EP0206748A2 - Additif pour huile lubrifiante et composition lubrifiante contenant ceux-ci - Google Patents
Additif pour huile lubrifiante et composition lubrifiante contenant ceux-ci Download PDFInfo
- Publication number
- EP0206748A2 EP0206748A2 EP86304680A EP86304680A EP0206748A2 EP 0206748 A2 EP0206748 A2 EP 0206748A2 EP 86304680 A EP86304680 A EP 86304680A EP 86304680 A EP86304680 A EP 86304680A EP 0206748 A2 EP0206748 A2 EP 0206748A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- succinimide
- lubricating oil
- borated
- catechol
- 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.)
- Granted
Links
- 239000010687 lubricating oil Substances 0.000 title claims abstract description 54
- 239000000203 mixture Substances 0.000 title claims description 75
- 239000000654 additive Substances 0.000 title claims description 18
- 230000000996 additive effect Effects 0.000 title claims description 11
- -1 alkyl catechol Chemical compound 0.000 claims abstract description 101
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims abstract description 79
- YCIMNLLNPGFGHC-UHFFFAOYSA-N o-dihydroxy-benzene Natural products OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims abstract description 78
- 229960002317 succinimide Drugs 0.000 claims abstract description 49
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 15
- 239000000446 fuel Substances 0.000 claims abstract description 15
- 238000002485 combustion reaction Methods 0.000 claims abstract description 14
- 239000003921 oil Substances 0.000 claims description 41
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 16
- 230000007935 neutral effect Effects 0.000 claims description 13
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 12
- 230000007062 hydrolysis Effects 0.000 claims description 11
- 238000006460 hydrolysis reaction Methods 0.000 claims description 11
- 230000001050 lubricating effect Effects 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 229920000768 polyamine Polymers 0.000 claims description 11
- 239000003513 alkali Substances 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 229920001281 polyalkylene Polymers 0.000 claims description 10
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 9
- 229910052791 calcium Inorganic materials 0.000 claims description 9
- 239000011575 calcium Substances 0.000 claims description 9
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052725 zinc Inorganic materials 0.000 claims description 8
- 239000011701 zinc Substances 0.000 claims description 8
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 7
- 229910052749 magnesium Inorganic materials 0.000 claims description 7
- 239000011777 magnesium Substances 0.000 claims description 7
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052788 barium Inorganic materials 0.000 claims description 5
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 claims description 5
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 4
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 239000003607 modifier Substances 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 13
- 239000004711 α-olefin Substances 0.000 description 11
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 10
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 10
- 150000001336 alkenes Chemical class 0.000 description 10
- 229940014800 succinic anhydride Drugs 0.000 description 10
- 150000003871 sulfonates Chemical class 0.000 description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 229920002367 Polyisobutene Polymers 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 238000005260 corrosion Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002199 base oil Substances 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000356 contaminant Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical class [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Chemical class 0.000 description 2
- 239000001257 hydrogen Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- 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 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 229910052712 strontium Inorganic materials 0.000 description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WJECKFZULSWXPN-UHFFFAOYSA-N 1,2-didodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1CCCCCCCCCCCC WJECKFZULSWXPN-UHFFFAOYSA-N 0.000 description 1
- ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 description 1
- DQTMTQZSOJMZSF-UHFFFAOYSA-N 3-pentadecylcatechol Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(O)=C1O DQTMTQZSOJMZSF-UHFFFAOYSA-N 0.000 description 1
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- AOZDHFFNBZAHJF-UHFFFAOYSA-N [3-hexanoyloxy-2,2-bis(hexanoyloxymethyl)propyl] hexanoate Chemical compound CCCCCC(=O)OCC(COC(=O)CCCCC)(COC(=O)CCCCC)COC(=O)CCCCC AOZDHFFNBZAHJF-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SAOKZLXYCUGLFA-UHFFFAOYSA-N bis(2-ethylhexyl) adipate Chemical compound CCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCC SAOKZLXYCUGLFA-UHFFFAOYSA-N 0.000 description 1
- OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006388 chemical passivation reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- GHKVUVOPHDYRJC-UHFFFAOYSA-N didodecyl hexanedioate Chemical compound CCCCCCCCCCCCOC(=O)CCCCC(=O)OCCCCCCCCCCCC GHKVUVOPHDYRJC-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 239000010707 multi-grade lubricating oil Substances 0.000 description 1
- 125000001802 myricyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- LSOWJXYTQNMRAE-UHFFFAOYSA-N undecyl catechol Natural products CCCCCCCCCCCC1=CC=CC(O)=C1O LSOWJXYTQNMRAE-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- 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
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Definitions
- This invention relates to lubricating oil additives which serve to reduce friction in internal combustion engines and to the use of such additives in lubricant compositions.
- U.S. Patent No. 2,795,548 discloses the use of lubricating-oil compositions containing borated alkyl catechols.
- the oil compositions are used in the crankcase of an internal combustion engine in order to reduce oxidation of the oil and corrosion of the metal parts of the engine.
- borated alkyl catechols may be stabilized against hydrolysis by reacting the borated alkyl catechol with an alkenyl or alkyl mono or bis succinimide, and that lubricating the crankcase of an internal combustion engine with a lubricating oil containing such a reaction product reduces the fuel consumption of the engine.
- a lubricating oil additive comprising a complex obtainable by reacting a borated alkyl catechol with an oil soluble alkyl or alkenyl mono or bis succinimide.
- a lubricating oil composition comprising an oil of lubricating viscosity and, in an amount effective to reduce friction, an additive prepared by reacting a borated alkyl catechol with an oil soluble alkyl or alkenyl mono or bis succinimide.
- additives may also be present in the lubricating oil in order to obtain a proper balance of properties such as dispersancy, corrosion, wear and oxidation inhibition which are critical for the proper operation of an internal combustion engine.
- a method of reducing the fuel consumption of an internal combustion engine comprising treating the moving surface thereof with the lubricating oil composition as described above.
- improvements in fuel mileage of from 1% to 2% may be obtained by employing the composition of this invention.
- This fuel economy improvement can be obtained in both compression-ignition engines, that is, diesel engines, and spark-ignition engines, that is, gasoline engines.
- lubricating oil compositions containing the borated alkyl catechol-succinimide complex of this invention have been found additionally to possess antioxidant properties and when employed in diesel engines they possess diesel deposit inhibition.
- the complex between the borated alkyl catechol and the alkenyl or alkyl succinimide may be prepared in situ. That is when borated alkyl catechol and a sufficient amount of an alkenyl or alkyl mono or bis succinimide to stabilize the borated alkyl catechol against hydrolysis are added to the lubricating oil, the complex is formed in situ.
- the present invention relates to a lubricating oil composition
- a lubricating oil composition comprising an oil of lubricating viscosity and an effective amount to reduce friction of a borated alkyl catechol and an effective amount of an alkenyl mono or bis succinimide to stabilize the borated alkyl catechol against hydrolysis.
- the lubricating oil When employed in this manner, other additives may also be present in.the lubricating oil in order to obtain a proper balance of properties such as dispersion, corrosion, wear and oxidation which are critical for the proper operation of an internal combustion engine.
- another aspect of the present invention is a lubricating oil composition especially useful in the crankcase of an internal combustion engine for the purpose of improving the fuel consumption of said engine comprising
- the borated alkyl catechols may be prepared by borating a alkyl catechol with boric acid with removal of the water of reaction.
- there is sufficient boron present such that each boron will react with from 1.5 to 2.5 hydroxyl groups present in the reaction mixture.
- the reaction may be carried out at a temperature in the range of 60°C to 135°C, in the absence or presence of any suitable organic solvent, such as methanol, benzene, xylenes, toluene, or neutral oil.
- any suitable organic solvent such as methanol, benzene, xylenes, toluene, or neutral oil.
- the alkyl catechols or mixtures thereof which may be used to prepare the borated alkyl catechols used in this invention are preferably monoalkyl catechols of Formula I wherein R is alkyl containing 10 to 30 carbon atoms and preferably from 16 to 26 carbon atoms. Also, up to 25% by weight but preferably less than 10% by weight of the monoalkyl catechols may have the R group in a position adjacent or ortho to one of the hydroxy groups and has the Formula II wherein R is defined above.
- alkyl catechols which may be used to prepare the borated alkyl catechols of this invention are dialkyl catechols which are generally of Formula III wherein R is defined above. Trialkyl catechols may also be employed although they are not preferred.
- alkyi catechols which may be employed are decyl catechol, undecyl catechol, dodecyl catechol, tetradecyl catechol, pentadecyl catechol, hexadecyl catechol, octadecyl catechol, eicosyl catechol, hexacosyl catechol, triacontyl catechol, and the like.
- a mixture of alkyl catechols may be employed such as a mixture of C 14 to C 26 alkyl catechols, for example C14-C18 alkyl catechols or C 16 -C 26 alkyl catechols, may be used.
- the alkyl catechols of the Formula III may be prepared by reacting a C 10 to C 30 olefin such as a branched olefin or straight-chained alpha-olefin containing 10 to 30 carbon atoms with pyrocatechol in the presence of a sulfonic acid catalyst at a temperature of from about 60°C to 200°C, and preferably 125°C to 180°C in an essentially inert solvent at atmospheric pressure.
- the inert solvents include benzene, toluene, chlorobenzene and 250 Thinner which is a mixture of aromatics, paraffins and naphthenes.
- branched olefin means that branching occurs at the double bond.
- straight chain alpha olefin means that the alpha olefin contains little (less than 10%) or no branching at the double bond or elsewhere.
- a product which is predominantly monoalkyl catechol may be prepared by using molar ratios of reactants and preferably a 10% by weight molar excess of branched olefin or alpha-olefin over catechol is used. When used at molar ratios, the resulting products are generally monoalkyl catechols but contain some amounts of dialkyl catechol. In any event, molar excess of pyrocatechol (i.e., 2 equivalents of pyrocatechol for each equivalent of olefin) can be used in order to enhance monoalkylation if predominantly monoalkyl catechol is desired. Predominantly dialkyl catechols may be prepared by employing two equivalents to pyrocatechol of the same or different olefin.
- Use of a branched olefin results in a greater proportion of alkyl catechols of Formula I than use of straight-chain alpha-olefins. Use of such branched olefins generally results in greater than 90% alkyl catechol of Formula I and less than 10% alkyl catechol of Formula II.
- the borated alkyl catechols are stabilized against hydrolysis by reacting the catechols with an alkyl or alkenyl mono or bis succinimide.
- an alkyl or alkenyl mono-succinimide is employed.
- the oil soluble alkenyl or alkyl mono- or bis-succinimides which are employed in this invention are generally known as lubricating oil detergents and are described in for example U.S. Patents Nos. 2,992,708 3,018,291, 3,024,237, 3,100,673, 3,219,666, 3,172,892 and 3,272,746.
- the alkenyl succinimides are the reaction product of a polyolefin polymer-substituted succinic anhydride with an amine, preferably a polyalkylene polyamine.
- the polyolefin polymer-substituted succinic anhydrides are obtained by reaction of a polyolefin polymer or a derivative thereof with maleic anhydride.
- the succinic anhydride thus obtained is reacted with the amine compound.
- the preparation of the alkenyl succinimides has been described many times in the art. See, for example, U.S. Patent Nos. 3,390,082, 3,219,666 and 3,172,892.
- a product comprising predominantly mono- or bis-succinimide can be prepared by controlling the molar ratios of the reactants. Thus, for example, if one mole of amine is reacted with one mole of the alkenyl or alkyl substituted succinic anhydride, a predominantly mono-succinimide product will be prepared. If two moles of the succinic anhydride are reacted per mole of polyamine, a bis-succinimide will be prepared.
- the alkenyl succinimide is a mono-succinimide prepared from a polyisobutene-substituted succinic anhydride of a polyalkylene polyamine.
- the polyisobutene from which the polyisobutene-substituted succinic anhydride is obtained by polymerizing isobutene can vary widely in its compositions.
- the average number of carbon atoms can range from 30 or less to 250 or more, with a resulting number average molecular weight of about 400 or less to 3,000 or more.
- the average number of carbon atoms per polyisobutene molecule will range from about 50 to about 100 with the polyisobutenes having a number average molecular weight of about 600 to about 1,500. More preferably, the average number of carbon atoms per polyisobutene molecule ranges from about 60 to about 90, and the number average molecular weight ranges from about 800 to 1,300.
- polyisobutene is reacted with maleic anhydride according to well-known procedures to yield the polyisobutene-substituted succinic anhydride. See, for example, U.S. Patent Nos. 4,388,471 and 4,450,281.
- each alkylene radical of the polyalkylene polyamine usually has up to about 8 carbon atoms.
- the number of alkylene radicals can range up to about 8.
- the alkylene radical is exemplified by ethylene, propylene, butylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, octamethylene, etc.
- the number of amino groups generally, but not necessarily, is one greater than the number of alkylene radicals present in the amine, i.e., if a polyalkylene polyamine contains 3 alkylene radicals, it will usually contain 4 amino radicals.
- the number of amino radicals can range up to about 9.
- the alkylene radical contains from about 2 to about 4 carbon atoms and all amine groups are primary or secondary. In this case, the number of amine groups exceeds the number of alkylene groups by 1.
- the polyalkylene polyamine contains from 3 to 5 amine groups.
- polyalkylene polyamines include ethylenediamine, diethylenetriamine, triethylenetetramine, propylenediamine, tripropylenetetramine, tetraethylenepentamine, trimethylenediamine, pentaethylenehexamine, di-(trimethylene)triamine, tri(hexamethylene)tetramine, etc.
- amines suitable for preparing the alkenyl succinimide useful in this invention include the cyclic amines such as piperazine, morpholine and dipiperazines.
- alkenyl succinimides used in the compositions of this invention have the following formula: wherein:
- the alkenyl succinimide is present in the lubricating oil compositions of the invention in an amount effective to stabilize the borated alkyl catechols against hydrolysis and to act as a dispersant and prevent the deposit of contaminants formed in the oil during operation of the engine.
- the exact structure of the complex of this invention is not known. For certain, however, while not limiting this invention to any theory, it is believed to be compounds in which boron is either complexed, by or the salt of, one or more nitrogen atoms of the basic nitrogen contained in the succinimide. Therefore, it is preferred that the alkenyl succinimide contain at least 2 and preferably 3-5 basic nitrogens per atoms.
- the complex may be formed by reacting the borated alkyl catechol and the succinimide together neat at a temperature above the melting point of the mixture of reactants and below the decomposition temperature, or in a diluent in which both reactants are soluble.
- the reactants may be combined in the proper ratio in the absence of a solvent to form a homogeneous product which may be added to the oil or the reactants may be combined in the proper ratio in a solvent such as toluene or chloroform, the solvent stripped off, and the complex thus formed may be added to the oil.
- the complex may be prepared in a lubricating oil as a concentrate containing from about 20 to 90% by weight of the complex, which concentrate may be added in appropriate amounts to the lubricating oil in which it is to be used or the complex may be prepared directly in the lubricating oil in which it is to be used.
- the diluent is preferably inert to the reactants and products formed and is used in an amount sufficient to insure solubility of the reactants and to enable the mixture to be efficiently stirred.
- Temperatures for preparing the complex may be in the range of from 25°C to 200°C and preferably 25°C to 100°C depending on whether the complex is prepared neat or in a diluent, i.e., lower temperatures may be used when a solvent is used.
- weight percent ratios of succinimide to borated alkyl catechol used to form the complex are in the range of 3:1 to 16:1 and preferably from 3:1 to 10:1 and most preferably 3:1 to 6:1. This latter ratio is preferred if the complex is made and/or stored neat or in the absence of solvent or lubricating oil and under atmospheric conditions.
- the term "stabilized against hydrolysis” means that the borated alkyl catechol-succinimide complex does not form a precipitate due to the hydrolysis of the borated catechol for a period of at least three months when stored at room temperature (about 15-25°C) and ambient humidity.
- the amount of the complex required to be effective for reducing friction in lubricating oil compositions may range from 0.5% to 20% by weight percent. However, in the preferred embodiment, it is desirable to add sufficient complex so that the amount of borated catechol is added at a range from 0.1% to about 4% by weight of the total lubricant composition and preferably is present in the range of from 0.2% to 2% by weight and most preferably 0.5% to 1%.
- the succinimide is present in the complex of the invention in an amount effective to stabilize the borated alkyl catechol against hydrolysis and which allows the borated alkyl catechol to function as effective friction reducing agents.
- the succinimide in the complex acts as a dispersant and prevents the deposition of contaminants formed in the oil during operation of the engine.
- complexes of this invention may also be used in combination with other additive systems in conventional amounts for their known purpose.
- the base composition described above will be formulated with supplementary additives to provide the necessary stability, detergency, dispersancy, anti-wear and anti-corrosion properties.
- the lubricating oils to which the complexes prepared by reacting the borated alkyl catechols and succinimides may contain an alkali or alkaline earth metal hydrocarbyl sulfonate, an alkali or alkaline earth metal phenate, and Group II metal salt dihydrocarbyl dithiophosphate.
- succinimides act as excellent dispersants
- additional succinimide may be added to the lubricating oil compositions, above the amounts added in the form of the complex with the borated alkyl catechols.
- the amount of succinimides can range up to about 20% by weight of the total lubricating oil compositions.
- the alkali or alkaline earth metal hydrocarbyl sulfonates may be either petroleum sulfonate, synthetically alkylated aromatic sulfonates, or aliphatic sulfonates such as those derived from polyisobutylene.
- One of the more important functions of the sulfonates is to act as a detergent and dispersant. These sulfonates are well known in the art.
- the hydrocarbyl group must have a sufficient number of carbon atoms to render the sulfonate molecule oil soluble.
- the hydrocarbyl portion has at least 20 carbon atoms and may be aromatic or aliphatic, but is usually alkylaromatic. Most preferred for use are calcium, magnesium or barium sulfonates which are aromatic in character.
- Certain sulfonates are typically prepared by sulfonating a petroleum fraction having aromatic groups, usually mono- or dialkylbenzene groups, and then forming the metal salt of the sulfonic acid material.
- Other feedstocks used for preparing these sulfonates include synthetically alkylated benzenes and aliphatic hydrocarbons prepared by polymerizing a mono- or diolefin, for example, a polyisobutenyl group prepared by polymerizing isobutene.
- the metallic salts are formed directly or by metathesis using well-known procedures.
- the sulfonates may be neutral or overbased having base numbers up to about 400 or more.
- Carbon dioxide and calcium hydroxide or oxide are the most commonly used material to produce the basic or overbased sulfonates.
- Mixtures of neutral and overbased sulfonates may be used.
- the sulfonates are ordinarily used so as to provide from 0.3% to 10% by weight of the total composition.
- the neutral sulfonates are present from 0.4% to 5% by weight of the total composition and the overbased sulfonates are present from 0.3% to 3% by weight of the total composition.
- the phenates for use in this invention are those conventional products which are the alkali or alkaline earth metal salts of alkylated phenols.
- One of the functions of the phenates is to act as a detergent and dispersant. Among other things, it prevents the deposit of contaminants formed during high temperature operation of the engine.
- the phenols may be mono- or polyalkylated.
- the alkyl portion of the alkyl phenate is present to lend oil solubility to the phenate.
- the alkyl portion can be obtained from naturally occurring or synthetic sources.
- Naturally occurring sources include petroleum hydrocarbons such as white oil and wax. Being derived from petroleum, the hydrocarbon moiety is a mixture of different hydrocarbyl groups, the specific composition of which depends upon the particular oil stock which was used as a starting material.
- Suitable synthetic sources include various commercially available alkenes and alkane derivatives which, when reacted with the phenol, yield an alkylphenol.
- Suitable radicals obtained include butyl, hexyl, octyl, decyl, dodecyl, hexadecyl, eicosyl, triacontyl, and the like.
- Other suitable synthetic sources of the alkyl radical include olefin polymers such as polypropylene, polybutylene, polyisobutylene and the like.
- the alkyl group can be straight-chained or branch-chained, saturated or unsaturated (if unsaturated, preferably containing not more than 2 and generally not more than 1 site of olefinic unsaturation).
- the alkyl radicals will generally contain from 4 to 30 carbon atoms. Generally when the phenol is monoalkyl-substituted, the alkyl radical should contain at least 8 carbon atoms.
- the phenate may be sulfurized if desired. It may be either neutral or overbased and if overbased will have a base number of up to 200 to 300 or more. Mixtures of neutral and overbased phenates may be used.
- the phenates are ordinarily present in the oil to provide from 0.2% to 27% by weight of the total composition.
- the neutral phenates are present from 0.2% to 9% by weight of the total composition and the overbased phenates are present from 0.2 to 13% by weight of the total composition.
- the overbased phenates are present from 0.2% to 5% by weight of the total composition.
- Preferred metals are calcium, magnesium, strontium or barium.
- the sulfurized alkaline earth metal alkyl phenates are preferred. These salts are obtained by a variety of processes such as treating the neutralization product of an alkaline earth metal base and an alkylphenol with sulfur. Conveniently the sulfur, in elemental form, is added to the neutralization product and reacted at elevated temperatures to produce the sulfurized alkaline earth metal alkyl phenate.
- Carbon dioxide and calcium hydroxide or oxide are the most commonly used material to produce the basic or "overbased” phenates.
- a process wherein basic sulfurized alkaline earth metal alkylphenates are produced by adding carbon dioxide is shown in Hanneman, U.S. Patent No. 3,178,368.
- the Group II metal salts of dihydrocarbyl dithiophosphoric acids exhibit wear, antioxidant and thermal stability properties.
- Group II metal salts of phos- phorodithioic acids have been described previously. See, for example, U.S. Patent No. 3,390,080, columns 6 and 7, wherein these compounds and their preparation are described generally.
- the Group II metal salts of the dihydrocarbyl dithiophosphoric acids useful in-the lubricating oil composition of this invention contain from about 4 to about 12 carbon atoms in each of the hydrocarbyl radicals and may be the same or different and may be aromatic, alkyl or cycloalkyl.
- Preferred hydrocarbyl groups are alkyl groups containing from 4 to 8 carbon atoms and are represented by butyl, isobutyl, sec.-butyl, hexyl, isohexyl, octyl, 2-ethylhexyl and the like.
- the metals suitable for forming these salts include barium, calcium, strontium, zinc and cadmium, of which zinc is preferred.
- the Group II metal salt of a dihydrocarbyl dithiophosphoric acid has the following formula: wherein:
- the dithiophosphoric salt is present in the lubricating oil compositions of this invention in an amount effective to inhibit wear and oxidation of the lubricating oil.
- the amount ranges from about 0.1 to about 4 percent by weight of the total composition, preferably the salt is present in an amount ranging from about 0.2 to about 2;5 percent by weight of the total lubricating oil composition.
- the final lubricating oil composition will ordinarily contain 0.025 to 0.25% by weight phosphorus and preferably 0.05 to 0.15% by weight.
- the finished lubricating oil may be single or multigrade.
- Multigrade lubricating oils are prepared by adding viscosity index (VI) improvers.
- Typical viscosity index improvers are polyalkyl methacrylates, ethylene propylene copolymers, styrene diene copolymers and the like.
- So-called decorated VI improvers having both viscosity index and dispersant properties are also suitable for use in the formulations of this invention.
- the lubricating oil used in the compositions of this invention may be mineral oil or in synthetic oils of lubricating viscosity and preferably suitable for use in the crankcase of an internal combustion engine.
- Crankcase lubricating oils ordinarily have a viscosity of about 1300 cst 0°F to 22.7 cst at 210°F (99°C).
- the lubricating oils may be derived from synthetic or natural sources.
- Mineral oil for use as the base oil in this invention includes paraffinic, naphthenic and other oils that are ordinarily used in lubricating oil compositions.
- Synthetic oils include both hydrocarbon synthetic oils and synthetic esters.
- Useful synthetic hydrocarbon oils include liquid polymers of alpha olefins having the proper viscosity.
- the hydrogenated liquid oligomers of C 6-12 alpha olefins such as 1-decene trimer.
- alkyl benzenes of proper viscosity such as didodecyl benzene
- useful synthetic esters include the esters of both monocarboxylic acid and polycarboxylic acids as well as monohydroxy alkanols and polyols. Typical examples are didodecyl adipate, pentaerythritol tetracaproate, di-2-ethylhexyl adipate, dilaurylsebacate and the like.
- Complex esters prepared from mixtures of mono and dicarboxylic acid and mono and dihydroxy alkanols can also be used.
- Blends of hydrocarbon oils with synthetic oils are also useful. For example, blends of 10 to 25 weight percent hydrogenated 1-decene trimer with 75 to 90 weight percent 150 SUS (100°F) mineral oil gives an excellent lubricating oil base.
- Additive concentrates are also included within the scope of this invention. They usually include from about 90 to 20 weight percent of an oil of lubricating viscosity and from about 20 to 90 weight percent of the complex additive of this invention. Typically, the concentrates contain sufficient diluent to make them easy to handle during shipping and storage. Suitable diluents for the concentrates include any inert diluent, preferably an oil of lubricating viscosity, so that the concentrate may be readily mixed with lubricating oils to prepare lubricating oil compositions.
- Suitable lubricating oils which can be used as diluents typically have viscosities in the range from about 35 to about 500 Saybolt Universal Seconds (SUS) at 100°F (38°C), although an oil of lubricating viscosity may be used.
- SUS Saybolt Universal Seconds
- additives which may be present in the formulation include rust inhibitors, foam inhibitors, corrosion inhibitors, metal deactivators, pour point depressants, antioxidants, and a variety of other well-known additives.
- the reaction mixture was heated at 150°C to 160°C for about 7 hours with stirring under a nitrogen atmosphere.
- the reaction mixture was stripped by heating to 160°C under vacuum (0.4 mm Hg).
- the product was filtered hot over super cell (SCC) to afford 908.5 gms. of C 14 -C 18 alkyl substituted pyrocatechol.
- the product had a hydroxyl number of 259.
- SCC super cell
- An oil blend was prepared as indicated in Table I using CitCon 100N oil and containing 1.0% by weight of the borated alkyl catechol prepared according to Example 3.
- One part by weight of the borated alkyl catechol prepared according to Example 3 and 3 parts by weight of a 48% by weight of polyisobutenyl succinimide prepared by reacting polyisobutenyl succinic anhydride wherein the number average molecular weight of the polyisobutenyl was about 950 and tetraethylenepentamine in a mole ratio of amine to anhydride of 0.87) solution in oil (CitCon 100N) were heated together with mixing on a hot plate at 100°C for 0.5 hours.
- the borated alkyl catechol hydrolyzed and formed a skin on its surface as it cooled down (approx. 1/4-hr).
- the borated alkyl catechol-succinimide complexed material remained bright and clear after one week in storage. Even after three weeks, the sample remained clear.
- Tests were carried out which demonstrate the improvements in fuel economy obtained by adding lubricating oil compositions of this invention to the crankcase of an automobile engine.
- crankcase oils each containing 0.5% to 2% by weight of borated C 18 -C 24 monoalkyl catechol, borated C 14 -C 18 dialkyl catechol and the like in the place of borated C 14 -C 18 alkyl catechol of Example 3 in the above formulations are also effective in reducing fuel consumption in an internal combustion engine.
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Organic Chemistry (AREA)
- Lubricants (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/745,661 US4629577A (en) | 1985-06-17 | 1985-06-17 | Method for improving fuel economy of internal combustion engines |
| US745565 | 1985-06-17 | ||
| US745661 | 1985-06-17 | ||
| US06/745,565 US4629578A (en) | 1985-06-17 | 1985-06-17 | Succinimide complexes of borated alkyl catechols and lubricating oil compositions containing same |
| BR8605801A BR8605801A (pt) | 1985-06-17 | 1986-11-26 | Composicao,composicao de oleo lubrificante e processo para reduzir o consumo de combustivel de um motor de combustao interna |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0206748A2 true EP0206748A2 (fr) | 1986-12-30 |
| EP0206748A3 EP0206748A3 (en) | 1989-04-05 |
| EP0206748B1 EP0206748B1 (fr) | 1992-09-02 |
Family
ID=27159992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP86304680A Expired - Lifetime EP0206748B1 (fr) | 1985-06-17 | 1986-06-17 | Additif pour huile lubrifiante et composition lubrifiante contenant ceux-ci |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0206748B1 (fr) |
| AU (1) | AU598769B2 (fr) |
| BE (1) | BE905818A (fr) |
| CA (1) | CA1273344A (fr) |
| NL (1) | NL8603048A (fr) |
| SE (1) | SE463770B (fr) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0285088A2 (fr) * | 1987-03-30 | 1988-10-05 | Ethyl Corporation | Base de Mannich aux propriétés dispersantes et améliorant l'indice de viscosité, procédé pour améliorer sa stabilité au stockage, son utilisation et son application comme additif pour huiles lubrifiantes |
| EP0317354A1 (fr) * | 1987-11-20 | 1989-05-24 | Exxon Chemical Patents Inc. | Compositions lubrifiantes pour réduire la consommation de carburant |
| EP0317348A1 (fr) * | 1987-11-20 | 1989-05-24 | Exxon Chemical Patents Inc. | Compositions lubrifiantes pour moteurs à combustion interne à basse température |
| EP0277729B1 (fr) * | 1987-01-21 | 1992-03-11 | Ethyl Corporation | Compositions lubrifiantes anti-usures ayant des teneurs faibles en phosphore |
| EP0478857A1 (fr) * | 1989-07-05 | 1992-04-08 | Chevron Research And Technology Company | Additif pour huile lubrifiante, et composition d'huile lubrifiante le contenant |
| EP1391500A1 (fr) * | 2002-08-21 | 2004-02-25 | Ethyl Corporation | Lubrifiants pour moteurs Diesel |
| US8791055B2 (en) | 2007-09-26 | 2014-07-29 | The Lubrizol Corporation | Titanium compounds and complexes as additives in lubricants |
| WO2016144639A1 (fr) * | 2015-03-10 | 2016-09-15 | The Lubrizol Corporation | Compositions lubrifiantes comprenant un agent anti-usure/modificateur de la friction |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9519668D0 (en) † | 1995-09-27 | 1995-11-29 | Exxon Chemical Patents Inc | Low chlorine low ash crankcase lubricant |
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|---|---|---|---|---|
| US3445498A (en) * | 1965-05-25 | 1969-05-20 | Universal Oil Prod Co | Boric acid esters |
| US4455243A (en) * | 1983-02-24 | 1984-06-19 | Chevron Research Company | Succinimide complexes of borated fatty acid esters of glycerol and lubricating oil compositions containing same |
| US4483775A (en) * | 1982-10-28 | 1984-11-20 | Chevron Research Company | Lubricating oil compositions containing overbased calcium sulfonates |
| US4563293A (en) * | 1981-08-03 | 1986-01-07 | Chevron Research Company | Method for improving fuel economy of internal combustion engines using borated 1,2-alkanediols |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2795548A (en) * | 1954-06-29 | 1957-06-11 | California Research Corp | Lubricant compositions |
| AU550869B2 (en) * | 1981-08-03 | 1986-04-10 | Chevron Research Company | Lubricating oil with borated long chain 1,2 alkane diol friction modifier |
| US4632771A (en) * | 1984-08-17 | 1986-12-30 | Chevron Research Company | Normally liquid C14 to C18 monoalkyl catechols |
-
1986
- 1986-06-10 CA CA000511183A patent/CA1273344A/fr not_active Expired - Fee Related
- 1986-06-17 EP EP86304680A patent/EP0206748B1/fr not_active Expired - Lifetime
- 1986-11-20 AU AU65530/86A patent/AU598769B2/en not_active Ceased
- 1986-11-26 SE SE8605064A patent/SE463770B/sv not_active IP Right Cessation
- 1986-11-27 BE BE0/217458A patent/BE905818A/fr not_active IP Right Cessation
- 1986-11-28 NL NL8603048A patent/NL8603048A/nl not_active Application Discontinuation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3445498A (en) * | 1965-05-25 | 1969-05-20 | Universal Oil Prod Co | Boric acid esters |
| US4563293A (en) * | 1981-08-03 | 1986-01-07 | Chevron Research Company | Method for improving fuel economy of internal combustion engines using borated 1,2-alkanediols |
| US4483775A (en) * | 1982-10-28 | 1984-11-20 | Chevron Research Company | Lubricating oil compositions containing overbased calcium sulfonates |
| US4455243A (en) * | 1983-02-24 | 1984-06-19 | Chevron Research Company | Succinimide complexes of borated fatty acid esters of glycerol and lubricating oil compositions containing same |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0277729B1 (fr) * | 1987-01-21 | 1992-03-11 | Ethyl Corporation | Compositions lubrifiantes anti-usures ayant des teneurs faibles en phosphore |
| EP0285088A2 (fr) * | 1987-03-30 | 1988-10-05 | Ethyl Corporation | Base de Mannich aux propriétés dispersantes et améliorant l'indice de viscosité, procédé pour améliorer sa stabilité au stockage, son utilisation et son application comme additif pour huiles lubrifiantes |
| EP0285088A3 (en) * | 1987-03-30 | 1989-01-25 | Amoco Corporation | Mannich dispersant viscosity index improver, method for improving its storage stability, its use and lubricants containing same |
| EP0317354A1 (fr) * | 1987-11-20 | 1989-05-24 | Exxon Chemical Patents Inc. | Compositions lubrifiantes pour réduire la consommation de carburant |
| EP0317348A1 (fr) * | 1987-11-20 | 1989-05-24 | Exxon Chemical Patents Inc. | Compositions lubrifiantes pour moteurs à combustion interne à basse température |
| EP0478857A1 (fr) * | 1989-07-05 | 1992-04-08 | Chevron Research And Technology Company | Additif pour huile lubrifiante, et composition d'huile lubrifiante le contenant |
| EP1391500A1 (fr) * | 2002-08-21 | 2004-02-25 | Ethyl Corporation | Lubrifiants pour moteurs Diesel |
| US6767871B2 (en) | 2002-08-21 | 2004-07-27 | Ethyl Corporation | Diesel engine lubricants |
| US8791055B2 (en) | 2007-09-26 | 2014-07-29 | The Lubrizol Corporation | Titanium compounds and complexes as additives in lubricants |
| WO2016144639A1 (fr) * | 2015-03-10 | 2016-09-15 | The Lubrizol Corporation | Compositions lubrifiantes comprenant un agent anti-usure/modificateur de la friction |
| US10501702B2 (en) | 2015-03-10 | 2019-12-10 | The Lubrizol Corporation | Lubricating compositions comprising an anti-wear/friction modifying agent |
Also Published As
| Publication number | Publication date |
|---|---|
| SE8605064L (sv) | 1988-05-27 |
| AU598769B2 (en) | 1990-07-05 |
| EP0206748A3 (en) | 1989-04-05 |
| AU6553086A (en) | 1988-05-26 |
| BE905818A (fr) | 1987-03-16 |
| SE463770B (sv) | 1991-01-21 |
| SE8605064D0 (sv) | 1986-11-26 |
| EP0206748B1 (fr) | 1992-09-02 |
| CA1273344A (fr) | 1990-08-28 |
| NL8603048A (nl) | 1988-06-16 |
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