WO2006088693A2 - Novel viscosity modifying dispersant - Google Patents
Novel viscosity modifying dispersant Download PDFInfo
- Publication number
- WO2006088693A2 WO2006088693A2 PCT/US2006/004238 US2006004238W WO2006088693A2 WO 2006088693 A2 WO2006088693 A2 WO 2006088693A2 US 2006004238 W US2006004238 W US 2006004238W WO 2006088693 A2 WO2006088693 A2 WO 2006088693A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil soluble
- molecular weight
- average molecular
- number average
- acylating agent
- Prior art date
Links
- 239000002270 dispersing agent Substances 0.000 title claims description 31
- 230000000051 modifying effect Effects 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims abstract description 68
- 230000001050 lubricating effect Effects 0.000 claims abstract description 40
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 38
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims abstract description 35
- 229920000768 polyamine Polymers 0.000 claims abstract description 23
- 229920005862 polyol Polymers 0.000 claims abstract description 18
- 150000003077 polyols Chemical class 0.000 claims abstract description 16
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 60
- 239000000047 product Substances 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 36
- 229920001577 copolymer Polymers 0.000 claims description 28
- 229920000642 polymer Polymers 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 229920002367 Polyisobutene Polymers 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 7
- 229940014800 succinic anhydride Drugs 0.000 claims description 7
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 claims description 6
- 229920001155 polypropylene Polymers 0.000 claims description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- 239000002174 Styrene-butadiene Substances 0.000 claims description 5
- 125000005024 alkenyl aryl group Chemical group 0.000 claims description 5
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 5
- 229920000098 polyolefin Polymers 0.000 claims description 5
- 239000011115 styrene butadiene Substances 0.000 claims description 5
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 5
- ROGIWVXWXZRRMZ-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical class CC(=C)C=C.C=CC1=CC=CC=C1 ROGIWVXWXZRRMZ-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 238000006446 extruder reaction Methods 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 2
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 2
- 239000001384 succinic acid Substances 0.000 claims description 2
- 238000002485 combustion reaction Methods 0.000 abstract description 4
- 239000003921 oil Substances 0.000 description 79
- 235000019198 oils Nutrition 0.000 description 79
- 239000004034 viscosity adjusting agent Substances 0.000 description 17
- -1 oxyalkylene amine Chemical class 0.000 description 16
- 239000000654 additive Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 239000002253 acid Chemical class 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000004711 α-olefin Substances 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 4
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical compound CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 4
- GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical compound C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- NHLUYCJZUXOUBX-UHFFFAOYSA-N nonadec-1-ene Chemical compound CCCCCCCCCCCCCCCCCC=C NHLUYCJZUXOUBX-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229920001038 ethylene copolymer Polymers 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920005652 polyisobutylene succinic anhydride Polymers 0.000 description 3
- 229920000193 polymethacrylate Polymers 0.000 description 3
- 229920001021 polysulfide Polymers 0.000 description 3
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 3
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical class C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- PTYXPKUPXPWHSH-UHFFFAOYSA-N 1-(butyltetrasulfanyl)butane Chemical compound CCCCSSSSCCCC PTYXPKUPXPWHSH-UHFFFAOYSA-N 0.000 description 2
- VQOXUMQBYILCKR-UHFFFAOYSA-N 1-Tridecene Chemical compound CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- TYLBURSJNXVZOU-UHFFFAOYSA-N CCCCCCCCCCCCCCCC=C.CCCCCCCCCCCCCCCCC=C Chemical compound CCCCCCCCCCCCCCCC=C.CCCCCCCCCCCCCCCCC=C TYLBURSJNXVZOU-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- 238000005698 Diels-Alder reaction Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- CIBXCRZMRTUUFI-UHFFFAOYSA-N [chloro-[[chloro(phenyl)methyl]disulfanyl]methyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)SSC(Cl)C1=CC=CC=C1 CIBXCRZMRTUUFI-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000002199 base oil Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003749 cleanliness Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
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- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
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- 239000012530 fluid Substances 0.000 description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
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- 239000007788 liquid 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
- 238000012986 modification Methods 0.000 description 2
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- 239000003607 modifier Substances 0.000 description 2
- VAMFXQBUQXONLZ-UHFFFAOYSA-N n-alpha-eicosene Natural products CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
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- 229920000058 polyacrylate Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
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- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical class CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GLOYGJPNNKTDIG-UHFFFAOYSA-N SC=1N=NSC=1S Chemical class SC=1N=NSC=1S GLOYGJPNNKTDIG-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- ORFOPKXBNMVMKC-DWVKKRMSSA-N ceftazidime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 ORFOPKXBNMVMKC-DWVKKRMSSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012612 commercial material Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- BTCAIDSTTKFARM-UHFFFAOYSA-N dec-1-ene undec-1-ene Chemical compound CCCCCCCCC=C.CCCCCCCCCC=C BTCAIDSTTKFARM-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 229940043276 diisopropanolamine Drugs 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 229940031098 ethanolamine Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 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 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- DZZRNEZNZCRBOT-UHFFFAOYSA-N hexane-1,2,4-triol Chemical compound CCC(O)CC(O)CO DZZRNEZNZCRBOT-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 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 1
- 239000010705 motor oil Substances 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- LQNPIBHEOATAEO-UHFFFAOYSA-N octanoate;octylazanium Chemical compound CCCCCCCCN.CCCCCCCC(O)=O LQNPIBHEOATAEO-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- OEPVTYSXFQUENG-UHFFFAOYSA-N tetracos-2-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCC=CC OEPVTYSXFQUENG-UHFFFAOYSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 229910052723 transition metal Chemical class 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- USEBTXRETYRZKO-UHFFFAOYSA-L zinc;n,n-dioctylcarbamodithioate Chemical compound [Zn+2].CCCCCCCCN(C([S-])=S)CCCCCCCC.CCCCCCCCN(C([S-])=S)CCCCCCCC USEBTXRETYRZKO-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M177/00—Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/86—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of 30 or more atoms
- C10M129/95—Esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
- C10M133/56—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/02—Pour-point; Viscosity index
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/04—Detergent property or dispersant property
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2070/00—Specific manufacturing methods for lubricant compositions
Definitions
- the present invention relates to a novel viscosity modifying dispersant.
- the invention further provides a method of preparing the novel viscosity modifying dispersant, compositions containing the novel viscosity modifying dispersant and its use in a lubricating composition.
- US Patent 4,517,104 discloses an ethylene copolymer viscosity index improving dispersant additive useful in oil compositions.
- the ethylene copolymer is the reaction product of (a) a copolymer comprising 15 wt % to 90 wt % ethylene, a comonomer derived from 10 wt % to 85 wt % of C 3 to C 28 alpha-olefin; (b) an alkylene or oxyalkylene amine; and (c) a long chain hydrocarbyl substituted succinic anhydride or acid.
- US Patent 5,512,192 discloses a dispersant viscosity modifier for lubricants.
- the dispersant viscosity modifier is prepared by reacting oil soluble substantially hydrogenated vinyl substituted aromatic-aliphatic diene block copolymers with an ethylenically unsaturated carboxylic acid or functional derivative thereof with at least one polyester, at least one polyamine and at least one hydrocarbyl substituted carboxylic acid or anhydride.
- US Patent 5,035,821 discloses a polymer with an end-capped multifunctional viscosity index improver with dispersant properties.
- the polymer is an ethylene copolymer grafted with (a) an ethylenically unsaturated carboxylic acid moiety (e.g., succinic anhydride); then further reacted with (b) a polyamine having two or more primary amino groups or a polyol; (c) a long chain hydrocarbyl substituted dicarboxylic acid material (e.g., alkenyl succinic anhydride) having a functionality of at least 1.2; and (d) a short chain hydrocarbyl substituted dicarboxylic acid or anhydride.
- an ethylenically unsaturated carboxylic acid moiety e.g., succinic anhydride
- a polyamine having two or more primary amino groups or a polyol
- a long chain hydrocarbyl substituted dicarboxylic acid material e.
- an oil soluble product with at least one property selected from acceptable cleanliness, acceptable viscometrics (i.e. low temperature viscosmetrics or acceptable high temperature viscometrics) and acceptable dispersant properties.
- acceptable viscometrics i.e. low temperature viscosmetrics or acceptable high temperature viscometrics
- dispersant properties i.e. low temperature viscosmetrics or acceptable high temperature viscometrics
- the present invention provides an oil soluble product with at least one such property.
- the present invention provides a process for preparing an oil soluble product comprising reacting: (a) an olefin copolymer having a number average molecular weight of more than about 5000 functionalised with an acylating agent; (b) an acylating agent substituted with a hydrocarbyl group having a number average molecular weight of about 350 to about 5000; and (c) a compound selected from the group consisting of (i) a polyamine; (ii) a polyol; and (iii) an aminoalcohol, wherein the oil soluble product has a mole ratio of acylating agents (a) : (b) of 1: greater than 2.
- the present invention provides a process for preparing an oil soluble product comprising reacting: (a) an olefin copolymer having a number average molecular weight of more than about 5000 functionalised with an acylating agent; and (b) a reaction product of an acylating agent substituted with a hydrocarbyl group having a number average molecular weight of about 350 to about 5000 and at least one of (i) a polyamine; (ii) a polyol; and (iii) an aminoalcohol, wherein the oil soluble product has a mole ratio of acylating agents (a) : (b) of 1: greater than 2.
- the present invention provides a lubricating composition
- a lubricating composition comprising: (I) an oil of lubricating viscosity; and (II) an oil soluble reaction product of: (a) an olefin copolymer having a number average molecular weight of more than about 5000 functionalised with an acylating agent; (b) an acylating agent substituted with a hydrocarbyl group having a number average molecular weight of about 350 to about 5000; and (c) a compound selected from the group consisting of (i) a polyamine; (ii) a polyol; and (iii) an aminoalcohol, wherein the oil soluble product has a mole ratio of acylating agents (a) : (b) of 1: greater than 2.
- the present invention provides a process for preparing an oil soluble product comprising reacting:
- the oil soluble product is prepared by reacting (a) + (b) + (c) in a one-step process.
- the reaction referred to here and elsewhere in this specification may involve grafting or other reactive processes.
- a one-step process generally involves adding all of the reactants into a vessel and reacting them to form a product has a mole ratio of (a) : (b) of 1: greater than 2.
- the oil soluble product of the invention is a product derived from (a) + (b) + (c).
- Components (a) + (b) + (c) may also react to give a by-product by reacting (a) + (b) and/or (a) + (c).
- (a) + (b) and/or (a) + (c) may form as intermediates in the formation of the oil soluble product.
- the process is carried out at a temperature in the range of 7O 0 C to 300 0 C, 100 0 C to 22O 0 C or 145°C to 200 0 C.
- the process is carried out for a period of time in the range of 30 seconds to 48 hours, 2 minutes to 24 hours, 5 minutes to 16 hours, or 30 minutes to 4 hours.
- the process is carried out at a pressure in the range of 86.4 kPa to 266 kPa (650 mm Hg to 2000 mm Hg), 91.8 IcPa to 200 kPa (690 mm Hg to 1500 mm Hg) or 95.1 IdPa to 133 kPa (715 mm Hg to 1000 mm Hg).
- the oil soluble product is prepared by reacting (a) + (b) in a two-step process.
- the two step process comprises (I) preparing a reaction product of an acylating agent substituted with a hydrocarbyl group having a number average molecular weight of 350 to 5000 and at least one of (i) a polyamine; (ii) a polyol; and (iii) an aminoalcohol; and (II) reacting the product of step (I) with an olefin copolymer having a number average molecular weight of more than about 5000 functionalised with an acylating agent.
- the reaction product of step (I) is a pre-formed dispersant.
- oil soluble product may be prepared in a two step process comprising pre- reacting (b) and (c) to form a dispersant and reacting the dispersant with (a).
- steps (I) and (II) of the two-step process may be conducted in either order.
- step one i.e. preparation of the dispersant
- step one i.e. preparation of the dispersant
- step two of the process are the same as described for the one step process described above.
- the oil soluble product is free or substantially free of a short chain hydrocarbyl substituted dicarboxylic acid.
- short chain means a carbon chain containing less than 16 carbon atoms.
- the present invention provides process for preparing an oil soluble product comprising reacting:
- the present invention further provides an oil soluble product obtained (or obtainable) by the process described above.
- the oil soluble product is believed to be formed by crosslinking of (a) an olefin copolymer having a number average molecular weight of more than about 5000 functionalised with an acylating agent; and (b) an acylating agent substituted with a hydrocarbyl group having a number average molecular weight of about 350 to about 5000 with (c) a compound selected from the group consisting of (i) a polyamine; (ii) a polyol; and (iii) an aminoalcohol.
- the compound (c) is believed to serve as a crosslinking agent by condensing or otherwise reacting, at least in part, with the acylating functionality of molecules of both components (a) and (b)
- the mole ratio of (a) : (b) may be modified such that amino and/or hydroxy groups sufficiently crosslink the oil soluble product to ensure the dispersant exhibits viscosity index improving properties. If the degree of crosslinking is too high the product gels and becomes oil-insoluble. Alternatively if the degree of crosslinking is too low, the oil soluble product typically has viscosity modifying properties with a modest degree of dispersancy (i.e. a conventional dispersant viscosity modifier). [0021] In several embodiments the mole ratio of (a) : (b) is 1:4 or more, or 1 :8 or more, or 1: 10 or more.
- Examples of suitable ranges for the mole ratio of (a) to (b) include 1:3 to 1:100, 1:6 to 1:85 or 1:12 to 1:75. A person skilled in the art will appreciate that the mole ratio of (b) is greater than the mole ratio of (a).
- the oil soluble product will typically have a mole ratio of (a) : (b) of 1:9 or more or 1:13. Typically the mole ratio of (a) to (b) is less than 1:30 or 1:25. It is believed that pre-forming the olefin copolymer provides an oil soluble product with the ratio of acylating agents (a) to (b) typically less than 1:30 because a portion of the acylating agent is grafted on to the medium.
- a medium e.g., an oil of lubricating viscosity
- the oil soluble product typically has mole ratio of (a) to (b) in several embodiments of 1: 10 or more, 1:20 or more, 1:30 or more or 1:35 or more.
- suitable ranges for the mole ratio of (a) to (b) include 1:35 to 1: 140, 1:45 to 1: 100 or 1:60 to 1:90.
- the oil soluble product is prepared in the presence of a medium.
- the medium is one in which the reactants are generally soluble, often a substantially inert normally liquid organic diluent.
- oils of lubricating viscosity such as an oil with low in halogen content or alkyl aromatic compounds such as toluene, xylene and naphthalene.
- the oil soluble product is formed in the absence of a medium for polymerisation. Generally processes that do not require a medium for polymerisation are carried out in an extruder reaction vessel. Olefin Copolymer Functionalised with Acylating Agent
- the olefin copolymer includes hydrogenated copolymers of styrene-butadiene, ethylene-propylene polymers, hydrogenated styrene-isoprene polymers, hydrogenated alkenyl aryl conjugated diene copolymers, or mixtures thereof.
- the olefin copolymer is selected from the group consisting of styrene-butadiene polymers, ethylene-propylene polymers, hydrogenated alkenyl aryl conjugated diene copolymers, and mixtures thereof.
- the olefin copolymer comprises hydrogenated styrene-isoprene polymers, with the proviso that mole ratio of (a) : (b) is 1:8 or more or any of the ratios or ratios described above that are 1:8 or more.
- the olefin copolymer functionalised with an acylating agent has a number average molecular weight of more than 5000, 10,000 or more, or 20,000 or 30,000 or more. Examples of suitable ranges for the number average molecular weight include 7500 to 350,000, 12,000 to 200,000, 25,000 to 100,000, 30,000 to 80,000 or 35,000 to 60,000.
- the alkyl radical contains 1 to 30, 1 to 10, 1 to 6 or 1 to 3 carbon atoms.
- the hydrocarbyl group includes an alkyl radical that has a straight chain, a branched chain or mixtures thereof.
- Examples of comonomers include propylene, 1-butene, 1-hexene, 1-octene, 4-methyl-l-pentene, 1-decene or mixtures thereof.
- the comonomer includes 1-butene, propylene or mixtures thereof.
- the olefin copolymers include ethylene-propylene copolymers, ethylene- 1-butene copolymers or mixtures thereof.
- the alpha-olefin includes a comonomer with 6 to 40, 10 to 34 or 14 to 22 carbon atoms.
- alpha-olefins include 1-decene 1-undecene, 1-dodecene, 1-tridecene, 1-butadecene, 1- pentadecene, 1-hexadecene, 1-heptadecene 1-octadecene, 1-nonadecene, 1-eicosene, 1-doeicosene, 2-tetracosene, 3-methyl-l-henicosene, 4-ethyl-2- tetracosene or mixtures thereof or reactive equivalents thereof.
- alpha-olefins include 1-pentadecene, 1-hexadecene, 1-heptadecene 1- octadecene, 1-nonadecene or mixtures thereof.
- the alpha-olefins are often commercially available as mixtures, especially as mixtures of C 16 -C 18 alpha olefins.
- the olefin copolymer is an ethylene-propylene copolymer and may contain up to 3, 4 or 5 monomer types, that is, it may contain additional monomers beside ethylene and propylene.
- the composition of the ethylene-propylene copolymer in several embodiments has an ethylene content from 15 wt % to 90 wt % or 30 wt % to 80 wt % of the copolymer; and a propylene content of 10 wt % to 85 wt % or 20 wt % to 70 wt % of the copolymer.
- olefin copolymer is an ethylene-propylene copolymer, with the ethylene content ranging from 15 wt % to 90 wt % of the copolymer and the propylene content ranging from 10 wt % to 85 wt % of the copolymer.
- the acylating agent which may be substituted onto the olefin copolymer of (a) or which may be substituted with the hydrocarbyl group of (b) in one embodiment is an unsaturated carboxylic acid anhydride or derivative thereof that may be wholly esterified, partially esterified or mixtures thereof.
- the acylating agent of component (a) comprises an unsaturated carboxylic acid or reactive equivalents thereof.
- partially esterified other derivatives include acids, salts or mixtures thereof.
- Suitable salts include alkali metals, alkaline earth metals or mixtures thereof.
- the salts include lithium, sodium, potassium, magnesium, calcium or mixtures thereof.
- the unsaturated carboxylic acids or derivatives thereof may comprise acrylic acid, methyl acrylate, methacrylic acid, maleic acid or anhydride, fumaric acid, itaconic acid or anhydride or mixtures thereof or reactive equivalents thereof.
- the acylating agent of (b) comprises a succinic anhydride.
- Suitable examples of the unsaturated dicarboxylic acid anhydride or derivatives include itaconic anhydride, maleic anhydride, methyl maleic anhydride, ethyl maleic anhydride, dimethyl maleic anhydride or mixtures thereof.
- the unsaturated carboxylic acid anhydrides or derivatives thereof functionality may be used alone or in combination.
- the acylating agent when reacted and/or grafted with (a) a olefin copolymer having a number average molecular weight of more than about 5000, may be incorporated into an olefin polymer backbone and/or grafted on to the backbone.
- the unsaturated carboxylic acid anhydride or derivatives thereof is grafted onto the backbone.
- the unsaturated carboxylic acid anhydride or derivatives thereof is incorporated into olefin polymer backbone.
- the acylating agent may be reacted with a hydrocarbon to form an acylating agent substituted with a hydrocarbyl group of (b).
- the acylating agent is substituted with a hydrocarbyl group derived from a hydrocarbon with a number average molecular weight of 350 to 5000, 400 to 3000, 450 to 2500, 500 to 2300, 550 to 1600 or 900 to 1600.
- the hydrocarbyl group substituted onto the acylating agent in one embodiment is a substituted or unsubstituted oxyalkylene or a polyolefin, such as a polyisobutylene or polybutene.
- the acylating agent substituted with a hydrocarbyl group comprises a polyisobutylene succinic acid or anhydride, wherein the polyisobutylene has a number average molecular weight of 350 to 3000.
- acylating agent may be grafted or reacted onto an olefin copolymer viscosity modifier by a similar process as taught in US Patent
- the oil soluble product is formed in the presence of a polyamine.
- Suitable polyamines are well known to a person skilled in the art of preparing a dispersant.
- suitable polyamines include alkylene amines or oxyalkylene amines.
- Alkylene amine typically contain alkylene groups containing 2 to 20 or 2 to 10 carbon atoms; and 2 to 14 or 2 to 10 nitrogen atoms.
- Suitable examples of polyamines include ethylenepolyamines, propylenepolyamines, butylenepolyamines or mixtures thereof.
- ethylenepolyamines examples include triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, amine still bottoms (often described as HP AXTM) or mixtures thereof. In one embodiment the polyamine is still bottoms.
- Polvola ethylenepolyamines
- the oil soluble product is formed in the presence of a polyol or mixtures thereof.
- suitable polyols include compounds containing 2 to 10 or 2 to 6 hydroxyl groups.
- suitable polyol compounds include glycol, and glycerol.
- polyol compounds examples include glycerol, erythritol, 2-hydroxymethyl-2- methyl- 1 ,3-propanediol (trimethylolethane), 2-hydroxymethyl-2-ethyl- 1,3- propanediol (trimethylolpropane), 1,2,4-hexanetriol, ethylene glycol, propylene glycol, butylene glycol, pentaerythritol, dipentaerythritol, mannitol, sorbitol or mixtures thereof.
- Aminoalcohol aminoalcohol
- the oil soluble product is formed in the presence of an aminoalcohol.
- aminoalcohols include ethanolamine, isopropanolamine, diethanolamine, triethanolamine, diethylethanolamine, dimethylethanolamine, dibutylethanolamine, 3-amino-l,2-propanediol, serinol, 2-amino-2-methyl-l,3-propanediol, tris(hydroxymethyl)-aminomethane, 1- amino-1-deoxy-D-sorbitol, diethanol amine; diisopropanolamine, N-methyl-N,N- diethanol amine, triethanolamine, N,N,N',N'-tetrakis(2- hydroxypropyl)ethylenediamine, 2-amino-2-methyl-l-propanol, 2- dimethylamino-methyl-1 -propanediol, 2-amino-2-ethyl-l,3-propanediol
- the present invention provides a lubricating composition comprising:
- the emulsion composition includes natural or synthetic oils of lubricating viscosity, oil derived from hydrocracldng, hydro gen ati on, hydrofinishing, unrefined, refined and re-refined oils or mixtures thereof.
- Natural oils include animal oils, vegetable oils, mineral oils or mixtures thereof.
- Synthetic oils include a hydrocarbon oil, a silicon-based oil, a liquid esters of phosphorus-containing acid. Synthetic oils may be produced by
- Fischer-Tropsch reactions and typically may be hydroisomerised Fischer-
- Oils of lubricating viscosity may also be defined as specified in the
- the oil of lubricating viscosity comprises an API Group I,
- oil of lubricating viscosity is an API Group II, III, IV, V or VI oil there may be up to a maximum of 40 wt % or up to a maximum of 5 wt % of the lubricating oil being an API Group I oil.
- the lubricating composition has a SAE viscosity grade from XW-Y, wherein X is an integer from 0 to 20 and Y is an integer from
- X is an integer chosen from 0, 5, 10, 15 or 20; and Y is an integer chosen from 20, 25, 30, 35, 40, 45 or 50.
- oil of lubricating viscosity is present from
- the composition optionally further includes at least one additional performance additive.
- additional performance additives include metal deactivators, detergents, dispersants, friction modifiers, viscosity modifiers, dispersant viscosity modifiers, extreme pressure agents, antiwear agents, antioxidants, corrosion inhibitors, foam inhibitors, demulsifiers, pour point depressants, seal swelling agents or mixtures thereof.
- the total combined amount of the additional performance additive compounds are present from 0 Wt % to 25 wt %, 0.01 wt % to 20 wt %, 0.1 wt % to 15 wt % or 0.5 wt % to 10 wt % of the composition.
- the additional performance additives may be present, it is common for the additional performance additives to be present in different amounts relative to each other.
- the present invention is in the form of a concentrate (which can be combined with additional oil to form, in whole or in part, a finished lubricant), the ratio of the oil soluble product of the invention and the optional additional performance additives in an oil of lubricating viscosity, to diluent oil including may be in the range of 80:20 to 10:90 or to 5:95 by weight.
- Antioxidants include molybdenum dithiocarbamates, sulphurised olefins, hindered phenols, diphenylamine.
- Detergents include neutral or overbased, Newtonian or non-Newtonian, basic salts of alkali, alkaline earth and transition metals with one or more of a phenate, a sulphurised phenate, a sulphonate, a carboxylic acid, a phosphorus acid, a mono- and/or a di- thiophosphoric acid, a saligenin, an alkylsalicylate, a salixarate.
- Dispersants include N-substituted long chain alkenyl succinimide as well as posted treated versions thereof.
- Post-treated dispersants include those treated by reaction with urea, thiourea, dimercaptothiadiazoles, carbon disulphide, aldehydes, ketones, carboxylic acids, hydrocarbon-substituted succinic anhydrides, nitriles, epoxides, boron compounds, or phosphorus compounds.
- Viscosity modifiers include hydrogenated copolymers of styrene-butadiene, olefin copolymers other than the oil soluble product of the invention (such as ethylene-propylene polymers, polyisobutenes, hydrogenated styrene-isoprene polymers, hydrogenated isoprene polymers), polymethacrylate acid esters, polyacrylate acid esters, polyalkyl styrenes, hydrogenated alkenyl aryl conjugated diene copolymers, polyalkylraethacrylates and esters of maleic anhydride-styrene copolymers.
- Antiwear agents include compounds such as metal thiophosphates, especially zinc dialkyldithiophosphates; phosphoric acid esters or salt thereof; phosphites; and phosphorus-containing carboxylic esters, ethers, and amides.
- Antiscuffing agents including organic sulphides and polysulphides, such as benzyldisulphide, bis-(chlorobenzyl) disulphide, dibutyl tetrasulphide, di- tertiary butyl polysulphide, di-tert-butylsulphide, sulphurised Diels-Alder adducts or alkyl sulphenyl N'N-dialkyl dithiocarbamates.
- EP agents including chlorinated wax, organic sulphides and polysulphides, such as benzyldisulphide, bis-(chlorobenzyl) disulphide, dibutyl tetrasulphide, sulphurised methyl ester of oleic acid, sulphurised alkylphenol, sulphurised dipentene, sulphurised terpene, and sulphurised Diels-Alder adducts; phosphosulphurised hydrocarbons, metal thiocarbamates, such as zinc dioctyldithiocarbamate and barium heptylphenol diacid. Any of the above classes of additives may also be used in the composition of the invention.
- the invention may also include friction modifiers including fatty amines, esters such as borated glycerol esters, fatty phosphites, fatty acid amides, fatty epoxides, borated fatty epoxides, alkoxylated fatty amines, borated alkoxylated fatty amines, metal salts of fatty acids, fatty imidazolines, condensation products of carboxylic acids and polyalkylene- polyamines, amine salts of alkylphosphoric acids.
- esters such as borated glycerol esters, fatty phosphites, fatty acid amides, fatty epoxides, borated fatty epoxides, alkoxylated fatty amines, borated alkoxylated fatty amines, metal salts of fatty acids, fatty imidazolines, condensation products of carboxylic acids and polyalkylene- polyamines, amine salts of alkylphosphoric acids.
- the formulation of the invention may also include dispersant viscosity modifiers (often referred to as DVM), including functionalised polyolefins, for example, ethylene-propylene copolymers that have been functionalized with the reaction product of maleic anhydride and an amine; polymethacrylates functionalised with an amine, or styrene-maleic anhydride copolymers reacted with an amine.
- DVM dispersant viscosity modifiers
- corrosion inhibitors including octylamine octanoate, condensation products of dodecenyl succinic acid or anhydride and a fatty acid such as oleic acid with a polyamine
- metal deactivators including derivatives of benzotriazoles, 1,2,4-triazoles, benzimidazoles, 2-alkyldithiobenzimidazoles or 2-alkyldithiobenzothiazoles
- foam inhibitors including copolymers of ethyl acrylate and 2-ethylhexylacrylate and optionally 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
- seal swell agents including Exxon Necton-37
- Mineral Seal Oil (FN 3200); may also be used in the composition of the invention.
- the oil soluble product of the present invention is useful as a dispersant with viscosity index improving properties for a transmission fluid, a gear oil, a hydraulic fluid or an internal combustion engine lubricant, for example, for diesel fuelled engines, gasoline fuelled engines, natural gas fuelled engines or mixed gasoline/alcohol fuelled engines.
- In one embodiment of the invention provides a method for lubricating an internal combustion engine, comprising supplying thereto a lubricant comprising the oil soluble product as described herein.
- a lubricant comprising the oil soluble product as described herein.
- the use of the oil soluble product in an internal combustion engine may impart one or more properties selected from acceptable cleanliness, acceptable viscometrics (i.e. low temperature viscosmetrics or acceptable high temperature viscometrics) and acceptable dispersant properties.
- the oil soluble product is present in a lubricating composition from 0.001 wt % to 30 wt %, 0.1 wt % to 20 wt %, 0.5 wt % to 15 wt %, 1 wt % to 10 wt % or from 2 wt % to 8 wt % of the lubricating composition.
- a mixture of a Group III oil of Nexbase 3050TM supplied by Fortum oil company (200Og) and toluene (360g) is heated to 125°C under N 2 in a 5-litre flask. At this temperature, a 25SSI ethylene-propylene copolymer (424g) is added portion wise and the mixture left to heat for a further three hours. The reaction is then heated to 160 0 C and tert-butylperoxide (24g) in toluene (80ml) is added drop wise to the polymer solution over 105 minutes. Ten minutes after the start of the initiator addition, maleic anhydride (41.6g) in acetone (80ml) is added drop wise to the mixture over 90 minutes. The solution is then left to heat at this temperature for a further two hours. The volatile solvents are removed by distillation under reduced pressure to give a viscous yellow oil (2453g, 99%). Examples 1 to 5
- Examples 1 to 5 are prepared by reacting/grafting a polyisobutylene (PIBSA) with a number average molecular weight of 1600 in the amounts shown in Table 1 (PIBSA is diluted to 70 % active ingredient in diluent oil) with the product of Preparative Example 1 and an amine (Methylene tetramine) at 180 0 C under a nitrogen atmosphere until a viscous product is formed.
- Table 1 summarises the amounts of chemicals reacted.
- Reference Examples 1 to 5 are prepared by reacting a 25 SSI ethylene- propylene copolymer (OCPl) a PIBSA (diluted to 70 % in diluent oil) with the product of an amine (tri ethylene tetramine) at 180 0 C under a nitrogen atmosphere until a viscous product is formed.
- OCPl ethylene- propylene copolymer
- PIBSA diluted to 70 % in diluent oil
- a series of lubricating compositions containing Examples 1 to 5 and Reference Examples 1 to 4 are prepared by blending 4.2 wt % of the product of said Examples in a base oil to form 5W-30 compositions; and optionally in the presence of a portion of a conventional olefin viscosity modifier.
- the lubricating compositions prepared are summarised in Table 3.
- LC is the lubricating composition.
- Reference Lubricating Compositions (REFLC) 1 to 4 are prepared in the same manner as Lubricating Compositions 6 to 10, except the product of
- Reference Lubricating Composition 5 contains a polyisobutylene dispersant with number average molecular weight of 1600 and a portion of an olefin viscosity modifier.
- Lubricating compositions 11 to 12 are prepared by blending 4.2 wt % of the oil soluble product of Example 4 into an oil of lubricating viscosity in a similar process as lubricating composition LC 9, except the amount of viscosity modifier is reduced by 24 wt % less and 30 wt % respectively.
- Lubricating compositions 13 to 14 are prepared by blending 4.2 wt % of the oil soluble product of Example 5 into an oil of lubricating viscosity in a similar process as lubricating composition LC 10, except the amount of viscosity modifier is reduced by 32 wt % less and 73 wt % respectively.
- Test 1 Viscosity Measurements
- hydrocarbyl substituent or “hydrocarbyl group” is used 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.
- hydrocarbyl groups include: hydrocarbon substituents, that is, aliphatic (e.g., alkyl or alkenyl), alicyclic (e.g., cycloalkyl, cycloalkenyl) substituents, and aromatic-, aliphatic-, and alicyclic-substituted aromatic substituents, as well as cyclic substituents wherein the ring is completed through another portion of the molecule (e.g., two substituents together form a ring); substituted hydrocarbon substituents, that is, substituents containing non- hydrocarbon groups which, in the context of this invention, do not alter the predominantly hydrocarbon nature of the substituent (e.g., halo (especially chloro and fluoro), hydroxy, alkoxy, mercapto, alkylmercapto, nitro, nitroso, and sulfoxy); hetero substituents, that is, substituents which, while having a predominantly hydrocarbon character, in the context of this invention,
Abstract
The present invention provides a process for preparing an oil soluble product comprising reacting: (a) an olefin copolymer having a number average molecular weight of more than about 5000 functionalised with an acylating agent; (b) an acylating agent substituted with a hydrocarbyl group having a number average molecular weight of about 350 to about 5000; and (c) a compound selected from the group consisting of (i) a polyamine; (ii) a polyol; and (iii) an aminoalcohol, wherein the oil soluble product has a mole ratio of acylating agents (a) to (b) of 1:greater than 2. The invention further provides the use of the oil soluble product in a lubricating composition for lubricating an internal combustion engine.
Description
TITLE
Novel Viscosity Modifying Dispersant
FIELD OF INVENTION
The present invention relates to a novel viscosity modifying dispersant. The invention further provides a method of preparing the novel viscosity modifying dispersant, compositions containing the novel viscosity modifying dispersant and its use in a lubricating composition.
BACKGROUND OF THE INVENTION
[0001] The use of polymers as rheology modifiers (or viscosity modifiers) or dispersants in oils of lubricating viscosity is well known. Typical dispersant chemistry is derived from a polyisobutylene succinimide; and a viscosity modifier is often based on an olefin copolymer, especially an ethylene-propylene copolymer. However, it is well known that said dispersant or viscosity modifier chemistry containing an olefinic chain may adversely affect low temperature viscometrics of a lubricating composition.
[0002] US Patent 4,517,104 discloses an ethylene copolymer viscosity index improving dispersant additive useful in oil compositions. The ethylene copolymer is the reaction product of (a) a copolymer comprising 15 wt % to 90 wt % ethylene, a comonomer derived from 10 wt % to 85 wt % of C3 to C28 alpha-olefin; (b) an alkylene or oxyalkylene amine; and (c) a long chain hydrocarbyl substituted succinic anhydride or acid. The patent discloses in the examples a reaction product having a mole ratio of copolymer to a long chain hydrocarbyl substituted succinic anhydride or acid of 1 to 1 or less. [0003] US Patent 5,512,192 discloses a dispersant viscosity modifier for lubricants. The dispersant viscosity modifier is prepared by reacting oil soluble substantially hydrogenated vinyl substituted aromatic-aliphatic diene block copolymers with an ethylenically unsaturated carboxylic acid or functional derivative thereof with at least one polyester, at least one polyamine and at least one hydrocarbyl substituted carboxylic acid or anhydride.
[0004] US Patent 5,035,821 discloses a polymer with an end-capped multifunctional viscosity index improver with dispersant properties. The polymer is an ethylene copolymer grafted with (a) an ethylenically unsaturated
carboxylic acid moiety (e.g., succinic anhydride); then further reacted with (b) a polyamine having two or more primary amino groups or a polyol; (c) a long chain hydrocarbyl substituted dicarboxylic acid material (e.g., alkenyl succinic anhydride) having a functionality of at least 1.2; and (d) a short chain hydrocarbyl substituted dicarboxylic acid or anhydride.
[0005] It would be desirable to have an oil soluble product with at least one property selected from acceptable cleanliness, acceptable viscometrics (i.e. low temperature viscosmetrics or acceptable high temperature viscometrics) and acceptable dispersant properties. The present invention provides an oil soluble product with at least one such property.
SUMMARY OF THE INVENTION
[0006] In one embodiment the present invention provides a process for preparing an oil soluble product comprising reacting: (a) an olefin copolymer having a number average molecular weight of more than about 5000 functionalised with an acylating agent; (b) an acylating agent substituted with a hydrocarbyl group having a number average molecular weight of about 350 to about 5000; and (c) a compound selected from the group consisting of (i) a polyamine; (ii) a polyol; and (iii) an aminoalcohol, wherein the oil soluble product has a mole ratio of acylating agents (a) : (b) of 1: greater than 2. [0007] In one embodiment the present invention provides a process for preparing an oil soluble product comprising reacting: (a) an olefin copolymer having a number average molecular weight of more than about 5000 functionalised with an acylating agent; and (b) a reaction product of an acylating agent substituted with a hydrocarbyl group having a number average molecular weight of about 350 to about 5000 and at least one of (i) a polyamine; (ii) a polyol; and (iii) an aminoalcohol, wherein the oil soluble product has a mole ratio of acylating agents (a) : (b) of 1: greater than 2.
[0008] In one embodiment the present invention provides a lubricating composition comprising: (I) an oil of lubricating viscosity; and (II) an oil soluble reaction product of: (a) an olefin copolymer having a number average molecular weight of more than about 5000 functionalised with an acylating agent; (b) an acylating agent substituted with a hydrocarbyl group having a number average molecular weight of about 350 to about 5000; and (c) a compound selected from the group consisting of (i) a polyamine; (ii) a polyol; and (iii) an aminoalcohol,
wherein the oil soluble product has a mole ratio of acylating agents (a) : (b) of 1: greater than 2.
DETAILED DESCRIPTION QF THE INVENTION
[0009] In one embodiment the present invention provides a process for preparing an oil soluble product comprising reacting:
(a) an olefin copolymer having a number average molecular weight of more than about 5000 functionalised with an acylating agent;
(b) an acylating agent substituted with a hydrocarbyl group having a number average molecular weight of about 350 to about 5000; and
(c) a compound selected from the group consisting of (i) a polyamine; (ii) a polyol; and (iii) an aminoalcohol, wherein the oil soluble product has a mole ratio of acylating agents (a) ; (b) of 1: greater than 2.
[0010] In one embodiment the oil soluble product is prepared by reacting (a) + (b) + (c) in a one-step process. The reaction referred to here and elsewhere in this specification may involve grafting or other reactive processes. A one-step process generally involves adding all of the reactants into a vessel and reacting them to form a product has a mole ratio of (a) : (b) of 1: greater than 2. Further a person skilled in the art will appreciate that the oil soluble product of the invention is a product derived from (a) + (b) + (c). Components (a) + (b) + (c) may also react to give a by-product by reacting (a) + (b) and/or (a) + (c). However, a person skilled in the art will also appreciate that (a) + (b) and/or (a) + (c) may form as intermediates in the formation of the oil soluble product. [0011] In several embodiment the process is carried out at a temperature in the range of 7O0C to 3000C, 1000C to 22O0C or 145°C to 2000C. In several embodiments the process is carried out for a period of time in the range of 30 seconds to 48 hours, 2 minutes to 24 hours, 5 minutes to 16 hours, or 30 minutes to 4 hours. In several embodiments the process is carried out at a pressure in the range of 86.4 kPa to 266 kPa (650 mm Hg to 2000 mm Hg), 91.8 IcPa to 200 kPa (690 mm Hg to 1500 mm Hg) or 95.1 IdPa to 133 kPa (715 mm Hg to 1000 mm Hg).
[0012] In one embodiment the oil soluble product is prepared by reacting (a) + (b) in a two-step process. Typically the two step process comprises (I) preparing a reaction product of an acylating agent substituted with a hydrocarbyl
group having a number average molecular weight of 350 to 5000 and at least one of (i) a polyamine; (ii) a polyol; and (iii) an aminoalcohol; and (II) reacting the product of step (I) with an olefin copolymer having a number average molecular weight of more than about 5000 functionalised with an acylating agent. Generally the reaction product of step (I) is a pre-formed dispersant. Therefore the oil soluble product may be prepared in a two step process comprising pre- reacting (b) and (c) to form a dispersant and reacting the dispersant with (a). A person skilled in the art will also appreciate that steps (I) and (II) of the two-step process may be conducted in either order.
[0013] Reaction conditions for step one (i.e. preparation of the dispersant) are well known in the art and are disclosed, for instance, in US Patent Numbers 3,361,673, 3,401,118 and 4,234,435.
[0014] The reaction conditions for step two of the process are the same as described for the one step process described above.
[0015] In one embodiment the oil soluble product is free or substantially free of a short chain hydrocarbyl substituted dicarboxylic acid. As used herein the term "short chain" means a carbon chain containing less than 16 carbon atoms. [0016] In one embodiment the present invention provides process for preparing an oil soluble product comprising reacting:
(a) an olefin copolymer having a number average molecular weight of more than about 5000 functionalised with an acylating agent; and
(b) a dispersant having hydrocarbyl group which has a number average molecular weight of less than about 5000, wherein the oil soluble product has a mole ratio of acylating agents (a) : (b) of 1: greater than 2.
[0017] In one embodiment the present invention provides process for preparing an oil soluble product comprising reacting:
(a) an olefin copolymer having a number average molecular weight of more than about 5000 functionalised with an acylating agent; and
(b) a reaction product of an acylating agent substituted with a hydrocarbyl group having a number average molecular weight of about 350 to about 5000 and at least one of (i) a polyamine; (ii) a polyol; and (iii) an aminoalcohol, wherein the oil soluble product has a mole ratio of acylating agents (a) : (b) of 1: greater than 2.
[0018] In one embodiment the present invention further provides an oil soluble product obtained (or obtainable) by the process described above. [0019] In one embodiment the oil soluble product is believed to be formed by crosslinking of (a) an olefin copolymer having a number average molecular weight of more than about 5000 functionalised with an acylating agent; and (b) an acylating agent substituted with a hydrocarbyl group having a number average molecular weight of about 350 to about 5000 with (c) a compound selected from the group consisting of (i) a polyamine; (ii) a polyol; and (iii) an aminoalcohol. The compound (c) is believed to serve as a crosslinking agent by condensing or otherwise reacting, at least in part, with the acylating functionality of molecules of both components (a) and (b)
[0020] A person skilled in the art will appreciate that the mole ratio of (a) : (b) may be modified such that amino and/or hydroxy groups sufficiently crosslink the oil soluble product to ensure the dispersant exhibits viscosity index improving properties. If the degree of crosslinking is too high the product gels and becomes oil-insoluble. Alternatively if the degree of crosslinking is too low, the oil soluble product typically has viscosity modifying properties with a modest degree of dispersancy (i.e. a conventional dispersant viscosity modifier). [0021] In several embodiments the mole ratio of (a) : (b) is 1:4 or more, or 1 :8 or more, or 1: 10 or more. Examples of suitable ranges for the mole ratio of (a) to (b) include 1:3 to 1:100, 1:6 to 1:85 or 1:12 to 1:75. A person skilled in the art will appreciate that the mole ratio of (b) is greater than the mole ratio of (a).
[0022] When the olefin copolymer (having a number average molecular weight of more than about 5000 functionalised with an acylating agent) is preformed in the presence of a medium (e.g., an oil of lubricating viscosity) the oil soluble product will typically have a mole ratio of (a) : (b) of 1:9 or more or 1:13. Typically the mole ratio of (a) to (b) is less than 1:30 or 1:25. It is believed that pre-forming the olefin copolymer provides an oil soluble product with the ratio of acylating agents (a) to (b) typically less than 1:30 because a portion of the acylating agent is grafted on to the medium.
[0023] When the olefin copolymer (having a number average molecular weight of more than about 5000 functionalised with an acylating agent) is preformed in the absence of a medium, e.g., in an extruder, the oil soluble product
typically has mole ratio of (a) to (b) in several embodiments of 1: 10 or more, 1:20 or more, 1:30 or more or 1:35 or more. Examples of suitable ranges for the mole ratio of (a) to (b) include 1:35 to 1: 140, 1:45 to 1: 100 or 1:60 to 1:90. [0024] In one embodiment the oil soluble product is prepared in the presence of a medium. The medium is one in which the reactants are generally soluble, often a substantially inert normally liquid organic diluent. Examples include oils of lubricating viscosity such as an oil with low in halogen content or alkyl aromatic compounds such as toluene, xylene and naphthalene. [0025] In one embodiment the oil soluble product is formed in the absence of a medium for polymerisation. Generally processes that do not require a medium for polymerisation are carried out in an extruder reaction vessel. Olefin Copolymer Functionalised with Acylating Agent
[0026] In one embodiment the olefin copolymer includes hydrogenated copolymers of styrene-butadiene, ethylene-propylene polymers, hydrogenated styrene-isoprene polymers, hydrogenated alkenyl aryl conjugated diene copolymers, or mixtures thereof.
[0027] In one embodiment the olefin copolymer is selected from the group consisting of styrene-butadiene polymers, ethylene-propylene polymers, hydrogenated alkenyl aryl conjugated diene copolymers, and mixtures thereof. [0028] In one embodiment the olefin copolymer comprises hydrogenated styrene-isoprene polymers, with the proviso that mole ratio of (a) : (b) is 1:8 or more or any of the ratios or ratios described above that are 1:8 or more. [0029] In several embodiments the olefin copolymer functionalised with an acylating agent has a number average molecular weight of more than 5000, 10,000 or more, or 20,000 or 30,000 or more. Examples of suitable ranges for the number average molecular weight include 7500 to 350,000, 12,000 to 200,000, 25,000 to 100,000, 30,000 to 80,000 or 35,000 to 60,000. [0030] In one embodiment the olefin copolymer which serves as a viscosity modifier is derived from an ethylene monomer and at least one other comonomer derived from an alpha-olefin having the formula H2C=CHR1, wherein R1 is a hydrocarbyl group, especially an alkyl radical. In several embodiments the alkyl radical contains 1 to 30, 1 to 10, 1 to 6 or 1 to 3 carbon atoms. The hydrocarbyl group includes an alkyl radical that has a straight chain, a branched chain or mixtures thereof. Examples of comonomers include propylene, 1-butene,
1-hexene, 1-octene, 4-methyl-l-pentene, 1-decene or mixtures thereof. In one embodiment the comonomer includes 1-butene, propylene or mixtures thereof. Examples of the olefin copolymers include ethylene-propylene copolymers, ethylene- 1-butene copolymers or mixtures thereof.
[0031] In several other embodiments the alpha-olefin includes a comonomer with 6 to 40, 10 to 34 or 14 to 22 carbon atoms. Examples of alpha-olefins include 1-decene 1-undecene, 1-dodecene, 1-tridecene, 1-butadecene, 1- pentadecene, 1-hexadecene, 1-heptadecene 1-octadecene, 1-nonadecene, 1-eicosene, 1-doeicosene, 2-tetracosene, 3-methyl-l-henicosene, 4-ethyl-2- tetracosene or mixtures thereof or reactive equivalents thereof. Useful examples of alpha-olefins include 1-pentadecene, 1-hexadecene, 1-heptadecene 1- octadecene, 1-nonadecene or mixtures thereof. The alpha-olefins are often commercially available as mixtures, especially as mixtures of C16-C18 alpha olefins.
[0032] In one embodiment the olefin copolymer is an ethylene-propylene copolymer and may contain up to 3, 4 or 5 monomer types, that is, it may contain additional monomers beside ethylene and propylene. The composition of the ethylene-propylene copolymer in several embodiments has an ethylene content from 15 wt % to 90 wt % or 30 wt % to 80 wt % of the copolymer; and a propylene content of 10 wt % to 85 wt % or 20 wt % to 70 wt % of the copolymer. In one embodiment olefin copolymer is an ethylene-propylene copolymer, with the ethylene content ranging from 15 wt % to 90 wt % of the copolymer and the propylene content ranging from 10 wt % to 85 wt % of the copolymer. Acylating Agent
[0033] The acylating agent which may be substituted onto the olefin copolymer of (a) or which may be substituted with the hydrocarbyl group of (b) in one embodiment is an unsaturated carboxylic acid anhydride or derivative thereof that may be wholly esterified, partially esterified or mixtures thereof. In one embodiment the acylating agent of component (a) comprises an unsaturated carboxylic acid or reactive equivalents thereof. When partially esterified other derivatives include acids, salts or mixtures thereof. Suitable salts include alkali metals, alkaline earth metals or mixtures thereof. The salts include lithium, sodium, potassium, magnesium, calcium or mixtures thereof. The unsaturated
carboxylic acids or derivatives thereof may comprise acrylic acid, methyl acrylate, methacrylic acid, maleic acid or anhydride, fumaric acid, itaconic acid or anhydride or mixtures thereof or reactive equivalents thereof. In another embodiment the acylating agent of (b) comprises a succinic anhydride.
[0034] Suitable examples of the unsaturated dicarboxylic acid anhydride or derivatives include itaconic anhydride, maleic anhydride, methyl maleic anhydride, ethyl maleic anhydride, dimethyl maleic anhydride or mixtures thereof. The unsaturated carboxylic acid anhydrides or derivatives thereof functionality may be used alone or in combination.
[0035] The acylating agent, when reacted and/or grafted with (a) a olefin copolymer having a number average molecular weight of more than about 5000, may be incorporated into an olefin polymer backbone and/or grafted on to the backbone. In one embodiment the unsaturated carboxylic acid anhydride or derivatives thereof is grafted onto the backbone. In one embodiment the unsaturated carboxylic acid anhydride or derivatives thereof is incorporated into olefin polymer backbone.
Acylating Agent Substituted with a Hydrocarbyl Group
[0036] The acylating agent may be reacted with a hydrocarbon to form an acylating agent substituted with a hydrocarbyl group of (b). In several embodiments the acylating agent is substituted with a hydrocarbyl group derived from a hydrocarbon with a number average molecular weight of 350 to 5000, 400 to 3000, 450 to 2500, 500 to 2300, 550 to 1600 or 900 to 1600.
[0037] The hydrocarbyl group substituted onto the acylating agent in one embodiment is a substituted or unsubstituted oxyalkylene or a polyolefin, such as a polyisobutylene or polybutene. In one embodiment the acylating agent substituted with a hydrocarbyl group comprises a polyisobutylene succinic acid or anhydride, wherein the polyisobutylene has a number average molecular weight of 350 to 3000.
[0038] The acylating agent may be grafted or reacted onto an olefin copolymer viscosity modifier by a similar process as taught in US Patent
4,160,739 and/or 4, 161,452.
Polyamine
[0039] In one embodiment the oil soluble product is formed in the presence of a polyamine. Suitable polyamines are well known to a person skilled in the
art of preparing a dispersant. Examples of suitable polyamines include alkylene amines or oxyalkylene amines. Alkylene amine typically contain alkylene groups containing 2 to 20 or 2 to 10 carbon atoms; and 2 to 14 or 2 to 10 nitrogen atoms. Suitable examples of polyamines include ethylenepolyamines, propylenepolyamines, butylenepolyamines or mixtures thereof. Examples of ethylenepolyamines include triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine, amine still bottoms (often described as HP AX™) or mixtures thereof. In one embodiment the polyamine is still bottoms. Polvol
[0040] In one embodiment the oil soluble product is formed in the presence of a polyol or mixtures thereof. Examples of suitable polyols include compounds containing 2 to 10 or 2 to 6 hydroxyl groups. Examples of a generic class of suitable polyol compounds include glycol, and glycerol. Examples of suitable polyol compounds include glycerol, erythritol, 2-hydroxymethyl-2- methyl- 1 ,3-propanediol (trimethylolethane), 2-hydroxymethyl-2-ethyl- 1,3- propanediol (trimethylolpropane), 1,2,4-hexanetriol, ethylene glycol, propylene glycol, butylene glycol, pentaerythritol, dipentaerythritol, mannitol, sorbitol or mixtures thereof. Aminoalcohol
[0041] In one embodiment the oil soluble product is formed in the presence of an aminoalcohol. Examples of aminoalcohols include ethanolamine, isopropanolamine, diethanolamine, triethanolamine, diethylethanolamine, dimethylethanolamine, dibutylethanolamine, 3-amino-l,2-propanediol, serinol, 2-amino-2-methyl-l,3-propanediol, tris(hydroxymethyl)-aminomethane, 1- amino-1-deoxy-D-sorbitol, diethanol amine; diisopropanolamine, N-methyl-N,N- diethanol amine, triethanolamine, N,N,N',N'-tetrakis(2- hydroxypropyl)ethylenediamine, 2-amino-2-methyl-l-propanol, 2- dimethylamino-methyl-1 -propanediol, 2-amino-2-ethyl-l,3-propanediol, 2- amino-2-methyl-l,3-propanediol, 2-amino-l-butanol or mixtures thereof. In one embodiment the aminoalcohol is ethanolamine. Lubricating Composition
[0042] In one embodiment the present invention provides a lubricating composition comprising:
(I) an oil of lubricating viscosity; and
(II) an oil soluble reaction product of:
(a) an olefin copolymer having a number average molecular weight of more than about 5000 functionalised with an acylating agent;
(b) an acylating agent substituted with a hydrocarbyl group having a number average molecular weight of about 350 to about 5000; and
(c) a compound selected from the group consisting of (i) a polyamine; (ii) a polyol; and (iii) an aminoalcohol, wherein the oil soluble product has a mole ratio of acylating agents (a) : (b) of
1: greater than 2.
Oil of Lubricating Viscosity
[0043] In one embodiment the emulsion composition includes natural or synthetic oils of lubricating viscosity, oil derived from hydrocracldng, hydro gen ati on, hydrofinishing, unrefined, refined and re-refined oils or mixtures thereof.
[0044] Natural oils include animal oils, vegetable oils, mineral oils or mixtures thereof. Synthetic oils include a hydrocarbon oil, a silicon-based oil, a liquid esters of phosphorus-containing acid. Synthetic oils may be produced by
Fischer-Tropsch reactions and typically may be hydroisomerised Fischer-
Tropsch hydrocarbons or waxes.
[0045] Oils of lubricating viscosity may also be defined as specified in the
American Petroleum Institute (API) Base Oil Interchangeability Guidelines. In several embodiments the oil of lubricating viscosity comprises an API Group I,
II, III, IV, V, VI or mixtures thereof, or an API Group I, II, III or mixtures thereof. If the oil of lubricating viscosity is an API Group II, III, IV, V or VI oil there may be up to a maximum of 40 wt % or up to a maximum of 5 wt % of the lubricating oil being an API Group I oil.
[0046] In one embodiment the lubricating composition has a SAE viscosity grade from XW-Y, wherein X is an integer from 0 to 20 and Y is an integer from
20 to 50.
[0047] In several embodiments X is an integer chosen from 0, 5, 10, 15 or 20; and Y is an integer chosen from 20, 25, 30, 35, 40, 45 or 50.
[0048] In several embodiments the oil of lubricating viscosity is present from
40 wt % to 99.9 wt %, or from 50 wt % to 91 wt %, or from 55 wt % to 95 wt %, or from 60 wt % to 90 wt % of the lubricating composition.
Additional Performance Additive
[0049] The composition optionally further includes at least one additional performance additive. The additional performance additives include metal deactivators, detergents, dispersants, friction modifiers, viscosity modifiers, dispersant viscosity modifiers, extreme pressure agents, antiwear agents, antioxidants, corrosion inhibitors, foam inhibitors, demulsifiers, pour point depressants, seal swelling agents or mixtures thereof.
[0050] In several embodiments the total combined amount of the additional performance additive compounds are present from 0 Wt % to 25 wt %, 0.01 wt % to 20 wt %, 0.1 wt % to 15 wt % or 0.5 wt % to 10 wt % of the composition. Although one or more of the additional performance additives may be present, it is common for the additional performance additives to be present in different amounts relative to each other.
[0051] If the present invention is in the form of a concentrate (which can be combined with additional oil to form, in whole or in part, a finished lubricant), the ratio of the oil soluble product of the invention and the optional additional performance additives in an oil of lubricating viscosity, to diluent oil including may be in the range of 80:20 to 10:90 or to 5:95 by weight. [0052] Antioxidants include molybdenum dithiocarbamates, sulphurised olefins, hindered phenols, diphenylamine. Detergents include neutral or overbased, Newtonian or non-Newtonian, basic salts of alkali, alkaline earth and transition metals with one or more of a phenate, a sulphurised phenate, a sulphonate, a carboxylic acid, a phosphorus acid, a mono- and/or a di- thiophosphoric acid, a saligenin, an alkylsalicylate, a salixarate. Dispersants include N-substituted long chain alkenyl succinimide as well as posted treated versions thereof. Post-treated dispersants include those treated by reaction with urea, thiourea, dimercaptothiadiazoles, carbon disulphide, aldehydes, ketones, carboxylic acids, hydrocarbon-substituted succinic anhydrides, nitriles, epoxides, boron compounds, or phosphorus compounds. Viscosity modifiers include hydrogenated copolymers of styrene-butadiene, olefin copolymers other than the oil soluble product of the invention (such as ethylene-propylene polymers, polyisobutenes, hydrogenated styrene-isoprene polymers, hydrogenated isoprene polymers), polymethacrylate acid esters, polyacrylate acid esters, polyalkyl
styrenes, hydrogenated alkenyl aryl conjugated diene copolymers, polyalkylraethacrylates and esters of maleic anhydride-styrene copolymers. [0053] Antiwear agents include compounds such as metal thiophosphates, especially zinc dialkyldithiophosphates; phosphoric acid esters or salt thereof; phosphites; and phosphorus-containing carboxylic esters, ethers, and amides. Antiscuffing agents including organic sulphides and polysulphides, such as benzyldisulphide, bis-(chlorobenzyl) disulphide, dibutyl tetrasulphide, di- tertiary butyl polysulphide, di-tert-butylsulphide, sulphurised Diels-Alder adducts or alkyl sulphenyl N'N-dialkyl dithiocarbamates. Extreme Pressure (EP) agents including chlorinated wax, organic sulphides and polysulphides, such as benzyldisulphide, bis-(chlorobenzyl) disulphide, dibutyl tetrasulphide, sulphurised methyl ester of oleic acid, sulphurised alkylphenol, sulphurised dipentene, sulphurised terpene, and sulphurised Diels-Alder adducts; phosphosulphurised hydrocarbons, metal thiocarbamates, such as zinc dioctyldithiocarbamate and barium heptylphenol diacid. Any of the above classes of additives may also be used in the composition of the invention. [0054] Additionally the invention may also include friction modifiers including fatty amines, esters such as borated glycerol esters, fatty phosphites, fatty acid amides, fatty epoxides, borated fatty epoxides, alkoxylated fatty amines, borated alkoxylated fatty amines, metal salts of fatty acids, fatty imidazolines, condensation products of carboxylic acids and polyalkylene- polyamines, amine salts of alkylphosphoric acids. The formulation of the invention may also include dispersant viscosity modifiers (often referred to as DVM), including functionalised polyolefins, for example, ethylene-propylene copolymers that have been functionalized with the reaction product of maleic anhydride and an amine; polymethacrylates functionalised with an amine, or styrene-maleic anhydride copolymers reacted with an amine. [0055] Other performance additives such as corrosion inhibitors including octylamine octanoate, condensation products of dodecenyl succinic acid or anhydride and a fatty acid such as oleic acid with a polyamine; metal deactivators including derivatives of benzotriazoles, 1,2,4-triazoles, benzimidazoles, 2-alkyldithiobenzimidazoles or 2-alkyldithiobenzothiazoles; foam inhibitors including copolymers of ethyl acrylate and 2-ethylhexylacrylate and optionally 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; and seal swell agents including Exxon Necton-37™ (FN 1380) and Exxon
Mineral Seal Oil (FN 3200); may also be used in the composition of the invention.
Industrial Application
[0056] The oil soluble product of the present invention is useful as a dispersant with viscosity index improving properties for a transmission fluid, a gear oil, a hydraulic fluid or an internal combustion engine lubricant, for example, for diesel fuelled engines, gasoline fuelled engines, natural gas fuelled engines or mixed gasoline/alcohol fuelled engines.
[0057] In one embodiment of the invention provides a method for lubricating an internal combustion engine, comprising supplying thereto a lubricant comprising the oil soluble product as described herein. The use of the oil soluble product in an internal combustion engine may impart one or more properties selected from acceptable cleanliness, acceptable viscometrics (i.e. low temperature viscosmetrics or acceptable high temperature viscometrics) and acceptable dispersant properties.
[0058] In several embodiments the oil soluble product is present in a lubricating composition from 0.001 wt % to 30 wt %, 0.1 wt % to 20 wt %, 0.5 wt % to 15 wt %, 1 wt % to 10 wt % or from 2 wt % to 8 wt % of the lubricating composition.
[0059] The following examples provide illustrations of the invention. These examples are non exhaustive and are not intended to limit the scope of the invention.
EXAMPLES
Preparative Example 1 (Prep EXl)
[0060] A mixture of a Group III oil of Nexbase 3050™ supplied by Fortum oil company (200Og) and toluene (360g) is heated to 125°C under N2 in a 5-litre flask. At this temperature, a 25SSI ethylene-propylene copolymer (424g) is added portion wise and the mixture left to heat for a further three hours. The reaction is then heated to 1600C and tert-butylperoxide (24g) in toluene (80ml) is added drop wise to the polymer solution over 105 minutes. Ten minutes after the
start of the initiator addition, maleic anhydride (41.6g) in acetone (80ml) is added drop wise to the mixture over 90 minutes. The solution is then left to heat at this temperature for a further two hours. The volatile solvents are removed by distillation under reduced pressure to give a viscous yellow oil (2453g, 99%). Examples 1 to 5
[0061] Examples 1 to 5 are prepared by reacting/grafting a polyisobutylene (PIBSA) with a number average molecular weight of 1600 in the amounts shown in Table 1 (PIBSA is diluted to 70 % active ingredient in diluent oil) with the product of Preparative Example 1 and an amine (Methylene tetramine) at 180 0C under a nitrogen atmosphere until a viscous product is formed. Table 1 summarises the amounts of chemicals reacted.
Table 1
Reference Examples 1 to 4
[0062] Reference Examples 1 to 5 are prepared by reacting a 25 SSI ethylene- propylene copolymer (OCPl) a PIBSA (diluted to 70 % in diluent oil) with the product of an amine (tri ethylene tetramine) at 180 0C under a nitrogen atmosphere until a viscous product is formed. Table 2 summarises the amounts of chemicals reacted.
Table 2
Lubricating Compositions
[0063] A series of lubricating compositions containing Examples 1 to 5 and Reference Examples 1 to 4 are prepared by blending 4.2 wt % of the product of said Examples in a base oil to form 5W-30 compositions; and optionally in the presence of a portion of a conventional olefin viscosity modifier. The lubricating compositions prepared are summarised in Table 3.
Table 3
Footnote to Table 3: LC is the lubricating composition.
[0064] Reference Lubricating Compositions (REFLC) 1 to 4 are prepared in the same manner as Lubricating Compositions 6 to 10, except the product of
Reference Examples 1 to 4 are used respectively.
[0065] Reference Lubricating Composition 5 (REFLC 5) contains a polyisobutylene dispersant with number average molecular weight of 1600 and a portion of an olefin viscosity modifier.
[0066] Lubricating compositions 11 to 12 are prepared by blending 4.2 wt % of the oil soluble product of Example 4 into an oil of lubricating viscosity in a similar process as lubricating composition LC 9, except the amount of viscosity modifier is reduced by 24 wt % less and 30 wt % respectively. [0067] Lubricating compositions 13 to 14 are prepared by blending 4.2 wt % of the oil soluble product of Example 5 into an oil of lubricating viscosity in a similar process as lubricating composition LC 10, except the amount of viscosity modifier is reduced by 32 wt % less and 73 wt % respectively. Test 1: Viscosity Measurements
[0068] The Kinematic viscosity at 1000C (KVlOO) and the Cold Crank Simulator (CCS run at -30 0C) viscosity are determined for Examples 1 to 5 and Reference Examples 1 to 4 by employing ASTM methods D445 and D5293 respectively. The results obtained are presented in Table 4.
Table 4
[0069] In Summary, the results in Table 4 and Table 5 demonstrate that the oil soluble product of the invention is capable of providing a lubricating composition with at least one of acceptable low temperature viscosmetrics or acceptable high temperature viscometrics. Furthermore, the oil soluble product of the invention demonstrates that the amount of a conventional viscosity modifier may be reduced without adversely affecting high temperature viscosmetrics whilst providing acceptable low temperature viscometrics. [0070] While the invention has been explained, it is to be understood that various modifications thereof will become apparent to those skilled in the art upon reading the specification. Therefore, it is to be understood that the invention disclosed herein is intended to cover such modifications as fall within the scope of the appended claims.
[0071] Each of the documents referred to above is incorporated herein by reference. Except in the Examples, or where otherwise explicitly indicated, all numerical quantities in this description specifying amounts of materials, reaction conditions, molecular weights, number of carbon atoms, and the like, are to be understood as modified by the word "about." Unless otherwise indicated, 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. However, 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. As used herein any member of a genus (or list) may be excluded from the claims.
[0072] As used herein, the term "hydrocarbyl substituent" or "hydrocarbyl group" is used 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: hydrocarbon substituents, that is, aliphatic (e.g., alkyl or alkenyl), alicyclic (e.g., cycloalkyl, cycloalkenyl) substituents, and aromatic-, aliphatic-, and alicyclic-substituted aromatic substituents, as well as cyclic substituents wherein the ring is completed through another portion of the molecule (e.g., two substituents together form a ring); substituted hydrocarbon substituents, that is, substituents containing non- hydrocarbon groups which, in the context of this invention, do not alter the predominantly hydrocarbon nature of the substituent (e.g., halo (especially chloro and fluoro), hydroxy, alkoxy, mercapto, alkylmercapto, nitro, nitroso, and sulfoxy); hetero substituents, that is, substituents which, while having a predominantly hydrocarbon character, in the context of this invention, contain other than carbon in a ring or chain otherwise composed of carbon atoms; and heteroatoms include sulphur, oxygen, nitrogen, and encompass substituents as pyridyl, furyl, thienyl and imidazolyl. In general, no more than two, in one aspect no more than one, non-hydrocarbon substituent will be present for every ten carbon atoms in the hydrocarbyl group; typically, there will be no non- hydrocarbon substituents in the hydrocarbyl group.
Claims
1. A process for preparing an oil soluble product comprising reacting:
(a) an olefin copolymer having a number average molecular weight of more than about 5000 functionalised with an acylating agent;
(b) an acylating agent substituted with a hydrocarbyl group having a number average molecular weight of about 350 to about 5000; and
(c) a compound selected from the group consisting of (i) a polyamine; (ii) a polyol; and (iii) an aminoalcohol, wherein the oil soluble product has a mole ratio of acylating agents (a) : (b) of 1: greater than about 2.
2. The process of claim 1, wherein the mole ratio of (a) : (b) is 1: about 4 or more, or l:about 8 or more.
3. The process of claim 1, wherein the oil soluble product is prepared in an extruder reaction vessel; and wherein the mole ratio of (a) : (b) is l:about 10 or more.
4. An oil soluble product obtained by the process of claim 1.
5. The process of claim 1, wherein the acylating agent of component (a) comprises an unsaturated carboxylic acid or reactive equivalents thereof.
6. The process of claim 5, wherein the acylating agent is acrylic acid, methyl acrylate, methacrylic acid, maleic acid or anhydride, fumaric acid, itaconic acid or anhydride or mixtures thereof.
7. The process of claim 1, wherein the oil soluble product is prepared in a two step process comprising (I) pre-reacting (b) and (c) to form a dispersant and (II) reacting the resulting dispersant with (a).
8. The process of claim 1, wherein the olefin copolymer comprises hydrogenated copolymers of styrene-butadiene, ethylene-propylene polymers, hydrogenated styrene-isoprene polymers, hydrogenated alkenyl aryl conjugated diene copolymers, or mixtures thereof.
9. The process of claim 1, wherein the olefin copolymer is selected from the group consisting of styrene-butadiene polymers, ethylene-propylene polymers, hydrogenated alkenyl aryl conjugated diene copolymers, and mixtures thereof.
10. The process of claim 8, wherein the olefin copolymer comprises ethylene-propylene polymers.
11. The process of claim 10, wherein the olefin copolymer comprises an ethylene-propylene copolymer, wherein the ethylene content is from about 15 wt % to about 90 wt % of the copolymer; and wherein the propylene content is from about 10 wt % to about 85 wt % of the copolymer.
12. The process of claim 1, wherein the olefin copolymer has a number average molecular weight from about 7500 to about 350,000.
13. The process of claim 1, wherein the hydrocarbyl group of (b) comprises a substituted oxyalkylene or a polyolefin having a number average molecular weight of about 400 to about 3000.
14. The process of claim 13, wherein the hydrocarbyl group of (b) comprises a polyisobutylene succinic acid or anhydride, and wherein the polyisobutylene has a number average molecular weight of about 450 to about 2500.
15. The process of claim 1, wherein the polyamine comprises an ethylenepolyamine, a propylenepolyamine, a butylenepolyamine or mixtures thereof.
16. The process of claim 1, wherein the polyol comprises a glycol, a glycerol or mixtures thereof.
17. A process for preparing an oil soluble product comprising reacting:
(a) an olefin copolymer having a number average molecular weight of more than about 5000 functionalised with an acylating agent; and
(b) a reaction product of an acylating agent substituted with a hydrocarbyl group having a number average molecular weight of about 350 to about 5000 and at least one of (i) a polyamine; (ii) a polyol; and (iii) an aminoalcohol, wherein the oil soluble product has a mole ratio of acylating agents (a) : (b) of l:greater than about 2.
18. A lubricating composition comprising:
(I) an oil of lubricating viscosity; and
(II) an oil soluble reaction product of:
(a) an olefin copolymer having a number average molecular weight of more than about 5000 functionalised with an acylating agent;
(b) an acylating agent substituted with a hydrocarbyl group having a number average molecular weight of about 350 to about 5000; and
(c) a compound selected from the group consisting of (i) a polyamine; (ii) a polyol; and (iii) an aminoalcohol, wherein the oil soluble product has a mole ratio of acylating agents (a) : (b) of l:greater than 2.
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EP0066953A2 (en) * | 1981-05-06 | 1982-12-15 | Exxon Research And Engineering Company | Ethylene copolymer viscosity index improver-dispersant additive useful in oil compositions |
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EP0730022A1 (en) * | 1995-03-02 | 1996-09-04 | The Lubrizol Corporation | Dispersant-viscosity improvers for lubricating oil compositions |
EP0730021A1 (en) * | 1995-03-02 | 1996-09-04 | The Lubrizol Corporation | Dispersant-viscosity improvers for lubricating oil compositions |
WO1999021902A1 (en) * | 1997-10-28 | 1999-05-06 | Castrol Limited | Processes for preparing grafted copolymers |
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2006
- 2006-02-03 WO PCT/US2006/004238 patent/WO2006088693A2/en active Application Filing
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EP0066953A2 (en) * | 1981-05-06 | 1982-12-15 | Exxon Research And Engineering Company | Ethylene copolymer viscosity index improver-dispersant additive useful in oil compositions |
US4670173A (en) * | 1985-12-19 | 1987-06-02 | The Lubrizol Corporation | Oil-soluble reaction products of an acylated reaction product, a polyamine, and mono-functional acid |
US5424367A (en) * | 1991-12-13 | 1995-06-13 | Exxon Chemical Patents Inc. | Multiple reaction process in melt processing equipment |
EP0730022A1 (en) * | 1995-03-02 | 1996-09-04 | The Lubrizol Corporation | Dispersant-viscosity improvers for lubricating oil compositions |
EP0730021A1 (en) * | 1995-03-02 | 1996-09-04 | The Lubrizol Corporation | Dispersant-viscosity improvers for lubricating oil compositions |
WO1999021902A1 (en) * | 1997-10-28 | 1999-05-06 | Castrol Limited | Processes for preparing grafted copolymers |
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WO2016044254A1 (en) * | 2014-09-15 | 2016-03-24 | The Lubrizol Corporation | Dispersant viscosity modifiers with amine functionality |
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WO2006088693A3 (en) | 2006-10-12 |
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