CA1042454A - Lubricant additives, their preparation and compositions containing them - Google Patents

Lubricant additives, their preparation and compositions containing them

Info

Publication number: CA1042454A
Authority: CA; Canada
Prior art keywords: group; amide; phenol; substituted; alkyl
Prior art date: 1973-04-19
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

Application number

CA198,657A

Other languages

English (en)

French (fr)

Other versions

CA198657S (en

Inventor

John S. Elliott

Bryan T. Davis

Richard M. Howlett

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.)

ETHYL COOPER Ltd

Original Assignee

ETHYL COOPER Ltd

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.)

1973-04-19

Filing date

1974-05-01

Publication date

1978-11-14

1974-05-01 Application filed by ETHYL COOPER Ltd filed Critical ETHYL COOPER Ltd

1978-11-14 Application granted granted Critical

1978-11-14 Publication of CA1042454A publication Critical patent/CA1042454A/en

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 39
238000002360 preparation method Methods 0.000 title description 9
239000003879 lubricant additive Substances 0.000 title description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 38
150000001408 amides Chemical class 0.000 claims abstract description 25
150000001875 compounds Chemical class 0.000 claims abstract description 24
229920000768 polyamine Polymers 0.000 claims abstract description 18
150000001735 carboxylic acids Chemical class 0.000 claims abstract description 16
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
230000001050 lubricating effect Effects 0.000 claims abstract description 7
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
239000000047 product Substances 0.000 claims description 42
239000000654 additive Substances 0.000 claims description 24
150000001412 amines Chemical class 0.000 claims description 23
238000000034 method Methods 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 19
-1 polyethylene Polymers 0.000 claims description 19
230000000996 additive effect Effects 0.000 claims description 18
229910052757 nitrogen Inorganic materials 0.000 claims description 17
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 16
229920002367 Polyisobutene Polymers 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
239000000376 reactant Substances 0.000 claims description 11
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 10
239000007858 starting material Substances 0.000 claims description 9
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 8
239000007859 condensation product Substances 0.000 claims description 8
125000002877 alkyl aryl group Chemical group 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 7
239000000314 lubricant Substances 0.000 claims description 7
125000002947 alkylene group Chemical group 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
239000010687 lubricating oil Substances 0.000 claims description 6
125000003368 amide group Chemical group 0.000 claims description 5
KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims description 4
239000012141 concentrate Substances 0.000 claims description 4
125000004185 ester group Chemical group 0.000 claims description 4
229940107700 pyruvic acid Drugs 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical class OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
239000004698 Polyethylene Substances 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
229920000573 polyethylene Polymers 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims 3
239000001257 hydrogen Substances 0.000 claims 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
150000003948 formamides Chemical group 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 abstract description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
238000012360 testing method Methods 0.000 description 24
239000000243 solution Substances 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 17
239000003921 oil Substances 0.000 description 15
239000003208 petroleum Substances 0.000 description 14
239000002480 mineral oil Substances 0.000 description 13
235000010446 mineral oil Nutrition 0.000 description 12
238000010992 reflux Methods 0.000 description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
229910052799 carbon Inorganic materials 0.000 description 11
239000002904 solvent Substances 0.000 description 10
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
239000002270 dispersing agent Substances 0.000 description 8
239000008096 xylene Substances 0.000 description 8
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
235000019647 acidic taste Nutrition 0.000 description 5
MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
238000007429 general method Methods 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
239000002966 varnish Substances 0.000 description 4
RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
235000008504 concentrate Nutrition 0.000 description 3
150000003949 imides Chemical class 0.000 description 3
229960001124 trientine Drugs 0.000 description 3
XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
229910015900 BF3 Inorganic materials 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
239000004743 Polypropylene Substances 0.000 description 2
239000005864 Sulphur Substances 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
239000007866 anti-wear additive Substances 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
230000003078 antioxidant effect Effects 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 2
239000003599 detergent Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
UPCIBFUJJLCOQG-UHFFFAOYSA-L ethyl-[2-[2-[ethyl(dimethyl)azaniumyl]ethyl-methylamino]ethyl]-dimethylazanium;dibromide Chemical compound [Br-].[Br-].CC[N+](C)(C)CCN(C)CC[N+](C)(C)CC UPCIBFUJJLCOQG-UHFFFAOYSA-L 0.000 description 2
235000010299 hexamethylene tetramine Nutrition 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
238000002955 isolation Methods 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
150000004682 monohydrates Chemical class 0.000 description 2
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 2
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
239000002245 particle Substances 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
229920013639 polyalphaolefin Polymers 0.000 description 2
229920001155 polypropylene Polymers 0.000 description 2
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
239000010802 sludge Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
MVMRYSSNWDNQEZ-UHFFFAOYSA-N 1,1-diethyl-2-pentylhydrazine Chemical compound CCCCCNN(CC)CC MVMRYSSNWDNQEZ-UHFFFAOYSA-N 0.000 description 1
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
YAXXOCZAXKLLCV-UHFFFAOYSA-N 3-dodecyloxolane-2,5-dione Chemical class CCCCCCCCCCCCC1CC(=O)OC1=O YAXXOCZAXKLLCV-UHFFFAOYSA-N 0.000 description 1
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
101000721172 Homo sapiens Protein DBF4 homolog A Proteins 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
241001024304 Mino Species 0.000 description 1
102100025198 Protein DBF4 homolog A Human genes 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000011149 active material Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
230000009435 amidation Effects 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000003749 cleanliness Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
230000000332 continued effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000001351 cycling effect Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000002950 deficient Effects 0.000 description 1
230000008021 deposition Effects 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
239000010696 ester oil Substances 0.000 description 1
239000000446 fuel Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
235000011167 hydrochloric acid Nutrition 0.000 description 1
229960000443 hydrochloric acid Drugs 0.000 description 1
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
210000005053 lamin Anatomy 0.000 description 1
229940040102 levulinic acid Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
GZUCMODGDIGMBI-UHFFFAOYSA-N n',n'-dipropylpropane-1,3-diamine Chemical compound CCCN(CCC)CCCN GZUCMODGDIGMBI-UHFFFAOYSA-N 0.000 description 1
UVSDKMISWYGPIQ-UHFFFAOYSA-N n'-butyl-n-propylethane-1,2-diamine Chemical compound CCCCNCCNCCC UVSDKMISWYGPIQ-UHFFFAOYSA-N 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
229920001281 polyalkylene Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
230000036647 reaction Effects 0.000 description 1
229940116351 sebacate Drugs 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 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
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
- 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
- C10M2207/34—Esters having a hydrocarbon substituent of thirty or more carbon atoms, e.g. substituted succinic acid derivatives
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
- C10M2215/082—Amides [having hydrocarbon substituents containing less than thirty carbon atoms] containing hydroxyl groups; Alkoxylated derivatives
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- C10M2215/086—Imides [having hydrocarbon substituents containing less than thirty carbon atoms]
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- C10M2215/26—Amines
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- C10M2217/042—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds between the nitrogen-containing monomer and an aldehyde or ketone
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- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/043—Mannich bases
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- C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
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- 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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- C10M2219/044—Sulfonic acids, Derivatives thereof, e.g. neutral salts
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- C10M2219/085—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing carboxyl groups; Derivatives thereof
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- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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- C10M2219/088—Neutral salts
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2070/00—Specific manufacturing methods for lubricant compositions
- C10N2070/02—Concentrating of additives

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Lubricants (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA198,657A 1973-04-19 1974-05-01 Lubricant additives, their preparation and compositions containing them Expired CA1042454A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB1917373A GB1459403A (en)	1973-04-19	1973-04-19	Lubricant additives their preparation and compositions containing them

Publications (1)

Publication Number	Publication Date
CA1042454A true CA1042454A (en)	1978-11-14

Family

ID=10124960

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA198,657A Expired CA1042454A (en)	1973-04-19	1974-05-01	Lubricant additives, their preparation and compositions containing them

Country Status (14)

Country	Link
JP (1)	JPS5918402B2 (de)
AR (1)	AR205535A1 (de)
AT (1)	AT346309B (de)
BE (1)	BE813916A (de)
BR (1)	BR7403100D0 (de)
CA (1)	CA1042454A (de)
CH (1)	CH605683A5 (de)
DE (1)	DE2418760A1 (de)
FR (1)	FR2226416B1 (de)
GB (1)	GB1459403A (de)
IT (1)	IT1012586B (de)
NL (1)	NL7405266A (de)
SE (1)	SE7405242L (de)
ZA (1)	ZA742476B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE102004005108A1 (de)	2004-02-02	2005-10-27	Basf Ag	Verfahren zur Herstellung von Polyisobutenylphenolen

1973
- 1973-04-19 GB GB1917373A patent/GB1459403A/en not_active Expired
1974
- 1974-01-01 AR AR253344A patent/AR205535A1/es active
- 1974-04-18 IT IT21642/74A patent/IT1012586B/it active
- 1974-04-18 NL NL7405266A patent/NL7405266A/xx not_active Application Discontinuation
- 1974-04-18 BR BR3100/74A patent/BR7403100D0/pt unknown
- 1974-04-18 DE DE2418760A patent/DE2418760A1/de not_active Ceased
- 1974-04-18 AT AT320274A patent/AT346309B/de not_active IP Right Cessation
- 1974-04-18 ZA ZA00742476A patent/ZA742476B/xx unknown
- 1974-04-18 SE SE7405242D patent/SE7405242L/sv unknown
- 1974-04-18 FR FR7413462A patent/FR2226416B1/fr not_active Expired
- 1974-04-18 BE BE143378A patent/BE813916A/xx not_active IP Right Cessation
- 1974-04-18 JP JP49044348A patent/JPS5918402B2/ja not_active Expired
- 1974-04-19 CH CH544574A patent/CH605683A5/xx not_active IP Right Cessation
- 1974-05-01 CA CA198,657A patent/CA1042454A/en not_active Expired

Also Published As

Publication number	Publication date
IT1012586B (it)	1977-03-10
DE2418760A1 (de)	1974-11-07
ZA742476B (en)	1975-12-31
AT346309B (de)	1978-11-10
JPS5918402B2 (ja)	1984-04-27
FR2226416B1 (de)	1978-10-27
AU6805674A (en)	1975-10-23
NL7405266A (de)	1974-10-22
BE813916A (fr)	1974-08-16
SE7405242L (de)	1974-10-21
AR205535A1 (es)	1976-05-14
JPS5030905A (de)	1975-03-27
ATA320274A (de)	1978-03-15
BR7403100D0 (pt)	1974-11-19
CH605683A5 (de)	1978-10-13
FR2226416A1 (de)	1974-11-15
GB1459403A (en)	1976-12-22

Publication	Publication Date	Title
US4617137A (en)	1986-10-14	Glycidol modified succinimides
US4645515A (en)	1987-02-24	Modified succinimides (II)
US4670170A (en)	1987-06-02	Modified succinimides (VIII)
US4617138A (en)	1986-10-14	Modified succinimides (II)
US4614603A (en)	1986-09-30	Modified succinimides (III)
US4666459A (en)	1987-05-19	Modified succinimides (VII)
US4113639A (en)	1978-09-12	Lubricating oil composition containing a dispersing-varnish inhibiting combination of an oxazoline compound and an acyl nitrogen compound
US4668246A (en)	1987-05-26	Modified succinimides (IV)
US4666460A (en)	1987-05-19	Modified succinimides (III)
US4173540A (en)	1979-11-06	Lubricating oil composition containing a dispersing-varnish inhibiting combination of polyol ester compound and a borated acyl nitrogen compound
US5670462A (en)	1997-09-23	Lubricating oil additives
US4051049A (en)	1977-09-27	Lubricating oil containing alkanoic amide or ester-bridged hydrocarbyl substituted phenols
US4071548A (en)	1978-01-31	Lubricating oil additive, process for the synthesis thereof and lubricating oil additive composition
US4242212A (en)	1980-12-30	Mannich additives modified by ditertiary alkyl phenol
JP3806950B2 (ja)	2006-08-09	潤滑添加剤組成物
US4083791A (en)	1978-04-11	Lubricating oil containing reaction products of polyisobutylphenol, esters of chloroacetic acid, and ethylene polyamine
EP0090629B1 (de)	1987-09-16	Borierter Zusatz für Schmieröl
US5069684A (en)	1991-12-03	Fuel and lube additives from polyether derivatives of polyamine alkenyl succinimides
US4927562A (en)	1990-05-22	Elastomer-compatible oxalic acid acylated alkenylsuccinimides
US4631070A (en)	1986-12-23	Glycidol modified succinimides and fuel compositions containing the same
CA1042454A (en)	1978-11-14	Lubricant additives, their preparation and compositions containing them
US4661274A (en)	1987-04-28	Additive for lubricants and hydrocarbon fuels comprising reaction products of olefins, sulfur, hydrogen sulfide and nitrogen containing polymeric compounds
US5846917A (en)	1998-12-08	Phenolic imidazoline antioxidants
US4031015A (en)	1977-06-21	Nitrile-amine reaction products
US3833618A (en)	1974-09-03	4-(high molecular weight alkyl-substituted carbophenoxy)phthalic anhydride and analogous diacid