US3723578A - Phosphate esters of ethers of thiol substituted phenols - Google Patents
Phosphate esters of ethers of thiol substituted phenols Download PDFInfo
- Publication number
- US3723578A US3723578A US00080477A US3723578DA US3723578A US 3723578 A US3723578 A US 3723578A US 00080477 A US00080477 A US 00080477A US 3723578D A US3723578D A US 3723578DA US 3723578 A US3723578 A US 3723578A
- Authority
- US
- United States
- Prior art keywords
- phosphate esters
- phenol
- sulfur containing
- containing phosphate
- alkylthio
- 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 - Lifetime
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- 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
- C10M137/06—Metal salts
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- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
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- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
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- 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
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- C10N2010/08—Groups 4 or 14
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- 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
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- 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
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- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
-
- C—CHEMISTRY; METALLURGY
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/044—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for manual transmissions
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/046—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for traction drives
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/22—Metal working with essential removal of material, e.g. cutting, grinding or drilling
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/24—Metal working without essential removal of material, e.g. forming, gorging, drawing, pressing, stamping, rolling or extruding; Punching metal
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/241—Manufacturing joint-less pipes
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/242—Hot working
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/243—Cold working
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/245—Soft metals, e.g. aluminum
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/246—Iron or steel
-
- 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
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/20—Metal working
- C10N2040/244—Metal working of specific metals
- C10N2040/247—Stainless steel
-
- 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
- C10N2050/00—Form in which the lubricant is applied to the material being lubricated
- C10N2050/10—Semi-solids; greasy
Definitions
- R is an alkyl group of one to 20 carbon atoms
- phenyl or aralkyl x is an integer of from 1 to 3 inclusive
- n is an integer of from 0 to 50 inclusive (preferably 1-20)
- m is an integer of l to 3 inclusive
- Y is hydrogen, methyl or ethyl
- Z is hydrogen or alkyl, of one to 20 carbons atoms
- M is a cation, e.g., H, alkali metal, alkaline earth metal, heavy metal, ammonium or amino.
- R is an alkyl group of one to 20 carbon atoms, (including alkylphenyl) of six to 18 carbon atoms or aralkyl of six to 18 carbon atoms.
- x is an integer of l
- 2 or 3 m is an integer of l
- 2 or 3 n is an integer of from 0 to 50, preferably of from 1 20,
- Y is hydrogen, methyl or ethyl Z is hydrogen or alkyl of from one to 20 carbon atoms, and
- M is a cation, e.g. H, alkali metal, alkaline earth metal, heavy metal, ammonium or amino, are characterized by outstanding anti-wear and extreme pressure properties and are valuable lubricants and lubricant additives.
- the sulfur containing phosphate esters of the present invention may conveniently be prepared by the reaction with P 0 of a thio ether of a phenol. Since the phosphate esters derived from an (alkylthio)-phenol, or more preferably an alkoxylated (alkylthio)-phenol are particularly preferred, the present invention will be described with particular reference to their production. This reaction can advantageously be carried out under the conditions disclosed in US Pats. No. 3,004,056 to Nunn and Hesse and No. 3,004,057 to Nunn for the preparation of mixed monoand di-esters of nonionic surfactants, and the disclosure of said patents is incorporated herein by reference.
- the reaction is preferably carried out by adding the P 0 gradually, with vigorous agitation, to the (alkylthio)-phenol or alkoxylated (alkylthio)-phenol in liquid form.
- the reaction is exothermic and cooling is necessary in some cases to keep the temperature below 110 C.
- the reaco XQ tion proceeds continuously during the addition of the P 0 and is preferably followed by maintenance of the reaction mixture at temperatures of from ambient up to 110 C., or even somewhat higher, for an additional period of time after completion of such addition to allow for complete solution of the P 0 and its reaction with the (alkylthio)-phenol or alkoxylated (alkylthio)- phenol.
- the reaction product obtained by carrying out the reaction as described above is a mixture of the primary esters (sometimes called monoesters) and secondary esters (sometimes called diesters) of phosphoric acid and the (alkylthio)-phenol or alkoxylated (alkylthio)- phenol, and may still contain appreciable amounts of unreacted (alkylthio)-phenol or alkoxylated (alkylthio)-phenol starting material.
- Such mixtures which will usually consist of about 20 to 50 percent of a secondary phosphate ester, 30 to percent of the primary phosphate ester and 0 to 50 percent of the unreacted (alkylthio)-phenol or alkoxylated (alkylthio)- phenol need not be separated, but are useful as is as lubricants and lubricant additives.
- the ratio of primary and secondary phosphate esters is not critical and the presence of unreacted (alkylthio)-phenols or alkoxylated (alkylthio)-phenols, even up to 50 percent by weight of the total reaction product, is not detrimental to the attainment of the objects of the present invention
- the mixture of products obtained directly as the reaction product in the process described above constitutes a preferred form of the sulfur containing phosphate esters of the present invention.
- the ratio of primary and secondary phosphate esters and the amount of unreacted starting material can, however, be controlled by various known techniques, if desired.
- the amount of unreacted (alkylthio)-phenol or alkoxylated (alkalthio)-phenol can be reduced to a minimum of less than 10 percent by choice of the molar ratio of hydroxyl containing compound to P 0
- the triester may be produced, by reacting the (alkylthio)-phenol or alkoxylated (alkylthio)- phenol with PCI;,, or a triaryl phosphite, to form a phosphite which can then be readily oxidized to the triester, or the triester may be formed directly by reaction of the (alkylthio)-phenol or alkoxylated (alkylthio)-phenol with POCI
- the thio ethers of phenols which may be used as such or preferably in the form of their alkoxylated derivatives for the production of the sulfur containing phosphate esters of the present invention may be represented by the general formula:
- R in the above formula is methyl
- R in the above formula is methyl
- R for R to be butyl or octyl, dibutylsulfide or dioctylsulfide, respectively, would be used.
- R to be aryl a diary] sulfide, e.g. diphenylsulfide, may be used, and if R is to be aralkyl, a di-aralkylsulfide, e.g. di-benzylsulfide, should be used.
- Other methods for the synthesis of thio ethers of phenols of the above formula are disclosed in US. Pat. No. 2,745,878 to Mavity, US. Pat. No. 2,923,743 to Delfs et al. and in' an article by Miller and Read in JACS 55, l,2241,226 (1933)and may be used.
- the (alkylthio)-phenol is condensed with an alkylene-oxide, by introducing the alkylene-oxide into the heated (alkylthio)-phenol, which preferably containsa small amount of alkali, such as sodium or potassium hydroxide, as catalyst, until the desired amount of alkylene-oxide has been condensed with the (alkylthio)-pheno1.
- alkali such as sodium or potassium hydroxide
- Ethyleneoxide, propylene-oxide or butylene-oxide maybe used for the production of the products of this invention, or if desired a mixture of such alkylene-oxides may be used, or if desired the (alkylthio)- phenol may first be condensed with one to several molar proportions of one alkylene-oxide, say propylene or butylene-oxide, and the thus obtained glycol ether then condensed with one or more molar proportions of another alkylene-oxide, say ethylene-oxide.
- the oil solubility of the (alkylthio)-phenols increases as the number of carbon atoms in alkyl group of the (alkylthio)-phenol, and/or in any other alkyl substituent thereon, is increased. Also as the number of carbon atoms present in such alkyl groups increases the amount of alkyleneoxide necessary to obtain products having a given degree of water-solubility also increases. Thus by selection of the particular (alkylthio)-phenol, and/or the amount of alkylene-oxide condensed therewith, products having any desired degree of oil or-water solubility can be tailor-made.
- novel sulfur containing primary and secondary phosphate esters ofthe present invention can be used as lubricants. either in their free acid form or in the form of their salts, such as their alkali metal salts, e.g. sodium, potassium or lithium salts, their alkaline earth metal salts, e.g. barium, calcium, magnesium and stron- 1 lubricating oilsof'petroleum origin and synthetic lubrica'nts, for these and other applications such as greases, rust-preventives, gear, turbine, transmission and similar oils and lubricants to improve the anti-wearextreme pressure properties thereof.
- their alkali metal salts e.g. sodium, potassium or lithium salts
- their alkaline earth metal salts e.g. barium, calcium, magnesium and stron- 1 lubricating oilsof'petroleum origin and synthetic lubrica'nts
- ester lubricants such as alkyl oxalates, malonates, succinates, glutarates, adipates, pimelates, suberates, azelates, sebacates, esters from polyols such as pentaerythritol, trimethylol propane and sorbitol, alkyl esters of aliphatic monocarboxylic acids such as lauric, oleic, palmitic, stearic and behenic acids and'the like.
- lubricants include silicone lubricants such as polysiloxane oils and greases of the type poly-alkyl, polyaryl, polyalkoxy, polyaryloxy such as polydimethoxy-phenoxy siloxane, silicate ester oils such as tetraalkyloxy and tetraaryloxy-silanes, and the like.
- fluorocarbon lubricants such as CF,CFC
- polyalkylene glycol lubricants such as ethylene oxide-propylene oxide copolymers and phosphate esters such as wherein R, R and R" represent hydrogen, phenyl, al-
- R is an alkyl group of one to 20 carbon atomsphenyl or benzyl x is an integer of from l to 3 inclusive n is an integer of from 0 to 50 inclusive m is an integer of 1 to 3 inclusive Y is hydrogen, methyl or ethyl Z is hydrogen or alkyl, ofone to 20 carbon atoms'and M is a cation, e.g. H, alkali metal, alkaline earth metal.
- R is methyl
- Z is alkyl of one to 20 carbon atoms.
- R is methyl
- n is an integer of l to 20 inclusive.
- a R is methyl
- Z is alkyl of one to 20 carbon atoms.
Abstract
WHEREIN: R is an alkyl group of one to 20 carbon atoms, phenyl or aralkyl X IS AN INTEGER OF FROM 1 TO 3 INCLUSIVE N IS AN INTEGER OF FROM 0 TO 50 INCLUSIVE (PREFERABLY 1-20) M IS AN INTEGER OF 1 TO 3 INCLUSIVE Y is hydrogen, methyl or ethyl Z is hydrogen or alkyl, of one to 20 carbons atoms and M is a cation, e.g., H, alkali metal, alkaline earth metal, heavy metal, ammonium or amino. These sulfur containing phosphate esters have valuable lubricating properties and exhibit good anti-wear extreme pressure properties both alone or in water or as additives to other lubricants, such as mineral oils, especially for use as cutting oils or other metal working applications, gear lubricants, etc.
Description
Claims (11)
- 2. Sulfur containing phosphate esters as defined in claim 1 wherein: x is 1 and n is an integer of 0 to 20 inclusive.
- 3. Sulfur containing phosphate esters as defined in claim 2 wherein: Z is hydrogen.
- 4. Sulfur containing phosphate esters as defined in claim 3 wherein: R is methyl.
- 5. Sulfur containing phosphate esters as defined in claim 2 wherein: Z is alkyl of one to 20 carbon atoms.
- 6. Sulfur containing phosphate esters as defined in claim 5 wherein: R is methyl.
- 7. Sulfur containing phosphate esters as defined in claim 2 wherein: n is an integer of 1 to 20 inclusive.
- 8. Sulfur containing phosphate esters as defined in claim 7 wherein: Z is methyl.
- 9. Sulfur containing phosphate esters as defined in claim 8 wherein: R is methyl.
- 10. Sulfur containing phosphate esters as defined in claim 7 wherein: Z is alkyl of one to 20 carbon atoms.
- 11. Sulfur containing phosphate esters as defined in claim 1 wherein m is 1 or 2.
- 12. Sulfur containing phosphate esters as defined in claim 1 wherein m is 3.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US8047770A | 1970-10-13 | 1970-10-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3723578A true US3723578A (en) | 1973-03-27 |
Family
ID=22157626
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00080477A Expired - Lifetime US3723578A (en) | 1970-10-13 | 1970-10-13 | Phosphate esters of ethers of thiol substituted phenols |
Country Status (3)
Country | Link |
---|---|
US (1) | US3723578A (en) |
DE (1) | DE2150786A1 (en) |
GB (1) | GB1345060A (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4151099A (en) * | 1977-01-03 | 1979-04-24 | Basf Wyandotte Corporation | Water-based hydraulic fluid and metalworking lubricant |
US4701448A (en) * | 1985-01-29 | 1987-10-20 | Asahi Denka Kogyo Kabushiki Kaisha | Metal salt of organic phosphate and an antihyperlipemic agent containing the same |
US4918211A (en) * | 1986-12-12 | 1990-04-17 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Surface active compounds having a polymerizable moiety |
US5512534A (en) * | 1992-10-03 | 1996-04-30 | Hoechst Aktiengesellschaft | Crop-protection formulations |
US6204257B1 (en) | 1998-08-07 | 2001-03-20 | Universtiy Of Kansas | Water soluble prodrugs of hindered alcohols |
US6541428B1 (en) * | 1996-11-25 | 2003-04-01 | Rhodia Chimie | Sulphur orthophosphate compositions, preparation and use |
US20050042280A1 (en) * | 2001-12-28 | 2005-02-24 | Rogers Tracey L. | Aqueous based pharmaceutical formulations of water-soluble prodrugs of propofol |
US20050203068A1 (en) * | 2002-04-08 | 2005-09-15 | Peggy Wingard | Pharmaceutical compositions containing water-soluble prodrugs of propofol and methods of administering same |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3151022A (en) * | 1962-03-08 | 1964-09-29 | Allied Chem | Omicron, omicron-dimethyl-omicron-(4-methylmercaptophenyl) phosphate and pesticidal use |
-
1970
- 1970-10-13 US US00080477A patent/US3723578A/en not_active Expired - Lifetime
-
1971
- 1971-10-06 GB GB4648271A patent/GB1345060A/en not_active Expired
- 1971-10-12 DE DE19712150786 patent/DE2150786A1/en active Pending
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3151022A (en) * | 1962-03-08 | 1964-09-29 | Allied Chem | Omicron, omicron-dimethyl-omicron-(4-methylmercaptophenyl) phosphate and pesticidal use |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4151099A (en) * | 1977-01-03 | 1979-04-24 | Basf Wyandotte Corporation | Water-based hydraulic fluid and metalworking lubricant |
US4701448A (en) * | 1985-01-29 | 1987-10-20 | Asahi Denka Kogyo Kabushiki Kaisha | Metal salt of organic phosphate and an antihyperlipemic agent containing the same |
US4918211A (en) * | 1986-12-12 | 1990-04-17 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Surface active compounds having a polymerizable moiety |
US5512534A (en) * | 1992-10-03 | 1996-04-30 | Hoechst Aktiengesellschaft | Crop-protection formulations |
US6541428B1 (en) * | 1996-11-25 | 2003-04-01 | Rhodia Chimie | Sulphur orthophosphate compositions, preparation and use |
US6204257B1 (en) | 1998-08-07 | 2001-03-20 | Universtiy Of Kansas | Water soluble prodrugs of hindered alcohols |
US6451776B2 (en) | 1998-08-07 | 2002-09-17 | University Of Kansas | Water soluble prodrugs of hindered alcohols |
US6872838B2 (en) | 1998-08-07 | 2005-03-29 | University Of Kansas | Water soluble prodrugs of hindered alcohols |
US7244718B2 (en) | 1998-08-07 | 2007-07-17 | University Of Kansas | Water soluble prodrugs of hindered alcohols |
US20050042280A1 (en) * | 2001-12-28 | 2005-02-24 | Rogers Tracey L. | Aqueous based pharmaceutical formulations of water-soluble prodrugs of propofol |
US20050203068A1 (en) * | 2002-04-08 | 2005-09-15 | Peggy Wingard | Pharmaceutical compositions containing water-soluble prodrugs of propofol and methods of administering same |
Also Published As
Publication number | Publication date |
---|---|
GB1345060A (en) | 1974-01-30 |
DE2150786A1 (en) | 1972-04-20 |
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Owner name: RHONE - POULENC SPECIALITY CHEMICALS Free format text: A CORRECTIVE ASSIGNMENT TO CORRECT THE SINGLE SERIAL NUMBER 07194,259 IDENTIFIED IN PREVIOUSLY RECORDED ASSIGMENT ON REEL 5315/FRAME 589.;ASSIGNOR:GAF CHEMICALS CORPORATION;REEL/FRAME:005722/0439 Effective date: 19910513 |
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