CA1340717C - Dithiophosphates dihydrocarbyles - Google Patents

Dithiophosphates dihydrocarbyles

Info

Publication number: CA1340717C
Authority: CA; Canada
Prior art keywords: zinc; copper; ddp; acid; basic
Prior art date: 1987-11-24
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

CA 583912

Other languages

English (en)

Inventor

Terence Colclough

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.)

ExxonMobil Chemical Patents Inc

Original Assignee

Exxon Chemical Patents Inc

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.)

1987-11-24

Filing date

1988-11-23

Publication date

1999-08-24

1988-11-23 Application filed by Exxon Chemical Patents Inc filed Critical Exxon Chemical Patents Inc

1999-08-24 Application granted granted Critical

1999-08-24 Publication of CA1340717C publication Critical patent/CA1340717C/fr

2016-08-24 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000011701 zinc Substances 0.000 claims abstract description 76
239000010949 copper Substances 0.000 claims abstract description 38
239000000203 mixture Substances 0.000 claims abstract description 32
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 27
229910052802 copper Inorganic materials 0.000 claims abstract description 27
229910052725 zinc Inorganic materials 0.000 claims abstract description 21
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 19
239000005749 Copper compound Substances 0.000 claims abstract description 18
150000001880 copper compounds Chemical class 0.000 claims abstract description 18
BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 claims abstract description 12
150000003752 zinc compounds Chemical class 0.000 claims abstract description 11
NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 claims abstract description 10
KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 claims abstract description 7
-1 zinc carboxylate Chemical class 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 21
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 16
238000000034 method Methods 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 8
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
229940112669 cuprous oxide Drugs 0.000 claims description 6
229910052698 phosphorus Inorganic materials 0.000 claims description 6
239000011574 phosphorus Substances 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
229960004643 cupric oxide Drugs 0.000 claims description 4
239000011787 zinc oxide Substances 0.000 claims description 4
JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims description 3
125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 3
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 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000005750 Copper hydroxide Substances 0.000 claims 1
239000005751 Copper oxide Substances 0.000 claims 1
229910001956 copper hydroxide Inorganic materials 0.000 claims 1
229910000431 copper oxide Inorganic materials 0.000 claims 1
229960001296 zinc oxide Drugs 0.000 claims 1
239000010687 lubricating oil Substances 0.000 abstract description 21
239000003963 antioxidant agent Substances 0.000 abstract description 5
ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 abstract description 4
239000004246 zinc acetate Substances 0.000 abstract description 4
230000003078 antioxidant effect Effects 0.000 abstract description 2
GTSXXKUNVPDLKY-UHFFFAOYSA-N 3-ethyloctan-3-ylsulfanyl-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCCC(CC)(CC)SP(O)(O)=S GTSXXKUNVPDLKY-UHFFFAOYSA-N 0.000 abstract 1
RRXLOAUROXSDNG-UHFFFAOYSA-L zinc;3-ethyloctan-3-ylsulfanyl-dioxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CCCCCC(CC)(CC)SP([O-])([O-])=S RRXLOAUROXSDNG-UHFFFAOYSA-L 0.000 abstract 1
239000000654 additive Substances 0.000 description 23
230000007797 corrosion Effects 0.000 description 18
238000005260 corrosion Methods 0.000 description 18
239000000047 product Substances 0.000 description 16
239000003921 oil Substances 0.000 description 14
239000003112 inhibitor Substances 0.000 description 13
239000002270 dispersing agent Substances 0.000 description 11
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 10
230000000996 additive effect Effects 0.000 description 9
238000007254 oxidation reaction Methods 0.000 description 9
239000012141 concentrate Substances 0.000 description 8
KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 8
229930195733 hydrocarbon Natural products 0.000 description 8
150000002430 hydrocarbons Chemical class 0.000 description 8
230000003647 oxidation Effects 0.000 description 8
238000012360 testing method Methods 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
229910052751 metal Inorganic materials 0.000 description 7
239000002184 metal Substances 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
239000004034 viscosity adjusting agent Substances 0.000 description 7
239000002199 base oil Substances 0.000 description 6
229920001577 copolymer Polymers 0.000 description 6
HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 6
229910019142 PO4 Inorganic materials 0.000 description 5
239000003599 detergent Substances 0.000 description 5
239000003607 modifier Substances 0.000 description 5
235000021317 phosphate Nutrition 0.000 description 5
150000003013 phosphoric acid derivatives Chemical class 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000004215 Carbon black (E152) Substances 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000012530 fluid Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000002480 mineral oil Substances 0.000 description 4
235000010446 mineral oil Nutrition 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
229960002317 succinimide Drugs 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
229920002367 Polyisobutene Polymers 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
150000007942 carboxylates Chemical class 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000012263 liquid product Substances 0.000 description 3
239000000314 lubricant Substances 0.000 description 3
150000002989 phenols Chemical class 0.000 description 3
239000000376 reactant Substances 0.000 description 3
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000002877 alkyl aryl group Chemical group 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
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 2
150000001735 carboxylic acids Chemical class 0.000 description 2
150000001991 dicarboxylic acids Chemical class 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
125000004119 disulfanediyl group Chemical group *SS* 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
230000000630 rising effect Effects 0.000 description 2
229920002545 silicone oil Polymers 0.000 description 2
239000010802 sludge Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
235000011044 succinic acid Nutrition 0.000 description 2
150000003444 succinic acids Chemical class 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
YGMLOGWOEDZXIJ-UHFFFAOYSA-N 2-ethylhexylsulfanyl-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCC(CC)CSP(O)(O)=S YGMLOGWOEDZXIJ-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
CDVAIHNNWWJFJW-UHFFFAOYSA-N 3,5-diethoxycarbonyl-1,4-dihydrocollidine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C CDVAIHNNWWJFJW-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
125000006539 C12 alkyl 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
GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
239000005083 Zinc sulfide Substances 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000003254 anti-foaming effect Effects 0.000 description 1
239000007866 anti-wear additive Substances 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
229940067597 azelate Drugs 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
150000001565 benzotriazoles Chemical class 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
OSMZVRQRVPLKTN-UHFFFAOYSA-N calcium;1-nonyl-7-thiabicyclo[4.1.0]hepta-2,4-dien-6-ol Chemical compound [Ca].C1=CC=CC2(CCCCCCCCC)C1(O)S2 OSMZVRQRVPLKTN-UHFFFAOYSA-N 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003518 caustics Substances 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000008021 deposition Effects 0.000 description 1
238000000151 deposition Methods 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
239000004205 dimethyl polysiloxane Substances 0.000 description 1
235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
239000010696 ester oil Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000005189 flocculation Methods 0.000 description 1
230000016615 flocculation Effects 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
150000002314 glycerols Chemical class 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
239000003879 lubricant additive Substances 0.000 description 1
230000001050 lubricating effect Effects 0.000 description 1
238000005461 lubrication Methods 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000012528 membrane Substances 0.000 description 1
239000010688 mineral lubricating oil Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000002751 molybdenum Chemical class 0.000 description 1
PTRSTXBRQVXIEW-UHFFFAOYSA-N n,n-dioctylaniline Chemical compound CCCCCCCCN(CCCCCCCC)C1=CC=CC=C1 PTRSTXBRQVXIEW-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003136 n-heptyl 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])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000005609 naphthenate group Chemical group 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
FATBGEAMYMYZAF-UHFFFAOYSA-N oleicacidamide-heptaglycolether Natural products CCCCCCCCC=CCCCCCCCC(N)=O FATBGEAMYMYZAF-UHFFFAOYSA-N 0.000 description 1
238000002103 osmometry Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
229920013639 polyalphaolefin Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 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
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
238000004062 sedimentation Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
238000013112 stability test Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000010689 synthetic lubricating oil Substances 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
150000004867 thiadiazoles Chemical class 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
229910021511 zinc hydroxide Inorganic materials 0.000 description 1
229940007718 zinc hydroxide Drugs 0.000 description 1
LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
229910000165 zinc phosphate Inorganic materials 0.000 description 1
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1

Landscapes

Lubricants (AREA)

CA 583912 1987-11-24 1988-11-23 Dithiophosphates dihydrocarbyles Expired - Fee Related CA1340717C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB878727500A GB8727500D0 (en)	1987-11-24	1987-11-24	Dihydrocarbyl dithiophosphates
GB87-27500		1987-11-24

Publications (1)

Publication Number	Publication Date
CA1340717C true CA1340717C (fr)	1999-08-24

Family

ID=10627458

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 583912 Expired - Fee Related CA1340717C (fr)	1987-11-24	1988-11-23	Dithiophosphates dihydrocarbyles

Country Status (5)

Country	Link
AR (1)	AR247399A1 (fr)
BR (1)	BR8806156A (fr)
CA (1)	CA1340717C (fr)
GB (1)	GB8727500D0 (fr)
SG (1)	SG49919A1 (fr)

1987
- 1987-11-24 GB GB878727500A patent/GB8727500D0/en active Pending
1988
- 1988-11-18 SG SG1996009185A patent/SG49919A1/en unknown
- 1988-11-23 BR BR888806156A patent/BR8806156A/pt not_active Application Discontinuation
- 1988-11-23 CA CA 583912 patent/CA1340717C/fr not_active Expired - Fee Related
- 1988-11-24 AR AR31255688A patent/AR247399A1/es active

Also Published As

Publication number	Publication date
BR8806156A (pt)	1989-08-15
AR247399A1 (es)	1994-12-29
SG49919A1 (en)	1998-06-15
GB8727500D0 (en)	1987-12-23

Legal Events

Date	Code	Title	Description
2002-08-26	MKLA	Lapsed

Publication	Publication Date	Title
US5110488A (en)	1992-05-05	Lubricating compositions containing reduced levels of phosphorus
AU597875B2 (en)	1990-06-14	Sulfurized compositions and lubricants containing them
EP0217591B1 (fr)	1989-11-23	Catéchols monoalcoylés en C18 à C24 normalement liquides
EP0336664A2 (fr)	1989-10-11	Additifs dispersants dérivés d'adducts amidoamines
EP0389237B1 (fr)	1993-05-05	Agent modifiant la friction
US4032461A (en)	1977-06-28	Phosphorus and sulfur containing amides and thioamides as lubricating oil additives and lubricating oil compositions containing same
US4629578A (en)	1986-12-16	Succinimide complexes of borated alkyl catechols and lubricating oil compositions containing same
US3359203A (en)	1967-12-19	Ashless dithiophosphoric acid derivatives
JP2552092B2 (ja)	1996-11-06	燐含有金属塩／オレフィン組成物と活性硫黄との反応生成物
GB2163162A (en)	1986-02-19	Normally liquid c14 to c18 monoalkyl catechols
EP0330523A2 (fr)	1989-08-30	Concentrats huileux de stabilité modifiée et ayant des caractéristiques de friction modifiée
US4208357A (en)	1980-06-17	Process for preparing phosphorus and sulfur containing amides and thioamides
EP0318218B1 (fr)	1996-07-17	Dithiophosphates de dihydrocarbyle
CA1338875C (fr)	1997-01-28	Complexes de diethylamine et de catechols alkyliques borates; compositions d'huiles lubrifiantes a base de ces complexes
US4629577A (en)	1986-12-16	Method for improving fuel economy of internal combustion engines
US4255589A (en)	1981-03-10	Process for the production of oil-soluble polyol esters of dicarboxylic acid materials in the presence of a metal salt of a hydroxy aromatic compound
US4153562A (en)	1979-05-08	Antioxidants for low ash and medium ash lubricating oils
EP0051998B1 (fr)	1985-04-10	Composition d'huile lubrifiante
US5013465A (en)	1991-05-07	Dithiophosphates
CA1273344A (fr)	1990-08-28	Complexes de type succinimide d'alkylcatechols borates et produits lubrifiants contenant ceux-ci
EP0456925A1 (fr)	1991-11-21	Compositions antioxydantes
EP0039998B1 (fr)	1984-04-18	Composition d'huile lubrifiante contenant un additif capable de réduire la formation de dépôts
US4436640A (en)	1984-03-13	Glycolate dithiophosphoric acids, metal salts thereof and oil compositions containing the salts
US4617134A (en)	1986-10-14	Method and lubricant composition for providing improved friction reduction
EP0275658B1 (fr)	1991-06-12	Compositions lubrifiantes de grande puissance