US20110263470A1 - Composition Containing a Block Copolymer and a Method of Lubricating an Internal Combustion Engine - Google Patents
Composition Containing a Block Copolymer and a Method of Lubricating an Internal Combustion Engine Download PDFInfo
- Publication number
- US20110263470A1 US20110263470A1 US13/127,114 US200913127114A US2011263470A1 US 20110263470 A1 US20110263470 A1 US 20110263470A1 US 200913127114 A US200913127114 A US 200913127114A US 2011263470 A1 US2011263470 A1 US 2011263470A1
- Authority
- US
- United States
- Prior art keywords
- meth
- alkyl
- acrylic units
- block
- units
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 122
- 230000001050 lubricating effect Effects 0.000 title claims abstract description 89
- 238000000034 method Methods 0.000 title claims abstract description 71
- 229920001400 block copolymer Polymers 0.000 title claims abstract description 53
- 238000002485 combustion reaction Methods 0.000 title claims abstract description 26
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 155
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims abstract description 85
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 85
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 42
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 41
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 58
- 230000008569 process Effects 0.000 claims description 35
- 229920000642 polymer Polymers 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- 239000005864 Sulphur Substances 0.000 claims description 18
- 229920000359 diblock copolymer Polymers 0.000 claims description 18
- 239000011574 phosphorus Substances 0.000 claims description 18
- 229910052698 phosphorus Inorganic materials 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 16
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 11
- 239000000446 fuel Substances 0.000 claims description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 238000012546 transfer Methods 0.000 claims description 8
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 4
- WWJCRUKUIQRCGP-UHFFFAOYSA-N 3-(dimethylamino)propyl 2-methylprop-2-enoate Chemical compound CN(C)CCCOC(=O)C(C)=C WWJCRUKUIQRCGP-UHFFFAOYSA-N 0.000 claims description 4
- UFQHFMGRRVQFNA-UHFFFAOYSA-N 3-(dimethylamino)propyl prop-2-enoate Chemical compound CN(C)CCCOC(=O)C=C UFQHFMGRRVQFNA-UHFFFAOYSA-N 0.000 claims description 4
- ZWAPMFBHEQZLGK-UHFFFAOYSA-N 5-(dimethylamino)-2-methylidenepentanamide Chemical compound CN(C)CCCC(=C)C(N)=O ZWAPMFBHEQZLGK-UHFFFAOYSA-N 0.000 claims description 4
- FLCAEMBIQVZWIF-UHFFFAOYSA-N 6-(dimethylamino)-2-methylhex-2-enamide Chemical compound CN(C)CCCC=C(C)C(N)=O FLCAEMBIQVZWIF-UHFFFAOYSA-N 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000129 anionic group Chemical group 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 238000013467 fragmentation Methods 0.000 claims description 3
- 238000006062 fragmentation reaction Methods 0.000 claims description 3
- 230000002441 reversible effect Effects 0.000 claims description 3
- 230000000994 depressogenic effect Effects 0.000 abstract description 16
- 239000003995 emulsifying agent Substances 0.000 abstract description 16
- 239000003921 oil Substances 0.000 description 61
- 235000019198 oils Nutrition 0.000 description 61
- -1 thiocarbonyl thio group Chemical group 0.000 description 54
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 41
- 239000000314 lubricant Substances 0.000 description 34
- 239000002270 dispersing agent Substances 0.000 description 32
- 239000000047 product Substances 0.000 description 26
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 24
- 239000003795 chemical substances by application Substances 0.000 description 23
- 229940063557 methacrylate Drugs 0.000 description 22
- 239000003599 detergent Substances 0.000 description 21
- 239000010705 motor oil Substances 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 17
- 229920001577 copolymer Polymers 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 15
- 239000003963 antioxidant agent Substances 0.000 description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 description 14
- 239000000654 additive Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000003607 modifier Substances 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 12
- 229960002317 succinimide Drugs 0.000 description 12
- 239000003112 inhibitor Substances 0.000 description 11
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 10
- 150000001336 alkenes Chemical class 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 230000003078 antioxidant effect Effects 0.000 description 10
- 239000004034 viscosity adjusting agent Substances 0.000 description 10
- 229920002367 Polyisobutene Polymers 0.000 description 9
- 230000005540 biological transmission Effects 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000005260 corrosion Methods 0.000 description 8
- 230000007797 corrosion Effects 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 239000003502 gasoline Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000012986 chain transfer agent Substances 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- 229910052791 calcium Inorganic materials 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000005078 molybdenum compound Substances 0.000 description 5
- 150000002752 molybdenum compounds Chemical class 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- ADOBXTDBFNCOBN-UHFFFAOYSA-N 1-heptadecene Chemical compound CCCCCCCCCCCCCCCC=C ADOBXTDBFNCOBN-UHFFFAOYSA-N 0.000 description 4
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 4
- NZUFSQKDRQFPNG-UHFFFAOYSA-N CCCCCCCCCCCC[S+](CCCC)C([S-])=S Chemical compound CCCCCCCCCCCC[S+](CCCC)C([S-])=S NZUFSQKDRQFPNG-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000002199 base oil Substances 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000000356 contaminant Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- VAMFXQBUQXONLZ-UHFFFAOYSA-N icos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 4
- 239000010687 lubricating oil Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 229910052750 molybdenum Inorganic materials 0.000 description 4
- 239000011733 molybdenum Substances 0.000 description 4
- 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 4
- 229920000768 polyamine Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- 229910000838 Al alloy Inorganic materials 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 239000004435 Oxo alcohol Substances 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 3
- 239000012990 dithiocarbamate Substances 0.000 description 3
- 230000001804 emulsifying effect Effects 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 150000002646 long chain fatty acid esters Chemical class 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 229920013639 polyalphaolefin Polymers 0.000 description 3
- 229920000193 polymethacrylate Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000003902 salicylic acid esters Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 3
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 3
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 3
- PJLHTVIBELQURV-UHFFFAOYSA-N 1-pentadecene Chemical compound CCCCCCCCCCCCCC=C PJLHTVIBELQURV-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- DJKKWVGWYCKUFC-UHFFFAOYSA-N 2-butoxyethyl 2-methylprop-2-enoate Chemical compound CCCCOCCOC(=O)C(C)=C DJKKWVGWYCKUFC-UHFFFAOYSA-N 0.000 description 2
- KQWDURCUENVKII-UHFFFAOYSA-N 2-ethoxyethoxymethyl 2-methylprop-2-enoate Chemical compound CCOCCOCOC(=O)C(C)=C KQWDURCUENVKII-UHFFFAOYSA-N 0.000 description 2
- NUXLDNTZFXDNBA-UHFFFAOYSA-N 6-bromo-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C(Br)C=C2NC(=O)C(C)OC2=C1 NUXLDNTZFXDNBA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- 241000640882 Condea Species 0.000 description 2
- 238000005698 Diels-Alder reaction Methods 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- GLOYGJPNNKTDIG-UHFFFAOYSA-N SC=1N=NSC=1S Chemical class SC=1N=NSC=1S GLOYGJPNNKTDIG-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 0 [1*]C([1*])(CC(=O)C(=C)C)N([2*])[2*] Chemical compound [1*]C([1*])(CC(=O)C(=C)C)N([2*])[2*] 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- AVVIDTZRJBSXML-UHFFFAOYSA-L calcium;2-carboxyphenolate;dihydrate Chemical compound O.O.[Ca+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O AVVIDTZRJBSXML-UHFFFAOYSA-L 0.000 description 2
- ZMRQTIAUOLVKOX-UHFFFAOYSA-L calcium;diphenoxide Chemical compound [Ca+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 ZMRQTIAUOLVKOX-UHFFFAOYSA-L 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000012612 commercial material Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical compound C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- SZVJSHCCFOBDDC-UHFFFAOYSA-N ferrosoferric oxide Chemical compound O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 2
- 239000013020 final formulation Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 150000004668 long chain fatty acids Chemical class 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical class O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000006078 metal deactivator Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 239000010688 mineral lubricating oil Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Natural products CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920002959 polymer blend Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920006389 polyphenyl polymer Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000010689 synthetic lubricating oil Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- YISRDGYZLHFSJW-UHFFFAOYSA-N (2-pentylphenyl) dihydrogen phosphite Chemical compound CCCCCC1=CC=CC=C1OP(O)O YISRDGYZLHFSJW-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- 150000000178 1,2,4-triazoles Chemical class 0.000 description 1
- RDAGYWUMBWNXIC-UHFFFAOYSA-N 1,2-bis(2-ethylhexyl)benzene Chemical class CCCCC(CC)CC1=CC=CC=C1CC(CC)CCCC RDAGYWUMBWNXIC-UHFFFAOYSA-N 0.000 description 1
- YEYQUBZGSWAPGE-UHFFFAOYSA-N 1,2-di(nonyl)benzene Chemical class CCCCCCCCCC1=CC=CC=C1CCCCCCCCC YEYQUBZGSWAPGE-UHFFFAOYSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- JQACBLYOTAYMHP-UHFFFAOYSA-N 1-(2-methylprop-2-enoyl)pyrrolidin-2-one Chemical compound CC(=C)C(=O)N1CCCC1=O JQACBLYOTAYMHP-UHFFFAOYSA-N 0.000 description 1
- INMCBHAUNITFAQ-UHFFFAOYSA-N 1-(2-oxopyrrolidin-1-yl)heptadecan-3-yl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCC(OC(=O)C(C)=C)CCN1CCCC1=O INMCBHAUNITFAQ-UHFFFAOYSA-N 0.000 description 1
- PYGSHOKARRMFTD-UHFFFAOYSA-N 1-(2-oxopyrrolidin-1-yl)pentadecan-2-yl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCC(OC(=O)C(C)=C)CN1CCCC1=O PYGSHOKARRMFTD-UHFFFAOYSA-N 0.000 description 1
- PTYXPKUPXPWHSH-UHFFFAOYSA-N 1-(butyltetrasulfanyl)butane Chemical compound CCCCSSSSCCCC PTYXPKUPXPWHSH-UHFFFAOYSA-N 0.000 description 1
- DDPGLQRMAQYQEQ-UHFFFAOYSA-N 1-butoxypropyl 2-methylprop-2-enoate Chemical compound CCCCOC(CC)OC(=O)C(C)=C DDPGLQRMAQYQEQ-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- WIWZLDGSODDMHJ-UHFFFAOYSA-N 1-ethoxybutyl 2-methylprop-2-enoate Chemical compound CCCC(OCC)OC(=O)C(C)=C WIWZLDGSODDMHJ-UHFFFAOYSA-N 0.000 description 1
- HVBADOTWUFBZMF-UHFFFAOYSA-N 1-ethoxyethyl 2-methylprop-2-enoate Chemical compound CCOC(C)OC(=O)C(C)=C HVBADOTWUFBZMF-UHFFFAOYSA-N 0.000 description 1
- QVXGKJYMVLJYCL-UHFFFAOYSA-N 2,3-di(nonyl)-N-phenylaniline Chemical compound C(CCCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCCC QVXGKJYMVLJYCL-UHFFFAOYSA-N 0.000 description 1
- OQYKKQQLTKPGSG-UHFFFAOYSA-N 2,5-dimethylhexane-1,6-diol Chemical compound OCC(C)CCC(C)CO OQYKKQQLTKPGSG-UHFFFAOYSA-N 0.000 description 1
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- SZATXRHXOOLEFV-UHFFFAOYSA-N 2,6-ditert-butyl-4-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SZATXRHXOOLEFV-UHFFFAOYSA-N 0.000 description 1
- STHGHFNAPPFPQV-UHFFFAOYSA-N 2,6-ditert-butyl-4-propylphenol Chemical compound CCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 STHGHFNAPPFPQV-UHFFFAOYSA-N 0.000 description 1
- PQDKOKTULASSPO-UHFFFAOYSA-N 2-(1,3-oxazolidin-2-yl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1NCCO1 PQDKOKTULASSPO-UHFFFAOYSA-N 0.000 description 1
- MGMSZKIPUNOMCS-UHFFFAOYSA-N 2-(2-ethenoxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC=C MGMSZKIPUNOMCS-UHFFFAOYSA-N 0.000 description 1
- DAVVKEZTUOGEAK-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl 2-methylprop-2-enoate Chemical compound COCCOCCOC(=O)C(C)=C DAVVKEZTUOGEAK-UHFFFAOYSA-N 0.000 description 1
- FPCPOLLWTJARLO-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)acetic acid Chemical compound CC(=C)C(=O)OCC(O)=O FPCPOLLWTJARLO-UHFFFAOYSA-N 0.000 description 1
- XVTPGZQPUZSUKS-UHFFFAOYSA-N 2-(2-oxopyrrolidin-1-yl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCN1CCCC1=O XVTPGZQPUZSUKS-UHFFFAOYSA-N 0.000 description 1
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 description 1
- PDTDJRYFNGKLHD-UHFFFAOYSA-N 2-(methoxymethoxy)ethyl 2-methylprop-2-enoate Chemical compound COCOCCOC(=O)C(C)=C PDTDJRYFNGKLHD-UHFFFAOYSA-N 0.000 description 1
- QDCPNGVVOWVKJG-VAWYXSNFSA-N 2-[(e)-dodec-1-enyl]butanedioic acid Chemical compound CCCCCCCCCC\C=C\C(C(O)=O)CC(O)=O QDCPNGVVOWVKJG-VAWYXSNFSA-N 0.000 description 1
- DRFWIQLQFIYNOA-UHFFFAOYSA-N 2-[cyano(methyl)amino]ethyl 2-methylprop-2-enoate Chemical compound N#CN(C)CCOC(=O)C(C)=C DRFWIQLQFIYNOA-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- AKVUWTYSNLGBJY-UHFFFAOYSA-N 2-methyl-1-morpholin-4-ylprop-2-en-1-one Chemical compound CC(=C)C(=O)N1CCOCC1 AKVUWTYSNLGBJY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- UMNGRRUQHFCWGR-UHFFFAOYSA-N 2-oxopropyl 2-methylprop-2-enoate Chemical compound CC(=O)COC(=O)C(C)=C UMNGRRUQHFCWGR-UHFFFAOYSA-N 0.000 description 1
- KOBJYYDWSKDEGY-UHFFFAOYSA-N 2-phenylpropan-2-yl benzenecarbodithioate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=S)C1=CC=CC=C1 KOBJYYDWSKDEGY-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- JTFIUWWKGBGREU-UHFFFAOYSA-N 3,4-dihydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC(O)CO JTFIUWWKGBGREU-UHFFFAOYSA-N 0.000 description 1
- SBWOBTUYQXLKSS-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propanoic acid Chemical compound CC(=C)C(=O)OCCC(O)=O SBWOBTUYQXLKSS-UHFFFAOYSA-N 0.000 description 1
- LOKFVYOYLXCQMI-UHFFFAOYSA-N 3-(2-oxopyrrolidin-1-yl)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCN1CCCC1=O LOKFVYOYLXCQMI-UHFFFAOYSA-N 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- WTWGHNZAQVTLSQ-UHFFFAOYSA-N 4-butyl-2,6-ditert-butylphenol Chemical compound CCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 WTWGHNZAQVTLSQ-UHFFFAOYSA-N 0.000 description 1
- YKXAYLPDMSGWEV-UHFFFAOYSA-N 4-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCO YKXAYLPDMSGWEV-UHFFFAOYSA-N 0.000 description 1
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 1
- LPNVATKBHBASAJ-UHFFFAOYSA-N 6-(dimethylamino)-2-methylidenehexanamide Chemical compound CN(C)CCCCC(=C)C(N)=O LPNVATKBHBASAJ-UHFFFAOYSA-N 0.000 description 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- HJRYTDKISXDCLR-UHFFFAOYSA-N C(CCCCCC)C1=C(C=CC=C1)O.[Ba] Chemical compound C(CCCCCC)C1=C(C=CC=C1)O.[Ba] HJRYTDKISXDCLR-UHFFFAOYSA-N 0.000 description 1
- UUNBFTCKFYBASS-UHFFFAOYSA-N C(CCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCC Chemical compound C(CCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCC UUNBFTCKFYBASS-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-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
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- CTROOSGUTHXSDG-UHFFFAOYSA-N [S].Cl[S] Chemical compound [S].Cl[S] CTROOSGUTHXSDG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 239000007866 anti-wear additive Substances 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 239000002551 biofuel Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000004074 biphenyls Chemical class 0.000 description 1
- ZLMKQJQJURXYLC-UHFFFAOYSA-N bis(2-ethylhexoxy)-oxophosphanium Chemical compound CCCCC(CC)CO[P+](=O)OCC(CC)CCCC ZLMKQJQJURXYLC-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- TXRSZLVALCTWSR-UHFFFAOYSA-N butyl 2-dodecylsulfanylcarbothioylsulfanyl-2-methylpropanoate Chemical compound CCCCCCCCCCCCSC(=S)SC(C)(C)C(=O)OCCCC TXRSZLVALCTWSR-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004517 catalytic hydrocracking Methods 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- KXTNMKREYTVOMX-UHFFFAOYSA-N cyanomethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC#N KXTNMKREYTVOMX-UHFFFAOYSA-N 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- XRXPHPJRVWEWKQ-UHFFFAOYSA-N cyclohexyloxymethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCOC1CCCCC1 XRXPHPJRVWEWKQ-UHFFFAOYSA-N 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DZQISOJKASMITI-UHFFFAOYSA-N decyl-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound CCCCCCCCCCP(O)(O)=O DZQISOJKASMITI-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- BVXOPEOQUQWRHQ-UHFFFAOYSA-N dibutyl phosphite Chemical compound CCCCOP([O-])OCCCC BVXOPEOQUQWRHQ-UHFFFAOYSA-N 0.000 description 1
- HEGXHCKAUFQNPC-UHFFFAOYSA-N dicyclohexyl hydrogen phosphite Chemical compound C1CCCCC1OP(O)OC1CCCCC1 HEGXHCKAUFQNPC-UHFFFAOYSA-N 0.000 description 1
- QBCOASQOMILNBN-UHFFFAOYSA-N didodecoxy(oxo)phosphanium Chemical compound CCCCCCCCCCCCO[P+](=O)OCCCCCCCCCCCC QBCOASQOMILNBN-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- CUKQEWWSHYZFKT-UHFFFAOYSA-N diheptyl hydrogen phosphite Chemical compound CCCCCCCOP(O)OCCCCCCC CUKQEWWSHYZFKT-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- OKXAFOJPRGDZPB-UHFFFAOYSA-N dioctadecoxy(oxo)phosphanium Chemical group CCCCCCCCCCCCCCCCCCO[P+](=O)OCCCCCCCCCCCCCCCCCC OKXAFOJPRGDZPB-UHFFFAOYSA-N 0.000 description 1
- CWIFFEDJNKOXKL-UHFFFAOYSA-N dipentyl phenyl phosphite Chemical compound CCCCCOP(OCCCCC)OC1=CC=CC=C1 CWIFFEDJNKOXKL-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical class CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- WMAFNLQQGPUKCM-UHFFFAOYSA-N ethoxymethyl 2-methylprop-2-enoate Chemical compound CCOCOC(=O)C(C)=C WMAFNLQQGPUKCM-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000013100 final test Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- NEEVIMDYMPGZPZ-UHFFFAOYSA-N formamido 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)ONC=O NEEVIMDYMPGZPZ-UHFFFAOYSA-N 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
- DWXAVNJYFLGAEF-UHFFFAOYSA-N furan-2-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CO1 DWXAVNJYFLGAEF-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- 239000010699 lard oil Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000005555 metalworking Methods 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- LVQPBIMCRZQQBC-UHFFFAOYSA-N methoxymethyl 2-methylprop-2-enoate Chemical compound COCOC(=O)C(C)=C LVQPBIMCRZQQBC-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- OWXJWNXGYIVLBV-UHFFFAOYSA-J molybdenum(4+) tetracarbamothioate Chemical compound C(N)([O-])=S.[Mo+4].C(N)([O-])=S.C(N)([O-])=S.C(N)([O-])=S OWXJWNXGYIVLBV-UHFFFAOYSA-J 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- YQZKGAILXKHVKY-UHFFFAOYSA-N n-ethenyl-2-hydroxyacetamide Chemical compound OCC(=O)NC=C YQZKGAILXKHVKY-UHFFFAOYSA-N 0.000 description 1
- RQAKESSLMFZVMC-UHFFFAOYSA-N n-ethenylacetamide Chemical compound CC(=O)NC=C RQAKESSLMFZVMC-UHFFFAOYSA-N 0.000 description 1
- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- IUWVWLRMZQHYHL-UHFFFAOYSA-N n-ethenylpropanamide Chemical class CCC(=O)NC=C IUWVWLRMZQHYHL-UHFFFAOYSA-N 0.000 description 1
- RCLLINSDAJVOHP-UHFFFAOYSA-N n-ethyl-n',n'-dimethylprop-2-enehydrazide Chemical compound CCN(N(C)C)C(=O)C=C RCLLINSDAJVOHP-UHFFFAOYSA-N 0.000 description 1
- RQVGZVZFVNMBGS-UHFFFAOYSA-N n-octyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCC)C1=CC=CC=C1 RQVGZVZFVNMBGS-UHFFFAOYSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- LQNPIBHEOATAEO-UHFFFAOYSA-N octanoate;octylazanium Chemical compound CCCCCCCCN.CCCCCCCC(O)=O LQNPIBHEOATAEO-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- VCAFTIGPOYBOIC-UHFFFAOYSA-N phenyl dihydrogen phosphite Chemical class OP(O)OC1=CC=CC=C1 VCAFTIGPOYBOIC-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- XGRBZUSXGVNWMI-UHFFFAOYSA-N phenylmethoxymethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCOCC1=CC=CC=C1 XGRBZUSXGVNWMI-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920005652 polyisobutylene succinic anhydride Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 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
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- 229940095068 tetradecene Drugs 0.000 description 1
- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical class CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
- VQOXUMQBYILCKR-UHFFFAOYSA-N tridecaene Natural products CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical group CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011787 zinc oxide 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
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M149/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
-
- 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
- C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
- C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
- C10M145/12—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate monocarboxylic
- C10M145/14—Acrylate; Methacrylate
-
- 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
- C10M101/00—Lubricating compositions characterised by the base-material being a mineral or fatty oil
- C10M101/04—Fatty oil fractions
-
- 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
- C10M103/00—Lubricating compositions characterised by the base-material being an inorganic material
-
- 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/02—Well-defined hydrocarbons
- C10M105/04—Well-defined hydrocarbons aliphatic
-
- 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/02—Well-defined hydrocarbons
- C10M105/06—Well-defined hydrocarbons aromatic
-
- 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
-
- 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/10—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
- C10M105/14—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms polyhydroxy
-
- 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
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/22—Carboxylic acids or their salts
- C10M105/24—Carboxylic acids or their salts having only one carboxyl group bound to an acyclic carbon atom, cycloaliphatic carbon atom or hydrogen
-
- 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
- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M149/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
-
- 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
- C10M151/00—Lubricating compositions characterised by the additive being a macromolecular compound containing sulfur, selenium or tellurium
- C10M151/02—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
-
- 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
- C10M153/00—Lubricating compositions characterised by the additive being a macromolecular compound containing phosphorus
- C10M153/02—Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
-
- 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
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/084—Acrylate; Methacrylate
-
- 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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
-
- 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
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/024—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
-
- 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
- C10N2030/26—Waterproofing or water resistance
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
- C10N2040/251—Alcohol-fuelled engines
Definitions
- the invention provides a lubricating composition containing an oil of lubricating viscosity and a block copolymer.
- the invention further relates to a method of lubricating an internal combustion engine by lubricating the engine with the lubricating composition.
- the invention further relates to the use of the block copolymer as an emulsifier and/or pour point depressant.
- Lubricants are often exposed to contaminant amounts of water.
- the contaminant amounts of water are believed to be caused by ingress of water through equipment seals during operation, or from combustion by-products that pass into the crankcase via blow-by.
- the water may form a second layer in the lubricant.
- emulsifiers and/or dispersants are employed to reduce the formation of the second layer. If the water concentration becomes high enough, an emulsion results. If the emulsion is unstable, the contaminant water may then cause additional difficulties such as corrosion. The corrosion may be from copper or lead bearings, or iron.
- lubricant base oils may also contain waxy components. Waxes may agglomerate and cause accumulation of crystals in a lubricant. When this occurs, problems arising include reduced low temperature oil pumpability, poorer cold temperature properties or reduced fuel economy. Accordingly, in one embodiment it may also be desirable to employ a pour point depressant that reduces wax agglomeration.
- FMVs flexible fuel vehicles
- E85 85% ethanol
- dispersants are designed to stabilise contaminants in the engine oil of gasoline-fuelled cars.
- Fuelling with E85 introduces the potential to transform the engine oil into a milky emulsion.
- RAFT polymers as viscosity index improvers in a variety of lubricants.
- the RAFT polymers may have a variety of architectures including diblock copolymers. All of polymers are derived from C 12-15 alkyl (meth)acrylates. There is no disclosure or teaching of linear or star polymers having emulsifier and/or pour point depressant properties.
- US Patent Application 2006/0189490 discloses a lubricating composition containing base oil and at least one additive having friction-modifying properties.
- the additive is a linear diblock copolymer which includes hydrophobic segments P and polar segments D, said hydrophobic segments being obtained by polymerisation of monomer compositions which comprises 0 to 40% of C 1-5 alkyl (meth)acrylates, 50 to 100% of C 6-30 alkyl (meth)acrylates, and 0 to 50% of a polar group containing ester, thioester or amide functionality. All of the examples disclose C 12-15 alkyl (meth)acrylates. There is no disclosure or teaching of linear or star polymers having emulsifier and/or pour point depressant properties.
- a lubricating composition containing a block copolymer and method as disclosed herein is capable of providing acceptable levels of at least one of (i) emulsifying properties, and (ii) pour point depressant properties.
- the lubricating composition containing the block copolymer provides both emulsifying properties and pour point depressant properties.
- polar in the state of the art is used in the ordinary sense of the word and is also known to mean hydrophilic.
- the invention provides a lubricating composition comprising an oil of lubricating viscosity and a diblock copolymer, wherein the diblock copolymer comprises:
- the second block having (meth)acrylic units which further have a non-carbonyl heteroatom-containing group providing a polar group to such units, whereby said second block exhibits greater hydrophilicity than does the hydrophobic first block, may also be described as a second block having (meth)acrylic units further having a heteroatom group providing a polar group.
- the invention provides a lubricating composition comprising an oil of lubricating viscosity and a diblock copolymer, wherein the diblock copolymer comprises:
- the invention provides a diblock copolymer product (and optionally a lubricating composition) obtained/obtainable by a process comprising:
- step (2) optionally contacting the polymer of step (1) with a polymerisation inhibitor
- step (3) contacting the polymer of step (1) or step (2) with one or more (meth)acrylic units typically at least 50 wt % or at least 75 wt % of the said units further containing a heteroatom-containing group; and
- step (3) optionally mixing the polymer of step (3) with an oil of lubricating viscosity to form a lubricating composition.
- the C 16-20 alkyl (meth)acrylic units may be C 16-18 alkyl (meth)acrylic units, or C 18-20 alkyl (meth)acrylic units.
- the C 16-20 alkyl (meth)acrylic units may also contain up to 10 wt % (or typically up to 5 wt %) of C 14 alkyl (meth)acrylic units.
- the C 16-20 alkyl (meth)acrylic units may be in the form of a mixture of (meth)acrylic compounds having alkyl groups containing 16 to 20, or 16 to 18 carbon atoms.
- the first step of the process may be performed in the presence of a mineral oil, synthetic oil, hexane, toluene, tetrahydrofuran, or other known polymerisation solvents.
- the invention provides a diblock copolymer product (and optionally a lubricating composition) obtained/obtainable by a process comprising:
- step (2) optionally contacting the polymer of step (1) with a polymerisation inhibitor
- step (3) contacting the polymer of step (1) or step (2) with one or more C 1-30 alkyl (meth)acrylic monomer units, wherein at least 50 wt % of the C 1-30 alkyl (meth)acrylic monomer units contain C 12-15 alkyl (meth)acrylic units, and up to 50 wt % of the C 1-30 alkyl (meth)acrylic units are C 16-20 alkyl (meth)acrylic units, with the proviso that alkyl groups of the C 1-30 alkyl (meth)acrylic units have an average total number of carbon atoms of at least 8, to form a polymer; and
- step (3) optionally mixing the polymer of step (3) with an oil of lubricating viscosity to form a lubricating composition.
- the first step of the process may be performed in the presence of a solvent such as toluene or tetrahydrofuran.
- the invention provides block copolymer obtained (or obtainable) by the process described above.
- the invention provides a method of lubricating a flexible fuel vehicle (flex fuel vehicle or FFV) internal combustion engine comprising supplying to the engine a lubricating composition comprising an oil of lubricating viscosity and a block copolymer, wherein the block copolymer comprises:
- the flexible fuel vehicle may be fuelled with gasoline typically containing 5 wt % to 85 wt %, or 10 wt % up to 85 wt %, or 15 wt % to up to 85 wt % alcohol.
- the alcohol may for instance be ethanol.
- the hydrophobic first block may contain 0 wt % to 5 wt % of a hydrophilic monomer (i.e., units derived from a monomer with a polar group such as a monomer containing a heteroatom group derived from a nitrogen or oxygen containing group. Monomers of this type are discussed in more detail below.
- the hydrophobic first block may contain 0 wt % a hydrophilic monomer.
- the invention provides a method of lubricating an internal combustion engine comprising supplying to the engine a lubricating composition comprising an oil of lubricating viscosity and a block copolymer, wherein the block copolymer comprises:
- the block copolymer may be an emulsifier and/or pour point depressant in an internal combustion engine.
- Emulsifier properties may occur for any block copolymer composition of the present invention.
- Emulsifier and pour point depressant properties typically occur when the diblock block copolymer contains C 16-20 alkyl (meth)acrylic units, and C 12-15 alkyl (meth)acrylic units.
- the internal combustion engine may be operated on gasoline, diesel, biofuels, ethanol, or mixtures thereof. In one embodiment the internal combustion engine may be operated on a mixture of gasoline and ethanol.
- the internal combustion engine may be referred to as a flexible fuel vehicle engine.
- block copolymer disclosed herein may be a linear diblock copolymer.
- the lubricating composition may be further characterised as having at least one of (i) a sulphur content of 0.8 wt % or less, (ii) a phosphorus content of 0.2 wt % or less, or (iii) a sulphated ash content of 2 wt % or less.
- the lubricating composition may be further characterised as having (i) a sulphur content of 0.5 wt % or less, (ii) a phosphorus content of 0.1 wt % or less, and (iii) a sulphated ash content of 1.5 wt % or less.
- the lubricating composition further includes at least one of a friction modifier, a viscosity modifier, an antioxidant, an overbased detergent, a succinimide dispersant, a pour point depressant, or mixtures thereof.
- the lubricating composition further includes a viscosity modifier and an overbased detergent.
- the lubricating composition further includes an overbased detergent and a succinimide dispersant.
- the invention provides a method for lubricating an engine oil comprising supplying to the engine a lubricating composition as disclosed herein.
- the block copolymer may be used at 0.01 wt % to 0.5 wt %, or 0.05 to 0.3 wt % of the lubricating composition disclosed herein.
- the present invention provides a lubricating composition and a method for lubricating a mechanical device as disclosed above.
- the mechanical device may be an internal combustion engine.
- (meth)acrylic units includes both acrylic and methacrylic units and the units are derived from an appropriate monomer.
- the (meth)acrylic units typically include methacrylates, acrylates, methacrylamides, acrylamides, or mixtures thereof.
- the molecular weight of the block copolymer has been determined using known methods, such as GPC analysis using polystyrene standards.
- Methods for determining molecular weights of polymers are well known. The methods are described for instance: (i) P. J. Flory, “Principles of Polymer Chemistry”, Georgia University Press 91953), Chapter VII, pp 266-315; or (ii) “Macromolecules, an Introduction to Polymer Science”, F. A. Bovey and F. H. Winslow, Editors, Academic Press (1979), pp 296-312.
- the block copolymer may be a diblock, a triblock, or a higher block copolymer.
- the diblock copolymer may have a AB composition, where A is a hydrophobic unit, and B is a hydrophilic unit.
- the triblock copolymer may have ABA or BAB, ABA′, or BAB′, where A and B are defined above, and A′ and B′ represent hydrophobic and hydrophilic units different from A and B respectively.
- Each block may be a tapered copolymer, a random copolymer, a sequential copolymer, or may have a random or sequential distribution of two or more monomer units.
- the weight average molecular weight of the block copolymer may be in the range of 1000 to 400,000, or 1000 to 150,000, or 15,000 to 100,000.
- the weight ratio of the second block to the first block may be in the range of 1:2 to 1:100, or 1:4 to 1:30, or 1:6 to 1:18.
- the length of the first block to the second block may have a ratio of 10:1 to 1:10, or 6:1 to 1:2.
- the C 1-30 alkyl (meth)acrylic units may be derived from an alkyl (meth)acrylate.
- the alkyl (meth)acrylate includes for example compounds derived from saturated alcohols, such as methyl methacrylate, butyl methacrylate, 2-methylpentyl (meth)acrylate, 2-propylheptyl (meth)acrylate, 2-butyloctyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, octyl (meth)acrylate, nonyl (meth)acrylate, isooctyl (meth)acrylate, isononyl (meth)acrylate, 2-tert-butyl-heptyl (meth)acrylate, 3-isopropylheptyl (meth)acrylate, decyl (meth)acrylate, undecyl (meth)acrylate, 5-methylundecyl (meth)acrylate, dodecyl (meth)-acrylate, 2-methyldodecyl (meth)acrylate, tridecyl (meth)
- the alkyl (meth)acrylates with long-chain alcohol-derived groups may be obtained, for example, by reaction of a (meth)acrylic acid (by direct esterification) or methyl methacrylate (by transesterification) with long-chain fatty alcohols, in which reaction a mixture of esters such as (meth)acrylate with alcohol groups of various chain lengths is generally obtained.
- These fatty alcohols include Oxo Alcohol® 7911, Oxo Alcohol® 7900 and Oxo Alcohol® 1100 of Monsanto; Alphanol® 79 of ICI; Nafol® 1620, Alfol® 610 and Alfol® 810 of Condea (now Sasol); Epal® 610 and Epal® 810 of Ethyl Corporation; Linevol® 79, Linevol® 911 and Dobanol® 25 L of Shell AG; Lial® 125 of Condea Augusta, Milan; Dehydad® and Lorol® of Henkel KGaA (now Cognis) as well as Linopol® 7-11 and Acropol® 91 of Ugine Kuhlmann.
- the block copolymer may be a methacrylate polymer.
- the hydrophobic first block may contain 70 wt % or more, or 80 wt % or more of the C 1-30 alkyl (meth)acrylic units containing C 12-15 alkyl (meth)acrylic units.
- the hydrophobic first block may contain up to 30 wt %, or up to 20 wt % of the C 1-30 alkyl (meth)acrylic units containing C 16-20 alkyl (meth)acrylic units.
- the hydrophobic first block contains C 1-30 alkyl (meth)acrylic units, wherein at least 70 wt % of the C 1-30 alkyl (meth)acrylic units may be C 12-15 alkyl (meth)acrylic units, and up to 30 wt % of the C 1-30 alkyl (meth)acrylic units are C 16-20 alkyl (meth)acrylic units, with the proviso that alkyl groups of the C 1-30 alkyl (meth)acrylic units have an average total number of carbon atoms of at least 8 (or at least 10 carbon atoms).
- the hydrophobic first block contains C 1-30 alkyl (meth)acrylic units, wherein at least 80 wt % of the C 1-30 alkyl (meth)acrylic units may be C 12-15 alkyl (meth)acrylic units, and up to 20 wt % of the C 1-30 alkyl (meth)acrylic units are C 16-20 alkyl (meth)acrylic units, with the proviso that alkyl groups of the C 1-30 alkyl (meth)acrylic units have an average total number of carbon atoms of at least 8 (or at least 10 carbon atoms).
- the hydrophobic first block contains C 1-30 alkyl (meth)acrylic units, wherein at least 50 wt % to 99 wt % of the C 1-30 alkyl (meth)acrylic units are C 12-15 alkyl (meth)acrylic units, and 1 up to 50 wt % of the C 1-30 alkyl (meth)acrylic units are C 16-20 alkyl (meth)acrylic units, with the proviso that alkyl groups of the C 1-30 alkyl (meth)acrylic units have an average total number of carbon atoms of at least 8 (or at least 10 carbon atoms).
- the hydrophobic first block contains C 1-30 alkyl (meth)acrylic units, wherein at least 75 wt % to 95 wt % of the C 1-30 alkyl (meth)acrylic units are C 12-15 alkyl (meth)acrylic units, and 5 up to 25 wt % of the C 1-30 alkyl (meth)acrylic units are C 16-20 alkyl (meth)acrylic units, with the proviso that alkyl groups of the C 1-30 alkyl (meth)acrylic units have an average total number of carbon atoms of at least 8 (or at least 10 carbon atoms).
- the hydrophobic first block contains C 1-30 alkyl (meth)acrylic units, wherein at least 80 wt % to 95 wt % of the C 1-30 alkyl (meth)acrylic units are C 12-15 alkyl (meth)acrylic units, and 1 up to 20 wt % of the C 1-30 alkyl (meth)acrylic units are C 16-20 alkyl (meth)acrylic units, with the proviso that alkyl groups of the C 1-30 alkyl (meth)acrylic units have an average total number of carbon atoms of at least 8 (or at least 10 carbon atoms).
- the second block having (meth)acrylic units have a heteroatom-containing group providing the polar group, with the heteroatom including sulphur, nitrogen, non-carbonyl oxygen, phosphorus, or mixtures thereof.
- the heteroatom may be nitrogen.
- non-carbonyl oxygen is not meant to exclude the presence of a carbonyl oxygen, but rather to indicate that if such is present, there will also be a heteroatom that is not a carbonyl oxygen (that is, neither an oxygen atom of an aldehyde, ketone or either oxygen atoms of a carboxylic acid or ester).
- the copolymer of the invention further includes a heteratom group derived from a nitrogen or oxygen containing group.
- the group may be derived from a nitrogen or oxygen containing compound capable of being incorporated during copolymerisation.
- the nitrogen or oxygen containing group may be derived from an aminoalkyl (meth)acrylamide or a nitrogen containing (meth)acrylate monomer that may be represented by the formula:
- nitrogen-containing compounds capable of being incorporated into the copolymer include N,N-dimethylacrylamide, N-vinyl carbonamides (such as, N-vinyl-formamide, N-vinylacetoamide, N-vinyl propionamides, N-vinyl hydroxyaceto amide, vinyl pyridine, N-vinyl imidazole, N-vinyl pyrrolidinone, N-vinyl caprolactam, dimethylaminoethyl acrylate, dimethylaminoethyl methacrylate, dimethylaminobutylacrylamide, dimethylaminopropyl methacrylate, dimethylaminopropyl acrylate, dimethyl-aminopropylacrylamide, dimethylaminopropylmethacrylamide, dimethylamino-ethylacrylamide or mixtures thereof.
- N-vinyl carbonamides such as, N-vinyl-formamide, N-vinylacetoamide, N-vinyl
- the heteratom group derived from a nitrogen containing group may include dimethylaminoethyl acrylate, dimethyl-aminoethyl methacrylate, dimethylaminopropyl methacrylate, dimethylamino-propyl acrylate, dimethylaminopropylacrylamide, dimethylaminopropyl-methacrylamide, nitriles of (meth)acrylic acid and other nitrogen-containing (meth)acrylates, such as N-(methacryloyloxyethyl)diisobutyl ketimine, N-(methacryloyloxyethyl)dihexadecyl ketimine, methacryloylamidoacetonitrile, 2-methacryloyloxyethylmethylcyanamide, cyanomethyl methacrylate, or mixtures thereof.
- suitable non-carbonyl oxygen containing compounds capable of being incorporated into the copolymer include hydroxyalkyl (meth)acrylates such as 3-hydroxypropyl methacrylate, 3,4-dihydroxybutyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2,5-dimethyl-1,6-hexanediol (meth)acrylate, 1,10-decanediol (meth)acrylate, carbonyl-containing methacrylates such as 2-carboxyethyl methacrylate, carboxymethyl methacrylate, oxazolidinylethyl methacrylate, N-(methacryloyl-oxy)formamide, acetonyl methacrylate, N-methacryloylmorpholine, N-methacryloyl-2-pyrrolidinone, N-(2-methacryloyloxyethyl)-2-pyrrolidinone, N-(3-
- suitable non-carbonyl oxygen containing compounds capable of being incorporated into the copolymer include methacrylates of ether alcohols, such as tetrahydrofurfuryl methacrylate, vinyloxyethoxyethyl methacrylate, methoxyethoxyethyl methacrylate, 1-butoxypropyl methacrylate, 1-methyl-(2-vinyloxy)ethyl methacrylate, cyclo-hexyloxymethyl methacrylate, methoxymethoxyethyl methacrylate, benzyloxy-methyl methacrylate, furfuryl methacrylate, 2-butoxyethyl methacrylate, 2-ethoxyethoxymethyl methacrylate, 2-ethoxyethyl methacrylate, allyloxymethyl methacrylate, 1-ethoxybutyl methacrylate, methoxymethyl methacrylate, 1-ethoxyethyl methacrylate, ethoxymethyl methacrylate and
- the block copolymer may be obtained/obtainable from controlled radical or other living polymerisation techniques such as RAFT (Reversible Addition Fragmentation Transfer), ATRP (Atom Transfer Radical Polymerisation), nitroxide-mediated and anionic. These polymerisation techniques are known to a person skilled in the art.
- Anionic polymerisation processes may be useful when the heteroatom of the second block contains a nitrogen heteroatom (from an amine) when steps are taken to quench the amine during polymerisation.
- Such techniques are known to a person skilled in the art.
- the controlled radical polymerisation process employed to prepare the block copolymer may be a RAFT process.
- RAFT processes A detailed description of RAFT processes is described in WO2006/047393 (see whole document for reagents, and reference to linear polymers) or US Patent Application 2006/0189490 (see paragraphs [0128] to [0131].
- the controlled radical polymerisation process employed to prepare the block copolymer may be an ATRP process.
- groups that may be transferred by a radical mechanism include halogens (from a halogen-containing compound) or various ligands.
- groups that may be transferred are described in U.S. Pat. No. 6,391,996, or paragraphs 61 to 65 of US Patent Application 2005/038146.
- Another detailed description of ATRP processes is described in US Patent Application 2006/0189490 (see paragraphs [0102] to [0126]).
- the controlled radical polymerisation process may be a RAFT process.
- chain transfer agents are important. A more detailed review of suitable chain transfer agents is found in paragraphs 66 to 71 of US Patent Application US 2005/038146.
- a suitable RAFT chain transfer agent includes 2-Dodecylsulphanylthiocarbonylsulphanyl-2-methyl-propionic acid butyl ester, cumyl dithiobenzoate or mixtures thereof.
- the lubricating composition comprises an oil of lubricating viscosity.
- oils include natural and synthetic oils, oil derived from hydrocracking, hydrogenation, and hydrofinishing, unrefined, refined and re-refined oils and mixtures thereof.
- Unrefined oils are those obtained directly from a natural or synthetic source generally without (or with little) further purification treatment.
- Refined oils are similar to the unrefined oils except they have been further treated in one or more purification steps to improve one or more properties.
- Purification techniques include solvent extraction, secondary distillation, acid or base extraction, filtration, percolation and the like.
- Re-refined oils are also known as reclaimed or reprocessed oils, and are obtained by processes similar to those used to obtain refined oils and often are additionally processed by techniques directed to removal of spent additives and oil breakdown products.
- Natural oils useful in making the inventive lubricants include animal oils, vegetable oils (e.g., castor oil), mineral lubricating oils such as liquid petroleum oils and solvent-treated or acid-treated mineral lubricating oils of the paraffinic, naphthenic or mixed paraffinic-naphthenic types and oils derived from coal or shale or mixtures thereof.
- animal oils e.g., castor oil
- mineral lubricating oils such as liquid petroleum oils and solvent-treated or acid-treated mineral lubricating oils of the paraffinic, naphthenic or mixed paraffinic-naphthenic types and oils derived from coal or shale or mixtures thereof.
- Synthetic lubricating oils are useful and include hydrocarbon oils such as polymerised and interpolymerised olefins (typically hydrogenated) (e.g., polybutylenes, polypropylenes, propyleneisobutylene copolymers); poly(1-hexenes), poly(1-octenes), poly(1-decenes), and mixtures thereof; alkyl-benzenes (e.g.
- dodecylbenzenes dodecylbenzenes, tetradecylbenzenes, dinonylbenzenes, di-(2-ethylhexyl)-benzenes); polyphenyls (e.g., biphenyls, terphenyls, alkylated polyphenyls); diphenyl alkanes, alkylated diphenyl alkanes, alkylated diphenyl ethers and alkylated diphenyl sulphides and the derivatives, analogs and homologs thereof or mixtures thereof.
- polyphenyls e.g., biphenyls, terphenyls, alkylated polyphenyls
- diphenyl alkanes alkylated diphenyl alkanes, alkylated diphenyl ethers and alkylated diphenyl sulphides and the derivatives, analogs and homologs thereof or mixtures thereof
- oils include polyol esters (such as Prolube®3970), diesters, liquid esters of phosphorus-containing acids (e.g., tricresyl phosphate, trioctyl phosphate, and the diethyl ester of decane phosphonic acid), or polymeric tetrahydrofurans.
- Synthetic oils may be produced by Fischer-Tropsch reactions and typically may be hydroisomerised Fischer-Tropsch hydrocarbons or waxes. In one embodiment oils may be prepared by a Fischer-Tropsch gas-to-liquid synthetic procedure as well as other gas-to-liquid oils.
- Oils of lubricating viscosity may also be defined as specified in the American Petroleum Institute (API) Base Oil Interchangeability Guidelines.
- the five base oil groups are as follows: Group I (sulphur content>0.03 wt %, and/or ⁇ 90 wt % saturates, viscosity index 80-120); Group II (sulphur content ⁇ 0.03 wt %, and ⁇ 90 wt % saturates, viscosity index 80-120); Group III (sulphur content ⁇ 0.03 wt %, and ⁇ 90 wt % saturates, viscosity index ⁇ 120); Group IV (all polyalphaolefins (PAOs)); and Group V (all others not included in Groups I, II, III, or IV).
- PAOs polyalphaolefins
- the oil of lubricating viscosity includes an API Group I, Group II, Group III, Group IV, Group V oil or mixtures thereof. Often the oil of lubricating viscosity is an API Group I, Group II, Group III, Group IV oil or mixtures thereof.
- the amount of the oil of lubricating viscosity present is typically the balance remaining after subtracting from 100 wt % the sum of the amount of the compound of the invention and the other performance additives.
- the lubricating composition may be in the form of a concentrate and/or a fully formulated lubricant. If the lubricating composition of the invention comprising the additives disclosed herein above is in the form of a concentrate (which may be combined with additional oil to form, in whole or in part, a finished lubricant), the ratio of the of these additives to the oil of lubricating viscosity and/or to diluent oil include the ranges of 1:99 to 99:1 by weight, or 80:20 to 10:90 by weight.
- the composition optionally includes other performance additives.
- the other performance additives comprise at least one of metal deactivators, viscosity modifiers, detergents, friction modifiers, antiwear agents, corrosion inhibitors, dispersants, dispersant viscosity modifiers, extreme pressure agents, antioxidants, foam inhibitors, demulsifiers, emulsifiers (other than the block copolymer of the invention), pour point depressants (other than the block copolymer of the invention), seal swelling agents and mixtures thereof.
- fully-formulated lubricating oil will contain one or more of these performance additives.
- the lubricating composition of the invention further includes at least one of a friction modifier, a viscosity modifier, an antioxidant, an overbased detergent, a succinimide dispersant, or mixtures thereof.
- the lubricating composition of the invention further includes at least one of a viscosity modifier, an antioxidant, an overbased detergent, a succinimide dispersant, or mixtures thereof.
- the lubricating composition further includes known neutral or overbased detergents.
- Suitable detergent substrates include phenates, sulphur containing phenates, sulphonates, salixarates, salicylates, carboxylic acid, phosphorus acid, mono- and/or di-thiophosphoric acids, alkyl phenols, sulphur coupled alkyl phenol compounds, or saligenins.
- overbased detergents and their methods of preparation are described in greater detail in numerous patent publications, including WO2004/096957 and references cited therein.
- the detergent substrate may be salted with a metal such as calcium, magnesium, potassium, sodium, or mixtures thereof.
- the overbased detergent is selected from the group consisting of phenates, sulphur containing phenates, sulphonates, salixarates, salicylates, and mixtures thereof.
- the selected overbased detergent include calcium or magnesium phenates, sulphur containing phenates, sulphonates, salixarates, saliginens, salicylates, or mixtures thereof.
- the detergent may be a calcium salicylate. In one embodiment the detergent may be a calcium sulphonate. In one embodiment the invention the detergent may be a mixture of a calcium sulphonate and a calcium salicylate.
- the detergent may be a calcium phenate. In one embodiment the detergent may be a calcium sulphonate. In one embodiment the invention the detergent may be a mixture of a calcium sulphonate and a calcium phenate.
- the detergent may be present (on an oil free basis i.e., an actives basis) at 0 wt % to 10 wt %, or 0.1 wt % to 8 wt %, or 1 wt % to 4 wt % of the lubricating composition.
- the amount of detergent may be 0 wt % to 40 wt %, or 2 wt % to 35 wt %, or 5 wt % to 30 wt % of the lubricating composition.
- Dispersants are often known as ashless-type dispersants because, prior to mixing in a lubricating oil composition, they do not contain ash-forming metals and they do not normally contribute any ash forming metals when added to a lubricant and polymeric dispersants.
- Ashless type dispersants are characterised by a polar group attached to a relatively high molecular weight hydrocarbon chain.
- Typical ashless dispersants include N-substituted long chain alkenyl succinimides. Examples of N-substituted long chain alkenyl succinimides include polyisobutylene succinimide with number average molecular weight of the polyisobutylene substituent in the range 350 to 5000, or 500 to 3000.
- Succinimide dispersants and their preparation are disclosed, for instance in U.S. Pat. No. 3,172,892 or U.S. Pat. No. 4,234,435.
- Succinimide dispersants are typically the imide formed from a polyamine, typically a poly(ethyleneamine).
- the invention further includes at least one dispersant which is a polyisobutylene succinimide derived from a polyisobutylene with number average molecular weight in the range 350 to 5000, or 500 to 3000.
- the polyisobutylene succinimide may be used alone or in combination with other dispersants.
- the invention further includes at least one dispersant derived from polyisobutylene succinic anhydride, an amine and zinc oxide to form a polyisobutylene succinimide complex with zinc.
- the polyisobutylene succinimide complex with zinc may be used alone or in combination.
- Mannich bases are the reaction products of alkyl phenols with aldehydes (especially formaldehyde) and amines (especially polyalkylene polyamines).
- aldehydes especially formaldehyde
- amines especially polyalkylene polyamines.
- the alkyl group typically contains at least 30 carbon atoms.
- the dispersants may also be post-treated by conventional methods by a reaction with any of a variety of agents. Among these are boron, urea, thiourea, dimercaptothiadiazoles, carbon disulphide, aldehydes, ketones, carboxylic acids, hydrocarbon-substituted succinic anhydrides, maleic anhydride, nitriles, epoxides, and phosphorus compounds.
- the dispersant may have a high total base number or the dispersant may have a high total acid number.
- dispersants with a high TAN number have a carbonyl to nitrogen ratio of 1 or higher, in one aspect 1.2 or higher, in another aspect 1.4 or higher and in yet another aspect 1.45 or higher, for example 1.5.
- dispersants with a high TBN number have a carbonyl to nitrogen ratio of less than 1, in one aspect 0.94 or lower, in another aspect 0.88 or lower and in another aspect 0.8 or lower, for instance 0.77.
- the carbonyl to nitrogen ratio is to be calculated on a molar basis, that is, the ratio of moles of carbonyl functionality (e.g., —C(O)O—) to the moles of nitrogen functionality (e.g., amine nitrogens).
- the dispersant may be in a mixture of (i) a dispersant with a carbonyl to nitrogen ratio of 1 or higher; and (ii) a dispersant with a carbonyl to nitrogen ratio of less than 1.
- the dispersant may be present (on an oil free basis i.e., an actives basis) at 0 wt % to 20 wt %, or 0.1 wt % to 15 wt %, or 0.1 wt % to 10 wt %, or 1 wt % to 6 wt % of the lubricating composition.
- Antioxidant compounds include for example, sulphurised olefins, alkylated diphenylamines (typically di-nonyl diphenylamine, octyl diphenylamine, di-octyl diphenylamine), hindered phenols, molybdenum compounds (such as molybdenum dithiocarbamates), or mixtures thereof. Antioxidant compounds may be used alone or in combination.
- the antioxidant may be present in ranges (on an oil free basis i.e., an actives basis) of 0 wt % to 20 wt %, or 0.1 wt % to 10 wt %, or 1 wt % to 5 wt %, of the lubricating composition.
- the hindered phenol antioxidant often contains a secondary butyl and/or a tertiary butyl group as a sterically hindering group.
- the phenol group may be further substituted with a hydrocarbyl group (typically linear or branched alkyl) and/or a bridging group linking to a second aromatic group.
- hindered phenol antioxidants examples include 2,6-di-tert-butylphenol, 4-methyl-2,6-di-tert-butylphenol, 4-ethyl-2,6-di-tert-butylphenol, 4-propyl-2,6-di-tert-butylphenol or 4-butyl-2,6-di-tert-butylphenol, or 4-dodecyl-2,6-di-tert-butylphenol.
- the hindered phenol antioxidant may be an ester and may include, e.g., IrganoxTM L-135 from Ciba.
- IrganoxTM L-135 from Ciba
- the lubricating composition further includes a molybdenum compound.
- the molybdenum compound is selected from the group consisting of molybdenum dialkyldithiophosphates, molybdenum dithiocarbamates, amine salts of molybdenum compounds, and mixtures thereof.
- molybdenum dithiocarbamates which may be used as an antioxidant include commercial materials sold under the trade names such as Molyvan 822TM, MolyvanTM A and Molyvan 855TM from R. T. Vanderbilt Co., Ltd., and Adeka Sakura-LubeTM S-100, S-165 S-515, S-600 and S-710 from Adeka; and mixtures thereof.
- the molybdenum compound may provide 5 ppm to 1000 ppm, or 20 ppm to 300 ppm of molybdenum to the lubricating composition.
- Viscosity modifiers include hydrogenated copolymers of maleic anhydride-(alpha olefin) copolymers, styrene-butadiene, ethylene-propylene copolymers, polyisobutenes, hydrogenated styrene-isoprene polymers, hydrogenated isoprene polymers, polymethacrylates, polyacrylates, polyalkyl styrenes, hydrogenated alkenyl arene conjugated diene copolymers, polyolefins, esters of maleic anhydride-styrene copolymers.
- Dispersant viscosity modifiers include functionalised polyolefins, for example, ethylene-propylene copolymers that have been functionalized with an acylating agent such as maleic anhydride and an amine; polymethacrylates functionalised with an amine, or esterified styrene-maleic anhydride copolymers reacted with an amine.
- an acylating agent such as maleic anhydride and an amine
- polymethacrylates functionalised with an amine or esterified styrene-maleic anhydride copolymers reacted with an amine.
- the lubricating composition further includes an antiwear agent.
- the additional antiwear agent may be either ashless or ash-forming. Typically ashless antiwear agents do not contain metal, whereas ash-forming do contain metal.
- the antiwear agent may be present (on an oil free basis i.e., an actives basis) in ranges including 0 wt % to 15 wt %, or 0 wt % to 10 wt %, or 0.05 wt % to 5 wt %, or 0.1 wt % to 3 wt % of the lubricating composition.
- the lubricating composition further includes a phosphorus-containing antiwear agent.
- a phosphorus-containing antiwear agent may be present in an amount to deliver the ranges of phosphorus described below in the subject matter under the sub-heading “Industrial Application”.
- Suitable antiwear agents include phosphate esters, sulphurised olefins, sulphur-containing anti-wear additives including metal dihydrocarbyldithiophosphates (such as primary or secondary zinc dialkyldithiophosphates, or molybdenum dialkyldithiophosphates), molybdenum thiocarbamate-containing compounds including thiocarbamate esters, alkylene-coupled thiocarbamates, and bis(S-alkyldithiocarbamyl) disulphides.
- metal dihydrocarbyldithiophosphates such as primary or secondary zinc dialkyldithiophosphates, or molybdenum dialkyldithiophosphates
- molybdenum thiocarbamate-containing compounds including thiocarbamate esters, alkylene-coupled thiocarbamates, and bis(S-alkyldithiocarbamyl) disulphides.
- Suitable zinc dialkyldithiophosphates include those disclosed in PCT Application US07/073,428 (entitled “Method of Lubricating an Internal Combustion Engine and Improving the Efficiency of the Emissions Control System of the Engine”) or in PCT Application US07/073,426 (entitled “Lubricating Oil Composition and Method of Improving Efficiency of Emissions Control System”). Both applications claim priority from Jul. 17, 2006.
- the zinc dialkyldithiophosphates or zinc dialkylphosphates may in one embodiment be defined as a zinc salt of a mixture of phosphorus-containing compounds represented by the formula.
- J 1 and J 2 are independently S or O, and R 3 and R 4 may be independently hydrocarbyl groups, the average total number of carbon atoms in R 3 plus R 4 for the mixture of phosphorus-containing compounds being at least 9.5; wherein R 3 and R 4 are characterised in that (i) 4 to 70 mole percent of such groups contain 2 to 4 carbon atoms and (ii) 30 to 96 mole percent such groups contain 5 to 12 carbon atoms; and wherein, in less than 8 mole percent of the molecules of the formula in the mixture of phosphorus-containing compounds, each of R 3 and R 4 contain 2 to 4 carbon atoms and in greater than 11 mole percent of the molecules of the formula in said mixture R 3 has 2 to 4 carbon atoms and R 4 has 5 to 12 carbon atoms; and wherein, within the formula, the average total number of hydrogen atoms in R 3 and R 4 on carbon atoms located beta to the O atoms is at least 7.25.
- the dithiocarbamate-containing compounds may be prepared by reacting a dithiocarbamate acid or salt with an unsaturated compound.
- the dithiocarbamate containing compounds may also be prepared by simultaneously reacting an amine, carbon disulphide and an unsaturated compound. Generally, the reaction occurs at a temperature of 25° C. to 125° C.
- U.S. Pat. Nos. 4,758,362 and 4,997,969 describe dithiocarbamate compounds and methods of making them.
- Suitable olefins that may be sulphurised to form an sulphurised olefin include propylene, butylene, isobutylene, pentene, hexane, heptene, octane, nonene, decene, undecene, dodecene, undecyl, tridecene, tetradecene, pentadecene, hexadecene, heptadecene, octadecene, octadecenene, nonodecene, eicosene or mixtures thereof.
- hexadecene, heptadecene, octadecene, octadecenene, nonodecene, eicosene or mixtures thereof and their dimers, trimers and tetramers are especially useful olefins.
- the olefin may be a Diels-Alder adduct of a diene such as 1,3-butadiene and an unsaturated ester, such as butylacrylate.
- sulphurised olefin includes fatty acids and their esters.
- the fatty acids are often obtained from vegetable oil or animal oil and typically contain 4 to 22 carbon atoms.
- suitable fatty acids and their esters include triglycerides, oleic acid, linoleic acid, palmitoleic acid or mixtures thereof.
- the fatty acids are obtained from lard oil, tall oil, peanut oil, soybean oil, cottonseed oil, sunflower seed oil or mixtures thereof.
- fatty acids and/or ester are mixed with olefins.
- EP agents include chlorinated wax; organic sulphides and polysulphides such as dibenzyldisulphide, bis-(chlorobenzyl) disulphide, dibutyl tetrasulphide, sulphurised methyl ester of oleic acid, sulphurised alkylphenol, sulphurised dipentene, sulphurised terpene, and sulphurised Diels-Alder adducts; phosphosulphurised hydrocarbons such as the reaction product of phosphorus sulphide with turpentine or methyl oleate; phosphorus esters such as the dihydrocarbon and trihydrocarbon phosphites, e.g., dibutyl phosphite, diheptyl phosphite,
- the lubricating composition further includes a friction modifier, or mixtures thereof.
- the friction modifier may be present (on an oil free basis i.e., an actives basis) in ranges including 0 wt % to 10 wt %, or 0.05 wt % to 8 wt %, or 0.1 wt % to 4 wt %.
- Suitable friction modifiers include long chain fatty acid derivatives of amines, esters, or epoxides; fatty imidazolines such as condensation products of carboxylic acids and polyalkylene-polyamines; amine salts of alkylphosphoric acids; fatty alkyl tartrates; fatty alkyl tartrimides; or fatty alkyl tartramides.
- Friction modifiers may also encompass materials such as fatty alkyl tartrates; fatty alkyl tartrimides, sulphurised fatty compounds and olefins, molybdenum dialkyldithiophosphates, molybdenum dithiocarbamates, sun-flower oil or monoester of a polyol and an aliphatic carboxylic acid (all these friction modifiers may also be described as antioxidants or antiwear agents).
- the friction modifier friction modifier is selected from the group consisting of long chain fatty acid derivatives of amines, esters, or epoxides; fatty alkyl tartrates; fatty alkyl tartrimides; and fatty alkyl tartramides.
- the friction modifier may be a long chain fatty acid ester (previously described above as an ashless antiwear agent).
- the long chain fatty acid ester may be a mono-ester, e.g., a monoglyceride, and in one embodiment the long chain fatty acid ester may be a (tri)glyceride.
- corrosion inhibitors include those described in paragraphs 5 to 8 of US Application US05/038319 (filed on Oct. 25, 2004 McAtee and Boyer as named inventors), octylamine octanoate, condensation products of dodecenyl succinic acid or anhydride and a fatty acid such as oleic acid with a polyamine.
- the corrosion inhibitors include the Synalox® corrosion inhibitor.
- the Synalox® corrosion inhibitor is typically a homopolymer or copolymer of propylene oxide.
- the Synalox® corrosion inhibitor is described in more detail in a product brochure with Form No. 118-01453-0702 AMS, published by The Dow Chemical Company.
- the product brochure is entitled “SYNALOX Lubricants, High-Performance Polyglycols for Demanding Applications.”
- Metal deactivators including derivatives of benzotriazoles (typically tolyltriazole), dimercaptothiadiazole derivatives, 1,2,4-triazoles, benzimid-azoles, 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 may be useful.
- benzotriazoles typically tolyltriazole
- dimercaptothiadiazole derivatives 1,2,4-triazoles
- benzimid-azoles 2-alkyldithiobenzimidazoles
- Foam inhibitors that may be useful in the compositions of the invention include 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 that may be useful in the compositions of the invention include polyalphaolefins, esters of maleic anhydride-styrene copolymers, fumarate ester-vinyl acetate copolymers, polyalkyl(meth)acrylates, polyalkylacrylates or polyalkylacrylamides.
- the mechanical device is an internal combustion engine.
- the internal combustion engine may be a diesel fueled engine, a gasoline fueled engine, a natural gas fueled engine or a mixed gasoline/alcohol fueled engine. In one embodiment the internal combustion engine may be a diesel fueled engine and in one embodiment a gasoline fueled engine.
- the internal combustion engine may be a 2-stroke or 4-stroke engine.
- Suitable internal combustion engines include marine diesel engines, aviation piston engines, low-load diesel engines, and automobile and truck engines.
- the components of the internal combustion engine include all of the parts of the engine derived from metal lubricated by an engine lubricant. This includes for example, cylinder liners, camshafts, pistons, bearings, oil coolers etc.
- the internal combustion engine contains components ferric (i.e., ferrous) components.
- the ferric components include Fe, FeO, Fe 3 O 4 or other materials containing iron.
- the internal combustion engine contains components of an aluminium-alloy.
- the aluminium-alloy includes aluminium silicates, aluminium oxides, or other ceramic materials.
- the aluminium-alloy is an aluminium-silicate surface.
- the lubricating composition for an internal combustion engine may be suitable for any engine lubricant irrespective of the sulphur, phosphorus or sulphated ash (ASTM D-874) content.
- the sulphur content of the engine oil lubricant may be 1 wt % or less, or 0.8 wt % or less, or 0.5 wt % or less, or 0.3 wt % or less. In one embodiment the sulphur content may be in the range of 0.001 wt % to 0.5 wt %, or 0.01 wt % to 0.3 wt %.
- the phosphorus content may be 0.2 wt % or less, or 0.1 wt % or less, or 0.085 wt % or less, or even 0.06 wt % or less, 0.055 wt % or less, or 0.05 wt % or less. In one embodiment the phosphorus content may be 100 ppm to 1000 ppm, or 200 ppm to 600 ppm.
- the total sulphated ash content may be 2 wt % or less, or 1.5 wt % or less, or 1.1 wt % or less, or 1 wt % or less, or 0.8 wt % or less, or 0.5 wt % or less. In one embodiment the sulphated ash content may be 0.05 wt % to 0.9 wt %, or 0.1 wt % to 0.2 wt % to 0.45 wt %.
- the lubricating composition may be an engine oil, wherein the lubricating composition may be characterised as having (i) a sulphur content of 0.5 wt % or less, (ii) a phosphorus content of 0.08 wt % or less, and (iii) a sulphated ash content of 1.5 wt % or less.
- the lubricating composition may be suitable for a 2-stroke or a 4-stroke marine diesel internal combustion engine.
- the marine diesel combustion engine is a 2-stroke engine.
- the block copolymer of the invention may also be used in a variety of lubricants requiring emulsifiers and/or pour point depressants.
- the block copolymer of the invention may be an emulsifier and/or pour point depressant in driveline devices, industrial gears, hydraulic devices, off-highway mobile equipment such as farm tractors, greases, metalworking fluids and fuels.
- the lubricant formulation may, as a person skilled in the art will appreciate, change due to the different additives and treat rates commonly employed in each lubricant type. None the less, the block copolymer is believed to function as an emulsifier and/or pour point depressant.
- Driveline devices include gearboxes, axle gears, traction drive transmissions, automatic transmissions or manual transmissions.
- Automatic transmissions include continuously variable transmissions (CVT), infinitely variable transmissions (IVT), Torroidal transmissions, continuously slipping torque converted clutches (CSTCC), stepped automatic transmissions or dual clutch transmissions (DCT).
- CVT continuously variable transmissions
- IVT infinitely variable transmissions
- CSTCC continuously slipping torque converted clutches
- DCT dual clutch transmissions
- diblock copolymer of (C 12-15 -alkyl methacrylate and 2-ethylhexylmethacrylate)-b-dimethylaminoethyl meth-acrylate.
- the diblock copolymer is prepared by charging reagents into a 4-necked flask equipped with a nitrogen inlet, thermocouple and a heating mantle.
- the reagents added include 99.2 g of C 12-15 -alkyl methacrylate, 48 g of 2-ethylhexylmethacrylate, 5.04 g of a chain transfer agent (dodecyl-trithiocarbonate butyl ester), 0.87 g of Trigonox®21 initiator and 41.48 g of PAO-4 diluent oil.
- the flask is stirred and purged with nitrogen for 30 minutes.
- the nitrogen flow rate is 0.028 m 3 /hr (or 1 SCFH).
- the flask is then heated to 90° C. and the nitrogen flow is reduced to 0.014 m 3 /hr (or 0.5 SCFH) and held for 150 minutes.
- the flask is then charged with 12.8 g of dimethylaminoethyl methacrylate.
- the flask is held for a further 3 hours at 90° C., before cooling.
- the product is a viscous liquid.
- C 12-15 -alkyl methacrylate and 2-ethylhexylmethacrylate is a diblock copolymer of (C 12-15 -alkyl methacrylate and 2-ethylhexylmethacrylate)-b-dimethylaminoethyl meth-acrylate.
- 111.6 g of C 12-15 -alkyl methacrylate, 54 g of 2-ethylhexyl-methacrylate, and 0.97 g of Trigonox®21 initiator are blended to form a blend.
- About one third of the blend is charged into a 4-necked flask equipped with a nitrogen inlet, thermocouple and a heating mantle. 5.67 g of a chain transfer agent (dodecyl-trithiocarbonate butyl ester) is then added to the flask.
- a chain transfer agent dodecyl-trithiocarbonate butyl ester
- the flask is stirred and purged with nitrogen for 30 minutes.
- the nitrogen flow rate is 0.028 m 3 /hr (or 1 SCFH).
- the flask is then heated to 80° C. and the nitrogen flow is reduced to 0.014 m 3 /hr (or 0.5 SCFH) and the remaining two thirds of the blend is added over a period of 90 minutes.
- the flask is maintained at 80° C. and held for 150 minutes.
- the flask is then charged with 14.4 g of dimethylaminoethyl methacrylate.
- the flask is held for a further 150 minutes at 80° C., before cooling.
- the product is a viscous liquid.
- C 12-15 -alkyl methacrylate and C 16-18 -alkyl methacrylate is a diblock copolymer of (C 12-15 -alkyl methacrylate and C 16-18 -alkyl methacrylate)-b-dimethylaminoethyl meth-acrylate.
- the flask is stirred and purged with nitrogen for 30 minutes.
- the nitrogen flow rate is 0.056 m 3 /hr (or 2 SCFH).
- the flask is then heated to 80° C. and the nitrogen flow is reduced to 0.014 m 3 /hr (or 0.5 SCFH) and the remaining two thirds of the blend is added over a period of 90 minutes.
- the flask is maintained at 80° C. and held for 15 hours.
- the flask is then charged with 240 g of dimethylaminoethyl methacrylate.
- the flask is held for at 90° C. for 2 hours.
- Three separate charges (each 1 g) of Trigonox®21 initiator are added over a period of 5 hours.
- the product is a viscous liquid before dilution with diluent oil to form a 40% polymer mixture in oil.
- diblock copolymer prepared by a process similar to EX3, except the final polymer is a block copolymer of (C 12-15 -alkyl methacrylate and C 16-18 -alkyl methacrylate)-b-(dimethylaminoethyl methacrylate and methylmethacrylate).
- the methyl methacrylate is added concurrently with dimethylaminoethyl methacrylate.
- the ratio of the weight percent of C 12-15 -alkyl methacrylate to C 16-18 -alkyl methacrylate is 85:15 (the C 16-18 -alkyl methacrylate also contains up to 5 wt % C 14 -alkyl methacrylate and up to 2 wt % C 20 -alkyl methacrylate).
- the ratio of the weight percent of dimethylaminoethyl methacrylate to methylmethacrylate is 91:9.
- the ratio weight percent of hydrophobic block to the second block containing a polar group is 87:13.
- the product is a viscous liquid before dilution with diluent oil to form a 50% polymer mixture in oil.
- the random polymer is a random polymer of C 12-15 -alkyl methacrylate, 2-ethylhexylmethacrylate, and dimethylaminoethyl methacrylate.
- the random polymer is prepared by charging reagents into a 4-necked flask equipped with a nitrogen inlet, thermocouple and a heating mantle.
- the reagents added include 99.2 g of C 12-15 -alkyl methacrylate, 48 g of 2-ethylhexylmethacrylate, 12.8 g of dimethylaminoethyl methacrylate, 5.04 g of a chain transfer agent (dodecyl-trithiocarbonate butyl ester), 0.87 g of Trigonox®21 initiator and 41.48 g of PAO-4 diluent oil. The flask is then heated to 90° C. as is described in EX1.
- the listed amount of the products from the preparative example or comparative preparative example includes the amount of diluent oil reported to be added or included therein.
- Comparative Lubricant Example 1 is a SAE 5W-30 engine lubricant.
- Comparative Lubricant Example 2 is a 5W-30 engine lubricant similar to CLC1, except it further contains 0.05 wt % of the product of CP1.
- Comparative Lubricant Example 3 is a 5W-30 engine lubricant similar to CLC1, except it further contains 0.12 wt % of the product of CP1.
- Comparative Lubricant Example 4 is a oil mixture of 80 wt % of ExxonMobil Group II EHCTM-45, with viscosity of 4.6 mm 2 /s at 100° C. and 20 wt % of ExxonMobil Group II EHCTM-60, with viscosity of 6.0 mm 2 /s at 100° C.
- Lubricant Example 1 is a 5W-30 engine lubricant similar to CLC1, except it further contains 0.05 wt % of the product of EX1.
- Lubricant Example 2 is a 5W-30 engine lubricant similar to CLC1, except it further contains 0.12 wt % of the product of EX1.
- Lubricant Example 3 is a 5W-30 engine lubricant similar to CLC1, except it further contains 0.05 wt % of the product of EX2.
- Lubricant Example 4 is a 5W-30 engine lubricant similar to CLC1, except it further contains 0.12 wt % of the product of EX2.
- Lubricant Example 5 is a 5W-30 engine lubricant similar to CLC1, except it further contains 0.07 wt % of the product of EX3.
- Lubricant Example 6 is a 5W-30 engine lubricant similar to CLC1, except it further contains 0.16 wt % of the product of EX3.
- Lubricant Example 7 is a 5W-30 engine lubricant similar to CLC1, except it further contains 0.06 wt % of the product of EX4.
- Lubricant Example 8 is a 5W-30 engine lubricant similar to CLC1, except it further contains 0.15 wt % of the product of EX4.
- Lubricant Example 9 is similar to CLC4, except it contains 0.26 wt % of the product of EX2.
- Lubricant Example 10 is similar to CLC4, except it contains 0.35 wt % of the product of EX3.
- Lubricant Example 11 (LC11) is similar to CLC4, except it contains 0.35 wt % of the product of EX4.
- Lubricant examples LC1 to LC8 and comparative Lubricant examples CLC1 to CLC3 are evaluated in the following ASTM tests D445, D4684-07 and D5985-02. The lubricants are also evaluated in Chrysler's FFV emulsion stability test.
- ASTM D445 relates to measurement of kinematic viscosity (units mm 2 /s) at 100° C.
- ASTM D4684-07 Mini-Rotary Viscometer or MRV
- MRV Minimum-Rotary Viscometer
- Yield stress and low-shear-rate viscosity are measured after cooling at controlled rates over a period exceeding 45 hour to a final test temperature between ⁇ 10° C. and ⁇ 40° C.
- the units are Centipoise (cP) or mPa-s.
- D5985-02 covers the determination of pour point of petroleum products by an automatic instrument that continuously rotates the test specimen against a suspended detection device during cooling of the test specimen.
- the Chrysler FFV emulsion stability test involves the steps of combining 10 volume % E85 fuel, 10% water, and 80% fully formulated engine oil and mixing them in a Waring blender. The resultant emulsion is stored in graduated cylinders at 0° C. and room temperature (25° C.) for 24 hours. At the end of the test, the volume percent oil (% oil), percent emulsion (% emul), and percent water (% H 2 O) are recorded. Typically, a formulated oil is considered to pass the FFV test if % H 2 O at both 0° C. and room temperature is zero.
- C 1-30 alkyl (meth)acrylic units relate to product formed by the polymerisation of C 1-30 alkyl (meth)acrylic monomer.
- the C 1-30 alkyl (meth)acrylic units may then be used to form the block(s) as described herein above.
- Reference to the percentage of C 1-30 alkyl (meth)acrylic units is considered as a mole percent.
- 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);
- aliphatic e.g., alkyl or alkenyl
- alicyclic e.g., cycloalkyl, cycloalkenyl
- 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 sulphoxy);
- 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 encompass substituents as pyridyl, furyl, thienyl and imidazolyl;
- heteroatoms including sulphur, oxygen, and nitrogen.
- no more than two, preferably 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.
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Lubricants (AREA)
- Graft Or Block Polymers (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/127,114 US20110263470A1 (en) | 2008-11-05 | 2009-11-03 | Composition Containing a Block Copolymer and a Method of Lubricating an Internal Combustion Engine |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11140808P | 2008-11-05 | 2008-11-05 | |
US13/127,114 US20110263470A1 (en) | 2008-11-05 | 2009-11-03 | Composition Containing a Block Copolymer and a Method of Lubricating an Internal Combustion Engine |
PCT/US2009/063046 WO2010053890A1 (en) | 2008-11-05 | 2009-11-03 | Composition containing a block copolymer and a method of lubricating an internal combustion engine |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2009/063046 A-371-Of-International WO2010053890A1 (en) | 2008-11-05 | 2009-11-03 | Composition containing a block copolymer and a method of lubricating an internal combustion engine |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US15/249,873 Continuation US20160362628A1 (en) | 2008-11-05 | 2016-08-29 | Composition Containing A Block Copolymer And A Method Of Lubricating An Internal Combustion Engine |
Publications (1)
Publication Number | Publication Date |
---|---|
US20110263470A1 true US20110263470A1 (en) | 2011-10-27 |
Family
ID=41506421
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/127,114 Abandoned US20110263470A1 (en) | 2008-11-05 | 2009-11-03 | Composition Containing a Block Copolymer and a Method of Lubricating an Internal Combustion Engine |
US15/249,873 Abandoned US20160362628A1 (en) | 2008-11-05 | 2016-08-29 | Composition Containing A Block Copolymer And A Method Of Lubricating An Internal Combustion Engine |
US15/730,879 Abandoned US20180030366A1 (en) | 2008-11-05 | 2017-10-12 | Composition Containing a Block Copolymer and a Method of Lubricating an Internal Combustion Engine |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US15/249,873 Abandoned US20160362628A1 (en) | 2008-11-05 | 2016-08-29 | Composition Containing A Block Copolymer And A Method Of Lubricating An Internal Combustion Engine |
US15/730,879 Abandoned US20180030366A1 (en) | 2008-11-05 | 2017-10-12 | Composition Containing a Block Copolymer and a Method of Lubricating an Internal Combustion Engine |
Country Status (9)
Country | Link |
---|---|
US (3) | US20110263470A1 (ja) |
EP (1) | EP2358849A1 (ja) |
JP (1) | JP5559803B2 (ja) |
KR (1) | KR101679090B1 (ja) |
CN (2) | CN105296063A (ja) |
AU (2) | AU2009311294A1 (ja) |
BR (1) | BRPI0921231A2 (ja) |
CA (1) | CA2742516C (ja) |
WO (1) | WO2010053890A1 (ja) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20120220505A1 (en) * | 2009-09-14 | 2012-08-30 | The Lubrizol Corporation | Farm Tractor Lubricating Composition with Good Water Tolerance |
US20130199482A1 (en) * | 2010-10-14 | 2013-08-08 | Evonik Oil Additives Gmbh | Motor having improved properties |
WO2014184362A1 (en) * | 2013-05-17 | 2014-11-20 | Shell Internationale Research Maatschappij B.V. | Lubricating oil composition for an internal-combustion engine |
WO2015041891A1 (en) * | 2013-09-17 | 2015-03-26 | Vanderbilt Chemical, Llc | A method of reducing aqueous separation in an emulsion composition suitable for engine fueled by e85 fuel |
JP2016017093A (ja) * | 2014-07-04 | 2016-02-01 | 第一工業製薬株式会社 | 粘度指数向上剤およびこれを含有する潤滑油組成物 |
US20170009178A1 (en) * | 2014-02-28 | 2017-01-12 | Cosmo Oil Lubricants Co., Ltd. | Engine oil composition |
US11059924B2 (en) * | 2018-09-24 | 2021-07-13 | Infineum International Limited | Polymers and lubricating compositions containing polymers |
US11124721B2 (en) | 2016-09-21 | 2021-09-21 | The Lubrizol Corporation | Polyacrylate antifoam components for use in diesel fuels |
CN113862064A (zh) * | 2021-10-13 | 2021-12-31 | 中国石油化工股份有限公司 | 一种发动机油组合物 |
US11365367B2 (en) * | 2017-06-27 | 2022-06-21 | The Lubrizol Corporation | Lubricating composition for and method of lubricating an internal combustion engine |
US12031128B2 (en) | 2021-04-07 | 2024-07-09 | Battelle Memorial Institute | Rapid design, build, test, and learn technologies for identifying and using non-viral carriers |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101725568B1 (ko) * | 2009-06-04 | 2017-04-10 | 더루우브리졸코오포레이션 | 마찰 조정제와 점도 조정제를 함유하는 윤활 조성물 |
US20130340325A1 (en) * | 2012-06-22 | 2013-12-26 | Baker Hughes Incorporated | Charged Block Co-polymers as Pour Point Depressants |
GB201217313D0 (en) * | 2012-09-27 | 2012-11-14 | Univ Sheffield | Block copolymer synthesis |
CN106414686A (zh) * | 2014-06-19 | 2017-02-15 | 国际壳牌研究有限公司 | 润滑组合物 |
JP5866700B1 (ja) * | 2015-05-12 | 2016-02-17 | 国立大学法人東北大学 | 潤滑油添加剤および潤滑油組成物 |
US9765487B2 (en) | 2015-09-08 | 2017-09-19 | Baldwin Paving Co., Inc. | Systems for applying roadway surface treatments, and methods of using same |
FR3041349B1 (fr) * | 2015-09-18 | 2020-01-24 | Total Marketing Services | Copolymere utilisable comme additif detergent pour carburant |
EP3680313B1 (en) * | 2016-06-17 | 2022-03-23 | Total Marketing Services | Lubricant polymers |
EP3257920A1 (en) * | 2016-06-17 | 2017-12-20 | Total Marketing Services | Lubricant polymers |
JP6813996B2 (ja) * | 2016-08-31 | 2021-01-13 | 大塚化学株式会社 | ブロック共重合体、および、これを含有する樹脂改質剤、エポキシ樹脂組成物 |
JP6965342B2 (ja) * | 2016-10-12 | 2021-11-10 | シェブロン・オロナイト・テクノロジー・ビー.ブイ. | 船舶用ディーゼル潤滑油組成物 |
EP3898907A1 (en) | 2018-12-19 | 2021-10-27 | Evonik Operations GmbH | Use of associative triblockcopolymers as viscosity index improvers |
US11680222B2 (en) * | 2020-10-30 | 2023-06-20 | Afton Chemical Corporation | Engine oils with low temperature pumpability |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4941984A (en) * | 1989-07-31 | 1990-07-17 | The Lubrizol Corporation | Lubricating oil compositions and methods for lubricating gasoline-fueled and/or alcohol-fueled, spark-ignited engines |
US20060189490A1 (en) * | 2003-03-31 | 2006-08-24 | Alexander Dardin | Lubricating oil composition with good frictional properties |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3816314A (en) * | 1972-05-31 | 1974-06-11 | Exxon Research Engineering Co | Block copolymers of unsaturated ester and a nitrogen containing monomer as v.i.improving and dispersant additives for oils |
JPS63117026A (ja) * | 1986-10-23 | 1988-05-21 | イー・アイ・デユポン・ド・ネモアース・アンド・コンパニー | 油添加剤 |
US4985160A (en) * | 1989-02-08 | 1991-01-15 | E. I. Du Pont De Nemours And Company | Branched polymers as fuel oil additives |
DE19603696A1 (de) * | 1996-02-02 | 1997-08-07 | Roehm Gmbh | Demulgatoren |
FR2833186B1 (fr) * | 2001-12-12 | 2004-01-23 | Rhodia Chimie Sa | Utilisation de copolymeres cationiques a blocs comme aide au depot d'emulsions simples ou multiples |
JP4139383B2 (ja) * | 2002-05-03 | 2008-08-27 | ビーエーエスエフ ソシエタス・ヨーロピア | (メタ)アクリルアミド単位を含む少なくとも1種の水溶性コポリマーを含む化粧品 |
WO2005056739A1 (en) * | 2003-11-26 | 2005-06-23 | Arkema Inc. | Controlled radical acrylic copolymer thickeners |
JP2007238663A (ja) * | 2006-03-06 | 2007-09-20 | Sanyo Chem Ind Ltd | 潤滑油添加剤および潤滑油組成物 |
DE102005015931A1 (de) * | 2005-04-06 | 2006-10-12 | Rohmax Additives Gmbh | Polyalkyl(meth) acrylat-Copolymere mit hervorragenden Eigenschaften |
JP5106778B2 (ja) * | 2006-01-24 | 2012-12-26 | 三洋化成工業株式会社 | 潤滑油用スラッジ分散剤 |
US8105990B2 (en) * | 2006-03-15 | 2012-01-31 | Nippon Oil Corporation | Lube base oil, lubricating oil composition for internal combustion engine, and lubricating oil composition for drive transmission device |
-
2009
- 2009-11-03 US US13/127,114 patent/US20110263470A1/en not_active Abandoned
- 2009-11-03 AU AU2009311294A patent/AU2009311294A1/en not_active Abandoned
- 2009-11-03 CA CA2742516A patent/CA2742516C/en active Active
- 2009-11-03 EP EP09748200A patent/EP2358849A1/en not_active Withdrawn
- 2009-11-03 CN CN201510634360.1A patent/CN105296063A/zh active Pending
- 2009-11-03 JP JP2011534870A patent/JP5559803B2/ja active Active
- 2009-11-03 CN CN2009801534821A patent/CN102272278A/zh active Pending
- 2009-11-03 KR KR1020117012684A patent/KR101679090B1/ko active IP Right Grant
- 2009-11-03 BR BRPI0921231A patent/BRPI0921231A2/pt not_active Application Discontinuation
- 2009-11-03 WO PCT/US2009/063046 patent/WO2010053890A1/en active Application Filing
-
2016
- 2016-08-24 AU AU2016219628A patent/AU2016219628A1/en not_active Abandoned
- 2016-08-29 US US15/249,873 patent/US20160362628A1/en not_active Abandoned
-
2017
- 2017-10-12 US US15/730,879 patent/US20180030366A1/en not_active Abandoned
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4941984A (en) * | 1989-07-31 | 1990-07-17 | The Lubrizol Corporation | Lubricating oil compositions and methods for lubricating gasoline-fueled and/or alcohol-fueled, spark-ignited engines |
US20060189490A1 (en) * | 2003-03-31 | 2006-08-24 | Alexander Dardin | Lubricating oil composition with good frictional properties |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20120220505A1 (en) * | 2009-09-14 | 2012-08-30 | The Lubrizol Corporation | Farm Tractor Lubricating Composition with Good Water Tolerance |
US9528072B2 (en) * | 2009-09-14 | 2016-12-27 | The Lubrizol Corporation | Farm tractor lubricating composition with good water tolerance |
US20130199482A1 (en) * | 2010-10-14 | 2013-08-08 | Evonik Oil Additives Gmbh | Motor having improved properties |
WO2014184362A1 (en) * | 2013-05-17 | 2014-11-20 | Shell Internationale Research Maatschappij B.V. | Lubricating oil composition for an internal-combustion engine |
WO2015041891A1 (en) * | 2013-09-17 | 2015-03-26 | Vanderbilt Chemical, Llc | A method of reducing aqueous separation in an emulsion composition suitable for engine fueled by e85 fuel |
US9550952B2 (en) | 2013-09-17 | 2017-01-24 | Vanderbilt Chemicals, Llc | Method of reducing aqueous separation in an emulsion composition suitable for engine fueled by E85 fuel |
US20170009178A1 (en) * | 2014-02-28 | 2017-01-12 | Cosmo Oil Lubricants Co., Ltd. | Engine oil composition |
US9879201B2 (en) * | 2014-02-28 | 2018-01-30 | Cosmo Oil Lubricants Co., Ltd. | Engine oil composition |
JP2016017093A (ja) * | 2014-07-04 | 2016-02-01 | 第一工業製薬株式会社 | 粘度指数向上剤およびこれを含有する潤滑油組成物 |
US11124721B2 (en) | 2016-09-21 | 2021-09-21 | The Lubrizol Corporation | Polyacrylate antifoam components for use in diesel fuels |
US11365367B2 (en) * | 2017-06-27 | 2022-06-21 | The Lubrizol Corporation | Lubricating composition for and method of lubricating an internal combustion engine |
US11059924B2 (en) * | 2018-09-24 | 2021-07-13 | Infineum International Limited | Polymers and lubricating compositions containing polymers |
US12031128B2 (en) | 2021-04-07 | 2024-07-09 | Battelle Memorial Institute | Rapid design, build, test, and learn technologies for identifying and using non-viral carriers |
CN113862064A (zh) * | 2021-10-13 | 2021-12-31 | 中国石油化工股份有限公司 | 一种发动机油组合物 |
Also Published As
Publication number | Publication date |
---|---|
AU2009311294A1 (en) | 2010-05-14 |
CN105296063A (zh) | 2016-02-03 |
CN102272278A (zh) | 2011-12-07 |
WO2010053890A1 (en) | 2010-05-14 |
JP5559803B2 (ja) | 2014-07-23 |
US20180030366A1 (en) | 2018-02-01 |
KR101679090B1 (ko) | 2016-11-23 |
BRPI0921231A2 (pt) | 2018-06-26 |
JP2012507613A (ja) | 2012-03-29 |
AU2016219628A1 (en) | 2016-09-08 |
CA2742516C (en) | 2019-06-04 |
EP2358849A1 (en) | 2011-08-24 |
KR20110095286A (ko) | 2011-08-24 |
CA2742516A1 (en) | 2010-05-14 |
US20160362628A1 (en) | 2016-12-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2742516C (en) | Composition containing a block copolymer and a method of lubricating an internal combustion engine | |
US9006159B2 (en) | Star polymer lubricating composition | |
US9528072B2 (en) | Farm tractor lubricating composition with good water tolerance | |
CA2781880C (en) | Lubricating composition containing viscosity modifier combination | |
US8835367B2 (en) | Polymethacrylates as high VI viscosity modifiers | |
US9528069B2 (en) | Lubricant and functional fluid compositions containing viscosity index improver | |
US8093191B2 (en) | Engine lubricant for improved fuel economy | |
JP2017533985A (ja) | 潤滑剤用途のための混合リン含有酸エステル | |
EP2714870A1 (en) | Lubricating composition comprising poly (isobutylene) /poly (vinyl aromatic) block copolymer | |
EP4377426A1 (en) | 1,4-benzoxazine compounds and lubricant compositions containing the same | |
US20220169944A1 (en) | Engine oils with low temperature pumpability |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: THE LUBRIZOL CORPORATION, OHIO Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:QIN, HAIHU;WANG, YING;BAUM, MARINA;AND OTHERS;SIGNING DATES FROM 20110507 TO 20110613;REEL/FRAME:026570/0878 |
|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |