US3654329A - Zinc dithiophosphates - Google Patents

Zinc dithiophosphates Download PDF

Info

Publication number: US3654329A
Authority: US; United States
Prior art keywords: zinc; dithiophosphate; butyl; tert; additives
Prior art date: 1967-12-06
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 - Lifetime

Application number

US780906A

Other languages

English (en)

Inventor

Luigi Imparato

Enzo Rossi

San Donato Milanese

Sergio Del Ross

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.)

SnamProgetti SpA

Original Assignee

SnamProgetti SpA

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.)

1967-12-06

Filing date

1968-12-03

Publication date

1972-04-04

1968-12-03 Application filed by SnamProgetti SpA filed Critical SnamProgetti SpA

1972-04-04 Application granted granted Critical

1972-04-04 Publication of US3654329A publication Critical patent/US3654329A/en

1989-04-04 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical class [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 title description 12
239000011701 zinc Chemical group 0.000 abstract description 17
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract description 8
239000004215 Carbon black (E152) Substances 0.000 abstract description 7
229930195733 hydrocarbon Natural products 0.000 abstract description 7
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract description 6
229910052725 zinc Chemical group 0.000 abstract description 6
-1 HYDROXY GROUP Chemical group 0.000 abstract description 5
239000003963 antioxidant agent Substances 0.000 abstract description 5
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract description 4
229910052788 barium Inorganic materials 0.000 abstract description 4
229910052793 cadmium Inorganic materials 0.000 abstract description 4
229910052791 calcium Inorganic materials 0.000 abstract description 4
239000011575 calcium Substances 0.000 abstract description 4
229910052759 nickel Inorganic materials 0.000 abstract description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
235000006708 antioxidants Nutrition 0.000 abstract description 2
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical group [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract description 2
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical group [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 abstract description 2
229910052739 hydrogen Inorganic materials 0.000 abstract description 2
239000001257 hydrogen Substances 0.000 abstract description 2
239000000654 additive Substances 0.000 description 17
239000000047 product Substances 0.000 description 11
150000001875 compounds Chemical class 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
230000003647 oxidation Effects 0.000 description 7
238000007254 oxidation reaction Methods 0.000 description 7
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
239000003921 oil Substances 0.000 description 6
230000000996 additive effect Effects 0.000 description 5
238000006386 neutralization reaction Methods 0.000 description 5
239000000314 lubricant Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
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 3
150000002989 phenols Chemical class 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000011787 zinc oxide Substances 0.000 description 3
125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 2
125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
230000003078 antioxidant effect Effects 0.000 description 2
XDFCIPNJCBUZJN-UHFFFAOYSA-N barium(2+) Chemical compound [Ba+2] XDFCIPNJCBUZJN-UHFFFAOYSA-N 0.000 description 2
RDVQTQJAUFDLFA-UHFFFAOYSA-N cadmium Chemical compound [Cd][Cd][Cd][Cd][Cd][Cd][Cd][Cd][Cd] RDVQTQJAUFDLFA-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
229910052745 lead Inorganic materials 0.000 description 2
WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 description 2
239000010687 lubricating oil Substances 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000007787 solid Substances 0.000 description 2
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-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
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
241001558496 Talpa caeca Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000002199 base oil Substances 0.000 description 1
238000009835 boiling Methods 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
239000003054 catalyst Substances 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
125000006289 hydroxybenzyl group Chemical group 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
238000000034 method Methods 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
125000000101 thioether group Chemical group 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio 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
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/02—Groups 1 or 11
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/08—Groups 4 or 14
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/10—Groups 5 or 15
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/14—Group 7
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/16—Groups 8, 9, or 10

Definitions

R0 OR" RO OR wherein M is calcium, barium, nickel, cadmium, lead or zinc and R, R, R" and R are substituted or unsubstituted hydrocarbon radicals, at least one having the formula:
A is a bivalent hydrocarbon radical and n is zero or a whole number from 1 to 20 and at least one of said R R R R and R groups is a hydroxy group sterically hindered by another of said groups which is an alkyl group.
the remaining groups are hydrogen or alkyl.
This invention relates to novel compounds which are suitable as anti-oxidant additives for lubricants, and to lubricants containing these compounds.
zinc dialkyldithiophosphates are used as additives for lubricating oils on account of the fact that these compounds impart to the lubricants to which they are added a strong resistance against oxidation, as well as anti wear and anti-corrosion properties.
an anti-oxidant additive for a lubricating oil a compound represented by the following general formula:
RIO OR!!! wherein M is a calcium, barium, nickel, cadmium, lead or zinc atom, and R, R, R" and R' are substituted or unsubstituted hydrocarbon radicals, at least one of R, R, R, R
A is non-existent or is a bivalent hydrocarbon radical containing from 1 to carbon atoms and optionally containing an ether, ester or thioether group, at least one of the radicals R R R R and R isa hydroxyl group,
At least one other of the radicals R R R R and R is an alkyl group which sterically hinders the said hydroxyl group, and each of the remainder of the radicals R R R R and R is a primary, secondary or tertiary alkyl group or a hydrogen atom.
A is a bivalent hydrocarbon radical containing from 2 to 10 carbon atoms.
the alkyl radical which sterically hinders the hydroxyl group is a secondary or tertiary alkyl group.
alkyl radicals having a steric hindrance on the hydroxyl, which are in a vicinal position with respect to the hydroxyl.
suitable radicals for this purpose include t.-butyl, dirnethyl-ethyl-methyl, methyldiethylmethyl, triethylmethyl, isopropyl and sbutyl.
the products of this invention possess approximately the anti wear and anti-corrosion properties found in the zinc dithiophosphates obtained from n-alcohols.
the metal dithiophosphates of the invention may be obtained by reacting P 5 and the appropriate alcohol or alcohols in the approximate molar ratio of 1:4, at an elevated temperature, generally at a temperature of from 50 C. to 200 C., preferably from C. to 120 C., and then neutralizing the resulting dithiophosphate acid with a metallic oxide, for example zinc oxide.
the infrared spectrographic analysis of the product confirmed the presence of a dithiophosphate group.
the comparative additives were selected 8'82 32 gg from zinc dithiophosphates obtained from aliphatic 0:03 2: Do: alcohols and mixtures thereof with 2,6-di-tert.butyl-para- 8'83 i h g' cresol in equimolar concentrations based on the additives 0:03 2:95 Slight. of the invention.
the zinc dithiophosphates of the invention have a high anti-oxidant activity, and the synergism existing between the dialkyl zinc dithiophosphates and sterically hindered phenols, increases when the sterically hindered phenol forms part of the dithiophosphate molecule.
A is the additive of the Example 1
B the additive of the Example 2
C the additive of the EX- ample 3
D the additive of the EX- ample 3
D the additive of the EX- ample 3
E and F are different known commercial additives based on Zinc dithiophosphates. The tests were carried out with a Shell 4 ball Wear Tester, each test lasting 60 seconds at a speed of 1200 r.p.m.
the additives of the invention generally have a better anti-rust characteristic than known additives.
M is a calcium, barium, nickel, cadmium, lead or zinc atom; and R, R, R" and R' are alkyl radicals containing up to 10 carbons, at least one of R, R, R" and R having the formula:
a compound as claimed in claim 1 wherein said hydroxy group is sterically hindered by vicinally positioned secondary or tertiary alkyl groups.
a compound as claimed in claim 1 wherein said hydroxy group is in the para position sterically hindered by vicinally positioned tertiary butyl groups.
a compound as claimed in claim 1 having the name bis[( 3,5 di-tert.butyl-4-hydroxy-benzy1)propyl] zinc dithiophosphate.
a compound as claimed in claim 1 having the name (4 methyl -2- pentyl) [(3,S-di-tert.butyl-4-hydroxy-benzyl)-propyl] zinc dithiophosphate.
a compound as claimed in claim 1 having the name cetyl[(3,5 di tert.buty1-4-hydroxy-benzyl)-propyl] zinc dithiophosphate.

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Lubricants (AREA)

US780906A 1967-12-06 1968-12-03 Zinc dithiophosphates Expired - Lifetime US3654329A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT2358267		1967-12-06

Publications (1)

Publication Number	Publication Date
US3654329A true US3654329A (en)	1972-04-04

Family

ID=11208305

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
US780906A Expired - Lifetime US3654329A (en)	1967-12-06	1968-12-03	Zinc dithiophosphates

Country Status (7)

Country	Link
US (1)	US3654329A (de)
AT (1)	AT291291B (de)
BE (1)	BE724936A (de)
CH (1)	CH505886A (de)
FR (1)	FR1594153A (de)
GB (1)	GB1204798A (de)
NL (1)	NL6817504A (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2636583A1 (de) *	1975-08-15	1977-02-24	Mobil Oil Corp	Schmiermittelzusammensetzung
US4226733A (en) *	1978-11-17	1980-10-07	Mobil Oil Corporation	Lubricant compositions stabilized against ultra-violet degradation
US5013465A (en) *	1987-12-23	1991-05-07	Exxon Chemical Patents, Inc.	Dithiophosphates
CN110563760A (zh) *	2019-10-16	2019-12-13	宜春学院	一种硫代磷酸酯类化合物的制备方法

1968
- 1968-11-04 GB GB52236/68A patent/GB1204798A/en not_active Expired
- 1968-12-03 US US780906A patent/US3654329A/en not_active Expired - Lifetime
- 1968-12-04 CH CH1814368A patent/CH505886A/fr not_active IP Right Cessation
- 1968-12-05 BE BE724936D patent/BE724936A/xx not_active IP Right Cessation
- 1968-12-06 AT AT1193768A patent/AT291291B/de not_active IP Right Cessation
- 1968-12-06 FR FR1594153D patent/FR1594153A/fr not_active Expired
- 1968-12-06 NL NL6817504A patent/NL6817504A/xx unknown

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2636583A1 (de) *	1975-08-15	1977-02-24	Mobil Oil Corp	Schmiermittelzusammensetzung
US4226733A (en) *	1978-11-17	1980-10-07	Mobil Oil Corporation	Lubricant compositions stabilized against ultra-violet degradation
US5013465A (en) *	1987-12-23	1991-05-07	Exxon Chemical Patents, Inc.	Dithiophosphates
CN110563760A (zh) *	2019-10-16	2019-12-13	宜春学院	一种硫代磷酸酯类化合物的制备方法

Also Published As

Publication number	Publication date
DE1808492A1 (de)	1969-06-19
BE724936A (de)	1969-05-16
NL6817504A (de)	1969-06-10
CH505886A (fr)	1971-04-15
FR1594153A (de)	1970-06-01
DE1808492B2 (de)	1976-12-16
AT291291B (de)	1971-07-12
GB1204798A (en)	1970-09-09

Publication	Publication Date	Title
US3654155A (en)	1972-04-04	Esters of phosphorodithioates
US2443264A (en)	1948-06-15	Compounded lubricating oil
US2565920A (en)	1951-08-28	Triesters of dithiophosphoric acid
US2736737A (en)	1956-02-28	Phosphate partial ester-aldehyde condensation product and lubricant containing the same
US2813830A (en)	1957-11-19	Hydrocarbon oil compositions
US3277133A (en)	1966-10-04	Phosphorus-, sulfur-, and metal-containing composition
US2589326A (en)	1952-03-18	Organic phosphorus ester-p2s5 reaction products and oil compositions containing the same
US3567638A (en)	1971-03-02	Novel phosphorus-containing adducts in oil compositions containing the same
US2365938A (en)	1944-12-26	Wax substituted diaryl dithiophosphoric acids and salts thereof
US2488134A (en)	1949-11-15	Sulfur-containing aromatic compounds
US2783204A (en)	1957-02-26	Corrosion preventing agent
US2619508A (en)	1952-11-25	Polyether-alcohols containing thioether side chains
US3089850A (en)	1963-05-14	Phosphorothiolothionates derived from glycols
GB1583690A (en)	1981-01-28	Thio-compounds derivable from epichlorohydrin and their use as lubricant additives
US4113634A (en)	1978-09-12	Metal aryl dithiophosphates and their manufacture
US2596141A (en)	1952-05-13	Monoalkyl diphenyl phosphate esters
US2472517A (en)	1949-06-07	Addition agents for mineral oil lubricants
DE3854250T2 (de)	1996-01-11	Schmieröl-Zusätze enthaltend Borat-Abkömmlinge gemischter Nichtaryldiolphosphorodithioate.
US2713557A (en)	1955-07-19	Basic phenates to inhibit silver corrosion in thiophosphate-containing lubricating oils
US3595792A (en)	1971-07-27	Lubricating oil additives
US3929653A (en)	1975-12-30	Lubricant additives
US2763616A (en)	1956-09-18	Alkylthiohydroquinones-formaldehyde-amine reaction products and petroleum fractions, containing the same
US2506570A (en)	1950-05-09	Lubricating oil compositions
US3637587A (en)	1972-01-25	Stabilization of organic substance with n n-disubstituted-aminoalkyl phosphite
US3291817A (en)	1966-12-13	Polymer coordinated metal compounds

US3654329A - Zinc dithiophosphates - Google Patents

Info

Links

Classifications

Definitions

Landscapes

Applications Claiming Priority (1)

Publications (1)

Family

ID=11208305

Family Applications (1)

Country Status (7)

Cited By (4)

Cited By (4)

Also Published As

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