conshohocken, PA. This test method determines the viscosity of an oil at 150 °C and 1.0 x 10 6 s -1 using a viscometer having a slightly tapered rotor and stator called the Tapered Bearing Simulator (TBS) Viscometer.
- TBS Tapered Bearing Simulator
- a succinimide intermediate is prepared by adding to a 3 L round bottom flask equipped with a mechanical stirrer, thermowell, nitrogen inlet, Dean-Stark trap and Friedrich's condenser, 852.0 grams of a maleated ethylene propylene copolymer, commercially available from Mitusi as Lucant TM A-5320H, and 852.0 g of diluent oil. The material is heated to 110°C with stirring and nitrogen purge. 25.8 grams of 3-aminopropanol is added to the mixture, resulting in the formation of a gel. Xylenes (54 g) are added to the flask with continued heating resulting in the gel eventually melting after about 20 minutes of agitation.
- the solution is then warmed to 175°C and agitated for 4.0 hours.
- the solution is cooled to 165°C and held an additional 1.5 hours at this temperature.
- the resulting polymer is stripped of solvents under deep vacuum at 165°C for 40 minutes. 1712.0 grams of the succinimide intermediate, appearing as a viscous yellow liquid, is recovered.
- Example 2 Preparation of a Maleated Ethylene Propylene Alkyl Sulfonic Acid Dispersant Viscosity Modifier
- a dispersant viscosity modifier is prepared by adding to a 2 L round bottom flask equipped with a mechanical stirrer, thermowell, nitrogen inlet, Dean-Stark trap and Friedrich's condenser, 300.0 grams of the succinimide intermediate of Example 1 and 328.2 g of diluent oil. The solution is heated to 110°C with agitation and nitrogen purge. Then, 11.1 grams of butanesultone are added, followed by toluene (50 ml). The solution is agitated at 125°C for 2 hours, then the temperature increased to 150°C for 6 hours. Solvent is then removed under deep vacuum at 150°C for 30 min to yield 625.0 grams of product, appearing as a viscous liquid. The resulting dispersant viscosity modifier is referred to below as 3.5% MAA alkyl sulfonic acid.
- a dispersant viscosity modifier is prepared by adding to a 2 L round bottom flask equipped with a mechanical stirrer, thermowell, nitrogen inlet, Dean-Stark trap and Friedrich's condenser, 430.0 grams of maleated ethylene propylene copolymer (Lucant TM A-5320H) and 486.0 g of diluent oil. The solution is heated to 120°C with agitation and nitrogen purge for 1 hour. 31.7 grams of tributylamine is added to the flask followed by 27.2 grams of sulfanilic acid. The flask is heated to 160°C for 7.5 hours. Additional tributylamine (31.7 g) is added to the flask with agitation at 160°C for 6.75 hours.
- Example 3 The product of Example 3 may be washed with aqueous acid to facilitate a cation exchange from a trialkylammonium ion to an H + ion, effectively converting the salt to an acid, as described in Example 4.
- Example 4 Preparation of a Maleated Ethylene Propylene Aryl Sulfonic Acid Dispersant Viscosity Modifier
- a dispersant viscosity modifier is prepared by adding to a 5 L round bottom flask equipped with a mechanical stirrer, thermowell, nitrogen inlet, Dean-Stark trap and Friedrich's condenser, 1372.5 grams of the succinimide intermediate of Example 3 and 1372.5 g of toluene. Flask contents are heated to 40 °C and stirred until homogenous.
- a 1 N solution of H 2 SO 4 is prepared and charged (274.5 ml) to the flask. Contents of the flask are stirred for 20 min at 40 °C. Flask contents are transferred to a separatory funnel and the phases allowed to separate. The aqueous phase is removed and the organic phase is returned to the flask.
- a 2 N solution of H 2 SO 4 is prepared and charged (137.3 ml) to the flask. Contents of the flask are stirred for 20 min at 40°C. Contents of the flask are transferred to a separatory funnel and the phases allowed to separate. The aqueous phase is removed and the organic phase is returned to the flask.
- 2 N H 2 SO 4 (137.3 ml) is charged a second time to the flask. Contents of the flask are stirred for 20 min at 40°C. Contents of the flask are transferred to a separatory funnel and the phases allowed to separate. The aqueous phase is removed and the organic phase is returned to the flask. 2 N H 2 SO 4 (137.3 ml) is again charged to the flask. Contents of the flask are stirred for 20 min at 40°C. Contents of the flask are transferred to a separatory funnel and the phases allowed to separate. The aqueous phase is removed and the organic phase is returned to the flask.
- Saturated aqueous NaCl (150 ml) is charged to the flask. Contents of the flask are stirred for 20 min at 40°C. Contents of the flask are transferred to a separatory funnel and the phases allowed to separate. The aqueous phase is removed and the organic phase is returned to the flask. Saturated aqueous NaCl (150 ml) is again charged to the flask. Contents of the flask are stirred for 20 min at 40°C. Contents of the flask are transferred to a separatory funnel and the phases allowed to separate. The aqueous phase is removed and the organic phase is returned to the flask.
- the contents of the flask are heated to 120°C resulting in the collection of water and toluene.
- the temperature is increased to 135°C and held, resulting in the collection of additional toluene.
- the temperature is increased to 150°C and held, resulting in the collection of additional toluene.
- Vacuum is applied to -250 mmHg (-33331 Pascal) at 150°C, resulting in the collection of toluene.
- Vacuum is further applied to 10-15 mmHg (1333-2000Pa) at 150°C, resulting in the collection of additional toluene. Vacuum is released and the product is filtered. The resulting product is a dark viscous oil.
- the dispersant viscosity modifier of Example 2 is prepared at 25 wt% polymer in 75 wt% diluent oil. This is blended into a group III base oil in amounts by weight to form lubricating compositions, as summarized in Table 2 below.
- Comparative Example 5 includes an amine-free dispersant viscosity modifier (a polymethacrylate (84% C12-15 methacrylate/16% methyl methacrylate), with a weight average molecular weight of 330,000).
- Examples 6 and 7 contain the dispersant viscosity modifiers of Examples 2 and 4 respectively as well as some of the amine-free dispersant viscosity modifier used in Example 5.
- Each of the blends is designed to have nearly equivalent kinematic viscosities at 100°C (KV 100 ) to allow for direct comparison:
- the data in parenthesis is the amount of actives for each component.
- the weight % actives are based on the entire composition.
- the Dispersant-Inhibitor Package may include some oil.
- the lubricating compositions of Examples 5-7 include about 0.75% zinc dialkyldithiophosphate (ZDDP) (which delivers about 0.076% phosphorus to the lubricating composition).
- Friction properties were determined using a Mini Traction Machine (MTM). The lubricants are evaluated in a commercially-available mini-traction tester machine. A simulated concentrated contact forms between a steel ball and a steel disc (Smooth disk). Traction measurements are made at a rolling speed (of the steel ball) of 2.5 m/s and a 20% slide to roll ratio. The temperature was 140 °C and load was 72N. FIGURE 1 shows the Stribeck curve obtained.
- MTM Mini Traction Machine
- the performance of the 3.5% MAA alkyl sulfonic acid in the finished fluid can be measured in all three regions of the Stribeck curve.
- the area of interest is the mixed regime, which can be found between the two vertical lines.
- the mixed regime is indicative of the durability of the friction modifier characteristics of the dispersant viscosity modifier, as determined by the Sequence VID engine test (ASTM D7589), which is heavily weighted towards the mixed regime.
- the 3.5% MAA alkyl sulfonic acid outperformed the baseline (Example 5) formulation.
- comparative Example 8 includes a conventional dispersant viscosity modifier (32 wt % active polymer, 68 wt % oil).
- this replaced with either 3.5% MAA alkyl sulfonic acid (prepared at 25 wt % polymer, 75 wt % oil) or 3.5% MAA aryl tributylammonium sulfonate (prepared at 29.7 wt % polymer, 70.3 wt % oil) at a treat rate to obtain the following viscometric parameters:
- the weight % actives are also based on the entire composition.
- the lubricating compositions of Examples 8-10 include about 1% zinc dialkyldithiophosphate (ZDDP) (which delivers about 0.11% phosphorus to the composition).
- ZDDP zinc dialkyldithiophosphate
- the compositions include about 1% sulfated ash and have a TBN of about 8.5.
- the film thickness of the blends in TABLE 3, when subjected to boundary, mixed and hydrodynamic lubrication conditions is measured by an elastohydrodynamic (EHD) ball on plate rig.
- EHD elastohydrodynamic
- a chamber is flooded with one of the blends from TABLE 3.
- the chamber is equipped with a ball that rolls on a glass plate and a chromium spacer.
- the film thickness is measured to the nanometer scale.
- the experiment is performed at 140°C over a variety of rolling speeds. Conditions are as follows: 0.5 GPa Hertz Pressure, 17 N.
- FIGURE 2 shows the EHD data obtained. It can be seen that the Example 9 and 10 NOCH-S DVMs both form a thicker film, as compared to comparative Example 8.
- each chemical or composition referred to herein should be interpreted as being a commercial grade material which may contain the isomers, by-products, derivatives, and other such materials which are normally understood to be present in the commercial grade.
- the amount of each chemical component is presented exclusive of any solvent or diluent oil, which may be customarily present in the commercial material, unless otherwise indicated. It is to be understood that the upper and lower amount, range, and ratio limits set forth herein may be independently combined. Similarly, the ranges and amounts for each element of the invention may be used together with ranges or amounts for any of the other elements.
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Claims (15)
- Schmierzusammensetzung, umfassend:ein Öl mit Schmierviskosität; undmindestens 0,05 Gew.-% eines öllöslichen dispergierenden Viskositätsmodifizierers, umfassend ein Polymerrückgrat auf Olefinbasis und mindestens eine seitenständige funktionelle Gruppe, ausgewählt aus Alkyl- und Arylsulfonatsalzen, Alkyl- und Arylsulfonsäuren und Kombinationen davon, das Polymerrückgrat auf Olefinbasis umfassend ein Copolymer auf Ethylenolefinbasis, wobei jede der mindestens einen seitenständigen funktionellen Gruppe an das Polymerrückgrat auf Olefinbasis durch eine Verknüpfungsgruppe unabhängig angelagert ist, die mindestens eine seitenständige funktionelle Gruppe umfassend ein Sulfonatmolekülteil, wobei die mindestens eine seitenständige funktionelle Gruppe von einer sulfonierten Hydrocarbylverbindung abstammt, die aus der Gruppe ausgewählt ist, bestehend aus:d von 1-10 ist,e mindestens 1 ist,B NH2 oder OH ist,R11, R12, R13 und R14 unabhängig H oder eine C1- bis C30-Alkylgruppe sind, undR15, R16, R17 und R18 unabhängig aus H, OH, NH2, Alkylgruppen und Alkoxygruppen ausgewählt sind
- Schmierzusammensetzung nach Anspruch 1, wobei der Sulfonatmolekülteil von dem Polymerrückgrat auf Olefinbasis durch eine C4-C24-Hydrocarbylgruppe beabstandet ist.
- Schmierzusammensetzung nach Anspruch 1 oder 2, wobei die mindestens eine seitenständige funktionelle Gruppe eine C3-C24-Alkylkette umfasst, die den Sulfonatmolekülteil von dem Polymerrückgrat beabstandet.
- Schmierzusammensetzung nach einem der Ansprüche 1 bis 3, wobei mindestens einige der Verknüpfungsgruppen von einem ethylenisch ungesättigten Carbonsäuremonomer abstammen.
- Schmierzusammensetzung nach Anspruch 2 oder 3, wobei die Verknüpfungsgruppen an die seitenständigen Gruppen durch Verknüpfereinheiten, die von mindestens einem von Hydroxylalkylaminen, Alkylenpolyaminen und Polyolen abstammen, angelagert sind.
- Zusammensetzung nach Anspruch 5, wobei mindestens einige der Verknüpfungsgruppen von Maleinsäureanhydrid abstammen und mindestens einige der Verknüpfereinheiten von einem Hydroxylalkylamin abstammen.
- Schmierzusammensetzung nach einem der Ansprüche 1 bis 6, wobei der Sulfonatmolekülteil ein Sulfonatsalz umfasst, das ein Kation der allgemeinen Form - (NR3R4R5) beinhaltet, wobei R3, R4 und R5 unabhängig aus H und C1- bis C30-Alkylgruppen ausgewählt sind.
- Schmierzusammensetzung nach einem der Ansprüche 1 bis 7, wobei ein Gewichtsverhältnis von Verknüpfungsgruppen zu dem Polymerrückgrat in dem dispergierenden Viskositätsmodifizierer mindestens 2 : 100 ist.
- Schmierzusammensetzung nach einem der Ansprüche 1 bis 8, wobei ein Gewichtsverhältnis von Verknüpfungsgruppen zu dem Polymerrückgrat in dem dispergierenden Viskositätsmodifizierer bis zu 10 : 100 ist.
- Schmierzusammensetzung nach einem der Ansprüche 1 bis 9, wobei der dispergierende Viskositätsmodifizierer einen HLB-Wert von bis zu 10 aufweist,
wobei HLB = 20*Mh/M, wobei Mh die Molekularmasse des hydrophilen Anteils des Moleküls ist und M die Molekülmasse des gesamten Moleküls ist. - Schmierzusammensetzung nach einem der Ansprüche 1 bis 10, wobei das Copolymer auf Ethylenolefinbasis mindestens 10 Molprozent Ethylen umfasst.
- Schmierzusammensetzung nach einem der Ansprüche 1 bis 11, wobei das Polymerrückgrat auf Olefinbasis ein Zahlenmittel einer Molekülmasse, wie durch Gelpermeationschromatographie unter Verwendung eines Polystyrolstandards gemessen, von mehr als mindestens 1000 aufweist.
- Schmierzusammensetzung nach einem der Ansprüche 1 bis 12, wobei die Zusammensetzung ferner mindestens eines von einem Dispergiermittel, einem Detergens, einem überbasischen Detergens, einem Antioxidans, einem Viskositätsmodifizierer, einem Reibungsmodifizierer, einem Korrosionsinhibitor, einem Stockpunkterniedriger, einem Dichtungsquellmittel, einem Demulgator und einem Antiverschleißmittel umfasst.
- Verwendung des dispergierenden Viskositätsmodifizierers nach einem der Ansprüche 1 bis 13 zum Erhöhen einer Filmdicke und/oder Antiverschleißleistung einer Motorschmierzusammensetzung.
- Verfahren zum Herstellen einer Schmierzusammensetzung, umfassend:(i) Bereitstellen eines Polymerrückgrates auf Olefinbasis mit einer oder mehreren Acylierungsverknüpfungsgruppen, die jeweils unabhängig entlang des Polymerrückgrates angelagert sind, das Polymerrückgrat auf Olefinbasis umfassend ein Copolymer auf Ethylenolefinbasis;(ii) optional, Reagieren jeder Acylierungsgruppe mit einem Hydroxyalkylamin, einem Alkylenpolyamin, einem Polyol oder einer Kombination davon, resultierend in einem Polymer auf Olefinbasis mit einer oder mehreren Verknüpfereinheiten, die jeweils unabhängig entlang des Polymerrückgrates angelagert sind; und(iii) Reagieren jeder Verknüpfungsgruppe oder Verknüpfereinheit mit einer Hydrocarbylsulfonatverbindung, ausgewählt aus Sulfonatsalzen und Sulfonsäuren, resultierend in einem dispergierenden Viskositätsmodifizierer, umfassend eine oder mehrere seitenständige Hydrocarbylsulfonatgruppen, die jeweils unabhängig an das Polymer auf Olefinbasis angelagert sind, wobei die sulfonierte Hydrocarbylverbindung aus der Gruppe ausgewählt ist, bestehend aus:d von 1-10 ist,e mindestens 1 ist,B NH2 oder OH ist,R11, R12, R13 und R14 unabhängig voneinander H oder eine C1- bis C30-Alkylgruppe sind, undR15, R16, R17 und R18 unabhängig aus H, OH, NH2, Alkylgruppen und Alkoxygruppen ausgewählt sind.
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Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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CN110114448B (zh) | 2016-12-27 | 2022-03-04 | 路博润公司 | 具有烷基化萘胺的润滑组合物 |
DK3562921T3 (da) | 2016-12-27 | 2022-06-07 | Lubrizol Corp | Smøremiddelsammensætning indbefattende n-alkyleret dianilin |
WO2019089177A1 (en) * | 2017-10-30 | 2019-05-09 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with engine wear protection |
JP7330721B2 (ja) * | 2019-03-06 | 2023-08-22 | 日本乳化剤株式会社 | 変性ポリオレフィン材料及びその製造方法、並びに、樹脂フィルム及び包装材料 |
WO2024158648A1 (en) | 2023-01-24 | 2024-08-02 | The Lubrizol Corporation | Lubricating composition with phenolic antioxidant and low active sulfur |
Family Cites Families (43)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3444170A (en) | 1959-03-30 | 1969-05-13 | Lubrizol Corp | Process which comprises reacting a carboxylic intermediate with an amine |
DE1248643B (de) | 1959-03-30 | 1967-08-31 | The Lubrizol Corporation, Cleveland, Ohio (V. St. A.) | Verfahren zur Herstellung von öllöslichen aeylierten Aminen |
DE1271877B (de) | 1963-04-23 | 1968-07-04 | Lubrizol Corp | Schmieroel |
US3381022A (en) | 1963-04-23 | 1968-04-30 | Lubrizol Corp | Polymerized olefin substituted succinic acid esters |
GB1054280A (de) | 1963-12-11 | |||
GB1052380A (de) | 1964-09-08 | |||
US3316177A (en) | 1964-12-07 | 1967-04-25 | Lubrizol Corp | Functional fluid containing a sludge inhibiting detergent comprising the polyamine salt of the reaction product of maleic anhydride and an oxidized interpolymer of propylene and ethylene |
GB1121641A (en) * | 1965-01-08 | 1968-07-31 | Castrol Ltd | Additives for lubricating compositions |
DE1595234A1 (de) | 1965-04-27 | 1970-03-05 | Roehm & Haas Gmbh | Verfahren zur Herstellung oligomerer bzw. polymerer Amine |
US3340281A (en) | 1965-06-14 | 1967-09-05 | Standard Oil Co | Method for producing lubricating oil additives |
US3433744A (en) | 1966-11-03 | 1969-03-18 | Lubrizol Corp | Reaction product of phosphosulfurized hydrocarbon and alkylene polycarboxylic acid or acid derivatives and lubricating oil containing the same |
US3501405A (en) | 1967-08-11 | 1970-03-17 | Rohm & Haas | Lubricating and fuel compositions comprising copolymers of n-substituted formamide-containing unsaturated esters |
US3642728A (en) | 1968-10-07 | 1972-02-15 | Exxon Research Engineering Co | Sulfonated polymers |
US3576743A (en) | 1969-04-11 | 1971-04-27 | Lubrizol Corp | Lubricant and fuel additives and process for making the additives |
US3632511A (en) | 1969-11-10 | 1972-01-04 | Lubrizol Corp | Acylated nitrogen-containing compositions processes for their preparationand lubricants and fuels containing the same |
US3749695A (en) * | 1971-08-30 | 1973-07-31 | Chevron Res | Lubricating oil additives |
US3870841A (en) | 1972-10-02 | 1975-03-11 | Exxon Research Engineering Co | Flexible polymeric compositions comprising a normally plastic polymer sulfonated to about 0.2 to about 10 mole % sulfonate |
US4144181A (en) * | 1977-04-29 | 1979-03-13 | Exxon Research & Engineering Co. | Polymeric additives for fuels and lubricants |
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 |
US4863623A (en) | 1988-03-24 | 1989-09-05 | Texaco Inc. | Novel VI improver, dispersant, and anti-oxidant additive and lubricating oil composition containing same |
GB8818711D0 (en) | 1988-08-05 | 1988-09-07 | Shell Int Research | Lubricating oil dispersants |
US6117825A (en) | 1992-05-07 | 2000-09-12 | Ethyl Corporation | Polyisobutylene succinimide and ethylene-propylene succinimide synergistic additives for lubricating oils compositions |
US5264139A (en) * | 1992-06-01 | 1993-11-23 | Texaco Inc. | Antioxidant dispersant antiwear VI improver additive and lubricating oil composition containing same |
GB9611318D0 (en) | 1996-05-31 | 1996-08-07 | Exxon Chemical Patents Inc | Overbased metal-containing detergents |
GB9611428D0 (en) | 1996-05-31 | 1996-08-07 | Exxon Chemical Patents Inc | Overbased metal-containing detergents |
GB9611316D0 (en) | 1996-05-31 | 1996-08-07 | Exxon Chemical Patents Inc | Overbased metal-containing detergents |
GB9611424D0 (en) | 1996-05-31 | 1996-08-07 | Exxon Chemical Patents Inc | Overbased metal-containing detergents |
US6165235A (en) | 1997-08-26 | 2000-12-26 | The Lubrizol Corporation | Low chlorine content compositions for use in lubricants and fuels |
US6107258A (en) | 1997-10-15 | 2000-08-22 | Ethyl Corporation | Functionalized olefin copolymer additives |
US6107257A (en) | 1997-12-09 | 2000-08-22 | Ethyl Corporation | Highly grafted, multi-functional olefin copolymer VI modifiers |
JP2003504487A (ja) | 1999-07-09 | 2003-02-04 | ザ ルブリゾル コーポレイション | 向上した酸化的安定性を有する窒素含有エステル化カルボキシ含有インターポリマーおよびそれを含有する潤滑剤 |
MXPA02004109A (es) | 1999-10-25 | 2002-10-17 | Lubrizol Corp | Interpolimeros que contienen composicion de aceite lubricante. |
US6559105B2 (en) | 2000-04-03 | 2003-05-06 | The Lubrizol Corporation | Lubricant compositions containing ester-substituted hindered phenol antioxidants |
WO2001098387A2 (en) | 2000-06-22 | 2001-12-27 | The Lubrizol Corporation | Functionalized isobutylene-polyene copolymers and derivatives thereof |
WO2003040273A2 (en) | 2001-11-05 | 2003-05-15 | The Lubrizol Corporation | Lubricating composition with improved fuel economy |
US7238650B2 (en) | 2002-06-27 | 2007-07-03 | The Lubrizol Corporation | Low-chlorine, polyolefin-substituted, with amine reacted, alpha-beta unsaturated carboxylic compounds |
US20050038319A1 (en) | 2003-08-13 | 2005-02-17 | Benad Goldwasser | Gastrointestinal tool over guidewire |
CN100560611C (zh) | 2004-04-19 | 2009-11-18 | 卢布里佐尔公司 | 基于马来酸酐-苯乙烯共聚物的分散剂粘度改性剂 |
US7790661B2 (en) | 2004-07-30 | 2010-09-07 | The Lubrizol Corporation | Dispersant viscosity modifiers containing aromatic amines |
US7253231B2 (en) * | 2005-01-31 | 2007-08-07 | Afton Chemical Corporation | Grafted multi-functional olefin copolymer VI modifiers and uses thereof |
CN102482607A (zh) | 2009-07-08 | 2012-05-30 | 卢布里佐尔公司 | 分散剂粘度改进剂 |
JP5575892B2 (ja) | 2009-07-08 | 2014-08-20 | ザ ルブリゾル コーポレイション | 分散性粘度調整剤 |
US20130303418A1 (en) | 2012-05-08 | 2013-11-14 | Shell Oil Company | High molecular weight polymers as viscosity modifiers |
-
2015
- 2015-09-15 WO PCT/US2015/050166 patent/WO2016044262A1/en active Application Filing
- 2015-09-15 US US15/508,638 patent/US20170283733A1/en not_active Abandoned
- 2015-09-15 EP EP15778794.6A patent/EP3209756B1/de active Active
Also Published As
Publication number | Publication date |
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WO2016044262A1 (en) | 2016-03-24 |
US20170283733A1 (en) | 2017-10-05 |
EP3209756A1 (de) | 2017-08-30 |
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