CA3046788A1 - Lubricating composition including n-alkylated dianiline - Google Patents
Lubricating composition including n-alkylated dianiline Download PDFInfo
- Publication number
- CA3046788A1 CA3046788A1 CA3046788A CA3046788A CA3046788A1 CA 3046788 A1 CA3046788 A1 CA 3046788A1 CA 3046788 A CA3046788 A CA 3046788A CA 3046788 A CA3046788 A CA 3046788A CA 3046788 A1 CA3046788 A1 CA 3046788A1
- Authority
- CA
- Canada
- Prior art keywords
- lubricating composition
- lubricating
- prior
- oil
- alkylated
- 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.)
- Pending
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- 239000000203 mixture Substances 0.000 title claims abstract description 276
- 230000001050 lubricating effect Effects 0.000 title claims abstract description 205
- QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical class C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 title claims description 17
- -1 N-alkylated dianiline compound Chemical class 0.000 claims abstract description 181
- 239000003599 detergent Substances 0.000 claims abstract description 80
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 56
- 239000011575 calcium Substances 0.000 claims abstract description 44
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 44
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 39
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 39
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 32
- 239000011574 phosphorus Substances 0.000 claims abstract description 32
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 31
- 125000005266 diarylamine group Chemical group 0.000 claims abstract description 17
- 239000002530 phenolic antioxidant Substances 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 239000002270 dispersing agent Substances 0.000 claims description 34
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 30
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 29
- 238000002485 combustion reaction Methods 0.000 claims description 28
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 239000011593 sulfur Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- 150000002576 ketones Chemical class 0.000 claims description 19
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 17
- 239000011777 magnesium Substances 0.000 claims description 17
- 229910052749 magnesium Inorganic materials 0.000 claims description 17
- 229960002317 succinimide Drugs 0.000 claims description 15
- 150000001336 alkenes Chemical class 0.000 claims description 13
- 150000001299 aldehydes Chemical class 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 10
- 229920000098 polyolefin Polymers 0.000 claims description 10
- 229910052725 zinc Inorganic materials 0.000 claims description 10
- 239000011701 zinc Substances 0.000 claims description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- UKJKXXKVCXIYTJ-UHFFFAOYSA-N 4-[1-(4-aminophenyl)-3-ethylheptyl]aniline Chemical compound C(C)C(CC(C1=CC=C(N)C=C1)C1=CC=C(N)C=C1)CCCC UKJKXXKVCXIYTJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000002015 acyclic group Chemical group 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
- MAIIVMNLKGOSLI-UHFFFAOYSA-N 4-[(4-aminophenyl)-cyclohexylmethyl]aniline Chemical compound C1=CC(N)=CC=C1C(C=1C=CC(N)=CC=1)C1CCCCC1 MAIIVMNLKGOSLI-UHFFFAOYSA-N 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 150000003873 salicylate salts Chemical class 0.000 claims 1
- 150000003871 sulfonates Chemical group 0.000 claims 1
- 239000003921 oil Substances 0.000 description 61
- 235000019198 oils Nutrition 0.000 description 60
- 239000003795 chemical substances by application Substances 0.000 description 30
- 239000000654 additive Substances 0.000 description 27
- 239000010705 motor oil Substances 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 23
- 150000002148 esters Chemical class 0.000 description 20
- 238000012360 testing method Methods 0.000 description 20
- 238000009472 formulation Methods 0.000 description 19
- 229910052751 metal Inorganic materials 0.000 description 19
- 239000002184 metal Substances 0.000 description 19
- 239000003607 modifier Substances 0.000 description 19
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 19
- 239000002585 base Substances 0.000 description 18
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 17
- 150000001412 amines Chemical class 0.000 description 16
- 150000003902 salicylic acid esters Chemical class 0.000 description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 15
- 239000003112 inhibitor Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 239000000314 lubricant Substances 0.000 description 14
- 229910052750 molybdenum Inorganic materials 0.000 description 14
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 14
- 239000004034 viscosity adjusting agent Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000010687 lubricating oil Substances 0.000 description 12
- 239000011733 molybdenum Substances 0.000 description 12
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 11
- 229920002367 Polyisobutene Polymers 0.000 description 11
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 11
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 150000004665 fatty acids Chemical class 0.000 description 11
- 125000000743 hydrocarbylene group Chemical group 0.000 description 11
- 238000007254 oxidation reaction Methods 0.000 description 11
- 239000002199 base oil Substances 0.000 description 10
- 229920000768 polyamine Polymers 0.000 description 10
- 239000003760 tallow Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 235000015278 beef Nutrition 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 150000003609 titanium compounds Chemical class 0.000 description 8
- 239000008186 active pharmaceutical agent Substances 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 238000005260 corrosion Methods 0.000 description 7
- 230000007797 corrosion Effects 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000006260 foam Substances 0.000 description 7
- 239000005078 molybdenum compound Substances 0.000 description 7
- 235000012424 soybean oil Nutrition 0.000 description 7
- 239000003549 soybean oil Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical class O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 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 6
- 229920000642 polymer Polymers 0.000 description 6
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 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 5
- 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 5
- 239000010685 fatty oil Substances 0.000 description 5
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 150000002752 molybdenum compounds Chemical class 0.000 description 5
- 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 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 229920013639 polyalphaolefin Polymers 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 238000007655 standard test method Methods 0.000 description 5
- 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 5
- 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 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
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 4
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 239000003502 gasoline Substances 0.000 description 4
- VAMFXQBUQXONLZ-UHFFFAOYSA-N icos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 150000002646 long chain fatty acid esters Chemical class 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 150000002924 oxiranes Chemical class 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920000193 polymethacrylate Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 235000011044 succinic acid Nutrition 0.000 description 4
- 150000003900 succinic acid esters Chemical class 0.000 description 4
- 229940095064 tartrate Drugs 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- ZCSHACFHMFHFKK-UHFFFAOYSA-N 2-methyl-1,3,5-trinitrobenzene;2,4,6-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)C1NC([N+]([O-])=O)NC([N+]([O-])=O)N1.CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O ZCSHACFHMFHFKK-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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- 235000019483 Peanut oil Nutrition 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 235000019486 Sunflower oil Nutrition 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 125000005263 alkylenediamine group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 235000018660 ammonium molybdate Nutrition 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 3
- 159000000007 calcium salts Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 235000012343 cottonseed oil Nutrition 0.000 description 3
- 239000002385 cottonseed oil Substances 0.000 description 3
- 125000005265 dialkylamine group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 159000000003 magnesium salts Chemical class 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 239000006078 metal deactivator Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000003345 natural gas Substances 0.000 description 3
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- 239000003209 petroleum derivative Substances 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
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 235000015393 sodium molybdate Nutrition 0.000 description 1
- 239000011684 sodium molybdate Substances 0.000 description 1
- TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical class O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003899 tartaric acid esters Chemical class 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940095068 tetradecene Drugs 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- VQOXUMQBYILCKR-UHFFFAOYSA-N tridecaene Natural products CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 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
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- USEBTXRETYRZKO-UHFFFAOYSA-L zinc;n,n-dioctylcarbamodithioate Chemical compound [Zn+2].CCCCCCCCN(C([S-])=S)CCCCCCCC.CCCCCCCCN(C([S-])=S)CCCCCCCC USEBTXRETYRZKO-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
-
- 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
- C10M163/00—Lubricating compositions characterised by the additive being a mixture of a compound of unknown or incompletely defined constitution and a non-macromolecular compound, each of these compounds being essential
-
- 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
- C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
- C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
- C10M2205/022—Ethene
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/028—Overbased salts thereof
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/26—Overbased carboxylic acid salts
- C10M2207/262—Overbased carboxylic acid salts derived from hydroxy substituted aromatic acids, e.g. salicylates
-
- 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/26—Amines
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—Amides; Imides
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
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- 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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/02—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
- C10M2219/022—Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds of hydrocarbons, e.g. olefines
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/046—Overbasedsulfonic acid salts
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
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- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
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- 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
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/04—Molecular weight; Molecular weight distribution
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/04—Detergent property or dispersant property
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- 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
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
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- 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
- C10N2030/40—Low content or no content compositions
- C10N2030/42—Phosphor free or low phosphor content compositions
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/52—Base number [TBN]
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- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
- C10N2060/14—Chemical after-treatment of the constituents of the lubricating composition by boron or a compound containing boron
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Abstract
A lubricating composition includes an oil of lubricating viscosity, an N-alkylated dianiline compound, and at least one of a) an ashless antioxidant, and b) an overbased calcium detergent. The ashless antioxidant may be selected from a diarylamine antioxidant, a phenolic antioxidant, and combinations thereof. The lubricating composition may contain less than 0.15 weight percent of phosphorus.
Description
To: Page 9 of 26 2018-10-26 16:16:13 EDT 12164728733 From: Attorney Fax PCT/US 2017/066 103 - 26.10.2018 Atty. Dkt. No. LBRZ 200040W001(4494-01-WO) LUBRICATING COMPOSITION INCLUDING N-ALKYLATED
DIANILINE
BACKGROUND
[0001] The exemplary embodiment relates to additives for lubricating compositions and finds particular application in connection with N-alkylated dianilines for improved deposit control in as deposit boosters in internal combustion engines.
DIANILINE
BACKGROUND
[0001] The exemplary embodiment relates to additives for lubricating compositions and finds particular application in connection with N-alkylated dianilines for improved deposit control in as deposit boosters in internal combustion engines.
[0002] U.S. Pat, No. 3,779,923 describes alkylateci methylenedianiline tars as antioxidants in lubricant compositions. The compounds are formed with a phosphorus-based catalyst.
[0003] U.S. Pat, No. 8,242,066 describes aniline compounds useful as ashless TBN
sources for lubricating oil compositions that are compatible with fluoroelastomeric engine seal materials.
sources for lubricating oil compositions that are compatible with fluoroelastomeric engine seal materials.
[0004] U.S. Pat. Nos. 3,011,976; 3,110,671.2_4,100,082; 4,200,545;
4,320,021, 4,370,246; an4-4,663,063; and 4,708.809 generally describe amino-phenol compounds as lubricating oil additives (e.g., dispersant/detergents/inhibitors), such as N,I\V-arylene diamines, 4,4', dl-(sec-alkvlamino)-diphenvl propane,¨ 4,4', di-(cyclohexvIalkylamino)-diphenyl propane. or 4.4. di-(sec-alkylamino)-diphenyl methane.
4,320,021, 4,370,246; an4-4,663,063; and 4,708.809 generally describe amino-phenol compounds as lubricating oil additives (e.g., dispersant/detergents/inhibitors), such as N,I\V-arylene diamines, 4,4', dl-(sec-alkvlamino)-diphenvl propane,¨ 4,4', di-(cyclohexvIalkylamino)-diphenyl propane. or 4.4. di-(sec-alkylamino)-diphenyl methane.
[0005] One test for assessing deposit formation is the "Standard Test Method for Determination of Moderately High Temperature Piston Deposits by Thermo-Oxidation Engine Oil Simulation Test-TEOST MHT," ASTM D7097 ¨ 09. WIT TEOST, as it wilt be referred to herein, is a bench test that is designed to predict the deposit-forming tendencies of engine oil in the piston ring belt and upper piston crown area during service, and is one of the required test methods in Specification 0 4485 to define API
Category-Identified engine oils.
Category-Identified engine oils.
[0006] Some methylenedianiline compounds (MDAs) have been found to improve thermal oxidation performance in engine oils and to boost thin-film antioxidancy.
However, formulating an engine oil for high performance on MHT TEOST can compromise performance in other key areas. For example, adding dispersants and detergents in large amounts can negatively impact the viscometric properties of the lubricating composition or seals performance.
However, formulating an engine oil for high performance on MHT TEOST can compromise performance in other key areas. For example, adding dispersants and detergents in large amounts can negatively impact the viscometric properties of the lubricating composition or seals performance.
[0007] It would be desirable for a lubricating composition to be able to provide good deposit control, both in fired engine tests and in bench tests such as MHT
TEOST, while also providing other performance properties.
AMENDED SHEET
Received at the EPO on Oct 26, 2018 22:29:51. Page 9 of 26 Duration: 10.26.2018 10:16:29 PM - 10.26.2018 10:29:51 PM. This page 9 of 26 was completed at 10.26.2018 10:22:02 PM
LUBRICATING COMPOSITION INCLUDING N-ALKYLATED DIANILINE
BACKGROUND
[0001] The exemplary embodiment relates to additives for lubricating compositions and finds particular application in connection with N-alkylated dianilines for improved deposit control in as deposit boosters in internal combustion engines.
[0002] U.S. Pat No. 3,779,923 describes alkylated methylenedianiline tars as antioxidants in lubricant compositions. The compounds are formed with a phosphorus-based catalyst.
[0003] U.S. Pat No. 8,242,066 describes aniline compounds useful as ashless TBN
sources for lubricating oil compositions that are compatible with fluoroelastomeric engine seal materials.
[0004] U.S. Pat. Nos. 4,100,082; 4,200,545; 4,320,021, and 4,663,063;
4,708.809 generally describe amino-phenol compounds as lubricating oil additives (e.g., dispersant/detergents).
[0005] One test for assessing deposit formation is the "Standard Test Method for Determination of Moderately High Temperature Piston Deposits by Thermo-Oxidation Engine Oil Simulation Test-TEOST MHT," ASTM D7097 ¨ 09. MHT TEOST, as it will be referred to herein, is a bench test that is designed to predict the deposit-forming tendencies of engine oil in the piston ring belt and upper piston crown area during service, and is one of the required test methods in Specification D 4485 to define API
Category-Identified engine oils.
[0006] Some methylenedianiline compounds (MDAs) have been found to improve thermal oxidation performance in engine oils and to boost thin-film antioxidancy.
However, formulating an engine oil for high performance on MHT TEOST can compromise performance in other key areas. For example, adding dispersants and detergents in large amounts can negatively impact the viscometric properties of the lubricating composition or seals performance.
[0007] It would be desirable for a lubricating composition to be able to provide good deposit control, both in fired engine tests and in bench tests such as MHT
TEOST, while also providing other performance properties.
BRIEF DESCRIPTION
TEOST, while also providing other performance properties.
AMENDED SHEET
Received at the EPO on Oct 26, 2018 22:29:51. Page 9 of 26 Duration: 10.26.2018 10:16:29 PM - 10.26.2018 10:29:51 PM. This page 9 of 26 was completed at 10.26.2018 10:22:02 PM
LUBRICATING COMPOSITION INCLUDING N-ALKYLATED DIANILINE
BACKGROUND
[0001] The exemplary embodiment relates to additives for lubricating compositions and finds particular application in connection with N-alkylated dianilines for improved deposit control in as deposit boosters in internal combustion engines.
[0002] U.S. Pat No. 3,779,923 describes alkylated methylenedianiline tars as antioxidants in lubricant compositions. The compounds are formed with a phosphorus-based catalyst.
[0003] U.S. Pat No. 8,242,066 describes aniline compounds useful as ashless TBN
sources for lubricating oil compositions that are compatible with fluoroelastomeric engine seal materials.
[0004] U.S. Pat. Nos. 4,100,082; 4,200,545; 4,320,021, and 4,663,063;
4,708.809 generally describe amino-phenol compounds as lubricating oil additives (e.g., dispersant/detergents).
[0005] One test for assessing deposit formation is the "Standard Test Method for Determination of Moderately High Temperature Piston Deposits by Thermo-Oxidation Engine Oil Simulation Test-TEOST MHT," ASTM D7097 ¨ 09. MHT TEOST, as it will be referred to herein, is a bench test that is designed to predict the deposit-forming tendencies of engine oil in the piston ring belt and upper piston crown area during service, and is one of the required test methods in Specification D 4485 to define API
Category-Identified engine oils.
[0006] Some methylenedianiline compounds (MDAs) have been found to improve thermal oxidation performance in engine oils and to boost thin-film antioxidancy.
However, formulating an engine oil for high performance on MHT TEOST can compromise performance in other key areas. For example, adding dispersants and detergents in large amounts can negatively impact the viscometric properties of the lubricating composition or seals performance.
[0007] It would be desirable for a lubricating composition to be able to provide good deposit control, both in fired engine tests and in bench tests such as MHT
TEOST, while also providing other performance properties.
BRIEF DESCRIPTION
[0008] In accordance with one aspect of the exemplary embodiment, a lubricating composition includes an oil of lubricating viscosity, an N-alkylated dianiline compound and an oil of lubricating viscosity, and at least one of an ashless antioxidant and an overbased calcium detergent. The ashless antioxidant may be selected from a diarylamine antioxidant, a phenolic antioxidant, and combinations thereof. The lubricating composition includes less than 0.15 weight percent of phosphorus.
[0009] In accordance with another aspect of the exemplary embodiment, a method for reducing deposit formation in an internal combustion engine which includes lubricating the internal combustion engine with the lubricating composition.
[0010] In accordance with another aspect of the exemplary embodiment, a method for forming a lubricating composition includes forming an N-alkylated dianiline compound and combining the N-alkylated dianiline compound with an oil of lubricating viscosity and at least one of an ashless antioxidant and an overbased calcium detergent. The ashless antioxidant may be selected from a diarylamine antioxidant, a phenolic antioxidant, and combinations thereof. The lubricating composition includes less than 0.15 weight percent of phosphorus.
[0011] In various aspects of the exemplary embodiment:
[0012] The N-alkylated dianiline compound is hydrocarbylene-coupled.
[0013] The lubricating composition has a TBN of at least 4 mg KOH/g, as measured in accordance with ASTM D-2896.
[0014] The N-alkylated dianiline includes at least one N-alkyl group selected from cyclic alkyl groups, acyclic alkyl groups, and combinations thereof.
[0015] The N-alkyl group is a cyclohexyl group.
[0016] The N-alkylated dianiline is an N,N'-alkylated dianiline compound.
[0017] The N-alkylated dianiline compound is at least 0.10 weight percent of the lubricating composition, or at least 0.15 wt. `)/0, or at least 0.2 wt. %, or at least 0.4 wt.
% of the lubricating composition.
% of the lubricating composition.
[0018] The N-alkylated dianiline compound is up to 4.0 weight percent of the lubricating composition, or up to 3 wt. %, or up to 1.5 wt. %, or up to 1.2 wt. % of the lubricating composition.
[0019] The N-alkylated dianiline compound is represented by the formula of any one of Structures I to IV and Al to A8, described below, and mixtures thereof.
[0020] The hydrocarbylene group is a C1-C3 alkylene group.
[0021] The N-alkylated dianiline compound is selected from 4,4'-2-ethylhexylmethylenedianiline, 4,4'-cyclohexylmethylenedianiline, and mixtures thereof.
[0022] The oil of lubricating viscosity is at least 40 weight percent of the lubricating composition.
[0023] The ashless antioxidant is at least 0.1 weight % of the lubricating composition, or at least 0.2 wt. %, or at least 0.4 wt. %, or at least 0.6 wt.
%, or up to 4 wt. %, or up to 1.2 wt. %, or up to 1 wt. % of the lubricating composition.
%, or up to 4 wt. %, or up to 1.2 wt. %, or up to 1 wt. % of the lubricating composition.
[0024] A ratio of the ashless antioxidant to the N-alkyl dianiline compound is from 20:1 to 1:20.
[0025] The ashless antioxidant includes a phenolic ester and a diarylamine.
[0026] The ashless antioxidant further includes a sulfurized olefin.
[0027] The overbased calcium detergent is selected from sulfonates, non-sulfur containing phenates, sulfur containing phenates, salixarates, salicylates, mixtures thereof, and borated equivalents thereof.
[0028] The overbased calcium detergent is present in an amount to deliver at least 2 mg KOH/g of total base number (TBN), as measured in accordance with ASTM D-2896, to the composition.
[0029] The overbased calcium detergent is least 0.01 wt. % or at least 0.1 wt. /0, or at least 0.5 wt. %, or up to 3 wt. %, or up to 2 wt. % of the lubricating composition.
[0030] A ratio of calcium to magnesium in the lubricating composition, by weight, is at least 9:10.
[0031] The lubricating composition further includes a polyolefin succinimide dispersant, wherein the polyolefin of the polyolefin succinimide has a number average molecular weight of at least 300.
[0032] The lubricating composition further includes a zinc dialkyldithiophosphate.
[0033] The lubricating composition includes at least 0.02 weight percent of phosphorus.
[0034] The N-alkylated dianiline compound is a reaction product of a dianiline with at least one of an aldehyde and a ketone.
DETAILED DESCRIPTION
DETAILED DESCRIPTION
[0035] Aspects of the exemplary embodiment relate to lubricating compositions and to methods of lubricating an internal combustion engine. The lubrication composition includes an N-alkylated dianiline compound, an oil of lubricating viscosity, and at least one of an ashless antioxidant and a calcium overbased detergent. The ashless antioxidant may be selected from diarylamine antioxidants phenolic antioxidants, and mixtures thereof. The exemplary lubricating composition includes less than 0.15 wt. %
phosphorus.
The N-Alkylated Dianiline
phosphorus.
The N-Alkylated Dianiline
[0036] In the lubricating composition, the exemplary N-alkylated dianiline compound improves deposit performance, as measured by the MHT TEOST, while providing good TBN, without negatively impacting (and in some cases, improving) antioxidancy performance, when formulated for heavy duty diesel engine (HD) and passenger car engine applications. For example, in testing, N,N'-dicyclohexyl methylenedianiline (Cy MDA) is able to provide improvements in the MHT TEOST
in both HD and passenger car formulations while also helping antioxidant performance, particularly under the Daimler Oxidation Test in a HD formulation.
in both HD and passenger car formulations while also helping antioxidant performance, particularly under the Daimler Oxidation Test in a HD formulation.
[0037] In the exemplary N-alkylated dianiline compound, the two aromatic rings are hydrocarbylene coupled, e.g., with a Ci-C3 hydrocarbylene group, in particular an alkylene group such as methylene, ethylene, methylmethylene, methylethylene, or dimethylmethylene. N-alkylated methylenedianiline compounds can be readily prepared. However, it is to be appreciated that other hydrocarbylene-coupled N-alkylated dianiline compounds are also contemplated.
[0038] By "N-alkylated" it is meant that an alkyl group is attached to the dianiline by one or both of the amine groups attached to the aromatic rings of the dianiline.
Each of these N-alkyl groups may be a Ci-C24 alkyl group, such as a C3 or higher alkyl group, and may be selected from acyclic alkyl groups, cyclic alkyl groups, and combinations thereof. In the exemplary embodiment, each amine group of the dianiline has no more than one alkyl group. The exemplary N-alkylated methylenedianiline is an N, N-alkylated methylenedianiline, where both amine groups are alkylated.
Each of these N-alkyl groups may be a Ci-C24 alkyl group, such as a C3 or higher alkyl group, and may be selected from acyclic alkyl groups, cyclic alkyl groups, and combinations thereof. In the exemplary embodiment, each amine group of the dianiline has no more than one alkyl group. The exemplary N-alkylated methylenedianiline is an N, N-alkylated methylenedianiline, where both amine groups are alkylated.
[0039] The exemplary N, N-alkylated methylenedianiline contains no more than two aromatic rings linked by a hydrocarbylene group. While methods of generating the N-alkylated dianiline compound may result in structures having more than two aromatic rings linked by hydrocarbylene groups, in the exemplary embodiment, a molar ratio of these N-alkylated polyaromatic aniline compounds to the N-alkylated dianiline compound in the lubricating composition may be no greater than 1:10.
[0040] The N-alkylated hydrocarbylene-coupled dianiline compound may be represented by the formula shown in Structure I:
Structure I, wherein R1 and R2 are independently selected from, or at least 3, or at least 4, or at least 5, or at least 6 carbon atoms, or up to 20, or up to 12, or up to 10, or up to 8 carbon atoms, R3 and R4 are independently selected from hydrocarbyl groups of 1 to 6 carbon atoms, each n is from 0 to 3, or 0 to 2, or 0 to 1, or 0, and X represents a hydrocarbylene group, as described above, such as ¨CH2¨.
Structure I, wherein R1 and R2 are independently selected from, or at least 3, or at least 4, or at least 5, or at least 6 carbon atoms, or up to 20, or up to 12, or up to 10, or up to 8 carbon atoms, R3 and R4 are independently selected from hydrocarbyl groups of 1 to 6 carbon atoms, each n is from 0 to 3, or 0 to 2, or 0 to 1, or 0, and X represents a hydrocarbylene group, as described above, such as ¨CH2¨.
[0041] In one embodiment, R1 and R2 are independently of the general form R5 _______ C ___ R6 where R5 and R6 are independently selected from H and alkyl groups of 1 to 20 carbon atoms or 1 to 12 carbon atoms, or 1 to 8 carbon atoms, and wherein at least one of R5 and R6 is not H, or wherein R5 and R6 together form a ling. In one embodiment, R5 is H
or a Ci - C3 alkyl group and R6 is a C2 - C8 alkyl group, or a C4 - C6 alkyl group. In another embodiment R5 and R6 together form a C4 - C8 ring.
or a Ci - C3 alkyl group and R6 is a C2 - C8 alkyl group, or a C4 - C6 alkyl group. In another embodiment R5 and R6 together form a C4 - C8 ring.
[0042] In one embodiment, the N-alkylated dianiline compound is represented by the formula:
__________________________ H2 H2 or I
(R3)11 ___________________ C ___________ (10n --C
Structure II Structure III.
__________________________ H2 H2 or I
(R3)11 ___________________ C ___________ (10n --C
Structure II Structure III.
[0043] The N-alkylated dianiline compound may be a 4,4'-N-alkylated dianiline compound represented by the formula:
Structure IV.
Structure IV.
[0044] Representative acyclic alkyl groups of the general formula C,71-12n+1 suitable for 131 and R2 include straight chain and branched chain alkyl groups, such as methyl, ethyl, n-propyl, n-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, hexadecyl, stearyl, icosyl, docosyl, tetracosyl, 1-methylpropyl, 2,2-dimethylpropyl, isobutyl, isopentyl, isohexyl, 2-ethylhexyl, isoheptyl, 2-ethylheptyl, 2-propylheptyl, isooctyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl, isodecyl, 2-butyldecyl, 2-hexydecyl, 2-octyldodecyl, 2-hexyldodecyl, isotridecyl, 2-dodecylhexadecyl, 2-decyltetradecyl, 4-methyl-2-pentyl, 2-tetradecyloctyldecyl, monomethyl branched-isostearyl, and isomers and combinations thereof. In particular embodiments, the acyclic alkyl group is branched at the second or higher carbon, such as 2-ethylhexyl, 2-ethylheptyl, 2-ethyloctyl, and the like.
[0045] Representative cyclic alkyl groups of the general formula C,71-12,_1 suitable for R1 and R2 include cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and combinations thereof.
[0046] Representative hydrocarbyl groups suitable for R3 and R4 include acyclic alkyl groups, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, and mixtures and isomers thereof. In one embodiment n is 0, i.e., there are no R3 and 1:14substituents on the aromatic rings.
[0047] Example N-alkylated dianiline compounds include compounds of formulas A-1 to A-8:
N
I I
H
I I
TDCCNXX
I I
I I
N
I I
H
I I
TDCCNXX
I I
I I
[0048]
In specific embodiments, the N-alkylated dianiline compound is selected from 4,4'-2-cyclohexylmethylenedianiline (CY-MDI) (Formula Al), and 4,4'-2-ethylhexylmethylenedianiline (EHL-MDI) (Formula A2).
In specific embodiments, the N-alkylated dianiline compound is selected from 4,4'-2-cyclohexylmethylenedianiline (CY-MDI) (Formula Al), and 4,4'-2-ethylhexylmethylenedianiline (EHL-MDI) (Formula A2).
[0049]
The N-alkylated dianiline compound may be present in the lubricating composition at a concentration of at least 0.1 wt. % and may be up to 5 wt. %.
For example, the concentration of the compound may be at least 0.15 wt. %, or at least 0.4 wt. %, or at least 1.5 wt. %, or up to 5.0 wt. %, or up to 2.5 wt. % of the lubricating composition. The compound may also be present in a concentrate, alone or with other additives and with a lesser amount of oil. In a concentrate, the amount of the compound may be at least 2, or at least 3 times the concentration in the lubricating composition.
The N-alkylated dianiline compound may be present in the lubricating composition at a concentration of at least 0.1 wt. % and may be up to 5 wt. %.
For example, the concentration of the compound may be at least 0.15 wt. %, or at least 0.4 wt. %, or at least 1.5 wt. %, or up to 5.0 wt. %, or up to 2.5 wt. % of the lubricating composition. The compound may also be present in a concentrate, alone or with other additives and with a lesser amount of oil. In a concentrate, the amount of the compound may be at least 2, or at least 3 times the concentration in the lubricating composition.
[0050]
As used herein, TBN is measured according to ASTM D2896 ¨ 15, Standard Test Method for Base Number of Petroleum Products by Potentiometric Perchloric Acid Titration, ASTM International, West Conshohocken, PA, 2011, DOI:
10.1520/D2896-15.
As used herein, TBN is measured according to ASTM D2896 ¨ 15, Standard Test Method for Base Number of Petroleum Products by Potentiometric Perchloric Acid Titration, ASTM International, West Conshohocken, PA, 2011, DOI:
10.1520/D2896-15.
[0051]
In various aspects, the N-alkylated dianiline compound has a TBN of at least 50 mg of KOH/g, or at least 100 mg of KOH/g, as measured according to ASTM
D2896.
In various aspects, the N-alkylated dianiline compound has a TBN of at least 50 mg of KOH/g, or at least 100 mg of KOH/g, as measured according to ASTM
D2896.
[0052] In various aspects, the compound has a TBN of at least.
[0053]
The lubricating composition of claim 1, wherein the composition has a TBN
of at least 4 mg KOH/g, as measured in accordance with ASTM D-2896.
The lubricating composition of claim 1, wherein the composition has a TBN
of at least 4 mg KOH/g, as measured in accordance with ASTM D-2896.
[0054]
The N-alkylated dianiline compound is particularly effective at improving deposit performance in lubricating compositions which are low in phosphorus.
In the exemplary lubricating composition, the phosphorus content of the lubricating composition is up to 0.15 wt. %, such as up to 0.12 wt. %, or up to 0.11 wt.
%, or up to 0.08 wt. %, or up to 0.05 wt. `)/0, or up to 0.04 wt. %, or up to 0.02 wt. %.
The phosphorus content of the lubricating composition may be at least 0.01 wt. %, or at least 0.02 wt. %, or at least 0.03 wt. %. Suitable additives for providing the lubricating composition with such low levels of phosphorus include zinc dialkyldithiophosphates (ZDDPs), as described below.
Methods of Preparing the N-alkvlated Dianiline Compound
The N-alkylated dianiline compound is particularly effective at improving deposit performance in lubricating compositions which are low in phosphorus.
In the exemplary lubricating composition, the phosphorus content of the lubricating composition is up to 0.15 wt. %, such as up to 0.12 wt. %, or up to 0.11 wt.
%, or up to 0.08 wt. %, or up to 0.05 wt. `)/0, or up to 0.04 wt. %, or up to 0.02 wt. %.
The phosphorus content of the lubricating composition may be at least 0.01 wt. %, or at least 0.02 wt. %, or at least 0.03 wt. %. Suitable additives for providing the lubricating composition with such low levels of phosphorus include zinc dialkyldithiophosphates (ZDDPs), as described below.
Methods of Preparing the N-alkvlated Dianiline Compound
[0055]
The exemplary compounds may be prepared, for example, from dianilines, such as 4,4'-methylenedianiline, 2,4'-methylenedianiline, 2,2'-methylenedianiline, and mixtures thereof.
The exemplary compounds may be prepared, for example, from dianilines, such as 4,4'-methylenedianiline, 2,4'-methylenedianiline, 2,2'-methylenedianiline, and mixtures thereof.
[0056]
In one embodiment, N-alkylated dianiline compounds are prepared by reacting a dianiline with one or more aldehydes or ketones in a 1:2 or excess molar ratio in an alcohol solvent, such as methanol or toluene.
In one embodiment, N-alkylated dianiline compounds are prepared by reacting a dianiline with one or more aldehydes or ketones in a 1:2 or excess molar ratio in an alcohol solvent, such as methanol or toluene.
[0057] The aldehyde or ketone can be of the general formula:
R6¨C:
R5 _____________________ C ___ R6 R6, where I
corresponds to R1 and R2 above, at least one of R6 and R6 is not H.
R6¨C:
R5 _____________________ C ___ R6 R6, where I
corresponds to R1 and R2 above, at least one of R6 and R6 is not H.
[0058]
In one embodiment, the aldehyde or ketone may be a C2-C12 aldehyde or ketone, such as a C2-Cs aldehyde, or a C2-C6 aldehyde or a C3-C10 ketone, or ketone.
In one embodiment, the aldehyde or ketone may be a C2-C12 aldehyde or ketone, such as a C2-Cs aldehyde, or a C2-C6 aldehyde or a C3-C10 ketone, or ketone.
[0059]
Example ketones useful in forming the compound include methyl alkyl ketones and ethyl alkyl ketones of from 3-12 carbon atoms where the alkyl group may be alicyclic or cyclic. Examples of such ketones include those in which the alkyl portions are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and as well as the various isomeric forms thereof.
Examples of ketones include acetone, 2-butanone, 2-pentanone, 3-pentanone, 4-methyl-2-butanone, 2-hexanone, 4-methyl-2-hexanone, 4-heptanone, 5-methyl-2-hexanone, 5,6-dimethy1-2-hexanone, 5,5-dimethy1-2-hexanone, 4,5-dimethy1-2-hexanone, 4-ethy1-2-hexanone, 5-ethyl-2-hexanone, 4,5,5-trimethy1-2-hexanone, 2-heptanone, 3-heptanone, 5,5-dimethy1-2-heptanone, 4,5-dimethy1-2-heptanone, 5-ethyl-2-heptanone, 4-ethy1-2-heptanone, 2-octanone, 3-octanone, 4-octanone, 6-methyl-2-octanone, 7,7-dimethy1-2-octanone, 6-methyl-3-octanone, 6-ethyloctanone, 2-nonanone, 3-nonanone, 4-nonanone, 5-nonanone, 2-decanone, 3-decanone, 4-decanone, 5-decanone, cyclobutanone, cyclopentanone, cyclohexanone, methyl-cyclohexanones, ethyl-cyclohexanones, cycloheptanone, cyclooctanone, and the like.
Example ketones useful in forming the compound include methyl alkyl ketones and ethyl alkyl ketones of from 3-12 carbon atoms where the alkyl group may be alicyclic or cyclic. Examples of such ketones include those in which the alkyl portions are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and as well as the various isomeric forms thereof.
Examples of ketones include acetone, 2-butanone, 2-pentanone, 3-pentanone, 4-methyl-2-butanone, 2-hexanone, 4-methyl-2-hexanone, 4-heptanone, 5-methyl-2-hexanone, 5,6-dimethy1-2-hexanone, 5,5-dimethy1-2-hexanone, 4,5-dimethy1-2-hexanone, 4-ethy1-2-hexanone, 5-ethyl-2-hexanone, 4,5,5-trimethy1-2-hexanone, 2-heptanone, 3-heptanone, 5,5-dimethy1-2-heptanone, 4,5-dimethy1-2-heptanone, 5-ethyl-2-heptanone, 4-ethy1-2-heptanone, 2-octanone, 3-octanone, 4-octanone, 6-methyl-2-octanone, 7,7-dimethy1-2-octanone, 6-methyl-3-octanone, 6-ethyloctanone, 2-nonanone, 3-nonanone, 4-nonanone, 5-nonanone, 2-decanone, 3-decanone, 4-decanone, 5-decanone, cyclobutanone, cyclopentanone, cyclohexanone, methyl-cyclohexanones, ethyl-cyclohexanones, cycloheptanone, cyclooctanone, and the like.
[0060]
As an example, 4,4'-methylenedianiline is reacted with an aldehyde/ketone in a 1:2 or excess molar ratio in a suitable solvent, such as toluene, at a temperature of over 100 C. Water formed in the reaction is removed. Once the reaction is complete, the solvent is removed. The product may be purified by redissolving it in a suitable solvent, such as methanol, and adding sodium borohydride. The mixture is poured into water and the product extracted using ethyl acetate. The solvent is removed yielding the purified product. An illustrative reaction scheme shown in Scheme 1:
Scheme 1:
Heat, reduction where R5 and R6 are as described above.
As an example, 4,4'-methylenedianiline is reacted with an aldehyde/ketone in a 1:2 or excess molar ratio in a suitable solvent, such as toluene, at a temperature of over 100 C. Water formed in the reaction is removed. Once the reaction is complete, the solvent is removed. The product may be purified by redissolving it in a suitable solvent, such as methanol, and adding sodium borohydride. The mixture is poured into water and the product extracted using ethyl acetate. The solvent is removed yielding the purified product. An illustrative reaction scheme shown in Scheme 1:
Scheme 1:
Heat, reduction where R5 and R6 are as described above.
[0061] N-alkylated dianiline compounds can also be prepared by reacting a methylenedianiline and one or more aldehydes or ketones in a 1:2 or excess molar ratio in the presence of hydrogen and a hydrogenation catalyst, such as platinum, palladium, cobalt or nickel, either as such or carried on a suitable support, such as carbon, in methanol solvent, as described, for example, in U.S. Pat. Nos.
2,045,574 and 3,779,923.
2,045,574 and 3,779,923.
[0062] In general, the reaction results in mono-substitution of each ¨NH2 group, although there may be a small amount of di-substituted compounds present.
[0063] A lubricating composition may be prepared by adding the N-alkylated dianiline compound and ashless antioxidant to an oil of lubricating viscosity, optionally in the presence of other performance additives (as described herein below), or by adding reagents for forming the N-alkylated dianiline compound to an oil of lubricating viscosity. The lubricating composition may further include additional performance additives, such as antioxidants, additional dispersants, antiwear agents, and friction modifiers. A method for forming a lubricating composition includes forming an N-alkylated dianiline compound and combining the N-alkylated dianiline compound with an oil of lubricating viscosity and at least one ashless antioxidant and/or overbased calcium detergent, to provide a lubricating composition comprising less than 0.15 weight percent of phosphorus.
The Ashless Antioxidant
The Ashless Antioxidant
[0064] The lubricating composition may include one or more ashless antioxidant(s) (AAO) selected from a diarylamine antioxidant, a phenolic antioxidant, and a mixture thereof. The AAO may be present in the lubricating composition at a concentration of at least 0.2 wt. %, such as at least 0.3 wt. 13/0., or up to 5 wt. %, or up to 2.5 wt. %, or up to 2 wt. %, or up to 1 wt. %. A weight ratio of the AAO to the N-alkylated dianiline compound may be at least 1:20 or up to 20:1.
[0065] Exemplary phenolic antioxidants useful herein include alkylated diphenylamine antioxidants, such as C1-C24 monoalkylated, dialkylated and polyalkylated diphenylamines, as described, for example, in U.S. Pat. Nos.
2,943,112;
4,824,601; 5,672,752; 6,204,412; 6,315,925; 6,355,839, and U.S. Pub. Nos.
2015/0307803 and 2016/0017252. Particularly useful are monoalkylated and dialkylated diphenylamines in which the alkyl group(s) include(s) at least 6 carbon atoms, such as at least 8, or at least 9 carbon atoms.
2,943,112;
4,824,601; 5,672,752; 6,204,412; 6,315,925; 6,355,839, and U.S. Pub. Nos.
2015/0307803 and 2016/0017252. Particularly useful are monoalkylated and dialkylated diphenylamines in which the alkyl group(s) include(s) at least 6 carbon atoms, such as at least 8, or at least 9 carbon atoms.
[0066] Exemplary phenolic antioxidants that may be used include 07-C9 branched alkyl esters of 3,5-bis(1,1-dimethyl-ethyl)-4-hydroxy-benzenepropanoic acid, 2-tert-butylphenol, 2-tert-butyl-4-methylphenol, 2-tert-butyl-5-methylphenol, 2,4-di-tert-butylphenol, 2,4-dimethy1-6-tert-butylphenol, 2-tert-butyl-4-methoxyphenol, 3-tert-buty1-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,6-di-tert-butyl-4-alkylphenols such as 2,6-di-tert-butylphenol, 2,6-di-tert-butyl-4-methylphenol and 2,6-di-tert-buty1-4-ethylphenol, 2,6-di-tert-butyl-4-alkoxyphenols such as 2,6-di-tert-buty1-4-methoxyphenol and 2,6-di-tert-butyl-4-ethoxyphenol, 3,5-di-tert-buty1-4-hydroxybenzylmercaptooctylacetate, alky1-3-(3,5-di-tert-buty1-4-hydroxyphenyl)propionates such as n-octadecy1-3-(3,5-di-tert-buty1-4-hydroxyphenyl)propionate, n-butyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate and 2'-ethylhexy1-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 2,6-di-tert-butyl-a-dimethylamino-p-cresol, 2,2'-methylene-bis(4-alkyl-6-tert-butylphenol) such as 2,2'-methylenebis(4-methy1-6-tert-butylphenol, and 2,2-methylenebis(4-ethy1-6-tert-butylphenol), bisphenols such as 4,4'-butylidenebis(3-methyl-6-tert-butylphenol, 4,4'-methylenebis(2,6-di-tert-butylphenol), 4,4'-bis(2,6-di-tert-butylphenol), 2,2-(di-p-hydroxyphenyl)propane, 2,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)propane, 4,4'-cyclohexylidenebis(2,6-tert-butylphenol), hexamethyleneglycol-bis[3-(3,5-di-tert-buty1-4-hydroxyphenyl)propionate], triethyleneglycolbis[3-(3-tert-buty1-4-hydroxy-5-methylphenyl)propionate], 2,2'-thio-[diethy1-3-(3,5-di-tert-buty1-4-hydroxyphenyl)propionate], 3,9-bis[1,1-dimethy1-243-(3-tert-buty1-4-hydroxy-5-methyl-phenyl)propionyloxy]ethy1}2,4,8,10-tetraoxaspiro[5,5]undecane, 4,4'-thiobis(3-methy1-6-tert-butylphenol) and 2,2'-thiobis(4,6-di-tert-butylresorcinol), polyphenols such as tetrakis[methylene-3-(3,5-di-tert-buty1-4-hydroxyphenyl)propionate]methane, 1,1,3-tris(2-methyl-4-hydroxy-5-tert-butylphenyl)butane, 1,3,5-trimethy1-2,4,6-tris(3,5-di-tert-buty1-4-hydroxybenzyl)benzene, bis-[3,3'-bis(41-hydroxy-3'-tert-butylphenyl)butyric acid]glycol ester, 2-(3',5'-di-tert-buty1-4-hydroxyphenyl)methy1-4-(2",4"-di-tert-buty1-3"-hydroxyphenyl)methy1-6-tert-butylphenol and 2,6-bis(21-hydroxy-3'-tert-buty1-5'-methylbenzy1)-4-methylphenol, p-t-butylphenol-formaldehyde condensates and p-t-butylphenol-acetaldehyde condensates.
[0067]
Phenol-based antioxidants often contain a secondary butyl and/or a tertiary butyl group as a steric hindering group. The phenol group may be further substituted with a hydrocarbyl group (e.g., a linear or branched alkyl) and/or a bridging group linking to a second aromatic group.
Phenol-based antioxidants often contain a secondary butyl and/or a tertiary butyl group as a steric hindering group. The phenol group may be further substituted with a hydrocarbyl group (e.g., a linear or branched alkyl) and/or a bridging group linking to a second aromatic group.
[0068]
Examples of particularly suitable hindered phenol antioxidants include 2,6-di-tert-butylphenol, 4,4'-methylenebis-(2,6-di-tert-butylphenol), 4-methy1-2,6-di-tert-butylphenol, 4-ethyl-2,6-di-tert-butylphenol, 4-propy1-2,6-di-tert-butylphenol, 4-butyl-2,6-di-tert-butylphenol, 4-dodecy1-2,6-di-tert-butylphenol, 2,2'-methylenebis(4-methy1-6-tert-butylphenol), 2,2'-methylenebis(4-ethyl-6-tert-butylphenol), as described, for
Examples of particularly suitable hindered phenol antioxidants include 2,6-di-tert-butylphenol, 4,4'-methylenebis-(2,6-di-tert-butylphenol), 4-methy1-2,6-di-tert-butylphenol, 4-ethyl-2,6-di-tert-butylphenol, 4-propy1-2,6-di-tert-butylphenol, 4-butyl-2,6-di-tert-butylphenol, 4-dodecy1-2,6-di-tert-butylphenol, 2,2'-methylenebis(4-methy1-6-tert-butylphenol), 2,2'-methylenebis(4-ethyl-6-tert-butylphenol), as described, for
69 example, in U.S. Pub. Nos. 2009/0111720, 2010/0269774, and 2012/0103290. In one embodiment, the hindered phenol antioxidant may be an ester, such as those described in U.S. Pat. No. 6,559,105, such as an alkyl alcohol esters of 3-(4-hydroxy-3,5-di-tert-butyl-phenyl)propionic acid. One such hindered phenol ester is sold as IrganoxTm L-135, obtainable from Ciba.
[0069] The phenolic antioxidant, where present in the lubricating composition, may be at least 0.1 weight % of the lubricating composition, or at least 0.5 wt.
%, or at least 1.5 wt. %, or at least 2.5 wt. %, and may be up to 5 wt. %, such as up to 4 wt. `)/0, or up to 3 wt. % of the lubricating composition.
[0069] The phenolic antioxidant, where present in the lubricating composition, may be at least 0.1 weight % of the lubricating composition, or at least 0.5 wt.
%, or at least 1.5 wt. %, or at least 2.5 wt. %, and may be up to 5 wt. %, such as up to 4 wt. `)/0, or up to 3 wt. % of the lubricating composition.
[0070] Examples of alkylated diphenylamines useful herein include those of the general formula:
I j Rlo where each of R7, R8, R9 and R10, is selected from H and C8-C24 or C8-C12 alkyl groups, and wherein at least one of R7, R8, R9, and F119 is not H. In one embodiment, R8 and R19 (and optionally also R9) are not H. Para-substitution by the alkyl group is common.
I j Rlo where each of R7, R8, R9 and R10, is selected from H and C8-C24 or C8-C12 alkyl groups, and wherein at least one of R7, R8, R9, and F119 is not H. In one embodiment, R8 and R19 (and optionally also R9) are not H. Para-substitution by the alkyl group is common.
[0071] Example alkylated diphenylamines include dinonyl diphenylamine, nonyl diphenylamine, octyl diphenylamine, dioctyl diphenylamine, dodecyl diphenylamine, decyl diphenylamine, and mixtures thereof.
[0072] Methods for producing monoalkylated diphenylamines are described in U.S.
Pat. No. 5,672,752. Methods for selectively producing p,p'-di-alkylated diphenylamines are described in U.S. Pub. No. 2016/0017252.
Pat. No. 5,672,752. Methods for selectively producing p,p'-di-alkylated diphenylamines are described in U.S. Pub. No. 2016/0017252.
[0073] Other exemplary diarylamine antioxidants include alkylated phenylnaphthylamines of the general form:
\N
where each of R7, R8 are as defined above and at least one of R7 and R8 is not H.
\N
where each of R7, R8 are as defined above and at least one of R7 and R8 is not H.
[0074]
Example alkylated phenylnaphthylamines include octyl, dioctyl, nonyl, dinonyl, decyl and dodecyl phenylnaphthylamines, such as N-, (Dodecylphenyl)naphthalen-1-amine:
FIN
Example alkylated phenylnaphthylamines include octyl, dioctyl, nonyl, dinonyl, decyl and dodecyl phenylnaphthylamines, such as N-, (Dodecylphenyl)naphthalen-1-amine:
FIN
[0075] In one embodiment, a ratio of the diarylamine to the N-alkyl dianiline compound is from 20:1 to 1:20.
[0076]
The alkylated diarylamine, where present in the lubricating composition, may be at least 0.1 weight % of the lubricating composition, or at least 0.2 wt. %, or at least 0.4 wt. %, or at least 0.5 wt. %, or at least 1.0 wt. %, or at least 2.5 wt. %, and may be up to 5 wt. %, such as up to 2.5 wt. %, or up to 1.5 wt. % of the lubricating composition.
The alkylated diarylamine, where present in the lubricating composition, may be at least 0.1 weight % of the lubricating composition, or at least 0.2 wt. %, or at least 0.4 wt. %, or at least 0.5 wt. %, or at least 1.0 wt. %, or at least 2.5 wt. %, and may be up to 5 wt. %, such as up to 2.5 wt. %, or up to 1.5 wt. % of the lubricating composition.
[0077]
Mixtures of phenolic and/or alkylated diarylamine antioxidants may be employed. When both an alkylated diarylamine and phenolic antioxidant are used, the combined amount of ashless antioxidant may be at least 0.1 weight % of the lubricating composition, or at least 0.8 wt. %, or at least 1.5 wt. %, or at least 3 wt.
%, and may be up to 5 wt. %, such as up to 4 wt. %, or up to 3.5 wt. % of the lubricating composition.
Overbased Calcium Detergent
Mixtures of phenolic and/or alkylated diarylamine antioxidants may be employed. When both an alkylated diarylamine and phenolic antioxidant are used, the combined amount of ashless antioxidant may be at least 0.1 weight % of the lubricating composition, or at least 0.8 wt. %, or at least 1.5 wt. %, or at least 3 wt.
%, and may be up to 5 wt. %, such as up to 4 wt. %, or up to 3.5 wt. % of the lubricating composition.
Overbased Calcium Detergent
[0078]
In one embodiment, the lubricating composition includes one or more overbased calcium detergents. In one embodiment, the lubricating composition includes an alkaline earth metal overbased detergent in an amount sufficient to deliver at least 2 mg KOH/g of total base number (TBN), as measured in accordance with ASTM D-2896-15, to the lubricating composition.
In one embodiment, the lubricating composition includes one or more overbased calcium detergents. In one embodiment, the lubricating composition includes an alkaline earth metal overbased detergent in an amount sufficient to deliver at least 2 mg KOH/g of total base number (TBN), as measured in accordance with ASTM D-2896-15, to the lubricating composition.
[0079]
The overbased calcium detergent may be chosen from sulfonates, non-sulfur containing phenates, sulfur containing phenates, salixarates, salicylates, and mixtures thereof, or borated equivalents thereof. The overbased detergent may be borated with a borating agent such as boric acid.
The overbased calcium detergent may be chosen from sulfonates, non-sulfur containing phenates, sulfur containing phenates, salixarates, salicylates, and mixtures thereof, or borated equivalents thereof. The overbased detergent may be borated with a borating agent such as boric acid.
[0080]
The overbased calcium-containing detergent may also include "hybrid"
detergents formed with mixed surfactant systems including phenate and/or sulfonate components, e.g., phenate/salicylates, sulfonate/phenates, sulfonate/salicylates, sulfonates/phenates/salicylates, as described, for example, in U.S. Pat. Nos.
6,429,178; 6,429,179; 6,153,565; and 6,281,179. Where a hybrid sulfonate/phenate detergent is employed, the hybrid detergent can be considered equivalent to amounts of distinct phenate and sulfonate detergents introducing like amounts of phenate and sulfonate soaps, respectively.
The overbased calcium-containing detergent may also include "hybrid"
detergents formed with mixed surfactant systems including phenate and/or sulfonate components, e.g., phenate/salicylates, sulfonate/phenates, sulfonate/salicylates, sulfonates/phenates/salicylates, as described, for example, in U.S. Pat. Nos.
6,429,178; 6,429,179; 6,153,565; and 6,281,179. Where a hybrid sulfonate/phenate detergent is employed, the hybrid detergent can be considered equivalent to amounts of distinct phenate and sulfonate detergents introducing like amounts of phenate and sulfonate soaps, respectively.
[0081] Example overbased calcium-containing detergents include calcium salts of sulfonates, phenates (including sulfur-containing and non-sulfur containing phenates), salixarates and salicylates. Such overbased sulfonates, salixarates, phenates and salicylates may have a total base number of 120 to 700, or 250 to 600, or 300 to 500 (on an oil free basis).
[0082] Overbased calcium sulfonates, salixarates, phenates and salicylates typically have a total base number of 120 to 700 TBN. Overbased sulfonates typically have a total base number of 120 to 700, or 250 to 600, or 300 to 500 (on an oil free basis).
[0083] By "overbased," it is meant that the calcium is in excess of stoichiometric amounts with respect to the soap counterion (e.g., sulfonate). The overbased calcium detergent may have a metal: counterion ratio of at least 3:1, or at least 4:1, or at least 6:1.
[0084] Example sulfonate detergents include linear and branched alkylbenzene sulfonate detergents, and mixtures thereof, which may have a metal ratio of at least 8, as described, for example, in U.S. Pub. No. 2005065045. Linear alkyl benzenes may have the benzene ring attached anywhere on the linear chain, usually at the 2, 3, or 4 position, or be mixtures thereof. Linear alkylbenzene sulfonate detergents may be particularly useful for assisting in improving fuel economy.
[0085] In one embodiment, the alkylbenzene sulfonate detergent may be a branched alkylbenzene sulfonate, a linear alkylbenzene sulfonate, or mixtures thereof.
[0086] In one embodiment, the lubricating composition may be free of linear alkylbenzene sulfonate detergent. The sulfonate detergent may be a calcium salt of one or more oil-soluble alkyl toluene sulfonate compounds as disclosed in U.S.
Pub.
No. 20080119378.
Pub.
No. 20080119378.
[0087] The lubricating composition may include at least 0.01 wt. % or at least 0.1 wt. %, or at least 0.5 wt. %, of overbased calcium detergent, and in some embodiments, up to 3 wt. %, or up to 2 wt. % overbased calcium detergent(s).
Oil of Lubricating Viscosity
Oil of Lubricating Viscosity
[0088] The lubricating composition may include the oil of lubricating viscosity as a minor or major component thereof, such as at least 5 wt. %, or at least 10 wt.
%, or at least 20 wt. %, or at least 30 wt. %, or at least 40 wt. %, or at least 60 wt.
%, or at least 80 wt. %, or up to 98 wt. %, or up to 95 wt. %, of the lubricating composition.
%, or at least 20 wt. %, or at least 30 wt. %, or at least 40 wt. %, or at least 60 wt.
%, or at least 80 wt. %, or up to 98 wt. %, or up to 95 wt. %, of the lubricating composition.
[0089] The amount of the oil of lubricating viscosity present may be typically the balance remaining after subtracting from 100 wt. %, the sum of the amount of the compound and antioxidant, as described above and any other performance additives.
[0090] Suitable oils include natural and synthetic oils, oil derived from hydrocracking, hydrogenation, and hydrofinishing, unrefined, refined, re-refined oils or mixtures thereof. Unrefined, refined and re-refined oils, and natural and synthetic oils are described, for example, in WO 2008/147704 and U.S. Pub. No. 2010/197536.
Synthetic oils may also be produced by Fischer-Tropsch reactions and typically may be hydroisomerized Fischer-Tropsch hydrocarbons or waxes. Oils may be prepared by a Fischer-Tropsch gas-to-liquid synthetic procedure as well as other gas-to-liquid procedures.
Synthetic oils may also be produced by Fischer-Tropsch reactions and typically may be hydroisomerized Fischer-Tropsch hydrocarbons or waxes. Oils may be prepared by a Fischer-Tropsch gas-to-liquid synthetic procedure as well as other gas-to-liquid procedures.
[0091] Oils of lubricating viscosity may also be defined as specified in April 2008 version of "Appendix E - API Base Oil Interchangeability Guidelines for Passenger Car Motor Oils and Diesel Engine Oils", section 1.3 Sub-heading 1.3. "Base Stock Categories". The API Guidelines are also summarized in U.S. Pat. No.
7,285,516. The five base oil groups are as follows: Group I (sulfur content >0.03 wt. %, and/or <90 wt.
% saturates, viscosity index 80-120); Group II (sulfur content <0.03 wt. %, and >90 wt.
% saturates, viscosity index 80-120); Group III (sulfur content <0.03 wt. %, and >90 wt.
% saturates, viscosity index >120); Group IV (all polyalphaolefins (PA0s));
and Group V (all others not included in Groups I, II, III, or IV). The exemplary oil of lubricating viscosity includes an API Group I, Group II, Group III, Group IV, Group V oil, or mixtures thereof. In some embodiments, the oil of lubricating viscosity is an API Group I, Group II, Group III, or Group IV oil, or mixtures thereof. In some embodiments, the oil of lubricating viscosity is an API Group I, Group II, or Group III oil, or mixture thereof.
In one embodiment the oil of lubricating viscosity may be an API Group II, Group III
mineral oil, a Group IV synthetic oil, or mixture thereof. In some embodiments, at least 5 wt. %, or at least 10 wt. %, or at least 20 wt. cY0, or at least 40 wt. % of the lubricating composition is a polyalphaolefin (Group IV).
7,285,516. The five base oil groups are as follows: Group I (sulfur content >0.03 wt. %, and/or <90 wt.
% saturates, viscosity index 80-120); Group II (sulfur content <0.03 wt. %, and >90 wt.
% saturates, viscosity index 80-120); Group III (sulfur content <0.03 wt. %, and >90 wt.
% saturates, viscosity index >120); Group IV (all polyalphaolefins (PA0s));
and Group V (all others not included in Groups I, II, III, or IV). The exemplary oil of lubricating viscosity includes an API Group I, Group II, Group III, Group IV, Group V oil, or mixtures thereof. In some embodiments, the oil of lubricating viscosity is an API Group I, Group II, Group III, or Group IV oil, or mixtures thereof. In some embodiments, the oil of lubricating viscosity is an API Group I, Group II, or Group III oil, or mixture thereof.
In one embodiment the oil of lubricating viscosity may be an API Group II, Group III
mineral oil, a Group IV synthetic oil, or mixture thereof. In some embodiments, at least 5 wt. %, or at least 10 wt. %, or at least 20 wt. cY0, or at least 40 wt. % of the lubricating composition is a polyalphaolefin (Group IV).
[0092] The lubricating composition disclosed herein may have a SAE
viscosity grade of XW-Y, wherein X may be 0, 5, 10 or 15; and Y may be 16, 20, 30 or 40.
viscosity grade of XW-Y, wherein X may be 0, 5, 10 or 15; and Y may be 16, 20, 30 or 40.
[0093] The oil of lubricating viscosity may have a kinematic viscosity of up to 12 mm2/s or up to 8 mm2/s (cSt) at 100 C and can be at least 12 mm2/s at 100 C, and in other embodiments at least 3.5 mm2/s. As used herein, kinematic viscosity is determined at 100 C by ASTM D445-14, "Standard Test Method for Kinematic Viscosity of Transparent and Opaque Liquids (and Calculation of Dynamic Viscosity),"
ASTM International, West Conshohocken, PA, 2003, DOI: 10.1520/D0445-14 and may be referred to as KV_100.
ASTM International, West Conshohocken, PA, 2003, DOI: 10.1520/D0445-14 and may be referred to as KV_100.
[0094] The viscosity grade of the oil depends on the end use. For passenger car and diesel engines, the viscosity grade may be SAE-5W-30, SAE 10W-30 or SAE
15W-40. The base oil may be a blend of two or more fractions having different oligomer distributions. A fraction rich in lower oligomers is typically blended with a fraction rich in higher oligomers to achieve the desired oligomer distribution. However, any combination of fractions which will yield a composite having the required distribution of oligomers is acceptable. The fractions employed for such blending may be different distillation cuts from the same process or may be obtained from entirely different oligomerization processes. A single fraction may be used to produce different multigrade oils, e.g. SAE 10W-30 and SAE 15W-40 oils. The composite obtained after blending can be hydrogenated or the individual fractions can be hydrogenated before they are blended.
15W-40. The base oil may be a blend of two or more fractions having different oligomer distributions. A fraction rich in lower oligomers is typically blended with a fraction rich in higher oligomers to achieve the desired oligomer distribution. However, any combination of fractions which will yield a composite having the required distribution of oligomers is acceptable. The fractions employed for such blending may be different distillation cuts from the same process or may be obtained from entirely different oligomerization processes. A single fraction may be used to produce different multigrade oils, e.g. SAE 10W-30 and SAE 15W-40 oils. The composite obtained after blending can be hydrogenated or the individual fractions can be hydrogenated before they are blended.
[0095] For 2-stroke marine diesel engines the viscosity grade may be from SAE-40 to SAE-60, which corresponds to a KV_100 of 12.5 to 26 mm2/s. SAE-50 grade oils, for example, have a KV_100 of 16.3-21.9 mm2/s. Cylinder oils for 2-stroke marine diesel engines may be formulated to achieve a KV_100 of 19 to 21.5 mm2/s. This viscosity can be obtained by a mixture of additives and base oils, for example containing mineral bases of Group I such as Neutral Solvent (for example 500 NS or 600 NS) and Bright Stock bases. Any other combination of mineral or synthetic bases or bases of vegetable origin having, in mixture with the additives, a viscosity compatible with the grade SAE 50 can be used.
[0096] As an example, an oil formulation suited to use as a cylinder lubricant for low-speed 2-stroke marine diesel engines contains 18 to 25 wt. % of a Group I
base oil of a BSS type (distillation residue, with a KV_100 of 28 - 32 mm2/s, with a density at 15 C of 895 - 915 kg/m3), and 50 to 60 wt. % of a Group I base oil of a SN 600 type (distillate, with a density at 15 C of 880 - 900 kg/m3, with a KV_100 of about 12 mm2/s).
base oil of a BSS type (distillation residue, with a KV_100 of 28 - 32 mm2/s, with a density at 15 C of 895 - 915 kg/m3), and 50 to 60 wt. % of a Group I base oil of a SN 600 type (distillate, with a density at 15 C of 880 - 900 kg/m3, with a KV_100 of about 12 mm2/s).
[0097]
In certain embodiments, the lubricating composition may contain synthetic ester base fluids. Synthetic esters may have a kinematic viscosity measured at of 2.5 mm2/s to 30 mm2/s. In one embodiment, the lubricating composition comprises less than 50 wt. % of a synthetic ester base fluid with a KV_100 of at least 5.5 mm2/s, or at least 6 mm2/s, or at least 8 mm2/s.
In certain embodiments, the lubricating composition may contain synthetic ester base fluids. Synthetic esters may have a kinematic viscosity measured at of 2.5 mm2/s to 30 mm2/s. In one embodiment, the lubricating composition comprises less than 50 wt. % of a synthetic ester base fluid with a KV_100 of at least 5.5 mm2/s, or at least 6 mm2/s, or at least 8 mm2/s.
[0098]
Exemplary synthetic oils include poly-alpha olefins, polyesters, poly-acrylates, and poly-methacrylates, and co-polymers thereof. Example synthetic esters include esters of a dicarboxylic acid (e.g., selected from phthalic acid, succinic acid, alkyl succinic acids, alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkyl malonic acids, and alkenyl malonic acids) with an alcohol (e.g., selected from butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether, and propylene glycol). Specific examples of these esters include dibutyl adipate, di(2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, the 2-ethylhexyl diester of linoleic acid dimer, and the complex ester formed by reacting one mole of sebacic acid with two moles of tetraethylene glycol and two moles of 2-ethylhexanoic acid.
Exemplary synthetic oils include poly-alpha olefins, polyesters, poly-acrylates, and poly-methacrylates, and co-polymers thereof. Example synthetic esters include esters of a dicarboxylic acid (e.g., selected from phthalic acid, succinic acid, alkyl succinic acids, alkenyl succinic acids, maleic acid, azelaic acid, suberic acid, sebacic acid, fumaric acid, adipic acid, linoleic acid dimer, malonic acid, alkyl malonic acids, and alkenyl malonic acids) with an alcohol (e.g., selected from butyl alcohol, hexyl alcohol, dodecyl alcohol, 2-ethylhexyl alcohol, ethylene glycol, diethylene glycol monoether, and propylene glycol). Specific examples of these esters include dibutyl adipate, di(2-ethylhexyl) sebacate, di-n-hexyl fumarate, dioctyl sebacate, diisooctyl azelate, diisodecyl azelate, dioctyl phthalate, didecyl phthalate, dieicosyl sebacate, the 2-ethylhexyl diester of linoleic acid dimer, and the complex ester formed by reacting one mole of sebacic acid with two moles of tetraethylene glycol and two moles of 2-ethylhexanoic acid.
[0099]
Esters useful as synthetic oils also include those made from C5 to C12 monocarboxylic acids and polyols and from polyol ethers such as neopentyl glycol, trimethylolpropane, pentaerythritol, dipentaerythritol, and tripentaerythritol. Esters can also be monoesters, such as are available under the trade name Priolube 1976TM
(C18-alkyl¨COO-020 alkyl).
Esters useful as synthetic oils also include those made from C5 to C12 monocarboxylic acids and polyols and from polyol ethers such as neopentyl glycol, trimethylolpropane, pentaerythritol, dipentaerythritol, and tripentaerythritol. Esters can also be monoesters, such as are available under the trade name Priolube 1976TM
(C18-alkyl¨COO-020 alkyl).
[0100]
Synthetic ester base oils may be present in the lubricating composition in an amount less than 50 wt. % of the composition, or less than 40 weight /0, or less than weight %, or less than 28 weight %, or less than 21 weight %, or less than 17 weight %, or less than 10 weight A, or less than 5 weight % of the composition. In one 30 embodiment, the lubricating composition is free of, or substantially free of, a synthetic ester base fluid having a KV_100 of at least 5.5 mm2/s.
Synthetic ester base oils may be present in the lubricating composition in an amount less than 50 wt. % of the composition, or less than 40 weight /0, or less than weight %, or less than 28 weight %, or less than 21 weight %, or less than 17 weight %, or less than 10 weight A, or less than 5 weight % of the composition. In one 30 embodiment, the lubricating composition is free of, or substantially free of, a synthetic ester base fluid having a KV_100 of at least 5.5 mm2/s.
[0101]
Example natural oils include animal and vegetable oils, such as long chain fatty acid esters. Examples include linseed oil, sunflower oil, sesame seed oil, beef tallow oil, lard oil, palm oil, castor oil, cottonseed oil, corn oil, peanut oil, soybean oil, olive oil, whale oil, menhaden oil, sardine oil, coconut oil, palm kernel oil, babassu oil, rape oil, and soya oil.
Example natural oils include animal and vegetable oils, such as long chain fatty acid esters. Examples include linseed oil, sunflower oil, sesame seed oil, beef tallow oil, lard oil, palm oil, castor oil, cottonseed oil, corn oil, peanut oil, soybean oil, olive oil, whale oil, menhaden oil, sardine oil, coconut oil, palm kernel oil, babassu oil, rape oil, and soya oil.
[0102] The amount of the oil of lubricating viscosity present is typically the balance remaining after subtracting from 100 weight % the sum of the amount of the exemplary N-alkylated methylenedianiline compound and the other performance additives.
Other Performance Additives
Other Performance Additives
[0103] In addition to the exemplary N-alkylated dianiline compound(s) disclosed herein, the lubricating composition may further include one or more of the following additional performance additives: antioxidants (different from above), dispersants, viscosity modifiers, antiwear/antiscuffing agents, metal deactivators, friction modifiers, extreme pressure agents, foam inhibitors, demulsifiers, pour point depressants, corrosion inhibitors, seal swelling agents, TBN boosters, and the like. The additional performance additive(s) may be suited to providing the performance properties of a fully formulated lubricating composition, e.g., a passenger car or HD engine lubricant.
A. Detergents
A. Detergents
[0104] The lubricating composition optionally further includes at least one detergent, in addition to the overbased calcium detergent discussed above.
Exemplary detergents useful herein include overbased metal-containing detergents, where the metal is other than calcium.
Exemplary detergents useful herein include overbased metal-containing detergents, where the metal is other than calcium.
[0105] The metal of the metal-containing detergent may be zinc, sodium, barium, or magnesium. In one embodiment, the lubricating composition includes an alkaline earth metal overbased detergent in an amount sufficient to deliver at least 2 mg KOH/g of total base number (TBN), as measured in accordance with ASTM D-2896-15, to the lubricating composition.
[0106] The overbased metal-containing detergent may be chosen from sulfonates, non-sulfur containing phenates, sulfur containing phenates, salixarates, salicylates, and mixtures thereof, or borated equivalents thereof. The overbased detergent may be borated with a borating agent such as boric acid.
[0107] The overbased metal-containing detergent may also include "hybrid"
detergents formed with mixed surfactant systems including phenate and/or sulfonate components, e.g., phenate/salicylates, sulfonate/phenates, sulfonate/salicylates, sulfonates/phenates/salicylates, as described, for example, in U.S. Pat. Nos.
6,429,178; 6,429,179; 6,153,565; and 6,281,179. Where a hybrid sulfonate/phenate detergent is employed, the hybrid detergent can be considered equivalent to amounts of distinct phenate and sulfonate detergents introducing like amounts of phenate and sulfonate soaps, respectively.
detergents formed with mixed surfactant systems including phenate and/or sulfonate components, e.g., phenate/salicylates, sulfonate/phenates, sulfonate/salicylates, sulfonates/phenates/salicylates, as described, for example, in U.S. Pat. Nos.
6,429,178; 6,429,179; 6,153,565; and 6,281,179. Where a hybrid sulfonate/phenate detergent is employed, the hybrid detergent can be considered equivalent to amounts of distinct phenate and sulfonate detergents introducing like amounts of phenate and sulfonate soaps, respectively.
[0108] Example overbased metal-containing detergents include zinc, sodium, and magnesium salts of sulfonates, phenates (including sulfur-containing and non-sulfur containing phenates), salixarates and salicylates. Such overbased sulfonates, salixarates, phenates and salicylates may have a total base number of 120 to 700, or 250 to 600, or 300 to 500 (on an oil free basis).
[0109] Typically, an overbased metal-containing detergent may be a zinc, sodium, or magnesium salt of a sulfonate, a phenate, sulfur-containing phenate, salixarate or salicylate. Overbased sulfonates, salixarates, phenates and salicylates typically have a total base number of 120 to 700 TBN. Overbased sulfonates typically have a total base number of 120 to 700, or 250 to 600, or 300 to 500 (on an oil free basis).
[0110] The overbased metal-containing detergent may be alkali metal or alkaline earth metal salts. In one embodiment, the overbased detergent may be sodium salts, calcium salts, magnesium salts, or mixtures thereof of the phenates, sulfur-containing phenates, sulfonates, salixarates and salicylates. In one embodiment, the overbased detergent is a calcium detergent, a magnesium detergent or mixtures thereof.
In one embodiment, the overbased calcium detergent may be present in an amount to deliver at least 500 ppm calcium by weight and no more than 3000 ppm calcium by weight, or at least 1000 ppm calcium by weight, or at least 2000 ppm calcium by weight, or no more than 2500 ppm calcium by weight to the lubricating composition. In one embodiment, the overbased detergent may be present in an amount to deliver no more than 500 ppm by weight of magnesium to the lubricating composition, or no more than 330 ppm by weight, or no more than 125 ppm by weight, or no more than 45 ppm by weight. In one embodiment, the lubricating composition is essentially free of (i.e., contains less than 10 ppm) magnesium resulting from the overbased detergent.
In one embodiment, the overbased detergent may be present in an amount to deliver at least 200 ppm by weight of magnesium, or at least 450 ppm by weight magnesium, or at least 700 ppm by weight magnesium to the lubricating composition. In one embodiment, both calcium and magnesium containing detergents may be present in the lubricating composition. Calcium and magnesium detergents may be present such that the weight ratio of calcium to magnesium is 10:1 to 1:10, or 8:3 to 4:5, or 1:1 to 1:3. In one embodiment, the overbased detergent is free of or substantially free of sodium.
In one embodiment, the overbased calcium detergent may be present in an amount to deliver at least 500 ppm calcium by weight and no more than 3000 ppm calcium by weight, or at least 1000 ppm calcium by weight, or at least 2000 ppm calcium by weight, or no more than 2500 ppm calcium by weight to the lubricating composition. In one embodiment, the overbased detergent may be present in an amount to deliver no more than 500 ppm by weight of magnesium to the lubricating composition, or no more than 330 ppm by weight, or no more than 125 ppm by weight, or no more than 45 ppm by weight. In one embodiment, the lubricating composition is essentially free of (i.e., contains less than 10 ppm) magnesium resulting from the overbased detergent.
In one embodiment, the overbased detergent may be present in an amount to deliver at least 200 ppm by weight of magnesium, or at least 450 ppm by weight magnesium, or at least 700 ppm by weight magnesium to the lubricating composition. In one embodiment, both calcium and magnesium containing detergents may be present in the lubricating composition. Calcium and magnesium detergents may be present such that the weight ratio of calcium to magnesium is 10:1 to 1:10, or 8:3 to 4:5, or 1:1 to 1:3. In one embodiment, the overbased detergent is free of or substantially free of sodium.
[0111] The overbased sulfonate detergent may have a metal ratio of 12 to less than 20, or 12 to 18, or 20 to 30, or 22 to 25.
[0112] Example sulfonate detergents include linear and branched alkylbenzene sulfonate detergents, and mixtures thereof, which may have a metal ratio of at least 8, as described, for example, in U.S. Pub. No. 2005065045. Linear alkyl benzenes may have the benzene ring attached anywhere on the linear chain, usually at the 2, 3, or 4 position, or be mixtures thereof. Linear alkylbenzene sulfonate detergents may be particularly useful for assisting in improving fuel economy.
[0113] In one embodiment, the alkylbenzene sulfonate detergent may be a branched alkylbenzene sulfonate, a linear alkylbenzene sulfonate, or mixtures thereof.
[0114] In one embodiment, the lubricating composition may be free of linear alkylbenzene sulfonate detergent. The sulfonate detergent may be a metal salt of one or more oil-soluble alkyl toluene sulfonate compounds as disclosed in U.S.
Pub. No.
20080119378.
Pub. No.
20080119378.
[0115] The lubricating composition may include at least 0.01 wt. % or at least 0.1 wt. %, detergent, and in some embodiments, up to 2 wt. %, or up to 1 wt. %
detergent.
B. Antioxidants
detergent.
B. Antioxidants
[0116] The lubricating composition optionally further includes at least one antioxidant, in addition to the AAOs listed above. Exemplary antioxidants useful herein include sulfurized olefins. Examples of suitable olefins that may be sulfurized to form the sulfurized olefin include propylene, butylene, isobutylene, pentene, hexene, heptene, octene, nonene, decene, undecene, dodecene, undecene, tridecene, tetradecene, pentadecene, hexadecene, heptadecene, octadecene, nonadecene, eicosene, and mixtures thereof. In one embodiment, hexadecene, heptadecene, octadecene, nonadecene, eicosene, or mixtures thereof and their dimers, trimers and tetramers are especially useful olefins.
[0117] Alternatively, the olefin may be a DieIs-Alder adduct of a diene such as 1,3-butadiene and an unsaturated ester, such as, butyl acrylate. Another class of sulfurized 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.
Examples of suitable fatty acids and their esters include triglycerides, oleic acid, linoleic acid, palmitoleic acid, and mixtures thereof. The fatty acids may be obtained from lard oil, tall oil, peanut oil, soybean oil, cottonseed oil, sunflower seed oil or mixtures thereof. In one embodiment fatty acids and/or ester are mixed with olefins. When present, the lubricating composition may include at least 0.1 wt. % or at least 0.5 wt. %, or at least 1 wt. % antioxidant, and in some embodiments, up to 3 wt. %, or up to 2.75 wt.
%, or up to 2.5 wt. %, or up to 1.2 wt. % of such additional antioxidants.
C. Dispersants
Examples of suitable fatty acids and their esters include triglycerides, oleic acid, linoleic acid, palmitoleic acid, and mixtures thereof. The fatty acids may be obtained from lard oil, tall oil, peanut oil, soybean oil, cottonseed oil, sunflower seed oil or mixtures thereof. In one embodiment fatty acids and/or ester are mixed with olefins. When present, the lubricating composition may include at least 0.1 wt. % or at least 0.5 wt. %, or at least 1 wt. % antioxidant, and in some embodiments, up to 3 wt. %, or up to 2.75 wt.
%, or up to 2.5 wt. %, or up to 1.2 wt. % of such additional antioxidants.
C. Dispersants
[0118] The lubricating composition optionally further includes at least one dispersant other than the exemplary compound. Exemplary dispersants include succinimide dispersants, Mannich dispersants, succinamide dispersants, and polyolef in succinic acid esters, amides, and ester-amides, and mixtures thereof.
[0119] The succinimide dispersant may be derived from an aliphatic polyamine, or mixtures thereof. The aliphatic polyamine may be an ethylenepolyamine, a propylenepolyamine, a butylenepolyamine, or a mixture thereof. In one embodiment the aliphatic polyamine may be an ethylenepolyamine. In one embodiment the aliphatic polyamine may be chosen from ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, polyamine still bottoms, and mixtures thereof.
[0120] In one embodiment, the dispersant may be a polyolef in succinic acid ester, amide, or ester-amide. A polyolefin succinic acid ester-amide may be a polyisobutylene succinic acid reacted with an alcohol (such as pentaerythritol) and a polyamine as described above. Example polyolefin succinic acid esters include polyisobutylene succinic acid esters of pentaerythritol and mixture thereof.
[0121] The dispersant may be an N-substituted long chain alkenyl succinimide. An example of an N-substituted long chain alkenyl succinimide is polyisobutylene succinimide. Typically the polyisobutylene from which polyisobutylene succinic anhydride is derived has a number average molecular weight of at least 300, or at least 350, or at least 500, or at least 550, or at least 750, and can be up to 5000, or up to 3000, or up to 2500. Such succinimides can be formed, for example, from high vinylidene polyisobutylene and maleic anhydride. Succinimide dispersants and their preparation are disclosed, for example, in U.S. Pat. Nos. 3,172,892, 3,219,666, 3,316,177, 3,340,281, 3,351,552, 3,381,022, 3,433,744, 3,444,170, 3,467,668, 3,501,405, 3,542,680, 3,576,743, 3,632,511, 4,234,435, Re 26,433, and 6,165,235, and 7,238,650 and EP Patent Application 0 355 895 A.
[0122] The exemplary dispersants may also be post-treated by conventional methods by a reaction with any of a variety of agents. Among these are boron compounds (such as boric acid), urea, thiourea, dimercaptothiadiazoles, carbon disulfide, aldehydes, ketones, carboxylic acids, such as terephthalic acid, hydrocarbon-substituted succinic anhydrides, maleic anhydride, nitrites, epoxides, and phosphorus compounds. In one embodiment the post-treated dispersant is borated. In one embodiment the post-treated dispersant is reacted with dimercaptothiadiazoles.
In one embodiment the post-treated dispersant is reacted with phosphoric or phosphorous acid. In one embodiment the post-treated dispersant is reacted with terephthalic acid and boric acid (as described in U.S. Pub. No. 2009/0054278.
In one embodiment the post-treated dispersant is reacted with phosphoric or phosphorous acid. In one embodiment the post-treated dispersant is reacted with terephthalic acid and boric acid (as described in U.S. Pub. No. 2009/0054278.
[0123] Dispersant viscosity modifiers (DVMs) are dispersants which provide both dispersancy and viscosity modification. Example DVMs are made from polymers such as an olefin polymer (e.g., ethylene propylene copolymer) and/or vinyl aromatic polymers (e.g., polystyrene) that have been radically grafted with an ethylenically unsaturated carboxylic acid material, such as maleic anhydride which is functionalized with one or more amines and/ or a pendent functional group which has sulfonate functionality. DVMs of this type are disclosed, for example, in U.S. Pat. Nos.
4,863,623; 5,264,140; 5,409,623; 6,107,257; 6,107,258; 6,117,825; U.S. Pub.
Nos.
2012/0178656; 2012/0178659; 2009/0305923, and WO 2016044262.
4,863,623; 5,264,140; 5,409,623; 6,107,257; 6,107,258; 6,117,825; U.S. Pub.
Nos.
2012/0178656; 2012/0178659; 2009/0305923, and WO 2016044262.
[0124] When present, the lubricating composition may include at least 0.01 wt. %, or at least 0.1 wt. %, or at least 0.5 wt. %, or at least 1 wt. % dispersant, and in some embodiments, up to 20 wt. %, or up to 15 wt. %, or up to 10 wt. %, or up to 6 wt. % or up to 3 wt. % dispersant.
D. Anti-wear Agents
D. Anti-wear Agents
[0125] The lubricating composition optionally further includes at least one antiwear agent. Examples of suitable antiwear agents suitable for use herein include titanium compounds, tartrates, tartrimides, oil soluble amine salts of phosphorus compounds, sulfurized olefins, metal dihydrocarbyldithiophosphates (such as zinc dialkyldithiophosphates (ZDDPs)), phosphites (such as dibutyl phosphite), phosphonates, thiocarbamate-containing compounds, such as thiocarbamate esters, thiocarbamate amides, thiocarbamic ethers, alkylene-coupled thiocarbamates, and bis(S-alkyldithiocarbamyl) disulfides. The antiwear agent may in one embodiment include a tartrate or tartrimide, as described in U.S. Pub. Nos. 2006/0079413;
2006/0183647; and 2010/0081592. The tartrate or tartrimide may contain alkyl-ester groups, where the sum of carbon atoms on the alkyl groups is at least 8. The antiwear agent may, in one embodiment, include a citrate as disclosed in U.S. Pub. No.
20050198894.
2006/0183647; and 2010/0081592. The tartrate or tartrimide may contain alkyl-ester groups, where the sum of carbon atoms on the alkyl groups is at least 8. The antiwear agent may, in one embodiment, include a citrate as disclosed in U.S. Pub. No.
20050198894.
[0126] When present, the lubricating composition may include at least 0.01 wt. %, or at least 0.1 wt. %, or at least 0.5 wt. % antiwear agent, and in some embodiments, up to 3 wt. %, or up to 1.5 wt. %, or up to 0.9 wt. antiwear agent.
[0127] In one embodiment, the lubricating composition is free or substantially free of phosphorus-containing antiwear agents. For example phosphorus-containing antiwear agents are present, if at all, in an amount which enables the lubricating composition to have no more than 0.15 wt. % phosphorus, or up to 1.1 wt. %
phosphorus, or up to 0.8 wt. ')/0 phosphorus. For example, C3/6 mixed secondary ZDDP's may be present at up to 1.2 wt. %, or up to 1 wt. %, or up to 0.5 wt.
%.
E. Oil Soluble Titanium Compounds
phosphorus, or up to 0.8 wt. ')/0 phosphorus. For example, C3/6 mixed secondary ZDDP's may be present at up to 1.2 wt. %, or up to 1 wt. %, or up to 0.5 wt.
%.
E. Oil Soluble Titanium Compounds
[0128] The lubricating composition may include one or more oil-soluble titanium compounds, which may function as antiwear agents, friction modifiers, antioxidants, deposit control additives, or more than one of these functions. Example oil-soluble titanium compounds are disclosed in U.S. Pat. No. 7,727,943 and U.S. Pub. No.
2006/0014651. Example oil soluble titanium compounds include titanium (IV) alkoxides, such as titanium (IV) isopropoxide and titanium (IV) 2-ethylhexoxide. Such alkoxides may be formed from a monohydric alcohol, a vicinal 1,2-diol, a polyol, or mixture thereof. The monohydric alkoxides may have 2 to 16, or 3 to 10 carbon atoms.
In one embodiment, the titanium compound comprises the alkoxide of a vicinal 1,2-diol or polyol. 1,2-vicinal dials include fatty acid mono-esters of glycerol, where the fatty acid may be, for example, oleic acid. Other example oil soluble titanium compounds include titanium carboxylates, such as titanium neodecanoate.
2006/0014651. Example oil soluble titanium compounds include titanium (IV) alkoxides, such as titanium (IV) isopropoxide and titanium (IV) 2-ethylhexoxide. Such alkoxides may be formed from a monohydric alcohol, a vicinal 1,2-diol, a polyol, or mixture thereof. The monohydric alkoxides may have 2 to 16, or 3 to 10 carbon atoms.
In one embodiment, the titanium compound comprises the alkoxide of a vicinal 1,2-diol or polyol. 1,2-vicinal dials include fatty acid mono-esters of glycerol, where the fatty acid may be, for example, oleic acid. Other example oil soluble titanium compounds include titanium carboxylates, such as titanium neodecanoate.
[0129] When present in the lubricating composition, the amount of oil-soluble titanium compounds is included as part of the antiwear agent.
F. Extreme Pressure (EP) Agents
F. Extreme Pressure (EP) Agents
[0130] The lubricating composition may include an extreme pressure agent.
Example extreme pressure agents that are soluble in the oil include sulfur-and chlorosulfur-containing EP agents, dimercaptothiadiazole or CS2 derivatives of dispersants (typically succinimide dispersants), derivative of chlorinated hydrocarbon EP agents and phosphorus EP agents. Examples of such EP agents include chlorinated wax; sulfurized olefins (such as sulfurized isobutylene), hydrocarbyl-substituted 2,5-dimercapto-1,3,4-thiadiazoles and oligomers thereof, organic sulfides and polysulfides, such as dibenzyl disulfide, bis¨(chlorobenzyl) disulfide, dibutyl tetrasulfide, sulfurized methyl ester of oleic acid, sulfurized alkylphenol, sulfurized dipentene, sulfurized terpene, and sulfurized DieIs-Alder adducts;
phosphosulfurized hydrocarbons such as the reaction product of phosphorus sulfide with turpentine or methyl oleate; phosphorus esters, such as di-hydrocarbon and tri-hydrocarbon phosphites, e.g., dibutyl phosphite, diheptyl phosphite, dicyclohexyl phosphite, pentylphenyl phosphite; dipentylphenyl phosphite, tridecyl phosphite, distearyl phosphite and polypropylene substituted phenol phosphite; metal thiocarbamates, such as zinc dioctyldithiocarbamate and barium heptylphenol diacid; amine salts of alkyl and dialkylphosphoric acids or derivatives including, for example, the amine salt of a reaction product of a dialkyldithiophosphoric acid with propylene oxide and subsequently followed by a further reaction with P205; and mixtures thereof.
Some useful extreme pressure agents are described in U.S. Pat. No. 3,197,405.
Example extreme pressure agents that are soluble in the oil include sulfur-and chlorosulfur-containing EP agents, dimercaptothiadiazole or CS2 derivatives of dispersants (typically succinimide dispersants), derivative of chlorinated hydrocarbon EP agents and phosphorus EP agents. Examples of such EP agents include chlorinated wax; sulfurized olefins (such as sulfurized isobutylene), hydrocarbyl-substituted 2,5-dimercapto-1,3,4-thiadiazoles and oligomers thereof, organic sulfides and polysulfides, such as dibenzyl disulfide, bis¨(chlorobenzyl) disulfide, dibutyl tetrasulfide, sulfurized methyl ester of oleic acid, sulfurized alkylphenol, sulfurized dipentene, sulfurized terpene, and sulfurized DieIs-Alder adducts;
phosphosulfurized hydrocarbons such as the reaction product of phosphorus sulfide with turpentine or methyl oleate; phosphorus esters, such as di-hydrocarbon and tri-hydrocarbon phosphites, e.g., dibutyl phosphite, diheptyl phosphite, dicyclohexyl phosphite, pentylphenyl phosphite; dipentylphenyl phosphite, tridecyl phosphite, distearyl phosphite and polypropylene substituted phenol phosphite; metal thiocarbamates, such as zinc dioctyldithiocarbamate and barium heptylphenol diacid; amine salts of alkyl and dialkylphosphoric acids or derivatives including, for example, the amine salt of a reaction product of a dialkyldithiophosphoric acid with propylene oxide and subsequently followed by a further reaction with P205; and mixtures thereof.
Some useful extreme pressure agents are described in U.S. Pat. No. 3,197,405.
[0131] When present, the lubricating composition may include at least 0.01 wt. %, or at least 0.1 wt. %, or at least 0.5 wt. % extreme pressure agent, and in some embodiments, up to 3 wt. /0, or up to 1.5 wt. %, or up to 0.9 wt. % of the extreme pressure agent.
G. Foam Inhibitors
G. Foam Inhibitors
[0132] The lubricating composition may include a foam inhibitor. Foam inhibitors that may be useful in the lubricant composition include polysiloxanes;
copolymers of ethyl acrylate and 2-ethylhexylacrylate and optionally vinyl acetate;
demulsifiers including fluorinated polysiloxanes, trialkyl phosphates, polyethylene glycols, polyethylene oxides, polypropylene oxides and (ethylene oxide-propylene oxide) polymers.
H. Viscosity Modifiers
copolymers of ethyl acrylate and 2-ethylhexylacrylate and optionally vinyl acetate;
demulsifiers including fluorinated polysiloxanes, trialkyl phosphates, polyethylene glycols, polyethylene oxides, polypropylene oxides and (ethylene oxide-propylene oxide) polymers.
H. Viscosity Modifiers
[0133] The lubricating composition may include a viscosity modifier.
Viscosity modifiers (also sometimes referred to as viscosity index improvers or viscosity improvers) useful in the lubricant composition are usually polymers, including polyisobutenes, polymethacrylates (PMA) and polymethacrylic acid esters, diene polymers, polyalkylstyrenes, esterified styrene-maleic anhydride copolymers, hydrogenated alkenylarene-conjugated diene copolymers and polyolefins also referred to as olefin copolymer or OCP. PMAs are prepared from mixtures of methacrylate monomers having different alkyl groups. The alkyl groups may be either straight chain or branched chain groups containing from 1 to 18 carbon atoms. Most PMAs are viscosity modifiers as well as pour point depressants. In one embodiment, the viscosity modifier is a polyolefin comprising ethylene and one or more higher olefin, such as propylene.
Viscosity modifiers (also sometimes referred to as viscosity index improvers or viscosity improvers) useful in the lubricant composition are usually polymers, including polyisobutenes, polymethacrylates (PMA) and polymethacrylic acid esters, diene polymers, polyalkylstyrenes, esterified styrene-maleic anhydride copolymers, hydrogenated alkenylarene-conjugated diene copolymers and polyolefins also referred to as olefin copolymer or OCP. PMAs are prepared from mixtures of methacrylate monomers having different alkyl groups. The alkyl groups may be either straight chain or branched chain groups containing from 1 to 18 carbon atoms. Most PMAs are viscosity modifiers as well as pour point depressants. In one embodiment, the viscosity modifier is a polyolefin comprising ethylene and one or more higher olefin, such as propylene.
[0134]
When present, the lubricating composition may include at least 0.01 wt. %, or at least 0.1 wt. %, or at least 0.3 wt. %, or at least 0.5 wt. % polymeric viscosity modifiers, and in some embodiments, up to 10 wt. %, or up to 5 wt. %, or up to 2.5 wt.
% polymeric viscosity modifiers.
I. Corrosion Inhibitors and Metal Deactivators
When present, the lubricating composition may include at least 0.01 wt. %, or at least 0.1 wt. %, or at least 0.3 wt. %, or at least 0.5 wt. % polymeric viscosity modifiers, and in some embodiments, up to 10 wt. %, or up to 5 wt. %, or up to 2.5 wt.
% polymeric viscosity modifiers.
I. Corrosion Inhibitors and Metal Deactivators
[0135]
The lubricating composition may include a corrosion inhibitor. Corrosion inhibitors/metal deactivators that may be useful in the exemplary lubricating composition include fatty amines, octylamine octanoate, condensation products of dodecenyl succinic acid or anhydride, and a fatty acid such as oleic acid with a polyamine, derivatives of benzotriazoles (e.g., tolyltriazole), 1,2,4-triazoles, benzimidazoles, 2-alkyldithiobenzimidazoles and 2-alkyldithiobenzothiazoles.
J. Pour Point Depressants
The lubricating composition may include a corrosion inhibitor. Corrosion inhibitors/metal deactivators that may be useful in the exemplary lubricating composition include fatty amines, octylamine octanoate, condensation products of dodecenyl succinic acid or anhydride, and a fatty acid such as oleic acid with a polyamine, derivatives of benzotriazoles (e.g., tolyltriazole), 1,2,4-triazoles, benzimidazoles, 2-alkyldithiobenzimidazoles and 2-alkyldithiobenzothiazoles.
J. Pour Point Depressants
[0136]
The lubricating composition may include a pour point depressant. Pour point depressants that may be useful in the exemplary lubricating composition include polyalphaolefins, esters of maleic anhydride-styrene copolymers, polymethacrylates, polyacrylates, and polyacrylamides.
K. Friction Modifiers
The lubricating composition may include a pour point depressant. Pour point depressants that may be useful in the exemplary lubricating composition include polyalphaolefins, esters of maleic anhydride-styrene copolymers, polymethacrylates, polyacrylates, and polyacrylamides.
K. Friction Modifiers
[0137]
The lubricating composition may include a friction modifier. Friction modifiers that may be useful in the exemplary lubricating composition include fatty acid derivatives such as amines, esters, epoxides, fatty imidazolines, condensation products of carboxylic acids and polyalkylene-polyamines and amine salts of alkylphosphoric acids. The friction modifier may be an ash-free friction modifier. Such friction modifiers are those which typically not produce any sulfated ash when subjected to the conditions of ASTM D 874 (see ASTM D874 - 13a, "Standard Test Method for Sulfated Ash from Lubricating Oils and Additives," ASTM
International, West Conshohocken, PA, 2013). An additive is referred to as "non-metal containing" if it does not contribute metal content to the lubricant composition. As used herein the term "fatty alkyl" or "fatty" in relation to friction modifiers means a carbon chain having 8 to 30 carbon atoms, typically a straight carbon chain.
The lubricating composition may include a friction modifier. Friction modifiers that may be useful in the exemplary lubricating composition include fatty acid derivatives such as amines, esters, epoxides, fatty imidazolines, condensation products of carboxylic acids and polyalkylene-polyamines and amine salts of alkylphosphoric acids. The friction modifier may be an ash-free friction modifier. Such friction modifiers are those which typically not produce any sulfated ash when subjected to the conditions of ASTM D 874 (see ASTM D874 - 13a, "Standard Test Method for Sulfated Ash from Lubricating Oils and Additives," ASTM
International, West Conshohocken, PA, 2013). An additive is referred to as "non-metal containing" if it does not contribute metal content to the lubricant composition. As used herein the term "fatty alkyl" or "fatty" in relation to friction modifiers means a carbon chain having 8 to 30 carbon atoms, typically a straight carbon chain.
[0138] The amount of the ash-free friction modifier in a lubricant may be 0.1 to 3 wt.
% (or 0.12 to 1.2 or 0.15 to 0.8 wt. %). The material may also be present in a concentrate, alone or with other additives and with a lesser amount of oil. In a concentrate, the amount of material may be two to ten times the above concentration amounts.
% (or 0.12 to 1.2 or 0.15 to 0.8 wt. %). The material may also be present in a concentrate, alone or with other additives and with a lesser amount of oil. In a concentrate, the amount of material may be two to ten times the above concentration amounts.
[0139] In one embodiment, the ash-free friction modifier may be represented by the formula:
R21_4..).( C E
where D and D' are independently selected from -0-, >NH, >NR23, an imide group formed by taking together both D and D" groups and forming a R21-N<
group between two >C=0 groups; E is selected from ¨R24-0_,R25_, >CH2, >CHR28, >0R28R27, >C(OH)(CO2R22), >C(CO2R22)2, and >CHOR28; where R24 and R25 are independently selected from >CH2, >CHR26, >cR26R27, >C(OH)(CO2R22), and >CHOR28; q is 0 to 10, with the proviso that when q=1, E is not >CH2, and when n=2, both Es are not >CH2; p is 0 or 1; R21 is independently hydrogen or a hydrocarbyl group, typically containing 1 to 150 carbon atoms, with the proviso that when R21 is hydrogen, p is 0, and q is more than or equal to 1; R22 is a hydrocarbyl group, typically containing 1 to 150 carbon atoms; R23, R24, R25, R26 and R27 are independently hydrocarbyl groups; and R28 is hydrogen or a hydrocarbyl group, containing 1 to 150 carbon atoms, or 4 to 32 carbon atoms, or 8 to 24 carbon atoms. In certain embodiments, the hydrocarbyl groups R23, R24, and R25, may be linear or predominantly linear alkyl groups.
R21_4..).( C E
where D and D' are independently selected from -0-, >NH, >NR23, an imide group formed by taking together both D and D" groups and forming a R21-N<
group between two >C=0 groups; E is selected from ¨R24-0_,R25_, >CH2, >CHR28, >0R28R27, >C(OH)(CO2R22), >C(CO2R22)2, and >CHOR28; where R24 and R25 are independently selected from >CH2, >CHR26, >cR26R27, >C(OH)(CO2R22), and >CHOR28; q is 0 to 10, with the proviso that when q=1, E is not >CH2, and when n=2, both Es are not >CH2; p is 0 or 1; R21 is independently hydrogen or a hydrocarbyl group, typically containing 1 to 150 carbon atoms, with the proviso that when R21 is hydrogen, p is 0, and q is more than or equal to 1; R22 is a hydrocarbyl group, typically containing 1 to 150 carbon atoms; R23, R24, R25, R26 and R27 are independently hydrocarbyl groups; and R28 is hydrogen or a hydrocarbyl group, containing 1 to 150 carbon atoms, or 4 to 32 carbon atoms, or 8 to 24 carbon atoms. In certain embodiments, the hydrocarbyl groups R23, R24, and R25, may be linear or predominantly linear alkyl groups.
[0140] In certain embodiments, the ash-free friction modifier is a fatty ester, amide, or imide of various hydroxy-carboxylic acids, such as tartaric acid, malic acid lactic acid, glycolic acid, and mandelic acid. Examples of suitable materials include tartaric acid di(2-ethylhexyl) ester (i.e., di(2-ethylhexyl)tartrate), di(C8-C10) tartrate, di(C12-15) tartrate, di-oleyl tartrate, ()ley' tartrimide, and oleyl maleimide.
[0141]
In certain embodiments, the ash-free friction modifier may be chosen from long chain fatty acid derivatives of amines, fatty esters, or fatty epoxides;
fatty imidazolines such as condensation products of carboxylic acids and polyalkylene-polyamines; amine salts of alkylphosphoric acids; fatty alkyl tartrates; fatty alkyl tartrimides; fatty alkyl tartramides; fatty phosphonates; fatty phosphites;
borated phospholipids, borated fatty epoxides; glycerol esters; borated glycerol esters; fatty amines; alkoxylated fatty amines; borated alkoxylated fatty amines; hydroxyl and polyhydroxy fatty amines including tertiary hydroxy fatty amines; hydroxy alkyl amides;
metal salts of fatty acids; metal salts of alkyl salicylates; fatty oxazolines; fatty ethoxylated alcohols; condensation products of carboxylic acids and polyalkylene polyamines; or reaction products from fatty carboxylic acids with guanidine, aminoguanidine, urea, or thiourea and salts thereof.
In certain embodiments, the ash-free friction modifier may be chosen from long chain fatty acid derivatives of amines, fatty esters, or fatty epoxides;
fatty imidazolines such as condensation products of carboxylic acids and polyalkylene-polyamines; amine salts of alkylphosphoric acids; fatty alkyl tartrates; fatty alkyl tartrimides; fatty alkyl tartramides; fatty phosphonates; fatty phosphites;
borated phospholipids, borated fatty epoxides; glycerol esters; borated glycerol esters; fatty amines; alkoxylated fatty amines; borated alkoxylated fatty amines; hydroxyl and polyhydroxy fatty amines including tertiary hydroxy fatty amines; hydroxy alkyl amides;
metal salts of fatty acids; metal salts of alkyl salicylates; fatty oxazolines; fatty ethoxylated alcohols; condensation products of carboxylic acids and polyalkylene polyamines; or reaction products from fatty carboxylic acids with guanidine, aminoguanidine, urea, or thiourea and salts thereof.
[0142]
Friction modifiers may also encompass materials such as sulfurized fatty compounds and olefins, sunflower oil or soybean oil monoester of a polyol and an aliphatic carboxylic acid.
Friction modifiers may also encompass materials such as sulfurized fatty compounds and olefins, sunflower oil or soybean oil monoester of a polyol and an aliphatic carboxylic acid.
[0143]
In another embodiment the friction modifier may be a long chain fatty acid ester. In another embodiment the long chain fatty acid ester may be a mono-ester and in another embodiment the long chain fatty acid ester may be a triglyceride.
In another embodiment the friction modifier may be a long chain fatty acid ester. In another embodiment the long chain fatty acid ester may be a mono-ester and in another embodiment the long chain fatty acid ester may be a triglyceride.
[0144]
Molybdenum compounds are also known as friction modifiers. The exemplary molybdenum compound does not contain dithiocarbamate moieties or ligands.
Molybdenum compounds are also known as friction modifiers. The exemplary molybdenum compound does not contain dithiocarbamate moieties or ligands.
[0145] Nitrogen-containing molybdenum materials include molybdenum-amine compounds, as described in U.S. Pat. No. 6,329,327, and organomolybdenum compounds made from the reaction of a molybdenum source, fatty oil, and a diamine as described in U.S. Pat. No. 6,914,037. Other molybdenum compounds are disclosed in U.S. Pub. No. 20080280795. Molybdenum amine compounds may be obtained by reacting a compound containing a hexavalent molybdenum atom with a primary, secondary or tertiary amine represented by the formula NR29R39R31, where each of R29, R39 and R31 is independently hydrogen or a hydrocarbyl group of 1 to 32 carbon atoms and wherein at least one of R29, R3 and R31 is a hydrocarbyl group of 4 or more carbon atoms or represented by the formula:
fOF
R32(,.
where R32 represents a chain hydrocarbyl group having 10 or more carbon atoms, s is 0 or 1, R33 and/or R34 represents a hydrogen atom, a hydrocarbyl group, an alkanol group or an alkyl amino group having 2 to 4 carbon atoms, and when s =
0, both R33 and R34 are not hydrogen atoms or hydrocarbon groups.
fOF
R32(,.
where R32 represents a chain hydrocarbyl group having 10 or more carbon atoms, s is 0 or 1, R33 and/or R34 represents a hydrogen atom, a hydrocarbyl group, an alkanol group or an alkyl amino group having 2 to 4 carbon atoms, and when s =
0, both R33 and R34 are not hydrogen atoms or hydrocarbon groups.
[0146]
Specific examples of suitable amines include monoalkyl (or alkenyl) amines such as tetradecylamine, stearylamine, oleylamine, beef tallow alkylamine, hardened beef tallow alkylamine, and soybean oil alkylamine; dialkyl(or alkenyl)amines such as N-tetradecylmethylamine, N-pentadecylmethylamine, N-hexadecylmethylamine, N-stearylmethylamine, N-oleylmethylamine, N-cocoyl methylamine, N-beef tallow alkyl methylamine, N-hardened beef tallow alkyl methylamine, N-soybean oil alkyl methylamine, ditetradecylamine, dipentadecylamine, dihexadecylamine, distearylamine, dioleylamine, bis(2-hexyldecyl)amine, bis(2-octyldodecyl)amine, bis(2-decyltetradecyl)amine, beef tallow dialkylamine, hardened beef tallow dialkylamine, and soybean oil dialkylamine; and trialk(en)ylamines such as tetradecyldimethylamine, hexadecyldimethylamine, octadecyldimethylamine, beef tallow alkyldimethylamine, hardened beef tallow alkyldimethylamine, soybean oil alkyldimethylamine, dioleylmethylamine, tritetradecylamine, tristearylamine, and trioleylamine.
Suitable secondary amines have two alkyl (or alkenyl) groups with 14 to 18 carbon atoms.
Specific examples of suitable amines include monoalkyl (or alkenyl) amines such as tetradecylamine, stearylamine, oleylamine, beef tallow alkylamine, hardened beef tallow alkylamine, and soybean oil alkylamine; dialkyl(or alkenyl)amines such as N-tetradecylmethylamine, N-pentadecylmethylamine, N-hexadecylmethylamine, N-stearylmethylamine, N-oleylmethylamine, N-cocoyl methylamine, N-beef tallow alkyl methylamine, N-hardened beef tallow alkyl methylamine, N-soybean oil alkyl methylamine, ditetradecylamine, dipentadecylamine, dihexadecylamine, distearylamine, dioleylamine, bis(2-hexyldecyl)amine, bis(2-octyldodecyl)amine, bis(2-decyltetradecyl)amine, beef tallow dialkylamine, hardened beef tallow dialkylamine, and soybean oil dialkylamine; and trialk(en)ylamines such as tetradecyldimethylamine, hexadecyldimethylamine, octadecyldimethylamine, beef tallow alkyldimethylamine, hardened beef tallow alkyldimethylamine, soybean oil alkyldimethylamine, dioleylmethylamine, tritetradecylamine, tristearylamine, and trioleylamine.
Suitable secondary amines have two alkyl (or alkenyl) groups with 14 to 18 carbon atoms.
[0147]
Examples of the compound containing the hexavalent molybdenum atom include molybdenum trioxides or hydrates thereof (Mo03.nH20), molybdenum acid (H2Mo04), alkali metal molybdates (Q2Mo04) wherein Q represents an alkali metal, such as sodium or potassium, ammonium molybdates ((NH4)2Mo04 or heptamolybdate (NH4)6[Mo7024].4H20), Mo0C14, MoO2C12, MoO2Br2, Mo203C16, and the like.
Molybdenum trioxides or hydrates thereof, molybdenum acid, alkali metal molybdates and ammonium molybdates are often suitable because of their availability. In one embodiment, the lubricating composition comprises molybdenum amine compound.
Examples of the compound containing the hexavalent molybdenum atom include molybdenum trioxides or hydrates thereof (Mo03.nH20), molybdenum acid (H2Mo04), alkali metal molybdates (Q2Mo04) wherein Q represents an alkali metal, such as sodium or potassium, ammonium molybdates ((NH4)2Mo04 or heptamolybdate (NH4)6[Mo7024].4H20), Mo0C14, MoO2C12, MoO2Br2, Mo203C16, and the like.
Molybdenum trioxides or hydrates thereof, molybdenum acid, alkali metal molybdates and ammonium molybdates are often suitable because of their availability. In one embodiment, the lubricating composition comprises molybdenum amine compound.
[0148]
Other suitable organomolybdenum compounds may be the reaction products of fatty oils, mono-alkylated alkylene diamines and a molybdenum source.
Materials of this sort are generally made in two steps, a first step involving the preparation of an aminoamide/glyceride mixture at high temperature, and a second step involving incorporation of the molybdenum.
Other suitable organomolybdenum compounds may be the reaction products of fatty oils, mono-alkylated alkylene diamines and a molybdenum source.
Materials of this sort are generally made in two steps, a first step involving the preparation of an aminoamide/glyceride mixture at high temperature, and a second step involving incorporation of the molybdenum.
[0149]
Examples of fatty oils that may be used include cottonseed oil, groundnut oil, coconut oil, linseed oil, palm kernel oil, olive oil, corn oil, palm oil, castor oil, rapeseed oil (low or high erucic acids), soyabean oil, sunflower oil, herring oil, sardine oil, and tallow. These fatty oils are generally known as glyceryl esters of fatty acids, triacylglycerols or triglycerides.
Examples of fatty oils that may be used include cottonseed oil, groundnut oil, coconut oil, linseed oil, palm kernel oil, olive oil, corn oil, palm oil, castor oil, rapeseed oil (low or high erucic acids), soyabean oil, sunflower oil, herring oil, sardine oil, and tallow. These fatty oils are generally known as glyceryl esters of fatty acids, triacylglycerols or triglycerides.
[0150]
Examples of some mono-alkylated alkylene diamines that may be used include methylaminopropylamine, methylaminoethylamine, butylaminopropylamine, butylaminoethylamine, octylaminopropylamine, octylaminoethylamine, dodecylaminopropylamine, dodecylaminoethylamine, hexadecylaminopropylamine, hexadecylaminoethylamine, octadecyl-aminopropylamine, octadecylaminoethylamine, isopropyloxypropy1-1,3-diaminopropane, and octyloxypropy1-1,3-diaminopropane.
Mono-alkylated alkylene diamines derived from fatty acids may also be used.
Examples include N-coco alkyl-1,3-propanediamine (Duomeen0C), N-tall oil alkyl-1,3-propanediamine (DuomeenOT) and N-oley1-1,3-propanediamine (Duomeene0), all commercially available from Akzo Nobel.
Examples of some mono-alkylated alkylene diamines that may be used include methylaminopropylamine, methylaminoethylamine, butylaminopropylamine, butylaminoethylamine, octylaminopropylamine, octylaminoethylamine, dodecylaminopropylamine, dodecylaminoethylamine, hexadecylaminopropylamine, hexadecylaminoethylamine, octadecyl-aminopropylamine, octadecylaminoethylamine, isopropyloxypropy1-1,3-diaminopropane, and octyloxypropy1-1,3-diaminopropane.
Mono-alkylated alkylene diamines derived from fatty acids may also be used.
Examples include N-coco alkyl-1,3-propanediamine (Duomeen0C), N-tall oil alkyl-1,3-propanediamine (DuomeenOT) and N-oley1-1,3-propanediamine (Duomeene0), all commercially available from Akzo Nobel.
[0151]
Sources of molybdenum for incorporation into the fatty oil/diamine complex are generally oxygen-containing molybdenum compounds include, similar to those above, ammonium molybdates, sodium molybdate, molybdenum oxides and mixtures thereof. One suitable molybdenum source comprises molybdenum trioxide (Mo03).
Sources of molybdenum for incorporation into the fatty oil/diamine complex are generally oxygen-containing molybdenum compounds include, similar to those above, ammonium molybdates, sodium molybdate, molybdenum oxides and mixtures thereof. One suitable molybdenum source comprises molybdenum trioxide (Mo03).
[0152] Nitrogen-containing molybdenum compounds which are commercially available include, for example, Sakuralube 710 available from Adeka which is a molybdenum amine compound, and Molyvan 855, available from R.T. Vanderbilt.
[0153] The nitrogen-containing molybdenum compound may be present in the lubricant composition at 0.005 to 2 wt. % of the composition, or 0.01 to 1.3 wt. %, or 0.02 to 1.0 wt. % of the composition. The molybdenum compound may provide the lubricant composition with 0 to 1000 ppm, or 5 to 1000 ppm, or 10 to 750 ppm 5 ppm to 300 ppm, or 20 ppm to 250 ppm of molybdenum.
L. Demulsifiers
L. Demulsifiers
[0154]
Demulsifiers useful herein include trialkyl phosphates, and various polymers and copolymers of ethylene glycol, ethylene oxide, propylene oxide, and mixtures thereof.
M. Seal Swell Agents
Demulsifiers useful herein include trialkyl phosphates, and various polymers and copolymers of ethylene glycol, ethylene oxide, propylene oxide, and mixtures thereof.
M. Seal Swell Agents
[0155] Seal swell agents useful herein include sulfolene derivatives such as Exxon Necton-37TM (FN 1380) and Exxon Mineral Seal OilTM (FN 3200).
N. TBN Boosters
N. TBN Boosters
[0156] Useful TBN boosters are anthranilate ester (esters of anthranilic acid) as described, for example, in U.S. Pub. No. 20140187458, such as decyl anthranilate.
Example Lubricatinci Compositions
Example Lubricatinci Compositions
[0157] An engine lubricant in different embodiments may have a composition as illustrated in Table 1. All additives are expressed on an oil-free basis.
[0158] The exemplary N-alkylated dianiline compound tends to be more effective in low magnesium lubricating compositions. In the lubricating composition, a ratio of calcium to magnesium by weight, may be at least 90:10 and in one embodiment, up to 10:90. Calcium can be provided by overbased detergents, such as calcium sulfonates, as discussed above. In one embodiment, the lubricating composition includes less than 500 ppm magnesium, or less than 200 ppm magnesium, or less than 100 ppm magnesium.
Table 1: Example Lubricating Composition Additive Embodiments (wt. %) A
Example compound 0.1 to 5 0.2 to 2.5 0.3 to 1 Ashless antioxidant selected from a diarylamine antioxidant, a phenolic antioxidant, 0.0 to 5 0.1 to 2.5 0.3 to 1 and mixtures thereof Overbased Calcium Detergent(s) 0.1 to 8 0.3 to 6 1 to 5 Dispersant Viscosity Modifier(s) 0 to 5 0.05 to 4 0.1 to 2 Dispersants 0 to 12 1.5 to 8 0.5 to 6 Other Antioxidants 0.0 to 13 0.1 to 10 2.0 to 5 Other Detergents 0.1 to 8 0.3 to 6 1 to 5 Antiwear Agent(s) 0.1 to 10 0.1 to 5 0.3 to 2 Friction Modifier(s) 0.01 to 4 0.05 to 2 0.1 to 1 Viscosity Modifier(s), other than DVMs 0 to 10 0.5 to 8 1 to 6 Any Other Performance Additive 0 to 10 0 to 8 0 to 6 Balance to Balance to Balance Oil of Lubricating Viscosity 100 % 100 % to 100 %
Use of the Lubricating Composition
Table 1: Example Lubricating Composition Additive Embodiments (wt. %) A
Example compound 0.1 to 5 0.2 to 2.5 0.3 to 1 Ashless antioxidant selected from a diarylamine antioxidant, a phenolic antioxidant, 0.0 to 5 0.1 to 2.5 0.3 to 1 and mixtures thereof Overbased Calcium Detergent(s) 0.1 to 8 0.3 to 6 1 to 5 Dispersant Viscosity Modifier(s) 0 to 5 0.05 to 4 0.1 to 2 Dispersants 0 to 12 1.5 to 8 0.5 to 6 Other Antioxidants 0.0 to 13 0.1 to 10 2.0 to 5 Other Detergents 0.1 to 8 0.3 to 6 1 to 5 Antiwear Agent(s) 0.1 to 10 0.1 to 5 0.3 to 2 Friction Modifier(s) 0.01 to 4 0.05 to 2 0.1 to 1 Viscosity Modifier(s), other than DVMs 0 to 10 0.5 to 8 1 to 6 Any Other Performance Additive 0 to 10 0 to 8 0 to 6 Balance to Balance to Balance Oil of Lubricating Viscosity 100 % 100 % to 100 %
Use of the Lubricating Composition
[0159] The lubricating composition described herein may be used in a method for reducing deposit formation in an internal combustion engine. The internal combustion engine is lubricated with the lubricating composition.
[0160] The end use of the lubricating composition described herein includes use as a cylinder lubricant for an internal combustion engine, such as in a passenger car or a heavy, medium, or light duty diesel vehicle, but may also find use as an engine oil for 2-stroke marine diesel engines, small engines such as motorcycle and 2-stroke oil engines, as a driveline lubricant, including gear and automatic transmission oils, and for other industrial oils, such as hydraulic lubricants.
[0161] An exemplary method of lubricating a mechanical device, such as a passenger car engine cylinder, includes supplying the exemplary lubricating composition to the device.
[0162] Generally, the lubricating composition is added to the lubricating system of an internal combustion engine, which then delivers the lubricating composition to the cylinder of the engine, during its operation.
[0163] The internal combustion engine may be a gasoline fuelled engine, a diesel-fuelled engine, such as a 2-stroke marine diesel engine, or a natural gas fuelled engine, a mixed gasoline/alcohol fuelled engine, or a biodiesel fuelled engine. The internal combustion engine may be a 2-stroke or 4-stroke engine.
[0164] In one embodiment the disclosed technology provides a method of lubricating a 2-stroke or 4-stroke internal combustion engine comprising supplying to the internal combustion engine a lubricating composition as disclosed herein.
[0165] The internal combustion engine may be a passenger car internal combustion engine. The passenger car internal combustion engine may have a reference mass not exceeding 2610 kg. The passenger car engine may be operated on unleaded gasoline.
Unleaded gasoline is well known in the art and is defined by British Standard BS EN
228:2008 (entitled "Automotive Fuels ¨ Unleaded Petrol ¨ Requirements and Test Methods"). The internal combustion engine may also be a heavy duty diesel internal combustion engine. The heavy duty diesel internal combustion engine may have a "technically permissible maximum laden mass" over 3,500 kg. The engine may be a compression ignition engine or a positive ignition natural gas (NG) or LPG
(liquefied petroleum gas) engine.
Unleaded gasoline is well known in the art and is defined by British Standard BS EN
228:2008 (entitled "Automotive Fuels ¨ Unleaded Petrol ¨ Requirements and Test Methods"). The internal combustion engine may also be a heavy duty diesel internal combustion engine. The heavy duty diesel internal combustion engine may have a "technically permissible maximum laden mass" over 3,500 kg. The engine may be a compression ignition engine or a positive ignition natural gas (NG) or LPG
(liquefied petroleum gas) engine.
[0166] The lubricating composition may be suitable for use as a cylinder lubricant irrespective of the sulfur, phosphorus or sulfated ash (ASTM D-874) content of the fuel.
The sulfur content of the lubricating composition, which is particularly suited to use as an engine oil lubricant, may be 1 wt. % or less, or 0.8 wt. % or less, or 0.5 wt. % or less, or 0.3 wt. % or less. In one embodiment, the sulfur content may be in the range of 0.001 wt. % to 0.5 wt. %, or 0.01 wt. % to 0.3 wt. %. The phosphorus content may be 0.2 wt. % or less, or 0.12 wt. % or less, or 0.1 wt. % or less, or 0.085 wt. %
or less, or 0.08 wt. % or less, or even 0.06 wt. % or less, 0.055 wt. % or less, or 0.05 wt. % or less. In one embodiment, the phosphorus content may be 100 ppm to 1000 ppm, or 200 ppm to 600 ppm. The total sulfated ash content may be 2 wt. % or less, or 1.5 wt.
% or less, or 1.1 wt. % or less, or 1 wt. % or less, or 0.8 wt. % or less, or 0.5 wt. % or less, or 0.4 wt. % or less. In one embodiment, the sulfated ash content may be 0.05 wt.
% to 0.9 wt. %, or 0.1 wt. % to 0.2 wt. % or to 0.45 wt. %.
The sulfur content of the lubricating composition, which is particularly suited to use as an engine oil lubricant, may be 1 wt. % or less, or 0.8 wt. % or less, or 0.5 wt. % or less, or 0.3 wt. % or less. In one embodiment, the sulfur content may be in the range of 0.001 wt. % to 0.5 wt. %, or 0.01 wt. % to 0.3 wt. %. The phosphorus content may be 0.2 wt. % or less, or 0.12 wt. % or less, or 0.1 wt. % or less, or 0.085 wt. %
or less, or 0.08 wt. % or less, or even 0.06 wt. % or less, 0.055 wt. % or less, or 0.05 wt. % or less. In one embodiment, the phosphorus content may be 100 ppm to 1000 ppm, or 200 ppm to 600 ppm. The total sulfated ash content may be 2 wt. % or less, or 1.5 wt.
% or less, or 1.1 wt. % or less, or 1 wt. % or less, or 0.8 wt. % or less, or 0.5 wt. % or less, or 0.4 wt. % or less. In one embodiment, the sulfated ash content may be 0.05 wt.
% to 0.9 wt. %, or 0.1 wt. % to 0.2 wt. % or to 0.45 wt. %.
[0167] Without intending to limit the scope of the exemplary embodiment, the following examples illustrate preparation and evaluation of example compounds.
EXAMPLES
EXAMPLES
[0168] All reactants and additives are expressed on an oil-free basis.
Example 1: Synthesis of 4,4'-cyclohexylmethylenedianiline (CY-MDI)
Example 1: Synthesis of 4,4'-cyclohexylmethylenedianiline (CY-MDI)
[0169] 4,4'-methylenedianiline (MDA) (1 eq.), cyclohexanone (2.1 eq.) and acetic acid (0.05 eq.) are charged to a flask with toluene and heated to ref lux with removal of water. Once imine formation is complete, the toluene and residual acetic acid are removed by vacuum. The resulting imine is dissolved in methanol and cooled to less than 10 C using an ice bath. Sodium borohydride (2.2 eq.) is added portion-wise, keeping the reaction temperature below 15 C. The solution is then allowed to warm to .. room temperature and stirred for an additional 2 hours. Once reduction is complete, the mixture is quenched with water and the product is extracted with ethyl acetate. No further purification is needed. The reaction results in the formation of compound A-1 shown in TABLE 2.
Example 2: Synthesis of 4,4'-2-ethylhexylmethylenedianiline (EHL-MDI)
Example 2: Synthesis of 4,4'-2-ethylhexylmethylenedianiline (EHL-MDI)
[0170] The process of Example 1 is repeated, using 2-ethylhexanal (2.1 eq.) in place of cyclohexanone as the ketone. The reaction results in the formation of compound A-2 shown in TABLE 2:
[0171] Using the method of Examples 1 and 2, with the product being either collected by filtration or by extraction with ethyl acetate, the products shown in TABLE
2 are formed using the following amines and ketones/aldehydes:
TABLE 2: Diamine Compounds Example Ketone/Aldehyde Amine ____ 7 , a, ,-- cyclohexanone MDA
N N
I
H 2-ethylhexanal MDA
I
N N 3-pentanone MDA
A-3 . H H .
)a I I 4-methyl N N cyclohexanone MDA
methyl isobutyl õ-.,N,-,.I =/==I N.--,.. MDA
ketone A-5 H , H
4-tert-butyl MDA
>laNcyclohexanone l , e N
isophorone MDA
N NO
A-7 H H . .
3,3,5-trimethyl MDA
cyclohexanone 76N ---HN4:
acetophenone MDA
A91 1=1. N 0 H H
-benzophenone MDA
H H
benzaldehyde MDA
I I
1101 "'-'--- /
H ii 0 , A-11 N m . , To: Page 10 of 26 2018-10-26 16:16113 EDT 12164728733 From: Attorney Fax PCT/US 2017/066 103 ¨ 26.10.2018 Example Ketone/Aldehyde ________________________________________________ Amine .
systehe,Kapana 2,4,6 tr-imethy4-N aniline 4-methy1 2,4,6 eyelahiamanene- tr-iFnethyi-A-4,3 Example 3: Lubricating ComDesilions
2 are formed using the following amines and ketones/aldehydes:
TABLE 2: Diamine Compounds Example Ketone/Aldehyde Amine ____ 7 , a, ,-- cyclohexanone MDA
N N
I
H 2-ethylhexanal MDA
I
N N 3-pentanone MDA
A-3 . H H .
)a I I 4-methyl N N cyclohexanone MDA
methyl isobutyl õ-.,N,-,.I =/==I N.--,.. MDA
ketone A-5 H , H
4-tert-butyl MDA
>laNcyclohexanone l , e N
isophorone MDA
N NO
A-7 H H . .
3,3,5-trimethyl MDA
cyclohexanone 76N ---HN4:
acetophenone MDA
A91 1=1. N 0 H H
-benzophenone MDA
H H
benzaldehyde MDA
I I
1101 "'-'--- /
H ii 0 , A-11 N m . , To: Page 10 of 26 2018-10-26 16:16113 EDT 12164728733 From: Attorney Fax PCT/US 2017/066 103 ¨ 26.10.2018 Example Ketone/Aldehyde ________________________________________________ Amine .
systehe,Kapana 2,4,6 tr-imethy4-N aniline 4-methy1 2,4,6 eyelahiamanene- tr-iFnethyi-A-4,3 Example 3: Lubricating ComDesilions
[0172] The NN'-dialkylmethylenedianilene compounds prepared according to Examples 1 and 2 are evaluated in various formulations.
A. Hiaher Internal Combustion Engine Lubricants
A. Hiaher Internal Combustion Engine Lubricants
[0173] Lubricating compositions suitable as 5W-30 engine lubricants are prepared using a baseline formulation as shown in TABLE 3. All concentrations are on an oil free (i.e., active basis).
TABLE 3: Baseline Lubricating Composition B1 Component Baseline B1 Base Oil Balance to 100%
Calcium alkylsulfonates (overbased detergent) 0.9 Secondary Zinc dialkyldithiophosphate (ZDDP) 0.86 Diarylamine antioxidant' 0.9 Phenol antioxidant2 0.35 Polyisobutylene succinimide dispersant3 2.12 Ethylene-propylene copolymer (viscosity modifier) 0.7 Additional performance additives (friction modifiers, corrosion inhibitors, foam inhibitors, pour point 0.51 depressants, etc.) % Phosphorus 0.075 1. Dinonylated diphenylamine 2. Alkyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanoate 3. Combination of Polyisobutylene succinimide dispersants with Mn ranging from
TABLE 3: Baseline Lubricating Composition B1 Component Baseline B1 Base Oil Balance to 100%
Calcium alkylsulfonates (overbased detergent) 0.9 Secondary Zinc dialkyldithiophosphate (ZDDP) 0.86 Diarylamine antioxidant' 0.9 Phenol antioxidant2 0.35 Polyisobutylene succinimide dispersant3 2.12 Ethylene-propylene copolymer (viscosity modifier) 0.7 Additional performance additives (friction modifiers, corrosion inhibitors, foam inhibitors, pour point 0.51 depressants, etc.) % Phosphorus 0.075 1. Dinonylated diphenylamine 2. Alkyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanoate 3. Combination of Polyisobutylene succinimide dispersants with Mn ranging from
[0174]
The alkylated dianilines of Examples 1 and 2 are added to the baseline composition, as shown in TABLE 4, to form lubricating compositions Li and L2, respectively.
AMENDED SHEET
Received at the EPO on Oct 26, 201822:29:51. Page 10 of 26 Duration: 10.26.2018 10:16:29 PM - 10.26.2018 10:29:51 PM. This page 10 of 26 was completed at 10.26.2018 10:22:38 PM
TABLE 4: Lubricating Oil Composition Formulations Composition B1 L1 L2 B1 100 99.5 99.5 A-1 0.5 A-2 0.5 % Phosphorus 0.075 0.075 0.075 D2896 TBN (mg KOH/kg) 7.5 9.1 8.7
The alkylated dianilines of Examples 1 and 2 are added to the baseline composition, as shown in TABLE 4, to form lubricating compositions Li and L2, respectively.
AMENDED SHEET
Received at the EPO on Oct 26, 201822:29:51. Page 10 of 26 Duration: 10.26.2018 10:16:29 PM - 10.26.2018 10:29:51 PM. This page 10 of 26 was completed at 10.26.2018 10:22:38 PM
TABLE 4: Lubricating Oil Composition Formulations Composition B1 L1 L2 B1 100 99.5 99.5 A-1 0.5 A-2 0.5 % Phosphorus 0.075 0.075 0.075 D2896 TBN (mg KOH/kg) 7.5 9.1 8.7
[0175] Lubricating compositions B1, L1, and L2 are evaluated in the following oxidation bench tests:
[0176] 1. Impact on thin-film antioxidancy: The Pressure Differently Scanning Calorimeter (PDSC) test measures the compositions' oxidative induction time (01T).
This is a standard test procedure in the lubricating oil industry, based on 99. In this testing the lubricating composition is heated to an elevated temperature, typically about 25 C below the average decomposition temperature for the sample being tested (in this case 215 C at 690kPa), and the time to when the composition begins to decompose is measured. The longer the test time, reported in minutes, the better the oxidative stability of the composition and the additives present within it.
This is a standard test procedure in the lubricating oil industry, based on 99. In this testing the lubricating composition is heated to an elevated temperature, typically about 25 C below the average decomposition temperature for the sample being tested (in this case 215 C at 690kPa), and the time to when the composition begins to decompose is measured. The longer the test time, reported in minutes, the better the oxidative stability of the composition and the additives present within it.
[0177] 2. Deposits (MHT TEOST): determined according to ASTM D7097 ¨
09. The MHT TEOST method evaluates deposit formation at temperatures closely related to those of the piston ring zone in reciprocating engines. An organo-metallic catalyst mixture of a predetermined concentration equaling approximately 8.5g is circulated for 24 hrs over a wire-wound depositor rod at 285 C along with 10m1/min of air.
The depositor rod is weighed before test and after testing. Any post-test deposits collected after washing the rod along with rod deposits equals total deposits. In the MHT
TEOST, a lower amount of deposit indicates better deposit control performance.
09. The MHT TEOST method evaluates deposit formation at temperatures closely related to those of the piston ring zone in reciprocating engines. An organo-metallic catalyst mixture of a predetermined concentration equaling approximately 8.5g is circulated for 24 hrs over a wire-wound depositor rod at 285 C along with 10m1/min of air.
The depositor rod is weighed before test and after testing. Any post-test deposits collected after washing the rod along with rod deposits equals total deposits. In the MHT
TEOST, a lower amount of deposit indicates better deposit control performance.
[0178] The results obtained are shown in TABLE 5.
TABLE 5: Oxidation Results for Lubricating Oil Composition Formulations Example PDSC OIT min L-85-99 OIT min MHT TEOST mg
TABLE 5: Oxidation Results for Lubricating Oil Composition Formulations Example PDSC OIT min L-85-99 OIT min MHT TEOST mg
[0179] The results shown in TABLE 5 suggest that the lubricating compositions (L1 and L2) (for example, an internal combustion engine lubricant) containing the alkylated dianilines of Examples 1 and 2 provide exceptional antioxidancy performance as well as unexpected deposit control performance when compared with the baseline formulation (B1).
B. Low-Phosphorus Internal Combustion Engine Lubricants
B. Low-Phosphorus Internal Combustion Engine Lubricants
[0180]
Lubricating compositions suitable as 5W-30 engine lubricants are prepared using a baseline formulation (B2) as shown in TABLE 6. All concentrations are on an oil-free (i.e., active) basis.
TABLE 6: Baseline lubricating composition B2 Component Baseline B2 Base Oil Balance to 100%
Calcium alkylsulfonates (overbased detergent) 0.9 Zinc dialkyldithiophosphate (ZDDP) 0.43 Antioxidants 1 1.73 Polyisobutylene succinimide dispersant2 2.65 Polymeric Viscosity Modifier 0.7 Additional performance additives (friction modifiers, corrosion 0.61 inhibitors, foam inhibitors, pour point depressants, etc.) % Phosphorus 0.038 1. Combination of diary/amine and hindered phenol 2. Combination of Polyisobutylene succinimide dispersants with Mn ranging from
Lubricating compositions suitable as 5W-30 engine lubricants are prepared using a baseline formulation (B2) as shown in TABLE 6. All concentrations are on an oil-free (i.e., active) basis.
TABLE 6: Baseline lubricating composition B2 Component Baseline B2 Base Oil Balance to 100%
Calcium alkylsulfonates (overbased detergent) 0.9 Zinc dialkyldithiophosphate (ZDDP) 0.43 Antioxidants 1 1.73 Polyisobutylene succinimide dispersant2 2.65 Polymeric Viscosity Modifier 0.7 Additional performance additives (friction modifiers, corrosion 0.61 inhibitors, foam inhibitors, pour point depressants, etc.) % Phosphorus 0.038 1. Combination of diary/amine and hindered phenol 2. Combination of Polyisobutylene succinimide dispersants with Mn ranging from
[0181]
The diamines A-1, A-3, and A-4 are added to the baseline composition B1 in the amounts shown in TABLE 7, to form lubricating compositions L3, L4, and L5.
A
further lubricating composition (C1) is prepared with an aminic antioxidant.
TABLE 7: Lubricating Oil Composition Formulations Composition B2 L3 L4 L5 Cl B2 100 99.5 99.5 99.5 99.5 A-1 0.5 A-4 0.5 A-3 0.5 Aminic AO 0.5 % Phosphorus 0.038 0.038 0.038 0.038 0.038 TBN, mg of KOH/g (D2896) 8.7 9.6 9.5 9
The diamines A-1, A-3, and A-4 are added to the baseline composition B1 in the amounts shown in TABLE 7, to form lubricating compositions L3, L4, and L5.
A
further lubricating composition (C1) is prepared with an aminic antioxidant.
TABLE 7: Lubricating Oil Composition Formulations Composition B2 L3 L4 L5 Cl B2 100 99.5 99.5 99.5 99.5 A-1 0.5 A-4 0.5 A-3 0.5 Aminic AO 0.5 % Phosphorus 0.038 0.038 0.038 0.038 0.038 TBN, mg of KOH/g (D2896) 8.7 9.6 9.5 9
[0182] Lubricating compositions B2, L3, L4, L5, and Cl are evaluated in the oxidation bench tests, as described above. The results obtained are shown in TABLE
8.
TABLE 8: Oxidation Results for Lubricating Oil Composition Formulations Example PDSC OIT min L-85-99 OIT min MHT TEOST mg
8.
TABLE 8: Oxidation Results for Lubricating Oil Composition Formulations Example PDSC OIT min L-85-99 OIT min MHT TEOST mg
[0183] The results shown in TABLE 8 suggest that the exemplary lubricating compositions (L3, L4, and L5) (for example, an internal combustion engine lubricant) containing the alkylated dianilines A-1, A-3, and A-4 provide exceptional antioxidancy performance as well as unexpected deposit control performance when compared with the baseline formulation (B2), indicating that the exemplary alkylated dianilines are very efficient in low phosphorus formulations. Additionally, 0.5% of these alkylated dianilines provides a much more significant performance enhancement to the baseline formulation in both the PDSC and the MHT TEOST tests than the addition of a further 0.5% of aminic antioxidant (C1).
C. Internal Combustion Engine Lubricants
C. Internal Combustion Engine Lubricants
[0184] Lubricating compositions suitable as 15W-40 engine lubricants are prepared using a baseline formulation (B3) as shown in TABLE 9. All concentrations are on an oil-free (i.e., active basis).
TABLE 9: Baseline lubricating composition B3 Component Baseline B3 Base Oil Balance to 100%
Calcium alkylsulfonate and calcium sulfur-coupled alkylphenol 2.7 (overbased detergent) Zinc dialkyldithiophosphate (ZDDP) 1.15 Antioxidants (combination of diarylamine and hindered phenol) 1.25 2200 Mn polyisobutylene succinimide, TBN - 55 (ashless 3.6 dispersant) Polymeric Viscosity Modifier 0.9 Additional performance additives (corrosion inhibitor, foam 0.86 inhibitors, pour point depressant, and surfactant etc.) % Phosphorus 0.11
TABLE 9: Baseline lubricating composition B3 Component Baseline B3 Base Oil Balance to 100%
Calcium alkylsulfonate and calcium sulfur-coupled alkylphenol 2.7 (overbased detergent) Zinc dialkyldithiophosphate (ZDDP) 1.15 Antioxidants (combination of diarylamine and hindered phenol) 1.25 2200 Mn polyisobutylene succinimide, TBN - 55 (ashless 3.6 dispersant) Polymeric Viscosity Modifier 0.9 Additional performance additives (corrosion inhibitor, foam 0.86 inhibitors, pour point depressant, and surfactant etc.) % Phosphorus 0.11
[0185] The diamines A-1 and A-2 are added to the baseline composition B3 in the amounts shown in TABLE 10, to form lubricating compositions L6 and L7. TABLE
10:
Lubricating Oil Composition Formulations Composition B3 L6 L7 B3 100 99.5 99.5 A-2 0.5 A-1 0.5 % Phosphorus 0.11 0.11 0.11 TBN mg of KOH/g (D2896) 11.8 12.7 13.2
10:
Lubricating Oil Composition Formulations Composition B3 L6 L7 B3 100 99.5 99.5 A-2 0.5 A-1 0.5 % Phosphorus 0.11 0.11 0.11 TBN mg of KOH/g (D2896) 11.8 12.7 13.2
[0186] Lubricating compositions B3, L6, and L7 are evaluated in the oxidation bench tests, as described above. The results obtained are shown in TABLE 11.
TABLE 11: Oxidation Results for Lubricating Oil Composition Formulations Example PDSC OIT min MHT TEOST mg L6 87 5.5 L7 89 4.6
TABLE 11: Oxidation Results for Lubricating Oil Composition Formulations Example PDSC OIT min MHT TEOST mg L6 87 5.5 L7 89 4.6
[0187] The results shown in TABLE 11 suggest that the exemplary lubricating compositions (L6 and L7) (for example, an internal combustion engine lubricant) containing the alkylated dianilines A-1 and A-2 provide exceptional antioxidancy performance as well as unexpected deposit control performance when compared with the baseline formulation (B3), indicating that the exemplary alkylated dianilines are very efficient in these formulations.
[0188] As used herein, the term "hydrocarbyl substituent" or "hydrocarbyl group" is used in its ordinary sense, which is well-known to those skilled in the art.
Specifically, it refers to a group having a carbon atom directly attached to the remainder of the molecule and having predominantly hydrocarbon character. By predominantly hydrocarbon character, it is meant that at least 70% or at least 80% of the atoms in the substituent are hydrogen or carbon.
Specifically, it refers to a group having a carbon atom directly attached to the remainder of the molecule and having predominantly hydrocarbon character. By predominantly hydrocarbon character, it is meant that at least 70% or at least 80% of the atoms in the substituent are hydrogen or carbon.
[0189] Examples of hydrocarbyl groups include:
(i) 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);
(ii) substituted hydrocarbon substituents, that is, substituents containing non-hydrocarbon groups which, in the context of this invention, do not alter the predominantly hydrocarbon nature of the substituent (e.g., halo (especially chloro and fluoro), hydroxy, alkoxy, mercapto, alkylmercapto, nitro, nitroso, and sulfoxy);
(iii) hetero substituents, that is, substituents which, while having a predominantly hydrocarbon character, may contain other than carbon in a ring or chain otherwise composed of carbon atoms.
(i) 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);
(ii) substituted hydrocarbon substituents, that is, substituents containing non-hydrocarbon groups which, in the context of this invention, do not alter the predominantly hydrocarbon nature of the substituent (e.g., halo (especially chloro and fluoro), hydroxy, alkoxy, mercapto, alkylmercapto, nitro, nitroso, and sulfoxy);
(iii) hetero substituents, that is, substituents which, while having a predominantly hydrocarbon character, may contain other than carbon in a ring or chain otherwise composed of carbon atoms.
[0190] Representative alkyl groups include n-butyl, iso-butyl, sec-butyl, n-pentyl, amyl, neopentyl, n-hexyl, n-heptyl, secondary heptyl, n-octyl, secondary octyl, 2-ethyl hexyl, n-nonyl, secondary nonyl, undecyl, secondary undecyl, dodecyl, secondary dodecyl, tridecyl, secondary tridecyl, tetradecyl, secondary tetradecyl, hexadecyl, secondary hexadecyl, stearyl, icosyl, docosyl, tetracosyl, 2-butyloctyl, 2-butyldecyl, 2-hexyloctyl, 2-hexydecyl, 2-octyldecyl, 2-hexyldodecyl, 2-octyldodecyl, 2-decyltetradecyl, 2-dodecylhexadecyl, 2-hexyldecyloctyldecyl, 2-tetradecyloctyldecyl, monomethyl branched-isostearyl, and the like.
[0191] Representative aryl groups include phenyl, toluyl, xylyl, cumenyl, mesityl, benzyl, phenethyl, styryl, cinnamyl, benzhydryl, trityl, ethylphenyl, propylphenyl, butylphenyl, pentylphenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, decylphenyl, undecylphenyl, dodecylphenyl, benzylphenyl, styrenated phenyl, p-cumylphenyl, a-naphthyl, 8-naphthyl groups, and mixtures thereof.
[0192] Heteroatoms include sulfur, oxygen, nitrogen, and encompass substituents, such as pyridyl, furyl, thienyl and imidazolyl. In general, no more than two, and in one embodiment, no more than one, non-hydrocarbon substituent will be present for every ten carbon atoms in the hydrocarbyl group. In some embodiments, there are no non-hydrocarbon substituents in the hydrocarbyl group.
[0193] Representative aliphatic groups may contain 4 to 14 carbon atoms, 6 to 12 carbon atoms, or 8 to 10 carbon atoms. Examples of suitable alkyl groups include butyl, isobutyl, pentyl, isopentyl, neopentyl, hexyl, amyl, heptyl, octyl, iso-octyl, 2-ethylhexyl, nonyl, decyl, iso-decyl, undecyl, dodecyl, 2-propylheptyl, tridecyl, isotridecyl, tetradecyl, 4-methyl-2-pentyl, propyl heptyl, and combinations thereof.
[0194] Hydrocarbylene groups are the divalent equivalents of hydrocarbyl groups, such as alkylene groups.
[0195] Each of the documents referred to above is incorporated herein by reference. Except in the Examples, or where otherwise explicitly indicated, all numerical quantities in this description specifying amounts of materials, reaction conditions, molecular weights, number of carbon atoms, and the like, are to be understood as modified by the word "about." Unless otherwise indicated, each chemical or composition referred to herein should be interpreted as being a commercial grade material which may contain the isomers, by-products, derivatives, and other such materials which are normally understood to be present in the commercial grade. However, the amount of each chemical component is presented exclusive of any solvent or diluent oil, which may be customarily present in the commercial material, unless otherwise indicated. It is to be understood that the upper and lower amount, range, and ratio limits set forth herein may be independently combined. Similarly, the ranges and amounts for each element of the invention may be used together with ranges or amounts for any of the other elements.
[0196] It will be appreciated that variants of the above-disclosed and other features and functions, or alternatives thereof, may be combined into many other different systems or applications. Various presently unforeseen or unanticipated alternatives, modifications, variations or improvements therein may be subsequently made by those skilled in the art which are also intended to be encompassed by the following claims.
To: Page 11 of 26 2018-10-26 16:16:13 EDT 12164728733 From: Attorney Fax PCT/US 2017/066 103 ¨ 26.10.2018 [0192] Heteroatoms include sulfur, oxygen, nitrogen, and encompass substituents, such as pyridyl, furyl, thienyl and imidazolyi. In general, no more than two, and in one embodiment, no more than one, non-hydrocarbon substituent will be present for every ten carbon atoms in the hydrocarbyl group. In some embodiments, there are no non-hydrocarbon substituents in the hydrocarbyl group.
[0193] Representative aliphatic groups may contain 4 to 14 carbon atoms, 6 to 12 carbon atoms, or 8 to 10 carbon atoms. Examples of suitable alkyl groups include butyl, isobutyl, pentyl, isopentyl, neopentyl, hexyl, amyl, heptyl, octyl, iso-octyl, 2-ethylhexyl, nonyl, decyl, iso-decyl, undecyl, dodecyl, 2-propylheptyl, tridecyl, isotridecyl, tetradecyl, 4-methy1-2-pentyl, propyl heptyl, and combinations thereof.
=
[0194] Hydrocarbylene groups are the divalent equivalents of hydrocarbyl groups, such as alkylene groups.
[0195] Each of the documents- -referred¨to¨above¨is¨i-Rear-piwateeleiR¨=igy reference. Except in the Examples, or where otherwise explicitly indicated, all numerical quantities in this description specifying amounts of materials, reaction conditions, molecular weights, number of carbon atoms, and the like, are to be understood as modified by the word "about" Unless otherwise indicated, each chemical or composition referred to herein should be interpreted as being a commercial grade material which may contain the isomers, by-products, derivatives, and other such materials which are normally understood to be present in the commercial grade. However, the amount of each chemical component is presented exclusive of any solvent or diluent oil, which may be customarily present in the commercial material, unless otherwise indicated. It is to be understood that the upper and lower amount, range, and ratio limits set forth herein may be independently combined. Similarly, the ranges and amounts for each element of the invention may be used together with ranges or amounts for any of the other elements, [0196] t=t--i.vili-lae-appr-esiate4-t4at-va-r-ian=ts--of4lle.--above,-stisolose4-and-other--featu-res-aod¨funot4eeey-er--attern.awes_thec..eefT.may 6e_eemt),iRed_wtle_fHa4,i_ogyir_ijiffefeRt appitoationo.
FROGlifiGatkanfrr improvomontsthorein skilled in the art-which are also intended to be encompassed by the following claims.
AMENDED SHEET
Received at the EPO on Oct 26, 2018 22:29:51. Page 11 of 26 Duration: 10.26.2018 10:16:29 PM - 10.26.2018 10:29:51 PM. This page 11 of 26 was completed at 10.26.2018 10:23:22 PM
To: Page 11 of 26 2018-10-26 16:16:13 EDT 12164728733 From: Attorney Fax PCT/US 2017/066 103 ¨ 26.10.2018 [0192] Heteroatoms include sulfur, oxygen, nitrogen, and encompass substituents, such as pyridyl, furyl, thienyl and imidazolyi. In general, no more than two, and in one embodiment, no more than one, non-hydrocarbon substituent will be present for every ten carbon atoms in the hydrocarbyl group. In some embodiments, there are no non-hydrocarbon substituents in the hydrocarbyl group.
[0193] Representative aliphatic groups may contain 4 to 14 carbon atoms, 6 to 12 carbon atoms, or 8 to 10 carbon atoms. Examples of suitable alkyl groups include butyl, isobutyl, pentyl, isopentyl, neopentyl, hexyl, amyl, heptyl, octyl, iso-octyl, 2-ethylhexyl, nonyl, decyl, iso-decyl, undecyl, dodecyl, 2-propylheptyl, tridecyl, isotridecyl, tetradecyl, 4-methy1-2-pentyl, propyl heptyl, and combinations thereof.
=
[0194] Hydrocarbylene groups are the divalent equivalents of hydrocarbyl groups, such as alkylene groups.
[0195] Each of the documents- -referred¨to¨above¨is¨i-Rear-piwateeleiR¨=igy reference. Except in the Examples, or where otherwise explicitly indicated, all numerical quantities in this description specifying amounts of materials, reaction conditions, molecular weights, number of carbon atoms, and the like, are to be understood as modified by the word "about" Unless otherwise indicated, each chemical or composition referred to herein should be interpreted as being a commercial grade material which may contain the isomers, by-products, derivatives, and other such materials which are normally understood to be present in the commercial grade. However, the amount of each chemical component is presented exclusive of any solvent or diluent oil, which may be customarily present in the commercial material, unless otherwise indicated. It is to be understood that the upper and lower amount, range, and ratio limits set forth herein may be independently combined. Similarly, the ranges and amounts for each element of the invention may be used together with ranges or amounts for any of the other elements, [0196] t=t--i.vili-lae-appr-esiate4-t4at-va-r-ian=ts--of4lle.--above,-stisolose4-and-other--featu-res-aod¨funot4eeey-er--attern.awes_thec..eefT.may 6e_eemt),iRed_wtle_fHa4,i_ogyir_ijiffefeRt appitoationo.
FROGlifiGatkanfrr improvomontsthorein skilled in the art-which are also intended to be encompassed by the following claims.
AMENDED SHEET
Received at the EPO on Oct 26, 2018 22:29:51. Page 11 of 26 Duration: 10.26.2018 10:16:29 PM - 10.26.2018 10:29:51 PM. This page 11 of 26 was completed at 10.26.2018 10:23:22 PM
Claims (27)
1. A lubricating composition comprising:
a) an oil of lubricating viscosity;
b) an N-alkylated dianiline compound;
c) an ashless antioxidant selected from a diarylamine antioxidant, a phenolic antioxidant, and combinations thereof, and d) an overbased calcium detergent;
wherein the lubricating composition comprises less than 0.15 weight percent of phosphorus; and wherein the N-alkylated dianiline is an N,N'-alkylated dianiline compound represented by the formula:
wherein R1 and R2 are independently selected from alkyl groups of 1 to 24 carbon atoms;
R3 and R4 are independently selected from hydrocarbyl groups of 1 to 6 carbon atoms;
each n is from 0 to 3, and X represents a C1-C3 alkylene group.
a) an oil of lubricating viscosity;
b) an N-alkylated dianiline compound;
c) an ashless antioxidant selected from a diarylamine antioxidant, a phenolic antioxidant, and combinations thereof, and d) an overbased calcium detergent;
wherein the lubricating composition comprises less than 0.15 weight percent of phosphorus; and wherein the N-alkylated dianiline is an N,N'-alkylated dianiline compound represented by the formula:
wherein R1 and R2 are independently selected from alkyl groups of 1 to 24 carbon atoms;
R3 and R4 are independently selected from hydrocarbyl groups of 1 to 6 carbon atoms;
each n is from 0 to 3, and X represents a C1-C3 alkylene group.
2. The lubricating composition of claim 1, wherein the lubricating composition has a TBN of at least 4 mg KOH/g, as measured in accordance with ASTM
D-2896.
D-2896.
3. The lubricating composition of any prior claim, wherein the N-alkylated dianiline compound includes at least one N-alkyl group selected from cyclic alkyl groups, acyclic alkyl groups, and combinations thereof.
4. The lubricating composition of claim 3, wherein the N-alkyl group is a cyclohexyl group.
5. The lubricating composition of any prior claim, wherein the N-alkylated dianiline compound is at least 0.10 weight percent of the lubricating composition, or at least 0.15 wt. %, or at least 0.2 wt. %, or at least 0.4 wt. % of the lubricating composition.
6. The lubricating composition of any prior claim, wherein the N-alkylated dianiline compound is up to 4.0 weight percent of the lubricating composition, or up to 3 wt. %, or up to 1.5 wt. %, or up to 1.2 wt. % of the lubricating composition.
7. The lubricating composition of any prior claim, wherein X is a methylene group.
8. The lubricating composition of any prior claim, wherein the N-alkylated dianiline compound is represented by the formula:
wherein R1 and R2 are independently selected from alkyl groups of 1 to 24 carbon atoms.
wherein R1 and R2 are independently selected from alkyl groups of 1 to 24 carbon atoms.
9. The lubricating composition of claim 8, wherein the N-alkylated dianiline compound is represented by the formula:
10. The lubricating composition of any prior claim, wherein the N-alkylated dianiline compound is selected from the group consisting of:
and mixtures thereof.
and mixtures thereof.
11. The lubricating composition of claim 10, wherein the N-alkylated dianiline compound is selected from 4,4'-2-ethylhexylmethylenedianiline, 4,4'-cyclohexylmethylenedianiline, and mixtures thereof.
12. The lubricating composition of any prior claim, wherein the oil of lubricating viscosity is at least 40 weight percent of the lubricating composition.
13. The lubricating composition of any prior claim, wherein the ashless antioxidant is at least 0.1 weight % of the lubricating composition, or at least 0.2 wt. %, or at least 0.4 wt. %, or at least 0.6 wt. %, or up to 4 wt. %, or up to 1.2 wt. %, or up to 1 wt. % of the lubricating composition.
14. The lubricating composition of any prior claim, wherein a ratio of the ashless antioxidant to the N-alkyl dianiline compound is from 20:1 to 1:20.
15. The lubricating composition of any prior claim, wherein the ashless antioxidant comprises a phenolic ester and a diarylamine.
16. The lubricating composition of any prior claim, wherein the ashless antioxidant further comprises a sulfurized olefin.
17. The lubricating composition of any prior claim, wherein the overbased calcium detergent is selected from sulfonates, non-sulfur containing phenates, sulfur containing phenates, salixarates, salicylates, mixtures thereof, and borated equivalents thereof.
18. The lubricating composition of any prior claim, wherein the overbased calcium detergent is present in an amount to deliver at least 2 mg KOH/g of total base number (TBN), as measured in accordance with ASTM D-2896, to the composition.
19. The lubricating composition of any prior claim, wherein the overbased calcium detergent is least 0.01 wt. % or at least 0.1 wt. %, or at least 0.5 wt.
%, or up to 3 wt. %, or up to 2 wt. % of the lubricating composition.
%, or up to 3 wt. %, or up to 2 wt. % of the lubricating composition.
20. The lubricating composition of any prior claim, wherein a ratio of calcium to magnesium in the lubricating composition, by weight, is at least 9:10.
21. The lubricating composition of any prior claim, further comprising a polyolefin succinimide dispersant, wherein the polyolefin group has a number average molecular weight of at least 300.
22. The lubricating composition of any prior claim, further comprising a zinc diaikyldithiophosphate.
23. The lubricating composition of any prior claim, wherein the lubricating composition comprises at least 0.02 weight percent of phosphorus.
24. The lubricating composition of any prior claim, wherein the N-alkylated dianiline compound is a reaction product of a dianiline with at least one of an aldehyde and a ketone.
25. A method for reducing deposit formation in an internal combustion engine comprising lubricating the internal combustion engine with the lubricating composition of any prior claim.
26. Use of the lubricating composition of any one of claims 1-24 for lubricating an internal combustion engine.
27. A method for forming a lubricating composition comprising:
forming an N,N'-alkylated dianiline compound represented by the formula:
wherein R1 and R2 are independently selected from alkyl groups of 1 to 24 carbon atoms;
R3 and R4 are independently selected from hydrocarbyl groups of 1 to 6 carbon atoms;
each n is from 0 to 3, and X represents a C1-C3 alkylene group; and combining the N-alkylated dianiline compound with an oil of lubricating viscosity and at least one of:
an ashless antioxidant selected from a diarylamine antioxidant, a phenolic antioxidant, and combinations thereof, and an overbased calcium detergent;
whereby the lubricating composition comprises less than 0.15 weight percent of phosphorus.
forming an N,N'-alkylated dianiline compound represented by the formula:
wherein R1 and R2 are independently selected from alkyl groups of 1 to 24 carbon atoms;
R3 and R4 are independently selected from hydrocarbyl groups of 1 to 6 carbon atoms;
each n is from 0 to 3, and X represents a C1-C3 alkylene group; and combining the N-alkylated dianiline compound with an oil of lubricating viscosity and at least one of:
an ashless antioxidant selected from a diarylamine antioxidant, a phenolic antioxidant, and combinations thereof, and an overbased calcium detergent;
whereby the lubricating composition comprises less than 0.15 weight percent of phosphorus.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201662439246P | 2016-12-27 | 2016-12-27 | |
US62/439,246 | 2016-12-27 | ||
PCT/US2017/066103 WO2018125569A1 (en) | 2016-12-27 | 2017-12-13 | Lubricating composition including n-alkylated dianiline |
Publications (1)
Publication Number | Publication Date |
---|---|
CA3046788A1 true CA3046788A1 (en) | 2018-07-05 |
Family
ID=60937905
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CA3046788A Pending CA3046788A1 (en) | 2016-12-27 | 2017-12-13 | Lubricating composition including n-alkylated dianiline |
Country Status (7)
Country | Link |
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US (1) | US20190367833A1 (en) |
EP (1) | EP3562921B1 (en) |
CN (1) | CN110114447A (en) |
CA (1) | CA3046788A1 (en) |
DK (1) | DK3562921T3 (en) |
ES (1) | ES2914785T3 (en) |
WO (1) | WO2018125569A1 (en) |
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-
2017
- 2017-12-13 CA CA3046788A patent/CA3046788A1/en active Pending
- 2017-12-13 ES ES17826048T patent/ES2914785T3/en active Active
- 2017-12-13 DK DK17826048.5T patent/DK3562921T3/en active
- 2017-12-13 CN CN201780080961.XA patent/CN110114447A/en active Pending
- 2017-12-13 WO PCT/US2017/066103 patent/WO2018125569A1/en active Search and Examination
- 2017-12-13 US US16/468,766 patent/US20190367833A1/en not_active Abandoned
- 2017-12-13 EP EP17826048.5A patent/EP3562921B1/en active Active
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WO2018125569A1 (en) | 2018-07-05 |
EP3562921B1 (en) | 2022-04-27 |
US20190367833A1 (en) | 2019-12-05 |
EP3562921A1 (en) | 2019-11-06 |
CN110114447A (en) | 2019-08-09 |
DK3562921T3 (en) | 2022-06-07 |
ES2914785T3 (en) | 2022-06-16 |
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