CA1273344A - Succinimide complexes of borated alkyl catechols and lubricating oil compositions containing same - Google Patents

Succinimide complexes of borated alkyl catechols and lubricating oil compositions containing same

Info

Publication number: CA1273344A
Authority: CA; Canada
Prior art keywords: alkyl; succinimide; borated; catechol; lubricating oil
Prior art date: 1985-06-17
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.): Expired - Fee Related

Application number

CA000511183A

Other languages

English (en)

French (fr)

Inventor

Thomas V. Liston

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Chevron USA Inc

Original Assignee

Chevron Research and Technology Co

Priority date (The priority date 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 date listed.)

1985-06-17

Filing date

1986-06-10

Publication date

1990-08-28

1985-06-17 Priority claimed from US06/745,661 external-priority patent/US4629577A/en

1985-06-17 Priority claimed from US06/745,565 external-priority patent/US4629578A/en

1986-06-10 Application filed by Chevron Research and Technology Co filed Critical Chevron Research and Technology Co

1986-11-26 Priority claimed from BR8605801A external-priority patent/BR8605801A/pt

1990-08-28 Application granted granted Critical

1990-08-28 Publication of CA1273344A publication Critical patent/CA1273344A/en

2007-08-28 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

-1 alkyl catechols Chemical class 0.000 title claims abstract description 126
239000000203 mixture Substances 0.000 title claims abstract description 91
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 title claims abstract description 85
239000010687 lubricating oil Substances 0.000 title claims abstract description 54
YCIMNLLNPGFGHC-UHFFFAOYSA-N o-dihydroxy-benzene Natural products OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims abstract description 84
229960002317 succinimide Drugs 0.000 claims abstract description 57
239000003921 oil Substances 0.000 claims abstract description 43
125000000217 alkyl group Chemical group 0.000 claims abstract description 38
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 26
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 18
239000000446 fuel Substances 0.000 claims abstract description 16
238000002485 combustion reaction Methods 0.000 claims abstract description 14
125000002947 alkylene group Chemical group 0.000 claims abstract description 5
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 37
150000003839 salts Chemical class 0.000 claims description 18
230000007935 neutral effect Effects 0.000 claims description 13
150000001342 alkaline earth metals Chemical class 0.000 claims description 12
230000001050 lubricating effect Effects 0.000 claims description 12
229920000768 polyamine Polymers 0.000 claims description 12
230000007062 hydrolysis Effects 0.000 claims description 11
238000006460 hydrolysis reaction Methods 0.000 claims description 11
238000000034 method Methods 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
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
229920001281 polyalkylene Polymers 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 7
238000009472 formulation Methods 0.000 claims description 6
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 5
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
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
229960001124 trientine Drugs 0.000 claims 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 abstract description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
229910052739 hydrogen Inorganic materials 0.000 abstract description 3
239000001257 hydrogen Substances 0.000 abstract description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 15
150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 10
150000001336 alkenes Chemical class 0.000 description 10
239000004711 α-olefin Substances 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 9
229940014800 succinic anhydride Drugs 0.000 description 9
150000003871 sulfonates Chemical class 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
239000000654 additive Substances 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
239000011541 reaction mixture Substances 0.000 description 7
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
229920002367 Polyisobutene Polymers 0.000 description 6
125000003277 amino group Chemical group 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
235000008504 concentrate Nutrition 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
239000002199 base oil Substances 0.000 description 5
238000005260 corrosion Methods 0.000 description 5
230000006872 improvement Effects 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
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
229930195733 hydrocarbon Natural products 0.000 description 4
150000002430 hydrocarbons Chemical class 0.000 description 4
239000000314 lubricant Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 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
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
150000007513 acids Chemical class 0.000 description 3
230000000996 additive effect Effects 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
230000006870 function Effects 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
235000001055 magnesium Nutrition 0.000 description 3
229940091250 magnesium supplement Drugs 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
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
239000002244 precipitate Substances 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
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
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
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
AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 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
150000003254 radicals Chemical class 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
TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-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
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
229910052770 Uranium Inorganic materials 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000002730 additional effect Effects 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
230000000536 complexating effect Effects 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
229940012017 ethylenediamine Drugs 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
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
239000003607 modifier Substances 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
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 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
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Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Chemistry (AREA)
Lubricants (AREA)

CA000511183A 1985-06-17 1986-06-10 Succinimide complexes of borated alkyl catechols and lubricating oil compositions containing same Expired - Fee Related CA1273344A (en)

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
US06/745,565 US4629578A (en)	1985-06-17	1985-06-17	Succinimide complexes of borated alkyl catechols and lubricating oil compositions containing same
US745,565		1985-06-17
US745,661		1985-06-17
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 (1)

Publication Number	Publication Date
CA1273344A true CA1273344A (en)	1990-08-28

Family

ID=27159992

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000511183A Expired - Fee Related CA1273344A (en)	1985-06-17	1986-06-10	Succinimide complexes of borated alkyl catechols and lubricating oil compositions containing same

Country Status (6)

Country	Link
EP (1)	EP0206748B1 (de)
AU (1)	AU598769B2 (de)
BE (1)	BE905818A (de)
CA (1)	CA1273344A (de)
NL (1)	NL8603048A (de)
SE (1)	SE463770B (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3868949D1 (de) *	1987-01-21	1992-04-16	Amoco Corp	Veschleissschutz-schmiermittelzusammensetzungen mit geringem phosphorgehalt.
US4808325A (en) *	1987-03-30	1989-02-28	Amoco Corporation	Mannich dispersant VI-improver blended with phenolic compound for improved storage stability
CA1337294C (en) *	1987-11-20	1995-10-10	Dale Robert Carroll	Lubricant compositions for enhanced fuel economy
CA1337293C (en) *	1987-11-20	1995-10-10	Emil Joseph Meny	Lubricant compositions for low-temperature internal combustion engines
US4975211A (en) *	1989-07-05	1990-12-04	Chevron Research Company	Diethylamine complexes of borated alkyl catechols and lubricating oil compositions containing the same
GB9519668D0 (en) †	1995-09-27	1995-11-29	Exxon Chemical Patents Inc	Low chlorine low ash crankcase lubricant
US6767871B2 (en) *	2002-08-21	2004-07-27	Ethyl Corporation	Diesel engine lubricants
CA2700650C (en)	2007-09-26	2015-06-30	The Lubrizol Corporation	Titanium compounds and complexes as additives in lubricants
EP3268454B1 (de) *	2015-03-10	2023-10-04	The Lubrizol Corporation	Schmiermittelzusammensetzungen mit anti-verschleiss-/reibungsmodifizierungsmittel

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2795548A (en) *	1954-06-29	1957-06-11	California Research Corp	Lubricant compositions
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
AU550869B2 (en) *	1981-08-03	1986-04-10	Chevron Research Company	Lubricating oil with borated long chain 1,2 alkane diol friction modifier
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
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/en not_active Expired - Fee Related
- 1986-06-17 EP EP86304680A patent/EP0206748B1/de 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

Also Published As

Publication number	Publication date
SE463770B (sv)	1991-01-21
AU6553086A (en)	1988-05-26
EP0206748A3 (en)	1989-04-05
SE8605064L (sv)	1988-05-27
SE8605064D0 (sv)	1986-11-26
BE905818A (fr)	1987-03-16
EP0206748B1 (de)	1992-09-02
EP0206748A2 (de)	1986-12-30
AU598769B2 (en)	1990-07-05
NL8603048A (nl)	1988-06-16

Legal Events

Date	Code	Title	Description
2004-08-30	MKLA	Lapsed

Publication	Publication Date	Title
US4455243A (en)	1984-06-19	Succinimide complexes of borated fatty acid esters of glycerol and lubricating oil compositions containing same
US4495088A (en)	1985-01-22	Method for improving fuel economy of internal combustion engines
CA1238345A (en)	1988-06-21	Normally liquid c in18 xx to c in24 xx monoalkyl catechols
US4394277A (en)	1983-07-19	Method for improving fuel economy of internal combustion engines using borated sulfur-containing 1,2-alkane diols
US4629578A (en)	1986-12-16	Succinimide complexes of borated alkyl catechols and lubricating oil compositions containing same
GB2103651A (en)	1983-02-23	Reduction of fuel consumption of internal combustion engines and composition therefor
EP0562062B1 (de)	1998-01-07	Abdichtungen aus fluorkohlenstoff schützende zusätze für schmieröle
US4632771A (en)	1986-12-30	Normally liquid C14 to C18 monoalkyl catechols
US4629577A (en)	1986-12-16	Method for improving fuel economy of internal combustion engines
CA1273344A (en)	1990-08-28	Succinimide complexes of borated alkyl catechols and lubricating oil compositions containing same
CA1338875C (en)	1997-01-28	Diethylamine complexes of borated alkyl catechols and lubricating oil compositions containing the same
US4394276A (en)	1983-07-19	Method for improving fuel economy of internal combustion engines using sulfur-containing alkanediols
US4153562A (en)	1979-05-08	Antioxidants for low ash and medium ash lubricating oils
CA1224470A (en)	1987-07-21	Succinimide complexes of borated fatty acid esters of glycerol and lubricating compositions containing same
US4548723A (en)	1985-10-22	Ortho-carboxy phenylphenone lubricating oil additives
US4550197A (en)	1985-10-29	Overbased ortho-carboxy phenylphenone lubricating oil additives
US5284594A (en)	1994-02-08	Dialkylamine complexes of borated alkyl catechols and lubricating oil compositions containing the same
US5160651A (en)	1992-11-03	Trialkylamine complexes of borated higher carbon number alkyl catechols and lubricating oil compositions containing the same
US5202039A (en)	1993-04-13	Trialkylamine complexes of certain borated alkyl catechols and lubricating oil compositions containing the same
US5141660A (en)	1992-08-25	Monoalkylamine complexes of borated alkyl catechols and lubricating oil compositions containing the same
JPS6236495A (ja)	1987-02-17	スクシンイミド錯体を含有する潤滑油添加剤の製造方法
WO1991004312A1 (en)	1991-04-04	Alkylamine complexes of borated alkyl catechols and lubricating oil compositions containing the same
NO170161B (no)	1992-06-09	Smoereolje inneholdende et kompleks av et succinimid og enborert alkylcatechol
JPH0260718B2 (de)	1990-12-18
JPH0251959B2 (de)	1990-11-09