GB1385324A - Lubricants containing dithiophosphoric acid derivatives - Google Patents

Lubricants containing dithiophosphoric acid derivatives

Info

Publication number
GB1385324A
GB1385324A GB3163471A GB3163471A GB1385324A GB 1385324 A GB1385324 A GB 1385324A GB 3163471 A GB3163471 A GB 3163471A GB 3163471 A GB3163471 A GB 3163471A GB 1385324 A GB1385324 A GB 1385324A
Authority
GB
United Kingdom
Prior art keywords
reacting
nco
diester
general formula
isocyanate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB3163471A
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.)
COOPER CO Ltd EDWIN
Edwin Cooper and Co Ltd
Original Assignee
COOPER CO Ltd EDWIN
Edwin Cooper and Co 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.)
Filing date
Publication date
Priority to BE785885D priority Critical patent/BE785885A/en
Application filed by COOPER CO Ltd EDWIN, Edwin Cooper and Co Ltd filed Critical COOPER CO Ltd EDWIN
Priority to GB3163471A priority patent/GB1385324A/en
Priority to US00269205A priority patent/US3844963A/en
Priority to IT26666/72A priority patent/IT962802B/en
Priority to BR4432/72A priority patent/BR7204432D0/en
Priority to FR7224243A priority patent/FR2144778A1/fr
Priority to AU44269/72A priority patent/AU4426972A/en
Priority to DE2233010A priority patent/DE2233010A1/en
Priority to NL7209386A priority patent/NL7209386A/xx
Priority to CA146,341A priority patent/CA990268A/en
Publication of GB1385324A publication Critical patent/GB1385324A/en
Expired legal-status Critical Current

Links

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
    • 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
    • C10M137/105—Thio derivatives not containing metal
    • 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
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
    • C07F9/165—Esters of thiophosphoric acids
    • C07F9/1654—Compounds containing the structure P(=X)n-X-acyl, P(=X)n-X-heteroatom, P(=X)n-X-CN (X = O, S, Se; n = 0, 1)
    • C07F9/1656—Compounds containing the structure P(=X)n-X-C(=X)- (X = O, S, Se; n = 0, 1)
    • 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
    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/06—Metal compounds
    • C10M2201/062—Oxides; Hydroxides; Carbonates or bicarbonates
    • C—CHEMISTRY; METALLURGY
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    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/108—Residual fractions, e.g. bright stocks
    • C—CHEMISTRY; METALLURGY
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/024—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings having at least two phenol groups but no condensed ring
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    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/027—Neutral salts thereof
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    • C10M2207/028—Overbased salts thereof
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    • C10M2207/122—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms monocarboxylic
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    • C10M2207/123—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of seven or less carbon atoms polycarboxylic
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    • C10M2207/12—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms
    • C10M2207/129—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to acyclic or cycloaliphatic carbon atoms having hydrocarbon chains of thirty or more carbon atoms
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    • C10M2207/10—Carboxylix acids; Neutral salts thereof
    • C10M2207/14—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/144—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups
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    • C10M2207/146—Carboxylix acids; Neutral salts thereof having carboxyl groups bound to carbon atoms of six-membered aromatic rings having carboxyl groups bound to carbon atoms of six-membeered aromatic rings having a hydrocarbon substituent of thirty or more carbon atoms
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    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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    • C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
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  • Organic Chemistry (AREA)
  • Crystallography & Structural 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)

Abstract

1385324 Dithiophosphate ester derivatives EDWIN COOPER & CO Ltd 4 July 1972 [6 July 1971] 31634/71 Headings C2P and C2C [Also in Division C5] A novel dithiophosphoric acid ester derivative of the general formula wherein R<SP>1</SP> and R<SP>2</SP> are the same or different and are alkyl, alkenyl, aryl, alkaryl or aralkyl groups, R<SP>4</SP> is alkyl, X is O or S, R<SP>3</SP> is a divalent aliphatic or aromatic group and n is 1 is obtained either (a) by reacting an isocyanate with a diester compound of formula or (b) by reacting a diester (R<SP>1</SP>O)(R<SP>2</SP>O)P(S)SH with one of the isocyanate groups of a diisocyanate R<SP>3</SP>(NCO) 2 and then reacting the remaining isocyanate group with an alcohol or mercaptan (R<SP>4</SP>XH). The carbon content of the various R groups is selected so as provide an oil-soluble compound. Oil-soluble compounds of the above general formula in which R<SP>3</SP> is a monovalent aliphatic or aromatic group and n is zero are also disclosed and may be obtained by reacting a diester (R<SP>1</SP>O)(R<SP>2</SP>O)P(S)SH with a monoisocyanate R<SP>3</SP>NCO. The products of Formula (I) in which n is 0 or 1 are useful as additives for lubricating oils. Isocyanates of the general formula wherein R<SP>3</SP> is a divalent aliphatic or aromatic radical and R<SP>4</SP> and X are as defined above are obtained by reacting one of the isocyanate groups of a diisocyanate R<SP>3</SP>(NCO) 2 . with an alcohol or mercaptan R<SP>4</SP>XH. In examples toluene diisocyanate is reacted with a commercial C 6 alcohol mixture, isobutanol, 3,5,5-trimethyl hexanol, tridecanol, 2.ethyl hexanol and isodecanol respectively.
GB3163471A 1971-07-06 1971-07-06 Lubricants containing dithiophosphoric acid derivatives Expired GB1385324A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
BE785885D BE785885A (en) 1971-07-06 LUBRICANT IMPROVEMENTS
GB3163471A GB1385324A (en) 1971-07-06 1971-07-06 Lubricants containing dithiophosphoric acid derivatives
FR7224243A FR2144778A1 (en) 1971-07-06 1972-07-05
IT26666/72A IT962802B (en) 1971-07-06 1972-07-05 IMPROVEMENTS RELATING TO LUBRICANTS
BR4432/72A BR7204432D0 (en) 1971-07-06 1972-07-05 A COMPOSITION AND ADDITIVE OF DITIOPHOSPHORIC ACID DERIVATIVES FOR LUBRICANTS AND PROCESS OF PREPARATION OF DERIVED DICTIONS
US00269205A US3844963A (en) 1971-07-06 1972-07-05 Lubricants
AU44269/72A AU4426972A (en) 1971-07-06 1972-07-05 Lubricants
DE2233010A DE2233010A1 (en) 1971-07-06 1972-07-05 DITHIOPHOSPHORIC ACID DERIVATIVES, PROCESS FOR THEIR PRODUCTION AND THEIR USE AS LUBRICATING OIL ADDITIVES
NL7209386A NL7209386A (en) 1971-07-06 1972-07-05
CA146,341A CA990268A (en) 1971-07-06 1972-07-05 Lubricants

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3163471A GB1385324A (en) 1971-07-06 1971-07-06 Lubricants containing dithiophosphoric acid derivatives

Publications (1)

Publication Number Publication Date
GB1385324A true GB1385324A (en) 1975-02-26

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Application Number Title Priority Date Filing Date
GB3163471A Expired GB1385324A (en) 1971-07-06 1971-07-06 Lubricants containing dithiophosphoric acid derivatives

Country Status (10)

Country Link
US (1) US3844963A (en)
AU (1) AU4426972A (en)
BE (1) BE785885A (en)
BR (1) BR7204432D0 (en)
CA (1) CA990268A (en)
DE (1) DE2233010A1 (en)
FR (1) FR2144778A1 (en)
GB (1) GB1385324A (en)
IT (1) IT962802B (en)
NL (1) NL7209386A (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5405545A (en) * 1993-03-02 1995-04-11 Mobil Oil Corporation Antiwear and antioxidant additives
US6001783A (en) * 1997-03-24 1999-12-14 The Lubrizol Corporation Mixed polysulfides and lubricants and functional fluids containing the same
US20080051307A1 (en) * 2004-07-27 2008-02-28 The Lubrizol Corporation Lubricating Compositions Containing An Ester Of A Polycarboxylic Acylating Agent
CN101466818B (en) * 2006-05-15 2013-03-27 国际壳牌研究有限公司 Lubricating oil composition

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL82724C (en) * 1951-06-19
US2743235A (en) * 1952-06-27 1956-04-24 Exxon Research Engineering Co Mineral oil composition
BE654329A (en) * 1963-10-15 1965-04-13
US3446738A (en) * 1964-02-10 1969-05-27 Sinclair Research Inc Ester base lubricant compositions containing an aromatic amine and an organic thiophosphite or thiophosphonate
US3537998A (en) * 1968-06-17 1970-11-03 Chevron Res Bis thiophosphoro carbamyl lubricating oil antioxidants

Also Published As

Publication number Publication date
CA990268A (en) 1976-06-01
IT962802B (en) 1973-12-31
NL7209386A (en) 1973-01-09
BR7204432D0 (en) 1973-05-24
DE2233010A1 (en) 1973-01-18
BE785885A (en) 1973-01-05
US3844963A (en) 1974-10-29
FR2144778A1 (en) 1973-02-16
AU4426972A (en) 1974-01-10

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PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee